US008157873B2

(12) United States Patent (10) Patent No.: US 8,157,873 B2

Murphy et al. (45) Date of Patent: *Apr. 17, 2012
(54). WAXAND WAX-BASED PRODUCTS 2,784,891 A 3, 1957 Thielke
3,448,178 A 6/1969 Flanagan
3,630,697 A 12/1971 Duling et al.
(75) Inventors: Timothy A. Murphy, Yorkville, IL (US); 3,645,705 A 2f1972 Miller et al.
Michael D. Shepherd, Rock Hill, SC 3.744.956 A 7, 1973 Hess
(US) 3,844,706 A 10/1974 Tsaras
4,118,203 A 10, 1978 Beardmore et al.
(73) Assignee: Elevance Renewable Sciences, Inc., (Continued)
Bolingbrook, IL (US)
c b disclai h f thi FOREIGN PATENT DOCUMENTS
(*) Notice: Su ject to any disc aimer, t eterm. Oths DE 19956226 5, 2001
patent is extended or adjusted under 35
U.S.C. 154(b) by 0 days. (Continued)
This patent is Subject to a terminal dis- OTHER PUBLICATIONS
claimer.
Behren et al., “Beeswax and other Non-Paraffin Waxes.” Presented at
(21) Appl. No.: 12/903,570 NCA Technical Meeting, Jun. 19-20, 1991, 6 pages.
(22) Filed: Oct. 13, 2010 (Continued)
(65) Prior Publication Data Primary Examiner — Cephia DToomer
US 2011 FO165529 A1 Jul. 7, 2011 (74) Attorney, Agent, or Firm — Brinks Hofer Gilson &
Lione
Related U.S. Application Data
(62) Division of application No. 1 1/502.977, filed on Aug. (57) ABSTRACT
11, 2006, now Pat. No. 7,833,294, which is a division The present lipid-based wax compositions commonly include
of application No. 10/434,447, filed on May 8, 2003, a polyol fatty acid ester component (made up of partial and/or
now Pat. No. 7,192,457. completely esterified polyols). Generally, at least a portion of
the polyol fatty acid ester has been subjected to a transesteri
(51) o:/00 2006.O1 fication reaction. Lipid-based wax compositions having a
CIIC5/00 R melting point of about 48°C. to about 75° C. can be particu
( .01) larly advantageous for use in forming candles. The wax may
(52) U.S. Cl. ........ grrrrr. 44/275; 431/288 contain other components such as mineral wax, plant wax,
(58) Field of Classification Search .................... 44/275; insect wax, and/or other components. The polyol fatty acid
431/288 ester component can include triacylglycerols such as those
See application file for complete search history. derived from plant oils (soybean oil, palm oil, etc.). The
polyolester component may be characterized based on one or
(56) References Cited more of its physical characteristics, such as SFI-40, SFI-10,
U.S. PATENT DOCUMENTS
typical crystal structure, IV, melting curve, and/or other prop
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1935,946 A 11/1933 Egan et al.
1954,659 A 4, 1934 W11
2.468,799 A 5, 1949 Ziels et al. 11 Claims, 6 Drawing Sheets

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Minutes
 US 8,157,873 B2
Page 2

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 US 8,157,873 B2
1. 2
WAXAND WAX-BASED PRODUCTS powder compression technology. However, the production of
a Superior candle product by wax powder compression is not
CROSS-REFERENCE TO RELATED PATENT readily achieved. The compression-molding of a wax powder
APPLICATIONS is affected by formulation variables, such as wax melting
point, particle size distribution, the number and quantity of
This application is a divisional of U.S. patent application additives such as air fresheners and colorants, and the like,
Ser. No. 1 1/502,977, filed Aug. 11, 2006 now U.S. Pat. No. and process variables, such as compression time and the
7,833,294, which is a divisional of U.S. patent application degree of compression.
Ser. No. 10/434.447, filed May 8, 2003, now U.S. Pat. No. There is continuing interest in the development of addi
7,192,457, dated Mar. 20, 2007. The contents of the afore- 10 tional wax materials and candle products which can be manu
mentioned applications are incorporated herein by reference factured by powder compression technology.
in their entirety.
SUMMARY
BACKGROUND
15 The present compositions relate to waxes which may be
For a longtime, beeswax was has been in common usage as used in candles. The waxes typically have a low paraffin
a natural wax for candles. Some time ago, paraffin came into content (less than 50%, and typically much lower amounts).
existence, in parallel with the development of the petroleum The candles are typically formed from a ester-based waxes,
refining industry. Paraffin is produced from the residue left Such as Vegetable oil-based wax, a biodegradable material
over from refining gasoline and motor oils. Paraffin was intro- 20 produced from renewable resources. Since the candles may
duced as a bountiful and low cost alternative to beeswax, be formed from a material with a low paraffin content and
which had become more and more costly and in more and may be substantially devoid of paraffin (e.g. contain no more
more scarce Supply. than about 0.5 wt.% paraffin), the candles are generally clean
Today, paraffin is the primary industrial wax used to pro burning, emitting very little soot. The combination of low
duce candles and other wax-based products. Conventional 25 Soot emission, biodegradability and production from renew
candles produced from a paraffin wax material typically emit able raw material makes the present waxes and candles par
a Smoke and can produce a bad Smell when burning. In addi ticularly environmentally friendly products.
tion, a small amount of particles (“particulates') can be pro The present wax is typically solid at room temperature,
duced when the candle burns. These particles may affect the firm but not brittle, generally somewhat malleable, has no free
health of a human when breathed in. A candle that has a 30 oil visible and is particularly Suited for use in forming many
reduced amount of paraffin would be preferable. types of candles, such as container candles, Votive candles,
Accordingly, it would be advantageous to have other mate and pillar candles. The present waxes are also generally
rials which can be used to form clean burning base wax for capable of providing consistent characteristics. Such as
forming candles. If possible, such materials would preferably appearance, upon cooling and resolidification (e.g., after
be biodegradable and be derived from renewable raw mate- 35 being burned in a candle) of the melted wax. In addition, it is
rials. The candle base waxes should preferably have physical desirable that the wax is capable of being blended with natural
characteristics, e.g., in terms of melting point, hardness and/ color additives to provide an even, solid color distribution. It
or malleability, that permit the material to be readily formed is also desirable that the wax is capable of being blended with
into candles having a pleasing appearance and/or feel to the other additives, such as perfumes or other fragrances, and
touch, as well as having desirable olfactory properties. 40 preferably be capable of exhibiting good fragrance throw
Additionally, there are several types of candles, including when the wax/fragrance blend is burned.
taper, Votive, pillar, container candles and the like, each of The present lipid-based wax compositions commonly
which places its own unique requirements on the wax used in include a polyol fatty acid ester component (made up of
the candle. For example, container candles, where the wax partial and/or completely esterified polyols), at least a portion
and wick are held in a container, typically glass, metal or the 45 of which have been subjected to a transesterification reaction.
like, require lower melting points, specific burning character The transesterification reaction may be catalyzed by an
istics such as wider melt pools, and should desirably adhere to enzyme or by a chemical catalyst (e.g., a basic catalyst). Very
the container walls. The melted wax should preferably retain often the polyol fatty acid ester component has been subjected
a consistent appearance upon resolidification. to an interesterification reaction, e.g., by treatment with a
In the past, attempts to formulate candle waxes from Veg- 50 basic catalyst, Such as a sodium alkoxide. For example the
etable oil-based materials have often suffered from a variety polyol ester component may include a polyol fatty acid ester
of problems. For example, relative to paraffin-based candles, component formed by a process which comprises interesteri
vegetable oil-based candles have been reported to exhibit one fying a polyol fatty acid ester precursor mixture. Due to their
or more disadvantages such as cracking, airpocketformation, desirable melting characteristics, the polyol ester based
and a natural product odor associated with soybean materials. 55 waxes having a melting point of about 48°C. to about 75° C.
Various soybean-based waxes have also been reported to can be particularly advantageous for use in forming candles.
Suffer performance problems relating to optimum flame size, Commonly, the polyol ester based waxes include at least
effective wax and wick performance matching for an even about 51 wt.% of a polyol fatty acid ester component (and
burn, maximum burning time, product color integration and/ more desirably at least about 70 wt.%). More typically, the
or product shelf life. In order to achieve the aesthetic and 60 wax includes at least about 51 wt.% of a completely esterified
functional product Surface and quality sought by consumers polyol ester component (e.g., a mixture of triacylglycerol
of candles, it would be advantageous to develop new Veg compounds optionally combined with complete esters of
etable oil-based waxes that overcome as many of these defi other polyols), and preferably includes at least 70 wt.% of the
ciencies as possible. completely esterified polyol. Very often, the completely
Candles are often prepared by means of melt-processing. 65 esterified polyolester component has been subjected to inter
For purposes of commercial-scale manufacture, there can be esterification conditions. The interesterification of a mixture
economic advantage in the prospective utilization of wax of completely esterified polyols may be conducted on a mix
 US 8,157,873 B2
3 4
ture which also includes one or more polyol partial esters, commonly be incorporated into the present candles include
e.g., a fatty acid monoglyceride and/or fatty acid diglyceride. colorants, fragrances (e.g., fragrance oils), insect repellants
In some embodiments, the wax composition may include and migration inhibitors.
other components such as a mineral wax, a free fatty acid, a If the present wax is used to produce a candle, the same
Solid natural wax (such as plant wax or insect wax), and/or standard wicks that are employed with other waxes (e.g.,
other renewable resource based wax. These waxes are pref paraffin and/or beeswax) can be utilized. In order to fully
erably only present in the composition up to about 49% by benefit from the environmentally-safe aspect of the present
weight, and often in much lower amounts. The mineral wax wax, it is desirable to use a wick which does not have a metal
may be a petroleum wax such as a medium paraffin wax, a core, such as a lead or Zinc core. One example of a Suitable
10 wick material is a braided cotton wick.
microcrystalline paraffin wax and/or a petroleum wax
obtained from crude oil refined to other degrees. In another The present candles may be formed by a method which
embodiment, the wax composition includes no more than includes heating the polyol ester-based wax to a molten state
about 25 wt.% of the alternate waxes. In still another embodi and introduction of the molten polyol ester-based wax into a
ment, the wax composition includes no more than about 10% mold which includes a wick disposed therein. The molten
15 polyol ester-based wax is cooled in the mold to solidify the
by weight of the alternate waxes. Wax.
The present waxes preferably include any number of char Alternatively, the present candles may be formed by com
acteristics. For instance, a glycerol based portion of the wax pression molding. This process is often carried out be intro
may maintain a generally B' crystal structure when Subjected ducing wax particles into a mold and applying pressure. The
to normal candle heating and cooling conditions. The wax resulting candles may be over-dipped, in the same type or a
may include no more than about 1 wt.% free fatty acids different type of wax than used in the compression molding
and/or no more than about 1 wt.% particulate matter. The wax process.
may include no more than about 5 to 15 wt.% 16:0 fatty acids
in its fatty acid profile, no more than about 10 wt.% fatty acids BRIEF DESCRIPTION OF THE DRAWINGS
having hydroxyl groups, and/or no more than about 25 wt.% 25
fatty acids having less than 16 carbon atoms or more than 18 FIG. 1 shows a triacylglycerol profile (“TAG profile') of
carbon atoms. In other embodiments, the wax composition the Sample 2 Precursor Mixture (of Table 1) prior to interes
may include at least about 51 wt.% of the polyol fatty acid terification.
ester component, and preferably include at least about 51 wt. FIG. 2 shows a TAG profile of the Sample 2 Mixture (of
% of a completely esterified polyol fatty acid ester compo 30 Table 1) after to interesterification (“Sample 2 Interesterified
nent. The wax may also include additives which impart useful Wax”).
characteristics such as color or scent. The wax can preferably FIG. 3 shows a TAG profile of the Sample 13 Precursor
pass a slump test; preferably passing it at least 120° F. The Mixture (of Table 1) prior to interesterification.
wax typically has an SFC-40 of at least about 15. Waxes FIG. 4 shows a TAG profile of the Sample 13 Mixture (of
according to these embodiments commonly do not have large 35 Table 1) after to interesterification (“Sample 13 Interesteri
spikes in their melting curves (which can be determined by an fied Wax”).
up-heat melting curve measured by DSC). The DSC curves FIG. 5 shows a DSC scan of up-heats of the Sample 2
for the precursor mixtures shown in FIGS. 5 and 6 are Precursor Mixture (2-pre) and the Sample 2 Interesterified
examples of triacylglycerol mixtures which exhibit large Wax (2-post) as described in Example 3.
spikes in their up-heat melting curves. 40 FIG. 6 shows a DSC scan of the first up-heat of the Sample
Waxes Suitable for use as pillar candles can have a melting 13 Precursor Mixture (13-pre) and the Sample 13 Interesteri
point of about 55° C. to about 70° C., and commonly have an fied Wax (13-post) as described in Example 3.
IV of about 15-50. The wax may be in a particulate form to
facilitate forming waxes by compression molding or to be DETAILED DESCRIPTION OF THE PREFERRED
included in candle making kits. Waxes suitable for use in 45 EMBODIMENTS
making Votive candles commonly have a melting point of
about 52°C. to about 60°C. These waxes commonly have an As used herein, a “fully hydrogenated vegetable oil refers
IV of about 35-65. Waxes suitable for use in forming con to a vegetable oil which has been hydrogenated to an Iodine
tainer candles typically have a melting point of about 48°C. Value of no more than about 5. The term “hydrogenated' is
to about 57°C. Such waxes generally have an IV of about 50 used herein to refer to fatty acid ester-based stocks that are
45-70. Further, these container candle waxes preferably have either partially or fully hydrogenated. Instead of employing a
an SFC-10 that is at least twice its SFC-40. highly hydrogenated vegetable oil, a highly unsaturated tria
It has been reported that a candle with a string-less wick cylglycerol material derived from precipitating a hard fat
can beformed by Suspending fine granular or powdered mate fraction from a vegetable oil may be employed. Hard fat
rial, such as silica gel flour or wheat fiber in a vegetable oil 55 fractions obtained in this manner are predominantly com
Such as soybean oil, cottonseed oil and/or palm oil. The posed of Saturated triacylglycerols and mono unsaturated
inclusion of particulate material in a candle wax can result in triacylglycerols.
a two phase material and alter the visual appearance of a Other polyol esters can be used in the transesterification of
candle. Accordingly, the present polyol ester-based wax is vegetable oils. As used herein, “polyol esters' refers to esters
preferably Substantially free (e.g., includes no more than 60 produced from polyols containing from two to about 10 car
about 0.5 wt.%) of particulate material. As used herein, the bon atoms and from two to six hydroxyl groups. Preferably,
term “particulate material” refers to any material that will not the polyols contain two to four hydroxyl moieties. Non-lim
dissolve in the polyol ester component of the wax, when the iting examples of polyols include 1.2-propanediol. 1,3-pro
wax is in a molten state. panediol. 1,2-butanediol. 1,3-butanediol. 2,3-butanediol,
The polyol ester-based wax may also include minor 65 2-ethyl-1,3-propanediol, 2-ethyl-2-butyl-1,3-propanediol,
amounts of other additives to modify the properties of the neopentylglycol, 2,2,4-trimethyl-1,3-pentanediol, trimethy
waxy material. Examples of types of additives which may lolpropane (TMP), and pentaerythritol. Neopentyl glycol,
 US 8,157,873 B2
5 6
TMP, and pentaerythritol are particularly useful polyols. a material with desirable properties for forming a candle.
Polyol esters can be produced by transesterification of a Although the solid fat content is generally determined by
polyol with methyl esters offatty acids. The fatty acid may be measurement of the Solid content of a triglycerol material as
a branched chain fatty acid. For example, 2-ethylhexanoic a function over a range of 5 to 6 temperatures, the triglycerol
acid is a potential branched chain fatty acid. Suitable TMP 5 based materials described herein can be characterized in
esters can include, for example, TMP tri(2-ethylhexanoate), terms of their solid fat contents at 10° C. (“SFC-10) and/or
TMP triheptanoate (TMPTH), TMP tricaprylate, TMP trica 40° C. (“SFC-40).
proate, and TMP tri(isononanoate). Esterification reactions are the processes by which an acyl
The mixture of acids isolated from complete hydrolysis of group is added onto a polyol. Such as glyceride, monoglyc
the polyolester in a specific sample is referred hereinto as the 10 eride, diglyceride, triglyceride, polyhydroxyl alcohol, and the
“acid composition' of that sample. By the term “acid com like, to form either a partial polyol ester or a completely
position” reference is made to the identifiable acid residues in esterified polyol ester. The acyl group(s) of a polyol ester can
the various esters. The distribution of acids in a particular be replaced and/or repositioned by reacting the polyol ester
mixture of esters may be readily determined by methods with another ester (e.g., another polyol ester and/or a simple
known to those skilled in the art. 15 alkyl ester, such as a fatty acid alkyl ester) in a transesterifi
In general, oils extracted from any given plant or animal cation reaction. As employed herein, transesterification refers
Source comprise a mixture of triacylglycerols characteristic to a chemical reaction which results either in the exchange of
of the specific source. The mixture offatty acids isolated from an acyl group between two positions of a polyol polyester or
complete hydrolysis of the triacylglycerols and/or other fatty of the exchange of an acyl group in one ester compound with
acid esters in a specific sample are referred herein to as the an acyl group in a second ester compound or a carboxylic
“fatty acid composition' of that sample. By the term “fatty acid. Interesterification as employed herein refers to a trans
acid composition” reference is made to the identifiable fatty esterification reaction, which results in the exchange of acyl
acid residues in the various esters. The distribution of fatty groups between a mixture of different ester compounds as
acids in a particular oil or mixture of esters may be readily well as between estergroups on different positions of a polyol
determined by methods known to those skilled in the art, e.g., 25 polyester. As used herein, the term polyol polyester refers to
via gas chromatography or conversion to a mixture of fatty any ester compound which contains more than one ester
acid methyl esters followed by analysis by gas chromatogra group. The polyols employed in the polyol esters used in the
phy. present waxes commonly have from 2 to 6 carbon atoms and
As employed herein, the term “interesterified when used 2 to 6 hydroxyl groups. The interesterification reaction may
in conjunction with “polyol fatty acid ester”, “triacylglyc 30 be run until the distribution of ester groups in a polyol mixture
erol’ or other polyol ester refers to an ester composition is substantially that predicted from a thermodynamic distri
which has been treated in a manner that results in the bution of the ester groups, both within individual polyolester
exchange of at least a portion of the acyl groups in the polyol compounds and between differing polyol esters. The result
esters present with other acyl groups, and/or other esters ing distribution of the ester groups is generally very similar to
present. The reaction may employ a catalyst which may be a 35 the distribution predicted from a randomized distribution
chemical reagent or a enzymatic catalyst, Such as a lipase. As (statistical distribution) of the ester groups. A mixture of
employed herein, the term “fully interesterified when used in polyol ester compounds which has such a randomized distri
conjunction with “polyol fatty acid ester', “triacylglycerol bution of ester groups will not exhibit any Substantial change
or other polyol ester refers to an ester composition for which in the distribution of its chemical components when subjected
the melting point when further treated with sodium methox 40 to further interesterification in the presence of a basic catalyst,
ide under the conditions described in Example 1 herein will Such as Sodium methoxide. Such a mixture of esters is
change by no more than about 3° F. referred to herein as a fully interesterified polyol ester and
The polyolester component may include apartial fatty acid after being subjected to further base catalyzed transesterifi
ester of one or more polyols and/or a polyol which is fully cation conditions will not exhibit a change in its melting point
esterified with fatty acids (“complete polyol fatty acid ester'). 45 of more than about 3° F (no more than about 1.5°C.).
Examples of complete polyol fatty acid esters include tria The acyl group in the present polyol esters can be derived
cylglycerols, propyleneglycol diesters and tetra esters of pen from any number of sources. For instance, it can be derived
taerythritol. Examples of suitable polyol partial esters include from monoglyceride, diglyceride, triglyceride, ester, free
fatty acid monoglycerides, fatty acid diglycerides and Sorbi fatty acid, and/or other source of acyl groups. The non-acyl
tan partial esters (e.g., diesters and triesters of Sorbitan). The 50 portion (“R group') of the acyl group can be straight or
polyol typically contains from 2 to 6 carbonatoms and 2 to 6 branched, saturated or unsaturated, and/or contain non-car
hydroxyl groups. Examples of suitable polyols include glyc bon Substituents including oxygen (such as hydroxyl groups),
erol, ethyleneglycol, propyleneglycol, pentaerythritol, Sorbi Sulfur and/or nitrogen. Typically the acyl group includes an R
tan and sorbitol. group which is an alkyl group, an alkenyl group, or a hydroxy
The method(s) described herein can be used to provide 55 Substituted alkyl group. The majority of the R groups are
candles from triglycerol-based materials having a melting typically straight chain Saturated hydrocarbon groups
point and/or solid fat content which imparts desirable mold (“straight chain alkyl groups') and/or straight chain mono
ing and/or burning characteristics. The Solid fat content as unsaturated hydrocarbon groups (“straight chain alkenyl
determined at one or more temperatures is a measure of the groups').
fluidity properties of a triglycerol stock. Solid fat content 60 Lipases are typically obtained from prokaryotic or eukary
(“SFC) can be determined by Differential Scanning calorim otic microorganisms and typically fall into one of three cat
etry (DSC) using the methods well known to those skilled egories (Macrae, A. R., J.A.O.C.S.60:243A-246A (1983);
in the art. Fats with lower solid fat contents have a lower “Macrae, 1983). A first category includes nonspecific
Viscosity, i.e., are more fluid, than their counterparts with high lipases capable of releasing or binding any fatty acid from or
Solid fat contents. 65 to any glyceride position. These lipases are similar to chemi
The melting characteristics of the triglycerol-based mate cal processes. Such lipases have been obtained from Candida
rial may be controlled based on its solid fat content to provide cylindracae, Corynebacterium acnes and Staphylococcus
 US 8,157,873 B2
7 8
aureus (Macrae, 1983). A second category of lipases only SFC-40 of at least about 15. More preferably, the wax has an
adds or removes specific fatty acids to or from specific glyc SFC-40 of at least about 20. The wax preferably has an Iodine
erides. Thus, these lipases generally tend to be useful for Value of about 40 to 75.
producing or modifying specific glycerides. Such lipases Another embodiment provides an ester-based composition
have been obtained from Geotrichum candidium and Rhizo which includes at least about 51 wt.% of an interesterified
pus, Aspergilus, and Mucor genera (Macrae, 1983). A third polyol fatty acid ester. The composition can also include a
category of lipases catalyze the removal or addition of fatty wax component such as an insect wax or other naturally
acids from the glyceride carbons on the end in the 1- and occurring wax and/or a petroleum wax. The ester-based wax
3-positions. Such lipases have been obtained from Thermo can also have a melting point of about 45° C. to 60° C. and/or
10 an SFC-40 of at least about 20.
myces lanuginosa, Rhizomucor miehei, Aspergillus niger,
Mucor javanicus, Rhizopus deleimar, and Rhizopus arrhizus Another embodiment is directed to a candle having a wick
(Macrae, 1983). and a wax. The wax has a melting point of about 45° C. to
about 75° C. and includes a triacylglycerol component. The
One embodiment is directed to a lipid-based wax compo triacylglycerol component preferably has a fractional con
sition having a melting point of about 48°C. to about 75° C. 15 centration by weight of tri(HC)-TAG (expressed as a percent
and including a polyol fatty acid ester component formed by age) which is equal to the cube of the percent concentration by
a process which includes interesterifying a polyol fatty acid weight of HC in the fatty acid profile+E wt.%. HC represents
ester precursor. The polyol fatty acid ester component can the fatty acid which is present in the greatest amount in the
include a fully esterified polyol fatty acid ester component. fatty acid composition of the triacylglycerol component, and
The wax composition commonly includes at least about 51 tri(HC)-TAG is a triacylglycerol having three HC fatty acid
wt.% of the fully esterified polyol fatty acid ester component, acyl groups.
and more commonly at least about 70 wt.%. The fully esteri Another embodiment is directed to a method for forming a
fied polyol fatty acid ester component can include triacylg wax. The method includes creating a precursor mixture which
lycerol. The wax preferably has a melting point of about 53° includes at least (a) a completely esterified polyol ester Such
C. to 70° C., or about 50° C. to 65° C., or about 48° C. to 58° 25 as triacylglycerol and (b) glycerin and/or other polyol (e.g.
C. The wax preferably has an SFC-40 of at least about 15, and propylene glycol and/or sorbitan). The method further
more preferably at least about 20. For waxes designed to be includes interesterifying the precursor mixture, preferably
used in container candles, it may be desirable to have an until the mixture is fully interesterified. The method may
SFC-10 that is at least about twice as much as its SFC-40 (i.e., further include removing portions of the resulting mixture,
the SFC-10:40 ratio is at least about 2.0). 30 Such as free fatty acids, glycerin molecules, or other portions.
Another embodiment is directed to a candle made from a Another embodiment is directed to a polyol-based wax
triacylglycerol containing wax. The candle includes a wick suitable for use as a candle wax. The polyol-based wax
and a wax. The wax has a melting point of about 45° C. to includes a completely esterified polyol fatty acid ester com
about 75°C. and includes a triacylglycerol component having ponent. The wax preferably has a melting point of about 130°
a fatty acid composition which includes Stearic acid. The
35 F. to 155° F (about 54° C. to 68°C.), and an SFI-40 of at least
triacylglycerol component preferably has a percent concen about 40. The wax also preferably has an Iodine Value of
about 20 to 45.
tration by weight of SSS-TAG which is equal to the cube of a Another embodiment provides a lipid-based wax suitable
fractional concentration by weight of Stearic acid in the fatty for use as a candle wax. The lipid-based wax includes at least
acid profile+E wt.%. E. can be selected to be no more than a 40 about 50 wt.% of a fully interesterified polyol fatty acid ester
preset amount, or no more than a percentage of the SSS-TAG component, and more typically at least about 70 wt.%. The
concentration. E is preferably selected to be no more than lipid-based wax preferably has a melting point of about 130°
about 5 or 7 wt.%, and desirably less than or equal to 3 wt.%. F. to 155° F (about 54° C. to 68°C.) and/oran SFI-40 of at
The wax preferably includes at least about 51 wt.% of the least about 40. The lipid-based wax may include a polyol fatty
triacylglycerol component. Stearic acid may often makeup 45 acid partial ester, and may include up to about 20 wt.% of a
about 30 wt.% or more of the fatty acid composition of the polyol fatty acid partial ester. The lipid-based wax may fur
triacylglycerol component. The 1.2:1.3-Sratio in the triacylg ther include a mineral wax, an insect wax, some other natu
lycerol component is preferably at least 1.5; the 1.2:1.3-S rally occurring wax. The lipid-based wax can also include a
ratio being the percent concentration by weight of 1.2-S-3- free fatty acid component. In some circumstances, the fatty
X-triacylglycerol divided by the percent concentration by 50 acid composition of the lipid-based wax does not include
weight of 1.3-S-2-X-triacylglycerol (the ratio also being more than about 15 wt.% palmitic acid. The fatty acid com
capable of being written as SSQ-TAG:SQS-TAG). position of the lipid-based wax often includes no more than
Another embodiment is directed to a candle comprising a about 1.0 wt.% 18:3 fatty acid. The lipid-based wax prefer
wick and a wax. The wax preferably has a melting point of ably has a slump temperature of at least about 118° F.
about 45° C. to about 75° C. and includes a fully interesteri 55 Another embodiment is directed to a candle having a wick
fied polyol fatty acid ester component. The polyol fatty acid and a wax. The wax preferably has a melting point of about
ester component is preferably a triacylglycerol component. 45° C. to about 75° C. The wax includes a triacylglycerol
Another embodiment provides a lipid-based wax suitable component formed by a process which includes interesteri
for use as a candle wax. The lipid-based wax includes a fying a precursor mixture. The precursor mixture can include
completely esterified polyol fatty acid ester component. The 60 triglycerides, fatty acid monoglycerides, fatty acid diglycer
wax has a melting point of about 50° C. to about 60° C.: an ides, fatty acid alkyl esters, free fatty acids, glycerin, and/or
Iodine Value of about 40 to 75; and an SFC at 10°C. that is at otheresters or polyols. Preferably, the precursor mixture con
least about twice that of the SFC at 40° C. tains at least about 70 wt.% triacylglycerols.
Another embodiment is directed to another polyol-based Transesterification of two polyol esters can randomize the
wax suitable for use as a candle wax. The polyol-based wax 65 distribution of fatty acids among the polyol backbones—
includes a complete polyol fatty acid ester component. The completely, between specific hydroxyl groups of the polyol
wax has a melting point of about 45° C. to 65° C. and an (e.g. between the 1 and 3 positions of the glycerol), and/or
 US 8,157,873 B2
10
between specific polyols or esters. The resulting transesteri Transesterification Methods
fied products have properties different from each of the origi In general, transesterification can be performed by adding
nal polyolesters. Various interesterification techniques can be polyolesters in the presence of a Suitable catalyst and heating
used to add useful properties to polyolester-based waxes. For the mixture. Non-limiting examples of catalysts that can be
example, base can be added to a mixture of ester compounds used to carry out interesterification include base catalysts
to allow random interchange of acyl groups between the (e.g. sodium methoxide), acid catalysts including inorganic
various esters. Alternatively, enzymes and other biological acids such as Sulfuric acid and acidified clays, organic acids
molecules can be added to facilitate interesterification. Other Such as methane Sulfonic acid, benzenesulfonic acid, and
interesterification methods may also be used. toluenesulfonic acid, and acidic resins such as Amberlyst 15.
Interesterification can be used to give waxes more desir
10 Metals such as Sodium and magnesium, and metal hydrides
able properties. For instance, interesterification tends to give may also be useful catalysts. Progress of the reaction can be
compounds a smoother melting curve. This tends to allow for monitored using standard techniques such as high perfor
mance liquid chromatography (HPLC), infrared spectrom
a smoother melt and cooling process. Interesterification can etry, thin layer chromatography (TLC), Raman spectroscopy,
also effect other properties of the waxes in manners that are 15 or UV absorption. Upon completion of the reaction, sodium
beneficial as will be discussed herein. methoxide catalyst can be neutralized, for example, by addi
Some enzymatic transesterification methods enzymes can tion of water, aqueous ammonium chloride, or aqueous phos
be used to generate candles with useful properties. For phoric acid. Acid catalysts can be neutralized by a base Such
example, cocoa butter consists primarily (about 70-80% by as a sodium bicarbonate solution. Deactivated catalyst and
weight) of saturated-oleic-saturated (SatOSat) triglycerides. Soaps (fatty acid salts) can be removed by a water wash,
It is this triglyceride composition which is thought to provide followed by centrifugation. The oil can be dried by addition of
the unique characteristics by which cocoa butter obtains its anhydrous magnesium Sulfate or sodium Sulfate. Remaining
smooth appearing B' structure. These SOS triglycerides water can be removed by heating to about 60° C. or higher
include 1,3-dipalmitoyl-2-monooleine (POP), 1(3)-palmi under vacuum. Methyl esters can be removed by distillation.
toyl-3(1)-stearoyl-2-monooleine (POS) and 1,3-distearoyl-2- 25 Enzymatic methods of transesterification tend to be more
monooleine (SOS). Thus, oleic acid-rich glycerides with an specific with respect to modifying acyl groups. Enzymatic
oleic ester group in the middle position can be incubated with methods of transesterification tend to be used with natural fats
palmitic and Stearic acid in the presence of a 1.3-specific and oils such as mono-, di-, and tri-esters of glycerol with
lipase to produce POP, POS and SOS. These reactions may be fatty acids. The enzymes capable of affecting this transesteri
useful to aid in the development of candles with a more 30 fication in glycerides are generally known as lipases.
uniform appearance. If a lipase is used for transesterification, it can be obtained
The described methods and techniques are applicable to from a cultured eukaryotic or prokaryotic cell line. The lipase
making waxes from polyol esters such as polyol fatty acid can be unspecific or specific with respect to its Substrate.
partial esters and triglycerol fatty acid esters. Waxes from Preferably, the lipase is a 1.3-selective lipase, which catalyzes
these materials can be suitably used to form candles. For 35 transesterification of the terminal esters in the 1 and 3 posi
esters offatty acids, the fatty acids can include any number of tions of a glyceride, or a non-selective, nonspecific lipase.
fatty acids including palmitic acid, Stearic acid, oleic acid, The present method can include batch slurry type reac
hydroxylated fatty acid esters such as ricinoleic acid. Other tions, in which the slurry of lipases and Substrates are mixed
fatty acids which may which may be present in esterified form vigorously to ensure a good contact between them. The trans
as part of a polyol ester include oleic acid, linoleic acid, 40 esterification reaction may be carried out in a fixed bed reac
arachidonic acid, erucic acid, caproic acid, caprylic acid, tor with immobilized lipases.
capric acid, lauric acid, myristic acid, eicosapentaenoic acid Resinous immobilized lipase can be mixed with initial or
(EPA), docosahexaenoic acid (DHA), 5-eicosenoic acid. purified starting material to form a slurry which is packed into
One sign that a polyol ester has been transesterified is that a suitable column. Initial Substrate is prepared from one or
when the polyol ester is further subjected to transesterifica 45 more acyl group Suppliers and/or polyol esters. The tempera
tion conditions, the additional resulting changes are either ture of the Substrate is regulated so that it can continuously
small (if the polyol ester had already been completely trans flow though the column for contact with the lipase and be
esterified) or less than would be ordinarily expected (if the transesterified. If solid glycerides or fatty acids are used, the
polyol ester had been only partially transesterified). This can solid substrates are heated to a fluid state. The substrate can be
be judged by applying the same or similar transesterification 50 caused to flow through the column(s) under the force of
technique to the polyol ester based wax. For instance, if gravity, by using a peristaltic or piston pump, under the influ
methoxide was used to completely randomize the polyol ence of a suction or vacuum pump, or using a centrifugal
esters of a polyol ester based wax, application of methoxide pump. The transesterified polyol esters produced are col
or a randomizing enzyme to the polyol ester based portion of lected and the desired portions are separated from the mixture
the wax would generally result in a polyolester based portion 55 of reaction products by methods well known in the art. This
that is not substantially different from the initial wax. Alter continuous method involves a reduced likelihood of permit
natively, if a 1.3 selective enzyme was used to transesterify a ting exposure of the materials to air during reaction. Alterna
fatty acid based triglycerol, application of a 1.3 selective tively, reaction tanks for batch slurry type production can also
enzyme to the fatty acid triglycerol portion would not result in be used. Preferably, these reaction tanks are also sealed from
a fatty acid based triglycerol component that was Substan 60 air so as to prevent exposure to oxygen, moisture, or other
tially different than the starting fatty acid triglycerol. One way ambient oxidizing species.
to measure this is to measure the properties of the polyol ester Enzymatic activity tends to be affected by factors such as
based wax that tend to change when transesterified (e.g. melt temperature, light and moisture content. Light can be kept out
ing point, ester composition, melting curve, SFC Values, etc.). by using various light blocking or filtering means known in
For instance, a polyol ester's melting point would likely 65 the art. Moisture content, which includes ambient atmo
exhibit little or no change if the polyol ester were further spheric moisture, is controlled by operating the process as a
transesterified. closed system. The closed system can be under a positive
 US 8,157,873 B2
11 12
nitrogenous pressure to expel moisture. Alternatively, a bed resin such a “DOWEX MWA-1’ (weakly basic anion
of nitrogen gas can be placed on top of the Substrate, purifi exchange resin manufactured by the Dow Chemical Co., hav
cation bed or column, or packed lipase column. Other inert ing a tertiary amine as the exchange group, composed basi
gasses such as helium or argon can also be used. These tech cally of polystyrene chains cross linked with divinylbenzene,
niques have the added benefit of keeping atmospheric oxida 150 ANG. in average pore radius and 20-50 mesh in particle
tive species (including oxygen) away from the Substrate, size), and hydrophilic cellulose resin Such as one prepared by
product or enzyme. masking the hydrophilic group of a cellulosic carrier, e.g.,
Enzymes “Cellulofine GC700-m” (product of Chisso Corporation,
There are many microorganisms from which lipases useful 45-105 um in particle size).
in forming lipid-based waxes can be obtained. U.S. Pat. No. 10
TriCX)-TAG
5.219,733 lists examples of Such microorganisms including Randomization of ester contents tends to reduce the num
those of the genus Achromobacter Such as A. iofiurgus and A. ber of polyesters with multiple acid chains of the same type to
lipolyticum, the genus Chronobacterium such as C. viscosum
var. parallipolyticum; the genus Corynebacterium such as C. a statistical amount. With natural oils such as fatty acid based
acnes; the genus Staphylococcus such as S. aureus; the genus 15 tri-esters of glycerol and/or their partially hydrogenated
Aspergillus such as A. niger and A. Oryzae; the genus Candida counterparts, the concentration of tri(X)-TAG esters (triglyc
Such as C. cylindracea, C. antarcticab, C. rosa and C. rugosa; erol esters where each of the three side chains is a given fatty
the genus Humicora Such as H. lanuginosa; the genus Peni acid-X) tend to be present in amounts greater than would be
cillium Such as P caseicolum, P. crustosum, P Cyclopium and statistically predicted. This is even more true when these
P roqueforti; the genus Torulopsis such as T. ernobii; the triglycerol esters have been at least partially hydrogenated
genus Mucor such as M. miehei, M. japonicus and M. javani (which is typical when trying to achieve Sufficient properties
cus; the genus Bacillus Such as B. subtilis; the genus Ther for candle applications). These interesterified esters tend to
momyces Such as T. ibadanensis and T. lanuginosa (see have tri(X)-TAG concentrations much closer to a statistical
Zhang, H. et al. J.A.O.C.S. 78: 57-64 (2001)); the genus distribution. For instance, triglycerol molecules having three
Rhizopus such as R. deleimar; R. japonicus, R. arrhizus and R. 25 stearic acid side chains (SSS-TAG) tend to be more common
neveus; the genus Pseudomonas Such as P. aeruginosa, P than expected in partially hydrogenated soybean oil deriva
fragi, P. cepacia, P. mephitica var. lipolytica and Pfluore tives.
scens; the genus Alcaligenes; the genus Rhizomucor Such as The triCX)-TAG amount can potentially affect the proper
R. miehei; the genus Humicolo such as H. rosa; and the genus ties of a triglycerol based wax. For instance, large amounts of
Geotrichum such as G. candidum. Several lipases obtained 30 SSS-TAG can tend to increase the melting point, and can lead
from these organisms are commercially available as purified to sharper melting curves. The triCX)-TAG composition for a
enzymes. given triglycerol ester based wax that has been randomly
Lipases obtained from the organisms above tend to be interesterified can be defined by the cube of the fractional
immobilized for the present method using suitable carriers by concentration (expressed as a percentage) of the acid plus or
a usual method known to persons of ordinary skill in the art. 35 minus an error factor (which represents that interesterifica
Examples of some potential methods of preparation include tion, in reality, will come close to giving but will not always
the entrapping method, inorganic carrier covalent bond give the exact statistical distribution). This can be expressed
method, organic carrier covalent bond method, and the as tri(X)-TAG =X+E, where tri(X)-TAG is the frac
adsorption method. The present methods also contemplate tional concentration of triCX)-TAG, DX is the fractional con
using crude enzyme preparations or cells of microorganisms 40 centration of X, and E is the error factor. E can be chosen as
capable of overexpressing lipase, a culture of Such cells, a a definite number, or as a percentage of X or XI. As an
Substrate enzyme solution obtained by treating the culture, or example, if X were 50 wt.%, tri(X)-TAG would be 12.5
a composition containing the enzyme. wt.%+E wt.%. This can also be written as (X/10)+E wt.%,
Useful carriers are preferably microporous and have a where X is the integer value of the Xby weight. Thus, if X
hydrophobic porous Surface. Usually, the pores have an aver 45 were 50 wt.%, this would be (50/10)+E wt.% or 12.5+Ewt.
age radius of about 10A to about 1,000 A, and a porosity from %.
about 20 to about 80% by volume, more preferably, from E is suitably selected as at least about 3 wt.%, and more
about 40 to about 60% by volume. The pores give the carrier preferably about 5 wt.%.
an increased enzyme bonding area per particle of the carrier. A preferable value of E where E is a percentage of X is
Examples of preferred inorganic carriers include porous 50 0.1XI, more preferable the value of E is 0.115X, and even
glass, porous ceramics, celite, porous metallic particles Such more preferably the value of E is 0.05X. When restricted to
as titanium oxide, stainless steel or alumina, porous silica gel. high DX triglycerol waxes, the value of E is preferably about
molecular sieve, active carbon, clay, kaolinite, perlite, glass 0.115X or 0.28XI when X is at least 40 wt.%.
fibers, diatomaceous earth, bentonite, hydroxyapatite, cal Some fatty acids that could be suitably be used for X
cium phosphate gel, and alkylamine derivatives of inorganic 55 include, but are not limited to, palmitic acid (PPP-TAG),
carriers. Examples of preferred organic carriers include stearic acid (SSS-TAG), and oleic acid (OOO-TAG). TriCX)-
microporous Teflon, aliphatic olefinic polymer (e.g., polyeth TAG values are best measured when value of the concentra
ylene, polypropylene, a homo- or copolymer of Styrene or a tion of X is at least a minimum amount. The concentration of
blend thereofor a pretreated inorganic Support) nylon, polya X is generally not less than 20% by weight. The concentration
mides, polycarbonates, nitrocellulose and acetylcellulose. 60 of X is typically not less than 30%, and preferably not less
Other suitable organic carriers include hydrophillic polysac than 40%. TriCX)-TAG values tend to give more significant
charides such as agarose gel with an alkyl, phenyl, trityl or results when the concentration of X is not less than 50% by
other similar hydrophobic group to provide a hydrophobic weight.
porous surface (e.g., “Octyl-Sepharose CL-4B”, “Phenyl X may be suitably chosen as the fatty acid which is present
Sepharose CL-4B', both products of Pharmacia Fine Chemi 65 in the highest percent concentration in the triglycerol ester
cals). Microporous adsorbing resins include those made of portion of a wax, written as tri(HC)-TAG. Preferably, all
styrene or alkylamine polymer, chelate resin, ion exchange tri(X)-TAGs meeting certain conditions meet these concen
 US 8,157,873 B2
13 14
tration requirements. For instance, all tri(X)-TAGs where X 10:40 would be expected to be low. The ASFC-10:40 of a
is at least about 20% or at least about 40% by weight meet the triglycerol ester portion of a wax would preferably be less
above triCX)-TAG criteria. than 0.5, more preferably be less than about 0.3, even more
The tri(X)-TAG values of a triglycerol ester portion of the preferably be less than about 0.15, and most preferably be less
wax can be measured. If an interesterified wax is subjected 5 than about 0.05.
again to randomizing interesterification, the tri(X)-TAG con Crystal Structures
centrations will tend not to change very much. Thus, the The crystalline structure of a wax can affect its appearance
tri(X)-TAG ratio of change, tri(X)-TAG.I/I tri(X)- and other qualities. B' structure tends to give a smooth even
TAG), will be about 1, where tri(X)-TAG, is the appearance to the wax, and tends to allow for a more even
percent concentration of tri(X)-TAG before the triglycerol 10 distribution when melted and cooled. For a candle, a B' struc
ester based wax has been subjected to randomizing interest ture tends to give a desirable appearance and texture to the
erification and tri(X)-TAG) is the ratio of tri(X)-TAG wax. Depending on its composition, a triglycerol ester por
after the triglycerol ester based wax has been subjected to tion of a wax preferably can maintain a 3' structure without
randomizing interesterification. While some change is always the use of additives. For waxes that are suitable for use as
possible in a given process, a ratio close to 1 tends to indicate 15 candles, this can be determined by heating the triglycerol
that the triglycerol ester had been formed by an interesterifi ester portion of the wax to its melting point, maintaining the
cation process. The tri(X)-TAG change ratio, tCX)-CR, can be triglycerol ester portion of the wax at its melting point for 20
used to characterize a given triglycerol ester based portion of minutes, allowing the triglycerol ester portion of the wax to
a wax. to X)-CR is generally at least 1+0.3, and more typically cool at room temperature, and determining the resulting crys
equal to 1-tabout 0.15. to X)-CR is suitably equal to 1+0.05. tal structure of the triglycerol ester portion of the wax. The
Since the amount of SSS-TAG can effect the melting prop crystal structure of the resulting triglycerol ester portion of
erties of a triglycerol ester based wax, since Stearic acid tends the wax can be determined using standard diffraction tech
to be a common component of many organic triglycerol niques (e.g., X-ray diffraction techniques), using methods
esters, and since SSS-TAG tends to be located separately known to those of skill inn the art. One example of a method
from the other triglycerol ester components when analyzed 25 for determining crystal structure can be found in van Malssen,
using reversed-phase liquid chromotography (RP-LC), SSS Peschar, and Schenk “Real-Time X-Ray Powder Diffraction
TAG changes are particularly well Suited for determining Investigations on Cocoa Butter, JAOCS 73, 1209-1215
t(X)-CR. (1996). The wax would preferably have substantially f' crys
SFC-10:40 tal structure (at least about 50 wt.%), and would more pref
One common effect of interesterification of triglycerol 30 erably have substantially complete B" structure (at least about
ester based waxes is that the wax tends to take on a more 90 wt.%).
uniform melting pattern. A uniform melting range tends to Slump Test
bring advantages such as wider melt pools and even melting One measure of a wax's suitability for use in a candle is the
of the wax. The advantages are particularly useful when mak slump test. The slump test involves placing a wax on an
ing low melting point waxes for use in container candles 35 angled platform in an oven. Although the test may be run on
because larger diameter candles can be burned out to the edge a free standing candle (e.g., a pillar candle), the test is typi
with smaller wicks than used before. The even melting of the cally run with a candle in a container (e.g., either a poured
wax allows for a gradual melting of the wax from the centerto container candle or a Votive candle that has been placed in a
the edge of the candle. holder). The oven is set at 110° F., and the wax is set on the
One sign of this more uniform melt range is that the SFC 40 angled platform. The wax is then left for an hour at 110° F.
40tends to decrease (less solid material at 40°C.) and SFC-10 The temperature of the oven is increased by 1. F. every hour
tends to increase (more solid material at 10° C.). This is until the wax has been at 120° F. for an hour. If desired, the
particularly true for waxes that have higher amounts of esters temperature can be raised beyond this point in a similar man
having unsaturated fatty acids and which have lower melting ner. The slump temperature' is that temperature at which the
points (generally considered waxes more Suitable for use in 45 wax loses its form and/or begins to slide.
container candles). This uniformity of melting can be mea A wax for use in forming a candle desirably have a slump
sured as the ratio of the SFC-10 of the triglycerol based temperature of at least 115°F. preferably would have a slump
portion of a wax compared to the SFC-40 of that portion. This temperature of 118° F., and more preferably would have a
ratio is expressed as SFC-10:40. Thus, an SFC-10:40 ratio of slump temperature of at least about 120°F. This is generally
2:1 means that twice as much material is solid at 10°C. than 50 more of a problem for low melting point candle waxes (below
at 40° C. 135°F) such as waxes typically considered to be useful as
For container candles, a resulting wax preferably has an container candle waxes.
SFC-10:40 of at least about 1.9, more preferably of at least Melting Curve
about 2, even more preferably of at least about 2.15, and most Post-interesterified candle waxes tend to have broader melt
preferably of at least about 2.5. This would generally apply to 55 curves. These broader melt curves would typically allow for
triglycerol ester based wax portions with melting points less better candle properties, such as wider melt pools and even
than about 135°F. and more typically with triglycerol ester melting of the wax. In a pillar candle this broader melt curve
based wax portions having melting points less than about usually allows the melt pool to reach the edge of the candle
1300 F. without becoming so soft that a hole develops and the wax
The transition to a more uniform melting range can also be 60 runs down the side of the candle.
characterized by the change in SFC-10:40 which can be writ For every 5° C. range near the melting point of the polyol
ten ASFC-10:40. Change in SFC-10:40 ratio is measured by ester based portion of a wax, the difference between the
subtracting the SFC-10:40 of the triglycerol based wax por smallest heat flow uptake value and the greatest heat flow
tion before random interesterification from the SFC-10:40 of uptake value would preferably be less than about 5 mW, more
the triglycerol based wax portion after interesterification. If a 65 preferably less than about 3 mW, and even more preferably no
triglycerol wax which has been randomly interesterified is more than 2 mV. For waxes to be used as candle waxes, the
subjected to random interesterification, then the wax's ASFC melt curve would preferably be measured for waxes which
 US 8,157,873 B2
15 16
have undergone standard candle conditions. For waxes that lanolin, shellac wax, chinese insect wax, and spermaceti.
are suitable for use as candles, this can be determined by Some of the examples of the various types of plant waxes are
heating the polyolester portion of the wax to its melting point, carnauba, candelila, japan wax, ouricury wax, rice-bran wax,
maintaining the polyol ester portion of the wax at its melting jojoba wax, castor wax, bayberry wax, Sugar cane wax, and
point for 20 minutes, allowing the polyol ester portion of the 5 maize wax. Additionally, synthetic waxes may be used. For
wax to cool at room temperature, and determining the result instance, waxes such as polyethylene wax, Fischer-TropSch
ing melting curve of the polyol ester portion of the wax. The wax, chlorinated naphthalene wax, chemically modified wax,
resulting melting curve of the polyol ester portion of the wax Substituted amide wax, alpha olefins and polymerized alpha
can be determined as in the process shown and described in olefin wax may be used.
Example 1 where the candle is allowed to cool at ambient 10 Kits
room temperatures (65 to 75°C.) after the first up-heat. The candle wax may be packaged as part of a candle
Mineral Wax Mixtures making kit, e.g., in the form of beads or flakes of wax, which
A composition may also be formed by combining a lipid includes also typically would include instructions with the
based wax with a mineral wax. Some examples of mineral candle wax. The candle-making kit typically would also
waxes include mineral waxes such as montan wax, peat wax, 15 include material which can be used to form a wick.
and petroleum waxes (petrolatum, paraffin wax, oZokerite Additives
and ceresin waxes). A wide variety of coloring and scenting agents, well known
Petroleum wax tends to be one of the more widely used in the art of candle making, are available for use with waxy
waxes for current candles. The petroleum wax can be a by materials. Typically, one or more dyes or pigments is
product of the petroleum refining process and may be employed provide the desired hue to the color agent, and one
obtained commercially from suppliers such as Witco. The or more perfumes, fragrances, essences or other aromatic oils
quality and quantity of the wax obtained from the refining is used provide the desired odor to the scenting agent. The
process is dependent upon the source of the crude oil and the coloring and scenting agents generally also include liquid
extent of the refining. The petroleum wax component of the carriers which vary depending upon the type of color- or
wax composition includes, for example, a paraffin wax, 25 scent-imparting ingredient employed. The use of liquid
including medium paraffin wax, microcrystalline paraffin organic carriers with coloring and scenting agents is preferred
wax or a combination thereof. However, petroleum wax because such carriers are compatible with petroleum-based
obtained from crude oil refined to other degrees may also be waxes and related organic materials. As a result, such color
used. ing and scenting agents tend to be readily absorbed into waxy
Although the exact chemical compositions of these waxes 30 materials. It is especially advantageous if a coloring and/or
are not known as the nature of these by-products vary from scenting agent is introduced into the waxy material when it is
one distillation process to the next, these waxes tend to be in the form of prilled granules.
composed of various types of hydrocarbons. For example, The colorant is an optional ingredient and is commonly
medium paraffin wax is generally composed primarily of made up of one or more pigments and dyes. Colorants are
straight chain hydrocarbons having carbon chain lengths 35 typically added in a quantity of about 0.001-2 wt.% of the
ranging from about 20 to about 40, with the remainder typi waxy base composition. If a pigment is employed, it is typi
cally comprising isoalkanes and cycloalkanes. The melting cally an organic toner in the form of a fine powder Suspended
point of medium paraffin wax is typically about 50° C. to in a liquid medium, Such as a mineral oil. It may be advanta
about 65° C. Microcrystalline paraffin wax is generally com geous to use a pigment that is in the form of fine particles
posed of branched and cyclic hydrocarbons having carbon 40 Suspended in a vegetable oil, e.g., an natural oil derived from
chain lengths of about 30 to about 100 and the melting point an oilseed source Such as Soybean or corn oil. The pigment is
of the wax is typically about 75° C. to about 85°C. Further typically a finely ground, organic toner so that the wick of a
descriptions of the petroleum wax that may be used may be candle formed eventually from pigment-covered wax par
found in Kirk-Othmer, Encyclopedia of Chemical Technol ticles does not clog as the wax is burned. Pigments, even in
ogy, 3rd Edition, Volume 24, pages 473-76, which is hereby 45 finely ground toner forms, are generally in colloidal Suspen
incorporated by reference. sion in a carrier.
The wax portions of Suitable compositions typically have If a dye constituent is utilized, it may be dissolved in an
mineral wax portions which are less than 50 wt.% of the wax organic solvent. A variety of pigments and dyes suitable for
portion of the composition, with polyol ester compositions candle making are listed in U.S. Pat. No. 4,614.625, the
making up at least half of the wax portion. The polyol ester 50 disclosure of which is herein incorporated by reference. The
portions can include transesterified polyol ester portions and/ preferred carriers for use with organic dyes are organic Sol
or untransesterified polyol ester portions. The polyol ester vents, such as relatively low molecular weight, aromatic
portions are preferably based on triglycerol and also prefer hydrocarbon solvents; e.g. toluene and Xylene. The dyes ordi
ably have fatty acid portions. Other suitable compositions narily form true solutions with their carriers. Since dyes tend
have up to about 25 wt.% and up to about 17 wt.% mineral 55 to ionize in solution, they are more readily absorbed into the
wax. Other suitable compositions have less than about 5 wt. prilled wax granules, whereas pigment-based coloring agents
% but more than 0 wt.% mineral wax. These compositions tend to remain closer to the surface of the wax.
preferably have less than about 3 wt.% mineral wax, and Candles often are designed to appeal to the olfactory as
more preferably, less than about 1 wt.% mineral wax. If a well as the visual sense. This type of candle usually incorpo
mineral wax is used, it is typically a petroleum wax, Such as 60 rates a fragrance oil in the waxy body material. As the waxy
paraffin wax. material is melted in a lighted candle, there is a release of the
Other Waxes fragrance oil from the liquefied wax pool. The scenting agent
Solid natural waxes and synthetic waxes may be used to may be an air freshener, an insect repellent or more serve
form the wax composition. For instance, many creatures more than one of Such functions.
(such as insects and animals) and plants form waxy Sub 65 The air freshener ingredient commonly is a liquid fra
stances that are generally solid at room temperature. Some grance comprising one or more Volatile organic compounds
example of the various types creature waxes are beeswax, which are available from perfumery suppliers such IFF, Fir
 US 8,157,873 B2
17 18
menich Inc., Takasago Inc., Belmay, Noville Inc., Quest Co., migration inhibitors can also enhance the flexibility of the
and Givaudan-Roure Corp. Most conventional fragrance base wax material and decrease its chances of cracking during
materials are volatile essential oils. The fragrance can be a the cooling processes that occurs in candle formation and
synthetically formed material, or a naturally derived oil such after extinguishing the flame of a burning candle. For
as oil of Bergamot, Bitter Orange, Lemon, Mandarin, Cara 5 example, it may be advantageous to add up to about 5.0 wt.%
way, Cedar Leaf, Clove Leaf, Cedar Wood, Geranium, Lav and, more commonly, about 0.1-2.0 wt.% of a migration
ender, Orange, Origanum, Petitgrain, White Cedar, Patchouli, inhibitor, such as an alpha olefin polymer, to the present wax
Lavandin, Neroli, Rose and the like. materials
A wide variety of chemicals are known for perfumery such Exemplary Properties of Waxes
as aldehydes, ketones, esters, alcohols, terpenes, and the like. 10 These exemplary waxes have a polyol ester component.
A fragrance can be relatively simple in composition, or can be The polyol ester component can be a complete ester (fully
a complex mixture of natural and synthetic chemical compo esterified), or can be an incomplete ester (having potential
nents. A typical scented oil can comprise woody/earthy bases ester bonding sites of the polyol not occupied by acyl groups).
containing exotic constituents such as Sandalwood oil, civet, The polyol components of the waxes are preferably formed
patchouli oil, and the like. A scented oil can have a light floral 15 by transesterification of a precursor mixture. The precursor
fragrance, Such as rose extract or violet extract. Scented oil mixture may include polyol esters, free fatty acids, polyols,
also can be formulated to provide desirable fruity odors, such other esters, and/or other components. Some polyol esters
as lime, lemon or orange. which are particularly well suited include polyol esters of
Synthetic types of fragrance compositions either alone or fatty acids. Some typical polyol esters include monoglycer
in combination with natural oils such as described in U.S. Pat. ide, diglyceride, and triglyceride. Linked glyceride esters
Nos. 4.314.915; 4,411,829; and 4,434,306; incorporated may also be used. Glycerin and other glycerol related mol
herein by reference. Other artificial liquid fragrances include ecules may be used as part of the polyol mixture.
geraniol, geranyl acetate, eugenol, isoeugenol, linalool, lina The precursor mixture could use natural, refined, and/or
lyl acetate, phenethyl alcohol, methyl ethyl ketone, meth hydrogenated oils/fats, such as plant oils, as part of the pre
ylionone, isobornyl acetate, and the like. The scenting agent 25 cursor mixture. Typical plant oils/fats include Palm oil, Soy
can also be a liquid formulation containing an insect repellent bean oil, Coconut oil, Cocoa butter, Corn oil, etc. For
Such as citronellal, or a therapeutic agent such as eucalyptus instance, soybean oil may be used in its natural state, can be
or menthol. Once the coloring and scenting agents have been fractionated to provide soy stearine, and/or may be fully or
formulated, the desired quantities are combined with waxy partially hydrogenated.
material which will be used to form the body of the candle. 30 The precursor mixture is preferably fully transesterified,
For example, the coloring and/or scenting agents can be but may be transesterified to other degrees while remaining
added to the waxy materials in the form of prilled wax gran within the scope of the exemplary embodiments. Transesteri
ules. When both coloring and scenting agents are employed, fication may include using a chemical or enzyme to random
it is generally preferable to combine the agents together and ize the distribution of acyl groups. Transesterification could
then add the resulting mixture to the wax. It is also possible, 35 also include using a selective enzyme Such as a 1.3 selective
however, to add the agents separately to the waxy material. enzyme.
Having added the agent or agents to the wax, the granules are These waxes may have other components as well. For
coated by agitating the wax particles and the coloring and/or instance, a wax may have a petroleum based wax component
scenting agents together. The agitating step commonly con Such as a paraffin component. The wax may also have a solid
sists of tumbling and/or rubbing the particles and agent(s) 40 natural wax component; examples of Such waxes including
together. Preferably, the agent or agents are distributed sub insect wax and plant wax. The wax may also contain non
stantially uniformly among the particles of wax, although it is waxy components such as free fatty acids, additives, etc. The
entirely possible, if desired, to have a more random pattern of additives may be used to add color or scent, give the wax
distribution. The coating step may be accomplished by hand, insect repellency, improve a wax's compression moldability,
or with the aid of mechanical tumblers and agitators when 45 inhibit migration of components, and/or performany number
relatively large quantities of prilled wax are being colored of other useful functions and/or give the wax any number of
and/or scented. useful properties. The wax composition would preferably
Certain additives may be included in the present wax com include at least about 51 wt.% of the polyol ester component.
positions to decrease the tendency of colorants, fragrance More preferably, the wax composition would include at least
components and/or other components of the wax to migrate to 50 about 70 wt.% of the polyol ester component.
an outer surface of a candle. Such additives are referred to These waxes preferably have a melting point of at least
herein as “migration inhibitors.” The wax may include 0.1 to about 48° C. and no more than about 70° C., but may have
5.0 wt.% of a migration inhibitor. One type of compounds lower or higher melting points if desired. The waxes also
which can act as migration inhibitors are polymerized alpha preferably have Iodine Values (IV) of at least about 15 and no
olefins, more particularly polymerization products formed 55 more than about 70, and more preferably of at least about 20.
alpha olefins having at least 10 carbon atoms and, more com The SFC-40 for the waxes is generally at least about 15, but is
monly from one or more alpha olefins having 10 to about 25 preferably at least about 20, and more preferably at least
carbon atoms. One Suitable example of Such as polymer is an about 30.
alpha olefin polymer sold under the tradename Vybar R 103 Waxes according to these exemplary embodiments prefer
polymer (mp 168° F. (circa 76° C.); available from Baker 60 ably include any number of characteristics. For instance, a
Petrolite, Sugarland,Tex.). The inclusion of sorbitan triesters, glycerol based portion of the wax preferably maintains a
Such as Sorbitan tristearate and/or sorbitan tripalmitate and generally B' crystal structure when Subjected to normal candle
related sorbitan triesters formed from mixtures of fully heating and cooling conditions.
hydrogenated fatty acids, in the present wax compositions Additionally, the wax or polyol wax component would
may also decrease the propensity of colorants, fragrance com 65 preferably include no more than about 5 to 15 wt.% 16:0 fatty
ponents and/or other components of the wax to migrate to the acids in its fatty acid profile. The wax would also preferably
candle surface. The inclusion of either of these types of contain no more than 10 wt.% fatty acids having hydroxyl
 US 8,157,873 B2
19 20
groups in its fatty acid profile. Further, the wax would pref use in a container candle that has an SFC-40 of no less than
erably contain no more than 25 wt.% fatty acids having less about 25. These waxes, like waxes suitable for use as Votive
than 16 carbonatoms or more than 18 carbonatoms in its fatty candle waxes, would preferably be able to pass a slump test at
acid profile. 120° F., but may also be acceptable if they pass at tempera
The wax can preferably pass a slump test, preferably pass tures as low as about 115° F or 117 F.
ing it at least 120°F. The wax also preferably has an SFC-40 There are likely some waxes which may be acceptable for
of at least 16. Waxes according to these embodiments also use as both votive and pillar waxes. Also, there are likely some
preferably do not have large spikes in their up-heat melting waxes which may be acceptable for use as both votive and
curves (which can be measured by calorimetry). container waxes. While generally less common, there may be
It may be advantageous to minimize the amount of free 10 Some waxes that are suitable for use as both pillar and con
fatty acid(s) in a polyol fatty acid ester-based wax. Since tainer waxes as well.
carboxylic acids are commonly somewhat corrosive, the pres Candles formed from the waxes generally include a wick in
ence offatty acid(s) in a the polyol fatty acid ester-based wax addition to the wax. The wick can be made of any number of
can increase its irritancy to skin. The present the polyol ester materials, but are preferably a natural wick such as a braided
based wax generally has free fatty acid content (“FFA) of no 15 cotton wick.
more than about 1.0 wt.% and, preferably no more than about Formation of Candles
O5 wt.%. Candles can be produced from the polyol ester based mate
Waxes having TAG components preferably have triCX)- rial using a number of different methods. In one common
TAG concentrations which are roughly equal to the cube of process, the polyolester based wax is heated to a molten state.
the concentration of the X acyl group in the acid profile. X is If other additives such as colorants and/or fragrance oils are to
preferably chosen as an acyl group having a relatively high be included in the candle formulation, these may be added to
concentration in the acid profile and/or is selected to be an the molten wax or mixed with polyol ester based wax prior to
acyl group that is readily identifiable in the acid profile. heating. The molten wax is then solidified around a wick. For
Also, preferably, waxes having TAG components prefer example, the molten wax can be poured into a mold which
ably have a 1.2:1.3-SS ratio that is at least about 1.5, and more 25 includes a wick disposed therein. The molten wax is then
preferably, at least about 1.8. Also, the 1.2:1.3-SS ratio is cooled to solidify the wax in the shape of the mold. Depend
typically no more than 4, and preferably no more than about ing on the type of candle being produced, the candle may be
25. unmolded or used as a candle while still in the mold. Where
A wax or wax component would preferably have properties the candle is designed to be used in unmolded form, it may
that were resistant to change when further transesterified. For 30 also be coated with an outer layer of higher melting point
instance, physical properties such as melting point, SFC-40, material.
SFC-10:40, crystal structure, tri(X)-TAG amounts, TAG pro Alternatively, the polyol ester based material can be
file, and others would preferably not change very much if the formed into a desired shape, e.g., by pouring molten polyol
wax or wax component were subjected to further transesteri ester based wax into a mold and removing the shaped material
fication. 35 from the mold after it has solidified. A wick may be inserted
Waxes suitable for use as pillar candles generally have a into the shaped waxy material using techniques known to
melting point of at least about 55° C. and generally no more those skilled in the art, e.g., using a wicking machine Such as
than about 70° C., preferably at least about 56° C. and no a Kurschner wicking machine.
more than about 60° C. or 65°C. These waxes typically have Polyol ester based waxes can also be formed into candles
an IV of at least about 15 or 20 and an IV of no more than 40 using compression molding techniques. This process often
about 50, and preferably no more than 45. These waxes pref involves forming the wax into a particulate form and then
erably have an SF-40 of at least about 30, and more preferably introducing the particulate wax into a compression mold.
of at least about 40. The wax may be in a particulate form, and The candle wax may be fashioned into a variety of particu
the wax particles may be used to form the pillar candle by late forms, commonly ranging in size from powdered or
compression molding. A pillar candle may be over-dipped, or 45 ground wax particles approximately one-tenth of a millimeter
go through some other processes to attempt to give the candle in length or diameter to chips, flakes or other pieces of wax
an even appearance. approximately two centimeters in length or diameter. Where
Waxes suitable for use in making votive candles have melt designed for use in compression molding of candles, the
ing points generally in the range of about 50° C. to about 60° waxy particles are generally spherical, prilled granules hav
C., and preferably have melting points of at least about 52°C. 50 ing an average mean diameter no greater than one (1) milli
and no more than about 58°C. These waxes preferably have meter.
an IV of about 35-65. Some votive waxes may be required to Prilled waxy particles may be formed conventionally, by
pass a slump test. These waxes would preferably be able to first melting a triacylglycerol-based material, in a vat or simi
pass a slump test at 120°F., but may also be acceptable if they lar vessel and then spraying the molten waxy material through
pass attemperatures as low as about 115° F. or 117 F. These 55 a nozzle into a cooling chamber. The finely dispersed liquid
waxes preferably have an SFC-40 of at least about 25. solidifies as it falls through the relatively cooler air in the
Waxes suitable for use as containers preferably have a chamber and forms the prilled granules that, to the naked eye,
melting point of about 48°C. to about 58° C. More preferably appear to be spheroids about the size of grains of sand. Once
the melting point is at least about 50° C. and no more than formed, the prilled triacylglycerol-based material can be
about 55° C. Also, these waxes preferably have an IV of at 60 deposited in a container and, optionally, combined with the
least about 45, and generally no more than 70. Further, these coloring agent and/or scenting agent.
waxes typically have an SFC-10:40 of at least 1.5, and gen Particulates, including prilled waxy particles, can be
erally have an SFC-10:40 of at least 1.8. Preferably, these formed into candles using compression techniques. The par
waxes have an SFC-10:40 of at least about 2.0, and more ticulates can be introduced into a mold using a gravity flow
preferably, at least about 2.5. These waxes preferably have an 65 tank. The mold is typically abronze or teflon mold. A physical
SFC-40 of at least 18, and more preferably of at least 20. press then applies between 1000 and 2000 pounds of pressure
Occasionally, it may be desirable to have a wax suitable for at the ambient room temperature (generally 65 to 85 F). The
 US 8,157,873 B2
21 22
pressure can be applied from the top or the bottom. The Good mold release, as a property of a candle wax, is defined
formed candle can then be pushed out of the mold. A candle by the amount of contraction in the molded wax at a given
formed by this method may not tend to have even appearing area (which can be defined by width and length, by diameter,
sides. A candle may experience Some heat (below the melting etc). A candle would preferably have good mold release for
point of the candle) when run through the extruder, which candles having a diameter of about 1.5 to about 3.5 inches and
heat will tend to glaze over the side and remove some of the candles having diameters of about 4 inches to about 7 inches.
uneven appearance. If desired, a candle formed by this The area by which mold release is defined is based on the
method may be over-dipped in hot liquid wax to give the outer particular application.
Surface of the candle a Smoother appearance. 10
The basic techniques that can be used to form candles, can
Equipment and procedures for wax powder compression also be used to form other wax-based structures.
are described in publications such as “Powder Compression Bleaching and Deodorizing
Of Candles” by M. Kheidr (International Group Inc., 1990), The polyol ester based wax may also be bleached and
incorporated by reference. Compression-molding can be con deodorized. Bleaching can be done using diatomaceous earth
ducted under conditions comprising a mold pressure between 15
which is acid activated and added under vacuum. This tends to
about 1000-4000 psi, a compression time between about 1-20 remove Soaps from the wax. Also, the polyol ester based wax
seconds, and a prilled wax temperature between about 15°C. can be deodorized by removing the free fatty acids. This can
to about 25° C. be done by distilling the free fatty acids at 450° F. to 500°F.
The particle size distribution specification of a prilled wax The polyol based ester may also be subject to other processing
composition may be important for achieving a Superior com and/or purifying steps.
bination of properties in the final candle product. The following examples are presented to illustrate the
The specified particle size distribution permits the prilled present invention and to assist one of ordinary skill in making
wax composition to have a powder density between about and using the same. The examples are not intended in any way
0.55-0.65 grams percentimeter, and subsequently allows the to otherwise limit the scope of the invention.
compression-molded candle product to have a density 25
between about 0.8-0.9 gram per cubic centimeter. Example 1
Additionally, the particle size distribution specification of a
prilled wax composition contributes other important property Interesterification was accomplished by mixing a polyol
improvements to the final candle product. A high degree of ester precursor mixture with about 0.1 wt.% sodium meth
particle fusion is effected by the compression-molding pro 30
oxide under a vacuum (s.10 mm) atmosphere. The resulting
cedure, and the final candle product is characterized by desir mixture was heated to about 90° C. to 100° C. for thirty to 60
able hardness and strength properties, and by a high gloss or minutes. The reaction was quenched using 80% aq. HPO.
satin candle Surface finish. The resulting product was heated and water was removed via
The present waxes can also incorporate between about vacuum. Table 1 shows a number of polyol compositions
0.1-5 weight percent of a wax fusion enhancing type of addi 35
(“precursor mixtures') that were interesterified under these
tive in the prilled wax composition which is being subjected conditions. Tables 2 and 3 show some physical properties
to a compression molding procedure. Suitable wax-fusion (melting point and solid fat content) of these mixtures before
enhancer additives include benzyl benzoate, dimethyl phtha and after, respectively, being Subjected to the interesterifica
late, dimethyl adipate, isobornyl acetate, cellusolve acetate, tion reaction.
TABLE 1
Percentages of Each Precursor Component By Weight
Sample # Soy RB Soy Stearine Soy Hardfat Palm Hardfat Dimodan H-SS C-RB Iodine Value
1 25 O 75 O O O O 34.5
2 O 55 45 O O O O S1.1
3 30 O 70 O O O O 40.O
4 O 60 40 O O O O 55.6
5 50 O 50 O O O O 66.5
6 O O 50 O O O 50 5.7
7 45 O 55 O O O O 60.0
8 O 50 50 O O O O 46.5
9 O 55 43 O 2 O O 50.7
10 O 40 60 O O O O 37.4
11 O 25 75 O O O O 23.8
12 40 O O 60 O O O 53.4
13 O O O O O 1OO O 40.O

H-SS represents the amount of hydrogenated soy stearine in the precursor mixture,

glucose pentaacetate, pentaerythritol tetraacetate, trimethyl TABLE 2

S-trioxane and N-methyl pyrrolidone. 60
The prill composition additive may also have a beneficial Physical Properties of Precursor Mixtures
effect on the combustion properties of a candle product which Sample Melt SFC 10 SFC 40
is compression molded. 1 1544 77.1 70.8
When waxes are placed in molds to form candles, the 2 148.9 75.0 44.0
waxes preferably have good mold release. To have good 65 3 153.0 75.1 68.5
mold release, the wax preferably contracts enough to leave 4 146.5 72.8 40.O
/16" of an inch between the formed candle and the mold.
 US 8,157,873 B2
23 24
TABLE 2-continued (although identification is tentative Due to retention time
shifting). The SSP peak appeared to be present in both
Physical Properties of Precursor Mixtures samples, at 10.82% and 6.97% w/w in Sample 2 Precursor
Sample Melt SFC 10 SFC 40 Mixture and Sample 2 Interesterified Wax, respectively
5 150.2 56.1 44.5
(again, this peak was tentatively identified). The TAG
6 1485 92.3 47.3 amounts in the hump peaks were 33.4% w/w in Sample 2
7 151.O 6O.S 49.2 Precursor Mixture and 54.4% w/w in Sample 2 Interesterified
8 1499 80.6 SO.1 Wax. Other unidentified peaks were not included in the total.
9
10
148.2
152.5
78.7
85.7
44.2
6O.S
Approximately 60-70% w/w of the TAGs were accounted for.
11 155.5 90.1 76.1
10 Referring to FIGS. 3 and 4, Sample 13 Precursor Mixture
12 135.7 64.8 S4.9 and Sample 13 Interesterified Wax TAG chromatograms are
13 1291 97 S1.9 shown in FIGS. 3 and 4. The tristearin concentrations were
5.5% and 4.4% w/w for Sample 13 Precursor Mixture and
Sample 13 Interesterified Wax, respectively. The SSP peak
15 concentration was 7.1% and 6.3% w/w for Sample 13 Pre
TABLE 3
cursor Mixture and Sample 13 Interesterified Wax, respec
Physical Properties of Waxes After Interesterification tively.
Sample Melt SFC 10 SFC 40 Example 3
1 147.0 81.1 53.7
2 127.1 87.9 34.8 Samples 2 and 13 from Example 1 were also evaluated
3 14.S.S 80.8 48.6 using differential scanning calorimetry (DSC). The thermal
4 122.8 79.0 23.0 profile performed on the samples included an initial cool from
5 125.3 48.7 16.8
6 118.0 91.4 16.O room temperature to -30°C. From -30°C., the sample was
7 128.1 57.6 23.1 25 heated to 90° C. cooledback to -30°C. and heated back to 90°
8 1294 87.7 40.4 C. The first up-heat erases all thermal history. The cool down
9 125.3 85.5 32.4
10 133.9 89.0 55.0
is controlled fast cooling at 40° C./minute. The second up
11 139.9 94.6 74.7 heat allows the direct comparison of sample melting charac
12 139.9 64.6 25.7 teristics of flash-chilled waxes because of their identical ther
13 125.3 97 47.2 30 mal histories.
Referring to FIG. 5, the first up-heat of Sample 2 Precursor
For tables 2 and 3, SFC values are listed as the percent, by Mixture (2-pre) and Sample 2 Interesterified Wax (2-post)
weight, of the composition which is solid at the given tem shows a broadening of the melting curve near the melting
perature. Melting point was determined by Mettlar dropping point when compared to the melting curve of the precursor
point (AOCS Ce 18-80).
35 mixture (2-pre). The high melting fraction and the low melt
ing fraction appeared to have migrated towards each other
Example 2 when the precursor mixture was interesterified and the “sharp
spike' observed in the first upheat melting curve of the
Each of Samples 2 and 13 from Example 1 were analyzed Sample 2 Precursor Mixture is essentially absent in the first
40 upheat melting curve of Sample 2 Interesterified Wax. The
for their TAG content and DSC curves both as a precursor samples were rapidly cooled, and the cool down and 2"
mixture and as an interesterified wax. upheat of the waxes were also measured.
Triacylglycerols (TAGs) were separated by Cs reversed Referring to FIG. 6, the first up-heat of Sample 13 Interes
phase liquid chromatography (RP-LC) coupled to an evapo terified Wax (13-post) shows a broadening of the melting
rative light scattering detector (ELSD). A gradient binary 45 curve near the melting point. The “sharp spike' observed in
mobile phase system consisting of acetonitrile and methylene the first upheat melting curve of the Sample 13 Precursor
chloride was used at 10°C. for the separation. During this run Mixture (13-pre) is essentially absent in the first upheat scan
the column chiller stopped working and separations were run of the Sample 13 Interesterified Wax. The samples were rap
at room temperature (approximately 25°C.). This caused a idly cooled, and the cool down and 2" upheat of the waxes
loss of resolution for some of the compounds. The mobile 50 were also measured.
phase flow rate was 0.7 mL/min. The ELSD settings were 35°
C., a pressure of 3.5 bar, and nitrogen was used as the nebu Example 4
lizing gas. Calibration curves were log-log linear and based
upon triolein (000) as the external standard. The internal A wax with a composition similar to that of Sample 2 was
standard was a C33 TAG at 10 mg. Standards and samples 55 formed into a container candle and Subjected to a burn test.
were diluted in methylene chloride. Soybean oil was used as Fragrance was added to the wax in the amount of 6 wt.%.
a reference material. A mixture of mono- and mixed acid along with 0.5 g of dye. An HTP 1212 cotton wick from
TAGS was used as retention time marker. Wicks Unlimited was placed in a 16 oz 4" diameter glass
Referring to FIGS. 1 and 2, the triacylglycerol (TAG) pro container. The wax was melted and the molten wax was
files of Sample 2 Precursor Mixture and Sample 2 Interest 60 poured in the container.
erified Wax are shown in FIGS. 1 and 2 respectively. The fatty During the burn test the flame reached a maximum flame
acid composition for both samples was nearly identical, how height of 30 mm. The melt pool melted all the way out to the
ever, the TAG composition profiles were different as evi edges of the container and achieved a depth of '4". The melt
denced by the chromatograms. The large SSS (tristrearin) pool reached a maximum temperature of 160°F. during the
peak in FIG. 1 should be correct since it matched retention 65 duration of the burn. The wax had a disappearance of 4.6 g/hr
time with a standard. It was present at 28.8% w/w. This peak during the burn test. There was no sooting noted during the
decreased in Sample 2 Interesterified Wax to 7.7% in FIG. 2 burn duration. Upon cooling the wax came back to a Smooth
 US 8,157,873 B2
25 26
surface with little or no marring. The sides of the resolidified point of about 50° C. to about 60°C.; an Iodine Value of about
candle were smooth with little to no whiting left where the 40 to 75; and an SFC at 10°C. that is at least about twice that
melt pool had been. The time for the wax to resolidify was 20 of the SFC at 40° C.
minutes. Another embodiment is directed to another polyol-based
wax suitable for use as a candle wax. The polyol-based wax
Illustrative Embodiments includes a complete polyol fatty acid ester component; and
has a melting point of about 45° C. to 65° C. and an SFC-40
A number of illustrative embodiments of the present lipid of at least about 16. The wax preferably has an Iodine Value of
based waxes and candles produced therefrom are discussed about 40 to 75.
herein. The embodiments described are intended to provide 10 Another embodiment provides an ester-based composition
illustrative examples of the present waxes and candles and are which includes at least about 51 wt.% of an interesterified
not intended to limit the scope of the invention. polyol fatty acid ester. The composition can also include a
In one embodiment, the wax composition includes of a wax component such as an insect wax or other naturally
petroleum wax, free fatty acid, and/or renewable resource occurring wax and/or a petroleum wax. The ester-based wax
wax (such as plant wax or insect wax). These waxes are 15 can also have a melting point of about 45° C. to 60° C. and/or
preferably only present in the composition up to about 49% an SFC-40 of at least about 16 or 20.
by weight. The petroleum wax may include a medium paraf Another embodiment is directed to a candle having a wick
fin wax, a microcrystalline paraffin wax and/or a petroleum and a wax. The wax has a melting point of about 45° C. to
wax obtained from crude oil refined to other degrees. In about 75° C. and includes a triacylglycerol component. The
another embodiment, the wax composition includes up to triacylglycerol component preferably has a percent concen
about 25% by weight of the alternate waxes. In still another tration by weight of tri(HC)-TAG which is equal to the cube
embodiment, the wax composition includes no more than of the percent concentration by weight of HC in the fatty acid
about 10% by weight of the alternate waxes. profile--E wt.%. HC is selected to be the fatty acid which is
One embodiment is directed to a lipid-based wax compo present in the greatest amount in the fatty acid composition of
sition having a melting point of about 48°C. to about 75° C. 25 the triacylglycerol component, and tri(HC)-TAG is a triacylg
and including a polyol fatty acid ester component formed by lycerol having three HC fatty acid acyl groups.
a process which includes interesterifying a polyol fatty acid Another embodiment is directed to a method for forming a
ester precursor. The polyol fatty acid ester component can wax. The method includes creating a precursor mixture which
include a fully esterified polyol fatty acid ester component. includes at least (a) triacylglycerol and (b) glycerin and/or
The wax composition commonly includes at least about 51 30 other polyol (e.g. propylene glycol and/or sorbitan). The
wt.% of the fully esterified polyol fatty acid ester component. method further includes interesterifying the precursor mix
The fully esterified polyol fatty acid ester component can ture.
include triacylglycerol. The wax preferably has a melting Another embodiment is directed to a polyol-based wax
point of about 53°C. to 70° C., about 50° C. to 65°C., or about suitable for use as a candle wax. The polyol-based wax
48° C. to 58°C. The wax preferably has an SFC-40 of at least 35 includes a complete polyol fatty acid ester component. The
about 14, and more preferably at least 16 or 20. For waxes wax preferably has a melting point of about 130°F. to 155° F.
designed to be used in container candles, it may be desirable (about 54° C. to 68° C.), and an SFI-40 of at least about 40.
to have an SFC-10 that is at least about twice as much as its The wax also preferably has an Iodine Value of about 20 to 45.
SFC-40 (i.e., the SFC-10:40 ratio is at least about 2.0). Another embodiment provides a lipid-based wax suitable
Another embodiment is directed to a candle made from a 40 for use as a candle wax. The lipid-based wax includes at least
triacylglycerol containing wax. The wax includes a wick and about 50 wt.% of a fully interesterified polyol fatty acid ester
a wax. The wax has a melting point of about 45° C. to about component. The lipid-based wax preferably has a melting
75° C. and includes a triacylglycerol component having a point of about 130° F. to 155° F (about 54° C. to 68° C.)
fatty acid composition which includes Stearic acid. The tria and/or an SFI-40 of at least about 40. The lipid-based wax
cylglycerol component preferably has a percent concentra 45 preferably includes a polyol fatty acid partial ester, and more
tion by weight of SSS-TAG which is equal to the cube of a preferably includes at least about 10% or 20% of a polyol
fractional concentration by weight of Stearic acid in the fatty fatty acid partial ester. The lipid-based wax can also include a
acid profile+E wt.%. E. can be selected to be no more than a petroleum wax, an insect wax, Some other naturally occurring
preset amount, or no more than a percentage of the SSS-TAG wax, or some other type of wax Such as a non- or partially
concentration. E is preferably selected to be no more than 50 interesterified polyol fatty acid component. The lipid-based
about 5 or 7 wt.%, and desirably less than or equal to 3 wt.%. wax can also include a free fatty acid component. The fatty
The wax preferably includes at least about 51 wt.% of the acid composition of the lipid-based wax preferably does not
triacylglycerol component. Stearic acid may often makeup include more than about 15 wt.% palmitic acid. The fatty acid
about 30 wt.% or more of the fatty acid composition of the composition of the lipid-based wax also preferably includes
triacylglycerol component. Also, the 1.2:1.3-S ratio is pref 55 no more than about 1.0 wt.% 18:3 fatty acid. The lipid-based
erably at least 1.5; the 1.2:1.3-S ratio being the percent con wax preferably has a slump temperature of at least about 118°
centration by weight of 1.2-S-3-X-triacylglycerol divided by F. Typically, the wax has at least about 70 wt.% of the fully
the percent concentration by weight of 1.3-S-2-X-triacylg interesterified polyol ester component, and preferably
lycerol. includes at least 85 wt.%.
Another embodiment is directed to a candle comprising a 60 Another embodiment is directed to a candle having a wick
wick and a wax. The wax preferably has a melting point of and a wax. The wax preferably has a melting point of about
about 45° C. to about 75° C. and includes a fully interesteri 45° C. to about 75° C. The wax includes a triacylglycerol
fied polyol fatty acid ester component. The polyol fatty acid component formed by a process which includes interesteri
ester component is preferably a triacylglycerol component. fying a precursor mixture. The precursor mixture can include
Another embodiment provides a lipid-based wax suitable 65 triglycerides, fatty acid monoglycerides, fatty acid diglycer
for use as a candle wax. The lipid-based wax includes a ides, fatty acid alkyl esters, free fatty acids, glycerin, and/or
complete polyol fatty acid ester component; and has a melting other esters or polyols.
 US 8,157,873 B2
27 28
Another embodiment is directed to a method for forming a acid profile, all acids whose concentration is at least 20 or 30
triglycerol based wax. The method comprises mixing glyc wt.% in the acid profile, or some other acid.
erin with free fatty acids to form a precursor mixture. The Another embodiment is directed to a wax suitable foruse as
method also includes interesterifying the precursor mixture. a candle wax. The wax has a polyol ester component and a
Another embodiment is directed to a wax suitable for use as melting point of about 45° C. to about 75°C. The wax can
a candle wax. The wax includes a triacylglycerol component have a melting point of about 50° C. to about 60° C., and
and has a melting point of about 48°C. to about 75°C. The preferably has a melting point of at least about 52°C. and no
triacylglycerol component preferably has a Substantially B' more than about 58°C. The wax preferably has an IV of about
structure when subjected to normal candle conditions. More 35-65. The wax would preferably be able to pass a slump test
preferably, the triacylglycerol component has a Substantially 10 at least about 117 F., and more preferably at least about 120°
complete B" structure when subjected to normal candle con F.The wax can have an SFC-40 of at least about 20, or at least
ditions. about 25. The polyol ester component preferably includes a
Another embodiment provides a wax suitable for use as a polyol polyester component Such as a triacylglycerol compo
candle wax. The wax includes a polyol ester component and nent. The triacylglycerol component preferably has a Sub
has a melting point of about 48° C. to about 75° C. The 15 stantially B' structure. The polyol ester component is prefer
properties of the wax are preferably resistant to change when ably at least 51 wt.% of the wax, and more preferably at least
subjected to interesterification. Measurement of resistance to 80 wt.% of the wax. The wax preferably does not have a large
change can be measured by a small change in melting point spike in its melting curve as measured by DSC. The polyol
after interesterification (no more than about 3 or 5°C.). Alter ester component preferably does not have a large spike in its
natively, measurement of resistance to change can be mea melting curve as measured by DSC. The wax may contain
sured by a small change in SFC-10 and/or SFC-40 (preferably other components such as solid natural waxes (insect waxes,
no more than about 1 or 3 wt.%). Further still, measurement plant waxes, etc), mineral waxes (paraffin), synthetic waxes,
of resistance to change can be measured by a small change in or other wax components. These wax components preferably
SFC-10:40, relative concentrations of the polyol esters (such comprise a smaller percentage of the wax than the polyol ester
as tri(X)-TAG), crystal structure, and/or other properties of 25 component. This wax may have additives that add color, that
the wax. add scent, that inhibit migration of components, that give the
Another embodiment is directed to a wax suitable for use as wax insect repellancy, and/or other additives. The polyol ester
a candle wax. The wax has a polyol ester component and a may be formed from a precursor mixture including one or
melting point of about 45° C. to about 75°C. The wax may more plant oils (such as Soybean oil or palm oil). The plant
have a melting point of about 48° C. to about 58° C. More 30 oils can be natural, refined, and/or hydrogenated. Transesteri
preferably the melting point is at least about 50° C. Further, fication preferably includes interesterifying a precursor mix
the melting point is preferably no more than about 55° C. The ture resulting in an interesterified precursor mixture. The wax
wax may have an IV of at least about 45. The wax have further can have TAG components having a 1.2:1.3-S ratio that is at
have an IV which is not greater than about 70. Further, the least about 1.5, and preferably, at least about 1.8. The wax can
wax may have an SFC-10:40 of at least 1.5, and potentially an 35 have TAG components where the triCX)-TAG concentrations
SFC-10:40 of at least 1.8. The SFC-10:40 of the wax is more is roughly equal to the cube of the concentration of the X acyl
preferably at least about 2.0, and more preferably, at least group in the acid profile. The X acyl group can be selected
about 2.5. The wax preferably has an SFC-40 of at least 16, from Stearic acid, the acid in the highest concentration in the
and more preferably of at least 20. The wax may be able to acid profile, all acids whose concentration is at least 20 or 30
pass a slump test at least about 117 F., and preferably at least 40 wt.% in the acid profile, or some other acid.
about 120°F. The polyol ester component preferably includes Another embodiment is directed to a wax suitable foruse as
a polyol polyester component Such as a triacylglycerol com a candle wax. The wax has a polyol ester component and a
ponent. The triacylglycerol component preferably has a Sub melting point of about 45° C. to about 75°C. The wax may be
stantially B' structure. The polyol ester component is prefer limited to having a melting point of at least about 55° C. and
ably at least 51 wt.% of the wax, and more preferably at least 45 no more than about 70° C. Further, the wax may have a
85 wt.% of the wax. The wax preferably does not have a large melting point of no more than about 65° C. Further still, the
spike in its melting curve as measured by DSC. The polyol wax may have a melting point of about 56°C. to about 60° C.
ester component preferably does not have a large spike in its The IV for the wax may be at least about 15. Additionally, the
melting curve as measured by DSC. The wax may contain IV of the wax may be no more than about 50. Further, the wax
other components such as solid natural waxes (insect waxes, 50 may have an IV of about 20 to about 45. The wax may have an
plant waxes, etc.), mineral waxes (paraffin), synthetic waxes, SFC-40 of at least 30. Further, the wax may have an SFC-40
or other wax components. These wax components preferably of about 40. The wax may be in particulate form. The polyol
comprise a smaller percentage of the wax than the polyolester ester component preferably includes a polyol polyester com
component. This wax may have additives that add color, that ponent such as a triacylglycerol component. The triacylglyc
add scent, that inhibit migration of components, that give the 55 erol component preferably has a substantially B' structure.
wax insect repellancy, and/or other additives. The polyol ester The polyol ester component is preferably at least 51 wt.% of
may be formed from a precursor mixture including one or the wax, and more preferably at least 80 wt.% of the wax. The
more plant oils (such as soybean oil or palm oil). The plant wax preferably does not have a large spike in its melting curve
oils can be natural, refined, and/or hydrogenated. Transesteri as measured by DSC. The polyol ester component preferably
fication preferably includes interesterifying a precursor mix 60 does not have a large spike in its melting curve as measured by
ture resulting in an interesterified precursor mixture. The wax DSC. The wax may contain other components such as Solid
can have TAG components having a 1.2:1.3-S ratio that is at natural waxes (insect waxes, plant waxes, etc.), mineral
least about 1.5, and preferably, at least about 1.8. The wax can waxes (paraffin), synthetic waxes, or other wax components.
have TAG components where the tri(X)-TAG concentrations These wax components preferably comprise a smaller per
is roughly equal to the cube of the concentration of the X acyl 65 centage of the wax than the polyol ester component. This wax
group in the acid profile. The X acyl group can be selected may have additives that add, color, that add scent, that
from Stearic acid, the acid in the highest concentration in the improve compression moldability, that inhibit migration of
 US 8,157,873 B2
29 30
components, and/or other additives. The polyol ester may be contains at least about 75 wt.% and, more desirably, at least
formed from a precursor mixture including one or more plant about 90 wt.% of the interesterified polyol fatty acid ester.
oils (such as Soybean oil or palm oil). The plant oils can be The interesterified polyol fatty acid ester generally includes a
natural, refined, and/or hydrogenated. Transesterification substantial amount of a completely esterified polyol fatty acid
preferably includes interesterifying a precursor mixture 5 ester. It is often quite desirable to employ a lipid-based wax
resulting in an interesterified precursor mixture. which includes at least about 51 wt.% of a fully interesterified
Another embodiment is directed to a wax suitable for use as fatty acid triacylglycerol.
a candle wax. The wax has a polyol ester component and a In another embodiment, a fatty acid ester-based composi
melting point of about 45° C. to about 75°C. The polyol ester tion includes a insect wax, e.g., beeswax, and at least about 51
component preferably includes a polyol polyester component 10
wt.% of an interesterified polyol fatty acid ester. In many
Such as a triacylglycerol component. The triacylglycerol instances, the lipid-based wax contains at least about 75 wt.%
component preferably has a substantially B' structure. The
polyol ester component is preferably at least 51 wt.% of the and, more desirably, at least about 90 wt.% of the interest
wax, and more preferably at least 80 wt.% of the wax. The erified polyol fatty acid ester. The interesterified polyol fatty
wax preferably does not have a large spike in its melting curve 15 acid ester generally includes a Substantial amount of a com
as measured by DSC. The polyol ester component preferably pletely esterified polyol fatty acid ester. It is often quite desir
does not have a large spike in its melting curve as measured by able to employ a lipid-based wax which includes at least
DSC. The wax may contain other components such as Solid about 51 wt.% of a fully interesterified fatty acid triacylglyc
natural waxes (insect waxes, plant waxes, etc.), mineral erol.
waxes (paraffin), synthetic waxes, or other wax components. In another embodiment, a fatty acid ester-based composi
These wax components preferably comprise a smaller per tion includes at least about 51 wt.% of an interesterified
centage of the wax than the polyol ester component. This wax polyol fatty acid ester and a crystal modifier Such as a insect
may have additives that add color, that add scent, that inhibit wax, e.g., beeswax. In many instances, the lipid-based wax
migration of components, that improve compression mold contains at least about 75 wt.% and, more desirably, at least
ability, that give the wax insect repellancy, and/or other addi 25 about 90 wt.% of the interesterified polyol fatty acid ester.
tives. The polyol ester may be formed from a precursor mix The interesterified polyol fatty acid ester generally includes a
ture including one or more plant oils (such as Soybean oil or substantial amount of a completely esterified polyol fatty acid
palm oil). The plant oils can be natural, refined, and/or hydro ester. It is often quite desirable to employ a lipid-based wax
genated. Transesterification preferably includes interesterify which includes at least about 51 wt.% of a fully interesterified
ing a precursor mixture resulting in an interesterified precur 30 fatty acid triacylglycerol.
Sor mixture. The wax can have TAG components having a Another embodiment is directed to a candle which includes
1.2:1.3-S ratio that is at least about 1.5, and preferably, at least a wick and a lipid-based wax. The wax has a melting point of
about 1.8. The wax can have TAG components where the about 48°C. to about 75° C. and may include a fully interes
tri(X)-TAG concentrations is roughly equal to the cube of the terified polyol fatty acid ester component. Very often, the
concentration of the X acyl group in the acid profile. The X 35 lipid-based wax includes a Substantial amount, e.g., at least
acyl group can be selected from Stearic acid, the acid in the about 51 wt.% of a fully interesterified triacylglycerol com
highest concentration in the acid profile, all acids whose ponent. The wax may also include a partially esterified polyol
concentration is at least 20 or 30 wt.% in the acid profile, or ester, such as a fatty acid monoglyceride and/or a fatty acid
some other acid. The wax may be in particulate form. The wax diglyceride.
would preferably be able to pass a slump test at least about 40 Other embodiments may provide a candle which includes
117 F., and more preferably at least about 120° F. The wax a wick and a wax. The wax can have a melting point of about
can have an SFC-40 of at least about 14 or 18. The properties 48° C. to about 70° C. and include a triacylglycerol compo
of the polyol ester component of the wax may be configured nent having a fatty acid composition which includes X wt.%
such that the properties of the polyol ester component would Stearic acid. The triacylglycerol component commonly has an
not change by very much if it were Subjected to transesteri 45 SSS-TAG content which is given by (X/10)+5 wt.%. In
fication. The wax may have free fatty acid concentrations certain waxes of this type, the SSS-TAG content which is
and/or particulate concentrations that are no more than about given by (X/10)+3 wt.%. The triacylglycerol component
1 wt.% each. The polyol ester component would preferably may have a ratio of SQS-TAG content:SSQ-TAG content of at
include no more than about 5 to 15 wt.% 16:0 fatty acids in its least about 1.0; wherein S represents stearic acid and Q rep
acid profile. The wax would also preferably contain no more 50 resents a fatty acid which is not stearic acid. In certain
than about 10 wt.% fatty acids having hydroxyl groups in its instances, the triacylglycerol component of the wax may have
fatty acid profile. Further, the wax would preferably contain a ratio of SQS-TAG content: SSQ-TAG content of no more
no more than 25 wt.% fatty acids having less than 16 carbon than about 0.7.
atoms or more than 18 carbon atoms in its fatty acid profile. In certain embodiments, in addition to an interesterified
The wax may have an IV of about 15 to 70. 55 polyol fatty acid ester, Such as an interesterified fatty acid
One illustrative embodiment provides a lipid-based wax triacylglycerol, the lipid-based wax may include a second
composition which has having a melting point of about 48°C. wax component. The second wax component may selected
to about 75°C. The lipid-based wax can include a completely from the group consisting of petroleum waxes, insect waxes,
esterified polyol fatty acid ester component, which formed by other plant-based waxes (e.g., bayberry wax, candidelia wax
a process which comprises interesterifying a polyol fatty acid 60 and carnuba wax) and/or free fatty acids.
ester precursor. The completely esterified polyol fatty acid Another embodiment is directed to a lipid-based wax suit
ester component generally accounts for at least about 51 wt. able for use as a candle wax. The lipid-based wax includes a
% of the wax, preferably accounts for at least about 70 wt.%. completely esterified polyol fatty acid ester component; and
In another embodiment, a fatty acid ester-based composi has a melting point of about 130° F to 155° F.; an SFI-40 of
tion includes a petroleum wax, e.g., a microcrystalline petro 65 at least about 40; and an Iodine Value of about 20 to 45. The
leum wax, and at least about 51 wt.% of an interesterified lipid-based wax may also include a polyol fatty acid partial
polyol fatty acid ester. In many instances, the lipid-based wax ester.
 US 8,157,873 B2
31 32
Yet another embodiment provides a lipid-based wax suit Another embodiment provides a candle comprising a wick
able for use as a candle wax, where the lipid-based wax and a lipid-based wax. The lipid-based wax has a melting
includes at least about 51 wt.% of a fully interesterified point of about 50° C. to about 70° C. and includes at least
polyol fatty acid ester component. The lipid-based wax has a about 51 wt.% of a triacylglycerol component having a fatty
melting point of about 130° F. to 155° F.; and an SFI-40 of at acid composition which includes X wt.% Z:0 fatty acid; the
least about 40. triacylglycerol component having an tri(Z:0)-TAG content
Another embodiment provides a lipid-based wax suitable which is given by (X/10)+5 wt.%; wherein the Z:0 fatty
acid is the Saturated fatty acid present in highest concentration
for use as a candle wax, where the lipid-based wax comprises in the fatty acid composition. More desirably, the tri(Z:0)-
a complete polyol fatty acid ester component; and has a 10 TAG content is given by (X/10)+3 wt.%.
melting point of about 50° C. to 60° C.; an SFI-40 of at least The invention has been described with reference to various
about 20; and an Iodine-Value of about 40 to 75. specific and illustrative embodiments and techniques. How
Another embodiment provides a A lipid-based wax suit ever, it should be understood that many variations and modi
able for use as a candle wax, where the lipid-based wax fications may be made while remaining within the spirit and
includes at least about 51 wt.% of an interesterified com 15
Scope of the invention.
The invention claimed is:
pletely esterified polyol fatty acid ester component. The lipid 1. A candle comprising a wick and a lipid-based wax:
based wax has a melting point of about 50° C. to 60° C.: an wherein the lipid-based wax comprises an interesterified
SFI-40 of at least about 20. polyol fatty acid ester component; and the lipid-based wax
Another embodiment is directed to a lipid-based wax suit has a melting point of about 55° C. to 75° C.; an SFI-40 of at
able for use as a candle wax. The lipid-based wax has a least about 20; and an Iodine Value of about 15 to 65.
melting point of about 48°C. to about 70° C. and includes at 2. The candle of claim 1 wherein the lipid-based wax has an
least about 51 wt.% of a triacylglycerol component having a SFI-40 of at least about 40.
fatty acid composition which includes X wt.% “HC fatty 3. The candle of claim 1 wherein the lipid-based wax has a
acid', where the HC fatty acid is the fatty acid present in slump temperature of at least about 120° F.
highest concentration in the fatty acid composition; and the 25 4. The candle of claim 1 wherein the lipid-based wax
triacylglycerol component has a tri(HC)-TAG content which includes at least about 51 wt.% of a fully interesterified
is given by (X/10)+5 wt.% and, more desirably, (X/10)+3 polyol fatty acid ester component.
wt.%. 5. The candle of claim 4 wherein the fully interesterified
Another embodiment provides a lipid-based wax suitable polyol fatty acid ester component includes a fully interesteri
for use as a candle wax, where the lipid-based wax includes a 30 fied triacylglycerol component.
complete polyol fatty acid ester component; and has a melting 6. The candle of claim 1 wherein the lipid-based wax has a
point of about 50° C. to about 60°C.; an Iodine Value of about melting point of at least about 60° C.
40 to 75; and an SFI-10:SFI-40 ratio of at least about 2.0. 7. The candle of claim 1 wherein the lipid-based wax
Another embodiment provides a candle comprising a wick further comprises a polyol fatty acid partial ester.
and a lipid-based wax. The lipid-based wax has a melting 35 8. The candle of claim 1 wherein the lipid-based wax
point of about 48° C. to about 75° C. and includes a fully includes a fatty acid monoglyceride ester, a fatty acid diglyc
eride ester or a mixture thereof.
interesterified polyol fatty acid ester component, such as a 9. The candle of claim 1 wherein the lipid-based wax
fully interesterified triacylglycerol component. The lipid further comprises a second component selected from the
based wax can include 75 wt.% or more of the fully interes 40 group consisting of petroleum waxes, insect waxes, free fatty
terified polyol fatty acid ester component. The lipid-based acids and mixtures thereof.
wax may also include a petroleum wax, an insect wax, 10. A candle comprising a wick and a lipid-based wax:
another plant-based wax (e.g., bayberry wax, candidelia wax wherein the lipid-based wax has a melting point of about 48°
and/or carnuba wax), a polyol fatty acid partial ester and/or C. to about 75° C. and includes at least about 51 wt.% of a
free fatty acids. 45 polyol fatty acid ester component formed by a process which
Another embodiment provides a lipid-based wax suitable comprises interesterifying a polyol fatty acid ester precursor
for use as a candle wax, where the lipid-based wax includes a mixture.
complete polyol fatty acid ester component; and has a melting 11. A candle comprising a wick and a lipid-based wax:
point of about 125° F. to about 140°F.; an SFI-40 of at least wherein the lipid-based wax has a melting point of about 48°
about 20; and an Iodine Value of about 30 to 65. 50 C. to about 75° C. and includes at least about 51 wt.% of a
Yet another embodiment is directed to lipid-based wax triacylglycerol component having a fatty acid composition
suitable for use as a candle wax, where the lipid-based wax which includes X wt.% stearic acid; and the triacylglycerol
includes a completely esterified polyol fatty acid ester com component has a SSS-TAG content which is given by (X/
ponent. The lipid-based wax has a melting point of about 50° 10)+/-3 wt. A).
C. to about 60° C.; an Iodine Value of about 40 to 75; and an
SFI-10:SFI-40 ratio of at least about 2.0.
 UNITED STATES PATENT AND TRADEMARK OFFICE
CERTIFICATE OF CORRECTION
PATENT NO. : 8,157,873 B2 Page 1 of 1
APPLICATIONNO. : 12/903570
DATED : April 17, 2012
INVENTOR(S) : Timothy A. Murphy et al.
It is certified that error appears in the above-identified patent and that said Letters Patent is hereby corrected as shown below:

In the Claims

In column 32, claim 11, line 54, after “10") +/-3 replace “wt. A). with --wt.%.--.

Signed and Sealed this

Twenty-sixth Day of June, 2012

David J. Kappos
Director of the United States Patent and Trademark Office