The JEFFAMINE® Polyetheramines

JEFFAMINE polytheramines are a part of an JEFFAMINE® DIAMINES

expanding family of Huntsman products. They (D, ED, and EDR series)
contain primary amino groups attached to the end JEFFAMINE diamines include the D, ED, and
of a polyether backbone. The polyether backbone EDR series products. The D signifies a diamine,
is normally based on either propylene oxide (PO), ED signifies a diamine with a predominately PEG
ethylene oxide (EO), or mixed PO/EO. Thus they backbone, and EDR designates a highly reactive,
are called “polyetheramines.” Historically, the PEG based diamine. As with the M series, the
JEFFAMINE polyetheramine family consisted of number represents the approximate molecular
monoamines, diamines, and triamines based on weight.
this core structure. Recently, the addition of
secondary, hindered, high-conversion, and
JEFFAMINE® D Series
polytetramethylene glycol (PTMEG) based
JEFFAMINE D series products are amine
polyetheramines has increased the utility of this
terminated PPGs with the following representative
unique product range. The JEFFAMINE
structure:
polyetheramines undergo typical amine reactions,
often imparting increased flexibility, toughness, low
viscosity, and low color. The wide range of
molecular weight, amine functionality, repeating
H2N ( O
) NH2

unit type, and distribution can provide flexibility in

x
the design of new compounds or mixtures. CH3 CH3
JEFFAMINE® MONOAMINES (M series)
JEFFAMINE monoamines are designated as JEFFAMINE® x MW*
the JEFFAMINE M series. The letter M signifies a D-230 ~2.5 230
monoamine and the number represents the D-400 ~6.1 430
approximate molecular weight. D-2000 ~33 2,000
JEFFAMINE M series products are prepared D-4000 (XTJ-510) ~68 4,000
by reaction of a mono-alcohol initiator with EO
and/or PO, followed by conversion of the resulting JEFFAMINE® ED Series
terminal hydroxyl groups to amines. M series JEFFAMINE ED series products are polyether
products have the following representative diamines based on a predominantly PEG
structure: backbone. PEG imparts complete water solubility
to each of the products in this series. The
O NH2 JEFFAMINE ED products have the following
H3C O representative structure:
x y
R H2N
( ) (O ) (O ) NH2
O
x y z
R= H for (EO), or CH3 for (PO) CH3 CH3 CH3

JEFFAMINE® PO/EO mol ratio MW* JEFFAMINE® y x+z MW*

M-600 (XTJ-505) 9/1 600 HK-511 2.0 ~1.2 220
M-1000 (XTJ-506) 3/19 1,000 ED-600 (XTJ-500) ~9.0 ~3.6 600
M-2005 29/6 2,000 ED-900 (XTJ-501) ~12.5 ~6.0 900
M-2070 10/31 2,000 ED-2003 (XTJ-502) ~39 ~6.0 2,000
* MW = approximate molecular weight
JEFFAMINE® EDR Series
JEFFAMINE M-600 and JEFFAMINE M-2005 JEFFAMINE EDR-148 (XTJ-504) and
polyetheramines are predominately polypropylene JEFFAMINE EDR-176 (XTJ-590) amines are much
glycol (PPG) based, whereas JEFFAMINE M-1000 more reactive than the other JEFFAMINE diamines
and JEFFAMINE M-2070 polyetheramines are and triamines. They are represented by the
predominately polyethylene glycol (PEG) based following structure:
and are therefore more hydrophilic.
 JEFFAMINE® Base Product MW*
H2N
(CH2) O
O
( CH2) NH SD-231 (XTJ-584) D-230 315
x 2 SD-401 (XTJ-585) D-400 515
x
SD-2001 (XTJ-576) D-2000 2050
ST-404 (XTJ-586) T-403 565
JEFFAMINE® x MW
EDR-148 (XTJ-504) 2.0 148 EXPERIMENTAL AMINES
EDR-176 (XTJ-590) 3.0 176 This next series of amines includes
monofunctional amines similar to the M series.
These products can be used in a number of They are oleophilic and not water soluble.
applications since they are unhindered diamines
miscible in a wide variety of solvents. Reactions XTJ-435 Chemical Intermediate
typical of aliphatic diamines (polyamide formation
through reaction with dibasic acids, epoxy resin CH3
curing, polyurea formation through reaction with
isocyanates) may be expected with these products. H3C
( CH2 ) O
NH2
12 O
®
JEFFAMINE TRIAMINES (T series) CH3
JEFFAMINE T series products are triamines
prepared by reaction of PO with a triol initiator, XTJ-435 is a monoamine derived from a PO
followed by amination of the terminal hydroxyl adduct of a C12-14 alcohol. This product is
groups. They are exemplified by the following “restricted” and may only be used as a chemical
structure: intermediate.
CH 3 XTJ-436

( H2C )
(O ) CH3
y NH 2
n C 9H19
H2N
( ) (O ) NH 2 (O ) NH2
O 13.5
x z
CH 3 R CH 3

Moles PO XTJ-436 is a 1000 molecular weight,

JEFFAMINE® R n (x+y+z) MW* nonylphenol initiated, polypropylene glycol derived
T-403 C2H5 1 5-6 440 monoamine.
T-3000 (XTJ-509) H 0 50 3000
T-5000 H 0 85 5000 Slower Amines
Slower amines analogous to JEFFAMINE D-
230 and JEFFAMINE T-403 polyetheramines are
JEFFAMINE® Secondary Amines now available under the names XTJ-568 and XTJ-
566, respectively. These unique materials are
(SD Series, ST Series) primary amines created by amination of butylene
The SD Series and ST Series products consist
oxide (BO) capped alcohols. This method results in
of secondary amine versions of the JEFFAMINE
primary amines with the terminal end group
core products. The SD signifies a secondary
structure represented below:
diamine and ST signifies a secondary triamine. The
amine end-groups are reacted with a ketone (e.g. NH2
acetone) and reduced to create hindered
secondary amine end groups represented by the
following terminal structure:
CH3
H3C NH
Higher Conversion Amines
Methods have been developed to increase
CH3 CH3 functionality and conversion to primary amines for
several of the core JEFFAMINE polyetheramines.
One reactive hydrogen on each end group Two such products are currently available: a high
provides for more selective reactivity and makes conversion 440 molecular weight diamine (XTJ-
these secondary di- and triamines useful for 582), and a high conversion 2000 molecular weight
intermediate synthesis and intrinsically slower diamine (XTJ-578). The higher functionality and
reactivity compared with the primary JEFFAMINE conversion are beneficial in polymerizations such
amines. as polyamide formation.
 JEFFAMINE® Polyetheramine Properties

Typical Properties Sales Specifications

JEFFAMINE® Product Avg. Density, Melting Color Primary Total Amine Max
AHEW 25oC, g/ml Point ºC Pt-Co Amine Meq/g % Water
g/eq (±0.01) APHA (% Min)
(Max)
Monoamines
M-600 (XTJ-505) 291 0.979 -40 75 95 1.58-1.79 0.35
M-1000 (XTJ-506) 489 1.066 ■ 29 75 90 0.94 Min 0.25
M-2005 1045 1.000 -36 75 95 0.44 Min 0.25
M-2070 1040 1.072 17 75 95 0.45 Min 0.25
Diamines
D-230 60 0.948 - 25 97 8.10-8.70 0.20
HK-511 ♣ 62 0.991 - 75 - 8.00-9.00 0.25
D-400 115 0.972 - 50 97 4.10-4.70 0.25
XTJ-582 (HC*) 110 0.972 - 50 98 4.20-4.80 0.25
D-2000 514 0.991 - 25 97 0.98-1.05 0.25
XTJ-578 (HC*) 500 0.991 - 40 98 0.94-1.04 0.25
D-4000 (XTJ-510) 1000 0.994 - 75 95 0.44-0.52 0.25
Diamines (EO-Based)
ED-600 (XTJ-500) 132 1.035 -10 75 95 3.00-3.43 0.35
ED-900 (XTJ-501) 250 1.065 ■ 22 100 95 1.80-2.25 0.35
ED-2003 (XTJ-502) 575 1.068 ╦ 43 75 95 0.90-1.05 0.35
Diamines (PTMEG-Based)
XTJ-542 260 0.976 9▲ 50 98 1.87-2.06 0.50
XTJ-548 380 0.965 ■ 33 400 - 1.40-1.70 0.50
XTJ-559 355 0.977 16▲ 50 98 1.35-1.46 0.50
Diamines (High Reactivity)
EDR-148 (XTJ-504) 37 0.998 - 50 98 (% 12.70 Min 0.35
TEGDA)
EDR-176 (XTJ-590) 44 0.980 - 50 99 11.00 Min 0.30
Triamines
T-403 81 0.978 - 50 90 6.10-6.60 0.25
T-3000 (XTJ-509) 530 0.996 - 75 97 0.90-0.98 0.25
T-5000 952 0.997 - 75 97 0.50-0.54 0.25
Secondary Amines
SD-231 (XTJ-584) 158 0.885 - 100 ● <5 ● 5.30-6.30 ● 0.20 ●
SD-401 (XTJ-585) 258 0.921 - 100 ● <5 ● 3.20-4.10 ● 0.20 ●
SD-2001 (XTJ-576) 1025 0.978 - 100 <5 0.90-1.03 0.20
ST-404 ♣ (XTJ-586) 189 0.923 - 100 ● <5 ● 4.40-5.40 ● 0.20 ●
Experimental Amines
XTJ-435 ♣ 157 0.907 - 100 96 2.80-3.20 0.50
XTJ-436 525 0.979 - 100 97 0.91-1.08 0.10
XTJ-566 ♣ 77 0.958 - 75 90 6.60-6.90 0.20
XTJ-568 55 0.943 - 75 93 8.60 Min 0.25

* HC = High Conversion (products have specification for high conversion of alcohol to amine)
● Proposed Sales Specification
▲ After standing for several months will partially crystallize at room temperature
♣ Not EINECS/ ELINCS registered
■ Measured at 38oC
╦ Measured at 50oC
CHEMICAL REACTIONS
JEFFAMINE® polyetheramines undergo reactions typical of primary amines.
General reactions which have proven to be useful include those listed below in the form:
JEFFAMINE Amine + Reactant → Product.
Reactant Product

Epoxy reactions occur by the non-catalyzed

addition of epoxides to JEFFAMINE amines. C C
This alkoxylates each NH functionality to produce
aminoalcohols. O
Epoxides Aminoalcohols
(“epoxy resins”)

Polyurea linkages are formed from the rapid,

uncatalyzed reaction of JEFFAMINE amines
with polyisocyanates. When applied to a RIM
or spray process, this reaction has found great
commercial utility in a variety of applications
including castings, coatings, and sealants. Isocyanates Ureas

The Michael addition of an activated double

bond compound to a JEFFAMINE amine is
a reversible reaction1.
Acrylonitrile Cyanoethylated
amines

Substituted ureas are formed by heating

JEFFAMINE amines with urea at temp-
eratures of 125-175°C, while removing
ammonia. This will result in mono- and di-
substituted ureas.
Urea Substituted ureas

Amides can be formed from JEFFAMINE

amines by an acid-catalyzed reaction with
carboxylic acids, lactams, anhydrides, or by
ester-amide interchange reactions.

Carboxylic acids Amides

(or esters, anhydrides,
etc.)

Imines are formed by reacting

JEFFAMINE amines with aldehydes or
ketones, at elevated temperatures, while
removing water.
Aldehydes Imines
or ketones
+ - + -
Salts of JEFFAMINE amines may be readily H X RNH3 X
formed with a variety of organic and inorganic Acids Salts
acids.
1
Acylonitrile addition leads to a cyanoethylated product that can be catalytically hydrogenated to a non-reversible and stable aminopropylated
polyetheramine.
STORAGE AND HANDLING
Materials of Construction
At temperatures of 75-100°F (24-38oC)
Tanks Carbon steel
Lines, valves Carbon steel
Pumps Carbon steel
Heat exchange Surfaces Stainless steel
Hoses Stainless steel, polyethylene, polypropylene, TEFLON®1
Gaskets, packaging Polypropylene or TEFLON®1 (elastomers such as neoprene, Buna
N, and VITON®1 should be avoided).
Atmosphere Nitrogen or dry air

At temperatures above 100°F (38oC)

Tanks Stainless steel
Lines, Valves Stainless steel
Pumps Stainless steel or Carpenter 20 equivalent
Atmosphere Nitrogen

1
Registered trademark of Dupont

JEFFAMINE® polyetheramines may be stored under air at ambient temperatures for

extended periods. A nitrogen blanket is suggested for all storage, however, to reduce the effect
of accidental exposure to high temperatures and to reduce the absorption of atmospheric
moisture and carbon dioxide. It should be noted that pronounced discoloration is likely to occur
at temperatures above 140°F (60oC), whatever the gaseous pad. Dispose of waste in strict
accordance with local, state, and federal regulations.
FOR MORE LITERATURE OR INFORMATION
Please call the nearest Huntsman Corporation office
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0507
Copyright © 2007 Huntsman Corporation or an affiliate thereof. All rights reserved.
JEFFAMINE® is a registered trademark of Huntsman Corporation or an affiliate thereof in one or more, but not all countries.

Huntsman Petrochemical Corporation warrants only that its products meet the specifications stated in the sales contract. Typical properties, where stated, are to be considered as representative of current
production and should not be treated as specifications. While all the information presented in this document is believed to be reliable and to represent the best available data on these products, NO
GUARANTEE, WARRANTY, OR REPRESENTATION IS MADE, INTENDED, OR IMPLIED AS TO THE CORRECTNESS OR SUFFICIENCY OF ANY INFORMATION, OR AS TO THE
MERCHANTABILITY OR SUITABILITY OR FITNESS OF ANY CHEMICAL COMPOUNDS FOR ANY PARTICULAR USE OR PURPOSE, OR THAT ANY CHEMICAL COMPOUNDS OR USE THEREOF
ARE NOT SUBJECT TO A CLAIM BY A THIRD PARTY FOR INFRINGEMENT OF ANY PATENT OR OTHER INTELLECTUAL PROPERTY RIGHT. EACH USER SHOULD CONDUCT A SUFFICIENT
INVESTIGATION TO ESTABLISH THE SUITABILITY OF ANY PRODUCT FOR ITS INTENDED USE. Liability of Huntsman Petrochemical Corporation and its affiliates for all claims is limited to the
purchase price of the material. Products may be toxic and require special precautions in handling. For all products listed, user should obtain detailed information on toxicity, together with proper shipping,
handling and storage procedures, and comply with all applicable safety and environmental standards.

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