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Surfadone LP

Specialty Surfactants
Product Pro le
Surfadone LP specialty surfactants are linear, N-alkyl-2-pyrrolidones with the following chemical structures: ISP PERFORMANCE CHEMICALS
www.ispcorp.com

Surfadone LP-100

Surfadone LP-300

Surfadone LP specialty surfactants combine the hydrophilic, dipolar pyrrolidone ring with a hydrophobic alkyl group and exhibit a unique combination of solvency and surface activity. ey are multifunctional and provide a variety of performance bene ts in a range of applications.

Applications
Dishwasher rinse aids Hard surface cleaning Laundry prespotters Specialty cleaning Fountain solutions Pigment dispersions Waterborne coatings adhesives Emulsi able concentrates

Performance Features and Bene ts

High surface activity at low concentrations Rapid wetting Low foam Synergism with anionic surfactants Excellent solvency Good compatibility Low ammability Exempt under California Air Resource Board VOC guideline de nitions Biodegradable Favorable toxicological pro les

Applications
Hard Surface Cleaners: Surfadone LP-100 and LP-300 are biodegradable, performance-enhancing co-surfactants and coupling solvents. ey are utilized1-7 in institutional/household kitchen, bathroom, glass, and all-purpose cleaners. e dynamic surface activity of LP-100 promotes rapid wetting, penetration and softening of oily/greasy soils, soap scum and mineral scale, to facilitate removal from a variety of substrates. LP-100 also minimizes streaking on glass, and LP-300 is a particularly e ective coupling solvent for fragrances. Use levels typically range from 0.01-2.0%. Dishwasher rinse aids: Rinse aids perform several functions, and although the most visible bene t is the reduction of spots and lm on glassware/ atware, they also reduce drying time and act as protein soil defoamers. Since high foam levels interfere with the mechanical operation of the dishwasher and reduce the e ectiveness of the rinse cycle, nonionic surfactants are frequently used. Formulations incorporating 2-4% Surfadone LP-100, which provides rapid/e ective wetting and low foam, exhibit minimal lming and spotting. Laundry prespotters: In aqueous formulations. Surfadone LP-100 at 0.5-2.0%, provides rapid/e ective wetting and facilitates the removal8 of oily soil and grease stains from cotton, polyester and cotton-polyester fabrics. Specialty cleaning: In addition to providing high surface activity and wetting, Surfadone LP-100 and LP-300 combine a broad spectrum solvent capability with favorable safety features. Consequently, they are frequently safer alternatives to hazardous solvents and provide solvency for a wide range of organic materials and resins. In aqueous metal cleaners, 1-2% LP-100 facilitates cleaning performance9, 10 and interacts with alkoxylated thiol surfactants11 to minimize odor. Lithographic dampening (fountain) solutions: Surfadone LP-100 is currently the preferred surfactant technology for alcohol-free, continuous dampening systems12 for web o set printing. Performance in such a dynamic process is determined by the speed with which the bulk surfactant in uences the interface. e high dynamic surface activity of LP-100 provides rapid wetting of the non-image area of the printing plate to ensure high print quality. LP-100 also provides low foam, low VOC, high ash points, and by minimization of ink build up, allows longer runs between clean up. Fountain solution concentrates typically incorporate 2-5% LP- 100. Pigment dispersions: To provide stable mill bases with high tinctorial strength, Surfadone LP-100 functions to enhance the wettability of organic pigments. At low use levels, LP-100 permits high pigment loading with low viscosity and is particularly e ective with phthalocyanine pigments. Photoresist strippers: In non-aqueous formulations, 10-20% Surfadone LP-100 is used as a co-solvent, usually in conjunction with M-Pyrol (N-methyl-2-pyrrolidone) and BLO (-butyroIactone), to enhance performance by broadening the solvency range. Printed circuit board cleaners: In aqueous formulations, 1-2% Surfadone LP-100 enhances wetting of aluminum and Te on substrates, and facilitates removal of polymerized rosin residues.13, 14 Waterborne coatings and adhesives: Achieving acceptable adhesion as well as good ow and leveling in water-based systems requires the use of high-performance wetting agents. e low dynamic surface tensions possible through the use of Surfadone surfactants (speci cally Surfadone LP-100), together with their low VOC, support their use as high-performance, low-foaming wetting agents in these applications. e low hydrophilic-lypophilic balance (HLB) values of Surfadone surfactants indicate that they will not add to the water sensitivity of the nished product. For example, Surfadone LP-300 has been shown to optimize the spray pattern and improve adhesion of a chloroprene latex adhesive.15

PAGE 2 SURFADONE LP

Surfadone LP Specialty Surfactants

Emulsi able concentrates: Emulsi able concentrates comprise a concentrated solution of agrochemical actives in solvent/surfactant mixtures, which, when added to water, a ord stable macro/micro emulsions. Surfadone LP-100 and LP-300 are excellent solvents for many crystalline pesticides,16, 17 and as a consequence of their low solubility in water, eliminate the problem of active crystallization, which can occur when the concentrate is added to water. Biodegradability, low volatility, high ash point, emulsion stability, low foam, rapid wetting, and compatibility with aromatic/aliphatic hydrocarbons are also vital features of Surfadone LP specialty surfactants. Use levels range from 1-40%. Table 1: Surfadone LP properties
Properties 7, 1829 Physical Form (25C) Purity (Area % GC) Color (APHA) Moisture (%) Boiling Point (C) Flash Point (C) Closed Cup Freezing Point (C) Vapor Pressure (mm Hg @ 20C) Density (g/cm3 @ 20C) Viscosity (m Pas @ 20C) Refractive Index @ 25C Dipole Moment (Debye) Hansen Solubility Parameters (J/cm3)1/2 HLB Solubility in water (g/L @ 25C) Biodegradable CAS Registry Number Molecular Weight Registration status Surfadone LP-100 Liquid 98 min. 100 max. 0.1 max. 100 @ 0.3 mm Hg 113 -25 <0.001 est. 0.922 9 1.471 3.83 T = 18.9 d = 16.9 p = 6.2 h = 5.8 6 0.124 Yes 2687-94-7 197 TSCA, EINECS, MITI Surfadone LP-300 Liquid 98 min. 180 max. 0.1 max. 145 0.2 mm Hg 116 10 <0.001 est. 0.903 18 1.466 3.82 T = 18.2 d = 16.9 p = 4.4 h = 5.0 3 0.02 Yes 2687-96-9 253 TSCA, EINECS, MITI

Note: Above data are typical of current production. Product speci cations may be obtained from ISP.

SURFADONE LP PAGE 3

Solubility
Surfadone LP specialty surfactants are readily soluble in most organic solvents and exhibit unique solubility characteristics in water. In aqueous solution at ambient temperature, single-phase systems are obtained with LP-100 concentrations <0.124% and LP-300 concentrations < 0.002%. As the concentration of Surfadone LP is increased, two phases separate until at 65% LP-100 and 80% LP-300, a single phase is obtained. As the temperature of two-phase systems is decreased, the solubility of both Surfadone LP-100 and LP-300 increases. Before the lower critical solution temperature (LCST) or cloud point can be reached, ice crystals form. Surfadone LP-100 and LP-300 interact with anionic surfactants and are solubilized in aqueous solution to a ord mixed micelles. Low-viscosity solutions of up to 8% LP-100 and up to 4% LP-300 may be obtained with 1-2% sodium dodecyl sulfate (SDS). Viscous solutions and gels are obtained with LP-300 concentrations > 4%. Surfadone LP specialty surfactants are also solubilized in water, although less e ciently, by water-miscible organic solvents e.g., 30% propylene glycol is required to dissolve 3% LP-100.

PAGE 4 SURFADONE LP

Surfadone LP Specialty Surfactants

Surface Tension Reduction, Wetting and Foaming

Both Surfadone LP-100 and LP-300 exhibit comparable e ectiveness in reducing the static (equilibrium) surface tension of water and do not reach a critical micelle concentration (CMC). Surfadone LP-300 exhibits greater e ciency in static surface tension reduction than LP-100. Dynamic surface tension is a measure of the kinetics of surfactant adsorption/orientation at the interface and may be correlated with wetting speed. Surfadone LP-100 is a more e ective dynamic surface tension reducer/wetting agent than LP-300, which may be attributed to the greater solubility/mobility of LP-100 in an aqueous environment. Anionic surfactants, such as SDS and linear alkyl benzene sulfonate (LAS) interact with Surfadone LP-100 and LP-300 to provide synergistic surface tension reduction and wetting enhancement. Surfadone LP-100 and LP-300 are low foaming, as determined by the Ross-Miles method. Mixtures of LP-100 with SDS, at total surfactant concentrations of 0.1%, exhibit minor synergistic increases in foam height, although no synergism was observed with LP-300. Surfadone LP specialty surfactants are compatible with cationic, nonionic and amphoteric surfactants, although no synergistic interactions have been reported. Surface tension (Graphs 1-3), Ross-Miles (Table 4) and Draves data (Graph 4 and Table 2) for Surfadone LP-100 and LP-300 are summarized.

Graph 1: Static Surface Tension on Various Surfactants

80 70

Static Surface Tension on Various Surfactant

Dynamic Surface Tension o

80

Surface Tension (mN/M)

50 40 30 20 10 0 0.00E+00

Surface Tension (mN/M)

60

60

40

20

0 2.00E02 4.00E02 6.00E02 8.00E02 1.00E01 1.20E01 1.40E01 1.60E01

Concentrations (Wt %) Surfadone LP-100 Alcohol Ethoxylate 9EO Linear NPE 9EO Branched NPE 9EO Linear

Surfadone LP-1

Alcohol Ethoxyla

Graph 2: Dynamic Surface Tension on Various Surfactant at 0.1% Concentration Dynamic Surface Tension on Various Surfactants at 0.1% Concentration
80

Surface Tension (mN/M)

60

40

20

10

Bubble Frequency (Hz) Surfadone LP-100 Alcohol Ethoxylate 9EO Linear NPE 9EO Branched NPE 9EO Linear

SURFADONE LP PAGE 5

Graph 3: Dynamic Surface Tension of Surfadone LP-100 with Sodium Dodecyl Sulfate*

PAGE 6 SURFADONE LP

Surfadone LP Specialty Surfactants

%LP-100 (+0.025% SDS) 1n 0.000 0.005 0.010 0.050 0.100 0.250 0.500 0.700 69 60 54 38 33 30 29 29

Surface Tension (dynes/cm) Bubbles/sec. 5l 70 65 60 41 31 31 30 29 10 71 67 64 44 32 32 31 30

* American Ink Maker, October 1994

Graph 4: Draves Wetting Surfadone LP-100 and Sodium Dodecyl Sulfate

Draves skein wetting 0.5 g/l 0.75 g/l x 1.0 g/l

Draves Wetting Surfadone LP-100 and Sodium Lauryl Sulfate

20

Wetting time (sec.)

15

10

x x

x x x x x x x

10

25

50

75

90

100

% C8P (w/w) in C8P-LAS Mixture

Draves skein wetting time vs. percentage of C8P in C8P-LAS mixtures at various total surfactant concentrations. JAOCS 66(7): 998-1001, 1989 Table 2. Draves Writing at 0.1%, seconds*
Name Poloxamer 182 Poloxamer 407 Nonoxynol 30 Dodecylphenol + 6EO Polysorbate 20 Nonoxynol 9 Phosphate Sodium dodecyl diphenyl oxide disulfonate Surfynol 104 LAS Surfadone LP-100 *JAOCS 72: 759-771, 199 Surfactant Alone >300 >300 >300 >300 >300 142 103 12 9 3.5 1:1 blend with Surfadone LP-100 41 48 13 44 33 20 11 Instantly 3.5

SURFADONE LP PAGE 7

PAGE 8 SURFADONE LP

Surfadone LP Specialty Surfactants

e wetting capability of Surfadone LP is also demonstrated by contact angle reduction on both high and low energy surfaces. LP-100 is particularly e ective on aluminum and representative data are summarized in Table 3. Table 3. Contact Angles
Aluminum Water Surfadone LP100 (0.1% in water) Surfadone LP300 (0.1% in water) 84 <5 36 Silicone 95 56 53 Polypropylene 95 34 33 Te on 113 54 54

Foaming
Surfadone LP products are low foaming in aqueous solutions. e initial foam heights in Ross-Miles tests are 25mm and 13mm for Surfadone LP-100 and LP-300 respectively. e initial and ve minute foam heights for Surfadone LP-100 and LP-300 mixed with SDS are shown in Table 4 below. Table 4. Surfadone LP/SDS Ratio
Pure Surfadone LP-100 Surfadone LP300 Sodium Dodecyl Sulfate (SDS) Foam Height (mm), initial/5 min Total concentration, 0.1% 25/5 13/11 156/156 3:1 159/159 139/139 1:1 164/161 135/135 1:3 58/157 151/151

Compatibility with Plastics and Elastomers

Quantitative results on weight and dimensional changes, for 15 plastics or elastomers exposed to Surfadone LP specialty surfactants, at ambient temperature for 7 days, are shown in Tables 5 and 6. Polyethylene, polypropylene, nylon, Kynar (polyvinylidene uoride) and Te on (polycarbonate), Noryl EN-265 (polyphenytene oxide), Viton (polyvinylidene uoride-hexa uoropropylene) ABS, EPDM-70 and PVC should be avoided.

Table 5: Surfadone LP-100 at ambient temperature for 7 days % change

Coupon ABS Butyl rubber EPDM-70 Kynar (PenwaIt) Lexan (GE) Noryl EN-265 (GE) Nylon Polyethylene (XL) Polyethylene (LD) Polyethylene (HD) Polypropylene Polyvinyl chloride Silicon rubber Te on (DuPont) Viton (DuPont) 17.6 0.01 201.4 4.8 -0.4 0.15 0.02 0.25 0.08 12.48 66.7 0.58 Weight Length Width Thickness

Coupons fragmented after 24 hours 3.23 20.06 0.19 0.39 19.73 0.32 3.23 25.66 2.13

Coupons dissolved after 48 hours 0.43 -0.1 0.03 0.42 0.07 0.2 0.98 -0.19 0 1.4 -0.13 0.33 3.19 0.07 0.24 0 -0.88 0

Coupons dissolved within 48 hours 5.16 0.07 65.0 7.4 0.26 75.5 6.7 0 71.7

Table 6: Surfadone LP-300 at ambient temperature for 7 days % change

Coupon ABS Butyl rubber EPDM-70 Kynar (PenwaIt) Lexan (GE) Noryl EN-265 (GE) Nylon Polyethylene (XL) Polyethylene (LD) Polyethylene (HD) Polypropylene Polyvinyl chloride Silicon rubber Te on (DuPont) Viton (DuPont) 9.7 4.68 197.9 12.5 66.7 0.02 18.9 0.13 0.3 0.09 0.24 0.19 0.10 Weight Length Width Thickness

Coupons fragmented after 24 hours 3.14 6.67 0.13 13.1 0.59 0.23 0.13 0.19 0.13 0.03 3.02 19.73 0 0.39 0.13 0.07 0.13 0.32 0.07 0.26 3.13 24.0 2.13 0.03 0.55 0 0.49 3.23 0.02 0.53

Coupons dissolved within 48 hours 2.05 0.07 64.5 11.09 -0.2 76.0 5.52 3.12 77.2

SURFADONE LP PAGE 9

Biodegradation Studies
Surfadone LP-100 and LP-300 were classi ed as ultimately biodegradable in the modi ed Semi-Continuous Activated Sludge (SCAS) test and readily biodegradable in the modi ed Sturm test. e modi ed SCAS test is designed to determine the removability/biodegradability of a test compound in activated sludge.Surfadone LP-100, at a test concentration of 20 mg carbon/L, achieved an average 99.8% removal following a 5-day acclimation period. In accordance with EPA test guidelines, 40 CFR 796.3340, these products may be classi ed as ultimately biodegradable. e modi ed Sturm test is designed to give an indication of the extent of ultimate biodegradation of a test compound. Surfadone LP-100 reached levels of 80.9% and 83.1% of the theoretical CO2 production in 28 days, for the test concentrations of 10 and 20 mg/L, respectively. Surfadone LP-300 reached levels of 87.4% and 74.2% of the theoretical CO2 production in 28 days, for the test concentrations of 10 and 20 mg/L, respectively. In accordance with EPA guidelines, 40 CFR 796.3260, these compounds may be classi ed as readily (highly) biodegradable in aerobic systems, and are fully compliant with European Parliament and the Council EC No. 648/2004 regulation.

PAGE 10 SURFADONE LP

Surfadone LP Specialty Surfactants

Toxicological Studies
An extensive study of Surfadone LP-100 and LP-300 has been carried out and both compounds exhibit a favorable toxicological pro le. e results are summarized in Table 7, and more detailed information, including aquatic toxicity, may be obtained from ISPs Product Stewardship Department. Table 7: Toxicological pro le
Test Acute oral LD50 in rats (g/kg) Acute dermal LD50 in rabbits (g/kg) Primary eye irritation in rabbits (2% aqueous suspension) Primary skin irritation in rabbits (as supplied) Primary skin irritation in rabbits (2% aqueous suspension) Dermal sensitization in humans (1% aqueous suspension) Mutagenicity (Ames assay) Comedogenicity (2% aqueous suspension) Surfadone LP-100 2.05 >2 Non-irritating Extremely irritating Mildly irritating Did not induce dermal contact sensitization Non-mutagenic Not expected to be comedogenic in humans Surfadone LP-300 >5 >2 Non-irritating Severely irritating Mildly irritating Did not induce dermal contact sensitization Non-mutagenic Not expected to be comedogenic in humans

Handling and Storage

Surfadone LP specialty surfactants are corrosive and can cause severe eye and skin burns. Normal good practices should be followed. Wear goggles and impervious gloves. In case of accidental contact with skin or eyes, wash area immediately with water. Refer to the MSDS for more datailed information. Surfadone LP specialty surfactants are available in tank wagon and tank car quantities, as well as various-size phenolic-lines drums. For bulk storage, unloading and handling, it is recommended that 304 stainless steel storage tanks, pumps and piping and Te on gaskets and seals be used. Rubber hosing is not recommended.

References
1. A. Liu and J. W. Miliner. Cleaning Compositions Based on N-Alkylpyrrolidones Having About 8 to 12 Carbon Atoms in the AlkyI Group and Corresponding Methods of Use, US Patent 5,503,778 2. D. I. Jon and J. C. Hornby. Conversion of Water-Insoluble Soap Scum Into A Stabilized Dispersion, US Patent 5,435,934 3. A .Garabedian Jr. et al. Reduced Residue Hard Surface Cleaner, US Patent 5,437,807 4. C. K. Choy et al. Reduced Residue Hard Surface Cleaner, US Patent 5,585,342 5. J A. McDonell. Multisurface Cleaning Composition and Method of Use, US Patent 5,573,710 6. S. Adamy et al. Microemulsion All Purpose Liquid Cleaning Compositions, US Patent 5,641,742 7. J. C. Hornby and D. Jon. Surface Active Specialty Solvents, Soap/Cosmetics/Chemical Specialties, September 1992 8. K. S Narayanan and P D. Taylor. Water Based Compositions for Removing Stains from Fabrics, US Patent 5,085,795 . 9. S. Dunn and A. E. Winston. Aqueous Metal Cleaner, WO 96/09368 10. L. R. Carlson et al. Composition and Method for Degreasing Metal Surfaces, US Patent 5,643,979 11. S. A. Bolkan et al. Aqueous Metal Cleaner with Zinc Phosphate Anti-Corrosion System, US Patent 5,712,236 12. J. C. Hornby and D. Jon. A Wetting Agent for Alcohol-Free Fountain Solutions, Amer. lnkmaker, October 1994 13. F. A .Cala and R. A. Reynolds. Flux Removing Composition, US Patent 5,688,753 14. H. Obuse. Composition for Cleaning and Process for Cleaning, European Patent Application 0,728,838 15. E. Simmler and T. Simmler. Sprayabie Dispersion and Process for Elastic Adhesive Joining of Two Substrate Surfaces, European Patent Application 0,624,634 16. K. S Narayanan and A. K Chaudhuri. Emulsi able Concentrate Formulations For Multiple Active Ingredients Using N-Alkylpyrrolidones. Pesticide Formulations and Application Systems: 11th Volume. ASTM STP 1112. L. F Bode et al. Eds.. American Society for Testing and Materials. Philadelphia. 1992 17. K. S. Narayanan and R. K. Chaudhuri. N-Alkylpyrrolidone Requirement For Stable Water-Based Microemulsions. Pesticide Formulations and Application Systems 12th Volume. ASTM 1146. B. N. Devisetty et al. Eds., American Society for Testing and Materials, Philadelphia. 1993 18. A. B Login. Pyrrolidone-Based Surfactants. JAOCS, 72,759, 1995 19. M J Rosen et al. Relationship of Structure to Properties of Surtactants 14. Some N-Alkyl-2-pyrrolidones at Various Interfaces. Langmuir. 4,1273, t998 20. M. J. Rosen et al. Synergism in Binary Mixture of SLirfactants 9 N-Alkyl-2-pyrrolidone-Anionic Mixtures, J Colloid Interface Sci. 129(2). 468,1989 21. Z. H. Zhu. Some Synergistic Properties of N-AlkyI-2-pyrroildones. A New Class of Surfactants. JAOCS. 66,998,1989 22. M. J. Rosen. Synergism in Mixtures Containing Zwitteriontc Surfactants. Langmuir. 7,885,1991 23. M. J. Rosen and Z H. Zhu. The Stability of Sodium Hypochlorite in the Presence of Surfactants. JAOCS, 69,667, 1992 24. M. J. Rosen and L. D. Song. Sliperspreading. Skein Wetting and Dynamic Surface Tension, Langmuir. 12,4945, 1996 25. S. T. Adamy. Phase Studies of Water/AlcoholOctyl-2-pyrrolidone/Alkane Systems. Langmuir. 11,3269, 1995 26. A. Lou, B. A. Pethica and P Somasundaran. Surface and Colloidal Properties of Cyclic Amides. I. Two-Dimensional Virial . Coef cients for Adsorbed Monolayers of N-Alkyl-2-pyrrolidones at the Air/Wafer Interface Langmuir. 12,5845, 1996 27. A. Lou, B. A. Pethica and P Somasundaran. Surface and Colloidal Properties of Cyclic Amides. II Phase Separation. . Surface Activity and Micellization in Mixtures of N-Hexyl-2-pyrrolidone and Water. Colloids And Surfaces A: Physicochemical and Engineering Aspects 129-130,297, 1997 28. A. Lou, B. A. Pethmca and P Somasundaran. Nonaqueous Liquid/Liquid Interfaces: Surface Activity at the Interface . between n-Paraf ns and N-Alkyl Derivatives of 2-Pyrrolidone. J Colloid and Interface Science. 202,318,1998 29. A. Lou, B. A. Pethica. P Somasundaran and A. Fan. Surface and Colloid Properties of Cyclic Amides. III. Activity and . Micellization of N-Butyl-2-pyrrolidone in Water. J Dispersion Science and Technology. 20,569,1999

SURFADONE LP PAGE 11

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Trademark registration applied for Registered trademark of the ISP group International Specialty Products. 2008 Designed & Printed in USA.

Product Code: PECH_C1007 06/2008

The information contained in this brochure and the various products described are intended for use only by persons having technical skill and at their own discretion and risk after they have performed necessary technical investigations, tests and evaluations of the products and their uses. While the information herein is believed to be reliable, we do not guarantee its accuracy and a purchaser must make its own determination of a products suitability for purchasers use, for the protection of the environment, and for the health and safety of its employees and the purchasers of its products. Neither ISP nor its affiliates shall be responsible for the use of this information, or of any product, method, formulation, or apparatus described in this brochure. Nothing herein waives any of ISPs or its affiliates conditions of sale, and WE MAKE NO WARRANTY, EXPRESS OR IMPLIED, OF MERCHANTABILITY OR FITNESS OF ANY PRODUCT FOR A PARTICULAR USE OR PURPOSE. We also make no warranty against infringement of any patents by reason of purchasers use of any information, product, method or apparatus described in this brochure.