Hydrocarbons Toluene M Aromatic-100 M Ethyl benzene M Aromatic-150 M Xylene PS Heptane I Tetralin M Aliphatic hydrocarbon petroleum naphtha SS

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1 Technical Bulletin FlexiSolv DBE Esters for Coatings Applications and Formulations FlexiSolv DBE esters is an important highboiling, oxygenated solvent for the coatings industry. FlexiSolv DBE esters has been successfully used in coatings for over 30 years and continues to be used in new coatings formulations that comply with changing regulations. Important FlexiSolv DBE esters benefits as coatings solvent include: Excellent solvency conferring good leveling and flow properties Improved coating flexibility and adhesion Superior pigment hiding power in certain industrial coatings Miscibility with most organic solvents (see Table 1) Solvency for a wide range of resins (see Table 2) Clean burning vapors with good Btu value Table 1: Solubility of Various Liquids in FlexiSolv DBE esters, 25 C (77 F) Compound Solubility Compound Solubility Alcohols Methanol M i-butanol M Ethanol M N-Butanol M i-propanol M Methyhl amyl alcohol M n-propanol M Cyclohexanol M t-butanol M 2-Ethylhexanol M M m-cresol M Glycol Ethers Propylene glycol monomethyl ether M Dipropylene glycol monomethyl ether M Ethylene glycol monomethyl ether M Diethylene glycol monomethyl ether M Ethylene glycol monoethyl ether M Diethylene glycol monoethyl ether M Ethylene glycol monobutyl ether M Diethylene glycol monobutyl ether M Hydrocarbons Toluene M Aromatic-100 M Ethyl benzene M Aromatic-150 M Xylene PS Heptane I Tetralin M Aliphatic hydrocarbon petroleum naphtha SS Esters Ethyl acetate M 2-Ethylhexyl acetate M n-butyl acetate M Butyrolactone M i-butyl i-butyrate M Propylene carbonate M Methyl amyl acetate M Dimethyl phthalate M Ethylene glycol diacetate M Hexylene glycol diacetate M Propylene glycol monomethyl ether acetate M Ethyl 3-ethoxypropyl acetate M Ethylene glycol monoethyl ether acetate M Texanol TM a M Ethylene glycol monobutyl ether acetate M Ketones Acetone M Cyclohexanone M Methyl ethyl ketone M Diacetone alcohol M Methyl i-butyl ketone M Isophorone M Methyl amyl ketone M Halogenated Solvents Methylene chloride M 1,1,1-Trichloroethane M Trichloroethylene M Perchloroethylene M Chlorobenzene M Glycols Propylene glycol M Ethylene glycol M Hexylene glycol M Diethylene glycol M

2 2 Other Solvents Tetrahydrofuran M N-Methyl-2-pyrrolidone M Dimethyl formamide M Water VSS Dimethylsulfoxide (DMSO) M Legend: M = Miscible I = Insoluble PS = Partly Soluble SS = Slightly Soluble VSS = Very Slightly Soluble a Eastman A variety of FlexiSolv DBE esters compositions are available from INVISTA and its authorized distributors to adjust solvent vapor pressure or composition to more specific needs. FlexiSolv DBE esters is a relatively slow evaporator at ambient conditions with a vapor pressure of 0.2 Torr at 20 C. In high temperature coatings operations where volatile vapors are captured and incinerated or burned for fuel, DBE esters burns cleanly with a fuel value of about 9,000 Btu/lb. Coalescing solvents reduce the glass transition temperature (Tg) of resins, allowing polymeric systems to form continuous films at ambient or sub-ambient temperatures. Table 2: Solubility of Coating Resins in FlexiSolv DBE esters ª Epoxy EPON TM 826 b EPON TM 1001F b EPON TM 1007F b DER TM 667 c Phenoxy UCAR PKHH c EPONOL TM 52 b Acrylic Poly(methyl methacrylate) Methyl methacrylate/nbutyl methacrylate copolymer Polyester CYPLEX c CYPLEX 1526 e Cargill 5770 d Polyester, wire enamel resin Cellulosic Nitrocellulose, RS, ½ sec Cellulose acetate butyrate Phenolics METHYLON resin #75108 f 709 Phenolic Amino CYMEL 303 e Vinyl UCAR TM Solution Vinyl VAGH c UCAR TM Solution Vinyl VYHH c UCAR TM Solution Vinyl VMCC c a Solubility at 25 C (77 F), 10% solids b MOMENTIVE c Dow Chemical d Cargill Strongly swollen, partly soluble h (DBE -2 esters only) e CYTEK f Durez Corp g Schnectady Chemicals h FlexiSolv DBE -2 esters differs from the others and gives a clear solution in this instance. For FlexiSolv DBE esters and FlexiSolv DBE -9 esters, the resin is strongly swollen and only partly soluble.

3 3 Without additions of coalescing species, polymers (acrylics) may be brittle and/or form films that do not adhere to the substrate. FlexiSolv DBE - IB esters possesses the properties desired for an outstanding coalescing agent. FlexiSolv DBE -IB esters properties are: Low volatility Good plasticizing ability Low solubility in water Biodegradable High flash point Low odor (sweet) Hydrolytically stable Scrub-resistant Applications Industrial Coating FlexiSolv DBE esters is recognized as an important high boiling solvent for industrial coatings. It has successfully replaced a number of solvents, including isophorone, cresylic acid, glycol ethers, glycol ether acetates, and cyclohexanone (see Formulations section for details). FlexiSolv DBE esters is compatible with a wide range of resins, reduces orange peel and solvent popping while improving flow and leveling characteristics, and has superior pigment hiding power in certain industrial coatings. Additional technical information is available on request. Coil, Sheet, and Can Coatings These applications are highly demanding and require high-speed application, good coverage without excess coating consumption, and the ability to be drawn and formed into a variety of shapes while maintaining the integrity of the coating. Coatings applied from FlexiSolv DBE esters formulations yield high performance finishes with good adhesion, lower friction in forming operations, and improved film flexibility. The coatings exhibit good flow and leveling properties. Typical applications include appliance and transportation parts, metal furniture, and food/beverage containers. Automotive Coatings Originally used as a key reflow ingredient in OEM acrylic lacquer topcoats, FlexiSolv DBE esters is now used in refinish formulations. FlexiSolv DBE esters formulations promote smooth surfaces and high gloss in enamel systems and smooth surfaces in epoxy and polyester primer surfaces. Formulations Solvency The coatings industry has widely accepted the use of solubility parameters to select solvents. The approach of Hansen, 1 when simplified to use only the hydrogen bonding and polar components, is convenient. The Hansen solubility parameters for FlexiSolv DBE esters are listed in Table 3. Figure 1 relates the Hansen parameters of FlexiSolv DBE esters to other active solvents. FlexiSolv DBE esters is similar in solvency to isophorone, acetone, methylene chloride, and 2-ethoxy-ethyl acetate (EE acetate). In coatings, FlexiSolv DBE esters as a solvent is normally used with other solvents to optimize cost, solvency, flash point, toxicity, viscosity, volatility, and other properties for the particular coatings resin being used. A preferred method to optimize uses the solubility parameter concept. 1,2 The envelope of solubility of a resin is determined by its behavior in a variety of standard solvents. Table 1 shows the solubility of various liquids in FlexiSolv DBE esters at 25 C (77 F). Its solubility envelope defines the solvent that dissolves the resin. Technical Assistance Using several computer models, INVISTA predict the resin solubility in a solvent. Table 3: Solvent Properties Property FlexiSolv DBE esters Solubility parameters a Hydrogen bonding 4.8 Polar 2.3 Nonpolar 8.3 Kauri-butanol value 51 Flash point, C( F) (Tag closed cup) 100(212) Surface tension at 20 C (68 F), dyh/cm 35.6 Viscosity at 25 C (77 F), cst. 2.4 Electrical resistance b at 24 C (75 F), megohms 0.5 Dielectric constant at 20 C (68 F) 5.1 VOC lb/gal 9.1 G/L 1,090 a Hansen Solubility Theory b Ransbury Paint Resistance Tester Model 219 CD

4 4 Figure 1: Hansen Solvent Map Evaporation Rate FlexiSolv DBE esters confers good flow and leveling characteristics to many coatings compositions. Solvent power is consistent throughout the evaporation period. Evaporation rate can be modified with the selection of various FlexiSolv DBE esters or by blending with other solvents and diluents if required. FlexiSolv DBE esters is composed of three esters, and its evaporation range is wider than the one- or two-component mixtures of the other FlexiSolv DBE esters fractions. In Shell thin film evaporometer tests, 90% of the original FlexiSolv DBE esters evaporates in 940 min compared to about 330 min for isophorone. Table 4 shows evaporation rates of FlexiSolv DBE esters and its fractions relative to several other solvents. An advantage of FlexiSolv DBE esters is that its rate of evaporation increases faster with increasing temperature than most other solvents, allowing more favorable drying cycles at elevated baking temperatures. For instance, at 25 C (77 F), the evaporation rate of isophorone is three times greater than FlexiSolv DBE esters s, while at a baking temperature of 135 C (275 F), the evaporation rates are nearly equal. Evaporation versus temperature are shown in Figure 2, illustrating that FlexiSolv DBE esters s evaporation rate increases faster than that of many common coatings solvents. 3

5 5 Figure 2: Coating Solvents Evaporation vs. Temperature Viscosity Viscosities of resin solutions formulated with FlexiSolv DBE esters are suitable for the application requirements of liquid coatings. In Table 5, the viscosity of FlexiSolv DBE esters is compared with other active solvents in coating formulations. For solvent-based coatings, the solvent viscosity is usually proportional to the solution viscosity. 2 Therefore, by changing to a less viscous solvent such as FlexiSolv DBE esters, the solution viscosity may be reduced without lowering molecular weight of solids content. Conversely, solids content may be increased while maintaining the same viscosity. This effect is illustrated in Figure 3. Use of ketones and/or hydrocarbons in solvent blends with FlexiSolv DBE esters will usually provide lowest viscosity, if such solvents are compatible with the coating system. Table 4: Solvent Evaporation Rates 90% Evaporation time in minutes FlexiSolv DBE esters 940 FlexiSolv DBE -2 esters 1300 FlexiSolv DBE -3 esters 2533 FlexiSolv DBE -4 ester 407 FlexiSolv DBE -5 ester 848 FlexiSolv DBE -6 ester 2920 FlexiSolv DBE -9 esters 750 FlexiSolv DBE -IB esters 6192 Isophorone 333 N-Methyl-2-pyrrolidone 257 Glycol ether EE acetate 46 n-butyl acetate 7.5 1,1,1-Trichloroethane 1.8 Acetone 1.4 Methylene chloride 0.8 Table 5: Viscosities of Active Solvents Viscosity (25 C [77 F]) Solvents centistokes Ethylene glycol monoethyl ether acetate 1.2 N-Methyl-2-Pyrrolidone 1.6 Ethylene glycol monoethyl ether 2.0 Cyclohexanone 2.1 FlexiSolv DBE esters 2.4 Isophorone 2.5 Diacetone alcohol 3.0 Ethylene glycol mono-n-butyl ether 3.2 Diethylene glycol monoethyl ether 3.9 Diethylene glycol mono-n-butyl ether 5.2 Cresylic acids: Merichem CA-43S 13.2 *Standard Shell Thin Film Evaporometer Test at 25 C (77 F) ASTM D

6 6 Figure 3: Viscosity of Polyester Resin Solutions As shown in Figure 4, solvent blends with FlexiSolv DBE esters fall well within the solubility envelope of common epoxy resins. Starting formulations for epoxy resin solvent blends are presented in Table 6. Polyester and Alkyd Resins FlexiSolv DBE esters offers polyester resin coating formulators a balance of high performance and low cost. Its combination of high solvency and slow evaporation makes FlexiSolv DBE esters an excellent choice to replace glycol ethers and glycol ether acetates in polyester formulations. FlexiSolv DBE esters is also gaining wide acceptance for cleanup of unsaturated polyester resins in the fiberglassreinforced plastics industry. Coatings Formulations Many commonly used resins are soluble in FlexiSolv DBE esters solvents as indicated in Table 2. Those few resins that are not completely soluble in pure FlexiSolv DBE esters can usually be dissolved with a blend of FlexiSolv DBE esters and another active solvent. As shown in Figure 5, solvent blends with FlexiSolv DBE esters fall well within the solubility envelope of a common polyester resin. Starting formulations for polyester resin solvent blends are presented in Table 7. 4 For example, the Bakelite vinyl resins, VAGH and VYHH, are soluble in a 60/40 FlexiSolv DBE esters/cyclohexanone blend. INVISTA can provide technical assistance on suggested blends with the use of its computer program based on the Hansen solubility parameters. Epoxy Resins FlexiSolv DBE esters is an excellent solvent for epoxy resins. FlexiSolv DBE esters solvent blends are being used as replacements for glycol ethers, glycol ether acetates, and isophorone in epoxy resin formulations for appliance, coil, and container coatings. The combination of solvency and evaporation rate of these blends ensures epoxy resin solubility through the baking cycle, thereby contributing to good leveling. The active solvency of FlexiSolv DBE esters also ensures compatibility with phenolic and amine-converting resins. Figure 4: Shell EPON 1004F

7 7 Table 6: Epoxy Resins Solvent Blend Suggestions Solvents Original Blend FlexiSolv DBE Blend #1 FlexiSolv DBE Blend #2 EE Acetate 50 Xylene DBE esters PM Acetate 25 n-butanol EEP* 20 Solubility Parameters Nonpolar Polar Hydrogen bonding Density, lb/gal *EEP = Ethyl-3-ethoxypropionate Acrylic Resins FlexiSolv DBE esters has a proven history in solvent blends for acrylic lacquer and nonaqueous dispersion enamel systems. FlexiSolv DBE esters also continues to play a significant role in the automotive refinish market. Figure 6 shows that DBE esters blends fall well within the solubility envelope of common acrylic resins. Starting formulations for acrylic resin solvent blends are presented in Table 8. Figure 6: Lucite International Elvacite 2013 Acrylic Resin Figure 5: Cargill Polyester Plastic 6608 Table 7: Polyester Resins Solvent Blend Suggestions DBE DBE DBE Original Blend Blend Blend Solvents Blend #1 #2 #3 EE Acetate 50 Aromatic DBE esters MIBK n-butanol PM Acetate Solubility Parameters Nonpolar Polar Hydrogen Bonding Density, lb/gal Table 8: Acrylic Resins Solvent Blend Suggestions DBE DBE Original Blend Blend Solvents Blend #1 #2 EE Acetate 13 Toluene MEK DBE esters 5 7 PM Acetate 8 n-butanol 6 Solubility Parameters Nonpolar Polar Hydrogen Bonding Density, lb/gal

8 8 Vinyl Solution Resins Blends of FlexiSolv DBE esters with cyclohexanone, diisobutyl ketone, methyl isobutyl ketone, or butyrolactone can replace isophorone in most formulations of vinyl solution resins. Table 9 gives two FlexiSolv DBE esters solvent blends that are satisfactory replacements for isophorone blends, while Figure 7 illustrates that FlexiSolv DBE esters solvent blends fall within the solubility envelope of a typical vinyl coating resin. Small amounts of FlexiSolv DBE esters may be used in organosol dispersion coatings as a dispersant or to lower fusion temperatures. FlexiSolv DBE esters can be considered to be a temporary plasticizer with very high solvency towards vinyl chloride resins when compared with high molecular weight diester plasticizers. Table 8: Vinyl Resins Solvent Blend Suggestions DBE DBE Original Blend Blend Solvents Blend #1 #2 Isophorone 37 MIBK Aromatic DBE esters MEK 9 Solubility Parameters Nonpolar Polar Hydrogen Bonding Density, lb/gal Other Information FlexiSolv DBE esters and its fractions are not included on the list of hazardous air pollutants (HAPs) under the U.S. Clean Air Act. Dispose in accordance with all applicable regulations. Biodegradability All of the components (dimethyl succinate, dimethyl glutarate, and dimethyl adipate) are readily biodegradable. (EPR), silicone, Teflon, and DuPont Performance Elastomers Kalrez. Ask for our separate technical sheet on the compatibility of FlexiSolv DBE esters for common elastomers and plastics. Waste Handling FlexiSolv DBE esters can be effectively recycled using commercially available vacuum distillation equipment at about 138 C (280 F) and 26 inches of mercury vacuum. Spent FlexiSolv DBE esters has a heating value of about 9,000 Btu/lb (depending on actual stream makeup), allowing it to be incinerated effectively or included in a fuels blending program. For More Information For more information on FlexiSolv DBE esters and their use in coatings applications and formulations, call (800) References: 1 Hansen, C. M., Journal of Paint Technology 39(505), (1967). Hansen, C. M. and Beerbower, A., in Standen A., (Ed.), Kirk-Othmer, Encyclopedia of Chemical Technology (Suppl. Vol. 2 nd Ed.), 1971, p Burrell, H., Official Digest 27 (369), (1955). Barton, A. F. M., Chemical Rev. 75 (6), (1975). These references discuss solubility theory. 2 Turner, G. P. A., Introduction to Paint Chemistry and Principles of Paint Technology, Chapman and Hall, London, 1980, p Jackson, H. L., Journal of Paint Technology 58 (741), (1986). 4 Maynard, D. M. and Jackson, H. L., Pitture and Vern. 65 (12), (1989). Compatibility with Elastomers FlexiSolv DBE esters is compatible with many elastomers, including ethylene propylene rubber

9 9 For Samples and Information: INVISTA TM Specialty Intermediates (800) This Product Data Sheet contains selected information about a specific INVISTA product, or group of products, and particular uses of the same. It relates only to the identified product and any identified uses, and is based on information available as of the date hereof. Additional information may be needed to evaluate other uses of the product, including use of the product in combination with any materials or in any processes other than those specifically referenced. Information provided herein with respect to any hazards that may be associated with the product is not meant to suggest that use of the product in a given application will necessarily result in any exposure or risk to workers or the general public. THIS PRODUCT DATA SHEET DOES NOT CONTAIN A COMPLETE STATEMENT OF, AND DOES NOT CONSTITUTE A REPRESENTATION, WARRANTY OR GUARANTY WITH REGARD TO, A PRODUCT'S CHARACTERISTICS, USES, QUALITY, MERCHANTABILITY, FITNESS FOR A PARTICULAR PURPOSE, OR THE SUITABILITY, SAFETY, EFFICACY, HAZARDS OR HEALTH EFFECTS OF THE PRODUCT, WHETHER USED SINGULARLY OR IN COMBINATION WITH ANY OTHER PRODUCT, EXCEPT TO THE EXTENT REQUIRED BY THE RELEVANT LAW AND REGULATIONS. Purchasers and users of the product are responsible for determining that the product is suitable for the intended use and that their workers and the general public are advised of any risks resulting from such use. Nothing contained in this Product Data Sheet shall be construed to modify any of the commercial terms pursuant to which the product was sold by INVISTA including, but not limited to, terms and conditions addressing each party's respective rights and obligations with regard to warranties, remedies and indemnification. If purchasers and users believe or have reason to believe that the Product Data Sheet or other information provided to them by INVISTA is inaccurate or in any way insufficient for any purpose, they should immediately notify INVISTA of the same, and of the basis for their belief (for example, studies, data, reports of incidents, etc.) so that INVISTA can determine whether modification or supplementation of the Product Data Sheet, or other measures, are appropriate. Failure of purchasers and users to timely provide such notice shall be deemed a waiver by purchasers and users of any and all claims, demands or causes of action, including causes of action based on an alleged failure to warn, for personal injury or damage to the environment or property arising from or attributable to the use of product. This disclaimer shall be effective to the extent allowed by law. Should any provision be deemed to be ineffective or unenforceable, that provision shall be deemed severed from the disclaimer and the remaining provisions shall continue to have full force and effect. INVISTA, FlexiSolv, and DBE are trademarks of INVISTA. Copyright 2013 INVISTA. All rights reserved.