# Patent

## Title
VOC-free coalescing agent

## Abstract

A film-forming composition including a coalescent aid comprising fatty acid esters of ethylene glycol and/or propylene glycol having the formula R1COO[(EO)x(PO)y]zH wherein R1CO is a linear saturated aliphatic acyl group, or a combination thereof, having from about 6 to about 22 carbon atoms, EO is —CH2CH2O—, PO is —CH2CH(CH3)O— or —CH(CH3)CH2O— or a combination thereof, where the acyl radical is bonded to a carbon atom of the EO or PO radical, and x=0 to about 5, y=about 0 to about 5, the sum of x and y is equal or greater than 0.5, z=1 to about 5, and (x+y)z is less than or equal to 6. It is to be understood that x, y, and z are average values for the composition.

## Background
This application claims the benefit of U.S. Provisional Application No. 61/116,735, filed Nov. 21, 2008, and is incorporated herein by reference in its entirety.


BACKGROUND
Aqueous dispersions and emulsions of water-insoluble polymers for use as paints, sealants, caulks, adhesives or other coatings are well-known, widely-used articles of commerce. The effectiveness of the dispersion in forming a film after the polymer dispersion has been deposited upon a surface depends upon the glass transition temperature of the dispersed polymer and the temperature at which the film is allowed to form.
Coalescent aids have been used in such aqueous dispersions to soften, i.e., plasticize, ideally temporarily, the dispersed polymer phase and facilitate the formation of a continuous film with optimum film properties once the water has evaporated. In addition to increasing the ease of film formation, the coalescent aid also promotes subsequent improvements in film properties by coalescing the water-insoluble polymers and forming an integral film at ambient temperatures. Without the coalescent aid, the films may crack and fail to adhere to the substrate surface when dry.
Coalescent aids, also known as coalescing solvents or simply coalescents, are particularly helpful in assisting in film formation at temperatures below the glass transition temperature of the dispersed polymer.
Various alcohol esters and ether alcohols have been proposed for use as coalescent aids. For example, in U.S. Pat. No. 4,131,580 Emmons et al. disclose water-based coating compositions based on vinyl addition polymers of monoethylenically unsaturated monomers which comprise dicyclopentenyl acrylate and/or dicyclopentenyl methacrylate as a coalescent aid. In U.S. Pat. No. 4,141,868, Emmons et al. suggest certain ester-ether compounds be used instead.
Two of the more widely used coalescent aids are ethylene glycol monobutyl ether (Butyl CELLOSOLVE®, Dow Chemical) and 2,2,4-trimethyl-1,3 pentanediol monobutyrate (TEXANOL®, Eastman Kodak). While Butyl CELLOSOLVE® and TEXANOL® are useful in facilitating film formation of coatings formulated with water insoluble polymers with high glass transition temperatures and are even useful in facilitating film formation of coatings with low glass transition temperatures if they are being applied at a temperature that is lower than ambient temperature which is higher than the glass transition temperature of the coating, they are relatively volatile and, as a result, are currently classified as VOCs (volatile organic compounds) in the US.
SUMMARY
According to some embodiments, the present invention includes a film-forming composition including a coalescent aid which comprises fatty acid esters of ethylene glycol and/or propylene glycol of Formula I:

R1COO[(EO)x(PO)y]zH  I

wherein R1CO is a linear saturated aliphatic acyl group, or a combination thereof, having from about 6 to about 22 carbon atoms, EO is —CH2CH2O—, PO is —CH2CH(CH3)O— or —CH(CH3)CH2O— or a combination thereof, where the acyl radical is bonded to a carbon atom of the EO or PO radical, and x=0 to about 5, y=about 0 to about 5, the sum of x and y is equal or greater than 0.5, z=1 to about 5, and (x+y)z is less than or equal to 6. It is to be understood that x, y, and z are average values for the composition.

In some embodiments, a film-forming composition includes one or more additives selected from wetting aids, dispersants, thickeners, defoaming agents, algicides, ultra-violet inhibitors, flow agents, leveling agents, rheology modifiers, freeze thaw stabilizing agents, pH modifiers, flash rust inhibitors, and biocides. The film-forming composition may also include pigments to impart hiding and/or color, and fillers such as talc, calcium carbonate, or clays.
In some embodiments, the film-forming composition comprises a mixture of coalescent aids and the fatty acid ester of Formula I is at least about 5 wt. % of the mixture. In other embodiments, the fatty acid ester of Formula I is greater than 50% of the coalescent aids. In a further embodiment, the fatty acid ester of Formula I comprises all of the coalescent aid. In certain embodiments, the film-forming composition contains at least about 20 wt. % water. In some embodiments, the film-forming composition contains at least about 20 wt. % water, at least about 10 wt. % dispersed polymer, and the weight of the fatty acid ester of Formula I is about 0.1% to about 50% of the weight of the dispersed polymer.



BRIEF DESCRIPTION OF THE DRAWINGS
The accompanying drawings, which are included to provide further understanding of the disclosure and are incorporated in and constitute a part of this specification, illustrate embodiments of the disclosure and, together with the description, serve to explain the principles of the disclosure.
In the drawings:
FIG. 1 illustrates the change in minimum film forming temperature as a function of coalescent concentration for an inventive composition and prior art composition;
FIG. 2 illustrates the decrease in minimum film forming temperature for an inventive composition and prior art composition;
FIG. 3 illustrates the change in minimum film forming temperature as a function of coalescent concentration for an inventive composition and prior art composition;
FIG. 4 illustrates the gloss value versus concentration of coalescent for an inventive composition and prior art compositions;
FIG. 5 illustrates the gloss value versus concentration of coalescent for an inventive composition and prior art compositions;
FIG. 6 illustrates the gloss value versus concentration of coalescent for an inventive composition and prior art compositions;
FIG. 7 illustrates the gloss value versus concentration of coalescent for an inventive composition and prior art compositions;
FIG. 8 illustrates the gloss value versus concentration of coalescent for an inventive composition and prior art compositions; and
FIG. 9 illustrates the gloss value versus concentration of coalescent for an inventive composition and prior art compositions.



DETAILED DESCRIPTION
The water-based film-forming compositions of the present invention generally contain a continuous aqueous phase and a polymeric film-forming phase. In general, they may be formulated to function as paint, sealant, caulk, adhesive or other coating. Thus, these film-forming compositions may have a wide range of viscosities, e.g., from about 50 to about 100,000 centipoise; paints, sealants and similar coatings typically have a viscosity from about 50 to about 10,000 centipoise, caulks typically have a viscosity from about 5,000 to about 1,000,000 centipoise, and adhesives typically have a viscosity from about 50 to about 50,000 centipoise. In addition, adhesives are formulated for cohesive strength as well as good contact with the substrate upon which the film-forming composition is deposited. As used herein, a water-based film-forming polymer means a film-forming polymer which is dissolved, dispersed or emulsified in water.
In some embodiments, the continuous aqueous phase comprises at least about 10 wt % water with the amount of water depending upon the application. For example, in some embodiments paints, sealants and similar coating compositions have at least about 10 wt % water and may contain about 20 wt % to about 80 wt % water with differing amounts being used for textured, high gloss, semi-gloss, flat, etc. coatings. In some embodiments, caulks have at least about 10 wt % water and may contain about 10 wt % to about 50 wt % water with differing amounts being used for different caulk applications. In certain embodiments, adhesives range from about 10 wt % to about 80 wt % water and may contain about 40 wt % to about 60 wt % water with differing amounts being used for different adhesive applications.
The continuous aqueous phase may optionally include one or more water-soluble volatile organic solvents, i.e., substituted hydrocarbon solvents. For the purposes of this application, volatile organic solvents shall be defined as those that have a boiling point of about 250° C. or less, or a boiling range beginning at about 250° C. or less. For example, in some embodiments 3-5 wt. % of ethylene glycol or another glycol may be included for freeze-thaw protection. In some embodiments, the proportion of water-soluble volatile organic solvents is minimized; that is, the continuous aqueous phase may contain less than about 20 wt. % volatile organic solvent, less than about 10 wt. % volatile organic solvent, or less than about 5 wt. % volatile organic solvent, based upon the weight of the continuous aqueous phase and exclusive of any amount which may be present in a micelle or other dispersed phase or material. To meet increasingly stringent environmental regulations, the volatile organic solvent content is negligible, less than about 0.1 wt %, in some embodiments.
In some embodiments, the dispersed phase comprises a water-based film-forming polymer and, optionally, one or more additives. In certain embodiments, the dispersed phase, including the water-based film-forming polymer, constitutes no more than about 90 wt % of the film forming composition with the amount of dispersed phase depending upon the application. In some embodiments, paints, sealants and similar coating compositions have no more than about 90 wt % dispersed phase and may contain about 20 wt % to about 80 wt % dispersed phase with differing amounts being used for textured, high gloss, semi-gloss, flat, etc. coatings. In some embodiments, caulks have no more than about 90 wt % dispersed phase and may contain about 75 wt % to about 90 wt % dispersed phase with differing amounts being used for different caulk applications. In some embodiments, adhesives range from about 20 wt % to about 90 wt % dispersed phase and may contain about 40 wt % to about 60 wt % dispersed phase with differing amounts being used for different adhesive applications.
In some embodiments, the dispersed polymer is insoluble in the aqueous phase and is otherwise suitable for use in water borne film-forming compositions. Because in some embodiments the dispersed polymer is the component which coalesces to form the desired film, the film-forming composition may comprise at least about 10 wt. %, at least about 15 wt. %, and some applications at least about 20 wt. % of a coalescible dispersed polymer.
According to some embodiments of the present invention, suitable dispersed polymers are generally of high molecular weight (e.g, greater than about 60,000 Daltons for a typical film-forming latex resin). For example, in some embodiments they may be either of the addition type, in particular a polymer or copolymer of one or more α,β-ethylenically unsaturated monomers, or of the condensation type, for example, a polyester or a polyamide. Suitable water-based film-forming polymers of the addition type may include the polymerization and copolymerization products of styrene, vinyl acetate, vinyl toluene, vinyl chloride, vinylidene chloride, butadiene, vinyl hydrocarbons, acrylonitrile, acrylic acid and esters thereof (hereinafter “acrylates”), and methacrylic acid and esters thereof (hereinafter “methacrylates”) containing monomers. Suitable condensation type water-based film-forming polymers may include epoxy, urethane, hydrocarbon, silicone, nitrocellulose, polyester, and alkyd polymers. In certain embodiments, particularly suitable water-based film-forming polymers include acrylates, methacrylates, styrene and vinyl acetate and mixtures thereof. Examples of suitable water-based film-forming polymers include the polymerizates or copolymerizates of one or more of the following: acrylates such as ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, as well as other acrylates, methacrylates, styrene and vinyl acetate. In some embodiments, the water-based film-forming polymer comprises a latex formulation.
In some embodiments, the film forming compositions are comprised of thermoplastic polymers; in these compositions, films may be formed by evaporation of the water. In other embodiments, the film forming compositions are comprised of crosslinkable formulations; these formulations may be comprised of crosslinking agents and water-based film-forming polymers or self-crosslinking water-based film-forming polymers.
In some embodiments, polymers dispersed as very small particles are more readily coalesced than polymers dispersed as larger particles. Accordingly, in some embodiments, dispersed polymers have a particle size of about 3 micrometers or less. For example, for latex resins, in some embodiments approximately 90 wt. % of the latex particles will have a size less than about 0.2 micrometers.
The film forming composition further comprises a coalescent aid (or solvent) which may be in the continuous phase, the dispersed phase, or partitioned between them.
In some embodiments, the coalescent aid of this invention is used in latex, also known as emulsion systems. In some embodiments, these coalescent aids may also find application in other systems such as those based on but not limited to alkyds, epoxies, nitrocellulose, and urethanes.
In some embodiments, the amount of coalescent aid needed to assist in film formation depends on the viscosity of the film-forming composition, the temperature at which the composition is being applied, the glass transition temperature of the film-former, and the minimum film formation temperature of the film-former. In certain embodiments, the amount of coalescent will be proportional to the amount and type of water-based film-forming polymer used with ratios in the range of about 0.1 wt % to about 50 wt. % (based upon the weight of the dry film forming polymer), about 0.1 wt % to about 40 wt. % (based upon the weight of the dry film forming polymer), about 0.1 wt % to about 25 wt. % (based upon the weight of the dry film forming polymer), about 0.1 wt % to about 15 wt. % (based upon the weight of the dry film forming polymer), about 0.1 wt % to about 10 wt. % (based upon the weight of the dry film forming polymer), or about 1 wt. % to about 4 wt. % range (based upon the weight of the dry film forming polymer).
As noted above, the coalescent aid may be in the continuous phase, in the dispersed phase, or partitioned between the two. Depending upon the type and amount of surfactants included in the film-forming composition, a fraction of the fatty acid ester coalescent aid may additionally be emulsified in the continuous aqueous phase and found in micelles along with surfactant.
The film-forming composition of the present invention may also contain various conventional additives which may be in the dispersed and/or continuous phases. Such additives may include but are not limited to thickening agents such as hydroxyethyl cellulose sold by Aqualon under the trade designation Natrasol 250 and thickeners sold under the trade designation RHEOLATE® associative thickeners by Elementis Specialties, pH modifiers such as ammonium hydroxide and N,N-dimethyl ethanolamine, defoaming agents such as mineral oil or silicone oils, wetting agents such as a nonionic surfactant sold by AKZO under the trade designation Interwet 43 and a nonionic surfactant sold by Dow Chemical under the trade designation Triton X-100, algicides such as organotin compounds and tetrachloroisophthalonitrile, fungicides such as tributyl tin oxide, and 3-iodo-2-propynyl butyl carbamate, dispersants such as lecithin and an anionic dispersant sold under the trade designation Busperse 39 by Buckman, ultraviolet inhibitors such as a benztriazol UV inhibitor sold under the trade designation Tinuvin 328 by Ciba-Geigy and a hindered amine UV inhibitor sold under the trade designation by Tinuvin 123 by Ciba-Geigy, flow and leveling agents such as a polyacrylate sold under the trade designation Byk 354 by Byk-Chemie and a polysiloxane copolymer sold under the trade designation Byk 310 by Byk-Chemie, flash rust inhibitors such as an inhibitor sold under the trade designation Raybo 63 by Raybo or a barium metaborate rust inhibitor sold under the trade designation Busan 11M1 by Buckman, and freeze/thaw inhibitors such as ethylene glycol. Additional additives may include driers such as cobalt driers carboxylate salts (0.0 to 0.15 wt. % Co based on the coalescent aid) and manganese driers carboxylate salts (0.0 to 0.15 wt. % based on the coalescent aid), accelerators such as 1,10-phenanthroline (0 to 0.2% based on the coalescent aid) and 2,2-bipyridine (0 to 0.2% based on the coalescent aid), and anti-skinning agents such as butanone oxime (0.1 lb/100 gal formulation). When present and depending upon the application for the film-forming composition, in some embodiments these additives will not constitute more than about 10 wt. % of the film-forming composition and may constitute about 3 wt. % to about 10 wt. % of the film-forming composition.
In some embodiments, the film forming compositions of this invention will contain pigments or dyes (ink application) to impart hiding and color to the applied film, and/or fillers such as talc, calcium carbonate, kaolin clays, etc.
The film-forming composition may be formed by conventional methods used to prepare paints, adhesives, except that the ester of the present invention is substituted, at least in part, for a conventional coalescent aid. The resulting film-forming composition may easily be applied conventionally using a brush, roller, air or airless spray or like means and requires no unusual methods of drying to form the desired film. Thus, films formed from the composition of the present invention may be dried under ambient conditions or baked at elevated temperature. Furthermore, the film-forming composition may be applied to a variety of materials.
Fatty Acid Esters
Accordingly, the present invention relates to coalescent aids including fatty acid esters of propylene glycol corresponding to Formula (I):

R1COO[(EO)x(PO)y]zH  (I)

in which R1CO is a linear or branched, saturated aliphatic acyl group, EO is —CH2CH2O—, PO is —CH2CH(CH3)O— or —CH(CH3)CH2O— or a combination thereof, where the acyl radical is bonded to a carbon atom of the EO or PO radical, and x=0 to about 5, y=about 0 to about 5, the sum of x and y is equal or greater than 0.5, z=1 to about 5, and (x+y)z is less than or equal to 6. It is to be understood that x, y, and z are average values for the composition. In one such embodiment, R1 contains 6 to 22 carbon atoms. In another such embodiment, R1 contains 9 to 15 carbon atoms, In some other such embodiment, R1 comprises at least about 80% C11-C13; at least about 90% C11-C13; at least about 95% C11-C13; or at least about 98% C11-C13.
In some embodiments, x=0, y=n, and z=1, resulting in fatty acid esters of propylene glycol corresponding to Formula (II):

R1COO(PO)nH  (II)

in which R1CO has the same meaning as defined for Formula (I), PO stands for —CH2CH(CH3)O— and/or —CH(CH3)CH2O—, where the acyl radical is bonded to a carbon atom of the EO or PO radical, and n is a number from 0.5 to 5. In some embodiments, n is a number from 0.8 to 1.
These coalescent aids of Formulas (I) or (II) may be prepared either by esterification of the fatty acids with the appropriate glycol or preferably by ethoxylation, propoxylation or propoxylation/ethoxylation of fatty acids. The acids may be derived from natural or synthetic sources. Suitable natural sources include naturally occurring oils such as palm oil, palm kernel oil, coconut oil, and other such oils. The desired fatty acids may also be obtained as a minor fraction from other naturally occurring oils.
The fatty acid ester of Formulas (I) or (II) may be prepared by ethoxylation, propoxylation or ethoxylation/propoxylation reactions of R1COOH wherein the reactions are carried out in the presence of a catalyst. Suitable catalysts include, for instance: basic catalysts such as sodium and potassium hydroxides and alkoxides, amines; alkanolamines including but not limited to monoethanolamine, diethanolamine and triethanolamine; acids such as mineral acids including hydrochloric acid and sulfuric acid, and Lewis acids such as chromium carboxylates, stannic chloride and boron trifluoride. In some embodiments, the alkanolamines are used in quantities of 0.1 to 5% by weight and in quantities of 0.5 to 3.0% by weight, based on the fatty acids. Synthesis of a fatty acid ester is described in U.S. Pat. No. 6,300,508, which is herein incorporated by reference in its entirety. In certain embodiments, the ethoxylation and/or propoxylation reactions are carried out using a phosphorus-containing catalyst, still more preferably a phosphine, and most preferably triphenylphosphine.
The ethoxylation, propoxylation and/or ethoxylation/propoxylation reaction may be carried out in a known manner. The fatty acid and the catalyst may be introduced into a stirred autoclave which is freed from traces of water before the reaction by alternate evacuation and purging with nitrogen. The fatty acid may then be reacted with the ethylene oxide, propylene oxide or with the ethylene oxide/propylene oxide mixture in a molar ratio of 1:0.5 to 1:5 which may be introduced into the autoclave in portions through a siphon tube after heating. The fatty acids may be reacted with less than or equal to 5 moles of ethylene oxide or propylene oxide or with less than or equal to 6 moles of the mixture of ethylene oxide and propylene oxide. The reaction may be carried out at temperatures of 80 to 180° C. or in some embodiments 100 to 160° C. under autogenous pressures of 1 to 5 bar and in some embodiments 2 to 3 bar. After the reaction, the reaction mixture may be stirred for a certain time (15-90 mins.) at the reaction temperature in order to complete the reaction. The autoclave may then be cooled, vented and, if desired, acids, for example, lactic acid or phosphoric acid, may be added to the product to neutralize the basic catalyst.
In certain embodiments, the fatty acid ester component comprises about 80% of the reaction mixture, about 90% of the reaction mixture, about 95% of the reaction mixture, or about 99% of the reaction mixture. In some embodiments, the ester component of the reaction mixture comprises about 80%, about 90%, about 95%, or about 99% of the monoester (i.e., formula (I) or (II)) of the analogous glycol. In certain embodiments, the diester content (that is, the product in which both hydroxyls of the glycol are esterified) is less than about 10%, less than about 5%, or less than about 3% of the coalescent aid. Achieving such levels of di-ester and monoester may be accomplished by fractional distillation of the reaction product and/or by judicious selection of the reaction conditions, including catalyst selection.
In some embodiments, the coalescent aid may contain the starting fatty acid at concentrations of up to about 50 wt %; up to about 40 wt %; up to about 30 wt %; up to about 20 wt %; up to about 15 wt %; up to about 10 wt %; up to about 5 wt %; or up to about 1 wt %.
In some embodiments, the coalescent aid contains a diester. The diester may be of the formula R1COO[(EO)x(PO)y]zCOOR1. In some such embodiments, the coalescent aid contains less than about 1% diester; less than about 3% diester; less than about 5% diester; less than about 10% diester; or less than 20% diester.
EXAMPLES
Synthesis and Purification of Propylene Glycol Monolaurate
Propylene Glycol Monolaurate (PGML) was prepared by three different methods as described below. The products were analyzed by Gas Chromatography (GC). The relative amounts of residual Lauric acid, PGML and Propylene Glycol Dilaurate (PGDL) were estimated based on peak areas.
The PGML-1 used in Examples 1-7 was obtained from the direct esterification of Lauric Acid with propylene glycol. The product was vacuum distilled to obtain the purified propylene glycol monolaurate. GC analysis showed the product to be 96% pure and free of Propylene Glycol Dilaurate. The material was prepared as follows:
A 250 mL 4-neck flask was fitted with a Dean/Stark trap and condenser, a thermocouple, a nitrogen inlet and outlet, and a magnetic stir bar. 77.5 grams of Lauric Acid (98%, TCI America) and 117.8 grams of 1,2-propanediol (99%, Aldrich) were added to the flask. 0.37 grams of p-toluene sulfonic acid monohydrate (TCI America) was then added and the solution placed under a nitrogen atmosphere. The solution was heated to 125° C. Five 10 mL portions of dry toluene were added over 40 minutes. The toluene was allowed to co-distill with water. The temperature was then raised to 156° C. over 2 hours at which point a vigorous reflux began. After collecting an additional 9 mL of distillate, the reaction was cooled. Base titration (KOH/MeOH) indicated less than 1% unreacted Lauric acid. The solution was diluted with 200 mL of cyclohexane and neutralized with 2 grams of sodium bicarbonate in 100 mL of water. The solution was further washed with 2×100 mL of water and dried over MgSO4 (anhydrous). The solvent was removed on a rotary evaporator to give 100 grams of a clear, light brown liquid. GC analysis showed the product to consist mainly of propylene glycol monolaurate (70%) and propylene glycol dilaurate (30%). Propylene Glycol Monolaurate was obtained by fractional distillation of this crude product (113° C. @ 18 microns Hg).
The PGML-2 used in Examples 8 and 12 was obtained by fractional distillation of the crude product resulting from the base catalyzed reaction of propylene oxide and lauric acid. It contains 94% PGML and 6% Lauric Acid. The catalyst was potassium laurate, generated in situ from lauric acid and potassium methoxide. The crude product was prepared as follows:
A 5 L autoclave was charged with 590 grams lauric acid and 3.4 grams Potassium methanolate (32.5% active content). The vessel was sparged with nitrogen and heated to 160° C. for 30 minutes to remove all methanol. 175 grams of propylene oxide (PO) were added over 40 minutes at 155-160° C. while keeping the pressure below 5 bar. After addition of all PO, the reaction mixture was heated for 1 hour. Any unreacted propylene oxide was removed via a Nitrogen sparge with a vacuum of 330 mbar. The end product had an acid value of 8.4 mg KOH/g.
The PGML-3 used in Examples 9-11 and 13-14 was obtained from the triphenylphosphine catalyzed reaction of propylene oxide and lauric acid: A 5 L autoclave was charged with 750 grams lauric acid and 3.75 grams TPP. The vessel was sparged with nitrogen while maintaining 300 mbar of vacuum. The vessel was heated to 105° C. and maintained at these conditions for 1 hour to remove any water. 220 grams of propylene oxide (PO) were added over 40 minutes at 100-110° C. while keeping the pressure below 3.3 bar. After all of the PO was added, the reaction was heated for 5.30 hours until an acid value of approximately 5-10 mg KOH/g was obtained. Any unreacted propylene oxide was removed via a Nitrogen sparge with a vacuum of 330 mbar. GC Analysis showed the reaction product consisted of 94% PGML, 1.3% PGDL, and 3.5% Lauric Acid.
Performance of Propylene Glycol Monolaurate in Acrylic, Vinyl Acrylic and Styrene Acrylic Resins and Paints: Gloss and Minimum Film Formation Temperature
Example 1
Effect of Propylene Glycol Monolaurate (PGML-1, Distilled) on Gloss in an Acrylic Resin
To a 4 oz. straight-sided polypropylene jar, 50 grams of Rhoplex® ML200TM was added. The latex was agitated using a Dispermat® CV high speed disperser fitted with a 30 mm high shear impeller. The disperser was run at a sufficient speed to maintain a vortex in the latex. To the latex 1.34 g of coalescent was added in a dropwise fashion. The blend was mixed for an additional 5 minutes and then allowed to equilibrate for at least 16 hours.
Approximately 2-3 grams of the coalescent/latex blend was added to one end of a byko-chart scrub-test panel (P121-10N). Immediately adjacent to this blend was added a control resin blend in which Texanol® (2,2,4-trimethyl-1,3-pentanediol monobutyrate) was used as the coalescent. Using a 3 mil wet film applicator, the material was drawn down at a constant rate. The films were allowed to dry for 16-hours in a constant temperature/humidity cabinet (25° C. @ 50% humidity). A 20° and 60° gloss measurement was made using a Novo-Gloss gloss meter (GARDCO). An average of 3 readings were recorded for both the experimental and control film. The results were recorded in Table 1 for these films. The results indicated that propylene glycol monolaurate is as effective as Texanol® in improving the gloss of a film for this acrylic resin.







TABLE 1







Gloss Readings for Films Prepared


from Coalescent/Acrylic Resin Blends*










Gloss Readings













Reference
Coalescent
20°
60°







PGML-1
Texanol ®
61
83




Propylene Oxide ester
62
84




of Lauric Acid




(distilled)







*5 wt % coalescent on resin solids. Film thickness: 3 mil.



*Resin: Rhoplex ® ML200 TM. 54 wt % solids, available from Rohm & Haas



*Tg of Resin = 9° C. Minimum Film Formation Temperature of Resin: 7° C.






Example 2
Effect of Propylene Glycol Monolaurate (PGML-1, Distilled) on Gloss in a Vinyl Acrylic Resin
A resin blend was prepared by mixing 1.93 g of coalescent with 50 g of UCAR 379GTM in the manner described in Example 1. As in Example 1, films were prepared and the gloss of these films was measured. The results are reported in Table 2. The results show that propylene glycol monolaurate performs as well or better than the Texanol® control in this vinyl acrylic resin.







TABLE 2







Gloss Readings for Films Prepared from


Coalescent/Vinyl Acrylic Resin Blends*










Gloss Readings













Reference
Coalescent
20°
60°







PGML-1
Texanol ®
67
85




Propylene Glycol
70
85




Monolaurate




(distilled)







*7 wt % coalescent on resin solids. Film thickness: 3 mil.



*Resin: UCAR 379G TM. 55 wt % solids; available from Dow Chemical



*Tg of Resin = 19° C. Minimum Film Formation Temperature of Resin: 12° C.






Example 3
Effect of Propylene Glycol Monolaurate (PGML-1, Distilled) on Gloss in a Styrene Acrylic Resin
A resin blend was prepared by mixing 3.15 g of coalescent with 50 g of Arolon® 847-W-42 in the manner described in Example 1. As in Example 1, films were prepared and the gloss of these films was measured. The results are reported in Table 3. The results show that propylene glycol monolaurate performs as well or better than the butyl Cellosolve® control in this styrene acrylic resin.







TABLE 3







Gloss Readings for Films Prepared from Coalescent/Styrene-Acrylic


Resin blends*










Gloss Readings













Reference
Coalescent
20°
60°







PGML-1
Butyl
58
91




Cellosolve ®




Propylene Glycol
75
93




Monolaurate




(distilled)







*15 wt % coalescent on resin solids. Film thickness: 3 mil.



*Resin: Reichold Arolon ® 847-W-42. 42 wt % solids.



*Tg of Resin = 23° C. Minimum Film Formation Temperature of Resin: 20° C.






Example 4
Effect of Propylene Glycol Monolaurate (PGML-1, Distilled) on Gloss in an Acrylic Paint
An Acrylic masterbatch was prepared as described below. To 57.4 g of this masterbatch was added 0.47 g of Propylene Glycol Monolaurate in a manner similar to that described in Example 1. As in Example 1, films were prepared and the gloss of these films was measured. The results are reported in Table 4. The results show that propylene glycol monolaurate performs as well or better than the Texanol control in this acrylic paint.










Rhoplex ® ML200 TM Masterbatch: Quality Exterior Flat Formula




















Raw Material
Pounds
Gallons
Weight %







Water
117.00
14.06
10.11



Natrosol 250 MHR
4.90
0.42
0.42



Ammonium
2.20
0.29
0.19



hydroxide









Add to water, mix and hydrate - then add while mixing:












Ethylene Glycol
25.00
2.69
2.16



Propylene Glycol
35.00
3.76
3.02



Tamol 1124
6.80
0.69
0.59



Triton CF10
1.00
0.11
0.09



BYK 022
2.00
0.24
0.17









Add slowly to vortex - HSD to 5 Hegman












TiPure R706
225.00
6.75
19.45



Minex 4
160.00
7.38
13.83



Iceberg
50.00
2.28
4.32









Letdown: RM and water holdout for adjustment:












Rhoplex
350.00
39.33
30.25



Mulitlobe 200



Drew Plus L 475
2.00
0.26
0.17



Water
166.90
20.06
14.42



Coalescent*
9.30
1.18
0.80



TOTAL
1157.10
99.51
100.00















Raw Material
Description
Supplier







Water
cellulosic
Hercules



Natrosol ® 250 MHR
thickener



Ammonium hydroxide
buffer



Ethylene Glycol
glycol



Propylene Glycol
glycol



Tamol TM 1124
dispersant
Rohm & Haas



Triton TM CF10
surfactant
Dow



BYK ® 022
defoamer
BYK-Chemie



TiPure ® R706
titanium dioxide
DuPont



Minex ® 4
extender
Unimin





Burgess



Iceberg
extender
Pigment



Rhoplex ® Mulitlobe TM
acrylic resin
Rohm & Haas



200



Drewplus ® L 475
defoamer
Drew Industrial







*held out













TABLE 4







Gloss Readings for Films Prepared from


Coalescent/Acrylic Masterbatch Blends*










Gloss Readings













Reference
Coalescent
20°
60°







PGML-1
Texanol ®
2
4




Propylene




Glycol
2
4




Monolaurate




(distilled)







*5 wt % coalescent on resin solids. Film thickness: 3 mil.



*Resin: Rhoplex ® ML200 TM



*Tg of Resin = 9° C. Minimum Film Formation Temperature of Resin: 7° C.






Example 5
Effect of Propylene Glycol Monolaurate (PGML-1, Distilled) on Gloss in a Vinyl Acrylic Paint
A Vinyl Acrylic masterbatch was prepared as described below. To 52.0 g of this masterbatch was added 1.0 g of Propylene Glycol Monolaurate in a manner similar to that described in Example 1. As in Example 1, films were prepared and the gloss of these films was measured. The results are reported in Table 5. The results show that propylene glycol monolaurate performs as well or better than the Texanol control in this vinyl acrylic paint.










Vinyl Acrylic UCAR 379G TM Masterbatch


Semigloss Enamel Formula




















Raw Material
Pounds
Gallons
Weight %







Water
268.20
32.24
25.30



Cellosize ER-
2.00
0.18
0.19



15,000



Nuosept 95
2.40
0.25
0.23



AMP 95
1.00
0.13
0.09









Add to water, mix and hydrate - then add while mixing:












Tamol 731A
9.20
1.00
0.87



Triton N-57
2.10
0.25
0.20



Propylene Glycol
43.20
4.65
4.08



BYK 035
1.00
0.14
0.09









Add slowly to vortex - HSD to 5 Hegman:












TiPure R706
250.00
7.50
23.59









Letdown: RM and water holdout for adjustment:












Ucar 379G
428.40
47.34
40.42



BYK 035
1.90
0.26
0.18



Propylene Glycol
10.00
1.08
0.94



Water
10.00
1.20
0.94



Acrysol SCT 275
10.00
1.20
0.94



Triton GR-7M
0.50
0.06
0.05



Coalescent*
20.00
2.53
1.89



Water
0.00
0.00
0.00



TOTAL
1059.90
99.99
100.00













Raw Material
Description
Supplier





Water
cellulosic
Dow


Cellosize TM ER-15,000
thickener


Nuosept ® 95
in-can biocide
ISP


AMP 95
buffer
Angus


Tamol TM 731A
dispersant
Rohm & Haas


Triton TM N-57
surfactant
Dow


Propylene Glycol
glycol


BYK ® 035
defoamer
BYK-Chemie


TiPure ® R706
titanium dioxide
DuPont


Ucar ® 379G
vinyl acrylic resin
Dow


BYK ® 035
defoamer
BYK-Chemie


Propylene Glycol
glycol


Acrysol TM SCT 275
associative thickener
Rohm & Haas


Triton TM GR-7M
surfactant
Dow





*held out













TABLE 5







Gloss Readings for Films Prepared from Coalescent/Vinyl


Acrylic Masterbatch Blends*










Gloss Readings













Reference
Coalescent
20 Degrees
60 degrees







PGML-1
Texanol ®
24
70




Propylene




Glycol
28
72




Monolaurate




(distilled)







*8.5 wt % coalescent on resin solids. Film thickness: 3 mil.



*Resin: UCAR 379G TM. 55 wt % solids



*Tg of Resin = 19° C. Minimum Film Formation Temperature of Resin: 12° C.






Example 6
Effect of Propylene Glycol Monolaurate (PGML-1, Distilled) on Gloss in a Styrene Acrylic Paint
A Styrene Acrylic masterbatch was prepared as described below. To 48.0 g of this masterbatch was added 2.05 g of Propylene Glycol Monolaurate and 1.25 g of water in a manner similar to that described in Example 1. As in Example 1, films were prepared and the gloss of these films was measured. The results are reported in Table 6. The results show that propylene glycol monolaurate performs better than the butyl Cellosolve® control in this styrene acrylic paint.










Styrene Acrylic Arolon ® 847-W-42


Masterbatch White Gloss Enamel Formula




















Raw Material
Pounds
Gallons
Weight %







Arolon 847-W-42
223.59
26.24
21.80



Tamol 731A
1.32
0.14
0.13



Patcote 841
1.32
0.18
0.13



Water
23.76
2.86
2.32



Ammonium
3.17
0.41
0.31



hydroxide









Add slowly to vortex - HSD to 5 Hegman:












TiPure R706
219.10
6.57
21.36









Letdown: RM and water holdout for adjustment:












Water
26.40
3.17
2.57



Arolon 847-W-42
428.43
50.29
41.78



Water
26.40
3.17
2.57



10% Sodium Nitrite
6.07
0.68
0.59



Coalescent*
41.00
5.16
4.00



Water*
25.00
3.00
2.44



TOTAL
1025.56
101.89
100.00













Raw Material
Description
Supplier





Arolon ® 847-W-42
styrene acrylic
Reichhold



resin


Tamol TM 731A
dispersant
Rohm & Haas


Patcote ® 841

Hydrite Chemical




Co.


Water


Ammonium
buffer


hydroxide


TiPure ® R706
titanium dioxide
DuPont


Arolon ® 847-W-42
styrene acrylic
Reichhold



resin


10% Sodium Nitrite
flash rust inhibitor





*held out













TABLE 6







Gloss Readings for Films Prepared from Coalescent/Styrene-Acrylic


Masterbatch Blends*










Gloss Readings













Reference
Coalescent
20°
60°







PGML-1
Butyl Cellosolve ®
40
78




Propylene Glycol
61
86




Monolaurate




(distilled)







*15 wt % coalescent on resin solids. Film thickness: 3 mil.



*Resin: Reichold Arolon ® 847-W-42.



*Tg of Resin = 23° C. Minimum Film Formation Temperature of Resin: 20° C.






Example 7
Effect of Propylene Glycol Monolaurate (PGML-1, Distilled) on the Minimum Film Formation Temperature (MFFT) of Acrylic, Vinyl Acrylic and Styrene Acrylic Resins
In a manner similar to Example 1, a series of resin/coalescent blends were prepared with varying levels of coalescent. The blends were allowed to equilibrate for 16 hours. The MFFT of these blends were determined according to ASTM 2354-98 using a Rhopoint MFFT BAR-90. The results of these tests are represented graphically in FIGS. 1-3. The results are compared to either Texanol® (TMB: 2,2,4-trimethyl-1,3-pentanediol mono(2-methylpropanoate) or Butyl Cellosolve®. The results show that Propylene Glycol Monolaurate is of similar efficiency to these commercial coalescents in lowering the MFFT of the resin.
Example 8
Effect of Lauric Acid on Gloss
A series of blends of PGML-2 (distilled, contains 6 wt % Lauric acid) was blended with increasing amounts of Lauric Acid. The mixtures were then added to Acronal Optive® 110 in a manner similar to that described in Example 1. The loading level was 7.7 wt % coalescent blend on resin solids. 3 mil films were prepared and the gloss of these films was measured as described in Example 1. The results are reported in Table 7. The results show that the PGML coalescent may contain up to at least 16 wt % Lauric acid without observing any effect on the gloss of the films prepared from this coalescent and Acronal Optive® 110.











TABLE 7









% Lauric Acid in
Gloss













Reference
Coalescent Blend*
20°
60°
















Ex. 9a
6
71.9
87.7



Ex. 9b
9
74.4
87.2



Ex. 9c
11
75.4
87.9



Ex. 9d
16
75.6
87.7







*total Lauric acid includes 6 wt % Lauric acid in PGML-2.



**Coalescent = 7.7% on resin solids






Example 9
Comparison of Propylene Glycol Monolaurate (PGML-3, Undistilled) With Commercial Coalescents in an Acrylic Resin
In a manner similar to Example 1, a series of blends consisting of increasing amounts of coalescent were added to Acronal Optive® 110. The coalescents included PGML-3, an undistilled propylene glycol monolaurate with <2% PGDL, and a number of commercial coalescents. Films of these blends were prepared as described in Example 1. Both 20° and 60° gloss readings were obtained. In addition, the MFFT of these coalescent resin blends were measured as described in Example 7. The gloss and MFFT data are shown graphically in FIGS. 4-6 where TMB: 2,2,4-trimethyl-1,3-pentanediol mono(2-methylpropanoate); Competitive Sample A which is believed to be triethylene glycol bis(2-ethylhexanoate); Competitive Sample B which is believed to consist mainly of propylene glycol monooleate; Competitive Sample C which is believed to consist mainly of propylene glycol monoesters of polyunsaturated C18 fatty acids. The data shows that PGML-3 gives equal or better performance in comparison to these commercial coalescents
Example 10
Comparison of Propylene Glycol Monolaurate (PGML-3, Undistilled) With Commercial Coalescents in a Vinyl Acrylic Resin
In a manner similar to Example 1, a series of blends consisting of increasing amounts of coalescent were added to UCAR 379GTM. The coalescents included PGML-3, an undistilled propylene glycol monolaurate with <2% PGDL, and a number of commercial coalescents. Films of these blends were prepared as described in Example 1. Both 20° and 60° gloss readings were obtained. In addition, the MFFT of these coalescent resin blends were measured as described in Example 7. The gloss and MFFT data are shown graphically in FIGS. 7-9 where TMB: 2,2,4-trimethyl-1,3-pentanediol mono(2-methylpropanoate); Competitive Sample A which is believed to be triethylene glycol bis(2-ethylhexanoate); Competitive Sample B which is believed to consist mainly of propylene glycol monooleate; Competitive Sample C which is believed to consist mainly of propylene glycol monoesters of polyunsaturated C18 fatty acids. The data shows that PGML-3 gives equal or better performance in comparison to these commercial coalescents.
Example 11
Comparison of the Block Resistance of Propylene Glycol Monolaurate to Commercial Coalescents in an Acrylic Paint
An Acrylic masterbatch was prepared as described below using Acronal Optive® 110. In a manner similar to Example 1, a series of coalescent/masterbatch blends were prepared. The series included PGML-3 (undistilled) and two commercial coalescents. In accordance with ASTM D4946-89, 6 mil wet films were drawn down on Leneta 7B sealed test charts. The charts were dried at 25° C. and 50% relative humidity for 7 days. Block resistance measurements were then carried out at 25° C. for 24 hours. The results of these tests are reported in Table 8. The results indicate that the block resistance of the paint containing PGML-3 is equal to the commercial coalescents tested.










Acrylic Acronal Optive ® 110 Masterbatch


Exterior Semi-Gloss Paint




















Raw Material
Pounds
Gallons
Weight %







Water
122.00
14.66
11.58



Natrosol 330 Plus
0.80
0.07
0.08



Proxel GXL
2.00
0.21
0.19



Ethylene Glycol
28.00
3.01
2.66



AMP 95
2.00
0.25
0.19



Drewplus L493
2.00
0.26
0.19



Tamol 731A
7.00
0.76
0.66









Add to water, mix and hydrate - then add while mixing:












Minex 7
25.00
1.15
2.37









Add slowly to vortex - HSD to 5 Hegman:












Water
70.50
8.47
6.69



TiPure R706
229.50
6.89
21.78









Letdown: RM and water holdout for adjustme












Drewplus L493
3.00
0.39
0.28



Optive 110
520.00
58.76
49.35



Aquaflow NHS 300
16.00
1.85
1.52



Texanol*
20.00
2.53
1.90



Water*
6.00
0.72
0.57















Raw Material
Description
Supplier







Water



Natrosol ® 330 Plus
cellulosic
Hercules




thickener



Proxel ® GXL
in-can biocide
Arch





Chemicals



Ethylene Glycol
glycol



AMP 95
buffer
Angus



Drewplus ® L 493
defoamer
Drew Industrial



Tamol TM 731A
dispersant
Rohm & Haas



Minex ® 7
extender
Unimin



TiPure ® R706
titanium dioxide
DuPont



Drewplus ® L 493
defoamer
Drew Industrial



Optive ® 110
acrylic resin
BASF



Aquaflow ® NHS
associative thickener
Hercules



300







*held out
















TABLE 8








Block



Coalescent*
Resistance**









Texanol ®
8



PGML-3
8



(undistilled)



Archer RC
8







*on a scale of 1-10 with 10 being the best



**Coalescent = 7.7% on resin solids






Example 12
Comparison of Propylene Glycol Monolaurate and Commercial Coalescents in an Acrylic Resin
An acrylic latex (Rhoplex SG10M) was blended with various levels of different coalescents (one example of an inventive coalescent and two commercial compositions) in a manner similar to Example 1. These coating compositions were applied to a scrub chart, as described in Table 9, and air dried. The resulting films were evaluated for film formation, gloss/haze, substrate wetting, and tackiness. The results for these parameters are included in Table 9, which shows that the coating including PGML-2 exhibited good film formation, clear films, good wetting of the substrate, etc. The results in Table 9 comprise subjective ratings on a scale of 1-10 (10 being the best) for each parameter.







TABLE 9







Rhoplex SG10M Acrylic Latex Coalesced


with Various Coalescents/Levels












Blank

Dapro
Com.



(no solvent)
PGML-2
FX513
Coalescent*















2.5% Loading






Film Formation
10
10
10
8


Gloss/Haze
10
10
8
7


Substrate
10
10
8 “orange
1: craters -


Wetting


peel”
crawling


Tackiness


6-hours
10
9
9
9


24-hours


5.0% Loading


Film Formation

10
10
8-micro mud-






cracking


Gloss/Haze

10
6
10 


Substrate

8 “orange
9 “orange
7 “orange


Wetting

peel”
peel”
peel”


Tackiness


6-hours

8
9
8


24-hours


10.0% Loading


Film Formation

10
10
8


Gloss/Haze

9
4
6


Substrate

10
7 “orange
4-orange


Wetting


peel”
peel/craters


Tackiness


6-hours

6
8
7


24-hours


15.0% Loading


Film Formation

10
10
7


Gloss/Haze

10
4
9


Substrate

9 “orange
9 “orange
9 “orange


Wetting

peel”
peel”
peel”


Tackiness


6-hours

5
7
6


24-hours





Clear Films Applied: Black Scrub Chart, #S222 rod, 72° F./39% RH


Films Air Dried: 25° C./50% RH






Believed to be triethylene glycol bis(2-ethylhexanoate)

Example 13
Comparison of Propylene Glycol Monolaurate (PGML-3, Undistilled) With Texanol in an Acrylic Paint
Two semi gloss acrylic based paints were prepared as described below. PGML was used in place of Texanol in the second paint. A number of standard tests were carried out on these paints using the procedures outlined in the associated ASTM methods. The results are listed in Table 10. The results show that PGML can be used in place of Texanol in this semi gloss acrylic paint without any significant reduction in the performance of the paint










SG-30-1: 150 g/L VOC Quality Interior Semigloss White


















Pounds
Gallons
Weight %
Raw Material










Add in order listed with good mixing:










325.50
16.75
31.01
Kronos 4311


79.30
9.52
7.56
Water


34.60
4.00
3.30
Propylene Glycol


1.80
0.21
0.17
Kathon LX 1.5%


501.40
56.75
47.78
Rhoplex SG30


12.50
1.61
1.19
Texanol


1.50
0.16
0.14
Aerosol OT-75


2.10
0.25
0.20
BYK 022


1.00
0.13
0.10
Ammonia (28%)







Add ingredients below separately with good mixing. Mix for 30 minutes










17.30
1.89
1.65
RM 2020


16.20
1.89
1.54
RM 825


56.30
6.76
5.36
Water


1049.50
99.95
100.00
TOTAL














Raw Material
Description
Supplier







Kronos 4311
TiO2 Slurry
Kronos



Propylene Glycol
glycol



Kathon LX 1.5%
Biocide
Rohm and Haas



Rhoplex SG30
Acrylic Latex
Rohm and Haas



Texanol
Coalescent
Eastman Chemical



Aerosol OT-75
Surfactant
Cytec



BYK 022
Defoamer
BYK-Chemie



Ammonia (28%)
Base



RM 2020
Rheology Modifier
Rohm and Haas



RM 825
Rheology Modifier
Rohm and Haas

















TABLE 10







Semi Gloss Acrylic Paint based on RHOPLEX SG30









Coalescent: 5% Weight



(based on resin solids)











Untinted
Units
ASTM
Texanol
PGML-3














White Base






Coalescent: (wt. %
Wt %

5.0
5.0


base on resin solids)


VOC (Coalescent)*
g/L

36.18
1.42


VOC (paint)
g/L

150.69
115.96


Viscosity, 25°


KU
KU
D 562
117
114


ICI
Poise
D 4287
1.3
1.5


3 mil WFT Drawdown


60° Gloss


74.3
79.5


20° Gloss

D 523
36.7
45.2


Contrast Ratio

D 2805
0.972
0.973


CIELab Values L*

D 5326
96.68
96.71


a*


−1.08
−1.07


b*


2.03
1.96


Sward Hardness 1-day
cycles
D 2134
12
12


7-days
cycles

12
12


Pencil Hardness (7-days)
lead #
D 3363
F
B


Zapon Tack Free Time
30′′/500 g


1-day
pass/fail

pass
fail


7-days
pass/fail

pass
pass


Sag Resistance
mils
D 4400
8
8


Leveling
0-10(best)
D 4062
10
10


Block Resistance (7-day)
1000 g
D 4946


Room temp: 1-day dwell
0-10(best)

10
9


120° F.: 30-min. dwell
0-10(best)

8
7


Scrub Resistance

D 2486


Cycles to failure
cycles

1331
1748


% of control
%

100
131





*Contribution of coalescent to the total VOC of paint. This calculation is based on the measured wt % VOC of the neat coalescent using EPA Method 24.






Example 14
Use of Propylene Glycol Monolaurate (PGML-3, Undistilled) in a Styrene Acrylic Paint
Three high gloss styrene acrylic based paints were prepared using the High Gloss DTM Enamel as described below. PGML was used as a partial replacement for dipropylene glycol n-butylether in some of the samples of Table 11. In addition, the total level of coalescent was reduced in some of the samples of Table 11. A number of standard tests were carried out on these paints using the procedures outlined in the associated ASTM methods. The results are listed in Table 11. The results show that PGML can be used as a partial replacement of dipropylene glycol n-butylether in this styrene acrylic paint without any significant reduction in the performance of the paint. In addition, the total coalescent level can be reduced without effecting the paint performance.










EPS 2535 WHT BT-1: High Gloss DTM Enamel - White



















Pounds
Gallons
Weight %
Raw Material
Note










Add with good aggitation











37.50
4.50
3.68
Water



13.00
1.50
1.28
Propylene Glycol


8.00
0.87
0.79
Tamol 681


5.00
0.69
0.49
Surfynol 104A


3.00
0.38
0.29
AMP 95


1.50
0.19
0.15
Dehydran 1620


225.00
6.45
22.08
RCL-535







Disperse to 7 Hegman, Adjust grind, rinse mill











6.00
0.72
0.59
Water








To Letdown tank charge:











584.80
68.00
57.40
EPS 2535



17.30
2.00
1.70
Propylene Glycol


1.50
0.16
0.15
Nuosept 95







Add grind from above


Add:











29.20
3.51
2.87
Water
Premix H20






and DPnB


10.00
1.15
0.98
Sodium Nitite, 4%


66.00
8.63
6.48
DPnB


0.00
0.00
0.00
Dapro FX514


5.00
0.55
0.49
RM 2020


3.00
0.34
0.29
RM 825
Premix with






H20







Adjust final viscosity











3.00
0.36
0.29
Water



1018.80
100.01
100.00
TOTAL












Raw Material
Description
Supplier





Propylene Glycol
Glycol


Tamol 681
Dispersant
Rohm and Haas


Surfynol 104A
Surfactant
Air Products


AMP 95
Base
Dow Chemical


Dehydran 1620
Defoamer
Cognis


RCL-535
Titanium Dioxide
Millenium


EPS 2535
Styrene Acrylic
EPS, Inc



Latex


Propylene Glycol
Glycol


Nuosept 95
Biocide
International Specialty




Products


Sodium Nitrite, 4%
Anticorrosion


DPnB
Coalescent
Dow Chemical


RM 2020
Rheology Modifier
Rohm and Haas


RM 825
Rheology Modifier
Rohm and Haas





*Contribution of coalescent to the total VOC of paint. This calculation is based on the measured wt % VOC of the neat coalescent using EPA Method 24.













TABLE 11







High Gloss Styrene Acrylic Paint based on EPS 2535











Untinted

A
B
C














White Base
Units
ASTM
DPnB
DPnB
PGML
DPnB
PGML

















Coalescent: (wt. % bors)
wt. %

25.00
20.00
5.00
18.75
6.25


VOC (from coalescent)*
g/l

157.96
126.56
1.27
121.74
1.58












VOC (paint)
g/l

249.80
219.80
212.29


Viscosity, 25°







KU
KU
D 562
106
107
115


ICI
Poise
D 4287
1.6
1.8
1.9


3 mil WFT Drawdown







60° Gloss


92.2
91.7
92.3


20° Gloss

D 523
73.7
72
74.8


Contrast Ratio

D 2805
0.974
0.977
0.973













CIELab Values
L*

D 5326
96.25
95.39
95.26



a*


−1.08
−1.57
−1.59



b*


2.51
1.38
1.37












Sward Hardness

D 2134





1-day
cycles

4
0
2


3-days
cycles

4
4
4


7-days
cycles

8
6
6


Zapon Tack Free Time
30′′/500 g






1-day
pass/fail

pass
fail
pass


3-days
pass/fail

pass
pass
pass


7-days
pass/fail

pass
pass
pass


Sag Resistance
mils
D 4400
10
8
8


fingers
yes/no

no
no
no


Leveling
0-10(best)
D 4062
10
10
10


Block Resistance (7-day)
1000 g
D 4946





Room temp: 1-day dwell
0-10(best)

8
8
7


120° F.: 30-min. dwell
0-10(best)

0
0
0


Scrub Resistance

D 2486





Cycles to failure
cycles

1707
1744
1623


% of control
%


102.2
95.1


Stain Removal

D 3450





Reflectance Recovery


98.56
100.32
99.85


Adhesion: Aged Gloss Alkyd

D 3359





Dry: 1-day


0B
1B
0B


Dry: 7 day


0B
1B
0B


Wet: 7 day
0-5B(best)

0B
0B
0B


40° C. Mud cracking







sealed
mils

>60
>60
>60


unsealed
mils

>60
>60
>60


Freeze Thaw Stability

D 2243





Cycles 1


gelled
gelled
gelled


120° F. Heat Age Stability (2-







wks)







Syneresis
mm

0
0
0


□KU
KU
D 562
−2
−1
1


□ICI
Poise
D 4287
0.4
0.0
0.1

## Claims

1. A film-forming composition comprising a water-based film-forming polymer, and a coalescent aid comprising a fatty acid ester of an ethylene glycol, propylene glycol, or ethylene-propylene glycol of the following formula:


R1COO[(EO)x(PO)y]zH

wherein R1CO is a linear saturated aliphatic acyl group and wherein R1 comprises at least about 80% C11-C13, EO is —CH2CH2O—, PO is —CH2CH(CH3)O— or —CH(CH3)CH2O— or a combination thereof, where the acyl radical is bonded to a carbon atom of the EO or PO radical, and x=0 to about 5, y=about 0 to about 5, the sum of x and y is equal or greater than 0.5, z=1 to about 5, and (x+y)z is less than or equal to 6.

2. The film-forming composition of claim 1, wherein x=0, y=n, and z=1, where n=0.5 to about 5.

3. The film-forming composition of claim 2, wherein x=0, y=n, and z=1, where n=0.5 to about 2.

4. The film-forming composition of claim 2, wherein n=0.8 to about 1.

5. The film-forming composition of claim 1, wherein R1 comprises at least about 90% C11-C13.

6. The film-forming composition of claim 1, wherein R1 comprises at least about 95% C11-C13.

7. The film-forming composition of claim 1, wherein R1 comprises at least about 98% C11-C13.

8. The film-forming composition of claim 1, wherein the water-based film-forming polymer comprises a latex.

9. The film-forming composition of claim 1 further comprising an additive selected from the group consisting of wetting aids, dispersants, thickeners, defoaming agents, algicides, ultra-violet inhibitors, flow agents, leveling agents, rheology modifiers, freeze thaw stabilizing agents, pH modifiers, flash rust inhibitors, biocides, pigments, fillers and dyes.

10. The film-forming composition of claim 1 wherein the film-forming composition comprises a mixture of coalescent aids and the fatty acid ester comprises at least about 5 wt. % of the mixture.

11. The film-forming composition of claim 1 wherein the film-forming composition contains at least about 20 wt. % water.

12. The film-forming composition of claim 1 wherein the film-forming composition contains at least about 20 wt. % water, at least about 10 wt. % water-based film-forming polymer, and the weight of the ester is about 0.1% to about 50% of the weight of the water-based film-forming polymer.

13. The film-forming composition of claim 1 wherein the weight of the fatty acid ester is about 0.1% to about 50% of the weight of the water-based film-forming polymer.

14. The film-forming composition of claim 1 wherein the weight of the fatty acid ester is about 0.1% to about 25% of the weight of the water-based film-forming polymer.

15. The film-forming composition of claim 1, wherein the water-based film-forming polymer comprises at least one acrylic resin.

16. The film-forming composition of claim 1, wherein the water-based film-forming polymer comprises at least one vinyl acrylic resin.

17. The film-forming composition of claim 1, wherein the water-based film-forming polymer comprises at least one styrene acrylic resin.

18. The film-forming composition of claim 1, wherein the water-based film-forming polymer comprises a blend of acrylic resin and/or vinyl acrylic resin and/or styrene acrylic resin.

19. The film-forming composition of claim 1, wherein the coalescent aid comprises less than about 10% diester, wherein the diester comprises the formula R1COO[(EO)x(PO)y]z—C(═O)R1.

20. The film forming composition of claim 1 wherein the fatty acid ester is formed by the direct esterification of a fatty acid with ethylene glycol and/or propylene glycol.

21. The film forming composition of claim 1 wherein the fatty acid ester is formed by reaction of a fatty acid with ethylene oxide and/or propylene oxide.

22. The film forming composition of claim 1 wherein the fatty acid ester is formed by reaction of a fatty acid with ethylene oxide and/or propylene oxide using a phosphine reaction catalyst.

23. The film forming composition of claim 1 wherein the fatty acid ester is formed by reaction of a fatty acid with ethylene oxide and/or propylene oxide using triphenylphosphine as a reaction catalyst.

24. A film-forming composition comprising a water-based film-forming polymer, and a coalescent aid comprising at least 70% of propylene glycol monolaurate.

25. A method of coalescing an aqueous film forming composition comprising use of the fatty acid ester of claim 1.