Abstract: Thermosetting aqueous anionic electrocoating composition are disclosed which comprise a carboxyl-functional anionic polymer dispersed in water with the aid of water miscible organic solvent and a volatile base, and from about 1% to about 5%, based on the weight of the polymer content of the composition, of an oxirane-free epoxy phosphate, this epoxy phosphate being produced by slowly and incrementally adding a resinous polyepoxide to a solvent solution containing from 0.05 to 0.9 mole of orthophosphoric acid per oxirane equivalent in the polyepoxide together with sufficient water to hydrolyze all of the oxirane functionality which is not consumed by the orthophosphoric acid. These epoxy phosphates improve the corrosion resistance of electrodeposited cured coatings without objectionably wrinkling their surface.

Abstract: Aqueous dispersions of partially cross-linked copolymer particles useful in aqueous coating compositions is produced by copolymerizing in aqueous emulsion a mixture of: (A) from 1% to 30% of polyethylenically unsaturated monomer; (B) from 3% to 30% of hydroxy-functional monoethylenically unsaturated monomer; (C) from 0.5% top 10% of a salt-forming monoethylenically unsaturated monomer selected from monoethylenic carboxylic acid monomer and monoethylenic amine monomer; and (D) the balance of the copolymer consisting essentially of copolymerizable monoethylenically unsaturated monomer, preferably nonreactive monomer such as vinyl acetate.

Abstract: Aqueous thermosetting coating compositions are disclosed in which water has dispersed therein: (1) an acidic hydroxy-functional resin dispersed in water as a salt with a volatile base; (2) a curing agent reactable with the hydroxy groups of the hydroxy-functional resin to cure the same, this curing agent being dispersed in the aqueous medium containing said component (1); and (3) an aqueous emulsion of cross-linked emulsion copolymer comprising, by weight: (A) from 2% to 20% of polyethylenically unsaturated monomer; (B) from 3% to 30% of hydroxy-functional monoethylenically unsaturated monomer (C) from 0% to 20% of monoethylenically unsaturated carboxylic acid monomer; and (D) the balance of the copolymer consisting essentially of copolymerizable nonreactive monoethylenically unsaturated monomer. The emulsion is used to provide the emulsion copolymer in an amount of from 10% to 80% of the total weight of resinous material.

Abstract: Cross-linked dispersion copolymers are disclosed which are produced by the aqueous emulsion copolymerization of from 15% to 80% of vinyl acetate, and from 5% to 70% of polyethylenically unsaturated cross-linking agent, like hexane diol diacrylate, from 1% to 40% of other copolymerizable monoethylenically unsaturated monomer being desirably present, preferably from 5% to 25% of a reactive monomer which is desirably hydroxyl-functional. The dispersion copolymers are suspended in active organic solvents which extensively swell the copolymer particles. These suspensions are useful in thermosetting solution coating compositions where they provide improved thermal sag resistance.

Abstract: Aqueous thermosetting cationic electrocoating compositions are disclosed in which an amine-functional cationic polymer is dispersed in water with the aid of an acid, a curing agent being added if the polymer is not self-curing, and there is added from 1% to 30% of the polymer content of the composition of an oxirane-free epoxy phosphate. This epoxy phosphate is produced by slowly and incrementally adding a resinous polyepoxide to a solvent solution containing from 0.05 to 0.9 mole of orthophosphoric acid per oxirane equivalent in said polyepoxide together with sufficient water to hydrolyze all of the oxirane functionality which is not consumed by the orthophosphoric acid. When the epoxy phosphate is made in the manner set forth, the salt spray resistance of electrodeposited cured films is improved.

Abstract: Monoethylenically unsaturated copolymerizable monomers are disclosed which improve the adhesion of copolymers (especially those produced by aqueous emulsion copolymerization to provide latex paint). These monomers are the reaction product of one equivalent of a monoethylenically unsaturated compound which resists homopolymerization and which carries a single isocyanate-reactive hydrogen atom, such as 2-hydroxy propyl monobutyl maleate, one mole of an organic polyisocyante, such as 2, 4-toluene diisocyanate, and sufficient alkyl alkylene urea carrying a single isocyanate-reactive hydrogen atom on the alkyl group, such as 2-hydroxyethyl ethylene urea, to consume the remaining isocyanate functionality on the polyisocyanate. An improved method of producing these monomers from a mixture of all three reactants is also disclosed.

Abstract: Monoethylenically unsaturated copolymerizable monomers are disclosed which improve the adhesion of copolymers (especially those produced by aqueous emulsion copolymerization to provide latex paint). These monomers are the reaction product of one equivalent of a monoethylenically unsaturated compound which resists homopolymerization and which carries a single isocyanate-reactive hydrogen atom, such as 2-hydroxypropyl monobutyl maleate, one mole of an organic polyisocyanate, such as 2,4-toluene diisocyanate, and sufficient alkyl alkylene urea carrying a single isocyanate-reactive hydrogen atom on the alkyl group, such as 2-hydroxyethyl ethylene urea, to consume the remaining isocyanate functionality on the polyisocyanate. An improved method of producing these monomers from a mixture of all three reactants is also disclosed.

Abstract: Ureido-functional ethylenically unsaturated copolymerizable amide monomers are disclosed which are the adduct formed by reacting an aminoalkyl alkylene urea, preferably aminoethyl ethylene urea, with substantially a stoichiometric amount, based on the amine functionality present, of a maleic anhydride compound in solution in N-methyl pyrollidone. The reaction is carried out at a temperature in the range of 80.degree. C. to 130.degree. C. to form an unsaturated carboxyl-functional amide. To provide amide monomers which are particularly useful for improving the adhesion of aqueous emulsion copolymer used to form latex paints, the carboxyl functionality in the amide is consumed by esterification with an epoxide, such as propylene oxide, to provide an acid value of less than 10.

Abstract: A process of producing a water dispersible epoxy phosphate-solvent mixture is disclosed which comprises heating the solvent with orthophosphoric acid to reaction temperature together with additional water so that the total amount of water is sufficient to hydrolyze at least about 50% of the oxirane functionality in the polyepoxide which is used, slowly adding a resinous polyepoxide to this heated mixture so that reaction with phosphoric acid and hydrolysis of the oxirane groups will occur simultaneously to minimize the concentration of oxirane functionality in the reaction mixture as the reaction proceeds, thus minimizing epoxy-epoxy reactions which tend to increase the molecular weight of the epoxy phosphate which is formed, and then adding volatile amine to destroy any remaining oxirane functionality and to neutralize the epoxy phosphate to provide a water dispersible epoxy phosphate-solvent mixture.

Abstract: There is disclosed solution copolymers of monoethylenically unsaturated monomers including a proportion of monoethylenically unsaturated carboxylic acid, with an oxirane-free epoxy acid ester phosphate having adducted onto the oxirane groups of a starting polyepoxide at least 10% thereof of ortho phosphoric acid as well as at least 0.5% by weight of a monoester of a saturated monohydric alcohol with a monoethylenically unsaturated dicarboxylic acid which resists homopolymerization, the remaining oxirane groups of the polyepoxide being esterified with monocarboxylic acid, etherified with monoalcohol or hydrolyzed with water. These copolymers can be neutralized with a volatile amine, especially ammonia and cured with aminoplast or phenoplast resins to provide coatings which cure to greater flexibility and better resistance to blushing on pasteurization exposure.

Abstract: An acrylate or methacrylate functional copolymerizable monomer which serves as an adhesion for emulsion polymers is disclosed. This monomer is the adduct formed by reacting an aminoalkyl alkylene urea with about 0.9 up to about 1.5 molar proportions of a saturated monoepoxide to consume most or all of one of the two amino hydrogen atoms available, and then reacting with about 0.8 up to about 2.0 molar proportions of glycidyl acrylate, glycidyl methacrylate, or a mixture thereof in the presence of at least 0.02%, based on the total weight of the reactants present, of an inhibitor which retards the free-radical polymerization of ethylenic unsaturation, such as hydroquinone, and phenothiazine.

Abstract: An acrylate or methacrylate functional copolymerizable monomer which serves as an adhesion for emulsion polymers is disclosed. This monomer is the adduct formed by reacting an aminoalkyl alkylene urea with about 0.9 up to about 1.5 molar proportions of a saturated monoepoxide to consume most or all of one of the two amino hydrogen atoms available, and then reacting with about 0.8 up to about 2.0 molar proportions of a monoisocyanate having a single acrylate or methacrylate group in the presence of at least 0.02%, based on the total weight of the reactants present, of an inhibitor which retards the free-radical polymerization of ethylenic unsaturation, such as hydroquinone, and phenothiazine.

Abstract: A thermosetting latex coating composition is disclosed and comprises a copolymer of monoethylenically unsaturated monomers copolymerized in aqueous emulsion in the presence of an anionic surfactant and about 1% to about 25% of a liquid water-insoluble polyhydric alcohol. The monomers include at least about 80% of nonreactive monomers and from about 0.5% to about 10% of a monomer carrying a reactive group capable of reacting with the hydroxy groups present when the latex is deposited and dried.

Abstract: Epoxy-free hydroxy functional polyethers are provided which are the reaction product of a diglycidyl ether of a bisphenol having a molecular weight of about 1000 with a stoichiometric proportion of oleyl alcohol. These oleyl alcohol-based polyethers can be copolymerized in organic solvent solution with monoethylenically unsaturated monomers to form solvent-soluble copolymers. When the monomers include carboxyl-functional monomers providing an acid number in the range of 12-60, the copolymers are particularly adapted to be dispersed in water with the aid of a base and then electrodeposited at the anode together with a heat-hardening formaldehyde condensate to form corrosion resistant coatings.

Abstract: An essentially linear polyester oligomer having hydroxyl and carboxyl terminal groups for subsequent cure and its production are disclosed. This polyester oligomer is produced by first adducting approximately equimolar amounts of diol carrying two primary hydroxyl groups and a dicarboxylic acid anhydride to form an hydroxy acid. The carboxyl groups of this hydroxy acid are then esterified by reaction with an approximately stoichiometric proportion of diol carrying one primary hydroxyl group and one secondary hydroxyl group, the stoichiometry being based on the total hydroxyl content of the diol and the carboxyl content of the hydroxy acid, to form an hydroxyl-terminated oligomer. This hydroxyl-terminated oligomer is then adducted with a polycarboxylic acid monoanhydride having a carboxyl functionality of at least 3, this monoanhydride being used in an amount of 0.01 to 0.15 equivalents of anhydride per hydroxyl equivalent in the hydroxyl-terminated oligomer.

Abstract: Epoxy phosphate-carboxyl copolymers substantially free of epoxy functionality and aqueous coatings containing the same are disclosed. These copolymers are formed by copolymerizing monoethylenically unsaturated monomers, including carboxyl-functional monomer, in an organic solvent solution containing an epoxy-functional epoxy phosphate, there being at least 5% of carboxyl-functional monomer and at least 10% of total monomers present in the copolymer. The copolymer is converted into a water soluble salt with volatile amine and phenoplast resins are preferably used to provide at least part of the curing agent.

Abstract: An acrylate or methacrylate functional copolymerizable monomer which serves as an adhesion for emulsion polymers is disclosed. This monomer is the adduct formed by reacting an aminoalkyl alkylene urea with about 0.9 up to about 1.5 molar proportions of a saturated monoepoxide to consume most or all of one of the two amino hydrogen atoms available, and then reacting with about 0.8 up to about 2.0 molar proportions of a monoisocyanate having a single acrylate or methacrylate group in the presence of at least 0.02%, based on the total weight of hte reactants present, of an inhibitor which retards the free-radical polymerization of ethylenic unsaturation, such as hydroquinone, and phenothiazine.

Abstract: An acrylate or methacrylate functional copolymerizable monomer which serves as an adhesion for emulsion polymers is disclosed. This monomer is the adduct formed by reacting an aminoalkyl alkylene urea with about 0.9 up to about 1.5 molar proportions of a saturated monoepoxide to consume most or all of one of the two amino hydrogen atoms available, and then reacting with about 0.8 up to about 2.0 molar proportions of glycidyl acrylate, glycidyl methacrylate, or a mixture thereof in the presence of at least 0.02%, based on the total weight of the reactants present, of an inhibitor which retards the free-radical polymerization of ethylenic unsaturation, such as hydroquinone, and phenothiazine.

Abstract: Aqueous thermosetting coating compositions are disclosed characterized by reduced curing requirements and which produce coatings having superior cured properties. These coatings comprise water containing water miscible organic solvent and the compositions have dispersed therein, based on total resin solids, from 25% to 85% of carboxy-functional organic solvent-soluble copolymer salt with a volatile amine in which the copolymer contains hydroxy groups providing an hydroxyl value in the range of 30 to 300, from 5% to 40% of a water soluble or water dispersible aminoplast or phenoplast curing agent, and from 2% to 35%, of a water dispersible epoxy phosphate ester polymer which is an oxirane-function-free, salt reaction product of (1) a monoester reaction product containing residual epoxy functionality, of (a) a resinous polyepoxide having at least about 1.4 oxirane groups per molecule, and (b) less than 0.

Abstract: An essentially linear polyester oligomer having hydroxyl and carboxyl terminal groups for subsequent cure and its production are disclosed. This polyester oligomer is produced by first adducting approximately equimolar amounts of diol carrying two primary hydroxyl groups and a dicarboxylic acid anhydride to form an hydroxy acid. The carboxyl groups of this hydroxy acid are then esterified by reaction with an approximately stoichiometric proportion of diol carrying one primary hydroxyl group and one secondary hydroxyl group, the stoichiometry being based on the total hydroxyl content of the diol and the carboxyl content of the hydroxy acid, to form an hydroxyl-terminated oligomer. This hydroxyl-terminated oligomer is then adducted with a polycarboxylic acid monoanhydride having a carboxyl functionality of at least 3, this monoanhydride being used in an amount of 0.01 to 0.15 equivalents of anhydride per hydroxyl equivalent in the hydroxyl-terminated oligomer.