Abstract: The invention relates to curable coating compositions containing at least one surface modifying amphiphilic additive; and at least one siloxane-polyurethane coating composition. The invention also relates to methods of making and using the curable coating compositions of the invention. The invention also relates to objects coated with the curable coating composition of the invention. The invention also relates to methods for reducing or preventing biofouling of a surface exposed to an aqueous environment comprising the steps of coating the surface with the curable coating composition of the invention to form a coated surface, and curing the coating composition on the coated surface. The invention also relates to a marine fouling-release coating containing the curable coating composition of the invention.

Abstract: The invention provides highly functional epoxy resins that may be used themselves in coating formulations and applications but which may be further functionalized via ring-opening reactions of the epoxy groups yielding derivative resins with other useful functionalities. The highly functional epoxy resins are synthesized from the epoxidation of vegetable or seed oil esters of polyols having 4 or more hydroxyl groups/molecule. In one embodiment, the polyol is sucrose and the vegetable or seed oil is selected from corn oil, castor oil, soybean oil, safflower oil, sunflower oil, linseed oil, tall oil fatty acid, tung oil, vernonia oil, and mixtures thereof. Methods of making of the epoxy resin and each of its derivative resins are disclosed as are coating compositions and coated objects using each of the resins.

Abstract: The invention provides highly functional epoxy resins that may be used themselves in coating formulations and applications but which may be further functionalized via ring-opening reactions of the epoxy groups yielding derivative resins with other useful functionalities. The highly functional epoxy resins are synthesized from the epoxidation of vegetable or seed oil esters of polyols having 4 or more hydroxyl groups/molecule. In one embodiment, the polyol is sucrose and the vegetable or seed oil is selected from corn oil, castor oil, soybean oil, safflower oil, sunflower oil, linseed oil, tall oil fatty acid, tung oil, vernonia oil, and mixtures thereof. Methods of making of the epoxy resin and each of its derivative resins are disclosed as are coating compositions and coated objects using each of the resins.

Abstract: The invention provides poiyfunctionai bio-based methacrylate oligomers, which are synthesized via the ring-opening reaction between at least one ethyienicaliy unsaturated acid selected from methacrylic acid, acrylic acid, and crotonic acid, and a poiyfunctionai bio-based epoxy resin, such as epoxidized sucrose soyate. The extent of reaction may be varied to generate a family of methacrylate oligomers with differing degrees of methacryiation. These methacrylate oligomers can optionally be mixed with a reactive diluent, such as styrene, and cured using, for example, a thermally-activated free radical initiator to form a thermoset polymer with high modulus. The thermosets can be used to form composites, adhesives, coatings, and dental restorative materials. Methods of making the methacrylate oligomers are disclosed as are coating compositions and coated objects, such as dental restorative materials, using the methacrylate oligomers.

Abstract: This invention relates to novel non-isocyanate siloxane-modified glycidol carbamate (GC) resins and coating compositions containing them. The non-isocyanate siloxane modified GC resins of the invention comprise the reaction product of at least one organic polyisocyanate, glycidol, and at least one bis(hydroxyl alkyl)-terminated polydimethylsiloxane. The coating compositions of the invention comprise at least one non-isocyanate siloxane modified GC resin of the invention and at least one curing agent. The invention also relates to methods of making the resins of the invention and coatings containing them. The invention also relates to a fouling-release (FR) coating system comprising the coating compositions of the invention and methods of applying said FR coating systems to substrates. The invention also relates to articles of manufacture comprising a coating composition of the invention and a method of making such articles.

Abstract: The invention relates to novel acetoacetylated lignin resin compositions comprising the reaction product of lignin and an acetoacetate ester. The invention also relates to novel (meth)acrylated lignin resin compositions comprising the reaction product of lignin and a (meth)acrylic compound. The invention also relates to methods of making the novel acetoacetylated lignin resin compositions and the novel (meth)acrylated lignin resin compositions. The invention also relates to curable coating compositions comprising the novel acetoacetylated lignin resin composition or (meth)acrylated lignin resin composition. The invention also relates to methods of making the curable coating compositions of the invention. The invention also relates to methods of applying curable coating compositions of the invention to substrates. The invention also relates to articles of manufacture comprising a curable coating composition of the invention and a method of making such article.

Abstract: The invention relates to a resin having a plurality of cyclic carbonate groups comprising the reaction product of: a) an epoxidized sucrose fatty acid ester resin, and b) carbon dioxide where a) and b) are reacted under conditions sufficient to carbonylate a plurality of the oxirane groups of the epoxidized sucrose fatty acid ester resin, and optionally in the presence of a catalyst or of a solvent. In one embodiment the epoxidized sucrose fatty acid ester resin is epoxidized sucrose soyate. The invention also relates to methods for producing a resin having a plurality of cyclic carbonate groups. In a method of the invention, an epoxidized sucrose fatty acid ester resin is contacted with carbon dioxide under conditions sufficient to carbonylate a plurality of the oxirane groups of the epoxidized sucrose fatty acid ester resin, and optionally in the presence of a catalyst or of a solvent.

Abstract: The invention provides polyfunctional bio-based methacrylate oligomers, which are synthesized via the ring-opening reaction between at least one ethylenically unsaturated acid selected from methacrylic acid, acrylic acid, and crotonic acid, and a polyfunctional bio-based epoxy resin, such as epoxidized sucrose soyate. The extent of reaction may be varied to generate a family of methacrylate oligomers with differing degrees of methacrylate. These methacrylate oligomers can optionally be mixed with a reactive diluent, such as styrene, and cured using, for example, a thermally-activated free radical initiator to form a thermoset polymer with high modulus. The thermosets can be used to form composites, adhesives, coatings, and dental restorative materials. Methods of making the methacrylate oligomers are disclosed as are coating compositions and coated objects, such as dental restorative materials, using the methacrylate oligomers.

Abstract: The invention relates to novel curable bio-based thermosetting compositions of a) at least one highly-functional bio-based epoxy resin; and b) at least one carboxylic acid crosslinker selected from the group consisting of a water-soluble multifunctional carboxylic acid, a dicarboxylic acid oligomer from a melt reaction between a diol and a dicarboxylic acid or its anhydride, and mixtures thereof and which are curable with water, an alcohol or a water and alcohol mixture. The bio-based thermosets of the invention may be free of VOCs and/or organic solvents. The bio-based thermosets of the invention can be used to form coatings, composites, adhesives, and films. Methods of making the bio-based thermosets of the invention are disclosed as are coating compositions and coated objects, such as coatings, composites, adhesives, and films, using the bio-based thermosets of the invention.

Abstract: The invention is directed to curable polyurethane coating compositions which may be used to form fouling release coatings, e.g., for use in protecting boat hulls. The curable polyurethane coating compositions of the invention comprise (a) a prepolymer made by reacting at least one polyisocyanate with (i) at least one monocarbinol-terminated poly(dimethylsiloxane), (ii) at least one methoxy-terminated poly(ethylene glycol), or (iii) mixtures thereof, (b) at least one polyol, and (c) at least one polyisocyanate crosslinker. The invention also relates to the prepolymer used in the curable coating compositions. The invention further relates to methods for reducing or preventing biofouling of a surface exposed to an aqueous environment comprising the steps of coating the surface with a curable coating composition of the invention to form a coated surface, and curing the coating coating composition on the coated surface.

Abstract: The invention relates to a polyfunctional bio-based oligomer which is the reaction product of a) at least one epoxidized sucrose fatty acid ester resin; b) at least one ethylenically unsaturated acid selected from methacrylic acid, acrylic acid, crotonic acid, and mixtures thereof; c) at least one acid anhydride selected from acetic acid anhydride, acrylic acid anhydride, methacrylic acid anhydride, crotonic acid anhydride, and mixtures thereof; d) optionally, at least one catalyst; and e) optionally, at least one inhibitor. In a polyfunctional bio-based oligomer of the invention, the ratio of ethylenically unsaturated acid to acid anhydride ranges from 90:1 to 1:90; at least one epoxide group of the at least one epoxidized sucrose fatty acid ester resin is esterified by at least one ethylenically unsaturated acid; and at least one epoxide group of the at least one epoxidized sucrose fatty acid ester resin is esterified by at least one acid anhydride.

Abstract: Photodegradable polymers derived from biomass are provided, together with methods of making and methods of using the polymers. The photodegradable polymers can be derived from at least a first monomeric unit and a second monomeric unit and an optional third monomeric unit. The first monomeric unit is a dicarboxylic acid and includes a furan group and the second monomeric unit includes a nitrobenzyl group. Methods of recycling the polymers including irradiating the polymers to yield recycled monomers and oligomers are also disclosed.

Abstract: This invention relates to bio-based polyfunctional carboxylic acids reacted with vinyl ether compounds to form liquid vinyl-blocked bio-based polyfunctional carboxylic acids. These liquid vinyl-blocked bio-based polyfunctional carboxylic acids can be mixed with a polyfunctional vegetable oil-based epoxy resin to form a homogeneous curable coating composition. Upon curing at elevated temperature, thermoset coatings are formed which have excellent hardness, solvent resistance, adhesion, and flexibility. The invention also relates to the use of a curable coating composition comprising at least one polyfunctional vegetable oil-based epoxy resin and at least one vinyl-blocked bio-based polyfunctional carboxylic acid, which may be coated onto a substrate and cured thermally. Methods of making the vinyl-blocked bio-based polyfunctional carboxylic acids and curable coating compositions and substrates containing the same are also disclosed.

Abstract: The invention relates to novel aqueous coating compositions containing epoxy urethane (glycidyl carbamate) functional resin. An aqueous coating composition comprises a polyfunctional oligomer having at least two epoxy urethane functional groups and a polyalkylene oxide chain, an optional surfactant, and water. The aqueous coating compositions of the invention can be dispersed in water with or without added surfactants to form a dispersion containing no volatile organic solvent. The invention provides a method for making aqueous coating compositions containing epoxy urethane functional resin as well. Water-dispersible epoxy urethane compounds of the aqueous coating compositions are also provided.

Abstract: The invention relates to alcohol-modified glycidyl carbamate resins wherein at least some of the glycidol groups in the resin have been replaced with an alcohol. The invention also relates to coating compositions containing the resins.

Abstract: The invention relates to enamine resins which are the reaction products of a) an acetoacetylated resin, and a C1-C20 alkyl amine or a mixture of C1-C20 alkyl amines. The acetoacetylated resin is the reaction product of a polyol having 4 or more hydroxyl groups; and at least one acetoacetate. The invention also relates to an acetoacetylated resin which is the reaction product of a polyol having 4 or more hydroxyl groups and at least one acetoacetate, where a portion of the hydroxyl groups of the polyol are replaced by acetoacetate groups and the remaining hydroxyl groups are replaced by a saturated monofunctional carboxylic acid ester, unsaturated monofunctional carboxylic acid ester, or a mixture thereof; as well as to enamine resins prepared from these acetoacetylated resins. The invention also relates to curable coating compositions containing such resins or a mixture of those resins, at least one metallic drier compound; and optionally one or more solvents.

Abstract: This invention relates to bio-based polyfunctional carboxylic acids reacted with vinyl ether compounds to form liquid vinyl-blocked bio-based polyfunctional carboxylic acids. These liquid vinyl-blocked bio-based polyfunctional carboxylic acids can be mixed with a polyfunctional vegetable oil-based epoxy resin to form a homogeneous curable coating composition. Upon curing at elevated temperature, thermoset coatings are formed which have excellent hardness, solvent resistance, adhesion, and flexibility. The invention also relates to the use of a curable coating composition comprising at least one polyfunctional vegetable oil-based epoxy resin and at least one vinyl-blocked bio-based polyfunctional carboxylic acid, which may be coated onto a substrate and cured thermally. Methods of making the vinyl-blocked bio-based polyfunctional carboxylic acids and curable coating compositions and substrates containing the same are also disclosed.

Abstract: The invention relates to a resin having a plurality of cyclic carbonate groups comprising the reaction product of: a) an epoxidized sucrose fatty acid ester resin, and b) carbon dioxide where a) and b) are reacted under conditions sufficient to carbonylate a plurality of the oxirane groups of the epoxidized sucrose fatty acid ester resin, and optionally in the presence of a catalyst or of a solvent. In one embodiment the epoxidized sucrose fatty acid ester resin is epoxidized sucrose soyate. The invention also relates to methods for producing a resin having a plurality of cyclic carbonate groups. In a method of the invention, an epoxidized sucrose fatty acid ester resin is contacted with carbon dioxide under conditions sufficient to carbonylate a plurality of the oxirane groups of the epoxidized sucrose fatty acid ester resin, and optionally in the presence of a catalyst or of a solvent.

Abstract: The invention relates to a polyfunctional bio-based oligomer which is the reaction product of a) at least one epoxidized sucrose fatty acid ester resin; b) at least one ethylenically unsaturated acid selected from methacrylic acid, acrylic acid, crotonic acid, and mixtures thereof; c) at least one acid anhydride selected from acetic acid anhydride, acrylic acid anhydride, methacrylic acid anhydride, crotonic acid anhydride, and mixtures thereof; d) optionally, at least one catalyst; and e) optionally, at least one inhibitor. In a polyfunctional bio-based oligomer of the invention, the ratio of ethylenically unsaturated acid to acid anhydride ranges from 90:1 to 1:90; at least one epoxide group of the at least one epoxidized sucrose fatty acid ester resin is esterified by at least one ethylenically unsaturated acid; and at least one epoxide group of the at least one epoxidized sucrose fatty acid ester resin is esterified by at least one acid anhydride.

Abstract: The invention provides structural biocomposites comprising cellulose-based bast natural fibers, glass fibers, or mixtures thereof, and polyurethanes. The polyurethanes are synthesized from the reaction of polyfunctional bio-based polyols with polyisocyanates. The resultant polyurethanes have higher moduli, hardness, and Tg compared to other bio- and petroleum-based polyols. Methods of making the structural biocomposites are also disclosed.