HK1214619B - Aqueous coating compositions including the reaction product of maleic anhydride with an unsaturated compound and an amine - Google Patents

Description

Aqueous coating compositions comprising the reaction product of maleic anhydride with an unsaturated compound and an amine

Background of the Invention

1. Field of the Invention

The present invention relates to coating compositions comprising substituted succinimide compounds, methods of preparing the coating compositions, substrates coated with the coating compositions, and methods of coating substrates with the coating compositions.

2. Description of Related Technologies

Coating compositions formed from epoxy resins are used to coat food and beverage packaging and containers. Despite the weight of scientific evidence, as interpreted by major global food safety agencies in the United States, Canada, Europe, and Japan, showing that the levels of bisphenol A to which consumers are exposed with existing commercial epoxy-based coatings are safe, some consumers and trademark owners continue to express safety concerns. Coating compositions that do not contain bisphenol A or any other potential endocrine disruptors are desirable. Additionally, styrene monomer and copolymers of styrene and maleic anhydride are widely used in coating compositions for protecting food and beverages to improve corrosion resistance and metal adhesion, but it is currently desirable to prepare such coating compositions without styrene.

SUMMARY OF THE INVENTION

Carbon dioxide present in soft drinks is known to permeate packaging coating compositions, potentially causing delamination of the coating. We have discovered that incorporating specific substituted succinimide compounds into coating compositions provides delamination resistance as well as improved adhesion and corrosion resistance on metal substrates.

The present invention relates to coating compositions comprising substituted succinimide compounds, methods for preparing the coating compositions, substrates coated with the coating compositions, and methods for coating substrates with the coating compositions. The coating compositions can be water-based protective coating packaging compositions that exhibit improved adhesion and corrosion resistance when applied to metal substrates such as aluminum, steel, or electrotin-plated steel. The coating compositions can be applied directly to metal substrates to provide a protective layer to prevent contact with the metal substrate.

In some embodiments of the present invention, an aqueous coating composition comprising a substituted succinimide compound is provided. The substituted succinimide compound may have an acid value of at least about 30 mg KOH/g substituted succinimide compound. The substituted succinimide compound may be the reaction product of an unsaturated oil comprising at least one non-aromatic unsaturated carbon-carbon bond, a polymer derived from an unsaturated oil, or a combination thereof, with maleic anhydride and a primary amine.

Also disclosed is a method for preparing an aqueous coating composition. The method may include the steps of: a) reacting an unsaturated oil containing at least one non-aromatic unsaturated carbon-carbon bond, a polymer derived from an unsaturated oil, or a combination thereof with maleic anhydride to form a substituted succinic anhydride compound; b) reacting the substituted succinic anhydride compound with a primary amine to form an amic acid intermediate; c) allowing water to precipitate from the amic acid intermediate to form a substituted succinimide compound; and d) neutralizing the substituted succinimide compound in the presence of water to form the aqueous coating composition. The substituted succinimide compound may have an acid value of at least about 30 mg KOH/g of the substituted succinimide compound.

BRIEF DESCRIPTION OF THE DRAWINGS

Figure 1 shows a reaction scheme for the formation of substituted succinimide compounds wherein the primary amine is the amino acid β-alanine.

Detailed Description of the Invention

The present invention relates to coating compositions comprising substituted succinimide compounds, methods for preparing the coating compositions, substrates coated with the coating compositions, and methods for coating substrates with the coating compositions. The coating compositions can be water-based protective packaging coating compositions that exhibit improved adhesion and corrosion resistance when applied to metal substrates such as aluminum, steel, or electrotin-plated steel. Additionally, the coating compositions can be prepared from renewable materials such as vegetable oils and amino acids and do not have the health concerns associated with epoxy resins and styrene-based compounds. The coating compositions can be applied directly to metal substrates to provide a protective layer to prevent contact with the metal substrate.

In some embodiments of the present invention, an aqueous coating composition comprising a substituted succinimide compound is provided. The substituted succinimide compound may have an acid value of at least about 30 mg KOH/g of the substituted succinimide compound. In some embodiments, the substituted succinimide compound may comprise from greater than 0 to about 10% by weight of the coating composition. If the percentage of the substituted succinimide compound is above about 10% by weight, the adhesion of the coating composition to the metal substrate may deteriorate, while a percentage below about 0.1% by weight may not significantly improve corrosion resistance.

The substituted succinimide compound can be a reaction product of an unsaturated oil containing at least one non-aromatic unsaturated carbon-carbon bond, a polymer derived from an unsaturated oil, or a combination thereof with maleic anhydride and a primary amine. The reaction of maleic anhydride with the unsaturated oil or the polymer derived from the unsaturated oil can be carried out by a Diels-Alder reaction or an Alder-ene reaction.

Unsaturated oils and polymers derived from unsaturated oils can have one or more unsaturated carbon-carbon bonds. Unsaturated carbon-carbon bonds can be double bonds. Double bonds can be monounsaturated (comprising only one double bond) or polyunsaturated (comprising more than one double bond). Unsaturated oils and polymers derived from unsaturated oils can be polyunsaturated compounds comprising conjugated and/or non-conjugated double bonds.

For non-limiting examples, unsaturated oil and the polymer derived from unsaturated oil can be prepared by esterifying one or more polyols, polycarboxylic acids, fatty acids and mixtures thereof. Due to the incorporation of unsaturated aliphatic compounds such as unsaturated fatty acids, at least a portion of unsaturated oil and the polymer derived from unsaturated oil can be oxidatively dried. Suitable examples of unsaturated fatty acids include myristoleic acid, palmitoleic acid, oleic acid, gadoleic acid, erucic acid, ricinoleic acid, oleic acid, linoleic acid, linolenic acid, tall oil fatty acid, sunflower fatty acid, safflower fatty acid, soybean fatty acid etc. The example of the fatty acid comprising conjugated double bonds includes dehydrated castor oil fatty acid and wood oil fatty acid. Suitable monocarboxylic acids include tetrahydrobenzoic acid and hydrogenated or non-hydrogenated rosin acid or its isomers. If necessary, monocarboxylic acids can be used as triglycerides, for example vegetable oils, in unsaturated oil and the preparation of the polymer derived from unsaturated oil. If desired, mixtures of two or more of these monocarboxylic acids or triglycerides can be used, optionally in the presence of one or more saturated (cyclo)aliphatic or aromatic monocarboxylic acids, such as pivalic acid, 2-ethylhexanoic acid, lauric acid, palmitic acid, stearic acid, 4-tert-butyl-benzoic acid, cyclopentanecarboxylic acid, cycloalkanecarboxylic acid, cyclohexanecarboxylic acid, 2,4-dimethylbenzoic acid, 2-methylbenzoic acid and benzoic acid.

Polycarboxylic acids can also be incorporated into unsaturated oils and polymers derived from unsaturated oils, such as phthalic acid, isophthalic acid, terephthalic acid, 5-tert-butylisophthalic acid, trimellitic acid, pyromellitic acid, succinic acid, adipic acid, 2,2,4-trimethyladipic acid, azelaic acid, sebacic acid, dimerized fatty acids, cyclopentane-1,2-dicarboxylic acid, cyclohexane-1,2-dicarboxylic acid, 4-methylcyclohexane-1,2-dicarboxylic acid, tetrahydrophthalic acid, butane-1,2,3,4-tetracarboxylic acid, endoisopropyl-cyclohexane-1,2-dicarboxylic acid, cyclohexane-1,2,4,5-tetracarboxylic acid, and butane-1,2,3,4-tetracarboxylic acid. If desired, the carboxylic acids can be used as anhydrides or in the form of esters, such as esters of alcohols having 1 to 4 carbon atoms.

Unsaturated oils and polymers derived from unsaturated oils may further comprise polyol structural blocks. Examples of suitable polyols include ethylene glycol, 1,3-propylene glycol, 1,6-hexanediol, 1,12-dodecanediol, 3-methyl-1,5-pentanediol, 2,2,4-trimethyl-1,6-hexanediol, 2,2-dimethyl-1,3-propanediol, and 2-methyl-2-cyclohexyl-1,3-propanediol. Suitable triols include glycerol, trimethylolethane, and trimethylolpropane. Suitable polyols having more than three hydroxyl groups include pentaerythritol, sorbitol, and etherification products such as di-trimethylolpropane and di-, tri-, and tetrapentaerythritol.

Unsaturated oils and polymers derived from unsaturated oils can be obtained by direct esterification of the constituent components, wherein a selected portion of these components is pre-converted into ester diols or polyester diols. In some embodiments, the unsaturated oils and polymers derived from unsaturated oils can be added in the form of a drying oil, such as linseed oil, fish oil, or dehydrated castor oil. Unsaturated oils and polymers derived from unsaturated oils can be prepared by transesterification with other acids or polyols at temperatures of about 200 to about 250° C., optionally in the presence of solvents such as toluene and/or xylene.

Suitable examples of polymers derived from unsaturated oils include alkyd resins. Such alkyd resins may be polyesters modified with unsaturated fatty acids or unsaturated oils containing unsaturated fatty acids.

In some embodiments, the primary amine may have the general formula _NH2RCOOH , where R may be an alkyl or aryl group having from about 2 to about 30 carbon atoms, or preferably from about 3 to about 12 carbon atoms. Non-limiting examples of suitable primary amines include, but are not limited to, glycine, β-alanine, arginine, aspartic acid, cysteine, leucine, glutamine, 5-aminopentanoic acid, 7-aminoheptanoic acid, 8-aminooctanoic acid, 6-aminohexanoic acid, 3-aminobutyric acid, and mixtures thereof. The acid group and amine group of an amino acid may be separated by more than one carbon atom, as such amino acids are generally more reactive than if the groups were separated by only one carbon atom.

The acid value of the substituted succinimide compound should be sufficient to allow the substituted succinimide compound to be dispersed in or soluble in an aqueous medium after neutralization. The solubility of the substituted succinimide compound may depend, at least in part, on the hydrophobicity of the substituted succinimide compound itself, its molecular weight, and the properties of the aqueous medium. In some embodiments, the number average molecular weight of the substituted succinimide compound is from about 400 to about 10,000 daltons or from about 700 to about 3000 daltons. The number average molecular weight described herein is measured using a polystyrene standard by gel permeation chromatography, sometimes referred to as so-called size exclusion chromatography. In some embodiments, the acid value of the substituted succinimide compound is from about 30 to about 300 mg KOH/g substituted succinimide compound or from about 50 to about 150 mg KOH/g substituted succinimide compound. The acid value described herein is measured by ASTM D1639, titled "Standard test method for acid value of organic coating materials."

When the unsaturated oil or polymer derived from the unsaturated oil contains acid groups, for example when the polymer is an unsaturated fatty acid, the primary amine need not necessarily contain acid groups. However, the unsaturated oil, polymer derived from the unsaturated oil and primary amine may all contain acid groups.

In certain embodiments, the aqueous coating compositions of the present invention may have a continuous phase having at least 50% water or at least 65% water. Suitable solvents may include n-butanol, ethylene glycol monobutyl ether, and the like. The remainder of the continuous phase may comprise an organic solvent, which may be water-soluble, partially water-soluble, or water-insoluble.

In certain embodiments, the substituted succinimide compound may be partially or completely neutralized to facilitate dispersion in the continuous aqueous phase of the aqueous coating composition. Suitable neutralizing agents include, but are not limited to, ammonia, amines, alkali metal bases, and mixtures thereof. Suitable amines include, but are not limited to, dimethylaminoethanol, triethylamine, amino-2-methylpropanol, dimethylaminopropanol, dimethylamino-2-methylpropanol, and mixtures thereof. Suitable alkali metal bases include, but are not limited to, potassium hydroxide, sodium hydroxide, and mixtures thereof.

In certain embodiments, the aqueous coating composition may include a binder polymer. In certain embodiments, the binder polymer may be present in an amount of at least about 50% by weight or about 90 to about 99.9% by weight of the coating composition. Suitable binder polymers include, but are not limited to, acrylic polymers, styrene-acrylic polymers, polyurethane polymers, alkyd polymers, epoxy polymers, and mixtures and/or hybrid copolymers thereof. In certain embodiments, the aqueous coating composition with the binder polymer may form an adhesive film when baked at an ambient temperature of about 0 to about 40° C. or at a temperature of about 130 to about 250° C.

The base polymer may comprise an aqueous dispersion of particles formed using known emulsion polymerization methods such as latex polymerization, mini-emulsion polymerization, or microsuspension polymerization. Such dispersions are generally referred to as latex dispersions. Alternatively, an emulsion of the polymer in an aqueous medium may be prepared by emulsifying the base polymer with or without a solvent and optionally in the presence of a surfactant. By way of non-limiting example, suitable monomers for preparing the base polymer include styrene, α-methylstyrene, and the like, and mixtures thereof; alkyl esters of acrylic or methacrylic acid, such as methyl methacrylate, ethyl methacrylate, butyl methacrylate, ethyl acrylate, butyl acrylate, hexyl acrylate, n-octyl acrylate, lauryl methacrylate, 2-ethylhexyl methacrylate, nonyl acrylate, decyl acrylate, benzyl methacrylate, isobutyl methacrylate, and isobornyl methacrylate; hydroxyalkyl esters of the foregoing acids, such as 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, and 2-hydroxypropyl methacrylate, glycidyl acrylate, glycidyl methacrylate, acrylic acid, and methacrylic acid; polyacrylates, such as butanediol dimethacrylate; and mixtures of the foregoing.

Without being bound by any theory, the inventors believe that there are two characteristics of the substituted succinimide compound that cause it to act as an adhesion promoter for the coating composition: the bonding site of the substituted succinimide compound and the hydrophobic nature of the substituted succinimide compound. Both the imide and carboxylic acid groups of the substituted succinimide compound help adhere the coating composition to the metal substrate, and having multiple bonding sites provides better bond strength. A skilled person can easily achieve multiple bonding sites with higher molecular weights. As the molecular weight increases, the hydrophobic portion of the substituted succinimide compound interacts with the base polymer to help prevent the base polymer from debonding from the substituted succinimide compound. If the molecular weight is too high, the chance of incompatibility with some base polymers may increase.

Figure 1 shows the steps of a reaction scheme for forming a substituted succinimide compound, wherein the primary amine is the amino acid β-alanine. Step 1 is the reaction of the unsaturated carbon chain with maleic anhydride to form the substituted succinimide compound (I). Step 2 shows the reaction of the substituted succinimide compound (I) with β-alanine to form the amic acid intermediate (II). The amic acid intermediate (II) loses water in step 3 to form the substituted succinimide compound (III).

The present invention also includes a method for coating a substrate, comprising the steps of applying the coating composition of the present invention to a substrate. Also included are substrates coated with such coating compositions. The method for preparing an aqueous coating composition may include the steps of a) reacting an unsaturated oil comprising at least one non-aromatic unsaturated carbon-carbon bond, a polymer derived from an unsaturated oil, or a combination thereof with maleic anhydride to form a substituted succinic anhydride compound, b) reacting the substituted succinic anhydride compound with a primary amine to form an amic acid intermediate, c) separating water from the amic acid intermediate to form a substituted succinimide compound, and d) neutralizing the substituted succinimide compound in the presence of water to form an aqueous coating composition. In some embodiments, the aqueous coating composition further comprises a binder polymer.

In certain embodiments of the present invention, unsaturated oil or the polymer derived from unsaturated oil can be heated in the presence of maleic anhydride to connect maleic anhydride to unsaturated oil or the polymer derived from unsaturated oil to form substituted succinic anhydride compound through the Alderene reaction. Primary amine is then added to the substituted succinic anhydride compound to form an amic acid intermediate. When the mixture is progressively heated, water is separated out to obtain the substituted succinimide compound. After cooling, a solvent and/or a neutralizing base can be added to the substituted succinimide compound along with water to form an aqueous dispersion. Thereafter, the aqueous dispersion of the substituted succinimide compound can be mixed with the base polymer to form coating composition of the present invention.

For non-limiting example, soybean oil can be heated to approximately 225°C in the presence of maleic anhydride to attach the anhydride to the soybean oil via an alderene reaction to form a substituted succinic anhydride soybean oil intermediate. β-Alanine can be added to the mixture at approximately 140°C to form an amic acid intermediate. As the mixture is gradually heated to approximately 170°C, water precipitates to form a soybean oil-substituted succinimide compound. After cooling to approximately 100°C, a neutralizing base, such as a tertiary amine or ammonia, can be added along with the water to form an aqueous dispersion of the soybean oil-substituted succinimide compound. This aqueous dispersion of the soybean oil-substituted succinimide compound can then be mixed with a base polymer to form the coating composition of the present invention.

The coating composition of the present invention may contain conventional additives known to those skilled in the art, such as, but not limited to, flow agents, surfactants, defoamers, anti-crater additives, lubricants, meat release additives, and curing catalysts.

In some embodiments, one or more coating compositions of the present invention may be applied to a substrate, such as, for non-limiting example, a can, a package, a container, a container, a can, or any portion thereof, that is used to hold or contact any type of food or beverage. In some embodiments, one or more coatings are applied in addition to the coating compositions of the present invention, such as, for non-limiting example, a primer coating may be applied between the substrate and the coating composition of the present invention.

The coating composition can be applied to the substrate in any manner known to those skilled in the art. In some embodiments, the coating composition is sprayed on the substrate. When spraying, for non-limiting examples, the coating composition can include approximately 10 to approximately 30 weight % polymer solids, relative to approximately 70% to approximately 90% water, including, if necessary, other volatiles, such as but not limited to a minimum amount of solvent. For some applications, generally different from those of spraying, for non-limiting examples, the aqueous polymer dispersion can include approximately 20 to approximately 60 weight % polymer solids. In some embodiments, an organic solvent is used to promote spraying or other application methods, and such solvents include but are not limited to n-butanol, 2-butoxy-ethanol-1, xylene, toluene and mixtures thereof. In some embodiments, n-butanol is used in combination with 2-butoxy-ethanol-1.

In some embodiments, the coating compositions of the present invention can be tinted and/or opacified with known pigments and opacifiers. For many applications, including, for non-limiting example, food applications, the pigment is titanium dioxide. In some embodiments, the resulting aqueous coating composition can be applied by conventional methods known in the coatings industry. Thus, for non-limiting example, spraying, roller coating, dipping, and flow coating application methods can be used to produce both clear and colored films. In some embodiments, after application to the substrate, the coating can be heat cured at temperatures ranging from about 130° C. to about 250° C., and optionally higher, for a time sufficient to allow for complete curing and volatilization of any labile components therein.

For substrates intended as beverage containers, in some embodiments, the coating composition can be applied at a rate of about 0.5 to about 15 mg of polymer coating per square inch of exposed substrate surface. In some embodiments, the water-dispersible coating is applied at a thickness of about 1 to about 25 μm.

Example

The invention will now be illustrated by the following examples.

test

The acid value is measured by dissolving approximately 0.1 g of sample in a 1:1 mixture of xylene and isopropanol. One drop of phenolphthalein in ethanol is added to the resulting mixture. The mixture is then titrated using 0.1 N potassium hydroxide solution to a light pink endpoint.

Example 1

Step 1—Preparation of substituted succinic anhydride compounds

150.0 g of soybean oil, 3.0 g of xylene, and 50.0 g of maleic anhydride (under a nitrogen blanket) were added to a 1-liter flask equipped with a stirrer and reflux condenser. The temperature was raised to 180° C. while stirring, and then further increased to 220° C. over 45 minutes. This temperature was maintained for 1.5 hours, after which the mixture was cooled to 100° C. The xylene flowed down, allowing the maleic anhydride to sublime, thereby obtaining a better conversion and a cleaner reaction. The xylene was distilled off with the water in step 2.

Step 2—Conversion of substituted succinic anhydride compounds into substituted succinimide compounds

The reflux condenser was removed from the flask and replaced with a Dean-Stark condenser, allowing vapors to be removed from the flask and collected. 45.5 g of β-alanine was added to the substituted succinic anhydride compound and the temperature was raised to 170°C over 1 hour. The exotherm and foaming generated by the reaction of maleic anhydride and the primary amine were monitored. When the foaming subsided, vacuum was applied at 170°C to drive the reaction to completion. During the formation of the substituted succinimide compound, approximately 7 g of water was collected at 170°C over approximately 2 hours.

Step 3 - Dispersion Formation

The substituted succinimide compound was cooled to about 90°C and 35g of dimethylethanolamine dissolved in 100g was added over about 2 minutes. As the dispersion formed and cooled, an additional 408g of water was added over about 15 minutes with stirring (400 rpm, 3-inch flat blade). The solids content of the dispersion was 20.4%.

Example 2

The same procedure as in Example 1 was carried out, except that 150.0 g of soybean oil was replaced by 135.0 g of gum rosin, 50.0 g of maleic anhydride was replaced by 45.0 g of maleic anhydride, 45.5 g of β-alanine was replaced by 41.0 g of β-alanine, 35 g of dimethylaminoethanol was replaced by 33 g of dimethylaminoethanol, and 408 g of water was replaced by 602 g of water.

Example 3

The following ingredients were reacted according to the method described below.

Step 1—Preparation of substituted succinic anhydride compounds

Soybean oil, xylene, and maleic anhydride (under a nitrogen blanket) are added to a 1-liter flask (equipped with a stirrer and condenser) while stirring. The temperature is raised to 180°C, then further increased to 220°C over 45 minutes. This temperature is maintained for 1.5 hours, after which the mixture is cooled to 100°C. Note: The xylene stream sublimes the maleic anhydride, thus resulting in better conversion and a cleaner reaction. It is distilled off with the water in Step 2.

Step 2—Conversion of substituted succinic anhydride compounds into substituted succinimide compounds

The reflux condenser was removed from the flask and replaced with a Dean-Stark condenser, allowing vapors to be removed from the flask and collected. β-Alanine was added and the temperature was raised to 170°C over 1 hour. Care was taken to control the exotherm and foaming generated by the reaction of the anhydride and amine. After the foaming subsided, vacuum was applied at 170°C to drive the reaction forward. Approximately 7 g of water was collected over approximately 2 hours at 170°C as the substituted succinimide compound was formed.

Step 3 - Emulsion Formation

The substituted succinimide compound was cooled to about 90°C and 35 g of dimethylethanolamine dissolved in 100 g was added over about 2 minutes. As the emulsion formed and cooled, an additional 408 g of water was added over about 15 minutes with good stirring (400 rpm, 3-inch flat blade). The solids content of the emulsion was 20.4%.

Example 4

The following ingredients were reacted according to the method described below.

Step 1—Preparation of substituted succinic anhydride compounds

Soybean oil, xylene, and maleic anhydride (under nitrogen blanket) were added to a 1-liter flask (equipped with a stirrer and condenser) while stirring. The temperature was raised to 180°C and then further increased to 220°C over 45 minutes. This temperature was maintained for 1.5 hours, after which the mixture was cooled to 100°C. A vacuum was applied.

Step 2—Conversion of substituted succinic anhydride compounds into substituted succinimide compounds

The reflux condenser was removed from the flask and replaced with a Dean-Stark condenser, allowing vapors to be removed from the flask and collected. β-Alanine was added and the temperature was raised to 150°C over 1 hour. Care was taken to control the exotherm and foaming generated by the reaction of the anhydride and amine.

Step 3 - Emulsion Formation

The substituted succinimide compound was cooled to about 90°C and 35 g of dimethylethanolamine dissolved in 100 g was added over about 2 minutes. As the emulsion formed and cooled, an additional 408 g of water was added over about 15 minutes with good stirring (400 rpm, 3-inch flat blade). The solids content of the emulsion was 20.4%.

Claims (18)

1. An aqueous coating composition comprising a substituted succinimide compound, wherein the substituted succinimide compound has an acid value of at least 30 mg KOH/g, and wherein the substituted succinimide compound is a reaction product of the following substances: a) A polyunsaturated oil containing at least one non-aromatic unsaturated carbon-carbon bond, a polymer derived from the polyunsaturated oil, or a combination thereof; b) Maleic anhydride; and c) Primary amines of the general formula _NH₂RCOOH , wherein R is an alkyl or aryl group having 2 to 30 carbon atoms, and wherein the amine ( _-NH₂ ) group and the acid (-COOH) group of the primary amine are separated by more than one carbon atom. 2. The waterborne coating composition of claim 1, wherein the waterborne coating composition further comprises a base polymer, and wherein the substituted succinimide compound accounts for more than 0 to 10% by weight of the coating composition. 3. The waterborne coating composition of claim 2, wherein the base polymer comprises acrylic polymers, polyurethane polymers, alkyd polymers, epoxy polymers, or mixtures or hybrid copolymers thereof. 4. The waterborne coating composition of claim 3, wherein the base polymer comprises a styrene-acrylic polymer. 5. The waterborne coating composition of claim 1, wherein the number average molecular weight of the substituted succinimide compound is from 400 to 10,000 Daltons. 6. The waterborne coating composition of claim 2, wherein the number average molecular weight of the substituted succinimide compound is from 400 to 10,000 Daltons. 7. The waterborne coating composition of claim 3, wherein the number average molecular weight of the substituted succinimide compound is from 400 to 10,000 Daltons. 8. The waterborne coating composition of claim 4, wherein the number average molecular weight of the substituted succinimide compound is from 400 to 10,000 Daltons. 9. The aqueous coating composition according to any one of claims 1-8, wherein the acid value of the substituted succinimide compound is 30 to 300 mg KOH/g of the substituted succinimide compound. 10. The waterborne coating composition according to any one of claims 1-8, wherein the succinimide compound is partially or completely neutralized to promote dispersion in the waterborne coating composition. 11. The aqueous coating composition according to any one of claims 1-8, wherein the primary amine is β-alanine. 12. The waterborne coating composition according to claim 1, wherein R is substituted with an acid group. 13. The aqueous coating composition according to any one of claims 1-8, wherein the polyunsaturated oil is a triglyceride. 14. The waterborne coating composition according to any one of claims 1-8, wherein the unsaturated carbon-carbon bond is a carbon-carbon double bond. 15. A substrate coated with an aqueous coating composition according to any one of claims 1-14. 16. A method for preparing a water-based coating composition, comprising: a) Reacting a polyunsaturated oil containing at least one non-aromatic unsaturated carbon-carbon bond, a polymer derived from the polyunsaturated oil, or a combination thereof with maleic anhydride to form a substituted succinic anhydride compound. b) Reacting a substituted succinic anhydride compound with a primary amine of the general formula _NH₂RCOOH to form an amide acid intermediate; wherein R is an alkyl or aryl group having 2 to 30 carbon atoms, and wherein the amine ( _-NH₂ ) group and the acid (-COOH) group of the primary amine are separated by more than one carbon atom; c) precipitate water from the amic acid intermediate to form a substituted succinimide compound; and d) Neutralizing the substituted succinimide compound in the presence of water to form a waterborne coating composition. The substituted succinimide compound has an acid value of at least 30 mg KOH/g. 17. The method of claim 16, wherein the polyunsaturated oil is a triglyceride. 18. The method of claim 16 or 17, wherein the unsaturated carbon-carbon bond is a carbon-carbon double bond.