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

Patent metadata

Field	Value
Publication number	US-9469785-B2
Application number	US-201314428523-A
Country	US
Kind code	B2
Filing date	Sep 19, 2013
Priority date	Sep 19, 2012
Publication date	Oct 18, 2016
Grant date	Oct 18, 2016

Abstract

The invention includes an aqueous coating composition having a substituted succinimide compound, wherein the substituted succinimide compound has an acid value of at least about 30 mg KOH/g of the 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 the unsaturated oil, or a combination thereof with maleic anhydride and a primary amine.

First claim

The invention claimed is:

1. An aqueous coating composition comprising a substituted succinimide compound, wherein the substituted succinimide compound has an acid value of at least about 30 mg KOH/g of the substituted succinimide compound, and wherein the substituted succinimide compound is the reaction product of
a) an unsaturated oil comprising at least one non-aromatic unsaturated carbon-carbon bond, a polymer derived from the unsaturated oil, or a combination thereof;
b) maleic anhydride; and
c) a primary amine of general formula NH 2 RCOOH, wherein R is an alkyl group or an aryl group with about 2 to about 30 carbon atoms and wherein the amine (—NH 2 ) group and the acid (—COOH) group of the primary amine are separated by more than one carbon atom.

2. The aqueous coating composition according to claim 1 , wherein the aqueous coating composition further comprises a binder polymer, and wherein the substituted succinimide compound comprises from greater than 0 to about 10 wt % of the coating composition.

3. The aqueous coating composition according to claim 2 , wherein the binder polymer comprises an acrylic polymer, a styrene-acrylic polymer, a polyurethane polymer, an alkyd polymer, an epoxy polymer, or a mixture or hybrid copolymer thereof.

4. The aqueous coating composition according to claim 1 , wherein the number average molecular weight of the substituted succinimide compound is from about 400 to about 10,000 Daltons.

5. The aqueous coating composition according to claim 1 , wherein the acid value of the substituted succinimide compound is from about 30 to about 300 mg KOH/g of the substituted succinimide compound.

6. The aqueous coating composition according to claim 1 , wherein the substituted succinimide compound is partially or fully neutralized to facilitate dispersion in the aqueous coating composition.

7. The aqueous coating composition according to claim 1 , wherein the primary amine is β-alanine.

8. The aqueous coating composition according to claim 1 , wherein R is substituted with an acid group.

9. A substrate coated with the aqueous coating composition according to claim 1 .

10. A method of preparing an aqueous coating composition comprising:
a) reacting an unsaturated oil comprising at least one non-aromatic unsaturated carbon-carbon bond, a polymer derived from the 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 of general formula NH 2 RCOOH, where R is an alkyl group or an aryl group with about 2 to about 30 carbon atoms and wherein the amine (—NH 2 ) group and the acid (—COOH) group of the primary amine are separated by more than one carbon atom to form an amic acid intermediate;
c) evolving 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 the aqueous coating composition,
wherein the substituted succinimide compound has an acid value of at least about 30 mg KOH/g of the substituted succinimide compound.

Assignees

• Akzo Nobel Coatings Int Bv

Inventors

• Craun Gary Pierce
• Rademacher Jude
• Geelen Patricia

Classifications

• C09D173/02

  Polyanhydrides · CPC title

• C09F7/00

  Chemical modification of drying oils (modifying by copolymerisation C08F; polycondensation C08G; factice C08H) · CPC title

• C07D207/408

  Radicals containing only hydrogen and carbon atoms attached to ring carbon atoms · CPC title

• C07D207/40

  2,5-Pyrrolidine-diones · CPC title

• C09D133/00

  Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers · CPC title