Cardanol-derivatives modified polymer and a coating composition comprising the same

Patent metadata

Field	Value
Publication number	US-12528909-B2
Application number	US-202017637295-A
Country	US
Kind code	B2
Filing date	Aug 24, 2020
Priority date	Aug 28, 2019
Publication date	Jan 20, 2026
Grant date	Jan 20, 2026

Abstract

Described herein is a cardanol-derivatives modified polymer obtained from a reaction of epoxy groups in a cardanol-derivative compound and carboxyl groups in a carboxyl-functional polymer, where the cardanol-derivative compound is the reaction product of cardanol-derivatives modified with haloalkylene oxide having a carbon number of from 3 to 10. Also described herein is a process of preparing the cardanol-derivatives modified polymer, a method of using the cardanol-derivatives modified polymer in automotive coatings, and the obtained coating composition thereof.

First claim

The invention claimed is:

1 . A cardanol-derivatives modified polymer obtained from a reaction of epoxy groups in a cardanol-derivative compound and carboxyl groups in a carboxyl-functional polymer, wherein the cardanol-derivative compound is a resultant product of cardanol reacted with haloalkylene oxide having a carbon number of from 3 to 10, and an acid number of the carboxyl-functional polymer is from 100 to 200 mg KOH/g, and at least 60% of carboxyl groups in the carboxyl-functional polymer is reacted with epoxy groups in the cardanol-derivative compound, and
wherein:
the carboxyl-functional polymer is obtained from copolymerization of monomers selected from the group consisting of hydroxy alkyl (meth)acrylate and monomers selected from the group consisting of a linear or cyclic alkyl dicarboxylic acid or anhydride and lactone; or
the carboxyl-functional polymer is at least one selected from the group consisting of carboxyl-functional polyurethanes and carboxyl-functional polyamides.

2 . The cardanol-derivatives modified polymer according to claim 1 , wherein a weight average molecular weight of the carboxyl-functional polymer is from 1000 g/mol to 12000 g/mol.

3 . A process of preparing the cardanol-derivatives modified polymer according to claim 1 , comprising steps of:
i). providing a mixture containing the cardanol-derivative compound and the carboxyl-functional polymer; and ii). heating the mixture obtained in step i) at a temperature of less than 200° C.

4 . The process according to claim 3 , wherein in the mixture obtained in step i), a molar ratio of a total epoxy group of the cardanol-derivative compound to a total carboxyl group of the carboxyl-functional polymer is no more than 1:1.

5 . A coating composition containing the cardanol-derivatives modified polymer according to claim 1 .

6 . A coating composition comprising:
(A) from 30% to 60% by weight of the cardanol-derivatives modified polymer according to claim 1 , based on a total weight of the coating composition, and (B) from 15% to 30% by weight of a curing agent, based on a total weight of a binder in the coating composition.

7 . A process of preparing automotive coatings comprising a step of introducing the cardanol-derivatives modified polymer according to claim 1 into the coatings.

8 . The cardanol-derivatives modified polymer according to claim 1 , wherein a weight average molecular weight of the carboxyl-functional polymer is from 1000 g/mol to 10000 g/mol.

9 . The cardanol-derivatives modified polymer according to claim 1 , wherein the carboxyl-functional polymer is obtained from copolymerization of monomers selected from the group consisting of hydroxy alkyl (meth)acrylate and monomers selected from the group consisting of a linear or cyclic alkyl dicarboxylic acid or anhydride and lactone, wherein the monomers for copolymerization further comprise a monomer selected from the group consisting of (meth)acrylic acid and styrene.

10 . A process of preparing the cardanol-derivatives modified polymer according to claim 1 , comprising steps of:
i). providing a mixture containing the cardanol-derivative compound and the carboxyl-functional polymer and further containing at least one catalyst selected from the group consisting of triphenyl phosphine, triphenyl antimony, and chromium (III) acetylacetonate; and ii). heating the mixture obtained in step i) at a temperature of less than 200° C.

11 . The process according to claim 3 , wherein in the mixture obtained in step i), a molar ratio of a total epoxy group of the cardanol-derivative compound to a total carboxyl group of the carboxyl-functional polymer is from 3:5 to 1:1.

12 . A coating composition comprising:
(A) from 45% to 65% by weight of the cardanol-derivatives modified polymer according to claim 1 , based on a total weight of the coating composition, and (B) from 20% to 30% by weight of a curing agent, based on a total weight of a binder in the coating composition, wherein the curing agent is at least one selected from the group consisting of isocyanate curing agent, aminoplast curing agent, amine curing agent, and remaining solvent.

13 . The cardanol-derivatives modified polymer according to claim 1 , wherein a molar ratio of a total epoxy group of the cardanol-derivative compound to a total carboxyl group of the carboxyl-functional polymer is no more than 1:1.

Assignees

• Basf Coatings Gmbh

Inventors

• Wang han bin
• Li Qiang
• Hirsemann Stefan

Classifications

• C09D167/07

  having terminal carbon-to-carbon unsaturated bonds · CPC title

• C08K5/0025

  Crosslinking or vulcanising agents; including accelerators · CPC title

• C08G2150/00

  Compositions for coatings · CPC title

• C08F8/14 Primary

  Esterification · CPC title

• C08F220/1804

  C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate · CPC title