Polymers with functional imide groups and pigment dispersions and coatings formed therefrom

Patent metadata

Field	Value
Publication number	US-10273317-B2
Application number	US-201615249732-A
Country	US
Kind code	B2
Filing date	Aug 29, 2016
Priority date	Aug 29, 2016
Publication date	Apr 30, 2019
Grant date	Apr 30, 2019

Abstract

A polymer having N-functional imide groups is prepared from reactants that include: (a) an ethylenically unsaturated anhydride or diacid monomer; (b) at least one co-monomer that is different from (a) having an ethylenically unsaturated group that is reactive with (a); and at least one compound reactive with the anhydride or diacid functional groups of (a) that is represented by Chemical Formula I: H2N—R1. With respect to Chemical Formula I, R1 is selected from NH2 or OH. Pigment dispersions and coating compositions are also prepared with the polymers having N-functional imide groups.

First claim

The invention claimed is:

1. A polymer comprising N-functional imide groups prepared from reactants comprising:
(a) an ethylenically unsaturated anhydride or diacid monomer;
(b) at least one co-monomer that is different from (a) comprising an ethylenically unsaturated group that is reactive with (a); and
(c) at least one compound reactive with the anhydride or diacid functional groups of (a) that is represented by Chemical Formula I:
H 2 N—R 1   (I),

wherein R 1 is NH 2 ,
wherein a molar ratio of the ethylenically unsaturated anhydride or diacid monomer (a) to the at least one co-monomer (b) is within a range from 1:1 to 1:100, and
wherein the at least one co-monomer comprises an ethylenically unsaturated non-aromatic compound.

2. The polymer comprising N-functional imide groups of claim 1 , wherein a glass transition temperature of the polymer comprising N-functional imide groups is 80° C. or less.

3. The polymer comprising N-functional imide groups of claim 1 , wherein a molar ratio of the ethylenically unsaturated anhydride or diacid monomer (a) to the at least one compound (c) is within a range from 10:1 to 1:1.

4. The polymer comprising N-functional imide groups of claim 1 , wherein the reactants are completely free of multifunctional hydrazine derivatives.

5. The polymer comprising N-functional imide groups of claim 1 , wherein the polymer comprising N-functional imide groups has a weight average molecular weight of 500 to 50,000 g/mol.

6. The polymer comprising N-functional imide groups of claim 1 , wherein the ethylenically unsaturated anhydride or diacid monomer (a) comprises a cyclic anhydride represented by Chemical Structure II:

wherein R 2 is a C 2 or C 3 carbon chain comprising the ethylenically unsaturated group.

7. The polymer comprising N-functional imide groups of claim 1 , wherein the ethylenically unsaturated anhydride or diacid monomer (a) comprises a diacid represented by Chemical Formula III:
R 3 (COOH) 2   (III),

wherein R 3 is a C 2 to C 5 carbon chain comprising the ethylenically unsaturated group.

8. The polymer comprising N-functional imide groups of claim 1 , wherein the polymer comprising N-functional imide groups comprises N-functional cyclic imide structures represented by at least one of Chemical Structure Iva and Chemical Structure IVb:

9. The polymer comprising N-functional imide groups of claim 8 , wherein the polymer comprising N-functional imide groups further comprises a cyclic structure represented by at least one of Chemical Structure VIa and Chemical Structure VIb:

10. A pigment dispersion comprising:
(1) a polymer comprising N-functional imide groups prepared from reactants comprising:
(a) an ethylenically unsaturated anhydride or diacid monomer;
(b) at least one co-monomer that is different from (a) comprising an ethylenically unsaturated group that is reactive with (a); and
(c) at least one compound reactive with the anhydride or diacid functional groups of (a) that is represented by Chemical Formula I:
H 2 N—R 1   (I),

wherein R 1 is selected from NH 2 or OH,
wherein a molar ratio of the ethylenically unsaturated anhydride or diacid monomer (a) to the at least one co-monomer (b) is within a range from 1:1 to 1:100, and
wherein the at least one co-monomer comprises an ethylenically unsaturated non-aromatic compound; and
(2) pigment.

11. The pigment dispersion of claim 10 , further comprising (3) a liquid carrier medium.

12. The pigment dispersion of claim 10 , wherein the polymer comprising N-functional imide groups comprises amino functional imide structures and the pigment comprises organic pigments.

13. The pigment dispersion of claim 10 , wherein the polymer comprising N-functional imide groups comprises hydroxyl functional imide structures and the pigment comprises inorganic pigments.

14. The pigment dispersion of claim 10 , wherein the ethylenically unsaturated anhydride or diacid monomer (a) of the reactants used to prepare the polymer comprising N-functional imide groups comprises a cyclic anhydride represented by Chemical Structure II:

wherein R 2 is a C 2 or C 3 carbon chain comprising the ethylenically unsaturated group.

15. The pigment dispersion of claim 10 , wherein the ethylenically unsaturated anhydride or diacid monomer (a) of the reactants used to prepare the polymer comprising N-functional imide groups comprises a diacid represented by Chemical Formula III:
R 3 (COOH) 2   (III),

wherein R 3 is a C 2 to C 5 carbon chain comprising the ethylenically unsaturated group.

16. The pigment dispersion of claim 10 , further comprising (4) an additional pigment dispersant that is different from the polymer comprising N-functional imide groups.

17. A coating composition comprising:
(1) a film-forming resin; and
(2) a pigment dispersion according to claim 10 .

18. The coating composition of claim 17 , wherein the film-forming resin is different from the polymer comprising N-functional imide groups.

19. The coating composition of claim 17 , further comprising a crosslinker.

20. The coating composition of claim 19 , wherein the crosslinker comprises a carbodiimide crosslinker, an epoxy crosslinker, an isocyanate crosslinker, an aziridine crosslinker, or a combination thereof.

21. A substrate at least partially coated with at least one coating formed from the coating composition of claim 17 .

Assignees

• Ppg Ind Ohio Inc

Inventors

• Breon Jonathan Paul
• Zhou Hongying
• Dillon Brian Thomas
• Coca Simion

Classifications

• C08F8/32 Primary

  by reaction with amines · CPC title

• C09D123/36

  by reaction with compounds containing nitrogen, e.g. by nitration · CPC title

• C09D7/65

  macromolecular (C09D7/41-C09D7/48 take precedence) · CPC title

• C08F8/48

  Isomerisation; Cyclisation · CPC title

• C08F8/14

  Esterification · CPC title