Polyfunctional hydrazide crosslinker

Patent metadata

Field	Value
Publication number	US-12173178-B2
Application number	US-202118256429-A
Country	US
Kind code	B2
Filing date	Dec 10, 2021
Priority date	Dec 10, 2020
Publication date	Dec 24, 2024
Grant date	Dec 24, 2024

Abstract

A crosslinker composition is prepared from a reaction mixture including: (a) a prepolymer including a reaction product of a prepolymer mixture including: (i) a polyfunctional isocyanate; and (ii) a first compound comprising two or more active hydrogen groups, where the polyfunctional isocyanate and/or the first compound comprising two or more active hydrogen groups includes a greater than two functional isocyanate and/or active hydrogen groups, respectively; and (b) a polyfunctional hydrazide. The crosslinker composition is not self-crosslinkable. The crosslinker composition has an acid value of at least 15 based on total resin solids of the crosslinker composition.

First claim

The invention claimed is:

1. A crosslinker composition prepared from a reaction mixture comprising:
(a) a prepolymer comprising a reaction product of a prepolymer mixture comprising:
(i) a polyfunctional isocyanate; and
(ii) a first compound comprising two or more active hydrogen groups; and

(b) a polyfunctional hydrazide,
wherein the crosslinker composition is not self-crosslinkable,
wherein the crosslinker composition has an acid value of at least 15 based on total resin solids of the crosslinker composition;
wherein the crosslinker composition comprises a hydrazide equivalent weight of from 200 to 3,000, based on the total resin solids content of the crosslinker composition.

2. The crosslinker composition of claim 1 , wherein the first compound comprising two or more active hydrogen groups comprises an acid group.

3. The crosslinker composition of claim 1 , wherein the first compound comprising two or more active hydrogen groups comprises greater than two active hydrogen functional groups.

4. The crosslinker composition of claim 1 , wherein the first compound comprising two or more active hydrogen groups comprises dimethylol propionic acid and/or an acid derived from trimellitic anhydride.

5. The crosslinker composition of claim 1 , wherein the prepolymer mixture further comprises (iii) a compound comprising an acid group, wherein the compound comprising the acid group is different from (i) and (ii).

6. The crosslinker composition of claim 1 , wherein the prepolymer comprises isocyanate functionality greater than two.

7. The crosslinker composition of claim 1 , wherein:
the polyfunctional isocyanate comprises greater than two isocyanate functional groups; and
the first compound comprising two or more active hydrogen groups comprises an acid group.

8. The crosslinker composition of claim 1 , wherein:
the first compound comprising two or more active hydrogen groups comprises greater than two active hydrogen groups; and
the prepolymer mixture further comprises (iii) a second compound comprising two or more active hydrogen groups comprising an acid group.

9. The crosslinker composition of claim 1 , wherein:
the polyfunctional isocyanate comprises greater than two isocyanate functional groups;
the first compound comprising two or more active hydrogen groups comprises dimethylol propionic acid, and
wherein the crosslinker composition comprises a hydrazide equivalent weight of up to 1,000, based on the total resin solids content of the crosslinker composition.

10. The crosslinker composition of claim 1 , wherein the first compound comprising two or more active hydrogen groups comprises a polyol comprising a polyester polyol, a polyether polyol, polycarbonate polyol, and/or a silicone-containing polyol.

11. The crosslinker composition of claim 1 , wherein the first compound comprising two or more active hydrogen groups comprises a cyclic-substituted polyester polyol.

12. The crosslinker composition of claim 1 , wherein the reaction mixture further comprises water and/or a neutralizing amine.

13. The crosslinker composition of claim 1 , wherein the reaction mixture and/or the prepolymer mixture are substantially free of vinyl unsaturation and/or an epoxy.

14. The crosslinker composition of claim 1 , wherein the crosslinker composition has a weight average molecular weight of from 30,000 to 500,000 g/mol.

15. The crosslinker composition of claim 1 , wherein the first compound comprising two or more active hydrogen groups comprises a polyol.

16. The crosslinker composition of claim 1 , wherein the crosslinker composition comprises greater than two hydrazide groups.

17. The crosslinker composition of claim 1 , wherein the crosslinker composition is substantially free of a keto and/or aldo-functional group.

18. A coating composition, comprising:
the crosslinker composition according to claim 1 ; and
a polymer reactive with the crosslinker composition, wherein the polymer comprises a carbonyl-functional group.

19. The coating composition of claim 18 , further comprising a polyester polymer obtained from components comprising polytetrahydrofuran and a carboxylic acid or anhydride thereof.

20. The coating composition of claim 18 , wherein the coating composition comprises a waterborne coating composition.

21. The coating composition of claim 18 , wherein the coating composition comprises a pH of greater than 7 at ambient temperature.

22. The crosslinker composition of claim 1 , wherein the polyfunctional isocyanate and/or the first compound comprising two or more active hydrogen groups comprises greater than two functional isocyanate and/or active hydrogen groups, respectively.

Assignees

• Ppg Ind Ohio Inc

Inventors

• Weis Jonathan Garrett
• Hensel Gereme
• Landis Chad Alan
• Velez-Herrera Pedro
• Wang Maria
• Swarup Shanti
• MIZUHARA Tsukasa
• Xu Xiangling

Classifications

• C08G18/3231

  Hydrazine or derivatives thereof · CPC title

• C09D175/08

  from polyethers · CPC title

• C08G2150/00

  Compositions for coatings · CPC title

• C08G18/348

  Hydroxycarboxylic acids · CPC title

• C08G18/302

  Water · CPC title