Crosslinking compositions and coatings formed therefrom

Patent metadata

Field	Value
Publication number	US-11242430-B2
Application number	US-201916655662-A
Country	US
Kind code	B2
Filing date	Oct 17, 2019
Priority date	Oct 17, 2019
Publication date	Feb 8, 2022
Grant date	Feb 8, 2022

Abstract

A crosslinking composition includes a compound having at least two functional groups that are each independently represented by Chemical Structure (I):

X is an oxygen, sulfur, or nitrogen; R 1 is an alkyl group, an aryl group, or an alkylaryl group; R 2 , R 3 , and R 4 are each independently an alkyl group, an aryl group, an alkylaryl group, or a hydrogen; R 5 is an alkyl group, an aryl group, an alkylaryl group, or a hydrogen; z is 0 when X is oxygen or sulfur and z is 1 when X is nitrogen; and when a double bond is formed between a carbon atom bonded to R 3 and an adjacent nitrogen, m is 0, and when a single bond is formed between the carbon atom bonded to R 3 and the adjacent nitrogen, m is 1.

First claim

The invention claimed is:

1. A crosslinking composition comprising:
a compound comprising at least two functional groups that are each independently represented by Chemical Structure (I):

X is an oxygen, sulfur, or nitrogen;
R 1 is an alkyl group, an aryl group, or an alkylaryl group;
R 2 , R 3 , and R 4 are each independently an alkyl group, an aryl group, an alkylaryl group, or a hydrogen; and
R 5 is an alkyl group, an aryl group, an alkylaryl group, or a hydrogen;
z is 0 when X is oxygen or sulfur and z is 1 when X is nitrogen;
when a double bond is formed between a carbon atom bonded to R 3 and an adjacent nitrogen, m is 0, and when a single bond is formed between the carbon atom bonded to R 3 and the adjacent nitrogen, m is 1; and
wherein: (i) the compound further comprises one or more additional functional groups that are reactive with the functional groups represented by Chemical Structure (I) such that the compound is self-crosslinkable; and/or
(ii) the composition further comprises a film-forming resin comprising functional groups that are reactive with the functional groups represented by Chemical Structure (I) of the compound.

2. The crosslinking composition of claim 1 , wherein X is an oxygen.

3. The crosslinking composition of claim 1 , wherein at least one of the functional groups of Chemical Structure (I) is represented by Chemical Structure (II):

4. The crosslinking composition of claim 1 , wherein at least one of the functional groups of Chemical Structure (I) is represented by Chemical Structure (III):

5. The crosslinking composition of claim 1 , wherein (i) the compound further comprises the one or more additional functional groups that are reactive with the functional groups represented by Chemical Structure (I) such that the compound is self-crosslinkable.

6. The crosslinking composition of claim 5 , wherein the additional functional groups comprise hydroxyl functional groups.

7. The crosslinking composition of claim 1 , wherein the compound further comprises ester linkages, ether linkages, aromatic groups, or a combination thereof.

8. The crosslinking composition of claim 1 , wherein the compound is obtained from reactants comprising:
(i) a reaction product of:
(a) a mono-aldo or keto functional compound comprising a hydroxyl functional group, an amino functional group, a carboxylic acid functional group, a thiol functional group, or any combination thereof; and
(b) a hydrazide or hydrazone comprising a group represented by —XR 1 (R 5 ) z that is attached to a carbon atom of the hydrazide or hydrazone, wherein R 1 is an alkyl group, an aryl group, or an alkylaryl group; X is an oxygen, sulfur, or nitrogen; R 5 is an alkyl group, an aryl group, an alkylaryl group, or a hydrogen; z is 0 when X is oxygen or sulfur and z is 1 when X is nitrogen; and

(ii) a component comprising two or more functional groups reactive with the hydroxyl functional group, the amino functional group, the carboxylic acid functional group, and/or the thiol functional group of the reaction product of (i).

9. The crosslinking composition of claim 8 , wherein (i) (a) the mono-aldo or keto functional compound comprises a hydroxyl functional group and (ii) the component comprises two or more epoxy functional groups reactive with the hydroxyl functional group of the reaction product of (i).

10. The crosslinking composition of claim 1 , wherein the compound is obtained from reactants comprising:
(i) a hydrazide or hydrazone comprising a group represented by —XR 1 (R 5 ) z that is attached to a carbon atom of the hydrazide or hydrazone, wherein R 1 is an alkyl group, an aryl group, or an alkylaryl group; X is an oxygen, sulfur, or nitrogen; R 5 is an alkyl group, an aryl group, an alkylaryl group, or a hydrogen; z is 0 when X is oxygen or sulfur and z is 1 when X is nitrogen; and
(ii) a component comprising two or more functional groups reactive with an amino group of the hydrazide or hydrazone of (i).

11. The crosslinking composition of claim 10 , wherein the two or more functional groups of component (ii) comprise ethylenically unsaturated functional groups, keto functional groups, aldo functional groups, epoxy functional groups, or any combination thereof that are reactive with the amino group of the hydrazide or hydrazone of (i).

12. The crosslinking composition of claim 1 , wherein the composition further comprises (ii) the film-forming resin comprising functional groups reactive with the functional groups represented by Chemical Structure (I) of the compound.

13. The crosslinking composition of claim 12 , wherein the film-forming resin comprises hydroxyl functional groups, amino functional groups, thiol functional groups, or a combination thereof.

14. The crosslinking composition of claim 13 , wherein the film-forming resin has an equivalent weight of 400 or less.

15. The crosslinking composition of claim 1 , wherein the crosslinking composition is a coating composition that forms a coating when cured.

16. The crosslinking composition of claim 15 , wherein the coating composition is an electrodepositable coating composition.

17. A substrate at least partially coated with the coating formed from the coating composition of claim 15 .

18. The substrate of claim 17 , wherein the coating is formed directly over at least a portion of the substrate.

19. The substrate of claim 17 , wherein the coating is formed over one or more additional coating layers formed over the substrate.

20. The substrate of claim 17 , wherein one or more additional coating layers are formed over the coating formed from the coating composition of claim 15 .

Assignees

• Ppg Ind Ohio Inc

Inventors

• Macdonald Melissa Joan
• Zheng Qi
• Ibrahim Abdulrahman Dawoud
• Lee Se Ryeon
• MIZUHARA Tsukasa
• Grenier Christophe René Gaston
• Eswarakrishnan Venkatachalam

Classifications

• C09D163/10

  Epoxy resins modified by unsaturated compounds · CPC title

• C09D163/06

  Triglycidylisocyanurates · CPC title

• C09D5/44 Primary

  for electrophoretic applications (processes for coating by electrophoresis C25D13/00) · CPC title

• C08G59/3227

  Compounds containing acyclic nitrogen atoms · CPC title

• C08G59/1477 Primary

  containing nitrogen · CPC title