Crosslinking compositions and coatings formed therefrom

Patent metadata

Field	Value
Publication number	US-11827740-B2
Application number	US-202217567526-A
Country	US
Kind code	B2
Filing date	Jan 3, 2022
Priority date	Oct 17, 2019
Publication date	Nov 28, 2023
Grant date	Nov 28, 2023

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; R1 is an alkyl group, an aryl group, or an alkylaryl group; R2, R3, and R4 are each independently an alkyl group, an aryl group, an alkylaryl group, or a hydrogen; R5 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 R3 and an adjacent nitrogen, m is 0, and when a single bond is formed between the carbon atom bonded to R3 and the adjacent nitrogen, m is 1.

First claim

The invention claimed is:

1. A crosslinking 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; 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, and wherein the crosslinking compound comprises a polymer that contains the functional groups represented by Chemical Structure (I), wherein the polymer comprises a (meth)acrylate polymer, a polyurethane polymer, a polyester polymer, a polyamide polymer, a polyether polymer, a polysiloxane polymer, an epoxy polymer, a vinyl polymer, copolymers thereof, and/or combinations thereof.

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

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

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

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

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

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

8. The crosslinking compound 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 compound 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 compound 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 compound 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. A coating composition, comprising:
the crosslinking compound of claim 1 ,
wherein: (i) the crosslinking compound further comprises one or more additional functional groups that are reactive with the functional groups represented by Chemical Structure (I) such that the crosslinking compound is self-crosslinkable; and/or
(ii) the coating composition further comprises a film-forming resin comprising functional groups that are reactive with the functional groups represented by Chemical Structure (I) of the crosslinking compound.

13. The coating composition of claim 12 , wherein the crosslinking compound comprises a monomer that contains the functional groups represented by Chemical Structure (I).

14. The coating composition of claim 1 , wherein the polymer comprises a (meth)acrylate polymer.

15. The coating composition of claim 12 , wherein (i) the crosslinking 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 crosslinking compound is self-crosslinkable,
wherein the one or more additional functional groups comprise hydroxyl functional groups.

16. The coating composition of claim 12 , wherein (ii) the coating composition further comprises the film-forming resin comprising functional groups that are reactive with the functional groups represented by Chemical Structure (I) of the crosslinking compound,
wherein the film-forming resin comprises hydroxyl functional groups, ammo functional groups, thiol functional groups, or a combination thereof.

17. The coating composition of claim 16 , wherein the film-forming resin comprises a hydroxyl-functional acrylic resin.

18. The coating composition of claim 12 , wherein the coating composition is an electrodepositable coating composition.

19. A substrate at least partially coated with a coating formed from the coating composition of claim 12 .

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

• C08G59/1477 Primary

  containing nitrogen · CPC title

• C08G59/063

  with epihalohydrins · CPC title

• C08G59/3227

  Compounds containing acyclic nitrogen atoms · CPC title

• C09D163/06

  Triglycidylisocyanurates · CPC title

• C09D163/10

  Epoxy resins modified by unsaturated compounds · CPC title