Hydroxy functional alkyl polyurea crosslinkers

Patent metadata

Field	Value
Publication number	US-11203701-B2
Application number	US-201716069736-A
Country	US
Kind code	B2
Filing date	Jan 13, 2017
Priority date	Jan 15, 2016
Publication date	Dec 21, 2021
Grant date	Dec 21, 2021

Abstract

A hydroxy functional alkyl polyurea is disclosed having the formula presented in claim 1, wherein R comprises an isocyanurate moiety, biuret moiety, allophonate moiety, glycoluril moiety, benzoguanamine moiety, polyetheramine moiety, and/or polymeric moiety different from a polyetheramine and having an Mn of 500 or greater; wherein each R 1 is independently a hydrogen, alkyl having at least 1 carbon, or a hydroxy functional alkyl having 2 or more carbons and at least one R 1 is a hydroxy functional alkyl having 2 or more carbons; and n is 2-6. Further disclosed is a coating comprising: a film-forming resin; and a hydroxy functional alkyl polyurea crosslinker having the formula presented in claim 4, wherein R 1 is a substituted or unsubstituted C 1 to C 36 alkyl group, an aromatic group, an isocyanurate moiety, biuret moiety, allophonate moiety, glycoluril moiety, benzoguanamine moiety, polyetheramine moiety, and/or polymeric moiety different from a polyetheramine having an Mn of 500 or greater, wherein each R 1 is independently a hydrogen, an alkyl having at least 1 carbon, or a hydroxy functional alkyl having 2 or more carbons and at least one R 1 is a hydroxy functional alkyl having 2 or more carbons; and n is 2-6, and when R 2 is a substituted or unsubstituted C 1 to C 36 alkyl group the film-forming resin comprises COOH functionality that reacts with the polyurea to form an ester linkage. Other hydroxy functional alkyl polyurea compounds, polymers made with the same, and compositions comprising the same are also disclosed as are substrates coated at least in part with or formed with any of the compositions described herein.

First claim

What is claimed is:

1. A hydroxy functional alkyl polyurea having the formula:

wherein R comprises an isocyanurate moiety, biuret moiety, allophonate moiety, glycoluril moiety, benzoguanamine moiety, polyetheramine moiety, and/or polymeric moiety different from a polyetheramine and having an Mn of 500 or greater; wherein each R 1 is independently a hydrogen, an alkyl having at least 1 carbon, or a hydroxy functional alkyl having 2 or more carbons and at least one R 1 is a hydroxy functional alkyl having 2 or more carbons; and n is 2-6.

2. The polyurea of claim 1 , wherein R comprises an isocyanurate moiety.

3. The polyurea of claim 1 , wherein at least one R 1 comprises a 2-hydroxyethyl or 2-hydroxypropyl group.

4. A substrate formed with the polyurea of claim 1 further comprising wood particles.

5. The hydroxy functional alkyl polyurea of claim 1 , wherein the polymeric moiety contains an acid functionality.

6. The hydroxy functional alkyl polyurea of claim 1 , wherein the polymeric moiety comprises a polyester polyurethane, a polyether polyurethane, and/or a polyamide polyurethane.

7. The hydroxy functional alkyl polyurea of claim 6 , wherein the polyester polyurethane contains an acid functionality.

8. A composition comprising:
a. A film-forming resin; and
b. A hydroxy functional alkyl polyurea crosslinker having the formula:

wherein R 2 is a substituted or unsubstituted C 1 to C 36 alkyl group, an aromatic group, an isocyanurate moiety, biuret moiety, allophonate moiety, glycoluril moiety, benzoguanamine moiety, polyetheramine moiety, and/or polymeric moiety different from a polyetheramine having an Mn of 500 or greater; wherein each Ri is independently a hydrogen, an alkyl having at least 1 carbon, or a hydroxy functional alkyl having 2 or more carbons and at least one R 1 is a hydroxy functional alkyl having 2 or more carbons; and n is 2-6.

9. The composition of claim 8 , wherein R 2 comprises a substituted or unsubstituted C 2 -C 12 alkyl or aromatic group.

10. The composition of claim 8 , wherein R 2 comprises a substituted or unsubstituted C 6 alkyl group.

11. The composition of claim 8 , wherein R 1 comprises a 2-hydroxyethyl or 3-hydroxypropyl group.

12. The composition of claim 8 , wherein the composition is substantially formaldehyde free.

13. The composition of claim 8 , wherein the R 1 groups do not contain an ether linkage.

14. The composition of claim 8 , wherein the film-forming resin comprises a polyolefin dispersion.

15. The composition of claim 8 , wherein the composition is formulated as a sound damping composition.

16. The composition of claim 8 , wherein the polymeric moiety contains an acid functionality.

17. The composition of claim 8 , wherein the film-forming resin comprises an acid functionality.

18. The composition of claim 8 , wherein when R 2 is a substituted or unsubstituted C 1 to C 36 alkyl group, the film-forming resin comprises COOH functionality that reacts with the polyurea to form an ester linkage.

19. The composition of claim 8 , further comprising a catalyst.

20. The composition of claim 12 , wherein the catalyst comprises tin and/or titanium.

21. The composition of claim 8 , formulated as a coating.

22. The composition of claim 21 , wherein the coating is a powder coating.

23. The composition of claim 22 , wherein R 2 comprises a polymeric moiety having an Mn of 500 or greater.

24. A substrate coated at least in part with the coating of claim 21 .

25. The substrate of claim 12 , wherein the substrate comprises a package.

26. The substrate of claim 24 , wherein the substrate comprises a metal can.

27. The substrate of claim 24 , wherein the substrate comprises a vehicle.

28. The substrate of claim 17 , wherein the substrate comprises rubber and/or plastic.

29. The substrate of claim 24 , wherein the substrate comprises metal sheet or coil.

30. The substrate of claim 24 , wherein the substrate comprises wood particles.

31. The composition of claim 8 , wherein the polymeric moiety comprises a polyester polyurethane, a polyether polyurethane, and/or a polyamide polyurethane.

32. The composition of claim 31 , wherein the polyester polyurethane contains an acid functionality.

Assignees

• Ppg Ind Ohio Inc

Inventors

• Swarup Shanti
• Zhou Hongying
• Chasser Anthony M
• Millero Jr Edward R
• Kurtz Christopher P
• Dudik John M
• Xu Xiangling
• Retsch Jr William H
• Chao Tien-Chieh
• Kabagambe Jr Benjamin
• Kralic Ronald

Classifications

• C09D175/16

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

• C09D175/12 Primary

  from compounds containing nitrogen and active hydrogen, the nitrogen atom not being part of an isocyanate group · CPC title

• C09D175/02

  Polyureas · CPC title

• C09D5/03

  Powdery paints · CPC title

• C09D5/02

  Emulsion paints {including aerosols} · CPC title