Carbamate functional monomers and polymers and use thereof

Patent metadata

Field	Value
Publication number	US-11274167-B2
Application number	US-201916454723-A
Country	US
Kind code	B2
Filing date	Jun 27, 2019
Priority date	Jun 27, 2019
Publication date	Mar 15, 2022
Grant date	Mar 15, 2022

Abstract

The present invention is directed to a compound of formula I,

wherein R 1 comprises hydrogen, an alkyl group, or an aryl group; R 2 comprises hydrogen or a methyl group; R 3 comprises a divalent organic group; R 4 comprises a divalent organic group; and X comprises oxygen, NH, or N(R 5 ), wherein R 5 comprises a monovalent organic group. The present invention is also directed towards polymers comprising a pendant carbamate-functional moiety comprising the structure:

wherein R 1 comprises hydrogen, an alkyl group, or an aryl group; R 2 comprises hydrogen or a methyl group; R 3 comprises a divalent organic group; R 4 comprises a divalent organic group; and X comprises oxygen, NH, or N(R 5 ) wherein R 5 comprises a monovalent organic group. The present invention is also directed to methods of preparing such compounds and polymers, compositions comprising such polymers, and coatings produced from such compositions.

First claim

We claim:

1. A compound of formula I,

wherein R 1 comprises hydrogen or an alkyl group; R 2 comprises hydrogen or a methyl group; R 3 comprises a divalent organic group; R 4 comprises a divalent organic group; and X comprises oxygen, NH, or N(R 5 ), wherein R 5 comprises a monovalent organic group.

2. The compound of claim 1 , wherein the compound comprises the structure:

wherein R 1 comprises hydrogen or an alkyl group; R 2 comprises hydrogen or a methyl group; R 6 comprises hydrogen or a methyl group; R 7 comprises hydrogen or a methyl group; X comprises oxygen, NH, or N(R 5 ) wherein R 5 comprises a monovalent organic group; m is a positive integer from 1 to 100; and n is a positive integer from 1 to 100.

3. The compound of claim 1 , wherein the compound comprises the structure:

wherein R 1 comprises hydrogen or an alkyl group; R 2 comprises hydrogen or a methyl group; R 4 comprises a divalent organic group; R 6 comprises hydrogen or a methyl group; X comprises oxygen, NH, or N(R 5 ) wherein R 5 comprises a monovalent organic group; and n is a positive integer from 1 to 100.

4. The compound of claim 1 , wherein the compound comprises the structure:

wherein R 1 comprises hydrogen or an alkyl group; R 2 comprises hydrogen or a methyl group; R 6 comprises hydrogen or a methyl group; R 7 comprises hydrogen or a methyl group; X comprises oxygen, NH, or N(R 5 ) wherein R 5 comprises a monovalent organic group; and n is a positive integer from 1 to 100.

5. The compound of claim 1 , wherein the compound comprises the structure:

wherein R 1 comprises hydrogen or an alkyl group; R 2 comprises hydrogen or a methyl group; R 4 comprises a divalent organic group; R 6 comprises hydrogen or a methyl group; and X comprises oxygen, NH, or N(R 5 ) wherein R 5 comprises a monovalent organic group.

6. The compound of claim 1 , wherein the compound comprises the structure:

wherein R 1 comprises hydrogen or an alkyl group; R 2 comprises hydrogen or a methyl group; R 3 comprises a divalent organic group; R 7 comprises hydrogen or a methyl group; X comprises oxygen, NH, or N(R 5 ) wherein R 5 comprises a monovalent organic group; and m is a positive integer from 1 to 100.

7. The compound of claim 1 , wherein the compound comprises the structure:

wherein R 1 comprises hydrogen or an alkyl group; R 2 comprises hydrogen or a methyl group; R 3 comprises a divalent organic group; R 7 comprises hydrogen or a methyl group; and X comprises oxygen, NH, or N(R 5 ) wherein R 5 comprises a monovalent organic group.

8. The compound of claim 1 , wherein the compound comprises the structure:

wherein R 1 comprises hydrogen or an alkyl group; R 2 comprises hydrogen or a methyl group; R 3 comprises a divalent organic group; and R 4 comprises a divalent organic group.

9. A compound comprising the structure:

wherein each R 1 independently comprises hydrogen, an alkyl group; R 2 comprises hydrogen or a methyl group; R 3 comprises a divalent organic group; and each R 8 independently comprises a divalent organic group.

10. The compound of claim 9 , wherein the compound comprises the structure:

wherein each R 1 independently comprises hydrogen, an alkyl group; R 2 comprises hydrogen or a methyl group; R 3 comprises a divalent organic group; and each R 7 independently comprises hydrogen or a methyl group.

11. The compound of claim 1 , wherein the compound comprises the structure:

12. The compound of claim 1 , wherein the compound comprises the structure:

13. A polymer comprising a pendant carbamate-functional moiety comprising the structure:

wherein R 1 comprises hydrogen or an alkyl group; R 2 comprises hydrogen or a methyl group; R 3 comprises a divalent organic group; R 4 comprises a divalent organic group; and X comprises oxygen, NH, or N(R 5 ) wherein R 5 comprises a monovalent organic group.

14. The polymer of claim 13 , wherein the polymer comprises the residue of the compound of claim 1 .

15. A curable film-forming composition comprising the polymer of claim 13 .

16. An aqueous dispersion comprising the polymer of claim 13 .

17. A coating comprising the polymer of claim 13 .

18. A substrate coated with the curable film-forming composition of claim 15 .

19. A substrate coated with the aqueous dispersion of claim 16 .

20. A method of preparing the compound of claim 1 , wherein X comprises oxygen, the method comprising the step of reacting an isocyanato functional unsaturated monomer of formula II with a hydroxyl functional, carbamate functional monomer according to formula III,

wherein R 1 comprises hydrogen or an alkyl group; R 2 comprises hydrogen or a methyl group; R 3 comprises a divalent organic group; and R 4 comprises a divalent organic group.

21. A method of preparing the compound of claim 1 , wherein X comprises N(R 5 ), the method comprising the steps of (1) reacting an isocyanato functional unsaturated compound of formula II with a dihydroxy alkyl amine compound of formula IV to form a reaction product,

and (2) further reacting the reaction product with a carbamate ester according to formula V,

wherein R 1 comprises hydrogen or an alkyl group; R 2 comprises hydrogen or a methyl group; R 3 comprises a divalent organic group; each R 8 independently comprises a divalent organic group; and R 9 comprises a monovalent organic group.

22. The compound of claim 1 , wherein R 1 is hydrogen.

Assignees

• Prc Desoto Int Inc

Inventors

• Dacko Christopher A
• Zhou Hongying

Classifications

• C09D133/14

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C09D133/04

  Homopolymers or copolymers of esters {(C09D143/04 takes precedence)} · CPC title

• C08F220/343

  in the form of urethane links · CPC title

• C08F20/36 Primary

  containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate} · CPC title

• C07C275/10 Primary

  being further substituted by singly-bound oxygen atoms · CPC title