Method using titanium catalyst for producing carbamate-functional materials

Patent metadata

Field	Value
Publication number	US-9334234-B2
Application number	US-201414272597-A
Country	US
Kind code	B2
Filing date	May 8, 2014
Priority date	May 8, 2014
Publication date	May 10, 2016
Grant date	May 10, 2016

Abstract

A carbamate-functional material is prepared by reacting a carbamate compound with a hydroxy-functional material using titanium (IV) alkoxide as catalyst.

First claim

What is claimed is:

1. A method of preparing a carbamate-functional material, comprising reacting a carbamate compound having the structure

with a hydroxy-functional material using a titanium (IV) alkoxide catalyst.

2. The method according to claim 1 , wherein the titanium (IV) alkoxide catalyst has n alkoxide groups, wherein n is an integer from one to four, and 4-n groups selected from halogen groups, acetylacetonate groups, and ethanolaminato groups.

3. The method according to claim 1 , wherein each alkoxide group has one to eight carbon atoms.

4. The method according to claim 1 , wherein the titanium (IV) alkoxide catalyst comprises titanium (IV) isopropoxide.

5. The method according to claim 1 , wherein the carbamate compound is an alkyl carbamate.

6. The method according to claim 1 , wherein the carbamate compound is selected from the group consisting of methyl carbamate, ethyl carbamate, n-propyl carbamate, isopropyl carbamate, n-butyl carbamate, isobutyl carbamate, tert-butyl carbamate, n-hexyl carbamate, 2-ethylhexyl carbamate, cyclohexyl carbamate, phenyl carbamate, and combinations thereof.

7. The method according to claim 1 , wherein the hydroxy-functional material is a monomeric compound having from 1 to 160 carbon atoms.

8. The method according to claim 1 , wherein the hydroxy-functional material has from 12 to 72 carbon atoms and at least two hydroxyl groups.

9. The method according to claim 1 , wherein the hydroxy-functional material comprises dimerized, trimerized, tetramerized or high oligomer addition products of unsaturated fatty acids having 12 to 18 carbon atoms and having carboxylic acid groups which have been reduced.

10. The method according to claim 1 , wherein the hydroxy-functional material is a hyperbranched polyol.

11. The method according to claim 10 , wherein reaction is carried out during a final step of making the hyperbranched polyol.

12. The method according to claim 1 , wherein the hydroxy-functional material is a member selected from the group consisting of polyester polyols, polyether polyols, polyhydroxy polycarbonates, polyurethane polyols, polyvinyl polymer polyols, polyhydroxy polyesteramides, polysiloxane polyols, and polyhydroxy polythioethers.

13. The method according to claim 12 , wherein the reaction is carried out during polymerization of the hydroxy-functional material.

14. The method according to claim 1 , wherein the titanium (IV) alkoxide is used in an amount of from about 0.13 wt. % to about 1.6 wt. % based on the total weight of the hydroxyl-functional material and the carbamate compound.

15. The method according to claim 1 , wherein the reaction is carried out at a temperature in the range of from about 125° C. to about 139° C.

16. The method according to claim 1 , wherein the reaction product has at least about 75% of theoretical total replacement of hydroxyl groups with carbamate groups.

17. A method of preparing a carbamate-functional material, comprising reacting a carbamate compound with a hyperbranched polyol using a titanium (IV) alkoxide catalyst.

Assignees

• Basf Coatings Gmbh

Inventors

• Jadhav Abhijit V

Classifications

• C09D175/04 Primary

  Polyurethanes · CPC title

• C08G71/04

  Polyurethanes · CPC title

• C07C269/06 Primary

  by reactions not involving the formation of carbamate groups · CPC title

• C08F220/36

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

• C07C271/12

  to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals · CPC title