Coating compositions comprising a compound with at least two cyclic carbonate groups and a siloxane group

Patent metadata

Field	Value
Publication number	US-9765238-B2
Application number	US-201414906208-A
Country	US
Kind code	B2
Filing date	Jul 11, 2014
Priority date	Jul 22, 2013
Publication date	Sep 19, 2017
Grant date	Sep 19, 2017

Abstract

Coating compositions comprising a compound having at least two cyclic carbonate groups and a siloxane group (called “carbonate compound”).

First claim

The invention claimed is:

1. A coating composition, comprising:
a carbonate compound of formula III

wherein R 2 to R 4 are independently hydrogen or an organic group comprising 1 to 10 C atoms, K is a divalent organic group comprising 2 to 10 C atoms, R 5 and R 6 are independently a hydrogen atom or an organic group comprising 1 to 10 C atoms, and m is an integer of from 1 to 99.

2. The coating composition according to claim 1 , which comprises from 0.1 to 50 wt% of the carbonate compound.

3. The coating composition according to claim 1 , further comprising:
a reactive compound comprising at least two reactive groups selected from the group consisting of a hydroxyl group, a primary amino group, a secondary amino group, and a mercapto group.

4. The coating composition according to claim 3 , wherein the reactive compound comprises a polyester polyol, a polyether polyol, a polyesteramide polyol, a polycarbonate polyol, a polyacrylate polyol, a polyetheramine, a polyamidoamine, or any mixture thereof.

5. A method for producing a coated substrate, the method comprising:
applying a coating composition to a substrate,
wherein the coating composition comprises
a carbonate compound comprising at least two cyclic carbonate groups and a siloxane group,
a reactive compound comprising at least two reactive groups selected from the group consisting of a hydroxyl group, a primary amino group, a secondary amino group, and a mercapto group, and

thereafter reacting the carbonate compound with the reactive compound.

6. A coating composition, comprising:
a carbonate compound comprising at least two cyclic carbonate groups and a siloxane group,
wherein the carbonate compound is obtained by hydrosilylation of a compound of formula IV

wherein radicals R1* to R4* are independently hydrogen or an organic group comprising 1 to 10 C atoms, but at least one of the radicals R1* to R4* comprises an ethylenically unsaturated group with a siloxane which comprises at least two silicon-bonded hydrogen atoms.

7. The coating composition according to claim 6 , wherein the compound of the formula IV is a compound in which R 1 * is a C2 to C10 alkenyl group or a C2-C10 alkynyl group, and R 2 *, R 3 * and R 4 * are independently a hydrogen atom or a C1 to C10 alkyl group.

8. The coating composition according to claim 6 , wherein R 1 * in the formula IV is a vinyl group.

9. The coating composition according to claim 6 , wherein the compound of the formula IV is a compound in which R 1 * is a vinyl group, R 2 * is a C1 to C4 alkyl group, and R 3 * and R 4 * are an H atom.

10. The coating composition according to claim 6 , which comprises from 0.1 to 50 wt % of the carbonate compound.

11. The coating composition according to claim 6 , further comprising:
a reactive compound comprising at least two reactive groups selected from the group consisting of a hydroxyl group, a primary amino group, a secondary amino group, and a mercapto group.

12. The coating composition according to claim 11 , wherein the reactive compound comprises a polyester polyol, a polyether polyol, a polyesteramide polyol, a polycarbonate polyol, a polyacrylate polyol, a polyetheramine, a polyamidoamine, or any mixture thereof.

13. A coating composition, comprising
a carbonate compound comprising at least two cyclic carbonate groups and a siloxane group, and
a reactive compound comprising at least two reactive groups selected from the group consisting of a hydroxyl group, a primary amino group, a secondary amino group, and a mercapto group; and
wherein the reactive compound comprises a polyester polyol, a polyether polyol, a polyesteramide polyol, a polycarbonate polyol, a polyacrylate polyol, a polyetheramine, a polyamidoamine, or any mixture thereof.

14. The coating composition according to claim 13 , wherein the carbonate compound comprises from two to fifty cyclic carbonate groups and a siloxane group comprising 2 to 100 silicon atoms.

15. The coating composition according to claim 13 , wherein the carbonate compound is a compound of formula III

wherein R 2 to R 4 are independently hydrogen or an organic group comprising 1 to 10 C atoms, K is a divalent organic group comprising 2 to 10 C atoms, R 5 and R 6 are independently a hydrogen atom or an organic group comprising 1 to 10 C atoms, and m is an integer of from 1 to 99.

16. The coating composition according to claim 13 , wherein the carbonate compound is obtained by hydrosilylation of a compound of formula IV

wherein radicals R1* to R4* are independently hydrogen or an organic group comprising 1 to 10 C atoms, but at least one of the radicals R1* to R4* comprises an ethylenically unsaturated group with a siloxane which comprises at least two silicon-bonded hydrogen atoms.

17. The coating composition according to claim 16 , wherein the compound of the formula IV is a compound in which R 1 * is a C2 to C10 alkenyl group or a C2-C10 alkynyl group, and R 2 * , R 3 * and R 4 * are independently a hydrogen atom or a C1 to C10 alkyl group.

18. The coating composition according to claim 16 , wherein R 1 * in the formula IV is a vinyl group.

19. The coating composition according to claim 16 , wherein the compound of the formula IV is a compound in which R 1 * is a vinyl group, R 2 * is a C1 to C4 alkyl group, and R 3 * and R 4 * are an H atom.

20. The coating composition according to claim 13 , which comprises from 0.1 to 50 wt % of the carbonate compound.

21. A carbonate compound of formula III

wherein R 2 to R 4 are independently hydrogen or an organic group comprising 1 to 10 C atoms, K is a divalent organic group comprising 2 to 10 C atoms, R 5 and R 6 are independently a hydrogen atom or an organic group comprising 1 to 10 C atoms, and m is an integer of from 1 to 99.

Assignees

• Basf Se

Inventors

• Klopsch Rainer
• Lanver Andreas
• Haaf-Kleinhubbert Christina
• Mormul Verena
• Hickmann Volker

Classifications

• C09D183/06 Primary

  containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence) · CPC title

• C07F7/0838

  Compounds with one or more Si-O-Si sequences (compounds with a ring containing only alternating Si and O atoms, i.e. cyclosilanes C07F7/21) · CPC title

• C08G77/14

  containing silicon bound to oxygen-containing groups · CPC title

• C08G2150/00

  Compositions for coatings · CPC title

• C09D201/08

  Carboxyl groups · CPC title