1K high hardness, high impact resistance coating

Patent metadata

Field	Value
Publication number	US-10752803-B2
Application number	US-201816135252-A
Country	US
Kind code	B2
Filing date	Sep 19, 2018
Priority date	Sep 19, 2017
Publication date	Aug 25, 2020
Grant date	Aug 25, 2020

Abstract

A coating composition can be made by providing an aminoalkoxysilane and, in the substantial absence of water, reacting at least a portion of the aminoalkoxysilane with at least one epoxide-containing compound including an aliphatic group to yield at least one alkoxysilylamine, and then reacting the alkoxysilylamine with at least one isocyanate reagent containing at least two isocyanate groups to yield a monomer having plural alkoxysilane groups and, in many embodiments, at least two branched aliphatic groups having at least six carbon atoms. A coating composition thus formed exhibits high durability and good flexibility. Also disclosed is a method of applying a coating composition to a substrate and allowing the coating composition to cure, and the cured coating resulting from such application.

First claim

What is claimed is:

1. A method of making a coating composition, the method comprising:
providing an aminoalkoxysilane;
in the substantial absence of water, reacting at least a portion of said aminoalkoxysilane with a compound of the following formula (2):

wherein A 1 -A 3 are the same or different and comprise hydrogen or a carbon-containing group with one to three carbon atoms, A 4 comprises a carbonyl-containing linking group, and R 1 comprises a branched aliphatic group having at least six carbon atoms, the reaction yielding an alkoxysilylamine; and
reacting said alkoxysilylamine with an isocyanate reagent containing at least two isocyanate groups to yield a monomer having plural alkoxysilane groups and at least two branched aliphatic groups having at least six carbon atoms.

2. The method according to claim 1 , 0.5 to 1.5 parts of said aminoalkoxysilane being blended with 0.25 to 1.5 parts of said compound of formula (2).

3. The method of claim 2 , said alkoxysilylamine being reacted with 0.05 to 0.75 parts of said isocyanate reagent.

4. The method according to claim 1 , further comprising providing a catalytic deprotectant in an amount catalytically effective to deprotect alkoxy groups when said monomer is exposed to ambient water, said catalytic deprotectant comprising at least one of an alkylamine and an organotin compound.

5. The method according to claim 4 , said catalytic deprotectant comprising at least one of dibutylamine and dibutyltin dilaurate.

6. The method according to claim 1 , said aminoalkoxysilane having a structure represented by the following formula (1):

where A 9 , A 10 , and A 11 are the same or different and comprise hydrogen or C 1 -C 4 alkyl, with the proviso that at least one of A 9 , A 10 , and A 11 comprises C 1 -C 4 alkyl, where B 1 and B 2 are the same or different and comprise hydrogen or C 1 -C 4 alkyl, with the proviso that at least one of B 1 and B 2 is hydrogen, and where R 3 is C 1 -C 4 alkyl.

7. The method according to claim 1 , said compound of formula (2) being a glycidyl aliphatic ester.

8. The method according to claim 7 , said glycidyl aliphatic ester having the following formula (3):

wherein R 1 comprises a branched aliphatic group having at least six carbon atoms.

9. The method according to claim 8 , said glycidyl aliphatic ester having the following formula (4):

10. The method according to claim 1 , said isocyanate reagent comprising at least one of (8) and (10):

wherein R 4 -R 6 are the same or different and comprise two to eight carbon atoms, and R 7 -R 9 are the same or different and comprise two to eight carbon atoms.

11. The method according to claim 10 , said isocyanate reagent comprising at least one of (9) and (11):

12. The method according to claim 1 , said monomer comprising at least one of (14) and (15):

wherein A 4 includes a carbonyl-containing linking group, A 9 , A 10 , and A 11 are the same or different and comprise hydrogen or C 1 -C 4 alkyl, with the proviso that at least one of A 9 , A 10 , and A 11 comprises C 1 -C 4 alkyl, R 1 comprises a branched aliphatic group having at least six carbon atoms, R 3 is C 1 -C 4 alkyl, R 4 -R 6 are the same or different and comprise two to eight carbon atoms, and R 7 -R 9 are the same or different and comprise two to eight carbon atoms.

13. The method according to claim 12 , said monomer comprising at least one of (16) and (17):

14. The method according to claim 1 , further including adding a pigment.

15. The method according to claim 14 , the pigment including titanium dioxide.

16. A coating composition prepared by the method according to claim 1 .

17. A coating composition comprising at least one of (14) and (15):

wherein A 4 includes a carbonyl-containing linking group, A 9 , A 10 , and A 11 are the same or different and comprise hydrogen or C 1 -C 4 alkyl, with the proviso that at least one of A 9 , A 10 , and A 11 comprises C 1 -C 4 alkyl, R 1 comprises a branched aliphatic group having at least six carbon atoms, R 3 is C 1 -C 4 alkyl, R 4 -R 6 are the same or different and comprise two to eight carbon atoms, and R 7 -R 9 are the same or different and comprise two to eight carbon atoms.

18. The coating composition according to claim 17 , comprising at least one of (16) and (17):

19. The coating composition according to claim 17 , further comprising a pigment.

20. The coating composition according to claim 19 , the pigment including titanium dioxide.

21. A method of applying a coating composition, the method comprising applying the coating composition according to claim 17 to a substrate, and allowing the coating composition to cure.

22. A cured coating comprising a cross-linked product of the coating composition according to claim 17 .

23. A method of making a coating composition, the method comprising:
providing an aminoalkoxysilane;
in the substantial absence of water, reacting a portion of said aminoalkoxysilane with a compound of the following formula (2) and reacting another portion of said aminoalkoxysilane with a compound of the following formula (5):

wherein A 1 -A 3 are the same or different and comprise hydrogen or a carbon-containing group with one to three carbon atoms, A 4 comprises a carbonyl-containing linking group, and R 1 comprises a branched aliphatic group having at least six carbon atoms,

wherein A 5 -A 7 are the same or different and comprise hydrogen or a carbon-containing group with one to three carbon atoms, A 8 comprises an ether-containing linking group, and R 2 comprises a linear aliphatic group having at least two carbon atoms, the reactions between said aminoalkoxysilane and said compounds of formulas (2) and (5) yielding a mixture of alkoxysilylamines; and
reacting said mixture of alkoxysilylamines with an isocyanate reagent containing at least two isocyanate groups to yield a monomer having plural alkoxysilane groups.

24. The method according to claim 23 , 0.5 to 1.5 parts of said aminoalkoxysilane being blended with 0.25 to 1.5 parts of said compound of formula (2) and 0.25 to 1.5 parts of said compound of formula (5).

25. The method of claim 24 , said mixtu

Assignees

• Sherwin Williams Co

Inventors

• Rectenwald Michael F
• Makowski Brian

Classifications

• C09D7/63

  organic · CPC title

• C08K2003/2241

  Titanium dioxide · CPC title

• C08G18/163

  covered by C08G18/18 and C08G18/22 · CPC title

• C09D175/02 Primary

  Polyureas · CPC title

• C08G18/283

  Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds · CPC title