Non-isocyanate siloxane-modified glycidyl carbamate resins and coatings containing them

Patent metadata

Field	Value
Publication number	US-10759950-B2
Application number	US-201716076395-A
Country	US
Kind code	B2
Filing date	Feb 28, 2017
Priority date	Feb 29, 2016
Publication date	Sep 1, 2020
Grant date	Sep 1, 2020

Abstract

This invention relates to novel non-isocyanate siloxane-modified glycidol carbamate (GC) resins and coating compositions containing them. The non-isocyanate siloxane modified GC resins of the invention comprise the reaction product of at least one organic polyisocyanate, glycidol, and at least one bis(hydroxyl alkyl)-terminated polydimethylsiloxane. The coating compositions of the invention comprise at least one non-isocyanate siloxane modified GC resin of the invention and at least one curing agent. The invention also relates to methods of making the resins of the invention and coatings containing them. The invention also relates to a fouling-release (FR) coating system comprising the coating compositions of the invention and methods of applying said FR coating systems to substrates. The invention also relates to articles of manufacture comprising a coating composition of the invention and a method of making such articles.

First claim

The claimed invention is:

1. A siloxane-modified glycidyl carbamate resin, comprising the reaction product of at least one organic polyisocyanate, glycidol, and at least one bis(hydroxyl alkyl)-terminated polydimethylsiloxane.

2. The siloxane-modified glycidyl carbamate resin of claim 1 , wherein the at least one organic polyisocyanate is selected from the group consisting of aliphatic, cycloaliphatic, araliphatic, aromatic polyisocyanate, and mixtures thereof.

3. The siloxane-modified glycidyl carbamate resin of claim 1 , wherein the at least one organic polyisocyanate is selected from the group consisting of:

wherein R is independently an optionally substituted, divalent C 1 -C 15 alkyl, an optionally substituted C 3 -C 15 cycloalkyl, or a group selected from:

4. The siloxane-modified glycidyl carbamate resin of claim 3 , wherein R is a C 2 -C 10 straight chain or branched alkyl.

5. The siloxane-modified glycidyl carbamate resin of claim 1 , wherein the at least one bis(hydroxyl alkyl)-terminated polydimethylsiloxane has the following structure of formula (III):

wherein R is a C 3 -C 12 straight chain alkyl or an alkylene ether;
wherein n ranges from 0 to about 680.

6. The siloxane-modified glycidyl carbamate resin of claim 5 , wherein the at least one bis(hydroxyl alkyl)-terminated polydimethylsiloxane is selected from a dicarbinol polydimethylsiloxane having the following structure of formula (IV):

wherein n ranges from 0 to about 680.

7. The siloxane-modified glycidyl carbamate resin of claim 6 , wherein the at least one dicarbinol polydimethylsiloxane has a molecular weight ranging from about 400 to about 50,000 Dalton.

8. The siloxane-modified glycidyl carbamate resin of claim 7 , wherein the at least one dicarbinol polydimethylsiloxane has a molecular weight of about 5,000 Dalton.

9. The siloxane-modified glycidyl carbamate resin of claim 1 , wherein the at least one bis(hydroxyl alkyl)-terminated polydimethylsiloxane is reacted with the at least one organic polyisocyanate in an amount ranging from about 0.5% to about 20% equivalents to the isocyanate groups in the at least one organic polyisocyanate.

10. The siloxane-modified glycidyl carbamate resin of claim 1 , wherein the ratio of stoichiometric equivalents of isocyanate:polydimethylsiloxane hydroxyl groups+glycidol is 1:1.

11. The siloxane-modified glycidyl carbamate resin of claim 1 , further comprising at least one solvent.

12. The siloxane-modified glycidyl carbamate resin of claim 1 , further comprising at least one catalyst.

13. A coating composition comprising:
a) at least one siloxane-modified glycidyl carbamate resin of claim 1 , and
b.

14. The coating composition of claim 13 , wherein the ratio of epoxy to amine hydrogen equivalent weight ranges from 1:1 to 1:2.

15. The coating composition of claim 13 , wherein said at least one curing agent is selected from at least one amine crosslinker.

16. A method for making the siloxane-modified glycidyl carbamate resin of claim 1 comprising:
a) reacting the at least one organic polyisocyanate;
b) the glycidol; and
c) the at least one bis(hydroxyl alkyl)-terminated polydimethylsiloxane.

17. A method for making a coating composition, comprising curing at least one siloxane-modified glycidyl carbamate resin of claim 1 with at least one curing agent.

18. A fouling-release coating system comprising at least one siloxane-modified glycidyl carbamate resin of claim 1 and at least one curing agent.

19. A method for applying a fouling-release coating system of claim 18 on at least a part of the surface of a substrate.

20. An article coated with a coating composition of claim 13 .

Assignees

• Ndsu Res Foundation

Inventors

• Webster Dean C
• Pade Madhura

Classifications

• C09D183/10 Primary

  Block or graft copolymers containing polysiloxane sequences (obtained by polymerising a compound having a carbon-to-carbon double bond on to a polysiloxane C09D151/08, C09D153/00) · CPC title

• C08G77/455

  containing polyamide, polyesteramide or polyimide sequences · CPC title

• C08G77/70

  Siloxanes defined by use of the MDTQ nomenclature · CPC title

• C09D5/1675 Primary

  Polyorganosiloxane-containing compositions · CPC title

• C08G2150/00

  Compositions for coatings · CPC title