Curable coating compositions containing glycidyl carbamate resins and amphiphilic glycidyl-carbamate-functional prepolymers having fouling-release and anti-icing properties

Patent metadata

Field	Value
Publication number	US-11827804-B2
Application number	US-202117162227-A
Country	US
Kind code	B2
Filing date	Jan 29, 2021
Priority date	Jan 29, 2021
Publication date	Nov 28, 2023
Grant date	Nov 28, 2023

Abstract

The invention relates to a curable coating composition comprising at least one glycidyl carbamate (GC) resin, at least one amphiphilic GC-functional prepolymer, and at least one curing agent. The invention also relates to a method of making the curable coating compositions. The invention also relates to an article of manufacture comprising the curable coating composition of the invention and a method of making such article. The invention also relates to a fouling-release (FR) coating system and an anti-coating system, each of which comprises the curable coating compositions of the invention, methods of applying the FR coating systems and anti-coating systems to substrates, and methods for reducing or preventing biofouling or icing of a surface exposed to an aqueous environment using the FR coating systems.

First claim

The claimed invention is:

1. A curable coating composition comprising:
a) at least one glycidyl carbamate (GC) resin comprising the reaction product of:
a1) at least one organic polyisocyanate, and
a2) glycidol,

b) at least one amphiphilic GC-functional prepolymer comprising the reaction product of:
b1) at least one organic polyisocyanate,
b2) glycidol,
b3) at least one poly(ethylene glycol) methyl ether (mPEG), and
b4) at least one polydimethylsiloxane (PDMS), and

c) at least one curing agent.

2. The curable coating composition of claim 1 , wherein the organic polyisocyanate a1) and b1) are, independent of one another, selected from the group consisting of aliphatic, cycloaliphatic, araliphatic, aromatic polyisocyanate, and mixtures thereof.

3. The curable coating composition of claim 2 , wherein the organic polyisocyanate a1) and b1) are, independent of one another, 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 curable coating composition of claim 1 , wherein the organic polyisocyanate a1) and b1) are each an isophorone diisocyanate trimer.

5. The curable coating composition of claim 1 , wherein the mPEG b3) has a molecular weight ranging from about 350 M n to 20,000 M n and is present in amount ranging from 0.01 to about 50 wt. %, based on the solid content of the amphiphilic GC-functional prepolymer, and the PDMS b4) has a molecular weight ranging from about 400 M n to 50,000 M n and is present in amount ranging from 0.01 to about 50 wt. %, based on the solid content of the amphiphilic GC-functional prepolymer.

6. The curable coating composition of claim 1 , wherein the PDMS b4) is a monocarbinol-terminated PDMS.

7. The curable coating composition of claim 6 , wherein the monocarbinol-terminated PDMS has the following structure:

wherein R, independent of one another, is a C 3 -C 12 straight chain alkyl or an alkylene ether;
wherein n ranges from 0 to about 270.

8. The curable coating composition of claim 1 , wherein the curing agent is an amine functional curing agent.

9. The curable coating composition of claim 8 , wherein the amine functional curing agent is selected from the group consisting of an amine crosslinker, a polyamide crosslinker, and mixtures thereof.

10. A cured coating composition, comprising the curable coating composition of claim 1 .

11. A method for making the curable coating composition of claim 1 , comprising:
reacting the at least one organic polyisocyanate, a1), with the glycidol, a2), to make the at least one GC resin, a),
reacting the at least one organic polyisocyanate, b1), with the glycidol, b2), the at least one mPEG, b3), and the at least one PDMS, b4) to make the at least one amphiphilic GC-functional prepolymer, b), and
mixing the at least one GC resin, a) and the at least one amphiphilic GC-functional prepolymer, b), with the at least one curing agent, c), to make the curable coating composition of claim 1 .

12. A method for making a cured coating composition, comprising curing the curable coating composition of claim 1 .

13. An article coated with the curable coating composition of claim 1 .

14. The article of claim 13 , wherein the curable coating composition is cured.

15. A fouling-release coating system, comprising the curable coating composition of claim 1 .

16. A method for applying the fouling-release coating system of claim 15 on at least a part of the surface of a substrate.

17. A method for reducing or preventing biofouling of a surface exposed to an aqueous environment comprising the steps of:
coating the surface with the curable coating composition of claim 1 to form a coated surface, and
curing the coating composition on the coated surface.

18. An anti-icing coating system, comprising the curable coating composition of claim 1 .

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

20. A method for reducing or preventing icing of a surface exposed to an aqueous environment comprising the steps of:
coating the surface with the curable coating composition of claim 1 to form a coated surface, and
curing the coating composition on the coated surface.

21. The curable coating composition of claim 4 , wherein, in the reaction to make the GC resin, the isophorone diisocyanate is reacted with glycidol in a 1:1 ratio of NCO:OH groups, wherein, in the reaction to make the amphiphilic GC-functional prepolymer, the glycidol functionalizes about 33.3% of the NCO groups in the isophorone diisocyanate are functionalized by the glycidol and about 66.6% of the NCO groups in the isophorone diisocyanate are converted to urethane linkages by attached of the chains of the mPEG and PDMS.

22. The curable coating composition of claim 21 , wherein the stoichiometric ratio of epoxy groups present in the GC resin and amphiphilic GC-functional prepolymer and amine hydrogen groups present in the amine functional curing agent ranges from about 1:0.1 to about 1:3.

23. The curable coating composition of claim 4 , wherein, in the reaction to make the GC resin, the isophorone diisocyanate is reacted with glycidol in a 1:1 ratio of NCO:OH groups, wherein, in the reaction to make the amphiphilic GC-functional prepolymer, the ratio of stoichiometric equivalents of NCO:OH groups of glycidol+PDMS+mPEG is 1:1.

24. The curable coating composition of claim 23 , wherein the stoichiometric ratio of epoxy groups present in the GC resin and amphiphilic GC-functional prepolymer and amine hydrogen groups present in the amine functional curing agent ranges from about 1:0.1 to about 1:3.

25. The curable coating composition of claim 1 , wherein:
the organic polyisocyanate a1) and b1) are, independent of one another, selected from the group consisting of aliphatic, cycloaliphatic, araliphatic, aromatic polyisocyanate, and mixtures thereof;
the mPEG b3) has a molecular weight ranging from about 350 M n to 20,000 M n and is present in amount ranging from about 0.01 to about 50 wt. %, based on the solid content of the amphiphilic GC-functional prepolymer;
the PDMS b4) is a monocarbinol-terminated PDMS having a molecular weight ranging from about 400 M n to 50,000 M n and is present in amount ranging from 0.01 to about 50 wt. %, based on the solid content of the amphiphilic GC-functional prepolymer; and
the curing agent is an amine functional curing agent.

26. The curable coating composition of claim 25 , wherein:
the organic polyisocyanate a1) and b1) are, independent of one another, selected from cycloaliphatic polyisocyanates;
the mPEG b3) has a molecular weight ranging from about 550 M n to 750 M n and is present in amount ranging from about 5 to about 20 wt. %, based on the solid content of the amphiphilic GC-functional prepolymer;
the PDMS b4) is a monocarbinol-terminated PDMS having a molecular weight ranging from about 5,000 M n to 10,000 M n and is present in am

Assignees

• Ndsu Res Foundation

Inventors

• Webster Dean C
• Rahimi Alireza

Classifications

• C09D175/04 Primary

  Polyurethanes · CPC title

• C08G18/12

  using two or more compounds having active hydrogen in the first polymerisation step · CPC title

• C08G18/2845

  Monohydroxy epoxy compounds · CPC title

• C08G18/4833

  Polyethers containing oxyethylene units · CPC title

• C08G18/61

  Polysiloxanes · CPC title