USE OF AMPHIPHILIC SURFACE MODIFYING ADDITIVES TO IMPROVE PERFORMANCE OF SILOXANE-POLYURETHANE FOULING-RELEASE COATINGS

• US 20190309187A1
• Filed: 04/05/2019
• Published: 10/10/2019
• Est. Priority Date: 04/06/2018
• Status: Active Grant

• Current Assignee: United States Navy (U.S. Department Of Defense)
• Original Assignee: Ndsu-Research Foundation
• Inventors: WEBSTER, Dean C., BENDA, Jackson
• Granted Patent: US 11,560,493 B2
• Time in Patent Office: Days
• CPC Class Codes: C08G 18/289 containing silicon
• CPC Class Codes: C08G 18/4063 Mixtures of compounds of group C08G18/62 with other macromolecular compounds
• CPC Class Codes: C08G 18/42 Polycondensates having carboxylic or carbonic ester groups in the main chain
• CPC Class Codes: C08G 18/48 Polyethers
• CPC Class Codes: C08G 18/61 Polysiloxanes
• CPC Class Codes: C08G 18/6229 Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
• CPC Class Codes: C08G 18/73 acyclic
• CPC Class Codes: C08G 18/74 cyclic
• CPC Class Codes: C08G 18/757 containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group
• CPC Class Codes: C08G 18/7692 containing at least one isocyanate or isothiocyanate group linked to an aromatic ring by means of an aliphatic group
• CPC Class Codes: C08G 18/792 formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
• CPC Class Codes: C08G 77/045 containing less than 25 silicon atoms
• CPC Class Codes: C08G 77/458 containing polyurethane sequences
• CPC Class Codes: C08G 77/46 containing polyether sequences
• CPC Class Codes: C08L 83/00 Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 83/12 containing polyether sequences
• CPC Class Codes: C09D 175/04 Polyurethanes
• CPC Class Codes: C09D 175/06 from polyesters
• CPC Class Codes: C09D 183/10 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 Class Codes: C09D 5/1637 Macromolecular compounds
• CPC Class Codes: C09D 5/1662 : Synthetic film-forming substance
• CPC Class Codes: C09D 5/1675 : Polyorganosiloxane-containing compositions

Abstract

The invention relates to curable coating compositions containing at least one surface modifying amphiphilic additive; and at least one siloxane-polyurethane coating composition. The invention also relates to methods of making and using the curable coating compositions of the invention. The invention also relates to objects coated with the curable coating composition of the invention. The invention also relates to methods 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 the invention to form a coated surface, and curing the coating composition on the coated surface. The invention also relates to a marine fouling-release coating containing the curable coating composition of the invention.

Claims

1. A curable coating composition comprising:

a) at least one surface modifying amphiphilic additive; and

b) at least one siloxane-polyurethane coating composition.

2. The curable coating composition of claim 1, wherein the surface modifying amphiphilic additive comprises poly(ethylene glycol) chains attached to a polydimethyl siloxane backbone.

3. The curable coating composition of claim 1, wherein the surface modifying amphiphilic additive comprises the reaction product of:

(1) at least one Si—

H functional siloxane;

(2) at least one allyl-functional poly(ethylene glycol) monomethyl ether; and

(3) optionally, at least one catalyst.

4. The curable coating composition of claim 3, wherein the Si—

H functional siloxane is selected from the group consisting of a 100 mol % Si—

H polymethylhydrosiloxane, a copolymer of methylhydrosiloxane-dimethylsiloxane of varying mol % Si—

H, a tetra functional Si—

H cyclosiloxane, and mixtures thereof.

5. The curable coating composition of claim 4, wherein the 100 mol % Si—

H polymethylhydrosiloxane is selected from at least one Si—

H trimethylsiloxyl terminated polymethylhydrosiloxane.

6. The curable coating composition of claim 3, wherein the tetra functional Si—

H cyclosiloxane is selected from Si—

H functional 1,3,5,7-tetramethylcyclotetrasiloxane (D′

4).

7. The curable coating composition of claim 3, wherein the allyl functional poly(ethylene glycol) monomethyl ether is selected from at least one allyl-terminated poly(ethylene glycol) monomethyl ether.

8. The curable coating composition of claim 3, wherein the Si—

H functional siloxane and the allyl functional poly(ethylene glycol) monomethyl ether are present in a ratio of 1.0;

1.0.

9. The curable coating composition of claim 1, wherein the siloxane-polyurethane coating composition comprises:

(1) at least one aminopropyl terminated polydimethyl siloxane;

(2) at least one polyol;

(3) at least one polyisocyanate crosslinker; and

(4) optionally, at least one additive.

10. The curable coating composition of claim 16, wherein the aminopropyl terminated polydimethyl siloxane is selected from at least one aminopropyl-terminated polydimethyl siloxane.

11. The curable coating composition of claim 16, wherein the polyol is an acrylic polyol, a polyester polyol, a polycarbonate polyol, a polyether polyol, or mixtures thereof.

12. The curable coating composition of claim 19, wherein the polyol consists of a polyether polyol.

13. The curable coating composition of claim 16, wherein the polyisocyanate crosslinker is a polyisocyanate derived from isophorone diisocyanate, hexamethylene diisocyanate, or methylene diphenyl diisocyanate.

14. The curable coating composition of claim 16, wherein the polyisocyanate crosslinker is a polyisocyanate derived from isophorone diisocyanate and the polyol is an acrylic polyol.

15. The curable coating composition of claim 16, wherein the polyol consists of a polyether polyol and the polyisocyanate crosslinker consists of a polyisocyanate derived from polyisomethylene diphenyl diisocyanate.

16. The curable coating composition of claim 1, wherein the surface modifying amphiphilic additive is incorporated into the siloxane-polyurethane coating composition in an amount ranging from 0.1-20 wt. % (of the total composition weight)

17. A cured coating composition of claim 1.

18. An object coated with the curable coating composition of claim 1.

19. A method for reducing or preventing biofouling of a surface exposed to an aqueous environment comprising the steps of:

coating the surface with a curable coating composition of claim 1 to form a coated surface, and

curing the coating composition on the coated surface.

20. A marine fouling-release coating having the curable coating composition of claim 1.