Amphiphilic siloxane polyurethane coating compositions and methods of making and using thereof

Patent metadata

Field	Value
Publication number	US-12466977-B2
Application number	US-202017119334-A
Country	US
Kind code	B2
Filing date	Dec 11, 2020
Priority date	Dec 12, 2019
Publication date	Nov 11, 2025
Grant date	Nov 11, 2025

Abstract

The invention relates to a curable amphiphilic siloxane polyurethane coating composition. The invention also relates to methods of making and using the curable amphiphilic siloxane polyurethane 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 use of the curable amphiphilic siloxane polyurethane coating composition of the invention.

First claim

The claimed invention is:

1 . A curable amphiphilic siloxane polyurethane coating composition comprising:
a) at least one pre-polymer selected from the group consisting of:
a2) a pre-polymer comprising:
a2.1) at least one hydrophilically modified polyisocyanate comprising the reaction product of:
a2.1.1) a polyisocyanate based on hexamethylene diisocyanate (HMDI) modified with a polyethylene glycol (PEG) and at least one sulfobetaine group; and
a2.1.2) at least one further PEG and/or at least one poly(dimethyl siloxane) (PDMS);

a3) a pre-polymer comprising:
a3.1) at least one hydrophilically modified polyisocyanate comprising the reaction product of:
a3.1.1) a polyisocyanate based on HMDI modified with a PEG; and
a3.1.2) at least one further PEG and/or at least one PDMS;

a3.2) at least one further PEG;
a3.3) at least one difunctional hydroxyalkyl terminated PDMS; and
a3.4) a sulfobetaine-modified polyisocyanate comprising the reaction product of at least one sulfobetaine group and a polyisocyanate based on isophorone diisocyanate (IPDI), or a PEG-modified polyisocyanate comprising the reaction product of at least one PEG and IPDI; and

a4) a pre-polymer comprising:
a4.1) at least one hydrophilically modified polyisocyanate comprising the reaction product of:
a4.1.1) a polyisocyanate based on HMDI modified with a PEG and at least one sulfobetaine group; and
a4.1.2) at least one further PEG and/or at least one PDMS;

a4.2) at least one further PEG;
a4.3) at least one difunctional hydroxyalkyl terminated PDMS; and
a4.4) a sulfobetaine-modified polyisocyanate comprising the reaction product of at least one sulfobetaine group and a polyisocyanate based on IPDI, or a PEG-modified polyisocyanate comprising the reaction product of at least one PEG and IPDI;

b) at least one polyol; c) at least one polyisocyanate; d) at least one PEG modified siloxane amphiphilic additive; e) optionally, at least one catalyst; f) optionally, at least one solvent; and g) optionally, at least one pot-life extender.

2 . The curable amphiphilic siloxane polyurethane coating composition of claim 1 , wherein the at least one polyol, b), is selected from the group consisting of at least one acrylic polyol, polyester polyol, polycarbonate polyol, polyether polyol, or mixtures thereof.

3 . The curable amphiphilic siloxane polyurethane coating composition of claim 2 , wherein the at least one polyol, b), is an acrylic polyol.

4 . The curable amphiphilic siloxane polyurethane coating composition of claim 3 , wherein the acrylic polyol is composed of 80% butyl acrylate and 20% 2-hydroxyethyl acrylate.

5 . The curable amphiphilic siloxane polyurethane coating composition of claim 1 , wherein the at least one polyisocyanate, c), is a polyisocyanate based on IPDI.

6 . A cured amphiphilic siloxane polyurethane coating composition of claim 1 .

7 . An object coated with the curable amphiphilic siloxane polyurethane coating composition of claim 1 .

8 . 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 amphiphilic siloxane polyurethane coating composition of claim 1 to form a coated surface, and curing the amphiphilic siloxane polyurethane coating composition on the coated surface.

9 . A marine fouling-release coating having the curable amphiphilic siloxane polyurethane coating composition of claim 1 .

10 . A method of making the curable amphiphilic siloxane polyurethane coating composition of claim 1 , comprising: reacting the at least one pre-polymer, a), with the at least one polyol, b), the at least one polyisocyanate, c), the at least one amphiphilic additive, d), optionally the at least one catalyst, e), optionally the at least one solvent, f), and optionally the at least one pot-life extender, g).

11 . The curable amphiphilic siloxane polyurethane coating composition of claim 1 , wherein the at least one pre-polymer a) further comprises a pre-polymer a1), wherein the pre-polymer a1) comprises:
a1.1) at least one hydrophilically modified polyisocyanate comprising the reaction product of:
a1.1.1) a polyisocyanate based on HMDI modified with a PEG; and
a1.1.2) at least one further PEG and at least one PDMS.

12 . The curable amphiphilic siloxane polyurethane coating composition of claim 1 , wherein
a) the at least one pre-polymer is selected from:
a2) the pre-polymer comprising:
a2.1) at least one hydrophilically modified polyisocyanate comprising the reaction product of:
a2.1.1) a polyisocyanate based on HMDI modified with a PEG and at least one sulfobetaine group; and
a2.1.2) at least one further PEG and/or at least one PDMS.

13 . The curable amphiphilic siloxane polyurethane coating composition of claim 1 , wherein
a) the at least one pre-polymer is selected from:
a3) the pre-polymer comprising:
a3.1) at least one hydrophilically modified polyisocyanate comprising the reaction product of:
a3.1.1) a polyisocyanate based on HMDI modified with a PEG; and
a3.1.2) at least one further PEG and/or at least one PDMS;

a3.2) at least one further PEG;
a3.3) at least one difunctional hydroxyalkyl terminated PDMS; and
a3.4) a sulfobetaine-modified polyisocyanate comprising the reaction product of at least one sulfobetaine group and a polyisocyanate based on IPDI, or a PEG-modified polyisocyanate comprising the reaction product of at least one PEG and IPDI.

14 . The curable amphiphilic siloxane polyurethane coating composition of claim 1 , wherein
a) the at least one pre-polymer is selected from:
a4) the pre-polymer comprising:
a4.1) at least one hydrophilically modified polyisocyanate comprising the reaction product of:
a4.1.1) a polyisocyanate based on HMDI modified with a PEG and at least one sulfobetaine group; and
a4.1.2) at least one further PEG and/or at least one PDMS;

a4.2) at least one further PEG;
a4.3) at least one difunctional hydroxyalkyl terminated PDMS; and
a4.4) a sulfobetaine-modified polyisocyanate comprising the reaction product of at least one sulfobetaine group and a polyisocyanate based on IPDI, or a PEG-modified polyisocyanate comprising the reaction product of at least one PEG and IPDI.

15 . The curable amphiphilic siloxane polyurethane coating composition of claim 11 , wherein:
b) the at least one polyol is selected from at least one acrylic polyol; and c) the at least one polyisocyanate is a polyisocyanate based on IPDI.

16 . The curable amphiphilic siloxane polyurethane coating composition of claim 12 , wherein:
b) the at least one polyol is selected from at least one acrylic polyol; and c) the at least one polyisocyanate is a polyisocyanate based on IPDI.

17 . The curable amphiphilic siloxane polyurethane coating composition of claim 13 , wherein:
b) the at least one polyol is selected from at least one acrylic polyol; and c) the at least one polyisocyanate is a polyisocyanate based on IPDI.

18 . The curable amphiphilic siloxane polyurethane coating composition of claim 14 , wherein:
b) the at least one polyol is selected from at least one acrylic polyol; and c) the at least one polyisocyanate is a polyisocyanate based on IPDI.

19 . The curable amphiphilic siloxane polyurethane coating composition of claim 1 , wherein the at least one PEG modified siloxane amphiphilic additive is selected from a dimethylsiloxane.

Assignees

• Ndsu Res Foundation

Inventors

• Webster Dean C
• Galhenage Teluka
• Burgett Ryan

Classifications

• C08G18/246 Primary

  containing also tin-carbon bonds · CPC title

• C09D175/08

  from polyethers · CPC title

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C08G18/706

  the liquid medium being water · CPC title

• C08G18/4833

  Polyethers containing oxyethylene units · CPC title