ANCHORED POLYSILOXANE-MODIFIED POLYURETHANE COATINGS AND USES THEREOF

• US 20130041099A1
• Filed: 09/13/2012
• Published: 02/14/2013
• Est. Priority Date: 06/11/2007
• Status: Active Grant

• Current Assignee: Ndsu-Research Foundation
• Original Assignee: Ndsu-Research Foundation
• Inventors: Webster, Dean C., Ekin, Abdullah, Sommer, Stacy
• Granted Patent: US 8,604,152 B2
• Time in Patent Office: Days
• US Class Current: 524/588
• CPC Class Codes: C08G 18/089 Reaction retarding agents
• CPC Class Codes: C08G 18/289 containing silicon
• CPC Class Codes: C08G 18/4277 Caprolactone and/or substituted caprolactone
• CPC Class Codes: C08G 18/61 Polysiloxanes
• CPC Class Codes: C08G 18/677 containing heteroatoms other than oxygen and the nitrogen of primary or secondary amino groups
• CPC Class Codes: C08G 18/725 Combination of polyisocyanates of C08G18/78 with other polyisocyanates
• CPC Class Codes: C08G 18/792 formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
• CPC Class Codes: C09D 175/04 Polyurethanes
• CPC Class Codes: C09D 175/16 having terminal carbon-to-carbon unsaturated bonds
• CPC Class Codes: C09D 5/1675 Polyorganosiloxane-containing compositions

Abstract

A polymeric material, prepared by reacting a mixture comprising a polyorganosiloxane having one or more isocyanate-reactive functional groups, polyisocyanate, and polyol, is provided. The isocyanate-reactive functional groups, typically one or two, are attached to only a single end of the polyorganosiloxane chains. The polymeric material may be used to form coatings on a substrate and to inhibit fouling on surfaces exposed to aqueous conditions.

Claims

1. A polymeric material formed from reactants which comprise:

polyorganosiloxane having two or more reactive functional groups attached to only a single end of the polyorganosiloxane;

wherein the reactive functional groups are hydroxyl alkyl carbamate groups or amino groups;

wherein the polyorganosiloxane constitutes about 2 to 20 wt. % (on a solids basis) of the total weight of the reactants;

about 30 wt. % to 85 wt. % polyisocyanate (on a solids basis) of the total weight of the reactants; and

polyol.

2. The polymeric material of claim 1, wherein the polyorganosiloxane is an amino functional polyorganosiloxane having one or more amino groups attached to only a single end of the polymer chain.

3. The polymeric material of claim 1, wherein the polyorganosiloxane has a formula I:

R′

Si

O—

SiMe₂

_n

LINK

X_y 

 

(I)

where R′

Si—

is a terminal group;

n is about 10 to 1,000;

LINK is a linking group;

X is —

NH₂; and

y is an integer from 1 to 4.

4. The polymeric material of claim 3, wherein LINK is an alkylene group which may have one or more oxygen, nitrogen or sulfur atoms substituted for a carbon atom of its backbone.

5. The polymeric material of claim 3, wherein the LINK has no more than about 10 atoms in its backbone and R′

Si—

is a trialkylsilyl group.

6. The polymeric material of claim 2, wherein the polyorganosiloxane includes poly(dialkylsiloxane) having one or more amino groups attached thereto.

7. The polymeric material of claim 2, wherein the polyisocyanate comprises hexamethylene diisocyanate trimer, isophorone diisocyanate trimer, or a mixture thereof.

8. The polymeric material of claim 2, wherein the polyol comprises hydroxy-functional poly(meth)acrylate.

9. The polymeric material of claim 1, wherein the polymeric material has an initial water contact angle of at least about 100°

.

10. The polymeric material of claim 1, wherein the mixture has a ratio of (isocyanate groups)/(amine+alcohol groups) of about 1.0 to 1.2.

11. A coating composition comprising the reactants of claim 1.

12. A method of inhibiting fouling on a surface exposed to aqueous conditions comprising applying the coating composition of claim 11 to the surface.

13. A substrate having a surface capable of being exposed to aqueous conditions;

wherein the surface has a fouling release coating thereon; and

the coating comprises the polymeric material of claim 1.

14. The polymeric material of claim 1, wherein the polyol comprises hydroxy-functional poly(meth)acrylate formed from monomers comprising hydroxyalkyl acrylate and alkyl acrylate.

15. The polymeric material of claim 1, wherein the polyol comprises polycaprolactone polyol.

16. The polymeric material of claim 1, wherein the mixture has a ratio of (isocyanate groups)/(amine+alcohol groups) of about 1.0 to 1.2.

17. A polymeric material formed from reactants which comprise:

amino functional polyorganosiloxane having one or more amino groups attached to only a single end of the polymer chain;

polyisocyanate; and

polyol;

wherein the polymeric material has an initial water contact angle of at least about 100°

.

18. The polymeric material of claim 17, wherein the amino functional polyorgano-siloxane constitutes about 5 to 15 wt. % (on a solids basis) of the total weight of the reactants;

about 57 wt. % to 65 wt. % polyisocyanate (on a solids basis) of the total weight of the reactants; and

the reactants have a ratio of (isocyanate groups)/(amine+alcohol groups) of about 1.0 to 1.2.

19. The polymeric material of claim 17, wherein the water contact angle changes by no more than about 10°

after immersion of the polymeric material in deionized water for 30 days.

20. A polymeric material formed from reactants which comprise:

polyisocyanate;

polyorganosiloxane having one or more hydroxyl alkyl carbamate groups attached to only a single end of the polyorganosiloxane; and

polyol.