Siloxane-modified binders and compositions thereof

Patent metadata

Field	Value
Publication number	US-11345828-B2
Application number	US-201816955196-A
Country	US
Kind code	B2
Filing date	Dec 20, 2018
Priority date	Dec 21, 2017
Publication date	May 31, 2022
Grant date	May 31, 2022

Abstract

A siloxane-modified latex binder includes a polymerization product of a monomer or a mixture of monomers for producing a latex polymer and a non-hydrolyzable siloxane. The non-hydrolyzable siloxane is represented by Formula (I): wherein: R1, R2, R3, R4, R5, R6, R7, and R8 are independently hydrogen, alkyl, —O-alkyl, —OH, —S-alkyl, —SH, amino, amido, epoxy, carboxyl, acrylate, (meth)acrylate, cycloalkyl, aryl, alkalyl, polyether, alkenyl, or alkynyl; and n is an integer from 0 to about 300; provided that at least one of R1, R2, R3, R4, R5, R6, R7, and R8 is an alkenyl or alkynyl.

First claim

What is claimed is:

1. A siloxane-modified latex binder comprising a polymerization product of a monomer or a mixture of monomers for producing a latex polymer and a non-hydrolyzable siloxane,
wherein the non-hydrolyzable siloxane is represented by Formula I:

wherein:
R 1 , R 3 , R 4 , R 5 , R 6 , and R 8 are independently C 1 -C 6 alkyl;
R 2 and R 7 are independently hydrogen, alkyl, —O-alkyl, —OH, —S-alkyl, —SH, amino, amido, epoxy, carboxyl, acrylate, (meth)acrylate, cycloalkyl, aryl, alkaryl, polyether, alkenyl, or alkynyl; and
n is an integer from 0 to about 300;
provided that at least one of R 2 and R 7 is an alkenyl or alkynyl.

2. The siloxane-modified latex binder of claim 1 , wherein R 1 , R 3 , R 4 , R 5 , R 6 , and R 8 are methyl.

3. The siloxane-modified latex binder of claim 1 , wherein R 2 and R 7 are independently C 2 -C 6 alkenyl.

4. The siloxane-modified latex binder of claim 1 , wherein n is an integer from about 50 to about 150.

5. A composition comprising a cross-linking agent and the siloxane-modified latex binder of claim 1 , wherein:
the siloxane-modified latex binder further comprises a cross-linkable monomer; and
the cross-linking agent comprises a compound of Formula III:

wherein:
X is a bond or divalent organic group;
R 9 is NH 2 or N═C(R 10 )(R 11 );
and R 10 and R 11 at each occurrence are independently hydrogen or an organic group.

6. The composition of claim 5 , wherein the cross-linkable monomer is selected from the group consisting of methyl vinyl ketone, ethyl vinyl ketone, butyl vinyl ketone, (meth)acrolein, crotonaldehyde, diacetone (meth)acrylamide, diacetone (meth)acrylate, mixed esters of aliphatic diols with (meth)acrylic acid or acetoacetic acid, diacetone acrylamide, diacetone methacrylamide acetoacetoxyethyl methacrylate (AAEM), maleic anhydride, itaconic anhydride, citraconic anhydride, diacetone acrylamide (DAAM), glycidyl meth(acrylate), β-methylglycidyl meth(acrylate), 3,4-epoxycyclohexylmethyl meth(acrylate), 3,4-epoxycyclohexylethyl meth(acrylate), 3,4-epoxycyclohexylpropyl meth(acrylate), allylglycidyl ether, N-methylol acrylamide, and oxidatively crosslinking monomers.

7. The composition of claim 6 , wherein the cross-linkable monomer is selected from the group consisting of acetoacetoxyethyl methacrylate (AAEM), diacetone acrylamide (DAAM), and a combination of any two or more thereof.

8. The composition of claim 5 comprising about 0.05 wt % to about 5 wt % of the non-hydrolyzable siloxane.

9. The composition of claim 5 further comprising one or more chain transfer agents.

10. The composition of claim 5 further comprising water, wherein the composition is an aqueous based paint or coating.

11. A paint or coating comprising a physically coalesced and/or chemically cured composition of claim 10 .

12. The paint or coating of claim 11 , wherein the paint or coating gloss measured at 60° is at least about 85 gloss units, the paint or coating gloss measured at 20° is at least about 65 gloss units, or both.

13. The paint or coating of claim 11 , wherein the paint or coating exhibits a gloss retention of at least about 70% after 2000 hours.

14. The paint or coating of claim 11 , wherein the paint or coating exhibits a smooth, tactile surface.

15. The composition of claim 5 , wherein R 10 and R 11 at each occurrence are independently a C 1 -C 6 alkyl and X is C 1 -C 6 alkylene.

16. A method of producing the siloxane-modified latex binder of claim 1 , the method comprising:
polymerizing the monomer or a mixture of monomers to form a latex binder;
contacting the non-hydrolyzable siloxane with the latex binder to produce the siloxane-modified latex binder; and
polymerizing additional amounts of the monomer or the mixture of monomers.

17. A siloxane-modified latex binder comprising a polymerization product of:
a monomer or a mixture of monomers for producing a latex polymer comprising butyl (meth)acrylate, (meth)acrylic acid, methyl (meth)acrylate, styrene, or a combination of any two or more thereof;
a non-hydrolyzable siloxane represented by Formula II:

wherein q is an integer from about 60 to about 120; and

a cross-linkable monomer comprising acetoacetoxyethyl methacrylate (AAEM), diacetone acrylamide (DAAM), or a combination thereof.

Assignees

• Columbia Insurance Co

Inventors

• Yang Yong
• Garcia De Visicaro Johanna L
• Shavel Luz Clarena
• Sheerin Robert

Classifications

• C09D183/08

  containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen · CPC title

• C08F220/1804

  C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate · CPC title

• C09D133/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C08F220/56

  Acrylamide; Methacrylamide · CPC title

• C09D143/04 Primary

  Homopolymers or copolymers of monomers containing silicon · CPC title