Curable composition and use thereof

• US 20050209410A1
• Filed: 02/09/2005
• Published: 09/22/2005
• Est. Priority Date: 03/16/2004
• Status: Active Grant

• Current Assignee: Rohm and Haas Company (Dow, Inc.)
• Original Assignee: Rohm and Haas Company (Dow, Inc.)
• Inventors: Weinstein, Barry, Tang, Xun, Bromm, Karl Allen
• Granted Patent: US 7,399,818 B2
• Time in Patent Office: Days
• US Class Current: 525/327.700
• CPC Class Codes: C08F 20/00 Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
• CPC Class Codes: C08F 220/06 Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
• CPC Class Codes: C08F 8/14 Esterification

Abstract

A curable composition including a compound, containing as polymerized units, carboxylic acid groups, anhydride groups, or salts thereof, and a styrene, α-methyl styrene, butyl (meth)acrylate, methyl methacrylate, ethyl (meth)acrylate, mono-alkyl (meth)acrylamide, or di-alkyl (meth)acrylamide ethylenically unsaturated monomer having a solubility in water of less than 2 g/100 g water at 25° C.; wherein the compound is either admixed with or copolymerized with a hydroxyl group-containing compound; the curable composition contains from about 3 to about 25 weight percent, based on the total weight of monomers in the curable composition, of the ethylenically unsaturated monomer; the ratio of the number of equivalents of the carboxylic acid groups, anhydride groups, or salts thereof to the number of equivalents of the hydroxyl groups is from about 1/0.01 to about 1/3, is provided. Also provided is a method for treating a substrate with the curable composition, articles prepared by the method of the invention.

Claims

1. A curable composition comprising:

(a) a polyacid copolymer comprising as polymerized units, a monomer comprising carboxylic acid groups, anhydride groups, or salts thereof, and from about 3 to about 25 weight percent, based on the total weight of monomers in the curable composition, of an ethylenically unsaturated monomer having a solubility of less than 2 g/100 g of water at 25°

C.,

wherein said ethylenically unsaturated monomer is selected from the group consisting of ethyl (meth)acrylate, methyl methacrylate, butyl (meth)acrylate, styrene, α

-methyl styrene, mono-alkyl (meth)acrylamide, and di-alkyl (meth)acrylamide; and

(b) a hydroxyl group-comprising compound bearing at least two hydroxyl groups;

wherein the ratio of the number of equivalents of said carboxylic acid groups, anhydride groups, or salts thereof to the number of equivalents of said hydroxyl groups is from about 1/0.01 to about 1/3.

3. The curable composition of claim 1 or 2, wherein said carboxylic acid groups, anhydride groups, or salts thereof are neutralized with a base selected from the group consisting of volatile base, fixed base, and a mixture thereof.

6. The curable composition of claim 1, 2 or 4, wherein said ethylenically unsaturated monomer is selected from the group consisting of from about 10 to about 25 weight percent ethyl (meth)acrylate, from about 10 to about 20 weight percent methyl methacrylate, from about 3 to about 15 weight percent butyl (meth)acrylate, from about 3 to about 15 weight percent styrene, from about 3 to about 15 weight percent α

-methyl styrene, from about 3 to about 8 weight percent t-octyl acrylamide, and from about 5 to about 15 weight percent t-butyl acrylamide, based on the total weight of monomers in the curable composition.

7. The curable composition of claim 1, 2 or 4, wherein said ethylenically unsaturated monomer has a solubility in water of less than 1 g/100 g water at 25°

C., and said curable composition comprises from about 3 to about 15 weight percent, based on the total weight of monomers in the curable composition, of said ethylenically unsaturated monomer.

8. The curable composition of claim 1, 2, or 4, wherein said ethylenically unsaturated monomer has a solubility in water of from 1 g/100 g to 2g/100 g water at 25°

C., and said curable composition comprises from about 10 to about 25 weight percent, based on the total weight of monomers in the curable composition, of said ethylenically unsaturated monomer.

9. The curable composition of claim 1, 2 or 4, further comprising a phosphorous-containing compound.

10. The curable composition of claim 1, 2 or 4, further comprising at least one low molecular weight polybasic carboxylic acid, anhydride, or salt thereof, having a molecular weight of 1000 or less.

11. The curable composition of claim 10, wherein said low molecular weight polybasic carboxylic acid, anhydride, or salt thereof, is mixed with said hydroxyl group-comprising compound, under reactive conditions, prior to mixing with said polyacid copolymer.

12. The curable composition of claim 1, 2 , 4, 10, or 11 wherein said curable composition has a pH of no greater than 3.5.

13. A method of treating a substrate, comprising:

(i) forming the curable composition of claim 1, 2 or 4;

(ii) contacting said substrate with said curable composition; and

(iii) heating said curable composition at a temperature of from 100°

C. to 400°

C.

14. An article prepared by the method of claim 10, wherein said article is selected from the group consisting of heat-resistant non-woven fabric, wood-containing article, and powder coated article.

2. A curable composition comprising:

(a) a polyacid copolymer comprising as polymerized units, a monomer comprising carboxylic acid groups, anhydride groups, or salts thereof, and an ethylenically unsaturated monomer having a solubility of less than 2 g/100 g of water at 25°

C.,

wherein said ethylenically unsaturated monomer is selected from the group consisting of ethyl (meth)acrylate, methyl methacrylate, butyl (meth)acrylate, styrene, α

-methyl styrene, mono-alkyl (meth)acrylamide, and di-alkyl (meth)acrylamide;

(b) a polyacid homopolymer; and

(c) a hydroxyl group-comprising compound bearing at least two hydroxyl groups;

wherein said curable composition comprises from about 3 to about 25 weight percent, based on the total weight of monomers in the curable composition, of said ethylenically unsaturated monomer,

wherein the ratio of the number of equivalents of said carboxylic acid groups, anhydride groups, or salts thereof to the number of equivalents of said hydroxyl groups is from about 1/0.01 to about 1/3.

4. A curable composition comprising a copolymer comprising as polymerized units:

(a) an acid monomer comprising carboxylic acid groups, anhydride groups, or salts thereof;

(b) from about 3 to about 25 weight percent, based on the total weight of monomers in the curable composition, of an ethylenically unsaturated monomer having a solubility of less than 2 g/100 g of water at 25°

C.,

wherein said ethylenically unsaturated monomer is selected from the group consisting of ethyl (meth)acrylate, methyl methacrylate, butyl (meth)acrylate, styrene, α

-methyl styrene, mono-alkyl (meth)acrylamide, and di-alkyl (meth)acrylamide; and

(c) a hydroxyl group-comprising compound.

5. The curable composition of claim 4, wherein said hydroxyl group-comprising compound has a formula selected from the group consisting of Formula I,

CH2═

C(R1)CH(R2)OR3 

 

(I)

wherein R1 and R2 are independently selected from hydrogen, methyl, and —

CH2OH, and R3 is selected from hydrogen, —

CH2CH(CH3)OH, —

CH2CH2OH, —

C(CH2OH)2C2H5 and (C3-C12) polyol residues; and

Formula II,