US4225480A
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Addition interpolymers having improved stability and two-package compositions comprising such interpolymers and polyepoxides
Assignee: PPG Industries Inc
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Filing: 1978-07-31
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Granted: 1980-09-30
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Expires: 1998-07-31
Abstract
Abstract Amine group-containing addition interpolymers having improved stability under conditions of storage and use are prepared by interpolymerizing at least one polymerizable ethylenically unsaturated carboxylic acid monomer and at least one polymerizable ethylenically unsaturated aminolysis-resistant organic monomer to form an addition interpolymer containing carboxyl groups pendent to the polymer chain and aminolysis-resistant organic groups pendent to the polymer chain, following which a portion of the pendent carboxyl groups of the addition interpolymer are reacted with an alkylenimine to form pendent amine groups and a portion of the pendent carboxyl groups of the addition interpolymer are neutralized with a basic compound to form pendent anionic salt groups. The addition interpolymer is preferably reducible with organic solvents, water or a mixture thereof, and can be utilized as pigment grinding vehicles or they can be formulated with conventional additives to form useful coating compositions. A preferred use for these interpolymers is in combination with a polyepoxide to provide two-package cocurable polymeric compositions for coatings and other uses.
Inventors
- 👤 Karl F. Schimmel
- 👤 Roger M. Christenson
- 👤 Jerome A. Seiner
- 👤 James A. Claar
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 07:23
CPC Classifications
C; C09; C09D; C09D133/00; C09D133/02; C08; C08L; C08L33/00; C08L33/02; C08L63/00; C09D157/00; C09D157/04
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
206 words
A two-package polymeric composition comprising cocurable resinous components consisting essentially of: (a) a polyepoxide having a 1,2-epoxy equivalence greater than 1.0; and (b) at addition interpolymer, containing pendent anionic salt groups, pendent carboxyl groups, pendent amine groups and pendent aminolysis-resistant organic groups, wherein said interpolymer is prepared by interpolymerizing from about 5 percent to about 60 percent by weight of at least one ethylenically unsaturated carboxylic acid monomer and from about 40 percent to about 95 percent by weight of at least one aminolysis resistant organic monomer selected from the group consisting of monoolefinic and diolefinic hydrocarbons, unsaturated carboxylic acid amides, unsaturated organonitriles, non-methyl esters of alpha, alkyl-substituted carboxylic acids, and mixtuures thereof so as to form an interpolymer having pendent carboxyl groups and pendent aminolysis-resistant organic groups and wherein said interpolymer is further reacted with sufficient alkylenimine to iminate from about 5 mole percent to about 95 mole percent of the carboxyl groups to form the pendent amine groups and sufficient base to form the pendent anionic salt groups and to result in a level of neutralization sufficient to give the interpolymer a pH of greater than about 6 in water, said components (a) and (b) being interreactive to form a hard, solvent-resistant crosslinked polymer.
Claim 2
Dependent Claim
206 words
A two-package polymeric composition comprising cocurable resinous components consisting essentially of: (a) a polyepoxide having a 1,2-epoxy equivalence greater than 1.0; and (b) at addition interpolymer, containing pendent anionic salt groups, pendent carboxyl groups, pendent amine groups and pendent aminolysis-resistant organic groups, wherein said interpolymer is prepared by interpolymerizing from about 5 percent to about 60 percent by weight of at least one ethylenically unsaturated carboxylic acid monomer and from about 40 percent to about 95 percent by weight of at least one aminolysis resistant organic monomer selected from the group consisting of monoolefinic and diolefinic hydrocarbons, unsaturated carboxylic acid amides, unsaturated organonitriles, non-methyl esters of alpha, alkyl-substituted carboxylic acids, and mixtuures thereof so as to form an interpolymer having pendent carboxyl groups and pendent aminolysis-resistant organic groups and wherein said interpolymer is further reacted with sufficient alkylenimine to iminate from about 5 mole percent to about 95 mole percent of the carboxyl groups to form the pendent amine groups and sufficient base to form the pendent anionic salt groups and to result in a level of neutralization sufficient to give the interpolymer a pH of greater than about 6 in water, said components (a) and (b) being interreactive to form a hard, solvent-resistant crosslinked polymer.
Claim 3
Dependent Claim
25 words
The polymeric composition of claim 1 in which either or both of components (a) and (b) are in a solvent medium comprised predominantly of water.
Claim 4
Dependent Claim
17 words
The polymeric composition of claim 1 in which said polyepoxide is a polyglycidyl ether of a polyphenol.
Claim 5
Dependent Claim
13 words
The polymeric composition of claim 3 in which said polyphenol is bisphenol A.
Claim 6
Dependent Claim
27 words
The polymeric composition of claim 1 wherein the pendent anionic salt groups are derived by neutralizing the carboxyl groups with an amine or an alkali metal hydroxide.
Claim 7
Dependent Claim
14 words
The polymeric composition of claim 5 wherein the carboxyl groups are neutralized with dimethylethanolamine.
Claim 8
Dependent Claim
21 words
The polymeric composition of claim 1 wherein the ethylenically unsaturated carboxylic acid is acrylic acid, methacrylic acid or a mixture thereof.
Claim 9
Dependent Claim
18 words
The polymeric composition of claim 7 wherein the alkylenimine is ethylenimine, 1,2-propylenimine, N-hydroxyethyl ethylenimine or a mixture thereof.
Claim 10
Dependent Claim
46 words
The polymeric composition of claim 1 wherein the interpolymer is prepared by interpolymerizing from about 10 percent to about 50 percent by weight of the ethylenically unsaturated carboxylic acid monomer and from about 50 percent to about 90 percent by weight of the aminolysis-resistant organic monomer.
Claim 11
Dependent Claim
21 words
The polymeric composition of claim 9 wherein the aminolysis-resistant organic monomer is a non-methyl ester of an alpha, alkyl-substituted carboxylic acid.
Claim 12
Dependent Claim
25 words
The polymeric composition of claim 10 wherein the aminolysis-resistant monomer is a sterically hindered branched chain or alicyclic ester of the alpha, alkyl-substituted carboxylic acid.
Claim 13
Dependent Claim
18 words
The polymeric composition of claim 11 wherein the sterically hindered branched chain or alicyclic ester is isobutyl methacrylate.
Claim 14
Dependent Claim
23 words
The polymeric composition of claim 9 in which said addition interpolymer has a pH of greater than 7.0 in the presence of water.
Claim 15
Dependent Claim
24 words
The polymeric composition of claim 13 wherein from about 15 mole percent to about 50 mole percent of the carboxylic acid groups are iminated.
Claim 16
Dependent Claim
21 words
The polymeric composition of claim 9 wherein the aminolysis-resistant organic monomer is styrene, alpha-methyl styrene, vinyl toluene or a mixture thereof.
Claim 17
Dependent Claim
212 words
A two-package polymeric composition comprising cocurable resinous components consisting essentially of: (a) a polyepoxide having a 1,2-epoxy equivalence greater than 1.0 and a molecular weight below about 4,000; and (b) an addition interpolymer containing pendent anionic salt groups, pendent carboxyl groups, pendent amine groups and pendent aminolysis-resistant organic groups, wherein said interpolymer is prepared by interpolymerizing from about 5 percent to about 60 percent by weight of at least one ethylenically unsaturated carboxylic acid monomer and from about 40 percent to about 95 percent by weight of at least one aminolysis-resistant organic monomer selected from the group consisting of monoolefinic and diolefinic hydrocarbons, unsaturated carboxylic acid amides, unsaturated organonitriles, non-methyl esters of alpha, alkylsubstituted carboxylic acids, and mixtures thereof so as to form an interpolymer having pendent carboxyl groups and pendent aminolysis-resistant organic groups and wherein said interpolymer is further reacted with sufficient alkylenimine to iminate from about 5 mole percent to about 95 mole percent of the carboxyl groups to form the pendent amine groups and sufficient base to form the pendent anionic salt groups and to result in a level of neutralization sufficient to give the interpolymer a pH of greater than about 6 in water, said components (a) and (b) being interreactive to form a hard, solvent-resistant crosslinked polymer.
Claim 18
Dependent Claim
212 words
A two-package polymeric composition comprising cocurable resinous components consisting essentially of: (a) a polyepoxide having a 1,2-epoxy equivalence greater than 1.0 and a molecular weight below about 4,000; and (b) an addition interpolymer containing pendent anionic salt groups, pendent carboxyl groups, pendent amine groups and pendent aminolysis-resistant organic groups, wherein said interpolymer is prepared by interpolymerizing from about 5 percent to about 60 percent by weight of at least one ethylenically unsaturated carboxylic acid monomer and from about 40 percent to about 95 percent by weight of at least one aminolysis-resistant organic monomer selected from the group consisting of monoolefinic and diolefinic hydrocarbons, unsaturated carboxylic acid amides, unsaturated organonitriles, non-methyl esters of alpha, alkylsubstituted carboxylic acids, and mixtures thereof so as to form an interpolymer having pendent carboxyl groups and pendent aminolysis-resistant organic groups and wherein said interpolymer is further reacted with sufficient alkylenimine to iminate from about 5 mole percent to about 95 mole percent of the carboxyl groups to form the pendent amine groups and sufficient base to form the pendent anionic salt groups and to result in a level of neutralization sufficient to give the interpolymer a pH of greater than about 6 in water, said components (a) and (b) being interreactive to form a hard, solvent-resistant crosslinked polymer.
Claim 19
Dependent Claim
23 words
The polymeric composition of claim 16 wherein the aminolysis-resistant monomer is a branched chain or alicyclic ester of the alpha, alkyl-substituted carboxylic acid.
Claim 20
Dependent Claim
21 words
The polymeric composition of claim 17 wherein the ethylenically unsaturated carboxylic acid is acrylic acid, methacrylic acid or a mixture thereof.
Claim 21
Dependent Claim
18 words
The polymeric composition of claim 18 wherein the alkylenimine is ethylenimine, 1,2-propylenimine, N-hydroxyethyl ethylenimine or a mixture thereof.
Claim 22
Dependent Claim
22 words
The polymeric composition of claim 19 wherein the addition interpolymer has a pH of greater than 7.0 in the presence of water.
Claim 23
Dependent Claim
74 words
The polymeric composition of claim 20 wherein the interpolymer is prepared by interpolymerizing from about 10 percent to about 50 percent by weight of the acrylic acid, methacrylic acid or mixture thereof, and from about 50 percent to about 90 percent by weight of the branched chain or alicyclic ester of the alpha, alkyl-substituted carboxylic acid and from about 15 mole percent to about 50 mole percent of the carboxylic acid groups are iminated.
Claim 24
Dependent Claim
22 words
The polymeric composition of claim 21 wherein the branched chain or alicyclic ester of the alpha, alkyl-substituted carboxylic acid is isobutyl methacrylate.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-09-30 | 1984-03-31 | 1984-09-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-09-30 | 1988-03-31 | 1988-09-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-09-30 | 1992-03-31 | 1992-09-30 | $7700.00 | Window Closed / Lapsed |