US 5,362,415 AGranted

Acrylic copolymer which is water-soluble or moderately water-soluble and may be crosslinked; and its use

AssigneeCoatex

InventorsJean-Bernard Egraz, Henri Grondin, Jean-Marc Suau

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Abstract

A copolymer comprised of at least one monomer having ethylenic unsaturation and a carboxylic acid group, optionally at least one monomer having ethylenic unsaturation and not having a carboxylic acid group, at least one oxyalkylated monomer having ethylenic unsaturation and terminated by a fatty hydrophobic chain having at least 26 C atoms, and optionally at least one monomer having at least two sites of ethylenic unsaturation. The copolymer is employed as a modifier of rheological properties, stabilizing agent, and/or an antisedimentation or suspension agent for coarse mineral of organic materials, in applications such as drilling muds, textile printing pies, cosmetics, detergents, plant protection, and paints and coatings.

Claims9

Dependent claims

An aqueous detergent formulation comprising a detergent component and a rheologically modifying effective amount of a water-soluble or moderately water-soluble copolymer which may be crosslinked, comprising:

(a) units of at least one monomer having ethylenic unsaturation and having at least one carboxylic acid group, which monomer is selected from the group consisting of monoacids, diacids, the anhydrides of carboxylic acids, and the hemiesters of diacids;
(b) optionally, unit(s) of at least one monomer having ethylenic unsaturation and not having a carboxylic acid group selected from the group consisting of the esters, amides, and nitriles of (meth)acrylic acid, or selected from the group consisting of vinyl acetate, styrene, methylstyrene, diisobutylene, vinylpyrrolidone, and vinylcaprolactam;
(c) units of at least one monomer having an oxyalkylated moiety, which monomer has ethylenic unsaturation and is terminated by a hydrophobic fatty chain, said monomer having formula I:
##STR3## where m and p represent numbers of oxyalkylene groups each .ltoreq.100;
n represents the number of oxyethylene groups .ltoreq.100;
q represents a number at least equal to 1 such that q(n+m+p) .ltoreq.100;
q represents a number at least equal to 10 such that q(n--m+p).ltoreq.100;
R.sub.1 represents hydrogen or a methyl group;
R.sub.2 represents hydrogen or a methyl group;
and
R' represents a hydrophoic fatty hydrocarbon chain having at least 26 carbon atoms;
and
R represents an unsaturated polymerizable group selected from the group consisting of vinyl group containing moieties, methacryloyl, maleoyl, itaconoyl, crotonyl, an unsaturated urethane moiety, hemiester maleoyl, hemiester itaconoyl, CH.sub.2 .dbd.CHCH.sub.2 --O--, methacrylamido and substituted methacrylamido;
and
(d) optionally, unit(s) of at least one monomer having at least two sites of ethylenic unsaturation selected from the group consisting of ethylene glycol dimethacrylate, 2,2-dihydroxymethylbutanol triacrylate, allyl acrylate, methylenebis(meth)acrylamide, tetraallyloxyethane, triallyl cyanurate, and allyl ethers obtained from polyols.

12 more elements

An aqueous cosmetic formulation comprising a cosmetic component and a rheologically modifying effective amount of a water-soluble or moderately water-soluble copolymer which may be crosslinked, comprising:

(a) units of at least one monomer having ethylenic unsaturation and having at least one carboxylic acid group, which monomer is selected from the group consisting of monoacids, diacids, the anhydrides of carboxylic acids, and the hemiesters of diacids;
(b) optionally, unit(s) of at least one monomer having ethylenic unsaturation and not having a carboxylic acid group selected from the group consisting of the esters, amides, and nitriles of (meth)acrylic acid, or selected from the group consisting of vinyl acetate, styrene, methylstyrene, diisobutylene, vinylpyrrolidone, and vinylcaprolactam;
(c) units of at least one monomer having an oxyalkylated moiety, which monomer has ethylenic unsaturation and is terminated by a hydrophobic fatty chain, said monomer having formula I:
##STR4## where m and p represent numbers of oxyalkylene groups each .ltoreq.100;
n represents the number of oxyethylene groups .ltoreq.100;
q represents a number at least equal to 1 such that q(n+m+p).ltoreq.100;
R.sub.1 represents hydrogen or a methyl group;
R.sub.2 represents hydrogen or a methyl group;
R' represents a hydrophobic fatty hydrocarbon chain having at least 26 carbon atoms;
and
R represents an unsaturated polymerizable group selected from the group consisting of vinyl group containing moieties, methacryloyl, maleoyl, itaconoyl, crotonyl, an unsaturated urethane moiety, hemiester maleoyl, hemiester itaconoyl, CH.sub.2 .dbd.CHCH.sub.2 --O--, methacrylamido and substituted methacrylamido;
and
(d) optionally, unit(s) of at least one monomer having at least two sites of ethylenic unsaturation selected from the group consisting of ethylene glycol dimethacrylate, 2,2-dihydroxymethylbutanol triacrylate, allyl acrylate, methylenebis(meth)acrylamide, tetraallyloxyethane, triallyl cyanurate, and allyl ethers obtained from polyols.

10 more elements

An aqueous textile printing pie formulation comprising a textile printing pie component and a rheologically modifying effective amount of a water-soluble or moderately water-soluble copolymer which may be crosslinked, comprising:

(a) units of at least one monomer having ethylenic unsaturation and having at least one carboxylic acid group, which monomer is selected from the group consisting of monoacids, diacids, the anhydrides of carboxylic acids, and the hemiesters of diacids;
(b) optionally, unit(s) of at least one monomer having ethylenic unsaturation and not having a carboxylic acid group selected from the group consisting of the esters, amides, and nitriles of (meth)acrylic acid, or selected from the group consisting of vinyl acetate, styrene, methylstyrene, diisobutylene, vinylpyrrolidone, and vinylcaprolactam;
(c) units of at least on monomer having an oxyalkylated moiety, which monomer has ethylenic unsaturation and is terminated by a hydrophobic fatty chain, said monomer having formula I:
##STR5## where m and p represent numbers of oxyalkylene groups each .ltoreq.100;
n represents the number of oxyethylene groups .ltoreq.100;
q represents a number at least equal to 1 such that q(n+p).ltoreq.100;
R.sub.1 represents hydrogen or a methyl group;
R.sub.2 represents hydrogen or a methyl group;
R' represents a hydrophobic fatty hydrocarbon chain having at least 26 carbon atoms;
and
R represents an unsaturated polymerizable group selected from the group consisting of vinyl group containing moieties, methacryloyl, maleoyl, itaconoyl, crotonyl, an unsaturated urethane moiety, hemiester maleoyl, hemiester itaconoyl, CH.sub.2 .dbd.CHCH.sub.2 --O--, methacrylamido and substituted methacrylamido;
and
(d) optionally, unit(s) of at least one monomer having at least two sites of ethylenic unsaturation selected from the group consisting of ethylene glycol dimethacrylate, 2,2-dihydroxymethylbutanol triacrylate, allyl acrylate, methylenebis(meth)acrylamide, tetraallyloxyethane, triallyl cyanurate, and allyl ethers obtained from polyols.

10 more elements

An aqueous drilling mud formulation comprising a drilling mud component and a rheologically modifying effective amount of a water-soluble or moderately water-soluble copolymer which may be crosslinked, comprising:

(a) units of at least one monomer having ethylenic unsaturation and having at least one carboxylic acid group, which monomer is selected from the group consisting of monoacids, diacids, the anhydrides of carboxylic acids, and the hemiesters of diacids;
(b) optionally, unit(s) of at least one monomer having ethylenic unsaturation and not having a carboxylic acid group selected from the group consisting of the esters, amides, and nitriles of (meth)acrylic acid, or selected from the group consisting of vinyl acetate, styrene, methylstyrene, diisobutylene, vinylpyrrolidone, and vinylcaprolactam;
(c) units of at least one monomer having an oxyalkylated moiety, which monomer has ethylenic unsaturation and is terminated by a hydrophobic fatty chain, said monomer having formula I:
##STR6## where m and p represent numbers of oxyalkylene groups each .ltoreq.100;
n represents the number of oxyethylene groups .ltoreq.100;
q represents a number at least equal to 1 such that q(n+m+p) .ltoreq.100;
R.sub.1 represents hydrogen or a methyl group;
R.sub.2 represents hydrogen or a methyl group;
and
R' represents a hydrophobic fatty hydrocarbon chain having at least 26 carbon atoms;
and
R represents an unsaturated polymerizable group selected from the group consisting of vinyl group containing moieties, methacryloyl, maleoyl, itaconoyl, crotonyl, an unsaturated urethane moiety, hemiester maleoyl, hemiester itaconoyl, CH.sub.2 .dbd.CHCH.sub.2 --O--, methacrylamido and substituted methacrylamido;
and
(d) optionally, unit(s) of at least one monomer having at least two sites of ethylenic unsaturation selected from the group consisting of ethylene glycol dimethacrylate, 2,2-dihydroxymethylbutanol triacrylate, allyl acrylate, methylenebis(meth)acrylamide, tetraallyloxyethane, triallyl cyanurate, and allyl ethers obtained from polyols.

11 more elements

An aqueous paint or coating formulation comprising a paint or coating component and a rheologically modifying effective amount of a water-soluble or moderately water-soluble copolymer which may be crosslinked, comprising:

(a) units of at least one monomer having ethylenic unsaturation and having at least one carboxylic acid group, which monomer is selected from the group consisting of monoacids, diacids, the anhydrides of carboxylic acids, and the hemiesters of diacids;
(b) optionally, unit(s) of at least one monomer having ethylenic unsaturation and not having a carboxylic acid group selected from the group consisting of the esters, amides, and nitriles of (meth)acrylic acid, or selected from the group consisting of vinyl acetate, styrene, methylstyrene, diisobutylene, vinylpyrrolidone, and vinylcaprolactam;
(c) units of at least one monomer having an oxyalkylated moiety, which monomer has ethylenic unsaturation and is terminated by a hydrophobic fatty chain, said monomer having formula I:
##STR7## where m and p represent numbers of oxyalkylene groups each .ltoreq.100;
n represents the number of oxyethylene groups .ltoreq.100;
q represents a number at least equal to 1 such that q(n+m+p) .ltoreq.100;
R.sub.1 represents hydrogen or a methyl group;
R.sub.2 represents hydrogen or a methyl group;
and
R' represents a fatty hydrocarbon chain having at least 26 carbon atoms;
and
R represents an unsaturated polymerizable group selected from the group consisting of vinyl group containing moieties, methacryloyl, maleoyl, itaconoyl, crotonyl, an unsaturated urethane moiety, hemiester maleoyl, hemiester itaconoyl, CH.sub.2 .dbd.CHCH.sub.2 --O--, methacrylamido and substituted methacrylamido;
and
(d) optionally, unit(s) of at least one monomer having at least two sites of ethylenic unsaturation selected from the group consisting of ethylene glycol dimethacrylate, 2,2-dihydroxymethylbutanol triacrylate, allyl acrylate, methylenebis(meth)acrylamide, tetraallyloxyethane, triallyl cyanurate, and allyl ethers obtained from polyols.

11 more elements

An aqueous medium comprising suspended coarse mineral or organic material comprising a suspending or an anti-sedimentation effective amount of a water-soluble or moderately water-soluble copolymer which may be crosslinked, comprising:

(a) units of at least one monomer having ethylenic unsaturation and having at least one carboxylic acid group, which monomer is selected from the group consisting of monoacids, diacids, the anhydrides of carboxylic acids, and the hemiesters of diacids;
(b) optionally unit(s) of at least one monomer having ethylenic unsaturation and not having a carboxylic acid group selected from the group consisting of the esters, amides, and nitriles of (meth)acrylic acid, or selected from the group consisting of vinyl acetate, styrene, methylstyrene, diisobutylene, vinylpyrrolidone, and vinylcaprolactam;
(c) units of at least one monomer having an oxyalkylated moiety, which monomer has ethylenic unsaturation and is terminated by a hydrophobic fatty chain, said monomer having formula I:
##STR8## where m and p represent numbers of oxyalkylene groups each .ltoreq.100;
n represents the number of oxyethylene groups .ltoreq.100;
q represents a number at least equal to 1 such that q(n+m+p) .ltoreq.100;
R.sub.1 represents hydrogen or a methyl group;
R.sub.2 represents hydrogen or a methyl group;
and
R' represents a fatty hydrocarbon chain having at least 26 carbon atoms;
and
R represents an unsaturated polymerizable group selected from the group consisting of vinyl group containing moieties, methacryloyl, maleoyl, itaconoyl, crotonyl, an unsaturated urethane moiety, hemiester maleoyl, hemiester itaconoyl, CH.sub.2 .dbd.CHCH.sub.2 --O--, methacrylamido and substituted methacrylamido;
and
(d) optionally, unit(s) of at least one monomer having at least two sites of ethylenic unsaturation selected from the group consisting of ethylene glycol dimethacrylate, 2,2-dihydroxymethylbutanol triacrylate, allyl acrylate, methylenebis(meth)acrylamide, tetraallyloxyethane, triallyl cyanurate, and allyl ethers obtained from polyols.

11 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/136,282Filed 15 Oct 1993 · division
Priority: FR 92 083991 Jul 1992
Granted: 8 Nov 1994
Term ends: Not estimatedThe source records don’t support an estimate.

Classification34 codes

A61K 8/8152
Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon…:…
A61Q 5/02
Preparations for care of the hair: preparations for cleaning the hair
A61Q 19/00
Preparations for care of the skin
C08F 220/04
Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof: acids; Metal salts or ammonium salts thereof