# US 8,784,786 B2 · Rheology modifier polymer

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- Number: US 8,784,786 B2
- Document ID: US8784786B2
- Status: Granted
- Kind: B2
- Application number: 12/931,903
- Filed: 2011-02-14
- Published: 2011-10-06
- Granted: 2014-07-22
- Earliest claimed: 2010-02-12
- Assignees: Rhodia Operations
- Applicants: Lawrence Hough; Wojciech Bzducha; Pascal Herve; Pierre Hennaux; Andrew Douglass; Monique Adamy; Inigo Gonzalez
- Inventors: Lawrence Hough; Wojciech Bzducha; Pascal Herve; Pierre Hennaux; Andrew Douglass; Monique Adamy; Inigo Gonzalez
- Web page: https://patentgrep.com/patent/US8784786B2

## CPC

- A61K 8/91: Graft copolymers (A61K8/89 takes precedence)
- A01N 25/10: Macromolecular compounds
- A61K 8/8152: {Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers}
- A61Q 5/02: Preparations for cleaning the hair
- A61Q 5/06: Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q 19/00: Preparations for care of the skin
- A61Q 19/10: Washing or bathing preparations
- C08F 220/68: Esters
- C08F 283/06: on to polyethers, polyoxymethylenes or polyacetals {(C08F283/004 takes precedence)}
- C08F 283/065: {on to unsaturated polyethers, polyoxymethylenes or polyacetals}
- C08F 290/062: {Polyethers}
- C08K 3/20: Oxides; Hydroxides {(graphene oxides C08K3/042)}
- C09D 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C11D 3/3951: {combined with specific additives}
- A61K 2800/10: General cosmetic use
- A61K 2800/48: Thickener, Thickening system
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C11D: DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL

## Abstract

A polymer includes (a) one or more first monomeric units, each independently comprising at least one bicycloheptyl-polyether, bicycloheptenyl-polyether or branched (C5-C50)alkyl-polyether group per monomeric unit, wherein the bicycloheptyl-polyether or bicycloheptenyl-polyether group may optionally be substituted on one or more ring carbon atoms by one or two (C1-C6)alkyl groups per carbon atom, and (b) one or more second monomeric units, each independently comprising at least one pendant linear or branched (C5-C50)alkyl-polyether group per monomeric unit, provided that the first and second monomeric units cannot both comprise a branched (C5-C50)alkyl-polyether group and is useful as a component in liquid compositions, such as aqueous latex coating compositions, personal care compositions, home care compositions, and institutional or industrial care compositions.

## Claims

### Claim 1

A polymer made by copolymerization of a mixture of polymerizable monomers, said polymerizable monomers which copolymerize to form the polymer comprising:
(a) one or more first monomers each independently selected from monomers according to structure (XIII):
wherein:
R19 is H or methyl,
i is an integer of from 10 to 40, and
j is an integer of from 1 to 20,
(b) one or more second monomers copolymerizable with the first monomer, wherein: the one or more second monomers are each independently selected from monomers according to structure (XX):
wherein
R21 is linear (C5-C50)alkyl,
R25 is methyl or ethyl
p and q are independently integers of from 2 to 5,
each r is independently an integer of from 1 to about 80,
each s is independently an integer of from 0 to about 80, and
t is an integer of from 1 to about 50, provided that the product obtained by multiplying the integer t times the sum of r+s is from 2 to about 100, and
(c) one or more third monomers each independently selected from monocarboxylic acid monomers according to structure (XXII):
R34—R32—R31 (XXII)
wherein:
R31 is a moiety that comprises a carboxylic acid, sulfonic acid, or phosphoric acid group,
R32 is absent or is a bivalent linking group, and
R34 is a moiety having a site of ethylenic unsaturation, and
(d) one or more fourth monomers each independently selected from compounds according to structure (XXIV):
R43—R42—R41 (XXIV)
wherein:
R41 is alkyl, hydroxyalkyl, alkoxyalkyl, cycloalkyl, aryl, aralkyl, or aryloxy,
R42 is absent or is a bivalent linking group, and
R43 is a moiety having a site of ethylenic unsaturation.

### Claim 2 (depends on 1)

The polymer of claim 1, wherein:
p=2
r is an integer of from 10 to 40,
s=0, and
t=1.

### Claim 3 (depends on 1)

The polymer of claim 1, wherein:
(a)
i is an integer of from 15 to 30,
j is an integer from 2 to 10,
(b)
p=2,
r is an integer of from 10 to 50,
s=0,
t=1,
(c) R31 is a carboxylic acid group, and
(d) R41 is (C1-C12)alkyl.

### Claim 4 (depends on 1)

The polymer of claim 1, wherein R21 is linear (C16-C22)alkyl, R25 is methyl or ethyl, p=2, s=0, and t=1.

### Claim 5 (depends on 1)

The polymer of claim 1, wherein the polymer is a non-crosslinked polymer.

### Claim 6 (depends on 1)

The polymer of claim 1, wherein the polymer is a crosslinked polymer.

### Claim 7 (depends on 1)

The polymer of claim 1, wherein:
R19 is H or methyl,
i is an integer of from 15 to 30, and
j is an integer of from 2 to 10.

### Claim 8 (depends on 1)

The polymer of claim 1, wherein:
the one or more second monomers comprise a mixture of second monomers, wherein, in each case:
R21 is selected from linear C16 alkyl, linear C18 alkyl, and linear C22 alkyl groups,
p=2
r is an integer of from 10 to 50,
s=0, and
t=1.

### Claim 9 (depends on 1)

The polymer of claim 1, wherein R31 is a carboxylic acid group.

### Claim 10 (depends on 1)

The polymer of claim 1, wherein R41 is (C1-C6)alkyl.

### Claim 11 (depends on 1)

The polymer of claim 1, wherein:
(a)
i is an integer of from 15 to 30,
j is an integer of from 2 to 10,
(b) the one or more second monomers comprise a mixture of second monomers, wherein, in each case, R21 is selected from linear C16 alkyl, linear C18 alkyl, and linear C22 alkyl groups,
p=2,
r is an integer of from 10 to 50,
s=0,
t=1,
(c) the one or more third monomers comprise at least one monocarboxylic monomer selected from acrylic acid and methacrylic acid, and
(d) the one or more fourth monomers comprise at least one monomer selected from (C1-C6)alkyl acrylic esters and (C1-C6)alkyl methacrylic esters.

### Claim 12 (depends on 11)

The polymer of claim 11, wherein the polymer is a crosslinked polymer.

### Claim 13 (depends on 1)

A process for making a polymer of claim 1, comprising polymerizing a mixture of monomers said mixture comprising:
(a) the one or more first monomers,
(b) the one or more second monomers,
(c) the one or more third monomers, and
(d) the one or more fourth monomers.

### Claim 14 (depends on 1)

A composition comprising a liquid medium and one or more polymers according claim 1.

### Claim 15 (depends on 14)

The composition of claim 14, further comprises one or more surfactants.

### Claim 16 (depends on 14)

The composition of claim 14, wherein the composition is an aqueous latex coating composition that further comprises a polymer latex.

### Claim 17 (depends on 14)

The composition of claim 14, wherein the composition is a personal care composition.

### Claim 18 (depends on 17)

The composition of claim 17, wherein the composition further comprises one or more surfactants.

### Claim 19 (depends on 17)

The composition of claim 17, wherein the composition is substantially free or free of sulfate surfactant compounds.

### Claim 20 (depends on 17)

The composition of claim 17, wherein the composition further comprises one or more personal care benefit agents.

### Claim 21 (depends on 17)

The composition of claim 17, wherein the composition comprises an amount of polymer effective to impart a yield strength of greater than 0 Pa to the composition.

### Claim 22 (depends on 17)

The composition of claim 17, wherein the composition exhibits a clear, transparent visual appearance.

### Claim 23 (depends on 17)

The composition of claim 17, wherein the composition comprises an amount of polymer effective to impart a yield strength of greater than 1 Pa to the composition and the composition further comprises suspended particles of one or more solid, liquid, or gas that are insoluble or are only partly soluble in the personal care composition.

### Claim 24 (depends on 14)

The composition of claim 14, wherein the composition is home care composition or institutional or industrial care composition.

### Claim 25 (depends on 24)

The composition of claim 24, wherein the composition further comprises one or more surfactants and, optionally, one or more additives selected from builders, bleaching agents, acids, bases, or abrasives, antibacterial agents, fungicides, enzymes, and opacifing agents.

### Claim 26 (depends on 1)

A composition comprising a liquid medium and one or more polymers according claim 1.

### Claim 27 (depends on 1)

The polymer of claim 1, wherein the polymerizable monomers consist of:
(a) the one or more first monomers,
(b) the one or more second monomers,
(c) the one or more third monomers,
and
(d) the one or more fourth monomers;
wherein the polymer is optionally crosslinked polymer by optional crosslinker monomer.

### Claim 28 (depends on 27)

The polymer of claim 27, wherein:
R19 is H or methyl,
i is an integer of from 15 to 30, and
j is an integer of from 2 to 10.

### Claim 29 (depends on 27)

The polymer of claim 27, wherein:
the one or more second monomers consist of a mixture of second monomers, wherein, in each case:
R21 is selected from linear C16 alkyl, linear C18 alkyl, and linear C22 alkyl groups,
p=2
r is an integer of from 10 to 50,
s=0, and
t=1.

### Claim 30 (depends on 27)

The polymer of claim 27, wherein R31 is a carboxylic acid group.

### Claim 31 (depends on 27)

The polymer of claim 27, wherein R41 is (C1-C6)alkyl.

### Claim 32 (depends on 27)

The polymer of claim 27, wherein:
(a) R19 is H or methyl,
i is an integer of from 15 to 30,
j is an integer of from 2 to 10,
(b) the one or more second monomers are a mixture of second monomers, wherein, in each case, R21 is selected from linear C16 alkyl, linear C18 alkyl, and linear C22 alkyl groups,
p=2,
r is an integer of from 10 to 50,
s=0,
t=1,
(c) the one or more third monomers are at least one monocarboxylic monomer selected from acrylic acid and methacrylic acid, and
(d) the one or more fourth monomers are at least one monomer selected from (C1-C6)alkyl acrylic esters and (C1-C6)alkyl methacrylic esters.

### Claim 33 (depends on 27)

The polymer of claim 27, wherein the crosslinker monomer is in the mixture and selected from the group consisting of:
polyfunctional monomers containing multiple reactive groups selected from epoxide groups, isocyanate groups, and hydrolyzable silane groups, polyunsaturated crosslinker monomers selected from polyunsaturated aromatic monomers, divinylbenzene, divinyl naphthalene, and trivinylbenzene, polyunsaturated alicyclic monomers, 1,2,4-trivinylcyclohexane, di-functional esters of phthalic acid, diallyl phthalate, polyunsaturated aliphatic monomers, dienes, trienes, and tetraenes, including isoprene, butadiene, 1,5-hexadiene, 1,5,9-decatriene, 1,9-decadiene, 1,5-heptadiene, polyalkenyl ethers, triallyl pentaerythritol, diallyl pentaerythritol, diallyl sucrose, octaallyl sucrose, and trimethylolpropane diallyl ether, polyunsaturated esters of polyalcohols or polyacids selected from 1,6-hexanediol di(meth)acrylate, tetramethylene tri(meth)acrylate, allyl acrylate, diallyl itaconate, diallyl fumarate, diallyl maleate, trimethylolpropane tri(meth)acrylate, trimethylolpropane di(meth)acrylate, poly(alkyleneoxy)glycol di(meth)acrylates, and polyethylene glycol di(meth)acrylate, alkylene bisacrylamides selected from methylenebisacrylamide and propylene bisacrylamide, hydroxy and carboxy derivatives of methylene bis-acrylamide, N,N′-bismethylol methylene bisacrylamide, polyalkyleneglycol di(meth)acrylates selected from ethyleneglycol di(meth)acrylate, diethyleneglycol di(meth)acrylate, and triethyleneglycol di(meth)acrylate, polyunsaturated silanes selected from dimethyldivinylsilane, methyltrivinylsilane, allyldimethylvinylsilane, diallydimethylsilane and tetravinylsilane, polyunsaturated stannanes, tetraallyl tin, diallyldimethyl tin, crosslinker monomers having more than one (meth)acrylic group per molecule selected from allyl methacrylate, ethylene glycol dimethacrylate, butylene glycol dimethacrylate, diallyl pentaerythritol, methylenebisacrylamide, pentaerythritol di-, tri- and tetra-acrylates, divinyl benzene, poly(alkyleneoxy)glycol di(meth)acrylates, polyethylene glycol diacrylates, bisphenol A diacrylates, butanediol dimethacrylate, 2,2-dimethylpropanediol dimethacrylate, ethylene glycol dimethacrylate, phenylene diacrylate, or a mixture thereof.

### Claim 34 (depends on 1)

The polymer of claim 1, wherein R43 of the one or more fourth monomers is according to structure (XI):
wherein
R19 is H or (C1-C4)alkyl.

### Claim 35 (depends on 1)

The polymer of claim 1, wherein the one or more fourth monomers are selected from the group consisting of, (meth)acrylic esters, styrene, and ethyl acrylate.

### Claim 36 (depends on 1)

The polymer of claim 1, wherein:
(a) the one or more first monomers are selected from monomers according to structure (XIII):
where R19 is methyl, i=25, and j=5;
(b) the one or more second monomers are selected from monomers according to structure (XX):
wherein R24 is methyl, R21 is a mixture of linear C16, linear C18, and linear C22 alkyl groups, p=2, r=25, s=0, and t=1;
(c) (Elected species) the one or more third monomers is methacrylic acid, and
(d) (Elected species) the one or more fourth monomers is ethyl acrylate.

### Claim 37 (depends on 36)

The polymer of claim 36, wherein the polymer is a crosslinked polymer.