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US 2006/0039939 A1Published application
Associative thickeners for aqueous systems
AssigneeLubrizol Advanced Materials, Inc.
InventorsJohn Lai, Shui-Jen Hsu, Krishnan Tamareselvy
Life of this patent
Estimating the term…
Abstract
Thiocarbonate compounds which, in one embodiment, are utilized as a rheology modifier or associative thickener. The thiocarbonate compounds thicken or increase the viscosity of a composition, preferably an aqueous composition when used in an effective amount. In one preferred embodiment, the thiocarbonate compounds include at least one hydrophilic group containing repeat unit such as derived from acrylic acid, and at least one hydrophobic group to enhance association with other compounds and thus increase viscosity of a composition. Aqueous composition comprising a latex and thiocarbonate associative thickeners are described.
Claims24
An aqueous composition, comprising:
- A) water;
- B) a latex polymer or copolymer;
- and
- C) a thiocarbonate associative thickener compound;
- said thiocarbonate compound comprising a reaction product polymerized from a) at least one hydrophobe group containing monomer;
- b) at least one hydrophilic group containing monomer;
- c) optionally at least one other monomer selected from branched and unbranched (C1 to C8) alkyl esters of (meth)acrylic acid, vinyl acetate;
- styrene;
- diene monomers having a total of from 4 to 12 carbon atoms, α-methyl styrene;
- and C1 to C12 alkyl styrenes with substituent groups either on the main alkyl chain or on the ring or both;
- and d) a thiocarbonate compound having the formula:
- wherein A independently represents hydrogen or a group represented by the formulae:
- wherein R14 is an alkyl group having from about 3 to about 50 carbon atoms;
- R1 and R2, independently, is a linear or branched alkyl having from 1 to about 6 carbon atoms, or a substituted C1 to about C6 alkyl having one or more substituents, or one or more aryls, or a substituted aryl having from 1 to 6 substituents on the aryl ring;
- or wherein R1 and R2 are part of a substituted or unsubstituted cyclic ring having from about 5 to about 12 total carbon atoms;
- wherein said one or more substituents, independently, comprise an alkyl having from 1 to 6 carbon atoms, or an aryl, or a halogen which can be the same or different, or a cyano, or an ether having a total of from 2 to about 20 carbon atoms, or a nitro group, or combinations thereof;
- or
- wherein A is as defined above;
- R3 is benzyl, a C1 to C18 alkyl, or a substituted C1 to C18 alkyl wherein said substituted group is halogen, hydroxyl, or alkoxy, or a C1 to C18 hydroxyalkyl, aralkyl, cyanoalkyl, aminoalkyl, carboxylalkyl, carboalkoxyalkyl, or mercaptoalkyl, and wherein R1 and R2, independently, are as set forth above;
- or
- wherein A is as defined above;
- j is 1 or 2, with the proviso that when j is 1, T is (—NR6R7), and when j is 2, T is a divalent radical having a nitrogen atom directly connected to each carbon atom of the two thiocarbonyl groups;
- wherein R4 and R5, independently, is the same or different, is optionally substituted as defined for R1 and R2, and is a linear or branched alkyl having from 1 to about 12 carbon atoms;
- or an aryl group having from 6 to about 18 carbon atoms, optionally containing heteroatoms;
- or R4 and R5 can form and be part of a substituted or unsubstituted cyclic ring having from 3 to about 12 carbon atoms;
- wherein R6 and R7, independently, is the same or different, optionally substituted as defined for R1 and R2, optionally contains heteroatoms, and is hydrogen;
- or a linear or branched alkyl having from 1 to about 18 carbons;
- or an aryl group or an aryl alkyl group having from 6 to about 18 carbon atoms, optionally saturated or unsaturated;
- or an arylalkyl having from 7 to about 18 carbons;
- or an alkenealkyl having from 3 to about 18 carbon atoms;
- or derived from polyalkylene glycol ether;
- or derived from an amine;
- or R6 and R7 are in the form of a substituted or unsubstituted cyclic ring with the nitrogen atom having a total of 4 to about 12 carbon atoms;
- or
- wherein A is as defined above;
- R4 and R5 are as defined above, wherein R13 is optionally substituted, and is a linear or branched alkyl having from 1 to about 12 carbon atoms, an aryl group optionally saturated or unsaturated;
- an arylalkyl having from about 7 to about 18 carbon atoms;
- an acyl group;
- an alkene group;
- an alkenealkyl having from 3 to about 18 carbon atoms;
- an alkylene group;
- an alkoxyalkyl;
- derived from a polyalkylene glycol;
- derived from a polyalkylene glycol monoalkyl ether having from about 3 to about 200 carbon atoms;
- derived from a polyalkylene glycol monoaryl ether having from about 3 to about 200 carbon atoms, a polyfluoroalkyl;
- a phosphorous containing alkyl;
- or a substituted or unsubstituted aryl ring containing heteroatoms, wherein the R13 substituents comprise an alkyl having from 1 to 6 carbon atoms;
- an aryl;
- a halogen such as fluorine or chlorine;
- a cyano group;
- an amino group;
- an alkene group;
- an alkoxycarbonyl group;
- an aryloxycarbonyl group;
- a carboxy group;
- an acyloxy group;
- a carbamoyl group;
- an alkylcarbonyl group;
- an alkylarylcarbonyl group;
- an arylcarbonyl group;
- an arylalkylcarbonyl group;
- a phthalimido group;
- a maleimido group;
- a succinimido group;
- amidino group;
- guanidimo group;
- allyl group;
- epoxy group;
- alkoxy group;
- an alkali metal salt;
- a cationic substituent;
- a hydroxyl group;
- an ether having a total of from 2 to about 20 carbon atoms;
- a nitro;
- sulfur;
- phosphorous;
- a carboalkoxy group;
- a heterocyclic group containing one or more sulfur, oxygen or nitrogen atoms, or combinations thereof, wherein said “a” is 1 to about 4.
75 more elements
A process for preparing a thickened aqueous composition, comprising the step of:
- mixing water, a latex polymer or copolymer, and a thiocarbonate associative thickener compound, said thiocarbonate compound comprising a reaction product derived from at least one a) hydrophobe group containing monomer;
- b) hydrophilic group containing monomer;
- c) optionally at least one other monomer selected from branched and unbranched (C1 to C8) alkyl esters of (meth)acrylic acid, vinyl acetate;
- styrene;
- diene monomers having a total of from 4 to 12 carbon atoms, a-methyl styrene;
- and C1 to C12 alkyl styrenes with substituent groups either on the main alkyl chain or on the ring or both;
- and d) a thiocarbonate compound having the formula:
- wherein A independently represents hydrogen or a group represented by the formulae:
- wherein R14 is an alkyl group having from about 3 to about 50 carbon atoms;
- wherein R1 and R2, independently, is a linear or branched alkyl having from 1 to about 6 carbon atoms, or a substituted C1 to about C6 alkyl having one or more substituents, or one or more aryls, or a substituted aryl having from 1 to 6 substituents on the aryl ring;
- or wherein R1 and R2 are part of a substituted or unsubstituted cyclic ring having from about 5 to about 12 total carbon atoms;
- wherein said one or more substituents, independently, comprise an alkyl having from 1 to 6 carbon atoms, or an aryl, or a halogen which can be the same or different, or a cyano, or an ether having a total of from 2 to about 20 carbon atoms, or a nitro group, or combinations thereof;
- or
- wherein A is as defined above;
- R3 is benzyl, a C1 through C18 alkyl, or a substituted C1 to C18 alkyl wherein said substituted group is halogen, hydroxyl, or alkoxy, or a C1 to C18 hydroxyalkyl, aralkyl, cyanoalkyl, aminoalkyl, carboxylalkyl, carboalkoxyalkyl, or mercaptoalkyl, and wherein R1 and R2, independently, are as set forth above;
- or
- wherein A is as defined above;
- j is 1 or 2, with the proviso that when j is 1, T is (—NR6R7), and when j is 2, T is a divalent radical having a nitrogen atom directly connected to each carbon atom of the two thiocarbonyl groups;
- wherein R4 and R5, independently, is the same or different, is optionally substituted as defined for R1 and R2, and is a linear or branched alkyl having from 1 to about 12 carbon atoms;
- or an aryl group having from 6 to about 18 carbon atoms, optionally containing heteroatoms;
- or R4 and R5 can form and be part of a substituted or unsubstituted cyclic ring having from 3 to about 12 carbon atoms;
- wherein R5 and R7, independently, is the same or different, optionally substituted as defined for R1 and R2, optionally contains heteroatoms, and is hydrogen;
- or a linear or branched alkyl having from 1 to about 18 carbons;
- or an aryl group or an aryl alkyl group having from 6 to about 18 carbon atoms, optionally saturated or unsaturated;
- or an arylalkyl having from 7 to about 18 carbons;
- or an alkenealkyl having from 3 to about 18 carbon atoms;
- or derived from polyalkylene glycol ether;
- or derived from an amine;
- or R6 and R7 are in the form of a substituted or unsubstituted cyclic ring with the nitrogen atom having a total of 4 to about 12 carbon atoms;
- or
- wherein A is as defined above;
- R4 and R5 are as defined above, wherein R13 is optionally substituted, and is a linear or branched alkyl having from 1 to about 12 carbon atoms, an aryl group optionally saturated or unsaturated;
- an arylalkyl having from about 7 to about 18 carbon atoms;
- an acyl group;
- an alkene group;
- an alkenealkyl having from 3 to about 18 carbon atoms;
- an alkylene group;
- an alkoxyalkyl;
- derived from a polyalkylene glycol;
- derived from a polyalkylene glycol monoalkyl ether having from about 3 to about 200 carbon atoms;
- derived from a polyalkylene glycol monoaryl ether having from about 3 to about 200 carbon atoms, a polyfluoroalkyl;
- a phosphorous containing alkyl;
- or a substituted or unsubstituted aryl ring containing heteroatoms, wherein the R13 substituents comprise an alkyl having from 1 to 6 carbon atoms;
- an aryl;
- a halogen such as fluorine or chlorine;
- a cyano group;
- an amino group;
- an alkene group;
- an alkoxycarbonyl group;
- an aryloxycarbonyl group;
- a carboxy group;
- an acyloxy group;
- a carbamoyl group;
- an alkylcarbonyl group;
- an alkylarylcarbonyl group;
- an arylcarbonyl group;
- an arylalkylcarbonyl group;
- a phthalimido group;
- a maleimido group;
- a succinimido group;
- amidino group;
- guanidimo group;
- allyl group;
- epoxy group;
- alkoxy group;
- an alkali metal salt;
- a cationic substituent such as a quaternary ammonium salt;
- a hydroxyl group;
- an ether having a total of from 2 to about 20 carbon atoms such as methoxy, or hexanoxy;
- a nitro;
- sulfur;
- phosphorous;
- a carboalkoxy group;
- a heterocyclic group containing one or more sulfur, oxygen or nitrogen atoms, or combinations thereof, wherein said “a” is 1 to about 4.
71 more elements
An aqueous composition comprising:
- i) a thiocarbonate associative polymer thickener, said polymer comprising a reaction product polymerized from at least a) a hydrophobe group containing monomer;
- b) a hydrophilic group containing monomer;
- c) optionally at least one other monomer selected from branched and unbranched (C1 to C8) alkyl esters of (meth)acrylic acid, vinyl acetate;
- styrene;
- diene monomers having a total of from 4 to 12 carbon atoms, oc-methyl styrene;
- and C1 to C12 alkyl styrenes with substituent groups either on the main alkyl chain or on the ring or both;
- and d) a thiocarbonate compound having the formula:
- wherein A independently represents hydrogen or a group represented by the formulae:
- wherein R14 is an alkyl group having from about 3 to about 50 carbon atoms;
- R1 and R2, independently, is a linear or branched alkyl having from 1 to about 6 carbon atoms, or a substituted C1 to about C6 alkyl having one or more substituents, or one or more aryls, or a substituted aryl having from 1 to 6 substituents on the aryl ring;
- or wherein R1 and R2 are part of a substituted or unsubstituted cyclic ring having from about 5 to about 12 total carbon atoms;
- wherein said one or more substituents, independently, comprise an alkyl having from 1 to 6 carbon atoms, or an aryl, or a halogen which can be the same or different, or a cyano, or an ether having a total of from 2 to about 20 carbon atoms, or a nitro group, or combinations thereof;
- or
- wherein A is as defined above;
- R3 is benzyl, a C1 to C18 alkyl, or a substituted C1 to C18 alkyl wherein said substituted group is halogen, hydroxyl, or alkoxy, or a C1 to C18 hydroxyalkyl, aralkyl, cyanoalkyl, aminoalkyl, carboxylalkyl, carboalkoxyalkyl, or mercaptoalkyl, and wherein R1 and R2, independently, are as set forth above;
- or
- wherein A is as defined above;
- j is 1 or 2, with the proviso that when j is 1, T is (—NR6R7), and when j is 2, T is a divalent radical having a nitrogen atom directly connected to each carbon atom of the two thiocarbonyl groups;
- wherein R4 and R5, independently, is the same or different, is optionally substituted as defined for R1 and R2, and is a linear or branched alkyl having from 1 to about 12 carbon atoms;
- or an aryl group having from 6 to about 18 carbon atoms, optionally containing heteroatoms;
- or R4 and R5 can form and be part of a substituted or unsubstituted cyclic ring having from 3 to about 12 carbon atoms;
- wherein R6 and R7, independently, is the same or different, optionally substituted as defined for R1 and R2, optionally contains heteroatoms, and is hydrogen;
- or a linear or branched alkyl having from 1 to about 18 carbons;
- or an aryl group or an aryl alkyl group having from 6 to about 18 carbon atoms, optionally saturated or unsaturated;
- or an arylalkyl having from 7 to about 18 carbons;
- or an alkenealkyl having from 3 to about 18 carbon atoms;
- or derived from polyalkylene glycol ether;
- or derived from an amine;
- or R6 and R7 are in the form of a substituted or unsubstituted cyclic ring with the nitrogen atom having a total of 4 to about 12 carbon atoms;
- or
- wherein A is as defined above;
- R4 and R5 are as defined above, wherein R13 is optionally substituted, and is a linear or branched alkyl having from 1 to about 12 carbon atoms, an aryl group optionally saturated or unsaturated;
- an arylalkyl having from about 7 to about 18 carbon atoms;
- an acyl group;
- an alkene group;
- an alkenealkyl having from 3 to about 18 carbon atoms;
- an alkylene group;
- an alkoxyalkyl;
- derived from a polyalkylene glycol;
- derived from a polyalkylene glycol monoalkyl ether having from about 3 to about 200 carbon atoms;
- derived from a polyalkylene glycol monoaryl ether having from about 3 to about 200 carbon atoms, a polyfluoroalkyl;
- a phosphorous containing alkyl;
- or a substituted or unsubstituted aryl ring containing heteroatoms, wherein the R13 substituents comprise an alkyl having from 1 to 6 carbon atoms;
- an aryl;
- a halogen such as fluorine or chlorine;
- a cyano group;
- an amino group;
- an alkene group;
- an alkoxycarbonyl group;
- an aryloxycarbonyl group;
- a carboxy group;
- an acyloxy group;
- a carbamoyl group;
- an alkylcarbonyl group;
- an alkylarylcarbonyl group;
- an arylcarbonyl group;
- an arylalkylcarbonyl group;
- a phthalimido group;
- a maleimido group;
- a succinimido group;
- amidino group;
- guanidimo group;
- allyl group;
- epoxy group;
- alkoxy group;
- an alkali metal salt;
- a cationic substituent;
- a hydroxyl group;
- an ether having a total of from 2 to about 20 carbon atoms;
- a nitro;
- sulfur;
- phosphorous;
- a carboalkoxy group;
- a heterocyclic group containing one or more sulfur, oxygen or nitrogen atoms, or combinations thereof, wherein said “a” is 1 to about 4;
- and
- ii) one or more components selected from chelators, conditioners, diluents, fragrances, pigments, dyes, colorings, antioxidants, humectant skin and hair conditioners, auxiliary fixatives, auxiliary rheology modifying agents, silicone oil, silicone fluids, moisturizers, plasticizers, pearlescenting agents, oxidizing agents, reducing agents, lubricants, moisture barriers, emollients, emulsifiers, neutralizers, opacifiers, pharmaceutical actives, preservatives, solvents, spreading aids, sunscreens, surfactants, conditioning polymers, vitamins, viscosity adjusters, proteins, protein derivatives, antimicrobial agents, antifungal agents, botanicals, UV absorbing agents, antidandruff agents, anticaries agents, antitartar agents, abrasives, and anti-acne agents.
73 more elements
Dependencies are inferred from the claim text.