WO2005092273A2 - Procedes de compatibilisation de materiaux cationiques avec des polymeres anioniques - Google Patents

Procedes de compatibilisation de materiaux cationiques avec des polymeres anioniques Download PDF

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WO2005092273A2
WO2005092273A2 PCT/US2005/003450 US2005003450W WO2005092273A2 WO 2005092273 A2 WO2005092273 A2 WO 2005092273A2 US 2005003450 W US2005003450 W US 2005003450W WO 2005092273 A2 WO2005092273 A2 WO 2005092273A2
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carbons
chloride
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anionic
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WO2005092273A3 (fr
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Brian Jay Vondruska
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Noveon IP Holdings Corp
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0091—Complexes with metal-heteroatom-bonds

Definitions

  • Anionic polymers are employed in many end-use applications.
  • Rheology modifiers thickeners
  • Some of the most useful anionic polymers are based on ethylenically unsaturated carboxylic acid monomers which includes crosslinked polyacrylic acid or copolymers of ethylenically unsaturated carboxylic acid monomers and copolymerizable vinyl monomers.
  • Such polymers yield anionic polymers that are extremely useful in various personal care products in the cosmetic and toiletry industries as well as in a variety of other applications, such as coatings (paper, textiles, nonwovens, fibers) and others.
  • U.S. Patent 4.210.161 discloses a cream rinse composition comprising an anionic polymer and a cationic surfactant capable of forming a water insoluble reaction product.
  • this patent clearly states that the anionic polymer and a cationic surfactant are incompatible and do form a precipitate but in this formulation, such a precipitate is desirable.
  • U.S. Patent 4,710.374 discloses cosmetic compositions containing a cationic polymer and an anionic polymer latex.
  • the patent disclosure clearly stresses that the cationic polymer is of a relatively high molecular weight of between 500 to 3,000,000 but most, if not all, appear to be at least 10,000 molecular weight and more often, about 500,000 molecular weight.
  • the cationic ingredient is a large molecule with a low charge density. For this reason, the cationic polymer and the anionic polymeric latex are not truly incompatible.
  • U.S. Patent 6,071.499 discloses cosmetic compositions with an anionic acrylic polymer and an oxyalkylenated silicone which is nonionic. Since the silicone is not anionic, it cannot complex with a cationic ingredient although it is said to improve the performance of such anionic polymer.
  • the invention is directed to a method of compatibilizing anionic polymers with cationic materials, such as cationic surfactants, cationic polymers or cationic salts, which method comprises complexing the cationic material with an anionic complexing agent before combining the complexed cationic material with an anionic polymer.
  • the invention is further directed to a composition comprising an anionic polymer and a complexed cationic material and to compositions containing an anionic polymer and a cationic material complexed with an anionic complexing agent.
  • cationic materials are incompatible with anionic polymers, when they are combined usually a precipitate forms, or turbidity develops and some of the properties, such as thickening, of the anionic polymers are generally substantially altered.
  • the incompatible anionic polymer thickeners and the cationic materials become compatibilized.
  • compatibilized cationic material(s) is combined with an anionic polymer, the viscosity/turbidity profile of the resulting compositions is substantially improved.
  • the complexing of the cationic materials prior to combining them with anionic polymers either reduced or eliminated excessive turbidity and the tendency to form precipitates.
  • the truly unexpected feature of the present invention is the fact that the cationic materials, which generally are not compatible with anionic polymers, can be made compatible by first complexing them with an anionic compatibilizing agent without negatively affecting the performance and function of the cationic materials.
  • the cationic materials that may be compatibilized with anionic polymers are quaternary ammonium salts, polyquaternary ammonium salts, organic or inorganic salts, alkyl amines, amidoamines, ethoxylated amines, alkyl imidazolines and various cationic polymers.
  • incompatible is meant that when such cationic materials are combined with anionic polymers, either a precipitate forms or turbidity develops.
  • cationic materials When cationic materials are added to a formulation containing an anionic polymer, generally a precipitate and/or turbidity develops which is unacceptable for many products, such as personal care, coatings, household products or in other uses.
  • This long existing difficulty can be overcome and such materials can be compatibilized by the instant invention, wherein cationic materials are first complexed with a compatibilizing agent which is an anionic bulky molecule containing an anionic group such as a sulfate, sulfonate, phosphate, phosphonate or carboxylate groups.
  • a compatibilizing agent which is an anionic bulky molecule containing an anionic group such as a sulfate, sulfonate, phosphate, phosphonate or carboxylate groups.
  • substantially reduction is meant a reduction to such a degree that such materials (the cationic materials and the anionic polymers) can be successfully employed in a particular end-use product.
  • reduction would constitute at least a 50% reduction of turbidity formation and preferably at least 80% reduction, such that the turbidity of compositions or formulations containing both cationic material(s) and anionic polymer(s) is not greater than 50, often 20 NTU and preferably 15 NTU or less.
  • the turbidity be 15 NTU or less and preferably 10 NTU or less. The level of turbidity that is considered acceptable always depends on the end-use application.
  • complexed anionic materials of this invention also aid in efficient use of anionic polymers by often enabling the use of a lesser amount of an anionic polymer yet obtaining desirable properties, thus making the resulting products more cost efficient. There should be practically a complete elimination of precipitate formation.
  • the cationic materials are not compatible with the anionic polymers. However, if the concentration of a cationic material is low enough, they may be compatible. Similarly, if the charge density is low enough (e.g. the charge moiety(s) is dispersed sparcely throughout the molecule) they may also be compatible. Consequently, this invention deals with compatibilizing cationic materials that are incompatible with the anionic polymers.
  • Cationic materials are commonly used as surfactants and as conditioning materials.
  • Quaternary ammonium compounds i.e. quats
  • Polyquats are the polymeric counterparts of quats and are used in the same manner as quats, and for the same general purposes. They have additional utility as fixatives and rheology modifiers, due to their high molecular weight. Any cationic materials that are incompatible with any anionic polymers may be made compatible employing the present invention.
  • cationic materials are listed below.
  • the cationic polymers that may be compatibilized with anionic polymers according to the invention are especially polymers of the polyamine, polyaminoamide or poly-(quaternary ammonium) type, the amino and/or ammonium group forming part of the polymer chain or being joined thereto.
  • anionic polymers are especially polymers of the polyamine, polyaminoamide or poly-(quaternary ammonium) type, the amino and/or ammonium group forming part of the polymer chain or being joined thereto.
  • these polymers the following may be mentioned in particular:
  • Vinylpyrrolidone/dialkylaminoalkyl acrylate or methacrylate copolymers such as those sold under the name Gafquat®, such as "copolymer 845" and Gafquat® 734 or 755, described in greater detail in particular in U.S. Patents 3,910,862 and 4,126,537 which are incorporated herein by reference.
  • Cellulose ether derivatives containing quaternary ammonium groups such as those described in U.S. Patent 3,472,840, and cationic cellulose derivatives, such as those described in U.S. Patent No. 4,131,576 which are incorporated herein by reference.
  • Cationic polysaccharides such as those described in U.S. Patent Nos. 3,589,978 > and 4,031,357, which are incorporated herein by reference, and in particular Jaguar® C, 13 S sold by Meyhall.
  • Cationic polymers chosen from the group comprising: (a) Polymers containing units of the formula: — A 4 — Z— A 4 — Z (I) in which A denotes a radical containing two amino groups, preferably a piperazinyl radical, and Z denotes the symbol B or B' .
  • B and B' which are identical or different, denote a divalent radical which is a straight-chain or branched-chain alkylene radical which contains up to 7 consecutive carbon atoms in the main chain, which is unsubstituted or substituted by hydroxyl groups and which can also contain oxygen, nitrogen and sulphur atoms and 1 to 3 aromatic and/or hetero-cyclic rings, the oxygen, nitrogen and sulphur atoms being present in the form of ether or thioethers, sulphoxide, sulphone, sulphonium, amine, alkylamine, alkenylamine, benzylamine, amine oxide, quaternary ammonium, amide, imide, alcohol, ester and/or urethane groups; these polymers and the process for their preparation are described in French Patent No.
  • A denotes a radical containing two amino groups, preferably a piperazinyl radical, and Zi denotes the symbol Bi or and denotes the symbol B' ⁇ at least once;
  • Bi denotes a divalent radical which is a straight-chain or branched-chain alkylene or hydroxyalkylene radical having up to 7 consecutive carbon atoms in the main chain, and
  • B' ⁇ is a divalent radical which is a straight-chain or branched-chain alkylene radical which has up to 7 consecutive carbon atoms in the main chain, which is unsubstituted or substituted by one or more hydroxyl radicals and which is interrupted by one or more nitrogen atoms, the nitrogen atom being substituted by an alkyl chain which has from 1 to 4 carbon atoms, and preferably 4 carbon atoms, which is optionally interrupted by an oxygen atom and which optionally contains one or more hydroxyl groups.
  • Optionally alkylated, crosslinked polyamino polyamides chosen from the group comprising at least one water-soluble crosslinked polymer obtained by crosslinking a polyaminopolyamide (A) prepared by the polycondensation of an acid compound with a polyamine.
  • the acid compound is chosen from (i) organic dicarboxylic acids, (ii) aliphatic monocarboxylic and dicarboxylic acids with a double bond, (iii) esters of the above- mentioned acids, preferably the esters with lower alkanols having from 1 to 6 carbon atoms, and (iv) mixtures of these compounds.
  • the polyamine is chosen from amongst bis-primary, mono-secondary or bis-secondary polyalkylenepolyamines. Up to 40 mol % of this polyamine can be replaced by a bis-primary amine, preferably ethylenediamine, or by a bis- secondary amine, preferably pipereazine, and up to 20 mol % can be replaced by hexamethylenediamine.
  • crosslinking is carried out by means of a crosslinking agent (B) chosen from amongst epihalogenohydrins, diepoxides, dianhydrides, unsaturated anhydrides and bis-unsaturated derivatives, suitably in proportions of 0.025 to 0.35 mol of crosslinking agent per amino group of the polyaminopolyamide (A).
  • the alkylation can be carried out, if appropriate with glycidol, ethylene oxide, propylene oxide or acrylamide.
  • polyaminopolyamides (A) themselves can also be used according to the invention.
  • crosslinked polyaminopolyamides obtained by crosslinking a polyaminopolyamide (A) described above by means of a crosslinking agent chosen from the group comprising: (I) compounds chosen from the group comprising (1) bis-halogenohydrins, (2) bis-azetidinium compounds, (3) bis-halogenoacyl-diamines and (4) bis-(alkyl halides); (II) the oligomers obtained by reacting a compound (a) chosen from the group comprising (1) bis-halogenohydrins, (2) bis-azetidinium compounds, (3) bis-halogenoacyl- diamines, (4) bis-(alkyl halides), (5) epihalogenohydrins, (6) diepoxides and (7) bis- unsaturated derivatives, with a compound (b) which is a difunctional compound reactive towards the compound (a); and (III) the quaternization product of a compound chosen from the group comprising the compounds (a) and the
  • polyaminopolyamide derivatives resulting from the condensation of a poly- alkylenepolyamine with a polycarboxylic acid, followed by alkylation by means of difunctional agents, such as adipic acid/dialkylaminohydroxyalkyl-dialkylenetriamine copolymers in which the alkyl radical contains 1 to 4 carbon atoms and preferably denotes methyl, ethyl or propyl, which are described in U.S. Patent No. 3,632,559, which is incorporated herein by reference.
  • Cyclic polymers generally having a molecular weight of 20,000 to 3,000,000, such as homopolymers containing, as the main constituent of the chain, units corresponding to the formula (III) or (III'): ⁇ ⁇
  • R 53 denotes hydrogen or methyl
  • R 51 and R 52 independently of one another denote an alkyl group having from 1 to 22 carbon atoms, a hydroxyalkyl group in which the alkyl group preferably has 1 to 5 carbon atoms, or a lower amidoalkyl group, and R and R can denote, together with the nitrogen atom to which they are attached, heterocyclic groups such as a piperidinyl or morpholinyl
  • Y ⁇ is an anion such as bromide, chloride, acetate, borate, citrate, tartrate, bisulphate, bisulphate, sulphate or phosphate and also copolymers containing units of the formulas III or IIP and units derived from acrylamide or from diacetone-acrylamide.
  • Rj. and R 2 , and R 3 and R which are identical or different, represent aliphatic, alicyclic or arylaliphatic radicals containing at most 20 carbon atoms, or lower hydroxyaliphatic radicals, or alternative ⁇ and R , and R 3 and R ⁇ together or separately form, with the nitrogen atoms to which they are attached, heterocyclic rings optionally containing a second hetero-atom other than nitrogen, or alternatively R ls R 2 , R 3 and j represent a group EU. — R'-
  • R' 3 denoting hydrogen or lower alkyl and R 4 denoting o o R'.
  • CN CN;— C— N ; — C — OR 5 ; - C R' 5 or ⁇ R'6 O O C II- O R' 7 — D; C II— NH— R' 7 -D,
  • R' 5 denoting lower alkyl
  • R' 6 denoting hydrogen or lower alkyl
  • R' denoting alkylene and D denoting a quaternary ammonium group
  • a 2 and B 2 can represent polymethylene groups containing from 2 to 20 carbon atoms, which can be linear or branched and saturated or unsaturated and which can contain, inserted into the main chain, one or more aromatic rings such as the group
  • a 2 and Rl and R3 form a piperazine ring with the two nitrogen atoms to which they are attached; moreover, if A 2 denotes a linear or branched, saturated or unsaturated alkylene or hydroxyalkylene radical, B 2 can also denote a group— (CH 2 -) n C(0)-D— (0)C-(CH )- n. in which D denotes: (a) a glycol radical of the formula — O — Z' — O — , in which Z' denotes a linear or branched hydrocarbon radical or a group corresponding to the formulae:
  • x and y denote an integer from 1 to 4, representing a definite and unique degree of polymerization (in the case of a single compound), or any number from 1 to 4, representing an average degree of polymerization (in the case of a mixture);
  • a bis-secondary diamine radical such as a piperazine derivative;
  • n is such that the molecular weight is generally from 1,000 to 100,000 and
  • X ⁇ denotes an anion.
  • R 10 is H or CH 3
  • a 3 is a linear or branched alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group having 1 to 4 carbon atoms
  • R 2 o, R o and R 4 which are identical or different, denote an alkyl group having 1 to 18 carbon atoms or a benzyl group
  • R 50 and R 60 denote H or alkyl having 1 to 6 carbon atoms
  • X denotes methosulphate or halogen, such as chlorine or bromine.
  • the comonomer or comonomers which can be used include: acrylamide, methacrylamide, diacetoneacrylamide, acrylamide and methacrylamide substituted on the nitrogen by one or more lower alkyls, acrylic and methacrylic acid esters, vinylpyrrolidone and vinyl esters.
  • the acrylamide/beta- methacryloyloxethyl-trimethylammonium methosulphate copolymers the aminoethylacrylate phosphate/acrylate copolymer, and the graft crosslinked cationic copolymers, having a molecular weight of 10,000 to 1,000,000 and preferably of 15,000 to 500,000.
  • These polymers are described in U.S. Patent No. 3,946,749, which is incorporated herein by reference.
  • the cosmetic monomer can be of a very wide variety of types, for example a vinyl ester, an allyl or methallyl ester, an acrylate or methacrylate of a saturated alcohol having from 1 to 18 carbon atoms, an alkyl vinyl ether, an olefin, a vinylic heterocyclic derivative, a dialkyl or N,N-dialkylaminoalkyl maleate or an unsaturated acid anhydride.
  • Quaternary polymers of vinylpyrrolidone and vinylimidazole such as LUVIQUAT FC 905.
  • Cationic silicone polymers such as those described in European Patent Nos. 0017121 BI and 0017122 BI and U.S. Patent No. 4,185,087, which are incorporated herein by reference.
  • Cationic derivatives of starches or of starch ethers such as those described in Great Britain Patent No. 2063282 which is incorporated herein by reference.
  • cationic polymers which can be used include polyalkyleneimines, in particular polyethyleneimines, polymers containing vinylpyridinium units in the chain, polyamine/ epichlorohydrin condensates, poly-(quaternary ureylene) compounds and chitin derivatives.
  • the compatibilizing agents or complexing agents which complex with the cationic materials may be any material that contains a "bulky” molecule having an anionic group.
  • the "bulky” molecule should not be reactive chemically with either the anionic polymer or the cationic material.
  • the "bulky” molecule will generally have a molecular weight of at leasat 500 Mn, preferably at least 1,000 Mn, and may have a molecular weight of up to 50,000 Mn, but generally up to 25,000 Mn.
  • the "bulky” molecule is a polymeric material having at least three repeat units.
  • composition of the polymeric materials may be heterogeneous and predominantly may be polysilicones, acrylic copolymers, polyalkylene glycol such as polyethylene glycol and polypropylene glycol, polyvinyl alcohol, polyvinyl acetate, polysaccharide such as starch and cellulose or polyurethane.
  • Polyalkylene glycols may contain terminal groups such as, but not limited to, allyl, propenyl, propyl and hydrogen or others. These polymeric or "bulky” groups must contain anionic groups that will complex with the cationic materials.
  • the preferred anionic groups are carboxylate (-COOH), sulfonate (-SO 3 H), sulfate (-OSO 3 H), phosphate (-OP(OH) 2 ) and phosphonate (-PO(OH) 2 ).
  • the anionic groups complex with the cationic materials preventing the cationic materials from interfering with the anionic polymer and permitting the anionic polymer to perform its function, such as the viscosity building function in the case of thickeners or a film forming function in the case of a coating.
  • any polymeric material containing anionic groups may be employed, it is preferable to employ silicones, especially in personal care products.
  • the compatibilizing agent can be any material that contains a "bulky” molecule having an anionic group, but the complexing agent must be compatible with the cationic material.
  • compatible is meant that the complexing agent and the cationic material do not form a precipitate. Consequently, it is possible that a particular complexing agent may be compatible with certain category or categories of cationic materials but incompatible with different cationic materials. It is also possible that a particular anionic polymer may be compatible with a particular type of cationic material and, therefore, can function as a complexing agent in compatibilizing such cationic material with anionic polymers which are not compatible with such cationic materials. In other words, certain anionic polymers may function as complexing agents, but with respect to other cationic materials, with which those certain anionic polymers are not compatible, different complexing agents must be employed to compatibilized those cationic materials with those certain anionic polymers.
  • the preferred silicone complexing agents may be represented generically ( I )
  • Me is methyl; R and R' are independently selected from methyl, -OH, -R 7 , and -R 9 -A or -(CH 2 ) 3 -O-(EO) a -(PO) b -(EO) c -G with the proviso that both R and R' are not methyl, -OH or R 7 ;
  • R 1 is selected from lower alkyl CH 3 (CH 2 ) n - or phenyl where n is an integer from 0 to 22; a, b, and c are integers independently ranging from 0 to 100; EO is -(CH 2 CH 2 O)-; CH 3 I PO is - (CH 2 CHO)-; o is an integer ranging from 1 to 200; q is an integer ranging from 0 to 1000; p is an integer ranging from 0 to 200;
  • R 7 is aryl, alkyl, aralkyl, alkaryl, or alkenyl group of 1-40 carbons;
  • R 8 is hydrogen or R 7 or C(O)-X wherein X is aryl, alkyl, aralkyl, alkaryl, alkenyl group of 1-
  • R 9 is divalent group selected from alkylene of 1-40 carbons which may be interrupted with arylene group of 6 to 18 carbons or an alkylene group containing unsaturation of 2 to 8 carbons;
  • a and G are independently are selected from
  • R is a divalent group selected from alkylene of 1-40 carbons which may be interrupted with an arylene group of 6 to 18 carbons or an alkylene group of 2 to 8 carbons, and is preferably selected from the
  • M is Na, K, Li, NIL; or an amine containing alkyl, aryl, akenyl, hydroxyalkyl, arylalkyl or alkaryl groups.
  • silicone complexing agents is silicone sulfates which may be represented by the following formula:
  • R is selected from lower alkyl having one to eight carbon atoms or phenyl
  • R 12 is -(CH 2 ) 3 -O-(EO) x -(PO) y -(EO) z -SO 3 JM ⁇
  • M is a cation and is selected from Na, K, Li, or NEU; x, y and z are integers independently ranging from 0 to 100;
  • R 13 is -(CH 2 ) 3 -O-(EO) x - (PO) y -(EO) z -H
  • R 14 is methyl or hydroxyl
  • a 1 and c 1 are independently integers ranging from 0 to 50
  • b 1 is an integer ranging from 1 to 50;
  • a still further category of silicone complexing agents may be represented as follows:
  • R is alkyl having from 1 to 22 carbon atoms;
  • R 31 is selected from lower alkyl (having 1-4 carbons), CH 3 (CH) n 1 - and phenyl;
  • n 1 is an integer from 0 to 8;
  • a 3 , b 3 and c 3 are integers independently ranging from 0 to 20;
  • EO is an ethylene oxide residue -(CH CH 2 -O)-;
  • PO is a propylene oxide residue -(CH 2 CH(CH 3 )-O- ) ;
  • o 1 is an integer ranging from 1 to 200;
  • q 1 is an integer ranging from 0 to 500. It should be noted that in the above structure units EO and PO may be in random and block structures.
  • Such silicone carboxylates are disclosed in greater detail in U.S. Patent 5,296,625, the disclosure of which is incorporated herein by reference.
  • Still fiirther silicone complexing agents are silicones containing a multiplicity of different anionic substituents.
  • Such silicones can be prepared by reacting two or more types of anionic silicones already disclosed using reactions well known to those in the art. The resulting molecule could be a hybrid of the starting silicones and would, therefore, contain multiple types of anionic functional groups. The properties of the silicone can be optimized in such a fashion.
  • One type of reaction, the silicone equilibration reaction involves charging a reactor with raw materials, adding a suitable catalyst, mixing with heat, and then neutralizing the catalyst. The Chemistry is discussed in Silicone in Organic, Organometallic and Polymer Chemistry (Michael Brook) - John Wiley and Sons, New York, 2000, pp. 261-266.
  • the amount of the anionic complexing agent required to complex the cationic materials will depend on the specific cationic materials (the quat, polyquat, organic salt, etc.), the amount of the cationic materials present and the overall pH of the final formulation. The lower the pH of the final formulation, the greater the amount of the complexing agent is required. In view of the above-mentioned variables, it will be necessary to conduct some routine testing to arrive at the optimum amount of the anionic complexing agent, such as a silicone, to be used in a particular formulation to provide the desired results.
  • the weight ratio of the anionic complexing agent, such as the anionic silicone complexing agent, to the cationic material or materials will be in the range of 0.1-10.1.
  • the weight ratio of the complexing agent to the cationic ingredient(s) will be 0.5-6 to 1 and most preferably 1.5-3 to 1.
  • the anionic polymers which are generally not compatible with cationic materials can be homopolymers obtained from ethylenically unsaturated monomers containing acid moieties, such as carboxyl, phosphate, phosphonate, sulfate, sulfonate, phenolic, or any other moiety having a labile hydrogen that can be removed from the moiety to provide a negatively charged site on the polymer or ethylenically unsaturated monomers derived from those that contain carboxylic groups, such as acid hydrides, anhydrides or esters.
  • acid moieties such as carboxyl, phosphate, phosphonate, sulfate, sulfonate, phenolic, or any other moiety having a labile hydrogen that can be removed from the moiety to provide a negatively charged site on the polymer or ethylenically unsaturated monomers derived from those that contain carboxylic groups, such as acid hydrides, anhydrides or esters.
  • the anionic polymers may also be copolymers of ethylenically unsaturated monomers containing the above-noted acid moieties and one or more monomer(s) that are copolymerizable with the acid group- containing monomers.
  • Such copolymers will contain at least 1% by weight of one or more acid groups containing monomer(s) or anhydride monomer(s), preferably at least 5% and more preferably at least 10% and often at least 25%.
  • Prior art discloses a variety of such homopolymers and copolymers, some of which may be rheology modifiers (thickeners) and others may be non-thickeners that do not substantially and effectively modify rheology of a composition to which an anionic polymer has been added.
  • non-thickener polymers are very similar, or in some cases identical, to those of thickener polymers.
  • the more notable difference between the two types of polymers are performance-related. Although chemical differences exist, they are subtle and not always evident.
  • An adjustment in polymer architecture or charge density, a small change in composition, a slight increase or decrease in the amount of a certain monomer or crosslinker can all make the difference between a thickener and a non-thickener.
  • a thickener is a material or an ingredient in a formulation whose function is to provide a viscosity increase, stabilize suspended ingredients such as solid particles or emulsion droplets, and/or to otherwise modify the rheology of the formulation.
  • Rheology modifiers are well known in the art and can be prepared from synthetic and/or natural polymers. Thickening may be the primary function of the ingredient, or a secondary effect. Thickeners are usually used at ⁇ 10 weight percent in a formulation, and more preferably ⁇ 5%. Some very efficient thickeners are used at ⁇ 1% levels.
  • anionic polymers includes anionic rheology modifiers (thickeners).
  • This category of polymers that includes homopolymers and copolymers, has been disclosed in the parent patent application, U.S. Serial No. 10/653,609, filed September 2, 2003, which disclosure is incorporated herein by reference.
  • the present application deals with compatibilizing cationic materials with anionic polymers that are preferably non- thickeners, that is, polymers that have useful properties other than as rheology modifiers.
  • Carboxylic monomers are an important category of acid moiety-containing monomers from which anionic homopolymers and copolymers, other than thickeners, may be prepared.
  • non-thickener is meant that such polymers may possess no thickener or rheology modifying property or that the polymers may exhibit some thickening property but not sufficient to be categorized as a commercially viable rheology modifier.
  • CH 2 C ⁇ .
  • the close proximity of the strongly polar carboxyl group to the double-bonded carbon atoms has a strong activating influence rendering the substances containing this structure very readily polymerizable.
  • the presence of a terminal methylene grouping in a carboxylic monomer makes this type of compound much more easily polymerizable than if the double bond were intermediate in the carbon structure.
  • Olefinically-unsaturated acids of this class include such widely divergent materials as the acrylic acids typified by acrylic acid itself, methacrylic acid, ethacrylic acid, alpha-chloroacrylic acid, alpha-cyano acrylic acid, beta methyl-acrylic acid (crotonic acid), alpha-phenyl acrylic acid, beta-acryloxy propionic acid, sorbic acid, alpha-chloro sorbic acid, angelic acid, cinnamic acid, p-chloro cinnamic acid, beta-styryl acrylic acid (l-carboxy-4-phenyl butadiene- 1,3), itaconic acid, citraconic acid, messaconic acid, glutaconic acid, aconitic acid, maleic acid, fumaric acid, and tricarboxy ethylene.
  • acrylic acids typified by acrylic acid itself, methacrylic acid, ethacrylic acid, alpha-chloroacrylic acid, alpha-cyano acrylic acid,
  • carboxylic acid includes the polycarboxylic acids and those acid anhydrides, such as maleic anhydride, wherein the anhydride group is formed by the elimination of one molecule of water from two carboxyl groups located on the same polycarboxylic acid molecule.
  • Anhydrides of the types formed by elimination of water from two or more molecule ' s of the same or different unsaturated acids, such as acrylic anhydride, are not included because of the strong tendency of their polymers to hydrolyze in water and alkali.
  • Maleic anhydride and the other acid anhydrides useful herein have the general structure:
  • R 40 and R 41 are independently selected from the group consisting of hydrogen, cyanogens (-C ⁇ N), hydroxyl, lactam and lactone groups and alkyl, aryl, alkaryl, aralkyl, and cycloalkyl groups such as methyl, ethyl, propyl, octyl, decyl, phenyl, tolyl, xylyl, benzyl, cyclohexyl and the like.
  • the preferred carboxylic monomers for use in preparing non-thickener anionic polymers are the monoolefmic acrylic acids having the general structure R 42
  • R 42 is a substituent selected from the class consisting of hydrogen, halogen, hydroxyl, lactone, lactam cyanogen (-CN), monovalent alkyl group (1 to 4 carbons), monovalent aryl group (6 to 12 carbons), monovalent aralkyl group (7 to 12 carbons), monovalent alkaryl group (7 to 12 carbons) and monovalent cycloaliphatic group (4 to 8 carbons).
  • R 42 is a substituent selected from the class consisting of hydrogen, halogen, hydroxyl, lactone, lactam cyanogen (-CN), monovalent alkyl group (1 to 4 carbons), monovalent aryl group (6 to 12 carbons), monovalent aralkyl group (7 to 12 carbons), monovalent alkaryl group (7 to 12 carbons) and monovalent cycloaliphatic group (4 to 8 carbons).
  • acrylic acid and methacrylic acid are most preferred because of its generally lower cost, ready availability, and ability to form superior polymers.
  • Another particularly preferred carboxylic monomer is maleic anhydr
  • other ethylenically unsaturated acid group-containing monomers may be vinyl sulfonic acids, vinylsulfuric acid, vinylphosphonic acids, vinylaromatic acids wherein the acid groups are carboxylic, sulfonic, sulfuric or phosphonic, and even phenolic; that is, any moiety having a labile hydrogen that can be removed from the moiety to provide a negatively charged site on the polymer.
  • Such acidic monomers are vinylsulfonic acid, styrenesulfonic acid, 2- methacroyloxyethane-1 -sulfonic acid, 3-(vinyloxy) propane- 1 -sulfonic acid, 3- methacryloxypropane-1 -sulfonic acid, vinylsulfuric acid, vinylphos- phine acid, 4- vinylbenzoic acid, 4-vinylphenol, 4-vinylphenyl sulfiiric acid, N-vinylsuccinamidic acid and other similar acids.
  • An anionic polymer containing an aromatic monomer can be sulfonated, sulfated or phosphonated to position an acid group on the aromatic monomer.
  • the above-discussed acid group-containing monomers may be homopolymerized or copolymerized with a variety of other monomers, especially vinyl type.
  • An important group of comonomers are acrylic ester monomers having long chain aliphatic groups which are derivatives of acrylic acid represented by the formula
  • R 44 O I II CH 2 C — C — O — R 43 wherein R 43 is hydrogen or an alkyl group having from 1 to 30 carbon atoms, preferably 10 to 22 carbon atoms and R 44 is hydrogen or a methyl group.
  • Representative acrylates include methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, butyl acrylate, isobutyl acrylate, methyl methacrylate, methyl ethacrylate, ethyl methacrylate, octyl acrylate, heptyl acrylate, octyl methacrylate, isopropyl methacrylate, 2-ethylhexyl acrylate, nonyl acrylate, hexyl acrylate, n-hexyl methacrylate, and the like; higher alkyl acrylic esters are decyl acrylate, isodecyl methacrylate, lau
  • acrylic nitriles, ⁇ , ⁇ - olefinically unsaturated nitriles useful are preferably the monoolefinically unsaturated nitriles having from 3 to 10 carbon atoms such as acrylonitrile, methacrylonitrile, ethacrylonitrile, chloroacrylonitrile, and the like.
  • Acrylic amides include monoolefinically unsaturated amides also may be used. These have at least one hydrogen on the amide nitrogen and the olefinic unsaturation is alpha-beta to the carbonyl group.
  • amides include acrylamide, methacrylamide, N-methylacrylamide, N-t-butyl acrylamide, N-cyclohexyl acrylamide, N-ethyl acrylamide and others.
  • Other N-alkylol amides of alpha, betaolefinically unsaturated carboxylic acids including those having from 4 to 10 carbon atoms such as N- methylol acrylamide, N-ethanol acrylamide, N-propanol acrylamide, N-methylol methacrylamide, N-ethanol methacrylamide, N-methylol maleimide, N-methylol maleamide, N-methylol maleamic acid, N-methylol maleamic acid esters, the N-alkylol amides of the vinyl aromatic acids such as N-methylol-p-vinyl benzamide, and the like and others.
  • N- alkoxymethyl acrylamides also may be used.
  • vinylidene comonomers include ⁇ -olef ⁇ ns containing from 2 to 12 carbon atoms, dienes containing from 4 to 10 carbon atoms; vinyl esters and allyl esters such as vinyl acetate; vinyl aromatics such as styrene, methylstyrene, cholorstyrene, vinyl and allyl ethers and ketones such as vinyl methyl ether and methyl vinyl ketone; chloroacrylates, cyanoalkyl acrylates such as ⁇ -cyanomethyl acrylate, the ⁇ -, ⁇ and ⁇ -cyanopropyl acrylate, alkoxyacrylates such as methoxy ethyl acrylate; haloacrylates as chloroethyl acrylate, vinyl halides and vinyl chloride, vinylidene chloride and the like; vinyl benzyl chlorides; esters of maleic and fumaric acid and the like; divinyls, diacrylates and other polyfunctional mono
  • copolymers are disclosed in greater detail in U.S. Patent 4,419,502 which is incorporated herein by reference.
  • Also useful comonomers are alkoxyalkyl acrylates, methacrylates or esters of the other above-metioined unsasturated carboxylic acids wherein the alkyl groups have 1 to 18 carbons.
  • Another class of comonomers that may be employed in preparing anionic polymers is associative monomers which is an ester of formula J-0-(CH 2 -CHR 22 0) r -(CH 2 ) s -R ⁇ wherein J is an ethylenically unsaturated acrylic residue, optionally containing an additional carboxylic group, wherein, optionally, said additional carboxylic group may be esterified with a (C !
  • R ⁇ is an alkyl, alkylphenyl or aralkyl residue having from 1 to 30 carbon atoms
  • R 2 is hydrogen or alkyl of 1 to4 carbons
  • r is comprised between 0 and 50
  • s is comprised between 0 and 30.
  • the associative monomer may be any compound falling within the above formula J-0-(CH 2 -CHR 22 0) r -(CH 2 ) s -R ⁇ wherein R ⁇ and R 22 are as above indicated, the sum of r and s may vary between 0 and 80 and J is the acrylic residue of an ethylenically unsaturated acid selected from acrylic, methacrylic, itaconic, maleic, sorbic, crotonic, oleic and linoleic acids. Preferred are the esters of cetylstearyl alcohol ethoxylated with 25 moles of ethylene oxide.
  • the associative monomers are commercially available products, or they can be prepared substantially according to procedures known in the art (U.S. Patent Nos. 3,652,497 and 4,075,411).
  • Crosslinking monomers may be employed in anionic polymers, if desired.
  • a preferred class is polyalkenyl polyether having more than one alkenyl ether grouping per molecule.
  • the most useful possess alkenyl groups in which an olefinic double bond is present attached to a terminal methylene grouping, CH 2 C ⁇ . They are made by the etherification of a polyhydric alcohol containing at least 4 carbon atoms and at least 3 hydroxyl groups.
  • Compounds of this class may be produced by reacting an alkenyl halide, such as allyl chloride or allyl bromide with a strongly alkaline aqueous solution of one or more polyhydric alcohols.
  • the product is a complex mixture of polyethers with varying numbers of ether groups. Analysis reveals only the average number of ether groupings on each molecule. Efficiency of the polyether crosslinking agent increases with the number of potentially polymerizable groups on the molecule. It is preferred to utilize polyethers containing an average of two or more alkenyl ether groupings per molecule.
  • crosslinking monomers include for example, diallyl esters, dimethallyl ethers, allyl or menthally acrylates and acrylamides, tetraallyl tin, tetravinyl silane, polyalkenyl methanes, diacrylates and dimethacrylates, divinyl compounds, polyallyl phosphate, diallyloxy compounds and phosphite esters and the like.
  • a more complete listing of crosslinkers may be found in U.S. Patents 4,190,562; 3,639,459 and 4,138,381 which are incorporated herein by reference.
  • Anionic polymers including thickening agents, are available commercially from many suppliers under a variety of trade names.
  • Noveon, Inc. (formerly The B.F. Goodrich Company) sells a variety of various acrylate copolymers containing an unsaturated carboxylic acid, usually acrylic acid and a variety of esters of acrylic or methacrylic acid, under the name of ANALURE AC; BASF sells xmder the names of LUNIMER MAE and LUNIFLEX. ⁇ oveon, Inc.
  • CARBOSET resins that are copolymers of unsaturated carboxylic acids having 1 to 3 carboxyl groups and acrylates or methacrylates having 1-18 carbon alkyl groups, including stearyl and GOOD-RITE resins which are copolymers containing acrylamidomethyl propane sulfonic acid or vinylphosphonic acid or itaconic acid.
  • Anionic copolymers are also available from Rohm & Haas as ACRYSOL, KARAMUL, FRA ⁇ CO ⁇ YX and PRIMAL which are aqueous acrylic emulsions.
  • anionic polymers are copolymerse of (meth)acrylic acid, of linear or branched C 1 -C 20 alkyl (meth)acrylate and of vinylpyrrolidone, such as that sold by the company ISP under the name ACRYLIDO ⁇ E LM; (meth)acrylic acid/alkyl acrylate/alkyl methacrylate copolymers, in particular the ethyl acrylate/methyl methacrylate/methacrylic acid/acrylic acid copolymer, such as the product sold under the name AMERHOLD DR 25 by the company Amerchol; copolymers of (meth)acrylic acid and of at least one acrylamide which are optionally ⁇ -substituted, sold for example under the names RETE ⁇ 421, 423 or 425 by the company Hercules or under the names ULTRAHOLD by the company BASF; copolymers of (meth)acrylic acid and of styrene; and copolymers of (meth)acryl
  • Still further anionic polymers are the acrylic acid/ethyl acrylate/N- tertbutylacrylamide copolymers sold under the name ULTRAHOLD STRONG by the company BASF and the copolymers of methacrylic acid and of methyl methacrylate sold under the name EUDRAGIT by the company Rohm Pharma.
  • vinyl acetate/crotonic acid copolymer LUVISET CA-66 and acrylates/dimethicone copolymer as LUVIFLEX SILK both from BASF.
  • Polymethacrylic acid/acrylamidomethyl propane sulfonic acid copolymer is sold by Ondea/Nalco as FIXOMER A-30 and various monoalkyl esters of ethyl, isopropyl and butyl of poly(methyl vinyl ether/maleic acid) are sold as GANTREZ copolymers by ISP which also sells acrylates/ hydroxyester acrylate copolymer as ACUDYNE; polyvinyl pyrrolidone/acrylates/lauryl methacrylate copolymer as STYLEZE 2000; vinyl acetate/butyl maleate/isobornyl acrylate copolymer under the name of ADVANTAGE; polydimethylsiloxane encapsulated in polyvinyl-
  • Useful neutralizing organic bases are primary, secondary and tertiary amines and the water soluble alkanol amines such as monoethanolamine (MEA), diethanolamine (DEA), triethanolamine (TEA), 2 ⁇ methyl-2-amino-l -propanol (AMP), 2-amino-2-methyl-propanol and 2-amino-2-methyl-l,3-propanediol, respectively, 2-dimethylaminoethanol N,N-dimethyl- ethanolamine), 3 -dimethylamino-1 -propanol, 3-dimethylamino-2-propanol, l-amino-2- propanol, and the like, monoamino glycols, and the like, which help solubilize the polymer in water solutions.
  • MEA monoethanolamine
  • DEA diethanolamine
  • TEA triethanolamine
  • AMP 2-amino-2-methyl-propanol
  • the level of neutralization required varies for each polymer.
  • the block copolymers become soluble in water and hydroalcoholic solutions at 20% to 100% neutralization.
  • the pH of these solutions usually ranges from 4 to 12 but generally will be between 5 and 8.
  • the lowest neutralization level needed to render the polymer water soluble or dispersible depends on the composition of the polymer and other materials
  • end-use products may benefit from the use of complexed cationic materials of this invention if anionic polymers are also employed in such products.
  • the end-use products usually will also contain additional additives to enhance the desired properties.
  • Such additional additives may include non-volatile silicone compound(s) or other conditioning agent(s), preferably a water- insoluble, emulsifiable conditioning agent, such as a polydimethylsiloxane compound, "silicone gums" which are the non-functional siloxanes having a viscosity of from about 5 to about 600,000 centistokes at 25°C; rigid silicones; "dimethicone copolyols” which may be inear or branched that may be block or random copolymers; volatile hydrocarbon, such as a hydrocarbon including from about 10 to about 30 carbon atoms.
  • a water- insoluble, emulsifiable conditioning agent such as a polydimethylsiloxane compound, "silicone gums" which are the non-functional siloxanes having a viscosity of from about 5 to about 600,000 centistokes at 25°C; rigid silicones; "dimethicone copolyols” which may be in
  • Another additive that may be incorporated is a soluble tension reducing compound, such as dimethiconecopolyols, panthenol, fluorosurfactants, glycerin POE, PPG 28 Buteth 35, PEG 75 lanolin, oxtoxynol-9, PEG-25 hydrogenated castol oil, polyethylene glycol 25 glyceryl trioleate, oleth-3 phosphate, PPG-5-ceteth-10 phosphate, PEG-20 methyl glucose ether, or glycereth-7-triacetate, glycereth-7 benzoate or combinations thereof.
  • a soluble tension reducing compound such as dimethiconecopolyols, panthenol, fluorosurfactants, glycerin POE, PPG 28 Buteth 35, PEG 75 lanolin, oxtoxynol-9, PEG-25 hydrogenated castol oil, polyethylene glycol 25 glyceryl trioleate, o
  • plasticizing compounds such as polycarboxylic acid esters that have a carbon backbone of from 3 to 12 carbon atoms and 3 or more C 1 -C5 alkyl carboxylate groups attached thereto.
  • plasticizing compounds such as polycarboxylic acid esters that have a carbon backbone of from 3 to 12 carbon atoms and 3 or more C 1 -C5 alkyl carboxylate groups attached thereto.
  • Illustrative examples are triethyl citrate, tributyl citrate, triethyl phthalate, tributyl phthalate, tripentyl phthalate or combinations thereof.
  • the polycarboxylic add esters are selected from triethyl citrate, tributyl citrate, tributyl phthalate, or combinations thereof.
  • Possible further useful additives are: UN Absorbers like butyloctyl salicylate, octylmethoxycinnamate, avobenzone, benzophenone-3 and benzophenone-4, octyl salicylate, para-aminobenzoric acid (PABA), octyldimethyl PABA, hindered cyclic amine UN-light stabilizers based on 3.5-hindered piperidines available as TI ⁇ UNI ⁇ ® series of products from Ciba Specialty Chemicals or 3.5- hindered-2-keto-piperazinones .
  • UN Absorbers like butyloctyl salicylate, octylmethoxycinnamate, avobenzone, benzophenone-3 and benzophenone-4, octyl salicylate, para-aminobenzoric acid (PABA), octyldimethyl PABA, hindered cyclic amine UN-light stabilizers based
  • Emollients like Guerbet alcohols and esters thereof, silicone derivatives, beeswax, C12-15 alcohols, benzoate, mineral oil, capric triglycerides, cetearyl alcohol, ceteareth-20, castor oil, isohexadecane, isopropyl myristate, isopropyl palmitate, cetearyl octanoate and petrolatum.
  • polar solvents such as water, glycols and alcohols
  • the optional alcohol employed in the composition is an aliphatic straight or branched chain monohydric alcohol having 2 to 4 carbon atoms.
  • the concentration of the alcohol in the composition may be less than about 40% by weight, and surprisingly can be as low as 0%, preferably 0-30%> by weight.
  • compositions of this invention may be used in a variety of end-use products.
  • Personal care products include: Hair conditioners, styling gels, hair sprays, mousses, shampoos, after shaves, foam baths, hair dyes, shine enhancers, creams, lotions, facial cleansers, skin gels, liquid soaps, body washes, shaving creams, sun care lotions, sun oils, hand cleansers, hand sanitizers, blushes, eye makeups, foundations, concealers, lipsticks and lip balms.
  • Other products include: Hydroalcoholic gels, wax emulsions, asphalt emulsions, cutting fluids, metal oxide suspensions, mastic adhesives, drawing compound, metalworking fluids, paint strippers, polishes for cars, boats, furniture, leather, marble, silver or chrome, wallpaper removers, liquid fire retarders, solder masks, lapping compounds, automatic dishwashing gels, hand dishwashing liquids or pastes, laundry liquid, laundry prespotter, glass cleaners, hard surface cleaners, abrasive cleaners, sanitizing gels, fragrance gels, and air deodorizers.
  • Hydroalcoholic gels wax emulsions, asphalt emulsions, cutting fluids, metal oxide suspensions, mastic adhesives, drawing compound, metalworking fluids, paint strippers, polishes for cars, boats, furniture, leather, marble, silver or chrome, wallpaper removers, liquid fire retarders, solder masks, lapping compounds, automatic dishwashing gels, hand dishwashing liquids or pastes, laundry liquid, laundry
  • PART A A 6.67 g sample of Avalure® AC-120 polymer, a 30%> active acid functional acrylate copolymer from Noveon, was dispersed in 73.3g water and neutralized.
  • PARTB A 0.3g cetrimonium chloride sample was dispersed in 19.7g water and neutralized.
  • PART C A 0.3g cetrimonium chloride sample was complexed with 1.75g dimethicone copolyol sulfate, dispersed in 17.95g water and neutralized.
  • FixateTM G-100 polymer from Noveon which is aminomethyipropanol (AMP) acrylates/allyl methacrylate copolymer was tested as the base anionic.
  • PART A A 3.15 g sample of A-30 was dispersed in 76.85g water at pH 7.
  • PARTB A 0.3 g olealkonium chloride sample was dispersed in 19.7g water and neutralized.
  • PART C A 0.3g olealkonium chloride sample was complexed with 1.75g dimethicone copolyol sulfate, dispersed in 17.95g water and neutralized.

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Abstract

L'invention concerne un procédé de compatibilisation de polymère anionique avec des matériaux cationiques, reposant sur la complexion d'un matériau cationique à un agent complexant anionique compatible, puis sur une combinaison matériau cationique complexé/polymère anionique. On décrit une composition qui comprend un polymère anionique et un matériau cationique complexé, ainsi qu'une composition, du type revêtement, qui contient un polymère anionique et un matériau cationique complexé à un agent anionique complexant.
PCT/US2005/003450 2004-03-04 2005-02-07 Procedes de compatibilisation de materiaux cationiques avec des polymeres anioniques Ceased WO2005092273A2 (fr)

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US9629361B2 (en) 2006-02-09 2017-04-25 Gojo Industries, Inc. Composition and method for pre-surgical skin disinfection
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