WO2008112200A1 - Polymères protéine-silicone cationiques - Google Patents

Polymères protéine-silicone cationiques Download PDF

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Publication number
WO2008112200A1
WO2008112200A1 PCT/US2008/003166 US2008003166W WO2008112200A1 WO 2008112200 A1 WO2008112200 A1 WO 2008112200A1 US 2008003166 W US2008003166 W US 2008003166W WO 2008112200 A1 WO2008112200 A1 WO 2008112200A1
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group
protein
polymer
produce
amine
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PCT/US2008/003166
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English (en)
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John C. Carson
Phillip G. Abend
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Carson Product Development, Inc.
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Publication of WO2008112200A1 publication Critical patent/WO2008112200A1/fr

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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
    • A61K8/72—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
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • 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
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • 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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q13/00—Formulations or additives for perfume preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q15/00—Anti-perspirants or body deodorants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • 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
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q9/00—Preparations for removing hair or for aiding hair removal
    • A61Q9/02—Shaving preparations

Definitions

  • the present invention relates to novel cationic polymers which contain proteins as bonded or complexed components, wherein the polymers exhibit highly favorable qualities for inclusion in personal care products, in particular including haircare, skincare and other products used in contact with keratinous tissue.
  • Cationic polymers and surfactants of various types have a long history of use in hair and skin care products.
  • the majority of the materials used in these products have been the fatty quaternary ammonium salt surfactants. These are composed of long chain alkyl dimethyl amines or di-long chain alkyl methyl amines that are quaternized by reaction with an alkyl halide, an aralkyl halide or a sulfuric acid dialkyl ester.
  • surfactants examples include stearyl dimethyl benzyl ammonium chloride (INCI name: Stearalkonium chloride), distearyl dimethyl ammonium chloride (INCI name: Quaternium — 18) and behenyl trimethyl ammonium methosulfate (INCI Name: Behentrimonium methosulfate).
  • stearyl dimethyl benzyl ammonium chloride INCI name: Stearalkonium chloride
  • distearyl dimethyl ammonium chloride INCI name: Quaternium — 18
  • behenyl trimethyl ammonium methosulfate INCI Name: Behentrimonium methosulfate.
  • These compounds provide several important formulation functions - among them are emulsification, hair conditioning, antistatic properties and improved product slip and feel.
  • cationic polymers are used in personal care products and are generally of the pendant quaternary type in which the quaternary ammonium groups are attached, through intermediate connective groups, to a pre- formed polymer backbone.
  • these polymers include: Ucare Polymer JR-400 ® from the Amerchol division of Dow Chemical (INCI name: Polyquaternium-10), which is a hydroxyethyl cellulose polymer with attached trimethylammonium 2-hydroxypropyl chloride groups and Jaguar C- 17 ® from Rhodia (INCI name: Guar hydroxypropyltrimonium chloride), which is a guar gum polymer with attached trimethylammonium 2-hydroxypropyl chloride groups.
  • Proteins, hydrolyzed proteins and amino acids have long histories of usage in hair care products as moisturizers, shine improving agents and materials that improve dry hair manageability. Quatemized proteins (made by reaction with trimethyl epoxypropyl ammonium chloride) are also well known and provide improved wet combing and give antistatic properties as well as providing the properties previously outlined for proteins.
  • Silicones (dimethylpolysiloxanes) of various molecular weights and with a wide range of functional groups including amines and quatemized ammonium salts have been used for many years in both skin and hair care products. In skin care products they provide exceptional barrier properties and a unique non-oily emolliency. In hair care products silicones improve both wet and dry hair combing properties and increase hair shine.
  • Combinations of silicones and proteins or amino acids have also been made (Croda - Crodasone W US Patent 5,412,074) by reacting epoxy containing (or terminated) siloxanes with the desired protein.
  • the epoxy functional silicones are prepared by reacting silicone polymers containing pendant or terminal hydroxy terminated alkoxy moieties.
  • the alkoxy groups are most often a short polymeric section (consisting of from 1 to 20 repeat units) made from ethylene and/or propylene oxides.
  • the terminal hydroxy group is reacted with epichlorohydrin to form a chlorohydroxy propyl ether from which an epoxide is generated by reaction with a base.
  • This epoxy moiety can then react with amino and hydroxy functions on a protein or an amino acid to form a 2-hydroxypropyl linkage that joins the protein (or amino acid) to the silicone polymer.
  • These silicone-protein molecules are substantive to skin and hair providing good film forming properties and shine.
  • silicone protein polymers In order to improve substantivity and antistatic properties, the following silicone protein polymers were developed.
  • U.S. Pat. No. 5,100,956 March, 1992 teaches the creation and uses of silicone protein polymers which are prepared by the phosphation of a pendant hydroxyl group which is present on a silicone polymer. The silicone phosphates are subsequently reacted with epichlorohydrin and then, in a subsequent step, reacted with the amino group of the protein. This results in a silicone phosphate hydroxypropyl protein.
  • the current invention describes protein silicone polymers that are linked via a quaternary ammonium salt and therefore are permanently cationically charged. This removes the dependency of their cationic charge upon the pH of their aqueous solutions and provides greater substantivity and antistatic properties.
  • chlorhydrol residues present on the quaternary ammonium salts are then reacted with base to form epoxides (glycidyl groups) at one or both distal ends of the polymer compound and/or pendant from the backbone of the silicone polymer, which are then further reacted with the desired protein to produce compositions according to the present invention.
  • Secondary amine (either the same as before or different) is then reacted with these newly formed glycidyl ether groups to produce new tertiary amines that are then reacted to form quaternary ammonium salts by treatment with an acid and subsequent reaction with epichlorohydrin. These quaternary ammonium chlorhydrol salts are the reacted with base to form glycidyl groups. This reaction scheme may be repeated to produce a linear string of 2, 3, 4 or more quaternary hydroxypropyl ammonium salt groups that can be finally terminated with glycidyl groups and reacted with the desired protein.
  • the chlorhydrol residues present on the quaternary ammonium salts are then reacted with base to form epoxides (glycidyl groups) which are then reacted with the desired tertiary amine salt to form a second quaternary ammonium salt.
  • tertiary amine salts may be formed from amines from the following group: trimethylamine, triethylamine, triethanolamine, triisopropylamine, triisopropanolamine and the like, or they may be mono, di or tri fatty amines, or they may be the reaction product of dimethylaminopropylamine and a fatty acid or fatty ester or they may be the reaction product of a secondary amine with an epoxide. It is an object of this invention to produce a cationic silicone polymer using the above described reaction scheme in which the silicone polymer initially contains multiple pendant epoxy groups.
  • an acid preferably a mineral acid, methanesulfonic acid or small organic acids such as acetic, lactic or glycolic
  • tertiary amine salts may be formed from amines from the following group: trimethylamine, triethylamine, triethanolamine, triisopropylamine, triisopropanolamine and the like, or they may be mono, di or tri fatty amines, or they may be the reaction product of dimethylaminopropylamine and a fatty acid or fatty ester or they may be the reaction product of a secondary amine with an epoxide.
  • the polymers according to the present invention are directed to polydialkylsiloxanes (preferably, polydimethylsiloxanes), which have been derivatized to contain quaternary amine groups as well as proteins/other amines, the proteins being covalently linked to the quaternary amine derivatized polydialkylsiloxane through epoxide groups which have been formed on an amine group at the distal ends or in the backbone (pendant groups) of the polymer and/or as pendant groups.
  • polydialkylsiloxanes preferably, polydimethylsiloxanes
  • the polymers of the present invention in exemplary embodiments are made from polydialkylsiloxanes (e.g., polydimethylsiloxanes) that contain reactive epoxy functional groups which are first reacted with a secondary amine to produce a tertiary amine.
  • This reaction product is acidified (preferably using mineral acids, methanesulfonic acid or small organic acids such as acetic, lactic or glycolic) and this polydimethylsiloxane ammonium salt is then reacted with epichlorohydrin to produce a silicone polymer that now contains both quaternary ammonium groups and chlorohydrols (chlorohydrol groups).
  • the chlorohydrol groups are next treated with base (preferably aqueous NaOH or KOH) to convert them to epoxides.
  • base preferably aqueous NaOH or KOH
  • These epoxy groups preferably, glycidyl groups
  • a protein is then reacted with a protein to make a final product which consists of a polydimethylsiloxane that is attached through a quaternized ammonium salt to a protein.
  • the intention of this reaction scheme is to combine in one molecule the improved hair combing and shine properties of a silicone polymer with the film forming and moisturizing benefits of a protein and to make this copolymer combination more substantive to hair and skin by joining them together through a cationically charged quaternized ammonium salt linkage.
  • the polydimethylsiloxane may be a linear polymer with terminal ( ⁇ ,co) epoxy groups, or the epoxy groups may be pendant from a "backbone" polydimethylsiloxane in which case, there may be one or more epoxy groups per polydimethylsiloxane molecule. Additionally, the epoxy functional polydimethylsiloxane may have terminal or pendant alkyl or alkoxy (ethoxy, propoxy, butoxy, or a combination) groups and these alkyl or alkoxy groups may be terminated by epoxy groups.
  • tertiary fatty amines i.e. amines which contain at least a C 8 (e.g. C 8 -C 24 ) saturated or unsaturated linear or branch-chained alkyl group, amino acids, diamines and polyamines may be reacted in place of the protein with the polydimethylsiloxane (or alkoxy polydimethylsiloxane) that has been reacted (as described above) to contain quaternary ammonium salts with reactive glycidyl groups, to produce other useful materials containing a variety of functional groups.
  • amines which contain at least a C 8 (e.g. C 8 -C 24 ) saturated or unsaturated linear or branch-chained alkyl group
  • amino acids, diamines and polyamines may be reacted in place of the protein with the polydimethylsiloxane (or alkoxy polydimethylsiloxane) that has been reacted (as described above) to contain
  • the reaction scheme described above may be modified as follows: the epoxy functional polydimethylsiloxane (or epoxy functional alkoxylated polydimethylsiloxane) may be reacted with a tertiary ammonium salt formed from a tertiary amine and an acid (as described above) to produce a polydimethylsiloxane quaternary ammonium salt.
  • the tertiary amine may be chosen from an exemplary group consisting of trimethylamine, triethylamine, triethanolamine, triisopropylamine, triisopropanolamine and the like, or may be a mono, di or tri fatty amine (such as: stearyldimethylamine, distearylmethylamine or tricetylamine), or a reaction product of dimethylaminopropylamine and a fatty acid or fatty ester or the reaction product of a secondary amine with an epoxide.
  • the present invention is directed to a copolymer of a polydimethylsiloxane and a protein or polypeptide that are combined through a cationically charged quaternary ammonium salt.
  • the present invention also relates to a copolymer of an alkoxylated polydimethylsiloxane and a protein or polypeptide that are combined through a cationically charged quaternary ammonium salt.
  • chlorhydrol residues present on the quaternary ammonium salts are then reacted with base to form epoxides (glycidyl groups) which are then reacted with an amine (preferably, at least mono-or di-substituted), a polypeptide or the desired protein.
  • Another embodiment of the present invention relates a silicone/protein copolymer of an epoxy containing alkoxylated polydimethylsiloxane and a protein formed in a reaction scheme in which a secondary amine is first reacted with the epoxy groups of the alkoxylated polydimethylsiloxane to produce tertiary amines that are then reacted to form quaternary ammonium salts by treatment with an acid and subsequent reaction with epichlorohydrin.
  • the chlorhydrol residues present on the quaternary ammonium salts are then reacted with base to form glycidyl groups which are then reacted with an amine (preferably, at least mono- or di-substituted), a polypeptide or the desired protein.
  • chlorhydrol residues present on the quaternary ammonium salts are then reacted with base to form glycidyl groups which are then reacted with an amine (preferably, at least mono-or di-substituted), a polypeptide or the desired protein.
  • the chlorhydrol residues present on the quaternary ammonium salts are then reacted with base to form glycidyl groups with an amine (preferably, at least mono-or di-substituted), a polypeptide or the desired protein.
  • Secondary amine (either the same as before or different) is then reacted with these newly formed glycidyl ether groups to produce new tertiary amines that are then reacted to form quaternary ammonium salts by treatment with an acid and subsequent reaction with epichlorohydrin. These quaternary ammonium chlorhydrol salts are the reacted with base to form glycidyl groups. This reaction scheme may be repeated to produce a linear string of 2, 3, 4 or more quaternary hydroxypropyl ammonium salt groups that can be finally terminated with glycidyl groups and reacted with the desired amine, polypeptide or protein.
  • the chlorhydrol residues present on the quaternary ammonium salts are then reacted with base to form epoxides (glycidyl groups) which are then reacted with the desired tertiary amine salt to form a second quaternary ammonium salt.
  • tertiary amine salts may be formed from amines from the following preferred group: trimethylamine, triethylamine, triethanolamine, triisopropylamine, triisopropanolamine and the like, or they may be mono, di or tri fatty amines, or they may be the reaction product of dimethylaminopropylamine and a fatty acid or fatty ester or they may be the reaction product of a secondary amine with an epoxide. It is a further embodiment of this invention to produce a cationic silicone polymer using the above described reaction scheme in which the silicone polymer initially contains multiple pendant epoxy groups.
  • an acid preferably a mineral acid, methanesulfonic acid or small organic acids such as acetic, lactic or glycolic
  • tertiary amine salts may be formed from amines from the following group: trimethylamine, triethylamine, triethanolamine, triisopropylamine, triisopropanolamine and the like, or they may be mono, di or tri fatty amines, or they may be the reaction product of dimethylaminopropylamine and a fatty acid or fatty ester or they may be the reaction product of a secondary amine with an epoxide.
  • each R 1 , R 2 , and R 3 is independently a Ci-C 3 alkyl group, and one or more but not all (generally 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or more) of Ri, R 2 or R 3 is a group according to the chemical structure:
  • A is H, an optionally substituted Ci-C 24 alkyl, or an optionally substituted C 2 -C 26 acyl group (preferably, a Ci-C 4 alkyl or alkanol group or an acyl or amide group derived from a fatty acid), or a
  • R is a -(CH 2 ) n - group, a Ci-C 24 alkoxy group, a C]-C 24 oxyalkoxy group, a poly(oxyethylene) group, a poly(oxypropylene) group or a poly(oxyethylene)-co-poly(oxypropylene) group wherein said poly(oxyethylene) group, said poly(oxypropylene) group or said poly(oxyethylene)-co-poly(oxypropylene) group has a molecular weight ranging from about 200 to 100,000, about 250 to 50,000, about 250 to 5,000, about 500 to 2500, about 500 to 2000, about 200 to 1,000 with the proviso that when j is more than 1, R is a -CH 2 - group;
  • Each R 4 is a Ci-C 24 alkyl, alkanol or acyl group (preferably, a Ci-C 4 alkyl or alkanol group or an acyl group derived from a fatty acid);
  • Each R 5 is a Ci-C 24 alkyl, alkanol or acyl group (preferably, a Ci-C 4 alkyl or alkanol group or an acyl group derived from a fatty acid);
  • T " is a counterion for the quaternary amine group (preferably, a Cl-, Br-, SO4 ⁇ , CH 3 SO 3 " , or a carboxylate group from an organic acid such as acetate, proprionate, lactate, glycolate, etc.);
  • R p is a -NR 3 Rb group, a quaternary ammonium group -NR 3 R b Rc + T " , a polypeptide or protein (preferably silk protein, keratin or mixtures thereof); wherein R a ,R b and R 0 are each independently H, or a Ci-C 26 optionally substituted (preferable substitution is a hydroxyl group to from an alkanol group) saturated or unsaturated alkyl (e.g., alkene or alkyne) or substituted acyl (including an amide) group (preferably, both R a and R b are not H), or optionally, R 0 is a group obtained by reacting an -NR 3 R
  • y is an integer from 0 to 1000 (also, 1 to 1000, 1 to 750, 1 to 500, 2 to 500, 5 to 250, 10 to
  • compounds according to the present invention may be represented by the chemical structure:
  • R p is a protein or polypeptide, a
  • group C or a quaternary group where m is 1-6, (preferably 1-3,) R' and Rc' is H or a Ci-C 24 optionally substituted (preferable substitution is a hydroxyl group to from an alkanol group) saturated or unsaturated alkyl (e.g., alkene or alkyne) or substituted acyl (including an amide) group or optionally a group obtained by reacting group C with a quaternizing agent and R 1 , is a Ci-C 24 saturated or unsaturated alkyl group (including an alkene, containing between 1 and up to 4 double bonds or an alkyne group).
  • A is a group, where m is 1-5, preferably 1-3, and R h is a Ci-C 24 saturated or unsaturated alkyl group (including an alkene, containing between 1 and up to 4 double bonds or an alkyne group).
  • each Rj 3 , R 2a , and R 3a is independently a CpC 3 alkyl group, and one or more (generally 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 or more) of Ri a , R 2a or R 3a is a glycidyl group
  • x and y are each independently an integer from 0 to 1000 (also, 1 to 1000, 1 to 750, 1 to 500,
  • R a and R b are each independently selected from H, or a Ci-C 24 optionally substituted (preferable substitution is a hydroxyl group to from an alkanol group) saturated or unsaturated alkyl (e.g., alkene or alkyne) or acyl group (preferably, both R a and R b are not H).;
  • the glycidyl group can be reacted with another — NR a R b to form a ⁇ -hydroxy amine group and the amine group formed can again follow the step 2 and 3 reaction steps to form a glycidyl group, which may be reacted with a protein or polypeptide to produce a final compound or alternatively an -NR 3 R b group, which may be quaternized to produce a final cationic silicone compound or subjected to another series of steps 2, 3 and 4 as described above.
  • a chain of quaternary groups may be produced which has a protein or polypeptide anchoring a distil end or other portion of the polymer.
  • subject is used to describe an animal, preferably a mammal (especially a human, pet, domesticated animal, etc.) capable of advantageously using compositions according to the present invention.
  • keratinous tissue shall mean skin, hair, ungual (nails) tissue on the subject.
  • personal care composition or "personal care product” is used to describe a chemical composition used for the purpose of cleansing, conditioning, grooming, beautifying, or otherwise enhancing the appearance of the human body.
  • personal care products include skin care products, cosmetic products, antiperspirants, deodorants, perfume, toiletries, soaps, bath oils, feminine care products, hair-care products, oral hygience products, depilatories, including shampoos, conditioners, hair straightening products and other haircare products, color cosmetics such as lipstick, creams, make-up, skin creams, lotions (preferably comprised of water-in-oil or oil-in- water emulsions), shave creams and gels, after-shave lotions and shave-conditioning compositions and sunscreen products, among numerous others.
  • personal care compositions according to the present invention include haircare and skin care products, especially shampoos, conditioners, rinses, detanglers, hair color products, body washes, make-up, lipstick, skin creams and other skin-care products
  • Personal care products according to the present invention comprise an effective amount of a cationic silicone polymer composition according to the present invention as otherwise described herein in admixture with additional components (one or more) selected from the group consisting of water, an aqueous solvent (e.g. alcohol or other compatible solvent), a non-aqueous solvent, emollients, humectants, oils (polar and non-polar) conditioning agents, surfactants, anti-static agents, thickeners/thickening agents, stiffening agents, emulsifiers, medicaments, fragrances, preservatives, deodorant components, anti- perspirant compounds, skin protecting agents, pigments, dyes, coloring agents, sunscreens and mixtures thereof, among others.
  • additional components one or more selected from the group consisting of water, an aqueous solvent (e.g. alcohol or other compatible solvent), a non-aqueous solvent, emollients, humectants, oils (polar and non-polar) conditioning agents, surfactants, anti-
  • the present invention relates to skin, nail and hair care compositions, in particular, shampoos, conditioners, hair color compositions, detanglers, body washes, bath oils, skin creams, lotions, color cosmetics and in particular, a lipstick, makeup, skin cream, skin conditioner or other composition to be used on the skin.
  • skin, nail and hair care compositions in particular, shampoos, conditioners, hair color compositions, detanglers, body washes, bath oils, skin creams, lotions, color cosmetics and in particular, a lipstick, makeup, skin cream, skin conditioner or other composition to be used on the skin.
  • Personal care products according to the present invention comprise about 0.01% to about 50% (about 0.1% to about 35%, about 0.25% to about 30%, about 0.5% to about 25%, about 0.5% to about 20%, about 0.75% to about 17.5% about about 1% to about 15%, about 1% to about 10%, about 1% to about 7.5% about 1% to about 5%, about 1% to about 3.5%, about 1% to about 3%, about 1% to about 2.5%, etc.) or more by weight of a cationic silicone compound(s) as otherwise described herein, the remainder of the composition comprising at least one additional component selected from the group consisting of water, an aqueous solvent (e.g.
  • a non-aqueous solvent emollients, humectants, oils (polar and non-polar), conditioning agents, emulsifiers, surfactants, thickeners, stiffening agents, medicaments, fragrances, preservatives, deodorant components, anti-perspirant compounds, skin protecting agents, pigments, dyes, coloring agents, sunscreens and mixtures thereof, among others.
  • conditioning agents emulsifiers, surfactants, thickeners, stiffening agents, medicaments, fragrances, preservatives, deodorant components, anti-perspirant compounds, skin protecting agents, pigments, dyes, coloring agents, sunscreens and mixtures thereof, among others.
  • emulsifiers surfactants
  • thickeners stiffening agents
  • medicaments medicaments
  • fragrances preservatives
  • deodorant components anti-perspirant compounds
  • skin protecting agents pigments, dyes, coloring agents, sunscreens and mixtures thereof, among others.
  • protein or "polypeptide” is used to describe a protein or polypeptide which is advantageously used in personal care products and includes such proteins and polypeptides such as silk protein, keratin, collagen, elastin, casein, milk, reticulin, fibronectin, vegetable-derived proteins, including wheat and corn gluten, soy (including soy gluten), rice and oat protein concentrates, and defatted oilseeds (peanuts, almond, sunflower), or hydrolyzed versions (hydrolysates) of these proteins, among others.
  • proteins and polypeptides such as silk protein, keratin, collagen, elastin, casein, milk, reticulin, fibronectin, vegetable-derived proteins, including wheat and corn gluten, soy (including soy gluten), rice and oat protein concentrates, and defatted oilseeds (peanuts, almond, sunflower), or hydrolyzed versions (hydrolysates) of these proteins, among others.
  • an “emulsion” according to the present invention is advantageously a cream or lotion (especially a skin cream or skin lotion) which is generally formed by the suspension of a very finely divided liquid, in this case water, in another liquid, in this case, an oil.
  • a cream or lotion especially a skin cream or skin lotion
  • an emulsion is formed when the water phase is compatabilized in the oil phase, such that the water phase becomes “hidden” within the oil phase.
  • an emulsion also may be formed when the oil phase is compatabilized in the water phase, such that the oil phase is "hidden" within the water phase.
  • the term emulsion is used to distinguish the present compositions from compositions which contain at least two visually distinct phases, i.e., an oil phase and a water phase.
  • Emulsions can be used to provide a number of personal care formulations including skin creams, skin lotions, color cosmetics, conditioners, shampoo formulations, etc.
  • Oil is used throughout the specification to describe any of various lubricious, hydrophobic and combustible substances obtained from animal, vegetable and mineral matter.
  • Oils for use in the present invention may include petroleum-based oil derivatives such as purified petrolatum and mineral oil.
  • Petroleum-derived oils include aliphatic or wax-based oils, aromatic or asphalt-based oils and mixed base oils and may include relatively polar and non-polar oils.
  • Non-polar oils are generally oils such as petrolatum or mineral oil or its derivatives which are hydrocarbons and are more hydrophobic and lipophilic compared to synthetic oils, such as esters, which may be referred to as "polar" oils.
  • non-polar and polar are relative within this very hydrophobic and lipophilic class, and all of the oils tend to be much more hydrophobic and lipophilic than the water phase which is used in the present invention.
  • oils in addition to the above-described oils, certain essential oils derived from plants such as volatile liquids derived from flowers, stems and leaves and other parts of the plant which may include terpenoids and other natural products including triglycerides may also be considered oils for purposes of the present invention.
  • Petrolatum mineral fat, petroleum jelly or mineral jelly
  • mineral oil products for use in the present invention may be obtained from a variety of suppliers. These products may range widely in viscosity and other physical and chemical characteristics such as molecular weight and purity.
  • Preferred petrolatum and mineral oil for use in the present invention are those which exhibit significant utility in cosmetic and pharmaceutical products and are "cosmetically compatible”.
  • Cosmetic grade oils are preferred oils for use in the present invention.
  • Additional oils for use in the present invention may include, for example, mono-, di- and tri- glycerides which may be natural or synthetic (derived from esterification of glycerol and at least one organic acid, saturated or unsaturated, such as for example, such as butyric, caproic, palmitic, stearic, oleic, linoleic or linolenic acids, among numerous others, preferably a fatty organic acid, comprising between 8 and 26 carbon atoms).
  • mono-, di- and tri- glycerides which may be natural or synthetic (derived from esterification of glycerol and at least one organic acid, saturated or unsaturated, such as for example, such as butyric, caproic, palmitic, stearic, oleic, linoleic or linolenic acids, among numerous others, preferably a fatty organic acid, comprising between 8 and 26 carbon atoms).
  • Glyceride esters for use in the present invention include vegetable oils derived chiefly from seeds or nuts and include drying oils, for example, linseed, iticica and rung, among others; semi-drying oils, for example, soybean, sunflower, safflower and cottonseed oil; non-drying oils, for example castor and coconut oil; and other oils, such as those used in soap, for example palm oil. Hydrogenated vegetable oils also may be used in the present invention. Animal oils are also contemplated for use as glyceride esters and include, for example, fats such as tallow, lard and stearin and liquid fats, such as fish oils, fish-liver oils and other animal oils, including sperm oil, among numerous others.
  • oils for use in the present invention include petrolatum, mineral oil or mixtures of petrolatum and mineral oil where the amount of petrolatum to mineral oil (on a weight/weight basis) ranges from about 1 :20 to about 10:1, about 1:5 to about 5: 1, about 1 :3 to about 1 :1, depending upon the end use of the emulsion composition.
  • petrolatum and/or mineral oil and/or the ratio of petrolatum to mineral oil in the present compositions will greatly influence the final viscosity of the emulsions and personal care compositions according to the present invention.
  • substituted is used throughout the specification to describe a moiety which may be substituted for a hydrogen group in compositions according to the present invention and may include (within the context of the use of the compositions) halogens such as fluorine, chlorine and bromine, nitro groups, amine groups (including mono and di- substituted amine groups), Ci-Ci 8 amide groups, hydroxyl groups, Ci-C 6 alkoxy groups, Ci- Ci 6 alkyl groups or Ci-C] 8 acyl groups, each of which substituents may be optionally substituted, within the context of the use of a substituent.
  • the substitutents in the present compositions are limited to hydroxyl groups or C 2 -Ci 8 acyl groups.
  • halogens such as fluorine, chlorine and bromine, nitro groups, amine groups (including mono and di- substituted amine groups), Ci-Ci 8 amide groups, hydroxyl groups, Ci-C 6 alkoxy groups, Ci- Ci 6 alkyl groups or Ci-C] 8
  • secondary amine is used to describe an amine to which is attached at least two carbon-containing groups and a hydrogen atom, each of the groups being covalently bonded to the amine group through a carbon atom within the group.
  • a secondary ammonium group is a secondary amine group which is protonated.
  • tertiary amine is used to describe an amine to which is attached at least three carbon-containing groups, each of the groups being covalently bonded to the amine group through a carbon atom within the group.
  • a tertiary ammonium group is a tertiary amine group which is protonated.
  • quaternary amine is used to describe an amine to which is attached to four carbon-containing groups, with the amine group carrying a positive charge and a counterion (an anionic group which balances the positive charge on the quaternized nitrogen) which is obtained when the tertiary amine group is quaternized (by reaction with epichlorohydrin, or alternatively, by reaction with a quaternizing agent (see below).
  • counterions represented as T " in the chemical structures
  • preferred counterions being obtained by acidifying a tertiary amine to produce a tertiary ammonium salt
  • the counterion T- being the same as the counterion from the acid used to protonate the tertiary amine group
  • Preferred counterion groups include, fro example, halogens, especially CI " and Br ' , SO 4 2" (from H 2 SO 4 ), methylsulfonate (CH 3 SO 3 " ), or carboxylate anions from organic acids, including, for example, acetate, propionate, lactate, glycolate, etc.).
  • Quaternizing agent is used throughout the specification to describe compounds which are used to react with tertiary amines to produce quarternary ammonium salts according to the present invention.
  • Quaternary ammonium salts are salts which are produced when a tertiary amine is reacted with a quaternizing agent to produce a quaternary amine (quaternium) which is substituted with four carbon-containing groups.
  • the quaternary amine produced is cationic and is generally found complexed with an anionic group or "counterion", which is generally derived from the quaternizing agent used to produce the quaternary amine.
  • Exemplary quaternizing agents for use in the present invention include, for example, dimethyl sulfate, diethyl sulfate, methyl bromide, benzyl chloride, ethyl benzyl chloride, methyl benzyl chloride, dichloroethyl ether, epichlorohydrin, ethylene chlorohydrin, methyl chloride and allyl chloride, among others, such that the group reactive with the
  • the counterion may be any group which is anionic as described hereinabove and that is compatible with the chemistry of the present invention and preferably is an anionic chloride, bromide, iodide, fluoride, carboxylate (from, for example the use of chloroacetic acid or sodium monochloroacetate as the quaternizing agent to provide an acetate which can provide both a quaternium group as well as the counterion) sulfate (mono- or di-anion, preferably alkyl substituted mono-anion such as methyl or ethyl sulfate, more preferably ethyl sulfate) and phosphate (mono-, di- and tri-anion, preferably tri-anion), among numerous others, with anionic chloride and sulfonate (alkyl substituted mono-anion) being the preferred counterion T.
  • anionic chloride and sulfonate alkyl substituted mono-anion
  • organic acid or "carboxyl acid”
  • carboxylic acid as used herein describes organic acids which may contain one or more carboxylic acid moieties preferably ranging in size from C 2 to C 50 or more, preferably C 2 to C 24 or more.
  • monocarboxylic acid is used to describe organic acids which contain only one carboxylic acid moiety. Acyl groups which substitute amines are generally obtained from organic acids, especially including certain fatty acids.
  • Exemplary carboxylic acids for use in the present invention include, for example, acetic acid, glycolic acid, lactic acid, propionic acid, butyric acid, pentanoic acid, neopentanoic acid, caproic acid, caprylic acid, capric acid, heptanoic acid, neoheptanoic acid, octanoic acid, iso-octanoic acid, 2-ethylhexanoic acid, nonanoic acid, isononanoic acid, decanoic acid, iso-decanoic acid, neodecanoic acid, undenanoic acid, undecylenic acid, lauric acid, isolauric acid, myristic acid, palmitic acid, stearic acid, hydroxy stearic acid, isostearic acid, arachidonic acid, tallow fatty acid, arachidic acid, behenic acid, lignoceric acid, lauroleic acid
  • compositions may exemplify the present invention.
  • compositions according to the present invention are included in personal care products/formulations in effective amounts, i.e., amounts which produce an intended effect.
  • the amount of cationic silicone polymers included in personal care products/composition is at least about 0.01% by weight, and generally ranges from about 0.05% to about 50% by weight or more of personal care formulations according to the present invention.
  • cationic silicone polymers according to the present invention may be included in amounts ranging from about 0.05% to about 15% by weight.
  • cationic silicone polymers according to the present invention are included in amounts ranging from about 0.05% to about 10% by weight of the formulation.
  • cationic silicone polymers according to the present invention comprise about 0.05% to about 10% by weight, about 0.25% to about 3% by weight of the final end-use hair-care composition.
  • Other components which may be included in hair-care formulations include standard components generally used in these formulations including, for example, a solvent or diluent such as water and/or alcohol, other surfactants, thickeners, coloring agents, dyes, emollients, preservatives, additional conditioning agents and humectants, among numerous others.
  • cationic silicone polymers according to the present invention are included in amounts ranging from about 0.025% to about 15% or more by weight, about 0.1% to about 10% by weight more preferably about 0.5% to about 3% by weight.
  • Other components which may be included in these end-use personal care compositions include, for example, water, and at least one or more of emollients, humectants and emulsifiers and optionally, other conditioning agents, medicaments, fragrances and preservatives.
  • cationic silicone polymers according to the present invention are included in amounts ranging from about 0.25% to about 15% by weight, about 0.5 to about 10% by weight, about 0.75% to about 3% by weight.
  • Additional components which may be employed in these compositions include, for example, water, emollients, dyes, coloring agents, humectants and emulsifiers and optionally, other conditioning agents, medicaments, fragrances and preservatives.
  • cationic silicone polymers according to the present invention are included in amounts ranging from about 0.025% to about 15%, about 0.5% to about 7.5% by weight, about 0.5% to about 5% of the final formulations.
  • Additional components which may be employed in these compositions may include, for example, a UV absorbing composition such as para-amino benzoic acid (PABA) or a related UV absorber or a pigment such as TiO 2 , water or oil, and optional components including, for example, one or more of an oil, water, suspending agents, other conditioning agents, humectants and emollients, among others.
  • PABA para-amino benzoic acid
  • a pigment such as TiO 2
  • water or oil water or oil
  • optional components including, for example, one or more of an oil, water, suspending agents, other conditioning agents, humectants and emollients, among others.
  • cationic silicone polymers according to the present invention may be included in amounts ranging from about 0.25% to about 20% by weight or more, preferably about 0.5% to about 10% by weight.
  • Additional components which may be included in bar and liquid soaps include water, optional solvents such as ethyl alcohol or isopropanol and surfactants, and optionally, bactericides, emollients, fragrances and colorants, among others.
  • Cationic silicone polymers according to the present invention may be supplied as dry powders or in solution/dispersions, wherein the cationic silicone polymer comprises up to about 75% by weight (preferably, 50% by weight or less) in combination with water and/or a cosmetically acceptable solvent such as ethanol and/or isopropanol.
  • a cosmetically acceptable solvent such as ethanol and/or isopropanol.
  • IPA Isopropyl Alcohol
  • R is an alkoxy ether formed
  • Product (6) is used as is without isolating the product or removing the salt (NaCl), generated by the final step ring closure.
  • This reaction links the quaternary ammonium glycidyl ether containing silicone polymer to a protein by reacting the glycidyl ether with reactive amine and/or hydroxyl groups on the protein.
  • the final product contains isopropyl alcohol and a final solids level of 61%.
  • the NaOH (50%) was further diluted with the water and added to the above reaction mixture with stirring.
  • the temperature increased to 27.1°C.
  • the temperature was raised to 50 0 C and held for one hour with stirring.
  • This procedure incorporates two changes that result in a preferred product.
  • First is the use of propylene glycol which results in a uniform, clear, one phase product.
  • Second is a ratio change for the secondary amine from 1 to 1 relative to the epoxy content of the Dow Corning BY 16-876 to 0.75 to 1. This ratio change reflects the reality of the reactivity of the amine with the silicone epoxide based upon separate experiments showing that this is the actual reaction ratio.
  • the heat was turned off and the pH was then adjusted to 5.5 using a 50:50 mixture of cone.
  • HCl water.
  • a 1% aqueous solution had a pH of 5.80.
  • Example 2 This Example is similar to that of Example 2 and produces Compound (7) except the solvent is propylene glycol and the solids were calculated to be 44%.
  • Trisun 80 (High Oleic Sunflower Oil) 295 1.0 295.00
  • Part B Begin stirring of the reactor containing the entire batch of PGA5-64 and add the
  • the solids were found to be 53.6% on drying.
  • This reaction links the oleamido quaternary ammonium glycidyl salt containing silicone polymer formed in Example 6 to a protein by reacting the glycidyl ether with reactive amines and/or hydroxyl groups on the protein.
  • Example 8
  • Vikolox 18 fstearyl epoxide 286.2 0.054 15.50
  • This reaction scheme first links an epoxy terminated fatty alkyl group to a secondary amine.
  • the tertiary amine that is formed is acidified with methanesulfonic acid and this tertiary amine salt is reacted with the epoxy containing silicone polymer.
  • the various examples were evaluated for their feel on skin, their substantivity to wool and their hair conditioning properties. All of the finished polymer examples (Examples 2,4,7 and 8) left a water shedding residue on skin when applied to the back of the hands from a 1% aqueous dispersion/solution. The skin felt soft, smooth and non-oily - as if a "silicone oil" had been deposited.
  • Example 2 None of the finished polymer examples (Examples 2,4,7 and 8) showed strong deposition on wool cloth as determined by visually by comparing the color change seen after first treating wool swatches with either a 1% aqueous polymer solution or water (control), then treating the swatches with an acidic 0.1% FD&C Blue No.l solution and comparing the intensity of the color change. In all cases, the polymer treated swatches had a more intense (darker) blue color than the control, although the difference was not great. Presumably, any difference in color is attributed to the deposition of the cationic polymer onto the wool substrate which then attracts the anionic dye more strongly than the untreated wool.
  • Example 2 The hair conditioning of Example 2 was not evaluated because the odor was strong and ethereal (due to the use of Isopropyl Alcohol as a solvent) and the product separated into two layers. Therefore, it was judged to be unacceptable for use in cosmetic products.
  • the hair conditioning of Example 4 showed significant drag for both the wet and dry combing evaluations, but the dried hair felt smooth (although raspy at the tress ends), was not coated or oily feeling, had good shine and showed very little static electricity effects after being combed 10 times. These dry hair effects make this a good candidate for use in a hair conditioner, especially if formulated with a wet hair detangling ingredient.
  • the hair conditioning of Example 7 showed poor wet combing and detangling.
  • the dry hair combing was also difficult and the hair felt raspy, but it was not coated and showed very little static electricity fly-away when combed 10 times. This is not a very favorable evaluation and this is not considered to be a viable hair conditioner ingredient, although it may have some value in improving the shine of dry hair.
  • Example 8 The hair conditioning of Example 8 showed excellent wet combing and detangling.
  • the dry hair combing was also very good and the hair felt soft and smooth. It was not coated had good shine and showed very little static electricity fly-away when combed 10 times. This is an excellent hair conditioning ingredient.
  • This reaction scheme links a fatty tertiary amine and an epoxy containing silicone polymer by converting the amine to an ammonium salt and then reacting it with the epoxide to form a quaternary ammonium salt.
  • wet combing is moderately good, the dry hair combing is good with some drag at the hair ends.
  • the hair does not feel raspy or coated and it does not feel oily.
  • the hair has good shine with no "static" fly away when combed.

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Abstract

L'invention concerne, dans un exemple représentatif, des polymères formés à partir de polydiméthylsiloxanes contenant des groupes fonctionnels époxy réactifs qu'on soumet à une première réaction avec une amine secondaire afin de produire une amine tertiaire. On acidifie ce produit réactionnel (de préférence au moyen d'acides minéraux, d'acide méthanesulfonique ou de petits acides organiques tels que l'acide acétique, lactique ou glycolique), et on fait réagir ce sel avec de l'épichlorhydrine pour produire un polymère de silicone qui contient à présent à la fois des groupes d'ammonium quaternaire et des chlorhydrols. On traite ensuite les groupes chlorhydrol avec une base (de préférence NaOH ou KOH aqueux) pour les convertir en époxydes, puis on fait réagir ces groupes époxy (en réalité des groupes glycidyle) avec une protéine pour obtenir un produit final consistant en un polydiméthylsiloxane rattaché à une protéine par l'intermédiaire d'un sel d'ammonium quaternarisé. Le but de ce schéma réactionnel est de combiner dans une seule molécule les caractéristiques de facilitation du peignage d'un polymère de silicone et les qualités filmogènes et hydratantes d'une protéine, et d'améliorer l'affinité de cette combinaison copolymère pour les cheveux et la peau en les reliant par l'intermédiaire d'une liaison sel d'ammonium quaternaire à charge cationique. Le polydiméthylsiloxane peut être un polymère linéaire comportant des groupes terminaux (α,ω) époxy, ou les groupes époxy peuvent être pendants sur une chaîne principale polydiméthylsiloxane, auquel cas le nombre de groupe époxy par molécule de polydiméthylsiloxane peut être supérieur à deux. Le polydiméthylsiloxane à fonction époxy peut en outre comprendre des groupes alcoxy (éthoxy, propoxy, butoxy ou une combinaison de ceux-ci) terminaux ou pendants et ces polyalcoxy peuvent être terminés par des groupes époxy.
PCT/US2008/003166 2007-03-13 2008-03-11 Polymères protéine-silicone cationiques WO2008112200A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2468790A (en) * 2009-04-22 2010-09-22 Pz Cussons Fluid composition for application to hair ahead of heat styling
CN113197220A (zh) * 2021-05-06 2021-08-03 维尼健康（深圳）股份有限公司 一种用于无纺布的除螨消毒剂及其制备方法
CN117143676A (zh) * 2023-09-01 2023-12-01 金欧(广东)生物科技有限公司 一种具有防真丝褪色/串色和柔顺功效的真丝洗衣液

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US4891166A (en) * 1987-06-06 1990-01-02 Th. Goldschmidt Ag Diquaternary polysiloxanes, their synthesis and use in cosmetic preparations
US4895964A (en) * 1988-07-01 1990-01-23 Union Carbide Chemicals And Plastics Company Inc. Quarternary ammonium pendant siloxane copolymers
US5098979A (en) * 1991-03-25 1992-03-24 Siltech Inc. Novel silicone quaternary compounds
US5243028A (en) * 1990-06-27 1993-09-07 Siltech Corporation Silicone protein polymers

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Publication number Priority date Publication date Assignee Title
US4891166A (en) * 1987-06-06 1990-01-02 Th. Goldschmidt Ag Diquaternary polysiloxanes, their synthesis and use in cosmetic preparations
US4895964A (en) * 1988-07-01 1990-01-23 Union Carbide Chemicals And Plastics Company Inc. Quarternary ammonium pendant siloxane copolymers
US5243028A (en) * 1990-06-27 1993-09-07 Siltech Corporation Silicone protein polymers
US5098979A (en) * 1991-03-25 1992-03-24 Siltech Inc. Novel silicone quaternary compounds

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2468790A (en) * 2009-04-22 2010-09-22 Pz Cussons Fluid composition for application to hair ahead of heat styling
CN113197220A (zh) * 2021-05-06 2021-08-03 维尼健康（深圳）股份有限公司 一种用于无纺布的除螨消毒剂及其制备方法
CN117143676A (zh) * 2023-09-01 2023-12-01 金欧(广东)生物科技有限公司 一种具有防真丝褪色/串色和柔顺功效的真丝洗衣液

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