US20070202064A1 - Rheology modifier/hair styling resin - Google Patents

Rheology modifier/hair styling resin Download PDF

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US20070202064A1
US20070202064A1 US11/786,639 US78663907A US2007202064A1 US 20070202064 A1 US20070202064 A1 US 20070202064A1 US 78663907 A US78663907 A US 78663907A US 2007202064 A1 US2007202064 A1 US 2007202064A1
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hair
care composition
rheology modifier
acid
composition according
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US11/786,639
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Michael Drzewinski
Joseph Albanese
Eduardo Yap
Jenn Shih
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ISP Investments LLC
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ISP Investments LLC
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Publication of US20070202064A1 publication Critical patent/US20070202064A1/en
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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
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • 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
    • A61K8/817—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • 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
    • A61K8/817—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8176—Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/48—Thickener, Thickening system
    • 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
    • A61Q17/005—Antimicrobial preparations
    • 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
    • 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
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • This invention relates to hair care compositions, and, more particularly, to a rheology modifier/hair styling resin which is a crosslinked, linear poly(vinyl amide/polymerizable carboxylic acid) copolymer for use in such compositions.
  • J. Shih in U.S. Pat. No. 5,015,708, described a process for making terpolymers of vinyl pyrrolidone, acrylic acid and lauryl methacrylate monomers by precipitation polymerization in an aliphatic hydrocarbon solvent.
  • the resultant crosslinked graft copolymer matrix contained 79.9-99.9% of acrylic acid.
  • a rheology modifier/hair styling resin which is a crosslinked, linear poly(vinyl amide/polymerizable carboxylic acid) copolymer; and a process for making same.
  • Another object herein is to provide a crosslinked, linear copolymer which is particularly advantageous for use in hair care compositions. Still another object is to provide hair care formulations which exhibits both high viscosity and long-lasting curl retention for the user.
  • rheology modifier/hair styling resin which is a crosslinked, linear poly(vinyl amide/polymerizable carboxylic acid) copolymer.
  • Suitable vinyl amides include vinyl pyrrolidone, vinyl caprolactam, N-vinyl formamide, N-vinylacetamide, N-vinyl-N-methylacetamide and mixtures thereof, preferably vinyl pyrrolidone.
  • Suitable polymerizable carboxylic acids include (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid and mixtures thereof, preferably acrylic acid.
  • Suitable crosslinkers have at least two free radical polymerizable groups in the molecule, e.g. pentaerythritol triallylether, pentaerythritol triacrylate, pentaerythritol tetraacrylate or methylene bisacrylamide.
  • the composition of the rheology modifier/hair styling resin of the present invention includes a vinyl amide, in an amount of by weight, 1-99% of the composition, a polymerizable carboxylic acid in an amount of 1-99% of the composition, and a crosslinker in an amount of 0.2-3%, based on total weight of monomers.
  • the vinyl amide monomer is present in an amount of 25-80%, the polymerizable carboxylic acid in an amount of 20-80%, and the crosslinker 0.4-2%, based on total weight of monomers.
  • the rheology modifier/hair styling resin may include one or more additional monomers, e.g. lauryl (meth)acrylate, stearyl (meth)acrylate, alkyl (meth)acrylamide or alkyl (meth)acrylate.
  • the alkyl can be C 1 to C 30 or polyethylene oxide.
  • a process of making the rheology modifier/hair styling resin which comprises precipitation polymerizing, by wt., 5-50%, preferably 10-25%, of a mixture of a vinyl amide, a polymerizable carboxylic acid and a crosslinker, in the presence of 50-95%, preferably 75-90%, of a non-polar, removable organic solvent, and 0.1-5%, preferably 0.5-2%, of a free radical initiator, based on total weight of monomers.
  • a personal care composition e.g. a hair care composition, which includes the rheology modifier/hair styling resin of the invention, suitably in an amount of 0.1-20% by wt. of the composition, preferably 0.2-10%, and most preferably 0.5-5%.
  • Typical hair care compositions which include the invention resin have an advantageously high viscosity of about 30,000 to 100,000 cps, preferably 40,000 to 70,000 cps, at a pH of about 5 to 9 and a long-lasting curl retention of 95 to 100% over a 4-hour period at 90% RH and 80° F.
  • the hair care compositions of the invention also exhibit other advantageous user properties, such as shine, stiffness, crunch, stiffness after 5 th and 10 th compression, curl snap, comb drag, residue on comb, manageability, hair feel and static.
  • FIG. 1 is a plot of Viscosity vs. pH for the rheology modifier/hair styling resin of the present invention.
  • FIG. 2 is a plot of Curl Retention vs. Time for a hair care formulation which includes the resin of the invention.
  • the process of making the rheology modifier/hair styling resin of the present invention is suitably carried out in a non-polar solvent, e.g. heptane, benzene, isopropyl acetate or cyclohexane, which can be removed easily after the polymerization, in the presence of a free radical initiator, at a polymerization temperature of 40°-150° C., preferably 55°-100° C., at monomer feeding times in 2 feeding lines of 0-10 hrs, preferably 3-5 hrs.
  • the reactants are monomers and crosslinker.
  • the product is a crosslinked, linear copolymer of a vinyl amide, e.g.
  • vinyl pyrrolidone and a polymerizable carboxylic acid, e.g. acrylic acid, which is crosslinked with a suitable crosslinking agent e.g. pentaerythritol triallyl ether in the form of a powder.
  • a suitable crosslinking agent e.g. pentaerythritol triallyl ether in the form of a powder.
  • FIG. 1 is a graph of viscosity vs. pH for a solution of fixative resin of the invention at a 1% solids level in water. As shown, the viscosity of the solution is a desirably high value of about 55,000 cps at a pH of about 5-9.
  • FIG. 2 shows the advantageous effective curl retention property of the resin for a typical hair care formulation which includes the resin of Example 1. Typically, a 95-100% curl retention is achieved for such formulation even after 4 hours.
  • Aqueous solutions of the resin of the invention also have the advantageous property of a high yield stress in dynes/cm 2 , generally 10 to 100,000, and preferably 100 to 10,000. Examples of the process are shown as follows.
  • Feeding Solution I was prepared by mixing 50 g of N-vinylpyrrolidone (VP) and 1.0 g of pentaerythritol triallylether (PETE).
  • Feeding Solution II was prepared by weighing 50 g of acrylic acid (AA) into a bottle. 200 microliter of Luperox® 11M75 as initiator was charged into the kettle.
  • Feeding Solutions I and II were simultaneously pumped into the kettle over a period of 4 hours at a constant feeding rate.
  • the resulting solution then was held at 65° C. for 1 hour and the reaction temperature was raised to 90° C.
  • an additional 100 microliter of Luperox® 11M75 was added every two hours for 4 times and the reactor was held at 90° C. for two additional hours after the last dose of Luperox® 11M75 was charged.
  • the contents then were cooled and discharged.
  • the solvent was removed at an oven temperature of 100° C.
  • the resultant resin powder was further dried in a vacuum oven at 100° C.
  • the product was a crosslinked, linear copolymer of VP and AA crosslinked with PETE in a wt. ratio of 50/50/1.
  • Example VP (g) AA (g) PETE (g) 2 75 25 0.5 3 50 50 0.5 4 25 75 0.5 5 75 25 1.0 6 50 50 2.0 7 25 75 1.0 8 75 25 1.5 9 50 50 1.5 10 25 75 1.5
  • Feeding Solution I was prepared by mixing 50 g of N-vinylcaprolactam (VCL) and 1.5 g of pentaerythritol triallylether (PETE).
  • Feeding solution II was prepared by weighing 50 g of acrylic acid (AA) into a bottle. Then 200 microliter of t-butyl peroxypivalate initiator was charged into the kettle.
  • the Feeding Solution I and Feeding Solution II were simultaneously charged into the kettle over 4 hours at a constant feeding rate.
  • the solution was held at 65° C. for 1 hour and the temperature was raised to 90° C.
  • an additional 200 microliter of t-butyl peroxypivalate was added every two hours for 4 times and the reactor was held at 90° C. for two additional hours after the last dose of t-butyl peroxypivalate was charged.
  • the contents then were cooled and discharged.
  • the solvent was removed at an oven temperature of 100° C.
  • the resultant resin powder was further dried in a vacuum oven at 100° C.
  • the product was a crosslinked, linear copolymer of VCL and AA crosslinked with PETE in a wt. ratio of 50/50/1.5.
  • Feeding Solution I was prepared by mixing 60 g of N-vinylpyrrolidone (VP), 15 g of stearyl methacrylate (SM) and 1.0 g of pentaerythritol triallylether (PETE).
  • Feeding Solution II was prepared by weighing 25 g of acrylic acid (AA) into a bottle.
  • Luperox® 11M75 was added every two hours for 4 times and the reactor was held at 90° C. for two additional hours after the last dose of Luperox® 11M75 was charged. The contents then were cooled and discharged. The solvent was removed at an oven temperature of 100° C. The resultant resin powder was further dried in a vacuum oven at 100° C. The product was a crosslinked, linear terpolymer of VP, AA and SM crosslinked with PETE in a wt. ratio of 600/25/15/1.
  • Example VCL (g) AA (g) PETE (g) 12 75 25 1.5 13 25 75 1.5 14 50 50 2.0
  • Feeding Solution I is prepared by mixing 50 g of
  • Feeding solution II is prepared by weighing 50 g of methacrylic acid (MAA) into a bottle. Then 300 microliter of t-butyl peroxypivalate initiator is charged into the kettle.
  • MAA methacrylic acid
  • the Feeding Solution I and Feeding Solution II are simultaneously pumped into the kettle over 5 hours at a constant feeding rate.
  • the solution is held at 70° C. for 1 hour and the solution is transferred to stainless high pressure reactor. Then an additional 0.5 g of di-t-butylperoxide is added.
  • the temperature of the reactor is raised to 130° C. and held for 10 hours.
  • the contents then are cooled and discharged.
  • the solvent is removed at an oven temperature of 100° C.
  • the resultant resin powder is further dried in a vacuum oven at 100° C.
  • the product is a crosslinked, linear copolymer of VP and MAA crosslinked with PETE in a wt. ratio of 50/50/1.
  • the mix time should be doubled is the polymer was “dumped;” 6) Pre-mix 0.44 parts of neutralizer AMP with 5 parts of DI water, and add to the main batch; 7) Lower the RPM's to avoid excessive aeration; 8) Mix for 30-60 minutes to ensure uniform gel; 9) Product should appear as clear gel, pH 6.7, and viscosity RV TC @ 10 rpm 50,000 cPs.
  • the resin of the invention is particularly useful for hair care, it will be understood that it can be used in other personal care applications, such as skin care or as an absorbent material in appropriate applications such as diapers, etc.
  • FIG. 1 herein shows the viscosity vs. pH property of the fixative resin of the invention t 1% solids in water.
  • the viscosity is a desirably high value of about 55,000 cps at a pH of about 5-9.
  • FIG. 2 herein shows the advantageous effective curl retention vs. time for a typical hair care formulation of the invention which includes the resin of Example 1. Substantially 95-100% curl retention is achieved even after 4 hours.
  • conditioning agents function to improve the cosmetic properties of the hair, particularly softness, thickening, untangling, feel, and static electricity and may be in liquid, semi-solid, or solid form such as oils, waxes, or gums.
  • any known skin altering agent is useful in the compositions of this invention.
  • Preferred conditioning agents include cationic polymers, cationic surfactants and cationic silicones.
  • Conditioning agents may be chosen from synthesis oils, mineral oils, vegetable oils, fluorinated or perfluorinated oils, natural or synthetic waxes, silicones, cationic polymers, proteins and hydrolyzed proteins, ceramide type compounds, cationic surfactants, fatty amines, fatty acids and their derivatives, as well as mixtures of these different compounds.
  • the synthesis oils include polyolefins, e.g., poly- ⁇ -olefins such as polybutenes, polyisobutenes and polydecenes.
  • the polyolefins can be hydrogenated.
  • the mineral oils suitable for use in the compositions of the invention include hexadecane and oil of paraffin.
  • Suitable animal and vegetable oils include sunflower, corn, soy, avocado, jojoba, squash, raisin seed, sesame seed, walnut oils, fish oils, glycerol tricaprocaprylate, Purcellin oil or liquid jojoba.
  • Suitable natural or synthetic oils include eucalyptus, lavender, vetiver, litsea cubeba, lemon, sandalwood, rosemary, chamomile, savory, nutmeg, cinnamon, hyssop, caraway, orange, geranium, cade, and bergamot.
  • Suitable natural and synthetic waxes include carnauba wax, candelila wax, alfa wax, paraffin wax, ozokerite wax, vegetable waxes such as olive wax, rice wax, hydrogenated jojoba wax, absolute flower waxes such as black currant flower wax, animal waxes such as bees wax, modified bees wax (cerabellina), marine waxes and polyolefin waxes such as polyethylene wax.
  • the cationic polymers (other than the poly (alkyl) vinyllactam polymers according to the invention) that may be used as a conditioning agent according to the invention are those known to improve the cosmetic properties of hair treated by detergent compositions.
  • the expression “cationic polymer” as used herein, indicates any polymer containing cationic groups and/or ionizable groups in cationic groups.
  • the cationic polymers used generally have a molecular weight the average number of which falls between about 500 and 5,000,000 and preferably between 1000 and 3,000,000.
  • the preferred cationic polymers are chosen from among those containing units including primary, secondary, tertiary, and/or quaternary amine groups that may either form part of the main polymer chain or a side chain.
  • Useful cationic polymers include known polyamine, polyaminoamide, and quaternary polyammonium types of polymers, such as:
  • the copolymers can contain one or more units derived from acrylamides, methacrylamides, diacetone acrylamides, acrylamides and methacrylamides, acrylic or methacrylic acids or their esters, vinyllactams such as vinyl pyrrolidone or vinyl caprolactam, and vinyl esters.
  • copolymers of acrylamide and dimethyl amino ethyl methacrylate quaternized with dimethyl sulfate or with an alkyl halide copolymers of acrylamide and methacryloyl oxyethyl trimethyl ammonium chloride; the copolymer of acrylamide and methacryloyl oxyethyl trimethyl ammonium methosulfate; copolymers of vinyl pyrrolidone/dialkylaminoalkyl acrylate or methacrylate, optionally quaternized, such as the products sold under the name GAFQUAT by International Specialty Products; the dimethyl amino ethyl methacrylate/vinyl caprolactam/vinyl pyrrolidone terpolymers, such as the product sold under the name GAFFIX VC 713 by International Specialty Products; the vinyl pyrrolidone/methacrylamidopropyl dimethylamine copolymer, marketed under
  • derivatives of cationic cellulose such as cellulose copolymers or derivatives of cellulose grafted with a hydrosoluble quaternary ammonium monomer, as described in U.S. Pat. No. 4,131,576, such as the hydroxy alkyl cellulose, and the hydroxymethyl-, hydroxyethyl- or hydroxypropyl-cellulose grafted with a salt of methacryloyl ethyl trimethyl ammonium, methacrylamidopropyl trimethyl ammonium, or dimethyl diallyl ammonium.
  • cationic polysaccharides such as described in U.S. Pat. Nos. 3,589,578 and 4,031,307, guar gums containing cationic trialkyl ammonium groups and guar gums modified by a salt, e.g., chloride of 2,3-epoxy propyl trimethyl ammonium.
  • polymers composed of piperazinyl units and alkylene or hydroxy alkylene divalent radicals with straight or branched chains, possibly interrupted by atoms of oxygen, sulfur, nitrogen, or by aromatic or heterocyclic cycles, as well as the products of the oxidation and/or quaternization of such polymers.
  • water-soluble polyamino amides prepared by polycondensation of an acid compound with a polyamine. These polyamino amides may be reticulated.
  • a dioxycarboxylic acid chosen from among diglycolic acid and saturated dicarboxylic aliphatic acids having 3 to 8 atoms of carbon.
  • quaternary polyammonium polymers including, for example, Mirapol® A 15, Mirapol® AD1, Mirapol® AZ1, and Mirapol® 175 products sold by Miranol.
  • cationic polymers that may be used within the context of the invention are cationic proteins or hydrolyzed cationic proteins, polyalkyleneimines such as polyethyleneimines, polymers containing vinyl pyridine or vinyl pyridinium units, condensates of polyamines and epichlorhydrins, quaternary polyurethanes, and derivatives of chitin.
  • Preferred cationic polymers are derivatives of quaternary cellulose ethers, the homopolymers and copolymers of dimethyl diallyl ammonium chloride, quaternary polymers of vinyl pyrrolidone and vinyl imidazole, and mixtures thereof.
  • the conditioning agent can be any silicone known by those skilled in the art to be useful as a conditioning agent.
  • the silicones suitable for use according to the invention include polyorganosiloxanes that are insoluble in the composition.
  • the silicones may be present in the form of oils, waxes, resins, or gums. They may be volatile or non-volatile.
  • the silicones can be selected from polyalkyl siloxanes, polyaryl siloxanes, polyalkyl aryl siloxanes, silicone gums and resins, and polyorgano siloxanes modified by organofunctional groups, and mixtures thereof.
  • Suitable polyalkyl siloxanes include polydimethyl siloxanes with terminal trimethyl silyl groups or terminal dimethyl silanol groups (dimethiconol) and polyalkyl (C 1 -C 20 ) siloxanes.
  • Suitable polyalkyl aryl siloxanes include polydimethyl methyl phenyl siloxanes and polydimethyl diphenyl siloxanes, linear or branched.
  • the silicone gums suitable for use herein include polydiorganosiloxanes preferably having a number-average molecular weight between 200,000 and 1,000,000, used alone or mixed with a solvent.
  • examples include polymethyl siloxane, polydimethyl siloxane/methyl vinyl siloxane gums, polydimethyl siloxane/diphenyl siloxane, polydimethyl siloxane/phenyl methyl siloxane and polydimethyl siloxane/diphenyl siloxane/methyl vinyl siloxane.
  • Suitable silicone resins include silicones with a dimethyl/trimethyl siloxane structure and resins of the trimethyl siloxysilicate type.
  • organo-modified silicones suitable for use in the invention include silicones such as those previously defined and containing one or more organofunctional groups attached by means of a hydrocarbon radical and grafted siliconated polymers. Particularly preferred are amino functional silicones.
  • the silicones may be used in the form of emulsions, nano-emulsions, or micro-emulsions.
  • the conditioning agent can be a protein or hydrolyzed cationic or non-cationic protein.
  • these compounds include hydrolyzed collagens having triethyl ammonium groups, hydrolyzed collagens having trimethyl ammonium and trimethyl stearyl ammonium chloride groups, hydrolyzed animal proteins having trimethyl benzyl ammonium groups (benzyltrimonium hydrolyzed animal protein), hydrolyzed proteins having groups of quaternary ammonium on the polypeptide chain, including at least one C 1 -C 18 alkyl.
  • Hydrolyzed proteins include Croquat L, in which the quaternary ammonium groups include a C 12 alkyl group, Croquat M, in which the quaternary ammonium groups include C 10 -C 18 alkyl groups, Croquat S in which the quaternary ammonium groups include a C 18 alkyl group and Crotein Q in which the quaternary ammonium groups include at least one C 1 -C 18 alkyl group.
  • Croda in which the quaternary ammonium groups include a C 12 alkyl group
  • Croquat M in which the quaternary ammonium groups include C 10 -C 18 alkyl groups
  • Croquat S in which the quaternary ammonium groups include a C 18 alkyl group
  • Crotein Q in which the quaternary ammonium groups include at least one C 1 -C 18 alkyl group.
  • the conditioning agent can comprise quaternized vegetable proteins such as wheat, corn, or soy proteins such as cocodimonium hydrolyzed wheat protein, laurdimonium hydrolyzed wheat protein and steardimonium hydrolyzed wheat protein.
  • the conditioning agent can be a ceramide type of compound such as a ceramide, a glycoceramide, a pseudoceramide, or a neoceramide. These compounds can be natural or synthetic. Compounds of the ceramide type are, for example, described in Patents pending DE4424530,
  • Ceramide type compounds useful herein include 2-N-linoleoyl amino-octadecane-1,3-diol, 2-N-oleoyl amino-octadecane-1,3-diol, 2-N-palmitoyl amino-octadecane-1,3-diol,
  • the conditioning agent can be a cationic surfactant such as a salt of a primary, secondary, or tertiary fatty amine, optionally polyoxyalkylenated, a quaternary ammonium salt, a derivative of imadazoline, or an amine oxide.
  • a cationic surfactant such as a salt of a primary, secondary, or tertiary fatty amine, optionally polyoxyalkylenated, a quaternary ammonium salt, a derivative of imadazoline, or an amine oxide.
  • Suitable examples include mono-, di-, or tri-alkyl quaternary ammonium compounds with a counterion such as a chloride, methosulfate, tosylate, etc. including, but not limited to, cetrimonium chloride, dicetyidimonium chloride, behentrimonium methosulfate, and the like.
  • the presence of a quaternary ammonium compound in conjunction with the polymer described above reduces static and enhances combing of hair in the dry state.
  • the polymer also enhances the deposition of the quaternary ammonium compound onto the hair substrate thus enhancing the conditioning effect of hair.
  • the conditioning agent can be any fatty amine known to be useful as a conditioning agent; e.g. dodecyl, cetyl or stearyl amines, such as stearamidopropyl dimethylamine.
  • the conditioning agent can be a fatty acid or derivatives thereof known to be useful as conditioning agents.
  • Suitable fatty acids include myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, and isostearic acid.
  • the derivatives of fatty acids include carboxylic ester acids including mono-, di-, tri- and tetra-carboxylic acids.
  • the conditioning agent can be a fluorinated or perfluorinated oil.
  • Fluorinated oils include perfluoropolyethers described in EP-A-486135 and the fluorohydrocarbon compounds described in WO 93/11103.
  • the fluoridated oils may also be fluorocarbons such as fluoramines, e.g., perfluorotributylamine, fluoridated hydrocarbons, such as perfluorodecahydronaphthalene, fluoroesters, and fluoroethers.
  • conditioning agent or agents can be present in an amount of 0.001% to 20%, preferably from 0.01% to 10%, and even more preferably from 0.1% to 3% by weight based on the total weight of the final composition.
  • composition of the invention can contain one or more protecting agents to prevent or limit the degrading effects of natural physical and/or chemical assaults on the keratinous materials.
  • the protecting agent can be chosen from hydrosoluble, liposoluble and water-insoluble UV filters, antiradical agents, antioxidants, vitamins and pro-vitamins.
  • the above-described cationic polymer enhances the deposition of these materials onto the hair or skin substrate enhancing protection of hair to UV damage.
  • Organic UV filters can be chosen from among hydrosoluble or liposoluble filters, whether siliconated or nonsiliconated, and mineral oxide particles, the surface of which may be treated.
  • Hydrosoluble organic UV filters may be chosen from para-amino benzoic acid and its salts, anthranilic acid and its salts, salicylic acid and its salts, hydroxy cinnamic acid and its salts, sulfonic derivatives of benzothiazoles, benzimidizoles, benzoxazoles and their salts, sulfonic derivatives of benzophenone and their salts, sulfonic derivatives of benzylidene camphor and their salts, derivatives of benzylidene camphor substituted by a quaternary amine and their salts, derivatives of phthalydene-camphosulfonic acids and their salts, sulfonic derivatives of benzotriazole, and mixtures thereof.
  • Hydrophilic polymers which have light-protective qualities against UV rays can be used. These include polymers containing benzylidene camphor and/or benzotriazole groups.
  • Suitable liposoluble organic UV filters include derivatives of para-aminobenzoic acid, such as the esters or amides of para-aminobenzoic acid; derivatives of salicylic acid; derivatives of benzophenone; derivatives of dibenzoyl methane; derivatives of diphenyl acrylates; derivatives of benzofurans; UV filter polymers containing one or more silico-organic residues; esters of cinnamic acid; derivatives of camphor; derivatives of trianilino-s-triazine; the ethylic ester urocanic acid; benzotriazoles; derivatives of hydroxy phenyl triazine; bis-resorcinol-dialkyl amino triazine; and mixtures thereof.
  • para-aminobenzoic acid such as the esters or amides of para-aminobenzoic acid
  • derivatives of salicylic acid such as the esters or amides of para-aminobenzo
  • the liposoluble (or lipophilic) organic UV filter according to the invention can be chosen from octyl salicylate; 4-tert-butyl-4′-methoxy dibenzoyl methane; octocrylene; 4-methoxy cinnamate; 2-ethylhexyl [2-ethylhexyl 4-methoxycinnamate]; and 2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethyl silyl)oxy]disiloxanyl]propynyl]phenol.
  • UV filters particularly preferred for use herein are derivatives of benzophenones such as 2-hydroxy-4-methoxy benzophenone-5-sulfonic acid, 2-hydroxy-4-methoxy benzophenone, derivatives of benzalmalonates such as poly dimethyl/methyl (3(4-(2,2-bis-ethoxy carbonyl vinyl)-phenoxy)-propenyl) siloxane, derivatives of benzylidene camphor such as b-b′camphosulfonic [1-4 divinylbenzene] acid and derivatives of benzimidazole such as 2-phenyl-benzimidazol-5-sulfonic acid.
  • benzophenones such as 2-hydroxy-4-methoxy benzophenone-5-sulfonic acid, 2-hydroxy-4-methoxy benzophenone
  • derivatives of benzalmalonates such as poly dimethyl/methyl (3(4-(2,2-bis-ethoxy carbonyl vinyl)-phenoxy)-propenyl) siloxane
  • Water-insoluble UV filters include various mineral oxides.
  • the mineral oxides may be selected from among titanium oxides, zinc oxides, and cerium oxides.
  • the mineral oxides can be used in the form of ultrafine nanoparticles.
  • Preferred UV filters include Escalol HP-610 (dimethylpabamido propyl laurdimonium tosylate and propylene glycol stearate) and Crodasorb HP (polyquaternium 59).
  • the antioxidants or antiradical agents can be selected from phenols such as BHA (tert-butyl-4-hydroxy anisole), BHT (2,6-di-tert-butyl-p-cresol), TBHQ (tert-butyl hydroquinone), polyphenols such as proanthocyanodic oligomers, flavonoids, hindered amines such as tetra amino piperidine, erythorbic acid, polyamines such as spermine, cysteine, glutathione, superoxide dismutase, and lactoferrin.
  • BHA tert-butyl-4-hydroxy anisole
  • BHT 2,6-di-tert-butyl-p-cresol
  • TBHQ tert-butyl hydroquinone
  • polyphenols such as proanthocyanodic oligomers, flavonoids, hindered amines such as tetra amino piperidine, erythorbic acid, polyamines such as sper
  • the vitamins can be selected from ascorbic acid (vitamin C), vitamin E, vitamin E acetate, vitamin E phosphate, B vitamins such as B3 and B5, vitamin PP, vitamin A, and derivatives thereof.
  • the provitamins can be selected from panthenol and retinol.
  • the protecting agent can be present in an amount 0.001% to 20% by weight, preferably from 0.01% to 10% by weight, and more preferably 0.1 to 5% by weight of the total weight of the final composition.
  • the composition of the invention can contain a fixing agent.
  • the fixing agent can be an anionic polymer chosen from polymers containing carboxylic units derived from unsaturated carboxylic mono- or polyacids of the formula: in which n is a whole number from 0 to 10, A 1 denotes a methylene group, optionally bonded to the carbon atom of the unsaturated group or to a neighboring methylene group when n is greater than 1 by means of a heteroatom like oxygen or sulfur, R 7 denotes a hydrogen atom, a phenyl or benzyl group, R 8 denotes a hydrogen atom, a lower alkyl or carboxyl group, R 9 denotes a hydrogen atom, a lower alkyl group, a —CH 2 —COOH, phenyl or benzyl group and polymers containing units derived from sulfonic acid like vinylsulfonic, styrenesulfonic, acrylamidoalkylsulf
  • the fixing agent can be an amphoteric polymer chosen from the polymer containing recurring units derived from: a) at least one monomer chosen from acrylamides or methacrylamides substituted on the nitrogen with an alkyl radical; b) at least one acid copolymer containing one or more reactive carboxyl groups; and c) at least one basic comonomer, such as esters with primary, secondary, tertiary, and quaternary amino substitutents of acrylic and methacrylic acids and the product of quaternization of dimethylaminoethyl methacrylate with dimethyl or diethyl sulfate.
  • an amphoteric polymer chosen from the polymer containing recurring units derived from: a) at least one monomer chosen from acrylamides or methacrylamides substituted on the nitrogen with an alkyl radical; b) at least one acid copolymer containing one or more reactive carboxyl groups; and c) at least one basic comonomer,
  • the fixing agent can be a nonionic polymer chosen from polyalkyloxazolines; vinyl acetate homopolymers; vinyl acetate and acrylic ester copolymers; vinyl acetate and ethylene copolymers; vinyl acetate and maleic ester copolymers; polyethylene and maleic anhydride copolymers; homopolymers of alkyl acrylates; homopolymers of alkyl methacrylates; copolymers of acrylic esters; copolymers of alkyl acrylates and alkyl methacrylates; copolymers of acrylonitrile and a nonionic monomer chosen from among butadiene and alkyl (meth)acrylates; copolymers of alkyl acrylate and urethane; and polyamides.
  • a nonionic polymer chosen from polyalkyloxazolines; vinyl acetate homopolymers; vinyl acetate and acrylic ester copolymers; vinyl acetate and ethylene copolymers; vinyl acetate and maleic este
  • the fixing polymer can be a functionalized or unfunctionalized, silicone or non-silicone polyurethane.
  • the fixing polymer can be a polymer of the grafted silicone type containing a polysiloxane portion and a portion consisting of a nonsilicone organic chain, with one of the two portions forming the main chain of the polymer, and with the other being grafted onto said main chain.
  • the fixing agent can be present in the composition in a relative weight concentration between 0.1 and 10%, preferably 0.5 and 5%.
  • the composition of the invention can contain an oxidizing agent.
  • the oxidizing agent can be chosen from the group of hydrogen peroxide, urea peroxide, alkali metal bromates, ferricyanides, persalts, and redox enzymes, optionally with their respective donor or cofactor.
  • the oxidizing agent is hydrogen peroxide.
  • the oxidizing agent can be a solution of oxygenated water whose titer varies from 1 to 40 volumes.
  • the composition of the invention can contain at least one reducing agent in amounts from 0.01 to 30 wt %, preferably 0.05 to 20 wt % of the total weight of the composition.
  • the reducing agents useful in the practice of this invention can be selected from thiols, like cysteine, thioglycolic acid, thiolacetic acid, their salts and esters, cysteamine, and its salts or sulfites.
  • ascorbic acid, its salts and its esters, erythorbic acid, its salts and its esters, and sulfinates like sodium hydroxymethanesulfinate can be used.
  • the composition of the invention can contain a dye selected from the group consisting of neutral acid or cationic nitrobenzene dyes, neutral acid or cationic azo dyes, quinone dyes, neutral, acid or cationic anthraquinone dyes, azine dyes, triarylmethane dyes, indoamine dyes and natural dyes.
  • the dye or dyes can be present in a concentration from 0.001 to 20% and preferably 0.005 to 10 wt % based on the total weight of the composition.
  • composition of the invention can contain at least one amphoteric polymer or a cationic polymer different from the cationic poly(vinyllactam) defined above.
  • Suitable cationic polymers include a poly(quaternary ammonium) consisting of recurrent units corresponding to the following formula (W) and (U):
  • Suitable amphoteric polymers include a copolymer containing at least one acrylic acid and a dimethyldiallyammonium salt as a monomer.
  • the cationic or amphoteric polymer or polymers can be present in an amount of 0.01 to 10%, preferably 0.05 to 5%, and more preferably 0.1 to 3% by weight of the total weight of the composition.
  • compositions according to the invention advantageously include at least one surfactant, which can be present in an amount of 0.1% and 60% preferably 1% and 40%, and more preferably 5% and 30% by weight based on the total weight of the composition.
  • the surfactant may be chosen from among anionic, amphoteric, or non-ionic surfactants, or mixtures of them known to be useful in personal care compositions.
  • composition of the invention can contain one or more additional cosmetically acceptable additives chosen from conditioning agents, protecting agents, such as, for example, hydrosoluble, liposoluble and water-insoluble UV filters, antiradical agents, antioxidants, vitamins and pro-vitamins, fixing agents, oxidizing agents, reducing agents, dyes, cleansing agents, anionic, cationic, nonionic and amphoteric surfactants, thickeners, perfumes, pearlizing agents, stabilizers, pH adjusters, filters, preservatives, hydroxy acids, cationic and nonionic polyether associative polyurethanes, polymers other than the cationic polymer described herein, vegetable oils, mineral oils, synthetic oils, polyols such as glycols and glycerol, silicones, aliphatic alcohols, colorants, bleaching agents, highlighting agents and sequestrants.
  • conditioning agents such as, for example, hydrosoluble, liposoluble and water-insoluble UV filters, antiradical agents, antioxidants, vitamins and pro-vitamins, fixing agents, oxid
  • composition of the invention may be included in the composition of the invention, such as:
  • Preferred thickeners or viscosity increasing agents include Carbomer, Aculyn and Stabileze, e.g. crosslinked acrylic acid, crosslinked poly(methylvinyl ether/maleic anhydride) copolymer, acrylamides, carboxymethyl cellulose and the like.
  • compositions according to the invention may be used to wash and treat keratinous material such as hair, skin, eyelashes, eyebrows, fingernails, lips, and hairy skin.
  • compositions according to the invention can be detergent compositions such as shampoos, bath gels, and bubble baths.
  • the compositions will comprise a generally aqueous washing base.
  • the surfactant or surfactants that form the washing base may be chosen alone or in blends, from known anionic, amphoteric, or non-ionic surfactants.
  • the quantity and quality of the washing base must be sufficient to impart a satisfactory foaming and/or detergent value to the final composition.
  • the washing base can be from 4% to 50% by weight, preferably from 6% to 35% by weight, and even more preferentially from 8% to 25% by weight of the total weight of the final composition.
  • the pH of the composition applied to the keratinous material is generally between 2 and 12. It is preferably between 3 and 8, and may be adjusted to the desired value by means of acidifying or alkalinizing agents that are well-known in the state of the art in compositions applied to keratinous materials.
  • the composition of the invention can contain at least one alkalizing or acidifying agent in amounts from 0.01 to 30 wt % of the total weight of the composition.
  • the alkalizing agent can be chosen from ammonia, alkali carbonates, alkanolamines, like mono-, di- and triethanolamines, as well as their derivatives, hydroxyalkylamines and ethoxylated and/or propoxylated ethylenediamines, sodium or potassium hydroxides and compounds of the following formula (XIX): in which R is a propylene residue optionally substituted with an hydroxyl group or a C 1 -C 4 alkyl radical; R 38 , R 39 , R 40 and R 41 , identical or different, represent a hydrogen atom, a C 1 -C 4 alkyl radical or C 1 -C 4 hydroxyalkyl radical.
  • the acidifying agent can be chosen from mineral or organic acids, like hydrochloric acid, orthophosphoric acid, carboxylic acids like tartaric acid, citric acid, or lactic acid, or sulfonic acids and the like.
  • the physiological and cosmetically acceptable medium may consist exclusively of water, a cosmetically acceptable solvent, or a blend of water and a cosmetically acceptable solvent, such as a lower alcohol composed of C 1 to C 4 , such as ethanol, isopropanol, t-butanol, n-butanol, alkylene glycols such as propylene glycol, and glycol ethers.
  • a cosmetically acceptable solvent such as a lower alcohol composed of C 1 to C 4 , such as ethanol, isopropanol, t-butanol, n-butanol, alkylene glycols such as propylene glycol, and glycol ethers.
  • a cosmetically acceptable solvent such as a lower alcohol composed of C 1 to C 4 , such as ethanol, isopropanol, t-butanol, n-butanol, alkylene glycols such as propylene glycol, and glycol ethers.
  • the compositions of the invention can be anhydr
  • compositions are prepared by simple mixing procedures well known in the art.
  • the invention also has as its object a process for treating keratinous material including the skin or hair, characterized in that it consists of applying to skin or keratinous materials a cosmetic composition as described above, and then eventually rinsing it with water. Accordingly, the process according to the invention makes it possible to maintain the hairstyle, treatment, care, washing, or make-up removal of the skin, the hair, and any other keratinous material.
  • compositions according to the invention may also take the form of after-shampoo compositions, to be rinsed off or not, for permanents, straightening, waving, dyeing, or bleaching, or the form of rinse compositions to be applied before or after dyeing, bleaching, permanents, straightening, relaxing, waving or even between the two stages of a permanent or straightening process.
  • compositions of the invention may also take the form of skin-washing compositions, and particularly in the form of solutions or gels for the bath or shower, or of make-up removal products.
  • compositions of the invention may also be in the form of aqueous or hydro-alcoholic solutions for skin and/or hair care.
  • compositions of this invention have demonstrated thermal protection from heat styling tools, more specifically curling or straightening irons.
  • the cationic polymer provides a continuous film on hair that does not degrade nor whiten upon regular exposure to curling irons at temperatures up to 152° C. Protection is observed via tryptophan measurements and perceived by consumer in combing force reduction.
  • compositions described herein are useful in products for personal care, including, but mot limited to, gels, lotions, glazes, glues, mousses, sprays, fixatives, shampoos, conditioners, 2n1 shampoos, temporary hair dyes, semi-permanent hair dyes, permanent hair dyes, straighteners, permanent waves, relaxers, creams, putties, waxes, pomades, moisturizers, mascaras, lip balms and foam enhancers.

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Abstract

A rheology modifier/hair styling resin which is a crosslinked, linear poly(vinyl amide/polymerizable carboxylic acid) copolymer exhibits advantageous hair care properties of high viscosity and long-lasting curl retention.

Description

    CROSS-REFERENCE TO RELATED APPLICATIONS
  • The present application is a Continuation application which claims the benefit of U.S. Nonprovisional application Ser. No. 10/964,948, filed on Oct. 14, 2004; which is incorporated herein by reference thereto.
    • FIELD OF THE INVENTION
  • This invention relates to hair care compositions, and, more particularly, to a rheology modifier/hair styling resin which is a crosslinked, linear poly(vinyl amide/polymerizable carboxylic acid) copolymer for use in such compositions.
    • BACKGROUND OF THE INVENTION
  • J. Shih, in U.S. Pat. No. 5,015,708, described a process for making terpolymers of vinyl pyrrolidone, acrylic acid and lauryl methacrylate monomers by precipitation polymerization in an aliphatic hydrocarbon solvent.
  • Frenz, V. in WO 02/32975, Apr. 25, 2002, described absorbent materials made by grafting acrylic acid monomer onto polyvinyl pyrrolidone polymer in water in the presence of a crosslinking agent. The resultant crosslinked graft copolymer matrix contained 79.9-99.9% of acrylic acid.
  • Accordingly, it is an object of this invention to provide a rheology modifier/hair styling resin which is a crosslinked, linear poly(vinyl amide/polymerizable carboxylic acid) copolymer; and a process for making same.
  • Another object herein is to provide a crosslinked, linear copolymer which is particularly advantageous for use in hair care compositions. Still another object is to provide hair care formulations which exhibits both high viscosity and long-lasting curl retention for the user.
    • SUMMARY OF THE INVENTION
  • What is described herein is a rheology modifier/hair styling resin which is a crosslinked, linear poly(vinyl amide/polymerizable carboxylic acid) copolymer.
  • Suitable vinyl amides include vinyl pyrrolidone, vinyl caprolactam, N-vinyl formamide, N-vinylacetamide, N-vinyl-N-methylacetamide and mixtures thereof, preferably vinyl pyrrolidone.
  • Suitable polymerizable carboxylic acids include (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid and mixtures thereof, preferably acrylic acid.
  • Suitable crosslinkers have at least two free radical polymerizable groups in the molecule, e.g. pentaerythritol triallylether, pentaerythritol triacrylate, pentaerythritol tetraacrylate or methylene bisacrylamide.
  • The composition of the rheology modifier/hair styling resin of the present invention includes a vinyl amide, in an amount of by weight, 1-99% of the composition, a polymerizable carboxylic acid in an amount of 1-99% of the composition, and a crosslinker in an amount of 0.2-3%, based on total weight of monomers.
  • Preferably, the vinyl amide monomer is present in an amount of 25-80%, the polymerizable carboxylic acid in an amount of 20-80%, and the crosslinker 0.4-2%, based on total weight of monomers.
  • Optionally, the rheology modifier/hair styling resin may include one or more additional monomers, e.g. lauryl (meth)acrylate, stearyl (meth)acrylate, alkyl (meth)acrylamide or alkyl (meth)acrylate. The alkyl can be C1 to C30 or polyethylene oxide.
  • As another feature of the invention, there is described a process of making the rheology modifier/hair styling resin which comprises precipitation polymerizing, by wt., 5-50%, preferably 10-25%, of a mixture of a vinyl amide, a polymerizable carboxylic acid and a crosslinker, in the presence of 50-95%, preferably 75-90%, of a non-polar, removable organic solvent, and 0.1-5%, preferably 0.5-2%, of a free radical initiator, based on total weight of monomers.
  • Yet another feature of the invention is the provision of a personal care composition, e.g. a hair care composition, which includes the rheology modifier/hair styling resin of the invention, suitably in an amount of 0.1-20% by wt. of the composition, preferably 0.2-10%, and most preferably 0.5-5%.
  • Typical hair care compositions which include the invention resin have an advantageously high viscosity of about 30,000 to 100,000 cps, preferably 40,000 to 70,000 cps, at a pH of about 5 to 9 and a long-lasting curl retention of 95 to 100% over a 4-hour period at 90% RH and 80° F.
  • The hair care compositions of the invention also exhibit other advantageous user properties, such as shine, stiffness, crunch, stiffness after 5th and 10th compression, curl snap, comb drag, residue on comb, manageability, hair feel and static.
    • BRIEF DESCRIPTION OF THE FIGURES
  • FIG. 1 is a plot of Viscosity vs. pH for the rheology modifier/hair styling resin of the present invention.
  • FIG. 2 is a plot of Curl Retention vs. Time for a hair care formulation which includes the resin of the invention.
    • DETAILED DESCRIPTION OF THE INVENTION
  • The scope of the invention is illustrated by the following Table:
    Suitable Preferred
    Compositional Compositional
    Monomer Example Range Range
    Vinyl amide Vinyl  1-99% 20-80%
    Pyrrolidone,
    Vinyl
    Caprolactam,
    N-vinyl-
    formamide,
    N-vinyl
    acetamide,
    N-vinyl-N-
    methyl acetamide
    Polymerizable (Meth)acrylic  1-99% 20-80%
    carboxylic acid acid, crotonic
    acid, itaconic
    acid, maleic acid
    Crosslinker, more Pentaerythritol 0.2-3% based 0.4-2  
    than two free radical triallylether, on total weight
    groups methylene of monomers
    polymerizable bisacrylamide,
    in the molecule Pentaerythritol
    triacrylate,
    Pentaerythritol
    tetraacrylate
    Optional monomers Lauryl
    (meth)acrylate,
    stearyl
    (meth)acrylate,
    alkyl
    (meth)acrylamide,
    alkyl
    (meth)acrylate
    Free radical t-Butylperoxy 0.1-5%, 0.5-2%  
    initiator, pivalate, based on total
    e.g. peroxide, 2,2′-azobis monomer
    perester, (2-methylbutane-
    percarbonate, Vazo nitrile) weight
    Volatile non-polar Heptane, 95-50% 85-75%
    organic solvent or benzene, (solvent) 15-25%
    mixed solvents isopropyl acetate,  5-50%
    cyclohexane (polymer)
    Process Conditions Suitable Range Preferred Range
    Polymerization temperature
     40° C.-150° C.  55° C.-100° C.
    Monomer feeding time, hrs  0-10 3-5
    (2 feeding lines)
  • The process of making the rheology modifier/hair styling resin of the present invention is suitably carried out in a non-polar solvent, e.g. heptane, benzene, isopropyl acetate or cyclohexane, which can be removed easily after the polymerization, in the presence of a free radical initiator, at a polymerization temperature of 40°-150° C., preferably 55°-100° C., at monomer feeding times in 2 feeding lines of 0-10 hrs, preferably 3-5 hrs. The reactants are monomers and crosslinker. The product is a crosslinked, linear copolymer of a vinyl amide, e.g. vinyl pyrrolidone, and a polymerizable carboxylic acid, e.g. acrylic acid, which is crosslinked with a suitable crosslinking agent e.g. pentaerythritol triallyl ether in the form of a powder.
  • FIG. 1 is a graph of viscosity vs. pH for a solution of fixative resin of the invention at a 1% solids level in water. As shown, the viscosity of the solution is a desirably high value of about 55,000 cps at a pH of about 5-9. FIG. 2 shows the advantageous effective curl retention property of the resin for a typical hair care formulation which includes the resin of Example 1. Typically, a 95-100% curl retention is achieved for such formulation even after 4 hours.
  • Aqueous solutions of the resin of the invention also have the advantageous property of a high yield stress in dynes/cm2, generally 10 to 100,000, and preferably 100 to 10,000. Examples of the process are shown as follows.
    • EXAMPLE 1 Crosslinked, Linear Poly(N-Vinyl Pyrrolidone) (VP)/Acrylic Aced (AA), Copolymer Crosslinked with Pentaerythritol Triallyl Ether (PETE)
  • Into a 1-liter, four-necked glass kettle, equipped with two feeding pumps, an anchor agitator, a thermocouple and a condenser, 500 g of heptane as solvent was charged and agitated at 200 rpm while being purged with nitrogen throughout the process. The solvent then was heated to 65° C. with an oil bath and held there for 30 minutes. Feeding Solution I was prepared by mixing 50 g of N-vinylpyrrolidone (VP) and 1.0 g of pentaerythritol triallylether (PETE). Feeding Solution II was prepared by weighing 50 g of acrylic acid (AA) into a bottle. 200 microliter of Luperox® 11M75 as initiator was charged into the kettle. Then Feeding Solutions I and II were simultaneously pumped into the kettle over a period of 4 hours at a constant feeding rate. The resulting solution then was held at 65° C. for 1 hour and the reaction temperature was raised to 90° C. Then an additional 100 microliter of Luperox® 11M75 was added every two hours for 4 times and the reactor was held at 90° C. for two additional hours after the last dose of Luperox® 11M75 was charged. The contents then were cooled and discharged. The solvent was removed at an oven temperature of 100° C. The resultant resin powder was further dried in a vacuum oven at 100° C. The product was a crosslinked, linear copolymer of VP and AA crosslinked with PETE in a wt. ratio of 50/50/1.
    • EXAMPLE 2-10
  • Example VP (g) AA (g) PETE (g)
    2 75 25 0.5
    3 50 50 0.5
    4 25 75 0.5
    5 75 25 1.0
    6 50 50 2.0
    7 25 75 1.0
    8 75 25 1.5
    9 50 50 1.5
    10 25 75 1.5
    • EXAMPLE 11 Crosslinked, Linear Poly(N-Vinyl Caprolactam) (VCL)/Acrylic Acid) Copolymer Crosslinked with Pentaerythritol Triallyl Ether
  • Into a 1-liter, four-necked glass kettle, equipped with an anchor agitator, a thermocouple and a condenser, 500 g of heptane as solvent was charged and agitated at 200 rpm while being purged with nitrogen throughout the process. The solvent then was heated to 65° C. with an oil bath and held there for 30 minutes. Feeding Solution I was prepared by mixing 50 g of N-vinylcaprolactam (VCL) and 1.5 g of pentaerythritol triallylether (PETE). Feeding solution II was prepared by weighing 50 g of acrylic acid (AA) into a bottle. Then 200 microliter of t-butyl peroxypivalate initiator was charged into the kettle. The Feeding Solution I and Feeding Solution II were simultaneously charged into the kettle over 4 hours at a constant feeding rate. The solution was held at 65° C. for 1 hour and the temperature was raised to 90° C. Then an additional 200 microliter of t-butyl peroxypivalate was added every two hours for 4 times and the reactor was held at 90° C. for two additional hours after the last dose of t-butyl peroxypivalate was charged. The contents then were cooled and discharged. The solvent was removed at an oven temperature of 100° C. The resultant resin powder was further dried in a vacuum oven at 100° C. The product was a crosslinked, linear copolymer of VCL and AA crosslinked with PETE in a wt. ratio of 50/50/1.5.
    • EXAMPLE 11A Crosslinked, Linear Poly(N-Vinyl Pyrrolidone) (VP)/Acrylic Acid (AA)/Stearyl Methacrylate (SM) Terpolymer Crosslinked with Pentaerythritol Triallyl Ether (PETE)
  • Into a 1-liter, four-necked glass kettle, equipped with two feeding pumps, an anchor agitator, a thermocouple and a condenser, 500 g of heptane as solvent was charged and agitated at 200 rpm while being purged with nitrogen throughout the process. The solvent then was heated to 65° C. with an oil bath and held there for 30 minutes. Feeding Solution I was prepared by mixing 60 g of N-vinylpyrrolidone (VP), 15 g of stearyl methacrylate (SM) and 1.0 g of pentaerythritol triallylether (PETE). Feeding Solution II was prepared by weighing 25 g of acrylic acid (AA) into a bottle. 200 microliter of Luperox® 11M75 as initiator was charged into the kettle. Then Feeding Solutions I and II were simultaneously pumped into the kettle over a period of 4 hours at a constant feeding rate. The resulting solution then was held at 65° C. for 1 hour and the reaction temperature was raised to 90° C. Then an additional 100 microliter of
  • Luperox® 11M75 was added every two hours for 4 times and the reactor was held at 90° C. for two additional hours after the last dose of Luperox® 11M75 was charged. The contents then were cooled and discharged. The solvent was removed at an oven temperature of 100° C. The resultant resin powder was further dried in a vacuum oven at 100° C. The product was a crosslinked, linear terpolymer of VP, AA and SM crosslinked with PETE in a wt. ratio of 600/25/15/1.
    • EXAMPLES 12-14
  • Example VCL (g) AA (g) PETE (g)
    12 75 25 1.5
    13 25 75 1.5
    14 50 50 2.0
    • EXAMPLE 15 Crosslinked, Linear Poly(N-Vinyl Pyrrolione)/Methacrylic Acid (MAA) Copolymer Crosslinked with Pentaerythritol Triallyl Ether
  • Into a 1-liter, four-necked glass kettle, equipped with two feeding pumps, an anchor agitator, a thermocouple and a condenser, 600 g of heptane as solvent is charged and agitated at 300 rpm while being purged with nitrogen throughout the process. The solvent then is heated to 70° C. with an oil bath and held there for 30 minutes. Feeding Solution I is prepared by mixing 50 g of
  • N-vinylpyrrolidone (VP) and 1.0 g of pentaerythritol triallylether (PETE). Feeding solution II is prepared by weighing 50 g of methacrylic acid (MAA) into a bottle. Then 300 microliter of t-butyl peroxypivalate initiator is charged into the kettle.
  • The Feeding Solution I and Feeding Solution II are simultaneously pumped into the kettle over 5 hours at a constant feeding rate. The solution is held at 70° C. for 1 hour and the solution is transferred to stainless high pressure reactor. Then an additional 0.5 g of di-t-butylperoxide is added. The temperature of the reactor is raised to 130° C. and held for 10 hours. The contents then are cooled and discharged. The solvent is removed at an oven temperature of 100° C. The resultant resin powder is further dried in a vacuum oven at 100° C. The product is a crosslinked, linear copolymer of VP and MAA crosslinked with PETE in a wt. ratio of 50/50/1.
  • Representative personal care formulations which include the resin of the invention are shown below.
    • EXAMPLE 16 Hair Styling Gel Composition
  • Ingredient Wt. %
    DI water 98.51
    AMP-95 (Aminomethylpropanol 95%) 0.49
    Polymer of Example 1 1.00
    100%

    Procedure: 1) Charge 93.51 parts of DI water into a suitable vessel; 2) Add 0.05 parts of pre-neutralizer 2-amino-2-methylpropanol (AMP); 3) Start agitation at medium speed; 4) Slowly sprinkle in 1.0 parts of the polymer powder. Alternatively the powder can be “dumped” it will eventually disperse throughout on its own; 5) Allow to mix for 30-60 minutes, at medium-low speed, to ensure complete dispersion, if white particles are present, continue mixing until particles have disappeared. The mix time should be doubled is the polymer was “dumped;” 6) Pre-mix 0.44 parts of neutralizer AMP with 5 parts of DI water, and add to the main batch; 7) Lower the RPM's to avoid excessive aeration; 8) Mix for 30-60 minutes to ensure uniform gel; 9) Product should appear as clear gel, pH 6.7, and viscosity RV TC @ 10 rpm 50,000 cPs.
    • EXAMPLE 16A —HAIR STYLING GEL COMPOSITION
  • Ingredient Wt. %
    DI water 98.35
    AMP-95 (Aminomethylpropanol 95%) 0.65
    Polymer of Example 1 0.50
    Carbomer 980 0.50
    100%
    • EXAMPLE 16B Hair Styling Gel Composition
  • Ingredient Wt. %
    DI water 97.95
    AMP-95 (Aminomethyl propanol 95%) 0.55
    Polymer of Example 1 0.50
    Aculyn 22 1.00
    100%
    • EXAMPLE 16C Hair Fixative Composition
  • Ingredient Wt. %
    DI water 98.51
    AMP-95 (Aminomethylpropanol 95%) 0.49
    Polymer of Example 1 1.00
    100%
    • EXAMPLE 17 Clear Bath Gel Composition
  • Ingredient Wt. %
    Water 42.07
    AMP-95 0.93
    Polymer of Example 1 2.00
    Sodium Laureth Sulfate (28%) 40.00
    Cocamidopropyl betaine (35%) 15.00
    100%
    • EXAMPLE 18 Antibacterial Liquid Hand Soap
  • Ingredient Wt. %
    Water 54.57
    AMP-95 0.49
    Polymer of Example 1 1.00
    Ammonium Lauryl Sulfate (30%) 25.00
    Disodium Laureth Sulfosuccinate (40%) 8.00
    Cocamidopropyl betaine (35%) 4.00
    Glycerin 2.00
    Propylene Glycol 2.00
    Triclosan 0.50
    Parfum 1.29
    Polysorbate-20 0.50
    Liquid Germall ® Plus 0.15
    Dimethicone (and) Gelatin (and) Gum
    Acacia (and) Xanthan Gum 0.50
    100%
    • EXAMPLE 19 Clear Shampoo Gel
  • Ingredient Wt. %
    Water 40.82
    AMP-95 0.93
    Polymer of Example 1 2.00
    Sodium Laureth Sulfate (28%) 40.00
    Cocamidopropyl betaine (35%) 15.00
    Polyquaternium-11 (Gafquat ® 755N) 0.10
    Propylene Glycol (and) Diazolidinyl Urea 0.15
    (and) lodopropynyl Butylcarbamate
    (Liquid Germall ® Plus)
    Halicrest blue beads (Shea butter) 0.50
    Hallcrest pink beads (Dimethicone) 0.50
    100%
    • EXAMPLE 20 Complex Conditioning Shampoo
  • Ingredient INCI name Wt. %
    Water DI water 52.77
    AMP-95 Amonomethyl Propanol (95%) 0.49
    Polymer of Example 1 Crosslinked VP/AA 1.00
    Stepanol WAT-K TEA Lauryl Sulfate 30.56
    (39.23% actives)
    Si-tech GE 3092 Cyclopentasiloxane (and) 1.00
    Dimethiconol
    Ninol CMP Cocamide MEA 3.00
    Maprosyl 30 Sodium Lauroyl Sarcosinate 1.26
    (30% actives)
    Dissolvene NA2-S Disodium EDTA 3.33
    Soy Tein NL Hydrolyzed Soy Protein 0.10
    Cerasynt IP Glycol Stearate (and) 1.25
    Other Ingredients
    Orchid complex Caprylic/Capric Triglyceride (and) 1.50
    Cymbidium Grandiflorum Flower
    Extract
    Conditioneze NT
    20 Polyquaternium-28 (19.4% actives) 1.30
    Parfum Fragrance 1.29
    Tween-20 Polysorbate-20 0.50
    Liquid Germall Plus Propylene Glycol (and) Diazolidinyl 0.15
    Urea (and) Iodopropynyl
    Butylcarbamate
    Hallcrest Pink Beads Dimethicone (and) Gelatin (and) 0.50
    Gum Acacia (and) Xanthan Gum
    100%
    • EXAMPLE 21 Hair Fixative Composition
  • Ingredient Wt. %
    Water 96.51
    AMP-95 0.49
    Polymer of Example 1 1.00
    Omnirez 2000 (50%) 2.00
    100%
    • EXAMPLE 22 Hair Fixative Composition
  • Ingredient Wt. %
    Water 79.81
    AMP-95 0.49
    Polymer of Example 1 1.00
    Gaffix VC 713 copolymer (37%) 3.70
    Advantage S (10%) 10.00
    Copolymer 845 (20%) 5.00
    100%
    • EXAMPLE 23 Hair Fixative Composition
  • Ingredient Wt. %
    Water 78.51
    AMP-95 0.49
    Polymer of Example 1 1.00
    Gafquat 755 (20%) 5.00
    Advantage S (10%) 10.00
    Copolymer 845 (20%) 5.00
    100%
    • EXAMPLE 24 Hair Fixative Composition
  • Ingredient Wt. %
    Water 79.81
    AMP-95 0.49
    Polymer of Example 1 1.00
    Ganex P 904 LC (10%) 3.70
    Advantage S (10%) 10.00
    Copolymer 845 (20%) 5.00
    100%
    • EXAMPLE 25 Hair Fixative Composition
  • Ingredient Wt. %
    Water 95.17
    AMP-95 0.49
    Polymer of Example 1 1.00
    Gafquat 440 (30%) 3.34
    100%
    • EXAMPLE 26 Hair Fixative Composition
  • Ingredient Wt. %
    Water 93.51
    AMP-95 0.49
    Polymer of Example 1 1.00
    Copolymer 845 (20%) 5.00
    100%
    • EXAMPLE 27 Hair Care Product
  • Ingredient Wt. %
    Water 93.51
    AMP-95 0.49
    Polymer of Example 1 1.00
    Styleze W-20 (20% sol'n) 5.00
    100%
    • EXAMPLE 28 Hair Care Product
  • Ingredient Wt. %
    Water 88.41
    AMP-95 0.49
    Polymer of Example 1 1.00
    Styleze CC-10 10.00
    100%
    • EXAMPLE 29 Hair Care Composition
  • Ingredient Wt. %
    Water 88.51
    AMP-95 0.49
    Polymer of Example 1 1.00
    Ganex P904LC (10%) 10.00
    100%
    • EXAMPLE 30 Personal Care Product
  • Ingredient Wt. %
    Water 93.51
    AMP-95 0.49
    Polymer of Example 1 1.00
    Conditioneze 7 (10%) 10.00
    100%
    • EXAMPLE 31 Personal Care Composition
  • Ingredient Wt. %
    Water 95.17
    AMP-95 0.49
    Polymer of Example 1 1.00
    Aquaflex XL-30 (30%) 3.34
    100%
    • EXAMPLE 32 Personal Care Composition
  • Ingredient Wt.%
    Water 93.51
    AMP-95 0.49
    Polymer of Example 1 1.00
    Gafquat 755 (20%) 5.00
    100%
    • EXAMPLE 33 Personal Care Composition
  • Ingredient Wt. %
    Water 93.51
    AMP-95 0.49
    Polymer of Example 1 1.00
    Gafquat HS-100 (20%) 5.00
    100%
    • EXAMPLE 34 Personal Care Composition
  • Ingredient Wt. %
    Water 93.51
    AMP-95 0.49
    Polymer of Example 1 1.00
    Gafquat 755N (20%) 5.00
    100%
    • EXAMPLE 35 Personal Care Composition
  • Ingredient Wt. %
    Water 94.81
    AMP-95 0.49
    Polymer of Example 1 1.00
    Gaffix VC 713 copolymer (37%) 3.70
    100%
    • EXAMPLE 36 Personal Care Composition
  • Ingredient Wt. %
    Water 95.18
    AMP-95 0.49
    Polymer of Example 1 1.00
    PVP K-30 (30%) 3.33
    100%
    • EXAMPLE 37 Personal Care Composition
  • Ingredient Wt. %
    Water 88.51
    AMP-95 0.49
    Polymer of Example 1 1.00
    AdvantageS (10% sol'n) 10.00
    100%
    • EXAMPLE 38 Night Cream Composition
  • Phase Ingredient % w/w
    A Water 70.60
    Na2EDTA 0.05
    Polymer of Example 1 1.00
    Propylene glycol 1.00
    B Ceraphyl 847 5.00
    Si-Tec DM 1000 2.00
    Ceraphyl 494 4.70
    Si-Tec PTM 200 (phenyl trimeticone) 2.00
    Si-Tec DMC 3071 2.50
    Si-Tec CM 040 2.50
    C NaOH (10%) 1.50
    D dl-alpha-tocopheryl acetate 0.30
    Actiphyte of Licorice Root BG50P 0.50
    Gluadin W-20 0.50
    Sheer Musk (71110M) 0.30
    Liquid Germall Plus 0.50
    E Escalol 577 (Benzophenone-4) 0.05
    Water 5.00
    100%
  • Procedure: 1) Combine ingredients in phase A with mixing; 2) Combine phase B. Mix until uniform; 3) Add phase B to phase A with mixing; 4) Add phase C; 5) Add ingredients in phase D; 6) Combine phase E. Mix until clear; 7) Add phase E with mixing.
    • EXAMPLE 39 Night Cream Composition
  • Phase Ingredient % w/w
    A Water 70.60
    Na2EDTA 0.05
    Polymer of Example 1 1.00
    Propylene glycol 1.00
    B Ceraphyl 847 5.00
    Si-Tec DM 1000 2.00
    Ceraphyl 494 4.60
    Si-Tec PTM 200 (phenyl trimeticone) 2.00
    Si-Tec CM 040 2.50
    C NaOH(10%) 2.00
    DI water 1.10
    D dl-alpha-tocopheryl acetate 0.30
    Actiphyte of Licorice Root BG50P 0.50
    Gluadin W-20 0.50
    Sheer Musk (71110M) 0.30
    Liquid Germall Plus 0.50
    E Escalol 577 (Benzophenone-4) 0.05
    Water 5.00
    100%
  • Procedure: 1) Combine ingredients in phase A with mixing; 2) Combine phase B. Mix until uniform; 3) Add phase B to phase A with mixing; 4) Add phase C; 5) Add ingredients in phase D; 6) Combine phase E. Mix until clear; 7) Add phase E with mixing.
    • EXAMPLE 40 Sunscreen Lotion
  • Phase Ingredient % w/w
    A DI water 76.65
    Versene NA 0.05
    Propylene glycol 1.00
    Polymer of Example 1 1.00
    B Escalol 557 7.00
    Escalol 567 2.00
    Escalol 587 3.00
    Ceraphyl 45 4.00
    Polysorbate-20 0.50
    C NaOH (50% w/w) 0.20
    DI water 3.30
    D Sheer Musk 0.30
    Germaben II-E 1.00
    100%
  • Procedure: 1) Disperse phase A ingredient into water with stirring; 2) Combine first five phase B ingredients. Stir until uniform; 3) Add phase B to phase A with homogenizing @ RT. Stir until uniform; 4) When uniform, add phase C; 5) Add phase D ingredient with stirring. QS for water loss.
    • EXAMPLE 41 Sunscreen Lotion
  • Phase Ingredient % w/w
    A DI water 76.65
    Versene NA 0.05
    Propylene glycol 1.00
    Polymer of Example 1 1.00
    B Escalol 557 7.00
    Escalol 567 2.00
    Escalol 587 3.00
    Ceraphyl 45 4.00
    Si-Tec 3071 1.00
    C NaOH (50% w/w) 0.20
    DI water 2.80
    D Sheer Musk 0.30
    Germaben II-E 1.00
    100%
  • Procedure: 1) Disperse phase A ingredient into water with stirring; 2) Combine first five phase B ingredients. Stir until uniform; 3) Add phase B to phase A with homogenizing @ RT. Stir until uniform; 4) When uniform, add phase C; 5) Add phase D ingredient with stirring. QS for water loss.
    • EXAMPLE 42 Day Cream
  • Phase Ingredient % w/w
    A DI water 69.80
    EDTA (di-sodium) 0.10
    Glycerin 1.00
    Polymer of Example 1 1.00
    Propylene glycol 1.00
    B Ceraphyl 230 4.00
    Ceraphyl 494 6.00
    Ceraphyl 368 10.00
    Prolipid 151 3.00
    C NaOH (50% w/w) 0.20
    DI water 2.80
    D Sheer Musk 0.50
    Liquid Germall Plus 0.60
    100%
  • Procedure: 1) Add ingredients in phase A to water with stirring. Heat to 65° C.; 2) Combine phase B. Heat with stirring until P-151 dissolve; 3) Add phase B to phase A with homogenizing; 4) When uniform, add phase C with homogenizing. Cool to 35° C.; 5) Add phase D with stirring. QS for water loss.
  • While the resin of the invention is particularly useful for hair care, it will be understood that it can be used in other personal care applications, such as skin care or as an absorbent material in appropriate applications such as diapers, etc.
  • FIG. 1 herein shows the viscosity vs. pH property of the fixative resin of the invention t 1% solids in water. The viscosity is a desirably high value of about 55,000 cps at a pH of about 5-9. FIG. 2 herein shows the advantageous effective curl retention vs. time for a typical hair care formulation of the invention which includes the resin of Example 1. Substantially 95-100% curl retention is achieved even after 4 hours.
  • Any known conditioning agent is useful in the hair compositions of this invention. Conditioning agents function to improve the cosmetic properties of the hair, particularly softness, thickening, untangling, feel, and static electricity and may be in liquid, semi-solid, or solid form such as oils, waxes, or gums. Similarly, any known skin altering agent is useful in the compositions of this invention. Preferred conditioning agents include cationic polymers, cationic surfactants and cationic silicones.
  • Conditioning agents may be chosen from synthesis oils, mineral oils, vegetable oils, fluorinated or perfluorinated oils, natural or synthetic waxes, silicones, cationic polymers, proteins and hydrolyzed proteins, ceramide type compounds, cationic surfactants, fatty amines, fatty acids and their derivatives, as well as mixtures of these different compounds.
  • The synthesis oils include polyolefins, e.g., poly-α-olefins such as polybutenes, polyisobutenes and polydecenes. The polyolefins can be hydrogenated. The mineral oils suitable for use in the compositions of the invention include hexadecane and oil of paraffin.
  • Suitable animal and vegetable oils include sunflower, corn, soy, avocado, jojoba, squash, raisin seed, sesame seed, walnut oils, fish oils, glycerol tricaprocaprylate, Purcellin oil or liquid jojoba.
  • Suitable natural or synthetic oils include eucalyptus, lavender, vetiver, litsea cubeba, lemon, sandalwood, rosemary, chamomile, savory, nutmeg, cinnamon, hyssop, caraway, orange, geranium, cade, and bergamot.
  • Suitable natural and synthetic waxes include carnauba wax, candelila wax, alfa wax, paraffin wax, ozokerite wax, vegetable waxes such as olive wax, rice wax, hydrogenated jojoba wax, absolute flower waxes such as black currant flower wax, animal waxes such as bees wax, modified bees wax (cerabellina), marine waxes and polyolefin waxes such as polyethylene wax.
  • The cationic polymers (other than the poly (alkyl) vinyllactam polymers according to the invention) that may be used as a conditioning agent according to the invention are those known to improve the cosmetic properties of hair treated by detergent compositions. The expression “cationic polymer” as used herein, indicates any polymer containing cationic groups and/or ionizable groups in cationic groups. The cationic polymers used generally have a molecular weight the average number of which falls between about 500 and 5,000,000 and preferably between 1000 and 3,000,000.
  • The preferred cationic polymers are chosen from among those containing units including primary, secondary, tertiary, and/or quaternary amine groups that may either form part of the main polymer chain or a side chain.
  • Useful cationic polymers include known polyamine, polyaminoamide, and quaternary polyammonium types of polymers, such as:
  • (1) homopolymers and copolymers derived from acrylic or methacrylic esters or amides. The copolymers can contain one or more units derived from acrylamides, methacrylamides, diacetone acrylamides, acrylamides and methacrylamides, acrylic or methacrylic acids or their esters, vinyllactams such as vinyl pyrrolidone or vinyl caprolactam, and vinyl esters. Specific examples include: copolymers of acrylamide and dimethyl amino ethyl methacrylate quaternized with dimethyl sulfate or with an alkyl halide; copolymers of acrylamide and methacryloyl oxyethyl trimethyl ammonium chloride; the copolymer of acrylamide and methacryloyl oxyethyl trimethyl ammonium methosulfate; copolymers of vinyl pyrrolidone/dialkylaminoalkyl acrylate or methacrylate, optionally quaternized, such as the products sold under the name GAFQUAT by International Specialty Products; the dimethyl amino ethyl methacrylate/vinyl caprolactam/vinyl pyrrolidone terpolymers, such as the product sold under the name GAFFIX VC 713 by International Specialty Products; the vinyl pyrrolidone/methacrylamidopropyl dimethylamine copolymer, marketed under the name STYLEZE CC 10 by International Specialty Products; and the vinyl pyrrolidone/quaternized dimethyl amino propyl methacrylamide copolymers such as the product sold under the name GAFQUAT HS 100 by International Specialty Products.
  • (2) derivatives of cellulose ethers containing quaternary ammonium groups, such as hydroxy ethyl cellulose quaternary ammonium that has reacted with an epoxide substituted by a trimethyl ammonium group.
  • (3) derivatives of cationic cellulose such as cellulose copolymers or derivatives of cellulose grafted with a hydrosoluble quaternary ammonium monomer, as described in U.S. Pat. No. 4,131,576, such as the hydroxy alkyl cellulose, and the hydroxymethyl-, hydroxyethyl- or hydroxypropyl-cellulose grafted with a salt of methacryloyl ethyl trimethyl ammonium, methacrylamidopropyl trimethyl ammonium, or dimethyl diallyl ammonium.
  • (4) cationic polysaccharides such as described in U.S. Pat. Nos. 3,589,578 and 4,031,307, guar gums containing cationic trialkyl ammonium groups and guar gums modified by a salt, e.g., chloride of 2,3-epoxy propyl trimethyl ammonium.
  • (5) polymers composed of piperazinyl units and alkylene or hydroxy alkylene divalent radicals with straight or branched chains, possibly interrupted by atoms of oxygen, sulfur, nitrogen, or by aromatic or heterocyclic cycles, as well as the products of the oxidation and/or quaternization of such polymers.
  • (6) water-soluble polyamino amides prepared by polycondensation of an acid compound with a polyamine. These polyamino amides may be reticulated.
  • (7) derivatives of polyamino amides resulting from the condensation of polyalcoylene polyamines with polycarboxylic acids followed by alcoylation by bifunctional agents.
  • (8) polymers obtained by reaction of a polyalkylene polyamine containing two primary amine groups and at least one secondary amine group with a dioxycarboxylic acid chosen from among diglycolic acid and saturated dicarboxylic aliphatic acids having 3 to 8 atoms of carbon. Such polymers are described in U.S. Pat. Nos. 3,227,615 and 2,961,347.
  • (9) the cyclopolymers of alkyl dialyl amine or dialkyl diallyl ammonium such as the homopolymer of dimethyl diallyl ammonium chloride and copolymers of diallyl dimethyl ammonium chloride and acrylamide.
  • (10) quaternary diammonium polymers such as hexadimethrine chloride. Polymers of this type are described particularly in U.S. Pat. Nos. 2,273,780, 2,375,853, 2,388,614, 2,454,547, 3,206,462, 2,261,002, 2,271,378, 3,874,870, 4,001,432, 3,929,990, 3,966,904, 4,005,193, 4,025,617, 4,025,627, 4,025,653, 4,026,945, and 4,027,020.
  • (11) quaternary polyammonium polymers, including, for example, Mirapol® A 15, Mirapol® AD1, Mirapol® AZ1, and Mirapol® 175 products sold by Miranol.
  • (12) the quaternary polymers of vinyl pyrrolidone and vinyl imidazole such as the products sold under the names Luviquat® FC 905, FC 550, and FC 370 by BASF.
  • (13) quaternary polyamines.
  • (14) reticulated polymers known in the art.
  • Other cationic polymers that may be used within the context of the invention are cationic proteins or hydrolyzed cationic proteins, polyalkyleneimines such as polyethyleneimines, polymers containing vinyl pyridine or vinyl pyridinium units, condensates of polyamines and epichlorhydrins, quaternary polyurethanes, and derivatives of chitin.
  • Preferred cationic polymers are derivatives of quaternary cellulose ethers, the homopolymers and copolymers of dimethyl diallyl ammonium chloride, quaternary polymers of vinyl pyrrolidone and vinyl imidazole, and mixtures thereof.
  • The conditioning agent can be any silicone known by those skilled in the art to be useful as a conditioning agent. The silicones suitable for use according to the invention include polyorganosiloxanes that are insoluble in the composition. The silicones may be present in the form of oils, waxes, resins, or gums. They may be volatile or non-volatile. The silicones can be selected from polyalkyl siloxanes, polyaryl siloxanes, polyalkyl aryl siloxanes, silicone gums and resins, and polyorgano siloxanes modified by organofunctional groups, and mixtures thereof.
  • Suitable polyalkyl siloxanes include polydimethyl siloxanes with terminal trimethyl silyl groups or terminal dimethyl silanol groups (dimethiconol) and polyalkyl (C1-C20) siloxanes.
  • Suitable polyalkyl aryl siloxanes include polydimethyl methyl phenyl siloxanes and polydimethyl diphenyl siloxanes, linear or branched.
  • The silicone gums suitable for use herein include polydiorganosiloxanes preferably having a number-average molecular weight between 200,000 and 1,000,000, used alone or mixed with a solvent. Examples include polymethyl siloxane, polydimethyl siloxane/methyl vinyl siloxane gums, polydimethyl siloxane/diphenyl siloxane, polydimethyl siloxane/phenyl methyl siloxane and polydimethyl siloxane/diphenyl siloxane/methyl vinyl siloxane.
  • Suitable silicone resins include silicones with a dimethyl/trimethyl siloxane structure and resins of the trimethyl siloxysilicate type.
  • The organo-modified silicones suitable for use in the invention include silicones such as those previously defined and containing one or more organofunctional groups attached by means of a hydrocarbon radical and grafted siliconated polymers. Particularly preferred are amino functional silicones.
  • The silicones may be used in the form of emulsions, nano-emulsions, or micro-emulsions.
  • The conditioning agent can be a protein or hydrolyzed cationic or non-cationic protein. Examples of these compounds include hydrolyzed collagens having triethyl ammonium groups, hydrolyzed collagens having trimethyl ammonium and trimethyl stearyl ammonium chloride groups, hydrolyzed animal proteins having trimethyl benzyl ammonium groups (benzyltrimonium hydrolyzed animal protein), hydrolyzed proteins having groups of quaternary ammonium on the polypeptide chain, including at least one C1-C18 alkyl.
  • Hydrolyzed proteins include Croquat L, in which the quaternary ammonium groups include a C12 alkyl group, Croquat M, in which the quaternary ammonium groups include C10-C18 alkyl groups, Croquat S in which the quaternary ammonium groups include a C18 alkyl group and Crotein Q in which the quaternary ammonium groups include at least one C1-C18 alkyl group. These products are sold by Croda.
  • The conditioning agent can comprise quaternized vegetable proteins such as wheat, corn, or soy proteins such as cocodimonium hydrolyzed wheat protein, laurdimonium hydrolyzed wheat protein and steardimonium hydrolyzed wheat protein.
  • According to the invention, the conditioning agent can be a ceramide type of compound such as a ceramide, a glycoceramide, a pseudoceramide, or a neoceramide. These compounds can be natural or synthetic. Compounds of the ceramide type are, for example, described in Patents pending DE4424530,
  • DE4424533, DE4402929, DE4420736, WO95/23807, WO94/07844, EP-A-0646572, WO95/16665, FR-2 673 179, EP-A-0227994, WO 94/07844, WO 94/24097, and WO 94/10131. Ceramide type compounds useful herein include 2-N-linoleoyl amino-octadecane-1,3-diol, 2-N-oleoyl amino-octadecane-1,3-diol, 2-N-palmitoyl amino-octadecane-1,3-diol,
  • 2-N-stearoyl amino-octadecane-1,3-diol, 2-N-behenoyl amino-octadecane-1,3-diol, 2-N-[2-hydroxy-palmitoyl]-amino-octadecane-1,3-diol, 2-N-stearoyl amino-octadecane-1,3,4-triol, N-stearoyl phytosphingosine, 2-N-palmitoyl amino-hexadecane-1,3-diol, bis-(N-hydroxy ethyl N-cetyl)malonamide, N(2-hydroxy ethyl)-N-(3-cetoxyl-2-hydroxy propyl)amide of cetylic,
  • N-docosanoyl N-methyl-D-glucamine and mixtures of such compounds.
  • The conditioning agent can be a cationic surfactant such as a salt of a primary, secondary, or tertiary fatty amine, optionally polyoxyalkylenated, a quaternary ammonium salt, a derivative of imadazoline, or an amine oxide. Suitable examples include mono-, di-, or tri-alkyl quaternary ammonium compounds with a counterion such as a chloride, methosulfate, tosylate, etc. including, but not limited to, cetrimonium chloride, dicetyidimonium chloride, behentrimonium methosulfate, and the like. The presence of a quaternary ammonium compound in conjunction with the polymer described above reduces static and enhances combing of hair in the dry state. The polymer also enhances the deposition of the quaternary ammonium compound onto the hair substrate thus enhancing the conditioning effect of hair.
  • The conditioning agent can be any fatty amine known to be useful as a conditioning agent; e.g. dodecyl, cetyl or stearyl amines, such as stearamidopropyl dimethylamine.
  • The conditioning agent can be a fatty acid or derivatives thereof known to be useful as conditioning agents. Suitable fatty acids include myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, and isostearic acid. The derivatives of fatty acids include carboxylic ester acids including mono-, di-, tri- and tetra-carboxylic acids.
  • The conditioning agent can be a fluorinated or perfluorinated oil. Fluorinated oils include perfluoropolyethers described in EP-A-486135 and the fluorohydrocarbon compounds described in WO 93/11103. The fluoridated oils may also be fluorocarbons such as fluoramines, e.g., perfluorotributylamine, fluoridated hydrocarbons, such as perfluorodecahydronaphthalene, fluoroesters, and fluoroethers.
  • Of course, mixtures of two or more conditioning agents can be used. The conditioning agent or agents can be present in an amount of 0.001% to 20%, preferably from 0.01% to 10%, and even more preferably from 0.1% to 3% by weight based on the total weight of the final composition.
  • The composition of the invention can contain one or more protecting agents to prevent or limit the degrading effects of natural physical and/or chemical assaults on the keratinous materials.
  • The protecting agent can be chosen from hydrosoluble, liposoluble and water-insoluble UV filters, antiradical agents, antioxidants, vitamins and pro-vitamins. The above-described cationic polymer enhances the deposition of these materials onto the hair or skin substrate enhancing protection of hair to UV damage.
  • Organic UV filters (systems that filter out UV rays) can be chosen from among hydrosoluble or liposoluble filters, whether siliconated or nonsiliconated, and mineral oxide particles, the surface of which may be treated.
  • Hydrosoluble organic UV filters may be chosen from para-amino benzoic acid and its salts, anthranilic acid and its salts, salicylic acid and its salts, hydroxy cinnamic acid and its salts, sulfonic derivatives of benzothiazoles, benzimidizoles, benzoxazoles and their salts, sulfonic derivatives of benzophenone and their salts, sulfonic derivatives of benzylidene camphor and their salts, derivatives of benzylidene camphor substituted by a quaternary amine and their salts, derivatives of phthalydene-camphosulfonic acids and their salts, sulfonic derivatives of benzotriazole, and mixtures thereof.
  • Hydrophilic polymers which have light-protective qualities against UV rays can be used. These include polymers containing benzylidene camphor and/or benzotriazole groups.
  • Suitable liposoluble organic UV filters include derivatives of para-aminobenzoic acid, such as the esters or amides of para-aminobenzoic acid; derivatives of salicylic acid; derivatives of benzophenone; derivatives of dibenzoyl methane; derivatives of diphenyl acrylates; derivatives of benzofurans; UV filter polymers containing one or more silico-organic residues; esters of cinnamic acid; derivatives of camphor; derivatives of trianilino-s-triazine; the ethylic ester urocanic acid; benzotriazoles; derivatives of hydroxy phenyl triazine; bis-resorcinol-dialkyl amino triazine; and mixtures thereof.
  • The liposoluble (or lipophilic) organic UV filter according to the invention can be chosen from octyl salicylate; 4-tert-butyl-4′-methoxy dibenzoyl methane; octocrylene; 4-methoxy cinnamate; 2-ethylhexyl [2-ethylhexyl 4-methoxycinnamate]; and 2-(2H-benzotriazol-2-yl)-4-methyl-6-[2-methyl-3-[1,3,3,3-tetramethyl-1-[(trimethyl silyl)oxy]disiloxanyl]propynyl]phenol.
  • Other UV filters particularly preferred for use herein are derivatives of benzophenones such as 2-hydroxy-4-methoxy benzophenone-5-sulfonic acid, 2-hydroxy-4-methoxy benzophenone, derivatives of benzalmalonates such as poly dimethyl/methyl (3(4-(2,2-bis-ethoxy carbonyl vinyl)-phenoxy)-propenyl) siloxane, derivatives of benzylidene camphor such as b-b′camphosulfonic [1-4 divinylbenzene] acid and derivatives of benzimidazole such as 2-phenyl-benzimidazol-5-sulfonic acid.
  • Water-insoluble UV filters include various mineral oxides. The mineral oxides may be selected from among titanium oxides, zinc oxides, and cerium oxides. The mineral oxides can be used in the form of ultrafine nanoparticles.
  • Preferred UV filters include Escalol HP-610 (dimethylpabamido propyl laurdimonium tosylate and propylene glycol stearate) and Crodasorb HP (polyquaternium 59).
  • The antioxidants or antiradical agents can be selected from phenols such as BHA (tert-butyl-4-hydroxy anisole), BHT (2,6-di-tert-butyl-p-cresol), TBHQ (tert-butyl hydroquinone), polyphenols such as proanthocyanodic oligomers, flavonoids, hindered amines such as tetra amino piperidine, erythorbic acid, polyamines such as spermine, cysteine, glutathione, superoxide dismutase, and lactoferrin.
  • The vitamins can be selected from ascorbic acid (vitamin C), vitamin E, vitamin E acetate, vitamin E phosphate, B vitamins such as B3 and B5, vitamin PP, vitamin A, and derivatives thereof. The provitamins can be selected from panthenol and retinol.
  • The protecting agent can be present in an amount 0.001% to 20% by weight, preferably from 0.01% to 10% by weight, and more preferably 0.1 to 5% by weight of the total weight of the final composition.
  • The composition of the invention can contain a fixing agent. The fixing agent can be an anionic polymer chosen from polymers containing carboxylic units derived from unsaturated carboxylic mono- or polyacids of the formula:
    Figure US20070202064A1-20070830-C00001
    in which n is a whole number from 0 to 10, A1 denotes a methylene group, optionally bonded to the carbon atom of the unsaturated group or to a neighboring methylene group when n is greater than 1 by means of a heteroatom like oxygen or sulfur, R7 denotes a hydrogen atom, a phenyl or benzyl group, R8 denotes a hydrogen atom, a lower alkyl or carboxyl group, R9 denotes a hydrogen atom, a lower alkyl group, a —CH2—COOH, phenyl or benzyl group and polymers containing units derived from sulfonic acid like vinylsulfonic, styrenesulfonic, acrylamidoalkylsulfonic units.
  • The fixing agent can be an amphoteric polymer chosen from the polymer containing recurring units derived from: a) at least one monomer chosen from acrylamides or methacrylamides substituted on the nitrogen with an alkyl radical; b) at least one acid copolymer containing one or more reactive carboxyl groups; and c) at least one basic comonomer, such as esters with primary, secondary, tertiary, and quaternary amino substitutents of acrylic and methacrylic acids and the product of quaternization of dimethylaminoethyl methacrylate with dimethyl or diethyl sulfate.
  • The fixing agent can be a nonionic polymer chosen from polyalkyloxazolines; vinyl acetate homopolymers; vinyl acetate and acrylic ester copolymers; vinyl acetate and ethylene copolymers; vinyl acetate and maleic ester copolymers; polyethylene and maleic anhydride copolymers; homopolymers of alkyl acrylates; homopolymers of alkyl methacrylates; copolymers of acrylic esters; copolymers of alkyl acrylates and alkyl methacrylates; copolymers of acrylonitrile and a nonionic monomer chosen from among butadiene and alkyl (meth)acrylates; copolymers of alkyl acrylate and urethane; and polyamides.
  • The fixing polymer can be a functionalized or unfunctionalized, silicone or non-silicone polyurethane.
  • The fixing polymer can be a polymer of the grafted silicone type containing a polysiloxane portion and a portion consisting of a nonsilicone organic chain, with one of the two portions forming the main chain of the polymer, and with the other being grafted onto said main chain.
  • The fixing agent can be present in the composition in a relative weight concentration between 0.1 and 10%, preferably 0.5 and 5%.
  • The composition of the invention can contain an oxidizing agent. The oxidizing agent can be chosen from the group of hydrogen peroxide, urea peroxide, alkali metal bromates, ferricyanides, persalts, and redox enzymes, optionally with their respective donor or cofactor. In a particularly preferred embodiment, the oxidizing agent is hydrogen peroxide. The oxidizing agent can be a solution of oxygenated water whose titer varies from 1 to 40 volumes.
  • The composition of the invention can contain at least one reducing agent in amounts from 0.01 to 30 wt %, preferably 0.05 to 20 wt % of the total weight of the composition. The reducing agents useful in the practice of this invention can be selected from thiols, like cysteine, thioglycolic acid, thiolacetic acid, their salts and esters, cysteamine, and its salts or sulfites. In the case of compositions intended for bleaching, ascorbic acid, its salts and its esters, erythorbic acid, its salts and its esters, and sulfinates, like sodium hydroxymethanesulfinate can be used.
  • The composition of the invention can contain a dye selected from the group consisting of neutral acid or cationic nitrobenzene dyes, neutral acid or cationic azo dyes, quinone dyes, neutral, acid or cationic anthraquinone dyes, azine dyes, triarylmethane dyes, indoamine dyes and natural dyes. The dye or dyes can be present in a concentration from 0.001 to 20% and preferably 0.005 to 10 wt % based on the total weight of the composition.
  • The composition of the invention can contain at least one amphoteric polymer or a cationic polymer different from the cationic poly(vinyllactam) defined above. Suitable cationic polymers include a poly(quaternary ammonium) consisting of recurrent units corresponding to the following formula (W) and (U):
    Figure US20070202064A1-20070830-C00002
    Figure US20070202064A1-20070830-C00003
  • Suitable amphoteric polymers include a copolymer containing at least one acrylic acid and a dimethyldiallyammonium salt as a monomer. The cationic or amphoteric polymer or polymers can be present in an amount of 0.01 to 10%, preferably 0.05 to 5%, and more preferably 0.1 to 3% by weight of the total weight of the composition.
  • In addition, the compositions according to the invention advantageously include at least one surfactant, which can be present in an amount of 0.1% and 60% preferably 1% and 40%, and more preferably 5% and 30% by weight based on the total weight of the composition. The surfactant may be chosen from among anionic, amphoteric, or non-ionic surfactants, or mixtures of them known to be useful in personal care compositions.
  • The composition of the invention can contain one or more additional cosmetically acceptable additives chosen from conditioning agents, protecting agents, such as, for example, hydrosoluble, liposoluble and water-insoluble UV filters, antiradical agents, antioxidants, vitamins and pro-vitamins, fixing agents, oxidizing agents, reducing agents, dyes, cleansing agents, anionic, cationic, nonionic and amphoteric surfactants, thickeners, perfumes, pearlizing agents, stabilizers, pH adjusters, filters, preservatives, hydroxy acids, cationic and nonionic polyether associative polyurethanes, polymers other than the cationic polymer described herein, vegetable oils, mineral oils, synthetic oils, polyols such as glycols and glycerol, silicones, aliphatic alcohols, colorants, bleaching agents, highlighting agents and sequestrants. These additives are present in the composition according to the invention in proportions that may range from 0 to 20% by weight in relation to the total weight of the composition. The precise amount of each additive may be easily determined by an expert in the field according to its nature and its function.
  • Additional thickeners or viscosity increasing agents may be included in the composition of the invention, such as:
  • Acetamide MEA
  • Acrylamide/Ethalkonium Chloride Acrylate Copolymer
  • Acrylamide/Ethyltrimonium Chloride Acrylate/Ethalkonium Chloride Acrylate Copolymer
  • Acrylamides Copolymer
  • Acrylamide/Sodium Acrylate Copolymer
  • Acrylamide/Sodium Acryloyldimethyltaurate Copolymer
  • Acrylates/Acetoacetoxyethyl Methacrylate Copolymer
  • Acrylates/Beheneth-25 Methacrylate Copolymer
  • Acrylates/C10-30 Alkyl Acrylate Crosspolymer
  • Acrylates/Ceteth-20 Itaconate Copolymer
  • Acrylates/Ceteth-20 Methacrylate Copolymer
  • Acrylates/Laureth-25 Methacrylate Copolymer
  • Acrylates/Palmeth-25 Acrylate Copolymer
  • Acrylates/Palmeth-25 Itaconate Copolymer
  • Acrylates/Steareth-50 Acrylate Copolymer
  • Acrylates/Steareth-20 Itaconate Copolymer
  • Acrylates/Steareth-20 Methacrylate Copolymer
  • Acrylates/Stearyl Methacrylate Copolymer
  • Acrylates/Vinyl Isodecanoate Crosspolymer
  • Acrylic Acid/Acrylonitrogens Copolymer
  • Adipic Acid/Methyl DEA Crosspolymer
  • Agar
  • Agarose
  • Alcaligenes Polysaccharides
  • Algin
  • Alginic Acid
  • Almondamide DEA
  • Almondamidopropyl Betaine
  • Aluminum/Magnesium Hydroxide Stearate
  • Ammonium Acrylates/Acrylonitrogens Copolymer
  • Ammonium Acrylates Copolymer
  • Ammonium Acryloyidimethyltaurate/Vinyl Formamide Copolymer
  • Ammonium Acryloyidimethyltaurate/VP Copolymer
  • Ammonium Alginate
  • Ammonium Chloride
  • Ammonium Polyacryloyidimethyl Taurate
  • Ammonium Sulfate
  • Amylopectin
  • Apricotamide DEA
  • Apricotamidopropyl Betaine
  • Arachidyl Alcohol
  • Arachidyl Glycol
  • Arachis Hypogaea (Peanut) Flour
  • Ascorbyl Methylsilanol Pectinate
  • Astragalus Gummifer Gum
  • Attapulgite
  • Avena Sativa (Oat) Kernel Flour
  • Avocadamide DEA
  • Avocadamidopropyl Betaine
  • Azelamide MEA
  • Babassuamide DEA
  • Babassuamide MEA
  • Babassuamidopropyl Betaine
  • Behenamide DEA
  • Behenamide MEA
  • Behenamidopropyl Betaine
  • Behenyl Betaine
  • Bentonite
  • Butoxy Chitosan
  • Caesalpinia Spinosa Gum
  • Calcium Alginate
  • Calcium Carboxymethyl Cellulose
  • Calcium Carrageenan
  • Calcium Chloride
  • Calcium Potassium Carbomer
  • Calcium Starch Octenylsuccinate
  • C20-40 Alkyl Stearate
  • Canolamidopropyl Betaine
  • Capramide DEA
  • Capryl/Capramidopropyl Betaine
  • Carbomer
  • Carboxybutyl Chitosan
  • Carboxymethyl Cellulose Acetate Butyrate
  • Carboxymethyl Chitin
  • Carboxymethyl Chitosan
  • Carboxymethyl Dextran
  • Carboxymethyl Hydroxyethylcellulose
  • Carboxymethyl Hydroxypropyl Guar
  • Carnitine
  • Cellulose Acetate Propionate Carboxylate
  • Cellulose Gum
  • Ceratonia Siliqua Gum
  • Cetearyl Alcohol
  • Cetyl Alcohol
  • Cetyl Babassuate
  • Cetyl Betaine
  • Cetyl Glycol
  • Cetyl Hydroxyethylcellulose
  • Chimyl Alcohol
  • Cholesterol/HDI/Pullulan Copolymer
  • Cholesteryl Hexyl Dicarbamate Pullulan
  • Citrus Aurantium Dulcis (Orange) Peel Extract
  • Cocamide DEA
  • Cocamide MEA
  • Cocamide MIPA
  • Cocamidoethyl Betaine
  • Cocamidopropyl Betaine
  • Cocamidopropyl Hydroxysultaine
  • Coco-Betaine
  • Coco-Hydroxysultaine
  • Coconut Alcohol
  • Coco/Oleamidopropyl Betaine
  • Coco-Sultaine
  • Cocoyl Sarcosinamide DEA
  • Cornamide/Cocamide DEA
  • Cornamide DEA
  • Croscarmellose
  • Crosslinked Bacillus/Glucose/Sodium Glutamate Ferment
  • Cyamopsis Tetragonoloba (Guar) Gum
  • Decyl Alcohol
  • Decyl Betaine
  • Dehydroxanthan Gum
  • Dextrin
  • Dibenzylidene Sorbitol
  • Diethanolaminooleamide DEA
  • Diglycol/CHDM/Isophthalates/SIP Copolymer
  • Dihydroabietyl Behenate
  • Dihydrogenated Tallow Benzylmonium Hectorite
  • Dihydroxyaluminum Aminoacetate
  • Dimethicone/PEG-10 Crosspolymer
  • Dimethicone/PEG-15 Crosspolymer
  • Dimethicone Propyl PG-Betaine
  • Dimethylacrylamide/Acrylic Acid/Polystyrene Ethyl Methacrylate Copolymer
  • Dimethylacrylamide/Sodium Acryloyldimethyltaurate Crosspolymer
  • Disteareth-100 IPDI
  • DMAPA Acrylates/Acrylic Acid/Acrylonitrogens Copolymer
  • Erucamidopropyl Hydroxysultaine
  • Ethylene/Sodium Acrylate Copolymer
  • Gelatin
  • Gellan Gum
  • Glyceryl Alginate
  • Glycine Soja (Soybean) Flour
  • Guar Hydroxypropyltrimonium Chloride
  • Hectorite
  • Hyaluronic Acid
  • Hydrated Silica
  • Hydrogenated Potato Starch
  • Hydrogenated Tallow
  • Hydrogenated Tallowamide DEA
  • Hydrogenated Tallow Betaine
  • Hydroxybutyl Methylcellulose
  • Hydroxyethyl Acrylate/Sodium Acryloyldimethyl Taurate Copolymer
  • Hydroxyethylcellulose
  • Hydroxyethyl Chitosan
  • Hydroxyethyl Ethylcellulose
  • Hydroxyethyl Stearamide-MIPA
  • Hydroxylauryl/Hydroxymyristyl Betaine
  • Hydroxypropylcellulose
  • Hydroxypropyl Chitosan
  • Hydroxypropyl Ethylenediamine Carbomer
  • Hydroxypropyl Guar
  • Hydroxypropyl Methylcellulose
  • Hydroxypropyl Methylcellulose Stearoxy Ether
  • Hydroxypropyl Starch
  • Hydroxypropyl Starch Phosphate
  • Hydroxypropyl Xanthan Gum
  • Hydroxystearamide MEA
  • Isobutylene/Sodium Maleate Copolymer
  • Isostearamide DEA
  • Isostearamide MEA
  • Isostearamide MIPA
  • Isostearamidopropyl Betaine
  • Lactamide MEA
  • Lanolinamide DEA
  • Lauramide DEA
  • Lauramide MEA
  • Lauramide MIPA
  • Lauramide/Myristamide DEA
  • Lauramidopropyl Betaine
  • Lauramidopropyl Hydroxysultaine
  • Laurimino Bispropanediol
  • Lauryl Alcohol
  • Lauryl Betaine
  • Lauryl Hydroxysultaine
  • Lauryl/Myristyl Glycol Hydroxypropyl Ether
  • Lauryl Sultaine
  • Lecithinamide DEA
  • Linoleamide DEA
  • Linoleamide MEA
  • Linoleamide MIPA
  • Lithium Magnesium Silicate
  • Lithium Magnesium Sodium Silicate
  • Macrocystis Pyrifera (Kelp)
  • Magnesium Alginate
  • Magnesium/Aluminum/Hydroxide/Carbonate
  • Magnesium Aluminum Silicate
  • Magnesium Silicate
  • Magnesium Trisilicate
  • Methoxy PEG-22/Dodecyl Glycol Copolymer
  • Methylcellulose
  • Methyl Ethylcellulose
  • Methyl Hydroxyethylcellulose
  • Microcrystalline Cellulose
  • Milkamidopropyl Betaine
  • Minkamide DEA
  • Minkamidopropyl Betaine
  • MIPA-Myristate
  • Montmorillonite
  • Moroccan Lava Clay
  • Myristamide DEA
  • Myristamide MEA
  • Myristamide MIPA
  • Myristamidopropyl Betaine
  • Myristamidopropyl Hydroxysultaine
  • Myristyl Alcohol
  • Myristyl Betaine
  • Natto Gum
  • Nonoxynyl Hydroxyethylcellulose
  • Oatamide MEA
  • Oatamidopropyl Betaine
  • Octacosanyl Glycol Isostearate
  • Octadecene/MA Copolymer
  • Oleamide DEA
  • Oleamide MEA
  • Oleamide MIPA
  • Oleamidopropyl Betaine
  • Oleamidopropyl Hydroxysultaine
  • Oleyl Betaine
  • Olivamide DEA
  • Olivamidopropyl Betaine
  • Oliveamide MEA
  • Palmamide DEA
  • Palmamide MEA
  • Palmamide MIPA
  • Palmamidopropyl Betaine
  • Palmitamide DEA
  • Palmitamide MEA
  • Palmitamidopropyl Betaine
  • Palm Kernel Alcohol
  • Palm Kernelamide DEA
  • Palm Kernelamide MEA
  • Palm Kernelamide MIPA
  • Palm Kernelamidopropyl Betaine
  • Peanutamide MEA
  • Peanutamide MIPA
  • Pectin
  • PEG-800
  • PEG-Crosspolymer
  • PEG-150/Decyl Alcohol/SMDI Copolymer
  • PEG-175 Diisostearate
  • PEG-190 Distearate
  • PEG-15 Glyceryl Tristearate
  • PEG-140 Glyceryl Tristearate
  • PEG-240/HDI Copolymer Bis-Decyltetradeceth-20 Ether
  • PEG-100/IPDI Copolymer
  • PEG-180/Laureth-50/TMMG Copolymer
  • PEG-10/Lauryl Dimethicone Crosspolymer
  • PEG-15/Lauryl Dimethicone Crosspolymer
  • PEG-2M
  • PEG-5M
  • PEG-7M
  • PEG-9M
  • PEG-14M
  • PEG-20M
  • PEG-23M
  • PEG-25M
  • PEG-45M
  • PEG-65M
  • PEG-90M
  • PEG-115M
  • PEG-160M
  • PEG-180M
  • PEG-120 Methyl Glucose Trioleate
  • PEG-180/Octoxynol-40/TMMG Copolymer
  • PEG-150 Pentaerythrityl Tetrastearate
  • PEG-4 Rapeseedamide
  • PEG-150/Stearyl Alcohol/SMDI Copolymer
  • Phaseolus Angularis Seed Powder
  • Polianthes Tuberosa Extract
  • Polyacrylate-3
  • Polyacrylic Acid
  • Polycyclopentadiene
  • Polyether-1
  • Polyethylene/Isopropyl Maleate/MA Copolyol
  • Polyglyceryl-3 Disiloxane Dimethicone
  • Polyglyceryl-3 Polydimethylsiloxyethyl Dimethicone
  • Polymethacrylic Acid
  • Polyquaternium-52
  • Polyvinyl Alcohol
  • Potassium Alginate
  • Potassium Aluminum Polyacrylate
  • Potassium Carbomer
  • Potassium Carrageenan
  • Potassium Chloride
  • Potassium Palmate
  • Potassium Polyacrylate
  • Potassium Sulfate
  • Potato Starch Modified
  • PPG-2 Cocamide
  • PPG-1 Hydroxyethyl Caprylamide
  • PPG-2 Hydroxyethyl Cocamide
  • PPG-2 Hydroxyethyl Coco/Isostearamide
  • PPG-3 Hydroxyethyl Soyamide
  • PPG-14 Laureth-60 Hexyl Dicarbamate
  • PPG-14 Laureth-60 Isophoryl Dicarbamate
  • PPG-14 Palmeth-60 Hexyl Dicarbamate
  • Propylene Glycol Alginate
  • PVP/Decene Copolymer
  • PVP Montmorillonite
  • Pyrus Cyclonia Seed
  • Pyrus Malus (Apple) Fiber
  • Rhizobian Gum
  • Ricebranamide DEA
  • Ricinoleamide DEA
  • Ricinoleamide MEA
  • Ricinoleamide MIPA
  • Ricinoleamidopropyl Betaine
  • Ricinoleic Acid/Adipic Acid/AEEA Copolymer
  • Rosa Multiflora Flower Wax
  • Sclerotium Gum
  • Sesamide DEA
  • Sesamidopropyl Betaine
  • Sodium Acrylate/Acryloyldimethyl Taurate Copolymer
  • Sodium Acrylates/Acrolein Copolymer
  • Sodium Acrylates/Acrylonitrogens Copolymer
  • Sodium Acrylates Copolymer
  • Sodium Acrylates Crosspolymer
  • Sodium Acrylate/Sodium Acrylamidomethylpropane Sulfonate Copolymer
  • Sodium Acrylates/Vinyl Isodecanoate Crosspolymer
  • Sodium Acrylate/Vinyl Alcohol Copolymer
  • Sodium Carbomer
  • Sodium Carboxymethyl Chitin
  • Sodium Carboxymethyl Dextran
  • Sodium Carboxymethyl Beta-Glucan
  • Sodium Carboxymethyl Starch
  • Sodium Carrageenan
  • Sodium Cellulose Sulfate
  • Sodium Chloride
  • Sodium Cyclodextrin Sulfate
  • Sodium Hydroxypropyl Starch Phosphate
  • Sodium Isooctylene/MA Copolymer
  • Sodium Magnesium Fluorosilicate
  • Sodium Oleate
  • Sodium Palmitate
  • Sodium Palm Kernelate
  • Sodium Polyacrylate
  • Sodium Polyacrylate Starch
  • Sodium Polyacryloyldimethyl Taurate
  • Sodium Polygamma-Glutamate
  • Sodium Polymethacrylate
  • Sodium Polystyrene Sulfonate
  • Sodium Silicoaluminate
  • Sodium Starch Octenylsuccinate
  • Sodium Stearate
  • Sodium Stearoxy PG-Hydroxyethylcellulose Sulfonate
  • Sodium Styrene/Acrylates Copolymer
  • Sodium Sulfate
  • Sodium Tallowate
  • Sodium Tauride Acrylates/Acrylic Acid/Acrylonitrogens Copolymer
  • Sodium Tocopheryl Phosphate
  • Solanum Tuberosum (Potato) Starch
  • Soyamide DEA
  • Soyamidopropyl Betaine
  • Starch/Acrylates/Acrylamide Copolymer
  • Starch Hydroxypropyltrimonium Chloride
  • Stearamide AMP
  • Stearamide DEA
  • Stearamide DEA-Distearate
  • Stearamide DIBA-Stearate
  • Stearamide MEA
  • Stearamide MEA-Stearate
  • Stearamide MIPA
  • Stearamidopropyl Betaine
  • Steareth-60 Cetyl Ether
  • Steareth-100/PEG-136/HDI Copolymer
  • Stearyl Alcohol
  • Stearyl Betaine
  • Sterculia Urens Gum
  • Synthetic Fluorphlogopite
  • Tallamide DEA
  • Tallow Alcohol
  • Tallowamide DEA
  • Tallowamide MEA
  • Tallowamidopropyl Betaine
  • Tallowamidopropyl Hydroxysultaine
  • Tallowamine Oxide
  • Tallow Betaine
  • Tallow Dihydroxyethyl Betaine
  • Tamarindus Indica Seed Gum
  • Tapioca Starch
  • TEA-Alginate
  • TEA-Carbomer
  • TEA-Hydrochloride
  • Trideceth-2 Carboxamide MEA
  • Tridecyl Alcohol
  • Triethylene Glycol Dibenzoate
  • Trimethyl Pentanol Hydroxyethyl Ether
  • Triticum Vulgare (Wheat) Germ Powder
  • Triticum Vulgare (Wheat) Kernel Flour
  • Triticum Vulgare (Wheat) Starch
  • Tromethamine Acrylates/Acrylonitrogens Copolymer
  • Tromethamine Magnesium Aluminum Silicate
  • Undecyl Alcohol
  • Undecylenamide DEA
  • Undecylenamide MEA
  • Undecylenamidopropyl Betaine
  • Welan Gum
  • Wheat Germamide DEA
  • Wheat Germamidopropyl Betaine
  • Xanthan Gum
  • Yeast Beta-Glucan
  • Yeast Polysaccharides
  • Zea Mays (Corn) Starch
  • Preferred thickeners or viscosity increasing agents include Carbomer, Aculyn and Stabileze, e.g. crosslinked acrylic acid, crosslinked poly(methylvinyl ether/maleic anhydride) copolymer, acrylamides, carboxymethyl cellulose and the like.
  • The compositions according to the invention may be used to wash and treat keratinous material such as hair, skin, eyelashes, eyebrows, fingernails, lips, and hairy skin.
  • The compositions according to the invention can be detergent compositions such as shampoos, bath gels, and bubble baths. In this mode, the compositions will comprise a generally aqueous washing base. The surfactant or surfactants that form the washing base may be chosen alone or in blends, from known anionic, amphoteric, or non-ionic surfactants. The quantity and quality of the washing base must be sufficient to impart a satisfactory foaming and/or detergent value to the final composition. The washing base can be from 4% to 50% by weight, preferably from 6% to 35% by weight, and even more preferentially from 8% to 25% by weight of the total weight of the final composition.
  • The pH of the composition applied to the keratinous material is generally between 2 and 12. It is preferably between 3 and 8, and may be adjusted to the desired value by means of acidifying or alkalinizing agents that are well-known in the state of the art in compositions applied to keratinous materials. Thus, the composition of the invention can contain at least one alkalizing or acidifying agent in amounts from 0.01 to 30 wt % of the total weight of the composition.
  • The alkalizing agent can be chosen from ammonia, alkali carbonates, alkanolamines, like mono-, di- and triethanolamines, as well as their derivatives, hydroxyalkylamines and ethoxylated and/or propoxylated ethylenediamines, sodium or potassium hydroxides and compounds of the following formula (XIX):
    Figure US20070202064A1-20070830-C00004
    in which R is a propylene residue optionally substituted with an hydroxyl group or a C1-C4 alkyl radical; R38, R39, R40 and R41, identical or different, represent a hydrogen atom, a C1-C4 alkyl radical or C1-C4 hydroxyalkyl radical.
  • The acidifying agent can be chosen from mineral or organic acids, like hydrochloric acid, orthophosphoric acid, carboxylic acids like tartaric acid, citric acid, or lactic acid, or sulfonic acids and the like.
  • The physiological and cosmetically acceptable medium may consist exclusively of water, a cosmetically acceptable solvent, or a blend of water and a cosmetically acceptable solvent, such as a lower alcohol composed of C1 to C4, such as ethanol, isopropanol, t-butanol, n-butanol, alkylene glycols such as propylene glycol, and glycol ethers. However, the compositions of the invention can be anhydrous.
  • Generally the present cosmetic compositions are prepared by simple mixing procedures well known in the art.
  • The invention also has as its object a process for treating keratinous material including the skin or hair, characterized in that it consists of applying to skin or keratinous materials a cosmetic composition as described above, and then eventually rinsing it with water. Accordingly, the process according to the invention makes it possible to maintain the hairstyle, treatment, care, washing, or make-up removal of the skin, the hair, and any other keratinous material.
  • The compositions according to the invention may also take the form of after-shampoo compositions, to be rinsed off or not, for permanents, straightening, waving, dyeing, or bleaching, or the form of rinse compositions to be applied before or after dyeing, bleaching, permanents, straightening, relaxing, waving or even between the two stages of a permanent or straightening process.
  • The compositions of the invention may also take the form of skin-washing compositions, and particularly in the form of solutions or gels for the bath or shower, or of make-up removal products.
  • The compositions of the invention may also be in the form of aqueous or hydro-alcoholic solutions for skin and/or hair care.
  • The compositions of this invention have demonstrated thermal protection from heat styling tools, more specifically curling or straightening irons. In this application, the cationic polymer provides a continuous film on hair that does not degrade nor whiten upon regular exposure to curling irons at temperatures up to 152° C. Protection is observed via tryptophan measurements and perceived by consumer in combing force reduction.
  • The compositions described herein are useful in products for personal care, including, but mot limited to, gels, lotions, glazes, glues, mousses, sprays, fixatives, shampoos, conditioners, 2n1 shampoos, temporary hair dyes, semi-permanent hair dyes, permanent hair dyes, straighteners, permanent waves, relaxers, creams, putties, waxes, pomades, moisturizers, mascaras, lip balms and foam enhancers.
  • While the invention has been described with particular reference to certain embodiments thereof, it will be understood that changes and modifications may be made which are within the skill of the art. Accordingly, it is intended to be bound only by the following claims.

Claims (30)

1. A rheology modifier/hair styling resin comprising a crosslinked, linear poly(vinyl amide/polymerizable carboxylic acid) copolymer.
2. A rheology modifier/hair styling resin according to claim 1 wherein said vinyl amide is selected from vinyl pyrrolidone, vinyl caprolactam, N-vinyl formamide, N-vinylacetamide, N-vinyl-N-methylacetamide and mixtures thereof.
3. A rheology modifier/hair styling resin according to claim 2 wherein said vinyl amide is vinyl pyrrolidone.
4. A rheology modifier/hair styling resin according to claim 1 wherein said polymerizable carboxylic acid is selected from (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid and mixtures thereof.
5. A rheology modifier/hair styling resin according to claim 4 wherein said polymerizable carboxylic acid is acrylic acid.
6. A rheology modifier/hair styling resin according to claim 1 wherein said crosslinker has at least two free radical polymerizable groups in the molecule.
7. A rheology modifier/hair styling resin according to claim 6 wherein said crosslinker is selected from pentaerythritol triallylether, pentaerythritol triacrylate, pentaerythritol tetraacrylate and methylene bisacrylamide.
8. A rheology modifier/hair styling resin according to claim 1 wherein said vinyl amide is present, by weight, in an amount of 1-99%, said polymerizable carboxylic acid in an amount of 1-99%, and said crosslinker in an amount of 0.2-3%, based on weight of total monomers.
9. A rheology modifier/hair styling resin according to claim 8 wherein said vinyl amide is present in an amount of 20-80%, said polymerizable carboxylic acid in an amount of 20-80%, and said crosslinker in an amount of 0.4-2%.
10. A rheology modifier/hair styling resin according to claim 1 which includes an optional monomer selected from lauryl (meth)acrylate, stearyl (meth)acrylate, alkyl (meth)acrylamide and alkyl (meth)acrylate, where alkyl is C1-C30 or polyethylene oxide.
11. A process of making the rheology modifier/hair styling resin of claim 1 which comprises precipitation polymerizing, by wt., 5-50% of a reaction, mixture of 1-99% of a vinyl amide and 1-99% of a polymerizable carboxylic acid, and 0.2-3% of a crosslinker, based on total monomers, in 50-95% of a non-polar removable organic solvent, in the presence of 0.1-5% of a free radical initiator, based on total weight of monomers, and removing the solvent, to provide the resin in powder form.
12. A process according to claim 11 wherein said mixture of monomers comprises 20-80% of said vinyl amide, 20-80% of said polymerizable carboxylic acid, 0.4-2% of said crosslinker and 0.5-2% of said initiator.
13. A process according to claim 11 wherein said reaction mixture comprises 10-25% of said monomers and 75-90% of said solvent.
14. A hair care composition including the rheology modifier/hair styling resin of claim 1.
15. A hair care composition according to claim 14 including 0.1-20% by wt. of said resin.
16. A hair care composition according to claim 14 which has a viscosity of about 30,000 to 100,000 cps at a pH of about 5 to 9.
17. A hair care composition according to claim 16 wherein said viscosity is 40,000 to 70,000 cps.
18. A hair care composition according to claim 14 which exhibits a curl retention of 80% to 100% over a 4-hour period at 90% RH and 80° F.
19. A hair care composition according to claim 18 wherein said retention is about 90%.
20. A personal care composition including the resin of claim 1.
21. A personal care composition according to claim 20 which is a skin care formulation.
22. A personal care composition according to claim 21 which is an absorbent composition.
23. A personal care composition according to claim 20 which includes a thickener.
24. A personal care composition according to claim 23 wherein said thickener is a crosslinked polyacrylic acid or its copolymer.
25. A personal care composition according to claim 23 wherein said thickener is crosslinked polymethylvinyl ether/maleic anhydride) copolymer.
26. An aqueous hair care composition according to claim 14 having a yield stress value of 10 to 100,000 dynes/cm2.
27. A composition according to claim 26 wherein said value is 100 to 10,000 dynes/cm2.
28. A hair care composition including the rheology modifier of claim 1 which is a hair fixative, a styling gel, a creme, a mousse, or a spray.
29. A hair care composition according to claim 15 which includes 0.2-10% by wt. of said resin.
30. A hair care composition according to claim 29 which includes 0.5-5% by wt. of said resin.
US11/786,639 2004-10-14 2007-04-12 Rheology modifier/hair styling resin Abandoned US20070202064A1 (en)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010144392A1 (en) * 2009-06-08 2010-12-16 Isp Investments Inc. The manipulation of cloud point for two-phase, aqueous polymeric systems
JP2012240987A (en) * 2011-05-23 2012-12-10 Mandom Corp Viscous composition
US8808672B2 (en) 2011-04-28 2014-08-19 Mitsubishi Pencil Company, Limited Liquid cosmetic
WO2017024016A1 (en) * 2015-08-03 2017-02-09 Isp Investments Llc Personal care compositions comprising polymers derived from vinyl alcohol ethers and applications thereof
US9909086B2 (en) 2012-06-13 2018-03-06 Marie-Esther Saint Victor Green glycine betaine derivative compounds and compositions containing same
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Families Citing this family (71)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7759296B2 (en) * 2003-06-19 2010-07-20 Lubrizol Advanced Materials, Inc. Cationic polymers and fixative application therefor
US7205271B2 (en) * 2004-10-14 2007-04-17 Isp Investments Inc. Rheology modifier/hair styling resin
US20060159642A1 (en) * 2004-12-22 2006-07-20 Avon Products, Inc. Mascara composition and method of using
ATE373462T1 (en) * 2005-06-14 2007-10-15 Kpss Kao Gmbh COSMETIC COMPOSITION
DE102005034412A1 (en) * 2005-07-22 2007-01-25 Basf Ag Ampholytic copolymer, its preparation and use
DE102005034906A1 (en) * 2005-07-26 2007-02-01 Basf Ag Silicone group-containing copolymer, its preparation and use
ES2405615T3 (en) * 2005-07-22 2013-05-31 Basf Se Use of anionic and cationic ampholytic copolymers
US20070134191A1 (en) * 2005-12-14 2007-06-14 L'oreal Hair styling compositions containing a nonionic amphiphilic polymer in combination with styling polymers and emulsifying agents
US7799321B2 (en) * 2006-03-31 2010-09-21 Isp Investments Inc. Color cosmetic compositions
EP1961450A1 (en) * 2007-02-20 2008-08-27 Wella Aktiengesellschaft Dyes for keratinic fibers comprising a special anionic thickener
DE102007029734A1 (en) * 2007-06-25 2009-01-08 Beiersdorf Ag Mixture of cross-linked polymer and water-soluble lipids
DE102007038413A1 (en) * 2007-08-09 2009-02-12 Beiersdorf Ag Cosmetic emulsifier combination
US20090088360A1 (en) * 2007-09-28 2009-04-02 Kimberly-Clark Worldwide Bath Treatment Compositions and Methods
EP2211831A1 (en) * 2007-10-25 2010-08-04 L'Oréal Fragrancing composition comprising an amphiphilic copolymer of 2 acrylamidomethylpropanesulphonic acid and optionally a cellulose alkyl ether and/or an alkylcellulose alkyl ether
DE102008011767B4 (en) * 2008-02-28 2012-07-26 Basf Se Process for the preparation of olefinically unsaturated carbonyl compounds by oxidative dehydrogenation of alcohols
FR2937533B1 (en) * 2008-10-29 2010-11-26 Oreal ASSOCIATION OF ORCHID EXTRACT AND SOY PROTEIN EXTRACT
US20110223123A1 (en) * 2008-12-16 2011-09-15 Hy Si Bui Washable waterproof and smudge-resistant mascara
DE102009009758A1 (en) * 2009-02-20 2010-08-26 Beiersdorf Ag Skin care formulations with an immediately noticeable tightening effect
US20120294818A1 (en) * 2009-03-11 2012-11-22 Isp Investments Inc. Antiperspirant Compositions
DE102009045933A1 (en) * 2009-10-22 2011-04-28 Henkel Ag & Co. Kgaa Composition for shaping keratinic fibers
US10034829B2 (en) 2010-10-27 2018-07-31 Noxell Corporation Semi-permanent mascara compositions
EP2504386B1 (en) 2009-11-23 2017-03-22 Lubrizol Advanced Materials, Inc. Surfactant-polymer blends
JP5174789B2 (en) * 2009-11-25 2013-04-03 花王株式会社 O / W emulsified cosmetic
ES2449305T3 (en) 2009-12-01 2014-03-19 Lubrizol Advanced Materials, Inc. Multipurpose hydrolytically stable polymers
EP2335675B1 (en) 2009-12-10 2015-02-18 Neubourg Skin Care GmbH & Co. KG Emulsifier-free, polymer stabilised foam formulas
EP2513151B1 (en) 2009-12-14 2014-09-10 Lubrizol Advanced Materials, Inc. Cassia derivatives
KR20130019374A (en) 2010-03-02 2013-02-26 바스프 에스이 Anionic associative rheology modifiers
US20110218295A1 (en) * 2010-03-02 2011-09-08 Basf Se Anionic associative rheology modifiers
PL2363108T3 (en) 2010-03-02 2018-04-30 Neubourg Skin Care Gmbh & Co. Kg Foam formulation containing at least one triterpenoid
JP5478742B2 (en) * 2010-03-02 2014-04-23 ビーエイエスエフ・ソシエタス・エウロパエア Anionic associative rheology modifier
EP2558525B2 (en) 2010-04-14 2018-04-04 Lubrizol Advanced Materials, Inc. Thickened amino acid surfactant compositions and methods therefor
EP2563818B1 (en) 2010-04-29 2014-12-17 Lubrizol Advanced Materials, Inc. Cassia derivatives
ES2526454T3 (en) 2010-07-09 2015-01-12 Lubrizol Advanced Materials, Inc. Mixtures of thickeners of acrylic copolymers
KR101984800B1 (en) 2010-07-09 2019-05-31 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 Structured acrylate copolymer thickners
WO2012022668A1 (en) 2010-08-16 2012-02-23 Basf Se Anionic associative rheology modifiers
WO2012030750A2 (en) 2010-09-02 2012-03-08 Lubrizol Advanced Materials, Inc. Polymers and compositions
DE102010041267A1 (en) * 2010-09-23 2012-03-29 Henkel Ag & Co. Kgaa Means for temporary deformation of keratinous fibers
CA2812409A1 (en) 2010-09-30 2012-04-05 Lubrizol Advanced Materials, Inc. Structured acrylate copolymer for use in multi-phase systems
US9931290B2 (en) 2010-10-05 2018-04-03 Lubrizol Advanced Materials, Inc. Acrylate copolymer thickeners
EP2646539B1 (en) * 2010-12-01 2019-04-03 ISP Investments LLC Durable styling compositions and the uses thereof
ITVA20110008A1 (en) * 2011-03-25 2012-09-26 Lamberti Spa DETERGENT COMPOSITIONS
JP2014156399A (en) * 2011-05-23 2014-08-28 Sumitomo Seika Chem Co Ltd Cosmetic
WO2012170171A1 (en) 2011-06-10 2012-12-13 Lubrizol Advanced Materials, Inc. Cassia derivatives
US9714376B2 (en) 2011-09-13 2017-07-25 Lubrizol Advanced Materials, Inc. Surfactant responsive dispersion polymerized micro-gels
EP2570190A1 (en) 2011-09-15 2013-03-20 Braun GmbH Spray nozzle for dispensing a fluid and sprayer comprising such a spray nozzle
DE102011088926A1 (en) * 2011-12-19 2013-06-20 Beiersdorf Ag Hairstyling formulation to create a flexible hold by using octanohydroxamic acid
ES2592564T3 (en) 2012-06-15 2016-11-30 Lubrizol Advanced Materials, Inc. Alkylglucoside based micellar thickeners for surfactant systems
MX357773B (en) 2013-02-06 2018-07-24 Lubrizol Advanced Mat Inc Semi-permanent hair straightening composition and method.
US10202533B2 (en) 2013-06-27 2019-02-12 Isp Investments Llc High-temperature high-pressure (HTHP) stable synthetic polymer for water based oil-well servicing fluids
WO2014210309A2 (en) 2013-06-28 2014-12-31 The Procter & Gamble Company Aerosol hairspray product comprising a spraying device
WO2015042013A1 (en) 2013-09-18 2015-03-26 Lubrizol Advanced Materials, Inc. Stable linear polymers
WO2015059084A1 (en) 2013-10-21 2015-04-30 Basf Se Precipitation polymerization in the presence of a tertiary amine and of an anhydride
KR20160077206A (en) 2013-11-08 2016-07-01 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 Semi-permanent hair straightening composition and method
WO2016178660A1 (en) 2014-05-02 2016-11-10 Hercules Inncorporated Personal care composition for a keratin substrate comprising conditioning and/or styling polymer
DE102014219580A1 (en) 2014-09-26 2016-03-31 Beiersdorf Ag Heat-generating anhydrous cleaning preparation
MX368467B (en) 2015-06-01 2019-10-03 Procter & Gamble Aerosol hairspray product comprising a spraying device.
ES2913120T3 (en) 2015-08-04 2022-05-31 Isp Investments Llc Polymers derived from aminofunctional vinyl alcohol ethers and applications thereof
WO2017044548A1 (en) * 2015-09-08 2017-03-16 Noxell Corporation Mascara composition
KR20180098330A (en) 2015-12-23 2018-09-03 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 Hydrophobic Modified Alkali-Swellable Emulsion Polymer
US10624835B2 (en) * 2016-03-22 2020-04-21 Kao Usa, Inc. Clear hair conditioner composition
JP6756506B2 (en) * 2016-03-31 2020-09-16 株式会社日本触媒 Crosslinked polymer for moisturizer
CN106866868A (en) * 2017-04-19 2017-06-20 广州天赐高新材料股份有限公司 A kind of thickening agent of copolymer and preparation method thereof
WO2018227516A1 (en) 2017-06-16 2018-12-20 Beiersdorf Daily Chemical (Wuhan) Co., Ltd. A hair cleansing composition containing cymbidium grandiflorum flower extract
WO2019094668A1 (en) 2017-11-10 2019-05-16 Lubrizol Advanced Materials, Inc. Process for preparing and compositions of macrosphere formulations
CN109988269A (en) * 2018-01-02 2019-07-09 博爱新开源医疗科技集团股份有限公司 A kind of novel powder tackifier and preparation method thereof
KR20210008483A (en) 2018-04-12 2021-01-22 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 Hair modification composition and method thereof
US11878067B2 (en) * 2019-07-31 2024-01-23 L'oreal Gel compositions containing copolymer of vinylpyrrolidone and acrylic acid
WO2021021978A1 (en) 2019-07-31 2021-02-04 L'oreal Compositions containing copolymer of vinylpyrrolidone and acrylic acid and film forming agent
JP2024519822A (en) 2021-05-17 2024-05-21 ルブリゾル アドバンスド マテリアルズ， インコーポレイテッド Hair color composition for reducing color fade
KR20240057426A (en) 2021-09-03 2024-05-02 루브리졸 어드밴스드 머티어리얼스, 인코포레이티드 Use of extracts of Myrothamnus species to promote hair growth
WO2023059784A1 (en) 2021-10-06 2023-04-13 Lubrizol Advanced Materials, Inc. Stabilized rheology modifier emulsions

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6361768B1 (en) * 1998-12-29 2002-03-26 Pmd Holdings Corp. Hydrophilic ampholytic polymer
US6566473B1 (en) * 2002-11-20 2003-05-20 Isp Investments Inc. Process for making a vinyl amide polymer composition for skin and hair compositions
US7205271B2 (en) * 2004-10-14 2007-04-17 Isp Investments Inc. Rheology modifier/hair styling resin

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5015708A (en) 1989-06-26 1991-05-14 Gaf Chemicals Corporation Precipitation polymerization of terpolymers of a vinyl lactam, a polymerizable carboxylic acid and a hydrophobic monomer in an aliphatic hydrocarbon solvent
JP3042546B2 (en) * 1991-04-23 2000-05-15 昭和電工株式会社 Fine-particle crosslinked N-vinylamide resin and microgel, production method and use thereof
JP3188283B2 (en) * 1991-05-21 2001-07-16 昭和電工株式会社 Liquid absorbent
US5711951A (en) * 1996-03-13 1998-01-27 Isp Investments Inc. Aqueous product comprising discrete, stabilized, microdroplets of an oil and an in situ polymerized vinyl monomer, containing a thickening agent to homogeneously suspend the microdroplets throughout the medium
JPH1017479A (en) * 1996-07-01 1998-01-20 Showa Denko Kk Salt-containing preparation for external use
JP2000016914A (en) * 1998-07-01 2000-01-18 Kanebo Ltd Cosmetic
US6368607B1 (en) * 1998-07-24 2002-04-09 Isp Investments Inc. Product-structurant composition for personal care formulations
JP2000351717A (en) * 1999-04-09 2000-12-19 Kose Corp Hair cosmetic
WO2002032975A1 (en) 2000-10-18 2002-04-25 Basf Aktiengesellschaft Hydrogel-forming polymers
CN100335032C (en) * 2002-10-09 2007-09-05 宝洁公司 Cosmetic compositions with reduced tack
DE10261750A1 (en) * 2002-12-30 2004-07-15 Basf Ag Ampholytic copolymer and its use

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6361768B1 (en) * 1998-12-29 2002-03-26 Pmd Holdings Corp. Hydrophilic ampholytic polymer
US6566473B1 (en) * 2002-11-20 2003-05-20 Isp Investments Inc. Process for making a vinyl amide polymer composition for skin and hair compositions
US7205271B2 (en) * 2004-10-14 2007-04-17 Isp Investments Inc. Rheology modifier/hair styling resin

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010144392A1 (en) * 2009-06-08 2010-12-16 Isp Investments Inc. The manipulation of cloud point for two-phase, aqueous polymeric systems
US8808672B2 (en) 2011-04-28 2014-08-19 Mitsubishi Pencil Company, Limited Liquid cosmetic
JP2012240987A (en) * 2011-05-23 2012-12-10 Mandom Corp Viscous composition
US9909086B2 (en) 2012-06-13 2018-03-06 Marie-Esther Saint Victor Green glycine betaine derivative compounds and compositions containing same
US10987284B2 (en) * 2014-07-14 2021-04-27 Michael V. Greene Volume boosting molding hair coloring creme formulation
WO2017024016A1 (en) * 2015-08-03 2017-02-09 Isp Investments Llc Personal care compositions comprising polymers derived from vinyl alcohol ethers and applications thereof
US11103437B2 (en) 2015-08-03 2021-08-31 Isp Investments Llc Personal care compositions comprising polymers derived from vinyl alcohol ethers and applications thereof
WO2018227517A1 (en) * 2017-06-16 2018-12-20 Beiersdorf Daily Chemical (Wuhan) Co. Ltd. A hair styling composition containing cymbidium grandiflorum flower extract
WO2018227515A1 (en) * 2017-06-16 2018-12-20 Beiersdorf Daily Chemical (Wuhan) Co., Ltd. A hair conditioning composition containing cymbidium grandiflorum flower extract

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KR101261080B1 (en) 2013-05-06
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