WO1995000108A1 - Compositions cosmetiques pour les cheveux - Google Patents

Compositions cosmetiques pour les cheveux Download PDF

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Publication number
WO1995000108A1
WO1995000108A1 PCT/US1994/005253 US9405253W WO9500108A1 WO 1995000108 A1 WO1995000108 A1 WO 1995000108A1 US 9405253 W US9405253 W US 9405253W WO 9500108 A1 WO9500108 A1 WO 9500108A1
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WO
WIPO (PCT)
Prior art keywords
silicone
weight
hair cosmetic
cosmetic composition
composition according
Prior art date
Application number
PCT/US1994/005253
Other languages
English (en)
Inventor
Rosemary Jane Welch
Philip John Marchant
Emma Louise Dodsworth
Gillian Chambers
William Thomas Skiba
Original Assignee
The Procter & Gamble Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Priority to JP7502799A priority Critical patent/JPH08511800A/ja
Priority to KR1019950705775A priority patent/KR960703003A/ko
Priority to EP95904335A priority patent/EP0723433A1/fr
Priority to AU69101/94A priority patent/AU6910194A/en
Priority to BR9406849A priority patent/BR9406849A/pt
Publication of WO1995000108A1 publication Critical patent/WO1995000108A1/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/91—Graft copolymers
    • 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
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/895—Polysiloxanes containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone

Definitions

  • the present invention relates to hair cosmetic compositions. More particularly, this invention relates to liquid hair cosmetic compositions containing silicone grafted hair styling polymer and non-silicone
  • compositions for centuries, typically to damp or dry hair. These compositions provide temporary setting benefits, and should be removable by water and/or by shampooing.
  • the materials used in the compositions to provide the setting benefits are generally applied in the form of mousses, gels, lotions or sprays.
  • Style retention is typically achieved by the use of resins, such as AMPHOMER (RTM), supplied by National Starch, and GANTREZ SP 225 (RTM), supplied by GAF. As used in commercially sold hairspray products, these resins generally have a weight average molecular weight of from about 40,000 to about
  • silicone macromer portions can provide good style retention benefits to the hair while also providing improved hair feel.
  • silicone macromer-containing polymers can impart a tactile sense of softness
  • Silicone macromer-containing hair styling polymers and formulations containing them are disclosed, for example, in EP-A-0,408,311 issued January 11th 1991, Hayama, et al., US-A- 5,061,481, issued October 29th 1991, Suzuki et al., US-A-5, 106,609, Bolich et al., issued April 21st 1992, US- A-5, 100,658, Bolich et al., issued March 31st 1992, US- A-5, 100,657, Ansher-Jackson, et al., issued March 31st 1992 and US- A-5, 104,646, Bolich et al., issued April 14th 1992. It is also known that at least partial neutralisation of the silicone macromer containing hair styling polymer is necessary to maximise its utility in hair styling compositions. Typically, silicone grafted copoly
  • a liquid hair cosmetic composition comprising:- a) from about 0.1 % by weight to about 10% by weight (acid basis) of a silicone-containing polycarboxylic acid hair styling copolymer having a vinyl polymeric backbone, and having grafted to the backbone a silicone containing macromer having a weight average molecular weight of from about 1,000 to about 50,000 ; b) from about 0.01 % by weight to about 10% by weight of a non-silicone-containing hair styling resin; and c) the balance comprising a carrier suitable for application to hair.
  • compositions for use herein comprise a combination of silicone-containing hair styling copolymer and a non-silicone containing hair styling resin.
  • the total hair styling agent (silicone and non-silicone) is preferably present at levels of from about 0.11 % to about 20%, more preferably from about 0.5% to about 15%, especially from about 1 % to about 10% by weight.
  • the weight ratio of the silicone-containing copolymer to non-silicone containing resin is from about 1000:1 to about 1:1000, preferably from about 100:1 to about 1:100, more preferably from about 10:1 to about 1:10 and especially from about 5:1 to about 1:5.
  • compositions of the present invention contain from about 0.1 % to about 10.0%, preferably from about 0.5% to about 8.0% and especially from about 1 % to about 6%, of specifically-defined silicone-containing copolymers. It is these polymers which provide the unique hair
  • the polymers preferably have a weight average molecular weight of from about 10,000 to about 1,000,000, preferably from about 30,000 to about 300,000, more preferably from about 90,000 to about 300,000 and, preferably, have a Tg of at least about -20°C.
  • Tg refers to the glass transition
  • Tm temperature of the non-silicone backbone
  • the molecular weights and molecular weight distributions of the polymers utilised in the compositions according to the present invention are determined by Size Exclusion Chromatography (SEC).
  • SEC Size Exclusion Chromatography
  • polymers comprise a distribution of molecular weight species that gives rise to their unique properties. Separation of the molecules is
  • Preferred polymers comprise a vinyl polymeric backbone, preferably having a Tg above about -20°C and, grafted to the backbone, a silicone containing macromer having a weight average molecular weight of from about 1,000 to about 50,000, preferably from about 5,000 to about 40,000, most preferably from about 10,000 to about 20,000.
  • the polymer is such that when it is formulated into the finished hair care composition, when dried, the polymer phase separates into a
  • discontinuous phase which includes the silicone containing macromer and a continuous phase which includes the backbone. It is believed that this phase separation property provides a specific orientation of the polymer on hair which results in the desired hair conditioning and setting benefits.
  • the copolymers utilized in the present application comprise a silicone-containing monomer (hereafter identified as C) together with a hydrophilic carboxylate-containing monomer (B) and optionally a lipophilic monomer (A).
  • copolymers examples include monomers A,B and C as defined above.
  • A comprises at least one free radically
  • B comprises at least one reinforcing monomer copolymerizable with A and selected from the group consisting of carboxylate-containing monomers and macromers having a Tg or a Tm above about -20°C.
  • B can be up to about 98%, preferably up to about 80%, more preferably up to about 30%, of the total monomers in the copolymer.
  • Monomer C comprises from about 0.1 % to about 50.0% of the total monomers in the copolymer.
  • a (hydrophobic) monomers are the acrylic or methacrylic acid esters of C 1 -C 18 alcohols, such as methanol, ethanol, methoxy ethanol, 1-pro ⁇ anol, 2-propanol, 1-butanol, 2-methyl-1-propanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-1-butanol, 1-methyl-1-butanol, 3-methyl-1-butanol, 1 -methyl-1-pentanol, 2-methyl-1-pentanol, 3-methyl-1-pentanol, t-butanol (2-methyl-1-propanol), cyclohexanol, neodecanol, 2-ethyl-1-butanol, 3-heptanol, benzyl alcohol, 2-octanol, 6-methyl-1-heptanol, 2-ethyl-1-hexanol, 3.5-dimethyl-1-
  • polystyrene macromer vinyl acetate; vinyl chloride; vinylidene chloride; vinyl propionate; alpha-methylstyrene; t-butylstyrene; butadiene;
  • Preferred A monomers include n-butyl methacrylate, isobutyl
  • methacrylate 2-ethylhexyl methacrylate, methyl methacrylate, t-butylacrylate, t-butylmethacrylate, and mixtures thereof.
  • B (hydrophilic) neutralisable monomers containing a carboxyl moiety include acrylic acid, methacrylic acid, maleic acid, maleic anhydride, half esters of maleic anhydride, crotonic acid, and itaconic acid.
  • Preferred B monomers include acrylic acid and methacrylic acid and mixtures thereof.
  • the C monomer preferably has the general formula (I):
  • X is a vinyl group copolymerizable with the A and B monomers
  • Y is a divalent linking group
  • R is hydrogen, C 1 -C 4 alkyl, aryl, alkyl amino, tri(C 1 -C 4 alkyl)siloxy or C 1 -C 4 alkoxy
  • Z is a monovalent siloxane polymeric moiety
  • n is 0 or 1
  • m is an integer from 1 to 3.
  • C has a number average molecular weight of, at least 500, preferably from 1,000 to 50,000.
  • the C monomer is selected from one or more monomers having the general formulae (II to VII):
  • R 1 is hydrogen or -COOH (preferably R 1 is hydrogen);
  • R 2 is hydrogen, methyl or -CH 2 COOH (preferably R 2 is methyl);
  • Z is
  • R 4 is alkyl, alkoxy, alkylamino, aryl, or hydroxyl (preferably R 4 is alkyl); and r is an integer from 5 to 700, preferably from 50 to 500, more preferably from 150 to 300.
  • the polymers utilized herein generally comprise from 0% to about 98% (preferably from about 5% to about 92%, more preferably from about 50% to about 90%) of monomer A, from about 1 % to about 98% (preferably from about 7.5% to about 80%) of monomer B, and from about 0.1 % to about 50% (preferably from about 0.5% to about 40% , most preferably from about 2% to about 25%) of monomer C.
  • the combination of the A and B monomers preferably comprises from about 50.0% to about 99.9% (more preferably about 60% to about 99.5% , most preferably from about 75% to about 98%) of the polymer.
  • Preferred silicone-containing copolymers for use herein are selected from: acrylic acid/n-butylmethacrylate/polydimethylsiloxane (PDMS)
  • the silicone-containing copolymers described above can be synthesized by free radical polymerization of silicone- or polysiloxane-containing monomers with non-silicone- or non-poly siloxane-containing monomers.
  • free radical polymerization methods are well understood. See, for example, Odian, "Principles of Polymerization", 2nd edition, John Wiley & Sons, 1981 , pp. 179 - 318.
  • compositions according to the invention it can be desirable to purify the silicone containing copolymer by removing unreacted silicone-containing monomer and silicone macromer-grafted polymer with viscosities at 25°C of about 10,000,000 centistokes and less. This can be done, for example, by hexane extraction. After drying the resin from its reaction solvent, hexane extraction of the reaction product can be performed by adding an excess of hexane to the reaction product and heating to near the Tg of the non-silicone portion of the polymer. The mixture is held at this
  • Low molecular weight polysiloxane-containing monomer and polymer is solubilized by supercritical carbon dioxide and transported away from the remaining polymer via a transfer line, which is maintained at identical temperature and pressure as the extraction vessel.
  • the extracted materials are collected in an extraction vessel. Following extraction, the system is depressurised and dry, extracted polymer is recovered from the extraction vessel.
  • compositions according to the invention comprise, as a second essential component, a non-silicone-containing hair styling resin.
  • This non-silicone containing hair styling resin is preferably colloidally dispersed or solubilized in the hair cosmetic carrier along with the silicone-containing hair styling copolymer. Keeping the two hair styling agents dispersed and solubilised in the hair spray solvent is believed to be important for providing the unique hair setting benefits in combination with excellent hair feel characteristics which are delivered by compositions according to the present invention.
  • the non-silicone-containing hair styling resin component of the liquid hair cosmetic compositions of the present invention comprises an anionic, amphoteric, nonionic or cationic polymeric material or mixture thereof.
  • Preferred hair setting resins for use in liquid hair cosmetic compositions according to the present invention are anionic or amphoteric.
  • the non-silicone-containing hair setting resin is preferably present in an amount of from about 0.5% to about 10%, more preferably from about 1 % to about 5% by weight of composition.
  • Hair setting resins suitable for use herein include any resin which is soluble or colloidally dispersible in the hair cosmetic carrier which in preferred embodiments is an alcoholic solvent which can optionally contain up to about 15%, preferably up to about 10%, more preferably up to about 7% water as a co-solvent. Solubility and dispersibility is determined at ambient conditions of temperature and pressure (25°C at and 101.3 kPa (1 Atm)).
  • Resins preferred for use in the compositions of the present invention include anionic, nonionic, and amphoteric resins and mixtured thereof.
  • Preferred resins for use herein are selected from : acrylate/ acrylamide copolymer, polyvinyl methyl ether/maleic anhydride copolymer, vinyl acetate/crotonic acid copolymer, octylacrylamide/
  • acrylate/butylaminoethyl methacrylate copolymer polyvinylpyrrolidone (PVP) , copolymers of polyvinylpyrrolidone and methylmethacrylate, copolymers of polyvinylpyrrolidone and vinylacetate (VA), polyvinyl alcohol, copolymers of polyvinylalcohol and crotonic acid, copolymers of polyvinylalcohol and maleic anhydride, hydroxypropyl cellulose, hydroxypropyl guar gum, sodium polystyrene sulfonate,
  • Particularity preferred resins for use in the compositions of the present invention include acrylate/ acrylamide copolymers available under the trade name Ultra Hold 8 (RTM) (from BASF Corp.), polyvinylmethylether/maleic anhydride copolymers available under the trade name Gantrez (RTM) (from GAF Corp.), vinyl acetate/crotonic acid copolymers available under the trade name Luviset CA-66 (RTM) (from BASF Corp.), octyl acrylamide/
  • Highly prefered resins in compositions according to the present invention are Ultra Hold 8 (RTM) and Amphomer (RTM) and mixtures thereof.
  • the mass average molecular weights of the desired hair setting polymer resins are generally in the range from about 2,000 to about 2,000,000.
  • cationic and nonionic resins may be utilised as detailed below.
  • Polycationic hair conditioning polymer resins suitable for use herein are described below.
  • monomeric units present in the polymers may be referred to as the monomers from which they can be derived.
  • the cationic monomers can be derived from polymerizable cationic starting monomers, or from polymerizable nonionic monomers which are modified subsequent to polymerization to be of cationic character.
  • cationic unsaturated monomers can be polymerized in cationic form, or as an alternative they can be polymerized in the form of their precursors, which are then modified to be cationic, for example, by a quaternizing agent (eg. ethyl monochloroacetate, dimethyl sulfate, etc.).
  • Preferred cationic monomers include dimethylaminoethyl methacrylate, quaternized dimethylaminoethyl methacrylate, diallyldimethyl ammonium chloride, vinylimidazolium quaternary ammonium monomers and mixtures thereof.
  • nonionic monomers are acrylic or methacrylic acid esters of C 1 -C 24 alcohols, such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-methyl-1-propanol, 1-pentanol, 2-pentanol, 3- pentanol, 2-methyl-1-butanol, 1 -methyl-1-butanol, 3-methyl-1-butanol, 1-methyl-1-pentanol, 2-methyl-1-pentanol, 3-methyl-1-pentanol, t-butanol, cyclohexanol, 2-ethyl-1-butanol, 3-heptanol, benzyl alcohol, 2-octanol, 6-methyl-1-heptanol, 2-ethyl-1-hexanol, 3,5-dimethyl-1-hexanol, 3,5,5-trimethyl-1-hexanol, 1-decanol, 1-dodecanol
  • vinylidene chloride acrylonitrile; alpha-methylstyrene; t-butylstyrene; butadiene; cyclohexadiene; ethylene; propylene; vinyl toluene;
  • alkoxyalkyl (meth)acrylate such as methoxy ethyl (meth)acrylate and butoxyethyl (meth)acrylate; and mixtures thereof.
  • Other nonionic monomers include acrylate and methacrylate derivatives such as allyl acrylate and methacrylate, cyclohexyl acrylate and methacrylate, oleyl acrylate and methacrylate, benzyl acrylate and methacrylate,
  • Preferred nonionic monomers include n-butyl methacrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, methyl methacrylate, t-butylacrylate, t-butylmethacrylate, and mixtures thereof.
  • Representative polar nonionic monomers include acrylamide, N,N-dimethylacrylamide, methacrylamide, N-t-butyl acrylamide,
  • methacrylonitrile acrylamide
  • acrylate alcohols eg. C 2 -C 6 acrylate alcohols such as hydroxyethyl acrylate, hdroxyproxyl acrylate
  • vinyl ethers such as methyl vinyl ether, acyl lactones and vinyl pyridine, allyl alcohols, vinyl alcohols and vinyl caprolactam.
  • Preferred polycationic polymer resins for use herein include cationic guar gum, cationic polysaccharides, homopolymers of dimethyldiallyl ammonium chloride, copolymers of dimethyldiallyl ammonium chloride and acrylamide, cationic amino-functional homopolymers and
  • copolymers derived from acrylic acid and/or methacrylic acid especially from alkylaminoalkyl acrylate and methacrylate monomers such as dimethylaminoethyl acrylate and methacrylate, polyalkylene imines and ethoxy polyalkylene imines, vinylimidazolium/vinylpyrrolidone
  • the hair styling polymers herein are preferably utilised in at least partially neutralised form in order to aid shampoo removability of the liquid hair cosmetic compositions.
  • the neutralisation of a hair fixative polymer eg silicone grafted tBA/AA copolymer
  • an inorganic base preferably KOH.
  • organic base preferably AMP (amino methyl propanol) and mixtures of inorganic and organic base may also be used to effect the desired level of neutralisation in hair cosmetic products according to the present invention.
  • AMP amino methyl propanol
  • Hydroxides of alkali, alkaline earth and amino alcohols are suitable neutralisers for use in the present liquid hair cosmetic
  • suitable organic neutralising agents which may be included in the hair cosmetic compositions of the present invention include amines, especially amino alcohols such as 2-amino-2-methyl-1,3-propanediol (AMPD), 2-amine-2-ethyl-1,3-propanediol (AEPD), 2-amino-2-methyl-1-propanol (AMP), 2-amino-1-butanol (AB), monethanolamine (MEA), diethanolamine (DEA), triethanolamine (TEA), monoisopropanolamine (MIPA), diisopropanolamine (DIPA), triisopropanolamine (TIPA), dimethyl steramine (DMS) and amino methyl propanol (AMP) and mixtures thereof.
  • Preferred neutralising agents for use in hair cosmetic compositions of the present invention are potassium and sodium hydroxides.
  • the amount in grams of base (Z) required to neutralise any given polymer can be deduced from calculations which take into account the acid value of the polymer (A); amount of polymer (W); mol wt of the base (B); mol wt of the acidic moiety (M) and the degree of neutralisation required (N).
  • the acid value can be experimentally determined by titrating a specific amount of the polymer with base or theoretically by considering the original acidic content of the co-polymer i.e. a polymer with 20% of acid monomer has an acid value of 20.
  • the liquid hair cosmetic compositions of the present invention also include a carrier.
  • a carrier can comprise any of those conventionally used in resin hairspray formulations inclusive of solvents, propellants and other optional ingredients of liquid hair cosmetics.
  • the carrier is generally present in the liquid hair cosmetic compositions at from about 60% to about 99.8%, preferably from about 68% to about 98% by weight. More preferably, the carrier is present at from about 70% to about 98% by weight of the total composition.
  • compositions include C 1 -C 6 alkanols, carbitol, acetone and mixtures thereof.
  • C 1 -C 6 alkanols preferred for use in the present compositions are C 2 -C 4 monohydric alcohols such as ethanol, isopropanol and mixtures thereof.
  • Liquid hair cosmetic compositions according to the present invention contain from 0% to about 15% by weight of water, preferably from 0% to about 10%, more preferably 0% to 5% by weight of water.
  • the performance of the liquid hair cosmetic compositions according to the invention can be improved through the optional incorporation of a nonvolatile plasticizer into the composition.
  • the plasticizer will generally be present in the compositions according to the invention up to a level of 25%, preferably from 1 % to 20%, more preferably from 1 % to 15%.
  • nonvolatile in regard to plasticizers means that the plasticizer exhibits essentially no vapour pressure at atmospheric pressure and 25°C.
  • the polymer-liquid vehicle solution should not suffer from substantial plasticizer weight loss while the hair cosmetic carrier is evaporating, since this may excessively reduce plasticization of the polymer during use.
  • the plasticizers for use herein should generally have boiling points of about 250°C or higher.
  • Plasticizers are well known in the art and are generally described in KirkOthmer Encyclopedia of Chemical Technology , second edition, Volume 15, pp. 720-789 (John Wiley & Sons, Inc. New York, 1968) under the topic heading "Plasticizers", and by J. Kern Sears and J. R. Darby in the text The Technology of Plasticizers (John Wiley & Sons, Inc., New York, 1982). See especially in the Appendix of Sears/Darby Table A.9 at pages 983-1063 where a wide variety of plasticizers are disclosed.
  • Plasticizers suitable for use in compositions of the present invention include both cyclic and acyclic nonvolatile materials. Suitable categories of nonvolatile plasticizers include adipates, phthalates, isophthalates, azelates, stearates, citrates, trimellitates, silicone copolyols, iso C 14 - C 22 alcohols, methyl alkyl silicones, carbonates, sebacates, isobutyrates, oleates, phosphates, myristates, ricinoleates, pelargonates, valerates, camphor, glycols, amine derivatives, selected short chain alcohols and castor oil.
  • nonvolatile plasticizers include adipates, phthalates, isophthalates, azelates, stearates, citrates, trimellitates, silicone copolyols, iso C 14 - C 22 alcohols, methyl alkyl silicones, carbonates, sebacates, isobutyrates
  • plasticizers for use herein include glycol and citrate based plasticizers such as propylene glycol, dipropylene glycol , acetyl tri-n-butyl citrate, tri-n-butyl and acetyl tri-2-ethoxyhexyl citrate (as supplied by Pfizer under the trade name Citroflex RTM) as well as glycerin, amino methyl propanol (AMP), diisobutyladipate (DIBA) and isopropanol.
  • glycol and citrate based plasticizers such as propylene glycol, dipropylene glycol , acetyl tri-n-butyl citrate, tri-n-butyl and acetyl tri-2-ethoxyhexyl citrate (as supplied by Pfizer under the trade name Citroflex RTM) as well as glycerin, amino methyl propanol (AMP), diisobutyladipate (DIBA) and is
  • compositions can be formulated as hairsprays in aerosol or non-aerosol forms. If an aerosol hairspray is desired, a propellant must be included in the composition. This agent is responsible for expelling the other materials from the container and forming the hairspray
  • the propellant gas can be any liquefiable gas conventionally used for aerosol containers.
  • the density of the propellant or mixture thereof is less than 1 so that pure propellant is not emitted from the container.
  • materials that are suitable for use as propellants are trichlorofluoromethane, dichlorodifluoromethane,
  • Dimel 152A supplied by Du Pont
  • propane propane, n-butane, isobutane, used singly or admixed and propane butane e.g. CAP 80 (RTM).
  • Dimel 152A (RTM) and propane butane are preferred.
  • the amount of the propellant gas is governed by normal factors well known in the aerosol art.
  • the level of propellant is generally from about 10% to about 40%, preferably from about 20% to about 30%, of the total composition. If a propellant such as dimethylether utilizes vapor pressure suppressant (e.g., trichloroethane or dichloromethane) the amount of suppressant is included as part of the propellant.
  • vapor pressure suppressant e.g., trichloroethane or dichloromethane
  • compositions of the present invention can be made using conventional formulation and mixing techniques.
  • Compositions of the present invention can be made by adding the polymers to ethanol and mixing for several hours until dissolved. Plasticizer and neutralising ingredients are then added and the resulting solution is stirred. Any remaining ingredients such as water, ethanol and perfume can then be added.
  • pressurised aerosol dispensers can be used where the propellant is separated from contact with the hairspray composition by use of specialised containers such as a two compartment can of the type sold under the tradename SEPRO from Americal National Can Corp.
  • Suitable aerosol dispensers are those characterized by the propellant being compressed air which can be filled into the dispenser by means of a pump or equivalent device prior to use. Such dispensers are described in US-A-4,077,441, March 7th 1978, Olofsson and US- A-4, 850,577, July 25th 1989, TerStege. Compressed air aerosol containers suitable for use are also currently marketed by The Procter & Gamble Company under their tradename VIDAL SASSOON AIRSPRAY (RTM) hairsprays.
  • RTM VIDAL SASSOON AIRSPRAY
  • Conventional non-aerosol pump spray dispensers i.e., atomizers, can also be used.
  • liquid hair cosmetic compositions of the present invention can also contain a variety of non-essential, optional components such as
  • preservatives surfactants, block polymers, thickeners and viscosity modifiers, electrolytes, fatty alcohols, pH adjusting agents, perfume oils, perfume solubilizing agents, sequestering agents, emollients; lubricants and penetrants such as various lanolin components; protein hydrolysates and other protein derivatives; ethylene adducts and polyoxyethylene cholesterol; sunscreens and volatile and non-volatile silicone fluids.
  • Such conventional optional ingredients are well known to a person skilled in the art, e.g.
  • surfactants such as anionics (e.g., sodium alkyl sulphates, nonionics (amine oxides) ; amphoterics (aliphatic secondary or tertiary amine derivatives) zwitter ionics (aliphatic quaternary ammonium;
  • anionics e.g., sodium alkyl sulphates, nonionics (amine oxides)
  • amphoterics aliphatic secondary or tertiary amine derivatives
  • zwitter ionics aliphatic quaternary ammonium
  • phosphonium or sulphonium derivatives phosphonium or sulphonium derivatives
  • fluorinated surfactants e.g. Zonyl FSK) (RTM)
  • thickeners and viscosity modifiers such as
  • diethanolamides of long chain fatty acids block polymers of ethylene oxide and propylene oxide such as Pluronic (RTM) F88 offered by BASF Wyandotte; fatty alcohols such as cetearyl alcohol; viscosity modifiers such as sodium chloride, sodium sulphate, and ethyl alcohol; electrolyte such as earth and alkaline-earth metal salts; quaternary ammonium ions and cationic amines and halogen ions; pH adjusting agents such as citric acid, succinic acid, sodium hydroxide and triethanolamine; perfume oils such as Florasynth (RTM) perfumes; perfume oil solubilizers such as polyethylene glycol fatty acid esters and sequestering agents such as ethylenediamine tetraacetic acid.
  • RTM Pluronic
  • fatty alcohols such as cetearyl alcohol
  • viscosity modifiers such as sodium chloride, sodium sulphate, and ethyl alcohol
  • electrolyte such
  • liquid hair cosmetic compositions of the present invention are used in conventional ways to provide the hair styling/holding benefits of the present invention.
  • Such method generally involves spraying an effective amount of the product to dry or damp hair before or after the hair is styled, or both.
  • effective amount is meant an amount sufficient to provide the hair volume and style benefits desired considering the length and texture of the hair.
  • silicone PDMS Weight average molecular weights (as measured using SEC) of 150,000.
  • KOH - Potassium hydroxide solution containing 45% potassium hydroxide and 55% water and minors.
  • liquid hair cosmetic compositions in the form of hairspray compositions suitable for pump spray dispensers and which are representative of the present invention:
  • the balance contains ethanol and any optional ingredients such as plasticizers, perfume and surfactants.
  • the hairspray formulations are prepared by adding the polymer directly to the ethanol.
  • a magnetic or air driven stirrer is used to mix the ingredients until the polymer is dissolved, typically about 1 to 2 hours.
  • the neutralizing agent is then added and mixed into the premix.
  • the optional ingredients and water, as may be applicable, are mixed into the composition.
  • compositions have excellent clarity and when applied to the hair impart excellent hair feel and good style retention properties.
  • liquid hair cosmetic compositions in the form of hairspray concentrate compositions suitable for aerosol dispensers and which are representative of the present invention:
  • Si Containing Copolymer 8.0 4.0 4.0 4.5 1.0 2.0 Non Si-Copolymer 1 2.0 - 1.0 - - 2.0 Non Si-Copolymer 2 - 0.5 - 0.5 8.0 - % poly KOH neutralised 60 55 55 60 60 50 % poly AMP neutralised 0 5 5 10 0 5 DRO Water 0 0 5 5 10 10 Balance - - - - - - to 100 percent with Ethanol - - - - - - - - - - -
  • the balance can contain ethanol and optional ingredients such as plasticizers, perfumes and surfactants.
  • the compositions are prepared as in Examples I-VI.
  • the concentrates are packaged in conventional aerosol spray cans and are charged with a conventional liquifiable propellant, such as CAP 80 (propane/butane) (RTM) at a propellant:concentrate weight ratio of 23:77.
  • compositions have excellent clarity and long term and stressed temperature stability characteristics and when applied to the hair impart excellent hair feel and good style retention properties.

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  • Cosmetics (AREA)

Abstract

L'invention concerne une composition cosmétique liquide pour cheveux comprenant: a) d'environ 0,1 à environ 10 % en poids (base acide) d'un copolymère d'acide polycarboxylique siliconé pour la tenue des cheveux, ayant un squelette de polymère vinylique sur lequel on a greffé un macromère siliconé d'un poids moléculaire moyen se situant dans une plage d'environ 1 000 à 50 000; b) d'environ 0,01 à environ 10 % en poids d'une résine pour la tenue des cheveux ne contenant pas de silicones; et c) le pourcentage restant comprenant un excipient approprié pour les cheveux. De tels produits cosmétiques liquides pour cheveux démontrent d'excellentes qualités de tenue de la chevelure et de toucher; ils facilitent en outre le brossage et possèdent une transparence améliorée
PCT/US1994/005253 1993-06-18 1994-05-11 Compositions cosmetiques pour les cheveux WO1995000108A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP7502799A JPH08511800A (ja) 1993-06-18 1994-05-11 ヘア化粧品組成物
KR1019950705775A KR960703003A (ko) 1993-06-18 1994-05-11 모발 화장품 조성물(hair cosmetic compositions)
EP95904335A EP0723433A1 (fr) 1993-06-18 1994-05-11 Procede de fabrication d'un conditionnement stenle de produits prets-a-l'emploi et recipient pour ce conditionnement
AU69101/94A AU6910194A (en) 1993-06-18 1994-05-11 Hair cosmetic compositions
BR9406849A BR9406849A (pt) 1993-06-18 1994-05-11 Composições cosméticas para cabelo

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB939312629A GB9312629D0 (en) 1993-06-18 1993-06-18 Hair cosmetic compositions
GB9312629.0 1993-06-18

Publications (1)

Publication Number Publication Date
WO1995000108A1 true WO1995000108A1 (fr) 1995-01-05

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1994/005253 WO1995000108A1 (fr) 1993-06-18 1994-05-11 Compositions cosmetiques pour les cheveux

Country Status (9)

Country Link
EP (1) EP0723433A1 (fr)
JP (1) JPH08511800A (fr)
KR (1) KR960703003A (fr)
CN (1) CN1129396A (fr)
AU (1) AU6910194A (fr)
BR (1) BR9406849A (fr)
CA (1) CA2165431A1 (fr)
GB (1) GB9312629D0 (fr)
WO (1) WO1995000108A1 (fr)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2291893A (en) * 1994-07-29 1996-02-07 Procter & Gamble Hair styling composition
WO1996032918A1 (fr) * 1995-04-21 1996-10-24 The Procter & Gamble Company Composition topique pour hygiene personnelle contenant un copolymere greffe silicone a coiffe terminale alkenyle ou styrene
FR2739285A1 (fr) * 1995-09-29 1997-04-04 Oreal Composition pour le traitement des matieres keratiniques comprenant au moins un polymere silicone greffe et au moins un polymere ou copolymere epaississant de (meth)acrylamide ou d'un derive de (meth)acrylamide et ses applications
FR2739283A1 (fr) * 1995-09-29 1997-04-04 Oreal Composition topique contenant un polymere a greffons silicones et un polymere amphiphile a chaine grasse
FR2739286A1 (fr) * 1995-09-29 1997-04-04 Oreal Composition capillaire comprenant un polymere silicone greffe par des monomeres anioniques, amphoteres ou non ioniques et un polymere amphotere
FR2739288A1 (fr) * 1995-09-29 1997-04-04 Oreal Composition topique comprenant l'association d'un polymere de squelette non-silicone a greffons silicones et d'un polymere de squelette polysiloxanique a greffons non silicones
FR2739282A1 (fr) * 1995-09-29 1997-04-04 Oreal Composition topique contenant un polymere a squelette polysiloxanique a greffons non-silicones et un polymere amphiphile a chaine grasse
FR2739289A1 (fr) * 1995-09-29 1997-04-04 Oreal Composition cosmetique comprenant au moins un polymere silicone greffe et au moins une association d'un polymere anionique et d'un polymere cationique
WO1997015275A1 (fr) * 1995-10-27 1997-05-01 The Procter & Gamble Company Compositions coiffantes contenant des polymeres greffes silicones ou non silicones ainsi qu'une faible quantite d'un solvant hydrocarbure volatil
WO1997030681A1 (fr) * 1996-02-22 1997-08-28 L'oreal Composition cosmetique de fixation et de brillance en aerosol et procedes
FR2755608A1 (fr) * 1996-11-12 1998-05-15 Oreal Composition cosmetique comprenant un polymere anionique ou non ionique et une silicone carboxylique
US6177063B1 (en) 1998-04-28 2001-01-23 The Procter & Gamble Company Anhydrous aerosol hairspray compositions containing silcone grafted copolymers
US6350439B1 (en) 1995-10-18 2002-02-26 L'oreal Aqueous lacquer packaged in an aerosol device and including at least one silicone graft polymer for treating keratinous materials, and uses thereof
US6368606B1 (en) 1995-10-18 2002-04-09 L'oreal Cosmetic composition for the treatment of keratinous materials comprising at least a grafted silicone polymer and at least an aqueous dispersion of insoluble particles of non ionic or cationic polymer
US6524564B1 (en) 1998-08-26 2003-02-25 Basf Aktiengesellschaft Urethane(meth)acrylates containing siloxane groups and able to undergo free-radical polymerization
WO2020084085A1 (fr) * 2018-10-25 2020-04-30 L'oreal Composition comprenant au moins un copolymère acrylique de silicone et au moins un copolymère acrylique cationique
WO2021219722A1 (fr) * 2020-04-30 2021-11-04 L'oreal Dispositif aérosol contenant une composition comprenant au moins un copolymère acrylique de silicone et au moins un propulseur

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3679569B2 (ja) * 1997-09-24 2005-08-03 花王株式会社 毛髪及び頭皮処理用水性ヘアトニック組成物
CN104822365B (zh) * 2012-11-29 2017-07-21 荷兰联合利华有限公司 头发护理组合物

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US4693935A (en) * 1986-05-19 1987-09-15 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer pressure sensitive adhesive composition and sheet materials coated therewith
US4728571A (en) * 1985-07-19 1988-03-01 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer release coating sheets and adhesive tapes
US5106609A (en) * 1990-05-01 1992-04-21 The Procter & Gamble Company Vehicle systems for use in cosmetic compositions
US5120531A (en) * 1990-04-06 1992-06-09 The Procter & Gamble Company Hair styling conditioners

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4728571A (en) * 1985-07-19 1988-03-01 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer release coating sheets and adhesive tapes
US4693935A (en) * 1986-05-19 1987-09-15 Minnesota Mining And Manufacturing Company Polysiloxane-grafted copolymer pressure sensitive adhesive composition and sheet materials coated therewith
US5120531A (en) * 1990-04-06 1992-06-09 The Procter & Gamble Company Hair styling conditioners
US5106609A (en) * 1990-05-01 1992-04-21 The Procter & Gamble Company Vehicle systems for use in cosmetic compositions

Cited By (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2291893A (en) * 1994-07-29 1996-02-07 Procter & Gamble Hair styling composition
GB2291893B (en) * 1994-07-29 1998-10-07 Procter & Gamble Hair styling compositions
WO1996032918A1 (fr) * 1995-04-21 1996-10-24 The Procter & Gamble Company Composition topique pour hygiene personnelle contenant un copolymere greffe silicone a coiffe terminale alkenyle ou styrene
WO1997012596A1 (fr) * 1995-09-29 1997-04-10 L'oreal Composition capillaire comprenant au moins un polymere silicone greffe par des monomeres anioniques, amphoteres ou non-ioniques et au moins un polymere amphotere
EP0773016A1 (fr) * 1995-09-29 1997-05-14 L'oreal Composition topique comprenant l'association d'un polymère à squelette non-siliconé à greffons siliconés et d'un polymère à squelette polysiloxanique à greffons non-siliconés
FR2739288A1 (fr) * 1995-09-29 1997-04-04 Oreal Composition topique comprenant l'association d'un polymere de squelette non-silicone a greffons silicones et d'un polymere de squelette polysiloxanique a greffons non silicones
FR2739282A1 (fr) * 1995-09-29 1997-04-04 Oreal Composition topique contenant un polymere a squelette polysiloxanique a greffons non-silicones et un polymere amphiphile a chaine grasse
FR2739289A1 (fr) * 1995-09-29 1997-04-04 Oreal Composition cosmetique comprenant au moins un polymere silicone greffe et au moins une association d'un polymere anionique et d'un polymere cationique
WO1997012588A1 (fr) * 1995-09-29 1997-04-10 L'oreal Composition cosmetique comprenant au moins un polymere silicone greffe et au moins une association d'un polymere anionique et d'un polymere cationique
US5976517A (en) * 1995-09-29 1999-11-02 L'oreal Hair care composition including at least one silicone polymer grafted by anionic, amphoteric or non-ionic monomers, and at least one amphoteric polymer
FR2739283A1 (fr) * 1995-09-29 1997-04-04 Oreal Composition topique contenant un polymere a greffons silicones et un polymere amphiphile a chaine grasse
WO1997012595A1 (fr) * 1995-09-29 1997-04-10 L'oreal Composition pour le traitement des matieres keratiniques comprenant au moins un polymere silicone greffe et au moins un polymere ou copolymere eppaississant de (meth)acrylamide ou d'un derive de (meth)acrylamide et ses applications
EP0769290A1 (fr) * 1995-09-29 1997-04-23 L'oreal Composition topique comprenant un polymère à greffons siliconés et un polymère amphiphile à chaîne grasse
FR2739286A1 (fr) * 1995-09-29 1997-04-04 Oreal Composition capillaire comprenant un polymere silicone greffe par des monomeres anioniques, amphoteres ou non ioniques et un polymere amphotere
US6132707A (en) * 1995-09-29 2000-10-17 L'oreal Topical composition containing a silicone polymer with a polysiloxane backbone having non-silicone grafts and a fatty-chain amphiphilic polymer
US6630136B1 (en) 1995-09-29 2003-10-07 L'oreal Topical composition containing a silicone polymer with a polysiloxane skeleton containing non-silicone grafts and a fatty-chain amphiphilic polymer
US6011126A (en) * 1995-09-29 2000-01-04 L'oreal Topical composition comprising the combination of a polymer with a non-silicone skeleton with silicone grafts and of a polymer with a polysiloxane skeleton with non-silicone grafts
US6503494B1 (en) 1995-09-29 2003-01-07 L'oreal S.A. Composition comprising silicone polymer containing non-silicone backbone and at least one thickening polymer or copolymer of (meth) crylamide or of a (meth) acrylamide derivative
US6471952B1 (en) 1995-09-29 2002-10-29 L'oreal, S.A. Cosmetic composition including at least one silicone-grafted polymer and at least one combination of an anionic polymer and a cationic polymer
US6090376A (en) * 1995-09-29 2000-07-18 L'oreal Topical composition comprising a polymer with silicone grafts and an amphiphilic polymer with a fatty chain
US6056945A (en) * 1995-09-29 2000-05-02 L'oreal Compositions containing silicone-grafted polymer and thickening polymer of (meth)acrylamide derivative
WO1997012586A1 (fr) * 1995-09-29 1997-04-10 L'oreal Composition topique contenant un polymere silicone a squelette polysiloxane a greffons non-silicones et un polymere amphiphile a chaine grasse
FR2739285A1 (fr) * 1995-09-29 1997-04-04 Oreal Composition pour le traitement des matieres keratiniques comprenant au moins un polymere silicone greffe et au moins un polymere ou copolymere epaississant de (meth)acrylamide ou d'un derive de (meth)acrylamide et ses applications
US6368606B1 (en) 1995-10-18 2002-04-09 L'oreal Cosmetic composition for the treatment of keratinous materials comprising at least a grafted silicone polymer and at least an aqueous dispersion of insoluble particles of non ionic or cationic polymer
US6440404B1 (en) 1995-10-18 2002-08-27 L'oreal S.A. Aqueous lacquer for treating keratin substances, packaged in an aerosol device and comprising at least one grafted silicone polymer, and uses thereof
US6350439B1 (en) 1995-10-18 2002-02-26 L'oreal Aqueous lacquer packaged in an aerosol device and including at least one silicone graft polymer for treating keratinous materials, and uses thereof
WO1997015275A1 (fr) * 1995-10-27 1997-05-01 The Procter & Gamble Company Compositions coiffantes contenant des polymeres greffes silicones ou non silicones ainsi qu'une faible quantite d'un solvant hydrocarbure volatil
CN1102041C (zh) * 1995-10-27 2003-02-26 普罗克特和甘保尔公司 含有非硅氧烷和硅氧烷接枝聚合物及低含量挥发性烃的头发定型组合物
WO1997030681A1 (fr) * 1996-02-22 1997-08-28 L'oreal Composition cosmetique de fixation et de brillance en aerosol et procedes
KR100296165B1 (ko) * 1996-02-22 2001-08-07 조지안느 플로 윤기를제공하는미용에어로졸고정용조성물,및이의제조법
US6503479B1 (en) 1996-02-22 2003-01-07 L'oreal Cosmetic aerosol composition for fixing and sheen of keratin substances, and processes
FR2745173A1 (fr) * 1996-02-22 1997-08-29 Oreal Composition cosmetique de fixation et de brillance en aerosol et procedes
US6592854B1 (en) 1996-11-12 2003-07-15 L'Oréal S. A. Cosmetic composition containing an anionic or nonionic polymer and a carboxylic silicon
WO1998020833A3 (fr) * 1996-11-12 1998-07-23 Oreal Composition cosmetique comprenant un polymere anionique ou non ionique et une silicone carboxylique
WO1998020833A2 (fr) * 1996-11-12 1998-05-22 L'oreal Composition cosmetique comprenant un polymere anionique ou non ionique et une silicone carboxylique
FR2755608A1 (fr) * 1996-11-12 1998-05-15 Oreal Composition cosmetique comprenant un polymere anionique ou non ionique et une silicone carboxylique
AU732427B2 (en) * 1996-11-12 2001-04-26 L'oreal Cosmetic composition comprising an anionic or nonionic polymer and a carboxylic silicon
US6177063B1 (en) 1998-04-28 2001-01-23 The Procter & Gamble Company Anhydrous aerosol hairspray compositions containing silcone grafted copolymers
US6524564B1 (en) 1998-08-26 2003-02-25 Basf Aktiengesellschaft Urethane(meth)acrylates containing siloxane groups and able to undergo free-radical polymerization
WO2020084085A1 (fr) * 2018-10-25 2020-04-30 L'oreal Composition comprenant au moins un copolymère acrylique de silicone et au moins un copolymère acrylique cationique
FR3087781A1 (fr) * 2018-10-25 2020-05-01 L'oreal Composition comprenant au moins un copolymere acrylique silicone et au moins un copolymere acrylique cationique
WO2021219722A1 (fr) * 2020-04-30 2021-11-04 L'oreal Dispositif aérosol contenant une composition comprenant au moins un copolymère acrylique de silicone et au moins un propulseur
FR3109730A1 (fr) * 2020-04-30 2021-11-05 L'oreal Dispositif aérosol contenant une composition comprenant au moins un copolymère acrylique siliconé et au moins un agent propulseur

Also Published As

Publication number Publication date
EP0723433A1 (fr) 1996-07-31
GB9312629D0 (en) 1993-08-04
CA2165431A1 (fr) 1994-12-19
KR960703003A (ko) 1996-06-19
BR9406849A (pt) 1996-04-16
CN1129396A (zh) 1996-08-21
AU6910194A (en) 1995-01-17
JPH08511800A (ja) 1996-12-10

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