EP0640105A1 - Agents adhesifs contenant un polymere a greffe polysiloxane et leur compositions cosmetiques - Google Patents

Agents adhesifs contenant un polymere a greffe polysiloxane et leur compositions cosmetiques

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Publication number
EP0640105A1
EP0640105A1 EP93911225A EP93911225A EP0640105A1 EP 0640105 A1 EP0640105 A1 EP 0640105A1 EP 93911225 A EP93911225 A EP 93911225A EP 93911225 A EP93911225 A EP 93911225A EP 0640105 A1 EP0640105 A1 EP 0640105A1
Authority
EP
European Patent Office
Prior art keywords
polysiloxane
monomers
vinyl
adhesive agent
weight
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
EP93911225A
Other languages
German (de)
English (en)
Inventor
Peter Marte Torgerson
Anthony Thomas Balchunas
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Co
Original Assignee
Procter and Gamble Co
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 Procter and Gamble Co filed Critical Procter and Gamble Co
Publication of EP0640105A1 publication Critical patent/EP0640105A1/fr
Ceased legal-status Critical Current

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Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • 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
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/14—Polymers provided for in subclass C08G
    • C08F290/148—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J155/00—Adhesives based on homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C09J123/00 - C09J153/00
    • C09J155/005—Homopolymers or copolymers obtained by polymerisation of macromolecular compounds terminated by a carbon-to-carbon double bond
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • the present invention relates to adhesive agents containing polysiloxane-grafted polymers and to compositions, such as cosme ⁇ tic compositions, containing such adhesive agents.
  • This invention especially relates to adhesive agents useful for hair setting purposes, and to hair setting compositions containing such adhe ⁇ sive agents.
  • compositions containing polysiloxane-grafted polymers can provide excellent hair style retention benefits, together with hair conditioning.
  • the compositions may be in any of the conventional forms includ- ing, but not limited to, shampoos, conditioners, hair sprays, tonics, lotions, gels, and mousses.
  • the compositions can provide these benefits to hair without leaving the hair stiff or sticky/tacky feel, as do conventional hair setting ingredients.
  • These types of adhesive, film-forming, polysiloxane-grafted polymers can also be used for other purposes, such as topical application to skin for cosmetic purposes or as a means for delivery of medicaments ⁇
  • the film forming agents can also be used in a wide variety of other adhesive areas, e.g. adhesive paper or binding materials, etc.
  • Polysiloxane-grafted polymers are disclosed for use in EPO Application 90307528.1, published January 16, 1991 as EPO Publication 0 408311 A2, Hayama, et al., U.S. Patent 5,061,481, issued October 29, 1991, Suzuki et al., U.S. Patent 5,106,609, Bolich et al., issued April 21, 1992, U.S. Patent 5,100,658, Bolich et al., issued March 31, 1992, U.S. Patent 5,100,657, Ansher-Jackson, et al., issued March 31, 1992, U.S. Patent 5,104,646, Bolich et al., issued April 14, 1992, U.S. Serial " No.
  • Adhesive compositions containing film-forming polysiloxane-grafted polymers are also disclosed in U.S. Patent 4,728,571, issued March 1, 1988, Clemens et al., U.S. Patent 5,021,477, issued June 4, 1991, Garbe et al., U.S. Patent 4,981,902, issued January 1, 1991, Garbe et al., U.S. Patent 4,988,506, issued January 29, 1991, Mitra et al., and U.S. Patent 4,981,903, Mitra et al., issued January 1, 1991, Mitra et al.
  • the present invention relates to a polymeric adhesive agent, especially a film-forming agent, comprising a polysiloxane-grafted polymer made by the polymerization of polymerizable, polysiloxane containing monomers with polymerizable non-polysiloxane-containing monomers, wherein said adhesive agent has a weight average molecular weight of at least about 20,000, contains from about 1% to about 50%, by weight, of the polysiloxane-containing monomer, and the weight percentage of silicon present as unreacted polysiloxane-containing monomers and polysiloxane-grafted polymers having a viscosity at 25'C of below about 10,000,000 centistokes based on the total silicon present as unreacted polysiloxane-containing monomer and polysiloxane-grafted polymer is about 15% or less.
  • the adhesive agent should contain no more than about 4%, by weight, of unreacted polysiloxane-containing monomer
  • the present invention provides cosmetic compositions, especially hair care compositions, eg. hair setting compositions, comprising the adhesive agent hereof and a carrier suitable for application to the hair.
  • the polymeric adhesive agent hereof comprises a film-forming polysiloxane-grafted polymer, made by the polymerization of polysiloxane-containing monomers with non-polysiloxane-containing monomers such that said adhesive agent has a weight average molecular weight of at least about 20,000, comprises from about 1% to about 50%, by weight, of the polysiloxane-containing monomers, and the weight percentage of unreacted polysiloxane-containing monomers and polysiloxane-grafted polymers having a viscosity at 25'C of below about 10,000,000 centistokes: to total silicon present as unreacted polysiloxane-containing monomer and polysiloxane-grafted polymer is about 15% or less, more preferably about 5% or less.
  • the level of polysiloxane-containing monomers in the adhesive agent includes monomer present in either unreacted (eg., unpoly erized)form as well as monomer incorporated into the adhesive agent in polymer form.
  • the adhesive agent should contain no more than about 4%, by weight, of unreacted polysiloxane-containing monomer and polysiloxane-grafted polymer having a viscosity at 25*C of below about 10,000,000, preferably less than about 3% more preferably less than about 2%, most preferably less than about 1%.
  • the limitation pertaining to the adhesive agent sets forth the maximum viscosity level, as described above, can also be limited to is preferably about 1,000,000, about 100,000 or about 10,000, etc.
  • Cosmetic compositions of the present invention typically contain from about 0.1% to about 10.0%, preferably from about 0.5% to about 8.0%, of the adhesive agent, although higher or lower amounts may be used for particular applications.
  • the adhesive agent hereof can also be used to advantage in other cosmetic products, such as make-up, mascara and eye-liner, nail polish, etc., as well as topical skin products such as creams and lotions, including for delivery of medicaments or other ingredients to the skin.
  • the adhesive agent hereof can further be used for other adhesive applications, such as adhesive paper and backing paper, etc.
  • the adhesive agent should have a weight average molecular weight of at least about 20,000. There is no upper limit for molecular weight except that which limits applicability of the invention for practical reasons, such as processing, aesthetic characteristics, for ulateability, etc.
  • the weight average molecular weight will be less than about 10,000,000, more generally less than about 5,000,000, and typically less than about 3,000,000.
  • the weight average molecular weight will be between about 50,000 and about 2,000,000, more preferably between about 75,000 and about 1,000,000, most preferably between about 100,000 and about 750,000.
  • the adhesive agents hereof when dried to form a film have a Tg of at least about -20 * C, preferably at least about 20'C, so that they are not sticky, or "tacky" to the touch.
  • Tg refers to the glass transition temperature of the non-silicone backbone
  • T refers to the crystalline melting point of the non-silicone backbone, if such a transition exists for a given polymer.
  • the Tm if any, is also above about -20 * C, more preferably above about 20'C.
  • the polymers useful in the compositions of the present invention are polysiloxane-grafted polymers of polymerizable "silicone-containing", or “polysiloxane-containing", monomers with non-silicone-containing monomers.
  • the polysiloxane-grafted polymers should satisfy the following four criteria:
  • the molecular weight of the silicone portion is at least about 500.
  • the non-silicone portion When used in a composition, such as a cosmetic composition for application to the hair or skin, the non-silicone portion should render the entire polymer soluble or dispersible in the composition vehicle and permit the polymer to deposit on the intended surface, eg. hair or skin.
  • the most preferred polymers comprise an organic backbone, especially a carbon backbone such as a vinyl polymeric backbone, and also preferably, a polydimethylsiloxane macromer having a weight average molecular weight of at least about 500, preferably from about 1,000 to about 100,000, more preferably from about 2,000 to about 50,000, most preferably about 5,000 to about 20,000, is grafted to the backbone.
  • Organic backbones contemplated include those that are derived from polymerizable, ethylenically unsaturated monomers. These include vinyl monomers, and other condensation monomers (eg., those that polymerize to form polyamides and polyesters) and ring-opening monomers (eg., ethyl oxazoline and caprolactone).
  • the polymer is such that when it is formulated into the finished composition, when dried, the polymer phase separates into a discontinuous phase which includes the polydimethylsiloxane macromer and a continuous phase which includes the backbone. It is believed that this phase separation property provides a specific orientation of the polymer which results in the desired combination of tactile feel and setting, film-forming, or adhesive benefits.
  • the phase-separating nature of the compositions of the present invention may be determined as follows:
  • the polymer is cast as a solid film out of a good solvent (i.e., a solvent which dissolves both the backbone and the sili ⁇ cone). This film is then sectioned and examined by transmission electron micrography. Hicrophase separation is demonstrated by the observation of inclusions in the continuous phase. These inclusions should have the proper size to match the size of the silicone chain (typically a few hundred nm or less) and the proper density to match the amount of silicone present. This behavior is well documented in the literature for polymers with this structure (see, for example, S. D. Smith, Ph.D. Thesis, University of Virginia, 1987, and references cited therein).
  • a second method for determining phase-separating character ⁇ istics involves examining the enrichment of the concentration of silicone at the surface of a polymer film relative to the concentration in the bulk polymer. Since the silicone prefers the low energy air interface, it preferentially orients on the polymer surface. This produces a surface with the silicone oreinted at the surface of the film. This can be demonstrated experimentally by ESCA (electron spectroscopy for chemical analysis) of the dried film surface. Such an analysis shows a high level of silicone and a greatly reduced level of backbone polymer when the film surface is analyzed. (Surface here means the first few tens of Angstroms of film thickness.) By varying the angle of the interrogating beam the surface can be analyzed to varying depths.
  • polymers are comprised of: at least one free radically polymerizable vinyl monomer or monomers (A); and optionally at least one reinforcing monomer copolymerizable with A which is more hydrophilic than A and is selected from the group consisting of hydrophilic monomers and macromers having a Tg or a Tm above about -20 * C (B).
  • the polymers also comprise polysiloxane-containing monomers.
  • Hydrophobic monomers means monomers which form substantially water insoluble homopolymers.
  • Hydrophilic monomers means monomers which do not form substantially water insoluble homopolymers.
  • Suitable polymers are also disclosed in EPO Application 90307528.1, published as EPO Application 0 408 311 A2 on January 11, 1991, Hayama, et al., U.S. Patent 5,061,481, issued October 29, 1991, Suzuki et al., U.S. Patent 5,106,609, Bolich et al., issued April 21, 1992, U.S.
  • the polysiloxane-grafted polymers hereof comprise from about 1% to about 50%, by weight of C monomers, i.e., the polysiloxane-containing monomers, and from about 50% to about 99% by weight, of non-polysiloxane-containing monomers, which can be monomers selected from the group consisting of A and B monomers, and mixtures thereof.
  • hydrophobic, A monomers are acrylic or methacrylic acid esters of Cx-Cj ⁇ alcohols, such as methanol, ethanol, methoxy ethanol, 1-propanol, 2-propanol, 1-butanol, 2-methyl-l-propanol, 1-pentanol, 2-pentanol, 3-penta- nol, 2-methyl-l-butanol, 1-methyl-l-butanol, 3-methyl-l-butanol, 1-methyl-1-pentanol, 2-methyl-l-pentanol, 3-methyl-l-pentanol, t-butanol(2-methyl-2-propanol), cyclohexanol, neodecanol, 2-ethyl- 1-butanol, 3-heptanol, benzyl alcohol, 2-octanol, 6-methyl-l- heptanol, 2-ethyl-l-hexanol, 3,5-di
  • Preferred A monomers include n-butyl methacrylate, isobutyl methacrylate, t-butyl acrylate, t-butyl methacrylate, 2-ethylhexyl methacrylate, methyl meth ⁇ acrylate, and mixtures thereof. Most preferably, A is selected from t-butyl acrylate, t-butyl methacrylate, and mixtures thereof.
  • hydrophilic, B monomers include acrylic acid, methacrylic acid, N,N-dimethylaery1amide, di ethyl- aminoethyl methacryl te, quaternized dimethylaminoethyl meth ⁇ acrylate, methacrylamide, N-t-butyl acrylamide, maleic acid, aleic anhydride and its half esters, crotonic acid, itaconic acid, acrylamide, acrylate alcohols, hydroxyethyl methacrylate, diallyldimethyl ammonium chloride, vinyl pyrrolidone, vinyl ethers (such as methyl vinyl ether), maleimides, vinyl pyridine, vinyl imidazole, other polar vinyl heterocyclics, styrene sulfonate, allyl alcohol, vinyl alcohol (produced by the hydrolysis of vinyl acetate after polymerization), vinyl caprolactam, and mixtures thereof.
  • Preferred B monomers include acrylic acid, N,N-dimethyl- acrylamide, dimethylaminoethyl methacrylate, quaternized dimethyl- a inoethyl methacrylate, vinyl pyrrolidone, salts of acids and amines listed above, and mixtures thereof.
  • C monomer The preferred polymerizable polysiloxane-containing monomer (C monomer) can be exemplified by the general formula:
  • X is a vinyl group copolymerizable with the A and B monomers
  • Y is a divalent linking group
  • R is a hydrogen, hydroxyl, lower alkyl (e.g. C x -C 4 ), aryl, alkaryl, alkoxy, or alkylamino
  • Z is a monovalent siloxane polymeric moiety having a number average molecular weight of at least about 500, is essentially unreactive under copoly erization conditions, and is pendant from the vinyl polymeric backbone described above
  • n is 0 or 1
  • m is an integer from 1 to 3.
  • C has a weight average molecular weight as described above.
  • the C monomer has a formula selected from the following group:
  • R 2 R 3 R 2 is hydrogen or -C00H (preferably R 2 is hydrogen); R 3 is hydrogen, m ⁇ thyl or -CH 2 C00H (preferably R 3 is methyl); Z is
  • the total of A and B monomers in the adhesive agent polymer will preferably be from about 50% to about 99%, more preferably from about 60% to about 98%, most preferably from about 75% to about 95)%, by weight of the polymer of the adhesive agent.
  • the level of A monomers can be from 0% to about 99%; the level of B monomers, from 0% to about 99%; and the level of C monomers, from 1% to about 50%, preferably from about 1% to about 40%, more preferably from about 2% to about 25%, of monomer C.
  • the composition of any particular adhesive agent polymer will help determine its formulational properties. In fact, by appropriate selection and combination of particular A, B and C components, the adhesive agent polymer can be optimized for inclusion in specific vehicles.
  • polymers which are soluble in an aqueous formulation or other polar or hydrophilic solvents preferably have from about 0% to about 85% (preferably from about 5% to about 70%) monomer A, from about 14% to about 95% (preferably from about 29% to about 80%) monomer B, and from about 1% to about 40% (preferably from about 2% to about 25%) monomer C.
  • Polymers which are dispersible in aqueous formulations have the preferred composition: from about 0% to about 70% (preferably from about 5% to about 70%) monomer A, from about 20% to about 80% (preferably from about 20% to about 60%) monomer B, and from about 1% to about 40% (preferably from about 2% to about 25%) monomer C.
  • the polysiloxane-grafted polymers can be synthesized as follows.
  • the polymers can be made by free radical polymerization of silicone- or polysiloxane-containing monomers with non-silicone- or non-polysiloxane-containing monomers.
  • the filming forming, cosmetic agent comprising this product is prepared by substantially removing the unreacted polysiloxane-containing monomers and polysiloxane-grafted polymers which have a fluid viscosity at 25 * C of below about 10,000,000, to the levels defined by silicon present as described above.
  • the monomer and polymeric material removed are both of relatively low molecular weight, compared to the molecular weight of the cosmetic agent hereof.
  • block copolymers of alternating organic block and silicone blocks are not included as polysiloxane-grafted polymers.
  • redox or radiation initiation can be used as desired.
  • the polymerization is allowed to proceed as long as needed for a high level of conversion to be achieved, typically from a few hours to a few days.
  • the solvent is then removed, usually by evaporation or by precipitating the polymer by addition of a nonsolvent.
  • the polymer is further purified, as needed.
  • Polymers I, II and III are synthesized in the following manner. There are numerous variations . on these procedures which are entirely up to the discretion of the synthetic chemist (e.g., choice of degassing method and gas, choice of initiator type, extent of conversion, reaction loading, etc). The choice of initiator and solvent are often determined by the requirements of the particular monomers used, since different monomers have different solubilities and different reactivities to a specific initiator.
  • Polymer I Place 20 parts acrylic acid, 60 parts t-butyl- acrylate, and 20 parts polysiloxane (10,000 MW)-containing monomer in a flask. Add sufficient ethyl acetate or acetone (preferably acetone) as the reaction solvent to produce a final monomer concentration of 40%. Add initiator, benzoyl peroxide, to a level of 0.5% by weight relative to the amount of monomer. Evacuate the vessel, and refill with nitrogen. Heat to 60"C and maintain this temperature for 48 hours while agitating. Terminate the reaction by cooling to room temperature, and dry off the reaction solvent by pouring the reaction mixture into a teflon-coated pan and placing in a vacuum oven.
  • Polymer III Place 10.5 parts N,N-dimethylmethacrylamide, 56 parts isobutyl methacrylate, 3.5 parts 2-ethylhexylmethacrylate, and 30 parts 10K PDMS macromer in a reaction vessel fitted with an argon sparge, temperature probe, reflux condenser and inlet port. Add sufficient toluene or isopropanol to bring the final monomer concentration to 20% by weight. Begin stirring and sparge with argon for 1 hour. While sparging, heat to 60'C in a water bath.
  • Removal of unwanted polysiloxane-containing monomer and/or polysiloxane-grafted polymeric material that has viscosity below 10,000,000 at 25 * C from free radically polymerized product can be done by any means known in the art.
  • the materials to be removed in general, will be of lower molecular weight than the average molecular weight of the polymer material prior to extraction. Also, such materials to be removed will contain a relatively high proportion of polysiloxane relative to the organic co ponent-generally, although not necessarily, in excess of 50% polysiloxane.
  • Techniques suitable for removing the unwanted material include a variety of standard procedures known in the art.
  • One method that can be used is supercritical fluid extraction, such as with supercritical carbon dioxide.
  • Supercritical fluid extraction is carried out on polymer which has been dried from the original reaction mixture to remove excess reaction solvent. Dried polymer is preferably ground to create a fine powder, which allows for increased surface area and maximum extraction efficiency. Extraction can be carried out using supercritical carbon dioxide in conventional extractors suitable for supercritical fluid extraction. The extraction should be conducted at a temperature of at least about 40 deg C and a pressure of between about 400-600 atmospheres. The particular temperature and pressure will depend upon criteria well known in the art, such as specific solvent, polymer sample size, fineness of the ground material, and the desired extraction efficiency. Extraction occurs via continuous purging under pressure with supercritical carbon dioxide, typically over a period of about 1-4 hours. Unreacted polysiloxane-containing monomer and low molecular weight polysiloxane-containing polymer is solubilized by carbon dioxide and is then transported away from the remaining polymer via standard procedures, e.g., by a transfer line.
  • a method which can be useful, particularly for adhesive agents utilizing polysiloxane-grafted polymers that are soluble in water, alcohol, or other polar solvents, is solvent extraction with a nonpolar solvent.
  • Suitable solvents include C 3 -C 8 hydrocarbons, preferably C 5 -C 6 hydrocarbons, such as hexane.
  • the polymer reaction product is precipitated out of the reaction solvent (e.g., with water), and dried.
  • the extraction solvent is preferably heated to near or slightly above the average Tg of the non-silicone backbone portion of the polysiloxane-grafted polymer of the adhesive agent.
  • the temperature should be high enough so that the polymer softens, but not so high such that it congeals.
  • the Tg of the polymer will vary from species to species of polymer.
  • the extraction solvent and reaction product can be mixed before, or after heating the solvent.
  • the extraction solvent and polymer reaction product should be held with mixing and preferably in an excess of solvent, for a reasonable period to effectuate removal of the soluble materials. This period will depend upon the reflux temperature of the solvent, the Tg of the polysiloxane-grafted polymer of the adhesive agent, the temperature to which the solvent is actually heated, the desired level of removal of unreacted monomer and the polysiloxane-containing polymer having viscosity at 25 * C below about 10,000,000, and the number of cycles of solvent extraction to be performed.
  • the solvent extraction periods will be from about one-half hour to about two hours, more typically from about one-half hour to about one hour.
  • the solvent can be removed after each cycle by conventional means, e.g., decanting, filtering, etc., with drying or distillation to remove trace extraction solvent remaining in the product after the final extraction cycle.
  • Analysis of the polymer reaction product and the extracted materials, and the purified film-forming agent can be done by conventional analysis techniques known in the art. These include, for example, nuclear magnetic resource (NMR), infrared molecular spectroscopies, gel permeation/size exclusion chromatography, and atomic absorption and emission spectroscopies.
  • NMR nuclear magnetic resource
  • infrared molecular spectroscopies gel permeation/size exclusion chromatography
  • atomic absorption and emission spectroscopies include, for example, nuclear magnetic resource (NMR), infrared molecular spectroscopies, gel permeation/size exclusion chromatography, and atomic absorption and emission spectroscopies.
  • compositions of the invention comprise the a carrier, or a mixture of such carriers, which are suitable for application to skin or hair.
  • the carriers are present at from about.0.5% to about 99.5%, preferably from about 5.0% to about 99.5%, " most preferably from about 10.0% to about 98.0%, of the composition.
  • suitable for application to hair means that the carrier does not damage or negatively affect the aesthetics of hair or cause irritation to skin.
  • Choice of appropriate solvent will also depend on the particular polymer to be used, and whether the product formulated is meant to be left on the surface to which it is applied (e.g., hair spray, mousse, tonic) or rinsed off (e.g., shampoo, conditioner) after use.
  • the carriers used herein include solvents, as well as other carrier or vehicle components conventionally used in hair care compositions.
  • the solvent selected must be able to dissolve or disperse the particular silicone-grafted polymer being used.
  • the silicone-grafted polymers can be designed, by appropriate combination of monomers, for formulation with a wide range of solvents. Suitable solvents for use in the present invention include, but are not limited to, water, lower alcohols (e.g.
  • C x -C 6 monohydric alcohols such as ethanol and isopropanol
  • hydro- alcoholic mixtures hydrocarbons (such as isobutane, hexane, decene, acetone), halogenated hydrocarbons (such as Freon), lina- Tool, hydrocarbon esters (such as ethyl acetate, dibutyl phtha- late), volatile silicon derivatives, especially siloxanes (such as phenyl pentamethyl disiloxane, methoxypropyl heptamethyl cyclo- tetrasiloxane, chloropropyl pentamethyl disiloxane, hydroxypropyl pentamethyl disiloxane, octamethyl cyclotetrasiloxane, decamethyl cyclopentasiloxane, cyclomethicone, and dimethicone (having for example, viscosity at 25 * C of about 15 centipoise or less
  • the carrier may include gel vehicle materials.
  • This gel vehicle comprises two essential components: a lipid vehicle material and a cationic surfactant vehicle material.
  • Cationic surfactant materials are described in detail below.
  • Gel-type vehicles are generally described in the following documents, all incorporated by reference herein: Barry, "The Self Bodying Action of the Mixed Emulsifier Sodium Dodecyl Sulfate/Cetyl Alcohol", 28 J. of Colloid and Interface Science 82-91 (1968); Barry, et al., "The Self-Bodying Action of Alkyltri ethylammonium Bromides/Cetostearyl Alcohol Mixed
  • the carrier may incorporate one or more lipid vehicle materials which are essentially water-insoluble, and contain hydrophobic and hydrophilic moieties.
  • Lipid vehicle materials include naturally or synthetically-derived acids, acid deriva ⁇ tives, alcohols, esters, ethers, ketones, and amides with carbon chains of from about 12 to about 22, preferably from about 16 to about 18, carbon atoms in length. Fatty alcohols and fatty esters are preferred; fatty alcohols are particularly preferred.
  • Lipid vehicle materials among those useful herein are dis ⁇ closed in Bailey's Industrial Oil and Fat Products. (3rd edition, D. Swern, ed., 1979), incorporated by reference herein.
  • the lipid vehicle material is present at from about 0.1% to about 10.0% of the composition; the cationic surfactant vehicle material is present at from about 0.05% to about 5.0% of the composition.
  • Preferred esters for use herein include cetyl palmitate and glyceryl onostearate.
  • Cetyl alcohol and stearyl alcohol are preferred alcohols.
  • a particularly preferred lipid vehicle material is comprised of a mixture of cetyl alcohol and stearyl alcohol containing from about 55% to about 65% (by weight of mixture) of cetyl alcohol.
  • Preferred carrier for use in the compositions of the present invention, especially for hair rinses include combinations of hydrophobically-modified hydroxyethyl cellulose materials with thickeners (such as locust bean gum), particular surfactants, quaternary ammonium compounds (such as ditallowdimethyl ammonium chloride), and/or chelating agents (such as EDTA).
  • thickeners such as locust bean gum
  • surfactants such as ditallowdimethyl ammonium chloride
  • quaternary ammonium compounds such as ditallowdimethyl ammonium chloride
  • chelating agents such as EDTA
  • Carriers, suitable for use with the present invention include, for example, those used in the formulation of tonics, mousses, gels and hair sprays.
  • Tonics, gels and non-aerosol hair sprays utilize a solvent such as water or alcohol while mousses and aerosol hair sprays additionally utilize a propel1ant such as trichlorof1uoromethane, dichlorodif1uoromethane, dif1uoroethane, dimethylether, propane, n-butane or isobutane.
  • a tonic or hair spray product having a low viscosity may also utilize an emul ⁇ sifying agent.
  • suitable emulsifying agents include nonionic, cationic, anionic surfactants, or mixtures thereof.
  • Fluorosurfactants are especially preferred, particularly if the product is a hair spray composition and most especially if it is a spray composition having relatively low levels of volatile organic solvents, such as alcohols, and relatively high levels of water (e-9-j in excess of about 10%, by weight water). If such an emulsifying agent is used, it is preferably present at a level of from about 0.01% to about 7.5% of the composition.
  • the level of propel1ant can be adjusted as desired but is generally from about 3% to about 30% of mousse compositions and from about 15% to about 50% of the aerosol hair spray compositions.
  • Suitable spray containers are well known in the art and include conventional, non-aerosol pump sprays i.e., "atomizers," aerosol containers or can having propellant, as described above, and also pump aerosol containers utilizing compressed air as the propellent.
  • Pump aerosol containers are disclosed, for example, in U.S. Patents 4,077,441, March 7, 1978, Olofsson and 4,850,577, July 25, 1989, TerStege, both incorporated by reference herein, and also in U.S. Serial No. 07/839,648, Gosselin, Lund, Sojka, and Lefebvre, filed February 21, 1992, "Consumer Product Package Incorporating A Spray Device Utilizing Large Diameter Bubbles.
  • Pump aerosols hair sprays using compressed air are also currently marketed by The Procter & Gamble Company under their tradename VIDAL SASSOON AIRSPRAY ® hair sprays.
  • compositions of the present invention may be formulated in a wide variety of product types, including mousses, gels, lotions, tonics, sprays, shampoos and conditioners.
  • additional components required to formulate such products vary with product type and can be routinely chosen by one skilled in the hair care product art. The following is a description of some of these additional components.
  • Surfactants are preferred optional ingredients in the compo ⁇ sitions of the invention, particularly shampoo and conditioner compositions.
  • the surfactant comprises from about 0.05% to about 50% of the composition.
  • the level is preferably from about 10% to about 30%, most preferably from about 12% to about 25%, of the composition.
  • the preferred level of surfactant is from about 0.2% to about 3%.
  • Surfactants useful in compositions of the present invention include anionic, nonionic, cationic, zwitterionic and amphoteric surfactants.
  • Synthetic anionic detergents useful herein, particularly for shampoo compositions include alkyl and alkyl ether sulfates. These materials typically have the respective formulae ROSO3M and R0(C2H40) X S03 , wherein R is alkyl or alkenyl of from about 10 to about 20 carbon atoms, x is 1 to 10, and M is a water-soluble cation such as ammonium, sodium, potassium and triethanolamine.
  • anionic surfactants are the water- soluble salts of the organic, sulfuric acid reaction products of the general formula: R1-SO3-M wherein Ri is chosen from the group consisting of a straight or branched chain, saturated aliphatic hydrocarbon radical having from about 8 to about 24, preferably about 12 to about 18, carbon atoms; and M is a cation.
  • salts of an organic sulfuric acid reaction product of a hydrocarbon of the methane series including iso-, neo-, and n-paraffins, having about 8 to about 24 carbon atoms, preferably about 12 to about 18 carbon atoms and a sulfonating agent, e.g., SO3, H2SO4, oleum, obtained according to known sulfonation methods, including bleaching and hydrolysis.
  • a sulfonating agent e.g., SO3, H2SO4, oleum
  • alkali metal and ammonium sulfonated C12-I8 n-paraffins are preferred.
  • anionic synthetic surfactants which come within the terms of the present invention are the reaction products of fatty acids esterified with isethionic acid and neutralized with sodium hydroxide where, for example, the fatty acids are derived from coconut oil; sodium or potassium salts of fatty acid amides of methyl tauride in which the fatty acids, for example, are derived from coconut oil.
  • Other anionic synthetic surfactants of this variety are set forth in U.S. Patents 2,486,921; 2,486,922; and 2,396,278.
  • Still other anionic synthetic surfactants include the class designated as succinamates.
  • This class includes such surface active agents as disodium N-octadecylsulfosuccinamate; tetrasodiu N-(1,2-dicarboxyethyl)-N-octadecylsulfosuccinamate; diamyl ester of sodium sulfosuccinic acid; dihexyl ester of sodium sulfosuc- . cinic acid; dioctyl esters of sodium sulfosuccinic acid.
  • olefin sulfonates having about 12 to about 24 carbon atoms.
  • olefin sulfonates is used herein to mean compounds which can be produced by the sulfonation of a-olefins by means of unco plexed sulfur trioxide, followed by neutralization of the acid reaction mixture in conditions such that any sultones which have been formed in the reaction are hydrolyzed to give the corresponding hydroxy-alkanesulfonates.
  • the ⁇ -olefins from which the olefin sulfonates are " derived are mono-olefins having about 12 to about 24 carbon atoms, preferably about 14 to about 16 carbon atoms.
  • Another class of anionic organic surfactants are the J-alkyloxy alkane sulfonates. These compounds have the following formula:
  • Rj is a straight chain alkyl group having from about 6 to about 20 carbon atoms
  • R2 is a lower alkyl group having from about 1 (preferred) to about 3 carbon atoms
  • M is a water-soluble cation as hereinbefore described.
  • Nonionic surfactants which are preferably used in combina ⁇ tion with an anionic, amphoteric or zwitterionic surfactant, can be broadly defined as compounds produced by the condensation of alkylene oxide groups (hydrophilic in nature) with an organic hydrophobic compound, which may be aliphatic or alkyl aromatic in nature. Examples of preferred classes of nonionic surfactants are: 2. Those derived from the condensation of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylene diamine products.
  • R1R23N > 0 wherein Ri contains an alkyl, alkenyl or monohydroxy alkyl radical of from about 8 to about 18 carbon atoms, from 0 to about 10 ethylene oxide moieties, and from 0 to about 1 glyceryl moiety, and R2 and R3 contain from about 1 to about 3 carbon atoms .and from 0 to about 1 hydroxy group, e.g., methyl, ethyl, propyl, hydroxyethyl, or hydroxypropyl radicals (the arrow in the formula is a conventional representation of a se ipolar bond). 5.
  • Long chain tertiary phosphine oxides corresponding to the following general formula:
  • R contains an alkyl, alkenyl or monohydroxyalkyl radical ranging from about 8 to about 18 carbon atoms in chain length, from 0 to about 10 ethylene oxide moieties and from 0 to about 1 glyceryl moiety and R' and R" are each alkyl or monohydroxyalkyl groups containing from about I to about 3 carbon atoms.
  • the arrow in the formula is a conventional representation of a semipolar bond. 6.
  • Examples include: octadecyl methyl sulfoxide, 2-ketotridecyl methyl sulfoxide, 3,6,9,-trixaoctadecyl 2-hydroxyethyl sulfoxide, dodecyl methyl sulfoxide, oleyl 3-hydroxypropyl sulfoxide, tetra- decyl methyl sulfoxide, 3-methoxytridecyl methyl sulfoxide, 3-hydroxytridecyl methyl sulfoxide, 3-hydroxy-4-dodecoxybutyl methyl sulfoxide.
  • Cationic surfactants useful in compositions of the present invention contain amino or quaternary ammonium hydrophilic moieties which are positively charged when dissolved in the aqueous composition of the present invention.
  • Cationic surfactants among those useful herein are disclosed in the following documents, all incorporated by reference herein: M.C. Publishing Co., McCutcheon's. Deter ⁇ gents & Emulsifiers. (North American edition 1979); Schwartz, et al., Surface Active Agents, Their Chemistry and Technology. New York: Interscience Publishers, 1949; U.S. Patent 3,155,591, Spotifyr, issued November 3, 1964; U.S.
  • the cationic surfactant is present at from about 0.05% to about 5%.
  • quaternary ammonium-containing cationic surfactant materials useful herein are those of the general formula:
  • the aliphatic groups may contain, in addition to carbon and hydrogen atoms, ether linkages, and other groups such as amino groups.
  • the longer chain aliphatic groups eg., those of about 12 carbons, or higher, can be saturated or unsaturated.
  • quaternary ammonium salts useful herein are diquaternary ammonium salts, such as tallow propane diammonium dichloride.
  • Quaternary ammonium salts include dialkyldimethyl-ammonium chlorides, wherein the alkyl groups have from about Tl to about 22 carbon atoms and are derived from long-chain fatty acids, such as hydrogenated tallow fatty acid (tallow fatty acids yield quaternary compounds wherein Rj and R2 have predominately from 16 to 18 carbon atoms).
  • Examples of quaternary ammonium salts useful in the present invention include ditallowdimethyl ammonium chlo ⁇ ride, ditallowdi ethyl ammonium methyl sulfate, dihexadecyl dimethyl ammonium chloride, di(hydrogenated tallow) dimethyl ammonium chloride, dioctadecyl dimethyl ammonium chloride, diei- cosyl dimethyl ammonium chloride, didocosyl dimethyl ammonium chloride, di(hydrogenated tallow) dimethyl ammonium acetate, dihexadecyl dimethyl ammonium chloride, dihexadecyl dimethyl ammonium acetate, ditallow dipropyl ammonium phosphate, ditallow dimethyl ammonium nitrate, di(coconutalkyl) dimethyl ammonium chloride, and stearyl dimethyl benzyl ammonium chloride.
  • Ditallow dimethyl ammonium chloride, dicetyl dimethyl ammonium chloride, stearyl dimethyl benzyl ammonium chloride and cetyl trimethyl ammonium chloride are preferred quaternary ammonium salts useful herein.
  • Di-(saturated or unsaturated tallow) dimethyl ammonium chloride is a particularly preferred quaternary ammonium salt.
  • Salts of primary, secondary and tertiary fatty amines are also suitable cationic surfactant materials.
  • the alkyl groups of such amines preferably have from about 12 to about 22 carbon atoms, and may be substituted or unsubstituted.
  • Such amines useful herein, include stearamido propyl dimethyl amine, diethyl a ino ethyl stearamide, dimethyl stearamine, dimethyl soyamine, soyamine, myristyl amine, tridecyl amine, ethyl stearylamine, " N-tallowpropane diamine, ethoxylated (5 moles E.O.) stearylamine, dihydroxy ethyl stearylamine, and arachidylbehenylamine.
  • Suitable amine salts include the halogen, acetate, phosphate, nitrate, citrate, lactate and alkyl sulfate salts.
  • Such salts include stearylamine hydrochloride, soyamine chloride, stearylamine formate, N-tallowpropane diamine dichloride and stearamidopropyl dimethylamine citrate.
  • Cationic amine surfactants included among those useful in the present invention are disclosed in U.S. Patent 4,275,055 " , demoigaTT et al., issued June 23, 1981, incorporated by reference herein.
  • Zwitterionic surfactants useful in shampoos as well as conditioners, are exemplified by those which can be broadly described as derivatives of aliphatic quaternary ammonium, phos- phonium, and sulfonium compounds, in which the aliphatic radicals can be straight or branched chain, and wherein one of the ali ⁇ phatic substituents contains from about 8 to about 18 carbon atoms and one contains an anionic water-solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
  • a general formula for these compounds is:
  • R- contains an alkyl, alkenyl, or hydroxy alkyl radical of from about 8 to about 18 carbon atoms, from 0 to about 10 ethylene oxide moieties and from 0 to about 1 glyceryl moiety;
  • Y is se ⁇ lected from the group consisting of nitrogen, phosphorus, and sulfur atoms;
  • R 3 is an alkyl or monohydroxyalkyl group containing about 1 to about 3 carbon atoms;
  • X is 1 when Y is a sulfur atom, and 2 when Y is a nitrogen or phosphorus atom;
  • R 4 is an alkylene or hydroxyalkylene of from about 1 to about 4 carbon atoms and Z is a radical selected from the group consisting of carboxylate, sulfonate, sulfate, phosphonate, and phosphate groups.
  • betaines are also useful in the present invention.
  • betaines useful herein include the high alkyl Detaines, such as coco dimethyl carboxymethyl betaine, lauryl dimethyl carboxymethyl betaine, lauryl dimethyl alpha- carboxyethyl betaine, cetyl dimethyl carboxymethyl betaine, lauryl bis-(2-hydroxyethyl) carboxymethyl betaine, stearyl bis-(2- hydroxypropyl) carboxymethyl betaine, oleyl dimethyl gamma- carboxypropyl betaine, and lauryl bis-(2-hydroxypropyl)alpha- carboxyethyl betaine.
  • the sulfobetaines may be represented by coco dimethyl sulfopropyl betaine, stearyl dimethyl sulfopropyl betaine, lauryl dimethyl sulfoethyl betaine, lauryl bis-(2-hy- droxyethyl) sulfopropyl betaine and the like; amidobetaines and amidosulfobetaines, wherein the RCONH(CH2)3 radical is attached to the nitrogen atom of the betaine are also useful in this invention.
  • amphoteric surfactants which can be used in the compositions of the present invention are those which are broadly described as derivatives of aliphatic secondary and tertiary amines in which the aliphatic radical can be straight or branched chain and wherein one of the aliphatic substituents contains from about 8 to about 18 carbon atoms and one contains an anionic water solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
  • an anionic water solubilizing group e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
  • Examples of compounds falling within this defini ⁇ tion are sodium 3-dodecyl-aminopropionate, sodium 3-dodecylamino- propane sulfonate, N-alkyltaurines such as the one prepared by reacting dodecylamine with sodium isethionate according to the teaching of U.S. Patent 2,658,072, N-higher alkyl aspartic acids such as those produced according to the teaching of U.S. Patent 2,438,091, and the products sold under the trade name "Miranol" and described in U.S. Patent 2,528,378.
  • Fluorosurfactant The compositions of the present invention can contain, fluorosurfactant.
  • Suitable fluorosurfactant can be cationic, anionic, amphoteric, zwitterionic, nonionic or a mixture thereof.
  • Fluorosurfactants include perfluorinated compounds such as those represented by the formula
  • Z is a water solubilizing group of either organic or in ⁇ organic character
  • x is an integer which is generally from 2 to 17, particularly from 7 to 11
  • y is an integer from 0 to 4
  • said compounds may be cationic, anionic, amphoteric or zwit- terionic, depending upon the nature of the grouping or groupings encompassed by Z.
  • the Z groups may be or may comprise sulfate, sulfonate, carboxylate, amine salt, quaternary ammonium, phos- phate, phosphonate, and combinations thereof.
  • the perfluorinated compounds are known in the art. These compounds are described in U.S.
  • Preferred fluorinated alkyl quaternary ammonium iodides are supplied under the tradename Fluorad FC-135 ® supplied by 3M.
  • Anionic fluorosurfactants include mono-, and bis-perfluoroalkyl phosphates, such as Zonyl FSP ® supplied by DuPont and conforming to the general formulae (R f CH 2 CH 2 0)P(0)(0NH 4 ) 2 (RfCH 2 CH 2 0) 2 P(0)(0NH 4 ) wherein
  • Amphoteric fluorosurfactants include fluorinated alkyl amphoterics such as Fluorad FC-100 ® supplied by 3M.
  • Fluorosurfactants can be used alone or in combination in the hair spray compositions of the present invention.
  • Fluorosurfactants when used, will typically be present at from about 0.01% to about 2%, preferably from about 0.01% to about 1.5%, by weight of the composition.
  • surfactants can be used alone or in combination in the compositions hereof.
  • the cosmetic compositions herein can contain a variety of other optional components suitable for rendering such compositions more cosmetically or aesthetically acceptable or to provide them with additional usage benefits.
  • Such conventional optional ingredients are well-known to those skilled in the art, e.g., pearlescent aids, such as ethylene glycol distearate; preserva- tives, such as benzyl alcohol, methyl paraben, propyl paraben and imidazolidinyl urea; thickeners and viscosity modifiers, such as a diethanolamide of a long chain fatty acid (e.g., PEG 3 lauric diethanolamide), cocomonoethanol amide, dimethicone copolyols, guar gum, methyl cellulose, starches and starch derivatives; fatty alcohols, such as cetearyl alcohol; sodium chloride; sodium sulfate; polyvinyl alcohol; ethyl alcohol; pH adjusting agents, such as citric acid, sodium citrate, succinic acid, phospho
  • the pH of the present compositions generally will be between about 3 and about 9, preferably between about 4 and about 8.
  • the present invention should not contain components which unduly interfere with the performance of the compositions.
  • the cosmetic compositions of the present invention can be made using conventional formulation and mixing techniques. Methods of making various types of cosmetic compositions are described more specifically in the following examples.
  • compositions of the present invention are used in conventional ways to provide the conditioning/styling/hold/adhesive/film-forming or other benefits of the present invention.
  • Such method of use depends upon the type of composition employed but generally involves application of an effective amount of the product to the hair or skin, which may then be rinsed from the hair or skin (as in the case of shampoos and some conditioning products) or allowed to remain on the hair (as in the case of spray, mousse, gel, skin lotion, film-forming skin lotion with medicament, and tonic products).
  • effective amount is meant an amount sufficient to provide the film-forming benefits desired.
  • hair rinse, mousse, and gel products are applied to wet or damp hair prior to drying and styling of the hair.
  • compositions are applied to the hair, the hair is dried and styled in the usual ways of the user.
  • Hair sprays are typically applied to dry hair after it has already been dried and styled.
  • Cosmetics and skin lotions are applied to face, skin, or eye area in the conventional manners of usage for those types of products.
  • adhesive agents containing polysiloxane-grafted polymers such as those described in U.S. Patent 4,693,935, Mazurek, issued September 15, 1987 and U.S. Patent 4,728,571, Clemens et al., issued March 1, 1988, can be used in adhesive proucts such as adhesive tapes and backing sheets for adhesive materials.
  • the adhesive agents hereof also can include non-pressure sensitive as well as pressure sensitive film-forming polymers.
  • the reaction product is precipitated out of the acetone by water addition and dried. Hexane extraction of the reaction product is then performed by adding an excess of hexane to the reaction product and heating to reflux, about 70'C.
  • the Tg of the non-silicone portion of the adhesive agent polymer is about 63 * C.
  • the mixture is held at this temperature with stirring for about 30 minutes and cooled to room temperature.
  • the hexane is removed by vacuum suction. Two more hexane extraction cycles are conducted in the same manner as above. After the third cycle, residual hexane remaining with the product is removed by distillation and vacuum drying.
  • hair spray compositions representative of the present invention are hair spray compositions representative of the present invention.
  • This product is prepared by dissolving the silicone polymer to the ethanol and mixing for several hours until all the polymer is dissolved. Plasticizer is then added, if applicable. Potassium hydroxide is then added. Water or water/surfactant, as applicable, is added. Fragrance is added last. All ingredients are added under mixing conditions.
  • the product can be packaged in conventional nonaerosol pump spray containers and compressed air pump spray aerosol containers.
  • EXAMPLE IV The following is a hair grooming tonic composition repre ⁇ sentative of the present invention.
  • Component Weight % is a hair grooming tonic composition repre ⁇ sentative of the present invention.
  • composition is made by mixing the above components together in a conventional manner.
  • EXAMPLE V The following is a shampoo composition representative of the present invention. Component Weight % Ammonium laureth sulfate 7.00
  • the shampoo is prepared by combining the ammonium laureth sulfate (normally supplied as a 28% solution in water) and Silicone Copolymer and heating to 70 * C for about 1/2 hour with mixing. The remaining ingredients are added and mixed for an additional 1/2 hour. The batch is then cooled to ambient temperature. Composition pH is adjusted to 6.5 by the addition of citric acid or sodium hydroxide, if necessary.
  • EXAMPLE VI The following is a cold-wave hair perm composition repre- sentative of the present invention.
  • composition is prepared by blending all the ingredients with agitation for about 1/2 hour at 60 * C and then cooling to ambient temperature.
  • the following is a styling gel composition representative of the present invention.
  • the following is a hair mousse composition representative of the present invention.
  • composition is made by blending all of the ingredients except isobutane at ambient temperature until well mixed. Alumi- num aerosol cans are then filled with 95 parts of this batch, affixed with a valve which is crimped into position, and lastly pressure filled with 5 parts isobutane.
  • compositions representative of the present invention Composition Citric Acid Sodium Citrate Cetyl Alcohol Stearyl Alochol
  • the styling polymer premix is prepared by combining the polymer, the octamethyl tetrasiloxane and decamethyl pentasiloxane, and butyl stearate.
  • the silicone gum premix is prepared by combining and mixing (in a separate vessel) the silicone gum and decamethyl cyclopenta ⁇ siloxane until homogeneous.
  • the conditioner premix is prepared by combining and mixing (in a separate vessel) DRO water, any primary and secondary thickeners (premelted if necessary to ensure ho ogenity) at 82 * the silicone gum premix, and amodiomethicone at 71*C, until homogeneous.
  • the DRO water is heated to 71 * C.
  • Citric acid, sodium citrate, cetyl alcohol, stearyl alcohol and Natrosol Plus CS grade D-67 are added and mixed until homogeneous.
  • the xanthan gum is added and mixed until homogeneous.
  • the styling polymer premix, Kathon CG and perfume are added and mixed until homogeneous.
  • the composition is further dispersed with an in-line homogenizer (such as Tekmar homogenizer) and then cooled to 38 * C.
  • the conditioner premix is also further dispersed with an in-line homogenizer and cooled to 38 * C and added to the final vessel, mixing until homogeneous to form the styling rinse composition.
  • an in-line homogenizer and cooled to 38 * C and added to the final vessel, mixing until homogeneous to form the styling rinse composition.
  • An aerosol hair spray composition of the present invention is prepared as follows:

Abstract

L'invention concerne des agents adhésifs polymères comprenant des polymères à greffe polysiloxane dans lesquels: (a) les polymères sont obtenus par polymérisation de monomères contenant du polysiloxane et de monomères ne contenant pas de polysiloxane, typiquement par polymérisation des radicaux libres; (b) l'agent adhésif a une masse moléculaire moyenne en poids d'au moins environ 20,000 et contient environ 1 à environ 50 %, en poids, de monomères contenant du polysiloxane; et (c) le pourcentage pondéral de silicium présent sous la forme d'un monomère contenant du polysiloxane non réagi et d'un polymère à greffre silicone ayant une viscosité à 25 °C inférieure à environ 10,000,000 centistokes, sur la base du silicium total présent sous la forme de monomère de silicium non réagi et de polymère à greffe de polysiloxane est d'environ 15 % ou moins. De plus, l'agent adhésif ne contient pas plus d'environ 4 %, en poids, de monomère contenant du polysiloxane non réagi, et de polymère à greffe polysiloxane ayant une viscosité à 25 °C inférieure à environ 10,000,000 centistokes. L'invention concerne également des compositions cosmétiques contenant lesdits agents adhésifs.
EP93911225A 1992-05-15 1993-05-11 Agents adhesifs contenant un polymere a greffe polysiloxane et leur compositions cosmetiques Ceased EP0640105A1 (fr)

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WO1997012593A1 (fr) * 1995-09-29 1997-04-10 L'oreal Composition cosmetique comprenant au moins un polymere silicone greffe et au moins un copolymere bloc lineaire polysiloxane-polyoxyalkylene
FR2739280A1 (fr) * 1995-09-29 1997-04-04 Oreal Composition cosmetique comprenant au moins un polymere silicone greffe et au moins un copolymere bloc lineaire polysiloxane-polyoxyalkylene
WO1997046210A1 (fr) 1996-06-07 1997-12-11 L'oreal Compositions cosmetiques detergentes a usage capillaire et utilisation
US7928087B2 (en) 2001-01-12 2011-04-19 L'oreal Cosmetic compositions containing fructan and a cationic polymer and their uses
WO2004043330A2 (fr) 2002-11-07 2004-05-27 L'oreal Composition cosmetique comprenant au moins un carbonate cyclique particulier apte a polymeriser
US7378103B2 (en) 2004-03-22 2008-05-27 L'oreal Cosmetic composition comprising a polyglycerolated silicone elastomer
EP1616557A2 (fr) 2004-07-16 2006-01-18 L'oreal Composition cosmétique comprenant un polymère de silicone defini et un agent filmogène
EP1629827A1 (fr) 2004-07-29 2006-03-01 L'oreal Composition cosmétique comprenant un polyester sulfonique linéaire et une gomme de guar modifiée, procédés mettant en oevre cette composition et utilisations
EP1629828A1 (fr) 2004-07-29 2006-03-01 L'oreal Composition cosmétique comprenant un polyester sulfonique linéaire et un polyuréthane particulier, procédés mettant en oeuvre cette composition et utilisations
EP1627664A1 (fr) 2004-07-30 2006-02-22 L'oreal Composition de coiffage comprenant des particules adhésives et des particules non-adhésives
EP1634580A1 (fr) 2004-09-09 2006-03-15 L'oreal Composition de coiffage comprenant l'association d'un materiau polymerique hydrophile de haute porosite et d'un polymere fixant
EP1634620A1 (fr) 2004-09-10 2006-03-15 L'oreal Composition cosmétique comprenant des composés ayant une structure cage
EP1642620A1 (fr) 2004-10-04 2006-04-05 L'oreal, S.A. Composition cosmétique capillaire à base de particules creuses et de polyuréthane fixant siliconé
EP1652510A1 (fr) 2004-10-28 2006-05-03 L'oreal Composition cosmétique comprenant un polyester sulfonique et un polyuréthane
EP1688127A1 (fr) 2005-01-18 2006-08-09 L'oreal Composition de traitement des fibres kératiniques comprenant un alcool aromatique, un acide carboxylique aromatique et un agent protecteur
US8790623B2 (en) 2005-01-18 2014-07-29 Il'Oreal Composition for treating keratin fibers, comprising at least one aromatic alcohol, at least one aromatic carboxylic acid, and at least one protecting agent
EP1685825A1 (fr) 2005-01-28 2006-08-02 L'oreal Procédé de traitement capillaire et utilisation dudit procédé
EP1695688A1 (fr) 2005-02-28 2006-08-30 L'oreal Composition anhydre sous forme de film comprenant un polymère filmogène et un colorant direct
EP1695689A1 (fr) 2005-02-28 2006-08-30 L'oreal Composition anhydre sous form de film comprenant un polymère filmogène et un colorant d'oxydation
EP1695687A1 (fr) 2005-02-28 2006-08-30 L'oreal Composition anhydre sous forme de film comprenant un polymère filmogène et un agent oxydant
EP1719545A1 (fr) 2005-04-29 2006-11-08 L'oreal Procédé de mise en forme semi-permanente des cheveux
US7799093B2 (en) 2006-10-25 2010-09-21 L'ORéAL S.A. Coloring composition of keratinous fibers comprising at least one polysiloxane/polyurea block copolymer
EP1935396A1 (fr) 2006-12-22 2008-06-25 L'Oreal Procédé de déformation permanente des fibres kératiniques comprenant une étape d'application d'une composition reéuctrice faiblement concentrée et une étape intermédiaire de séchage
EP1961490A1 (fr) 2007-02-23 2008-08-27 L'Oreal Dispositif de pulverisation d'une composition de fixation
EP1961489A1 (fr) 2007-02-23 2008-08-27 L'Oreal Dispositif de pulvérisation d'une composition de brillance
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HUT70074A (en) 1995-09-28
CN1081195A (zh) 1994-01-26
MY131313A (en) 2007-08-30
WO1993023446A3 (fr) 1994-01-20
HU9403267D0 (en) 1995-02-28
MX9302865A (es) 1994-02-28
WO1993023446A2 (fr) 1993-11-25
CA2135186A1 (fr) 1993-11-25
NO944303D0 (no) 1994-11-11
AU4243393A (en) 1993-12-13
CZ277394A3 (en) 1995-08-16
FI945358A (fi) 1994-11-14
KR950701654A (ko) 1995-04-28
MA22892A1 (fr) 1993-12-31
BR9306363A (pt) 1998-06-30
TR28139A (tr) 1996-03-01
SK136194A3 (en) 1995-08-09
JPH07508060A (ja) 1995-09-07
FI945358A0 (fi) 1994-11-14
AU677005B2 (en) 1997-04-10
NO944303L (no) 1995-01-13

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