WO1995031173A1 - Compositions de soin pour les cheveux contenant une double dispersion d'un agent conditionneur au polysiloxane et d'un agent de brillance au polysiloxane - Google Patents

Compositions de soin pour les cheveux contenant une double dispersion d'un agent conditionneur au polysiloxane et d'un agent de brillance au polysiloxane Download PDF

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Publication number
WO1995031173A1
WO1995031173A1 PCT/US1995/004579 US9504579W WO9531173A1 WO 1995031173 A1 WO1995031173 A1 WO 1995031173A1 US 9504579 W US9504579 W US 9504579W WO 9531173 A1 WO9531173 A1 WO 9531173A1
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Prior art keywords
hair
shine
polysiloxane
agent
conditioning
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PCT/US1995/004579
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English (en)
Inventor
Thomas Sebastian Patterson
William Dale Murdock
Mark David Evans
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The Procter & Gamble Company
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Publication of WO1995031173A1 publication Critical patent/WO1995031173A1/fr

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    • 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
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/41—Particular ingredients further characterized by their size
    • A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns

Definitions

  • This invention relates to hair care compositions that provide conditioning and shine to the hair, through the use of polysiloxane hair conditioning agents and polysiloxane hair shine agents.
  • the shampooing of hair conventionally is performed utilizing any of numerous detersive surfactant-containing compositions known in the art. Whereas it is well known how to formulate shampoos that can efficiently clean the hair, substantial segments of consumers also want to condition their hair so that it is more manageable and has a softer feel. They also want their hair to look pleasing and healthy.
  • hair conditioning agents such as cationic, quaternary ammonium surfactants and polymers, silicone fluids, and hydrocarbons and other organic oils (e.g. fatty esters, fatty alcohols).
  • hair shine agents such as shellac, high refractive index silicones (e.g. phenylated dimethicone), and organic oils.
  • the effect of hair shine actives is to increase the amount of light reflecting off the hair surface.
  • Hair shine can be defined as the contrast between the specular and diffuse light reflected off the hair fibers. This contrast creates a perception of "sheen” or "gloss" strongly associated by the consumer with healthy hair.
  • high refractive index silicones can be quite effective at enhancing shine, they are generally not as effective as would be desired for conditioning the hair
  • Low refractive index polysiloxanes e.g. dimethicone
  • Cationic surfactants provide good wet hair conditioning, but are generally not as effective as dimethicone for providing dry hair conditioning.
  • Some hair care ingredients are effective at both conditioning and enhancing shine. These include hydrocarbon oils and fatty esters.
  • hair care compositions which can provide both excellent hair conditioning, particularly dry hair conditioning, and hair shine from a single composition.
  • the invention hereof can comprise, consist of, or consist essentially of the essential elements described herein as well as any of the preferred or optional ingredients also described herein.
  • a hair care composition that comprises:
  • a dispersed hair conditioning component comprising from about 0.01 % to about 10%, by weight of the composition, of a nonvolatile, insoluble polysiloxane fluid, said polysiloxane fluid having a viscosity at 25°C of at least about 5,000 centipoise, and said hair conditioning component having a refractive index of less than 1.48;
  • a dispersed hair shine component comprising from about 0.005% to about 5%, by weight of the composition, of a nonvolatile, insoluble polysiloxane fluid, said hair shine component having a refractive index of 1.48 or more;
  • compositions and methods of the present invention are advantageous for utilization in connection with a wide variety of hair care products including but not limited to leave-on compositions, such as hair lotions, tonics, gels, mousses, sprays, etc., as well as rinse-off compositions, such as shampoos and hair conditioning rinses.
  • leave-on compositions such as hair lotions, tonics, gels, mousses, sprays, etc.
  • rinse-off compositions such as shampoos and hair conditioning rinses.
  • the present invention including various optional and preferred embodiments thereof, is described in more detail below.
  • Insoluble in reference to a particular ingredient, refers to insolubility in the product composition unless otherwise specifically indicated.
  • nonvolatile means the material referred to exhibits very low or no significant vapor pressure at ambient conditions, as well-known and understood in the art.
  • the nonvolatile materials hereof will generally exhibit no more than 0.2mm Hg at 25°C and one atmosphere.
  • the nonvolatile materials hereof will also o generally have a boiling point at one atmosphere of at least 275 C, preferably at least 300°C.
  • polysiloxane fluid encompasses all such fluids, including the high molecular weight, high viscosity polysiloxanes commonly referred to as polysiloxane “gums”, which are further described below.
  • compositions hereof will contain a hair shine component, dispersed in the composition, which comprises a nonvolatile, insoluble, high refractive index polysiloxane fluid as a hair shine agent.
  • the hair shine component may further comprise other ingredients that are compatible with the hsir shine agent, such as a spreading agent or diluent.
  • the polysiloxane fluid-containing hair shine component includes the polysiloxane fluids present, as well as any additional ingredients present in the same dispersed phase of the composition.
  • compatible what is meant is that the ingredients can stably coexist in the same phase, such as by being soluble or miscible.
  • compositions hereof will comprise from about 0.005% to about 5%, by weight, of such hair shine component, preferably from about 0.01 % to about 3%, more preferably from about 0.1 % to about 3%, most preferably from about 0.2% to about 2%.
  • the level of the high refractive index polysiloxane hair shine agent will also preferably be within the above ranges.
  • the hair shine component, as well as the hair shine agent will have a refractive index of 1.48 or more, preferably at least about 1.50, more preferably at least about 1.52.
  • the refractive index will generally be about 1.70 or less, preferably about 1.60 or less, more preferably about 1.56 or less, most preferably about 1.54 or less.
  • Refractive index refers to the change in direction (i.e. apparent bending) of a light ray passing from one medium to another.
  • Refractive index shall herein refer to the light ray passing from air to a polysiloxane fluid, hair shine component, or hair conditioning component.
  • Refractive index of a polysiloxane fluid hair shine component can be determined using standard equipment commonly available and know in the art, such as an Abbe refractometer. Techniques for measuring refractive index are described, for example, in the Handbook of Chemical Microscopy, Volume I - Chemical Methods and Inorganic Qualitative Analysis, Chemot and Mason, ed., John Wiley & Sons, Inc., New York, 1958, pp 311-334.
  • the polysiloxane fluid hair shine component for use herein will generally have an average viscosity of at least about 10 centipoise at 25°C, preferably from about 50 to about 1,000,000 centipoise, more preferably from about 100 to about 100,000 centipoise, more preferably from about 200 to about 50,000 centipoise, most preferably from about 500 to about 10,000 centipoise.
  • the average viscosity can be measured by means of a glass capillary viscometer as set forth in Dow Corning Corporate Test Method CTM0004, July 20, 1970. Viscosity above or below these ranges can be used in the present invention as long as the other requirements and objects of the invention are met.
  • polysiloxane fluid suitable for purposes hereof includes those represented by general Formula (I):
  • each R independently is substituted or unsubstituted aliphatic (e.g. alkyl or alkenyl), aryl, aryloxy, alkaryl, alkoxy, alkamino (e.g. alkyl or alkenyl amino groups), hydroxy, or hydrogen, or combinations thereof; and n is an integer of at least about 1 , preferably from about 1 to about 10,000, more preferably from about 1 to about 1 ,000.
  • the R substituents can also include combinations of ether groups, hydroxy groups, and amine groups, as well as other functional groups, such as halogens and halogen-substituted functionalities, e.g. halogen-substituted aliphatic and aryl groups.
  • the polysiloxane fluid can be cyclic or linear. Linear polysiloxanes are exemplified above by Formula I. Branched chain can also be used. Cyclic polysiloxanes include those represented by Formula (II):
  • n is from 3 to 7, preferably from 3 to 5.
  • the substituents on the siloxane chain (R) may have any structure as long as the resulting polysiloxanes remain fluid at room temperature, are hydrophobic, are neither irritating, toxic nor otherwise harmful when applied to the hair, are compatible with the other components of the composition, are chemically stable under normal use and storage conditions, are capable of being deposited on the hair, and the resulting polysiloxane fluid has a refractive index as set forth above.
  • Preferred alkyl and alkenyl substitutes are C-.-C5 alkyls and alkenyls, more preferably from C 1 -C 4 , most preferably from C ⁇ -C ⁇
  • the aliphatic portions of other alkyl-, alkenyl-, or alkynyl- containing groups can be straight or branched chains and preferably have from one to five carbon atoms, more preferably from one to four carbon atoms, even more preferably from one to three carbon atoms, most preferably from one to two carbon atoms.
  • the R substituents hereof can also, contain amino functionalities, e.g., alkamino groups, which can be primary, secondary or tertiary amines or quaternary ammonium. These include mono-, di-, and tri- alkylamino and alkoxyamino groups wherein the aliphatic portion chain length is preferably as described above.
  • the R substituents can also be substituted with other groups, such as halogens (e.g. chloride, fluoride, and bromide), halogenated aliphatic or aryl groups, and hydroxy (e.g. hydroxy substituted aliphatic groups).
  • Suitable halogenated R groups could include, for example, t -halogenated (preferably fluoro) 8
  • High refractive index polysiloxane are available commercially from General Electric Silicones (Waterford, New York, U.S.A.), Dow Corning Corporation (Midland, Michigan, U.S.A.), Huls America (Piscataway, New Jersey, U.S.A.).
  • the high refractive index polysiloxanes that are used as the hair shine agents herein provide the hair with an enhanced shinny appearance.
  • Specular reflectance is a useful means for measuring shininess of hair. In general, specular reflectance refers to the fraction, or percentage, of incident light reflected from a surface in the mirror direction (i.e.
  • Specular reflectance that is measured from a coating of the compositions hereof on a collagen-coated black ceramic plate correlates with shininess of hair. Specular reflectance on such collagen-coated black ceramic plates for purposes of the present invention may be determined according to the procedure as described below and set forth in the Experimental section, referred to herein as "Glossmeter Specular Reflectance.” In general, Glossmeter Specular Reflectance (“GSR”) is measured as follows. A 1.0% solution is prepared using the high refractive index polysiloxane fluid hair shine component. The same solvent or diluent used in the composition, if any, for the hair shine agent is used to dilute the 1.0% solution.
  • cyclomethicone should be used to prepare the 1.0% solution. If necessary for solubility or miscibility purposes, cyclomethicone/ethanol solutions can be used to form the 1.0% solution for purposes of the GSR test.
  • the test solution is deposited on a collagen-coated, black ceramic tile and allowed to dry. Specular reflectance is measured with a spectrophotometer suitable for measuring specular reflectance from flat surfaces, e.g. a glossmeter. Suitable glossmeters are commercially available and known in the art. These include the "micro-gloss" glossmeter available from BYK-Gardner, Ind., 7
  • 1 1 alkyl groups such as -R -C(F) 3 , wherein R is C ⁇ Cg alkyl.
  • examples of such polysiloxanes include polymethyl -3,3,3 trifluoropropylsiloxane.
  • the high refractive index polysiloxane fluids hereof will generally contain aryl-containing R substituents at a sufficient level to increase the refractive index to the desired level.
  • Aryl-containing substituents contain alicyclic and heterocyclic five and six membered aryl rings, and substituents containing fused five or six membered rings.
  • the aryl rings themselves can be substituted or unsubstituted.
  • Substituents include aliphatic substituents, and can also include alkoxy substituents, acyl substituents, ketones, halogens (e.g., Cl and Br), amines, etc.
  • Exemplary aryl-containing groups include sub ⁇ stituted and unsubstituted arenes, such as phenyl, and phenyl derivatives such as phenyls with C..-Cc alkyl or alkenyl substituents, e.g., allylphenyl, methyl phenyl and ethyl phenyl, vinyl phenyls such as styrenyl, and phenyl alkynes (e.g. phenyl C 2 -C 4 alkynes).
  • Heterocyclic aryl groups include substituents derived from furan, imidazole, pyrrole, pyridine, etc.
  • Fused aryl ring substituents include, for example, napthalene, coumarin, and purine.
  • the high refractive index polysiloxane fluids hereof will have a degree of aryl-containing substituents of at least about 15%, preferably at least about 20%, more preferably at least about 25%, even more preferably at least about 35%, most preferably at least about 50%.
  • the degree of aryl substitution will be less than about 90%, more generally less than about 85%, preferably from about 55% to about 80%.
  • the high refractive index polysiloxane fluids may also be characterized by relatively high surface tensions as a result of their aryl substitution.
  • the polysiloxane fluids hereof will have a
  • the preferred polysiloxane fluids hereof will have a combination of phenyl or phenyl derivative substituents (preferably phenyl), with alkyl substituents, preferably C..-C ., alkyl (most preferably methyl) hydroxy,
  • the hair shine component hereof should provide an increase (" ⁇ ") in Glossmeter Specular Reflectance relative to the control of at least about ⁇ 1.0% (based on 100% of the original light intensity) preferably at least about ⁇ 5%, more preferably at least about ⁇ 10%, more preferably at least about ⁇ 20%, most preferably at least about ⁇ 30%.
  • the hair shine component in the compositions of the present invention optionally, and preferably, comprise a compatible nonvolatile spreading agent for the high refractive index polysiloxane fluid.
  • nonvolatile is as defined previously herein.
  • compatible what is meant is that the spreading agent is soluble in, dispersible in, or miscible with the high refractive index polysiloxane fluid, such that these two components can remain intermixed in the same phase of the composition.
  • the spreading agent and the polysiloxane fluid form a mixture wherein the spreading agent reduces the Surface Tension of the polysiloxane fluid.
  • compositions hereof preferably contain a sufficient amount of the spreading agent to reduce the Surface Tension of the high refractive index polysiloxane fluid, or the polysiloxane-containing hair shine component, by at least about 5%, preferably at least about 10%, more preferably at least about 15%, even more preferably at least about 20%, most preferably at least about 25%.
  • Reductions in Surface Tension of the high refractive index polysiloxane fluid/spreading agent mixture can result in improved shine enhancement of the hair.
  • the spreading agent will also preferably reduce the Surface
  • the 2 product is preferably 30 dynes/cm or less, more preferably about 28 2 2 dynes/cm or less most preferably about 25 dynes/c or less.
  • the Surface Tension will be in the range of from about 15 to about 30, more typically from about 18 to about 28, and most generally from about 2 20 to about 25 dynes/cm . Changes in Surface Tension can be measured according to the above test method or according to ASTM
  • the hair shine component also preferably contains a sufficient amount of the spreading agent to increase the Glossmeter Specular
  • delta 1.0% Reflectance by at least about “delta 1.0%” (hereinafter “ ⁇ 1.0%”, wherein delta refers to a change in percentage specular reflectance based upon
  • Glossmeter Specular Reflectance is at least about ⁇ 2.0%, more preferably at least about ⁇ 5.0%, even more preferably at least about ⁇ 7.5%, most preferably at least about ⁇ 10.0%.
  • the weight ratio of the high refractive index polysiloxane fluid to the spreading agent will preferably be between about 1000:1 and about 1 :10, preferably between about 100:1 and about 1 :1 , more preferably between about 50:1 and about 2:1, most preferably from about 25:1 to about 2:1.
  • the ratio is particularly preferred for the ratio to be between about 10:1 and about 2:1.
  • fluorinated surfactants particularly high refractive index polysiloxane: spreading agent ratios may be effective due to the efficiency of these surfactants.
  • ratios significantly above 1000:1 may be used.
  • Preferred spreading agents for use herein include silicone resins, and surfactants, which include both polyether siloxane copolymers and non-silicone-containing organic surfactants.
  • Especially preferred spreading agents are the silicone resins.
  • Silicone resins are highly crosslinked polymeric siloxane systems.
  • the crosslinking is introduced through the incorporation of trifunctional and tetrafunctional silanes with monofunctional or difunctional monomer units, or both, during manufacture of the silicone resin.
  • the degree of crosslinking that is required in order to result in a silicone resin will vary according to the specific silane units incorporated into the silicone resin.
  • silicone materials which have a sufficient level of trifunctional and tetrafunctional siloxane monomer units (and hence, a sufficient level of crosslinking) such that they dry down to a rigid, or hard, film are considered to be silicone resins.
  • the ratio of oxygen atoms to silicon atoms is indicative of the level of crosslinking in a particular silicone material.
  • Silicone resins will generally have at least about 1.1 oxygen atoms per silicon atom. Preferably, the ratio of oxygen:silicon atoms is at least about 1.2:1.0.
  • Typical silanes used in the manufacture of silicone resins are monomethyl-, dimethyl-, monophenyl-, diphenyl-, methylphenyl-, monovinyl-, and methylvinyl-chlorosilanes, and tetrachlorosilane.
  • Preferred resins are the methyl substituted silicone resins, such as those offered by General Electric as GE SS4230 and SS4267. Commercially available silicone resins will generally be supplied in an unhardened form in a low viscosity volatile or, preferably, nonvolatile silicone fluid.
  • silicone resins for use herein will be present in the compositions hereof in non-hardened form rather than as a hardened resin, as will be readily apparent to those skilled in the art.
  • Background material on silicones including sections discussing silicone fluids, gums, and resins, as well as manufacture of silicones, can be found in Encyclopedia of Polymer Science and Engineering, Volume 15, Second Edition, pp 204-308, John Wiley & Sons, Inc., 1989, and Chemistry and Technology of Silicones, Walter Noll, Academic Press, Inc. (Harcourt Bruce Javanovich, Publishers, New York), 1968, pp 282-287 and 409-426, both incorporated herein by reference.
  • Silicone materials and silicone resins in particular can conveniently be identified according to a shorthand nomenclature system well known to those skilled in the art as "MDTQ" nomenclature. Under this system, the silicone is described according to presence of various siloxane monomer units which make up the silicone. Briefly, the symbol M denotes the monofunctional unit (CH3)3SiO)o.5, D denotes the difunctional unit (CH3)2SiO; T denotes the trifunctional unit (CH3)Sr-j 5; and Q denotes the quadri- or tetra-functional unit Si ⁇ 2- Primes of the unit symbols, e.g., M', D', T, and Q' denote substituents other than methyl, and must be specifically defined for each occurrence.
  • MDTQ the symbol M denotes the monofunctional unit (CH3)3SiO)o.5
  • D denotes the difunctional unit (CH3)2SiO
  • T denotes the trifunctional unit (CH3)Sr-j 5
  • Typical alternate substituents include groups such as vinyl, phenyls, amines, hydroxyls, etc.
  • the molar ratios of the various units either in terms of subscripts to the symbols indicating the total number of each type of unit in the silicone (or an average thereof) or as specifically indicated ratios in combination with molecular weight complete the description of the silicone material under the MDTQ system.
  • Higher relative molar amounts of T, Q, T and/or Q' to D, D', M and/or or M' in a silicone resin is indicative of higher levels of crosslinking.
  • the overall level of crosslinking can also be indicated by the oxygen to silicon ratio.
  • silicone resins for use herein which are preferred are MQ,
  • the preferred silicone substituent is methyl.
  • MQ resins particularly those wherein the M:Q molar ratio is from about 0.5:1.0 to about 1.5:1.0 and the average molecular weight of the resin is from about 500 to about 10,000, generally from about 1 ,000 to about 10,000.
  • Surfactants that are compatible with the high refractive index polysiloxane fluid hereof and which is suitable for application to the hair can also be used as spreading agents.
  • the surfactants can be anionic, cationic, nonionic, or amphoteric or a combination thereof.
  • Surfactants can also be utilized for other purposes that are known in the art.
  • anionic, nonionic, amphoteric, and zwitterionic surfactants can be used as cleansing agents and emulsifying agents.
  • Cationic surfactants can be used as conditioning agents.
  • a wide variety of surfactants suitable for use herein are further described in the nonlimiting disclosure below.
  • Polvether Siloxane Copolvmer Polyether siloxane copolymers or silicone "copolyols" as they are sometimes referred to, are silicone-containing surfactants that can be utilized as spreading agents for the polysiloxane fluid, for emulsifying agents for polysiloxane fluids, or for conditioning agents for the hair.
  • Silicone copolyols are surfactants characterized by a hydrophobic polysiloxane chain and a hydrophilic alkoxy portion.
  • Silicone copolyols which may be used include polyalkylene oxide modified polydimethylsiloxanes of the following formulae: and
  • Silicone copolyols among those useful herein are also disclosed in the following patent documents, all incorporated by reference herein: U.S. Patent 4,122,029, Geen, et al., issued October 24, 1978; U.S. Patent 4,265,878, Keil, issued May 5, 1981 ; and U.S. Patent 4,421 ,769, Dixon, et al., issued December 20, 1983.
  • Such silicone copolyol materials are also disclosed, in hair compositions, in British Patent Application 2,066,659, Abe, published July 15, 1981 (incorporated by reference herein) and Canadian Patent 727,588, Kuehns, issued February 8, 1966 (incorporated by reference herein).
  • silicone copolyols which can be used herein, include Silwet Surface Active Copolymers (manufactured by the Union Carbide Corporation); and Dow Corning Silicone Surfactants (manufactured by the Dow Corning Corporation).
  • Silwet Surface Active Copolymers manufactured by the Union Carbide Corporation
  • Dow Corning Silicone Surfactants manufactured by the Dow Corning Corporation
  • non-silicone- containing organic surfactants can also be used in the present invention. A wide variety are described below.
  • Anionic surfactants useful herein include alkyl and alkyl ether sulfates. These materials typically have the respective formulae ROSO 3 M and RO(C 2 H 4 O) ⁇ SO 3 M, 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.
  • R alkyl or alkenyl of from about 10 to about 20 carbon atoms
  • x is 1 to 10
  • M is a water-soluble cation such as ammonium, sodium, potassium and triethanolamine.
  • Another suitable class of anionic surfactants are the water-soluble salts of the organic, sulfuric acid reaction products of the general formula:
  • R 1 -S0 3 -M wherein R 1 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.
  • R 1 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.
  • Important examples are the 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., S0 3 , H2S0 4 , oleum, obtained according to known sulfonation methods, including bleaching and hydrolysis.
  • alkali metal and ammonium sulfonated n-paraffins Preferred are alkali metal and ammonium sulfonated n-paraffins.
  • Additional examples of anionic 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 surfactants of this variety are set forth in U.S. Patents 2,486,921; 2,486,922; and 2,396,278.
  • anionic surfactants include the class designated as succinamates. This class includes such surface active agents as disodium N-octadecylsulfosuccinamate; tetrasodium
  • N-(1 ,2-dicarboxyethyl)-N-octadecylsulfosuccinamate N-(1 ,2-dicarboxyethyl)-N-octadecylsulfosuccinamate; diamyl ester of sodium sulfosuccinic acid; dihexyl ester of sodium sulfosuccinic 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 uncomplexed 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 a-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 b-alkyloxy alkane sulfonates.
  • anionic surfactants include N-acyl amino acid surfactants and salts thereof (alkali, alkaline earth, and ammonium salts) such as those represented by the Formula
  • R 1 is a C8-C24 alkyl or alkenyl radical, preferably C10-C18' R ⁇ is -H, C1-C4 alkyl, phenyl, or -CH2COOM, preferably C1-C4 alkyl, more preferably C1-C2 alkyl;
  • R 3 is -CR 4 2- or C1-C2 alkoxy, wherein each R 4 independently is -H or C ⁇ -CQ alkyl or alkylester, and n is from 1 to 4, preferably 1 or 2; and M is -H or a salt-forming cation as described above, preferably an alkali metal such as sodium or potassium.
  • N-acyl acid surfactants A wide variety of N-acyl acid surfactants and their synthesis are described in Anionic Surfactants, Part II, Surfactant Science Series, Vol. VII, edited by Warner M. Linfield, Marcel Dekker, Inc. (New York and Basel), 1976; pp 581-617.
  • N-acyl sarcosinates which are known as the N-acyl sarcosinates, and acids thereof.
  • Specific examples include lauroyl sarcosinate, myristoyl sarcosinate, cocoyl sarcosinate, and oleoyl sarcosinate, preferably in their sodium and potassium salt forms.
  • Another common anionic surfactant includes the water soluble soaps, e.g., salts of C10-C20 fatty acids, such as coconut-and tallow- based soaps. Preferred salts are ammonium, potassium, and sodium salts.
  • Nonionic Surfactants include the water soluble soaps, e.g., salts of C10-C20 fatty acids, such as coconut-and tallow- based soaps. Preferred salts are ammonium, potassium, and sodium salts.
  • Nonionic surfactants can be broadly defined as compounds produced by the condensation of alkylene oxide groups (hydrophilic in nature) with a hydrophobic compound, which may be aliphatic or alkyl aromatic in nature. Examples of preferred classes of nonionic surfactants are:
  • the polyethylene oxide condensates of alkyl phenols, e.g., the condensation products of alkyl phenols having an alkyl group containing from about 6 to about 20 carbon atoms in either a straight chain or branched chain configuration, with ethylene oxide, the said ethylene oxide being present in amounts equal to from about 10 to about 60 moles of ethylene oxide per mole of alkyl phenol.
  • ethylene oxide e.g., a coconut alcohol ethylene oxide condensate having from about 10 to about 30 moles of ethylene oxide per mole of coconut alcohol, the coconut alcohol fraction having from about 10 to about 14 carbon atoms.
  • R 1 R 2 R 3 N > O wherein R ⁇ 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 R 2 and R 3 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 represents a semipolar bond).
  • R contains an alkyl, alkenyl or monohydroxyalkyi 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 monohydroxyalkyi groups containing from about 1 to about 3 carbon atoms.
  • the arrow in the formula represents a semipolar bond.
  • sucrose esters of fatty acids Such materials are described in U.S. Patent 3,480,616, e.g., sucrose cocoate (a mixture of sucrose esters of a coconut acid, consisting primarily of monoesters, and sold under the tradenames GRILLOTEN LSE 87K from RITA, and CRODESTA SL-40 from Croda).
  • Alkyl polysaccharide nonionic surfactants are disclosed in U.S. Patent 4,565,647, Llenado, issued January 21 , 1986, having a hydrophobic group containing from about 6 to about 30 carbon atoms, preferably from about 10 to about 16 carbon atoms and a polysaccharide, e.g., a polyglycoside, hydrophilic group.
  • the polysaccharide can contain from about 1.0 to about 10, preferably from about 1.3 to about 3, most preferably from about 1.3 to about 2.7 saccharide units.
  • Any reducing saccharide containing 5 or 6 carbon atoms can be used, e.g., glucose, galactose and galactosyl moieties can be substituted for the glucosyl moieties.
  • the hydrophobic group is attached at the 2-, 3-, 4-, etc. positions thus giving a glucose or galactose as opposed to a glucoside or galactoside.
  • the intersaccharide bonds can be, e.g., between the one position of the additional saccharide units and the 2-, 3-, 4-, and/or 6-positions on the preceding saccharide units.
  • the alkyl group preferably contains up to about 3 hydroxy groups and/or the polyalkyleneoxide chain can contain up to about 10, preferably less than 5, alkylene moieties.
  • Suitable alkyl polysaccha des are octyl, nonyldecyl, undecyldodecyl, t decyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl, di-, tri-, tetra-, penta-, and hexaglucosides, galactosides, lactosides, glucoses, fructosides, fructoses and/or galactoses.
  • Polyethylene glycol (PEG) glyceryl fatty esters as depicted by the formula RC(0)OCH 2 CH(OH)CH 2 (OCH 2 CH 2 ) n OH wherein n is from about 5 to about 200, preferably from about 20 to about 100, more preferably from about 30 to about 85, and RC(O)- is an ester wherein R comprises an aliphatic radical having from about 7 to 19 carbon atoms, preferably from about 9 to 17 carbon atoms, more preferably from about 11 to 17 carbon atoms, most preferably from about 11 to 14 carbon atoms.
  • R comprises an aliphatic radical having from about 7 to 19 carbon atoms, preferably from about 9 to 17 carbon atoms, more preferably from about 11 to 17 carbon atoms, most preferably from about 11 to 14 carbon atoms.
  • the combinations of n from about 20 to about 100, with esters . f° r minimized adverse effect on foaming, is preferred.
  • surfactants that can be used include the C10-C18 N- alkyl (Ci-C ⁇ ) polyhydroxy fatty acid amides. Typical examples include the C12-C18 N-methylglucamides. See WO 9,206,154 and US Patent 5,194,639, incorporated herein by reference.
  • Other sugar-derived surfactants include the N-alkoxy polyhydroxy fatty acid amides, such as C-
  • Cationic Surfactants include the C10-C18 N- alkyl (Ci-C ⁇ ) polyhydroxy fatty acid amides. Typical examples include the C12-C18 N-methylglucamides. See WO 9,206,154 and US Patent 5,194,639, incorporated herein by reference.
  • Other sugar-derived surfactants include the N-alk
  • 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, Detergents & 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.
  • quaternary ammonium-containing cationic surfactant materials useful herein are those of the general formula:
  • R1-R4 are independently an aliphatic group of from about 1 to about 22 carbon atoms, or an aromatic, alkoxy, polyoxyalkylene, alkylamido, hydroxyalkyl, aryl or alkylaryl group having from about 12 to about 22 carbon atoms; and X is an anion selected from halogen, acetate, phosphate, nitrate and alkylsulfate radicals.
  • 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 e.g., those of about 12 carbons, or higher, can be saturated or unsaturated.
  • 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 amino 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, Nachtigal, et al., issued June 23, 1981 , incorporated by reference herein.
  • 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.
  • amphoteric surfactant hereof include the imidazolinium amphoteric surfactants such as those depicted by the Formula:
  • R 4 R2 wherein R1 is C8-C22 alkyl or alkenyl, preferably C12-C16' R ⁇ ' s hydrogen or CH2CO2M, R 3 is CH 2 CH 2 OH or CH 2 CH 2 OCH2CH COOM, R 4 is hydrogen, CH 2 CH 2 OH, or CH 2 CH 2 OCH 2 CH2COOM, Z is C0 2 M or CH2CO2M, n is 2 or 3, preferably 2, M is hydrogen or a cation, such as alkali metal, alkaline earth metal, ammonium, or alkonol ammonium.
  • Suitable materials of this type are marketed under the tradename MIRANOL and are understood to comprise a complex mixture of species, and can exist in protonated and non-protonated species depending upon pH with respect to species that can have a hydrogen at R2.
  • the imidazolinum amphoteric surfactant hereof can be derived via an imidazolinium intermediate. However, it will be recognized by thosed in the art that it needn't necessarily be derived via an imidazolinium.
  • Preferred amphoteric surfactants of are monocarboxylates and dicarboxylates.
  • these materials include cocoamphocarboxypropionate, cocoamphocarboxypropionic acid, cocoamphocarboxyglycinate (alternately referred to as cocoamphodiacetate), and cocoamphoacetate.
  • Specific commercial products providing the imidazolinium derivative component of the present compositions include those sold under the trade names MIRANOL C2M CONC. N.P., MIRANOL C2M CONC. O.P., MIRANOL C2M SF, MIRANOL CM SPECIAL (Miranol, Inc.); ALKATERIC 2CIP (Alkaril Chemicals); AMPHOTERGE W-2 (Lonza, Inc.); MONATERIC CDX-38, MONATERIC CSH-32 (Mona Industries); REWOTERIC AM-2C (Rewo Chemical Group); and SCHEROTERIC MS- 2 (Scher Chemicals).
  • Amphoteric surfactants also include aminoalkanoates of the formula:
  • R-N [(CH 2 ) m COOM]2 and mixtures thereof; wherein n and m are numbers from 1 to 4, R is Cs- C22 alky' or alkenyl, and M is hydrogen, alkali metal, alkaline earth metal, ammonium or alkanolammonium.
  • amphoteric surfactants include n- alkylaminopropionates and n-alkyliminodipropionates. Such materials are sold under the tradename DERIPHAT by Henkel and MIRATAINE by Miranol, Inc. Specific examples include N-lauryl-beta-amino propionic acid or salts thereof, and N-lauryl-beta-imino-dipropionic acid or salts thereof.
  • Zwitterionic surfactants can be considered as amphoteric surfactants exemplified by those which are broadly described as derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, in which the aliphatic radicals 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.
  • a general formula for these compounds is:
  • R2 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 selected from the group consisting of nitrogen, phosphorus, and sulfur atoms
  • R3 is an alkyl or monohydroxyalkyi 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
  • R4 is an alkylene or hydroxyalkylene of from about 1 to about 4 carbon atoms
  • Z is a radical selected from the group consisting of carboxylate, sulfonate, sulfate, phosphonate, and phosphate groups.
  • Zwitterionics include, for example, betaines.
  • betaines include the high alkyl betaines, such as coco dimethyl carboxymethyl betaine, lauryl dimethyl carboxymethyl betaine, lauryl dimethyl alphacarboxyethyl 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-hydroxyethyl) sulfopropyl betaine and the like; amidobetaines and amidosulfobetaines, wherein the RCONH(CH 2 ) 3 radical is attached to the nitrogen atom of the betaine are also useful in this invention.
  • compositions hereof will also contain a hair conditioning component dispersed in the composition which comprises from about 0.01 % to about 10%, by weight of the composition, preferably from about 0.05% to about 5%, more preferably from about 0.5% to about 3%, of a nonvolatile, insoluble polysiloxane fluid as the hair conditioning agent.
  • a hair conditioning component dispersed in the composition which comprises from about 0.01 % to about 10%, by weight of the composition, preferably from about 0.05% to about 5%, more preferably from about 0.5% to about 3%, of a nonvolatile, insoluble polysiloxane fluid as the hair conditioning agent.
  • the level of the dispersed hair conditioning component, as a whole will also generally fall within the above ranges.
  • the polysiloxane-containing hair conditioning component and preferably the polysiloxane hair conditioning agent therein will have a refractive index of less than 1.48, preferably about 1.46 or less, more preferably from about 1.40 to about 1.45, most preferably from about 1.42 to about 1.44.
  • the polysiloxane hair conditioning agent, and preferably the hair conditioning component will also have an average viscosities at 25°C of at least about 5,000 centipoise, preferably from about 50,000 to about 5,000,000 centipoise, more preferably from about 75,000 to about 2,000,000 centipoise, most preferably from about 100,000 to about 1 ,500,000 centipoise. Viscosity can be measured as previously described.
  • the polysiloxane fluid hair conditioning agent can have other ingredients in the same dispersed phase, e.g., silicone resins (such as described above) to aid in disposition on the hair.
  • silicone resins such as described above
  • the combination of any such additional ingredients in the same dispersed phase as the polysiloxane fluid hair conditioning agent is referred to herein as the polysiloxane fluid- containing hair conditioning component.
  • the polysiloxane fluid can have a structure as set forth above under Formula I, except that the level of aryl substitution must be sufficiently low such that the refractive index is as described above.
  • the degree of aryl substitution will be less than about 15%, more preferably less than about 10%, even more preferably less than about 5%, most preferably zero percent.
  • the most preferred conditioning agent is polydimethylsiloxane.
  • Preferred hair conditioning agents are combinations of lower viscosity nonvolatile silicone fluids, having average viscosities at 25°C of about 50 to about 10,000 centipoise, more preferably from about 100 to about 1000 centipoise, and silicone gums having viscosities of greater than 1 ,000,000 centipoise, at 25°C.
  • the gums will generally, though not necessarily, have an average viscosity of from about 2,000,000 to about 10,000,000 centipoise at 25°C.
  • Solvent Depending upon the particular choice of spreading agent (if any) and high refractive index polysiloxane fluid, it may be necessary or desirable to incorporate an additional solvent in the hair shine component phase to ensure that the resin and polysiloxane fluid are compatible with one another.
  • the solvent has a refractive index below about 1.46, or is otherwise below the refractive index of the polysiloxane fluid, it may be desirable to use a solvent which is volatile (materials that exhibit greater than 0.2mmHg at 25° C and one atmosphere, generally with a boiling point of less than 275° C), so that it does not remain on the hair and potentially impair the shine performance obtained according to the present invention.
  • Suitable solvents include: cyclomethicone, other cyclic siloxanes such as those described herein as carrier fluids, linear polysiloxane polymers such as dimethicone, and other low viscosity analogues of the polysiloxane materials described in Formulas I and II, preferably having viscosity at 25°C of about 10 centistokes or less, such materials generally having lower (or zero) degree of aryl-containing substituents than the highly arylated, high refractive index polysiloxane of the present invention; volatile liquid hydrocarbons, such as straight or branched chain hydrocarbons having from about 4 to about 16 carbon atoms (e.g., hexane, isobutane, decane, dodecane, tetradecane, tridecane); lower alcohols (e.g.
  • C 2 -C 4 alcohols such as ethanol and isopropanol
  • hydrocarbon esters preferably with a total of about 10 carbon atoms or less (e.g. ethyl acetate); halogenated hydrocarbons (e.g. freon); volatile ketones (e.g. acetone); and mixtures thereof.
  • cyclomethicone Especially preferred is cyclomethicone.
  • the present invention does not, however, exclude the use of nonvolatile solvents for the resin/phenylated polysiloxane solvent.
  • solvents as described above will be used typically at a weight ratio of (solvent) to (highly arylated nonvolatile polysiloxane plus spreading agent) of up to about 100:1 , more typically up to about 50:1 , for rinse-off hair care products, preferably from about 2:1 to about 10:1 for hair rinse products.
  • high levels of volatile solvents may be used as carrier ingredients, as described later.
  • the polysiloxane-containing hair conditioning component and polysiloxane- containing hair shine component be dual dispersed in the composition.
  • the hair shine and hair conditioning components each exist in the composition as distinct, discontinuous phases.
  • the dispersed components will be present in the composition in the form of droplets.
  • distinct, discontinuous phases what is meant is that the droplets of the hair shine component and the droplets of the hair conditioning component exist in the composition as separate species of droplets. This has been found to be critical for providing conditioning with the unexpectedly improved hair shine.
  • intermixing of the components of the high refractive index hair shine agent and the lower refractive index hair conditioning agent to form a single type of droplet would result in shine performance that would be substantially degraded.
  • compositions of the present invention can be made by first preparing, or otherwise obtaining, separate dispersions of the polysiloxane hair shine agent and the polysiloxane hair conditioning agent, and then combining the two dispersions together, together with any additional ingredients, to form the final product.
  • Conventional methods known in the art for preparing premix dispersions may be utilized.
  • the dispersions will be in the form of emulsions, formulated by separately mixing the ingredients of the polysiloxane hair shine component and the ingredients of the polysiloxane hair conditioning component, respectively, in water with an emulsifying agent.
  • Suitable emulsifying agents include surfactants, including the anionic, nonionic, cationic, and amphoteric surfactants, and combinations thereof, as previously described.
  • surfactants including the anionic, nonionic, cationic, and amphoteric surfactants, and combinations thereof, as previously described.
  • anionic, amphoteric and nonionic surfactants are especially preferred.
  • anionic and nonionic surfactants are especially preferred.
  • alkyl and alkyl ethoxyglated sulfates are especially preferred.
  • the weight ratio of the surfactant to polysiloxane hair conditioning agent or polysiloxane hair shine agent in the premix dispersions is preferably from about 1 :30 to about 6:5, more preferably from about 1 :12 to about 1 :4 It is also contemplated to add soluble salts such as sodium chloride or other viscosity modifying agents to the premix, to thicken the surfactant phase and ease emulsification, particularly when viscous polysiloxanes are to be emulsified. In general, from about 0.01 % to about 10%, by weight of the premix, of such salts are used. In general, the level of water in the premixes will be from about 1 % to about 20%, preferably from about 5% to about 10%, by weight of the premix.
  • the weight average droplet size (diameter) in the dispersions hereof will generally be from about 0.1 microns to about 500 microns, preferably from about 2 microns to about 250 microns, more preferably from about 5 microns to about 100 microns, most preferably from about 5 microns to about 50 microns.
  • Carrier The compositions of the present invention will comprise an aqueous carrier for the hair shine agent and conditioning agent suitable for application to the hair.
  • the aqueous carrier will comprise water at a level of from about 50% to about 99.99%, by weight of the composition, generally from about 50% to about 99.98%, preferably from about 60% to about 95%, more preferably from about 70% to about 90%.
  • compositions used herein can include other fluids, as well as other carrier components suitable for application to the hair.
  • suitable for application to hair means that the carrier does not damage or negatively affect the aesthetics of hair and is safe for application to the hair and to skin.
  • the choice of appropriate carrier will also depend on the particular polysiloxane fluids to be used, and whether the product is meant to be left on the hair (e.g., hair spray, mousse, tonic) or to be rinsed off after use (e.g., shampoo, hair conditioning rinse).
  • Optional Ingredients e.g., hair spray, mousse, tonic
  • 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, in addition to the carrier, required or desirable to formulate such products vary with product type and can be routinely chosen by one skilled in the hair care product art. Additional Carrier Fluids
  • Suitable additional carrier fluids for use in the present invention include, but are not limited to, lower alcohols (e.g. C ⁇ -CQ) monohydhc alcohols, such as ethanol and isopropanol), hydrocarbons (such as isobutane, hexane, decene, acetone), halogenated hydrocarbons (such as Freon), linalool, and hydrocarbon esters (such as ethyl acetate, dibutyl phthalate).
  • lower alcohols e.g. C ⁇ -CQ
  • monohydhc alcohols such as ethanol and isopropanol
  • hydrocarbons such as isobutane, hexane, decene, acetone
  • halogenated hydrocarbons such as Freon
  • linalool and hydrocarbon esters (such as ethyl acetate, dibutyl phthalate).
  • a preferred component in the present composition is a suspending agent for suspending the polysiloxane hair shine component and polysiloxane hair conditioning components in the compositions.
  • suspending agents include crystalline suspending agents, gel vehicles, and other suspending and/or thickening agents.
  • Thickening agents may be added to aid in suspending the dispersed, insoluble phases in the aqueous carrier or to merely modify rheology, or both.
  • suspending agents, and thickeners are used at levels of from about 0.1% to about 10%, by weight, of the composition.
  • Gel vehicles can comprises two components: a lipid and a cationic surfactant. Suitable cationic surfactants are described in detail above. Gel 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.
  • Lipid gel vehicle materials are essentially water-insoluble, and contain hydrophobic and hydrophilic moieties. They include naturally or synthetically-derived acids, acid derivatives, 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.
  • Preferred lipids are esters, such as cetyl palmitate and glycerylmonostearate. 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.
  • Lipid vehicle materials among those useful herein are also dis ⁇ closed in Bailey's Industrial Oil and Fat Products. (3rd edition, D. Swern, ed., 1979), incorporated by reference herein. Fatty alcohols included among those useful herein are disclosed in the following documents, all incorporated by reference herein: U.S. Patent 3,155,591 , Spotifyr, issued November 3, 1964; U.S. Patent 4,165,369, Watanabe, et al., issued August 21 , 1979; U.S.
  • the lipid vehicle material is preferably present at from about 0.1 % to about 8.0% of the composition; the cationic surfactant gel vehicle material is preferable present at from about 0.05% to about 5.0% of the composition.
  • Suspending agents or thickeners for use in the compositions of the present invention, especially for hair rinses also 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 quaternary ammonium compounds (such as ditallowdimethyl ammonium chloride)
  • quaternary ammonium compounds such as ditallowdimethyl ammonium chloride
  • chelating agents such as EDTA
  • Crystalline suspending agents are preferred components for suspending the hair shine component and hair conditioning component, as well as other immiscible or particulate ingredients (e.g. insoluble, anti-static cationic surfactants which are anti-dandruff actives, such as zinc pyridinethione, selenium disulfite, ant the like).
  • a crystalline suspending agent is particularly preferred in pourable liquid formulations containing hair cleansing-effective amounts of detersive surfactants, such as shampoos.
  • suspending agents useful in the present compositions include any of several long chain acyl derivative materials or mixtures of such materials, such as long chain acyl derivatives, long chain amine oxides, and mixtures thereof, wherein such suspending agents are present in the composition in crystalline form.
  • These suspending agents are described in U.S. Patent 4,741 ,855, Grote and Russell, issued May 3, 1988, and U.S. Reissue Patent RE 34,584, Grote and Russell, issued April 12, 1994, both incorporated herein by reference. Included are ethylene glycol esters of fatty acids having from about 16 to about 22 carbon atoms.
  • Other crystalline suspending agents found useful are alkanol amides of fatty acids, having from about 16 to about 22 carbon atoms, preferably about 16 to 18 carbon atoms.
  • Preferred alkanol amides are stearic monoethanolamide, stearic diethanoiamide, stearic monoisopropanolamide and stearic monoethanolamide stearate.
  • long chain acyl derivatives include long chain esters of long chain fatty acids (e.g., stearyl stearate, cetyl palmitate, etc.); glyceryl esters (e.g., glyceryl distearate and poly(2-8)glyceryl distearate) and long chain esters of long chain alkanol amides (e.g., stearamide DEA distearate, stearamide MEA stearate).
  • long chain esters of long chain fatty acids e.g., stearyl stearate, cetyl palmitate, etc.
  • glyceryl esters e.g., glyceryl distearate and poly(2-8)glyceryl distearate
  • long chain esters of long chain alkanol amides e.g., stearamide DEA distearate, stearamide MEA stearate.
  • suspending agents are alkyl (C16-C22) dimethyl amine oxides such as stearyl dimethyl amine oxide. If the compositions contain an amine oxide or a long chain acyl derivative as a surfactant, the suspending function could also be provided by such surfactant and additional suspending agent may not be needed if the level of those materials are at least the minimum level given below.
  • Other crystalline long chain acyl derivatives that can be used include N,N-dihydrocarbyl amido benzoic acid and soluble salts thereof (e.g., Na and K salts), particularly N.N-di(hydrogenated) C-
  • the long chain acyl derivative materials when utilized as the suspending agent, are typically present in pourable, liquid formulations at a level of from about 0.1 % to about 5.0%, preferably from about 0.5% to about 3.0%.
  • the suspending agent serves to assist in suspending the silicone material and may give pearlescence to the product. Mixtures of suspending agents are also suitable for use in the compositions of this invention.
  • xanthan gum Another type of suspending agent that can be used is xanthan gum.
  • Compositions utilizing xanthan gum as a suspending agent for a silicone hair conditioning component are described in U.S. Patent 4,788,006, Bolich and Williams, issued November 29, 1988, incorporated herein by reference.
  • the gum, when used as the silicone hair conditioning component suspending agent, will typically be present in pourable, liquid formulations at a level of from about 0.3% to about 3%, preferably from about 0.4% to about 1.2% in the compositions of the present invention.
  • Combinations of long chain acyl derivatives and xanthan gum are disclosed as a suspending agent for silicone hair conditioners in U.S. Patent 4,704,272, Oh et al., issued November 3, 1987, incorporated herein by reference, and may also be used in the present compositions.
  • thickening agents include, for example, acrylates/C ⁇ ⁇ o-C30 acrylate crosspolymers.
  • a preferred type of product formulation of the present invention is a shampoo containing from about 1 % to about 35%, preferably from about 5% to about 30%, more preferably from about 8% to about 25%, most preferably from about 15% to about 22%, by weight, of a detersive surfactant selected from the group consisting of anionic surfactants, amphoteric surfactants, and nonionic surfactants.
  • the preferred shampoos will also contain a suspending agent for suspending the dispersed phases of the polysiloxane hair shine and conditioning agents in the shampoo.
  • crystalline suspending agents and combinations of crystalline suspending agents with other thickening agents are especially preferred. Suitable anionic, amphoteric, and nonionic surfactants for use as detersive surfactants herein have been described above. Conditioning Agents
  • compositions hereof may comprise additional conditioning agents, such as cationic surfactants and cationic polymers, organic oils and waxes such as hydrocarbon oils, and fatty acid esters, and alcohols.
  • Suitable cationic polymers include, for example, copolymers of vinyl monomers having cationic amine or quaternary ammonium functionalities with water soluble spacer monomers such as acrylamide, methacrylamide, alkyl and dialkyi acrylamides, alkyl and dialkyi methacrylamides, alkyl acrylate, alkyl methacrylate, vinyl caprolactone, and vinyl pyrrolidone.
  • the alkyl and dialkyi substituted monomers preferable have C ⁇ -Cy alkyl groups, more preferably C--C 3 alkyl groups.
  • suitable spacer monomers include vinyl esters, vinyl alcohol (made by hydrolysis of polyvinyl acetate), maleic anhydride, propylene glycol and ethylene glycol.
  • Other cationic polymers include cationic-modified polysaccharides, such as cationic ammonium modified cellulose. A variety of cationic surfactants are generally described above. Especially preferred are di(C-
  • compositions hereof can contain film forming polymers, i.e. adhesive polymers, to aid in styling or setting the hair.
  • Exemplary hair setting polymers include polyvinylpyrrolidone (PVP), particularly poly N-vinyl pyrrolidone, copolymers of PVP and methylmetharylate, copolymers of PVP and vinyl acetate (VA), and polyvinyl alcohol (PVA).
  • PVP polyvinylpyrrolidone
  • VA vinyl acetate
  • PVA polyvinyl alcohol
  • Exemplary hair setting polymers also include copolymers of VA and crotonic acid, copolymers of methylvinylether and maleic hemiesters (e.g. maleic ethyl ester and maleic butyl ester), hydroxypropyl cellulose, hydroxypropyl guar gum, polystyrene sulfonate salts, polyacrylic polymers such as polymers and copolymers of acrylic acid and methacrylic acid, co- and ter- polymers of acrylic acid and/or methacylic acid with acrylamide and/or vinyl pyrrolidone such as terpolymers of vinyl pyrrolidone/methyl methacrylate/methacrylic, terpolymers of vinyl pyrrolidone/ethylmethacrylate/methacrylic acid, terpolymers of t-butyl acrylamide/ethyl acrylate/acrylic acid, and terpolymers of VA/crotonic acid/vinyl
  • hair setting polymers are crotonic acid and a vinyl ester of an alpha-branched saturated aliphatic monocarboxylic acid such as vinyl neodecanoate; and copolymers of methyl vinyl ether and maleic anhydride (e.g. molar ratio about 1:1) wherein such copolymers are 50% esterfied with a saturated aliphatic alcohol containing from 1 to 4 carbon atoms such as ethanol or butanol; and acrylic copolymers and te ⁇ olymers containing acrylic acid or methacrylic acid as the anionic radical-containing moiety such as copolymers with, butyl acrylate, ethyl methacrylate, etc.
  • Polymeric hair setting polymers also include amphoteric polymers.
  • amphoteric polymers One class of amphoteric polymers that can be used are acrylic resins with both cationic and carboxylic groups. Examples include terpolymers of octyl and acrylamide/acrylic acid/ butylaminoethyl methacrylate, copolymers of acrylic acid/betaine methacrylate, and copolymers of octylacrylamide/acrylates.
  • Silicone-containing adhesive copolymers can also be used as hair setting polymers, such as those containing polysiloxane-containing monomers and non-polysiloxane-containing monomers, wherein the polymer has a weight average molecular weight of at least about 20,000, and comprises from about 1 % to about 50%, by weight, of the poly ⁇ siloxane-containing monomers.
  • the silicone-containing polymers can comprise an organic backbone, especially a carbon backbone such as a vinyl polymeric backbone, with 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, grafted to the backbone.
  • Organic backbones contemplated include those that are derived from polyme zable, ethylenically unsaturated monomers. These include vinyl monomers, and other condensation monomers (e.g., those that polymerize to form polyamides and polyesters) and ring-opening monomers (e.g., ethyl oxazoline and caprolactone).
  • the preferred polymehzable polysiloxane-containing monomer (C monomer) can be exemplified by the general formula: X ' Y >n Si ⁇ R >3-m Z m wherein X is a vinyl group copolymerizabie with the A and B monomers;
  • Y is a divalent linking group
  • R is a hydrogen, hydroxyl, lower alkyl (e.g.
  • n is a monovalent siloxane polymeric moiety having a number average molecular weight of at least about 500, is essentially unreactive under copolymerization conditions, and is pendant from the vinyl polymeric backbone described above; n is a monovalent siloxane polymeric moiety having a number average molecular weight of at least about 500, is essentially unreactive under copolymerization conditions, and is pendant from the vinyl polymeric backbone described above; n is
  • n 0 or 1 ; and m is an integer from 1 to 3.
  • 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 mica, mother of pearl, ethylene glycol distearate preservatives, such as benzyl alcohol, methyl paraben, propyl paraben and imidazolidinyl urea; viscosity modifiers, such as a diethanolamide of a long chain fatty acid (e.g., PEG 3 lauric diethanolamide), cocomonoethanol amide; sodium chloride; sodium sul- fate; polyvinyl alcohol; pH adjusting agents, such as citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide, sodium car ⁇ bonate; salts, in general, such as potassium acetate and sodium chloride; coloring agents, such as any of the FD&C or D&C dyes; anti- d
  • the pH of the present compositions generally will be between about 3 and about 9, preferably between about 4 and about 8.
  • the hair care compositions of the present invention can be made using conventional formulation and mixing techniques, as set forth below.
  • the hair care compositions of the present invention are used in conventional ways to provide the conditioning and shine benefits of the present invention. Such method of use depends upon the type of composition employed.
  • the compositions may be applied to dry hair or hair that has been wetted or dampened with water.
  • An effective amount of the product to provide conditioning and shine is applied to the hair.
  • the product may be applied to the hair via any means effective, such as by spraying, pouring, applying with the hands, and the like, and may be further worked into the hair with the hands or a hair styling implement (e.g., a brush and/or comb).
  • the composition may be left on the hair or rinsed off.
  • Shampoos and hair rinses are preferably applied to wet or dampened hair, and subsequently rinsed off.
  • sprays, mousses, gels, and tonics may be applied to wet or dry hair, and are generally left on the hair. After application to the hair, the hair is generally styled or dried. Alternately, especially for sprays, the hair may be styled prior to application of the composition.
  • effective amount is meant an amount sufficient to provide hair shine and conditioning benefits. In general, from about 0.1g to about 60g will be applied to the hair, although amounts outside this range may be effective depending upon the length and amount of the users hair, the type of hair and amount of shine and conditioning desired, the particular product formulations, and whether excess product is applied by the user.
  • a collagen solution is prepared by dissolving 10.0g of gelatin (175 bloom) in 83.0g DRO (double reverse osmosis) water at 155°C , with stirring. Next, 0.05g propylparaben is dissolved in the gelatin solution. Next, 4.5g 1M NaOH is added, followed by 3.0g of Ceraphyl GA-D (a mixture of 10-15% soy bean oil and 85-90% maleated soy bean oil available from VanDyk Inc., Belleville, NJ, USA) to form a stable, white emulsion. Next, 1.2g of lactic acid is stirred into the emulsion, referred hereinafter as Solution A.
  • Solution A a mixture of 10-15% soy bean oil and 85-90% maleated soy bean oil available from VanDyk Inc., Belleville, NJ, USA
  • a 3.0%, by weight, formaldehyde in water solution, Solution B, is prepared and contained separately from Solution A.
  • Ceramic tiles approximately 7.3cm x 7.3cm in size having a black glazed top and an average peak height ("roughness") of 5.0 -7.0 microns (can be measured with a Rodenstock RM600-2D/3-D Measuring Station (Rodenstock Meterology, Munich, W. Germany)) are prepared and coated with the collagen on their top surfaces.
  • Glossmeter Specular Reflectance of the collagen-coated tile should be from 8.0 - 12.0%.
  • Specular reflectance of the collagen-coated tile is measured utilizing a glossmeter, such as a BYK-Gardner "micro-gloss” glossmeter. Specular reflection measurements are made as described in ASTM Method D 523 at an angle of incidence of 60°. Specular reflectance measured this way is referred to herein as "Glossmeter Specular Reflectance.”
  • the tiles can be prepared as follows. Syringe A is filled with 3.0cc of Solution A. Syringe B is filled with 0.2cc of Solution B. Syringe B contents are emptied onto the top surface of a tile. Syringe A contents are emptied onto the top of Solution B, on the top surface of the tile.
  • the solutions are mixed for five seconds and spread uniformly on the top surface of the tile with a spatula.
  • a 1.0 inch inside diameter metal ring is placed on the top surface of the tile.
  • the collagen film is allowed to dry for eight hours.
  • the metal ring is removed.
  • the roughness of the collagen coated surface of the tile should be from 3.0 to 5.0 microns.
  • a polysiloxane hair shine agent or polysiloxane-containing hair shine component is prepared, as previously described, at a 1.00% concentration in a compatible diluent. Any spreading agents or other additives in the shine agent phase of the product should be present at a weight ratio corresponding to that found in this phase of the composition.
  • a syringe is used to deposit 0.05cc of the mixture at the center of the area encompassed by the ring on the surface of the collagen-coated tile. The mixture is allowed to dry. Glossmeter Specular Reflectance is measured.
  • PREMIX EXAMPLES 1-9 The following are a variety of exemplary polysiloxane hair conditioning agent dispersions useful in the present invention. These premixes can be used in a variety hair care compositions containing other cosmetically or pharmaceutically active ingredients, carrier ingredients, or other ingredients.
  • Pentaphenyl Siloxane (9) 0.00 25.00 0.00
  • the premixes are prepared by blending all the components with agitation for about 1/2 hour at room temperature, to form a stable dispersion or emulsion.
  • the premixes are prepared by blending all of the components with agitation for about 1/2 hour at room temperature, to form a stable dispersion or emulsion.
  • the exemplary hair care compositions which follow can be made utilizing any of premix Examples 10-12, above (hereinafter referred to as "Conditioning Premix Examples").
  • the Conditioning and Shine Premixes, plasticizer, if applicable, potassium hydroxide, and water are combined with mixing.
  • the perfume is then added with mixing.
  • the product can be packaged in conventional nonaerosol pump spray containers and compressed air pump spray aerosol containers.
  • composition is made by mixing the above components together in a conventional manner.
  • the following is a shampoo composition representative of the present invention.
  • Ammonium lauryl sulfate and citric acid are added to the distilled water at about 15 C.
  • the mixture is heated to from 70 C. to 80 C.
  • the cocamide MEA and glycol distearate are added at this point.
  • the ammonium laureth-3 sulfate, cetyl alcohol, stearyl alcohol conditioning premix, and shine premix are blended at from 70 C to 90 C.
  • This mixture is added to the batch following the ethylene glycol distearate.
  • the preservative is then added.
  • the batch is mixed for 5 minutes then cooled to room temperature (15 C to 25 C).
  • the fragrance is added, then the batch is milled under high shear for at least 5 minutes using conventional milling apparatus.
  • EXAMPLE V 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.
  • Aluminum 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.
  • Emulsifying Wax 0.50 0.00 0.00
  • Hydroxyethyl cellulose is added to the water at a temperature of 15 C to 40 C and mixed to disperse the hydroxyethyl cellulose. This mixture is then heated to a temperature of from 60 C to 90 C. Materials listed 2 through 10 (counted from the top of the list) are added to the batch while the temperature is maintained in this range. The mixture is stirred for approximately 10 minutes, then cooled to approximately 50 C. The remaining materials are added at this temperature. The mixture is milled under high shear for approximately 2 minutes using a conventional milling apparatus, then cooled to room temperature. EXAMPLE X - XIV
  • dimethicone gum SE 76, General Electric Silicone Products Division
  • dimethicone fluid 350 centipoise, 25° C
  • the shampoo formulations are prepared as follows. As applicable, premixes are prepared for ethylene glycol distearate, the polysiloxane-containing hair shine component, the polysiloxane- containing hair conditioning component, and the polyquaternium 10. For the premix preparations described below, all percentages are based on the total weight of the particular premix.
  • the ethylene glycol distearate premix is prepared as follows: 72.71 % ammonium laureth (3) sulfate aqueous solution (28% active) and 19.33% added water are mixed and heated to 73° C in a tank. Then 4.00% ethylene glycol distearate, 2.00% cocamide MEA, 0.40% disodium phosphate, 0.36% ammonium chloride, 0.26 % ethylene diamine tetraacetic acid (EDTA), and 0.20% sodium phosphate are sequentially added and mixed in the tank. The mixture is then mixed for an additional 15 minutes, and 0.74% Glydant is finally added with mixing.
  • the ethylene glycol distearate premix is prepared as follows: 88.15% ammonium laureth (3) sulfate aqueous solution (28% active) is heated to 73° C in a tank. Then 6.00% ethylene glycol distearate, 0.40% lauryl alcohol, and 3.50% sodium sulfate are sequentially added to the tank with mixing, and then the mixture is mixed for an additional 15 minutes. 1.50% Glydant is finally added with mixing.
  • the hair shine component premix is prepared by mixing 40.8% ammonium laureth (3) sulfate (28 % active in aqueous solution), 40.80 % diphenyl dimethyl siloxane, 17.00% of the trimethylsiloxysilicate/dimethicone and 1.40% sodium chloride in a tank for about 30 minutes at ambient temperature.
  • the hair conditioning premix is prepared by mixing 70.00% dimethicone, 29.00% ammonium laureth(3)sulfate, and 1.00% sodium chloride to a tank at ambient temperature and mixing for about 30 minutes.
  • a polyquaternium 10 premix is prepared by mixing 3.80% polyquaternium 10 and 96.2% water in a tank for about 10 minutes.
  • the shampoo formulations are prepared as follows.
  • the ethylene glycol distearate, polyquaternium 10, hair shine component, and hair conditioning premixes are incorporated into the final mix at the appropriate amounts to provide the indicated level of ethylene glycol distearate, polyquaternium 10, dimethicone, diphenyl dimethyl siloxane, and dimethicone for each of the above shampoo formulations.
  • the EGDS premix is milled with a high shear mill, cooled to 32° C, and added to a mix tank.
  • any remaining surfactant not accounted for in the premixes is then added to the tank, with mixing.
  • the polyquaternium 10 premix (if applicable), hair shine component premix, and hair conditioning component premix are then added sequentially to the tank and the composition is mixed for about 15 minutes.
  • pH is adjusted, as desired, to pH 5.5-6.5 with sodium phosphate, and viscosity is adjusted, as desired, to 2500-5500 centipoise (at 25° C) with sodium chloride.
  • Examples XII and XIII pH is adjusted, as desired, to pH 5.5-6.5 with sodium hydroxide, and viscosity is adjusted, as desired, to 2500-5500 centipoise (at 25° C) with sodium sulfate.
  • any water not accounted for in the premixes and surfactants is then added, with mixing.
  • the shampoo formulations hereof can provide excellent conditioning to the hair, particularly dry hair conditioning, in combination with improved hair shine.

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Abstract

Composition de soin pour les cheveux servant à traiter et donner de la brillance aux cheveux, cette composition comprenant (a) un conditionneur capillaire dispersé comprenant entre environ 0,01 % et 10 % en poids de la composition d'un fluide au polysiloxane insoluble et non volatil, ce dernier se caractérisant par une viscosité d'au moins 5,000 centipoise environ à 25 °C, ledit conditionneur capillaire ayant un indice de réfraction inférieur à 1,48; (b) un agent de brillance capillaire dispersé comprenant entre environ 0,005 % et 5 % en poids de la composition d'un fluide au polysiloxane insoluble et non volatil, cet agent de brillance capillaire ayant un indice de réfraction supérieur ou égal à 1,48; (c) un véhicule aqueux adapté à l'application topique sur les cheveux; les deux agents de conditionnement et de brillance capillaire existant dans ladite composition sous forme de phases distinctes et discontinues.
PCT/US1995/004579 1994-05-13 1995-04-18 Compositions de soin pour les cheveux contenant une double dispersion d'un agent conditionneur au polysiloxane et d'un agent de brillance au polysiloxane WO1995031173A1 (fr)

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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999006017A1 (fr) * 1997-07-31 1999-02-11 Rhodia Chimie Composition parfumante utilisant des organopolysiloxanes
WO1999033433A2 (fr) * 1997-12-23 1999-07-08 Henkel Kommanditgesellschaft Auf Aktien Produits de traitement capillaire
US5989533A (en) * 1997-07-21 1999-11-23 Revlon Consumer Products Corporation Hair conditioning compositions containing alpha or beta hydroxy acid esters
WO2000021495A1 (fr) * 1998-10-09 2000-04-20 Colgate-Palmolive Company Compositions de soins capillaires volumatrices contenant des siloxysilicates
EP1088545A1 (fr) * 1999-09-30 2001-04-04 The Procter & Gamble Company Compositions de soin pour cheveux
EP2022489A1 (fr) * 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Composition de conditionnement pour cheveux sans rinçage
EP2022535A1 (fr) * 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Composition pour la mise en forme permanente des cheveux humains
EP2022486A1 (fr) * 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Composition de coloration
EP2022488A1 (fr) * 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Composition de coloration
EP2022485A1 (fr) * 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Composition de nettoyage
EP2022487A1 (fr) * 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Composition de conditionnement pour fibres de kératine
EP2022476A1 (fr) * 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Procédé de conditionnement des fibres kératiniques
WO2009045339A1 (fr) * 2007-10-01 2009-04-09 Corning Cable Systems Llc Gel adaptateur d'indice pour fibres optiques a nanostructure, ensemble epissure mecanique et connecteur l'utilisant
US7742670B2 (en) 2007-10-01 2010-06-22 Corning Cable Systems Llc Index-matching gel for nanostructure optical fibers and mechanical splice assembly and connector using same
WO2010089199A1 (fr) * 2009-02-04 2010-08-12 Unilever Plc Composition de traitement capillaire
EP2025325B1 (fr) * 2007-08-07 2013-01-02 Kao Germany GmbH Composition pour fibres de kératine
US20150216772A1 (en) * 2009-12-23 2015-08-06 L'oreal Composition containing a volatile linear alkane and a nonionic associative polymer, useful for conditioning the hair
JP2019073467A (ja) * 2017-10-13 2019-05-16 タカラベルモント株式会社 毛髪処理剤および毛髪処理剤セット

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EP0240349A2 (fr) * 1986-04-04 1987-10-07 The Procter & Gamble Company Mousse à coiffer
EP0463780A2 (fr) * 1990-06-20 1992-01-02 Unilever N.V. Composition sous forme de shampooing
WO1994008557A1 (fr) * 1992-10-22 1994-04-28 The Procter & Gamble Company Compositions pour soins favorisant la coiffure et le brillant

Patent Citations (3)

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Publication number Priority date Publication date Assignee Title
EP0240349A2 (fr) * 1986-04-04 1987-10-07 The Procter & Gamble Company Mousse à coiffer
EP0463780A2 (fr) * 1990-06-20 1992-01-02 Unilever N.V. Composition sous forme de shampooing
WO1994008557A1 (fr) * 1992-10-22 1994-04-28 The Procter & Gamble Company Compositions pour soins favorisant la coiffure et le brillant

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5989533A (en) * 1997-07-21 1999-11-23 Revlon Consumer Products Corporation Hair conditioning compositions containing alpha or beta hydroxy acid esters
WO1999006017A1 (fr) * 1997-07-31 1999-02-11 Rhodia Chimie Composition parfumante utilisant des organopolysiloxanes
WO1999033433A2 (fr) * 1997-12-23 1999-07-08 Henkel Kommanditgesellschaft Auf Aktien Produits de traitement capillaire
WO1999033433A3 (fr) * 1997-12-23 1999-09-02 Henkel Kgaa Produits de traitement capillaire
WO2000021495A1 (fr) * 1998-10-09 2000-04-20 Colgate-Palmolive Company Compositions de soins capillaires volumatrices contenant des siloxysilicates
EP1088545A1 (fr) * 1999-09-30 2001-04-04 The Procter & Gamble Company Compositions de soin pour cheveux
WO2001022929A1 (fr) * 1999-09-30 2001-04-05 The Procter & Gamble Company Compositions pour les soins des cheveux
EP2025365A3 (fr) * 2007-08-07 2011-03-09 KPSS-Kao Professional Salon Services GmbH Composition de mise en forme permanente de cheveux humains
US7744656B2 (en) 2007-08-07 2010-06-29 Kpss-Kao Professional Salon Services Gmbh Colouring composition
EP2022486A1 (fr) * 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Composition de coloration
EP2022488A1 (fr) * 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Composition de coloration
EP2022485A1 (fr) * 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Composition de nettoyage
EP2022487A1 (fr) * 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Composition de conditionnement pour fibres de kératine
EP2022476A1 (fr) * 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Procédé de conditionnement des fibres kératiniques
EP2025330A3 (fr) * 2007-08-07 2015-07-29 Kao Germany GmbH Composition de nettoyage
EP2022490A3 (fr) * 2007-08-07 2015-07-01 Kao Germany GmbH Composition de coloration
US7662760B2 (en) 2007-08-07 2010-02-16 Kpss - Kao Professional Salon Services Gmbh Cleansing composition comprising a ternary surfactant mixture and polyaryl siloxane
EP2022491A3 (fr) * 2007-08-07 2015-07-01 Kao Germany GmbH Composition de coloration
EP2022535A1 (fr) * 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Composition pour la mise en forme permanente des cheveux humains
US7758658B2 (en) 2007-08-07 2010-07-20 Kpss-Kao Professional Salon Services Gmbh Colouring composition
EP2025325B1 (fr) * 2007-08-07 2013-01-02 Kao Germany GmbH Composition pour fibres de kératine
EP2022489A1 (fr) * 2007-08-07 2009-02-11 KPSS-Kao Professional Salon Services GmbH Composition de conditionnement pour cheveux sans rinçage
US8152387B2 (en) 2007-10-01 2012-04-10 Corning Cable Systems Llc Index-matching gel for nanostructure optical fibers and mechanical splice assemble and connector using same
US7742670B2 (en) 2007-10-01 2010-06-22 Corning Cable Systems Llc Index-matching gel for nanostructure optical fibers and mechanical splice assembly and connector using same
US7628548B2 (en) 2007-10-01 2009-12-08 Corning Cable Systems Llc Index-matching gel for nanostructure optical fibers and mechanical splice assembly and connector using same
WO2009045339A1 (fr) * 2007-10-01 2009-04-09 Corning Cable Systems Llc Gel adaptateur d'indice pour fibres optiques a nanostructure, ensemble epissure mecanique et connecteur l'utilisant
JP2012516866A (ja) * 2009-02-04 2012-07-26 ユニリーバー・ナームローゼ・ベンノートシヤープ ヘアトリートメント組成物
WO2010089199A1 (fr) * 2009-02-04 2010-08-12 Unilever Plc Composition de traitement capillaire
US20150216772A1 (en) * 2009-12-23 2015-08-06 L'oreal Composition containing a volatile linear alkane and a nonionic associative polymer, useful for conditioning the hair
US9566220B2 (en) * 2009-12-23 2017-02-14 L'oreal Composition containing a volatile linear alkane and a nonionic associative polymer, useful for conditioning the hair
JP2019073467A (ja) * 2017-10-13 2019-05-16 タカラベルモント株式会社 毛髪処理剤および毛髪処理剤セット

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