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WO2001091707A1 - Compositions de soin capillaire contenant un agent de lissage - Google Patents

Compositions de soin capillaire contenant un agent de lissage Download PDF

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Publication number
WO2001091707A1
WO2001091707A1 PCT/US2000/014881 US0014881W WO0191707A1 WO 2001091707 A1 WO2001091707 A1 WO 2001091707A1 US 0014881 W US0014881 W US 0014881W WO 0191707 A1 WO0191707 A1 WO 0191707A1
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Prior art keywords
hair care
care composition
composition according
group
cationic
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PCT/US2000/014881
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English (en)
Inventor
Daniel Wayne Michael
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The Procter & Gamble Company
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Priority to PCT/US2000/014881 priority Critical patent/WO2001091707A1/fr
Priority to AU2000255909A priority patent/AU2000255909A1/en
Publication of WO2001091707A1 publication Critical patent/WO2001091707A1/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
    • A61Q5/12—Preparations containing hair conditioners
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A61K8/342—Alcohols having more than seven atoms in an unbroken chain
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • 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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • 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
    • A61K8/73—Polysaccharides
    • A61K8/731—Cellulose; Quaternized cellulose derivatives
    • 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
    • A61K8/86—Polyethers
    • 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
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • 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
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/542—Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5422—Polymers characterized by specific structures/properties characterized by the charge nonionic

Definitions

  • the present invention relates to hair care compositions comprising pentaerythritol ester oils as frizz control agents.
  • Hair is often subjected to a wide variety of insults that can cause damage. These include shampooing, rinsing, drying, heating, combing, styling, perming, coloring, exposure to the elements, etc.
  • insults include shampooing, rinsing, drying, heating, combing, styling, perming, coloring, exposure to the elements, etc.
  • the hair is often in a dry, rough, lusterless or frizzy condition due to abrasion of the hair surface and removal of the hair's natural oils and other natural conditioning and moisturizing components.
  • hair is subjected to weather-related changes, such as changes in humidity, which can leave hair in a frizzy condition.
  • Frizzy condition of the hair often causes an expanded and unruly hair and makes it difficult to control the hair style. For consumers who desire well aligned hair, such expanded and unruly hair is not desirable.
  • the term "frizz control” as used herein means to control hair frizz, i.e., to reduce frizz condition of the hair or to prevent the hair from causing frizzy condition.
  • leave-on conditioner type hair formulations provide advantages over other more permanent frizz reduction approaches. For example, leave-on formulations are typically less damaging to the hair. Also, leave-on formulations are more convenient because the consumer can use the product at any time and then wash the product out of the hair with one washing. Another benefit is that the product may be applied to parts of the hair most in need of the frizz control benefits.
  • hair conditioning benefits are provided through the use of hair conditioning agents such as cationic surfactants, cationic polymers, silicone conditioning agents, hydrocarbon and other organic oils and solid aliphatics such as fatty alcohols.
  • hair conditioning agents such as cationic surfactants, cationic polymers, silicone conditioning agents, hydrocarbon and other organic oils and solid aliphatics such as fatty alcohols.
  • hair conditioning agents are often impractical for using in the large amounts necessary to reduce hair frizz. Usage of large amounts of conditioning agents that work to control hair frizz by coating and weighing down the hair commonly results in a poor perception of hair cleanliness and hair feel, for example, leaving the hair and hands with a tacky, dirty, feeling.
  • hair care compositions comprising a pentaerythiritol ester oil, in combination with a polysiloxane resin, a vehicle comprising a lipid compound and a cationic surfactant, and a hydrophobically modified hydroxyalkyl cellulose thickener, have increased efficacy for frizz control while retaining good conditioning/shine benefits and good hair feel and appearance, i.e., it provides improved frizz control benefit in addition to shine benefit and other conditioning benefits such as smoothness, softness, and reduction of friction, while reducing sticky and greasy feeling.
  • the present invention provides hair care compositions comprising by weight: a) from about 0.001 % to about 5% of a non-volatile polysiloxane resin; b) from about 1 % to about 50% of a pentaerythritol ester oil having the formula:
  • R 1 , R 2 , R 3 , and R 4 independently, are branched, straight, saturated, or unsaturated alkyl, aryl, and alkylaryl groups having from 1 to about 30 carbons; c) from about 1.1 % to about 13% of a vehicle which comprises a lipid material and a cationic surfactant; d) from about 0.01 % to about 5% of a hydrophobically modified hydroxyalkyl cellulose thickener; and e) an aqueous carrier.
  • compositions of the present invention comprising of and consisting essentially of. AH percentages, parts and ratios are based upon the total weight of the compositions of the present invention, unless otherwise specified. All such weights as they pertain to listed ingredients are based on the active level and, therefore, do not include carriers or by-products that may be included in commercially available materials.
  • the aspects and embodiments of the present invention set forth in this document have many advantages.
  • the hair conditioning compositions of the present invention have increased efficacy for frizz control while retaining good conditioning/shine benefits and good hair feel and appearance, i.e., the hair conditioning compositions of the present invention provide improved frizz control benefit in addition to other conditioning benefits such as smoothness, softness, shine and reduction of friction, and leave the hair and hands with a clean feeling.
  • compositions of this invention contain four essential ingredients: a non-volatile polysiloxane resin, a pentaerythritol ester oil, a vehicle, and a hydrophobically modified hydroxyalkyl cellulose thickener.
  • These compositions encompass any composition form intended for human use on hair, including, for example, mousses, tonics, creams, and balms.
  • Such composition forms may be dispensed through devices such as a pump or bottle and/or applied directly to the hair with the hands or another implement such as a comb or brush.
  • specific essential components may be selected, and other optional ingredients may be incorporated, in forming the final hair care product.
  • the balance of the products is made up of water, preferably distilled water.
  • compositions of the present invention comprise from about 0.001 % to about 5%, preferably from about 0.005% to about 3%, more preferably from about 0.01 % to about 2%, even more preferably from about 0.1 % to about 1 %, by weight of the composition, of the non-volatile polysiloxane resin.
  • Polysiloxane resins are highly crosslinked polymeric siloxane systems.
  • the crosslinking is introduced through the incorporation of trifunctional and tetrafunctional silanes with monofunctional or difunctional, or both, silanes 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 materials which have at least about 1.1 oxygen atoms per silicon atom will generally be silicone resins herein. Preferably, the ratio of oxygen atoms to silicon atoms is at least about 1.2:1.0.
  • Silanes used in the manufacture of silicone resins include monomethyl, dimethyl, trimethyl, monophenyl, diphenyl, methylphenyl, ethylphenyl, propylphenyl, monovinyl, and methylvinylchlorosilanes, and tetrachlorosilane.
  • 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.
  • M denotes the monofunctional unit (CH3)3SiOfj.5
  • D denotes the difunctional unit (CH3)2SiO
  • T denotes the trifunctional unit (CH3)SiO-
  • Q denotes the quadri- or tetra-functional unit Si ⁇ 2- Primes of the unit symbols, e.g., M', D', T', and Q' denote siloxane units with one or more substituents other than methyl, and must be specifically defined for each occurrence.
  • the polysiloxane resins for use herein preferably have at least one M', D ⁇
  • T' or Q' functionality that possesses a substituent group with delocalised electrons.
  • 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.
  • Preferred polysiloxane resins for use herein are M'Q resins, more preferred are M' 6 Q 3 , M' 8 Q 4 M' 10 Q 5 , M' 12 Q 6 resins and mixtures thereof. Preferred
  • M'Q resins are those which have at least one group containing delocalised electrons substituted on each M' functionality. More preferred are resins where the other substituent groups are alkyl groups, especially preferred are methyl groups.
  • the polysiloxane resin for use herein preferably have at least one substituent group possessing delocalised electrons.
  • This substituent or substituents can be independently selected from alkyl groups, aryl groups, alkoxy groups, alkaryl groups, arylalkyl arylalkoxy groups, alkaryloxy groups, and combinations thereof.
  • at least one of the resin substituent groups comprises an aryl group, arylalkyl group and/or alkaryl group. More preferably, at least one of the resin substituent groups comprises an alkaryl group and/or arylalkyl group substituent. More preferably, at least one of the resin substituent groups comprises an alkaryl group substituent.
  • a particularly preferred alkaryl group substituent is 2-phenyl propyl.
  • the resins herein will also generally have other substituents without delocalised electrons.
  • substituents can include hydrogen, hydroxyl groups, alkyl groups, alkoxy groups, amino functionalities groups, and mixtures thereof.
  • Preferred substituents without delocalised electrons are selected from alkyl group substituents, especially methyl group substituents.
  • a particularly preferred methyl group substituent for use herein is dimethyl (2-phenylpropyl) silyl ester.
  • aryl means a functionality containing one or more homocyclic or heterocyclic rings.
  • the aryl functionalities herein can be unsubstituted or substituted and generally contain from 3 to 16 carbon atoms.
  • Preferred aryl groups include, but are not limited to, phenyl, naphthyl, cyclopentadienyl, anthracyl, pyrene, pyridine, pyrimidine
  • alkyl means a saturated or unsaturated, substituted or unsubstituted, straight or branched-chain, hydrocarbon having from 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms.
  • alkyl therefore includes alkenyls having from 2 to 8, preferably 2 to 4, carbons and alkynyls having from 2 to 8, preferably 2 to 4, carbons.
  • Preferred alkyl groups include, but are not limited to, methyl, ethyl, propyl, isopropyl, and butyl. More preferred are methyl, ethyl and propyl.
  • alkaryl means a substituent comprising an alkyl moiety and an aryl moiety wherein the alkyl moiety is bonded to the siloxane resin.
  • arylalkyl means a substituent comprising an aryl moiety and an alkyl moiety wherein the aryl moiety is bonded to the siloxane resin.
  • the polysiloxane resins employed herein are non-volatile polysiloxane resins.
  • volatile refers to those materials that are liquid under ambient conditions and have a vapor pressure as measured at 25°C of at least about 0.01 mmHg, typically from about 0.01 mmHg to about 6.0 mmHg
  • nonvolatile refers to those materials which are not volatile as that term is defined herein. Such “nonvolatile” materials will typically be in the form of a liquid, semi-solid or solid, and have no measurable vapor pressure as measured at 25°C.
  • the polysiloxane resins for use herein preferably have a viscosity of less than about 5000 m ⁇ V, more preferably less than about 2000 mmV, even more preferably less than about 1000 mnrV 1 , even more still preferably less than about 600 mrrrV 1 , at 25°C.
  • the viscosity can be measured by means of a Cannon-Fenske Routine Viscometer (ASTM D-445). Background material on silicones including sections discussing silicone fluids, gums, and resins, as well as manufacture of silicones, can be found in Encyclopaedia of Polymer Science and Engineering (Volume 15, Second Edition, pp. 204-308, John Wiley & Sons, Inc., 1989), incorporated herein by reference.
  • a preferred commercially available non-volatile polysiloxane resin useful herein includes Styryl MQ Silicone available from GE Silicones.
  • compositions of the present invention comprises from about 1% to about 50%, preferably from about 2% to about 25%, more preferably from about
  • the pentaerythritol ester oil useful herein is believed to provide improved frizz control benefit, in combination with a polysiloxane resin, a vehicle comprising a lipid compound and a cationic conditioning compound, while retaining good conditioning/shine benefits and good hair feel and appearance.
  • Pentaerythritol ester oils useful herein are those having the formula:
  • R ⁇ R 2 , R 3 , and R 4 are branched, straight, saturated, or unsaturated alkyl, aryl, and alkylaryl groups having from 1 to about 30 carbons.
  • R 1 , R 2 , R 3 , and R 4 independently, are branched, straight, saturated, or unsaturated alkyl groups having from about 8 to about 22 carbons. More preferably, R 1 , R 2 , R 3 and R 4 are defined so that the molecular weight of the compound is from about 800 to about 1200.
  • pentaerythritol ester oils herein include pentaerythritol tetraisostearate, pentaerythritol tetraoleate, and mixtures thereof.
  • Such compounds are available from Kokyu Alcohol with tradenames KAKPTI, KAKTTI.
  • the present invention employs from about 1.1 % to about 13%, preferably from about 1.1 % to about 6%, more preferably from about 1.1 % to about 3.5%, by weight of the composition, of a vehicle.
  • the vehicle comprises two essential components: a lipid material and a cationic surfactant.
  • Such gel-type vehicles are generally described in the following documents, both incorporated by reference herein: Barry, et al., "The Self-Bodying Action of Alkyltrimethylammonium Bromides/Cetostearyl Alcohol Mixed Emulsifiers; Influence of Quaternary Chain Length", 35 J.
  • the vehicles of the present invention comprise one or more lipid materials, (herein referred to as comprising a "lipid material", singly or in combination) which are essentially water-insoluble, and contain hydrophobic and hydrophilic moieties.
  • the compositions of the present invention comprises from about 1 % to about 10%, preferably from about 1% to about 5%, and more preferably from about 1 % to about 3%, by weight of the composition, of the lipid material.
  • Lipid materials useful herein include naturally or synthetically-derived acids, acid derivatives, alcohols, esters, ethers, ketones, and amides having carbon chains of from 12 to 22, preferably from 16 to 18, carbon atoms in length. Fatty alcohols and fatty esters are preferred; fatty alcohols are particularly preferred.
  • the fatty alcohols useful herein are those having from about 14 to about 30 carbon atoms, preferably from about 16 to about 22 carbon atoms. These fatty alcohols can be straight or branched chain alcohols and can be saturated or unsaturated. Nonlimiting examples of fatty alcohols include, cetyl alcohol, stearyl alcohol, behenyl alcohol, and mixtures thereof.
  • the fatty acids useful herein are those having from about 10 to about 30 carbon atoms, preferably from about 12 to about 22 carbon atoms, and more preferably from about 16 to about 22 carbon atoms. These fatty acids can be straight or branched chain acids and can be saturated or unsaturated. Also included are diacids, triacids, and other multiple acids which meet the requirements herein. Also included herein are salts of these fatty acids. Nonlimiting examples of fatty acids include lauric acid, palmitic acid, stearic acid, behenic acid, sebacic acid, and mixtures thereof.
  • the fatty alcohol derivatives and fatty acid derivatives useful herein include alkyl ethers of fatty alcohols, alkoxylated fatty alcohols, alkyl ethers of alkoxylated fatty alcohols, esters of fatty alcohols, fatty acid esters of compounds having esterifiable hydroxy groups, hydroxy-substituted fatty acids, and mixtures thereof.
  • Nonlimiting examples of fatty alcohol derivatives and fatty acid derivatives include materials such as methyl stearyl ether; the ceteth series of compounds such as ceteth-1 through ceteth-45, which are ethylene glycol ethers of cetyl alcohol, wherein the numeric designation indicates the number of ethylene glycol moieties present; the steareth series of compounds such as steareth-1 through 10, which are ethylene glycol ethers of steareth alcohol, wherein the numeric designation indicates the number of ethylene glycol moieties present; ceteareth 1 through ceteareth-10, which are the ethylene glycol ethers of ceteareth alcohol, i.e.
  • Hydrocarbons useful herein include compounds having at least about 20 carbons.
  • Steroids useful herein include compounds such as cholesterol.
  • Commercially available high melting point compounds useful herein include: cetyl alcohol, stearyl alcohol, and behenyl alcohol having tradenames KONOL series available from Shin Ninon Rika (Osaka, Japan), and NAA series available from NOF (Tokyo, Japan); pure behenyl alcohol having tradename 1- DOCOSANOL available from WAKO (Osaka, Japan), various fatty acids having tradenames NEO-FAT available from Akzo (Chicago Illinois, USA), HYSTRENE available from Witco Corp. (Dublin Ohio, USA), and DERMA available from Vevy (Genova, Italy); and cholesterol having tradename NIKKOL AGUASOME LA available from Nikko.
  • Preferred esters for use herein include cetyl palmitate and glycerol monostearate.
  • Cetyl alcohol and stearyl alcohol are preferred alcohols.
  • a particularly preferred lipid 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 and from about 35% to about 45% (by weight of mixture) of stearyl alcohol.
  • the vehicle employed in the present invention also comprises one or more cationic surfactants.
  • the compositions of the present invention comprise from about 0.1% to about 3%, preferably from about 0.1 % to about 1 %, more preferably from about 0.1 % to about 0.8%, by weight of the composition, of the cationic surfactants.
  • Such cationic surfactants contain amino or quaternary ammonium hydrophilic moieties which are positively charged when dissolved in the aqueous composition of the present invention.
  • Cationic surfactant vehicle materials among those useful herein are disclosed in the following documents, all incorporated by reference herein: M.C.
  • cationic surfactants useful herein are those corresponding to the general formula (I):
  • the aliphatic groups can 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. Preferred is when R 71 , R 72 , R 73 and R 74 are independently selected from C 1 to about C 22 alkyl.
  • Nonlimiting examples of cationic surfactants useful in the present invention include the materials having the following CTFA designations: quaternium-8, quaternium-14, quaternium-18, quatemium-18 methosulfate, quaternium-24, and mixtures thereof.
  • cationic surfactants of general formula (I) preferred are those containing in the molecule at least one alkyl chain having at least 16 carbons.
  • preferred cationic surfactants include: behenyl trimethyl ammonium chloride available, for example, with tradename INCROQUAT TMC-80 from Croda and ECONOL TM22 from Sanyo Kasei; cetyl trimethyl ammonium chloride available, for example, with tradename CA-2350 from Nikko Chemicals, hydrogenated tallow alkyl trimethyl ammonium chloride, dialkyl (14-18) dimethyl ammonium chloride, ditallow alkyl dimethyl ammonium chloride, dihydrogenated tallow alkyl dimethyl ammonium chloride, distearyl dimethyl ammonium chloride, dicetyl dimethyl ammonium chloride, di(behenyl/arachidyl) dimethyl ammonium chloride, dibehenyl dimethyl ammonium chloride, stearyl dimethyl benz
  • hydrophilically substituted cationic surfactants in which at least one of the substituents contain one or more aromatic, ether, ester, amido, or amino moieties present as substituents or as linkages in the radical chain, wherein at least one of the R 71 -R 74 radicals contain one or more hydrophilic moieties selected from alkoxy (preferably C ⁇ C-a alkoxy), polyoxyalkylene (preferably C,-C 3 polyoxyalkylene), alkylamido, hydroxyalkyl, alkylester, and combinations thereof.
  • the hydrophilically substituted cationic ⁇ conditioning surfactant contains from 2 to about 10 nonionic hydrophile moieties located within the above stated ranges.
  • Preferred hydrophilically substituted cationic surfactants include those of the formula (II) through (VIII) below:
  • n 1 is from 8 to about 28, m 1 +m 2 is from 2 to about 40, Z 1 is a short chain alkyl, preferably a C 1 -C 3 alkyl, more preferably methyl, or (CH 2 CH 2 O) m3 H wherein m 1 +m 2 +m 3 is up to 60, and X is a salt forming anion as defined above;
  • n 2 is 1 to 5
  • R 75 , R 76 , and R 77 are independently an C ⁇ C ⁇ alkyl
  • the remainder are CH 2 CH 2 OH
  • one or two of R 78 , R 79 , and R 80 are independently an C 1 -C 30 alkyl
  • remainder are CH 2 CH 2 OH
  • X is a salt
  • Z 2 is an alkyl, preferably C,-C 3 alkyl, more preferably methyl
  • Z 3 is a short chain hydroxyalkyl, preferably hydroxymethyl or hydroxyethyl
  • n 3 and n 4 independently are integers from 2 to 4, inclusive, preferably from 2 to 3, inclusive, more preferably 2, R 81 and R 82 , independently, are substituted or unsubstituted hydrocarbyls, C 12 -C 20 alkyl or alkenyl
  • X is a salt forming anion as defined above;
  • R 83 is a hydrocarbyl, preferably a C,-C 3 alkyl, more preferably methyl
  • Z 4 and Z 5 are, independently, short chain hydrocarbyls, preferably C 2 -C 4 alkyl or alkenyl, more preferably ethyl
  • m 4 is from 2 to about 40, preferably from about 7 to about 30, and
  • X is a salt forming anion as defined above;
  • R 84 and R 85 are C.,-C 3 alkyl, preferably methyl
  • Z 6 is a C 12 - C 22 hydrocarbyl, alkyl carboxy or alkylamido
  • A is a protein, preferably a collagen, keratin, milk protein, silk, soy protein, wheat protein, or hydrolyzed forms thereof
  • X is a salt forming anion as defined above;
  • Nonlimiting examples of hydrophilically substituted cationic surfactants useful in the present invention include the materials having the following CTFA designations: quaternium-16, quaternium-26, quaternium-27, quaternium-30, quaternium-33, quaternium-43, quaternium-52, quatemium-53, quaternium-56, quaternium-60, quatemium-61 , quaternium-62, quatemium-70, quaternium-71 , quatemium-72, quaternium-75, quaternium-76 hydrolyzed collagen, quatemium-77, quaternium-78, quaternium- 79 hydrolyzed collagen, quaternium-79 hydrolyzed keratin, quaternium-79 hydro
  • hydrophilically substituted cationic surfactants include dialkylamido ethyl hydroxyethylmonium salt, dialkylamidoethyl dimonium salt, dialkyloyl ethyl hydroxyethylmonium salt, dialkyloyl ethyldimonium salt, and mixtures thereof; for example, commercially available under the following tradenames; VARISOFT 110, VARISOFT 222, VARIQUAT K1215 and VARIQUAT 638 from Witco Chemical, MACKPRO KLP, MACKPRO WLW, MACKPRO MLP, MACKPRO NSP, MACKPRO NLW, MACKPRO WWP, MACKPRO NLP, MACKPRO SLP from Mclntyre, ETHOQUAD 18/25, ETHOQUAD 0/12PG, ETHOQUAD C/25, ETHOQUAD S/25, and ETHODUOQUAD from Akzo, DEHYQUAT SP from Henkel, and ATLAS G265
  • Amines are suitable as cationic surfactants.
  • Primary, secondary, and tertiary fatty amines are useful. Particularly useful are tertiary amido amines having an alkyl group of from about 12 to about 22 carbons.
  • Exemplary tertiary amido amines include: stearamidopropyldimethylamine, stearamidopropyldiethylamine, stearamidoethyldiethylamine, stearamidoethyldimethylamine, palmitamidopropyldimethylamine, palmitamidopropyldiethylamine, palmitamidoethyldiethylamine, palmitamidoethyldimethylamine, behenamidopropyldimethylamine, behenamidopropyldiethylamine, behenamidoethyldiethylamine, behenamidoethyldimethylamine, arachidamidopropy
  • dimethylstearamine dimethylsoyamine, soyamine, myristylamine, tridecylamine, ethylstearylamine, N-tallowpropane diamine, ethoxylated (with 5 moles of ethylene oxide) stearylamine, dihydroxyethylstearylamine, and arachidylbehenylamine.
  • Useful amines in the present invention are disclosed in U.S. Patent 4,275,055, Nachtigal, et al.
  • amines can also be used in combination with acids such as l- glutamic acid, lactic acid, hydrochloric acid, malic acid, succinic acid, acetic acid, fumaric acid, tartaric acid, citric acid, i?-glutamic hydrochloride, maleic acid, and mixtures thereof; more preferably -glutamic acid, lactic acid, citric acid.
  • the amines herein are preferably partially neutralized with any of the acids at a molar ratio of the amine to the acid of from about 1 : 0.3 to about 1 : 2, more preferably from about 1 : 0.4 to about 1 : 1.
  • Preferred cationic surfactants useful herein are selected from the group consisting of cetyl trimethyl ammonium chloride, stearyl trimethyl ammonium chloride, tetradecyltrimethyl ammonium chloride, dicetyl dimethyl ammonium chloride, dicocodimethyl ammonium chloride, and mixtures thereof.
  • compositions of the present invention comprise from about 0.01 % to about 5%, preferably from about 0.05% to about 3%, more preferably from about 0.1 %) to about 1 %, by weight of the composition, of a hydrophobically modified hydroalkyl cellulose thickener.
  • a hydrophobically modified hydroalkyl cellulose thickener preferred are nonionic hydrophobically modified hydroalkyl cellulose thickeners having an average molecular weight in the range of from about 2,000 to about 2,000,000, preferably from about 10,000 to about 1 ,000,000, more preferably from about 20,000 to about 800,000.
  • the hydrophobically modified hydroalkyl cellulose thickeners suitable for use in the compositions of the present invention include, but are not limited to, hydrophobically modified hydroxyethyl cellulose (HMHEC).
  • Cellulose ethers suitable for use herein have, prior to hydrophobic modification, a sufficient degree of nonionic substitution selected from methyl, ethyl, hydroxyethyl and hydroxypropyl to cause them to be water-soluble.
  • the preferred degree of nonionic substitution is in the range of from about 1.8 to about 4.0, preferably from about 2 to about 3, and especially from about 2.2 to about 2.8 by weight.
  • the cellulose ethers are then further substituted with alkyl or alkenyl groups having from about 8 to about 30, preferably from about 10 to about 24, more preferably from about 14 to about 18 carbon atoms in an amount of from about 0.1 to about 1 , preferably from about 0.3 to about 0.8, and especially from about 0.4 to about 0.6 weight percent.
  • the cellulose ether to be modified is preferably one of low to medium molecular weight, i.e., less than 800,000 and preferably between 20,000 and 700,000 (75 to 2500 D.P.).
  • Degree of polymerization (D.P.) as defined herein, means, the average number of glycoside units in the polymer.
  • Preferred cellulose ethers for use herein are selected from commercially available nonionic cellulose ethers such as hydroxyethylcellulose, hydroxy propylmethylcellulose, hydroxymethylcellulose, ethyl hydroxyethylcellulose and mixtures thereof.
  • the preferred cellulose ether substrate for use herein, is a hydroxyethylcellulose (HEC) having a molecular weight ranging from about 50,000 to about 700,000. Hydroxyethylcellulose of this molecular weight is the most hydrophilic of the materials completed. Accordingly, control of the modification process and control of the properties of the modified product can be more precise with this substrate. Hydrophilicity of the most commonly used nonionic cellulose ethers varies in the general direction: hydroxyethyl > hydroxypropyl > hydroxypropyl methyl > methyl.
  • the long chain alkyl modifier for the cellulose ether, can be attached to the cellulose ether substrate via an ether, ester or urethane linkage.
  • the ether linkage is preferred.
  • the modified cellulose ether materials are referred to as being "alkyl modified ", (the term alkyl as used generally herein also includes using alkenyl) it will be recognized that, except in the case where modification is effected with an alkyl halide, the modifier is not a simple long chain alkyl group.
  • the group is actually an alphahydroxyalkyl radical in the case of an epoxide, a urethane radical in the case of an isocyanate, or an acyl radical in the case of an acid or acyl chloride.
  • Landoll (19277) at column 2, lines 36-65.
  • NATROSOL PLUS Grade 330 C TM
  • TM hydrophobically modified hydroxyethylcellulose
  • cetyl hydroxyethylcellulose available from Aqualon Company, Wilmington, Delaware.
  • This material has a C 16 alkyl substitution of from 0.4% to 0.8% by weight.
  • the hydroxyethyl molar substitution for this material is from 3.0 to 3.7.
  • the average molecular weight for the water-soluble cellulose prior to modification is approximately 300,000.
  • NATROSOL PLUS Grade 430 CS TM
  • NATROSOL PLUS CS Grade D-67 TM
  • This material has a C 16 substitution of from 0.50% to 0.95%, by weight.
  • the hydroxyethyl molar substitution for this material is from 2.3 to 3.7.
  • the average molecular weight for the water soluble cellulose prior to modification is approximately 700,000.
  • compositions of the present invention comprise an aqueous carrier.
  • the aqueous carrier is included in an aqueous composition of the present invention.
  • the level and species of the carrier are selected according to the compatibility with other components, and other desired characteristic of the product.
  • Carriers useful in the present invention include water and water solutions of lower alkyl alcohols.
  • Lower alkyl alcohols useful herein are monohydric alcohols having 1 to 6 carbons, more preferably ethanol and isopropanol.
  • the aqueous carrier is substantially water. Deionized water is preferably used. Water from natural sources including mineral cations can also be used, depending on the desired characteristic of the product.
  • the aqueous compositions of the present invention comprise preferably from about 10% to about 98%.
  • composition of the present invention may further comprise a cationic conditioning polymer.
  • the cationic conditioning polymer can be included in the compositions of the present invention, at a level by weight of, preferably from about 0.5% to about 10%, more preferably from about 2% to about 5%, even more preferably from about 1% to about 3%.
  • the term "polymer” shall include materials whether made by polymerization of one type of monomer or made by two (i.e., copolymers) or more types of monomers.
  • the cationic polymer is a water soluble cationic polymer.
  • water soluble cationic polymer is a polymer which is sufficiently soluble in water to form a substantially clear solution to the naked eye at a concentration of 0.1% in water (distilled or equivalent) at 25°C.
  • the preferred polymer will be sufficiently soluble to form a substantially clear solution at 0.5% concentration, more preferably at 1.0% concentration.
  • the cationic polymers hereof will generally have a weight average molecular weight which is at least about 5,000, typically at least about 10,000, and is less than about 10 million. Preferably, the molecular weight is from about 100,000 to about 2 million.
  • the cationic polymers will generally have cationic nitrogen-containing moieties such as quaternary ammonium or cationic amino moieties, and mixtures thereof.
  • the 'cationic charge density" of a polymer refers to the ratio of the number of positive charges on a monomeric unit of which the polymer is comprises to the molecular weight of said monomeric unit.
  • the cationic charge density of the cationic polymers useful herein are preferably at least about 0.1 meq/gram, more preferably at least about 0.5 meq/gram, even more preferably at least about 1.1 meq/gram, and still more preferably at least about 1.2 meq/gram, and most preferably at least about 1.5 meq/g.
  • the cationic polymers will have a cationic charge density of less than about 5 meq/g, preferably less than 3.5 meq/g, more preferably less than about 2.5 meq/g and most preferably less than about 2.2 meq/g.
  • Cationic charge density of the cationic polymer may be determined according to the Kjeldahl Method. Those skilled in the art will recognize that the charge density of amino-containing polymers may vary depending upon pH and the isoelectric point of the amino groups. The charge density should be within the above limits at the pH of intended use.
  • any anionic counterions can be utilized for the cationic polymers so long as the water solubility criteria is met. Suitable counterions include halides (e.g., Cl, Br, I, or F, preferably Cl, Br, or I), sulfate, and methylsulfate. Others can also be used, as this list is not exclusive.
  • the cationic nitrogen-containing moiety will be present generally as a substituent, on a fraction of the total monomer units of the cationic hair conditioning polymers.
  • the cationic polymer can comprise copolymers, terpolymers, etc. of quaternary ammonium or cationic amine-substituted monomer units and other non-cationic units referred to herein as spacer monomer units.
  • the cationic amines can be primary, secondary, or tertiary amines, depending upon the particular species and the pH of the composition. In general, secondary and tertiary amines, especially tertiary amines, are preferred.
  • Amine-substituted vinyl monomers can be polymerized in the amine form, and then optionally can be converted to ammonium by a quaternization reaction.
  • Amines can also be similarly quaternized subsequent to formation of the polymer.
  • tertiary amine functionalities can be quaternized by reaction with a salt of the formula R 88 X wherein R 88 is a short chain alkyl, preferably a C, - C 7 alkyl, more preferably a C 1 - C 3 alkyl, and X is a salt forming anion as defined above.
  • Suitable cationic amino and quaternary ammonium monomers include, for example, vinyl compounds substituted with dialkylaminoalkyl acrylate, dialkylaminoalkyl methacrylate, monoalkylaminoalkyl acrylate, monoalkylaminoalkyl methacrylate, trialkyl methacryloxyalkyl ammonium salt, trialkyl acryloxyalkyl ammonium salt, diallyl quaternary ammonium salts, and vinyl quaternary ammonium monomers having cyclic cationic nitrogen-containing rings such as pyridinium, imidazolium, and quaternized pyrrolidone, e.g., alkyl vinyl imidazolium, alkyl vinyl pyridinium, alkyl vinyl pyrrolidone salts.
  • the alkyl portions of these monomers are preferably lower alkyls such as the C 1 - C 3 alkyls, more preferably C ⁇ and C 2 alkyls.
  • Suitable amine-substituted vinyl monomers for use herein include dialkylaminoalkyl acrylate, dialkylaminoalkyl methacrylate, dialkylaminoalkyl acrylamide, and dialkylaminoalkyl methacrylamide, wherein the alkyl groups are preferably C., - C 7 hydrocarbyls, more preferably C, - C 3 , alkyls.
  • the cationic polymers hereof can comprise mixtures of monomer units derived from amine- and/or quaternary ammonium-substituted monomer and/or compatible spacer monomers.
  • Suitable cationic hair conditioning polymers include, for example: copolymers of 1-vinyl-2-pyrrolidone and 1-vinyl-3-methylimidazolium salt (e.g., chloride salt) (referred to in the industry by the Cosmetic, Toiletry, and Fragrance Association, "CTFA", as Polyquaternium-16), such as those commercially available from BASF Wyandotte Corp.
  • CTFA Cosmetic, Toiletry, and Fragrance Association
  • Preferred cationic polymers for use herein include cationic polysaccharide polymers, such as cationic cellulose derivatives and cationic starch derivatives.
  • Cationic polysaccharides useful in the present invention also include those polymers based on 5,6 or 7 carbon sugars and derivatives which have been made water-soluble by, for example, derivatizing them with ethylene oxide. These polymers may be bonded via any of several arrangements, such as 1 ,4- ⁇ , 1 ,4- ⁇ , 1 ,3- ⁇ , 1 ,3- ⁇ and 1 ,6 linkages.
  • the monomers may be in straight or branched chain geometric arrangements.
  • Suitable examples include polymers based on arabinose monomers, polymers derived from xylose monomers, polymers derived from fucose monomers, polymers derived from fructose monomers, polymers based on acid-containing sugar monomers such as galacturonic acid and glucuronic acid, polymers based on amine sugar monomers such as galactosamine and glucosamine, particularly actylglucosamine, polymers based on 5 or 6 membered ring polyalcohol monomers, polymers based on gallactose monomers, polymers based on mannose monomers and polymers based on galcatomannan monomers.
  • Cationic polysaccharide polymer materials suitable for use herein include those of the formula:
  • Z 7 is an anhydroglucose residual group, such as a starch or cellulose anhydroglucose residual
  • R 89 is an alkylene oxyalkylene, polyoxyalkylene, or hydroxyalkylene group, or combination thereof
  • R 90 , R 91 , and R 92 independently are alkyl, aryl, alkylaryl, arylalkyl, alkoxyalkyl, or alkoxyaryl groups, each group containing up to about 18 carbon atoms, and the total number of carbon atoms for each cationic moiety (i.e., the sum of carbon atoms in R 90 , R 91 and R 92 ) preferably being about 20 or less
  • X is as previously described.
  • Cationic cellulose is available from Amerchol Corp. (Edison, NJ, USA) in their Polymer JR ® and LR ® series of polymers, as salts of hydroxyethyl cellulose reacted with trimethyl ammonium substituted epoxide, referred to in the industry (CTFA) as Polyquatemium 10.
  • CTFA trimethyl ammonium substituted epoxide
  • Another type of cationic cellulose includes the polymeric quaternary ammonium salts of hydroxyethyl cellulose reacted with lauryl dimethyl ammonium-substituted epoxide, referred to in the industry (CTFA) as Polyquatemium 24. These materials are available from Amerchol Corp. (Edison, NJ, USA) under the tradename Polymer LM-200 ® .
  • cationic polymers that can be used include cationic guar gum derivatives, such as guar hydroxypropyltrimonium chloride commercially available from Celanese Corp. in their Jaguar R series.
  • Other materials include quaternary nitrogen-containing cellulose ethers as described in U.S. Patent 3,962,418, and copolymers of etherified cellulose and starch as described in U.S. Patent 3,958,581.
  • the hair conditioning composition of the present invention may further comprise a nonionic surfactant.
  • the nonionic surfactant can be included in the composition of the present invention at a level by weight of, preferably from about
  • Nonionic surfactants include those compounds produced by condensation of alkylene oxide groups, hydrophilic in nature, with an organic hydrophobic compound, which may be aliphatic or alkyl aromatic in nature.
  • nonionic surfactants for use in the shampoo compositions include the following:
  • 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;
  • 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 1 glyceryl moieties and R' and R" are each alkyl or monohydroxyalkyl groups containing from about 1 to about 3 carbon atoms;
  • R long chain dialkyl sulfoxides containing one short chain alkyl or hydroxy alkyl radical of from 1 to about 3 carbon atoms (usually methyl) and one long hydrophobic chain which include alkyl, alkenyl, hydroxy alkyl, or keto alkyl radicals containing from about 8 to about 20 carbon atoms, from 0 to about 10 ethylene oxide moieties and from 0 to 1 glyceryl moieties;
  • alkyl polysaccharide (APS) surfactants e.g. alkyl polyglycosides
  • alkyl polysaccharide (APS) surfactants e.g. alkyl polyglycosides
  • APS surfactants having a hydrophobic group with about 6 to about 30 carbon atoms and a polysaccharide (e.g., polyglycoside) as the hydrophilic group; optionally, there can be a polyalkylene-oxide group joining the hydrophobic and hydrophilic moieties; and the alkyl group (i.e., the hydrophobic moiety) can be saturated or unsaturated, branched or unbranched, and unsubstituted or substituted (e.g., with hydroxy or cyclic rings); a preferred material is alkyl polyglucoside, which is commercially available from Henkel, ICI Americas, and Seppic; and
  • polyoxyethylene alkyl ethers such as those of the formula RO(CH2CH2 ⁇ ) n H and polyethylene glycol (PEG) glyceryl fatty esters, such as those of the formula R(0)OCH2CH(OH)CH2(OCH2CH2) n OH, wherein n is from 1 to about 200, preferably from about 20 to about 100, and R is an alkyl having from about 8 to about 22 carbon atoms.
  • ethylene glycol ethers of fatty alcohols as described in the above (3) or (8) are used as the nonionic surfactants in the composition of the present invention.
  • Ethylene glycol ethers of fatty alcohols useful herein include any ethylene glycol ethers of fatty alcohols which are suitable for use in a hair conditioning composition.
  • ethylene glycol ethers of fatty alcohols include; the ceteth series of compounds such as ceteth-1 through ceteth-45, which are ethylene glycol ethers of cetyl alcochol, wherein the numeric designation indicates the number of ethylene glycol moieties present; the steareth series of compounds such as steareth-1 through 100, which are ethylene glycol ethers of steareth alcohol, wherein the numeric designation indicates the number of ethylene glycol moieties present; ceteareth 1 through ceteareth-50, which are the ethylene glycol ethers of ceteareth alcohol, i.e.
  • Preferred for use herein is ceteareth-20.
  • polyethylene glycol derivatives of glycerides as described in the above (8) are used as the nonionic surfactants in the composition of the present invention.
  • Polyethylene glycol derivatives of glycerides useful herein include any polyethylene glycol derivative of glycerides which are water-soluble and which are suitable for use in a hair conditioning composition.
  • Suitable polyethylene glycol derivatives of glycerides for use herein include derivatives of mono-, di- and tri-glycerides and mixtures thereof.
  • polyethylene glycol derivatives of glycerides suitable herein are those which conform to the general formula (I):
  • n the degree of ethoxylation, is from about 4 to about 200, preferably from about 5 to about 150, more preferably from about 20 to about 120, and wherein R comprises an aliphatic radical having from about 5 to about 25 carbon atoms, preferably from about 7 to about 20 carbon atoms.
  • Suitable polyethylene glycol derivatives of glycerides can be polyethylene glycol derivatives of hydrogenated castor oil.
  • PEG-20 hydrogenated castor oil PEG-30 hydrogenated castor oil, PEG-40 hydrogenated castor oil, PEG-45 hydrogenated castor oil, PEG-50 hydrogenated castor oil, PEG-54 hydrogenated castor oil, PEG-55 hydrogenated castor oil, PEG-60 hydrogenated castor oil, PEG-80 hydrogenated castor oil, and PEG-100 hydrogenated castor oil.
  • Preferred for use in the compositions herein is PEG-60 hydrogenated castor oil.
  • polyethylene glycol derivatives of glycerides can be polyethylene glycol derivatives of stearic acid.
  • Preferred for use in the compositions herein is PEG-100 stearate.
  • compositions of the present invention may further comprise an additional frizz control agent.
  • the additional frizz control agents can be included in the composition of the present invention at a level by weight of, preferably from about 1% to about 40%, more preferably from about 2% to about 25%, still more preferably from about 2% to about 10%.
  • the additional frizz control agent useful herein is selected from the group consisting of (i), (ii), (iii), (iv), (v), and (vi).
  • x is an integer from 1 to 2000
  • y is an integer from 1 to 1000
  • a is zero or greater
  • b is zero or greater
  • the average sum of a+b is at least 1 , and having an HLB value of about 20 or less.
  • the dimethicone copolyols have an HLB of about 15 or less and more preferably the dimethicone copolyols have an HLB of about 11 or less.
  • x is an integer from 1 to 1000
  • y is an integer from 1 to 200.
  • a is an integer from 0 to 100
  • b is an integer from 0 to 100
  • the average sum of a+b is from 1 to 200
  • the ratio of propylene oxide substituents (b) to ethylene oxide substituents (a) is at least about 2:1 , more preferably at least about 3:1 , even more preferably at least about 4:1 , and most preferably the dimethicone copolyols have only propylene oxide substituents and no ethylene oxide substituents.
  • Preferred commercially available comb type dimethicone copolyols include Abil B 8852®, and Abil B 8873 ® (manufactured by the Goldschmidt Chemical Corporation), (ii) dimethicone copolyols having the structure:
  • R is selected from the group consisting of hydrogen, methyl, and combinations thereof, m is an integer from 1 to 2000, x is independently zero or greater, y is independently zero or greater, wherein the dimethicone copolyol has at least one ethylene oxide and/or propylene oxide, and has an HLB value of about 20 or less.
  • R is hydrogen
  • the dimethicone copolyols have an HLB of about 15 or less and more preferably the dimethicone copolyols have an HLB of about 1 1 or less.
  • m is an integer from 1 to 1000, more preferably from 1 to 500.
  • x is an integer from 0 to 100
  • y is an integer from 0 to 100, wherein the dimethicone copolyol has from 1 to 200 of ethylene oxide units and/or propylene oxide units.
  • the ratio of propylene oxide substituents (y) to ethylene oxide substituents (x) is at least about 2:1 , more preferably at least about 3:1 , even more preferably at least about 4:1 , and most preferably the dimethicone copolyols have only propylene oxide substituents and no ethylene oxide substituents.
  • a preferred commercially available linear type dimethicone copolyol, useful herein, is Abil B 8830® (manufactured by the Goldschmidt Chemical Corporation).
  • R groups is selected from saturated or unsaturated fatty acid moieties derived from animal or vegetable oils such as palmitic acid, lauric acid, oleic acid or linoleic acid wherein the fatty acid moieties have a carbon length chain of from 12 and 22, any other R groups are hydrogen, x, y, z are independently zero or more, the average sum of x+y+z (the degree of ethoxylation) is equal to from about 10 to about 45.
  • the PEG-modified glycerides have an HLB value of about 20 or less, more preferably about 15 or less, still preferably about 1 1 or less.
  • the PEG-modified glyceride has from 2 to 3 fatty acid R groups, more preferred are 3 fatty acid R groups (PEG-modified triglycerides).
  • the average sum of x+y+z (the degree of ethoxylation) is equal to from about 20 to 30, more preferred is an average sum of 25. Most preferred are
  • PEG-substituted triglycerides having 3 oleic acid R groups, wherein the average degree of ethoxylation is about 25 PEG-25 glyceryl trioleate.
  • Preferred commercially available PEG-modified triglycerides include
  • Tagat TO ® Tegosoft GC
  • Tagat BL 276® All three manufactured by
  • R is an aliphatic group having from 12 to 22 carbon chain length
  • n the degree of ethoxylation
  • the PEG-modified glyceryl fatty acid esters have an HLB value of about 20 or less, more preferably about 15 or less, still preferably about 1 1 or less.
  • n has an average value of from about 15 to about 30, more preferred is an average value of from about 20 to about 30, and most preferably has an average value of 20.
  • Preferred PEG-modified glyceryl fatty acid esters include PEG-30 glyceryl stearate and PEG-20 glyceryl stearate.
  • Preferred commercially available PEG-modified glyceryl fatty acid esters include Tagat S ® and Tagat S 2 ® (manufactured by Goldschmidt Chemical Corporation), (v) polypropylene glycol
  • Polypropylene glycol useful herein has a weight average molecular weight of preferably from about 200 g/mol to about 100,000 g/mol, more preferably from about 1 ,000 g/mol to about 60,000 g/mol. Without intending to be limited by theory, it is believed that the polypropylene glycol herein deposits onto, or is absorbed into hair to act as a moisturizer buffer, and/or provides one or more other desirable hair conditioning benefits.
  • polypropylene glycol includes single-polypropylene glycol-chain segment polymers, and multi-polypropylene glycol-chain segment polymers.
  • the general structure of branched polymers such as the multi-polypropylene glycol-chain segment polymers herein are described, for example, in "Principles of Polymerization,” pp. 17-19, G. Odian, (John Wiley & Sons, Inc., 3 rd ed., 1991 ).
  • the polypropylene glycol herein are typically polydisperse polymers.
  • the polypropylene glycols useful herein have a polydispersity of from about 1 to about 2.5, preferably from about 1 to about 2, and more preferably from about 1 to about 1.5.
  • the term "polydispersity" indicates the degree of the molecular weight distribution of the polymer sample. Specifically, the polydispersity is a ratio, greater than 1 , equal to the weight average molecular weight divided by the number average molecular weight.
  • the polypropylene glycol useful herein may be either water-soluble, water- insoluble, or may have a limited solubility in water, depending upon the degree of polymerization and whether other moieties are attached thereto.
  • the desired solubility of the polypropylene glycol in water will depend in large part upon the form (e.g., leave-on, or rinse-off form) of the hair care composition.
  • the solubility in water of the polypropylene glycol herein may be chosen by the artisan according to a variety of factors. Accordingly, for a leave-on hair care composition, it is preferred that the polypropylene glycol herein be a water- soluble polypropylene glycol.
  • Solubility information is readily available from polypropylene glycol suppliers, such as Sanyo Kasei (Osaka, Japan).
  • the present invention may also take the form of a rinse-off hair care composition. Without intending to be limited by theory, it is believed that in such a composition, a water-soluble polypropylene glycol may be too easily washed away before it effectively deposits on hair and provides the desired benefit(s). For such a composition, a less soluble, or even a water-insoluble polypropylene glycol is therefore preferred.
  • the polypropylene glycol herein has a solubility in water at 25 °C of less than about 1 g/100 g water, more preferably a solubility in water of less than about 0.5 g/100 g water, and even more preferably a solubility in water of less than about 0.1 g/100 g water.
  • the polypropylene glycol is selected from the group consisting of a single-polypropylene glycol-chain segment polymer, a multi-polypropylene glycol-chain segment polymer, and mixtures thereof, more preferably selected from the group consisting of a single-polypropylene glycol-chain segment polymer of Formula I, below, a multi-polypropylene glycol-chain segment polymer of Formula II, below, and mixtures thereof.
  • a highly preferred single-polypropylene glycol-chain segment polymer has the formula: HO-(C 3 H 6 0) a H (III), wherein a is a value from about 4 to about 400, preferably from about 20 to about 100, and more preferably from about 20 to about 40.
  • the single-polypropylene glycol-chain segment polymer useful herein is typically inexpensive, and is readily available from, for example, Sanyo Kasei (Osaka, Japan), Dow Chemicals (Midland, Michigan, USA), Calgon Chemical, Inc. (Skokie, Illinois, USA), Arco Chemical Co. (Newton Square Pennsylvania, USA), Witco Chemicals Corp. (Greenwich, Connecticut, USA), and PPG Specialty Chemicals (Gurnee, Illinois, USA).
  • a highly preferred multi-polypropylene glycol-chain segment polymer has the formula:
  • n is a value from about 0 to about 10, preferably from about 0 to about 7, and more preferably from about 1 to about 4.
  • each R" is independently selected from the group consisting of H, and C,-C 30 alkyl, and preferably each R" is independently selected from the group consisting of H, and C,-C 4 alkyl.
  • c and d are independently a value from about 0 to about 2, preferably from about 0 to about 1.
  • the total of b + c + d is at least about 2, preferably the total of b + c + d is from about 2 to about 3.
  • Each e is independently a value of 0 or 1 , if n is from about 1 to about 4, then e is preferably equal to 1.
  • x, y, and z is independently a value of from about 1 to about 120, preferably from about 7 to about 100, and more preferably from about 7 to about 100, where x + y + z is greater than about 20. Examples of the multi-polypropylene glycol-chain segment polymer of
  • one or more of the propylene repeating groups in the polypropylene glycol is an isopropyl oxide repeating group. More preferably one or more of the propylene oxide repeating groups of the polypropylene glycol of Formula III and/or the polypropylene glycol of Formula IV is an isopropyl oxide repeating group. Even more preferably, substantially all of the propylene oxide repeating groups of the polypropylene glycol of Formula III and/or the polypropylene glycol of Formula IV are isopropyl oxide repeating groups. Accordingly, a highly preferred single-polypropylene glycol-chain segment polymer has the formula: wherein a is defined as described above for Formula III. Similarly, a highly preferred multi-polypropylene glycol-chain segment polymer has the formula:
  • n, R", b, c, d, e, x, y, and z are defined as above, for Formula IV. It is recognized that the isopropyl oxide repeating groups may also correspond either alone, or in combination with the above depicted, to:
  • the polypropylene glycol useful herein is readily available from, for example, Sanyo Kasei (Osaka, Japan) as New pol PP-2000, New pol PP-4000, New pol GP-4000, and New pol SP-4000, from Dow Chemicals (Midland, Michigan, USA), from Calgon Chemical, Inc. (Skokie, Illinois, USA), from Arco Chemical Co. (Newton Square Pennsylvania, USA), from Witco Chemicals Corp. (Greenwich, Connecticut, USA), and from PPG Specialty Chemicals (Gurnee, Illinois, USA).
  • the hair care compositions of the present invention may also comprise a sensate.
  • a sensate means a substance that, when applied to the skin, causes a perceived sensation of a change in conditions, for example, but not limited to, heating, cooling, refreshing and the like. Sensates are preferably utilized at levels of from about 0.001 % to about 10%, more preferably from about 0.005% to about 5%, even more preferably from about 0.01 % to about 1%, by weight, of the total composition. Any sensate suitable for use in hair care compositions may be used herein.
  • sensates can be found in GB-B-1315626, GB-B-1404596 and GB-B- 1411785, all incorporated by reference herein.
  • Preferred sensates for use in the compositions herein are camphor, menthol, l-isopulegol, ethyl menthane carboxamide and trimethyl isopropyl butanamide.
  • compositions of this invention may also contain optional components which may modify the physical and performance characteristics of the conditioning product.
  • Such components include additional surfactants, salts, buffers, thickeners, solvents, opacifiers, pearlescent aids, preservatives, fragrance, colorants, dyes, pigments, chelators, sunscreens, vitamins, and medicinal agents.
  • Optional components that are among those useful herein are disclosed in U.S. Pat. No. 4,387,090, Bolich, Jr., issued Jun. 7, 1983, incorporated by reference herein.
  • compositions of the present invention may also optionally contain an anti-dandruff agent.
  • the anti-dandruff agent provides the shampoo compositions with anti-microbial activity.
  • the anti-dandruff agent may be particulate or soluble.
  • the preferred type of anti-dandruff agents are particulate, crystalline anti- dandruff agents, such as sulfur, selenium sulfide and heavy metal salts of pyridinethione.
  • Especially preferred is zinc pyridinethione.
  • Soluble anti-dandruff agents, such as ketoconazole, are also known in the art.
  • the anti-dandruff agent comprises from about 0.1 % to about 4%, by weight of the composition, preferably from about 0.1% to about 3%, most preferably from about 0.3% to about 2%, of the composition.
  • Such anti-dandruff agent should be physically and chemically compatible with the essential components of the composition, and should not otherwise unduly impair product stability, aesthetics or performance.
  • compositions of the present invention may also optionally contain one or more hair growth agents, such as zinc pyridinethione.
  • the compositions of the present invention may also optionally contain a compound useful for regulating the growth and loss of hair.
  • Such compounds known in the art include lupane triterpenes, derivatives of lupane triterpenes, derivatives of oleanane triterpenes, derivatives of ursane triterpenes, and salts and mixtures thereof, minoxidil (Rogaine®)(6-(1-piperidinyl)-2,4-pyrimidinediamine 3-oxide). See, U.S.
  • Another currently marketed product for promoting hair growth is Finasteride (Propecia®). See. EP 823436; US 5,670,643; WO 97/15564; and WO 97/15558.
  • Such hair growth/regulators should be physically and chemically compatible with the essential components of the composition and should not otherwise unduly impair product stability, aesthetics or performance.
  • compositions of the present invention may contain additional surfactant materials, at levels such that the total level of surfactant present in the composition (including the essential cationic surfactant vehicle material, described above) is from about 0.01% to about 20%.
  • optional surfactant materials may be anionic, nonionic or amphoteric, such as ceteareth-20, steareth-20, sorbitan monoesters, sodium tallow alkylsulfate and tallow betaine.
  • Optional surfactant materials are described in the following documents, all incorporated by reference herein: M. C.
  • Salts and buffers may also be added in order to modify the product rheology.
  • salts such as potassium chloride and sodium chloride, may be added at levels of from about 0.001% to about 1%.
  • Buffers such as citrate or phosphate buffers, may also be used.
  • pH of the present compositions modified to a pH of from about 3 to about 10, preferably from about 3 to about 7.
  • a wide variety of other additional components can be formulated into the present compositions. These include: other conditioning agents such as hydrolysed collagen with tradename Peptein 2000 available from Hormel, vitamin E with tradename Emix-d available from Eisai, panthenol available from Roche, panthenyl ethyl ether available from Roche, hydrolysed keratin, proteins, plant extracts, and nutrients; hair-fixative polymers such as amphoteric fixative polymers, cationic fixative polymers, anionic fixative polymers, nonionic fixative polymers, and silicone grafted copolymers; preservatives such as benzyl alcohol, methyl paraben, propyl paraben and imidazolidinyl urea; pH adjusting agents, such as glutamic acid, citric acid, sodium citrate, succinic acid, phosphoric acid, sodium hydroxide, sodium carbonate; salts, in general, such as potassium acetate and sodium chloride; coloring agents, such as any of the FD&C or D
  • Optional components may be incorporated which provide additional conditioning benefits.
  • proteins may be added at levels of from about 0.1 %) to about 10%.
  • Cationic proteins may also serve as surfactant vehicle materials in the present invention.
  • Styryl Silicone Styryl MQ Silicone available from GE Silicones *10 Cetyl Hydroxyethyl cellulose: Natrosol Plus CS Grade 330 available from
  • Pentaerythritol ester oil pentaerythritol tetraoleate with tradename KAKTTI available from Koukyu Alcohol Kogyo *13 Dimethicone copolyol-2: Abil B 8852 available from Goldschmidt Chemical
  • Crovol A-40 available from Croda Chemical
  • the mixture is then cooled at a rate controlled to protect overall product integrity (this can occur by any convenient means).
  • compositions according the present invention is from about 6.0 to about 7.5.
  • Examples I through IX are hair conditioning compositions of the present invention which are particularly useful for leave-on use. These examples have many advantages. For example, they can provide have increased efficacy for frizz control while retaining good conditioning/shine benefits and good hair feel and appearance, i.e., they can provide improved frizz control benefit in addition to other conditioning benefits such as smoothness, softness, shine and reduction of friction, and leave the hair and hands with a clean feeling. It is understood that the examples and embodiments described herein are for illustrative purposes only and that various modifications or changes in light thereof will be suggested to one skilled in the art without departing from its spirit and scope.

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Abstract

La présente invention concerne des compositions de soin capillaire comprenant en poids: a) d'environ 0,001 % à environ 5 % d'une résine polysiloxane non volatile; b) d'environ 1 % à environ 50 % d'une huile d'ester pentaérythritol en tant qu'agent de lissage; c) d'environ 1,1 % à environ 13 % d'un excipient qui comprend une substance lipidique et un tensioactif cationique; d) d'environ 0,01 % à environ 5 % d'un épaississant hydroxyalkyl cellulose rendu hydrophobe; et (e) un support aqueux. La composition de soin capillaire de l'invention permet d'obtenir un lissage amélioré des cheveux et une sensation plus agréable au toucher.
PCT/US2000/014881 2000-05-30 2000-05-30 Compositions de soin capillaire contenant un agent de lissage WO2001091707A1 (fr)

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PCT/US2000/014881 WO2001091707A1 (fr) 2000-05-30 2000-05-30 Compositions de soin capillaire contenant un agent de lissage
AU2000255909A AU2000255909A1 (en) 2000-05-30 2000-05-30 Hair care compositions comprising a frizz control agent

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004028496A1 (fr) * 2002-09-27 2004-04-08 Unilever Plc Compositions aqueuses revitalisantes a laisser sur le cheveu
WO2007019160A1 (fr) * 2005-08-03 2007-02-15 Alberto-Culver Company Composition de conditionneur capillaire a dispersion rapide
EP1792604A1 (fr) * 2005-12-02 2007-06-06 Cognis IP Management GmbH Composition de traitement capillaire
WO2010055039A2 (fr) * 2008-11-14 2010-05-20 Unilever Plc Composition
WO2021134463A1 (fr) * 2019-12-31 2021-07-08 L'oreal Composition permettant le conditionnement de matières kératiniques

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5106609A (en) * 1990-05-01 1992-04-21 The Procter & Gamble Company Vehicle systems for use in cosmetic compositions
WO1994008557A1 (fr) * 1992-10-22 1994-04-28 The Procter & Gamble Company Compositions pour soins favorisant la coiffure et le brillant
US6024946A (en) * 1991-06-03 2000-02-15 L'oreal Silicon and latex-based composition for the treatment of keratinous substances

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5106609A (en) * 1990-05-01 1992-04-21 The Procter & Gamble Company Vehicle systems for use in cosmetic compositions
US6024946A (en) * 1991-06-03 2000-02-15 L'oreal Silicon and latex-based composition for the treatment of keratinous substances
WO1994008557A1 (fr) * 1992-10-22 1994-04-28 The Procter & Gamble Company Compositions pour soins favorisant la coiffure et le brillant

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004028496A1 (fr) * 2002-09-27 2004-04-08 Unilever Plc Compositions aqueuses revitalisantes a laisser sur le cheveu
US7192574B2 (en) 2002-09-27 2007-03-20 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Stable cosmetic sprayable products with a desirable narrow conical spray pattern
WO2007019160A1 (fr) * 2005-08-03 2007-02-15 Alberto-Culver Company Composition de conditionneur capillaire a dispersion rapide
AU2006278686B2 (en) * 2005-08-03 2011-03-31 Alberto-Culver Company Quick dispersing hair conditioning composition
EP2340873A1 (fr) * 2005-08-03 2011-07-06 Alberto-Culver Company Composition de conditionneur capillaire a dispersion rapide
US8277788B2 (en) 2005-08-03 2012-10-02 Conopco, Inc. Quick dispersing hair conditioning composition
EP1792604A1 (fr) * 2005-12-02 2007-06-06 Cognis IP Management GmbH Composition de traitement capillaire
WO2010055039A2 (fr) * 2008-11-14 2010-05-20 Unilever Plc Composition
WO2010055039A3 (fr) * 2008-11-14 2011-09-09 Unilever Plc Composition
WO2021134463A1 (fr) * 2019-12-31 2021-07-08 L'oreal Composition permettant le conditionnement de matières kératiniques
CN114901249A (zh) * 2019-12-31 2022-08-12 莱雅公司 用于调理角蛋白材料的组合物

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