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WO2020092031A1 - Compositions après-shampoing - Google Patents

Compositions après-shampoing Download PDF

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Publication number
WO2020092031A1
WO2020092031A1 PCT/US2019/057132 US2019057132W WO2020092031A1 WO 2020092031 A1 WO2020092031 A1 WO 2020092031A1 US 2019057132 W US2019057132 W US 2019057132W WO 2020092031 A1 WO2020092031 A1 WO 2020092031A1
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WO
WIPO (PCT)
Prior art keywords
weight
meth
composition
hair
polymers
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2019/057132
Other languages
English (en)
Inventor
Lu Bai
Liang Chen
Yunshen CHEN
Bethany Johnson
Jennifer KOENIG
Lyndsay M. LEAL
Fanwen Zeng
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Global Technologies LLC
Rohm and Haas Co
Dow Silicones Corp
Original Assignee
Dow Global Technologies LLC
Rohm and Haas Co
Dow Silicones Corp
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Filing date
Publication date
Application filed by Dow Global Technologies LLC, Rohm and Haas Co, Dow Silicones Corp filed Critical Dow Global Technologies LLC
Publication of WO2020092031A1 publication Critical patent/WO2020092031A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • 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
    • A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners

Definitions

  • This invention relates generally to hair conditioning compositions containing
  • polyacrylate oil gels containing hydrophobic ester oils and acrylic polymers.
  • Personal care hair conditioning compositions contain a variety of components that provide a wide array of benefits to the composition.
  • One class of additives are oil thickeners that provide viscosity enhancements and impart good aesthetics, such as good sensory feel and clarity.
  • Oil thickening agents that are known in the art include, for example, styrene- ethylene/butadiene- styrene copolymers, polyamide polymers, and cellulose-based polymers. These thickeners, however, come with certain drawbacks, including insufficient viscosity enhancement, high formulation temperature, and lack of consistency in viscosity control in consumer product formulations.
  • polyacrylate oil gels have been utilized in the art.
  • WO 2017/105957 Al discloses personal care compositions comprising a polyacrylate oil gel containing a cosmetically acceptable hydrophobic ester oil and a polymer including at least two polymerized units.
  • the prior art does not, however, disclose a hair conditioning formulation containing polyacrylate oil gels according to the present invention which achieves the significant conditioning performance such as ease of detangling, smoothness, pliability, slipperiness, and luster.
  • One aspect of the invention provides a hair conditioning composition
  • a hair conditioning composition comprising (a) of a polyacrylate oil gel, based on the total weight of the composition, wherein the polyacrylate oil gel comprises (i) at least one cosmetically acceptable hydrophobic ester oil, and (ii) one or more polymers comprising polymerized structural units of (1) 96 to 99.89 weight % of C 4 -Cs
  • (meth)acrylate monomers (2) 0.1 to 2 weight % of (meth)acrylic acid monomer, and (3) 0.01 to 2 weight % of at least one crosslinker, (b) a dermatologically acceptable carrier, and (c) a surface active agent.
  • Another aspect of the invention provides (a) 0.1 to 20 weight % of a polyacrylate oil gel, based on the total weight of the composition, wherein the polyacrylate oil gel comprises (i) at least one cosmetically acceptable hydrophobic ester oil comprising one or more aliphatic C 8 -C 24 alkyl triglycerides, and (ii) one or more polymers comprising polymerized structural units of (1) 96 to 99.89 weight % of C 4 -Cs (meth)acrylate monomers selected from the group consisting of ethylhexyl (meth)acrylate, butyl (meth)acrylate, and mixtures thereof, (2) 0.1 to 2 weight % of (meth)acrylic acid monomer, and (3) 0.01 to 2 weight % of at least one crosslinker selected from the group consisting of trimethylolpropane trimethacrylate, trimethylolpropane diallyl ether, ethylene glycol dimethylacrylate, and mixtures thereof, (b) 50 to 99.
  • the invention provides a method for conditioning hair, comprising topically administering to the hair an effective amount of a hair conditioning composition
  • a hair conditioning composition comprising (a) of a polyacrylate oil gel, based on the total weight of the composition, wherein the polyacrylate oil gel comprises (i) at least one cosmetically acceptable hydrophobic ester oil, and (ii) one or more polymers comprising polymerized structural units of (1) 96 to 99.89 weight % of C4-C8 (meth) acrylate monomers, (2) 0.1 to 2 weight % of (meth)acrylic acid monomer, and (3) 0.01 to 2 weight % of at least one crosslinker, (b) a dermatologically acceptable carrier, and (c) a surface active agent.
  • hair conditioning compositions comprising a polyacrylate oil gel containing one or more polymers having a high weight percent of polymerized structural units of C4-C8 (meth) acrylate monomer, a small weight percent of (meth)acrylic acid monomer, and a small weight percent of crosslinker, a dermatologically acceptable carrier, and a surface active agent, provide significant conditioning enhancements such as ease of detangling, smoothness, pliability, slipperiness, and luster, while avoiding the greasiness associated with oil-containing hair conditioning formulations.
  • the present invention provides in one aspect a conditioning composition
  • a conditioning composition comprising (a) a polyacrylate oil gel comprising (i) a hydrophobic ester oil, (1) 96 to 99.89 weight % of C 4 - C 8 (meth)acrylate monomers, (2) 0.1 to 2 weight % of (meth)acrylic acid monomer, and (3) 0.01 to 2 weight % of at least one crosslinker, (b) a dermatologically acceptable carrier, and (c) a surface active agent.
  • hair conditioning is intended to refer to cosmetic
  • compositions for application to hair including, for example, leave-on conditioners and rinse-off conditioners.
  • the personal care composition is cosmetically acceptable.
  • compositions of the invention may be manufactured by processes well known in the art, for example, by means of conventional mixing, dissolving, granulating, emulsifying, encapsulating, entrapping or lyophilizing processes.
  • the term“polymer” refers to a polymeric compound prepared by polymerizing monomers, whether of the same or a different type.
  • the generic term“polymer” includes the terms“homopolymer,”“copolymer,” and“terpolymer.”
  • the term “polymerized structural units” of a given monomer refers to the remnant of the monomer after polymerization.
  • the term“(meth)acrylate” refers to either acrylate or methacrylate
  • the term“(meth) acrylic” refers to either acrylic or methacrylic.
  • the term“substituted” refers to having at least one attached chemical group, for example, alkyl group, alkenyl group, vinyl group, hydroxyl group, carboxylic acid group, other functional groups, and combinations thereof.
  • the inventive hair conditioning compositions include polyacrylate oil gels containing one or more polymers and one or more hydrophobic ester oils.
  • the polyacrylate oil gels are present in the hair conditioning composition in an amount of from 0.1 to 20 weight %, preferably from 0.5 to 10, and more preferably from 1 to 6 weight %, based on the total weight of the hair conditioning composition.
  • the polyacrylate oil gels of the invention contain one or more polymers comprising structural units of C 4 - C 8 (meth)acrylate monomers and (meth)acrylic acid monomers.
  • Suitable C 4 -C 8 (meth)acrylate monomers include, for example, n-butyl (meth)acrylate, i-butyl
  • the C4-C8 (meth)acrylate monomers comprise one or more of i-butyl methacrylate, n-butyl methacrylate, and 2-ethylhexyl methacrylate.
  • the polymer comprises polymerized structural units of C 4 -C 4 (meth) acrylate monomers in an amount of from 96 to 99.89, preferably from 97.5 to 99.5 weight %, more preferably from 98.2 to 99.3 weight %, and more preferably from 98.9 to 99.1 weight %, based on the total weight of the polymer.
  • the C 4 -C 4 (meth)acrylate monomers comprise i-butyl methacrylate and 2- ethylhexyl methacrylate in a ratio of from 9:1 to 2:3, preferably from 3:2 to 2:3, and more preferably from 1:1 to 2:3.
  • the polymers of the inventive hair conditioning compositions also comprise structural units of (meth)acrylic acid monomer.
  • the polymer comprises polymerized structural units of (meth)acrylic acid monomer in an amount of from 0.1 to 2 weight %, preferably from 0.5 to 1.5 weight %, and more preferably from 0.75 to 1.25 weight %, based on the total weight of the polymer.
  • the polymers of the inventive hair conditioning composition also comprise polymerized structural units of at least one crosslinker.
  • Crosslinkers are monomers having two or more non- conjugated ethylenically unsaturated groups.
  • Suitable crosslinkers include, for example, di- or tri-allyl ethers and di- or tri- (meth) aery lyl esters of diols or polyols (e.g., trimethylolpropane diallyl ether (TMPDE), trimethylolpropane trimethacrylate (TMPTMA), and ethylene glycol dimethacrylate (EGDMA)), di- or tri-allyl esters of di- or tri-acids (e.g., diallyl phthalate), allyl (meth)acrylate, divinyl sulfone, triallyl phosphate, and divinylaromatics (e.g., divinylbenzene).
  • TMPDE trimethylolpropane diallyl ether
  • the polymer comprises polymerized structural units of crosslinker in an amount of from 0.01 to 2 weight %, preferably from 0.05 to 1.6 weight %, and more preferably from 0.1 to 1.4 weight %, based on the total weight of the polymer.
  • the polymers have an average particle size of from 50 to 2,000 nm, preferably of from 75 to 1,100 nm, and more preferably of from 100 to 200 nm. Polymer molecular weights can be measured by standard methods such as, for example, size exclusion chromatography or intrinsic viscosity.
  • the polymers are present in the polyacrylate oil gel in an amount of from 3 to 15 weight %, preferably from 4 to 10, and more preferably from 5 to 7 weight %, based on the total weight of the polyacrylate oil gel.
  • the polymers are present in the hair conditioning composition in an amount of from 0.05 to 10 weight %, preferably from 0.10 to 5 weight %, and more preferably from 0.15 to 1.5 weight %, based on the total weight of the composition.
  • Suitable polymerization techniques for preparing the polymers contained in the inventive personal care compositions include, for example, emulsion polymerization.
  • Aqueous emulsion polymerization processes typically are conducted in an aqueous reaction mixture, which contains at least one monomer and various synthesis adjuvants, such as the free radical sources, buffers, and reductants in an aqueous reaction medium.
  • a chain transfer agent may be used to limit molecular weight.
  • the aqueous reaction medium is the continuous fluid phase of the aqueous reaction mixture and contains more than 50 weight % water and optionally one or more water miscible solvents, based on the weight of the aqueous reaction medium.
  • Suitable water miscible solvents include, for example, methanol, ethanol, propanol, acetone, ethylene glycol ethyl ethers, propylene glycol propyl ethers, and diacetone alcohol.
  • the aqueous reaction medium contains more than 90 weight % water, preferably more than 95 weight % water, and more preferably more than 98 weight % water, based on the weight of the aqueous reaction medium.
  • the polymers of the present invention may be isolated by a spray drying process. While spray drying is one preferred embodiment of how to produce the dry powder, other suitable methods include, for example, freeze drying, a two-step process including the steps of (i) pan drying the emulsion and then (ii) grinding the pan dried material into a fine powder, coagulation of the acrylic emulsion and collection of the powder by filtration followed by washing and drying, fluid bed drying, roll drying, and freeze drying. Suitable techniques for spray drying the polymer beads of the present invention are known in the art, for example, as described in US 2014/0113992 Al. In certain embodiments, anti-caking agents are used when spray drying the polymer beads.
  • Suitable anti-caking agents include, for example, mineral fillers (e.g., calcium carbonate, kaolin, titanium oxide, talc, hydrated alumina, bentonite, and silica), solid polymer particles with a T g or T m greater than 60°C (e.g., polymethylmethacrylate, polystyrene, and high density polyethylene), and water soluble polymers with a T g greater than 60°C (e.g., polyvinyl alcohol and methylcellulose).
  • the anti-caking agent can be mixed in the acrylic suspension prior to spray drying or introduced as a dry powder in the spray drying process.
  • the anti-caking agent coats the polymer beads to prevent the beads from sticking to each other inner wall of the dryer.
  • the anti-caking agent is present in an amount of from 0 to 20 weight %, and more preferably from 0.01 to 10 weight %, based on the total weight of the polymer beads.
  • the polyacrylate oil gels of the present invention also contain a cosmetically acceptable hydrophobic ester oil.
  • a cosmetically acceptable hydrophobic ester oil In general, any hydrophobic ester oil or mixtures thereof which are toxicologically safe for human or animal use may constitute the oil base of the present invention.
  • the hydrophobic ester oil comprises aliphatic C 8 -C 24 alkyl
  • Suitable hydrophobic ester oils include, for example, caprylic/capric triglycerides, saturated fatty esters and diesters (e.g., isopropyl palmitate, octyl palmitate, butyl stearate, isocetyl stearate, octadodecyl stearate, octadodecyl stearoyl stearate, diisopropyl adipate, and dioctyl sebacate), and animal oils and vegetable oils (e.g., mink oil, coconut oil, soybean oil, palm oil, corn oil, cocoa butter, sesame oil, sunflower seed oil, jojoba oil, olive oil, lanolin oil, almond oil, and argan oil).
  • caprylic/capric triglycerides saturated fatty esters and diesters (e.g., isopropyl palmitate, octyl palmitate, butyl stearate, iso
  • the hydrophobic ester oil is diffused in an oil base.
  • oil bases include any oil or mixture of oils which are conventionally used in personal care products including, for example, paraffin oils, paraffin waxes, and fatty alcohols (e.g., stearyl alcohol, isostearyl alcohol, and isocetyl alcohol).
  • paraffin oils paraffin waxes
  • fatty alcohols e.g., stearyl alcohol, isostearyl alcohol, and isocetyl alcohol.
  • the hydrophobic ester oil comprises one or more of caprylic/capric triglycerides and sunflower seed oil.
  • the hydrophobic ester oils are present in the polyacrylate oil gel in an amount of from 85 to 99.95 weight %, preferably from 90 to 99.8 weight %, and more preferably from 93 to 99 weight %, based on the total weight of the polyacrylate oil gel.
  • the hydrophobic ester oils are present in the hair conditioning composition in an amount of from 0.25 to 40 weight %, preferably from 0.9 to 15 weight %, and more preferably from 2.85 to 8.5 weight %, based on the total weight of the composition.
  • the hair conditioning compositions of the present invention also include a
  • dermatologically acceptable carrier Such material is typically characterized as a carrier or a diluent that does not cause significant irritation to the skin and does not negate the activity and properties of active agent(s) in the composition.
  • dermatologically acceptable carriers include, without limitation, water, such as deionized or distilled water, emulsions, such as oil-in-water or water-in-oil emulsions, alcohols, such as ethanol, isopropanol or the like, glycols, such as propylene glycol, glycerin or the like, creams, aqueous solutions, oils, ointments, pastes, gels, lotions, milks, foams, suspensions, powders, or mixtures thereof.
  • the aqueous solutions may contain cosolvents, e.g., water miscible cosolvents.
  • Suitable water miscible cosolvents include, for example, ethanol, propanol, acetone, ethylene glycol ethyl ethers, propylene glycol propyl ethers, and diacetone alcohol.
  • the composition contains from about 50 to about 99.7 percent by weight of the dermatologically acceptable carrier, based on the total weight of the composition.
  • the hair conditioning compositions of the present invention also contain at least one surface active agent.
  • Suitable surface active agents include, for example, glyceryl esters, fatty alcohols, nonionic surfactants, cationic surfactants, anionic surfactants, and amphoteric surfactants.
  • Suitable glyceryl esters include, for example, glyceryl distearate, PEG- 100 Stearate, 2- ethyl hexyl oleate, glycerol trioleate, glyceryl monooleate, glyceryl monotallate, n-butyl stearate, neopentylglycol dioleate, pentaerythritol monooleate, pentaerythritol tetraoleate, and tmp- trioleate.
  • Suitable fatty aclohols include, for example, decyl alcohol, decyl lauryl alcohol, lauryl alcohol, lauryl myristyl alcohol, lauryl cetyl alcohol, lauryl stearyl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, octyl decyl alcohol, cetearyl alcohol, and octyldodecanol.
  • Suitable nonionic surfactants include, for example, polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, alkylglucosides, polyoxyethylene fatty acid esters, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters.
  • Suitable nonionic surfactants also include poly(oxyethylene)-poly(oxypropylene)-poly (oxy ethylene) tri -block copolymers .
  • Poly(oxyethylene)-poly(oxypropylene)-poly(oxyethylene) tri-block copolymers are also commonly known as Poloxamers.
  • suitable nonionic surfactants include, for example, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenol ethers, polyoxyethylene lauryl ethers, polyoxyethylene sorbitan monooleates, polyoxyethylene alkyl esters, polyoxyethylene sorbitan alkyl esters, polyethylene glycol, polypropylene glycol, diethylene glycol, ethoxylated trimethylnonanols, and polyoxyalkylene glycol modified polysiloxane surfactants.
  • the nonionic surfactant may be selected from polyoxyalkylene-substituted silicones, silicone alkanolamides, silicone esters, and silicone glycosides.
  • Suitable cationic surfactants include, for example, ester quat, dodecyltrimethyl ammonium chloride/lauryltrimethyl ammonium chloride (LTAC), cetyltrimethyl ammonium chloride (CTAC), didodecyldimethyl ammonium bromide, dihexadecyldimethyl ammonium chloride, dihexadecyldimethyl ammonium bromide, dioctadecyldimethyl ammonium chloride, dieicosyldimethyl ammonium chloride, and didocosyldimethyl ammonium chloride, and fatty acid amines and amides and their salts and derivatives (e.g., as aliphatic fatty amines and their derivatives).
  • LTAC dodecyltrimethyl ammonium chloride/lauryltrimethyl ammonium chloride
  • CTAC cetyltrimethyl ammonium chloride
  • didodecyldimethyl ammonium bromide di
  • Suitable anionic surfactants include, for example: (i) sulfonic acids and their salt derivatives, including alkyl, aralkyl, alkyl naphthalene, alkyl diphenyl ether sulfonic acids, and their salts, having at least 6 carbon atoms in the alkyl substituent (e.g., dodecyl benzene sulfonic acid, and its sodium salt or its amine salt); (ii) alkyl sulfates having at least 6 carbon atoms in the alkyl substituent (e.g., sodium lauryl sulfate); (iii) the sulfate esters of polyoxyethylene monoalkyl ethers; (iv) long chain carboxylic acid surfactants and their salts (e.g., lauric acid, steric acid, oleic acid, and their alkali metal and amine salts).
  • sulfonic acids and their salt derivatives including alkyl,
  • anionic surfactants are alkali metal sulfosuccinates, sulfonated glyceryl esters of fatty acids (e.g., sulfonated monoglycerides of coconut oil acids), salts of sulfonated monovalent alcohol esters (e.g., sodium oleyl isothionate), amides of amino sulfonic acids (e.g., the sodium salt of oleyl methyl tauride), sulfonated products of fatty acid nitriles (e.g., palmitonitrile sulfonate), sulfonated aromatic hydrocarbons (e.g., sodium alpha-naphthalene monosulfonate), condensation products of naphthalene sulfonic acids with formaldehyde, sodium octahydro anthracene sulfonate, alkali metal alkyl sulfates, ether sulfates having al
  • Suitable amphoteric surfactants include, for example, betaines (e.g., betaines (e.g., betaines),
  • cocamidopropylbetaine cocamidopropylbetaine
  • sultaines e.g., cocamidopropylhydroxysultaine
  • lecithin lecithin
  • hydrogenated lecithin hydrogenated lecithin
  • the hair conditioning compositions include surface active agents in an amount of from 0.1 to 20 weight %, preferably 1 to 10 weight %, and more preferably from 2 to 5 weight %, based on the total weight of the hair conditioning composition.
  • the hair conditioning compositions further contain a
  • conditioning agent include, for example, cationic polymers, proteins, natural oils, silicones, waxes, and hydrocarbon oils.
  • Suitable cationic polymers include, for example, cationically charge-modified polymers derived from various animal and plant sources, e.g., guar gum and guar gum derivatives, cellulose, proteins, polypeptides, chitosan, lanolin, starches, silicones, and cationically charge-modified cellulose polymers (e.g., polyquaternium-lO and polyquaternium-67).
  • Suitable proteins include, for example, cocodimonium hydroxypropyl hydrolyzed casein, cocodimonium hydroxypropyl hydrolyzed collagen, cocodimonium hydroxypropyl hydrolyzed hair keratin, cocodimonium hydroxypropyl hydrolyzed keratin, cocodimonium hydroxypropyl hydrolyzed rice protein, cocodimonium hydroxypropyl hydrolyzed silk, cocodimonium hydroxypropyl hydrolyzed soy protein, cocodimonium hydroxypropyl hydrolyzed wheat protein, cocodimonium hydroxypropyl silk amino acids, cocoyl hydrolyzed collagen, cocoyl hydrolyzed keratin, hydrolyzed keratin, hydrolyzed oat flour, hydrolyzed silk, hydrolyzed silk protein, hydrolyzed soy protein, hydrolyzed wheat protein, hydrolyzed wheat protein, keratin, potassium cocoyl hydrolyzed collagen, TEA
  • Suitable natural oils include, for example, castor oil, triisocetyl citrate, sorbitan sesquioleate, Cio-is triglycerides, caprylic/capric/triglycerides, coconut oil, corn oil, cottonseed oil, glyceryl triacetyl hydroxystearate, glyceryl triacetyl ricinoleate, glyceryl trioctanoate, hydrogenated castor oil, linseed oil, mink oil, olive oil, palm oil, illipe butter, rapeseed oil, soybean oil, sunflower seed oil, tricaprin, trihydroxystearin, triisostearin, trilaurin, trilinolein, trimyristin, triolein, tripalmitin, tristearin, walnut oil, wheat germ oil, and cholesterol, perhydrosqualene or arara oil, and sweet almond, calophyllum, palm, castor, avocado, jojoba, argan, olive, and cereal
  • Suitable silicones include, for example, silicone fluids, gums, resins, elastomers, silicone surfactants and emulsifiers (e.g., silicone poly ethers), organofunctional silicones (e.g., aminofunctional silicones and alkylmethylsiloxanes).
  • Suitable waxes include, for example, synthetic wax, ceresin, paraffin, ozokerite, illipe butter, beeswax, carnauba, microcrystalline, lanolin, lanolin derivatives, candelilla, cocoa butter, shellac wax, spermaceti, bran wax, capok wax, sugar cane wax, montan wax, whale wax, bayberry wax, animal waxes (e.g, beeswax), vegetable waxes (e.g., camauba, candelilla, ouricury or japan wax or cork fibre or sugarcane waxes), mineral waxes (e.g., paraffin or lignite wax or microcrystalline waxes), synthetic waxes (e.g., polyethylene waxes, waxes obtained by the Fischer-Tropsch synthesis, silicone waxes (e.g., polymethylsiloxane alkyls, alkoxys, and/or esters).
  • the hair e.g.,
  • conditioning compositions include conditioning agents in an amount of from 0.1 to 10 weight %, preferably 0.2 to 5 weight %, and more preferably from 0.3 to 2 weight %, based on the total weight of the hair conditioning composition.
  • the hair conditioning compositions further contain a thickener.
  • Suitable thickeners include, for example, acrylates copolymers (e.g., ACULYNTM 33 available from The Dow Chemical Company), acrylates cross-polymers, urethanes (e.g., ACULYNTM
  • cellulose derivatives e.g., hydroxy ethylecellulose, methylcellulose, methylhydroxypropylcellulose, hydroxypropylcellulose, and polypropylhydroxyethylcellulose
  • starch, and starch derivatives e.g., hydroxy
  • the thickeners are selected from the group consisting of acrylates copolymers, acrylates cross-polymers, urethanes, cellulose derivatives, saccharide derivatives, electrolytes, and mixtures thereof.
  • the thickener is used in an amount sufficient to provide a viscosity in the hair conditioner composition of 500 mm 2 /s to 25,000 mm 2 /s.
  • the hair conditioning compositions include thickeners in an amount of from 0.05 to 10 weight %, and preferably 0.05 to 5 weight %, based on the total weight of the hair conditioning composition.
  • the hair conditioning compositions according to the present invention may be formulated by conventional mixing processes known to those skilled in the art.
  • the formulation temperature is from 5 to l50°C, preferably from 25 to 70°C.
  • the order of addition of the polymer particles, hydrophobic ester oil, surface active agent, and dermatologically acceptable carrier is not consequential, and thus can be mixed in any order of addition.
  • polymer particles are pre-mixed with hydrophobic ester oil, and then emulsified into the dermatologically acceptable carrier.
  • compositions of the invention may be included in the compositions of the invention such as, but not limited to, abrasives, absorbents, aesthetic components such as fragrances, pigments, colorings/colorants, essential oils, skin sensates, astringents (e.g., clove oil, menthol, camphor, eucalyptus oil, eugenol, menthyl lactate, witch hazel distillate), preservatives, anti-caking agents, a foam building agent, antifoaming agents, antimicrobial agents (e.g., iodopropyl butylcarbamate), antioxidants, binders, biological additives, buffering agents, bulking agents, chelating agents, chemical additives, cosmetic astringents, cosmetic biocides, denaturants, drug astringents, external analgesics, film formers or materials, e.g., polymers, for aiding the film forming properties and substantivity of the composition (e.g., copolymer of
  • the hair conditioning compositions of the present invention are useful for the conditioning of hair, including, for example, ease of detangling, smoothness, pliability, slipperiness, and luster.
  • the hair conditioning compositions may be used in a method for conditioning hair comprising topically administering to the hair a composition comprising (a) a polyacrylate oil gel, based on the total weight of the composition, wherein the polyacrylate oil gel comprises (i) at least one cosmetically acceptable hydrophobic ester oil, and (ii) one or more polymers comprising polymerized structural units of (1) 96 to 99.89 weight % of C 4 -Cs (me th) acrylate monomers, (2) 0.1 to 2 weight % of (meth)acrylic acid monomer, and (3) 0.01 to 2 weight % of at least one crosslinker, (b) a dermatologically acceptable carrier; and (c) a surface active agent.
  • the hair conditioning compositions are generally administered topically by applying or spreading the compositions onto the hair.
  • the frequency may depend, for example, on the level of dryness an individual is likely to encounter in a given day and/or the sensitivity of the individual to humidity.
  • administration on a frequency of at least once per day may be desirable.
  • Exemplary polymers in accordance with the present invention and comparative polymers contain the components recited in Table 1.
  • iBMA ⁇ o-butyl methacrylate
  • EHMA 2-ethylhexyl methacrylate
  • MAA methacrylic acid
  • TMPTMA trimethylolpropane trimethacrylate
  • EGDMA ethylene glycol dimethylacrylate
  • Synthesis of exemplary polymer P-El was carried out as follows. A three liter round bottom flask was equipped with a mechanical overhead stirrer, heating mantle, thermocouple, condenser and inlets for the addition of monomer, initiator and nitrogen. The kettle was charged with 470 grams deionized water and 7.46 grams of DS-4 (Polystep A-16-22: sodium
  • a kettle buffer solution of 1.92 grams of ammonium bicarbonate and 12.71 grams of deionized water was prepared and set aside.
  • a preform seed of 22.38 grams was removed from the stable monomer emulsion and put into a small beaker.
  • a rinse of 16.8 grams of deionized water was prepared.
  • a co-feed catalyst charge of 0.28 grams of ammonium persulfate and 49.22 grams of deionized water was prepared and set aside.
  • the kettle buffer solution and initial catalyst solution were added to the reactor, followed by the perform seed and rinse.
  • the reaction was monitored for a small exotherm. After the exotherm, the temperature control was adjusted to 83-85°C.
  • the monomer emulsion feed was added to the kettle, sub-surface, at a rate of 4.40 grams/minute for 15 minutes. After 15 minutes, the rate was increased to 8.80 grams/minutes for 75 minutes, giving a total feed time of 90 minutes. While the monomer emulsion feed was added to the kettle, the co-feed catalyst solution was also added over 90 minutes at a rate of 0.55
  • a chase promoter of 3.77 grams of a 0.15% iron sulfate heptahydrate solution was prepared.
  • a chase activator solution of 1.12 grams of D-isoascorbic acid dissolved in 36.40 grams of deionized water was prepared.
  • a chase catalyst solution of 2.14 grams of 70% ieri-butyl hydroperoxide in 35.40 grams of deionized water was prepared.
  • the chase promoter solution was added as a shot to the kettle.
  • the kettle contents were then cooled to 70°C, while adding the chase activator and chase catalyst solutions separately by syringe over 60 minutes at a feed rate of 0.7 grams/minute.
  • the reaction was held for 10 minutes, and then cooled to room temperature.
  • the emulsion was filtered through a 100 mesh bag.
  • Exemplary polymers as prepared in Example 1 were evaluated for particle size as shown in Table 2. Table 2. Particle Size Characterization
  • the particle size distributions was determined by light scattering using a Malvern Mastersizer 2000 Analyzer equipped with a 2000uP module. Approximately 0.5 g of polymer emulsion samples were pre-diluted into 5 mL of 0.2 weight % active Triton 405 in degassed, DI water (diluents). The pre-diluted sample was added drop-wise to the diluent filled 2000uP module while the module was pumped at 1100 rpm. Red light obscurations were targeted to be between 4 and 8%. Samples were analyzed using a Mie scattering module (particle real refractive index of 1.48 and absorption of zero: Diluent real refractive index of 1.330 with absorption of zero).
  • a general purpose (spherical) analysis model with“normal sensitivity” was used to analyze the diffraction patterns and convert them into particle size distributions.
  • Exemplary polymers as prepared in Example 1 were spray dried according to the following procedure.
  • a two-fluid nozzle atomizer was equipped on a Mobile Minor spray dryer (GEA Process Engineering Inc.).
  • the spray drying experiments were performed under an inert atmosphere of nitrogen.
  • the nitrogen supplied to the atomizer at ambient temperature was set at 1 bar and 50% flow, which is equivalent to 6.0 kg/hour of flow rate.
  • the polymer emulsion was fed into the atomizer at about 30 mL/min using a peristaltic pump (Masterflex L/S). Heated nitrogen was used to evaporate the water.
  • the inlet temperature was set at l40°C, and the outlet temperature was equilibrated at 40-50°C by fine tuning the emulsion feed rate.
  • the resulting polymer powder was collected in a glass jar attached to the cyclone and subsequently vacuum dried at room temperature to removed residual moisture.
  • Exemplary conditioning oil formulations according to the present invention including exemplary polymers as prepared in Example 3, and control leave-in hair conditioning formulations, contain the components recited in Table 3.
  • Exemplary conditioning oil formulations were formulated by mixing the exemplary polymers as prepared in Example 3 together with the other components in the amounts specified in Table 3 under stirring at 500 rpm at 50°C for 1 hour.
  • the conditioning effect of exemplary conditioning oil formulations as prepared in Example 4 was measured using the INSTRON Dry Combing Method.
  • Medium bleached European human hair from International Hair Importers was used for testing the conditioning oil formulations prepared herein.
  • Each tress weighed about 2.0 grams.
  • Each tress was rinsed for 15 seconds under a stream of 40°C tap water.
  • 0.4 grams (0.2 ml per gram of hair) of a solution containing nine percent of sodium lauryl sulfate was applied and lathered through the tress for 30 seconds.
  • the tress was rinsed for 30 seconds under running water. Excess water was removed from the tress by passing the tress between the index and middle fingers of the hand.
  • the tresses were clipped to vertical racks and dried.
  • the conditioning oil formulations were applied to the tresses in the amount of 0.3 grams (0.15 ml per gram of hair), and the tresses were stroked 10 times with fingers to distribute evenly on hair. After 16 hours, 0.18 grams (0.4 ml per gram of hair) grams of EverSleek Sulfate-Free shampoo (available from L’Oreal) were applied to the tresses and lathered through the tresses for 30 seconds. The tresses were then rinsed for 30 second under running water. Excess water was removed from the tresses by passing the tresses between the index and middle fingers of the hand. The tresses were clipped to vertical racks and dried.
  • the tresses were combed once before performing an INSTRON study.
  • INSTRON combing is used for determining conditioning performance by the ease of dry combing.
  • the test employs an INSTRON strain gauge, which is equipped to measure the force required to comb the hair.
  • the conditioning performance is based on the ability of a particular hair treatment formulation, such as a shampoo or a hair conditioner, to reduce the force required to comb the hair with the INSTRON strain gauge.
  • the force is reported as an Average Combing Load (“ACL”). The lower the ACL value, the better the conditioning effect imparted by the formulation being tested. Three tresses per treatment and 5 measurements per tress were averaged to generate the combing data.
  • hair is detangled by combing the tress 3 times. Then hair is retangled by swirling the tress clockwise 3 times and swirling it counter clockwise 3 times. The tress is then placed on a hanger and INSTRON combed. Retangle and INSTRON combing are repeated until all data points are collected. An ACL for three tresses is measured for each treatment. The effectiveness of a treatment can then be expressed as an ACL of the treated tress or percent reduction in ACL, calculated using the relationship:
  • Exemplary hair conditioner formulations according to the present invention including exemplary polymers as prepared in Example 3, and control leave-in hair conditioning formulations, contain the components recited in Table 5. Table 5. Exemplary and Control Hair Conditioner Formulations
  • Deionized water was added to the mixing vessel and heated to 70°C. With moderate agitation, the hydroxyethyl cellulose was dispersed until fully dissolved. Heat was decreased to 60°C and cetearyl alcohol, PEG- 100 stearate, glyceryl stearate, and silicone fluid were added. The hair conditioner was mixed for 3 minutes and then tetrasodium EDTA was added and mixed for 3 minutes. When temperature was below 40°C, the phenoxyethanol and
  • the conditioning effect of exemplary hair conditioner formulations as prepared in Example 6 were measured using the INSTRON Dry Combing Method.
  • Medium bleached European human hair from International Hair Importers was used for testing the conditioning oil formulations prepared herein.
  • Each tress weighed about 2.0 grams.
  • Each tress was rinsed for 15 seconds under a stream of 40°C tap water.
  • 0.4 grams of a solution containing nine percent of sodium lauryl sulfate was applied and lathered through the tress for 30 seconds.
  • the tress was rinsed for 30 seconds under running water. Excess water was removed from the tress by passing the tress between the index and middle fingers of the hand.
  • the tresses were clipped to vertical racks and dried.
  • hair tresses were rinsed with tap water for 30 seconds at 40°C.
  • the test conditioner was applied to the tresses in the amount of 0.8 grams, and the tresses were stroked for 60 seconds.
  • the tress were rinsed for 30 seconds under tap water at 40°C. Excess water was removed by pulling the tress through the index and middle fingers of the hand. The tresses were allowed to dry separately on a paper towel overnight at room temperature.
  • the tresses were combed once before performing an INSTRON study as described in Example 5.

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Abstract

L'invention concerne des compositions après-shampoing et leurs procédés d'utilisation, lesquelles compositions après-shampoing comprennent (a) un gel d'huile de polyacrylate, par rapport au poids total de la composition, le gel d'huile de polyacrylate comprenant (i) au moins une huile ester hydrophobe de qualité cosmétique et (ii) un ou plusieurs polymères comprenant des motifs structuraux polymérisés formés de (1) 96 à 99,89 % en poids de monomères de (méth)acrylate en C4-C8, (2) 0,1 à 2 % en poids de monomères d'acide (méth)acrylique et (3) 0,01 à 2 % en poids d'au moins un agent de réticulation, (b) un excipient de qualité dermatologique et (c) un agent tensioactif. L'invention concerne également des procédés de soin des cheveux comprenant l'administration topique desdites compositions sur les cheveux.
PCT/US2019/057132 2018-10-30 2019-10-21 Compositions après-shampoing Ceased WO2020092031A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013095993A2 (fr) * 2011-12-22 2013-06-27 Dow Global Technologies Llc Polymères d'hygiène personnelle résistant à l'eau
WO2013148614A2 (fr) * 2012-03-29 2013-10-03 Rohm And Haas Chemicals Llc Polymères résistant à l'eau pour soin personnel
US20140113992A1 (en) 2011-06-23 2014-04-24 Dow Global Technologies Llc Water redispersible epoxy polymer powder and method for making the same
WO2014204937A1 (fr) * 2013-06-21 2014-12-24 Rohm And Haas Company Gel d'huile de polyacrylate et procédés correspondants
WO2017105957A1 (fr) 2015-12-14 2017-06-22 Dow Global Technologies Llc Composition de gel d'huile de polyacrylate
WO2018231953A1 (fr) * 2017-06-16 2018-12-20 Dow Global Technologies Llc Composition nettoyante huileuse

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140113992A1 (en) 2011-06-23 2014-04-24 Dow Global Technologies Llc Water redispersible epoxy polymer powder and method for making the same
WO2013095993A2 (fr) * 2011-12-22 2013-06-27 Dow Global Technologies Llc Polymères d'hygiène personnelle résistant à l'eau
WO2013148614A2 (fr) * 2012-03-29 2013-10-03 Rohm And Haas Chemicals Llc Polymères résistant à l'eau pour soin personnel
WO2014204937A1 (fr) * 2013-06-21 2014-12-24 Rohm And Haas Company Gel d'huile de polyacrylate et procédés correspondants
WO2017105957A1 (fr) 2015-12-14 2017-06-22 Dow Global Technologies Llc Composition de gel d'huile de polyacrylate
WO2018231953A1 (fr) * 2017-06-16 2018-12-20 Dow Global Technologies Llc Composition nettoyante huileuse

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