WO2018017570A1 - Une composition de défrisage et de coiffage des cheveux, procédé de son préparation et procédé d'utilisation de celle-ci - Google Patents

Une composition de défrisage et de coiffage des cheveux, procédé de son préparation et procédé d'utilisation de celle-ci Download PDF

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WO2018017570A1
WO2018017570A1 PCT/US2017/042598 US2017042598W WO2018017570A1 WO 2018017570 A1 WO2018017570 A1 WO 2018017570A1 US 2017042598 W US2017042598 W US 2017042598W WO 2018017570 A1 WO2018017570 A1 WO 2018017570A1
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methacrylate
acrylate
hair
ethyl
acid
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Manuel Gamez-Garcia
Solomon T. WOSSENE
Andrea Louise BURRON
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ISP Investments LLC
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ISP Investments LLC
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/91—Graft copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring

Definitions

  • the present application relates to a hair straightening or hair styling composition, and more particularly, to a hair straightening or hair styling composition comprising a hybrid graft polymer and at least one carrier, a process for preparing the same and method of use thereof.
  • the methods to achieve temporary or non-permanent shaping or style of hair include using styling products such as hair spray, mousse, styling gel in combination with styling implements such as flat irons to make straight hair style and curling iron and hair rollers to form curls on hair, which allows one to have a different hair style even from one day to the next.
  • styling products such as hair spray, mousse, styling gel in combination with styling implements such as flat irons to make straight hair style and curling iron and hair rollers to form curls on hair, which allows one to have a different hair style even from one day to the next.
  • the temporary setting of hair created by these traditional methods lasts not long, typically a few hours or up to a day and it disappears when hair becomes wet under high humidity condition or is washed.
  • a durable non-permanent styling that can last a few days and survive multiple shampoo washes is highly desired as many consumers want to retain a nice temporary hair style longer beyond multiple wash cycles, especially good curl retention under high humidity condition after hair is washed, reducing the frequency of repeatedly treating the hair with a styling product. Therefore, there is a need for a composition and methods which can offer benefit of durable non-permanent hair styling of hair fibers over multiple shampoo washes and multiple conditioner rinsing.
  • U.S. Patent No. 5,037,930 assigned to GAF Chemicals Corporation discloses at least two monomers grafted onto hydroxy-containing cellulose polymer.
  • the invention provides a polymer of a cellulose containing a hydroxy group on which is grafted, by replacement of the hydrogen atom of the hydroxy group, with a copolymer having a polymerized lactam-containing moiety and a polymerized quatemized ammonium-containing moiety.
  • the ratio of the polymerized lactam group of the quatemized ammonium moiety in the grafted copolymer can be predetermined to provide polymers which are particularly useful in the hair treatment industry.
  • U.S. Pub. No. 20060029561 assigned to Gunn Euen et al. discloses a graft copolymer comprising a polysaccharide polymer grafted with a polymer capable of bonding to human hair useful in hair care compositions.
  • the method comprise mixing a polysaccharide polymer and a polymer capable of bonding to human hair, and irradiating the polymer mixture with electron beam irradiation to form the graft copolymer.
  • U.S. Patent. No. 4,803,071 assigned to National Starch and Chemical Corporation discloses improved hair care compositions containing a specified cationic water soluble graft copolymer of ⁇ , ⁇ -dialkyldiallyl ammonium halide on a substrate of cellulose, galactomannan gum or derivative thereof.
  • PCT Publication No. 2014/116560 assigned to ISP Investments Inc. discloses hemi- aminal ethers and thioethers of N-alkenyl cyclic compounds optionally having one or more polymerizable moieties for various applications including but not limited to personal care (e.g. , hair care, sun care, skin care, color cosmetic, and oral care), adhesives, coatings, paints, electronics, Household, Industrial and Institutional (HI&I) compositions, inks, membranes, metal working fluids, oilfield chemicals, plastics and plasticizers, textiles, industrial products, biocides, pharmaceuticals/nutritionals, and agrochemical compositions.
  • personal care e.g. , hair care, sun care, skin care, color cosmetic, and oral care
  • adhesives coatings, paints, electronics, Household, Industrial and Institutional (HI&I) compositions, inks, membranes, metal working fluids, oilfield chemicals, plastics and plasticizers, textiles, industrial products, biocides, pharmaceutical
  • the present application provides a hair straightening or hair styling composition
  • a hair straightening or hair styling composition comprising: (A) a polymeric compound selected from a reaction product of (i) at least one hybrid graft polymer derived from (a) a functionalized or unfunctionalized cellulose moiety and (b) at least one functionalized or unfunctionalized acryloyl moiety; or a reaction product of (ii) at least one hybrid graft polymer derived from (a) a functionalized or unfunctionalized galactomannan moiety and (b) at least one functionalized or unfunctionalized acryloyl moiety, and (B) at least one carrier.
  • this application provides a hair straightening or hair styling composition of (A) about O.lwt. % to about 50.0 wt. % of at least one graft polymer selected from: (a) ethyl acrylate (EA)/methacrylic acid (MA) copolymer grafted on hydroxy ethyl cellulose (HEC); (b) ethyl acrylate (EA) copolymer grafted on hydroxy ethyl cellulose (HEC); (c) ethyl acrylate (EA) copolymer grafted on carboxymethyl cellulose (CMC); (d) ethylacrylate (EA)/ methacrylic acid (MA) copolymer grafted on cationic guar; (e) trimethylaminoethyl methacrylate grafted on at least one CMC/HEC; (f) copolymer of APT AC grafted on at least
  • a method of straightening or styling of hair tresses comprises: (a) washing the hair tresses with shampoo; (b) reducing or eliminating the moisture of hair tresses of step (a); (c) applying the hair straightening or styling composition of the present application to the dried hair of step (b); (d) leaving the treated hair for about 15 to 30 minutes for penetration; (e) hot air drying the treated hair of step (d) by mechanically straightening hair with either brushing or combing with a slow uniform motion from root to tip; (f) ironing the hair resulted from step (e) for at least 4 to 8 times using flat iron pre-heated to 375-450°F; and (g) allowing the hair tresses of step (f) to remain as such for at least 15 to 20 minutes to obtain straightened or styled hair.
  • Another aspect of the present application provides a hair straightening or hair styling composition formulated as straightening spray lotion, non-aerosol straightening mousse, smoothing and straightening fluid, straightening serum, straightening solution, straightening perm, emulsion, gel, vesicle dispersion, paste, cream, solid stick, shampoo, balm, wipe, milk, foam, jellies, liquid, tonics, and/or enamel.
  • a hair straightening or hair styling composition formulated as straightening spray lotion, non-aerosol straightening mousse, smoothing and straightening fluid, straightening serum, straightening solution, straightening perm, emulsion, gel, vesicle dispersion, paste, cream, solid stick, shampoo, balm, wipe, milk, foam, jellies, liquid, tonics, and/or enamel.
  • composition refers to optional compatible components that can be used provided that the important ingredients are present in the suitable form and concentrations.
  • the term “comprising” thus encompasses and includes the more restrictive terms “consisting of” and “consisting essentially of” which can be used to characterize the essential ingredients such as cellulose ethers, galactomannans, acrylates, quaternary ammonium compounds, organic acids, amides, cross linking groups and/or hybrid polymers.
  • references herein to "one embodiment” or “one aspect” or “one version” or “one objective” of the application include one or more such embodiment, aspect, version or objective, unless the context clearly dictates otherwise.
  • hair straightening refers to the state where the natural curl of the hair has been removed and that the resulting straight configuration effectively resists reversion (i.e. resumption of a curly pattern) on being subjected to more than one washing, preferably at least four washings, and more preferably, at least eight washings or lasts until the scalp hair grows sufficiently to visibly warrant another hair straightening procedure.
  • the term 'hair styling' refers to hair setting agents that are hair fixatives and film formers and which are topically applied to the hair to actively contribute to the ease of styling and/or holding of a hair set, and to maintain the restylability of the hair set.
  • hair straightening iron refers to device used in association with a combination of heat and pressure to straighten hair. It is generally composed of two flat heating elements, covered with various materials, between which a lock of hair is pressed at a time. Hair straightening irons are commercially available that are known to a person skilled in the relevant art.
  • the source of energy of heating can be electric, solar, light, magnetic, chemical, and electromagnetic or combinations thereof.
  • washed and “washing” refers to rinsing of hair with water.
  • cosmetically acceptable ingredient means any ingredient/compound or mixture of ingredients/compounds or compositions that are typically employed to produce other desirable effects in personal care compositions.
  • personal care composition refers to such illustrative non-limiting compositions as skin, sun, oil, hair, and preservative compositions, including those to alter the color and appearance of the skin.
  • hybrid polymer refers to a compound comprising repeating structural units (monomers) connected by covalent chemical bonds. Polymers can be further derivatized, crosslinked, grafted or end-capped. Non-limiting examples of polymers include copolymers, terpolymers, quaternary polymers, and homologues, and the like, wherein the polymer is random, block, or alternating polymer.
  • copolymer refers to a polymer consisting essentially of two or more different types of repeating structural units (monomers).
  • the term "homopolymer” refers to a molecule that comprises one type of monomer and the term “non-homopolymer” refers to a polymer that comprises more than one type of monomer and includes such polymers wherein a small amount of polymerization solvent can or can not be covalently bonded into the polymer.
  • the non-homopolymer can be a copolymer, terpolymer, tetramer, or the like.
  • graft copolymer means a polymer having two or more (co)polymeric blocks connected to a polymer backbone as side chains.
  • grafting means the forming of a polymer by the bonding or growing of side chains or species at some point(s) along the backbone or terminal or in pendant of a parent polymer.
  • Three approaches are generally used for synthesis graft copolymers.
  • “Grafting onto” involves the reaction between functional groups on two different polymers.
  • “Grafting from” involves a polymer with functional groups (initiator) that initiates the polymerization of vinyl monomers.
  • “Grafting through” involves (co)polymerization of monomer(s).
  • hybrid graft polymer refers to a polymer derived from: (a) a functionalized or unfunctionalized cellulose moiety and (b) at least one functionalized or unfunctionalized acryloyl moiety; or a polymer derived from (a) a functionalized or unfunctionalized galactomannan moiety and (b) at least one functionalized or unfunctionalized acryloyl moiety.
  • the present application provides a hair straightening or hair styling composition comprising a hybrid graft polymer and at least one carrier. Particularly, it provides a hair straightening and hair styling composition comprising: (A) a polymeric compound selected from a reaction product of (i) at least one hybrid graft polymer derived from (a) a functionalized or unfunctionalized cellulose moiety and (b) at least one functionalized or unfunctionalized acryloyl moiety; or a reaction product of (ii) at least one hybrid graft polymer derived from (a) a functionalized or unfunctionalized galactomannan moiety and (b) at least one functionalized or unfunctionalized acryloyl moiety, and (B) at least one carrier.
  • the cellulose selected from a reaction product of (i) at least one hybrid graft polymer derived from (a) a functionalized or unfunctionalized cellulose moiety and (b) at least one functionalized or unfunctionalized acryloyl moiety.
  • cellulose ether moieties of the present application have the structure set out below:
  • R H, alkyl, alkoxy. alkoxy alkyl, carboxy group wherein R is independently selected from the group consisting of hydrogen; C1-C50 straight- or branched-chain, functionalized or unfunctionalized alkyl groups; hydroxyalkyl groups; alkylcarboxy groups; and functionalized and non-functionalized, substituted or unsubstituted carbonyl groups.
  • the functional groups can be with or without heteroatoms; n is 1 to about 2000.
  • the cellulose moiety can be a cellulose ether moiety.
  • cellulose refers to a polymer having repeated saccharide units, including lingocellulose, cellulose and derivatives of these (e.g., cellulose ether moiety is an alkyl cellulose selected from methyl cellulose (MC), ethylcellulose (EC) and propyl cellulose (PC); a hydroxyalkyl cellulose selected from methyl hydroxyethyl cellulose (MHEC), ethyl hydroxyethyl cellulose (EHEC), methyl ethyl hydroxyethyl cellulose (MEHEC), hydroxypropyl hydroxyethyl cellulose (HPHEC), methyl hydroxypropyl hydroxyethyl cellulose (MHPHEC), hydroxypropyl cellulose (HPC), methyl hydroxypropyl cellulose (MHPC) and ethyl hydroxypropyl cellulose (EHPC); a carboxy alkyl cellulose selected from carboxymethylcellulose (CMC), carboxyethyl cellulose (CMC), carboxyethy
  • the cellulose ether includes but is not limited to:
  • HEC Hydroxy ethylcellulose
  • CMC Carboxy methylcellulose
  • HPMC Hydroxymethylpropyl cellulose
  • Galactomannans refers to Galactomannans consisting mainly of the monosaccharides mannose and galactose.
  • the mannose-elements form a chain consisting of many hundreds of (l ⁇ 4)- -D-mannopyranosyl-residues, with 1 ⁇ 6 linked a-D- galactopyranosyl-residues at varying distances, dependent on the plant of origin.
  • the galactomannans of the present application can be obtained from numerous sources.
  • galactomannans of the present application can also be obtained by various synthetic routes known to a person skilled in the pertinent art or can be obtained by chemical modification of naturally occurring galactomannans.
  • the galactomannan is guar or cationic guar as provided below:
  • Guar gum often called “guar flour” after grinding, refers to the mucilage found in the seed of the leguminous plant Cyamopsis tetragonolobus.
  • the water soluble fraction (85%) is called “guaran,” which consists of linear chains of (1 ⁇ 4)- ⁇ - ⁇ mannopyranosyl units-with a-D-galactopyranosyl units attached by (1 ⁇ 6) linkages.
  • the ratio of D-galactose to D- mannose in guaran is about 1:2.
  • Guar gum can take the form of a whitish powder which is dispersible in hot or cold water.
  • Guar gum can be obtained, for example, from Rhodia, Inc. (Cranbury, N.J.), Hercules, Inc. (Wilmington, Del.) and TIC Gum, Inc. (Belcamp, Md.).
  • non-limiting examples of galactomannans include carrageenan gum, alginate, starch, or guar; Guar Splits, Locust Bean Gum, a non-ionic guar selected from alkyl guar, hydroxyalkyl guar; a cationic guar, an anionic guar selected from carboxymethyl guar, carboxypropyl guar, carboxybutyl guar, carboxymethylhydroxypropyl guar; sulfate esters of guar, phosphate esters of guar and sulfonic esters of guar.
  • galactomannans of interest include but not limited to modified galactomannans, including carboxymethyl guar, carboxymethylhydroxypropyl guar, cationic hydroxpropyl guar, hydroxyalkyl guar, including hydroxyethyl guar, hydroxypropyl guar, hydroxybutyl guar and higher hydroxylalkyl guars, carboxylalkyl guars, including carboxymethyl guar, carboxylpropyl guar, carboxybutyl guar, and higher alkyl carboxy guars, the hydroxyethylated, hydroxypropylated and carboxymethylated derivative of Guaran, the hydroxethylated and carboxymethylated derivatives of Carubin and the hydroxypropylated and carboxymethylated derivatives of Cassia-Gum.
  • modified galactomannans including carboxymethyl guar, carboxymethylhydroxypropyl guar, cationic hydroxpropyl gu
  • Xanthan gum is a polysaccharide gum produced by Xathomonas campestris. Xanthan gum contains D-glucose, D-mannose, D- glucuronic acid as the main hexose units and also contains pyruvate acid and is partially acetylated.
  • functionalization reactions include epoxidation, sulfonation, hydrolysis, amidation, esterification, hydroxylation, dihydroxylation, animation, ammonolysis, acylation, nitration, oxidation, dehydration, elimination, hydration, dehydrogenation, hydrogenation, acetalization, halogenation, dehydrohalogenation, Michael addition, aldol condensation, Canizzaro reaction, Mannich reaction, Clasien condensation, Suzuki coupling, and the like.
  • functionalization of a moiety replaces one or more hydrogens in the moiety with one or more non-hydrogen groups, e.g., alkyl, alkoxyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, and/or aryl groups.
  • non-hydrogen groups e.g., alkyl, alkoxyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, and/or aryl groups.
  • cycloalkyl groups include cyclopentane, cyclohexane, cycloheptane, and the like.
  • alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, and the like.
  • alkyl refers to a functionalized or unfunctionalized monovalent straight- chain, branched-chain or cyclic alkyl with C1-C60 carbons and optionally having one or more heteroatoms.
  • an alkyl is a C1-C45 group and more particularly, a C1-C30 group.
  • alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, cyclobutyl, n-pentyl, isopentyl, cyclopentyl, n-hexyl, cyclohexyl, n-heptyl, cyclyheptyl, methylcyclohexyl, n-octyl, 2-ethylhexyl, tert-octyl, iso-norbornyl, n- dodecyl, tert-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, and n-eicosyl.
  • alkyl (alk) acrylate refers to an alkyl ester of an acrylic acid or an alkyl acrylic acid.
  • alkyl (alk) acrylamide refers to an alkyl amide of an acrylic acid or an alkyl acrylic acid.
  • alkylene refers to a functionalized or unfunctionalized divalent straight- chain, branched-chain or cyclic C1-C40 group optionally having one or more heteroatoms. Particularly, an alkylene is a C1-C45 group and more particularly, a C1-C30 group.
  • alkylene groups include -CH 2 - -CH2-CH2-, -CH(CH3)-CH 2 - -CH 2 -CH(CH 3 )-, -C(CH 3 )2-CH2- -CH 2 -C(CH 3 )2-, -CH(CH 3 )-CH(CH 3 )-, -C(CH 3 ) 2 - C(CH 3 )2- -CH2-CH2-CH2-, -CH(CH 3 )-CH2-CH 2 -, -CH 2 -CH(CH 3 )-CH2-, -CH2-CH2- CH(CH 3 )-, -CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2- CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-, cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, and the like
  • aryl refers to a functional group derived from an aromatic hydrocarbon.
  • the aromatic hydrocarbon can be mononuclear or polynuclear.
  • aryl group of the mononuclear type include phenyl, tolyl, xylyl, mesityl, cumenyl, and the like.
  • aryl group of the polynuclear type include naphthyl, anthryl, phenanthryl, and the like.
  • the aryl group can have at least one substituent selected from halogen, hydroxy, cyano, carboxy, carbamoyl, nitro, amino, aminomethyl, lower alkyl, lower alkoxy, mercapto, trichloroethyl, or trifluoromethyl.
  • substituents selected from halogen, hydroxy, cyano, carboxy, carbamoyl, nitro, amino, aminomethyl, lower alkyl, lower alkoxy, mercapto, trichloroethyl, or trifluoromethyl.
  • substituted aryl groups include 2-fluorophenyl, 3- nitrophenyl, 4-nitrophenyl, 4-methoxyphenyl, 4-hydroxyphenyl, and the like.
  • branched and unbranched alkyl groups refers to alkyl groups, which can be straight chained or branched.
  • the alkyl groups have from 1 to about 60 carbon atoms, more particularly, from 1 to about 30 carbon atoms, and yet more particularly from 1 to about 6 carbon atoms.
  • Branched groups include isopropyl, tert-butyl, and the like.
  • cycloalkyl group refers to a non-aromatic mono- or multicyclo ring system having from about 3 to about 10 carbon atoms. The cycloalkyl group can be partially unsaturated.
  • the cycloalkyl group can also be substituted with an alkyl group substituent as defined herein.
  • the cycloalkyl chain can contain an oxygen, sulfur, or substituted or unsubstituted nitrogen atom, wherein the nitrogen substituent can be hydrogen, alkyl, substituted alkyl, aryl, or substituted aryl, thus providing a heterocyclo group.
  • Representative monocyclo cycloalkyl rings include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like.
  • cycloalkyl group can be substituted with a linking group, such as an alkyl group, alkylene group, and the like, to form cyclopropylmethyl group, cyclobutylmethyl group, and the like.
  • the cycloalkyl group can also be a multicyclo cycloalkyl rings such as adamantyl, octahydronaphthyl, decalin, camphor, camphane, and noradamantyl.
  • heteroatom refers to atoms such as oxygen, nitrogen, sulfur, silicon, phosphorous, and/or halogen.
  • the heteroatom(s) can be present as a part of one or more heteroatom-containing functional groups and/or as a part of one or more heterocyclic rings.
  • Non-limiting examples of heteroatom-containing functional groups include ether, hydroxy, epoxy, carbonyl, carboxamide, carboxylic ester, carboxylic acid, imine, imide, amine, sulfonic, sulfonamide, phosphonic, and silane groups.
  • halogen refers to chloro, bromo, iodo and fluoro, and in one embodiment is bromo and/or chloro.
  • the term "monomer” refers to the repeat units that comprise a polymer.
  • a monomer is a compound that chemically bonds to other molecules, including other monomers, to form a polymer.
  • Typical graft monomers mixed with the cellulose/galactomannan to provide the functional groups grafted onto the cellulose/galactomannan include monomers having at least one functionalized or unfunctionalized acryloyl moieties.
  • each Ri, R2, and R3 is independently selected from the group consisting of hydrogen and functionalized and unfunctionalized alkyl, alkenyl, aryl, nitrile, formyl, carboxyl, carboxylate salt, carboxylic ester, carboxamide, halogen, thiocarboxylate, and combinations thereof.
  • the monomer having at least one functionalized or unfunctionalized acryloyl moiety is selected from the group acrylic acid, methacrylic acid, maleic acid, sodium acrylate, sodium methacrylate, potassium acrylate, potassium methacrylate, ammonium acrylate, ammonium methacrylate, calcium acrylate, calcium methacrylate, 2-bromoacrylic acid, 2-(bromomethyl)acrylic acid, 2-ethylacrylic acid, 2- propylacrylic acid, 2- (trifluoromethyl) acrylic acid, zinc acrylate, zirconium acrylate, zinc methacrylate, zirconium methacrylate, methyl acrylate, ethyl acrylate, 2-(2-ethoxyethoxy)ethyl acrylate, 2-phenoxyethyl acrylate, alkoxylated phenol acrylates, ethoxylated hydroxyethyl acrylates, ethoxylated nonyl phenol acrylates
  • the monomer comprising at least one acryloyl moiety with at least one lactam moiety functionality has the structure:
  • each Rl R2 and R3 is independently selected from the group consisting of
  • each X ected from the group consisting of OR4, OM, halogen, N(R5)(R6), , and combinations thereof; each Y is independently oxygen, NR7 or sulfur; each R4, R5, R6 and R7 is independently selected from the group consisting of hydrogen and functionalized and unfunctionalized alkyl; each M is independently selected from the group consisting of metal ions, ammonium ions, organic ammonium cations, and combinations thereof; and each Ql, Q2, Q3, and Q4 is independently selected from the group consisting of functionalized and unfunctionalized alkylene.
  • each Ql, Q2, Q3, and Q4 is independently selected from the group consisting of functionalized and unfunctionalized CI - C12 alkylene.
  • alkylene groups include -CH2-. -CH2-CH2-, -CH(CH3)-CH2- - CH2-CH(CH3)-, -C(CH3)2-CH2- -CH2-C(CH3)2- -CH(CH3)-CH(CH3)-, -C(CH3)2- C(CH3)2- -CH2-CH2-, -CH(CH3)-CH2-CH2- -CH2-CH(CH3)-CH2- CH2-CH(CH3)-, -CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-, -CH2-CH2-CH2- CH2-CH2-CH2-CH2-, and -CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-.
  • each Rl, R2 and R3 is independently selected from the group consisting of hydrogen, methyl and combinations thereof. Particularly, Rl and R2 are hydrogens and R3 is hydrogen or methyl.
  • each Rl and R3 is independently hydrogen or
  • R2 is C X ;
  • X is selected from the group consisting of OR4, OM, halogens, and N(R5)(R6); each R4, R5, and R6 is independently selected from the group consisting of hydrogen and functionalized and unfunctionalized alkyl; and each M is independently selected from the group consisting of metal ions, ammonium ions, organic ammonium cations, and
  • Rl and R3 are hydrogens and R2 is C X ;
  • X is selected from the group consisting of OR4, OM and N(R5)(R6);
  • each R4, R5, and R6 is independently selected from the group consisting of hydrogen and functionalized and unfunctionalized Cl- C4 alkyl;
  • each M is independently selected from the group consisting of metal ions, ammonium ions, organic ammonium cations, and combinations thereof.
  • the acryloyl moiety with at least one lactam moiety functionality can be synthesized using methods recorded in the art, e.g., by reaction of an N-hydroxylalkyl lactam with an acrylate, (meth)acrylate, anhydride, or similar compounds.
  • Production methods include those described in patents: U.S. Patent Nos. 2,882,262; 5,523,340; 6,369,163; U.S. Patent Application Publication 2007/123673; GB 924,623; 930,668; and 1,404,989; WO 03/006569; and EP 385918.
  • the acryloyl moiety with at least one lactam moiety functionality containing monomers shown in structures (2)-(57) below can be obtained from condensation reactions that include an N-hydroxyalkyl lactam and an unsaturated carboxylic acid, an acrylate, a (meth)acrylate, or an anhydride.
  • Suitable N-hydroxyalkyl lactams include N-hydroxymethyl pyrrolidone and caprolactam, N-hydroxyethyl pyrrolidone and caprolactam, and N-hydroxypropyl pyrrolidone and caprolactam.
  • Non-limiting examples of carboxylic acids that can be used include: acrylic acid, methacrylic acid, itaconic acid, crotonic acid, fumaric acid, succinic acid, and maleic acid.
  • acrylates and (meth)acrylates include (without limitation) methyl, ethyl, butyl, octyl, ethyl hexyl acrylates and their (meth)acrylate analogues.
  • Representative anhydrides include formic anhydride, succinic anhydride, maleic anhydride and acetic anhydride.
  • the monomer having the acryloyl moiety with at least one lactam moiety functionality containing monomer has a structure selected from the group consisting of:
  • Non-limiting, but preferred examples of (a) a monomer comprising at least one functionalized acryloyl moiety with at least one lactam moiety functionality are represented below (I).
  • the monomer having at least one functionalized acryloyl moiety is a cationic monomer or quaternized ammonium-containing monomer.
  • the monomer having at least one functionalized acryloyl moiety is selected from the group acrylamidopropyl trimethylammonium chloride (APT AC), diallyl dimethyl ammonium chloride (DADMAC); Aery loyloxy ethyl trimethylammonium chloride (AETAC); Methacrylamidopropyltrimethylammonium chloride (M APT AC); Dimethylaminoethyl methacrylate (DMAEMA or MADAME); Methyloyloxy ethyl trimethyl ammonium chloride (MET AC); Dimethylaminopropylmethacrylamide-N-(3-chloro-2- hydroxypropyl)-trimethylammonium chloride (DIQUAT chloride), and Methacryloylaminopropyl Lauryl-Dimethyl Ammonium Chloride (MAPLDMAC).
  • APT AC acrylamidopropyl trimethylammonium chloride
  • DADMAC diallyl dimethyl ammonium
  • the hair straightening or hair styling composition further comprises an "organic acids or/and inorganic acids".
  • organic/inorganic acids including but not limited to monocarboxylic acids, dicarboxylic acids, and tricarboxylic acids such as glyoxylic acid, acetic acid, glycolic acid, pyruvic acid, oxolacetic acid, formic acid, oxalic acid, lactic acid, dihydroxyfumaric acid, tartaric acid, citric acid, oxolacetic acid, tartaric acid, maleic acid, malic acid, hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, and combinations thereof and combinations thereof.
  • the concentration of hybrid polymer and/or the second optional polymeric compound used for preparing hair styling or hair straightening composition is in the range of from about 0.1% wt./wt. to about 60% wt./wt. of the total composition.
  • Other non-limiting ranges of hybrid polymer and second polymer include from about 0.1% wt./wt. to about 10% wt./wt., about 10% wt./wt. to about 20% wt./wt., about 20% wt./wt., to about 30% wt./wt. about 30% wt./wt. to about 40% wt./wt., about 40% wt./wt. to about 50% wt./wt., or about 50% wt./wt. to about 60% wt./wt., of the total composition.
  • the present application further optionally comprises a cross-linking monomeric unit having alcohol, thiol, carboxylic acids, poly carboxylic acids, poly epoxides, aldehydes, epoxides, acrylate esters of epoxides, acid aldehydes, anhydrides, epichlorohydrins, diepoxides, acetals, diisocyanates, divinyl sulfones, amino or ammonium compounds, modified silicones; functionalized and unfunctionalized acryloyloxy, methacryloyloxy, acryloylamino, methacryloylamino, alkenyl, vinyl, allyl, alkylallyl; functionalized and unfunctionalized ethylenically unsaturated carboxylic acids; dihydric alcohols, siloxanes, alkoxy silanes or sulfate containing compounds.
  • the (i) at least one functionalized or unfunctionalized cellulose moiety or at least one functionalized or unfunctionalized galactomannan moiety is chemically connected with (ii) at least one monomer selected from functionalized or unfunctionalized acrylate moiety by chemical reaction to yield the desired hybrid polymer of the present application.
  • another important embodiment of the present application provides or contemplates physical mixtures comprising (i) at least one functionalized or unfunctionalized cellulose ether moiety or at least one functionalized or unfunctionalized galactomannan moiety and (ii) at least one functionalized or unfunctionalized acrylate moiety.
  • the resulting hybrid polymer and physical mixture both are capable of providing better and differentiated effects on hair styling and straightening properties.
  • R H, alkyl, alkoxy. alkoxy alkyl, carboxy group
  • *G is one or more functionalized or unfunctionalized acryloyl moiety containing monomer.
  • the probable position for grafting of guar or its derivative (III) occurs at one or more positions.
  • Degree of crystallinity, initiators, reaction medium, grafting agent and its functionality plays a key role in chemical functionalization of galactomannan.
  • the structures of grafted guar include:
  • *G is one or more functionalized or unfunctionalized acryloyl moiety containing monomer.
  • the graft polymer according to the application can be made in accordance with any of a variety of polymerization methods known to a person having ordinary skill in the art.
  • methods of polymerization include free radical polymerization, living radical polymerization (LRP) also referred to as controlled radical polymerization (CRP) such as atom transfer radical polymerization (ATRP), reversible addition-fragmentation chain transfer (RAFT), stable free radical polymerization (SFRP), cationic polymerization, and ionic polymerization.
  • LRP living radical polymerization
  • CRP controlled radical polymerization
  • ATRP atom transfer radical polymerization
  • RAFT reversible addition-fragmentation chain transfer
  • SFRP stable free radical polymerization
  • cationic polymerization cationic polymerization
  • ionic polymerization ionic polymerization
  • Free radical polymerization can be used, especially when using water-dispersible and/or water-soluble reaction solvent(s). This type of polymerization method is described in "Decomposition Rate of Organic Free Radical Polymerization” by K.W. Dixon (section II in Polymer Handbook, Volume 1, 4th edition, Wiley-Interscience, 1999), which is herein incorporated in its entirety by reference.
  • the polymers according to the application can be synthesized by free radical polymerization in the presence of one or more free radical initiators.
  • free radical initiators include peroxides, azo compounds and halogenated compounds.
  • Suitable redox free radical initiators for the above reaction include peroxide such as hydrogen peroxide, t-butyl hydroperoxide, employed with a ferrous salt activator such as ferrous citrate, ferrous chloride, ferrous gluconate, ferrous nitrate, ferrous sulfate heptahydrate, ferrous ammonium sulfate hexahydrate, ferrous ethylene diaminetetraacetic acid complex, etc.
  • ferrous salt activator such as ferrous citrate, ferrous chloride, ferrous gluconate, ferrous nitrate, ferrous sulfate heptahydrate, ferrous ammonium sulfate hexahydrate, ferrous ethylene diaminetetraacetic acid complex, etc.
  • ferrous salt activator such as ferrous citrate, ferrous chloride, ferrous gluconate, ferrous nitrate, ferrous sulfate heptahydrate, ferrous ammonium sulfate hexahydrate
  • the graft polymers are present in the form of their quaternary salts. Quaternization of the polymer can take place before or after polymerization. When quaternization is carried out after polymerization, the grafted product is subjected to a treatment conductive to quaternization of the tertiary amino group, utilizing a conventional quaternizing agent.
  • suitable quaternizing agents include, such as, dialkyl sulfates, e.g., dimethyl sulfate, diethyl sulfate, etc.; alkyl sulfonic acid, e.g., methyl sulfonic acid, ethyl sulfonic acid, etc.; benzyl halides, e.g., benzyl chloride, benzyl bromide, benzyl iodide, etc.; alkyl halide, etc.
  • the cellulose/ galactomannan graft polymer can be prepared by any method known in the art for grafting monomers onto cellulose/ galactomannan, such as free radical synthesis with chemical initiators, high energy radiation initiation or thermal initiation.
  • the copolymerization can occur in solution, suspension, emulsion or in any medium which is known in the art, or which can become known in the art for graft copolymerization.
  • the cellulose/ galactomannan and the monomer or comonomers can be used in any proportion suitable for synthesis of a graft copolymer which is characterized by resistance to loss of intrinsic viscosity in the presence of electrolytes and dispersibility in water.
  • the emulsion method of this application is used for the graft copolymerization of cellulose/galactomannan
  • the amount of cellulose/ galactomannan can range from 15 to 95%, preferably from 20 to 50%, by weight of the final graft copolymer.
  • the amount of the monomer or comonomer can range from 95 to 30%, preferably from 80 to 50%, by weight of the final graft copolymer.
  • the resulting product from the emulsion method is a mixture of approximately 20% degraded HEC, 40% graft copolymer and 40% copolymer of EA/MAA.
  • cellulose/ galactomannan moieties having a molecular weight range from about 10,000 to about 1000,000 g/mol are reacted with a functionalized or unfunctionalized acryloyl moiety to provide cellulose/galactomannan polymers containing pendant functionalized or unfunctionalized acryloyl moieties functionality with a degree of substitution (DS) ranging from 0.1 to 2.0, dependent on the initial level of ether capping on the starting cellulose/galactomannan as well as the stoichiometry of the functionalized or unfunctionalized acryloyl moiety containing reagent relative to the level of free hydroxyl groups present on the cellulose/galactomannan.
  • DS degree of substitution
  • the degree of substitution (DS) or molar substitution (MS) is in the range of from about 0.01 to about 2.0.
  • Other non-limiting DS or MS suitable for the present application is from about 0.01 to about 0.1, about 0.1 to about 0.2, about 0.2 to about 0.4, about 0.4 to about 0.6, about 0.6 to about 0.8, about 0.8 to about 1.0, about 1.0 to about 1.2, about 1.2 to about 1.4, about 1.4 to about 1.6, about 1.6 to about 1.8, or about 1.8 to about 2.0.
  • the degree of substitution (DS) or molar substitution (MS) is measured according to the techniques that are known to a person skilled in the relevant art.
  • the molecular weight of the cellulose/galactomannan hybrid polymer can be measured by gel permeation chromatography.
  • the weight average molecular weight of the cellulose/galactomannan -hybrid polymer is in the range of from about 10,000 to about 1,000,000.
  • Other preferred molecular weight ranges include but are not limited to about 10,000 to about 100,000; about 100,000 to about 200,000; about 200,000 to about 300,000; about 300,000 to about 400,000; about 400,000 to about 500,000; about 500,000 to about 600,000; about 600,000 to about 700,000; about 700,000 to about 800,000; about 800,000 to about 900,000; and/or about 900,000 to about 1000,000.
  • the composition comprises at least one carrier selected from the group consisting of water, alcohol, hydro alcoholic moiety, an emulsion, an ester, a hydrocarbon or an organic or inorganic oil carrier.
  • An emulsion is a fluid colloidal system in which liquid droplets and/or liquid crystals are dispersed in a liquid. It is denoted by the symbol O/W (Oil in Water) if the continuous phase is an aqueous solution and by W/O (Water in Oil) if the continuous phase is an organic liquid (an 'oil'). More complicated emulsions such as 0/W/O (i.e. oil droplets contained within aqueous droplets dispersed in a continuous oil phase) are also possible.
  • a hair straightening or hair styling composition comprises (A) about 0.1 to about 50.0 wt. % of at least one graft polymer selected from: (a) ethyl acrylate/methacrylic acid copolymer grafted on hydroxy ethyl cellulose (HEC); (b) ethyl acrylate or methacrylic acid grafted on hydroxy ethyl cellulose (HEC); (c) ethyl acrylate or methacrylic acid grafted on carboxymethyl cellulose (CMC); (d) ethylacrylate monomer, methacrylic acid monomer, or ethylacrylate/ methacrylic acid copolymer grafted on cationic guar; (e) trimethylaminoethyl methacrylate grafted on CMC/HEC; (f) APT AC or its copolymer grafted on CMC/HEC; (g) Me
  • a hair straightening or hair styling composition comprising (A) physical mixture of (i) 0.1 wt. % to about 99.9 wt. % of at least one functionalized or unfunctionalized cellulose ether moiety or at least one galactomannan moiety chemically grafted with (ii) 0.1 wt. % to about 99.9 wt. % of at least one functionalized or unfunctionalized acrylate moiety; and (B) about 40 to about 99 wt. % of at least one carrier.
  • a hair straightening or hair styling composition comprising (A) at least one physical mixture selected from: (a) a physical mixture of ethyl acrylate, methacrylic acid, and hydroxy ethyl cellulose (HEC); (b) a physical mixture of ethyl acrylate, and hydroxyethyl cellulose (HEC); (c) a physical mixture of ethyl acrylate, and carboxymethyl cellulose (CMC); (d) a physical mixture of ethylacrylate, methacrylic acid, and cationic guar; (e) a physical mixture of trimethylaminoethyl methacrylate, and CMC or HEC; (f) a physical mixture of APT AC, and CMC or HEC; (g) a physical mixture of -Methacrylate-Hydroxyethylpyrrolidone, and CMC or HEC; and (h)
  • the amount of each monomer present either in physical mixture or in hybrid polymers ranges from about 95 wt. % to 30 wt. % of the total monomer in the final graft copolymer or physical mixture. Further, the amounts of monomer used for preparing hybrid polymer or physical mixture would vary based upon the intended end-use of the hybrid polymer or physical mixture.
  • the hair straightening or hair styling composition comprises about 40 to about 99.9 wt. % of the carrier.
  • the composition of the present application further comprises personal care or cosmetically acceptable ingredients or conventional additives.
  • Suitable personal care or cosmetically acceptable ingredients or conventional additives that are employed for the preparing composition of the present application is well known in the relevant art and can be readily chosen by an artisan includes but not limited to functional silicones, acidifying or alkalizing pH adjusting agents and buffering agents; auxiliary fixatives and film formers that modify the on hair attributes of the polymer of the present application, such as gums, resins, polymers of synthetic or natural origin, and the like; auxiliary rheology modifiers such as viscosity enhancing polymeric thickeners or gellants; additives such as emulsifiers, detergents, emulsion stabilizers, waxes, dispersants, oxidizing agents, antioxidants, viscosity control agents such as solvents, electrolytes; hair and skin conditioning agents such as antistatic agents, synthetic oils, vegetable or animal oils, silicone oils, monomeric or polymeric quaternized ammonium salts
  • the composition of the present application further comprises at least one protein selected from following non-limiting the group components including cysteine, histidine, lysine, arginine, aspartate, glutamate, asparagine, glutamine; alpha and/or beta-keratins, silk proteins, wheat protein, oat protein, milk protein, glycoprotein, soy protein, barley protein, quinoa protein, collagen protein, vegetable protein, chickpea protein, avacado protein, egg protein, honey protein, rice protein, casein, light protein, gelatin, or their hydrolyzed counterparts.
  • group components including cysteine, histidine, lysine, arginine, aspartate, glutamate, asparagine, glutamine; alpha and/or beta-keratins, silk proteins, wheat protein, oat protein, milk protein, glycoprotein, soy protein, barley protein, quinoa protein, collagen protein, vegetable protein, chickpea protein, avacado protein, egg protein, honey protein, rice protein
  • the composition of the present application further optionally comprises personal care or cosmetic based active ingredients.
  • Suitable personal care or cosmetic based active ingredients can be selected from the group consisting of allantoin, tocopherol nicotinate, niacinamide, retinyl propionate, palmitoyl-gly-his-lys, phytosterol, isoflavone, dexpanthenol, panthenol, bisabolol, farnesol, phytantriol, salicylic acid, zinc/sodium pyridinethione salts, piroctone olamine, selenium disulfide, tetrahydrocurcumin, glucosamine, N-acteyl glucosamine, vitamin B3, retinoids, peptides, phytosterol, dialkanoyl hydroxyproline, hexamidine, salicylic acid, N-acyl amino acids, escolols, sunscreen actives, UV-A
  • the thickening polymers of the present application are capable of contributing to hair straightening; retaining the "hair style" as such for a longer duration, providing higher humidity control and increasing body or fullness.
  • the functional silicones are selected from the group consisting of silicone quat, silicone fluid and silicone wax. These silicones are able to decrease friction during hair combing and flat ironing, smooth gliding; increase conditioning and smoothing to hair by adding flexibility; help reducing heat damage and style retention; and contribute to shine depending on the refractive index.
  • the reducing agents are selected from but are not limited to thioglycolate, thiosulfate, sulfite, bisulfite, and urea. These agents target disulfide bonds to create additional disulfide interchange and rearrangement.
  • the oxidizing agents are selected from but are not limited to hydrogen peroxide, bromides and peracetic acid to fix the disulfide bond back.
  • the conditioning agent can be a protein or hydrolyzed cationic or non-cationic protein.
  • these compounds include hydrolyzed collagens having trimethyl ammonium and trimethyl stearyl ammonium chloride groups, hydrolyzed animal proteins having trimethyl benzyl ammonium groups (benzyltrimonium hydrolyzed animal protein), hydrolyzed proteins having groups of quaternary ammonium on the polypeptide chain, including at least one Ci-Cu alkyl.
  • Ceramide type of compound include a ceramide, a glycoceramide, a pseudoceramide, or a neoceramide.
  • Possible ceramide type compounds useful herein include 2-N-linoleoyl amino-octadecane-1 ,3-diol, 2-N-oleoyl amino- octadecane-l,3-diol, 2-N-palmitoyl amino-octadecane-1 ,3-diol, 2-N-stearoyl amino- octadecane-l,3-diol, 2-N-behenoyl amino-octadecane-l,3-diol, 2-N-[2-hydroxy-palmitoyl]- amino-octadecane-1 ,3-diol, 2-N-stearoyl amino-octadecane-1, 3, 4-triol, N-stearoyl phytosphingosine, 2-N-palmitoyl amino-hexadecane-1 ,3-diol, bis-(N-hydroxy ethyl
  • conditioning agents include cationic surfactants such as a salt of a primary, secondary, or tertiary fatty amine, optionally polyoxyalkylenated, a quaternary ammonium salt, a derivative of imadazoline, or an amine oxide.
  • cationic surfactants such as a salt of a primary, secondary, or tertiary fatty amine, optionally polyoxyalkylenated, a quaternary ammonium salt, a derivative of imadazoline, or an amine oxide.
  • Suitable examples include mono-, di-, or tri- alkyl quaternary ammonium compounds with a counterion such as a chloride, methosulfate, tosylate, etc. including, but not limited to, cetrimonium chloride, dicetyldimonium chloride, behentrimonium methosulfate, and the like.
  • the presence of a quaternary ammonium compound in conjunction with the resin described above reduces static and enhances combing of hair in the dry state.
  • the resin also enhances the deposition of the quaternary ammonium compound onto the hair substrate thus enhancing the conditioning effect of hair.
  • the conditioning agent can be any fatty amine known to be useful as a conditioning agent; e.g. dodecyl, cetyl or stearyl amines, such as stearamidopropyl dimethylamine.
  • Other conditioning agents can be selected from but are not limited to polymeric and small quaternary ammonium compounds such as tertiary amines quaternium and polyquaternium compounds.
  • the conditioning agent can be a fatty acid or derivatives thereof known to be useful as conditioning agents.
  • Suitable fatty acids include myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, linoleic acid, and isostearic acid.
  • the derivatives of fatty acids include carboxylic ester acids including mono-, di-, tri- and tetra- carboxylic acids.
  • the humectants are selected from but are not limited to glycols, sugars, oils, silicones, emollients and proteins. These humectants create a cage effect by adding moisture to the hair.
  • humectants which can be incorporated into a product of the present application are glycerine, propylene glycol, polypropylene glycol, polyethylene glycol, lactic acid, sodium lactate, pyrrolidone carboxylic acid, urea, phospholipids, collagen, elastin, ceramides, lecithin sorbitol, PEG-4, and mixtures thereof.
  • moisturizers are polymeric moisturizers that belong to water soluble and/or water swellable in nature.
  • Polysaccharides such as hyaluronic acid and chitosan can also be employed along with moisturizers of the present application as binder to enhance their property.
  • the suitable non-limiting moisturizers employed in the present application include glycols, glycerols, propylene glycol, diethylene glycol monoethyl ether, sorbitol, sodium salt of pyroglutamic acid, glycerol, glycerol derivatives, glycerin, trehalose, sorbitol, maltitol, dipropylene glycol, 1,3-butylene glycol, sodium hyaluronate, and the like.
  • the pH adjusting buffers are selected from but are not limited to glyoxylic acid, maleic acids, succinic acid, formic acid and other organic and inorganic acids. These buffers promote active penetration of the composition of the present application and facilitate the reactions if any for effective results of the composition.
  • the preservatives are selected from but are not limited to propylene glycol, paraben, phenoxyethanol, Caprylyl glycol, iodopropynyl butyl carbamate, and diazolidinyl urea, triazoles, imidazoles, naphthalene derivatives, benzimidazoles, morphline derivatives, dithiocarbamates, benzisothiazoles, benzamides, boron compounds, formaldehyde donors, isothiazolones, thiocyanates, quaternary ammonium compounds, iodine derivates, phenol derivatives, pyridines, dialkylthiocarbamates, nitriles, alkyl parabens and salts thereof
  • the functional polymer further aids in permanent fixation onto the hair fiber.
  • These polymers include acidic, alcoholic, thiol, or amino/amide bearing at least one hydrogen atom.
  • the presence of one or more of these groups on the straightening product will react with the straightening agents described to form a crosslinked matrix that remains affixed to hair for several shampoo cycles.
  • the presence of the polymer and/or biopolymer on the hair after several shampoo cycles is quite evident by the feel of the treated fiber as compared to the control fiber containing all the same components, but lacking the polymer component in this composition.
  • the hair composition of the present application can be employed for oxidatively dyed hair without extreme color changes that are observed by the other hair straightening treatments even before the thermal activation step is applied. In this regard, lower straightening temperatures with multiple passes are required to minimally affect the dye molecules need to be employed, and to provide some straightening effects.
  • the hair tresses are selected from Caucasian, Asian and African origins selected from fine, medium and coarse virgin, damaged, colored, grey, bleached hairs, and wherein, the hair tress has textures comprising wavy, curly, coily or kinky patterns.
  • the present application discloses a hair care composition capable of styling, straightening or conditioning hair by providing a "virgin feel condition" to the hair after multiple washes particularly provides at least one of the following result including (1) increased hydrophobicity, (2) improved detangling and wet combability, (3) improved deposition, and (4) no build-up.
  • the composition employs hybrid polymers providing the following non-limiting benefits: (i) during straightening: hybrid polymer reduces friction and assist straightening by aligning hair fibers in straight configuration so that the small reactive molecule lock straightened shape in place, and (ii) after straightening: hybrid polymer offers durability of straightening, hair conditioning or hair styling including shine, anti-frizz, volume etc.
  • the hair straightening process of the present application provides a hair styling and/or hair straightening that lasts for at least 10 to 30 hair washes even after using strong sulfate based shampoo and conditioner.
  • a method of straightening or styling hair has following steps: a) washing the hair tresses with shampoo; b) reducing or eliminating the moisture of hair tresses of step (a); c) applying the hair straightening or styling composition of present application to the dried hair of step (b); d) leaving the treated hair for about 15 to 30 minutes for penetration; e) hot air drying the treated hair of step (d) by mechanically straightening hair with either brushing or combing with a slow uniform motion from root to tip; f) ironing the hair resulted from step (e) for at least 4 to 8 times using flat iron pre-heated to 375-450°F; and g) allowing the hair tresses of step (f) to remain as such for at least 15 to 20 minutes to obtain straightened or styled hair.
  • the hybrid polymer comprising hair care, hair straightening or hair styling composition of the present application can be advantageously formulated in different types of end use products including but not limited to an emulsion, a suspension, an ointment, a lotion, a gel, vesicle dispersion, a paste, a cream, a solid stick, a mousse, a shampoo, or a spray.
  • the composition of the present application can be formulated as different types of hair-care products including but not limited to shampoos, hair conditioners, leave in and rinse off conditioners, styling and treating hair compositions, hair perming products, hair relaxants, hair straighteners, hair sprays and lacquers, permanent hair dyeing systems, hair styling mousses, hair gels, semi-permanent hair dyeing systems, temporary hair dyeing systems, hair bleaching systems, permanent hair wave systems, hair setting formulations, straightening spray lotion, smoothing and straightening fluid, straightening serum, straightening solution, emulsion, gel, vesicle dispersion, paste, cream, solid stick, shampoo, balm, wipe, milk, foam, jellies, liquid, tonics, and/or enamel.
  • hair-care products including but not limited to shampoos, hair conditioners, leave in and rinse off conditioners, styling and treating hair compositions, hair perming products, hair relaxants, hair straighteners, hair sprays and lacquers, permanent hair dyeing systems, hair styling mousses,
  • the above hybrid polymer composition can be employed in various end-user applications including pharmaceuticals, food and beverages, coatings, paints, oil and energy sectors, performance materials, oral care, skin care, hair care, cosmetics, toiletry, household and cleaning products, industrial and institutional cleaning products, disinfecting products, opthalmics, injectables, sanitary products, agricultural products, textiles, biocides, preservatives, consumer products, and laundry products.
  • hybrid polymers of the present application in skin-care products including but not limited to bath products, shower products, liquid soaps, bar soaps, fragrances and/or odoriferous ingredients consisting preparations, dentifrices, deodorizing and antiperspirant preparations, decorative preparations, light protection formulations, shaving lotions, body oils, body lotions, body gels, treatment creams, body cleaning products, skin protection ointments, shaving and aftershave preparations, skin powders, lipsticks, nail varnishes, eye shadows, mascaras, dry and moist make-up, rouge, powders, depilatory agents, sun care products, and/or compositions comprising UV blockers and UV protectors.
  • certain aspects of the present application are illustrated in detail by way of the following examples. The examples are given herein for illustration of certain aspects of the present application and are not intended to be limiting thereof.
  • HEC Hydroxyethyl cellulose
  • CMC carboxymethyl cellulose
  • EA Ethyl acrylate
  • MAA Methacrylic acid
  • *G is one or more functionalized or unfunctionalized acryloyl moiety containing monomer.
  • the reactor vessel was submerged in a water bath to maintain a temperature of 80°C throughout the reaction.
  • the required weight of sodium persulphate (SPS) and lOg of water were combined to produce two separate initiator solutions; the first shot (0.18g SPS) and the second shot (0.42g SPS).
  • SPS sodium persulphate
  • 42g of ethyl acrylate (EA) and 28g methacrylic acid (MAA) was weighed into a separate container.
  • the nitrogen feed was raised from in the water to the head space with no change to the nitrogen flow rate.
  • the first initiator shot was added to the reactor vessel.
  • the polymerization was held for 60 minutes.
  • the monomer was added to the reactor vessel in a single shot.
  • the polymerisation was held for 5 minutes.
  • the second initiator shot was added to the reactor vessel.
  • the polymerisation was held for a further 120 minutes.
  • the reaction was then cooled to room temperature by removing the water bath and allowing the reactor to cool in air. 5g Germaben II preservative was added when the polymer was ⁇ 40°C.
  • the final product was a white emulsion with a pH approx. 2.6 and average viscosity 4000cPs.
  • the dry weight of the product was 10%.
  • the process was depicted in scheme 1.
  • *G is one or more functionalized or unfunctionalized acryloyl moiety containing monomer.
  • *G is one or more functionalized or unfunctionalized acryloyl moiety containing monomer.
  • *G is one or more functionalized or unfunctionalized acryloyl moiety containing monomer.
  • the mechanical stirrer was restarted at 400 rpm.
  • the reactor charge was purged with nitrogen for 30 minutes without heating and a further 60 minutes with heating submerged below the solution surface at a rate of 0.21/min.
  • the reactor vessel was submerged in a water bath to maintain a temperature of 80°C throughout the reaction.
  • the required weight of sodium persulphate (SPS) and lOg of water were combined to produce two separate initiator solutions; the first shot (0.09g SPS) and the second shot (0.21g SPS). 21g of ethyl acrylate and 14g methacrylic acid was weighed into a separate container.
  • the nitrogen feed was raised from in the water to the head space with no change to the nitrogen flow rate.
  • the first initiator shot was added to the reactor vessel.
  • the polymerisation was held for 60 minutes.
  • the monomer was added to the reactor vessel in a single shot.
  • the polymerisation was held for 5 minutes.
  • the second initiator shot was added to the reactor vessel.
  • the polymerisation was held for a further 120 minutes.
  • the reaction was then cooled to room temperature by removing the water bath and allowing the reactor to cool in air. 5g Germaben II preservative was added when the polymer was ⁇ 40°C.
  • the final product was a white emulsion with a pH approx. 3.7 and average viscosity 175CPS.
  • the dry weight of the product was 5%.
  • the process was depicted in scheme 4.
  • EXAMPLE 2 STRAIGHTENING SPRAY LOTION
  • Procedure Water was charged to a suitable mixing vessel and began agitation to create medium to deep vortex. Sodium Bicarbonate and hybrid polymer were added into the vortex and mixed until the dissolution of the compounds, and then agitation was reduced. The remaining ingredients were added one by one and mixed well after each addition.
  • EXAMPLE 5 STRAIGHTENING SERUM
  • Phase-A was prepared by adding water to a main container and began mixing, then each of the ingredients viz., water, Disodium EDTA, Glyoxylic acid, Lactic acid and Hybrid polymer were added one by one. The batch was heated to 70-75 °C and mixed; 2. Phase-B was prepared by melting Behenyl Alcohol (and) Cetearyl Alcohol (and) Hydroxyethyl Cetearamidopropyldimonium Chloride flake at 75 °C, then added to Phase-A while vigorously mixing and the temperature was maintained for 20 minutes; 3. The batch was slowly cooled to 60°C and then amodimethicone mixture was added with thorough mixing; 4. Cooling was continued and Benzyl Alcohol mixture was added as last ingredient by maintaining the temperature around 40°C.
  • EXAMPLE 7 STRAIGHTENING PERM
  • Premix In separate kettle, Laureth-23 was melted and mixed in fragrance; this mixture was added to the main part, the pH of the batch was checked and adjusted, if the pH is more than 3.
  • HEC/EA/MAA Hydrophilethylcellulose/Ethyl acrylate/methacrylic acid
  • HEC/EA/APRAC Hydroxethylcellulose/Ethyl acrylate/_acrylamidopropyltrimethyl ammonium chloride

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Abstract

La présente invention concerne une composition de défrisage ou de coiffage des cheveux constituée d'un polymère hybride greffé et d'au moins un support. Le polymère hybride greffé est dérivé de (i) au moins un groupement de cellulose fonctionnalisé ou non fonctionnalisé et au moins un groupement acryloyle fonctionnalisé ou non fonctionnalisé; ou (ii) un groupement de galaetomannan fonctionnalisé ou non fonctionnalisé et au moins un groupement acryloyle fonctionnalisé ou non fonctionnalisé. Le support peut être de l'eau, de l'alcool, de l'hydroalcool, une émulsion, un ester, un hydrocarbure ou un support d'huile organique ou inorganique. La présente invention concerne également un procédé de préparation de la composition comprenant les polymères hybrides et des procédés d'utilisation de la composition comprenant de tels polymères hybrides greffés.
PCT/US2017/042598 2016-07-18 2017-07-18 Une composition de défrisage et de coiffage des cheveux, procédé de son préparation et procédé d'utilisation de celle-ci Ceased WO2018017570A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021025254A1 (fr) * 2019-08-05 2021-02-11 주식회사 엘지생활건강 Agent de revêtement polymère possédant simultanément d'excellentes propriétés hydrofuges et oléofuges, et composition cosmétique comprenant celui-ci et présentant une excellente persistance de maquillage
CN112985970A (zh) * 2021-03-01 2021-06-18 上海屹尧仪器科技发展有限公司 一种利用可充气的微波消解装置快速水解乳制品中蛋白质的方法
EP3801775A4 (fr) * 2018-06-03 2022-05-04 EasyFix Hair Design Ltd. Composition acrylique d'auto-durcissement pour le coiffage des cheveux
CN119161536A (zh) * 2023-06-20 2024-12-20 宁德时代新能源科技股份有限公司 聚合物、负极极片、电池和用电装置

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Publication number Priority date Publication date Assignee Title
EP3801775A4 (fr) * 2018-06-03 2022-05-04 EasyFix Hair Design Ltd. Composition acrylique d'auto-durcissement pour le coiffage des cheveux
WO2021025254A1 (fr) * 2019-08-05 2021-02-11 주식회사 엘지생활건강 Agent de revêtement polymère possédant simultanément d'excellentes propriétés hydrofuges et oléofuges, et composition cosmétique comprenant celui-ci et présentant une excellente persistance de maquillage
KR20210016732A (ko) * 2019-08-05 2021-02-17 주식회사 엘지생활건강 발수 및 발유 특성이 동시에 우수한 고분자 피막제 및 이를 포함하는 화장 지속성이 우수한 화장료 조성물
KR102260329B1 (ko) 2019-08-05 2021-06-02 주식회사 엘지생활건강 발수 및 발유 특성이 동시에 우수한 고분자 피막제 및 이를 포함하는 화장 지속성이 우수한 화장료 조성물
CN114173748A (zh) * 2019-08-05 2022-03-11 株式会社Lg生活健康 同时具有优异的拒水和拒油特性的聚合物被膜剂以及包含其的具有优异的妆容持久性的化妆料组合物
CN114173748B (zh) * 2019-08-05 2024-03-08 株式会社Lg生活健康 同时具有优异的拒水和拒油特性的聚合物被膜剂以及包含其的具有优异的妆容持久性的化妆料组合物
US12485081B2 (en) 2019-08-05 2025-12-02 Lg Household & Health Care Ltd. Polymer coating agent having concurrently excellent water and oil repellent properties and cosmetic composition comprising same showing excellent make-up persistency
CN112985970A (zh) * 2021-03-01 2021-06-18 上海屹尧仪器科技发展有限公司 一种利用可充气的微波消解装置快速水解乳制品中蛋白质的方法
CN119161536A (zh) * 2023-06-20 2024-12-20 宁德时代新能源科技股份有限公司 聚合物、负极极片、电池和用电装置
WO2024259966A1 (fr) * 2023-06-20 2024-12-26 宁德时代新能源科技股份有限公司 Polymère, feuille d'électrode négative, batterie et appareil électrique

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