WO2018017408A1 - Composition de soin capillaire, son procédé de préparation et son procédé d'utilisation - Google Patents

Composition de soin capillaire, son procédé de préparation et son procédé d'utilisation Download PDF

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Publication number
WO2018017408A1
WO2018017408A1 PCT/US2017/042093 US2017042093W WO2018017408A1 WO 2018017408 A1 WO2018017408 A1 WO 2018017408A1 US 2017042093 W US2017042093 W US 2017042093W WO 2018017408 A1 WO2018017408 A1 WO 2018017408A1
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Prior art keywords
acrylate
hair
cellulose
methacrylate
straightening
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Solomon T. WOSSENE
Manuel Gamez-Garcia
Andrea Louise BURRON
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ISP Investments LLC
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ISP Investments LLC
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    • A—HUMAN NECESSITIES
    • A45—HAND OR TRAVELLING ARTICLES
    • A45D—HAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
    • A45D7/00—Processes of waving, straightening or curling hair
    • A45D7/04—Processes of waving, straightening or curling hair chemical
    • A—HUMAN NECESSITIES
    • A45—HAND OR TRAVELLING ARTICLES
    • A45D—HAIRDRESSING OR SHAVING EQUIPMENT; EQUIPMENT FOR COSMETICS OR COSMETIC TREATMENTS, e.g. FOR MANICURING OR PEDICURING
    • A45D7/00—Processes of waving, straightening or curling hair
    • A45D7/06—Processes of waving, straightening or curling hair combined chemical and thermal
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61Q5/04—Preparations for permanent waving or straightening the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring

Definitions

  • the present application relates to a hair care composition, and more particularly, to a hair straightening or hair styling composition comprising at least one hydroxy ketone, at least one hybrid polymer, at least one organic base and optionally, a functional polymer.
  • the present application further relates to a process for preparing the composition and method of hair straightening.
  • Human hair is made up of a protein called keratin which forms a long helical chain like a very thin strand of rope. Groups of these thin strands form filaments. Groups of filaments in turn form the bulk of the hair strand's inner layer called the cortex. Outermost layer of the filament is called cuticle. The cuticle protects the hair from external factors like light and heat but is sensitive to pH changes. Any change in the pH causes outermost layer to open up and allows for different modifications to hair such as coloring or straightening. Hair straighteners change how strands of keratin stick together.
  • U.S. Pub. No. 20130139845 assigned to L'Oreal S.A. discloses a method for straightening keratinous fibers including: (i) a step of applying on the keratinous fibers a hair straightening composition containing at least one alpha-hydroxy and/or keto acid derivative, the pH of said composition being not more than 9 (ii) a step of increasing the temperature of the keratinous fibers, using heating means, to a temperature ranging between 110 and 250° C.
  • PCT Publication Number WO2012/084533A1 assigned to Henkel AG & Co. KGAA discloses a 1,3-dihydroxyacetone in hydroalcoholic solution for heat assisted shaping of keratin fibers.
  • the application further discloses optional use of a conditioning polymer and a fixative polymer for thermal straightening.
  • the present application provides a hair straightening or hair styling composition which lasts for at least 10 wash cycles and employs environment friendly ingredients that are compliant with global regulatory norms.
  • the present application provides a hair straightening or hair styling composition
  • a hair straightening or hair styling composition comprising: A) at least one a or ⁇ - hydroxy ketone; B) a first polymeric compound selected from: (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 (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; C) at least one organic or inorganic base; D) optionally, at least one functional polymer; and E) at least one carrier.
  • the present application further provides a second polymeric compound selected from (a) a functionalized or unfunctionalized cellulose moiety, or (b) a functionalized or unfunctionalized galactomannan moiety.
  • the present application provides a hair straightening or hair styling composition
  • a hair straightening or hair styling composition comprising: (i) about 0.1 % wt./wt. to about 70.0% wt./wt. of at least one of dihydroxyacetone, 4-hydroxy-2-butanor!e, i -hydroxy-2-butanone and combinations thereof; (ii) about 0.1 % wt./wt. to about 50.0% wt./wt.
  • hybrid polymer selected from: (a) hydroxyethyl cellulose / ethyl acrylate / methacrylic acid copolymer; (b) hydroxyethyl cellulose / ethyl acrylate copolymer; (c) carboxymethyl cellulose / ethyl acrylate copolymer; or (d) cationic guar / ethylacrylate / methacrylic acid copolymer; (iii) about 0.1 % wt./wt. to about 20.0% wt./wt. of sodium bicarbonate or propylene carbonate; (iv) optionally, about 0.1 % wt./wt.
  • composition has a pH of about 5 to about 11.
  • the present application provides a hair straightening or hair styling composition formulated into a straightening spray lotion, non-aerosol straightening mousse, hair relaxant, semi-permanent hair dyeing system, temporary hair dyeing system, hair bleaching system, permanent hair wave system, hair setting formulation, 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.
  • the present application provides a method of straightening or styling hair, the method comprises: step (a) washing the hair tresses with shampoo; step (b) eliminating or reducing the moisture of hair tresses of step (a); step (c) applying the hair straightening or styling composition comprising: (A) dihydroxy acetone, 4-hydroxy-2- butanone, l-hydroxy-2-butanone or combinations thereof; (B) first polymeric compound selected from: (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 (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; (C) sodium bicarbonate; (D) at least one functional polymer, and (E) at least one carrier, to the
  • the present hair styling or hair straightening composition does not require highly acidic pH (1 to 4) or highly basic pH (12 to 14) conditions for straightening/styling applications, and requires less time to wash the straightened hair immediately and makes it advantageous over the commercial compositions which require high pH and long waiting hours (around 24-36 hours) before washing.
  • Fig. 1 illustrates effect of hydroxyacetone in combination with hybrid polymer (HEC/EA/MAA) on hair stresses, wherein ( A) is untreated hair stresses; ( B) is hair stresses treated with hydroxyacetone; and (C) is hair treated with hydroxyacetone and hybrid graft polymer HEC/EA/MAA.
  • HEC/EA/MAA hybrid polymer
  • 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 ⁇ , ⁇ -hydroxy ketones, cellulose ethers, galactomannans, acryloyl moieties, organic or inorganic bases, functional polymers, hybrid polymers, and/or carrier.
  • the terms “include,” “includes,” and “including,” are meant to be non-limiting and are understood to mean “comprise,” “comprises,” and “comprising,” respectively.
  • cosmetically acceptable ingredient means any ingredient/compound or mixture of ingredients/compounds or compositions that are typically employed to produce other aesthetic or cosmetic based desirable effects in personal care compositions.
  • the preferred cosmetically acceptable excipients include but not limited to preservatives, antioxidants, chelating agents, sunscreen agents, proteins, amino acids, vitamins, dyes, hair coloring agents, plant extracts, humectants, fragrances, emollients, lubricants, butters, penetrants, thickeners, viscosity modifiers, polymers, resins, hair fixatives, film formers, surfactants, detergents, emulsifiers, pacifying agents, volatiles, propellants, liquid vehicles, carriers, salts, pH adjusting agents, neutralizing agents, buffers, hair conditioning agents, anti-static agents, anti-frizz agents, anti-dandruff agents, hair waving agents, hair straightening agents, relaxers, absorbents, fatty substances, gelling agents, moisturizers,
  • the term "functional polymer” refers to IUPAC nomenclature ,i.e., a polymer that bears specified chemical groups or has specified physical, chemical, biological, pharmacological, or other uses which depend on specific chemical groups. Accordingly, the term “functional polymer” of the present application refers to a non-hybrid polymer which is capable of demonstrating thickening, styling or conditioning properties for the purpose of the present application.
  • the term "functionalized” refers to the state of a moiety that has one or more functional groups introduced to it by way of one or more functionalization reactions known to a person having ordinary skill in the art.
  • 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, ior e.g. , alkyl, alkoxyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, and/or aryl groups.
  • non-hydrogen groups ior e.g. , alkyl, alkoxyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, and/or aryl groups.
  • Non-limiting examples of cycloalkyl groups include cyclopentane, cyclohexane, cycloheptane, and the like;
  • Non-limiting examples of alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, and the like;
  • Non-limiting examples of aryl groups include benzenes, naphthalenes (2 rings), anthracenes (3 rings), and the like.
  • hair straightening refers to the state where the natural curl of the hair has been removed and 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.
  • 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.
  • the term "homopolymer” refers to a molecule that comprises one type of monomer
  • 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 may or may not be covalently bonded into the polymer.
  • the non-homopolymer is copolymers, terpolymers, tetramers, and the like.
  • hybrid graft polymer or “hybrid polymer” refers to polymer derived from: (a) a functionalized or unfunctionalized cellulose moiety and (b) at least one functionalized or unfunctionalized acryloyl moiety; or polymer derived from (a) a functionalized or unfunctionalized galactomannan moiety and (b) at least one functionalized or unfunctionalized acryloyl moiety.
  • 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. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, and is not intended to exclude other embodiments from the scope of the invention.
  • polymer refers to a compound comprising repeating structural units (monomers) connected by covalent chemical bonds. Polymers may be further derivatized, crosslinked, grafted or end-capped. Non-limiting examples of polymer include copolymer, terpolymer, quaternary polymer, and their homologues.
  • copolymer refers to a polymer consisting essentially of two or more different types of repeating structural units (monomers).
  • washed and “washing” refers to rinsing of hair with water.
  • a hair straightening or hair styling composition comprising:
  • a first polymeric compound selected from: (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 (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;
  • the present composition further comprises a second polymeric compound selected from (a) a functionalized or unfunctionalized cellulose moiety, or (b) a functionalized or unfunctionalized galactomannan moiety.
  • the hair straightening or styling composition of the present application comprises at least one hydroxy ketone compound in the concentration range of from about 0.1% wt./wt. to about 70% wt./wt. of the total composition.
  • a hydroxy ketone (often referred to simply as ketol) is a functional group wherein ketone functionality is flanked by a hydroxyl group, and wherein, based on the position of hydroxyl group with respect to ketone functionality, the alpha- hydroxy ketone or beta- hydroxy ketone results.
  • ketol a functional group wherein ketone functionality is flanked by a hydroxyl group, and wherein, based on the position of hydroxyl group with respect to ketone functionality, the alpha- hydroxy ketone or beta- hydroxy ketone results.
  • R and R t are the same or different and are each H or a straight chain or branched and optionally substituted Q to C 12 alkyl radical
  • R 2 is t-butyl, n-butyl, sec-butyl, n- propyl, iso-propyl, an optionally heteroatom-substituted C 6 -C 18 aryl, heteroaryl, C 6 -C 18 arylalkyl, especially phenylmethyl, where phenyl may again be heteroatom substituted, or heteroalkyl or any combination thereof.
  • the suitable and non-limiting hydroxy ketones employed in the present application are present in an amount of from about 0.1 % wt./wt. to about 70% wt./wt. of the total hair straightening or styling composition.
  • Preferred hydroxy ketones are selected from dihydroxyacetone, 4-hydroxy-2-butanone, l-hydroxy-2-butanone or combinations thereof.
  • the hydroxy ketones of the present application are capable of penetrating into the hair fiber's cortex to modify the hair fiber's natural shape while the styling polymer provides additional shape control, styling, and aesthetic qualities like body, shine, feel, conditioning and luster.
  • the present application provides a functionalized or unfunctionalized cellulose moiety that is a cellulose ether moiety having the general structure represented below:
  • R is (i) independently hydrogen, (ii) Ci to C50 straight or branched chain functionalized or unfunctionalized hydrocarbyl groups including but not limited to alkyl, cycloalkyl, aryl, cycloaryl, alkoxyl, aryloxyl, alkylaryloxyl, cycloalkoxy, cycloaryloxy, cycloarylalkoxyl groups; (iii) hydroxyalkyl functional groups excluding hydroxy ethyl specifically, (iv) alkylcarboxy groups; and/or (v) functionalized/non-functionalized, substituted or free carbonyl groups, and wherein said functional groups are provided with or without heteroatoms; and n is 1 to 2000 and wherein, at least one R is substituted with at least one acrylate moiety.
  • Cellulose is a naturally available homopolymer commonly found in plant cell walls. Chemically, it is a linear assembly of ⁇ -D-anhydroglucopyranose units which are covalently connected through a linkage between Ci anomeric carbon and C 4 carbon atom to provide ⁇ -1,4- glycosidic bonds.
  • One repeating unit of cellulose molecule has one methyl and two hydroxyl groups as its functional groups, and wherein, two hydroxyl groups includes a primary hydroxyl in the methylol group at C-6 and two secondary hydroxyl groups (-OH) at C-3 and C-4 position.
  • Chemical modification of the hydroxyl groups at C2, C3, and/or C6 positions of cellulose has been developed to confer novel properties including hydrophilic, antimicrobial, and thermoplastic character, where the degree of substitution (DS) and distribution of the substituents determine the modified cellulose structure and behavior.
  • Reactivity of these hydroxyl groups with ether functional groups results in formation of cellulose ethers.
  • the order of reactivity for etherification performed in an alkaline medium is 2 > 6 > 3.
  • Cellulose ethers have numerous advantages over other cellulose derivatives in terms of availability, economic efficiency, easy handling, low toxicity, and great variety of types. Combined effects of flow control, stabilization, water retention, film formation, etc. provided by cellulose ethers are not generally obtainable using fully synthetic polymers.
  • Non-limiting examples of the cellulose ether moieties of the present application include hydroxyalkyl celluloses, alkyl celluloses, carboxyalkyl celluloses, for example, methyl cellulose (MC), ethylcellulose (EC), propyl cellulose (PC), methylhydroxyethylcellulose (MHEC), ethyl hydroxyethyl cellulose (EHEC), methylethyl hydroxyethyl cellulose (MEHEC), hydroxypropyl hydroxyethyl cellulose (HPHEC), methyl hydroxypropyl hydroxyethyl cellulose (MHPHEC), hydroxypropyl cellulose (HPC), ethyl hydroxypropyl cellulose (EHPC), hydroxypropyl methyl cellulose (HPMC), ethylhydroxyethylcellulose (EHEC), carboxyalkyl celluloses, carboxyalkyl hydroxyalkyl cellulose, carboxymethyl cellulose, carboxymethylcellulose, carboxypropy
  • the preferred cellulose ether for the present application are methylcellulose (MC), ethylcellulose (EC), carboxymethylcellulose (CMC), hydroxypropyl methyl cellulose (HPMC), ethylhydroxyethylcellulose (EHEC), and methylhydroxyethylcellulose (MHEC).
  • Most preferred cellulose ether moieties include hydroxyethyl cellulose (HEC 250 HV, Natrosol TM hydroxyethyl cellulose, Ashland), hydroxypropyl cellulose (HPC HF pharma, Klucel TM, Ashland) and Carboxymethyl cellulose (CMC).
  • the present application provides at least one functionalized or unfunctionalized galactomannan moiety having a general structure represented below:
  • Galactomannans are heterogeneous polysaccharides composed of a-(1 ⁇ 4)-d-mannan backbone with a single d-galactose branch linked (1-6). They differ from each other by the mannose/galactose (M/G) ratio. These gums are seed polysaccharides mostly obtained from the endosperm of dicotyledonous seeds of numerous plants, particularly the Leguminosae.
  • locust bean (Ceratonia siliqua), guar (Cyamopsis tetragonoloba), Tara (Caesalpinia spinosa Kuntze), and fenugreek (Trigonella foenum-graecumL.).
  • locust bean Ceatonia siliqua
  • guar Cyamopsis tetragonoloba
  • Tara Caesalpinia spinosa Kuntze
  • fenugreek Trigonella foenum-graecumL.
  • the distribution of the galactose units over the mannose backbone varies with plant origin but is typically in the range of 1.0: 1.0-1.1 for fenugreek, 1.0: 1.6-1.8 for Guar, 1.0:3.0 for tara, and 1.0:3.9-4.0 for locust bean gum.
  • M/G ratio varies considerably depending on the galactomannan source and variations in the galactomannan' s structure, particularly in M/G ratio and fine structure, causes significant changes in the solubility, viscosity and in the interactions between galactomannans and other polysaccharides.
  • galactomannans with higher galactose content such as Guar Gum
  • galactomannans with a lower M/G ratio such as Locust Bean Gum
  • the higher solubility of Guar Gum has been attributed to the presence of a higher number of side chains, which keep the main mannose chains far enough to prevent effective intermolecular interactions.
  • galactomannans with fewer side chains can interact with other polysaccharides due to their long blocks of unsubstituted mannose units.
  • the average molecular weight of the Galactomannan is in the range of l-2xl0 6 Da.
  • Galactomannan forms viscous, colloidal dispersion when hydrated in water.
  • the galactose side groups are considered to sterically disturb the interchain association and crystallization, thereby imparting certain water solubility to the galactomannans.
  • the solubility of the galactomannans increases with the degree of galactosyl substitution: fenugreek and guar gums are readily dissolved in cold water, but heating is needed to reasonably solubilize locust bean gum in water.
  • Galactomannan gum and ether derivatives when added to water increase the viscosity of the resulting aqueous composition.
  • Derivatives of galactomannan gums are also valuable thickeners.
  • Galactomannan gums when substituted by addition of hydroxy alkyl or carboxy alkyl groups to the hydroxyl radical result in ether derivatives and impart improved properties to the galactomannan gum.
  • the degree of etherification may vary from 0.01 to 0.9 moles. Normally, the degree of substitution is from 0.05 to 0.5.
  • a viscosity increasing amount of galactomannan gum is about 0.01 to 10 parts by weight per 100 parts by weight of water.
  • galactomannans The great advantage of galactomannans is their ability to form very viscous solutions at relatively low concentrations that are only slightly affected by pH, ionic strength and heat processing.
  • Galactomannan' s viscosity tends to remain constant over a broad pH range (1- 10.5), mainly due the neutral character of their molecules, and is not expected that their properties will change with ionic strength.
  • the viscosity and the stability of the galactomannan solutions upon storage depend on the time and temperature used during the film-forming solution preparation. Heating the galactomannans at temperatures above 60°C tend to provide a high initial viscosity but lead to an inferior stability (in terms of time-dependent changes in viscosity). The most convenient temperature depends on the galactomannan source.
  • locust bean gum must be heated at 80°C for 20-30 min to guarantee its full dispersion, while the optimal conditions to disperse guar gum involve heating at 25-40°C for 2hrs.
  • Galactomannan solutions usually exhibit a non-Newtonian behavior, in which the viscosity decreases with the increase of shear rate.
  • Galactomannans are widely utilized in the industry due to their suitable functional properties, such as thickening, binding, and stabilizing abilities. These functional properties are led by rheological behavior of galactomannans in an aqueous phase and by intermolecular binding in certain conditions. Hydrated galactomannan molecules occupy a large hydrodynamic volume in aqueous solution and control the rheological behavior of the entire solution. Galactomannans themselves are non-gelling agents, while some galactomannans show synergistic interactions with other polysaccharides such as agar, xanthan, carrageenan, and yellow mustard gum to form a three-dimensional gel network in appropriate conditions.
  • Galactomannans thus find a wide range of applications as texture modifiers or stabilizers in food and pet food industries.
  • Galactomannans are able to form gels with certain metal salts and are used in the field of textiles to print vat-dyestuffs in two phases, which yield bright and sharp prints. Transport of solid powders like coal or ores suspended in such gels through pipeline is also possible as these gels have excellent suspending force, which can be destroyed immediately when reaching the final point of destination by heating to only about 50°C.
  • Galactomannans replace the natural hemicellulose in paper bonding. Since galactomannans absorb onto the hydrated cellulose fibers, as the hydrogen bonding effect is one of the major factors in fiber bonding. Carboxymethyl derivatives of Cassia gum also show excellent hydrogen bonding effects, especially when used as wet end additives and as sizing agent in paper manufacturing.
  • Locust bean gum is a natural polymer conventionally used as an excipient in manufacturing different formulation which mainly depends on its thickening and gelling property.
  • Locust bean gum is a non-starch polysaccharide consisting of galactose and mannose in the ratio 1 :4 and hence they are known as galactomannan.
  • Locust bean gum consists mainly of a neutral galactomanan polymer made up of 1,4-linked d-mannopyronosyl units and every fourth of fifth chain is substituted on C6 with a d-galactopyranosyl unit. Since it is a neutral polymer and its viscosity and solubility are therefore little affected by pH changes within the range.
  • Tara gum is extracted from the endosperm with warm or hot water.
  • the industrial manufacturing process is essentially the same as that of locust beam gum and guar gum.
  • the average molecular weight typically ranges from 0.2 to 2 million.
  • Guar is a water-soluble polysaccharide derived from the Cyamopsis tetragonoloba, family Leguminosae. Chemically, guar gum is a straight chain galactomannan, which is 75- 85% of the endosperm, has a chain of (1 ⁇ 4) -linked-- ⁇ i-mannopyranosyl units with single galactopyranosyl units connected by (1 ⁇ 6) linkages to, on the average, every second main chain unit.
  • the guar gum containing compounds of the present invention can include a guar gum backbone that includes at least one H, OH, an alkoxy group, an acyloxy group, an amino group, an amido group, an ester group, a sulfate group, a sulfonate group, a phosphate group, a phosphonate group, a silicone group, a surfactant, a urethane group (including polyurethanes attached to the backbone). Due to its unique rheology modifying properties, it is being widely used across a broad spectrum of industries viz. oil well drilling, textile, paper, paint, cement, cosmetic, food, pharmaceutical, etc. This observation makes guar gum the most soluble and the most widely used of all galactomannans.
  • Non-limiting examples of galactomannan are cationic galactomannan, amphoteric galactomannan base on type of functional group attached to the galactomannan moiety.
  • Examples include cassia gum, tara gum, carrageenan gum, alginate, starch, or guar; a non-ionic guar selected from methyl guar, ethyl guar, allyl guar, hydroxyethyl guar, hydroxypropyl guar, hydroxybutyl guar; a cationic guar selected from guar hydroxypropyltrimonium chloride, guar hydroxypropyl dimethyl alkyl ammonium chloride, and guar hydroxyethyl dimethyl alkyl ammonium chloride; an anionic guar selected from carboxymethyl guar, carboxypropyl guar, carboxybutyl guar, carboxymethylhydroxypropyl guar; sulfate esters
  • biopolymer gelling agents are GalactasolTM carboxymethyl hydroxypropyl guar (CMHPG), GalactasolTM guar gum, and GalactasolTM hydroxypropyl guar (HPG) from Ashland.
  • CMHPG carboxymethyl hydroxypropyl guar
  • HPG GalactasolTM hydroxypropyl guar
  • present application provides a functionalized or unfunctionalized acryloyl moiety represented by:
  • each Ri, R2, R3 is independently selected from the group consisting of hydrogen, halogens, functionalized and unfunctionalized C1-C4 alkyl groups optionally having one or more heteroatoms, and combinations thereof, and M is selected from the group consisting of hydrogen, metal ions, ammonium ion, organic amino cations and functionalized or unfunctionalized C1-C60 hydrocarbyl group, vinyl pyrrolidone and vinyl caprolactam optionally having one or more hetero atoms.
  • Non-limiting examples of acryloyl moiety include acrylic acid, methacrylic acid, sodium acrylate, sodium methacrylate, potassium acrylate, potassium methacrylate, ammonium acrylate, ammonium methacrylate, calcium acrylate, calcium methacrylate, 2-ethylacrylic acid, 2-propylacrylic acid, methacrylate, methyl acrylate, ethyl acrylate, 2-(2-ethoxyethoxy)ethyl acrylate, 2-phenoxyethyl acrylate, alkoxylated phenol acrylates, ethoxylated hydroxyethyl acrylates, ethyl 2-ethylacrylate, 2-ethylhexyl acrylate, ethyl 2-propylacrylate, 4-acetoxyphenethyl acrylate, n-propyl acrylate, isopropyl acrylate, n- butyl acrylate, isobutyl acrylate, sec
  • the monomer comprising at least one acryloyl moiety with at least one lactam moiety functionality has the structure:
  • each Ri R2 and R3 is independently selected from the group consisting of
  • each X is ted from the group consisting of OR4, OM, halogen, N(R 5 )(R6), , and combinations thereof; each Y is independently oxygen, NR7 or sulfur; each R 4 , R5, R 6 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 Qi, Q2, Q3, and Q 4 is independently selected from the group consisting of functionalized and unfunctionalized alkylene.
  • each Qi, Q2, Q3, and Q 4 is independently selected from the group consisting of functionalized and unfunctionalized Ci - C12 alkylene.
  • alkylene groups include -CH2-. -CH2-CH2-, -CH(CH3)-CH2- -CH 2 - CH(CH 3 )-, -C(CH 3 )2-CH 2 -, -CH2-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-, -CH 2 -CH 2 -CH(CH 3 )-, - CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-, -CH2-CH2-CH2-CH2-CH2-CH
  • each Ri and R3 is independently hydrogen or methyl; R2 is C X ; ⁇ is selected from the group consisting of OR 4 , OM, halogens, and N(R 5 )(R6); each R 4 , R5, and R 6 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 combinations thereof.
  • 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).
  • Non-limiting examples include N-hydroxyethyl-2-pyrrolidoneacrylate, N- hydroxymethyl-2-pyrrolidoneacrylate, N-hydroxypropyl-2-pyrrolidoneacrylate, N- hydroxymethyl-2-pyrrolidonemethacrylate, N-hydroxyethyl-2-pyrrolidonemethacrylate, N- hydroxypropyl-2-pyrrolidonemethacrylate, N-hydroxymethyl-2-pyrrolidone methyl methacrylate, N-hydroxyethyl-2-pyrrolidone methyl methacrylate, N-hydroxypropyl-2- pyrrolidone methyl methacrylate, N-hydroxymethyl-2-caprolactamacrylate, N-hydroxyethyl- 2-caprolactamacrylate, N-hydroxypropyl-2-caprolactamacrylate, N-hydroxyethyl-2- caprolactam methacrylate, N-hydroxymethyl-2-caprolactam methacrylate, N-hydroxypropyl-2-cap
  • 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 (APTAC), diallyl dimethyl ammonium chloride (DADMAC); Acryloyloxy ethyl trimethylammonium chloride (AETAC); Methacrylamidopropyl trimethylammonium chloride (M APT AC); Dimethylaminoethyl methacrylate (DMAEMA or MADAME); Methyloyloxy ethyl trimethyl ammonium chloride (METAC); Dimethylaminopropyl methacrylamide-N-(3-chloro-2- hydroxypropyl)-trimethylammonium chloride (DIQUAT chloride), and Methacryloylaminopropyl
  • APITAC acrylamidoprop
  • the present application provides, (i) at least one cellulose moiety or at least one galactomannan moiety chemically connected with (ii) at least one acrylate moiety connected by chemical reaction to yield desired hybrid polymer of the present application.
  • the present application provides or contemplates a physical mixture comprising (i) at least one cellulose moiety or at least one galactomannan moiety and (ii) at least one acrylate moiety. The resulting hybrid polymer and physical mixture both are capable of providing a better and differentiated effects on hair styling and straightening when used along with at least one hydroxyacetone and/or at least one organic base.
  • the cellulose ether moieties are grafted with desired acrylate moieties, and wherein, such grafting methods are expected to modify the surface of polymers to offer desired properties.
  • the non-limiting representative cellulose ether-acrylate hybrid polymer are disclosed below:
  • R is any functionalized or non-functionalized monomers selected from the group comprising but not limited to acrylates and acids based compounds that are grafted onto hydroxy functionality of cellulose or galactomannan moieties.
  • Another non-limiting embodiment of the present application discloses a hybrid polymer of cellulose ether or galactomannan moiety employing amides, quaternary ammonium compounds,
  • the concentration of hybrid polymer and optional second polymer used for preparing hair styling or hair straightening composition is in the range of from about 0.1 % wt./wt. to about 70% wt./wt. of the total composition.
  • Other non-limiting ranges of hybrid 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. , about 50% wt./wt. to about 60% wt./wt. , or about 60% wt./wt. to about 70% wt./wt. of the total composition.
  • the present application provides a hybrid graft polymer derived from reaction product of: (a) about 20% wt./wt. to about 50% wt./wt. of at least one functionalized or unfunctionalized cellulose ether moiety; and (b) about 20% wt./wt. to about 60% wt./wt. of at least one functionalized or unfunctionalized acryloyl moiety.
  • the present application provides a hybrid graft copolymer derived from reaction product of (a) about 20% wt./wt. to about 50% wt./wt.
  • the present application provides a hybrid graft copolymer comprising: a reaction product of (i) about 10% wt./wt. to 40% wt./wt. of hydroxy ethyl cellulose (HEC); (ii) about 20% wt./wt. to 60% wt./wt. of ethyl acrylate (EA); and (iii) about 10% wt./wt. to 40% wt./wt. of methacrylic acid (MA A).
  • HEC hydroxy ethyl cellulose
  • EA ethyl acrylate
  • MA A methacrylic acid
  • hybrid graft copolymer comprising: (i) about 30% wt./wt. of hydroxy ethyl cellulose (HEC); (ii) about 42% wt./wt. of ethyl acrylate (EA); and (iii) about 28% wt./wt. of methacrylic acid (MAA), and the process for preparing above said hybrid polymer is represented by the following general reaction scheme:
  • hybrid graft copolymer comprising: a reaction product of (i) about 10% wt./wt. to 40% wt./wt. of carboxy methyl cellulose (CMC); (ii) about 20% wt./wt. to 60% wt./wt. of ethyl acrylate (EA); and (iii) about 10% wt./wt. to 40% wt./wt. of methacrylic acid (MA A).
  • CMC carboxy methyl cellulose
  • EA ethyl acrylate
  • MA A methacrylic acid
  • Another non-limiting embodiment discloses a hybrid graft copolymer comprising: (i) about 30% wt./wt. of carboxy methyl cellulose (CMC); (ii) about 42% wt./wt. of ethyl acrylate (EA); and (iii) about 28% wt./wt. of methacrylic acid (MAA), and the process for preparing above said hybrid polymer is represented by the following general reaction scheme:
  • Another embodiment of the present application discloses a hybrid graft copolymer comprising: a reaction product of (i) about 30% wt./wt. to about 60% wt./wt. of carboxy methyl cellulose (CMC); and (ii) about 30% wt./wt. to about 60% wt./wt. of ethyl acrylate (EA).
  • CMC carboxy methyl cellulose
  • EA ethyl acrylate
  • hybrid graft copolymer comprising: (i) about 50% wt./wt. of carboxy methyl cellulose (CMC); and (ii) about 50% wt./wt. of ethyl acrylate (EA), and the process for preparing above said hybrid polymer is represented by the fo
  • Carboxy metbylcellulose graft polymer [0075]
  • the present application provides a hybrid graft polymer derived from: a reaction product of (a) about 20% wt./wt. to about 60% wt./wt. of at least one functionalized or unfunctionalized galactomannan moiety and (b) about 20% wt./wt. to about 60% wt./wt. of at least one functionalized or unfunctionalized acryloyl moiety.
  • Another non-limiting hybrid graft copolymer comprises: (i) about 20% wt./wt. to about 40% wt./wt. of cationic guar; (ii) about 30% wt./wt. to 60% wt./wt. of ethyl acrylate (EA); and (iii) about 20% wt./wt. to 40% wt./wt. of methacrylic acid (MAA).
  • a hybrid graft copolymer comprising: a reaction product of (i) about 30% wt./wt. of cationic guar; (ii) about 42% wt./wt. of ethyl acrylate (EA); and (iii) about 28% wt./wt. of methacrylic acid (MAA), and the process for preparing above said hybrid polymer is represented by the following general reaction scheme:
  • the present application provides a hybrid graft polymer derived from: a reaction product of (a) about 20% wt./wt. to about 60% wt./wt. of at least one functionalized or unfunctionalized cationic guar moiety and (b) about 20% wt./wt. to about 60% wt./wt. of at least one functionalized or unfunctionalized ethyl acrylate moiety, the process for preparing above said hybrid polymer is represented by the following general reaction scheme:
  • the hybrid graft polymer is prepared by any known polymerization methods for grafting monomers onto cellulose, galactomannan, or acrylate moieties, such as free radical synthesis with chemical initiators, high energy radiation initiation or thermal initiation.
  • the copolymerization may occur in solution, suspension, emulsion or in any medium which is known in the art, or which may become known in the art for graft copolymerization.
  • methods of polymerization include free radical polymerization, 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.
  • CRP controlled radical polymerization
  • ARP atom transfer radical polymerization
  • RAFT reversible addition-fragmentation chain transfer
  • SFRP stable free radical polymerization
  • cationic polymerization ionic polymerization
  • ionic polymerization ionic polymerization
  • Free radical polymerization may 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.
  • hybrid polymers of the present application are synthesized by free radical polymerization in the presence of one or more free radical initiators.
  • the radical polymerization initiators are known initiators including but not limited to sodium persulphate (SPS), potassium persulfate, ammonium persulfate, 2,2'- azobis(2-amidinopropane)dihydrochloride, benzoyl peroxide, hydrogen peroxide, sodium peracetate, cumene hydroperoxide, azobisisobutyronitrile and the like.
  • promotors may be used include, for example, sodium sulfite, sodium thiosulfate, ammonium ferrous sulfate and the like.
  • the amount of the radical polymerization initiator varies depending on the type and is generally in the range of from about 0.01 % wt./wt. to about 5 % wt./wt. of the total monomer.
  • the present application discloses a physical mixture comprising: (a) about 20% wt./wt. to about 60% wt./wt. of at least one functionalized or unfunctionalized galactomannan moiety and (b) about 20% wt./wt. to about 60% wt./wt. of at least one functionalized or unfunctionalized acryloyl moiety.
  • Another non-limiting embodiment provides a physical mixture comprising: (i) about 20% wt./wt. to about 40% wt./wt. of cationic guar; (ii) about 30% wt./wt. to about 60% wt./wt. of ethyl acrylate (EA); and (iii) about 20% wt./wt. to about 40% wt./wt. of methacrylic acid (MAA).
  • Yet another non-limiting embodiment discloses to comprise: physical mixture of (i) about 30% wt./wt. of cationic guar; (ii) about 42% wt./wt. of ethyl acrylate (EA); and (iii) about 28% wt./wt. of methacrylic acid (MAA).
  • Still another specific non-limiting embodiment discloses a physical mixture of (a) about 20% wt./wt. to about 60% wt./wt. of galactomannan moiety selected from cationic guar, hydroxypropyl guar; and (b) about 20% wt./wt. to about 60% wt./wt. of cellulose ether moiety selected from hydroxy ethyl cellulose (HEC) and carboxy methyl cellulose (CMC).
  • HEC hydroxy ethyl cellulose
  • CMC carboxy methyl cellulose
  • the hair straightening or styling composition of the present application comprises at least one organic or inorganic base in the concentration range of from about 0.1 % wt./wt. to about 20% wt./wt. of the total composition.
  • Suitable base for the hair care composition of the present application is an organic or inorganic carbonate or bicarbonate selected from the following non-limiting compounds including sodium bicarbonate, potassium bicarbonate, disodium or dipotassium carbonate, sodium- potassium carbonate; lithium, magnesium, calcium, zinc, aluminum, guanidine, or imidazolium carbonates or bicarbonates; diammonium carbonate, ammonium bicarbonate or ammonium sodium carbonate; alkyl or aryl ammonium bicarbonates selected from propylene carbonate; dialkyl ammonium carbonates or bicarbonates; alkylaryl ammonium carbonates or bicarbonates; diaryl ammonium bicarbonates, trialkyl ammonium carbonates or bicarbonates; alkylaryl ammonium carbonate or triaryl ammonium bicarbonates, hydroxyl alkyl or hydroxyl aryl ammonium bicarbonates; dihydroxyl alkyl ammonium carbonates or bicarbonates; hydroxyl alkyl hydroxyl aryl ammonium carbonates and
  • the hair straightening or styling composition of the present application comprises optionally, at least one functional polymer in the concentration range of from about 0.1 % wt./wt. to about 20% wt./wt. of the total composition.
  • the functional polymer as used herein is a non-hybrid polymer which has a styling, thickening or conditioning property. Additionally, the functional polymer possibly has either at least one individual property, for example, (i) styling and thickening, (ii) thickening and conditioning, (iii) styling and conditioning or (iv) styling, thickening and conditioning.
  • the functional polymers suitable for the present application include but are not limited to organic hair styling polymers that are well known in the relevant art for an artisan.
  • the organic styling polymers are homopolymers, copolymers, terpolymers or other higher polymers, but should comprise one or more polymerizable hydrophobic monomers to render the resulting styling polymer hydrophobic and water insoluble as defined herein.
  • the styling polymers possibly therefore further comprise other water soluble, hydrophilic monomers provided that the resulting styling polymers have the requisite hydrophobicity and water insolubility.
  • an optional functional polymer is employed for preparing the hair care composition of the present application, and wherein, a polymer or blend of polymers from synthetic and/or natural origin with weight average molecular weight from about 500 to about 20,000,000 daltons, containing at least one or more of the following monomeric components selected the group including but not limited to styrenics, and/or sulfonated styrenics, acrylates, methacrylates, acrylamides, methacrylamides, vinyl lactams like vinyl pyrrolidone, vinyl caprolactam, vinyl amides, urethanes, ethoxylates, propoxylates, vinyl carboxylates, vinyl esters, vinyl ethers, maleates, itaconates, crotonates, and olefinics.
  • a polymer or blend of polymers from synthetic and/or natural origin with weight average molecular weight from about 500 to about 20,000,000 daltons containing at least one or more of the following monomeric components selected the group
  • Natural polymers are polysaccharides containing a-1,4 and/or -l,4-glycosidic linkages with optionally a- 1,6 and/or ⁇ -1,6 linkages, or optionally modified with (i) hydroxyalkyl, (ii) cationic functionality, (iii) hydrophobic groups including methyl, ethyl, propyl, and/or carboxymethyl groups, or (iv) hydrophilic groups including hydroxy ethyl, hydroxyl propyl, acetates, succinates, phosphates, sulfates and/or carbonates. Accordingly, in one specific embodiment, the natural polymer is cellulose, starch, guar, alginate, and carrageen gum.
  • the functional polymer is cationic, anionic, amphoteric or nonionic in nature.
  • Suitable functional polymers include but are not limited to acrylamide/sodium acrylate copolymer, acrylate/ammonium methacrylate copolymer, acrylic/acrylate copolymer, allylstearate/vinyl acetate (VA) copolymer, aminoethylacrylate phosphate/acrylate copolymer, allyl stearate/VA copolymer, butyl ester of ethylene/maleic anhydride copolymer, isopropyl ester of methyl vinyl ether/ maleic anhydride (PVM/MA) copolymer, octyacrylamide / acrylate /butylaminoethyl methacrylate copolymer, octylacrylamide/acrylates copolymer, polyethylacrylate, poly( vinyl pyrroli
  • Non-ionic styling polymers with broad ingredient compatibility - Polyvinylpyrrolidones such as PVP K-30, PVP K-60 and PVP K-90, Vinylpyrrolidone/vinyl acetate copolymers such as PVP/VA (E, I or W) 735, PVP/VA (E or W) 635, PVP/VA (E or I) 535, PVP/VA (E or I) 335 and PVP/VA S-630, and poly(vinylpyrrolidone/ dimethyla
  • 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.
  • present application further comprises from about 40% wt./wt. to about 95% wt./wt. of at least one carrier.
  • at least one carrier is 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').
  • the present application further comprises an optional cross-linking monomeric unit having alcohol, thiol, carboxylic acid or anhydride, amino or ammonium, modified silicone or siloxane, alkoxy silane, or sulfate group functionality.
  • the cross-linking agent is present in an amount of about 0.1 % wt./wt. to about 20% wt./wt. of the total composition.
  • the composition of the present application further comprises about 0.1 % wt./wt. to about 20% wt./wt. of at least one protein, peptide, dipeptide, tripeptide, tetrapeptide, pentapeptide, hexapeptide, heptapeptide, octapeptide, nona- peptide, and decapeptide 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, avocado protein, egg protein, honey protein, rice protein, casein, light protein, gelatin, or their hydrolyzed counterparts.
  • group components including cysteine, histidine, lysine, arginine, aspartate, glut
  • the present application further comprises about 0.1% wt./wt. to about 20% wt./wt. of at least one cosmetically acceptable ingredient.
  • Suitable personal care or cosmetically acceptable ingredients or conventional additives that are employed for the preparing composition of the present application are 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, neutralizing agents, 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, antioxidants, solvents, electrolytes; hair and skin conditioning agents such as antistatic agents, synthetic oils, vegetable or animal oils, monomeric or polymeric quaternized ammonium
  • the chelating agents used in the present application are present in an amount of about 0.1 % wt./wt. to about 5% wt./wt., about 5% wt./wt. to about 10% wt./wt. , 10% wt./wt. to about 15 % wt./wt. or about 15% wt./wt. to about 20% wt./wt.
  • ethylene diamine tetra acetic acid EDTA
  • diisopropyl oxalate disodium EDTA
  • disodium EDTA-copper hexaethylene diamine tetra acetic acid
  • oxalic acid potassium or sodium citrate
  • sodium oxalate trimethylamine-EDTA
  • tetrasodium EDTA trisodium EDTA
  • trisodium HEDTA trisodium HEDTA.
  • the conditioning agents used in the present application are present in an amount of about 0.1 % wt./wt. to about 5% wt./wt., about 5% wt./wt. to about 10% wt./wt. , 10% wt./wt. to about 15% wt./wt. or about 15% wt./wt. to about 20% wt./wt. of the total composition and are selected from but not limited to polymeric and small quaternary ammonium compounds such as tertiary amines quaternium and polyquaternium compounds.
  • Preferred conditioning agents are proteins or hydrolyzed cationic or non-cationic proteins selected from hydrolyzed collagens having trimethylammonium and trimethylstearyl ammonium chloride groups, hydrolyzed animal proteins having trimethyl benzyl ammonium groups, hydrolyzed proteins having groups of quaternary ammonium on the polypeptide chain, including at least one Cl- C12 alkyl, Ceramide compounds ceramide, a glycoceramide, a pseudoceramide, or a neoceramide selected from 2-N-linoleoyl amino-octadecane-l,3-diol, 2-N-oleoyl amino- octadecane-l,3-diol, 2-N-palmitoyl amino-octadecane-l,3-diol, 2-N-stearoyl amino- octadecane-l,3-diol, 2-N-behenoyl amino-octa
  • cetrimonium chloride dicetyldimonium chloride, behentrimonium methosulfate, and the like
  • fatty amine selected from dodecyl, cetyl or stearamidopropyl dimethylamine
  • fatty acid or derivatives selected from mono-, di-, tri- and tetra- carboxylic acids selected from lactic acid, tartaric acid, gluconic acid, acetic acid, hydrochloric acid, phosphoric acid or combinations thereof.
  • Preferred conditioning agent is combination of Cetearyl Alcohol (and) Behenyl Alcohol (and) Hydroxyethyl Cetearamidopropyldimonium Chloride commercially available as ProLipidTM 161 lamellar gel (Ashland), and stearamidopropyl dimethylamine.
  • the emollients used in the present application are present in an amount of about 0.1 % wt./wt. to about 5% wt./wt., about 5% wt./wt. to about 10% wt./wt. , 10% wt./wt. to about 15% wt./wt. or about 15% wt./wt. to about 20% wt./wt. of the total composition and include but are not limited to cetyl alcohol, stearyl alcohol.
  • the emulsifiers used in the present application are present in an amount of about 0.1 % wt./wt. to about 5% wt./wt., about 5% wt./wt. to about 10% wt./wt. , 10% wt./wt. to about 15% wt./wt. or about 15% wt./wt. to about 20% wt./wt.
  • ethoxylated C10-C22 fatty alcohols selected from oleth-20, trideceth-6, trideceth- 7, trideceth-9, trideceth-10, trideceth-11, trideceth-12, trideceth-15, trideceth 20, trideceth-30, trideceth-40, trideceth-50, or mixtures thereof, a C10-C22 fatty alcohol ether, ethoxylated oleic alcohol, an ethoxylated branched CIO alcohol, a stearic acid ester, or mixtures thereof.
  • the humectants used in the present application are present in an amount of about 0.1 % wt./wt. to about 5% wt./wt., about 5% wt./wt. to about 10% wt./wt. , 10% wt./wt. to about 15% wt./wt. or about 15 % wt./wt. to about 20% wt./wt. of the total composition and 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.
  • Non-limiting examples of humectants include hydrolyzed silk protein, 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 suitable non-limiting moisturizers employed in the present application are present in an amount of about 0.1 % wt./wt. to about 2% wt./wt., about 2% wt./wt. to about 5 % wt./wt. , or 5 % wt./wt. to about 10% wt./wt.
  • glycol examples include but are not limited to glycol, glycerol, 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 oxidizing agents are selected from but not limited to hydrogen peroxide, bromides and per acetic acid to fix the disulfide bond.
  • the pH adjusting buffers are selected from but 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.
  • the preservatives used in the present application are present in an amount of about 0.1 % wt./wt. to about 5% wt./wt., about 5% wt./wt. to about 10% wt./wt. , 10% wt./wt. to about 15 % wt./wt. or about 15% wt./wt. to about 20% wt./wt.
  • Preferred preservatives are combination of benzoic acid and Sorbic acid in benzyl alcohol - commercially available as RokonsalTM BSB-N (Ashland.); Propylene Glycol (and) Diazolidinyl Urea (and) Methyl paraben (and) Propyl paraben - commercially available as Germaben II (Ashland); and stearalkonium chloride.
  • the reducing agents are selected from but not limited to thioglycolate, thiosulfate, sulfite, bisulfite, and urea. These agents target disulfide bonds to create additional disulfide interchange and rearrangement.
  • the salts used in the present application are present in an amount of about 0.1 % wt./wt. to about 5% wt./wt., about 5% wt./wt. to about 10% wt./wt. , 10% wt./wt. to about 15% wt./wt. or about 15 % wt./wt. to about 20% wt./wt.
  • the total composition includes but are not limited to sodium acetate, potassium acetate, ammonium acetate, sodium citrate, potassium citrate, ammonium citrate, sodium nitrate, potassium nitrate, ammonium nitrate, sodium phosphate, potassium phosphate, ammonium phosphate, sodium chloride, potassium chloride, ammonium chloride, sodium sulfate, potassium sulfate, ammonium sulfate, sodium ethylene diamine tetra acetic acid, disodium ethylene diamine tetra acetic acid and trisodium ethylene diamine tetra acetic acid, tetra sodium ethylene diamine tetra acetate and mixtures thereof. Most preferred is disodium ethylene diamine tetra acetic acid.
  • the functional silicones used in the present application are present in an amount of about 0.1 % wt./wt. to about 5% wt./wt., about 5% wt./wt. to about 10% wt./wt. , 10% wt./wt. to about 15% wt./wt. or about 15% wt./wt. to about 20% wt./wt. of the total composition and are selected from but not limited to dimethicone, amodimethicone, vinyldimethicone, cyclopentasiloxane, dimethicone/vinyldimethicone cross polymer, silicone quat, silicone fluid and silicone wax. These silicones decrease friction during hair combing and flat ironing, smooth gliding, increase conditioning and smoothing to hair by adding flexibility, help reduce heat damage and style retention; and contribute to shine depending on the refractive index.
  • the smoothing or straightening agents used in the present application are present in an amount of about 0.1 % wt./wt. to about 5% wt./wt., about 5% wt./wt. to about 10% wt./wt. , 10% wt./wt. to about 15% wt./wt. or about 15% wt./wt. to about 20% wt./wt.
  • cysteine selected from cysteine, homocycsteine, homocysteine hydrate, N-acetyl- L-cysteine and N-carbamoylcysteine glyoxylol carbocysteine, N-propionylcysteine, N- butyrylcysteine, N-valerylcysteine, N-caproylcysteine and N-heptanoylcysteine, N- benzoylcysteine, N-toluoylcysteine, N-(ethylbenzyl) cysteine and N-(propylbenzoyl) cysteine, and N-acylated cysteine.
  • a catalyst is employed to facilitate the reaction speed of active ingredients, and wherein, the suitable catalyst can be n on- metallic (N-methylimidazole, Perfluoroalkanesulfonates, N-dimethylaminopyridine) or metallic (tin, aluminum, iron, scandium, yttrium, zinc, bismuth, ruthenium, zirconocene) in nature.
  • metallic N-methylimidazole, Perfluoroalkanesulfonates, N-dimethylaminopyridine
  • metallic tin, aluminum, iron, scandium, yttrium, zinc, bismuth, ruthenium, zirconocene
  • the present application also contemplates fatty alcohols or waxes as structuring agents, anionic or non-anionic surfactants or wetting agents, petrolatum as thickeners protectants, mineral oils as lubricating agents, mica or silica, bentonite, or other inorganic powders as thickening agents and heat transfer agents.
  • the present application discloses a hair care composition capable of styling, straightening or conditioning hair by providing "virgin feel condition" to the hair after multiple washes particularly providing at least one of the following results including (1) increased hydrophobicity, (2) improved detangling and wet combability, (3) improved deposition, and (4) no build-up.
  • the hybrid polymer described in the present application improves hair straightening by improving the hair fiber alignment, improving contact heat transfer, reducing friction between hot iron and hair.
  • Hybrid polymer along with a or ⁇ - hydroxy ketone is semipermanently affixed to hair and survives multiple shampoo cycles. Even after washing the hair treated with present hair styling composition, the polymer helps in conditioning, smoothness, frizz reduction, shine, manageability, durability, humidity resistance, and restyle- ability.
  • Functional polymer will react with itself and/or with the straightening components. In doing so, the hair tress will have significant improvement in providing or enhancing life to it and still maintain same desired aesthetic attributes like shine, conditioning, luster, and feel, etc.
  • the present application provides a hair straightening or hair styling composition
  • a hair straightening or hair styling composition comprising: (A) about 0.1 % wt./wt. to about 70% wt./wt. of dihydroxyacetone, 4-hydroxy-2-butanone, l-hydroxy-2-butanone or mixtures thereof; (B) about 0.1 % wt./wt. to about 70% wt./wt.
  • a first polymeric compound selected from: (i) at least one hybrid graft polymer derived from (a) a functionalized or unfunctionalized cellulose ether moiety and (b) at least one functionalized or unfunctionalized acryloyl moiety; or (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; (C) about 0.1 % wt./wt. to about 20% wt./wt. of sodium bicarbonate and/or propylene carbonate; (D) optionally, about 0.1 % wt./wt. to about 20% wt./wt. of at least one functional polymer, and (E) at least one a carrier, wherein said composition has a pH of about 5 to about 11.
  • the present application further comprises about 0.1 % wt./wt. to about 70% wt./wt. of a second polymeric compound selected from: (a) a functionalized or unfunctionalized cellulose ether moiety, or (b) functionalized or unfunctionalized galactomannan moiety.
  • a second polymeric compound selected from: (a) a functionalized or unfunctionalized cellulose ether moiety, or (b) functionalized or unfunctionalized galactomannan moiety.
  • the straightening effect is not that pronounced as desired whereas the present composition with hydroxy acetone, hybrid graft polymer and sodium bicarbonate has long lasting straightening effect.
  • consumer safety is of premier importance, the neutral to slightly alkaline pH region for hair straightening is observed to be superior as compared to that of highly acidic or highly alkaline condition based straightening effects.
  • the present hair styling composition can be applied on damp or dry hair and provides longer lasting straightening effects, shorter processing times as hair can be washed right away immediately once the hair is straightened unlike the formaldehyde treatment which requires long waiting period to wash the hair.
  • the present composition does not damage the hair, and is safer to scalp and hair.
  • the present composition enables treatment of hair at wide pH ranges of about 1- 14, but most preferably in neutral to slightly alkaline conditions at pH 7-12 which is much safer and less corrosive to scalp and hair.
  • the hair composition of the present application is employed for oxidatively dyed hair without extreme color changes that are observed by 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, and to provide some straightening effects.
  • the present hair care composition comprising at least one hydroxy ketone, at least one hybrid polymer, at least one organic or inorganic base, and optionally, at least one functional polymer
  • hair care compositions and components that are commercially available and very well known in relevant literature as prior art for a person skilled in the relevant art, and wherein, such non-limiting compositions that are known in the prior art include glyoxylic acid / dimethyl urea, polyacrylate cross polymer, polysaccharides, film forming agents and N-alkyl-2-mercaptoacetamide.
  • the present application comprises a hair straightening or styling composition which is formulated as per the requirement, and wherein, the non-limiting forms include straightening spray lotion, non-aerosol straightening mousse, hair relaxant, semi-permanent hair dyeing system, temporary hair dyeing system, hair bleaching system, permanent hair wave system, hair setting formulation, 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.
  • the non-limiting forms include straightening spray lotion, non-aerosol straightening mousse, hair relaxant, semi-permanent hair dyeing system, temporary hair dyeing system, hair bleaching system, permanent hair wave system, hair setting formulation, smoothing and straightening fluid, straightening serum, straightening solution, straightening perm, emulsion, gel, vesicle dispersion
  • the present application provides a method of straightening or styling hair, the method comprises: step (a): washing the hair tresses with shampoo; step (b): eliminating the moisture of hair tresses of step (a); step (c): applying the hair straightening or styling composition comprising (A) dihydroxy acetone, 4-hydroxy-2- butanone, l-hydroxy-2-butanone or combinations thereof; (B ) first polymeric compound selected from: (i) at least one hybrid graft polymer derived from (a) functionalized or unfunctionalized cellulose ether moiety and (b) at least one functionalized or unfunctionalized acryloyl moiety; or (ii) at least one hybrid graft polymer derived from (a) functionalized or unfunctionalized galactomannan moiety and (b) at least one functionalized or unfunctionalized acryloyl moiety; (C) sodium bicarbonate; (D) at least one functional polymer, and (E) at least one carrier, to
  • 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 composition employs molecules which are much safer, allows the hair treatment for straightening, conditioning or styling to be performed at wide pH range of highly basic to highly acidic, and does not emit formaldehyde during the process, and capable of providing long term hair straightening.
  • 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 the strong sulfate based shampoo and conditioner.
  • the combination of hydroxy ketone/s, hybrid polymer and organic/inorganic base penetrate into the hair fiber's cortex and modifies the hair fiber's natural shape.
  • the functional polymer of the present application provides additional shape control, styling, shine, feel, conditioning, luster to the hair etc.
  • EXAMPLE 1 Polymerization of Cellulose / Acrylate Hybrid Copolymer
  • DIW Deionized Water
  • HEC Hydroxyethyl Cellulose
  • HEC or CMC solution as prepared above was taken into a reactor flask fitted with condenser, thermometer, seal and nitrogen pipette in a water bath. Condenser and nitrogen inlet were turned ON and pipette was placed below the surface of the cellulose. Nitrogen purging was done for 30 min at room temperature. Contents of the flask were heated to 80°C and maintained for 60 min. After 50 min of heating, nitrogen inlet was raised above the surface of the HEC or CMC solution maintaining nitrogen blanket through the reaction. After heating for 60 minutes, first shot of initiator was added to HEC or CMC polysaccharide solution via a syringe. Contents were allowed to react for 60 min at 80°C.
  • Phase A Water was added to the main container and mixed well. Phase ingredients were added one by one. Contents were heated to 70-75°C while mixing.
  • Phase B Behenyl Alcohol (and) Cetearyl Alcohol (and) Hydroxyethyl Cetearamidopropyl dimonium Chloride flakes were separately melt at 75°C which was then added to Phase - A contents with vigorous mixing. Temperature was maintained for 20 min at 75 °C. The reaction contents were cooled to 60°C slowly and amodimethicone was added with thorough mixing. The reaction contents were further cooled to 40°C and Phase D ingredients was added. Finally, hair straightening serum was obtained.
  • Hybrid polymer was dispersed into water with propeller agitation. When dispersed, the reaction contents were heated to 70 °C and temperature was maintained for 15 minutes while adding disodium EDTA. Phase B ingredients were separately heated to 70°C and then later added to Phase A contents while maintaining the temperature for 30 minutes. Batch was cooled to 45°C and Phase C ingredients were added. Cooling was continued at 30°C and then Phase D ingredients were added. Finally, hair styling or straightening solution was obtained.
  • Example 5 Method of hair straightening or hair styling
  • Hair tress was washed thoroughly with shampoo and warm water (35-40°C) followed by second wash, and rinsed for 30 seconds. Excess water was removed, and moisture was removed using blot with towel. Hair styling product of any of the above formulations of examples 1 to 3 was applied; through from root to tip with fingers and combed until uniformly distributed to remove excess. Treated hair was left for 30 minutes for the styling product to penetrate. (Hang tress in straight position). After 30 minutes, tress was hot blow- dried as straight as possible with much tension using a round brush or comb with slow uniform motion from root to tip. Flat iron was pre-heated and hair was treated with pre- heated flat iron from root to tip for about six times.
  • FIG. 1 The results of treating natural hair are shown in Figure 1. It shows the results of treating untreated hair (A) with hydroxy acetone (B), with hydroxy acetone and hybrid polymer HEC/EA/MAA (C). It is observed that hybrid polymer not only conducts heat but also gives hair styling and conditioning benefits as seen in the Figure 1.

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Abstract

La présente invention concerne une composition de soin capillaire, et plus particulièrement une composition de défrisage ou de coiffage des cheveux comprenant (A) au moins une cétone α ou β-hydroxy, (B) un premier composé polymère choisi parmi (i) au moins un polymère greffé hybride dérivé (a) d'une fraction de cellulose fonctionnalisée ou non fonctionnalisée et (b) d'au moins une fraction acryloyle fonctionnalisée ou non fonctionnalisée, ou (ii) au moins un polymère greffé hybride dérivé (a) d'une fraction de galactomannane fonctionnalisée ou non fonctionnalisée et (b) d'au moins une fraction acryloyle fonctionnalisée ou non fonctionnalisée ; (C) au moins une base organique ou inorganique ; (D) éventuellement au moins un polymère fonctionnel ; et (E) au moins un vecteur. En outre, l'invention porte sur un procédé de préparation de la composition de défrisage ou de coiffage des cheveux et sur un procédé de défrisage ou de coiffage des cheveux.
PCT/US2017/042093 2016-07-18 2017-07-14 Composition de soin capillaire, son procédé de préparation et son procédé d'utilisation Ceased WO2018017408A1 (fr)

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Cited By (6)

* Cited by examiner, † Cited by third party
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PL424632A1 (pl) * 2018-02-20 2019-08-26 Aero-Bw K. Domagała Spółka Jawna Sposób wytwarzania preparatu z komórkami macierzystymi do pielęgnacji włosów i skóry głowy oraz urządzenie do nasączania aplikatorów tego preparatu i metoda nasączania
EP3801775A4 (fr) * 2018-06-03 2022-05-04 EasyFix Hair Design Ltd. Composition acrylique d'auto-durcissement pour le coiffage des cheveux
WO2022215069A1 (fr) * 2021-04-05 2022-10-13 EasyFix Hair Design LTD. Formulations acryliques auto-durcissantes contenant de la n-acétyl cystéine pour le lissage des cheveux
CN115260331A (zh) * 2022-08-26 2022-11-01 南京林业大学 一种功能性半乳甘露聚糖及其制备方法与应用
WO2023164152A1 (fr) * 2022-02-25 2023-08-31 Isp Investments Llc Composition multimodale de soins capillaires comprenant des mélanges cationiques de guar et son procédé de préparation
RU2831532C1 (ru) * 2024-04-11 2024-12-09 Спартак Спартакович Киракосян Состав для ухода за волосами

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US5037930A (en) * 1989-09-22 1991-08-06 Gaf Chemicals Corporation Heterocyclic quaternized nitrogen-containing cellulosic graft polymers
US6306377B1 (en) * 1998-01-29 2001-10-23 Shiseido Co., Ltd. Hair straightening/smoothing composition
WO2010016543A1 (fr) * 2008-08-08 2010-02-11 ハイモ株式会社 Additif pour produit cosmétique capillaire, produit cosmétique capillaire, et procédé de production de cet additif
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US20150374604A1 (en) * 2013-02-06 2015-12-31 Lubrizol Advanced Materials, Inc. Semi-permanent hair straightening composition and method
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US20160058683A1 (en) * 2014-08-31 2016-03-03 Cosphatech LLC Hair-Straightening Compositions and Methods

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL424632A1 (pl) * 2018-02-20 2019-08-26 Aero-Bw K. Domagała Spółka Jawna Sposób wytwarzania preparatu z komórkami macierzystymi do pielęgnacji włosów i skóry głowy oraz urządzenie do nasączania aplikatorów tego preparatu i metoda nasączania
EP3801775A4 (fr) * 2018-06-03 2022-05-04 EasyFix Hair Design Ltd. Composition acrylique d'auto-durcissement pour le coiffage des cheveux
WO2022215069A1 (fr) * 2021-04-05 2022-10-13 EasyFix Hair Design LTD. Formulations acryliques auto-durcissantes contenant de la n-acétyl cystéine pour le lissage des cheveux
WO2023164152A1 (fr) * 2022-02-25 2023-08-31 Isp Investments Llc Composition multimodale de soins capillaires comprenant des mélanges cationiques de guar et son procédé de préparation
CN115260331A (zh) * 2022-08-26 2022-11-01 南京林业大学 一种功能性半乳甘露聚糖及其制备方法与应用
RU2831532C1 (ru) * 2024-04-11 2024-12-09 Спартак Спартакович Киракосян Состав для ухода за волосами

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