WO2017174213A1 - Composition contenant un polymère et procédé associé - Google Patents

Composition contenant un polymère et procédé associé Download PDF

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Publication number
WO2017174213A1
WO2017174213A1 PCT/EP2017/025076 EP2017025076W WO2017174213A1 WO 2017174213 A1 WO2017174213 A1 WO 2017174213A1 EP 2017025076 W EP2017025076 W EP 2017025076W WO 2017174213 A1 WO2017174213 A1 WO 2017174213A1
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WO
WIPO (PCT)
Prior art keywords
composition
hyperbranched
polymer
hydrophilic polymer
pigment
Prior art date
Application number
PCT/EP2017/025076
Other languages
English (en)
Inventor
Jonathan George Collett
Ghislaine Monique Nicole ROBERT-NICOUD
Original Assignee
The Boots Company Plc
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Publication date
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Publication of WO2017174213A1 publication Critical patent/WO2017174213A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/85—Polyesters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/88—Polyamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
    • A61Q1/06—Lipsticks
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/08—Preparations containing skin colorants, e.g. pigments for cheeks, e.g. rouge
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/12—Face or body powders for grooming, adorning or absorbing
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/44—Polyester-amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/005—Dendritic macromolecules
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
    • C08L77/12—Polyester-amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54—Polymers characterized by specific structures/properties
    • A61K2800/544—Dendrimers, Hyperbranched polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04—Dispersions; Emulsions
    • A61K8/06—Emulsions
    • A61K8/064—Water-in-oil emulsions, e.g. Water-in-silicone emulsions

Definitions

  • the disclosed technology relates to a composition
  • a composition comprising: (a) a pigment, (b) a hyperbranched or dendrimer hydrophilic polymer, (c) a film forming polymer different from (b), and wherein the composition comprises a polar solvent present at up to 95 wt % of the composition.
  • the disclosed technology further relates to the use and method of the disclosed technology in cosmetic applications.
  • Cosmetic compositions such as a foundation, lip-stick, mascara, and nail varnishes are often coloured using a pigment.
  • the cosmetic compositions are applied to skin, eyelashes, eyebrows or nails to form a coating/film.
  • the coating/film is susceptible to stresses and rubbing due to factors such as changes to facial expression, or contact with other bodies/surfaces. The result of these changes is believed to have a greater impact on the amount of pigment retained in the cosmetic. With stresses and/or rubbing pigment is believed to have a tendency to wear away because it is less resistant to changes in stresses and rubbing. Consequently with increased wear away, the coating of the cosmetic on the skin, eyelashes, eyebrows or nails is reduced and a loss of colour occurs.
  • Hyperbranched or dentritic polymers are known in personal care formulations such as hair care products as described in US2011/0293552 (published 1 December 2011, Derici et al), US7914773 (published 29 March, 2011, Derici et al.) and US2014/0348771 (published 27 November 2014, Beumer et al.).
  • hair care products such as shampoo and conditioner remain in contact with skin for a prolonged period of time as they are washed off during use.
  • WO2012/131068 (published 4 October 2012, Gavillion et al.) relates to the cosmetic treatment of human perspiration, and optionally underarm odours, in which an antiperspirant polymeric cosmetic material comprising at least two zones A and B is applied to the skin, zone A being formed from at least one hydrophilic film- forming polymer and zone B being formed from at least one non- pressure-sensitive-adhesive, hydrophobic film-forming polymer.
  • the polymers disclosed therein may include a hyperbranched polymer.
  • Antiperspirant compositions are believed to work by blocking sweat ducts rather than forming a coating on skin that acts as a cosmetic.
  • WO2006/118460 discloses a hydrogel that consists of gellants of a hydrophilic polymer to which at least two 4H-units are covalently attached, wherein the 4H-unit has a defined formula and requires a N- containing heterocyclic moiety.
  • CA2781185 (published 3 June 2011, Wendel et al.) and US2011124729 (published 26 May 2011, Wendel et al.) both disclose highly branched polyester which is completely or partly substituted by linear or branched C4- to C40- alkyl- or alkenyl radicals.
  • the polyester may be used in a cosmetic formulation as a thickener.
  • US2014/0057998 discloses a cosmetic or dermatological composition
  • a cosmetic or dermatological composition comprising at least one highly-branched polycarbonate which is substituted completely or partly with linear or branched C4-C40-alkyl or alkenyl radicals, wherein the substitution takes place with a compound.
  • WO2008/074846 discloses a kit comprising two separately packaged compositions intended for application to the skin: at least one first composition comprising a compound X; at least one second composition comprising a compound Y; one of at least of the compounds X and Y being a silicone compound, and said compounds X and Y reacting together by a hydrosilylation reaction, thus forming a hydrosilylated product.
  • the compound X disclosed therein may include a hyperbranched polymer.
  • compositions may be applied topically to provide at least one of increased rub (or wear) resistance, increased coating flexibility, and/or reduced colour loss.
  • the composition may also be easier to apply topically as the composition may be more spreadable.
  • the transitional term "comprising,” which is synonymous with “including,” “containing,” or “characterized by,” is inclusive or open-ended and does not exclude additional, un-recited elements or method steps.
  • the term also encompass, as alternative embodiments, the phrases “consisting essentially of and “consisting of,” where “consisting of excludes any element or step not specified and “consisting essentially of permits the inclusion of additional un-recited elements or steps that do not materially affect the basic, essential and novel characteristics of the composition, method or use under consideration.
  • gel As used herein reference to gel is used in the ordinary sense defined by IUPAC and is intended to include a non-fluid colloidal network or polymer network that is expanded throughout its whole volume by a fluid.
  • the fluid may for instance be water or alcohol.
  • skin As used herein reference to skin is intended to include skin that covers the surface of the epidermis or stratum corneum e.g., facial, or body or lip skin.
  • eyelashes is intended to include hair that grows at the edge of the eyelid.
  • Compositions intended for application to the eyelashes include mascaras.
  • eyebrows is intended to include hair that grows above the eye that follows the shape of the lower margin of the brow ridges.
  • Compositions intended for application to the eyebrows include mascaras and eyebrow gloss.
  • the disclosed technology relates to a composition
  • a composition comprising:
  • composition comprises a polar solvent present at up to 95 wt %, or up to 90 wt % of the composition.
  • composition disclosed herein is not a hydrogel (as defined by IUPAC as a gel in which the swelling agent is water).
  • composition a film forming polymer different from (b), and wherein the composition comprises a polar solvent present at up to 95 wt %, or up to 90 wt % of the composition.
  • the disclosed technology relates to a method of imparting a benefit to a cosmetic of at least one of increased rub resistance, increased coating flexibility, and/or reduced colour loss and/or more spreadable to skin or nail comprising supplying/administering to skin (for example human skin) or nail the composition disclosed herein.
  • the disclosed technology relates to a method of imparting a benefit to a cosmetic of at least one of increased rub resistance, increased coating flexibility, and/or reduced colour loss and/or more spreadable to skin, nail, eyelashes or eyebrows comprising supplying/administering to skin, nail, eyelashes or eyebrows (for example human skin, nail, eyelashes or eyebrows) the composition disclosed herein.
  • the disclosed technology relate to the use of the composition disclosed herein to increase rub resistance and/or increase coating flexibility of a foundation or a mascara, or a nail varnish (for example a foundation or a mascara). In one embodiment there may be an increase in rub resistance and an increase coating flexibility of a foundation or a mascara.
  • the disclosed technology relate to a method for protecting human skin against the deleterious effects of ultraviolet irradiation, comprising topically applying thereto an effective amount of the composition disclosed herein to skin.
  • compositions such as shampoos and conditioners known in the prior art have their compositions in contact with or on the skin for up to a few minutes until being washed off or otherwise removed from skin.
  • the compositions disclosed here are typically intended to remain in contact with or on skin for a prolonged period of time.
  • the compositions disclosed herein may be in contact with or on skin for at least one or two hours.
  • the composition disclosed herein may be on nails for up to 7 days, or 48 hours, or for a foundation, BB cream, CC cream, lip-stick, eyebrow gloss and/or mascara (eye-lashes) up to 24 hours, or up to 18 or 12, or 8 hours.
  • composition disclosed herein may be a colour cosmetic.
  • the cosmetic may be a foundation, lip-stick, tinted moisturiser, BB cream (also referred to as a blemish balm, or beauty balm), CC cream (also referred to as colour control cream, or a colour correcting cream), or mascara.
  • BB cream also referred to as a blemish balm, or beauty balm
  • CC cream also referred to as colour control cream, or a colour correcting cream
  • mascara may be a foundation, tinted moisturiser, or lip-stick.
  • the cosmetic composition may be a foundation or a lip-stick.
  • BB cream and CC cream are believed to be a tinted moisturiser containing sun protection.
  • BB creams and CC creams typically comprise a primer, serum, moisturiser, foundation and sun protection, with a greater focus on skin care (for example a higher level of sun protection) in the CC cream.
  • the composition may be in the form of a gel, cream, lotion, spray or serum. In one embodiment the composition may be a cream, serum, or lotion.
  • the composition may be an emulsion or gel.
  • the composition when the composition is a gel, the composition further comprises a thickener.
  • the disclosed technology relates to the cosmetic use of a composition disclosed herein (for example a foundation, a lip-stick, a mascara, or a nail varnish/polish).
  • a composition disclosed herein for example a foundation, a lip-stick, a mascara, or a nail varnish/polish.
  • the disclosed technology relates to the cosmetic use of a composition disclosed herein (for example a foundation, a lip-stick, or a mascara composition).
  • a composition disclosed herein for example a foundation, a lip-stick, or a mascara composition.
  • the pigment may be organic or inorganic.
  • the pigment When organic, the pigment may be carbon black, an azo compound, xanthene, quinone, FD&C pigment, D&C pigment, or a lake pigment.
  • a FD&C pigment is known in the art and approved by the Federal Food, Drug and Cosmetic Act (FD&C Act).
  • a D&C pigment is known in the art and approved by US Food and Drug Administration.
  • a lake pigment is known in the art and may be manufactured by precipitating a dye with an inert binder, or mordant, usually a metallic salt.
  • examples of a lake pigment include aluminum lakes, strontium lakes, or barium lakes.
  • FD&C and D&C pigments examples include Red 6, Red 7, Red 30, Red 34,
  • the pigment may be surface treated, often with alkyl silanes, to improve dispersion in a hydrophobic media.
  • the most common pigment surface treatment is triethoxycaprylylsilane .
  • the pigment may be iron oxide, especially red, yellow and black iron oxides, titanium dioxide, zinc oxide, potassium ferricyanide (K 3 3Fe(CN)6, potassium ferrocyanide K Fe(CN)6.3H20, or potassium ferrocyanide dehydrate, or an oxide of, zinc, zirconium and/or cerium.
  • the pigment may be black iron oxide, red iron oxide, yellow iron oxide and/or titanium dioxide.
  • the composition comprises pigment present at 0.1 to 20 wt %, or 2.5 to 18 wt %, or 5 to 15 wt % of the composition.
  • the composition may be in the form of a foundation.
  • the composition comprises pigment present at 0.1 to 15 wt %, or 2.5 to 12 wt %, or 5 to 10 wt % of the composition.
  • the composition may be in the form of a mascara.
  • the composition comprises pigment present at 0.1 to 35 wt %, or 1 to 20 wt %, or 2 to 15 wt % of the composition.
  • the composition may be in the form of a lip-stick.
  • the hyperbranched or dendrimer hydrophilic polymer may be considered as water- soluble.
  • Water soluble is considered to mean that at least 0.1 g of hydrophilic polymer is dissolved in 100 mL of water.
  • hyperbranched or dendrimer hydrophilic polymer classes include a polyamide, polyethyleneimine, polyesteramide (e.g. commercially sold under HybraneTM S series), polyether (e.g. polyglycerol), polyphosphoester (e.g. polyphosphates and polyphosphonates), polyester (e.g. BoltornTM H series), polyamidoamine (e.g. PAMAM), polyacrylate and polymethacrylate.
  • the weight average molecular weight of the hydrophilic polymer may range from 500 to 50,000, or 750 to 20,000, or 1000 to 10,000.
  • hyperbranched or dendrimer hydrophilic polymer end groups are hydroxyl, amine, carboxylate, phosphate, phosphonate, sulphate, sulphonate, a zwitterioninic group (e.g. carboxybetaine, sulfobetaine or phosphorylcholine), or a sugar moieties (e.g. glucose).
  • the hyperbranched or dendrimer hydrophilic polymer having a weight average molecular weight of greater than 20,000 has a hydrophilic core, and polymer end groups (such as -OH, or -NH 2 ) have been further reacted with solubilising groups such as ethylene oxide- chains.
  • the hyperbranched or dendrimer hydrophilic polymer having a weight average molecular weight of 750 to 20,000.
  • the hyperbranched or dendrimer hydrophilic polymer include a polyamide, polyethyleneimine, polyesteramide (e.g. HybraneTM S series), polyether (e.g. polyglycerol), or polyphosphoester (e.g. polyphosphates and polyphosphonates).
  • the hyperbranched or dendrimer hydrophilic polymer may include a polyesteramide (e.g. HybraneTM S series) and/or a polyether (e.g. polyglycerol).
  • a polyesteramide e.g. HybraneTM S series
  • a polyether e.g. polyglycerol
  • the polyesteramide may be a condensation polymer containing ester groups and at least one amide group in the backbone, having at least one hydroxyalkylamide end group and having a weight average molecular mass of greater than 800 g/mol.
  • the polyesteramide may be prepared by a process comprising reacting a cyclic anhydride with an alkanolamine to form a hydroxylalkylamide, after which the polymer is obtained through polycondensation.
  • the polyesteramide may be prepared by a process comprising reacting alkanolamine with a compound containing an acid group and an activated acid group, after which the polymer is obtained through polycondensation.
  • the polyesteramide may be prepared by a process comprising reacting a cyclic anhydride with an alcohol after which the reaction product obtained reacts in situ with an alkanolamine and the polymer is subsequently obtained through polycondensation.
  • the alkanolamine may be an alkyl-substituted p-hydroxyalkylamide such as (di)isopropanolamine, l-(m)-ethylisopropanolamine, (di)isobutanolamine, cyclohexylisopropanolamine, di-cyclohexanolamine and/or n-butylisopropanolamine.
  • polyesteramide A more detailed description of the polyesteramide is presented in WO99/16810
  • the polyesteramide is unmodified i.e., the polyesteramide does not react with a monomer, oligomer, or polymer containing reactive groups that can react with a hydroxyalkylamide.
  • the polyesteramide may be a polymer from claims 1-14 of WO99/16810.
  • the polyether may be homopolymer or copolymer.
  • the homopolymer may be polyglycerol formed via ring-opening multibranching polymerization of glycidol (see for example disclosure in Macromolecules, 1999, 32 (13), pp 4240-4246, DOI: 10.1021/ma990090w).
  • a copolymer may include copolymers of glycidol and one or more of ethylene oxide and propylene oxide or other epoxides.
  • the polyether may be a homopolymer or copolymer.
  • the homopolymer may be formed by polymerising ethylene oxide.
  • a copolymer may include copolymers of ethylene oxide and one or more of propylene oxide and butylene oxide.
  • the resultant copolymer may be a random or block copolymer having hyperbranched or dendrimer architecture.
  • the hyperbranched or dendrimer hydrophilic polymer disclosed herein may have a weight average molecular weight of 500 to 50,000, or 750 to 20,000, or 1000 to 10,000.
  • the weight average molecular weight may be determined using size exclusion chromatography techniques and using a polymethyl methacrylate standard.
  • composition disclosed herein may comprise 0.2 to 8.5 wt %, or 0.5 to 7 wt %, or 1 to 5 wt %, or 1.5 to 3 wt % of the hyperbranched or dendritic polymer.
  • the hyperbranched or dendrimer hydrophilic polymer may be solubilised in the polar solvent.
  • the film forming polymer is a different polymer to the hyperbranched or dendrimer hydrophilic polymer disclosed herein.
  • the film-forming polymer may be silicon-containing or non-silicon containing. In one embodiment the film forming polymer may be non-silicon containing.
  • the film forming polymer may be silicon containing.
  • the non-silicon containing film forming polymer may include synthetic gum, natural gum, synthetic polymer, natural polymer, polysaccharide thickening agent, associative thickener, anionic associative rheology modifier, nonionic associative rheology modifier, acrylates/C 10-30 alkylacrylate crosspolymer, acrylates/aminoacrylates /CI 0-30 alkyl PEG- 20 itaconate copolymer, acrylates copolymer, acrylates/steareth-20 methacrylate copolymer, acrylates/beheneth-25 methacrylate copolymer, PEG-150/decyl alcohol/SMDI copolymer, PVP (polyvinylpyrrolidone homopolymer or copolymer e.g., alkylated polyvinylpyrrolidone), PVM/MA decadiene crosspolymer, carbomer, PEG crosspolymer, acrylates/palmeth-25
  • the film forming polymer may include polyvinyl alcohol, VP/hexadecene copolymer, alkylated polyvinylpyrrolidone, acrylates copolymer, acrylates /actylacrylamide copolymer, polybutene, adipic acid/diethylene glycol/glycerin crosspolymer, trimethylpentanediol/adipic acid/glycerin crosspolymer, or polyurethane.
  • the silicon-containing film-forming polymer may include a silicone acrylate copolymer, silicone methacrylate copolymer or a silicone gum or resin or elastomer, such as butyl acrylate/ hydroxypropyl dimethicone acrylate copolymer, acrylate/polytrimethyl siloxymethacrylate, isobutylmethacrylate/bis-hydroxypropyl dimethicone acrylate copolymer, acrylates/ polytrimethylsiloxymethacrylate copolymer, dimethiconol, divinyldimethicone/ dimethicone copolymer, trimethylsiloxysilicate, polysilsesquioxane or trimethylsiloxysilicate/dimethiconol crosspolymer.
  • a silicone acrylate copolymer silicone methacrylate copolymer or a silicone gum or resin or elastomer, such as butyl acrylate/ hydroxypropyl dimethicon
  • the film forming polymer may be present at 0.01 to 60 wt %, or 0.03 to 30 wt % of the composition.
  • the film forming polymer may be present at 0.05 to 10 wt %, or 0.05 to 5 wt %, or
  • the polar solvent is a cosmetically acceptable medium, or a skin care acceptable medium.
  • the polar solvent may include water, or an alcohol having 1 to 4 (or 2 to 3) carbon atoms.
  • suitable alcohols include ethanol, propanol or iso-propanol.
  • the polar solvent is water; and in another embodiment the polar solvent is ethanol.
  • composition disclosed herein may optionally further comprise other ingredients.
  • the other ingredients include, an antioxidant, a skin conditioning agent, a salicyclic acid compound, a sunscreen agent, preservatives and/or gelling agents sequestering agents, wax, diluents, carriers, propellants perfumes, pH adjusting agents or emulsifiers.
  • the antioxidant polyphenolic agents may include extracts from plants chosen from
  • Mulberry e.g. morus alba
  • Ginseng e.g. Panax ginseng
  • Raspberry Oregano
  • Green tea e.g. green leaves of camellia sinensis
  • White tea e.g. camellia sinensis
  • Blueberry extract e.g. vaccinium cyanococcus
  • French maritime pine bark e.g. pinus pinaster, sold under the tradename Pycnogenol
  • Rosemary e.g. rosmarinus officialis
  • Grape including grape seed (e.g. vitis vinifera), Fennel (e.g. foeniculi fructus),
  • Caragana sinica Marjoram (e.g. origanum majorana), Crocus (e.g. crocus sativus), Apple (e.g. malus domestica), Coffee, Green coffee, Cherry (e.g. prunus avium), Snow algae (e.g. chlamydomonas nivalis), Emblica (e.g. Phyllanthus emblica), Gingko (e.g. Gingko biloba), Moringa (e.g. moringa oleilera), Ginger (e.g. zingiberaceae), Magnolia (e.g. magnolioideae virginiana), French saffron, Edelweiss (e.g.
  • leontopodium alpinium white lotus (e.g. nymphaea alba), Turmeric root, Marshmallow (e.g. althaea officianlis), Burdock (e.g. arctium lappa) , Bilberry (e.g. vaccinium myrtillus), Cranberry (e.g. vaccinium oxycoccus), Pomegranate nectar (e.g. Punica granatum), Sage (e.g. salvia officinalis), Thyme (e.g. thymus vulgaris), Sunflower (e.g. helianthus annuus), wild carrot (e.g. daucus carota), Hop (e.g.
  • humulus lupulus humulus lupulus
  • Witch Hazel e.g. hamamelis
  • Oak e.g. Quercus
  • Camellia e.g. theacea
  • Red clover e.g. tritolium pratense
  • Flax e.g. linium usitatissimum
  • lemon e.g. citrus limon
  • birch e.g. betula
  • cornflower e.g. centaurea cyanus
  • geranium polygonum, or soy (e.g. glycine max).
  • antioxidant plant polyphenolic agents used in the present invention are expressed as dry weights of the extract, as understood by a man skilled in the art.
  • the antioxidant plant extract
  • the composition of the present invention may optionally comprise a skin conditioning agent.
  • the skin conditioning agents may be chosen from humectants, emollients, moisturisers, or mixtures thereof. Where present, the skin conditioning agent may be present from 0 or 0.01 to 20 wt %, or 0.1 to 10 wt %, or 0.5 to 7 wt % of the composition.
  • the skin conditioning agents may be chosen from guanidine, urea, glycolic acid and glycolate salts, salicylic acid, lactic acid and lactate salts, aloe vera, shea butter, polyhydroxy alcohols, such as sorbitol, mannitol, xylitol, erythritol, glycerol, hexanetriol, butanitriol, (di) propylene glycol, butylene glycol, hexylene glycol, polyethylene glycol, sugars (e.g.
  • the skin conditioning agent may be chosen from glycerine, arabinoglactan, butylene glycol, hyaluronic acid, shea butter, propylene glycol, ethylhexyl glycerine, or hyaluronate.
  • compositions disclosed herein may optionally comprise a salicylic acid compound, its esters (such as alkylated salicylate e.g., octyl salicylate), its salts, or combinations thereof.
  • a salicylic acid compound at 0 or 0.0001 to 25 wt %, or 0.001 to 15 wt %, or 0.01 to 10 wt %, or 0.1 to 5 wt %, or 0.01 to 2 wt % of the composition, of salicylic acid.
  • the salicylic acid compound is salicylic acid or octyl salicylic acid.
  • compositions disclosed herein may optionally comprise an emulsifier.
  • the emulsifier helps disperse and suspend an aqueous water phase within an oil phase or vice versa.
  • Suitable emulsifiers include all those suitable for the purpose and known by those skilled in the art for use in skin care products.
  • these emulsifiers have an HLB value of or less than 14, more preferably from 2 to 14, and still more preferably from 4 to 14.
  • silicone emulsifiers are useful herein. These silicone emulsifiers are typically organically modified organopolysiloxanes, also known to those skilled in the art as silicone surfactants.
  • Useful silicone emulsifiers include dimethicone copolyols. These materials are polydimethyl siloxanes which have been modified to include polyether side chains such as polyethylene oxide chains, polypropylene oxide chains, mixtures of these chains, and chains comprising moieties derived from both ethylene oxide and propylene oxide.
  • Other examples include alkyl-modified dimethicone copolyols, i.e., compounds which comprise C2-C30 pendant side chains.
  • Still other useful dimethicone copolyols include materials having various cationic, anionic, amphoteric and zwitterionic pendant moieties.
  • emulsifiers include various non-ionic and anionic emulsifying agents such as sugar esters and polyesters, alkoxylated sugar esters and polyesters, C1-C30 fatty acid esters of C1-C30 fatty alcohols, alkoxylated derivatives of C1-C30 fatty acid esters of C1-C30 fatty alcohols, alkoxylated ethers of C1-C30 fatty alcohols, polyglyceryl esters of C1-C30 fatty acids, C1-C30 esters of polyols, C1-C30 ethers of polyols, alkyl phosphates, polyoxyalkylene fatty ether phosphates, fatty acid amides, acyl lactylates, soaps, and mixtures thereof.
  • non-ionic and anionic emulsifying agents such as sugar esters and polyesters, alkoxylated sugar esters and polyesters, C1-C30 fatty acid esters of C1-C30
  • Nonlimiting preferred examples of these non-silicon-comprising emulsifiers include: polyethylene glycol 20 sorbitan monolaurate (Polysorbate 20), polyethylene glycol 5 soya sterol, Steareth-20, Ceteareth-20, PPG-2 methyl glucose ether distearate, Ceteth-10, Polysorbate 80, cetyl phosphate, potassium cetyl phosphate, diethanolamine cetyl phosphate, Polysorbate 60, glyceryl stearate, PEG- 100 stearate, polyoxyethylene 20 sorbitan trioleate (Polysorbate 85), sorbitan monolaurate, polyoxyethylene 4 lauryl ether sodium stearate, polyglyceryl-4 isostearate, hexyl laurate, steareth-20, ceteareth-20, PPG-2 methyl glucose ether distearate, ceteth-10, diethanolamine cetyl phosphate, glyceryl stearate, PEG- 100
  • Preservatives may be added to the composition such as benzoic acid, sodium benzoate, sorbic acid, potassium sorbate, 2-bromo2-nitropropane-l,3-diol (bronopol, which is available commercially under the trade name Myacide ®), benzyl alcohol, diazolidinyl urea, imidazolidinyl urea, methyl paraben, phenoxyethanol, ethyl paraben, propyl paraben, sodium methyl paraben, sodium dehydroacetate, polyhexamethylenebiguanide hydrochloride, isothiazolone and sodium propyl paraben, suitably in an amount of from 0.01 to 10 wt % of the composition.
  • bronopol which is available commercially under the trade name Myacide ®
  • benzyl alcohol diazolidinyl urea, imidazolidinyl urea, methyl paraben, phenoxyethanol, ethyl paraben
  • Sequestering agents may be added to the composition, such as ethylenediamine tetraacetic acid and salts thereof, for example in an amount from 0 or 0.005 to 0.5 wt % of the composition.
  • composition may include waxes such as cetearyl alcohol, Candelilla wax,
  • Carnauba wax, lanolin wax, microcrystalline wax, ozokerite wax, paraffin wax, polyethylene wax or beeswax, cocoa butter suitably in an amount of from 0.1 to 25 wt % (often for a mascara), 0.1 to 60 wt % (often for a lip-stick), or 0 to 10 wt % (often for a foundation) of the composition.
  • the composition may also comprise suitable, cosmetically acceptable diluents, carriers and/or propellants such as dimethyl ether.
  • the composition may also include pearlising agents such as stearic monoethanolamide and/or mica, suitably in an amount of from 0 or 0.01 to 10 wt % of the composition.
  • Perfumes may be added suitably in an amount of from 0 or 0.01% to 2 wt % of the composition, as may water soluble dyes such as tartrazine, suitably in an amount of from a trace amount such as 0 or lxl 0 "5 to 0.1 wt % of the composition.
  • the composition may also include pH adjusting agents such as sodium hydroxide, amino methyl propanol, triethanolamine, suitably in an amount of from 0 or 0.01 % to lO wt % of the composition.
  • pH adjusting agents such as sodium hydroxide, amino methyl propanol, triethanolamine, suitably in an amount of from 0 or 0.01 % to lO wt % of the composition.
  • the composition may be buffered by means well known in the art, for example by use of buffer systems comprising succinic acid, citric acid, lactic acid, and acceptable salts thereof, phosphoric acid, mono-or disodium phosphate and sodium carbonate.
  • the composition may have a pH between 3 and 10, between 4 and 8, or between 4.5 and 6.5.
  • a thickener, viscosity modifying agent and/or gelling agent may be added to the composition in addition to the film forming polymer, and the hyperbranched or dendrimer hydrophilic polymer disclosed herein.
  • the thickener, viscosity modifying agent and/or gelling agent such as acrylic acid polymers e.g.
  • a taurate copolymer such as acryloyl methyl taurate-vinylpyrrolidone copolymers, alkylated polyvinylpyrrolidone copolymers (such as AnatronTMV220) or hydroxyethylacrylate/sodium acryloyldimethyl taurate copolymers, or modified celluloses e. g.
  • hydroxyethylcellulose available commercially under the trade name Natrosol® (Hercules) or hydroxypropylmethyl cellulose, amine oxides, block polymers of ethylene oxide and propylene oxide (for example, those available from BASF Wyandotte under the trade name "Pluronic”®), PVM, MA, or a decadiene crosspolymer (available under the trade name Stabilez® 60), ethoxylated fatty alcohols, salt (magnesium chloride, sodium chloride), Aristoflex®AVC (Clariant), phthalic acid amide, xanthan gum, starch, or modified starch (such as a metal salt of starch e.g., aluminum salt of the reaction product of 1-octenylsuccinic anhydride with starch), sodium polyacrylate, polyvinyl alcohols, fatty alcohols and alkyl galactmanans available under the trade name N-Hance® from Hercules.
  • the composition disclosed herein may optionally contain 0.1 to 10 wt %, or 0.5 to 5 wt %, or 0.5 to 3 wt % of a thickener such as a viscosity modifying agent and/or gelling agent, and may be a polymeric thickener.
  • a thickener such as a viscosity modifying agent and/or gelling agent
  • the gel may comprise: 50 to 95 wt % water and 0.1 to l0 wt % of a thickener, or 60 to 95 wt % water, and 0.5 to 5 wt % of a thickener, or 70 to 90 wt % of water; and 0.5 to 3 wt % of a thickener.
  • the thickener may be organic or inorganic.
  • Inorganic thickeners include silica and clay materials such as bentonite, hectorite and montmorillonite. Specific examples of clay materials include disteardimonium hectorite and stearalkonium hectorite (these materials form part of the Bentone® gel range from Elementis).
  • These inorganic thickeners may be hydrophobically modified. Examples of silica that have been hydrophobically modified are silica silylate and silica dimethyl silylate (available as part of the Aerosil® range from Evonik).
  • the emulsion disclosed herein may be a water-in-oil, oil-in-water, or water-in- silicone composition. In one embodiment the emulsion is an oil-in-water composition.
  • the emulsion may comprise an oil phase and have a polar solvent content of 30 to 85 wt %, or 50 to 80 wt %, or 60 to 75 wt % of the composition.
  • the polar solvent may contain water present at 40 to 80 wt %, or 50 to 75 wt %, or 60 to 75 wt % of the composition.
  • the emulsion may comprise an oil phase having 15 to 70 wt %, or 30 to 50 wt %, or 25 to 40 wt % of the composition.
  • the emulsion may be an oil-in-water composition comprising 15 to 70 wt % of an oil phase; and 30 to 85 wt % of an aqueous phase.
  • the emulsion may be an oil-in-water composition comprising 25 to 40 wt % of an oil phase; and 60 to 75 wt % of an aqueous phase.
  • the emulsion may be in the form of a water-in-silicone emulsion, and the water phase may be present at 30 to 85 wt % of an aqueous phase; and silicone present at 15 to 70 wt % of a silicone phase.
  • the emulsion may be in the form of a water-in-silicone emulsion, and the water phase may be present at 60 to 75 wt % of an aqueous phase; and silicone present at 25 to 40 wt % of a silicone phase.
  • the oil phase may be provided by any suitable silicate, dimethiconols, or silicone elastomer.
  • the oil phase may be provided by a silicone elastomer.
  • the silicone oil phase may be formed from an organopolysiloxane.
  • the organopolysiloxane may be chosen from one or more of a polyalkylsiloxane, alkyl substituted dimethicone, cyclomethicone, trimethylsiloxysilicate. dimethiconol, or polyalkylaryl siloxane,.
  • the polyalkylsiloxane may be for example a cyclomethicone, or dimethicone, often a dimethicone.
  • a water-in-silicone composition disclosed herein may include an emulsifying crosslinked organopolysiloxane elastomer, a non-emulsifying crosslinked organopolysiloxane elastomer, or a mixture thereof.
  • non-emulsifying as used herein, defines crosslinked organopolysiloxane elastomers from which polyoxyalkylene units are absent.
  • the elastomers may include dimethyl polysiloxanes crosslinked by Si-H sites on a molecularly spherical MQ resin.
  • Emulsifying crosslinked organopolysiloxane elastomers include the crosslinked polymers described in US Patents 5,412,004; 5,837,793; and 5,811 ,487.
  • the emulsifying elastomer comprised of dimethicone copolyol crosspolymer (and) dimethicone is commercially available from Shin Etsu under the trade name KSG-21.
  • the non-emulsifying elastomers may include dimethicone crosspolymers.
  • dimethicone crosspolymers are supplied by a variety of suppliers including Dow Corning (EL9240).
  • Other dimethicones crosspolymer are available from General Electric (SFE 839), Shin Etsu (KSG-15, 16, 18 [dimethicone/phenyl vinyl dimethicone crosspolymer]), and Grant Industries (GRANSILTM line of elastomers).
  • SFE 839 General Electric
  • Shin Etsu KSG-15, 16, 18 [dimethicone/phenyl vinyl dimethicone crosspolymer]
  • Grant Industries GRANSILTM line of elastomers.
  • Cross-linked organopolysiloxane elastomers useful in the present invention and processes for making them are further described in US Patents 4,970,252; 5,760,116; and 5,654,362.
  • An oil-in-water or water-in-oil emulsion may comprise an organic oil.
  • the organic oil may be volatile or non-volatile.
  • the organic oil may include a diluent, a solvent, a polyolefm polymer, or an ester oil.
  • ester oil means an oil that is liquid at room temperature (25 °C.) comprising at least one ester functional group.
  • the ester oil used herein is chosen, for example, from monoesters.
  • the ester oil may, for example, be chosen from the monoesters of formula R ⁇ COOR 2 wherein R 1 may be selected from linear and branched hydrocarbon-based chains comprising from 4 to 30, or 6 to 24, or 7 to 20 carbon atoms, and R 2 may be chosen from branched hydrocarbon-based chains comprising from 3 to 40 carbon atoms, such as from 10 to 30 carbon atoms and further such as from 16 to 26 carbon atoms.
  • R 1 may be selected from linear and branched hydrocarbon-based chains comprising from 4 to 30, or 6 to 24, or 7 to 20 carbon atoms
  • R 2 may be chosen from branched hydrocarbon-based chains comprising from 3 to 40 carbon atoms, such as from 10 to 30 carbon atoms and further such as from 16 to 26 carbon atoms.
  • ester oils examples include isodecyl neopentanoate; isocetyl octanoate; isononyl isononanoate, isodecyl isononanoate, tridecyl isononanoate; hexyl laurate, 2-hexyldecyl laurate; isopropyl myristate, isocetyl myristate, isotridecyl myristate, 2-octyldodecyl myristate; isopropyl palmitate, 2-ethylhexyl palmitate, isooctyl palmitate, isocetyl palmitate, isodecyl palmitate, isostearyl palmitate, 2-octyldecyl palmitate; isopropyl isostearate, 2-octyldodecyl stearate, isostearyl isostearate, and 2-
  • the ester oil may be present in the emulsion disclosed herein in an amount ranging, for example, from 0 to 20 wt %, or 0.1 to 15 wt %, or 1 to 10 wt % of the composition.
  • Each of the following W/Si emulsion foundation examples has a base formulation containing 25.5-27.5 wt % caprylyl methicone, 2 wt % PEG-9 dimethicone, 8 wt % bentone VS-5PC V (cyclopentasiloxane, disteardimonium hectorite and propylene carbonate)/cyclomethicone D5, 1.5 wt % bis-isobutyl PEG/PPG 10/7 dimethicone copolymer, 8 wt % triethoxycaprylylsilane treated pigments (titanium dioxide, iron oxide yellow, iron oxide red and iron oxide black), 8 wt % talc, 0.92 wt % of a mixture (of phenoxyethanol, methyl paraben, and ethyl paraben), 1.0 wt % magnesium sulphate, 0.05 wt % Sequestrene Na4 (tetrasodium ethylenedi
  • Comparative Example 2 comprises 40 wt % water, 5 wt % of hyperbranched polymer (HybraneTMS1200), and 0 wt % of resin composed of Cyclopentasiloxane and trimethylsiloxysilicate.
  • Comparative Example 3 comprises 40 wt % water, 3 wt % of hyperbranched polymer (HybraneTMS1200), and 0 wt % of resin composed of Cyclopentasiloxane and trimethylsiloxysilicate.
  • Inventive Example 1 comprises 40 wt % water, 3 wt % of hyperbranched polymer (HybraneTMS1200), and 2 wt % of resin composed of Cyclopentasiloxane and trimethylsiloxysilicate.
  • Comparative Example 4 comprises 43 wt % water, 0 wt % of hyperbranched polymer, and 2 wt % of resin composed of cyclopentasiloxane and trimethylsiloxysilicate.
  • the examples are prepared by adding in a main vessel caprylyl methicone, PEG-9 dimethicone, bis-isobutyl PEG/PPG 10/7 dimethicone copolymer, bentone/cyclomethicone D5, phenoxyethanol, methyl paraben, and ethyl paraben.
  • the contents of the vessel are homogenised at 3500 rpm for 2 minutes.
  • Triethoxycaprylylsilane treated pigments titanium dioxide and black, red and yellow iron oxide
  • Talc is added and the mixture is homogenised at 4500 rpm for a further 5 minutes.
  • the remaining ingredients are added to a second vessel with water and added slowly to the main vessel whilst stirring at 500 rpm to form a coarse emulsion.
  • the contents of the vessel are homogenised at 4000 rpm for up to 5 minutes to form a fine emulsion.
  • Areas of 3x4 cm are marked on a silicone rubber mat by placing adhesive tape in vertical and horizontal lines. A sufficient amount of example is placed at the top of a 3x4 cm area. Using a 3.5cm wide palette knife, each example drowned down so that it filled the area between the tape lines with even coverage from top to bottom. The tape is removed. The rubber mat is placed in a 30 °C oven for 20 minutes. The samples are equilibrated back to room temperature for 5 minutes. The following observations are made in triplicate for each example are summarised below. Each sample is rated with 100 % equivalent to the film remaining intact. Reductions in film for samples are calculated as a percentage of the amount of film remaining intact.
  • Transfer resistance test a two-ply tissue is placed over the samples; and a 300g weight is placed on top of the tissue for 30s. Record any transfer on the tissue.
  • Water resistance test cold water is run on the top of the rubber mat (not directly over the samples but flowing over each film for 30s). Record the approximate percentage of film left intact.
  • Rub resistance Rubbed with firm pressure over each film once up and once down using a 4x5 cm silicone rubber rectangle. Record the approximate percentage of film left intact.
  • Flexibility Flex the rubber mat by folding it in half along the vertical and horizontal middle lines of each sample. Record the approximate percentage of film left intact and any instances of cracking.
  • CE2, CE4 and EX1 has a higher rating for rub resistance than the comparative examples CE1 and CE4.
  • CE1, CE4 and EX1 also have acceptable coating flexibility, with EX1 having benefits of increased rub resistance and coating flexibility performance.

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Abstract

L'invention concerne une composition comprenant : (a) un pigment, (b) un polymère hydrophile hyperramifié ou dendrimère, (c) un polymère filmogène différent de (b), la composition comprenant un solvant polaire constituant jusqu'à 95 % en poids de la composition. L'invention concerne en outre l'utilisation et le procédé de l'invention dans des applications cosmétiques.
PCT/EP2017/025076 2016-04-07 2017-04-05 Composition contenant un polymère et procédé associé WO2017174213A1 (fr)

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US20130251659A1 (en) * 2008-06-19 2013-09-26 Franciscus Johannes Marie Derks Shampoo preparations
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