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WO2017174214A1 - Composition contenant un polymère et procédé associé - Google Patents

Composition contenant un polymère et procédé associé Download PDF

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Publication number
WO2017174214A1
WO2017174214A1 PCT/EP2017/025077 EP2017025077W WO2017174214A1 WO 2017174214 A1 WO2017174214 A1 WO 2017174214A1 EP 2017025077 W EP2017025077 W EP 2017025077W WO 2017174214 A1 WO2017174214 A1 WO 2017174214A1
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WO
WIPO (PCT)
Prior art keywords
composition
hyperbranched
polymer
hydrophilic polymer
sunscreen agent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/EP2017/025077
Other languages
English (en)
Inventor
Jonathan George Collett
Paul James Tomlinson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boots Co PLC
Original Assignee
Boots Co PLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Boots Co PLC filed Critical Boots Co PLC
Publication of WO2017174214A1 publication Critical patent/WO2017174214A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8158—Homopolymers or copolymers of amides or imides, e.g. (meth) acrylamide; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8176—Homopolymers of N-vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86—Polyethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/88—Polyamides
    • 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
    • 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

Definitions

  • the disclosed technology relates to a composition
  • a composition comprising: (a) a sunscreen agent, (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 or sun care applications.
  • Sun care products are applied to skin to form a coating/film.
  • the coating/film is susceptible to stresses and rubbing, or contact with other bodies/surfaces e.g., washed off by water. The result of these stresses, rubbing and contact is believed to have a negative impact on the amount of sunscreen agent retained on the skin.
  • stresses and/or rubbing sunscreen agent 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, or washing off, the coating of the skin with a sun care composition is reduced and a loss of performance 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.
  • US2008/081025 discloses a cosmetic composition
  • a cosmetic composition comprising a conjugate comprising a hyperbranched polymer covalently bonded to at least three UV absorbing chromophores having an UV absorption maximum lambda max of at least >270 nm.
  • US2013/022560 (published 24 January 2013, Schlifkeposchalko) relates to a UV filter obtained by a process that prepared hyperbranched polyether-polyol followed by a partial or total etherification with 3-[l-(4-Hydroxymethyl-phenyl)-meth-(E)-ylidene]-l,7,7- trimethyl-bicyclo [2.2.1] heptan-2-one.
  • US2014/178318 (published 26 June 2014, Janssen et al.) relates to a UV filter obtained by a process that prepared hyperbranched polyether-polyol followed by esterifying 30-80% of hydroxyl groups with 2-(4-Diethylamino-2-hydroxybenzoyl)benzoic acid.
  • US2012/0282201 (published 8 November 2012, Schlifkeposchalko) relates to a UV filter obtained by a process that prepared hyperbranched polyether-polyol followed by a partial or total esterification of the hydroxyl groups with a p-alkoxycinnamic acid of a defined formula.
  • US2012/0288456 (published 15 November 2012, Schlifkeposchalko) relates to relates to a UV filter obtained by a process that prepared hyperbranched polyether-polyol followed by a partial or total, esterification of the hydroxyl groups with 2-cyano-3,3- diphenylacrylic acid.
  • US2013034511 (published 7 February 2013, Schlifkeposchalko) relates to a UV filter obtained by a process that prepared hyperbranched polyether-polyol followed by a partial or total esterification of the hydroxyl groups with p-dimethylamino benzoic acid.
  • US2014/0093459 (published 3 April 2014, Schlifkeposchalko) relates to a method to enhance solubility of butyl methoxydibenzoylmethane and/or bis-ethylhexyloxyphenol methoxyphenyl triazine in a cosmetic oil suitable as a solvent for butyl methoxydibenzoylmethane and/or bis-ethylhexyloxyphenol methoxyphenyl triazine, which method comprises incorporating a solubility enhancing effective amount in a cosmetic oil suitable as a solvent for butyl methoxydibenzoylmethane and/or bis-ethylhexyloxyphenol methoxyphenyl triazine of a polyglycerol based UV filter obtained by a process comprising a UV filter obtained by a process that prepared hyperbranched polyether-polyol followed by a and 2-(4-diethylamino-2-hydroxybenzoyl)benz
  • compositions disclosed herein may have increased rub (or wear) resistance and/or increased coating flexibility.
  • 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.
  • 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 skin.
  • 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.
  • 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.
  • the disclosed technology relate to a method for cosmetically protecting human skin against the deleterious effects of ultraviolet irradiation, comprising topically applying thereto a cosmetically effective amount of the composition disclosed herein to skin.
  • the disclosed technology relates to the use of the composition disclosed as a sun care composition for skin to provide the benefit of spreadability without losing UV absorbance.
  • the disclosed technology provides a composition, methods and uses as disclosed above.
  • compositions such as shampoos, 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.
  • compositions disclosed herein 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 skin for up to 8, or 4 (or 3) hours as a sun care composition.
  • the composition disclosed herein comprises a sunscreen agent component.
  • the sunscreen may comprise an organic or inorganic sunscreen agent (may be known as sun screen filter, or blocker for UVA and/or UVB, or a UVA and/or UVB active) or a combination of the two.
  • the sunscreen agent when it is inorganic, it may be a pigment.
  • the pigment may also be referred to as a SPF enhancer, and typically the particle size of the pigment is finer. Finer particle size allows for the particles to affect light scattering. Black iron oxide, and/or titanium dioxide are typical pigment examples.
  • the pigment may be organic or inorganic.
  • 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.
  • suitable inorganic sunscreen agent may include those chosen from microfme titanium dioxide, and microfme zinc oxide, or boron nitride.
  • the disclosed technology comprising a sunscreen agent may have the advantage of easier to apply topically as the composition may be more spreadable.
  • the pigment when the pigment is organic, the pigment may be carbon black, an azo compound, xanthene, quinone, FD&C pigment, D&C pigment, or a lake pigment.
  • 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
  • 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, Yellow 5, Blue 1, or derivatives thereof.
  • 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 sunscreen agent of the disclosed technology may be organic.
  • Suitable organic sunscreen agent include those chosen from: a) p-aminobenzoic acids, their esters and derivatives (for example, 2-ethylhexyl p-dimethylaminobenzoate), b) methoxycinnamate esters (for example, 2-ethylhexyl p-methoxycinnamate, 2-ethoxyethyl p- methoxycinnamate or a, p-di- (p-methoxycinnamoyl)-a'- (2ethylhexanoyl)-glycerin, c) benzophenones (for example oxybenzone), d) dibenzoylmethanes such as 4-(tert-butyl)-4'- methoxydibenzoylmethane, e) 2-phenylbenzimidazole-5 sulfonic acid and its salts, f) alkyl-
  • the sunscreening agent may for instance be 4-(l,l -dimethyl ethyl)-4'- methoxydibenzoyl methane (also known as butylmethoxy dibenzoylmethane) or 4- isopropyidibenzoylmethane.
  • the organic sunscreen agent may for example include butyl methoxydibenzoylmethane (sold commercially as ParsolTM1789 or referred to as Avobenzone), diethylhexyl butamido triazone (also known as Iscotrizinol), bis- ethylhexyloxyphenol methoxyphenyl MPT, or bis-ethylhexyloxyphenol methoxyphenyl triazine (also known as bemotrizinol).
  • butyl methoxydibenzoylmethane sold commercially as ParsolTM1789 or referred to as Avobenzone
  • diethylhexyl butamido triazone also known as Iscotrizinol
  • bis- ethylhexyloxyphenol methoxyphenyl MPT bis-ethylhexyloxyphenol methoxyphenyl triazine (also known as bemotrizinol).
  • sunscreen ingredients include those chosen from homosalate, ethylhexyl salicylate, diethylhexylbutamido triazone, bis-ethylhexyloxyphenol methoxyphenyl triazine, diethylamino hydroxybenzoyl hexyl benzoate, butyl methoxydibenzoylmethane, methylene bis-benzotriazoyl tetramethylbutylphenol, Polysilicone-15 and/or mixtures thereof.
  • the disclosed technology is not a reaction product of hyperbranched or dendrimer hydrophilic polymer and an organic sunscreen agent.
  • the disclosed technology comprising a sunscreen agent may be a cream, lotion, or spray; and may be aqueous based or anhydrous (water free, but comprising alcohol as polar solvent).
  • a sunscreen agent may be present from 0.1 to 10 wt %, or 0.5 to 7 wt %, or 1 to 6 wt % of the composition.
  • 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 (published 8 April, 1999, Van Benthem et al.), for example see claims 1 to 16 of WO99/16810; and Examples I to IV on page 29 line 26 to page 32, line 26 for outline of the synthesis of representative examples of the polyesteramide.
  • 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/C 10-30 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 acryl
  • 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 1 to 3 wt % of the composition.
  • Polar Solvent
  • 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, preservatives and/or gelling agents sequestering agents, wax, diluents, carriers, propellants perfumes, or 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 (e.g. origanum vulgare), 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.
  • 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 helianthus annuus
  • wild carrot e.g. daucus carota
  • Hop e.g. 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 antioxidant may be present at 0.005 to 10 wt, or 0.01 to 7 wt %, or 0.01 to 5 wt % of the composition.
  • 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.
  • fructose glucose, xylose, honey, mannose, xylose
  • gluconodeltalactone and starches and their derivatives, pyrrolidone, carboxylic acid, hyaluronic acid and salts thereof, lactamide monoethanolamine, acetamide monoethanolamine, panthenol, or allantoin.
  • the skin conditioning agent may be chosen from glycerine, arabinoglactan, butylene glycol, hyaluronic acid, shea butter, propylene glycol, ethylhexyl glycerine, or hyaluronate.
  • Salicylic Acid Compound 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.
  • 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' luronic”®), 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. Emulsion
  • the emulsion disclosed herein may be a water-in-oil, oil-in-water, or water-in- silicone composition, often an oil-in-water composition.
  • the emulsion may be an oil-in-water emulsion, or a water-in-silicone oil emulsion, often an oil-in-water emulsion.
  • the emulsion may comprise an oil phase and have a polar solvent content of 30 to
  • 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.
  • 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 O/W emulsion sun care examples has a base formulation containing octyl salicylate, shea butter, silicone fluid, tribehenin, diethylhexyl butamido triazone, bis-ethylhexyloxyphenol metoxyphenyl triazine, octocrylene, butylene glycol, denatured ethanol, polyglyceryl-3 methylglucose distearate, potassium cetyl phosphate, acrylates/C 10-30 alkyl acrylate crosspolymer, phenoxyethanol, triethanolamine, water and 4.8 wt % of butyl methoxydibenzoylmethane.
  • Comparative Example 1 comprises 11.1 wt % of C12-15 alcohols benzoate, 58.1 wt % water, and 2 wt % of hyperbranched polymer (HybraneTMS1200).
  • Comparative Example 2 comprises 11.1 wt % of C12-15 alcohols benzoate, 55.1 wt % water, and 5 wt % of hyperbranched polymer (HybraneTMS1200).
  • Inventive Example 1 comprises 9.2 wt % of C12-15 alcohols benzoate, 58.1 wt % water, 2 wt % of hyperbranched polymer (HybraneTMS 1200), and 1.9 wt % of alkylated polyvinylpyrrolidone copolymer.
  • Comparative Example 3 comprises 9.2 wt % of C12-15 alcohols benzoate, 60.1 wt % water, and 1.9 wt % of alkylated polyvinylpyrrolidone copolymer.
  • Comparative Example 4 comprises 11.1 wt % of C12-15 alcohols benzoate, and 60.1 wt % water.
  • Each example is evaluated for viscosity using a rotational viscometer (Brookfield LVDV-I) at 23°C.
  • Each example is also evaluated for UV absorbance. The viscosity and UV absorbance measurements obtained are presented below. Typically better results are obtained for examples with a lower viscosity (suggesting the example is more spreadable), and higher UV absorbance.
  • a SPF tester system is calibrated and optimised to ensure the maximum signal over the required 290 to 400 nm wavelength range, according to the operation manual.
  • a polymethylmethacrylate (PMMA) plate with a homogeneous layer of isopropyl myristate is scanned as a reference to determine 100% transmission of UV light (290 nm-400 nm).
  • 22.5 mg of the product is applied and is spread evenly over a total area of 22.5 cm 2 .
  • the sample is left to dry for 15 minutes prior to scanning.
  • the plate with sunscreen on is then scanned in 9 different locations.
  • a scan consists of UV transmission measurements taken at 5nm increments from 290 to 400 nm. Transmission readings are converted to absorbance units.
  • Three different plates were used for each product, and the average is reported below for each:

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Abstract

L'invention concerne une composition comprenant : (a) un agent écran solaire, (b) un polymère hydrophile hyperramifié ou dendrimère, (c) un polymère filmogène différent de (b), laquelle composition comprend 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 ou des applications de soins solaires.
PCT/EP2017/025077 2016-04-07 2017-04-05 Composition contenant un polymère et procédé associé Ceased WO2017174214A1 (fr)

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WO2020109264A1 (fr) * 2018-11-26 2020-06-04 Dsm Ip Assets B.V. Composition cosmétique comprenant des copolymères hyperramifiés spécifiques et des émulsifiants anioniques
WO2020109262A1 (fr) * 2018-11-26 2020-06-04 Dsm Ip Assets B.V. Composition cosmétique comprenant des copolymères et des huiles spécifiques hyperramifiés
WO2020109263A1 (fr) * 2018-11-26 2020-06-04 Dsm Ip Assets B.V. Composition cosmétique comprenant des copolymères hyperramifiés spécifiques et des filtres uv organiques

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CN109401081A (zh) * 2018-10-31 2019-03-01 江苏达胜高聚物股份有限公司 一种耐热型电缆料及其制备方法和用途
WO2020109264A1 (fr) * 2018-11-26 2020-06-04 Dsm Ip Assets B.V. Composition cosmétique comprenant des copolymères hyperramifiés spécifiques et des émulsifiants anioniques
WO2020109262A1 (fr) * 2018-11-26 2020-06-04 Dsm Ip Assets B.V. Composition cosmétique comprenant des copolymères et des huiles spécifiques hyperramifiés
WO2020109263A1 (fr) * 2018-11-26 2020-06-04 Dsm Ip Assets B.V. Composition cosmétique comprenant des copolymères hyperramifiés spécifiques et des filtres uv organiques
JP2022508094A (ja) * 2018-11-26 2022-01-19 ディーエスエム アイピー アセッツ ビー．ブイ． 特定の超分岐コポリマー及び有機ｕｖフィルターを含む化粧品組成物
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JP7436109B2 (ja) 2018-11-26 2024-02-21 ディーエスエム アイピー アセッツ ビー．ブイ． 特定の超分岐コポリマー及び有機ｕｖフィルターを含む化粧品組成物
JP2024112992A (ja) * 2018-11-26 2024-08-21 ディーエスエム アイピー アセッツ ビー．ブイ． 特異的超分岐コポリマー及びアニオン性乳化剤を含む化粧品組成物
US12220477B2 (en) 2018-11-26 2025-02-11 Dsm Ip Assets B.V. Cosmetic composition comprising specific hyperbranched copolymers and organic UV filters

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