WO2016075074A1 - Copolymère phosphonique et son utilisation en cosmétique - Google Patents

Copolymère phosphonique et son utilisation en cosmétique Download PDF

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Publication number
WO2016075074A1
WO2016075074A1 PCT/EP2015/076051 EP2015076051W WO2016075074A1 WO 2016075074 A1 WO2016075074 A1 WO 2016075074A1 EP 2015076051 W EP2015076051 W EP 2015076051W WO 2016075074 A1 WO2016075074 A1 WO 2016075074A1
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WIPO (PCT)
Prior art keywords
weight
denotes
acid
copolymer
monomer
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Application number
PCT/EP2015/076051
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English (en)
Inventor
Bertrand Lion
Laurent SABATIE
Original Assignee
L'oreal
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.)
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Publication date
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Publication of WO2016075074A1 publication Critical patent/WO2016075074A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q3/00—Manicure or pedicure preparations
    • A61Q3/02—Nail coatings
    • 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)
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
    • 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
    • A61K2800/20—Chemical, physico-chemical or functional or structural properties of the composition as a whole
    • A61K2800/26—Optical properties
    • A61K2800/262—Transparent; Translucent

Definitions

  • the present invention relates to a phosphonic acid group-containing copolymer, a cosmetic composition comprising such a copolymer and the use thereof as a nail varnish.
  • copolymers of tetrahydrofurfuryl (meth)acrylate and of phosphonic acid group-containing monomers make it possible to obtain a uniform transparent film which does not chip, unlike similar copolymers containing acrylic acid instead of the phosphonic acid monomer.
  • the film obtained has good properties of adhesion.
  • a subject of the present invention is a copolymer derived from the polymerization of:
  • Such a copolymer is referred to hereinbelow as a phosphonic polymer.
  • a subject of the invention is also a composition comprising, in a physiologically acceptable medium, a phosphonic polymer as described previously.
  • a subject of the invention is also a cosmetic process for making up and/or non- therapeutically caring for the nails, comprising the application to the nails of a composition as defined previously.
  • Another subject of the invention is the use of a composition as defined previously, for obtaining a transparent, uniform film applied to the nails.
  • the phosphonic polymer according to the invention comprises a tetrahydrofurfuryl (meth)acrylate, a vinylphosphonic acid monomer of formula (I) and optionally an additional monomer as defined hereinafter.
  • R1 denotes H or -CH 3 ;
  • X denotes a covalent bond and n denotes an integer ranging from 0 to 14;
  • X denotes a -COO- group and n denotes an integer ranging from 2 to 6.
  • X denotes a covalent bond and n is an integer ranging from 0 to 6 or X denotes a -COO- group and n is an integer ranging from 2 to 4.
  • X denotes a covalent bond and n denotes an integer ranging from 0 to 4.
  • monomer (I) is vinylphosphonic acid.
  • the additional monomer optionally present is different to the tetrahydrofurfuryl (meth)acrylate monomers and the vinylphosphonic acid monomer of formula (I).
  • the additional monomer may be chosen from the monomers of formula (II):
  • R1 denotes a hydrogen atom or a methyl radical
  • X denotes O or NH or NR 3 ;
  • R3 denotes a linear C Ci 2 or branched C 3 -Ci 2 alkyl radical.
  • alkyl radical mention may be made of the methyl, ethyl, propyl, isopropyl, butyl, tert- butyl, pentyl, isopentyl, hexyl, heptyl, octyl, isooctyl, nonyl, decyl, undecyl, lauryl, myristyl, palmityl, stearyl, eicosyl and behenyl radicals.
  • the copolymer is free of any additional monomer.
  • the copolymer is chosen from copolymers of tetrahydrofurfuryl (meth)acrylate and of vinylphosphonic acid.
  • the polymer according to the invention is preferably chosen from the copolymers derived from the polymerization of:
  • the polymer according to the invention is chosen from the copolymers derived from the polymerization of:
  • the polymer is chosen from the copolymers derived from the polymerization of: - 70% to 95% by weight, of the total weight of the monomers, of tetrahydrofurfuryl (meth)acrylate;
  • copolymers according to the invention mention may be made of tetrahydrofurfuryl methacrylate/vinyphosphonic acid copolymers, in particular (80/20) or (90/10) (weight/weight) tetrahydrofurfuryl methacrylate/vinylphosphonic acid copolymers.
  • the copolymer may be a random, alternating (block) or gradient polymer. Preferably, the copolymer is random.
  • the copolymer according to the invention may be prepared by radical polymerization of the monomers described previously, especially as a mixture or sequentially added during the polymerization, especially using an organic solvent with a boiling point of greater than or equal to 60°C, for instance isododecane, ethanol, ethyl acetate, tetrahydrofuran, methyltetrahydrofuran or methyl ethyl ketone.
  • the organic solvent makes it possible to dissolve the monomers used and the polymer formed.
  • the polymerization is especially performed in the presence of a radical initiator especially of peroxide type (for example tert-butyl peroxy-2-ethylhexanoate: Trigonox® 21 S; 2,5- dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane:Trigonox® 141 ; tert-butyl peroxypivalate: Trigonox® 25C75 from Akzo Nobel) or of azo type (for example AIBN: azobisisobutyronitrile; V50: 2,2'-azobis(2-amidinopropane) dihydrochloride).
  • a radical initiator especially of peroxide type (for example tert-butyl peroxy-2-ethylhexanoate: Trigonox® 21 S; 2,5- dimethyl-2,5-bis(2-ethylhexanoylperoxy)hexane:Trigonox® 141 ; tert-butyl peroxy
  • the polymerization may be performed at a temperature ranging from 60 to 100°C, and preferably ranging from 60 to 85°C.
  • the polymerization time may be about 24 hours.
  • the phosphonic polymer according to the invention has a weight-average molecular weight ranging from 5000 to 1 000 000 daltons, more preferably ranging from 10 000 to 500 000 daltons, and even more preferably ranging from 15 000 to 350 000 daltons.
  • the phosphonic polymer as defined previously may be present in the composition in a content ranging from 0.1 % to 60% by weight and preferably ranging from 0.1 % to 40% by weight, relative to the total weight of the composition.
  • composition according to the invention may also comprise an additional film-forming polymer, commonly referred to as resin, such as sulfonamide resins, alkyd resins, nitrocellulose, cellulose esters such as cellulose acetobutyrate, cellulose acetate, cellulose acetopropionate.
  • resin such as sulfonamide resins, alkyd resins, nitrocellulose, cellulose esters such as cellulose acetobutyrate, cellulose acetate, cellulose acetopropionate.
  • the additional film-forming polymer may be present in a content ranging from 0.01 % to 50% by weight and preferably ranging from 1 % to 30% by weight, relative to the total weight of the composition.
  • composition according to the invention may comprise an auxiliary film-forming agent to improve the film-forming properties of the composition.
  • the auxiliary film-forming agent may be chosen from any compound known to those skilled in the art as being capable of performing the desired function, and may be chosen especially from plasticizers.
  • plasticizer As examples of plasticizer, the following can be cited:
  • citrates such as triethyl citrate, tributyl citrate, triethyl acetylcitrate, tributyl acetylcitrate, 2- triethylhexyl acetylcitrate,
  • phthalates such as diethyl phthalate, dibutyl phthalate, dioctyl phthalate, dipentyl phthalate, dimethoxyethyl phthalate,
  • tricresyl phosphate benzyl benzoate, tributyl phosphate, butyl acetyl ricinoleate, glyceryl acetyl ricinoleate, butyl glycolate, tributoxyethyl phosphate, triphenyl phosphate, dibutyl tartrate, camphor, glyceryl triacetate, N-ethyl-o,p-toluenesulfonamide, and mixtures thereof.
  • the plasticizer may be present in the composition in a content ranging from 0.01 % to 10% by weight and preferably ranging from 0.1 % to 5% by weight, relative to the total weight of the composition.
  • the plasticizer is present in the composition in a weight ratio of film-forming polymer/plasticizer ranging from 1.5 to 3.
  • composition according to the invention may comprise an organic solvent medium.
  • the composition may especially be anyhdrous.
  • the organic solvent medium of the composition may comprise one or more organic solvents chosen from:
  • ketones that are liquid at room temperature (25°C), such as methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, isophorone, cyclohexanone or acetone;
  • - alcohols that are liquid at room temperature, such as ethanol, isopropanol, n-propanol, n-butanol, diacetone alcohol, 2-butoxyethanol or cyclohexanol;
  • glycols that are liquid at room temperature, such as ethylene glycol, propylene glycol, pentylene glycol or glycerol;
  • propylene glycol ethers that are liquid at room temperature, such as propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate or dipropylene glycol n- butyl monoether; - short-chain esters (having from 3 to 8 carbon atoms in total), such as ethyl acetate, methyl acetate, propyl acetate, n-butyl acetate or isopentyl acetate;
  • - ethers that are liquid at room temperature, such as diethyl ether, dimethyl ether or dichlorodiethyl ether;
  • alkanes that are liquid at room temperature, such as decane, heptane, dodecane, isododecane or cyclohexane;
  • aldehydes that are liquid at room temperature, such as benzaldehyde or acetaldehyde. - mixtures thereof.
  • the organic solvent is preferably chosen from the short-chain esters described previously.
  • the organic solvent content in the composition may range from 10% to 95% by weight, preferably from 40% to 90% by weight and better still from 60% to 85% by weight, relative to the total weight of the composition.
  • the composition may comprise a thickener, especially for imparting a consistency to the composition which enables good application of the composition to the nails.
  • the thickener is more particularly an organic solvent thickener and may be chosen from the hydrophobic silicas such as those described in document EP-A-898960, and for example sold under the references "AEROSIL R812®” by the company Degussa, "CAB-O-SIL TS-530®", “CAB-O-SIL TS-610®” and “CAB-O-SIL TS-720®” by the company Cabot, "AEROSIL R972®” and “AEROSIL R974®” by the company Degussa; clays such as montmorillonite, stearalkonium hectorite, stearalkonium bentonite; polysaccharide alkyl ethers (especially those in which the alkyl group comprises from 1 to 24 carbon atoms, preferably from 1 to 10, better still from 1 to 6 and more especially from 1 to
  • composition according to the invention may also comprise any cosmetic adjuvant known to those skilled in the art as being able to be incorporated into such a composition, such as fillers, spreading agents, wetting agents, dispersants, antifoams, preservatives, UV-screening agents, active agents, surfactants, moisturizers, fragrances, neutralizing agents, stabilizers, antioxidants or colorants. Needless to say, a person skilled in the art will take care to select this or these optional additional compound(s), and/or the amount thereof, such that the advantageous properties of the corresponding composition according to the invention are not, or are not substantially, adversely affected by the envisaged addition.
  • any cosmetic adjuvant known to those skilled in the art as being able to be incorporated into such a composition, such as fillers, spreading agents, wetting agents, dispersants, antifoams, preservatives, UV-screening agents, active agents, surfactants, moisturizers, fragrances, neutralizing agents, stabilizers, antioxidants or colorants.
  • composition according to the invention is preferably in the form of a nail varnish.
  • Example 1 (90/10 by weight) Tetrahydrofurfuryl methacrylate/vinylphosphonic acid copolymer
  • 2,5-Dimethyl-2,5-di(2-ethylhexanoylperoxy)hexane initiator (Trigonox® T141 from Akzo Nobel) were added.
  • the reaction medium was heated at reflux of the ethyl acetate for 24 hours with stirring. After cooling to room temperature (25°C), the reaction medium was diluted with 300 g of a (50/50 by weight) mixture of butanone and methyltetrahydrofuran.
  • the product obtained was precipitated from cyclohexane, recovered and dried in an oven at 60°C under vacuum.
  • the copolymer was prepared according to the procedure from Example 1 using 160 g of tetrahydrofurfuryl methacrylate and 40 g of vinylphosphonic acid.
  • the acid number is 176 mg/g.
  • the copolymer was prepared according to the procedure from Example 1 using 160 g of tetrahydrofurfuryl methacrylate, 20 g of vinylphosphonic acid and 20 g of methyl methacrylate.
  • Example 4 (70/10/20 by weight) Tetrahydrofurfuryl methacrylate/vinylphosphonic acid/methyl methacrylate copolymer
  • the copolymer was prepared according to the procedure from Example 1 using 140 g of tetrahydrofurfuryl methacrylate, 20 g of vinylphosphonic acid and 40 g of methyl methacrylate.
  • the copolymer was prepared according to the procedure from Example 1 using 180 g of methyl methacrylate and 20 g of vinylphosphonic acid.
  • the copolymer was prepared according to the procedure from Example 1 using 160 g of methyl methacrylate and 40 g of vinylphosphonic acid.
  • the acid number is 149 mg/g.
  • Example 7 (outside the invention): (90/10 by weight) Cyclohexyl methacrylate/vinylphosphonic acid copolymer
  • the copolymer was prepared according to the procedure from Example 1 using 180 g of cyclohexyl methacrylate and 20 g of vinylphosphonic acid.
  • Example 8 (outside the invention): (80/20 by weight) Cyclohexyl methacrylate/vinylphosphonic acid copolymer
  • the copolymer was prepared according to the procedure from Example 1 using 160 g of cyclohexyl methacrylate and 40 g of vinylphosphonic acid.
  • the acid number is 138 mg/g.
  • methacrylate/acrylic acid copolymer The copolymer was prepared according to the procedure from Example 1 using 180 g of tetrahydrofurfuryl methacrylate and 20 g of acrylic acid.
  • Example 10 (outside the invention): (80/20 by weight) Tetrahydrofurfuryl
  • methacrylate/acrylic acid copolymer The copolymer was prepared according to the procedure from Example 1 using 160 g of tetrahydrofurfuryl methacrylate and 40 g of acrylic acid.
  • Each polymer was placed in solution at 30% AM in a (50/50) mixture of ethyl acetate/ethanol.
  • a nail varnish having the following composition was prepared: - polymer of Example 1 25 g
  • composition obtained, applied to the nails makes it possible to obtain, after drying, a transparent and uniform film which is glossy and has no cracking.
  • Example 13 (comparative): The wear property of the gloss of the films obtained with the polymer of Example 1 (invention) and the polymer of Example 10 (outside the invention) was measured.
  • a solution at 25% AM of the polymer in a (50/50 by weight) mixture of ethyl acetate/ethanol was prepared.
  • Each solution was poured onto a metal (steel) support to obtain, after drying for 5 days at 23 ⁇ 2°C and at 55 ⁇ 5% relative humidity, a film with a thickness of approximately 100 ⁇ (after drying).
  • the gloss of the film obtained after drying was measured.
  • the film was then subjected to abrasion for 10 revolutions using a Taber abrasion tester (reference 5130 Abraser) equipped with two abrasive discs, sold under the name CS1 OF by the company Taber Industries, with application of a force of 2.5 N to each disc. After the abrasion operation, the gloss of the film was measured (gloss T1 ).

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

L'invention concerne un copolymère dérivé de la polymérisation de : (i) 70 % à 95 % en poids, du poids total des monomères, de (méth)acrylate de tétrahydrofurfuryle; (ii) 1 % à 30 % en poids de monomère acide vinylphosphonique; (iii) 0 à 20 % en poids d'un monomère supplémentaire. L'invention concerne également une composition cosmétique comprenant le copolymère et un procédé cosmétique de maquillage ou de soin des matières kératiniques, plus particulièrement les ongles, comprenant l'application topique de la composition sur les matières kératiniques.
PCT/EP2015/076051 2014-11-13 2015-11-09 Copolymère phosphonique et son utilisation en cosmétique WO2016075074A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR1460961A FR3028513B1 (fr) 2014-11-13 2014-11-13 Copolymere phosphonique et son utilisation cosmetique
FR1460961 2014-11-13

Publications (1)

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WO2016075074A1 true WO2016075074A1 (fr) 2016-05-19

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WO (1) WO2016075074A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0085370A2 (fr) * 1982-01-25 1983-08-10 Wickhen Products, Inc. Compositions pour vernis à ongles exemptes de nitrocellulose
EP0522756A1 (fr) * 1991-06-28 1993-01-13 Calgon Corporation Terpolymères ampholyte avec des propriétés de conditionnement supérieur employer dans des shampooings et d'autres produits pour les soins des cheveux
US20130263875A1 (en) * 2012-04-10 2013-10-10 Esschem, Inc. Curable nail enhancements

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0085370A2 (fr) * 1982-01-25 1983-08-10 Wickhen Products, Inc. Compositions pour vernis à ongles exemptes de nitrocellulose
EP0522756A1 (fr) * 1991-06-28 1993-01-13 Calgon Corporation Terpolymères ampholyte avec des propriétés de conditionnement supérieur employer dans des shampooings et d'autres produits pour les soins des cheveux
US20130263875A1 (en) * 2012-04-10 2013-10-10 Esschem, Inc. Curable nail enhancements

Also Published As

Publication number Publication date
FR3028513B1 (fr) 2016-11-25
FR3028513A1 (fr) 2016-05-20

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