EP1725545A1 - Zusammensetzung, die eine optisch aktive monomere verbindung enthält, verfahren für die anwendung der zusammensetzung, monomere verbindung, diese enthaltendes polymer, und anwendung davon - Google Patents

Zusammensetzung, die eine optisch aktive monomere verbindung enthält, verfahren für die anwendung der zusammensetzung, monomere verbindung, diese enthaltendes polymer, und anwendung davon

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Publication number
EP1725545A1
EP1725545A1 EP05732470A EP05732470A EP1725545A1 EP 1725545 A1 EP1725545 A1 EP 1725545A1 EP 05732470 A EP05732470 A EP 05732470A EP 05732470 A EP05732470 A EP 05732470A EP 1725545 A1 EP1725545 A1 EP 1725545A1
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EP
European Patent Office
Prior art keywords
group
chosen
alkyl
weight
groups
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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.)
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EP05732470A
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English (en)
French (fr)
Inventor
Timo Luukas
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LOreal SA
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LOreal SA
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Priority claimed from FR0450474A external-priority patent/FR2867471A1/fr
Priority claimed from FR0450475A external-priority patent/FR2867383B1/fr
Application filed by LOreal SA filed Critical LOreal SA
Publication of EP1725545A1 publication Critical patent/EP1725545A1/de
Withdrawn legal-status Critical Current

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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
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
    • 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
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4953—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom containing pyrimidine ring derivatives, e.g. minoxidil
    • 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
    • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
    • A61K8/585—Organosilicon compounds
    • 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
    • A61K8/73—Polysaccharides
    • A61K8/732—Starch; Amylose; Amylopectin; Derivatives thereof
    • 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
    • A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • 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
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A61K2800/30—Characterized by the absence of a particular group of ingredients
    • A61K2800/31—Anhydrous
    • 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
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/434—Luminescent, Fluorescent; Optical brighteners; Photosensitizers

Definitions

  • composition comprising a monomeric compound with optical effect, method using said composition, monomeric compound, polymer comprising it and use
  • the present invention relates to new cosmetic or pharmaceutical compositions, in particular for topical application, and in particular new makeup compositions, comprising organic polymers having specific optical properties, in particular of fluorescence.
  • the present invention also relates to new monomeric compounds exhibiting optical properties, in particular of fluorescence, as well as to polymers capable of being prepared from these compounds.
  • Cosmetic compositions and in particular makeup compositions such as loose or compact powders, foundations, blush or eyeshadows, lipsticks or nail varnishes, generally consist of a suitable vehicle. property and of one or more coloring agents intended to impart a certain color to said compositions before and / or after their application to the skin, mucous membranes, semi-mucous membranes and / or integuments such as nails, eyelashes or hair.
  • coloring agents intended to impart a certain color to said compositions before and / or after their application to the skin, mucous membranes, semi-mucous membranes and / or integuments such as nails, eyelashes or hair.
  • lacquers mineral pigments, organic pigments and pearlescent pigments.
  • the pigments and lacquers used in the make-up field are of very diverse origin and chemical nature. Their physico-chemical properties, in particular grain size, specific surface, density, etc., are therefore very different. These differences translate into variations in behavior: their ease of implementation, of dispersion in the environment; their stability to light and temperature; their mechanical properties. Mineral pigments, in particular mineral oxides are on the contrary very stable to light and to pH but give rather dull and pale colors. It is therefore necessary to introduce a large amount of it in cosmetic formulations to obtain a sufficiently saturated trait. This high percentage of mineral particles can nevertheless affect the gloss of the composition. Pearlescent pigments mean that varied but not very intense colors can be obtained, which lead to iridescent effects, but most often quite weak.
  • the subject of the invention is a cosmetic or pharmaceutical composition
  • a cosmetic or pharmaceutical composition comprising, in a physiologically acceptable medium, at least one polymer comprising at least one monomeric compound as defined below.
  • Another subject of the invention is a cosmetic method for making up or caring for keratin materials, in particular the skin of the body or of the face, lips, nails, eyelashes, eyebrows and / or hair, comprising application to said materials of such a cosmetic composition.
  • the polymers according to the invention can be in solid or liquid form, and confer remarkable optical effects on the compositions which comprise them as well as on the deposited makeup; in particular, they can provide lightening or color effects. These optical effects can advantageously be modulated as a function of the chemical nature and / or of the position of the various substituents present on the optical effect monomer used to form the polymer.
  • the group X is an oxygen
  • the monomer and the resulting polymer will be rather blue / white in color
  • the group X comprises a nitrogen atom
  • the monomer and the resulting polymer will rather be in the field of orange.
  • the polymers according to the invention can provide their good temperature, pH and light stability. It was also found that the polymers according to the invention exhibited good solubility in fatty substances, solubility which could vary and be adjusted, depending on the nature of the monomers. This good lipid solubility can also facilitate their subsequent implementation, in particular in cosmetic compositions which generally comprise an oily phase.
  • compositions according to the invention are maintained, when they comprise the polymers according to the invention.
  • the polymers according to the invention can exhibit, depending on the nature of the substituents, a wide variety of optical effects, which can range from blue / purple to orange / red, passing by yellow.
  • This makes it possible to have a range of compounds, belonging to the same chemical family, and therefore formulating in a similar manner, which offer diverse colors or remarkable optical properties; this notably facilitates the work of the formulators by allowing them to keep an architecture common to all of their compositions, whatever the polymers with optical property employed.
  • the polymers used according to the invention exhibit good fluorescence properties, and for some of them, properties of optical brightener.
  • optical brighteners have fluorescence properties; in general, the fluorescent compounds absorb in the ultraviolet and the visible, and re-emit energy by fluorescence for a wavelength between 380 nm and 830 nm; when this wavelength is between 380 nm and 480 nm, that is to say in the blue of the visible range, the compounds are then optical brighteners.
  • the polymers according to the invention have the advantage of removing makeup more easily than monomolecular optical brightening or fluorescent compounds of the prior art, such as bis (tert-butyl-1,3-benzoxazole) 2,5 -thiophene, in particular that known under the name UVITEX OB.
  • composition according to the invention therefore comprises, in a physiologically acceptable medium, in particular a cosmetically or pharmaceutically acceptable medium, at least one polymer capable of being obtained by polymerization, in particular radical) of at least one monomer of formula (I).
  • - R2 and R3, present on the same cycle or each on a different cycle represent, independently of one another, a hydrogen, a halogen, or a group of formula -XGP (II), provided that at least one of the radicals R2 and / or R3 represents a group of formula (II), in which:
  • - P is a polymerizable group chosen from one of the following formulas:
  • X represents O, NH or NR" with R "representing a radical chosen from the radicals C1-6 alkyl, C6-10 aryls, (C6-10) aryl (C1-6) alkyl or (C1) alkyl -
  • aryls C6-10
  • the alkyl and / or aryl groups possibly also being substituted by one or more groups chosen from OH, halogen, C 1-6 alkoxy and C6-10 aryloxy; and - m is 0 or 1; n is 0 or 1 and p is 0, 1 or 2.
  • R1 is a C1-C6 alkyl radical, a C6-C10 aryl radical, a (C6-C10) aryl- (C1-C6) alkyl radical or a (C1-C6) alkyl- radical (C6-C10) aryl, the alkyl and / or aryl radicals being optionally substituted by a hydroxyl, a halogen, a (C1-C6) alkoxy or a (C6-C10) aryloxy, can be known.
  • cyclic radical is understood to mean a monocyclic or polycyclic radical, which therefore presents itself in the form of one or more cycles, saturated and / or unsaturated, optionally substituted (for example cyclohexyl , cyclodecyl, benzyl or fluorenyl), but also a radical which comprises one or more of said cycles (for example p-tertbutylcyclohexyl or 4-hydroxybenzyl).
  • saturated and / or unsaturated radical is understood to mean totally saturated radicals, totally unsaturated radicals, including aromatic radicals, as well as radicals comprising one or more double and / or triple bonds, the rest of the bonds being single bonds.
  • R1 may in particular be a cyclic, linear and / or branched, saturated or unsaturated hydrocarbon radical, optionally comprising a hydrocarbon ring itself saturated or unsaturated, comprising 3 to 18, in particular 4 to 14, carbon atoms, and may comprise at least one heteroatom, in particular one or two nitrogen, oxygen or silicon atoms.
  • R1 can be a linear, branched and / or cyclic, saturated or unsaturated hydrocarbon radical, comprising 6 to 13 carbon atoms.
  • R1 can be an n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, cyclopentyl, n-hexyl, cyclohexyl, n-heptyl, n-octyl, cyclooc-tyl, decyl, cyclodecyl radical.
  • R2 is preferably a hydrogen atom, and therefore R3 is a group of formula (II).
  • X is preferably chosen from -O-, -S-, - NH- or -NR4-.
  • R4 can be an ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl radical, cyclohexyl, octyl, decyl, dodecyl, phenyl or benzyl.
  • G is chosen from saturated linear or branched divalent hydrocarbon radicals optionally comprising a saturated hydrocarbon ring, comprising in total 2 to 18, in particular 3 to 10 carbon atoms.
  • G can be chosen from the ethylene, n-propylene, isopropylene (or methyl-1 ethylene and methyl-2 ethylene), n-butylene, isobutylene, pentylene in particular n-pentylene, hexylene in particular n-hexylene, heptylene, cyclohexylene radicals.
  • the polymerizable group P is preferably chosen from one of the following formulas:
  • Another subject of the invention is a monomeric compound of formula (I) as defined below:
  • - P is a polymerizable group chosen from one of the following formulas:
  • - R ' represents H or a hydrocarbon radical, linear or branched, saturated in C1-6
  • - X' represents O, NH or NR "with R” representing a radical chosen from alkyl radicals in C1-6, aryls in C6- 10, aryl (C6-10) alkyls (C1-6) or alkyl (C1-6) aryls (C6-10), the alkyl and / or aryl groups can also be substituted by one or more groups chosen from OH, halogen , C1-6 alkoxy and C6-10 aryloxy.
  • - m is 0 or 1;
  • - n is equal to 0 or 1.
  • R1 is a C1-C6 alkyl radical, a C6-C10 aryl radical, a (C6-C10) aryl- (C1-C6) alkyl radical or a (C1-C6) alkyl- (C6-C10) radical aryl, said alkyl and / or aryl radicals being optionally substituted by a hydroxyl, a halogen, a (C1-C6) alkoxy or a (C6-C10) aryloxy.
  • Another subject of the invention is a polymer comprising at least one such monomeric compound.
  • Another object of the invention is the use of at least one such monomeric compound or of such a polymer comprising it, in a composition, to confer on said composition optical effects, in particular of fluorescence or optical brightener.
  • the new monomers, and the polymers comprising them have good optical properties and are capable of being prepared more easily than those of the prior art.
  • the polymerization is easier, in particular by the presence of a spacer group (G).
  • the polymers and the monomeric compounds according to the invention find a very particular use for conferring on a composition optical effects, in particular of fluorescence or optical brightener.
  • Some of these compounds can in particular be prepared according to the state of the art, for example according to the teaching of document EP728745, in particular the compounds for which X is N.
  • the appropriate naphthalic anhydride is present in slight excess relative to the amine, in particular at a rate of 1 to 1.5 equivalents, preferably 1, 1 equivalent, for 1 equivalent of amine.
  • the reaction can be carried out in a solvent chosen by the solvents in which the anhydride is soluble, and in particular toluene, xylene, acetic acid, NMP or ethanol; the reaction is preferably carried out at reflux of the solvent, for example at a temperature of 50-250 ° C, preferably 75-150 ° C.
  • the formed acid can be reacted with a diol, an amino alcohol or a thioalcohol.
  • R'2 is a halogen (preferably chlorine or bromine)
  • R'2 is a halogen (preferably chlorine or bromine)
  • an aromatic nucleophilic substitution for example by using a diol such as 1, 3-propane-diol or 1, 5 -propane-diol, optionally in the form of alkali metal alcoholate (sodium for example).
  • the reaction can be carried out in the absence of solvent, or in the presence of an aprotic dipolar solvent such as dichloromethane, THF (tetrahydrofuran), in particular at a temperature of 20-150 ° C.
  • the corresponding alcoholic derivative is then obtained which can then be reacted with a (meth) acryloyl halide, in particular a chloride, so as to form the corresponding (meth) acrylate.
  • a (meth) acryloyl halide in particular a chloride
  • This reaction can be carried out in the presence of a base such as triethanolamine, in a solvent such as tetrahydrofuran or dichloromethane, in particular at a temperature of -30 ° C to 100 ° C, preferably 0 to 60 ° C .
  • a base such as triethanolamine
  • a solvent such as tetrahydrofuran or dichloromethane
  • the monomeric compounds for which X is S can be prepared in a similar manner.
  • the acid formed in the first step above can be reacted with an alkali metal alcoholate of thioalcohol so as to form the alcoholic derivative according to the diagram below:
  • This derivative can then be oxidized under mild conditions so as to lead to the corresponding sulfoxide.
  • These sulfides, sulfoxides and sulfones can then be transformed to obtain the desired methacrylates or acrylates.
  • These monomeric compounds can be used as the first monomer to prepare copolymers comprising them.
  • the monomeric compounds with optical effect according to the invention can be used to prepare homopolymers or copolymers comprising only monomeric compounds with optical effect, which can then, for example, each be present in an amount of 0.5 to 99.5% by weight, in particular 5 to 95% by weight, or even 10 to 90% by weight, even better each at a rate of 30 to 70% by weight, relative to the total weight of the polymer.
  • This can in particular make it possible to prepare polymers having a wide range of optical effect (color in particular, optical brightener or other).
  • block copolymers for example diblock or triblock, comprising said monomeric compounds with optical effect according to the invention and additional comonomers as defined below.
  • the monomeric compounds according to the invention can form all or part of a block, or sequence, or even of several blocks or sequences. It is thus possible to prepare block copolymers of the type AB, ABA, BAB, ABC where A is a block comprising the monomeric compound or compounds according to the invention, optionally in admixture with additional comonomers, B and C being distinct blocks, comprising additional comonomers, alone or as a mixture, and identical or different from the comonomers present in sequence A.
  • copolymers comprising the monomeric compounds according to the invention can also be of the gradient type.
  • the monomeric compounds with an optical effect may be present in an amount of 0.01 to 70% by weight relative to the weight of the final polymer, in particular in an amount of 0.1% to 50% by weight, in particular from 0.5 to 30% by weight, or even from 1 to 20% by weight, even better from 2 to 10% by weight, the additional comonomers, alone or in mixture, representing the complement to 100% by weight.
  • copolymers according to the invention may comprise, in addition to the monomeric compound or compounds with an optical effect, at least one additional comonomer which is hydrophilic, or a mixture of such comonomers.
  • hydrophilic comonomers can be present in an amount of 1 to 99.99% by weight, especially 2-70% by weight, even better 5-50% by weight, or even 10-30% by weight, relative to the total weight of the copolymer .
  • hydrophilic monomer denotes indifferently the monomers whose homopolymers are soluble or dispersible in water, or of which an ionic form Test.
  • a homopolymer is said to be water-soluble if it forms a clear solution when it is in solution at 5% by weight in water, at 25 ° C.
  • a homopolymer is said to be water-dispersible if, at 5% by weight in water, at 25 ° C., it forms a stable suspension of fine particles, generally spherical.
  • the average size of the particles constituting said dispersion is less than 1 ⁇ m and, more generally, varies between 5 and 400 nm, preferably from 10 to 250 nm. These particle sizes are measured by light scattering.
  • a monomer will be called 'hydrophobic' if it is not hydrophilic.
  • the additional hydrophilic comonomer (s) has a Tg greater than or equal to 20 ° C., in particular greater than or equal to 50 ° C., but may possibly have a Tg less than or equal to 20 ° C.
  • copolymers according to the invention can comprise at least one additional hydrophobic comonomer, or a mixture of such comonomers.
  • hydrophobic comonomers can be present in an amount of 1 to 99.99% by weight, in particular 30-98% by weight, even better 50-95% by weight, or even 70-90% by weight, relative to the total weight of the copolymer.
  • the hydrophobic comonomer has a Tg greater than or equal to 20 ° C., in particular greater than or equal to 30 ° C., but can optionally have a Tg less than or equal to 20 ° C.
  • the Tg (or glass transition temperature) is measured according to standard ASTM D3418-97, by differential enthalpy analysis (DSC "Differential Scanning Calorimetry") on a calorimeter, over a temperature range between -100 ° C. and + 150 ° C at a heating rate of 10 ° C / min in 150 ⁇ l aluminum crucibles.
  • DSC differential enthalpy analysis
  • ethylenic hydrocarbons having 2 to 10 carbons such as ethylene, Tisoprene, or butadiene;
  • a C 3 to C 2 o aryl group such as the phenyl group, a C 4 to C 30 aralkyl group (C 1 to C 6 alkyl group) such as 2-phenylethyl, t-butylbenzyl or benzyl,
  • heterocycloalkyl group (alkyl of 1 to 4 C), such as furfurylmetyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups which may be optionally substituted by one or more substituents chosen from hydroxyl groups, atoms halogen, and C1-4 alkyl groups, linear or branched in which there is (are) optionally intercalated one or more heteroatoms chosen from O, N, S and P, said alkyl groups being able, in addition, be optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (R 4 R 5 ), where R 4 and R 5 , which are identical or different, represent a C1 to Ce alkyl group, or a phenyl group, - R 3 can also be a group - (C 2 H 4 0) m -
  • R8 R6 / H, C C CO-N 2 ⁇ R7 in which R 8 denotes H or methyl; and R 7 and R 6, which are identical or different, represent:
  • R3 may be a methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, hexyl, ethylhexyl, octyl, lauryl, isooctyl, isodecyl, dodecyl, cyo-clohexyl, t-butylcyclohexyl or stearyl group; eth
  • aralkyl group such as 2-phenylethyl, t-butylbenzyl or benzyl, - a 4 to 12-membered heterocyclic group containing one or more heteroatoms chosen from O, N, and S, the cycle being aromatic or not,
  • heterocycloalkyl group (alkyl of 1 to 4 C), such as furfurylmethyl or tetrahydrofurfurylmethyl, said cycloalkyl, aryl, aralkyl, heterocyclic or heterocycloalkyl groups which may be optionally substituted by one or more substituents chosen from hydroxyl groups, atoms of 'halogen, and C1-C4 alkyl groups, linear or branched in which is (are) optionally intercalated ⁇ ) one or more heteroatoms chosen from O, N, S and P, said alkyl groups being able, in addition, to be optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (R 4 R 5 ), where R 4 and R 5 are identical or different represent alkyl to C 6, or a phenyl group.
  • R 4 and R 5 are identical or different represent alkyl to C 6, or a phenyl group.
  • (meth) acrylamide monomers are (meth) acrylamide, N-ethyl (meth) acrylamide, N-butylacrylamide, Nt-butylacrylamide, N-isopropylacrylamide, N, N-dimethyl (meth) acrylamide, the
  • N N-dibutylacrylamide, N-octylacrylamide, N-dodecylacryiamide, Tundecylacrylamide, and N (2-hydroxypropylmethacrylamide).
  • alkyl group a linear or branched alkyl group, from 1 to 18 carbon atoms, in which there are optionally intercalated one or more heteroatoms chosen from O, N, S and P; said alkyl group being able, in addition, to be optionally substituted by one or more substituents chosen from hydroxyl groups, halogen atoms (Cl, Br, I and F), and Si groups (R4R5), where R4 and R 5, which are identical or different, represent a C1 to alkyl group This or a phenyl group;
  • a C 3 to C 12 cycloalkyl group such as isobornyl, cyclohexane, a C 3 to C 2 o aryl group such as phenyl,
  • aralkyl group such as 2-phenylethyl; benzyl,
  • vinyl monomers are vinylcyclohexane, and styrene.
  • vinyl esters are vinyl acetate vinyl propionate, vinyl butyrate, vinyl ethyl hexhexanoate, vinyl neononanoate and vinyl neododecanoate.
  • vinyl ethers mention may be made of vinyl methyl ether, vinyl ethyl ether and vinyl isobutyl ether.
  • silicone (meth) acrylic, (meth) acrylamides or vinyl monomers such as methacryloxypropyltris (trimethylsiloxy) silane or Tacryloxypropylpoly-dimethylsiloxane.
  • ethylenically unsaturated monomers comprising at least one carboxylic, phosphoric or sulphonic acid or anhydride function, such as, for example, acrylic acid, methacrylic acid, crotonic acid, maleic anhydride , Itaconic acid, fumaric acid, maleic acid, acrylamide-dopropanesulfonic acid, vinylbenzoic acid, vinylphosphoric acid and the salts thereof, - (viii) ethylenically unsaturated monomers comprising at least one tertiary amine function such as 2-vinylpyridine, 4-vinylpyridine, dimethylaminoethyl methacrylate, diethylaminoethyl methacrylate, dimethylaminopropyl methacrylamide and the salts thereof.
  • tertiary amine function such as 2-vinylpyridine, 4-vinylpyridine, dimethylaminoethyl methacrylate, diethylaminoethyl me
  • the salts can be formed by neutralization of the anionic groups using a mineral base, such as LiOH, NaOH, KOH, Ca (OH) 2 , NH 4 OH or Zn (OH) 2 ; or with an organic base such as a primary, secondary or tertiary alkylamine, in particular triethylamine or butylamine.
  • a mineral base such as LiOH, NaOH, KOH, Ca (OH) 2 , NH 4 OH or Zn (OH) 2
  • an organic base such as a primary, secondary or tertiary alkylamine, in particular triethylamine or butylamine.
  • This primary, secondary or tertiary alkylamine can comprise one or more nitrogen and / or oxygen atoms and can therefore comprise, for example, one or more alcohol functions; mention may especially be made of Tamino-2-methyl-2-propanol, triethanolamine and dimethylamino-2-propanol. Mention may also be made of lysine or 3-
  • mineral acids such as sulfuric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid, boric acid.
  • the additional comonomer (s) may be present in an amount from 30% to 99.99% by weight relative to the weight of the final polymer, in particular in an amount from 50% to 99.9% by weight, in particular from 70% to 99.5% by weight, even from 80 to 99% by weight, even better from 90 to 98% by weight.
  • the additional comonomers are chosen more particularly from, alone or as a mixture, C1-C18 alkyl (meth) acrylates or C3-C12 cycloalkyl, and in particular from methyl tacrylate, methyl methacrylate, isobornyl tacrylate , isobornyl methacrylate, Isobutyl tacrylate, isobutyl methacrylate, ethyl-2-hexyl tacrylate, ethyl-2-hexyl methacrylate, dodecyl tacrylate, dodecyl methacrylate, stearyl tacrylate, stearyl methacrylate, trifluoroethylacrylate, trifluoroethyl methacrylate.
  • acrylic acid methacrylic acid, methacryloxypropyltris (trimethylsiloxy) silane, Tacryloxypropyltris (trimethylsiloxy) silane, Tacryloxypropylpolydimethylsiloxane and methacryloxypropylpolydimethylsiloxane.
  • Said polymers can be prepared according to methods known to those skilled in the art, in particular by radical polymerization; controlled radical polymerization, for example with xanthans, dithiocarbarnates or dithioesters; by polymerization using nitro type precursors: xides; by radical atom transfer polymerization (ATRP); by group transfer polymerization.
  • the polymerization can be carried out in the presence of a polymerization initiator, which can be a radial initiator, and in particular which can be chosen from organic peroxide compounds such as dilauroyl peroxide, dibenzoyl peroxide, ter-butyl peroxy-2-ethylhexanoate; or among diazotized compounds such as Tazobisisobutyronitri le or Tazobisdimethylvaleronitrile.
  • the reaction can also be initiated using photoinitiators or by UV-type radiation, by neutrons or by plasma.
  • the monomeric compounds with an optical effect preferably have an absorption wavelength between 200 and 500 nm, in particular between 220 and 450 nm, or even between 240 and 440 nm. They preferably have an emission wavelength between 350 and 700 nm, in particular between 390 and 650 nm, or even between 400 and 600 nm.
  • the weight average molecular mass (Mw) of the copolymers according to the invention is preferably between 5000 and 600,000 g / mol, in particular between 10,000 and 300,000 g / mol, and even better between 20,000 and 150,000 g / mol .
  • the average molecular weights in weight (Mw) and in number (Mn) are determined by gel permeation liquid chromatography (GPC), eluent THF, calibration curve established with linear polystyrene standards, refractometric detector).
  • the polymers according to the invention can be present, alone or as a mixture, in the compositions according to the invention in an amount of 0.01 to 60% by weight, preferably 0.1 to 50% by weight, in particular 1 to 25% by weight, or even 3 to 15% by weight, and even better 5 to 12% by weight, relative to the total weight of the composition.
  • compositions according to the invention comprise, in addition to said polymers, a physiologically acceptable medium, in particular cosmetically, dermatologically or pharmaceutically acceptable, that is to say a medium compatible with keratin materials such as the skin of the face or body, hair, eyelashes, eyebrows and nails.
  • the composition may thus comprise a hydrophilic medium comprising water or a mixture of water and organic solvent (s) hydrophilic (s) such as alcohols and in particular linear or branched lower monoalcohols having from 2 to 5 atoms. carbon such as tethanol, tisopropanol or n-propanol, and polyols such as glycerin, diglycerin, propylene glycol, sorbitol, pentylene glycol, and polyethylene glycols, or alternatively C 2 ethers and C aldehydes 2 -C 4 hydrophilic.
  • organic solvent s
  • hydrophilic such as alcohols and in particular linear or branched lower monoalcohols having from 2 to 5 atoms.
  • carbon such as tethanol, tisopropanol or n-propanol
  • polyols such as glycerin, diglycerin, propylene glycol, sorbitol, pentylene glycol, and poly
  • the water or the mixture of water and hydrophilic organic solvents may be present in the composition according to the invention in a content ranging from 0.1% to 99% by weight, relative to the total weight of the composition, and preferably 10% to 80% by weight.
  • the composition can also be anhydrous.
  • the composition may also comprise a fatty phase which may comprise fatty substances liquid at room temperature (25 ° C. in general) and / or fatty substances solid at ambient temperature such as waxes,> pasty fatty substances, gums and their mixtures. These fatty substances can be of animal, vegetable, mineral or synthetic origin. This fatty phase can, in addition, contain lipophilic organic solvents.
  • oils As fatty substances liquid at room temperature, often called oils, which can be used in the invention, mention may be made of: hydrocarbon oils of animal origin such as perhydrosqualene; vegetable hydrocarbon oils such as liquid triglycerides of fatty acids with 4 to 10 carbon atoms such as heptanoic or octanoic acid triglycerides, or even sunflower, corn, soybean, grape seed, sesame oils, apricot, macadamia, castor, avocado, caprylic / capric acid triglycerides, jojoba oil, shea butter; linear or branched hydrocarbons, of mineral or synthetic origin such as paraffin oils and their derivatives, petroleum jelly, polydecenes, hydrogenated polyisobutene such as parieam; synthetic esters and ethers, in particular of fatty acids, for example Purcellin oil, isopropyl myristate, ethyl-2-hexyl palmitate, octyl-2-dode
  • composition according to the invention can also comprise one or more organic solvents, physiologically acceptable. These solvents can generally be present in a content ranging from 0.1 to 90%, preferably from 0.5 to 85%, more preferably from 10 to 80% by weight, relative to the total weight of the composition, and better still from 30 to 50%.
  • ketones which are liquid at room temperature such as methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, tisophorone, cyclohexanone, acetone
  • propylene glycol ethers which are liquid at room temperature such as propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, dipropylene glycol mono n-butyl ether
  • short chain esters (having 3 to 8 carbon atoms in total) such as ethyl acetate, methyl acetate, propyl acetate, n-butyl acetate, isopentyl acetate
  • ethers liquid at 25 ° C such as diethyl ether, dimethyl ether or dichlorodieth ylether
  • alkanes liquid at 25 ° C such as decane, Theptane, dodecan
  • wax within the meaning of the present invention is meant a lipophilic compound, solid at room temperature (25 ° C.), with reversible solid / liquid state change, having a melting point greater than or equal to 25 ° C. up to 'at 120 ° C.
  • melting By bringing the wax to the liquid state (melting), it is possible to make it miscible with the oils possibly present and to form a homogeneous mixture microscopically, but by bringing the temperature of the mixture to room temperature, a recrystallization is obtained. wax in the oils of the mixture.
  • the melting point of the wax can be measured using a differential scanning calorimeter (D.S.C.), for example the calorimeter sold under the name DSC 30 by the company METLER.
  • D.S.C. differential scanning calorimeter
  • the waxes can be hydrocarbon, fluorinated and / or silicone and be of vegetable, mineral, animal and / or synthetic origin. In particular, the waxes present a melting point above 30 ° C and better still above 45 ° C.
  • wax which can be used in the composition of the invention mention may be made of beeswax, Carnauba or Candellila wax, paraffin, microcrystalline waxes, ceresin or Tozokerite; synthetic waxes such as polyethylene or Fischer Tropsch waxes, silicone waxes such as alkyl or alkoxy-dimethicone having from 16 to 45 carbon atoms.
  • the gums are generally high molecular weight polydimethylsiloxanes (PDMS) or cellulose gums or polysaccharides and the pasty bodies are generally hydrocarbon compounds such as lanolines and their derivatives or PDMS.
  • PDMS polydimethylsiloxanes
  • cellulose gums or polysaccharides and the pasty bodies are generally hydrocarbon compounds such as lanolines and their derivatives or PDMS.
  • the composition may contain from 0.1 to 50% by weight of waxes, relative to the total weight of the composition and better still from 1 to 30% by weight.
  • composition according to the invention can also comprise, in a particular phase, pigments and / or nacres and / or fillers usually used in cosmetic compositions.
  • the composition can also comprise other coloring materials chosen from water-soluble dyes and / or liposoluble dyes well known to those skilled in the art.
  • pigments should be understood to mean particles of any shape, white or colored, mineral or organic, insoluble in the physiological medium, intended to color the composition.
  • fillers it is necessary to understand colorless or white, mineral or synthetic particles, lamellar or non-lamellar, intended to give body or rigidity to the composition, and / or softness, mattness and uniformity. makeup.
  • nacres it is necessary to understand particles of any iridescent shape, in particular produced by certain molluscs in their shell or else synthesized.
  • the pigments can be present in the composition in an amount of 0.01 to 25% by weight of the final composition, and preferably in an amount of 3 to 10% by weight. They can be white or colored, mineral or organic. Mention may be made of titanium, zirconium or cerium oxides, as well as zinc, iron or chromium oxides, ferric blue, chromium hydrate, carbon black, ultramarines (aluminosilicate polysulphides) , manganese pyrophosphate and certain metallic powders such as those of silver or aluminum. Mention may also be made of the D&C pigments and the lacquers commonly used to give the lips and the skin a make-up effect, which are calcium, barium, aluminum, strontium or zirconium salts.
  • the nacres can be present in the composition in an amount of 0.01 to 20% by weight, preferably at a rate of the order of 3 to 10% by weight.
  • liposoluble or water-soluble which may be present in the composition, alone or as a mixture, at a rate of 0.001 to 15% by weight, preferably 0.01 to 5% by weight and in particular from 0.1 to 2% by weight, relative to the total weight of the composition, there may be mentioned the disodium salt of culvert, the sodium salt of alizarin green, quinoline yellow, the trisodium salt of amaranth, the disodium salt of tartrazine, monosodium salt of rhodamine, disodium salt of fuchsin, xanthophyll, methylene blue, cochineal carmine, halo-acid, azo, anthraquinone dyes, copper or iron sulfate, Sudan brown , Sudan red and annatto, as well as beet juice and carotene.
  • the disodium salt of culvert the sodium salt of alizarin green, quinoline yellow
  • the trisodium salt of amaranth the disodium
  • composition according to the invention may also further comprise one or more fillers, in particular in a content ranging from 0.01% to 50% by weight, relative to the total weight of the composition, preferably ranging from 0.02% at 30% by weight.
  • the fillers can be mineral or organic in any form, platelet, spherical or oblong.
  • talc Mention may be made of talc, mica, silica, kaolin, polyamide (Nylon®), poly- ⁇ -alanine and polyethylene powders, powders of tetrafluoroethylene polymers (Teflon®), lauroyl-lysine, starch, boron nitride, hollow polymeric microspheres such as those of polyvinylidene chloride / acrylonitrile such as TExpancel® (Nobel Industry), of acrylic acid copolymers (Polytrap® of the company Dow Corning) and the microbeads silicone resin (Tospearls® from Toshiba, for example), elastomeric polyorganosiloxane particles, precipitated calcium carbonate, carbonate and magnesium hydrocarbon, Hydroxyapatite, hollow silica microspheres (Silica Beads® from Maprecos), glass or ceramic microcapsules, metallic soaps derived from ayani organic carboxylic acids: from 8 to 22 carbon atoms,
  • the composition may further comprise an additional polymer such as a film-forming polymer.
  • film-forming polymer means a polymer capable of forming on its own or in the presence of an ageni: film-forming aid, a continuous and adherent film on a support, in particular: on keratin materials.
  • film-forming polymers capable of being used in the composition of the present invention mention may be made of synthetic polymers, of radical type or of polycondensate type, polymers of natural origin and their mixtures, in particular acrylic polymers, polyurethanes , polyesters, polyamides, polyureas, cellulose polymers such as nitrocellulose.
  • composition according to the invention can also comprise ingredients commonly used in cosmetics, such as vitamins, thickeners, gelling agents, trace elements, softeners, sequestering agents, perfumes, alkalizing or acidifying agents, preservatives, sunscreens, surfactants, antioxidants, hair loss agents, dandruff agents, propellants, ceramides, or mixtures thereof.
  • ingredients commonly used in cosmetics such as vitamins, thickeners, gelling agents, trace elements, softeners, sequestering agents, perfumes, alkalizing or acidifying agents, preservatives, sunscreens, surfactants, antioxidants, hair loss agents, dandruff agents, propellants, ceramides, or mixtures thereof.
  • ingredients commonly used in cosmetics such as vitamins, thickeners, gelling agents, trace elements, softeners, sequestering agents, perfumes, alkalizing or acidifying agents, preservatives, sunscreens, surfactants, antioxidants, hair loss agents, dandruff agents, propellants, ceramides,
  • the composition according to the invention can be in the form of a suspension, a dispersion in particular of oil in water thanks to vesicles; an oily solution possibly thickened or even gelled; an oil-in-water, water-in-oil, or multiple emulsion; a gel or foam; an oily or emulsified gel; a dispersion of vesicles, in particular lipid vesicles; a biphasic or multiphase lotion; a spray; loose, compact or poured powder; an anhydrous paste.
  • This composition may have the appearance of a lotion, a cream, an ointment, a flexible paste, an ointment, a cast or molded solid and in particular in stick or in a cup, or alternatively of compacted solid.
  • the cosmetic composition according to the invention may be in the form of a product for caring for and / or making up the skin of the body or of the face, lips, nails, eyelashes, eyebrows and / or hair, a sun or self-tanning product, a hair product for caring for, treating, shaping, making up or coloring hair.
  • a makeup composition in particular a product for the complexion such as a foundation, a blush or an eyeshadow; a lip product such as lipstick or lip care; a concealer; a blush, a mascara, an eyeliner; an eyebrow makeup product, a lip or eye pencil; a nail product such as nail polish or nail care; a body makeup product; a hair makeup product (mascara or hair spray).
  • a composition for protecting or caring for the skin of the face, neck, hands or body in particular an anti-wrinkle composition, a hydrating or treating composition; an anti-sun or artificial tanning composition.
  • It can also be in the form of a hair product, in particular for coloring, maintaining the hairstyle, shaping the hair, caring for, treating or cleaning the hair, such as shampoos, gels, styling lotions, brushing lotions, fixing and styling compositions such as lacquers or spray.
  • a hair product in particular for coloring, maintaining the hairstyle, shaping the hair, caring for, treating or cleaning the hair, such as shampoos, gels, styling lotions, brushing lotions, fixing and styling compositions such as lacquers or spray.
  • the subject of the invention is also a cosmetic method for making up or caring for keratin materials, in particular the skin of the body or of the face, lips, nails, eyelashes, eyebrows and / or hair, comprising the application on said materials of a cosmetic composition as defined above.
  • Wavelength measurement method emission and absorption
  • Wavelength measurement is performed using a Varian Cary fluorimeter
  • this measurement is carried out as follows: 20 mg of product are placed in a 50 ml cylinder. In order to dissolve the product, said cylinder is made up to 50 ml, using an appropriate solvent, for example dichloromethane (DCM), chloroform or dimethylsulfoxide (DMSO). The resulting solution is mixed and 250 microliters are taken, which is placed in a 50 ml cylinder, then which is again made up with the solvent to 50 ml. The whole is mixed and one takes a sample of the solution which is placed in a closed tank, made of quartz and 10 mm thick, which is then placed in the measuring chamber.
  • DCM dichloromethane
  • DMSO dimethylsulfoxide
  • a random copolymer is prepared comprising a monomer according to the invention.
  • Trigonox 21 S t-butyl peroxy-2-ethylhexanoate
  • the reaction mixture is heated to 90 ° C; stirring and heating are continued for 6 hours and then cooled to room temperature.
  • the resulting polymer is purified by precipitation.
  • a statistical polymer is obtained comprising (% by weight): 78% isobornyl acrylate, 20% ethylhexyl acrylate and 2% of monomer according to the invention.
  • a homopolymer is prepared from a monomer according to the invention
  • a random copolymer comprising a monomer according to the invention.
  • 20 g of isododecane, then 38.25 g of isobornyl acrylate and 10.0 g of ethylhexyl acrylate are introduced into a reactor, under argon, equipped with a condenser and stirring.
  • Trigonox 21 S t-butyl peroxy-2-ethylhexanoate
  • a statistical polymer comprising (% by weight): 76.5% of isobornyl acrylate, 20% ethylhexyl acrylate and 3.5% of monomer according to the invention.
  • a statistical copolymer comprising a monomer according to the invention.
  • 20 g of isododecane are introduced into a reactor, under argon, equipped with a condenser and stirring, followed by 39.75 g of isobornyl acrylate and 10.0 g of ethylhexyl acrylate.
  • the mixture is mixed and a mixture consisting of 0.25 N-hexyl-1,8-naphthalimide-4-oxypropane acrylate (monomer of Example 1) in 20.0 g of toluene is added.
  • Trigonox 21 S t-butyl peroxy-2-ethylhexanoate
  • the reaction mixture is heated to 90 ° C; stirring and heating are continued for 6 hours and then cooled to room temperature.
  • the resulting polymer is purified by precipitation.
  • a statistical polymer is obtained comprising (% by weight): 79.5% of isobornyl acrylate, 20% ethylhexyl acrylate and 0.5% of monomer according to the invention.
  • a statistical copolymer comprising a monomer according to the invention.
  • 20 g of isododecane are introduced, then 37 ′, 0 g of isobornyl acrylate and 10.0 g of ethylhexyl acrylate.
  • the mixture is mixed and a mixture consisting of 3.0 g of N-hexyl-1,8-naphthalimide-4-oxypropane acrylate (monomer of Example 1) in 20.0 g of toluene is added.
  • Trigonox 21 S t-butyl peroxy-2-ethylhexanoate
  • a statistical polymer comprising (% by weight): 74% isobornyl acrylate, 20% ethylhexyl acrylate and 6% of monomer according to the invention.
  • a random copolymer comprising a monomer according to the invention.
  • 20 g of isododecane are translated, then 35.0 g of isobornyl acrylate and 10.0 g of ethylhexyl acrylate .
  • the mixture is mixed and a mixture consisting of 5.0 of N-hexyl-1,8-naphthalimide-4-oxypropane acrylate (monomer of Example 1) in 20.0 g of toluene is added.
  • Trigonox 21 S t-butyl peroxy-2-ethylhexanoate
  • a statistical polymer comprising (% by weight): 70% isobornyl acrylate, 20% ethylhexyl acrylate and 10% of monomer according to the invention.
  • a random copolymer comprising a monomer according to the invention.
  • a mixture consisting of 15 g of N-hexyl-1,8-naphthalimide-4-oxypropane acrylate (monomer of Example 1) in 55 g of toluene, in the presence of 0.5 g of Trigonox 21 S (t-butyl peroxy-2-ethylhexanoate).
  • Trigonox 21 S t-butyl peroxy-2-ethylhexanoate
  • a homogeneous solution is obtained, to which 20 g of isobutyl methacrylate and 15 g of isobutyl acrylate, diluted in 5 g of toluene, are added.
  • the reaction mixture is heated to 90 ° C; stirring and heating are continued for 6 hours and then cooled to room temperature.
  • a 50% solution of dry matter, of polymer in Tisododecane is obtained.
  • a random polymer is obtained comprising (% by weight): 40% isobutyl methacrylate, 30% isobutyl acrylate and 30% monomer according to the invention.
  • the polymer has a weight-average mass (Mw) of 63,000 and a number-average mass (Mn) of 16,600, ie a polydispersity index Ip of 3.8.
  • a random copolymer comprising a monomer according to the invention.
  • a mixture consisting of 15 g of N-hexyl-1,8-naphthalimide-4-oxypropane acrylate (monomer of Example 1) is introduced into a reactor, under argon, equipped with a condenser and stirring. ) in 55 g of toluene, in the presence of 0.5 g of Trigonox 21 S (t-butyl peroxy-2-ethylhexanoate).
  • Trigonox 21 S t-butyl peroxy-2-ethylhexanoate.
  • a homogeneous solution is obtained, to which 10 g of isobutyl methacrylate and 7.5 g of isobutyl acrylate, diluted in 5 g of toluene, are added.
  • a statistical polymer comprising (% by weight): 31% of isobutyl methacrylate, 23% of isobutyl acrylate and 46% of monomer according to the invention.
  • a random copolymer comprising a monomer according to the invention.
  • a mixture consisting of 6 g of INI-hexyl-1,8-naphthalimide-4-oxypropane acrylate (monomer of Example 1) in 10 g of toluene.
  • a homogeneous solution is obtained to which 14 g of ethyl-2-hexyl acrylate, 0.4 g of Trigonox 21 S (t-butyl peroxy-2-ethylhexanoate) and 15 g of isododecane are added.
  • the reaction mixture is heated to 90 ° C; stirring and heating are continued for 7 hours and then cooled to room temperature.
  • the resulting polymer is purified by precipitation.
  • a statistical polymer comprising (% by weight): 70% of ethyl acrylate -2-hexyl and 30% of monomer according to the invention.
  • the polymer has a weight average mass (Mw) of 29,100 and a number average weight (Mn) of 8,300, ie a polydispersity index Ip of 3.5.
  • An anhydrous foundation comprising (% by weight): - polyethylene wax 12%
  • the waxes are melted then, when everything is clear, the phenyl trimethionone is added with stirring, and the silicone oils; the microspheres, Tisododecane and the polymer are then added. The mixture is homogenized for 15 minutes and then the resulting composition is poured in and allowed to cool. An anhydrous foundation is obtained.

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EP05732470A 2004-03-09 2005-02-28 Zusammensetzung, die eine optisch aktive monomere verbindung enthält, verfahren für die anwendung der zusammensetzung, monomere verbindung, diese enthaltendes polymer, und anwendung davon Withdrawn EP1725545A1 (de)

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FR0450474A FR2867471A1 (fr) 2004-03-09 2004-03-09 Composes monomeriques possedant des proprietes optiques, polymeres les comprenant et utilisation
FR0450475A FR2867383B1 (fr) 2004-03-09 2004-03-09 Composition comprenant un compose monomerique a effet optique et procede employant ladite composition
US56061704P 2004-04-09 2004-04-09
US56070504P 2004-04-09 2004-04-09
PCT/FR2005/000475 WO2005097776A1 (fr) 2004-03-09 2005-02-28 Composition comprenant un compose monomerique a effet optique, proce­de employant ladite composition, compose monomerique, polymere le com­prenant et utilisation

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FR2871470B1 (fr) * 2004-06-11 2007-01-12 Oreal Copolymere a gradient, composition et procede cosmetique de maquillage ou de soin
FR2927077B1 (fr) * 2008-01-31 2012-05-25 Commissariat Energie Atomique Derives du 1,8-naphtalimide en tant qu'agents de scintillation notamment pour la discrimination entre les neutrons rapides et les rayons gamma
JP5515430B2 (ja) * 2009-06-01 2014-06-11 日油株式会社 共重合体および毛髪用化粧料
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JP6497676B2 (ja) * 2015-03-12 2019-04-10 シプロ化成株式会社 ベンゾトリアゾール誘導体化合物及びそれらの重合体

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US20070189987A1 (en) 2007-08-16
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KR20060105056A (ko) 2006-10-09

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