EP1207843A2 - Preparations cosmetiques et/ou pharmaceutiques renfermant des polymerisats contenant des polysiloxanes et leur application - Google Patents

Preparations cosmetiques et/ou pharmaceutiques renfermant des polymerisats contenant des polysiloxanes et leur application

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Publication number
EP1207843A2
EP1207843A2 EP00962362A EP00962362A EP1207843A2 EP 1207843 A2 EP1207843 A2 EP 1207843A2 EP 00962362 A EP00962362 A EP 00962362A EP 00962362 A EP00962362 A EP 00962362A EP 1207843 A2 EP1207843 A2 EP 1207843A2
Authority
EP
European Patent Office
Prior art keywords
preparations
weight
acrylate
acid
integers
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.)
Withdrawn
Application number
EP00962362A
Other languages
German (de)
English (en)
Inventor
Wilma M. Dausch
Jacqueline Engesser
Helmut Witteler
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.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1207843A2 publication Critical patent/EP1207843A2/fr
Withdrawn legal-status Critical Current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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
    • A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/24—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients to enhance the sticking of the active ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
    • 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
    • A61K8/8147—Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; 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
    • A61K8/8141—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
    • 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)
    • 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)
    • A61K8/8182—Copolymers of 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
    • A61K8/87—Polyurethanes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
    • A61Q1/02—Preparations containing skin colorants, e.g. pigments
    • A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
    • 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
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes

Definitions

  • the present invention relates to cosmetic and / or pharmaceutical preparations containing water-soluble or water-dispersible polysiloxane-containing polymers and further polymers and / or UV light protection filters. It further relates to the use of these preparations and that of the polysiloxane-containing polymers.
  • Polymers with film-forming properties are used for cosmetic and / or pharmaceutical preparations and are particularly suitable as additives for hair and skin cosmetics.
  • polymers can have a particular effect.
  • the polymers can contribute, among other things, to moisturizing and conditioning the skin and to improving the feeling on the skin.
  • the skin becomes smoother and more supple.
  • polymers are used to strengthen, improve the structure and shape of the hair. They increase the combability and improve the feel of the hair.
  • These hair treatment compositions generally contain a solution of the film former in an alcohol or a mixture of alcohol and water.
  • hair treatment agents One requirement for hair treatment agents is to give the hair shine, flexibility and a natural, pleasant feel.
  • EP-A 408 311 describes graft copolymers with a carbon main chain, to which polydimethylsiloxane side chains are bound. Only polymers are described which are produced with the aid of unsaturated monomers which carry a polysiloxane chain. Graft copolymers with a carbon backbone to which polydimethylsiloxane side chains are attached are not described.
  • EP-A 670 342 describes the use of alkoxylated silicones in hair care products.
  • the use of polymers of unsaturated compounds in hair care products is not disclosed.
  • the use of alkoxylated silicones as an additive to commercially available hair setting polymers improves their grip, but at the same time leads to a reduced setting effect.
  • EP-A 412 704 and EP-A 412 707 describe polysiloxane groups in the form of macromonomers with molecular weights from 1000 to 50,000, which are polymerized with conventional hydrophobic and hydrophilic monomers. The synthesis of these monomers is extremely complex. Unreacted macromonomers and their unreactive impurities can hardly be separated from the polymers due to their high molecular weight. They represent a toxicological and allergenic risk. In addition, in order to achieve a good effect, the copolymers obtained can often only be formulated in combination with other polymers, carriers and other auxiliaries, such as the abovementioned. Teach patents.
  • WO 99/04750 describes polymers which are obtainable by free-radical polymerization of ethylenically unsaturated monomers in the presence of polyalkylene oxide-containing silicone derivatives.
  • One object of the invention relates to the use of a polymer which can be obtained by free-radical polymerization of a monomer mixture
  • Solid pharmaceutical dosage forms such as tablets, capsules, pellets, granules, crystals etc. are coated for very different reasons, i.e. covered with a film.
  • a bad smell or taste can be masked 5 and the swallowability can be improved.
  • the stability of the active ingredient can be increased by the coating, since less water vapor and oxygen reach the inside of the tablet.
  • the dosage forms look better and can be better distinguished by incorporating dyes.
  • the release rate of the active ingredient can in particular be set by the film coating.
  • the disintegration of the tablet and the release of the active ingredient from the dosage form should, if possible, not be influenced by the coating, so the film coating must dissolve quickly in the gastric juice. Q In addition, he must have good film properties. The tensile strength and the elongation at break should be high so that the film coating can withstand mechanical influences such as those that occur during pharmaceutical processing - in particular packaging - and also during shipping or storage. 5
  • HPMC hydroxypropylmethyl cellulose
  • the viscosity may have a certain limit (between 150 and 250 mPas), which depends on the type of spray nozzle and the device, not exceed. For this reason, only relatively low concentrations of film formers can be used in the case of HPMC.
  • hydroxypropylmethyl cellulose has other disadvantages, among others. in wetting behavior, in the adhesiveness on the tablet surface, in the pigment binding capacity, in the mechanical properties of the films, in the hygroscopicity and in the permeability to water vapor and oxygen, in the dissolution rate and in the disintegration time difference between film tablets and core.
  • the low elasticity of the films made of hydroxypropylmethyl cellulose often leads to the film tablets tearing open when stored in a moist state due to the swelling of the core.
  • the use of plasticizers also does not result in any noteworthy improvements to this problem. Rather, it can lead to sticky films and changes in tablet properties due to migration.
  • Oral dosage forms with a drug release over a longer period of time with the aim of prolonging the action of the active component are becoming increasingly important. It is associated with improved patient compliance through a reduced intake frequency, a reduction in side effects by avoiding plasma peaks, more uniform blood levels of the drug and the avoidance of local irritation.
  • the control and prolongation of the release can be achieved by embedding the drug in matrices.
  • ion exchange resins and therapeutic systems e.g. OROS
  • Binders are used in pharmaceutical dosage forms to increase processability and mechanical strength. They are usually used in tablets, granules and pellets and lead to improved flowability, higher breaking strength and lower friability.
  • binders currently used such as maltodextrin or polyvinylpyrrolidone, often lead to unsatisfactory breaking strength and friability.
  • Other binders such as starch paste and hydroxypropylmethyl cellulose (HPMC) can only be used in low concentrations due to their high viscosity.
  • film-forming auxiliaries are used in solutions and sprays that are applied to the skin or mucous membrane or that are systemically supplied to the body. Examples of this are preparations for wound treatment, spray dressings but also preparations for application to intact skin or mucous membranes.
  • the skin is protected by a film and the active ingredients can penetrate or through the skin.
  • An object of the present invention was to provide water-soluble or water-dispersible polymers as coating agents, binders and / or film formers in pharmaceutical preparations which do not have the disadvantages mentioned above. It has surprisingly been found that the polymers according to the invention are suitable for use in pharmaceutical preparations.
  • the polymers according to the invention can be used in a large number of pharmaceutical preparations.
  • film-coated tablets for example, film-coated tablets, film microtablets, coated tablets, coated lozenges, 5 capsules, crystals, granules or pellets can be mentioned as coated preparations.
  • Preparations containing binders are, for example, tablets, microtablets, cores, granules or pellets.
  • the polymers according to the invention can be used to produce solutions and sprays which, when applied to the skin or mucous membrane, form a film. Due to the enormous stretchability and adhesiveness, the films adhere to the skin or mucous membrane for a long time. The application frequency can be reduced and the wearing comfort is increased. Examples of this are spray dressings for wounds, disinfection sprays, solutions with Mycostica, mouth sprays or solutions with antibiotics etc. Because of the flexibility, use in transdermal therapeutic systems is also advantageous.
  • the polymers used according to the invention slightly wet lipophilic surfaces and have excellent protective colloid properties. Incorporated in suspensions and emulsions 5, they attach themselves to the particles of the disperse phase and stabilize them. They can therefore be used as wetting aids and stabilizers in disperse systems.
  • the polymers used according to the invention can optionally also be processed in combination with other auxiliaries together with active ingredients to give polymer-active ingredient melts, which are either extruded and calendered into medicinal substances or are broken down into granules or powders after extrusion and are only subsequently processed into medicinal forms, for example to Tablets are pressed.
  • the polymers according to the invention incorporate the properties already listed above into the preparations.
  • the polymers according to the invention can excellently perform the following functions:
  • Dispersing aid for the formulation of active ingredients in retardant formulations, active ingredients to formulate the active ingredient in retardants ,
  • the polymers according to the invention which are insoluble or only slightly soluble in water, can also be used as retardation polymers and as adhesives for active ingredient plasters.
  • the polymers When used for the manufacture of suppositories and vaginal globules, the polymers ensure on the one hand the flexibility of the dosage form and on the other hand promote disintegration and the dissolution of the active ingredient, and they line the mucous membrane with an active ingredient-containing film which increases absorption.
  • Tablets swell to different extents depending on the auxiliary and active ingredients used, the storage time and the storage conditions, such as temperature and humidity.
  • a rigid film coating suffers cracks when the core swells. That is why the elasticity of film formers is an important factor.
  • the polymers can be applied to the active substance-containing core in pure form or together with the customary auxiliaries.
  • Typical auxiliaries are, for example, color pigments for coloring, white pigments, such as titanium dioxide, for increasing opacity, talc and silicon dioxide as anti-adhesive, polyethylene glycols, glycerol, propylene glycol, triacetin, triethyl citrate as plasticizers and various surface-active substances, such as sodium lauryl sulfate, Polysorbate 80, Pluronics and Cremophore, to improve the wetting behavior.
  • the substances mentioned by way of example do not represent any limitation. All additives known to be suitable for gastric juice-soluble film coatings can be used.
  • the coating process can be used as the coating process.
  • the polymers according to the invention can also be used for the coating of other pharmaceutical preparations, such as granules, pellets, crystals or capsules.
  • the new coating compositions are applied in a thickness of 5 to 200 ⁇ m, preferably 10 to 100 ⁇ m.
  • wet and dry binders When used as a binder, a distinction is made between wet and dry binders depending on the processing method. The latter are among others used for direct tableting and for dry granulation or compacting.
  • the binder is mixed with the active ingredient and, if appropriate, further auxiliaries and then directly tableted or granulated or compacted.
  • the active ingredient / auxiliary mixture is moistened with a solution of the binder in water or an organic solvent, the moist mass is passed through a sieve and then dried. Humidification and drying can also take place in parallel, e.g. in fluidized bed granulation.
  • the binder in solution should be of low viscosity, since viscous solutions lead to inhomogeneous granules.
  • a binder should lead to uniform, hard, abrasion-resistant granules or tablets.
  • the breaking strength is of particular importance, since many active ingredients are difficult to compress and thus tablets with inadequate mechanical stability result.
  • the disintegration of the pharmaceutical forms and the rate of release of the active substances should not be significantly adversely affected by the binder.
  • binders are, for example, polyvinyl pyrrolidone, vinyl acetate-vinyl pyrrolidone copolymers, gelatin, starch paste, maltodextrins, hydroxyalkylated or carboxy- alkylated cellulose derivatives such as hydroxypropylmethyl cellulose, methyl cellulose, sodium carboxymethyl cellulose and natural types of gum such as gum arabic, pectin or alginate.
  • binders have a high viscosity in solution and are difficult to process. Due to the high viscosity, the powder particles to be granulated are poorly and unevenly wetted, resulting in insufficient granule strength and an unfavorable particle size distribution.
  • binders are also hygroscopic and swell when water is absorbed. This can dramatically change the properties of the granules and tablets.
  • the polymers according to the invention have excellent binder effects and, in addition, do not significantly influence the disintegration in concentration ranges from 0.5 to 20% by weight, preferably 1 to 10% by weight, of the total amount of the formulation. Due to the good wetting behavior, the release of poorly soluble active ingredients can also improve.
  • the polymers as binders result in mechanically extremely stable granules or tablets that are stable even over long storage times.
  • the present invention was also based on the object of providing novel preparations which, in particular, enable improved hair and skin care.
  • the application properties of hair care products should be improved.
  • One object of the invention relates to preparations which contain these polymers and a further polymer, the further polymer being selected from the group formed by
  • polyvinylpyrrolidones Polyvinylcaprolactarnen; polyurethanes;
  • Copolymers of ethyl acrylate and methacrylic acid Copolymers of N-tert-butyl acrylamide, ethyl acrylate and acrylic acid;
  • Copolymers of vinyl acetate and crotonic acid and / or (vinyl) neodecanoate
  • Copolymers of vinyl acetate and / or vinyl propionate and N-vinylpyrrolidone are also known as copolymers.
  • preparations which contain the polymers in combination with these other polymers have unexpected properties.
  • the preparations according to the invention are superior in particular to the preparations of the prior art with regard to their skin and hair care properties. Furthermore, they have very good film-forming and strengthening properties.
  • Copolymers of tert-butyl acrylate, ethyl acrylate and methacrylic acid are available, for example, as commercial products Luvimer TM 100 P, Luvimer TM 36 D, Luvimer TM 30 E (BASF).
  • Copolymers of ethyl acrylate and methacrylic acid are available, for example, as commercial products Luviflex TM Soft (BASF).
  • Copolymers of N-tert-butyl acrylamide, ethyl acrylate and acrylic acid are available, for example, as commercial products Ultrahold Strong TM, Ultrahold 8 TM (BASF).
  • Polyvinylpyrrolidones are available, for example, under the trade names Luviskol K TM, Luviskol K 30 TM (BASF) and PVP K (ISP).
  • Polyvinylcaprolactams (INCI: Polyvinylcaprolactame) are available, for example, under the trade name Luviskol Plus TM (BASF).
  • Copolymers of vinyl acetate and crotonic acid are available, for example, under the trade names Luviset CA 66 TM (BASF), Resyn TM 28-1310 (National Starch) and Aristoflex TM A (Celanese).
  • Copolymers of vinyl acetate, crotonic acid and (vinyl) neodecanoate are available, for example, under the trade names Resyn TM 28-2930 (National Starch) and Luviset TM CAN (BASF).
  • Copolymers of vinyl acetate and N-vinylpyrrolidone are available, for example, under the trade names Luviskol VA TM (BASF) and PVP / VA (ISP).
  • Polyurethanes (INCI: Polyurethane -1) are available, for example, under the trade name Luviset TM PUR.
  • Copolymers of acrylic acid, methyl methacrylate, octylacrylamide, butylaminoethyl methacrylate, hydroxypropyl methacrylate are known, for example, under the trade names Amphomer TM 28-4910 and Amphomer TM LV-71 (National Starch).
  • Another object of the invention relates to the use of these preparations in cosmetic and / or pharmaceutical preparations.
  • Another object of the invention relates to preparations which contain the polymers and at least one UV light protection filter and their use in cosmetic and / or pharmaceutical preparations.
  • the purpose of the light protection filters used in cosmetic and pharmaceutical preparations is to prevent or at least to reduce the harmful effects of sunlight on human skin. Besides these light protection filters also protect other ingredients from destruction or degradation by UV radiation. In hair cosmetic formulations, damage to the keratin fiber by UV rays is to be reduced.
  • Sunlight reaching the earth's surface has a share of UV-B (280 to 320 nm) and UV-A radiation (> 320 nm), which are directly connected to the range of visible light.
  • UV-B 280 to 320 nm
  • UV-A radiation > 320 nm
  • the narrower range around 308 nm is given as a maximum of the erythema effectiveness of sunlight.
  • Numerous compounds are known for protection against UVB radiation, which include are derivatives of 3-benzylidene camphor, 4-aminobenzoic acid, cinnamic acid, salicylic acid, benzophenone and 2-phenylbenzimidazole.
  • UVA range For the range between about 320 nm and about 400 nm, the so-called UVA range, it is important to have filter substances available, since their rays can cause reactions in light-sensitive skin. It has been proven that UVA radiation leads to damage to the elastic and collagen fibers of the connective tissue, which causes the skin to age prematurely, and that it is to be seen as the cause of numerous phototoxic and photoallergic reactions. The damaging influence of UVB radiation can be intensified by UVA radiation.
  • UV light protection filters ..
  • Oil-soluble organic UV-A filters and / or UV-B filters and / or water-soluble organic UV-A filters and / or UV-B filters can be used as UV light protection filters.
  • the total amount of UV light protection filters is generally 0.1% by weight to 30% by weight, preferably 0.5 to 15% by weight, in particular 1 to 10% by weight, based on the total weight of the preparations.
  • the UV light protection filters are advantageously chosen so that the preparations protect the skin from the entire range of ultraviolet radiation.
  • Examples include:
  • combinable light stabilizers include the following compounds:
  • UV light protection filters which can be used in combination with the polymers according to the invention, is of course not intended to be limiting.
  • Another object of the invention relates to the use of these preparations in cosmetic and / or pharmaceutical preparations.
  • Suitable suitable polymerizable monomers (a) are ethylenically unsaturated monomers. Either single monomers or combinations of two or more monomers can be used.
  • Monomers that can be polymerized with a free radical initiated reaction are preferred.
  • ethylenically unsaturated means that the monomers have at least one polymerizable carbon-carbon double bond which can be mono-, di-, tri- or tetrasubstituted.
  • the ethylenically unsaturated monomers (a) can be described by the following general formula:
  • X is selected from the group consisting of -OH, -0M, -OR 8 , NH 2 , -NHR 8 , N (R 8 ) 2 ;
  • M is a cation selected from the group consisting of: Na +, K +, Mg ++, Ca ++, Zn ++, NH4 +, alkylammonium, dialkylammonium, trialkylammonium and tetraalkylammonium;
  • radicals R 8 can be selected identically or differently from the group consisting of -H, C1-C40 linear or branched-chain alkyl radicals, N, N-dimethylaminoethyl, 2-hydroxyethyl,
  • R 7 and R 6 are independently selected from the group consisting of: -H, Ci-Cs linear or branched chain alkyl chains, methoxy, ethoxy, 2-hydroxyethoxy, 2-met oxyethoxy and 2-ethoxyethyl.
  • Suitable monomers (a) are, for example, acrylic acid and its salts, esters and amides.
  • the salts can be derived from any non-toxic metal, ammonium or substituted ammonium counterions.
  • the esters can be derived from C 1 -C 40 linear, C 3 -C 40 branched chain, or C 3 -C 4 o carbocyclic alcohols, from polyfunctional alcohols with 2 to about 8 hydroxyl groups such as ethylene glycol, hexylene glycol, glycerol, and 1, 2, 6-hexanetriol, of amino alcohols or of alcohol ethers such as methoxyethanol and ethoxyethanol or polyethylene glycols.
  • N, N-dialkylaminoalkyl acrylates and methacrylates and N-dialkylaminoalkyl acrylates and methacrylamides are also suitable.
  • R 9 H, alkyl with 1 to 8 C atoms
  • the amides can be unsubstituted, N-alkyl or N-alkylamino monosubstituted, or N, N-dialkyl-substituted or N, N-dialkylamino disubstituted, in which the alkyl or alkylamino groups of C 1 -C 40 linear, C 3 -C 4 o branched chain, or C3-C40 carbocyclic units are derived.
  • the alkylamino groups can be quaternized.
  • Preferred monomers of the formula II are N, N-dimethylaminomethyl (meth) acrylate, N, N-diethylaminomethyl (eth) acrylic, N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate.
  • Monomers (a) which can also be used are substituted acrylic acids and salts, esters and amides thereof, where the substituents on the carbon atoms are in the two or three positions of acrylic acid and are selected independently of one another from the group consisting of C 1 -C 4 alkyl, -CN, COOH particularly preferably methacrylic acid, ethacrylic acid and 3-cyanoacrylic acid.
  • These salts, esters and amides of these substituted acrylic acids can be selected as described above for the salts, esters and amides of acrylic acid.
  • Suitable monomers (a) are vinyl and allyl esters of C 1 -C 40 linear, C 3 -C 4 o branched-chain or C 3 -C 40 carbocyclic carboxylic acids (eg: vinyl acetate, vinyl propionate, vinyl neononanoate, vinyl neoundecanoic acid or t- butyl-benzoic acid vinyl- ester); Vinyl or allyl halides, preferably vinyl chloride and allyl chloride, vinyl ethers, preferably methyl, ethyl, butyl or dodecyl vinyl ether, vinylformamide, vinylmethylacetamide, vinylamine; Vinyllacta e, preferably vinylpyrrolidone and vinylcaprolactam, vinyl- or allyl-substituted heterocyclic compounds, preferably vinylpyridine, vinyloxazoline and allylpyridine.
  • N-vinylimidazoles of the general formula III in which R 14 to R 16 independently of one another are hydrogen, C 1 -C 4 -alkyl or phenyl:
  • Suitable monomers (a) are vinylidene chloride; and hydrocarbons with at least one carbon-carbon double bond, preferably styrene, alpha-methylstyrene, tert-butylstyrene, butadiene, isoprene, cyclohexadiene, ethylene, propylene, 1-butene, 2-butene, isobutylene, vinyl toluene, and mixtures of these monomers ,
  • Particularly suitable monomers (a) are acrylic acid, methacrylic acid, ethyl acrylic acid, methyl acrylate, ethyl acrylate, propyl acrylate, n-butyl acrylate, isobutyl acrylate, t-butyl acrylate, 2-ethylhexyl acrylate, decyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, propyl methacrylate -Butyl methacrylate, t-butyl methacrylate, 2-ethylhexyl methacrylate, decyl methacrylate, methyl ethacrylate, ethyl ethacrylate, n-butyl ethacrylate, iso-butyl ethacrylate, t-butyl ethacrylate, 2-ethylhexyl ethacrylate, decyl ethacrylate,
  • vinyl ether for example: methyl, ethyl, butyl or dodecyl vinyl ether
  • vinyl formamide vinyl methylacetamide
  • vinylamine Methyl vinyl ketone
  • maleimide vinyl pyridine
  • vinyl imidazole vinyl furan
  • styrene styrene sulfonate
  • allyl alcohol and mixtures thereof.
  • acrylic acid methacrylic acid, maleic acid, fumaric acid, crotonic acid, maleic anhydride and its half esters, methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-butyl acrylate, n-butyl methacrylate, t-butyl acrylate, t-butyl methacrylate, isobutyl acrylate acrylate, 2-ethylhexyl acrylate, Nt-butylacrylamide, N-octyl acrylamide, 2-hydroxyethyl acrylate, hydroxypropyl acrylate, 2-hydroxyethyl methacrylate, hydroxypropyl methacrylate, alkylene glycol (meth) acrylates, unsaturated sulfonic acids such as acrylamidopropanesulfonic acid, vinyl ether pyrrolidone, vinyl pyrrolidone,
  • Monomers with a basic nitrogen atom can be quaternized in the following way:
  • alkyl halides with 1 to 24 carbon atoms in the alkyl group e.g. Methyl chloride, methyl bromide, methyl iodide, ethyl chloride, ethyl bromide, propyl chloride, hexyl chloride, dodecyl chloride, lauryl chloride and benzyl halides, especially benzyl chloride and benzyl bromide.
  • Other suitable quaternizing agents are dialkyl sulfates, especially dimethyl sulfate or diethyl sulfate.
  • the quaternization of the basic amines can also be carried out with alkylene oxides such as ethylene oxide or propylene oxide in the presence of acids.
  • alkylene oxides such as ethylene oxide or propylene oxide
  • Preferred quaternizing agents are: methyl chloride, dimethyl sulfate or diethyl sulfate.
  • (meth) acrylates are used as monomers (a).
  • the quaternization can be carried out before the polymerization or after the polymerization.
  • reaction products of unsaturated acids such as acrylic acid or methacrylic acid
  • Examples include: (meth) acryloyloxyhydroxy-propyltrimethylammonium chloride and (meth) acryloyloxyhydroxypropyltriethylammonium chloride
  • the basic monomers can also be cationized by neutralizing them with mineral acids, such as sulfuric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid or nitric acid, or with organic acids, such as formic acid, acetic acid, lactic acid or citric acid.
  • mineral acids such as sulfuric acid, hydrochloric acid, hydrobromic acid, hydroiodic acid, phosphoric acid or nitric acid
  • organic acids such as formic acid, acetic acid, lactic acid or citric acid.
  • macromonomers such as, for example, silicone-containing macromonomers with one or more radical-polymerizable groups or alkyloxazoline macromonomers as described, for example, in EP 408 311 can be used as monomers (a).
  • crosslinking compounds or compounds which regulate the molecular weight can be used in combination or alone.
  • the usual compounds known to the person skilled in the art such as, for example, sulfur compounds (for example: mercaptoethanol, 2-ethylhexylthioglycolate, thioglycolic acid or dodecyl mercaptan) and tribromochloromethane or other compounds which have a regulating effect on the molecular weight of the polymers obtained, can be used as regulators.
  • sulfur compounds for example: mercaptoethanol, 2-ethylhexylthioglycolate, thioglycolic acid or dodecyl mercaptan
  • tribromochloromethane or other compounds which have a regulating effect on the molecular weight of the polymers obtained can be used as regulators.
  • silicone compounds containing thiol groups can also be used. Silicone-free controllers are preferably used.
  • Crosslinking monomers which can be used are compounds having at least two ethylenically unsaturated double bonds, for example esters of ethylenically unsaturated carboxylic acids, such as acrylic acid or methacrylic acid and polyhydric alcohols, ethers of at least dihydric alcohols, for example vinyl ether or allyl ether. Also suitable are straight-chain or branched, linear or cyclic aliphatic or aromatic hydrocarbons which have at least two double bonds which must not be conjugated to the aliphatic hydrocarbons.
  • amides of acrylic and methacrylic acid and N-allylamines of at least divalent amines such as (1, 2-diaminoethane, 1,3-di-a-inopropane).
  • triallylamine or corresponding ammonium salts N-vinyl compounds of urea derivatives, at least divalent amides, cyanurates or urethanes.
  • Other suitable crosslinkers are divinyldioxane, tetraallylsilane or tetravinylsilane.
  • crosslinking agents are, for example, methylene bisacrylamide, triallylamine and triallylammonium salts, divinyl imidazole, N, N'-divinylethylene urea, reaction products of polyhydric alcohols with acrylic acid or methacrylic acid, methacrylic acid esters and acrylic acid esters of polyalkylene oxides or polyhydric alcohols with ethylene oxide and / or propylene / or epichlorohydrin have been implemented. If they contain ionizable groups, the monomers (a) according to the invention can be partially or completely neutralized with acids or bases before or after the polymerization in order, for example, to adjust the water solubility or dispersibility to a desired level.
  • Mineral bases such as sodium carbonate, alkali metal hydroxides and ammonia
  • organic bases such as amino alcohols, especially 2-amino-2-methyl-1-propanol, monoethanolamine, diethanolamine, triethanolamine, triisopropanolamine, tri [(2- hydroxy) 1-propyl] amine, 2-amino-2-methyl-l, 3-propanediol, 2-amino-2-hydroxymethyl-1, 3-propanediol and diamines such as lysine can be used.
  • mineral acids such as hydrochloric acid, sulfuric acid or phosphoric acid
  • organic acids such as carboxylic acids, lactic acid, citric acid or others can be used as neutralizing agents for monomers bearing cationizable groups.
  • Particularly suitable polyalkylene oxide-containing silicone derivatives (b) are those which contain the following structural elements:
  • R 6 is an organic radical of 1 to 40 carbon atoms
  • R 1 can be identical or different and either come from the group of aliphatic hydrocarbons with 1 to 20 carbon atoms, are cyclic aliphatic hydrocarbons with 3 to 20 C atoms, are aromatic in nature or are equal to R 5 , where:
  • radicals R 1 , R 2 or R 3 are a polyalkylene oxide-containing radical as defined above, and n is an integer from 1 to 6, x and y are integers such that the molecular weight of the polysiloxane Blocks is between 300 and 30000, a, b can be integers between 0 and 50, with the proviso that the sum of a and b is greater than 0 and C is 0 or 1.
  • Preferred radicals R 2 and R 5 are those in which the sum of a + b is between 5 and 30.
  • the groups R 1 are preferably selected from the following group: methyl, ethyl, propyl, butyl, isobutyl, pentyl, isopentyl, hexyl, octyl, decyl, dodecyl and octadecyl, cycloaliphatic radicals, especially cyclohexyl, aromatic groups, especially phenyl or naphthyl, mixed aromatic-aliphatic radicals such as benzyl or phenylethyl as well as tolyl and xylyl and R 5 .
  • compounds according to the following formula are used as the silicone derivative (b) containing polyalkylene oxide:
  • R 4 -H; -COCH 3 , alkyl with C 1 -C 4
  • n 1 to 6, in particular 2 to 4, preferably 3
  • x and y are integers such that the molecular weight of the polysiloxane block is between 1000 and 5000, a, b can be integers between 0 and 50, with the proviso that the sum of a and b is greater than 0.
  • Such particularly preferred silicone derivatives are listed under CAS no. 872 44-72-2 known. As commercial products they are available under the names Belsil DMC 6031 TM (Wacker), Dabco DC 193, Dabco DC 5357, Dow Corning 198 TM, Dow Corning 5039 TM and Silwet 7600 TM (Witco).
  • Such particularly preferred silicone derivatives are listed under CAS no. 71965-38-3 known. They are available as commercial products under the names Abil B 8842, Abil B 8843, Silwet L 7607 (Witco).
  • silicone derivatives which are available under the trade names Belsil DMC 6032 TM (Wacker) and Dow Corning 190 TM (Dow Chemicals).
  • the monomers (a) of the polysiloxane-containing polymers of the present invention can make up from 50 to 99.9% by weight, preferably 70 to 99% by weight, particularly preferably 85 to 98% by weight. If the ethylenically unsaturated monomers (a) are used as a combination of two monomers (al and a2), it has proven to be Partially proven to use 49.5 to 99 wt .-% (al) and 0.5 to 40 wt .-% (a2).
  • the silicone derivatives (b) are generally present in the polymer according to the invention in amounts of 0.1 to 50, preferably 0.5 to 20, particularly preferably 2 to 15% by weight.
  • a polymer which can be obtained by radical polymerization of a monomer mixture from
  • R 1 -CH 3
  • R 4 -H; -COCH 3 , alkyl with C 1 -C 4
  • n 1 to 6, in particular 2 to 4, preferably 3
  • x and y are integers such that the molecular weight of the polysiloxane block is between 1000 and 5000,
  • a, b can be integers between 0 and 50, with the proviso that the sum of a and b is greater than 0. If the silicone compounds (b) are not present during the polymerization, but are mixed in after the polymerization, generally very soft sticky films are obtained which are unsuitable for the applications according to the invention in cosmetics for skin and hair 5.
  • polymerizable it is meant that the monomers used can be polymerized using any conventional synthetic method.
  • this can be solution polymerization, emulsion polymerization, reverse emulsion polymerization, suspension polymerization, reverse suspension polymerization or precipitation polymerization, without the methods which can be used being restricted thereto.
  • solution polymerization water, conventional organic solvents or the silicone derivatives according to the invention themselves can be used as solvents.
  • the polymers according to the invention preferably have a K value (according to Fickentscher, Cellulosechemie, Vol. 13, pp. 58-64 (1932) measured at 250 ° C. 0.1 5% in 0.5 molar saline solution) of 30 to 30 50 on, preferably 37 to 41.
  • K value accordinging to Fickentscher, Cellulosechemie, Vol. 13, pp. 58-64 (1932) measured at 250 ° C. 0.1 5% in 0.5 molar saline solution
  • water-dispersible means polymers which come into contact with the water within 24 hours
  • polymers such as, for example, homopolymers and copolymers of ethylenically unsaturated monomers, and also polyamides, polyurethanes or polyesters, may also be present in the polymerization of the monomers.
  • the polyamides, polyurethanes, polyesters are preferably ionically modified, e.g. with carboxylate or sulfonate groups.
  • a particularly preferred polymer according to the invention is, for example, a polymer available under the trade name Luviflex® Silk (INCI name: PEG / PPG-25/25 Dimethicone / Acrylates / t-Butyl Acrylates; BASF Aktiengesellschaft).
  • the preparations according to the invention can be present in final preparations as aqueous or aqueous-alcoholic solutions, 0 / W and W / O emulsions in the form of shampoos, creams, foams, lotion, mousse, sprays (pump spray or aerosol), gels or gel sprays and accordingly with customary ones other auxiliary substances can be formulated.
  • auxiliaries are: surfactants, oil bodies, emulsifiers, co-emulsifiers, superfatting agents, pearlescent waxes, consistency agents, thickeners, fats, waxes, silicone compounds, hydrotropes, preservatives, perfume oils, dyes, stabilizers, pH value regulators, cosmetic care agents and Active ingredients such as AHA acids, fruit acids, ceramides, phytantriol, bisabolol, panthenol, collagen, provitamins and vitamins, e.g. Vitamins A, E and C, proteins and protein hydrolyzates (e.g.
  • Suitable anionic surfactants include for example alkyl sulfates, alkyl ether sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl succinates, alkyl sulphosuccinates, N-carboxylate Alkoylsarkosinate, acyl taurates, acyl isethionates, alkyl phosphates, alkyl ether phosphates, alkyl ether, alpha-olefin sulfonates, especially the alkali metal and alkaline earth metal salts, eg sodium, potassium , Magnesium, calcium, and ammonium and triethanolamine salts.
  • alkali metal and alkaline earth metal salts eg sodium, potassium , Magnesium, calcium, and ammonium and triethanolamine salts.
  • the alkyl ether sulfates, alkyl ether phosphates and alkyl ether carboxylates can have between 1 and 10 ethylene oxide or propylene oxide units, preferably 1 to 3 ethylene oxide units in the molecule.
  • Suitable amphoteric surfactants are, for example, alkylbetaines, alkylamidopropylbetaines, alkylsulfobetaines, alkylglycinates, alkylcarboxyglycinates, alkylamphoacetates or propionates, alkylamphodiacetates or dipropionates.
  • cocodimethylsulfopropyl betaine cocodimethylsulfopropyl betaine, lauryl betaine, cocamidopropyl betaine or sodium cocamphopropionate can be used.
  • Suitable nonionic surfactants are, for example, the reaction products of aliphatic alcohols or alkylphenols with 6 to 20 carbon atoms in the alkyl chain, which can be linear or branched, with ethylene oxide and / or propylene oxide.
  • the amount of alkylene oxide is about 6 to 60 moles per mole of alcohol.
  • Alkylamine oxides, mono- or dialkylalkanolamides, fatty acid esters of polyethylene glycols, ethoxylated fatty acid amides, alkyl polyglycosides or sorbitan ether esters are also suitable.
  • the agents can contain conventional cationic surfactants, e.g. quaternary ammonium compounds, for example cetyltrimethylammonium chloride.
  • conventional cationic surfactants e.g. quaternary ammonium compounds, for example cetyltrimethylammonium chloride.
  • the agents according to the invention in particular in the form of shampoo formulations, usually contain anionic surfactants as the base side and amphoteric and nonionic surfactants as the side side.
  • compositions usually contain 2 to 50% by weight of surfactants, preferably 5 to 40% by weight, particularly preferably 8 to 30% by weight.
  • Animal and vegetable oils such as e.g. Sunflower oil, coconut oil, avocado oil, olive oil or lanolin.
  • Suitable emulsifiers are nonionic surfactants from at least one of the following groups:
  • alkyl mono- and oligoglycosides with 8 to 22 carbon atoms in the alkyl radical and their ethoxylated analogs
  • polyol and especially polyglycerol esters such as e.g. Polyglycerol polyricinoleate, polyglycerol poly-12-hydroxystearate or polyglycerol dimerate. Mixtures of compounds from several of these classes of substances are also suitable;
  • adducts of 2 to 15 moles of ethylene oxide with castor oil and / or hardened castor oil (8) partial esters based on linear, branched, unsaturated or saturated C 6/2 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (for example sorbitol), alkyl glucosides (for example methyl glucoside, butyl glucoside, Lauryl glucoside) and polyglucosides (eg cellulose);
  • the adducts of ethylene oxide and / or of propylene oxide with fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters, and sorbitan mono- and diesters with fatty acids or with castor oil are known, commercially available products. whose average degree of alkoxylation corresponds to the ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out.
  • C ⁇ / i 8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE-PS 2024051 as refatting agents for cosmetic preparations.
  • Cs / is alkyl mono- and oligoglycosides
  • their preparation and their use are known from the prior art. They are produced in particular by reacting glucose or oligosaccharides with primary alcohols with 8 to 18 carbon atoms.
  • the glycoside ester both monoglycosides in which a cyclic sugar residue is glycosidically bonded to the fatty alcohol and oligomeric glycosides with a degree of oligomerization of up to preferably about 8 are suitable.
  • the degree of oligomerization is a statistical mean value which is based on a homolog distribution customary for such technical products.
  • Zwitterionic surfactants can also be used as emulsifiers.
  • Zwitterionic surfactants are surface-active compounds that contain min- at least carry a quaternary ammonium group and at least one carboxylate and one sulfonate group.
  • Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the coconut alkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example the coconut acylaminopropyl dimethylammonium glycinate, and 2-alkyl- 3-carboxylmethyl-3-hydroxyethyl idazolines each having 8 to 18 carbon atoms in the alkyl or acyl group as well as the coconut acylaminoethyl hydroxyethyl carboxy ethyl glycinate.
  • betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the coconut alkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethyl
  • fatty acid amide derivative known under the CTFA name Cocamidopropyl Betaine is particularly preferred.
  • Suitable emulsifiers are ampholytic surfactants.
  • Ampholytic surfactants are understood to mean those surface-active compounds which, in addition to a Cs / is alkyl or acyl group, contain at least one free amino group and at least one -C00H or -S0 3 H group in the molecule and are capable of forming internal salts.
  • ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkyl sarcosine, 2-alkylaminopropionic acid and alkyl inoacetic acid with each about 8 to 18 carbon atoms in the alkyl group.
  • ampholytic surfactants are N-cocoalkylamino propionate, cocoacylaminoethylaminopropionate and Ci 2 i 8 ⁇ Ac Yl sarcos; '- n -
  • ampholytic emulsifiers quaternary emulsifiers are contemplated, where such are especially preferred of the esterquat type, preferably methyl-Difettklatriethanolaminester- salts.
  • Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers,
  • Pearlescent waxes for example, are: alkylene glycol esters, special ethylene glycol masterate; Fatty acid alkanolamides, especially coconut fatty acid diethanoamide; Partial glycerides, especially stearic acid monoglyceride; Esters of polyvalent, optionally hydroxy-substituted carboxylic acids with fatty alcohols having 6 to 22 carbon atoms, especially long-chain esters of tartaric acid; Fatty substances, such as, for example, fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which have a total of at least 24 carbon atoms, especially lauron and distearyl ether; Fatty acids such as stearic acid, hydroxystearic acid or behenic acid, ring opening products of olefin epoxides with 12 to 22 carbon atoms with fatty alcohols with 12 to 22 carbon atoms and / or polyols with 2 to 15 carbon atoms and
  • Suitable consistency agents are primarily fatty alcohols or hydroxy fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and, in addition, partial glycerides, fatty acids or hydroxy fatty acids.
  • a combination of these substances with alkyl oligoglucosides and / or fatty acid N-methylglucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates is preferred.
  • Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar-guar, agar-agar, alginates and tyloses, cellulose derivatives such as carboxymethyl cellulose and hydroxyethyl cellulose, also relatively high molecular weight polyethylene glycol monoesters and diesters acids of fat, polyacrylates (for example Carbopol ® of Goodrich or
  • Synthalene® from Sigma polyacrylamides, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with a narrow homolog distribution or
  • Alkyl oligoglucosides as well as electrolytes such as table salt and ammonium chloride.
  • Typical examples of fats are glycerides, waxes include Beeswax, carnauba wax, candelilla wax, montan wax, paraffin wax or micro waxes, optionally in combination with hydrophilic waxes, e.g. Cetylstearyl alcohol or partial glycerides in question.
  • Metal salts of fatty acids such as e.g. Magnesium, aluminum and / or zinc stearate or ricinoleate are used.
  • Suitable silicone compounds are, for example, dirnethyl polysiloxanes, methylphenylpolysiloxanes, cyclic silicones and also ino-, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl-modified silicone compounds, which can be both liquid and resinous at room temperature .
  • Typical examples of fats are glycerides; waxes include beeswax, carnauba wax, candelilla wax, montan wax, paraffin wax or microwaxes, optionally in combination with hydrophilic waxes, for example cetylstearyl alcohol or partial glycerides.
  • Metal salts of fatty acids such as magnesium, aluminum and / or zinc stearate can be used as stabilizers.
  • Suitable solvents are in particular water and lower monoalcohols or polyols with 1 to 6 carbon atoms and mixtures thereof; preferred monoalcohols or polyols are ethanol, i-propanol, propylene glycol, glycerin and sorbitol.
  • Hydrotropes such as ethanol, isopropyl alcohol or polyols can also be used to improve the flow behavior.
  • Polyols that come into consideration here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. Typical examples are
  • Alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1000 daltons; technical oligoglycerol mixtures with a degree of self-condensation of 1.5 to 10 such as technical diglycerol mixtures with a diglycerol content of 40 to 50% by weight; Methyl compounds, such as, in particular, trimethylolethane,
  • Trimethyl propane Trimethyl butane, pentaerythritol and dipentaerythritol;
  • Sugar alcohols containing 5 to 12 carbon atoms such as ⁇ example, sorbitol or mannitol;
  • Sugars with 5 to 12 carbon atoms such as glucose or sucrose; - aminosugars, such as glucamine.
  • Suitable preservatives are, for example, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and the other classes of substances listed in Appendix 6, Parts A and B, of the Cosmetics Ordinance.
  • triclosan 2, 4, 4 'trichloro-2' hydroxydiphenyl ether
  • chlorhexidine l, l , -hex-ii ⁇ ethylenbis [5- (4-chlorophenyl) - biguanide
  • TTC 3,4,4'-trichlorocarbanilide
  • Quaternary ammonium compounds are also suitable in principle, but are preferably used for disinfectant soaps and washing lotions.
  • Numerous fragrances also have antimicrobial properties.
  • Special combinations with particular effectiveness against gram-positive bacteria are used for the composition of so-called deoparfums.
  • a large number of essential oils or their characteristic ingredients such as clove oil (eugenol), mint oil (menthol) or thyme oil (thymol) show a pronounced antimicrobial effectiveness.
  • the preservatives are usually used in concentrations of approximately 0.1 to 0.3% by weight.
  • Perfume oils include mixtures of natural and synthetic fragrances.
  • Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, cumin, juniper), fruit peel (bergamot, lemon, Oranges), roots (mace, angelica, celery, cardamom, costus, iris, cal us), woods (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, leon grass, sage, thyme ), Needles and twigs (spruce, fir, pine, mountain pine), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax). Animal raw materials, such as civet and castoreum, are also suitable.
  • Typical synthetic fragrance compounds are products of the
  • Fragrance compounds of the ester type are, for example, benzyl acetate, phenoxyethyl isobutyrate, p-tert. -Butylcyclohexyl acetate, linalyl acetate, dimethylbenzylcarbinylacetate, phenylethyl acetate, linalyl benzoate, benzyl formate, ethyl methylphenyl glycinate, allyl cyclohexyl propionate, styrallyl propionate and benzyl salicylate.
  • the ethers include, for example, benzyl ethyl ether
  • the aldehydes include, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cycl menaldehyde, hydroxycitronellal, lilial and bourgeonate
  • the ketones include, for example, the ionones, cc-isomethyl ions and methyl cedryl ketone Alcohols Anethof, Citronellol, Eugenol, Isoeugenol, Geraniol, Linalool, Phenylethylalkohol and Terioneol
  • the hydrocarbons mainly include the terpenes and balms.
  • fragrance oils of lower volatility which are mostly used as aroma components, are also suitable as perfume oils, e.g. sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon leaf oil, linden blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and lavandin oil.
  • the dyes which can be used are those which are suitable and approved for cosmetic purposes, as compiled, for example, in the publication "Cosmetic Dyes” by the Dye Commission of the German Research Foundation, Verlag Chemie, Weinheim, 1984, pp. 81-106. These dyes are usually used in concentrations of 0.001 to 0.1% by weight, based on the mixture as a whole.
  • anionic, cationic, amphoteric and neutral polymers are suitable as other polymers.
  • anionic polymers are homopolymers and copolymers of acrylic acid and acrylamide and their salts, sodium salts of polyhydroxycarboxylic acids, water-soluble or water-dispersible polyesters, polyurethanes and polyureas.
  • Particularly suitable polymers are copolymers of tert-butyl acrylate, ethyl acrylate, methacrylic acid (for example Luvimer® 100 P), copolymers of ethyl acrylate and methacrylic acid (for example Luviflex® Soft), copolymers of N-tert-butyl acrylamide, ethyl acrylate, acrylic acid (ultrahold strong ®), copolymers of vinyl acetate, crotonic acid and optionally other vinyl esters (eg Luviset CA66®), maleic anhydride copolymers, optionally reacted with alcohols, anionic polysiloxanes, eg carboxy-functional copolymers of vinyl pyrrolidone,
  • Still other polymers are cationic polymers having the INCI name Polyquaternium, eg copolymers of vinylpyrrolidone / N-vinylimidazolium salts (Luviquat ® FC, Luviquat ® HM, Luviquat MS, Luviquat Care), copolymers of N-vinylpyrrolidone / hylaminoethylmethacrylat whore quaternized with diethyl sulfate (Luviquat® PQ 11), copolymers of N-vinylcaprolactam / N-vinyl- pyrrolidone / N-vinylimidazolium salts (Luviquat ® Hold).
  • cationic cellulose derivatives Polyquaternium-4 and -10
  • acrylamide copolymers Polyquaternium-
  • Styleeze TM CC-10 Aquaflex® SF-40 and chitosan derivatives.
  • Neutral polymers such as polyvinylpyrrolidones, copolymers of N-vinylpyrrolidone and vinyl acetate and / or vinyl propionate, polysiloxanes, polyvinylcaprolactam and copolymers with N-vinylpyrrolidone, polyethyleneimines and their salts, polyvinylamines and their salts, cellulose derivative derivatives, polyasparagine derivatives, polyasparas derivatives, are also suitable as further polymers , These include the polymer Luviskol® (K, VA, Plus), PVP K, PVP / VA, Advantage ® HC and H 2 0LD EP-1 known under the following trade names.
  • biopolymers i.e. Polymers that are obtained from naturally renewable raw materials and are built up from natural monomer components, e.g. Cellulose derivatives, chitin, chitosan, DNA, hyaluronic acid and RNA derivatives.
  • polymers include betaine polymers such as Yukaformer (R205, SM) and Diaformer.
  • the total proportion of auxiliaries and additives can be 1 to 50, preferably 5 to 40,% by weight, based on the composition.
  • the auxiliaries can be present during the polymerization and / or can be added after the polymerization.
  • components are selected according to the invention as the oil phase which have a positive effect on the cosmetic formulation (appearance, skin feel).
  • Such components are native, for example Oils such as sunflower oil, almond oil, avocado oil, wax esters such as jojoba oil, fatty acid isopropyl esters such as isopropyl palmitate, isopropyl myristate, di- and triglycerides of fatty acids, such as, for example, caprylic acid / capric glyceride.
  • the proportion of the oil phase in the total emulsion is 15 to 70% by weight, preferably 20 to 35% by weight.
  • Known W / O emulsifiers are used to disperse the water phase in the organic phase.
  • Such emulsifiers are e.g. Sorbitan monooleate, sorbitan monostearate, glyceryl monostearate, block copolymers of hydroxy fatty acid polyesters and polyoxyethylene. They can be used alone or in combination in total concentrations of 2 to 10% by weight, preferably 2 to 5% by weight, based on the total emulsion.
  • Emulsifiers with an HLB value of over 8 can also be added to the emulsion, in concentrations of 0.25 to 7% by weight, based on the total emulsion.
  • Such emulsifiers are, for example, ethoxylated Cg -C 2 nonylphenols or C 1 -C 8 fatty alcohols, the degree of ethoxylation is 5 to 20 mol%.
  • the aqueous monomer phase can be stirred in a standard polymerization vessel, e.g. emulsify with an anchor stirrer.
  • the speed is between 30 and 400 rpm depending on the boiler geometry.
  • Water-in-oil emulsions having a solids content of 10 to 40% by weight, preferably 15 to 35% by weight, are obtained after the polymerization.
  • the emulsions can be partially or completely dewatered by distillation.
  • the W / O emulsions of the polymers according to the invention are preferably used as thickeners in skin cosmetic or pharmaceutical preparations.
  • the polymers can be used directly in the form of the W / O emulsion.
  • the thickening effect of the W / O emulsion occurs immediately after the W / O emulsion has been mixed with a cosmetic and / or pharmaceutical O / W emulsion; in order to achieve the optimal effect, no addition of an inverting agent is necessary. Purely aqueous systems can also be thickened. You get a cream gel.
  • the preparations according to claims 10 and / or 11 are particularly suitable for use in cosmetic products. For example, they can be used in cosmetic products for cleaning the skin.
  • Such cosmetic cleaning agents are selected from 5 bar soaps, such as toilet soaps, core soaps, transparent soaps, luxury soaps, deodorant soaps, cream soaps, baby soaps, skin protection soaps, abrasive soaps and syndets, liquid soaps, such as pasty soaps, soft soaps and washing pastes, and liquid washing and showering agents.
  • bath preparations such as washing lotions, shower baths and gels, foam baths, oil baths and scrub preparations, shaving foams, lotions and creams.
  • the preparations according to the invention can also be used in cosmetic preparations for skin care.
  • the skin care products are available in particular as W / O or O / W skin creams, day and night creams, eye creams, face creams, anti-wrinkle creams, moisturizing creams, bleaching creams, vitamin creams, skin lotions, care lotions and moisturizing lotions.
  • preparations according to the invention can be used as strips for pore cleansing or skin tightening, in anti-acne agents, repellents, shaving agents, hair removal agents, intimate hygiene products, foot care products and in baby care.
  • the preparations according to the invention according to claims 10 and / or 30 11 are particularly suitable for hair cosmetics, preferably in preparations such as hair treatments, hair lotions, hair rinses, hair emulsions, tip fluids, leveling agents for perms, hot oil treatment preparations, conditioners, curl relaxers, styling wrap lotions, setting lotions, shampoos, hair dyes or 35 hair sprays.
  • compositions according to the invention are preferred as film formers and / or coating agents in cosmetic and / or pharmaceutical preparations, in particular for those containing keratin and keratin-like surfaces such as hair, skin and nails.
  • the preparations according to claims 10 and / or 11 are used in cosmetic preparations for nail care.
  • Another object relates to the use of a polymer which is obtainable by radical polymerization of a monomer mixture from
  • R4 -H; -COCH 3 , alkyl with C ⁇ -C 4
  • n 1 to 6, in particular 2 to 4, preferably 3
  • x and y are integers such that the molecular weight of the polysiloxane block is between 1000 and 5000,
  • a, b can be integers between 0 and 50, with the proviso that the sum of a and b is greater than 0, in preparations of decorative cosmetics.
  • Preparations for decorative cosmetics include, for example, concealers, theater paint, mascara and eyeshadow, lipsticks, kohl pencils, eyeliner, makeup, foundations, blushes and powders and eyebrow pencils, and in particular nail polishes.
  • the polymers are usually contained in the cosmetic and / or pharmaceutical preparations in an amount in the range from about 0.001 to 20% by weight, preferably 0.1 to 10% by weight, based on the total weight of the preparations.
  • feed 1 and 3.75 g of feed 2 are added dropwise to a stirred receiver.
  • the mixture is then heated to 78 ° C.
  • the rest of feed 1 and feed 2 are then added dropwise within 1.5 h.
  • the mixture is stirred for a further 2 hours.
  • Feed 3 is then added dropwise within 15 minutes and the mixture is stirred at 78 ° C. for a further 3 h.
  • Feed 2 2 g of t-butyl perpivalate, 100 g of ethanol.
  • Feed 3 1.5 g of t-butyl perpivalate, 57 g of ethanol
  • Feed 2 2 g of t-butyl perpivalate, 100 g of ethanol.
  • Feed 3 1.5 g of t-butyl perpivalate, 57 g of ethanol
  • Phase A and phase B are each produced and phase B incorporated into phase A.
  • Phase B 1.00% by weight of polymer according to Example 1 or Example 5 0.12% by weight of 2-amino-2-methylpropanol 2.00% by weight of Uvinul MS 40
  • Univul MS 40 0.50% by weight of Belsil DMC 6031® (Wacker) 1.00% by weight of macadamia nut oil (e.g. Huile de Macadamio from Wacker)
  • Vitamin E Acetate® 1.00% by weight of Cremophor RH 40® (BASF) 0.40% by weight of perfume oil
  • Phase B 4.00% by weight of polymer according to Example 1 or example 0.46% by weight of 2-amino-2-methylpropanol 0.10% by weight of Euxyl K 100® (Schulke & Mayr) ad 100.00 Demineralized water
  • Example 8 with ad 0.40% Pemulen TR 1® (Goodrich) instead of 3.00% Luvigel EM ® (BASF) 100.00 demineralized water
  • Example 10 as Example 8 but with 3.5% Luvigel EM® instead of 3.00% Luvigel EM ® (BASF) 100.00 demineralized water
  • Luviskol K30® 1.00% by weight Luviskol K30® (BASF)
  • Luviflex Silk® (BASF)
  • diisobutyl adipates e.g. Crodanol DiBA from Croda
  • Example 44 15 hair spray VOC 80 with HFC 152A
  • Prapellant 152a e.g. Dymel 152a from DuPont
  • Example 45 25 hair spray VOC 55 with vitamins
  • hydrolized wheat protein e.g. Cropesol W® from Croda
  • stearic acid e.g. Emersol 120 ® from Kenkel
  • Phase C 50% phenoxyethanol (e.g. Phenoxetol® from Nipa-Hardwicke)
  • Luviflex SiLK® BASF
  • 2-amino-methylpropanol 0.50% Luviskol K30 ® (BASF) 15% Tego-Betaine L7 10.00
  • Example 5 150 g of a polymer (Example 5) were dissolved in 375 demineralized water and 375 g of ethanol were added. 100 g of polyvinylpyrrolidone-iodine (PVP-iodine 30/06, BASF Aktiengesellschaft) were then dissolved in this polymer solution with stirring and the preparation was poured into pump spray bottles. The disinfection spray showed very good film properties on the skin and showed no iodine loss after storage under stress conditions (7 days at 52 ° C).
  • PVP-iodine 30/06 polyvinylpyrrolidone-iodine 30/06
  • the bending stiffness is measured on 5 to 10 strands of hair (approx. 3 g and 24 cm in length) at 20 ° C. and 65% rel. Moisture carried out.
  • the weighed, dry strands of hair are dipped in the 3% polymer solution, with three dips in and out ensuring an even distribution.
  • the strand of hair is placed symmetrically on two cylindrical rollers of the sample holder. Exactly in the middle, the strand is bent 40 mm from above with a rounded punch (breaking the polymer film). The force required for this is measured with a load cell (50 N) and specified in Newtons.
  • Table 1 shows the values of the flexural strength of the individual polymers and the flexural strength of the preparations according to the invention in ethanolic solution, which contain the polymer and the further polymer in different weight ratios (2: 8; 1: 1; 8: 2).
  • Luviflex Silk ® was used as the polymer (BASF) used, which has a bending stiffness of 109 cN.
  • Table 2 shows the values of the bending strength of the individual polymers and the bending stiffness of the preparations according to the invention in VOC 80 formulations which contain the polymer and the further polymer in different weight ratios (2: 8; 1: 1; 8: 2).
  • Luviflex Silk ® (BASF) was used as polymer, which has a bending stiffness in VOC 80 formulation of 120 cN.
  • the bending stiffness of the preparations according to the invention is significantly greater than the sum of the bending stiffnesses of the individual polymers, both in ethanolic solution and in VOC 80 formulations.
  • the curl was hung at one end and the curl length (LO) measured.
  • the curl was placed in a climatic chamber (25 ° C, 90% relative humidity) and its length (Lt) measured after 15, 30, 60 and 90 minutes, as well as after 2, 3, 4, 5 and 24 hours.
  • the test was carried out on at least 5 strands of hair.
  • Lt length of hair after climatic treatment
  • Table 3 shows the values for the curl retention of the individual polymers and the curl retention of the preparations according to the invention in ethanol, which contain the polymer and the further polymer in different weight ratios (2: 8; 1: 1; 8: 2).
  • Luviflex Silk ® BASF
  • BASF which has a curl retention of 93%, was used as the polymer.
  • Table 4 shows the values for the curl retention of the individual polymers and the curl retention of the preparations according to the invention in VOC 80 formulations which contain the polymer and the further polymer in different weight ratios (2: 8; 1: 1; 8: 2).
  • Luviflex Silk® BASF was used as the polymer, which has a curl retention in VOC 80 formulation of 87%.

Abstract

L'invention concerne des préparations cosmétiques et/ou pharmaceutiques renfermant des polymérisats contenant des polysiloxanes solubles dans l'eau ou dispersibles dans l'eau et d'autres polymères et/ou des filtres protecteurs contre les UV. L'invention concerne en outre l'application de ces préparations ainsi que les polymérisats contenant des polysiloxanes.
EP00962362A 1999-08-26 2000-08-23 Preparations cosmetiques et/ou pharmaceutiques renfermant des polymerisats contenant des polysiloxanes et leur application Withdrawn EP1207843A2 (fr)

Applications Claiming Priority (3)

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DE19940642 1999-08-26
DE19940642 1999-08-26
PCT/EP2000/008220 WO2001013884A2 (fr) 1999-08-26 2000-08-23 Preparations cosmetiques et/ou pharmaceutiques renfermant des polymerisats contenant des polysiloxanes et leur application

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FR2798587B1 (fr) * 1999-09-16 2001-11-30 Oreal Composition cosmetique comprenant au moins un copolymere silicone/acrylate et au moins un agent photoprotecteur
FR2801198B1 (fr) 1999-09-16 2002-01-11 Oreal Composition cosmetique comprenant au moins un copolymere silicone/acrylate et au moins un agent de conditionnement
FR2798589B1 (fr) 1999-09-16 2001-11-30 Oreal Composition cosmetique comprenant au moins un copolymere silicone/acrylate et au moins un agent epaississant
FR2801199B1 (fr) 1999-09-16 2002-01-11 Oreal Composition cosmetique comprenant au moins un copolymere silicone/acrylate et au moins un polymere non ionique a motif vynil lactame
FR2801200B1 (fr) * 1999-11-19 2003-04-25 Oreal Composition cosmetique capillaire procurant de bonnes proprietes de tenue et comprenant des polymeres filmogenes
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WO2001013884A2 (fr) 2001-03-01
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JP2003507407A (ja) 2003-02-25
CN1371268A (zh) 2002-09-25

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