WO2012049146A2 - Composition de protection solaire à base de polyuréthanne comprenant des substances filtrantes spéciales - Google Patents

Composition de protection solaire à base de polyuréthanne comprenant des substances filtrantes spéciales Download PDF

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Publication number
WO2012049146A2
WO2012049146A2 PCT/EP2011/067684 EP2011067684W WO2012049146A2 WO 2012049146 A2 WO2012049146 A2 WO 2012049146A2 EP 2011067684 W EP2011067684 W EP 2011067684W WO 2012049146 A2 WO2012049146 A2 WO 2012049146A2
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Prior art keywords
acid
composition according
polyurethane
polyols
amino
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PCT/EP2011/067684
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German (de)
English (en)
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WO2012049146A3 (fr
Inventor
Sophie Viala
Sebastian Dörr
Steffen Hofacker
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Bayer Materialscience Ag
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Publication of WO2012049146A3 publication Critical patent/WO2012049146A3/fr

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • 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
    • A61K8/4966—Triazines or their condensed derivatives
    • 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

Definitions

  • the present invention relates to a composition
  • a composition comprising a polyurethane obtainable by reaction of one or more water-insoluble, non-water-dispersible, isocyanate-functional polyurethane prepolymers A) with one or more amino-functional compounds B).
  • Further objects of the invention are the use of the composition as a sunscreen and a cosmetic method for protecting the skin from negative effects of solar radiation, in which the composition is applied to the skin.
  • brown skin has been synonymous with attractive, healthy, athletic and successful people.
  • people expose their skin to solar radiation.
  • the sun's rays have a damaging effect on the skin, as they penetrate different depths into the skin, depending on the wavelength.
  • the short-wave radiation in the UVB range (wavelength: 280-320 nm) reaches the uppermost skin layer. Radiation in the UVB range causes sunburn and is responsible for an increased skin cancer risk.
  • the longer-wave UVA rays (wavelength: 320-400 nm) penetrate into deeper skin layers. They cause damage to the collagen and elastin fibers, which are essential to the structure and firmness of the skin. In addition, this leads to premature aging of the skin (formation of wrinkles and wrinkles, formation of an irregular relief of the skin, etc.).
  • sunscreen filters have been developed which are used in cosmetic and dermatological compositions.
  • the sunscreen products are often used on vacation or at leisure on the beach or during outdoor sports activities where the body is in contact with water or sweat. Therefore, there is a need to develop waterproof and / or perspiration resistant sunscreen compositions.
  • the preparation of such products is made possible by the use of selected technologies such as water-in-oil (W / O) emulsions or by the use of hydrophilic film formers such as alkylated polyvinylpyrrolidones.
  • W / O water-in-oil
  • hydrophilic film formers such as alkylated polyvinylpyrrolidones.
  • polyurethanes in sunscreen compositions belongs to the state of the art.
  • DE 1 0223 693 A describes the use of polyurethanes which are prepared by polyaddition of 3-isocyanatomethyl-3,5,5-trimethylcyclohexyl-1-isocyanate and polyhydric alcohols, glycerides, hydroxyesters, silicone derivatives and / or amines.
  • EP 1 214 929 A discloses the use of a film-forming, water-soluble or water-dispersible polyurethane for improving the water resistance of a cosmetic or dermatological preparation containing at least one UV filter.
  • US 2003044364 A in turn, the use of polyurethanes to improve the water resistance of sunscreen formulations is disclosed.
  • EP 2 105 124 A discloses the use of special polyurethanes to simplify the application and to improve the feel on the skin when using the sunscreen formulations.
  • compositions of the prior art with high sun protection factor (SPF) so a high protection effect against solar radiation, due to the necessary significant content of sunscreen filter substances are difficult to distribute on the skin and cause an unpleasant, waxy, sticky feeling on the skin after use.
  • legal provisions limit the maximum allowable amounts of certain sunscreen filter substances, so that high SPF with the known, these sunscreen filter substances containing formulations can not always be realized.
  • the present invention is therefore based on the object to develop a composition of the type mentioned, which causes a h hem SPF when used as a sunscreen while a good, in addition to excellent water resistance, i. a non-sticky and greasy skin feeling causes ..
  • the present invention is therefore based on the object to develop a composition of the type mentioned, which causes a h hem SPF when used as a sunscreen while a good, in addition to excellent water resistance, i. a non-sticky and greasy skin feeling causes ..
  • composition easy to apply and provide a high level of comfort This object is achieved in a composition of the type mentioned in that it contains at least one organic sunscreen filter substance X), with the exception of Octocry- lene, having at least two aromatic groups.
  • composition according to the invention comprising both a polyurethane and at least one organic sunscreen filter substance X), with the exception of octocrylenes having at least two aromatic groups, surprisingly has a significantly higher SPF than the corresponding sunscreen filter substance alone.
  • This effect is hereafter referred to as Termed SPF boosting effect. Its occurrence was not to be expected from the state of the art and offers the advantage of being able to realize a high SPF with smaller amounts of sun protection substances.
  • Iter substance X) has at least one keto group and / or at least 3 nitrogen atoms.
  • the sunscreen filter substance X is a benzophenone, a benzophenone derivative or a derivative derived from triazine.
  • sunscreen absorbency X is selected from the group of benzophenone-3 ((2-hydroxy-4-ethoxyphenyl) -phenylmethanone), ethylhexyl triazone or bisphenol. Ethylhexyloxyphenol methoxyphenyl triazines is selected.
  • water-insoluble, non-water-dispersible polyurethane prepolymer means that the water solubility of the prepolymer according to the invention at 23 ° C less than 10 g / liter, more preferably less than 5 g / liter and the prepolymer at 23 ° C no sedimentation-stable dispersion in water, especially deionized water, in other words, the prepolymer settles when trying to disperse in water.
  • Polyurethanes in the context of the invention are polymeric compounds which have at least two, preferably at least three urethane-group-containing repeat units of the following formula:
  • compositions of the invention are preferably water-containing, i. aqueous compositions in which the polyurethane disperses, i. in the public domain it is not solved.
  • water forms the main constituent (> 50% by weight of the liquid dispersing media) in addition to optionally present other liquid media, such as, for example, solvents; if appropriate, it is also the sole liquid dispersing medium.
  • compositions of the invention preferably have a VOC of less than 80% by weight, more preferably less than 55% by weight, and most preferably less than 40% by weight of the composition ,
  • the aqueous polyurethane dispersions which can be used to prepare the compositions according to the invention preferably have a volatile organic compound (VOC) content of less than 10% by weight, more preferably less than 3% by weight, more preferably less than 1% by weight. %, based on the aqueous polyurethane dispersion on.
  • VOC volatile organic compound
  • VOC volatile organic compounds
  • the non-water-soluble and non-water-dispersible, isocyanate-functional polyurethane prepolymers used according to the invention preferably have essentially neither ionic nor ionogenic groups.
  • the water insolubility or lack of dispersibility in water refers to deionized water without the addition of surfactants.
  • this means that the proportion of ionic and / or ionogenic (ion-forming) groups, in particular anionic groups, such as carboxylate or sulfonate, or cationic groups is less than 15 milliequivalents per 100 g of polyurethane prepolymer.
  • A preferably less than 5 milliequivalents, more preferably less than a milli-equivalent and very particularly preferably less than 0.1 milliequivalents per 100 g of polyurethane prepolymer A).
  • the acid number of the prepolymer is expediently below 30 mg KOH / g prepolymer, preferably below 10 mg KOH / g prepolymer.
  • the Acid value indicates the mass of potassium hydroxide in mg required to neutralize 1 g of the sample to be tested (measurement according to DI EN ISO 21 1).
  • the neutralized acids, ie the corresponding salts naturally have no or a reduced acid number.
  • the acid number of the corresponding free acid is decisive.
  • the prepolymers A) used to prepare the polyurethanes are preferably obtainable by reacting one or more polyols selected from the group of polyether polyols, polycarbonate polyols, polyether polycarbonate polyols and / or polyester polyols with one or more a plurality of polyisocyanates, as explained in more detail below.
  • the polyurethanes contained in the compositions according to the invention therefore preferably contain at least one sequence from the prepolymer which is selected from the group consisting of: polyether, polycarbonate, polyether-polycarbonate and polyester sequences.
  • the polyurethanes contain ether group and / or carbonate group-containing or ester group repeat units.
  • the polyurethanes may for example contain exclusively polyether sequences or exclusively polycarbonate sequences or exclusively polyester sequences. However, they can also have both polyether and polycarbonate sequences, as are formed, for example, in the preparation of polycarbonate polyols using polyether diols, as will be described in detail below. In addition, they may have polyether-polycarbonate sequences derived from polyether-polycarbonate polyols.
  • polyurethanes are obtained using polymeric polyether polyols and / or polymeric polycarbonate polyols and / or polyether olycarbonate polyols or polyester polyols each having number average molecular weights of preferably from about 400 to about 6000 g / mol (here and in the following Molecular weight data determined by gel permeation chromatography over polystyrene standard in
  • Tetrahydrofuran at 23 ° C Tetrahydrofuran at 23 ° C.
  • Their use in the preparation of the polyurethanes or polyurethane prepolymers results by reaction with polyisocyanates to form corresponding polyether and / or polycarbonate and / or polyether-polycarbonate sequences or polyester sequences in the polyurethanes with the corresponding molecular weight of these sequences.
  • polyurethanes which are composed of polymeric polyether Diols and / or polymeric polycarbonate diols and / or polyether-polycarbonate polyols or polyester polyols can be obtained with a linear structure.
  • the isocyanate-functional polyurethane prepolymer A) used according to the invention preferably has terminal isocyanate groups, i. the isocyanate groups are located at the chain ends of the prepolymer. Most preferably, all chain ends of the prepolymer have isocyanate groups.
  • the polyurethane prepolymer A) used according to the invention preferably has essentially neither ionic nor ionogenic groups (capable of forming ionic groups), i. the content of ionic and ionogenic groups is expediently below 15 milliequivalents per 100 g of polyurethane prepolymer A), preferably below 5 milliequivalents, more preferably below one milliequivalent and most preferably below 0.1 milliequivalents per 100 g of polyurethane prepolymer A).
  • the polyurethanes of the invention are preferably substantially linear molecules, but may also be branched, which is less preferred.
  • the average molecular weight of the polyurethanes preferably used according to the invention is for example from about 1000 to 200,000 and preferably from 5000 to 150,000.
  • polyurethanes contained in the compositions according to the invention are added to the compositions mentioned in particular as aqueous dispersions.
  • Preferred polyurethanes or polyurethane dispersions to be used according to the invention are obtainable in which
  • polymeric polyols preferably having number-average molecular weights of from 400 to 8000 g / mol, more preferably from 400 to 6000 g / mol and more preferably from 600 to 3000 g / mol, and oil (functionalities of preferably from 1.5 to 6, more preferably 1, 8 to 3, and more preferably from 1, 9 to 2.1, A3) optionally hydroxy-functional compounds having molecular weights of preferably 62 to 399 g mol, and
  • the polyurethanes used according to the invention are preferably dispersed in water before, during or after step B). Particular preference is given in step B) the reaction with a diamine or a plurality of diamines with chain extension.
  • monofunctional amines can be added as chain terminators for molecular weight control.
  • component B it is possible in particular to use amines which have no ionic or ionogenic, such as anionically hydrophilicizing groups (in the following component B l)). It is also possible to use amines which have ionic or ionogenic, in particular anionic, hydrophilicizing groups (in the following, component B2)).
  • step B) of the reaction of the prepolymer a mixture of component Bl) and component B2) is reacted.
  • component Bl a high molecular weight can be established without the viscosity of the previously prepared isocyanate-functional Prepoly mers increases to an extent that would prevent processing.
  • an optimal balance between lydrophilia and chain length can be established, which leads to a pleasant skin feel of the corresponding composition.
  • the polyurethanes used according to the invention preferably have anionic groups, preferably sulfonate groups. These anionic groups can be introduced into the polyurethanes used according to the invention via the amine component B2) reacted in step B).
  • the polyurethanes used according to the invention optionally additionally comprise nonionic components for hydrophilization. Particular preference is given in the The polyurethanes used according to the invention for the hydrophilization contain exclusively sulfonate groups, which can be introduced into the polyurethane via corresponding diamines as component B2).
  • the number average particle size of the specific polyurethane dispersions is preferably less than 750 nm, more preferably less than 500 nm, determined by laser correlation spectroscopy after dilution with deionized water (apparatus: Malvem Zetasizer 1000, Malver Inst Limited).
  • the solids content of the polyurethane dispersions which are preferably used to prepare the composition of the invention is generally from 10 to 70, preferably from 30 to 65, particularly preferably from 40 to 60,% by weight.
  • the solids contents are determined by heating a weighed sample at 125 '(' to constant weight. At constant weight of the solid content is calculated by reweighing the sample.
  • polyurethane dispersions preferably have less than 5% by weight, more preferably less than 0.2% by weight, based on the mass of the dispersions, of unbound organic amines.
  • the content in the compositions is correspondingly even lower.
  • Suitable polyisocyanates of component AI) are, in particular, the aliphatic, aromatic or cycloaliphatic polyisocyanates known per se to a person skilled in the art of an NC () functionality of greater than or equal to 2.
  • polyisocyanates examples include 1, 4-butylene diisocyanate, 1,6-hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), 2,2,4- and / or 2,4,4-trimethylhexamethylene diisocyanate, the isomeric bis ( 4,4'-isocyanatocyclohexyl) methanes or their mixtures of any desired isomeric, 1,4-cyclohexylene diisocyanate, 4-isocyanatomethyl-1,8-oetandiisocyanate (nonane triisocyanate), 1,4-phenylene diisocyanate, 2,4- and / or 2,6 Tolylene diisocyanate, 1,5-naphthylene diisocyanate, 2,2'-and / or 2,4'- and / or 4,4'-diphenylmethane diol oxy an, 1,3- and / or 1,4-bis- (2-isocyanato
  • modified diisocyanates having a functionality of> 2 with uretdione, isocyanurate, urethane, allophanate, biuret, Iminooxadiazindion- or Oxadiazintrion Modell and mixtures thereof are used proportionately.
  • polyisocyanates or polyisocyanate mixtures of the abovementioned type having exclusively aliphatically or cycloaliphatically bound isocyanate groups or mixtures of these having an average NCO functionality of the mixture of from 2 to 4, preferably from 2 to 2.6 and more preferably from 2 to 2.4, most preferably from 2.
  • Hexamethylene diisocyanate, isophorone diisocyanate or the isomeric bis (4,4'-isocyanatocyclohexyl) methanes and mixtures of the abovementioned diisocyanates are particularly preferably used in Al).
  • A2 are polymeric polyols having a number average molecular weight M "from 400 to
  • polymeric polyols here means in particular that the said polyols have at least two, more preferably at least three interconnected repeat units.
  • Such polymeric polyols are the polyester polyols known per se in polyurethane coating technology, polyacrylate polyols, polyurethane polyols, polycarbonate polyols, polyether polyols, polyester polyacrylate polymers, polyester polyacrylate polyols, polyurethane polyester polyols, polyurethane polyether polyols, polyurethane polycarbonate polyol and polyester polycarbonate polyols. These can be used in A2) individually or in any mixtures with each other.
  • the preferred polyester polyols used are the known polycondensates of di- and optionally tri- and tetra-ols and di- and optionally tri- and tetracarboxylic acids or hydroxycarboxylic acids or lactones. Instead of the free polycarboxylic acids, it is also possible to use the corresponding polycarboxylic acid anhydrides or corresponding polycarboxylic acid esters of lower alcohols to prepare the polyesters.
  • diols examples include ethylene glycol, butylene glycol, diethylene glycol, triethylene glycol, polyalkylene glycols such as polyethylene glycol, furthermore 1,2-propanediol, 1,3-propanediol, butanediol (1,3), butanediol (1,4 ), Hexanediol (1,6) and isomers, neopentyl glycol or! 1-hydroxypivalic acid neopentyl glycol ester, with hexanediol (1,6) and isomeric, butanediol (1,4), neopentyl glycol and neopentyl glycol hydroxypivalate being preferred.
  • polyalkylene glycols such as polyethylene glycol, furthermore 1,2-propanediol, 1,3-propanediol, butanediol (1,3), butanediol (1,4 ), Hexane
  • polyols such as trimethylolpropane, glycerol, erythritol, pentaerythritol, trimethylolbenzene or trishydroxyethyl isocyanurate.
  • phthalic acid As dicarboxylic acids, phthalic acid, isophthalic acid, terephthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, cyclohexanedicarboxylic acid, adipic acid, azelaic acid, sebacic acid, glutaric acid, trichlorophthalic acid, maleic acid, fumaric acid, itaconic acid, malonic acid, suberic acid, 2-methylsuccinic acid, 3 3-diethyl glutaric acid and / or 2,2-dimethylsuccinic acid.
  • the acid source used may also be the corresponding anhydrides.
  • the average functionality of the polyol to be esterified is greater than 2, it is additionally possible to use monocarboxylic acids, such as benzoic acid and hexanecarboxylic acid.
  • Preferred acids are aliphatic or aromatic acids of the abovementioned type. Particular preference is given to adipic acid, isophthalic acid and phthalic acid.
  • Hydroxycarboxylic acids which can be used as reactants in the preparation of a hydroxyl-terminated polyester polyol include hydroxycaproic acid, hydroxybutyric acid, hydroxydecanoic acid, hydroxystearic acid and the like.
  • Suitable lactones are caprolactone, butyrolactone and homologs. Preference is given to caprolactone.
  • polyester polyols having a number average molecular weight of 600 to 3000 g / mol.
  • Particularly preferred here are aliphatic polyester polyols based on aliphatic
  • Carboxylic acids and aliphatic polyols in particular based on adipic acid and aliphatic alcohols, such as hexanediol and / or neopentyl glycol.
  • hydroxyl-end-blocking polycarbonates preferably polycarbonatediols, having number-average molecular weights M "of preferably 400 to 8000 g / mol, and more preferably 600 to 3000 g / mol. These are through Reaction of carbonic acid derivatives, such as diphenyl carbonate, dimethyl carbonate or phosgene, with polyols, preferably diols. available.
  • diols examples include ethylene glycol, 1,2- and 1,3-propanediol, 1,3- and 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, neopentyl glycol, 1,4-bishydroxymethylcyclohexane, 2-Methyl-1,3-propanediol 2,2,4-trimethylpentanediol 1, 3, dipropylene glycol, polypropylene glycols, dibutylene glycol, polybutylene glycols, bisphenol A and lactone-modified diols of the abovementioned type.
  • the diol component preferably contains from 40 to 100% by weight of hexanediol; preference is given to 1,6-hexanediol and / or hexanediol derivatives.
  • hexanediol derivatives are based on hexanediol and have ester or ether groups in addition to terminal OH groups.
  • Such derivatives are obtainable by reaction of hexanediol with excess caprolactone or by etherification of hexanediol with itself to give di- or tri-ethylene glycol.
  • polyether-polycarbonate diols instead of or in addition to pure polycarboxylate diols, it is also possible to use polyether-polycarbonate diols in A2). Hydroxyl-containing polycarbonates are preferably built linear.
  • component A2 may be polyether polyols.
  • polytetramethylene glycol polyethers known per se in polyurethane chemistry such as are obtainable by polymerization of tetrahydrofuran by means of cationic ring opening, are particularly suitable.
  • suitable polyether polyols are the per se known addition products of styrene oxide, ethylene oxide, propylene oxide, butylene oxide and / or epichlorohydrin to di- or polyfunctional starter molecules.
  • polyalkylene glycols such as polyethylene, polypropylene and / or polybutylene glycols are applicable, in particular those having the above-mentioned preferred molecular weights.
  • starter molecules it is possible to use all compounds known from the prior art, for example water, butyldiglycol, glycerol, diethylene glycol, trimethylolpropane, propylene glycol, sorbitol, ethylenediamine, triethanolamine, 1,4-butanediol.
  • Particularly preferred components in Al) are polytetramethylene glycol polyethers and polycarboxylate polyols or mixtures thereof, and polytetra methylene glycol polyethers are particularly preferred.
  • component A2) is accordingly:
  • polyols in particular nonpolymeric polyols, of the preferred molecular weight range from 62 to 399 moi / g with up to 20 carbon atoms, such as ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propanediol, 1,3-propanediol, 1, 4-butanediol, 1,3-butylene glycol, cyclohexanediol, 1,4-cyclohexanedimethanol, 1,6-hexanediol, neopentyl glycol, hydroquinone dihydroxyethyl ether, bisphenol A (2,2-bis (4-hydroxyphenyl) propane), hydrogenated bisphenol A ( 2,2-bis (4-hydroxycyclohexyl-1-propane), trimethylolpropane, trimethylolethane, glycerol, pentaerythritol and any desired mixtures thereof with one another.
  • polyols in particular nonpolymeric polyo
  • ester diols of the stated molecular weight range such as ⁇ -hydroxybutyl ⁇ -hydroxy-caproic acid ester, ro-hydroxyhexyl- ⁇ -hydroxybutyric acid ester, adipic acid ( ⁇ -hydroxyethyl) ester or terephthalic acid bis ( ⁇ -hydroxyethyl) ester.
  • component A3 it is also possible to use monofunctional isocyanate-reactive compounds containing hydroxyl groups.
  • monofunctional compounds are ethanol, n-butanol, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monomethyl ether, dipropylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monobutyl ether, tripropylene glycol monobutyl ether, 2-ethylhexanol, 1-octanol. 1 -Dodecanoi, 1-hexadecanol.
  • the polyurethane used according to the invention contains less than about 10% by weight and preferably less than 5% by weight of component A3), in each case based on the total mass of the polyurethane.
  • component A3) is particularly preferably not used for the preparation of the polyurethane.
  • component A4) one or more in particular isocyanate-reactive nonionic hydrophilicizing agents are optionally used to prepare the polyurethanes used according to the invention.
  • the hydrophilicizing agents used as component A4) are in particular different from components A2) and A3).
  • Suitable nonionically hydrophilicizing compounds of component A4) are e.g. Polyoxyalkylene ethers which have isocyanate-reactive groups, such as hydroxyl, amino or thiol groups. Preference is given to monobydroxy-functional, on average 5 to 70, preferably 7 to 55 ethylene oxide units per molecule having polyalkylene oxide poly oly ether alcohols, as they are accessible in a conventional manner by alkoxylation of suitable starter molecules (eg described in Ullmann's Encyclopaedia der ischen Chemistry, 4th Edition, Volume 19, Verlag Chemie, Weinheim p. 31-38). These are either pure
  • Polyethylene oxide ethers or mixed polyalkylene oxide ethers wherein they contain at least 30 mol%, preferably at least 40 mol%, based on all alkylene oxide units contained, of ethylene oxide units.
  • Particularly preferred nonionic compounds are monofunctional mixed polyalkylene oxide polyethers which have 40 to 100 mol% of ethylene oxide and 0 to 60 mol% of propylene oxide units.
  • Suitable starter molecules for such nonionic Hydrophil istsmittei are in particular saturated monoalcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, sec-butanol, the isomeric pentanols, hexanols, octanols and nonanols, n-decanol, n-dodecanol , n-tetradecanol, n-hexadecanol, n-octadecanol, cyclohexanol, the isomeric methylcyclohexanols or hydroxymethylcyclohexane, 3-ethyl-3-hydroxymethyloxetane or tetrahydahydrofurfuryl alcohol, diethylene glycol monoalkyl ethers, such as diethylene glycol monobutyl ether, unsaturated alcohols
  • Preferred starter molecules are saturated monoalcohols of the abovementioned type. Particular preference is given to using diethylene glycol monobutyl ether or n-butanol as starter molecules.
  • Alkylene oxides suitable for the alkoxylation reaction are, in particular, ethylene oxide and propylene oxide. which can be used in any order or in a mixture in the alkoxylation reaction.
  • Component B) is preferably selected from primary or secondary amine and / or diamines. It includes in particular diamines.
  • component B it is possible in particular to use amines which have no ionic or ionogenic, such as anionically hydrophilicizing groups (in the following component
  • step B) of the reaction of the prepolymer a mixture of component Bl) and component B2) is reacted.
  • the amino-functional compounds B) are preferably selected from primary and / or secondary amines and / or diamines. In particular, the amino-functional compounds B) comprise at least one diamine.
  • the amino-functional compounds B) can comprise at least one amino-functional compound B1) which has no ionic and / or ionogenic groups, the amino-functional compound B 1) preferably being a diamine which has no ionic and / or ionogenic groups , can act.
  • the amino-functional compounds B) comprise at least one amino-functional compound B2) which has ionic and / or ionogenic (ion-forming) groups.
  • the ionic and / or ionogenic group used is particularly preferably the sulfonate or sulfonic acid group, more preferably the sodium sulfonate group.
  • the amino-functional compound B2) can be 2- (2-aminoethylamino) ethanesulfonic acid and / or salts thereof.
  • the amino-functional compounds B) comprise both amino-functional compounds B2) which have ionic and / or ionogenic groups and also amino-functional compounds BI) which have no ionic or ionogenic group.
  • organic di- or polyamines such as 1, 2-ethylenediamine, 1, 2- and 1, 3-diaminopropane, 1, 4-diaminobutane, 1, 6-diaminohexane, isophoronediamine.
  • component B l compounds which, in addition to a primary amino group, also have secondary amino groups or, in addition to an amino group (primary or secondary), also Ol I groups, can be used.
  • primary / secondary amines such as diethanolamine, 3-amino-1-methylaminopropane, 3-amino-1-ethylaminopropane, 3-amino-1-cyclohexylaminopropane, 3-amino-1-methylaminobutane, alkanolamines such as N-aminoethylethanolamine , Ethanolamine, 3-aminopropanol, neopentanolamine.
  • component Bl it is also possible to use monofunctional isocyanate-reactive amine compounds, such as, for example, methylamine, ethylamine, propylamine. Butylamine, octylamine, laurylamine, stearylamine, isononyloxypropylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, N-methylaminopropylamine, diethyl (methyl) aminopropylamine, morphine.
  • monofunctional isocyanate-reactive amine compounds such as, for example, methylamine, ethylamine, propylamine. Butylamine, octylamine, laurylamine, stearylamine, isononyloxypropylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, N-methylaminopropylamine, diethyl (methyl) aminopropylamine, morphine.
  • Piperidine or suitable substituted derivatives thereof, amide amines from diprimary amines and monocarboxylic acids, monoketim of diprimary amines, primary / tertiary amines, such as N, N-methylaminopropylamine.
  • 1, 2-ethylenediamine, bis (4-aminocyclohexyl) methane, 1, 4-diaminobutane, isophoronediamine, ethanolamine, diethanolamine and diethylenetriamine are preferably used as component Bl).
  • component B) comprises at least one component B2).
  • Suitable anionically hydrophilicizing compounds as component B2) preferably contain a sulfonic acid or sulfonate group, more preferably a sodium sulfonate group.
  • Suitable anionically hydrophilicizing compounds as component 62) are, in particular, the alkali metal salts of ono- and diaminosulfonic acids. Examples of such anionic iridylating agents are salts of 2- (2-aminoethylamino) ethanesulfonic acid, ethylenediamine-propyl- or -butylsulfonic acid, 1,2- or 1,3-propylenediamine- ⁇ -ethylsulfonic acid or taurine.
  • anionic hydrophilicizing agents B2 are those which contain sulfonate groups as ionic groups and two amino groups such as the salts of 2- (2-aminoethylamino) ethylsulfonic acid and 1, 3-propylenediamine-.beta.-ethylsulfonic acid.
  • the polyurethanes used according to the invention particularly preferably contain at least one sulfonate group.
  • the anionic group in component 62) may also be a carboxylate or carboxylic acid group.
  • Component B2) is then preferably selected from diaminocarboxylic acids. However, this embodiment is less preferred, the carboxylic acid-based components B2) must be used in higher concentrations.
  • hydrophilization it is also possible to use mixtures of anionic hydrophilicizing agents 62) and nonionic hydrophilicizing agents A4).
  • the components Al) to A4) and Bl) to B2) are used in the following amounts, the individual amounts always adding up to 100% by weight:
  • the components Al) to A4) and Bl) to B2) are used in the following amounts, the individual amounts always adding up to 100% by weight:
  • the components Al) to A4) and Bl) to 62) are used in the following amounts, the individual amounts always adding up to 100% by weight:
  • component Al 10 to 30% by weight of component Al), 65 to 85% by weight of A2), 0.5 to 14 wt .-% sum of the components A3) and / or Bl)
  • the preparation of the polyurethane dispersions can be carried out in one or more stages in homogeneous or multistage reaction, partially disperse phase. After complete or partial polyaddition from Al) to A4), a dispersing, emulsifying or dissolving step is preferably carried out. This is followed, if appropriate, by a further polyaddition or modification in disperse phase.
  • Polyurethane polymers submitted in whole or in part and optionally diluted with a water-miscible but isocyanate-inert solvent and heated to temperatures ranging from 50 to 120 ° C. To accelerate the Isocyanatadditionsre force known in polyurethane chemistry catalysts can be used.
  • Suitable solvents are the customary aliphatic, ketofunctional solvents such as acetone, 2-butanone, which may be added not only at the beginning of the preparation, but optionally also in parts later. Preference is given to acetone and 2-butanone, particular preference to acetone. The addition of other solvents without isocyanate-reactive groups is possible, but not preferred.
  • the components of Al) to A4) which are optionally not added at the beginning of the reaction, are metered in.
  • the molar ratio of isocyanate groups to isocyanate-reactive groups is generally from 1.05 to 3.5, preferably from 1.1 to 3.0, particularly preferably from 1.1 to 2, 5th
  • reaction of components AI) to A4) to the prepolymer takes place partially or completely, but preferably completely.
  • polyurethane prepolymers containing free isocyanate groups are obtained in bulk or in solution.
  • bases such as tertiary amines, for example trialkylamines having 1 to 12, preferably 1 to 6 ( “ atoms, particularly preferably 2 to 3 (. " in each alkyl radical or most preferably used alkali metal bases such as the corresponding hydroxides.
  • inorganic bases such as aqueous ammonia solution or sodium or potassium hydroxide can be used. Preference is given to sodium hydroxide and potassium hydroxide.
  • the molar amount of the bases is generally 50 and 125 mol%, preferably 70 and 100 mol% of the molar amount of the acid groups to be neutralized.
  • the neutralization can also take place simultaneously with the dispersion in which the dispersing water already contains the neutralizing agent. Subsequently, in a further process step, if not yet or only partially done, the resulting prepolymer with the aid of aliphatic ketones such as acetone or 2-butanone dissolved.
  • reaction of components AI) to A4) / prepolymer takes place partially or completely, but preferably completely. In this way, polyurethane prepolymers which contain free isocyanate groups are obtained in bulk or in solution.
  • Suitable components B) for chain extension are in particular organic di- or polyamines B1) such as, for example, ethylenediamine, 1,2- and 1,3-diaminopropane, 1,4-diaminobutane, 1,6-diaminohexane, isophoronediamine, isomer mixture of 2 , 2,4- and 2,4,4-trimethylhexamethylenediamine, 2-methylpentamethylenediamine, diethylenetriamine, diaminodicyclohexylmethane and / or dimethylethylenediamine.
  • organic di- or polyamines B1 such as, for example, ethylenediamine, 1,2- and 1,3-diaminopropane, 1,4-diaminobutane, 1,6-diaminohexane, isophoronediamine, isomer mixture of 2 , 2,4- and 2,4,4-trimethylhexamethylenediamine, 2-methylpentamethylenediamine, diethylenetri
  • compounds B1) which, in addition to a primary amino group, also have secondary amino groups or, in addition to an amino group (primary or secondary), also Ol I groups.
  • primary / secondary amines such as diethanolamine, 3-amino-1-methylaminopropane, 3-amino-1-ethylaminopropane, 3-amino-1-cyclohexylaminopropane, 3-amino-1-methylaminobutane, alkanolamines, such as N-aminoethylethanolamine , Ethanolamine, 3-aminopropanol, neopentanolamine to chain extension b / w. Termination be used.
  • amines Bl are usually used with an isocyanate-reactive group, such as methylamine, ethylamine, propylamine, butylamine, octylamine, laurylamine, stearylamine, isononyloxypropylamine, dimethylamine, diethylamine, dipropylamine.
  • an isocyanate-reactive group such as methylamine, ethylamine, propylamine, butylamine, octylamine, laurylamine, stearylamine, isononyloxypropylamine, dimethylamine, diethylamine, dipropylamine.
  • anionic hydrophilicizing agents corresponding to the deletion B2) with NI F or Nl 1 groups are used for chain extension, the chain extension of the prepolymers is preferably carried out before the dispensing.
  • the degree of chain extension that is to say the equivalent ratio of NCO-reactive groups of the compounds used for chain extension and ketene to reduce free NCO groups of the prepolymer, is generally between 40 and 150%, preferably between
  • the aminic components B1) and B2) can, if appropriate, be used in aqueous or solvent-dense form in the process according to the invention individually or in mixtures, it being possible in principle for any order of addition to be possible.
  • the diluent content in the chain-extending component used in B) is preferably 40 to 95% by weight.
  • the dispersion preferably takes place after the chain extension.
  • the dissolved and chain extended polyurethane polymer is optionally sheared under high shear, e.g. vigorous stirring, either added to the dispersing water or, conversely, the dispersing water is stirred into the chain-extended polyurethane polymer solutions.
  • the water is added to the dissolved chain-extended polyurethane polymer.
  • the solvent still present in the dispersions after the dispersion step is then usually removed by distillation. A removal already during the dispersion is also possible.
  • the residual content of organic solvents in the polyurethane dispersions thus prepared is typically less than 10 wt .-%, preferably less than 3 wt .-%, based on the total dispersion.
  • the pH of the aqueous polyurethane dispersions used according to the invention is typically less than 8.0, preferably less than 7.5 and is more preferably between 5.5 and 7.5.
  • compositions according to the present invention may in particular be in the following forms: cream, lotion, milk, gel, oil, balm, aqueous solution.
  • the composition according to the invention preferably contains from 0.1 to 20% by weight and in particular from 0.5 to 10% by weight, based in each case on the total weight of the composition, of the above-described polyurethane.
  • compositions may be in the form of, for example, oil-in-water, water-in-oil, water-in-silicone, silicone-in-water, oil-in-water-in-oil, water-in-oil in water emulsion.
  • the composition may further be foamed with a propellant gas.
  • the emulsions can be stabilized, for example, by O / W, W / O or W / Si emulsifiers, thickeners (such as, for example, a hydrodispersion) or solids (such as, for example, a Pickering emulsion).
  • compositions may also contain one or more emuigators or surface-active agents.
  • oil-in-water emulsions (O / W) preferably contain at least one emulsifier having an I IL B value> 7 and optionally a co-emulsifier.
  • O / W emuigators can be chosen in particular from the group of nonionic, anionic, cationic or amphoteric emuigators.
  • nonionic emuigators are, for example: a) partial fatty acid esters and fatty acid esters of polyhydric alcohols and their ethoxylated derivatives
  • alkylphenol polyglycol ethers e.g., Triton * X
  • nonionic O / W emulsifiers are ethoxylated fatty alcohols or
  • Fatty acids preferably PEG-100 stearates, PEG-40 stearates, PEG-50 stearates, ceteareth-20, ceteth-20, steareth-20, ceteareth-12, ceteth-12, steareth-12, esters of mono-, oligo- or polysaccharides with fatty acids, preferably cetearyl glucoside, methyl glucose distearate, glycerol rylmonostearate (self-emulsifying), sorbitan esters such as sorbitan stearate (Tween ® 20 and Tween ® 60 from Uniqema), sorbitan palmitates (Span ® 40, Uniqema), glyceryl stearyl citrates, sucrose esters such as sucrose stearate, PEG-20 methylglucose sequistearate) dicarboxylic acid esters of fatty alcohol (dimyristyl tartrate).
  • anionic emuigators are soaps (for example sodium or triethanolamine salts of stearic or palmitic acid), esters of citric acid such as glyceryl stearate citrate, fatty alcohol sulfates and mono-, di- and trialkylphosphoric acid esters and their ethoxylates.
  • cationic emulsifiers are quaternary ammonium compounds with a long-chain aliphatic radical, for example distearyldimonium chlorides.
  • Amphoteric emulsifiers are, for example: a) alkylamininoalkanecarboxylic acids
  • emulsifiers which include, for example, beeswax, wool wax, lecithin and sterols.
  • Suitable coemulsifiers for the novel O / W emulsions are fatty alcohols having 8 to 30 carbon atoms, monoglycene esters of saturated or unsaturated, branched or unbranched alkane carboxylic acids having a chain length of 8 to 24 carbon atoms, in particular 12 to 18 carbon atoms, propylene glycol esters saturated or unsaturated, branched or unbranched AikancarbonTexren having a chain length of 8 to 24 carbon atoms, in particular 12 to 18 carbon atoms, and sorbitan esters of saturated or unsaturated, branched or unbranched Aikancarbonklaren with a Ketteniaenge of 8 to 24 carbon atoms, in particular 12 to 18 carbon atoms, are used.
  • co-emulsifiers are glyceryl monostearate, glyceryl monooleate, diglyceryl monostearate, sorbitan monoisostearate, sucrose distearate, cetyl alcohol, stearyl alcohol, behenyl alcohol, isobehenyl alcohol and polyethylene glycol (2) stearyl ether (steareth-2).
  • emulsifiers are z.
  • Lecithin glyceryl isostearate, polyglyceryl-3-oleate, polyglyceryl-3-diisostearate, PEG-7 hydrogenated ricinus oil, polyglyceryl-4-isostearate, acrylate / C 10.30-alkyl acrylate crosspolymer, sorbitan isostearate, poloxamer 101, polyglyceryl-2-dipolyhydroxystearate, polyglyceryl -3- diisostearate, polyglyceryl-4-dipolyhydroxystearate, PEG-30-dipolyhydroxystearate, diisoste- aroylpolyglyceryl-3-diisostearate, glycol distearate and polyglyceryl-3-dipolyhydroxystearate.
  • compositions of the invention may advantageously contain thickeners of the water phase.
  • Suitable thickeners are: crosslinked or non-crosslinked acrylic acid or methacrylic acid homo- or copolymers. These include crosslinked homopolymers of methacrylic acid or acrylic acid, copolymers of acrylic acid and / or methacrylic acid, and monomers derived from other acrylic or vinyl monomers, e.g. C10-30 alkyl acrylates, C10-3 O-alkyl methacrylates, vinyl acetate and vinyl pyrrolidones. Thickening polymers of natural origin, for example based on cellulose,
  • Nonionic, anionic, cationic or amphoteric associative polymers e.g. based on polyethylene glycols and their derivatives or polyurethanes.
  • Crosslinked or non-crosslinked homopolymers or copolymers based on acrylamide or methacrylamide such as homopolymers of 2-acrylamido-2-methylpropanesulfonic acid, copolymers of acrylamide or methacrylamide and methacryloyloxyethyltrimethylammonium chloride or copolymers of acrylamide and 2-acrylamido-2-methylpropanesulfonic acid.
  • Particularly advantageous thickeners are thickening polymers of natural origin, crosslinked acrylic or methacrylic acid homopolymers or copolymers and crosslinked copolymers of 2-acrylamido-2-methylpropanesulfonic acid.
  • xanthan gum such as the products supplied under the names Keltrol ® and Kelza ® by CP Kelco or the products of
  • Rhodopol and guar gum such as those sold under the name Jaguar ® HP 105 by the company Rhodia.
  • Very particularly advantageous thickeners are re also crosslinked homopolymers of methacrylic or acrylic acid, from Lubrizol under the names Carbopol ® 940
  • Very particularly advantageous thickeners are crosslinked copolymers of acrylic acid or methacrylic acid and a C i OJ 0 - Alky lacrylat Ciojo or alkyl methacrylate and Coplymere of acrylic acid or methacrylic acid and vinyl pyrrolidones.
  • Such copolymers are beispielswei- se from the Finna Lubrizol under the names Carbopol * 1342, Carbopol ® 1382, Pemulen TRI ® or Pemulen ® TR2 and (Finna from ISP under the designations Ultra thix ® P-100 INCI: Acrylic Acid / VP Crosspolymer) commercially available.
  • Very particular advantageous thickeners are crosslinked copolymers of 2-acrylamido-2-methylpropanesulfonic acid.
  • Such copolymers are, for example, by the company Clariant under the names Aristoflex ® AVC (INCI: Ammonium Acryloyldimethyltaurate / VP
  • thickeners are generally present at a level of from about 0% to about 2% by weight, preferably from about 0% to about 1% by weight, based on the total weight of the composition of the present invention.
  • Other compositions of the invention may be water-in-oil or water-in-silicone emulsions.
  • the silicone emulsifiers can advantageously be selected from the group comprising alkyldimethicone copolyols, such as, for example, B. Cetyl PEG / PPG 10/1 Dimethicone (ABIL ® EM 90 from the company.
  • Lauryl PEG / PPG 18/18 dimethicone (Dow Corning ® 5200 from the company. Dow Corning Ltd.), and Dimethiconecopolyole such.
  • PEG-10 Dimethicone KF-6017 from Shin Etsu
  • PEG / PPG-18/18 Dimethicone Dow Corning 5225C from Dow Corning Ltd.
  • PEG / PPG Dimethicone Dow Corning BY-1 1030 from Dow Corning Ltd.
  • trimethylsilylamodimethicone can be selected.
  • the W / O emulsifiers having an I IL B value ⁇ 7 can advantageously be selected from the following group: fatty alcohols having 8 to 30 carbon atoms, monoglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids of a chain length of 8 to 24, in particular 12-18 ( " -toms, diglycerol esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 8 to 24, in particular 12-18, carbon atoms, monoglycerol ethers, saturated and / or unsaturated, branched and / or or unbranched alcohols having a chain length of 8 to 24, in particular 12 to 18, carbon atoms, diglycerol ethers of saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of 8 to 24, in particular 12 to 18 carbon atoms, diglyce
  • W / O emulsifiers are: glyceryl Glycerylmonoisostea- advice, glyceryl monomyristate, glyceryl, diglyceryl monostearate, Diglycerylmo- noisostearat, propylene glycol, propylene glycol monoisostearate, Propylenglycolmo- nocaprylat, anmonocaprylat propylene glycol, sorbitan, sorbitan, sorbitol, Sorbitanmonoisooleat, sucrose, cetyl alcohol, stearyl , Arachidyl alcohol, behenyl alcohol, isobehenyl alcohol, selachyl alcohol, chimyl alcohol, polyethylene glycol (2) stearyl ether (steareth-2), glyceryl monolaurate, glyceryl monocaprinate and glyceryl monocaprylate.
  • glyceryl Glycerylmonoisostea- advice
  • W / O emulsifiers are selected from the group of the compounds polyglyceryl-2-dipolyhydroxystearate, PEG-30 dipolyhydroxystearate, cetyl dimethicone copolyol and polyglyceryl-3 diisostearate.
  • the O / W emulsifiers having an HLB value> 10 can advantageously be selected from the group comprising lecithin, trilaureth-4-phosphate, polysorbate-20, polysorbate-60, PEG-22-dodecylglycol copolymer, sucrose stearate and sucrose laurate.
  • an oil thickener can advantageously be used.
  • Particularly advantageous oil thickeners are organo-modified clays such as organically modified bentonites (Bentone ® 34 from Rheox) organomodified Hectorite (Bentone * 27 and Bentone ® 38 from Rheox) or organo-montmorillonite, hydrophobic fumed silica, wherein the silanol groups with trimethylsiloxy groups are subtituiert (AEROSIL ® RS 12 from Degussa) or dimethylsiloxy groups or polydimethylsiloxane (Aerosil ® R972, Aerosil ® R974 by Degussa, CAB-O-SIL ® TS-610, "CAB-O-SIL ® TS-720 from Cabot), magnesium or aluminum stearate, or styrene copolymers such as styrene-butadiene-styrene, styrene-isoprene-styrene, styrene
  • the fat phase thickener may be contained in an amount of from 0.1 to 5% by weight, and preferably from 0.4 to 3% by weight, based on the total weight of the emulsion.
  • the aqueous phase may further contain stabilizing agents.
  • the stabilizing agent may be, for example, sodium chloride, magnesium chloride or magnesium sulfate and a mixture thereof.
  • Oils can be used in W / O, W / Si and O / W emulsions.
  • the fat phase of the composition of the invention may contain a non-volatile oil and / or volatile oils and waxes.
  • the O / W composition advantageously contains from 0.01 to 45% by weight of oils, based on the total weight of the composition, and more preferably contains from 0.01 to 20% by weight of oils.
  • the W / O od he W / Si composition advantageously contains at least 20 wt.% Oils, based on the total weight of the composition.
  • the non-volatile oil is advantageously selected from the group of mineral, animal, vegetable or synthetic origin, polar or nonpolar oils and mixtures thereof.
  • the lipid phase of the cosmetic or dermatological emulsions according to the invention can advantageously be selected from the following substance group: mineral oils, mineral waxes, polar Oils, such as triglycerides of capric or caprylic acid, and also natural oils, such as castor oil; Fats, waxes and other natural and synthetic fatty substances, preferably esters of fatty acids with alcohols of low C number, for example with isopropanol, propylene glycol or glycerol, or esters of fatty alcohols with alkanoic acids of low C number or with fatty acids; Alkyl benzoates; Silicone oils such as dimethylpolysiloxanes, diethylpolysiloxanes, diphenylpolysiloxanes and mixed forms thereof.
  • mineral oils mineral waxes, polar Oils, such as triglycerides of capric or caprylic acid, and also natural oils, such as castor oil
  • the polar oils are advantageously selected from the following group: a) esters of saturated and / or unsaturated, branched and / or unbranched alkanecarboxylic acids having a chain length of 3 to 30 carbon atoms and saturated and / or unsaturated, branched and / or or unbranched alcohols having a chain length of 3 to 30 carbon atoms, b) esters of aromatic carboxylic acids and saturated and / or unsaturated, branched and / or unbranched alcohols having a chain length of 3 to 30 carbon atoms.
  • alkyl benzoates C12-15 alkyl benzoate (Finsolv ® TN from Finetex), or 2-phenylethyl benzyl Zoate (X-Tend 226 from ISP ®)
  • lecithins and fatty acid triglycerides namely the triglycerol esters of saturated and / or unsaturated, branched and or unbranched alkanecarboxylic acids of a chain length of 8 to 24, in particular 12 to 18 carbon atoms are selected.
  • the fatty acid triglycerides may be selected from the group of cocoglyceride, olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil, coconut oil, castor oil, wheat germ oil, grape seed oil, thistle oil, evening primrose oil, macadamia nut oil, apricot oil, avocado oil and the like ,
  • the dialkyl ethers and dialkyl carbonates are, for example, dicaprylyl ether (Cetiol OE from Cognis ®) and / or dicaprylyl carbonate (Cetiol ® CC, for example, from Cognis).
  • the nonvolatile oil may also advantageously be a nonpolar oil selected from the group of branched and unbranched hydrocarbons, in particular mineral oil, vaseline oil, paraffin oils, squalane and squalene, polyolefins, for example polydecenes, hydrogenated polyisobutenes, C 13-16 isoparaffin and isohexadecane ,
  • the nonpolar non-volatile oil may be selected from nonvolatile silicone oils.
  • non-volatile silicone oils in particular the polydimethylsiloxanes (PDMS) can be used.
  • PDMS polydimethylsiloxanes
  • Particular advantageous oils are 2-ethylhexyl isostearate, octyldodecanol, isotridecylisononane, isoeicosane, 2-ethylhexyl cocoate, C 12-15 alkyl benzoate, caprylic / capric triglyceride, dicaprylyl ether, mineral oil, dicaprylyl carbonates, cocoglycerides, butylenes glycol dicarbyrene late / Dic apr ate, hydrogenated polyisobutenes, cetaryl isononanoates, isodecyl neopentanoates, squalane, C 13-16 isoparaffin.
  • composition of the invention may further contain a wax.
  • a wax is defined as lipophilic fatty substance, which in
  • Room temperature (25 ° C) is fixed and at a melting temperature between 30 ° C and 200 ° C shows a reversible change in state solid / liquid. Above the melting point, the wax becomes low viscous and miscible with oils.
  • the wax is advantageously from the groups of natural waxes such as cotton wax, carnauba wax, C andelilla wax, Espartoawachs, Japan wax, montan wax, sugarcane wax, beeswax, wool wax, shellac, microwaxes, ceresin, Ozo kerit, Ouricuriwachs, cork fiber wax, lignite waxes, Berrenwachs , Shea butter or synthetic waxes such as paraffin waxes, polyethylene waxes, Fischer-Tropsch synthesis waxes, hydrogenated oils, fatty acid esters and glycerides solid at 25 ° C, silicone waxes and derivatives (alkyl derivatives, alkoxy derivatives and / or esters of polymethylsiloxane) and mixtures thereof.
  • the waxes may be in the form of stable dispersions of colloidal wax particles which can be prepared by known methods, for example, according to "Microemulsion Theory and Practice", LM Prince Ed., Academic Press (1977),
  • the waxes may be present in amounts of from 0 to 10% by weight, and preferably from 0 to 5% by weight, based on the total weight of the composition.
  • the composition of the invention may further comprise a volatile oil selected from the group of volatile hydrocarbon oils, siliconized oils or fluorinated oils.
  • the volatile oil may be contained in an amount of from 0 to 25% by weight, preferably from 0 to 20% by weight, and more preferably from 0 to 15% by weight, based on the total weight of the emulsion.
  • a volatile oil is an oil that dissipates in contact with the skin at room temperature and atmospheric pressure in less than one hour.
  • the volatile oil is liquid at room temperature and has a vapor pressure of from 0.13 to 40,000 Pa (10 -3 to 300 mg Hg) at room temperature and atmospheric pressure, preferably from 1.3 to 13,000 Pa (0.01 to 100 mm Hg ) and more preferably from 1.3 to 1300 Pa (0.01 to 10 mm Hg) and has a boiling point of 150 to 260 ° C and preferably 170 to 250 ° C.
  • a hydrocarbon oil is understood as meaning an oil which is formed essentially from carbon atoms and hydrogen atoms and optionally oxygen atoms or nitrogen atoms and contains no silicon atoms or fluorine atoms. It may contain ester groups, ether groups, amino groups or amide groups.
  • a siliconized oil is understood to mean an oil which contains at least one silicon atom and in particular Si-O groups.
  • a fluorinated oil is meant an oil containing at least one fluorine atom.
  • the volatile hydrocarbons may be selected from hydrocarbon oils having a flash point of from 40 to 102 ° C, preferably from 40 to 55 ° C, and more preferably from 40 to 50 ° C.
  • Suitable volatile hydrocarbon oilles are those having 8 to 16 carbon atoms and mixtures thereof, in particular branched Cg-IE alkanes, such as the isoalkanes (which are also referred to as isoparaffins) having 8 to 16 carbon atoms, isododecane, isodecane, isohexadecane and, for example, the oils be offered under the trade names Isopars ® or Permethyls ® ; and the branched such as isohexyineopentanoate and their mixtures.
  • volatile hydrocarbon oils such as isododecane, isodecane and isohexadecane.
  • the inventively volatile siliconized oil can be selected from among the siliconized oils having a flash point of 40 to 102 ° C.
  • the volatile siliconized oils may be straight-chain or cyclic silicone oils having 2 to 7 silicon atoms, which silicones may optionally contain alkyl or alkoxy groups having 1 to 10 carbon atoms.
  • volatile siliconized oils such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasiloxane, dodecamethylpentasiloxane and mixtures thereof.
  • volatile siliconized oils such as octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, heptamethylhexyltrisiloxane, heptamethyloctyltrisiloxane, hexamethyldisiloxane, octamethyltrisiloxane, decamethyltetrasilox
  • the volatile fluorinated oil generally has no flash point.
  • Examples are the volatile fluorinated oils nonafluoroethoxybutane, nonafluoromethoxybutane,
  • the cosmetically acceptable medium of the composition of the invention contains water and optionally a water-miscible, suitable organic solvent.
  • the water used in the composition according to the invention may be a sewage water, pure demineralized water, mineral water, thermal water and / or seawater.
  • the water content in the range of 40 to 95 wt.
  • the water content in the range of 0 up to 60% by weight, preferably in the range from 10 to 50% by weight, very preferably in the range from 30 to 50% by weight, based on the total weight of the composition.
  • the preferred solvents are C 1-4 aliphatic alcohols such as ethanol and isopropanol; Glycol ethers such as propylene glycol, dipropylene glycol, butylene-1, 3-glycol, polypropylene glycol alkyl (Cl-4) ether of mono-, di- or tripropylene glycol or mono-; Di- or triethylene glycol, and mixtures thereof.
  • the proportion of the solvent or solvents in the composition of the invention may be, for example, in the range of 0 to 25% by weight, and preferably in the range of 0 to 10% by weight, based on the total weight of the composition.
  • composition of the invention contains a total of 5 to 40 wt .-%, preferably 10 to 40 wt .-%, particularly preferably 20 to 40 wt .-% sunscreen filter substances, based on the total weight of the composition.
  • the stated amount is the sum of the amounts of all sunscreen filter substances contained in the composition according to the invention.
  • Sunscreen filter substances can also be referred to as sunscreen or sunscreen mediating substances.
  • the sunscreen filter substance X is present in an amount of from 1 to 30% by weight, preferably from 1 to 20% by weight, particularly preferably from 1 to 15% by weight, in the composition.
  • the sun protection filters are, in particular, UV filters which filter UV light. Usually, the UV wavelength range is divided as follows:
  • the UV filters can be selected among the organic filters, the physical filters and their mixtures.
  • the composition according to the invention may in particular comprise UV-A filters, UV-B filters,
  • composition of the invention preferably contains mixtures of at least two of these aforementioned types of sunscreen filter substances.
  • the composition of the invention may also contain a plurality of sunscreen filter substances associated with one of these types of sunscreen filter substances, i. e.g. multiple UV filters and / or multiple UV-B filters. Any combinations are possible here.
  • UV filters used may be oil-soluble or water-soluble.
  • the following list of UV filters is obviously not limiting.
  • UV-B filters are, for example: (1) salicylic acid derivatives, especially homomenthyl salicylate, octyl salicylate and 4-isopropylbenzyl salicylate;
  • liquid ⁇ , ⁇ '-diphenylacrylate derivatives especially 2-ethylhexyl ⁇ , ⁇ '- diphenylacrylate or octocrylene, which is available from BASF under the name Uvinul N539 ®;
  • 3-benzylidenecamphor derivatives especially 3- (4-methylbenzylidene) camphor of from Merck under the name Eusolex ® 6300 is commercially, 3- benzylidene camphor, benzylidene camphor sulfonic acid and Polyacrylamidomethylbenzylidenecamphor
  • 1, 3, 5-triazine derivatives in particular: - 2,4,6-tris [p- (2'-ethylhexyl-l'-oxycarb onyl) anilino] - 1, 3, 5-triazine, the of the company BASF is offered under the name UVINUL T150 ® , and - Dioctylbutamidotriazon, which is offered by Sigma 3V under the name VASOR B HEB ® ;
  • Esters of benzalmaionic acid in particular 4-methoxyb enalmalonic acid edi (2-ethylhexyl) ester and 3- (4- (2,2-ethoxycarbonylvinyl) phenoxy) properenyl) methoxysiloxane / dimethylsiloxane copolymer, U.S.Pat from DSM Nutritional
  • UV-A filters are:
  • composition of the invention as a sunscreen filter substance, preferably as at least a UV-A filter, at least one
  • Dibenzoylmethane derivative preferably 4- (t-butyl) -4'-methoxydibenzoylmethane.
  • This dibenzoylmethane derivative preferably 4- (t-butyl) -4'-methoxydibenzoylmethane, may preferably be used in an amount of from I to 5% by weight, more preferably from 2 to 5% by weight, based on the total weight of the composition in which be included in the composition according to the invention.
  • a broadband filter for example:
  • triazine derivatives in particular the 2,4-bis ⁇ [4-2-ethylhexyloxy) -2-hydroxy] -phenyl ⁇ -6- (4-methoxyphenyl) -1,3,5-triazine obtained from Ciba Corporation under the name TINOSORB S ® , and the 2,2'-methylenebis [6- (2H-benzotriazol-2-yl) 4- (1,1,3,3-tetramethylbutyl) phenol], which from Ciba Corporation is available under the name Tinosorb M ®; and
  • a mixture of multiple filters and a mixture of UV-B filters, UV filters and broadband filters, as well as mixtures with physical filters can also be used.
  • the sulfates of barium, oxides of titanium (titanium dioxide, amorphous or crystalline in the form of rutile and / or anatase), zinc, iron, zirconium, cerium, silicon, manganese or mixtures thereof be specified.
  • the metal oxides may be present in particle form with a size in the micrometer or nanometer range (nanopigments).
  • the average particle sizes for the nanopigments are, for example, 5 to 100 nm.
  • the compositions according to the invention in preferred embodiments have a Sun Protection Factor (SPF) of more than 15, preferably more than 20, measured according to the international Sun Protection Factor (SPF) test method according to COLIPA.
  • SPF Sun Protection Factor
  • compositions according to the invention may additionally contain one or more further additives customary in cosmetics, such as antioxidants, and / or other auxiliaries and additives, such as emulsifiers, surfactants, defoamers, thickeners, surfactants, active ingredients, humectants, fillers, film formers, Solvents, coalescents, flavoring agents, odor absorbers, perfumes, gelling agents and / or other polymer dispersions such as dispersions based on polyacrylates, fillers, plasticizers, pigments, dyes, flow control agents, thixotropic agents, plasticizers, plasticizers, preservatives, etc. included.
  • auxiliaries and additives such as emulsifiers, surfactants, defoamers, thickeners, surfactants, active ingredients, humectants, fillers, film formers, Solvents, coalescents, flavoring agents, odor absorbers, perfumes, gelling agents and / or other polymer dispersions such
  • composition of the invention may also contain sensory additive.
  • sensory additives include colorless or white, mineral or synthetic, lamellar, spherical or elongated inert particles or a non-particulate sensory
  • additive which e.g. further improve the sensory properties of the formulations and, for example, leave a velvety or silky feel on the skin.
  • the sensory additives may be included in the composition of the present invention, for example, in an amount of up to 10% by weight, preferably 0.1 to 10% by weight and more preferably 0.1 to 7%, based on the total weight of the composition ,
  • Advantageous particulate sensory additives for the purposes of the present invention are talc, mica, silica, kaolin, starch and derivatives thereof (for example tapioca starch, distarch phosphate, aluminum or sodium starch octenylsuccinate and the like), fumed silica, pigments, which have no predominantly UV filter or coloring action (such as, for example, boron nitride, etc.), boron nitride, calcium carbonate, dicalcium phosphate, magnesium carbonate, magnesium hydrogencarbonate, hydroxyapatites, microcrystalline celluloses, powders of synthetic polymers, such as polyamides (for example, those which are commercially available).
  • synthetic polymers such as polyamides (for example, those which are commercially available).
  • Nylon® polymers available), polyethylene, poly- ⁇ -alanines, polytetrafluoro- polyethylene (“Teflon®”), polyacrylate, polyurethane, lauroyl lysines, silicone resin (for example the polymers available under the trade name "Tospearl®” from the company obo Products Inc.), hollow particles of polyvinylidene acrylonitriles (Expancel® from Akzo Nobel) or Hollow particles of silica (Silica Beads® from MAPRECOS).
  • Advantageous non-particulate sensory additives may be selected from the (dimethiconols) (eg Dow Corning 1503 Fluid from Dow Corning Ltd.), the silicone copolymers (eg, di-vinyldimethicone / dimethicone copolymer, Dow Corning II MW 2220 the company Dow Corning
  • composition according to the invention may comprise one or more humectants (moisturizers).
  • humectants are, for example, glycerol, polyglycerol, sorbitol, dimethylisosorbide, lactic acid and / or lactates, in particular sodium lactate, butylene glycol, propylene glycol, biosaccharide gum-1, glycine soya, hydroxyethyl urea, ethylhexyloxyglycerol, pyrrolidonecarboxylic acid and urea.
  • polymeric moisturizers from the group of water-soluble and / or water-swellable and / or water-gellable polysaccharides; particularly advantageous are, for example, hyaluronic acid, chitosan and / or a high-fucose polysaccharide.
  • antioxidants such as water-soluble antioxidants may be used, such as vitamins, e.g.
  • Ascorbic acid and its derivatives are especially advantageous.
  • vitamin E and its derivatives are especially advantageous as well as vitamin A and its derivatives.
  • compositions according to the invention include: hydroxycarboxylic acids such as glycolic acid, lactic acid, malic acid, tartaric acid, citric acid and mandelic acid, ⁇ -hydroxycarboxylic acids such as salicylic acid and their acylated derivatives, 2-hydroxyalkanoic acid and its derivatives; natural active ingredients and / or their derivatives, such as, for example, lipoic-lipoic acid, folic acid, phytoene, D-biotin, coenzyme Q10, alpha-glucosylrutin, carnitine, camosine, natural and / or synthetic isofiavonoids, creatine, creatinine, taurine and / or [beta ] -Alanine and 8-1 lexadeene-1.
  • hydroxycarboxylic acids such as glycolic acid, lactic acid, malic acid, tartaric acid, citric acid and mandelic acid
  • ⁇ -hydroxycarboxylic acids such as salicylic acid and their acylated derivatives
  • the present invention further relates to the use of a composition according to the invention as a sons ons chutzmitt el.
  • the present invention furthermore relates to the use of a composition according to the invention for all types of cosmetics for application to the skin, which can bring about protection of the skin from UV radiation, for example face cream, hand cream, nail cream, lipsticks.
  • a cosmetic process for the protection of the skin against negative effects of solar radiation, in which a composition according to the invention is applied to the skin, is the subject of the invention.
  • the composition after application to the skin remains at least partially on this.
  • the solids or solid contents are determined by heating a balanced sample to 125 ° C to constant weight. If the weight is constant, the solids content is calculated by reweighing the sample.
  • NCO contents were determined volumetrically in accordance with DIN-EN ISO 1 1909, unless expressly stated otherwise.
  • Control for free NCO groups was performed by IR spectroscopy (band at 2260 cm -1 ).
  • the indicated viscosities were determined by means of rotary viscosimetry according to DIN 53019 at 23 ° C. with a rotational viscometer from Anton Paar Germany GmbH, Ostfildern, DE.
  • the determination of the mean particle sizes (indicated by the number average) of the polyurethane dispersions was carried out after dilution with deionized water by means of laser correlation spectroscopy (apparatus: Mäh ern Zetasizer 1000, Malver Inst. Limited).
  • the SPF measurements were carried out with a KONTRON 930 spectrophotometer equipped with a UV source and a double monochromator (energy flux between 290 and 400 nm).
  • Vorstrahlung was a UV source CPS + Suntest (Atlas) with a Standard filter and a bulkhead WG 320 filter used.
  • the product was exposed to 2 to 4 MED (minimal erythema can).
  • the selected MED values corresponds to a UV spectroradiometric flux of 0.365 mW / cm 2 from 290 to 320 nm and a UVA spectroradiometric flux of 6.0 mW / cm2 between 320 and 400 nm.
  • PMMA plate Helio Plate ® HD6 was as substrates of the company HelioScreen ® Labs used. 1.3 mg / cm 2 of the formulations was applied to an area of 25 cm 2 .
  • Examples 1 to 3 according to Table 1 were prepared by heating the aqueous phase with stirring to 80 ° C, the oil phase in a separate vessel while stirring and simultaneously heated to 80 ° C, then the oil phase with continuous stirring to the aqueous Phase was added and the resulting emulsion was homogenized.
  • the amount of polyurethane dispersion corresponding to the data in Table 1 was then added and mixed with the emulsion. Subsequently, the resulting emulsion was homogenized again.
  • Polyurethane Baycusan ® C 1000 (Bayer Materials cience AG, Leverkusen, DE), is an aqueous dispersion of a polyurethane having a solids content of 40 +.
  • UV filters according to the invention having at least 2 aromatic groups per molecule, ethylhexyl triazone, bis-ethylhexyloxyphenol were methoxyphenyl triazines and benzophenones-3. Examples 1 (wt%) 2 (wt%) 3 (wt%)
  • Comparative Examples 4-6 according to Table 2 were prepared analogous to the formulations of Examples 1-3. The only difference was that Comparative Examples 4-6 did not contain a polyurethane film former.
  • the comparative examples according to Table 3 were prepared analogously to the formulations of Examples 1-3. The only difference was that no sunscreen filter substance according to the invention having at least two aromatic groups was used here. On the contrary, known ionic filter substances having an aromatic group were used here (flomosalates, ethylhexyl methoxycinnamates, ethylhexyl salicylates).
  • Figure 1 clearly shows that only in the combination according to the invention of a polyurethane with an organic ion protective substance X) with at least two aromatic groups is an SPF boosting effect achieved, i. compared to a formulation with the protective filter substance X) but without polyurethane (Comparative Examples 4 to 6), a doubling to a tripling of the protective effect (of the SPF) can be achieved.
  • FIG. 2 again shows that an SPF boosting effect does not occur in a combination of sunscreen filter substances with a polyurethane, if a sunscreen filter substance X) with at least two aromatic groups is not used, as provided by the invention.
  • the formulations of the comparative examples 7 to 12 each contain known sunscreen filter substances with only one aromatic group. When combining these sunscreen filters with a polyurethane, there is no SPF boosting effect.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Cosmetics (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne une composition comprenant un polyuréthanne, pouvant être obtenu par réaction d'un ou de plusieurs prépolymères de polyuréthanne A) non hydrosolubles et non hydrodispersables à fonction isocyanate avec un ou plusieurs composés B) à fonction amine, et au moins une substance filtrante de protection solaire organique X), à l'exception de l'octocrylène, comportant au moins deux groupes aromatiques. L'invention concerne également l'utilisation de cette composition comme produit de protection solaire, ainsi qu'un procédé cosmétique pour protéger la peau contre les effets néfastes du rayonnement solaire, ce procédé consistant à appliquer ladite composition sur la peau.
PCT/EP2011/067684 2010-10-13 2011-10-11 Composition de protection solaire à base de polyuréthanne comprenant des substances filtrantes spéciales WO2012049146A2 (fr)

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US9566221B2 (en) 2012-11-09 2017-02-14 L'oreal Methods for altering the color and appearance of hair
US9565915B2 (en) 2011-11-09 2017-02-14 L'oreal Compositions and methods for altering the appearance of hair
US9565916B2 (en) 2011-11-09 2017-02-14 L'oreal Compositions and methods for altering the appearance of hair
US9750678B2 (en) 2014-12-19 2017-09-05 L'oreal Hair coloring compositions comprising latex polymers
US9789050B2 (en) 2013-06-28 2017-10-17 L'oreal Compositions and methods for treating hair
US9788627B2 (en) 2013-06-28 2017-10-17 L'oreal Compositions and methods for treating hair
US9795555B2 (en) 2013-06-28 2017-10-24 L'oreal Compositions and methods for treating hair
US9801808B2 (en) 2014-12-19 2017-10-31 Loreal Hair styling compositions comprising latex polymers and wax dispersions
US9801804B2 (en) 2013-06-28 2017-10-31 L'oreal Compositions and methods for treating hair
US9814668B2 (en) 2014-12-19 2017-11-14 L'oreal Hair styling compositions comprising latex polymers
US9884002B2 (en) 2013-06-28 2018-02-06 L'oreal Compositions and methods for treating hair
US9884003B2 (en) 2013-06-28 2018-02-06 L'oreal Compositions and methods for treating hair
US9884004B2 (en) 2013-06-28 2018-02-06 L'oreal Compositions and methods for treating hair
CN109077974A (zh) * 2018-08-27 2018-12-25 天津市康婷生物工程有限公司 一种具有防水抗汗型全波段防晒护肤品
US10195122B2 (en) 2014-12-19 2019-02-05 L'oreal Compositions and methods for hair
US10378731B2 (en) 2015-10-09 2019-08-13 Signify Holding B.V. Lighting system and a method of generating a light output
US10813853B2 (en) 2014-12-30 2020-10-27 L'oreal Compositions and methods for hair
US10864156B2 (en) 2013-06-28 2020-12-15 L'oreal Compositions and methods for treating hair
EP3889196A1 (fr) * 2020-03-31 2021-10-06 Covestro Deutschland AG Dispersions de polyuréthane biobasées pour applications de protection solaire
EP3888627A1 (fr) * 2020-03-31 2021-10-06 Covestro Deutschland AG Dispersions de polyuréthane biobasées pour applications cosmétiques décoratives

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US9565916B2 (en) 2011-11-09 2017-02-14 L'oreal Compositions and methods for altering the appearance of hair
US9578944B2 (en) 2011-11-09 2017-02-28 L'oreal Compositions and methods for altering the appearance of hair
US9474700B2 (en) 2012-11-09 2016-10-25 L'oreal Methods for altering the color and appearance of hair
US9566221B2 (en) 2012-11-09 2017-02-14 L'oreal Methods for altering the color and appearance of hair
US9884002B2 (en) 2013-06-28 2018-02-06 L'oreal Compositions and methods for treating hair
US10709658B2 (en) 2013-06-28 2020-07-14 L'oreal Compositions and methods for treating hair
US9788627B2 (en) 2013-06-28 2017-10-17 L'oreal Compositions and methods for treating hair
US9795555B2 (en) 2013-06-28 2017-10-24 L'oreal Compositions and methods for treating hair
US10973752B2 (en) 2013-06-28 2021-04-13 L'oreal Compositions for treating hair
US9801804B2 (en) 2013-06-28 2017-10-31 L'oreal Compositions and methods for treating hair
US9789050B2 (en) 2013-06-28 2017-10-17 L'oreal Compositions and methods for treating hair
US10898427B2 (en) 2013-06-28 2021-01-26 L'oreal Compositions and methods for treating hair
US9884003B2 (en) 2013-06-28 2018-02-06 L'oreal Compositions and methods for treating hair
US9884004B2 (en) 2013-06-28 2018-02-06 L'oreal Compositions and methods for treating hair
US10874601B2 (en) 2013-06-28 2020-12-29 L'oreal Compositions and methods for treating hair
US10864156B2 (en) 2013-06-28 2020-12-15 L'oreal Compositions and methods for treating hair
US9814668B2 (en) 2014-12-19 2017-11-14 L'oreal Hair styling compositions comprising latex polymers
US10195122B2 (en) 2014-12-19 2019-02-05 L'oreal Compositions and methods for hair
US9750678B2 (en) 2014-12-19 2017-09-05 L'oreal Hair coloring compositions comprising latex polymers
US9801808B2 (en) 2014-12-19 2017-10-31 Loreal Hair styling compositions comprising latex polymers and wax dispersions
US10813853B2 (en) 2014-12-30 2020-10-27 L'oreal Compositions and methods for hair
US10378731B2 (en) 2015-10-09 2019-08-13 Signify Holding B.V. Lighting system and a method of generating a light output
CN109077974A (zh) * 2018-08-27 2018-12-25 天津市康婷生物工程有限公司 一种具有防水抗汗型全波段防晒护肤品
EP3889196A1 (fr) * 2020-03-31 2021-10-06 Covestro Deutschland AG Dispersions de polyuréthane biobasées pour applications de protection solaire
EP3888627A1 (fr) * 2020-03-31 2021-10-06 Covestro Deutschland AG Dispersions de polyuréthane biobasées pour applications cosmétiques décoratives
WO2021198051A1 (fr) * 2020-03-31 2021-10-07 Covestro Deutschland Ag Dispersions de polyuréthane à base biologique pour applications cosmétiques décoratives

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