EP2178494A2 - Neue zwitterionische verbindungen enthaltende formulierungen und deren verwendung - Google Patents
Neue zwitterionische verbindungen enthaltende formulierungen und deren verwendungInfo
- Publication number
- EP2178494A2 EP2178494A2 EP08761321A EP08761321A EP2178494A2 EP 2178494 A2 EP2178494 A2 EP 2178494A2 EP 08761321 A EP08761321 A EP 08761321A EP 08761321 A EP08761321 A EP 08761321A EP 2178494 A2 EP2178494 A2 EP 2178494A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- compound
- skin
- formula
- care
- acid
- 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.)
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
Definitions
- the invention relates to formulations containing novel zwitterionic compounds, such as the use of these formulations as cosmetics.
- the hitherto known surface-active glycinate compounds such as e.g. Cocoamidopropyl betaines are used, for example, as amphoteric surfactants, in particular for hair and skin cleansing preparations such as shampoos, skin-friendly foam and shower gels, intimate and personal care products.
- these improve the dermatological properties of anionic and nonionic surfactants and cause a pleasant feeling on the skin.
- betaines can be used with advantage in detergents, such as dishwashing detergents and mild detergents.
- the betaines of the prior art are, in particular, fatty acid amidopropylbetaines whose fatty acid radicals in the mixture generally have from 8 to 18 carbon atoms. Compounds of this type are described, for example, in EP 711545.
- R 3 is the alkyl radical of a fatty acid
- the alkyl radical R 3 is derived in this case usually from the natural or synthetic fatty acids having 6 to 20 carbon atoms and mixtures thereof.
- Suitable fatty acids are, for example, caprylic acid, capric acid, lauric acid, palmitic acid, stearic acid, behenic acid, linoleic acid, caproic acid, linolenic acid, ricinoleic acid.
- fatty acid mixtures having a chain length of 8-18 carbon atoms such as coconut fatty acid or palm kernel fatty acid, which can optionally be cured by suitable hydrogenation methods.
- the cornea which is the outermost layer of the skin, is considered important Barrier layer of particular importance for protection against
- NMF natural moisturizing factors
- Drastic environmental conditions such as Low temperatures or too low humidity in winter, contribute significantly to the fact that the skin becomes rough and dry.
- the moisturizers contained in the epidermis are also easily removed by frequent washing or bathing. This allows more water to escape from deeper skin layers and the so-called transepidermal water loss (TEWL) increases, causing a drying of the skin. It is believed that the loss of natural moisturizers correlates with a reduction in water content and reduced softness of the keratin layer.
- Careful care to prevent permanently dry skin is not only an aesthetic requirement, but also a tried and tested remedy to effectively prevent chronic skin diseases.
- the moisture regulation of the skin can be effectively supported by topical application of appropriate formulations.
- moisturizers are also able to reduce transepidermal water loss and can therefore be considered as a kind of moisturizer.
- Another common approach is the addition of humectants as activating ingredients to cosmetic emulsions, gels or cleansing personal care products, which are intended to ensure the supply of the keratin layer with a sufficient amount of moisture over defined periods of time.
- Moisturizers are also referred to as moisturizers or humectants and are intended, on the one hand, to retain water in the epidermis and, on the other hand, to reduce the TEWL by stabilizing the barrier function in the upper horny layer.
- hygroscopic substances such as, in particular, polyhydric alcohols, ethoxylated polyols, sugars and polysaccharides, such as, for example, hyaluronic acid and its salts, which play an important role in moisture regulation because they can bind water in the stratum corneum. This ultimately results in an improvement in skin elasticity.
- body cleansing agents such as shower gels or shampoos
- body cleansing agents result in a marked change in the lipid composition of the skin, which leads to a reduction in the barrier function of the skin and thus to an increased transepidermal water loss.
- the literature describes a large number of moisturizers which are used to compensate for this effect, for example bis-PEG / PPG-20/20 dimethicone (Abil® B 8832, US Pat. Goldschmidt GmbH), glycerol or PEG-7 glyceryl cocoate (Tegosoft® GC, Goldschmidt GmbH).
- micellar components the lipophilic refatting agents, the surfactants and solubilizers
- the refatting agents become insoluble again.
- lipophilic substances both skin-specific lipids and emollients / cosmetic oils
- an ideal moisturizer should produce a clear effect even at low concentrations, be non-toxic, very well tolerated by the skin, have high compatibility with other ingredients, have good long-term stability and can be easily incorporated into skin treatment.
- a moisturizer can be prepared simply and inexpensively; During production, it should be obtained in a form which ensures easy handling and additionally satisfies the high purity conditions imposed on cosmetic or dermatological active ingredients.
- a moisturizer should have further, multifunctional properties, ie in addition to the normalization of the water content of the skin continue to have, for example, protective, calming or anti-inflammatory properties.
- the object of the invention was to provide new moisturizers which meet the above criteria.
- the present invention therefore relates to formulations as described in claim 1 and the use of these as cosmetics.
- Another object of the invention is the use of compounds according to formula I for increasing and / or stabilizing the moisture content of the skin
- R 1 and R 2 independently of one another are identical or different, aliphatic hydrocarbon radicals having 1 to 6 carbon atoms, preferably to C3-hydrocarbon radicals and are preferably CH3 radicals
- Y is a divalent hydrocarbon radical, preferably -CH 2 -
- formulations according to the invention contain at least one compound of the formula I in which Y is CH 2 .
- formulations according to the invention comprise at least one compound of the formula I in an amount of 0.05 to 10 wt .-%, and preferably in an amount of 0.1 to 5 wt .-% based on the total formulation.
- Formulations of the invention may e.g. contain at least one additional component selected from the group of
- Emulsifiers and surfactants Thickener / Viscosity regulator / Stabilizers
- UV light protection filters
- all cosmetic oils in particular mono- or diesters of linear and / or branched mono- and / or dicarboxylic acids having 2 to 44 carbon atoms with linear and / or branched saturated or unsaturated alcohols having 1 to 22 carbon atoms, can be used.
- the esterification products of aliphatic, difunctional alcohols having 2 to 36 carbon atoms with monofunctional aliphatic carboxylic acids having 1 to 22 carbon atoms used.
- long-chain aryl esters such as esters of benzoic acid, for example benzoic acid esters of linear or branched, saturated or unsaturated alcohols having 1 to 22 carbon atoms, or isostearyl benzoate or
- Benzoic acid octyl dodecyl ester Benzoic acid octyl dodecyl ester.
- Other monoesters suitable as emmolients and oil components are e.g. the methyl esters and isopropyl esters of fatty acids having 12 to 22 carbon atoms such as e.g. Methyl laurate, methyl stearate, methyl oleate, methyl erucate, isopropyl palmitate, isopropyl myristate, isopropyl stearate, isopropyl oleate.
- Other suitable monoesters are e.g.
- Octyldodecyl palmitate, oleyl oleate, oleyl erucate, erucyl oleate and esters which are obtainable from technical aliphatic alcohol cuts and technical aliphatic carboxylic acid mixtures, for example esters of unsaturated fatty alcohols having 12 to 22 carbon atoms and saturated and unsaturated fatty acids having 12 to 22 carbon atoms, as is known animal and vegetable fats are accessible. Also suitable, however, are naturally occurring monoester or wax ester mixtures, as present, for example, in jojoba oil or in sperm oil.
- Suitable dicarboxylic esters are, for example, di-n-butyl adipate, di-n-butyl sebacate, di- (2-ethylhexyl) adipate, di (2-hexyldecyl) succinate, D-isotridecyl acelate.
- Suitable diol esters are, for example, ethylene glycol dioleate, ethylene glycol diisotridecanoate, propylene glycol di- (2-ethylhexanoate), butanediol diisostearate and neopentyl glycol di-caprylate.
- fatty acid esters used as emmolients may, for example, Ci2-i5-alkyl benzoate, dicaprylyl carbonate, diethylhexyl carbonate.
- emollients and oil component are longer chain triglycerides, ie, triple esters of glycerol with three acid molecules, at least one of which is longer chain.
- fatty acid triglycerides are mentioned;
- natural, vegetable oils such as olive oil, sunflower oil, soybean oil, peanut oil, rapeseed oil, almond oil, palm oil but also the liquid portion of coconut oil or palm kernel oil and animal oils such as tallow oil, the liquid portions of beef tallow or synthetic triglycerides of Caprylic-capric acid mixtures, triglycerides from technical oleic acid, triglycerides with isostearic acid, or from palmitic acid-oleic acid mixtures as emollients and oil components.
- hydrocarbons in particular liquid paraffins and isoparaffins can be used.
- Examples of usable hydrocarbons are paraffin oil, isohexadecane, polydecene, vaseline, paraffin perliquidum, squalane. Furthermore, linear or branched fatty alcohols such as oleyl alcohol or octyldodecanol, and fatty alcohol ethers such as dicaprylyl ethers can be used.
- Suitable silicone oils and waxes are, for example, polydimethylsiloxanes, cyclomethylsiloxanes, and also aryl- or alkyl- or alkoxy-substituted polymethylsiloxanes or cyclomethylsiloxanes.
- Nonionic, anionic, cationic or amphoteric surfactants can be used as emulsifiers or surfactants.
- non-ionic emulsifiers or surfactants compounds from at least one of the following groups can be used:
- Partial esters based on linear, branched, unsaturated or saturated C 6 -C 22 fatty acids, ricinoleic acid and
- Pentaerythritol dipentaerythritol, sugar alcohols (e.g., sorbitol), alkyl glucosides (e.g., methyl glucoside,
- Tri-PEG-alkyl phosphates and their salts Polysiloxane-polyether copolymers (dimethicone copolyols), such as eg PEG / PPG-20/6 dimethicones, PEG / PPG-20/20 dimethicones, bis-PEG / PPG-20/20 dimethicones, PEG -12 or PEG-14 Dimethicone, PEG / PPG-14/4 or 4/12 or 20/20 or 18/18 or 17/18 or 15/15.
- Polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives such as, for example, lauryl or cetyl dimethicone copolyols, in particular cetyl PEG / PPG-10/1
- Dimethicone (ABIL ® EM 90 (Degussa) mixed esters of pentaerythritol, fatty acids, citric acid and
- Polyglycerol Citric acid esters e.g. Glyceryl Stearate Citrate
- Anionic emulsifiers or surfactants can be water-solubilizing anionic groups such as e.g. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic radical.
- Skin-compatible anionic surfactants are known to the skilled worker in large numbers and are commercially available. These may be alkyl sulfates or alkyl phosphates in the form of their alkali, ammonium or alkanolammonium salts, alkyl ether sulfates,
- cationic emulsifiers and surfactants can be added.
- quaternary ammonium compounds in particular those provided with at least one linear and / or branched, saturated or unsaturated alkyl chain having 8 to 22 carbon atoms, are used, such as alkyltrimethylammonium halides such as cetyltrimethylammonium chloride or bromide or Behenyltrimethylammonium chloride, but also
- Dialkyldimethylammonium halides e.g. Distearyldimethylammoniumchlorid be used.
- monoalkylamidoquats e.g. Palmitamidopropyltrimethylammonium chloride or corresponding Dialkylamidoquats be used.
- readily biodegradable quaternary ester compounds can be used, which may be quaternized fatty acid esters based on mono-, di- or triethanolamine.
- alkylguanidinium salts may be added as cationic emulsifiers.
- amphoteric surfactants such as e.g. Betaine, amphoacetates or amphopropionates to use together with the polyglycerol esters according to the invention.
- Suitable thickeners for thickening oil phases are all thickeners known to the person skilled in the art.
- waxes such as hydrogenated castor wax, beeswax or microwax are to be mentioned.
- inorganic thickeners such as silica, alumina or sheet silicates (for example hectorite, laponite, saponite).
- These inorganic oil phase thickeners may be hydrophobically modified.
- aerosils, phyllosilicates and / or metal salts of fatty acids such as e.g. Zinc stearate can be used.
- viscosity regulators for aqueous surfactant systems include NaCl, low molecular weight nonionic surfactants, such as cocoamides DEA / MEA and laureth-3, or polymers, high molecular weight, associative, highly ethoxylated fatty derivatives, such as PEG-200 Hydrogenated Glyceryl Palmate.
- UV light protection filters for example, organic substances capable of absorbing ultraviolet rays and those picked up can be used
- UVB filters can be oil-soluble or water-soluble.
- oil-soluble UVB sunscreens e.g. to call:
- 4-aminobenzoic acid derivatives e.g. 4- (dimethylamino) benzoic acid 2-ethylhexyl ester
- (Octocrylene) esters of salicylic acid e.g. Salicylic acid 2-ethylhexyl ester, 4-isopropylbenzyl salicylate,
- Salicylic acid homomenthyl ester Derivatives of benzophenone, e.g. 2-hydroxy
- 4-methoxybenzmalonic acid di-2-ethylhexyl ester triazine derivatives such as 2, 4, 6-trianilino (p-carbo-2'-ethyl-1 '-hexyloxy) -1, 3, 5-triazine and octyltriazone.
- Propane-1,3-diones such as 1- (4-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1,3-dione.
- Suitable water-soluble UVB sunscreen filters are:
- 4-methoxybenzophenone-5-sulfonic acid and its salts sulfonic acid derivatives of the 3-benzylidene camphor e.g. 4- (2-oxo-3-bomylidenemethyl) benzenesulfonic acid and 2-methyl-5- (2-oxo-3-bomylidene) -sulfonic acid and its salts.
- UVA sunscreen in particular derivatives of benzoylmethane come into question, such as 1- (4 'tert. Butylphenyl) -3- (4' -methoxyphenyl) propane-1, 3-dione or 1-phenyl-3- (4 '-isopropylphenyl) propane-1,3-dione.
- the UV-A and UV-B filters can also be used in mixtures.
- insoluble pigments are also suitable for this purpose, namely finely dispersed metal oxides or salts, for example titanium dioxide, zinc oxide, iron oxide, aluminum oxide, cerium oxide, zirconium oxide, silicates (talc), barium sulfate and zinc stearate.
- the particles should have an average diameter of less than 100 nm, for example between 5 and 50 nm and in particular between 15 and 30 nm. They may have a spherical shape, but it is also possible to use those particles which have an ellipsoidal or otherwise deviating shape from the spherical shape.
- a relatively new class of sunscreen filters are micronized organic pigments, such as 2, 2'-methylene-bis- ⁇ 6- (2H-) benzotriazole-2-yl) -4- (1, 1, 3, 3-tetramethylbutyl) phenol ⁇ having a particle size of less than 200 nm, which is obtainable, for example, as a 50% aqueous dispersion.
- micronized organic pigments such as 2, 2'-methylene-bis- ⁇ 6- (2H-) benzotriazole-2-yl) -4- (1, 1, 3, 3-tetramethylbutyl) phenol ⁇ having a particle size of less than 200 nm, which is obtainable, for example, as a 50% aqueous dispersion.
- UV light protection filters can be found in the review by P. Finkel in S ⁇ FW Journal 122, 543 (1996).
- antioxidants e.g. Superoxide dismutase, tocopherols (vitamin E), dibutylhydroxytoluene and ascorbic acid (vitamin C).
- hydrotropes for example, ethanol, isopropyl alcohol or polyols may be used to improve flowability and application properties.
- Polyols contemplated herein may have from 2 to 15 carbon atoms and at least two hydroxyl groups. Typical examples are:
- Glycerol alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols having an average molecular weight of 100 to 1000 daltons
- Trimethylolpropane trimethylolbutane, pentaerythritol and
- Niedrigalkylgucoside in particular those having 1 to 4 carbon atoms in the alkyl radical, such as
- Methyl and butyl glucoside sugar alcohols having 5 to 12 carbon atoms such as sorbitol or mannitol
- Sugars having 5 to 12 carbon atoms such as glucose or sucrose
- Amino sugars such as glucamine.
- iron oxide pigments, titanium dioxide or zinc oxide particles which are additionally used under "UV protection agents” can be used as solids, and it is also possible to use particles which lead to special sensory effects, such as nylon-12, boron nitride, polymer particles, such as Polyacrylate or polymethacrylate particles or silicone elastomers.
- pearlescing additives e.g. Glycol distearate or PEG-3 distearate can be used.
- Suitable deodorant active ingredients are, for example, odor maskers such as the customary perfume ingredients, odor absorbers, for example the phyllosilicates described in patent publication DE-P 40 09 347, montmorillonite, kaolinite, ileite, beidelite, nontronite, saponite, bentorite, smectite, furthermore zinc salts, for example of ricinoleic acid.
- Germ-inhibiting agents are also suitable for incorporation.
- Germ-inhibiting substances are, for example, 2, 4, 4-trichloro-2'-hydroxydiphenyl ether (Irgasan), 1,6-di- (4-chlorophenylbiguanido) hexane (chlorhexidine),
- astringents can be used, for example, basic aluminum chlorides such as aluminum chlorohydrate (“ACH”) and aluminum-zirconium-glycine salts ("ZAG").
- insect repellents for example, N, N-diethyl-m-toluamide, 1, 2-pentanediol or insect repellent 3535 can be used.
- alkylparaben esters may be methylparaben, ethylparaben, propylparaben and / or butylparaben.
- phenoxyethanol other alcohols can be used, such as benzyl alcohol or ethanol.
- other common preservatives such as sorbic or benzoic acid, salicylic acid, 2-bromo-2-nitropropane-l, 3-diol,
- Ethylhexylglycerin or caprylyl glycol are used.
- conditioning agents e.g. organic quaternary compounds such as cetrimonium chloride,
- Distearyldimonium chloride behemmonium methosulfate, distearoylethyldimonium chloride,
- Hydroxypropyltrimonium chloride or quaternium-80 or also amine derivatives such as e.g. Aminopropyldimethicone or Stearamidopropyldimethylamine be used.
- Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot,
- Typical synthetic perfume compounds are ester type products, ethers, aldehydes, ketones, alcohols and hydrocarbons. Fragrance compounds of the ester type are known e.g. Benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linalyl acetate,
- Linalyl benzoate benzyl formate, ethyl methyl phenylglycinate, Allyl cyclohexyl propionate, styrallyl propionate and benzyl salicylate.
- the ethers include, for example, benzyl ethyl ether, to the aldehydes, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydrocitronellal, lilial and bourgeonal, to the ketones such as the Jonone, CC isomethylionone and methyl cedrylketone to the alcohols include anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol; the hydrocarbons mainly include the terpenes and balsams.
- fragrances can be used, which together create an appealing scent.
- low-volatility volatile oils which are mostly used as aroma components, are suitable as perfumes, for example sage oil, chamomile oil, clove oil, lemon balm oil, mint oil, cinnamon oil, lime blossom oil, juniper berry oil, vetiver oil, oliban oil, galbanum oil, labolanum oil and lavandin oil.
- Dyes which may be used are those which are suitable and approved for cosmetic purposes, as described, for example, in the publication "Kosmetician Anlagenrbesch" of the Dye Commission of the Germans Research Community, Verlag Chemie, Weinheim, 1984, pp 81 - 106 are compiled. These dyes are usually used in concentrations of 0.001 to 0.1 wt .-%, based on the total mixture.
- biogenic active ingredients include tocopherol and derivatives, ascorbic acid and derivatives, retinol and derivatives, deoxyribonucleic acid, coenzyme Q10, bisabolol, allantoin, phytantriol, panthenol, alpha-hydroxy acids, salicylic acid, amino acids, amino acid derivatives, hyaluronic acid, glucans, creatine and creatine derivatives, guanidine and Guanidine derivatives, ceramides, phytosphingosine and phytosphingosine derivatives, sphingosine and sphingosine derivatives, pseudoceramides, essential oils, peptides, protein hydrolysates, plant extracts and vitamins and vitamin mixtures. These substances can be combined with the novel zwitterionic compounds described in any proportions.
- ethoxylated glycerol fatty acid esters such as PEG-7 glycerol cocoate
- cationic polymers such as polyquaternium-7 or polyglycerol esters
- solvent e.g. Propylene glycol, dipropylene glycol, glycerol, glycerol carbonate, water, ethanol, propanol, 1, 3-propanediol can be used.
- An object of the invention is the use of formulations according to the invention as a cosmetic.
- the compounds of the formula I may be present here preferably in a concentration of 0.05 to 10 wt .-%.
- the formulation can be prepared as an emulsion; a typical emulsion (W / O or O / W) may contain, for example:
- 0 to 10 wt .-% preferably> 0 to 10 wt .-% of one or more emulsifiers, 0 to 10 wt .-%, preferably> 0 to 10 wt .-% of one or more viscosity regulators or thickeners, 0 to 30 wt .-%, preferably> 0 to 10 wt .-% of one or more oil bodies or emollients, and customary auxiliaries and additives in conventional
- Preferred emulsifiers and surfactants are the following nonionic, anionic, cationic or amphoteric surfactants:
- Alkyl mono- and oligoglycosides having 8 to 22 carbon atoms in the alkyl radical and their
- Glyceryl oleates citrates and dilauryl citrates, anionic emulsifiers or surfactants with water-solubilizing anionic groups such as e.g. a carboxylate, sulfate, sulfonate or phosphate group and a lipophilic moiety, e.g. Alkyl sulfates or alkyl phosphates in the form of their alkali, ammonium or alkanolammonium salts, alkyl ether sulfates,
- Alkyl ether carboxylates acyl sarcosinates and sulfosuccinates and acyl glutamates in the form of their alkali metal or ammonium salts, cationic emulsifiers and surfactants, such as e.g. quaternary ammonium compounds, such as
- Alkyltrimethylammoniumhalogenide such as Cetyltrimethylammonium chloride or
- Dialkyldimethylammonium halides e.g. Distearyldimethylammonium chloride, monoalkylamidoquats, e.g.
- Biodegradable quaternary ester compounds such as e.g. quaternized fatty acid esters based on mono-, di- or triethanolamine, and
- Alkylguanidinium salts such as e.g. Betaines, amphoacetates or amphopropionates.
- Preferred emollients are:
- Esters which are obtainable from technical aliphatic alcohol cuts and technical aliphatic carboxylic acid mixtures for example esters of unsaturated fatty alcohols having 12 to 22 carbon atoms and saturated and unsaturated fatty acids having 12 to 22 carbon atoms, such as Naturally occurring monoester or wax ester mixtures as present, for example, in jojoba oil or in sperm oil, dicarboxylic acid esters such as, for example, di-n-butyl adipate, di-n-butyl sebacate, di- ( 2-ethylhexyl) adipate, diol esters such as, for example, ethylene glycol dioleate, propylene glycol di- (2-ethylhexanoate), dicaprylyl carbonate,
- dicarboxylic acid esters such as, for example, di-n-butyl adipate, di-n-butyl sebacate, di- ( 2-ethylhexyl) adipate
- Olive oil sunflower oil, soybean oil, peanut oil, rapeseed oil,
- Triglycerides of caprylic-capric acid mixtures liquid paraffins and isoparaffins
- Squalane Linear or branched fatty alcohols such as oleyl alcohol or
- Octyldodecanol as well as fatty alcohol ethers such as dicaprylyl ether can be used.
- Silicone oils and waxes e.g. polydimethylsiloxanes
- Propoxylated emollients such as e.g. PPG-3 myristyl ether,
- Preferred viscosity regulators are:
- NaCl low molecular weight nonionic surfactants, such as cocoamides DEA / MEA and laureth-3, or polymeric, high molecular weight, associative, highly ethoxylated fatty derivatives such as PEG-200 Hydrogenated Glyceryl Palmate.
- Preferred thickeners for thickening oil phases are:
- Waxes such as hydrogenated castor wax, beeswax or
- Microwax, inorganic thickening agents such as optionally hydrophobically modified silica, alumina or phyllosilicates, and aerosils, phyllosilicates and / or metal salts of fatty acids, e.g. Zinc stearate.
- Formulations according to the invention may be hair care formulations such as shampoos and / or conditioners which exert a mitigating effect on irritated scalp.
- formulations according to the invention can also be used in cosmetic cleansing products.
- Formulations according to the invention in particular those for use as a cosmetic cleansing product such as, for example, shower gels, liquid soaps, facial cleansers, bath shampoos, may contain, for example:
- Preferred surfactants are anionic, amphoteric, nonionic and zwitterionic structure.
- Preferred anionic surfactants may be the salts of various cations
- Alkyl ether sulfates such as lauryl sulfate, lauryl ether sulfate,
- Myristyl ether sulfate or sulfosuccinic acid derivatives Myristyl ether sulfate or sulfosuccinic acid derivatives.
- Preferred zwitterionic surfactants are i.a. Cocoamidopropyl betaine or sultaine.
- Preferred amphoteric surfactants are amphoaceteins or glycinates, e.g. Sodium cocoamphoacetate or disodium cocoamphodiacetate.
- Preferred nonionic surfactants may be, for example, alkyl polyglycosides, polyether derivatives (ethoxylated fatty alcohols or fatty acids), polyglycerol derivatives or sugar esters.
- Preferred viscosity regulators are NaCl, low molecular weight nonionic surfactants such as Cocoamide DEA / MEA and Laureth-3, or polymeric, high molecular weight, associative, highly ethoxylated fatty derivatives such as PEG-200 Hydrogenated Glyceryl Palmate.
- Preferred conditioning agents are organic quaternary compounds such as cetrimonium chloride,
- Hydroxypropyltrimonium chloride or quaternium-80 or also amine derivatives such as e.g. Aminopropyldimethicone or Stearamidopropyldimethylamine
- a formulation according to the invention may be used alone or in combination with one or more active ingredients in cleansing or nourishing cosmetic formulations for regulating and improving the moisture content of the skin.
- Formulations of the invention may therefore find utility as a skin care, facial, head care, personal care, intimate care, foot care, hair care, nail care, dental care or oral care product.
- Formulations of the invention may be used in the form of an emulsion, suspension, solution, cream, ointment, paste, gel, oil, powder, aerosol, stick, spray, cleansing product, make-up or sunscreen preparation or a tonic.
- Formulations according to the present invention have a moisturizing and soothing effect.
- the invention therefore relates to the use of the formulation according to the invention for increasing and / or stabilizing the moisture content of the skin.
- Formulations according to the invention lower the roughness of stressed skin. Therefore, another object of the invention is the use of the formulations according to the invention for reducing skin roughness.
- the compounds according to formula I can e.g. be prepared by the method described below.
- carboxylic acids in process step A it is possible to use all mono-, di- or polycarboxylic acids or else mixtures of these which fulfill the conditions mentioned for formula II.
- carboxylic acids in process step A are oxalic acid (HOOC-COOH), tartronic acid (HOOC-CH 2 (OH) -COOH), malic acid (HOOC-CH 2 (OH ) -CH 2 -COOH) and tartaric acid (HOOC)
- amine component it is possible to use all suitable amine compounds which satisfy the conditions of the formula III. Preference is given to using 3- (diethylamino) propylamine, 2- (diethylamino) ethylamine or 2- (dimethylamino) ethylamine. Particularly preferred as the amine component is dimethylaminopropylamine (DMAPA).
- DMAPA dimethylaminopropylamine
- step A of the process an acid component according to formula II with an amine component of the formula III at a temperature of 90 0 C to 220 0 C, particularly preferably at a temperature of about 180 0 C is preferably converted to an amide amine of formula IV.
- Process step A of the process is particularly preferably carried out using a suitable catalyst.
- suitable catalysts strong base catalysts such as alkoxides are used, particularly preferred are sodium ethylate, potassium ethylate, sodium methoxide and potassium.
- the resulting water in the reaction can be removed from the product.
- the water is distilled off under the reaction conditions and so removed from the product mixture.
- the application of a negative pressure is advantageous to accelerate the removal of water by distilling off.
- the amidamines of relatively long chain fatty acids known from the state of the art should be taken into account in the salt formation between amine according to formula III and acid according to formula II due to the low molecular weights and thus higher Substance concentration is conditional.
- specially adapted process parameters may be used in such a way that the addition of the carboxylic acid component to the amine component is so slow that the temperature of the reaction mixture does not exceed 130 ° C., preferably 100 ° C. during the addition.
- larger amounts of the amine component could be driven off by the resulting water, which can adversely affect the stoichiometry of the feed components. It is preferred to countercool to maintain the said temperature ranges, in order to achieve an economically meaningful dosing.
- Process B can be carried out in the presence of a suitable solvent in an amount which ensures the stirring and pumpability of the reaction mixture at any point in the process.
- the reaction preferably takes place in the presence of water as solvent.
- the process step B is preferably carried out at a temperature of about 70-100 0 C.
- the by-produced halide Z can be removed from or left in the reaction solution. If the halide is to be removed, for example, precipitation be used with a suitable solvent or dialysis. Preferred solvent for precipitation is ethanol.
- the halide Z remains in the solution.
- monohalogencarboxylic acid or monohalogen carboxylic acid salt having an acid radical according to formula V it is possible to use all halocarboxylic acids whose acid radicals satisfy the conditions mentioned for formula V.
- Particularly preferred as the monohalocarboxylic acid salt according to formula V is the monochloroacetate.
- the process step B should also take into account the exothermic effect which, due to the low molecular weight of the short-chain amidine amine component, is greatly increased, in contrast to the processes of the prior art. Therefore, in process step B, the reaction is preferably carried out in the form that during and after complete addition of the halocarboxylic acid component to amide amine component until the decay of the heat of reaction, the reaction temperature is maintained at a maximum of about 70 0 C, which can be optionally countercooled. The subsequent reaction is preferably carried out slightly below the boiling point of the solvent, wherein preferably temperatures in the range of 95-99 0 C are used when using water as a solvent.
- amidamines of the formula IV to the corresponding compounds of the formula I is carried out as described, preferably in a solvent.
- the amidamines are preferably used in concentrations of 3 to 75%, preferably 5 to 50%.
- the solution of compounds according to formula I obtained in this process step can be used with or without further concentration or desalting steps, e.g. for the preparation of cosmetic preparations.
- Figure 3 IL-l ⁇ -concentration 24h after injury
- Figure 4 Sum of the IL-l ⁇ -concentration 24 and 48h after damage with SDS
- Figure 5 Viability of the cells 24h after two applications of the test formulations
- Figure 6 Viability of the skin cells 24 after damage with SDS
- Figure 7 Water retention of various short-chain zwitterionic compounds
- Figure 9 Long-term moisturizer effect of compound 2.1
- Figure 10 Decrease of the protein concentration relative to the vehicle
- Figure 11 Corneometry data of the panel test
- Salt formation exothermic and the mixture heats up to about 150 ° C and is about 4 - 5 h at a temperature of 175
- Thermometer, reflux condenser and dropping funnel are weighed 85 g of Na monochloroacetate and 185 g of water and 40
- the LDH concentration was determined using a commercially available test kit (LDH test kit, Roche Diagnostics, Mannheim, Germany). The test formulation was applied twice on the skin models 24 hours apart. Figure 1 shows the LDH release 24h after the last application.
- Test Formulation 3.1 A 4% aqueous solution of the short-chain zwitterionic compounds was applied. Since the compounds contain about 0.3% saline per 1% active substance, the corresponding saline concentration was additionally tested.
- the LDH release from the cells was not changed or even slightly smaller compared to the untreated skin model. This means that the short-chain zwitterionic compounds do not attack the cell membrane, so they do not have a cell damaging effect.
- SDS Sodium dodecyl sulfate
- Test formulation 3.2 The skin models were damaged with SDS for 40 min. Subsequently, the test formulation, an O / W cream with 1 or 4% compound 2.1, was applied. LDH release was measured at 24 and 48 hours after application of the test formulation.
- Figure 2 shows the total LDH concentration after 24 and 48 h.
- ILl- ⁇ is a messenger substance that plays a central role in inflammatory reactions in the body.
- SDS skin irritant surfactant which is an irritant
- Model stimulus is used in subjects studies and among other things induces the release of IL-1OC.
- the determination of IL-I ⁇ concentration was carried out with a commercially available test kit (human IL-1 ⁇ immunoassay,
- test formulation a 4% aqueous solution of the short chain zwitterionic compounds, was applied to the skin models. 24 h after the application was damaged for 40 min with 0.25% SDS solution. Subsequently, the test formulation was applied a second time. After a further incubation period of 24 h, the determination of the released cytokine IL-1 ⁇ was carried out. Since the test solutions contain about 0.3% NaCl per 1% active substance, a correspondingly concentrated one was also obtained
- Figure 3 shows the measurements of the IL-1 ⁇ concentration 24h after injury.
- Figure 4 shows the summed IL-1 ⁇ concentration at 24 and 48 h.
- the XTT test is based on the ability of the cells to reduce the dye XTT, which can be detected photometrically. This reaction is catalyzed by mitochondrial succinate dehydrogenase and requires NAD (P) H, which can only be produced by metabolically active cells. In summary, the XTT test describes the viability of the cells.
- the XTT test was carried out with a commercially available test kit and took place according to the manufacturer's instructions (XTT Test, Roche Diagnostics, Mannheim, Germany).
- the test formulation a 4% aqueous solution of the short chain, zwitterionic compounds, was applied twice on the skin models 24 hours apart. 24 hours after the second application, the XTT concentration was determined. In addition to the zwitterionic compounds, the concentration of common salt contained in the test solutions was again tested.
- the negative control used was 0.25% SDS.
- Figure 5 shows the viability of the cells relative to the control.
- test formulation s.
- Figure 6 shows the viability of the test formulations relative to the control, i. untreated cells, again.
- the IMS film is a membrane that is covered with peptides, lipids and polymers and represents a greatly simplified skin model.
- the active ingredient interacts with the film from the formulation. It is bound water and thus prevents or impedes the evaporation of water.
- the weight of the IMS membrane is determined (Wl).
- Figure 7 shows the measurement data of the water retention capacity of various short-chain zwitterionic compounds.
- the skin moisture of the "outer layer" of the epidermis is determined by measuring the capacitance. This principle is based on the fact that different dielectric constants of water and other substances are used. An appropriately shaped measuring capacitor responds to the samples introduced into its measuring volume with different ones Capacity changes that are automatically recorded and evaluated by the device.
- the special glass coated active probe is pressed onto the skin area to be measured, and after 1 second, the display shows the Corneometermesswert, ie the degree of moisture on the skin surface (www.dermatest.de/de/ueberuns.html).
- a Corneometer CM 825 from Courage & Khazaka is used.
- Skin moisture was measured before and 2 hours after application of the test formulations. Four test fields were marked on the forearms of 14 subjects, to which the various test formulations were applied. Before each measurement, the subjects had to spend at least 15 minutes in an air-conditioned room (21-22 ° C, 55% RH).
- Figure 8 shows the increase in corneometer units ( ⁇ CU) 2 hours after application of the test formulations.
- Compound 2.1 increased the skin moisture very clearly. The effectiveness increased significantly with increasing use concentration. It could therefore be shown that compound 2.1 has very good moisturizing properties.
- the skin roughness can be easily quantified by means of tape stripping.
- the rougher the skin surface is, for example because the skin lipid barrier is damaged, the weaker is the binding of the skin cells. This can be seen partly with the naked eye on very rough skin.
- Tape stripping removes the top corneocytes. The more corneocytes stick to the tape, the rougher the skin.
- the corneocytes are then quantitatively determined by means of a commercially available Bradford test. This is based on the following principle:
- the triphenylmethane dye Coomassie Brilliant Blue G-250 (CBBG) forms complexes in acidic solution with both the cationic and the non-polar, hydrophobic side chains of the proteins.
- the absorption spectrum of the unbound (cationic), red-colored form has an absorption maximum at 470 nm.
- the dye is stabilized in its blue, unprotonated, anionic sulfate form, the absorption spectrum shifts to an absorption maximum at 595 nm. Since the extinction coefficient of In addition, the dye-protein complex is much higher than that of the free dye, the increase in absorption at 595 nm may be due to the Formation of the complex with high sensitivity to the free color reagent can be measured photometrically and is a measure of the protein concentration of the solution.
- test formulation s.
- Example 3.9 The study was conducted on 12 subjects who received two test formulations, one with 2% Compound 2.1 and one without. These formulations had to be applied twice daily to the inside of each forearm. Tape strips were taken and analyzed before the start of the application and after 2 and 4 weeks. Test formulation: s. Example 3.9
- Figure 10 shows the decrease in the amount of protein relative to the vehicle.
- test panel consisted of 15 panelists.
- the test persons were instructed to use no cosmetic products (shower bath, body lotion) on the forearms from 3 days before the start of the test.
- Figure 11 shows the values listed above. From Figure 11, it can be seen that the reduction in corneometry observed in a skin cleansing application is diminished by the use of Formulation 4.1a to a level observed in untreated skin. Without use of Compound 2.1, a typical, significant decrease in skin moisture is observed.
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Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE200710040001 DE102007040001A1 (de) | 2007-08-23 | 2007-08-23 | Neue zwitterionische Verbindungen enthaltende Formulierungen und deren Verwendung |
PCT/EP2008/058003 WO2009024374A2 (de) | 2007-08-23 | 2008-06-24 | Neue zwitterionische verbindungen enthaltende formulierungen und deren verwendung |
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EP2178494A2 true EP2178494A2 (de) | 2010-04-28 |
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EP08761321A Withdrawn EP2178494A2 (de) | 2007-08-23 | 2008-06-24 | Neue zwitterionische verbindungen enthaltende formulierungen und deren verwendung |
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Country | Link |
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US (1) | US20110206623A1 (de) |
EP (1) | EP2178494A2 (de) |
DE (1) | DE102007040001A1 (de) |
WO (1) | WO2009024374A2 (de) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
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DE102009028156A1 (de) | 2009-07-31 | 2011-02-03 | Evonik Stockhausen Gmbh | Schäumbare O/W-Emulsion |
DE102010000993A1 (de) | 2010-01-19 | 2011-07-21 | Evonik Goldschmidt GmbH, 45127 | Neuartige Polysiloxane mit quatären Ammoniumgruppen, Verfahren zu deren Herstellung und deren Verwendung in reinigenden und pflegenden Formulierungen |
DE102011004815A1 (de) | 2011-02-28 | 2012-08-30 | Evonik Stockhausen Gmbh | Haut- und Handreinigungsmittel enthaltend superabsorbierende Partikel |
DE102013218981A1 (de) | 2013-09-20 | 2015-03-26 | Evonik Industries Ag | Raumtemperaturhärtendes Silikon-Polyester-Bindemittel |
DE102013218976A1 (de) | 2013-09-20 | 2015-04-16 | Evonik Industries Ag | Hydroxylgruppenhaltiges Silikon-Polyester-Acrylat-Bindemittel |
EP2997959B1 (de) | 2014-09-22 | 2019-12-25 | Evonik Operations GmbH | Formulierung enthaltend esterquats basierend auf isopropanolamin und tetrahydroxypropylethylenediamin |
EP3061442A1 (de) | 2015-02-27 | 2016-08-31 | Evonik Degussa GmbH | Zusammensetzung enthaltend Rhamnolipid und Siloxan |
EP3478655B1 (de) | 2016-06-29 | 2020-09-30 | Evonik Operations GmbH | Verfahren zur herstellung von tensiden |
MX2019000424A (es) | 2016-07-19 | 2019-03-28 | Evonik Degussa Gmbh | Uso de poliolesteres para la produccion de revestimientos plasticos porosos. |
EP3467052B1 (de) | 2017-10-06 | 2022-04-13 | Evonik Operations GmbH | Wässrige dispersion enthaltend siliziumdioxid und trimethyl 1,6-hexamethylendiamin |
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US3225074A (en) | 1959-12-28 | 1965-12-21 | American Cyanamid Co | Betaines |
DE1165574B (de) | 1960-08-08 | 1964-03-19 | Dehydag Gmbh | Verfahren zur Herstellung von als Emulgiermittel fuer Salbengrundlagen dienenden Mischestern |
US3836537A (en) * | 1970-10-07 | 1974-09-17 | Minnesota Mining & Mfg | Zwitterionic polymer hairsetting compositions and method of using same |
US4465491A (en) * | 1982-01-18 | 1984-08-14 | Ciba-Geigy Corporation | Solid dye preparation of water soluble dyes with aliphatic aminocarboxylic acid |
DE3740186A1 (de) | 1987-06-24 | 1989-01-05 | Beiersdorf Ag | Desodorierende und antimikrobielle zusammensetzung zur verwendung in kosmetischen oder topischen zubereitungen |
DE3938140A1 (de) | 1989-11-16 | 1991-08-08 | Beiersdorf Ag | Desodorierende kosmetische mittel |
DE4009347A1 (de) | 1990-03-23 | 1991-09-26 | Beiersdorf Ag | Desodorierende kosmetische mittel |
JPH05198768A (ja) | 1992-01-21 | 1993-08-06 | Mitsubishi Electric Corp | 半導体記憶装置およびその製造方法 |
DE4204321A1 (de) | 1992-02-13 | 1993-08-19 | Beiersdorf Ag | Verfahren zur isolierung und reinigung von fettsaeuren und hydroxyfettsaeuren und verwendungen von hydroxyfettsaeuren sowie zubereitungen, die sie enthalten |
DE4229707A1 (de) | 1992-09-05 | 1994-03-10 | Beiersdorf Ag | Germicide Wirkstoffkombinationen |
DE4229737C2 (de) | 1992-09-05 | 1996-04-25 | Beiersdorf Ag | Desodorierende kosmetische Mittel mit einem Gehalt an Fettsäuren |
DE4237081C2 (de) | 1992-11-03 | 1996-05-09 | Beiersdorf Ag | Verwendung von Di- oder Triglycerinestern als Deowirkstoffe |
JP3274522B2 (ja) * | 1993-02-02 | 2002-04-15 | 花王株式会社 | 新規カルボキシベタイン、その製造方法及びその用途 |
DE4309372C2 (de) | 1993-03-23 | 1997-08-21 | Beiersdorf Ag | Kosmetische Desodorantien, enthaltend Gemische aus Wollwachssäuren oder Wollwachssäurekomponenten und Fettsäurepartialglyceriden unverzweigter Fettsäuren |
DE4324219C2 (de) | 1993-07-20 | 1995-08-10 | Beiersdorf Ag | Desodorierende Wirkstoffkombinationen auf der Basis von alpha, omega-Alkandicarbonsäuren und Wollwachssäuren |
EP0649834A1 (de) * | 1993-10-20 | 1995-04-26 | Kao Corporation | Carboxybetaine und Sulfobetaine und diese enthaltende Reinigungszusammensetzung und kosmetische Zusammensetzung |
EP0656346B1 (de) * | 1993-12-02 | 1997-02-05 | Witco Surfactants GmbH | Verfahren zur Herstellung hochkonzentrierter fliessfähiger wässriger Lösungen von Betainen |
DE4439642C1 (de) | 1994-11-07 | 1996-01-11 | Goldschmidt Ag Th | Milde, wäßrige, tensidische Zubereitungen für kosmetische Zwecke und Reinigungsmittel |
DE19855934A1 (de) | 1998-12-04 | 2000-06-08 | Beiersdorf Ag | Verwendung von Betainen als Antitranspirantien |
DE10327871A1 (de) * | 2003-06-18 | 2005-01-05 | Goldschmidt Ag | Verwendung von Alkylguanidin-Verbindungen zur Behandlung und Nachbehandlung von Haaren |
DE102004055549A1 (de) * | 2004-11-17 | 2006-05-18 | Goldschmidt Gmbh | Verfahren zur Herstellung hochkonzentrierter fließfähiger wässriger Lösungen von Betainen |
JP2006143634A (ja) * | 2004-11-18 | 2006-06-08 | Sanyo Chem Ind Ltd | カルボキシベタイン |
DE102007040000A1 (de) * | 2007-08-23 | 2009-02-26 | Evonik Goldschmidt Gmbh | Zwitterionische Verbindungen und deren Verwendung |
-
2007
- 2007-08-23 DE DE200710040001 patent/DE102007040001A1/de not_active Withdrawn
-
2008
- 2008-06-24 EP EP08761321A patent/EP2178494A2/de not_active Withdrawn
- 2008-06-24 US US12/674,831 patent/US20110206623A1/en not_active Abandoned
- 2008-06-24 WO PCT/EP2008/058003 patent/WO2009024374A2/de active Application Filing
Non-Patent Citations (1)
Title |
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See references of WO2009024374A2 * |
Also Published As
Publication number | Publication date |
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WO2009024374A3 (de) | 2009-08-13 |
WO2009024374A2 (de) | 2009-02-26 |
DE102007040001A1 (de) | 2009-02-26 |
US20110206623A1 (en) | 2011-08-25 |
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