CN101132765B - Emollients and cosmetic compositions based on special branched hydrocarbons - Google Patents
Emollients and cosmetic compositions based on special branched hydrocarbons Download PDFInfo
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- CN101132765B CN101132765B CN2006800070807A CN200680007080A CN101132765B CN 101132765 B CN101132765 B CN 101132765B CN 2006800070807 A CN2006800070807 A CN 2006800070807A CN 200680007080 A CN200680007080 A CN 200680007080A CN 101132765 B CN101132765 B CN 101132765B
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- Prior art keywords
- acid
- fatty acid
- hydrocarbon
- electrolysis
- ester
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 58
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 46
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 45
- 239000002537 cosmetic Substances 0.000 title claims abstract description 22
- 239000003974 emollient agent Substances 0.000 title description 8
- 239000000194 fatty acid Substances 0.000 claims abstract description 80
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 53
- 229930195729 fatty acid Natural products 0.000 claims abstract description 53
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 45
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- -1 isodecyl Chemical group 0.000 claims description 55
- 238000005868 electrolysis reaction Methods 0.000 claims description 44
- 150000004665 fatty acids Chemical class 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 31
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 7
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 6
- 239000000839 emulsion Substances 0.000 claims description 5
- 239000004615 ingredient Substances 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
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- 239000003513 alkali Substances 0.000 claims description 4
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- 239000000178 monomer Substances 0.000 claims description 3
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- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- YPIFGDQKSSMYHQ-UHFFFAOYSA-N 7,7-dimethyloctanoic acid Chemical compound CC(C)(C)CCCCCC(O)=O YPIFGDQKSSMYHQ-UHFFFAOYSA-N 0.000 claims description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 2
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- 230000010534 mechanism of action Effects 0.000 abstract 1
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000003921 oil Substances 0.000 description 25
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- 239000000243 solution Substances 0.000 description 9
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
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- 241001597008 Nomeidae Species 0.000 description 5
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- 210000003491 skin Anatomy 0.000 description 5
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
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- 239000007788 liquid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- 241001465754 Metazoa Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 206010040904 Skin odour abnormal Diseases 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
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- 238000009833 condensation Methods 0.000 description 3
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- 238000001816 cooling Methods 0.000 description 3
- 239000008406 cosmetic ingredient Substances 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 3
- 238000006471 dimerization reaction Methods 0.000 description 3
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- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 3
- 229960003656 ricinoleic acid Drugs 0.000 description 3
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 3
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- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 2
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- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- 239000008251 pharmaceutical emulsion Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- CGIHFIDULQUVJG-UHFFFAOYSA-N phytantriol Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)(O)C(O)CO CGIHFIDULQUVJG-UHFFFAOYSA-N 0.000 description 1
- CGIHFIDULQUVJG-VNTMZGSJSA-N phytantriol Natural products CC(C)CCC[C@H](C)CCC[C@H](C)CCC[C@@](C)(O)[C@H](O)CO CGIHFIDULQUVJG-VNTMZGSJSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 235000014774 prunus Nutrition 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229960003471 retinol Drugs 0.000 description 1
- 235000020944 retinol Nutrition 0.000 description 1
- 239000011607 retinol Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920002477 rna polymer Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000012176 shellac wax Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 244000005714 skin microbiome Species 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- LUPNKHXLFSSUGS-UHFFFAOYSA-M sodium;2,2-dichloroacetate Chemical compound [Na+].[O-]C(=O)C(Cl)Cl LUPNKHXLFSSUGS-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 150000003408 sphingolipids Chemical class 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical class 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 description 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/31—Hydrocarbons
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/29—Coupling reactions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/83—Electrophoresis; Electrodes; Electrolytic phenomena
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Abstract
Cosmetic and/or pharmaceutical composition (I) comprises 10C hydrocarbon, which is obtained by kolbe electrolysis of at least one branched 6-26C fatty acids or a mixture of at least one linear 3-26C fatty acids and/or branched 4-26C fatty acids. An independent claim is also included for the preparation of (I). - ACTIVITY : Dermatological. - MECHANISM OF ACTION : None given.
Description
Invention field
The present invention relates to the cosmetic composition of hydrocarbonaceous base oil body, it the invention still further relates to the application of this class hydrocarbon by Cole primary (Kolbe)-synthetic obtaining.
Background technology
In being suitable for the cosmetic emulsion field of skin nursing and hair nursing, the user proposition is a large amount of to be required: except the cleaning and the nursing role of decision application purpose, important value also is as good skin-friendliness, good oil return characteristic, perfect vivid, best sensory impression and the various different parameters of bin stability.
The ingredients that is used to clean and nurse human skin and hair is also main eleoplast and water except that containing a series of surfactant generally.For example use the oil/fat/wax of hydrocarbon, ester oil and plant and animal as oil body/emollient.For satisfying market, constantly develop and test novel oil body and emulsifier-mixture in the requirement aspect the sense quality and the optimum skin compatibility.
The known for a long time hydrocarbon that in make-up composition, uses.As using mineral oil and paraffin oil as the inertia oil body.It all has shortcoming, is promptly seen by the sensation aspect, stays the skin sense of " heavy " and the extensibility of difference.Also known use has the product mixture of the various hydrocarbon of improved deployable property, as the example that makes by DE 10317781 or DE 10324508 described methods.This class mixture is difficult to characterize, and contains a large amount of each different compositions, and it also is difficult to estimate to the effect of deployable property separately.
Therefore the purpose of this invention is to provide the volatile hydrocarbon that other are applicable to the height extensibility of cosmetics, it can be simply and with produced in high yields.Another aspect of the present invention provides a class hydrocarbon, and it is suitable for the composition that substitutes as siloxanes, even has the sensation characteristic of volatile siloxane.
Unexpected discovery, the hydrocarbon of the Cole uncle electrolytic preparation by fatty acid are suitable in the cosmetics emollient as volatile height extensibility, and can high yield obtain especially.Cole's primary-electrolysis itself be a kind of morning for preparing hydrocarbon known method (H.Kolbe, Liebig Ann.Chem.1849,69,257-294), and be a kind of prior art.But the hydrocarbon of also not describing the symmetry structure for preparing as required thus so far is applicable in the cosmetics.
Summary of the invention
The purpose of this invention is to provide a kind of cosmetic compositions, it comprises at least a hydrocarbon with at least 10 carbon atoms, and this hydrocarbon makes by the C6-C26-fatty acid of at least a side chain of Cole's primary-electrolysis (a) or the mixture of (b) being made up of the C4-C26-fatty acid of at least a straight chain C 3-C26-fatty acid and at least a side chain.By the present invention, this hydrocarbon must have the chain length of at least 10 carbon atoms, to be suitable for cosmetic applications.If have the fatty acid and straight chain C 3-fatty acid (propanoic acid) reaction of side chain, then this branched chain fatty acid must contain at least 9 carbon atoms, and the hydrocarbon of gained contains 10 carbon atom total amounts at least thus.Otherwise when using the C4-fatty acid of side chain, this straight chain fatty acid must contain at least 8 carbon atoms.In the present invention, cosmetic or medicinal compositions both can contain the single hydrocarbon that produces by Cole's primary-electrolysis, also can contain product-mixture that C6-C26-fatty acid by the various side chains of Cole's primary-electrolysis or fatty acid and side chain C4-C26 fatty acid by Cole's primary-electrolysis straight chain C 3-C26 are produced.According to the difference of each application purpose, it is advantageous under each situation.
Cole primary-electrolytic advantage is the isomerization that does not cause free radical.Metal cation is shifted to negative electrode under galvanic influence, and electronegative carboxylate radical is shifted to anode, carries out decarboxylating by anodic oxidation on anode.Follow the alkyl-free radical dimerization that forms.The product that forms by dimerization is symmetric and has and wherein accurately reproduce the structure that the fatty acid structure characteristic promptly keeps architectural characteristic.Should have substitute mode by the emollient of Cole's primary-electrolysis gained thus, this is unavailable by other preparation method (as low dimerization).Be different from known branched alkane-emollient by the synthetic alkane that obtains of Cole uncle.For example Cole's primary-electrolysis of 2-ethyl hexane can cause especially symmetrical structure the diethyl decane (J.E.Barry, M.Finkelstein, E.A.Mayeda, S.D.Ross, J.Am.Chem.Soc.1976,98,8098-8101).
Fig. 1
By situation and whether opinion is to use single fatty acid or fatty acid mixt as raw material, can accurately control estimate the number of product.When the mixture of carboxylic acids electrolysis, produce the product of all possible symmetric and asymmetric free radical-combination.Be different from the hydrocarbon-mixture situation that obtains by condensation reaction and polymerization, when Cole's primary-electrolysis the composition of this product mixtures be more easy to control, can accurately define very complicated.Therefore can introduce the hydrocarbon mixture that side chain position and development have optimization expansion cascade as required in hydrocarbon, its application in cosmetics causes sensorial advantage.By the present invention, for example can carry out Cole's primary-electrolysis, and product is introduced in the cosmetic ingredients the mixture of forming at 1: 1 with mol ratio by neopentanoic acid and isostearic acid.Using the C6-C22-fatty acid to carry out Cole's primary-electrolysis is that the present invention is preferred, because the hydrocarbon that is produced has the better characteristic that is suitable for cosmetic applications.
Particularly preferred compositions is characterised in that among the present invention, and the hydrocarbon by Cole's primary-electrolytic preparation contains maximum 22 carbon atoms.The feature that contains the hydrocarbon of maximum 22 carbon atoms is that volatility and sensation advantage are preferably arranged in end formulation, and is particularly suitable as the siloxanes substitute.
In another preferred version of the present invention, contained compositions contains the hydrocarbon that the electrolysis of at least a any mixture by thylhexoic acid, different n-nonanoic acid, isodecyl acid, isostearic acid, fatty acid monomer, neodecanoic acid or these fatty acids obtains, or the hydrocarbon that obtains of the electrolysis of the mixture of above-mentioned one or more fatty acids and neopentanoic acid or cyclohexane carboxylic.
Fatty acid monomer is the known term that is used for the mixture be made up of the unsaturated fatty acid of side chain of this professional people.Also be suitable for using Cekanoic C8 (isooctyl acid), Cekanoic C9 (different n-nonanoic acid: 3,5,5-tri-methyl hexanoic acid and 2,5,5-tri-methyl hexanoic acid) and the Cekanoic C10 (isodecyl acid) of Exxon Mobile company among the present invention, it is an isomeric mixtures.
In another preferred version, said composition contains at least a saturated hydrocarbons that obtains by Cole's primary-electrolysis.It is favourable using saturated hydrocarbons, because it is not too responsive to oxidation.
Compositions of the present invention contains the hydrocarbon that makes by Cole's primary-electrolysis, and its content is preferably 0.1-50 weight % by total composition.
Use is favourable at the unbranched branched chain fatty acid of alpha-position to the present invention.Side chain at alpha-position can cause Cole primary-electrolytic low-yield once in a while.
The present invention also aims to contain at least 10 carbon atoms hydrocarbon its in cosmetic composition, be used as the oil body of height extensibility or as the siloxanes substitute, this hydrocarbon is to make by the C6-C26-fatty acid of at least a side chain of Cole's primary-electrolysis (a) or the mixture (b) be made up of at least a straight chain C 3-C26-fatty acid and at least a side chain C4-C26-fatty acid.
Another object of the present invention provides a kind of method for preparing cosmetic and/or Pharmaceutical composition, the hydrocarbon with at least 10 carbon atoms that will make by the C6-C26-fatty acid of at least a side chain of Cole's primary-electrolysis (a) or the mixture of (b) being made up of at least a straight chain C 3-C26-fatty acid and at least a side chain C4-C26-fatty acid in the method is as oil phase, also contain other oil-soluble composition when needing, and and water, also contain other water soluble ingredient when needing, and other auxiliary agent and the additive commonly used when needing is processed into emulsion together.Preferably this Cole's primary-electrolysis is carried out or is carried out with the fatty acid in solvent with the fatty acid of non-dilution, and at this moment the fatty acid of 1-25 mole % neutralizes with alkali, and at 100-1000mA/cm
2Electric current density and 0-70 ℃ under carry out electrolysis.
Cole's primary-electrolysis(general purpose discipline)
Application of pure or in solvent (particular methanol; The methanol of especially preferably moisture (1-5 weight %, preferred 2.5-3 weight %)) fatty acid in.With alkali (preferred alkali is Feldalat NM) neutralization part acid (1-25 mole %, preferred 5-15 mole %).This electrolysis is carried out on platinum electrode, platinum/niobium electrode, graphite electrode or vitreous carbon (vitreous carbon) electrode.Electric current density is 100-1000mA/cm
2(preferred 150-700mA/cm
2, preferred especially 200-600mA/cm
2).This electrolysis is carried out under 0-70 ℃ (preferred 35-50 ℃).
Because the hydrocarbon of gained does not mix mutually with polar reaction solution (carboxylic acid in the methanol), so product is separated out in mutually second.This is told mutually, and this contains highly purified required hydrocarbon (emollient) mutually.
The hydrocarbon that makes through Cole's primary-electrolysis has better extensibility (see figure 1) than comparable hydrocarbon.For this reason under 24 ℃ and 40% air humidity with the droplets of 25 μ 1 on filter paper.Draw this automatic broadening and time relation in the drawings, this broadening must be fast more, and then its extensibility is good more.
Cosmetic/medicinal ingredients
The hydrocarbon that should make by Cole's primary-electrolysis can be used for preparing stable cosmetic and pharmaceutical emulsion, the expansion cascade is arranged when needing, and this hydrocarbon is applicable to also in cosmetic and Pharmaceutical composition as the siloxanes substituent.
Compositions of the present invention can be to be used for the preparation of body nursing such as precursor emulsion, frost, washing liquid, sprayable emulsion, to be used to remove the product of bromhidrosis flavor etc.This hydrocarbon also can be used in the preparation that contains surfactant as foam bath agent and shower agent, shampoo and hair conditioner.According to this Toiletry preparation of application purpose can contain a series of other auxiliary agents and additive such as surfactant, other oil body, emulsifying agent, pearlescent waxes, denseness imparting agent, thickening agent, oil spilling agent, stabilizing agent, polymer, fat, wax, lecithin, phospholipid, biogen activating agent, the anti-light factor of UV-, antioxidant, deodorizer, antiperspirant, anti-dandruff agent, film former, extender, insect-proof agent, from brown dose, tyrosinase inhibitor (depigmenting agent), hydrotropic agent, solubilizing agent, antiseptic, perfumery oil, dyestuff etc., below exemplary illustration.
Surfactant
Surfactant can comprise anion surfactant, non-ionic surface active agent, cationic surfactant and/or amphoteric surfactant or zwitterionic surfactant.In containing the cosmetic ingredients of surfactant, preferably contain at least a anion surfactant as shower gels, foam bath agent, shampoo etc.The content of this surfactant is generally about 1-30, preferred 5-25 and preferred especially 10-20 weight %.
The representative instance of anion surfactant is a soap; the alkyl phenyl sulphonic acid ester; the alkane sulphonic acid ester; the alkene sulfonic acid ester; the alkyl ether sulphonic acid ester; the glycerin ether sulphonic acid ester; Alpha-Methyl ester sulphonic acid ester; sulfo-fatty acid; alkyl sulfate; fatty alcohol ether sulfate; the glycerin ether sulfuric ester; fatty acid ether sulfuric ester; hydroxyl mixing-ether sulfuric ester; monoglyceride (ether) sulfuric ester; fatty acid amide (ether) sulfuric ester; monoalkyl sulfosuccinate and two alkyl sulfosuccinate; the sulfo group triglyceride; the amide soap; ether carboxylic acid and its salt; the fatty acid isethionic acid ester; the fatty acid sarcosinate; fatty acid taurine ester; N-acylamino acid such as acyl group lactoyl ester; the acyl group tartaric acid ester; acyl glutamic acid ester and acylaspartic acid ester; the oligomeric alkyl glucoside sulfuric ester; the albumen fatty acid condensation substance plant product of Semen Tritici aestivi (particularly based on) and alkyl (ether) phosphate ester.As long as anion surfactant contains the polyglycol ether chain, then it has common but preferred a kind of narrow homologue distributes.The representative instance of non-ionic surface active agent is fatty alcohol polyglycol ether, alkyl phenol polyglycol ether, fatty acid polyethylene glycol ester, fatty acid amide polyglycol ether, fatty amine polyglycol ether, oxyalkylated triglyceride, compound ether or basic oligoglycosides of alkane (alkene) or the glucuronic acid that mixes formal, optional part oxidation
Derivant, fatty acid-N-alkyl glucose amide, the protolysate plant product of Semen Tritici aestivi (particularly based on), polyol fatty acid ester, sugar ester, Isosorbide Dinitrate, polysorbate and amine oxide.As long as non-ionic surface active agent contains the polyglycol ether chain, then it has common but preferably a kind of narrow homologue distributes.The representative instance of cationic surfactant is quaternary ammonium compound such as dimethyl distearyl ammonium chloride and season ester (Esterquate), particularly quaternised fatty acid trialkanolamine ester salt.The representative instance of both sexes or zwitterionic surfactant is alkyl betaine, alkylamidoalkyl betanin, alanine ester, amino glycinate, imidazolinium betaine and sulfobetaines.Described surfactant fully comprises compound known.Structure about these materials can be consulted the relevant general introduction paper in this field with preparation.The surfactant promptly special and skin-compatible of the gentleness of particularly suitable is fatty alcohol polyglycol ether sulfuric ester, monoglyceride sulfuric ester, monoalkyl sulfosuccinate and/or two alkyl sulfosuccinate, fatty acid isethionic acid ester, fatty acid sarcosinate, fatty acid taurine ester, fatty acid glutamate, alpha-alefinically sulphonic acid ester, ether carboxylic acid, oligomeric alkyl glucoside, fatty acid glucamide, alkylamidoalkyl betanin, both sexes acetal and/or albumen fatty acid condensation substance, and this albumen fatty acid condensation substance is preferably based on wheat protein.
Oil body
The body nursing agent contains a series of optimized other oil body of sense quality and the emollient of helping usually as frost, lotion and emulsion.The common content of this oil body accounts for the 1-50 weight % of total amount, preferred 5-25 weight %, particularly 5-15 weight %.For example be based on as other oil body and contain 6-18, the Guerbet alcohol of the aliphatic alcohol of preferred 8-10 carbon atom, the C of straight chain
6-C
22-fatty acid and straight or branched C
6-C
22The ester of-aliphatic alcohol or the C of side chain
6-C
13The C of-carboxylic acid and straight or branched
6-C
22The ester of-aliphatic alcohol is as nutmeg base nutmeg acid esters, nutmeg base cetylate, nutmeg base stearate, nutmeg base isostearate, nutmeg base oil acid esters, nutmeg Ji behenic acid ester, nutmeg base eruciate, cetyl nutmeg acid esters, the cetyl cetylate, the cetyl stearate, the cetyl isostearate, the cetyl oleate, cetyl behenic acid ester, the cetyl eruciate, stearic acid-base nutmeg acid esters, the stearic acid-base cetylate, the stearic acid-base stearate, the stearic acid-base isostearate, the stearic acid-base oleate, stearic acid-base behenic acid ester, the stearic acid-base eruciate, isostearic acid base nutmeg acid esters, isostearic acid base cetylate, isostearic acid base stearate, isostearic acid base isostearate, isostearic acid base oil acid esters, isostearic acid Ji behenic acid ester, isostearic acid base oil acid esters, oil base nutmeg acid esters, the oil base cetylate, the oil base stearate, the oil base isostearate, the oil base oleate, oil base behenic acid ester, oil base eruciate; behenic acid base nutmeg acid esters; behenic acid base cetylate; behenic acid base stearate; behenic acid base isostearate; behenic acid base oil acid esters; behenic acid base behenic acid ester; behenic acid base eruciate, erucic acid base nutmeg acid esters, erucic acid base cetylate, erucic acid base stearate, erucic acid base isostearate, erucic acid base oil acid esters, erucic acid Ji behenic acid ester and erucic acid base eruciate.That be suitable in addition, is the C of straight chain
6-C
22The ester of-fatty acid and branched-chain alcoho, particularly 2-Ethylhexyl Alcohol, C
18-C
38The C of-alkyl hydroxy carboxylic acid and straight or branched
6-C
22The ester of the ester of-aliphatic alcohol, particularly dioctyl maleate, straight chain and/or branched chain fatty acid and polyhydric alcohol (as propylene glycol, dimer diol or trimerization triol) and/or Guerbet alcohol, based on C
6-C
10The triglyceride of-fatty acid, based on C
6-C
18The liquid glycerin one ester/diglyceride/triglyceride mixture of-fatty acid, C
6-C
22The pure and mild aromatic carboxylic acid of-aliphatic alcohol and/or Guerbet, particularly benzoic ester, C
2-C
12The C of ester, vegetable oil, branched-chain primary alcohol, substituted cyclohexane, straight chain and the side chain of the polyhydric alcohol of the straight or branched alcohol of-dicarboxylic acids and 1-22 carbon atom or 2-10 carbon atom and 2-6 hydroxyl
6-C
22-aliphatic alcohol carbonic ester, as dicaprylyl carbonate (
CC), based on 6-18, Guerbet carbonic ester, benzoic acid and straight chain and/or the side chain C of the aliphatic alcohol of preferred 8-10 carbon atom
6-C
22-alcohol (as
TN) ester, contain straight or branched, symmetry or asymmetric dialkyl ether that the 6-22 carbon atom is arranged in each alkyl, as dicaprylyl ether (
OE), the open-loop products of epoxidised fatty acid and polyhydric alcohol.
Fat and wax
Fat and wax can be added in the body care product as nursing agent, the denseness of also available its increase cosmetics.The representative instance of fat is a glyceride, promptly solid plant or animal product, and it mainly is made up of the mixed glyceride of higher fatty acids.Also can use fatty acid partial glycerides, promptly contain the technical grade monoesters of glycerol of fatty acid and/or dibasic acid esters such as glycerol list with 12-18 carbon atom/pair-laurate, glycerol list/pair-cetylate or glycerol list/pair-stearate.Can use particularly native paraffin as wax, as candelilla wax, Brazil wax, Japan wax, esparto wax, cork wax, Guaruma wax, rice embryo oil
Wax, sugarcane wax, ouricury wax, montan wax, Cera Flava, shellac wax, spermaceti, lanoline (lanocerin), tail fat fat, microwax, ceresine, pertroleum wax, paraffin, little wax; Chemical modification wax (hard wax) is as brown coal ester type waxes, Sasol wax, hydrogenation jojoba wax and synthetic wax such as polyalkylene wax and polyethylene glycol wax.Also available class fatty material is as additive such as lecithin and phospholipid except that fat.The example of natural phosphatidyl choline is a cephalin, and it is also referred to as phosphatidic acid, and is 1, the derivant of 2-diacyl-sn-glycerol-3-phosphate.In contrast, phospholipid means the monoesters and the preferred dibasic acid esters (glycerophosphate) of phosphoric acid and glycerol usually, and it belongs to fat usually.Available in addition sphingol or sphingolipid.
Be suitable for use as thickening agent for example for the silica gel-class of high dispersive (hydrophilic silicate), polysaccharide, particularly Xanthan gum, guar gum, agar, alginate and tylose, carboxymethyl cellulose and hydroxyethyl-cellulose and hydroxypropyl cellulose, polyvinyl alcohol, polyvinylpyrrolidone and bentonite as
Gel VS-5PC (Rheox).
The anti-light factor of UV-means the organic substance (filtering agent against sunshine) that for example at room temperature exists with liquid state or crystalloid, and it can absorb ultraviolet rays and the energy that absorbs is emitted once more with long-wave radiation such as heat.The UV-B-filtering agent can be dissolved in oil or water-soluble.Typical UV-A-filtering agent can use the derivant of benzoyl methane especially.This UV-A-filtering agent and UV-B-filtering agent can certainly mixture use, for example by the derivant of benzoyl methane, as 4-tert-butyl-4 '-methoxy dibenzoyl methylmethane (
1789) and 2-cyano group-3, the ester of 3 '-phenyl-cinnamic acid-2-ethyl-hexyl ester (octocrylene) and cinnamic acid, the compositions of preferred 4-methoxy cinnamic acid-2-ethyl hexyl ester and/or 4-methoxy cinnamic acid propyl diester and/or 4-methoxy cinnamic acid isopentyl ester.This based composition is often combined with its alkali metal salt, alkali salt, ammonium salt, alkylammonium salt, alkanol ammonium salts and glucose ammonium salt with water-soluble filtering agent such as 2-Phenylbenzimidazole-5-sulfonic acid.
Except that described solable matter, also can use insoluble anti-delustering pigment is finely divided metal-oxide.The example of the metal-oxide that is suitable for is zinc oxide and titanium dioxide particularly.Except that these two groups of main antisun materials, also can use the inferior preventing light agent of the antioxidant that can interrupt the photochemical reaction chain, it causes this chain when UV-injects in the skin.
The biogen activating agent for example means tocopherol, tocopherol acetas, tocopherol cetylate, ascorbic acid, (deoxidation) ribonucleic acid and its fragment product, beta glucan, retinol, bisabolol, allantoin, phytantriol, pantothenylol, AHA-acid, aminoacid, ceramide, false vitalility through amide, quintessence oil, plant extraction liquid such as Prunus extracting solution, bambarra groundnut extracting solution (Bambaranusextrakt) and vitamin complex.
Deodorant active agent stops body odour, covers or remove body odour.Body odor acts on apocrine sweat gland by skin bacteria and produces, and at this moment forms unpleasant catabolite.Therefore be suitable for particularly antibacterial inhibitor, the agent of resistance enzyme, odour adsorbent or stink masking agent as deodorant active agent.
Can use for example N as anthelmintic, the N-diethyl--toluamide, 1,2-pentanediol or 3-(N-just-butyl-N-acetyl group-amino)-propanoic acid ethyl ester, its by Merck KGaA company with trade mark Insect
3535 sell, and also have butyl acetyl-amino propionic ester.
As from brown dose suitable be dihydroxy acetone.Can use the tyrosine kinase inhibitors such as arbutin, ferulic acid, kojic acid, coumarin acid and the ascorbic acid (vitamin C) that prevent that melanocyte from forming and using in depigmenting agent.
What be suitable for as antiseptic is to be as phenyl phenol, formalin, p-Hydroxybenzoate, pentanediol or Pyrusussuriensis saccharic acid and the known trade mark
Silver complex and the part A of the adnexa 6 in cosmetics regulations and B in other material type of mentioning.
Can mention the mixture of forming with synthetic spice by natural as perfumery oil.Natural perfume material is the extract of flower, stem and leaf, fruit, shell, root, timber (Holzern), Rhizoma et radix valerianae and grass, needle and branch, resin and face cream.In addition, also can use the flavor compounds of animal material such as civet and beaver perfume and synthetic ester, ether, aldehyde, ketone, pure and mild hydrocarbon.
As pearlescent waxes, the pearlescent waxes that particularly is applicable to surfactant formulations for example: alkylidene glycol ester, particularly glycol distearate; Marlamid, particularly fatty acid distribution of coconut oil diglycollic amide, partial glyceride, especially glycerol monostearate; Polybasic ester, the carboxylic acid that optional hydroxyl replaces and the ester that contains the aliphatic alcohol of 6-22 carbon atom, particularly tartaric long-chain ester; Aliphatic alcohol, aliphatic ketone, fatty aldehyde, aliphatic ether and aliphatic carbonate ester, particularly laurone and distearyl acid ether that fat is at least 24 carbon atoms as containing sum; Fatty acid such as stearic acid, hydroxy stearic acid or behenic acid, contain the olefinic epoxide of 12-22 carbon atom and contain the 12-22 carbon atom aliphatic alcohol open-loop products and/or contain the 2-15 carbon atom and the polyhydric alcohol of 2-10 hydroxyl with and composition thereof.
Can use lanolin derivative and lecithin derivant, polyol fatty acid ester, monoglyceride and the Marlamid of material such as lanoline and lecithin and poly-ethoxyquin or acyl groupization as the fat agent of overflowing, this Marlamid is simultaneously also as foam stabiliser.
Can use slaine such as magnesium stearate, aluminium stearate and/or zinc stearate or ricinoleic acid magnesium, ricinoleic acid aluminum and/or the ricinoleic acid zinc of fatty acid as stabilizing agent.
For improving flow behavior, also can use hydrotropic agent, as ethanol, isopropyl alcohol or polyhydric alcohol.Polyhydric alcohol considered here preferably has 2-15 carbon atom and at least two hydroxyls.It is particularly amino or use the nitrogen modification that this polyhydric alcohol also can contain other functional group.
Embodiment
Embodiment 1:
Electrolysis is to carry out in the beaker groove of indiscrete 200ml.Area respectively is 1cm
2Two platinized platinum electrodes be 1-3mm location with the interelectrode distance.This electrode is connected into power-supply device (3A/30V).In electrolysis bath, add 40g (0.28 mole) thylhexoic acid, 2.5g Feldalat NM (0.014 mole, 30% solution in methanol) and 4.2g water, and be charged to 150ml with methanol.Under agitation this solution is with the constant current electrolysis of 0.5A, and required for this reason voltage is 26V.This electrolysis bath is with ice/water cooling, so that temperature is adjusted to 40 ℃.Stop electrolysis after 15 hours.This colourless product is separated out mutually as second.Output is 16.0g.The gas chromatographic analysis of product shows content＞95% (seeing figure) of diethyl decane.
Embodiment 2:
Electrolysis is to carry out in the beaker groove of indiscrete 200ml.Area respectively is 1cm
2Two platinized platinum electrodes be 1-3mm location with the interelectrode distance.This electrode is connected into power-supply device (3A/30V).In electrolysis bath, add 40g (0.28 mole) Cekanoic C8 (Exxon company), 2.5g Feldalat NM (0.014 mole, 30% solution in methanol) and 4.2g water, and be charged to 150ml with methanol.Under agitation this solution is with the constant current electrolysis of 0.5A, and required for this reason voltage is 26V.This electrolysis bath is with ice/water cooling, so that temperature is adjusted to 40 ℃.Stop electrolysis after 15 hours.This colourless product is separated out mutually as second.The gas chromatographic analysis of product shows content＞95% of the side chain C14-hydrocarbon that comprises a plurality of isomers with methyl branch.This methyl branch has the distribution pattern identical with raw material Cekanoic C8.Output is 17.0g.
Embodiment 3:
Electrolysis is to carry out in the beaker groove of indiscrete 200ml.Area respectively is 1cm
2Two platinized platinum electrodes be 1-3mm location with the interelectrode distance.This electrode is connected into power-supply device (3A/30V).In electrolysis bath, add 23g (0.16 mole) thylhexoic acid, 18.5g (0.16 mole) caproic acid, 2.9g Feldalat NM (0.016 mole, 30% solution in methanol) and 4.2g water, and be charged to 150ml with methanol.Under agitation this solution is with the constant current electrolysis of 0.4A, and required for this reason voltage is 26V.This electrolysis bath is with ice/water cooling, so that temperature is adjusted to 40 ℃.Stop electrolysis after 15 hours.This colourless product is separated out mutually as second.Output is 18.5g.The gas chromatographic analysis of product shows total content＞95% of the mixture of being made up of three kinds of different hydrocarbon.These three kinds of hydrocarbon are decane, ethyl decane and diethyl decane.(seeing figure)
Output described in the embodiment is not best, can be improved by program optimization by the professional.
Cosmetic composition
The used consumption of representing in weight % is all by the weight of cosmetic ingredients
*) measure 4Upm+Helipath, 23 ℃ with TE-Spindel
| Commercially available name | The INCI title | Weight % |
| Cutina GMS-SE | The glyceryl stearate | 5.50 |
| Eumulgin B1 | Ceteareth-12 | 0.20 |
| Cutina FS45 | Stearic acid (with) Palmic acid | 2.00 |
| Lanette 16 | Spermol | 1.50 |
| Fitoderm | Squalane | 6.00 |
| Commercially available name | The INCI title | Weight % |
| The diethyl decane | - | 5.00 |
| Cegesoft SH | Shorea Stenoptera | 5.00 |
| Cegesoft PFO | Passiflora Incarnata | 1.00 |
| Cetiol MM | Nutmeg base nutmeg acid esters | 1.00 |
| 99% glycerol | Glycerol | 5.00 |
| Formalin 37.5% | 0.15 | |
| Distillation H 2O | 93.85 | |
| Viscosity [mPas] *) | 187500 |
*) measure 4Upm+Helipath, 23 ℃ with TE-Spindel
Claims (9)
1. cosmetic composition, it comprises at least a hydrocarbon that contains at least 10 carbon atoms, and this hydrocarbon is by Cole's primary-electrolysis
(a) the C6-C26-fatty acid of at least a side chain or
(b) mixture of the C4-C26-fatty acid of at least a straight chain C 3-C26-fatty acid and at least a side chain
Make.
2. the compositions of claim 1 is characterized in that, this hydrocarbon contains maximum 22 carbon atoms.
3. one of at least compositions among the claim 1-2 is characterized in that this branched chain fatty acid is unbranched at alpha-position.
4. one of at least compositions among the claim 1-3 is characterized in that this hydrocarbon is a saturated hydrocarbons.
5. one of at least compositions among the claim 1-2, it is characterized in that, employed fatty acid is any mixture of thylhexoic acid, different n-nonanoic acid, isodecyl acid, isostearic acid, fatty acid monomer, neodecanoic acid or these fatty acids, or the mixture of above-mentioned one or more fatty acids and neopentanoic acid or cyclohexane carboxylic.
6. one of at least compositions among the claim 1-5 is characterized in that the amount of hydrocarbon is counted 0.1-50 weight % by total composition.
7. the hydrocarbon that contains at least 10 carbon atoms in cosmetic and/or Pharmaceutical composition as the good oil body of extensibility or as the application of siloxanes substitute, this hydrocarbon is by Cole's primary-electrolysis
(a) the C6-C26-fatty acid of at least a side chain or
(b) mixture of the C4-C26-fatty acid of at least a straight chain C 3-C26-fatty acid and at least a side chain
Make.
8. method that is used to prepare cosmetic and/or Pharmaceutical composition will be by Cole's primary-electrolysis in the method
(a) the C6-C26-fatty acid of at least a side chain or
(b) mixture of the C4-C26-fatty acid of at least a straight chain C 3-C26-fatty acid and at least a side chain
The hydrocarbon that contains at least 10 carbon atoms that makes is processed into emulsion as oil phase with water, and can also add other accessory ingredient of in common use and additive when needing, and this oil phase also contains other oil-soluble composition when needing, and this water also contains other water soluble ingredient when needing.
9. the method for claim 8 is characterized in that, carries out Cole's primary-electrolysis with the fatty acid of not diluted or the fatty acid that is used in the solvent, and wherein the fatty acid of 1-25 mole % neutralizes through alkali, and is 100-1000mA/cm in electric current density
2With temperature is to carry out electrolysis under 0-70 ℃.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005009853.3 | 2005-03-04 | ||
| DE102005009853A DE102005009853A1 (en) | 2005-03-04 | 2005-03-04 | Cosmetic and/or pharmaceutical composition, useful for cleaning and protecting the human skin and hair, comprises hydrocarbon, which is obtained by kolbe electrolysis of fatty acids |
| DE102005011691.4 | 2005-03-11 | ||
| DE102005011691A DE102005011691A1 (en) | 2005-03-11 | 2005-03-11 | Cosmetic and/or pharmaceutical composition, useful for cleaning and protecting the human skin and hair, comprises hydrocarbon, which is obtained by kolbe electrolysis of fatty acids |
| PCT/EP2006/001641 WO2006094642A1 (en) | 2005-03-04 | 2006-02-23 | Emollients and cosmetic compositions based on special branched hydrocarbons |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101132765A CN101132765A (en) | 2008-02-27 |
| CN101132765B true CN101132765B (en) | 2010-05-19 |
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ID=36933662
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2006800070807A Expired - Fee Related CN101132765B (en) | 2005-03-04 | 2006-02-23 | Emollients and cosmetic compositions based on special branched hydrocarbons |
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| Country | Link |
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| CN (1) | CN101132765B (en) |
| DE (1) | DE102005009853A1 (en) |
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| CN107944639A (en) * | 2017-12-15 | 2018-04-20 | 天津大学 | A kind of Distribution system method based on optimal flow pattern algorithm Yu Mayeda spanning tree practical algorithms |
| CN110016688B (en) * | 2019-04-08 | 2020-11-06 | 天津大学 | Electrochemical preparation method of alcohol substance |
| CN110016686B (en) * | 2019-04-08 | 2021-01-15 | 天津大学 | Method for producing hydrocarbons by electrolysis of mixed carboxylic acids |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2760926A (en) * | 1955-09-14 | 1956-08-28 | Colgate Palmolive Co | Process for the preparation of aliphatic ethers |
| US4853217A (en) * | 1986-05-10 | 1989-08-01 | Toyo Seikan Kaisha, Ltd. | Methods and compositions for controlling the pear leaf blister moth, Leucoptera scitella |
| US5627056A (en) * | 1992-11-03 | 1997-05-06 | Elizabeth Arden Co., Division Of Conopco, Inc. | Method of synthesizing lipids and cosmetic composition comprising them |
-
2005
- 2005-03-04 DE DE102005009853A patent/DE102005009853A1/en not_active Withdrawn
-
2006
- 2006-02-23 CN CN2006800070807A patent/CN101132765B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2760926A (en) * | 1955-09-14 | 1956-08-28 | Colgate Palmolive Co | Process for the preparation of aliphatic ethers |
| US4853217A (en) * | 1986-05-10 | 1989-08-01 | Toyo Seikan Kaisha, Ltd. | Methods and compositions for controlling the pear leaf blister moth, Leucoptera scitella |
| US5627056A (en) * | 1992-11-03 | 1997-05-06 | Elizabeth Arden Co., Division Of Conopco, Inc. | Method of synthesizing lipids and cosmetic composition comprising them |
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| Publication number | Publication date |
|---|---|
| CN101132765A (en) | 2008-02-27 |
| DE102005009853A1 (en) | 2006-09-21 |
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