JP6067753B2 - ワセリン代替物としてのゲルベアルコール - Google Patents
ワセリン代替物としてのゲルベアルコール Download PDFInfo
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- JP6067753B2 JP6067753B2 JP2014556990A JP2014556990A JP6067753B2 JP 6067753 B2 JP6067753 B2 JP 6067753B2 JP 2014556990 A JP2014556990 A JP 2014556990A JP 2014556990 A JP2014556990 A JP 2014556990A JP 6067753 B2 JP6067753 B2 JP 6067753B2
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- alcohol
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims description 61
- 235000019271 petrolatum Nutrition 0.000 title claims description 37
- 239000004264 Petrolatum Substances 0.000 title claims description 34
- 229940066842 petrolatum Drugs 0.000 title claims description 34
- 239000000203 mixture Substances 0.000 claims description 149
- 238000002844 melting Methods 0.000 claims description 59
- 230000008018 melting Effects 0.000 claims description 59
- 150000002191 fatty alcohols Chemical class 0.000 claims description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 239000002537 cosmetic Substances 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 12
- 238000009826 distribution Methods 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 6
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 5
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims description 4
- 238000005259 measurement Methods 0.000 claims description 4
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- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 28
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- 125000000217 alkyl group Chemical group 0.000 description 19
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- 150000003839 salts Chemical class 0.000 description 18
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- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 12
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 11
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- HEAHZSUCFKFERC-IWGRKNQJSA-N [(2e)-2-[[4-[(e)-[7,7-dimethyl-3-oxo-4-(sulfomethyl)-2-bicyclo[2.2.1]heptanylidene]methyl]phenyl]methylidene]-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonic acid Chemical group CC1(C)C2CCC1(CS(O)(=O)=O)C(=O)\C2=C\C(C=C1)=CC=C1\C=C/1C(=O)C2(CS(O)(=O)=O)CCC\1C2(C)C HEAHZSUCFKFERC-IWGRKNQJSA-N 0.000 description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 10
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 10
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- 230000001953 sensory effect Effects 0.000 description 9
- 229940099259 vaseline Drugs 0.000 description 9
- WSSJONWNBBTCMG-UHFFFAOYSA-N 2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C1=CC=CC=C1O WSSJONWNBBTCMG-UHFFFAOYSA-N 0.000 description 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
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- 229930195733 hydrocarbon Natural products 0.000 description 8
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- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 7
- 229920002125 Sokalan® Polymers 0.000 description 7
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- 239000000839 emulsion Substances 0.000 description 7
- 150000002170 ethers Chemical class 0.000 description 7
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 7
- 239000004310 lactic acid Substances 0.000 description 7
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- 238000000034 method Methods 0.000 description 7
- 239000012188 paraffin wax Substances 0.000 description 7
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 150000003863 ammonium salts Chemical class 0.000 description 6
- 239000003945 anionic surfactant Substances 0.000 description 6
- XNEFYCZVKIDDMS-UHFFFAOYSA-N avobenzone Chemical compound C1=CC(OC)=CC=C1C(=O)CC(=O)C1=CC=C(C(C)(C)C)C=C1 XNEFYCZVKIDDMS-UHFFFAOYSA-N 0.000 description 6
- 239000003093 cationic surfactant Substances 0.000 description 6
- 229920006037 cross link polymer Polymers 0.000 description 6
- 150000005690 diesters Chemical class 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
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- 239000010695 polyglycol Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 150000003626 triacylglycerols Chemical class 0.000 description 6
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 5
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
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- 125000002091 cationic group Chemical group 0.000 description 5
- 239000000077 insect repellent Substances 0.000 description 5
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 5
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 5
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- 238000003786 synthesis reaction Methods 0.000 description 5
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 5
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 4
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 4
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
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- 230000001166 anti-perspirative effect Effects 0.000 description 4
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- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 4
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
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- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 4
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- 125000005456 glyceride group Chemical group 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 3
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- 230000001960 triggered effect Effects 0.000 description 1
- FAGMGMRSURYROS-UHFFFAOYSA-M trihexadecyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC FAGMGMRSURYROS-UHFFFAOYSA-M 0.000 description 1
- 229940118576 triisostearyl citrate Drugs 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- OEIXGLMQZVLOQX-UHFFFAOYSA-N trimethyl-[3-(prop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCNC(=O)C=C OEIXGLMQZVLOQX-UHFFFAOYSA-N 0.000 description 1
- UKBHVNMEMHTWQO-UHFFFAOYSA-N trioctadecyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CC(O)(C(=O)OCCCCCCCCCCCCCCCCCC)CC(=O)OCCCCCCCCCCCCCCCCCC UKBHVNMEMHTWQO-UHFFFAOYSA-N 0.000 description 1
- ICWQKCGSIHTZNI-UHFFFAOYSA-N tris(16-methylheptadecyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)CC(O)(C(=O)OCCCCCCCCCCCCCCCC(C)C)CC(=O)OCCCCCCCCCCCCCCCC(C)C ICWQKCGSIHTZNI-UHFFFAOYSA-N 0.000 description 1
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 description 1
- 229940040064 ubiquinol Drugs 0.000 description 1
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
- 229940035936 ubiquinone Drugs 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 235000019386 wax ester Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/32—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups
- C07C29/34—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions without formation of -OH groups by condensation involving hydroxy groups or the mineral ester groups derived therefrom, e.g. Guerbet reaction
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/06—Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/125—Monohydroxylic acyclic alcohols containing five to twenty-two carbon atoms
-
- 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
- A61K2800/10—General cosmetic use
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/59—Mixtures
- A61K2800/592—Mixtures of compounds complementing their respective functions
- A61K2800/5922—At least two compounds being classified in the same subclass of A61K8/18
-
- 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
- A61Q19/10—Washing or bathing preparations
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Cosmetics (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
示差走査熱量測定(DSC)は、試料物質の物理的および化学的構造の温度および時間依存性変化の故に生じる熱流量の変化を測定する。DSCにより、一定の加熱速度で試料を溶融する際の、試料物質の熱吸収が確定される。
a)45〜95重量%のセチルステアリルアルコール、
b)5〜55重量%のC8〜22脂肪アルコール、および
c)場合により5重量%の少なくとも3個の炭素原子を有する脂肪族ジオール
の反応により得られることが見出された。
a)60〜70重量%のセチルステアリルアルコール、
b)30〜40重量%のC8〜22脂肪アルコール、および
c)場合により5重量%の少なくとも3個の炭素原子を有する脂肪族ジオール
の反応により得られ、−20℃〜+70℃の間の示差走査熱量測定(DSC)により測定した融点範囲を有しており、融点範囲の幅は少なくとも30℃であり、融点範囲の極大値は35±10℃である。特に好ましくは、融点範囲は−10℃〜+60℃の間にあり、融点範囲の幅は少なくとも40℃であり、融点範囲の極大値は35±10℃である。
45〜55重量%のC16、
45〜55重量%のC18。
48〜58重量%のC12アルコール、
18〜24重量%のC14アルコール、
8〜12重量%のC16アルコール、
11〜15重量%のC18アルコール
である。
ゲルベ反応は、200℃〜260℃の温度範囲で行われる。220℃〜250℃の温度範囲が好ましい。
本発明の組成物は、局所塗布のための全医薬品並びにボディケアおよび洗浄のための全化粧品、例えば、ボディーオイル、ベビーオイル、ボディミルク、クリーム、ローション、噴霧可能なエマルション、日焼け防止組成物および制汗剤における基剤として適している。本発明の組成物は特に、界面活性剤含有組成物、例えば、液体石鹸、固形石鹸、フォームバスおよびシャワーバス、ヘアシャンプーおよびヘアリンスにおいて使用される。また、衛生およびケア分野において広く使用されているティシュー、紙材、ワイプ、不織製品、スポンジ、パフ、絆創膏および包帯(乳幼児衛生およびベビーケアのためのウェットワイプ、クレンジングワイプ、フェイスクレンジングワイプ、スキンケアワイプ、皮膚の老化を防止するための活性成分を含むケアワイプ、日焼け防止組成物および虫除け剤を含むワイプ、装飾用化粧品のためのワイプ、日焼け後の手入れのためのワイプ、トイレ用ウェットワイプ、制汗用ワイプ、オムツ、ポケットティシュー、ウェットワイプ、衛生用品、セルフタニングワイプ)におけるケア成分として使用することもできる。本発明の組成物はまた、とりわけ、毛髪の手入れ、洗浄またはカラーリングのための組成物においても使用される。更に、本発明の組成物は、装飾用化粧品、例えば、口紅、リップグロス、メーキャップ、ファンデーション、粉おしろい、アイシャドウ、マスカラなどの組成物においても使用される。
本発明の1つの態様では、本発明の製剤は、少なくとも1種の界面活性物質を含んでなる。本発明の製剤は、製剤の総重量に基づいて、0〜80重量%、特に0〜40重量%、好ましくは0.1〜20重量%、好ましくは0.1〜15重量%、特に0.1〜10重量%の量で、界面活性物質を含んでなる。
非イオン性乳化剤の群は、例えば以下を包含する:
(1)8〜40個の炭素原子を有する直鎖脂肪アルコール、12〜40個の炭素原子を有する脂肪酸およびアルキル基中に8〜15個の炭素原子を有するアルキルフェノールへの、エチレンオキシド2〜50molおよび/またはプロピレンオキシド1〜20molの付加生成物。
(2)グリセロールへのエチレンオキシド1〜50molの付加生成物の、C12〜C18脂肪酸モノエステルおよびジエステル。
(3)6〜22個の炭素原子を有する飽和および不飽和脂肪酸のスルビタンモノエステルおよびジエステル、並びにそれらのエチレンオキシド付加生成物。
(4)アルキル基中に8〜22個の炭素原子を有するアルキルモノグリコシドおよびアルキルオリゴグリコシド、並びにそれらのエトキシル化類似体。
(5)ヒマシ油および/または硬化ヒマシ油へのエチレンオキシド7〜60mol付加生成物。
(6)ポリオールエステル、特にポリグリセロールエステル、例えば、ポリオールポリ−12−ヒドロキシステアレート、ポリグリセロールポリリシノレエート、ポリグリセリル−4 ラウレート、ポリグリセロールジイソステアレートまたはポリグリセロールジメレート。同様に適しているものは、これら物質類の2種以上の化合物の混合物、例えばポリグリセリル−4 ジイソステアレート/ポリヒドロキシステアレート/セバケートである。
(7)ヒマシ油および/または硬化ヒマシ油へのエチレンオキシド2〜15molの付加生成物。
(8)直鎖、分岐、不飽和または飽和C6〜C22脂肪酸、リシノール酸、12−ヒドロキシステアリン酸、ポリグリセロール、ペンタエリスリトール、ジペンタエリスリトール、糖アルコール(例えばソルビトール)、アルキルグルコシド(例えばメチルグルコシド、ブチルグルコシド、ラウリルグルコシド)およびポリグルコシド(例えばセルロース)に基づく部分エステル、または混合エステル、およびスクロースポリステアレート(Emulgade(登録商標)SUCRO(Cognis GmbH)として市販)。
(9)ポリシロキサン−ポリアルキルポリエーテルコポリマーおよび対応する誘導体。
(10)ペンタエリスリトール、脂肪酸、クエン酸および脂肪アルコールの混合エステル、および/またはC6〜22脂肪酸、メチルグルコースおよびポリオール、好ましくはグリセロールまたはポリグリセロールの混合エステル。
に従って計算することもできる。
を特徴とする化合物の群から選択することができる。
本発明の1つの態様では、本発明の製剤は、界面活性化合物として少なくとも1種の界面活性剤を含有する。存在してよい界面活性物質は、アニオン性界面活性剤、非イオン性界面活性剤、カチオン性界面活性剤および/または両性界面活性剤或いは双性イオン性界面活性剤である。界面活性剤含有化粧品、例えば、シャワージェル、フォームバス、シャンプーなどでは、少なくとも1種のアニオン性界面活性剤が好ましくは存在する。
本発明の1つの態様では、本発明の製剤は、少なくとも1種のワックス成分を含有する。本発明の組成物は、組成物の総重量に基づいて、0〜40重量%、特に0〜20重量%、好ましくは0.1〜15重量%、とりわけ0.1〜10重量%の量でワックス成分を含有する。
本発明の1つの態様では、本発明の製剤は、少なくとも1種のポリマーを含有する。本発明の製剤は、製剤の総重量に基づいて、0〜20重量%、好ましくは0.05〜18重量%、好適には0.05〜15重量%、特に好ましくは0.05〜10重量%、とりわけ0.1〜1重量%の量でポリマーを含有する。本発明の好ましい態様では、本発明の製剤は、製剤の総重量に基づいて、0.1〜5重量%、特に0.1〜3重量%、とりわけ0.1〜2重量%の量でポリマーを含有する。
例えばクリーム、ボディオイル、ローションおよびミルクのようなボディケア組成物は通常、官能特性の更なる最適化に寄与する、一連の別の油体およびエモリエントを含有する。油体(本発明の組成物および更なる油体)は、通常0.1〜80重量%、特に0.5〜70重量%、好ましくは1〜60重量%、とりわけ1〜50重量%、特に1〜40重量%、好適には5〜25重量%、とりわけ5〜15重量%の総量で存在する。別の油体は、通常0.1〜40重量%の量で存在する。
・3−(4’−トリメチルアンモニウム)ベンジリデンボルナン−2−オンメチルスルフェート(Mexoryl SO);
・3,3’−(1,4−フェニレンジメチン)ビス(7,7−ジメチル−2−オキソビシクロ[2.2.1]ヘプタン−1−メタンスルホン酸)およびその塩(Mexoryl SX);
・3−(4’−スルホ)−ベンジリデンボルナン−2−オンおよびその塩(Mexoryl SL);
・N−{(2および4)−[2−オキソボルン−3−イリデン)メチル}ベンジル]アクリルアミドのポリマー(Mexoryl SW);
・2−(2H−ベンゾトリアゾール−2−イル)−4−メチル−6−(2−メチル−3−(1,3,3,3−テトラメチル−1−(トリメチルシリルオキシ)ジシロキサニル)プロピル)フェノール(Mexoryl SL);
・4−アミノ安息香酸誘導体、好ましくは、2−エチルヘキシル 4−(ジメチルアミノ)ベンゾエート、2−オクチル 4−(ジメチルアミノ)ベンゾエート、およびアミル 4−(ジメチルアミノ)ベンゾエート;
・桂皮酸エステル、好ましくは、2−エチルヘキシル 4−メトキシシンナメート、プロピル 4−メトキシシンナメート、イソアミル 4−メトキシシンナメート、2−エチルヘキシル 2−シアノ−3,3−フェニルシンナメート(オクトクリレン);
・サリチル酸エステル、好ましくは、2−エチルヘキシルサリチレート、4−イソプロピルベンジルサリチレート、ホモメンチルサリチレート;
・ベンゾフェノン誘導体、好ましくは、2−ヒドロキシ−4−メトキシベンゾフェノン、2−ヒドロキシ−4−メトキシ−4’−メチルベンゾフェノン、2,2’−ジヒドロキシ−4−メトキシベンゾフェノン;
・ベンザルマロン酸エステル、好ましくはジ−2−エチルヘキシル 4−メトキシベンズマロネート;
・トリアジン誘導体、例えば、2,4,6−トリアニリノ−(p−カルボ−2’−エチル−1’−ヘキシルオキシ)−1,3,5−トリアジンおよびEP 0818450 A1に記載されているような2,4,6−トリス[p−(2−エチルヘキシルオキシカルボニル)−アニリノ]−1,3,5−トリアジン(Uvinul T 150)、またはビス(2−エチルヘキシル)4,4’−[(6−[4−((1,1−ジメチルエチル)アミノカルボニル)フェニルアミノ]−1,3,5−トリアジン−2,4−ジイル)ジイミノ]ベンゾエート(Uvasorb(登録商標)HEB);
・2,2−メチレンビス(6−(2H−ベンゾトリアゾール−2−イル)−4−(1,1,3,3−テトラメチルブチル)フェノール(Tinosorb M);
・2,4−ビス[4−(2−エチルヘキシルオキシ)−2−ヒドロキシフェニル]−6−(4−メトキシフェニル)−1,3,5−トリアジン(Tinosorb S);
・プロパン−1,3−ジオン、例えば1−(4−tert−ブチルフェニル)−3−(4’−メトキシフェニル)プロパン−1,3−ジオン;
・EP 0694521 B1に記載されているようなケトトリシクロ(5.2.1.0)デカン誘導体;
・ジメチコジエチルベンザルマロネート(Parsol SLX)。
・2−フェニルベンズイミダゾール−5−スルホン酸、およびそのアルカリ金属塩、アルカリ土類金属塩、アンモニウム塩、アルキルアンモニウム塩、アルカノールアンモニウム塩およびグルカンモニウム塩;
・2,2−(1,4−フェニレン)ビス(1H−ベンズイミダゾール−4,6−ジスルホン酸、モノナトリウム塩)(Neo Heliopan AP);
・ベンゾフェノンのスルホン酸誘導体、好ましくは、2−ヒドロキシ−4−メトキシベンゾフェノン−5−スルホン酸およびその塩;
・3−ベンジリデンカンファーのスルホン酸誘導体、例えば、4−(2−オキソ−3−ボルニリデンメチル)−ベンゼンスルホン酸および2−メチル−5−(2−オキソ−3−ボルニリデン)スルホン酸およびそれらの塩。
適当な増粘剤は、例えば、Aerosilグレード(親水性シリカ)、カルボキシメチルセルロースおよびヒドロキシエチルセルロースおよびヒドロキシプロピルセルロース、ポリビニルアルコール、ポリビニルピロリドンおよびベントナイト、例えばBentone(登録商標)Gel VS 5PC(Rheox)である。適当な増粘剤は例えば、Cosmedia(登録商標)Gel CCの商品名で入手可能な、INCI名ジカプリリルカーボネート、ステアラルコニウムヘクトライトおよびプロピレンカーボネートを有する製品である。
実験室におけるゲルベアルコールの合成
以下の市販品を用いて、合成を実施した。
Lanette O:45〜55%のC16および45〜55%のC18の鎖長分布を有するセチルステアリルアルコール
Lorol(登録商標):「Lorol technical grade」、下記鎖長分布を有するC12〜18脂肪アルコール:
C12 48〜58%
C14 18〜24%
C16 8〜12%
C18 11〜15%
2700gのLanette Oを1160gのLorolと混合し、この溶解物に、0.08gの酸化亜鉛、および少しずつ50%濃度水酸化ナトリウム水溶液70gを添加した。
部分還流しながら混合物をまず220℃に加熱した。この温度では、アルコールは保持されたが、反応水は除去された。数時間後、温度を250℃に段階的に上昇させた。
目的の添加率に達するとすぐ、混合物を水で1回洗浄し、残留アルカリを乳酸で中和し、真空乾燥し、濾過助剤を用いて深層濾過機により濾過した。
845gのLanette Oを455gのLorolと混合し、この溶解物に、0.025gの酸化亜鉛、および少しずつ50%濃度水酸化カリウム水溶液22gを添加した。
部分還流しながら混合物をまず220℃に加熱した。この温度では、アルコールは保持されたが、反応水は除去された。数時間後、温度を250℃に段階的に上昇させた。
目的の添加率に達するとすぐ、混合物を水で1回洗浄し、残留アルカリを乳酸で中和し、真空乾燥し、濾過助剤を用いて深層濾過機により濾過した。
300gのLanette Oを200gのLorolと混合し、この溶解物に、0.01gの酸化亜鉛、および少しずつ50%濃度水酸化カリウム水溶液10gを添加した。
部分還流しながら混合物をまず220℃に加熱した。この温度では、アルコールは保持されたが、反応水は除去された。数時間後、温度を250℃に段階的に上昇させた。
目的の添加率に達するとすぐ、混合物を水で1回洗浄し、残留アルカリを乳酸で中和し、真空乾燥し、濾過助剤を用いて深層濾過機により濾過した。
1235gのLanette Oを65gのHD Ocenol 60/65と混合し、この溶解物に、0.025gの酸化亜鉛、および少しずつ50%濃度水酸化カリウム水溶液22gを添加した。
部分還流しながら混合物をまず220℃に加熱した。この温度では、アルコールは保持されたが、反応水は除去された。数時間後、温度を250℃に段階的に上昇させた。
目的の添加率に達するとすぐ、混合物を水で1回洗浄し、残留アルカリを乳酸で中和し、真空乾燥し、濾過助剤を用いて深層濾過機により濾過した。
312.5gのLanette Oを162.5gのLorolおよび25gのヘキサン−1,6−ジオールと混合し、この溶解物に、0.08gの酸化亜鉛、および少しずつ50%濃度水酸化カリウム水溶液80gを添加した。
部分還流しながら混合物をまず220℃に加熱した。この温度では、アルコールは保持されたが、反応水は除去された。数時間後、温度を250℃に段階的に上昇させた。
目的の添加率に達するとすぐ、混合物を水で1回洗浄し、残留アルカリを乳酸で中和し、真空乾燥し、濾過助剤を用いて深層濾過機により濾過した。
A)ゲルベアルコールの適用性を、1重量%のCosmedia(登録商標)SP(ポリアクリル酸ナトリウム)、10重量%のCetiol(登録商標)LC(ココカプリレート/カプレート)および3重量%のグリセロールを含有する化粧品において調べた。ゲルベアルコールおよび/またはワセリンの使用濃度は、それぞれの場合において6重量%であった。
5人の被験者が、所定の基準に従って、組成物の官能特性を評価した。ワセリン含有組成物を比較の標準品とした(+は、1人の被験者の評価を示す)。ゲルベアルコール混合物B(63:35)を含有する組成物は、ワセリン含有組成物と同程度の官能特性を示した。特に、この組成物は、標準品と比べて、幾分より迅速に皮膚に吸収され、より小さい油性およびワックス様の感覚が認められた。
ゲルベアルコールの適用性を、16.1%のTexapon(登録商標)N70(ラウレス硫酸ナトリウム2EO)、11.1%のDehyton(登録商標)PK45(コカミドプロピルベタイン)、2.15%のComperlan(登録商標)CMEA(コカミドMEA)、4%のヒマワリ油、4%のEdenor(登録商標)C12(ラウリン酸)、0.2%のDehyquart(登録商標)GUAR N(グアーヒドロキシプロピルトリモニウムクロリド)、0.2%のEDTA BD、0.5%のグリセロール、0.5%の安息香酸ナトリウムおよび1.2%のクエン酸を含んでなる界面活性剤含有組成物において調べた。ゲルベアルコールおよび/またはワセリンの使用濃度は、それぞれの場合において4%であった。
30℃および15°のドイツ硬度で、1%濃度溶液において、Sita Rotorfoam測定装置を用いて、発泡特性を測定した。ゲルベアルコール含有組成物の発泡挙動、特に約30秒後の初期発泡特性は、ワセリン含有組成物と同程度であった。後続の測定過程において、ゲルベアルコールに基づく試験組成物は、ワセリン含有組成物より、多量のフォームを生成した。従って、調べた新規なゲルベアルコールは、ワセリンと同等であるか、またはワセリンより優れた適用性を発揮した。
TEWL(経皮水分喪失量)を測定することによって、ゲルベアルコールの吸蔵性を調べた。
蒸気圧計法を用いて、皮膚の水分蒸散率の低下を介して吸蔵効果を調べた。このため、温湿度制御環境中で、2つの測定用プローブを用いて、油状物で処理した前腕皮膚または油状物で処理していない前腕皮膚の上方の水蒸気勾配を測定し、これから皮膚の水分蒸散率を調べた。
1.ワセリン − 明らかにまたは強力に吸蔵
2.ゲルベアルコール混合物B − 中程度にまたは強力に吸蔵
3.ゲルベアルコール混合物D − 中程度にまたは強力に吸蔵
4.IPM−CE92010016 − 明らかにまたは僅かに吸蔵
調べたゲルベアルコールはいずれも、強力な吸蔵性を示した。従って、ワセリン代替物として非常に適当であることが分かった。
Claims (11)
- a)55〜95重量%のセチルステアリルアルコール、
b)5〜45重量%のC8〜22脂肪アルコール、および
c)場合により5重量%の少なくとも3個の炭素原子を有する脂肪族ジオールに基づき、−20℃〜+70℃の間に示差走査熱量測定(DSC)により測定した融点範囲を有するゲルベアルコール混合物含有組成物であって、融点範囲の幅が少なくとも30℃であり、融点範囲の極大値が35±15℃である、組成物。 - a)60〜70重量%のセチルステアリルアルコール、
b)30〜40重量%のC8〜22脂肪アルコール、および
c)場合により5重量%の少なくとも3個の炭素原子を有する脂肪族ジオールに基づき、−20℃〜+70℃の間に示差走査熱量測定により測定した融点範囲を有するゲルベアルコール混合物含有組成物であって、融点範囲の幅が少なくとも30℃であり、融点範囲の極大値が35±15℃である、組成物。 - −10℃〜+60℃の間に融点範囲を有する請求項1または2に記載の組成物であって、融点範囲の幅が少なくとも40℃であり、融点範囲の極大値が35±10℃である、組成物。
- 成分a)は、下記鎖長分布:
45〜55%のC16、
45〜55%のC18
を有する非分岐脂肪アルコールからなる、請求項1〜3のいずれかに記載の組成物。 - 成分b)はC12〜18脂肪アルコールからなる、請求項1〜4のいずれかに記載の組成物。
- 成分b)は、下記鎖長分布:
48〜58%のC12、
18〜24%のC14、
8〜12%のC16、
11〜15重量%のC18
を有する非分岐飽和脂肪アルコールからなる、請求項1〜5のいずれかに記載の組成物。 - 成分c)はヘキサンジオールである、請求項1〜6のいずれかに記載の組成物。
- ゲルベアルコール混合物含有組成物の出発アルコールを200〜260℃の温度でゲルベ反応させることを含む、請求項1〜7のいずれかに記載の組成物の製造方法。
- ゲルベ反応は、出発アルコールの60〜80%が転化するまで行われる、請求項8に記載の製造方法。
- 請求項1〜7のいずれかに記載の組成物を含んでなる、化粧品および/または医薬品。
- 化粧品または医薬品においてワセリンの代替とするための、請求項1〜7のいずれかに記載の組成物の使用。
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US61/599,965 | 2012-02-17 | ||
PCT/EP2013/052417 WO2013120757A1 (de) | 2012-02-17 | 2013-02-07 | Guerbetalkohole als vaseline-ersatz |
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US9422469B2 (en) | 2013-03-15 | 2016-08-23 | Chevron U.S.A. Inc. | Mixed carbon length synthesis of primary guerbet alcohols |
CN104634896B (zh) * | 2015-02-12 | 2016-08-24 | 广州天赐高新材料股份有限公司 | 三乙醇胺酯的快速检测方法 |
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US3553192A (en) * | 1968-07-15 | 1971-01-05 | Robugen Gmbh | Substituted (2'-deoxyribosyl) uracil compounds, compositions containing same and process of making and using same |
JPS5352630A (en) * | 1976-10-20 | 1978-05-13 | Itoh Oil Mfg | Cosmetics |
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DE4420516C2 (de) | 1994-06-13 | 1998-10-22 | Henkel Kgaa | Polyglycerinpolyhydroxystearate |
DE4426216A1 (de) | 1994-07-23 | 1996-01-25 | Merck Patent Gmbh | Benzyliden-Norcampher-Derivate |
DE4426215A1 (de) | 1994-07-23 | 1996-01-25 | Merck Patent Gmbh | Ketotricyclo [5.2.1.0] decan-Derivate |
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DE19712033A1 (de) | 1997-03-21 | 1998-09-24 | Basf Ag | Photostabile UV-Filter enthaltende kosmetische und pharmazeutische Zubereitungen |
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DE19928112A1 (de) * | 1999-06-19 | 2000-12-21 | Cognis Deutschland Gmbh | Guerbetalkohole |
DE10126253A1 (de) * | 2001-05-29 | 2002-12-05 | Clariant Gmbh | Neuartig konfektionierte quaternäre Ammoniumverbindungen |
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