WO2000027343A2 - Cosmetic and/or pharmaceutical preparations containing quaternary esters and partial glycerides - Google Patents
Cosmetic and/or pharmaceutical preparations containing quaternary esters and partial glycerides Download PDFInfo
- Publication number
- WO2000027343A2 WO2000027343A2 PCT/EP1999/008287 EP9908287W WO0027343A2 WO 2000027343 A2 WO2000027343 A2 WO 2000027343A2 EP 9908287 W EP9908287 W EP 9908287W WO 0027343 A2 WO0027343 A2 WO 0027343A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- acid
- alkyl
- carbon atoms
- alcohol
- Prior art date
Links
- 125000005456 glyceride group Chemical group 0.000 title claims abstract description 16
- 239000002537 cosmetic Substances 0.000 title claims abstract description 15
- 239000000825 pharmaceutical preparation Substances 0.000 title claims abstract description 8
- 125000004185 ester group Chemical group 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 28
- 150000002191 fatty alcohols Chemical class 0.000 claims abstract description 26
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 17
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
- 210000004209 hair Anatomy 0.000 claims abstract description 10
- 150000005676 cyclic carbonates Chemical class 0.000 claims abstract description 8
- -1 alkyl phosphate Chemical group 0.000 claims description 69
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 41
- 150000002148 esters Chemical class 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 239000003921 oil Substances 0.000 claims description 22
- 235000019198 oils Nutrition 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 17
- 229920005862 polyol Polymers 0.000 claims description 14
- 150000003077 polyols Chemical class 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229910019142 PO4 Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000008051 alkyl sulfates Chemical group 0.000 claims description 6
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 6
- 150000004820 halides Chemical group 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 235000000346 sugar Nutrition 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229940114069 12-hydroxystearate Drugs 0.000 claims description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000002453 shampoo Substances 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 244000062730 Melissa officinalis Species 0.000 claims description 3
- 235000010654 Melissa officinalis Nutrition 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229940007550 benzyl acetate Drugs 0.000 claims description 3
- 239000000839 emulsion Substances 0.000 claims description 3
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims description 2
- 239000005792 Geraniol Substances 0.000 claims description 2
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 2
- 241000234269 Liliales Species 0.000 claims description 2
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 235000000484 citronellol Nutrition 0.000 claims description 2
- 229940019836 cyclamen aldehyde Drugs 0.000 claims description 2
- 229940113087 geraniol Drugs 0.000 claims description 2
- SDQFDHOLCGWZPU-UHFFFAOYSA-N lilial Chemical compound O=CC(C)CC1=CC=C(C(C)(C)C)C=C1 SDQFDHOLCGWZPU-UHFFFAOYSA-N 0.000 claims description 2
- 229930007744 linalool Natural products 0.000 claims description 2
- 229940067107 phenylethyl alcohol Drugs 0.000 claims description 2
- 239000010670 sage oil Substances 0.000 claims description 2
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 claims description 2
- 235000019502 Orange oil Nutrition 0.000 claims 3
- 239000000975 dye Substances 0.000 claims 3
- 239000010502 orange oil Substances 0.000 claims 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- UUQHKWMIDYRWHH-UHFFFAOYSA-N Methyl beta-orcinolcarboxylate Chemical group COC(=O)C1=C(C)C=C(O)C(C)=C1O UUQHKWMIDYRWHH-UHFFFAOYSA-N 0.000 claims 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 claims 2
- 230000000052 comparative effect Effects 0.000 claims 2
- 230000003750 conditioning effect Effects 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 claims 2
- 239000001147 (3aR,5aS,9aS,9bR)-3a,6,6,9a-tetramethyl-2,4,5,5a,7,8,9,9b-octahydro-1H-benzo[e][1]benzofuran Substances 0.000 claims 1
- MTVBNJVZZAQKRV-BJMVGYQFSA-N (e)-2-methyl-4-(2,2,3-trimethylcyclopent-3-en-1-yl)but-2-en-1-ol Chemical compound OCC(/C)=C/CC1CC=C(C)C1(C)C MTVBNJVZZAQKRV-BJMVGYQFSA-N 0.000 claims 1
- FVUGZKDGWGKCFE-UHFFFAOYSA-N 1-(2,3,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl)ethanone Chemical compound CC1(C)CCCC2=C1CC(C(C)=O)(C)C(C)C2 FVUGZKDGWGKCFE-UHFFFAOYSA-N 0.000 claims 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- DNRJTBAOUJJKDY-UHFFFAOYSA-N 2-Acetyl-3,5,5,6,8,8-hexamethyl-5,6,7,8- tetrahydronaphthalene Chemical compound CC(=O)C1=C(C)C=C2C(C)(C)C(C)CC(C)(C)C2=C1 DNRJTBAOUJJKDY-UHFFFAOYSA-N 0.000 claims 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 claims 1
- ORMHZBNNECIKOH-UHFFFAOYSA-N 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)(O)CCCC1=CCC(C=O)CC1 ORMHZBNNECIKOH-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 claims 1
- YXAGIRHBJJLWHW-UHFFFAOYSA-N Ethyl 2-ethylhexanoate Chemical group CCCCC(CC)C(=O)OCC YXAGIRHBJJLWHW-UHFFFAOYSA-N 0.000 claims 1
- 235000019501 Lemon oil Nutrition 0.000 claims 1
- 235000006679 Mentha X verticillata Nutrition 0.000 claims 1
- 235000002899 Mentha suaveolens Nutrition 0.000 claims 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 244000182022 Salvia sclarea Species 0.000 claims 1
- 235000002911 Salvia sclarea Nutrition 0.000 claims 1
- 240000007313 Tilia cordata Species 0.000 claims 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 claims 1
- YPZUZOLGGMJZJO-LQKXBSAESA-N ambroxan Chemical compound CC([C@@H]1CC2)(C)CCC[C@]1(C)[C@@H]1[C@]2(C)OCC1 YPZUZOLGGMJZJO-LQKXBSAESA-N 0.000 claims 1
- 235000017803 cinnamon Nutrition 0.000 claims 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 claims 1
- 239000001071 citrus reticulata blanco var. mandarin Substances 0.000 claims 1
- 239000000973 cosmetic coloring agent Substances 0.000 claims 1
- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 claims 1
- 229930008394 dihydromyrcenol Natural products 0.000 claims 1
- VQNUNMBDOKEZHS-UHFFFAOYSA-N ethoxymethoxycyclododecane Chemical compound CCOCOC1CCCCCCCCCCC1 VQNUNMBDOKEZHS-UHFFFAOYSA-N 0.000 claims 1
- 239000001148 ferula galbaniflua oil terpeneless Substances 0.000 claims 1
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 claims 1
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 239000001851 juniperus communis l. berry oil Substances 0.000 claims 1
- 239000001469 lavandula hydrida abrial herb oil Substances 0.000 claims 1
- 239000010501 lemon oil Substances 0.000 claims 1
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 claims 1
- 239000001298 pelargonium graveolens oil Substances 0.000 claims 1
- 229930007790 rose oxide Natural products 0.000 claims 1
- WXETUDXXEZHSCS-MAVITOTKSA-N vertofix coeur Chemical compound C[C@@H]1CC[C@@]2(C(/CC3)=C\C(C)=O)[C@@H]3C(C)(C)[C@@H]1C2 WXETUDXXEZHSCS-MAVITOTKSA-N 0.000 claims 1
- 239000010679 vetiver oil Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 49
- 239000000194 fatty acid Substances 0.000 description 49
- 229930195729 fatty acid Natural products 0.000 description 49
- 150000004665 fatty acids Chemical class 0.000 description 36
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 22
- 235000002639 sodium chloride Nutrition 0.000 description 22
- 150000003839 salts Chemical class 0.000 description 14
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 235000011187 glycerol Nutrition 0.000 description 9
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 8
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 229960004488 linolenic acid Drugs 0.000 description 8
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 8
- 229920000223 polyglycerol Polymers 0.000 description 8
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 7
- 150000005690 diesters Chemical class 0.000 description 7
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 7
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 7
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- 229920000642 polymer Polymers 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 6
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 6
- 235000013162 Cocos nucifera Nutrition 0.000 description 6
- 244000060011 Cocos nucifera Species 0.000 description 6
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- 150000001298 alcohols Chemical class 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 6
- 239000003205 fragrance Substances 0.000 description 6
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 6
- 239000001993 wax Substances 0.000 description 6
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 5
- 229920001661 Chitosan Polymers 0.000 description 5
- 235000019438 castor oil Nutrition 0.000 description 5
- 125000002091 cationic group Chemical group 0.000 description 5
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
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- 239000002781 deodorant agent Substances 0.000 description 4
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
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- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 3
- 102000008186 Collagen Human genes 0.000 description 3
- 108010035532 Collagen Proteins 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
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- 229940043230 sarcosine Drugs 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
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- 229920005573 silicon-containing polymer Polymers 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
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- 235000010199 sorbic acid Nutrition 0.000 description 1
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- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- ARCJQKUWGAZPFX-UHFFFAOYSA-N stilbene oxide Chemical compound O1C(C=2C=CC=CC=2)C1C1=CC=CC=C1 ARCJQKUWGAZPFX-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
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- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000005555 sulfoximide group Chemical group 0.000 description 1
- CXVGEDCSTKKODG-UHFFFAOYSA-N sulisobenzone Chemical compound C1=C(S(O)(=O)=O)C(OC)=CC(O)=C1C(=O)C1=CC=CC=C1 CXVGEDCSTKKODG-UHFFFAOYSA-N 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 210000000106 sweat gland Anatomy 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
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- 150000003573 thiols Chemical class 0.000 description 1
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- 108060008226 thioredoxin Proteins 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000002640 tocopherol group Chemical class 0.000 description 1
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- AQWHMKSIVLSRNY-UHFFFAOYSA-N trans-Octadec-5-ensaeure Natural products CCCCCCCCCCCCC=CCCCC(O)=O AQWHMKSIVLSRNY-UHFFFAOYSA-N 0.000 description 1
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- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 1
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- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LOIYMIARKYCTBW-UHFFFAOYSA-N trans-urocanic acid Natural products OC(=O)C=CC1=CNC=N1 LOIYMIARKYCTBW-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
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- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 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
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- FQAZRHVERGEKOS-UHFFFAOYSA-N tripropan-2-yl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CC(C)OC(=O)CC(O)(C(=O)OC(C)C)CC(=O)OC(C)C FQAZRHVERGEKOS-UHFFFAOYSA-N 0.000 description 1
- ODHUFJLMXDXVRC-UHFFFAOYSA-N tripropyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCOC(=O)CC(O)(C(=O)OCCC)CC(=O)OCCC ODHUFJLMXDXVRC-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-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
- 229940057402 undecyl alcohol Drugs 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
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- 239000011719 vitamin A Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
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- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 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
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
-
- 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
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
-
- 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
- A61K8/41—Amines
- A61K8/416—Quaternary ammonium compounds
-
- 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
- A61K8/60—Sugars; Derivatives thereof
- A61K8/604—Alkylpolyglycosides; Derivatives thereof, e.g. esters
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
Definitions
- the invention relates to cosmetic and / or pharmaceutical preparations with improved sensory properties for use in skin and hair care, containing esterquats, partial glycerides and selected surfactants in binary or ternary mixtures.
- Esterquats are cationic surfactants which, due to their excellent ecotoxicological properties, are becoming increasingly important both for the area of fabric softeners and for cosmetic and pharmaceutical applications. Overviews on this topic are, for example, by R. Puchta et al. in tens. Surf. Det., 30, 186 (1993), M. Brock in Tens. Surf. Det. 30, 394 (1993), R. Lagerman et al. in J. Am. Oil. Chem. Soc, 71, 97 (1994) and I. Shapiro et al. in Cosm.Toil. 109, 77 (1994) appeared.
- esterquats preferably together with fatty alcohols, are used to achieve a pleasant, soft skin and hair feeling. They can be contained in emulsions and lotions for skin care as well as in surfactants such as shampoos, shower baths, rinses, conditioners and the like for hair care.
- surfactants such as shampoos, shower baths, rinses, conditioners and the like for hair care.
- the disadvantage here is that the desired soft feel of the skin and hair is sometimes felt as dull and dry, while the consumer desires a soft, smooth feel.
- the object of the present invention was to improve the properties of ester quats by adding additives so that low-viscosity, storage-stable concentrates result which have the desired sensory properties and are self-emulsifying in water. Description of the invention
- the invention relates to cosmetic and / or pharmaceutical preparations containing
- esters which form component (a) is generally understood to mean quaternized fatty acid triethanolamine ester salts. These are known substances which can be obtained by the relevant methods of preparative organic chemistry. In this connection, reference is made to the International Reference is made to patent application WO 91/01295 (Henkel), according to which triethanolamine is partially esterified with fatty acids in the presence of hypophosphorous acid, air is passed through and then quaternized with dimethyl sulfate or ethylene oxide. German Patent DE 4308794 C1 (Henkel) also describes a process for the preparation solid ester quats, in which the quaternization of triethanolamine esters is carried out in the presence of suitable dispersants, preferably fatty alcohols.
- suitable dispersants preferably fatty alcohols.
- R 1 CO represents an acyl radical with 6 to 22 carbon atoms
- R 2 and R 3 independently of one another for hydrogen or R 1 CO
- R 4 represents an alkyl radical with 1 to 4 carbon atoms or a (CH2CH2 ⁇ ) r H group
- m, n and p in total stand for 0 or numbers from 1 to 12, r for numbers from 1 to 12
- X for halide, alkyl sulfate or alkyl phosphate.
- ester quats which can be used in the context of the invention are products based on caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, isostearic acid, stearic acid, oleic acid, elaidic acid, arachic acid, behenic acid and erucic acid and their technical mixtures, such as they occur, for example, in the pressure splitting of natural fats and oils.
- Technical Ci2 / i8 coconut fatty acids and in particular partially hardened Ci6 / 18 tallow or palm fatty acids as well as high elaidic acid Ci6 / 18 fatty acid cuts are preferably used.
- the fatty acids and the triethanolamine can be used in a molar ratio of 1.1: 1 to 3: 1 to produce the quaternized esters.
- an application ratio of 1.2: 1 to 2.2: 1, preferably 1.5: 1 to 1.9: 1 has proven to be particularly advantageous.
- the preferred esterquats are technical mixtures of mono-, di- and triesters with an average degree of esterification of 1.5 to 1.9 and are derived from technical C16 / 18-tallow or palm fatty acid (iodine number 0 to 40).
- quaternized fatty acid triethanolamine ester salts of the formula (I) have proven to be particularly advantageous in which R 1 CO for an acyl radical having 16 to 18 carbon atoms, R 2 for R 1 CO, R 3 for hydrogen, R 4 for a methyl group, m , n and p is 0 and X is methyl sulfate.
- quaternized ester salts of fatty acids with diethanolalkylamines of the formula (II) are also suitable as esterquats,
- R 5 in which R 1 CO for an acyl radical with 6 to 22 carbon atoms, R 2 for hydrogen or R 1 CO, R 4 and R 5 independently of one another for alkyl radicals with 1 to 4 carbon atoms, m and n in total for 0 or numbers from 1 to 12 and X represents halide, alkyl sulfate or alkyl phosphate.
- suitable ester quats are the quaternized ester salts of fatty acids with 1,2-dihydroxypropyl dialkylamines of the formula (III),
- R 1 CO for an acyl radical with 6 to 22 carbon atoms
- R 2 for hydrogen or R 1 CO
- R 4 , R 5 and R 6 independently of one another for alkyl radicals with 1 to 4 carbon atoms
- m and n in total for 0 or numbers from 1 to 12
- X represents halide, alkyl sulfate or alkyl phosphate.
- esterquats of the formulas (II) and (III).
- the esterquats usually come on the market in the form of 50 to 90% strength by weight alcoholic solutions, which can be diluted with water if required.
- Partial glycerides that is, monoglycerides, diglycerides and their technical mixtures, which form component (b), can still contain small amounts of triglycerides due to the production process.
- the partial glycerides preferably follow the formula (IV)
- R 7 CO is a linear or branched, saturated and / or unsaturated acyl radical having 6 to 22, preferably 12 to 18 carbon atoms
- R 8 and R 9 independently of one another for R 7 CO or H and the sum (x + y + z ) stands for 0 or numbers from 1 to 100, preferably 5 to 25, with with the proviso that at least one of the two radicals R 8 and R 9 is H.
- Typical examples are mono- and / or diglycerides based on capric acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linoleic acid, linolenic acid, linolenic acid, linolenic acid, linolenic acid, linolenic acid, linolenic acid, linolenic acid, linolenic acid, linolenic acid, linolenic acid Arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures.
- Alcohol ethoxylates which form component (d), are referred to as fatty alcohol or oxo alcohol ethoxylates for production reasons and preferably follow the formula (V),
- R 10 represents a linear or branched alkyl and / or alkenyl radical having 6 to 22 carbon atoms and a represents numbers from 1 to 50.
- Typical examples are the adducts of on average 1 to 50, preferably 5 to 40 and in particular 10 to 25, moles of capron alcohol, capryl alcohol, 2-ethylhexyl alcohol, caprinal alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol Elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyla alcohol and brassidyl alcohol and their technical mixtures, which are used, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as unsaturated monomer alcohol in the
- Alkyl and alkenyl oligoglycosides which form component (c2) are known nonionic surfactants which follow the formula (VI)
- the alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose.
- the preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides.
- the index number q in the general formula (VI) indicates the degree of oligomerization (DP), ie the distribution of mono- and oligoglycosides, and stands for a number between 1 and 10.
- Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization q of 1.1 to 3.0 are preferably used. From an application point of view, preference is given to those alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4.
- the alkyl or alkenyl radical R 11 can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capronic alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis.
- the alkyl or alkenyl radical R 11 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms.
- Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and their technical mixtures, which can be obtained as described above.
- Alkyl oligoglucosides based on hydrogenated Ci2 / i4 coconut alcohol with a DP of 1 to 3 are preferred.
- polyol poly-12-hydroxystearates which form component (c3) are known substances which are sold, for example, under the "Dehymuls® PGPH” or “Eumulgin® VL” brands
- the polyol component of the emulsifiers can be derived from substances which have at least two, preferably 3 to 12 and in particular 3 to 8 hydroxyl groups and 2 to 12 carbon atoms, typical examples being:
- alkylene glycols such as ethylene glycol, diethylene glycol, propylene glycol
- methyl compounds such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
- alkyl oligoglucosides with 1 to 22, preferably 1 to 8 and in particular 1 to 4 carbons in the alkyl radical, such as methyl and butyl glucoside;
- sugar alcohols having 5 to 12 carbon atoms such as sorbitol or mannitol
- sugars with 5 to 12 carbon atoms such as glucose or sucrose
- reaction products based on polyglycerol are of particular importance because of their excellent performance properties. It has proven particularly advantageous to use selected polyglycerols which have the following homolog distribution (the preferred ranges are given in brackets):
- Glycerins 5 to 35 (15 to 30)% by weight
- Triglycerins 10 to 35 (15 to 25)% by weight
- Tetragiycerins 5 to 20 (8 to 15)% by weight
- Pentaglycerins 2 to 10 (3 to 8) wt%
- Oligoglycerins ad 100% by weight
- Fatty alcohols which form component (d1) are to be understood as primary aliphatic alcohols of the formula (VII) R1 0H (VII)
- R 12 represents an aliphatic, linear or branched hydrocarbon radical having 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds.
- Typical examples are capronic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolenyl alcohol, linolenyl alcohol, linoleyl alcohol Technical mixtures which are obtained, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as a monomer fraction in the dimerization of unsaturated fatty alcohols.
- Technical fatty alcohols with 12 to 18 carbon atoms such as, for example, coconut
- Cyclic carbonates which form component (d2), are usually produced by transesterification of dimethyl carbonate or diethyl carbonate with glycerol or vicinal diols, preferably 1, 2-diols.
- suitable cyclic carbonates are the esterification products of the lower dialkyl carbonates mentioned with ethylene glycol, 1, 2-pentanediol, 1, 2-hexanediol, 1, 2-octanediol, 1, 2-decanediol, 1, 2-dodecanediol and 1, 2-hexadecanediol.
- the diols mentioned are generally prepared by opening the corresponding terminal olefin epoxides with water; analog, of course, 1, 2-diols can also serve as starting materials, which are obtained on the basis of internal olefin epoxides. From an application point of view, the use of glycerol carbonate is preferred.
- the proportion of the cyclic carbonates in the cosmetic compositions can be 0.01 to 50, preferably 0.1 to 30 and in particular 5 to 10% by weight.
- the pharmaceutical and cosmetic preparations according to the invention can be used for the production of skin and hair treatment compositions. In the simplest case, it is sufficient to dilute the mixtures with water to an application concentration.
- the agents such as, for example, hair shampoos, hair lotions, bubble baths, creams, gels, lotions or ointments and the like, can furthermore, as further auxiliaries and additives, mild surfactants, oil bodies, Emulsifiers, superfatting agents, oil polishing waxes, consistency enhancers, thickening agents, polymers, silicone compounds, fats, waxes, stabilizers, biogenic agents, deodorant agents, anti-dandruff agents, film formers, swelling agents, UV light protection factors, antioxidants, hydrotropes, preservatives, insect repellents, self-tanning agents, perfumes, solubilizers and the like included.
- a typical preparation according to the invention has the following composition:
- component (a) 0.5 to 30, preferably 1 to 10% by weight of component (a), 0.5 to 5, preferably 1 to 3% by weight of component (b), 0.5 to 10, preferably 1 to 5% by weight.
- % Component (d) 0.5 to 10, preferably 1 to 5% by weight component (c2), 0.5 to 5, preferably 1 to 3% by weight component (c3),
- component (d1) 0 to 30, preferably 0.5 to 10% by weight of component (d1),
- component (d2) 0 to 5, preferably 0.5 to 2% by weight of component (d2).
- Suitable mild, i.e. particularly skin-compatible surfactants are fatty alcohol polyglycolethersulfate, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, fatty acid glutamates, ether carboxylic acids, Alkyloiigoglucoside, fatty acid glucamides, Alkyiamidobetaine and / or protein fatty acid condensates, the latter preferably based on wheat proteins.
- Guerbet alcohols based on fatty alcohols with 6 to 18, preferably 8 to 10 carbon atoms esters of linear C6-C22 fatty acids with linear C6-C22 fatty alcohols, esters of branched C6-Ci3-carboxylic acids with linear C6-C22- Fatty alcohols, esters of linear C6-C22 fatty acids with branched alcohols, especially 2-ethylhexanol, esters of hydroxycarboxylic acids with linear or branched C6-C22 fatty alcohols, especially dioctyl malates, esters of linear and / or branched fatty acids with polyhydric alcohols (e.g.
- Finsolv® TN linear or branched, symmetrical or asymmetrical dialkyl ethers with 6 to 22 carbon atoms per Alkyl group, ring opening products of epoxidized fatty acid esters with polyols, silicone oils and / or aliphatic or naphthenic hydrocarbons.
- suitable emulsifiers are nonionic surfactants from at least one of the following groups:
- polyol and especially polyglycerol esters such as e.g. Polyglycerol polyricinoleate, polyglycerol poly-12-hydroxystearate or polyglycerol dimer isostearate. Mixtures of compounds from several of these classes of substances are also suitable;
- partial esters based on linear, branched, unsaturated or saturated C6 / 22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (eg sorbitol), alkyl glucosides (eg methyl glucoside, butyl glucoside, butyl glucoside , Lauryl glucoside) and polyglucosides (eg cellulose);
- adducts of ethylene oxide and / or of propylene oxide with fatty acids, aikylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters with fatty acids or with castor oil are known, commercially available products. These are mixtures of homologs, the average degree of alkoxylation of which is Ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out corresponds.
- Ci2 / i8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE 2024051 PS as refatting agents for cosmetic preparations.
- Zwitterionic surfactants can also be used as emulsifiers.
- Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
- Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxyl -3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate.
- betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate,
- Suitable emulsifiers are ampholytic surfactants.
- Ampholytic surfactants are surface-active compounds which, in addition to a C ⁇ / i ⁇ -alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -SOßH group in the molecule and are capable of forming internal salts.
- ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkylsarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid each with about 8 to 18 C. Atoms in the alkyl group.
- Particularly preferred ampholytic surfactants are N-coconut alkyl aminopropionate, coconut acylaminoethyl aminopropionate and Ci ⁇ -acyl sarcosine.
- quaternary emulsifiers are also suitable, those of the esterquat type, preferably methylquaternized difatty acid triethanolamine ester salts, being particularly preferred.
- Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
- Pearlescent waxes are: alkylene glycol esters, especially ethylene glycol distearate; Fatty acid alkanolamides, especially coconut fatty acid diethanolamide; Partial glycerides, especially stearic acid monoglyceride; Esters of polyvalent, optionally hydroxy-substituted carboxylic acids with fatty alcohols with 6 to 22 carbon atoms, especially long-chain esters of tartaric acid; Fatty substances, such as, for example, fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which have a total of at least 24 carbon atoms, especially lauron and distearyl ether; Fatty acids such as stearic acid, hydroxystearic acid or behenic acid, ring opening products from
- Olefin epoxides with 12 to 22 carbon atoms with fatty alcohols with 12 to 22 carbon atoms and / or polyols with 2 to 15 carbon atoms and 2 to 10 hydroxyl groups and mixtures thereof.
- Suitable consistency agents are primarily fatty alcohols or hydroxy fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and, in addition, partial glycerides, fatty acids or hydroxy fatty acids.
- a combination of these substances with alkyl oligoglucosides and / or fatty acid N-methyl glucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates is preferred.
- Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, (for example Carbopole® from Goodrich or Synthalene® from Sigma ), Polyacrylamides, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with a restricted homolog distribution or alkyl oligoglucosides as well as electrolytes such as sodium chloride and ammonium chloride.
- polysaccharides in particular xanthan gum, guar guar, agar
- Suitable cationic polymers are, for example, cationic cellulose derivatives, e.g. a quaternized hydroxyethyl cellulose available under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers such as e.g.
- Luviquat® condensation products of polyglycols and amines, quaternized collagen polypeptides, such as lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers, e.g. Amidomethicones, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine (Cartaretine® / Sandoz), copolymers of acrylic acid with dimethyldiallylammonium chloride (Merquat® 550 / Chemviron), polyamino polyamides, e.g.
- cationic chitin derivatives such as quaternized chitosan, optionally microcrystalline, condensation products of dihaloalkylene, such as e.g. Dibromobutane with bisdialkylamines, e.g. Bis-dimethylamino-1, 3-propane, cationic guar gum, e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese, quaternized ammonium salt polymers, e.g. Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol.
- dihaloalkylene such as e.g. Dibromobutane with bisdialkylamines, e.g. Bis-dimethylamino-1, 3-propane
- cationic guar gum e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese
- quaternized ammonium salt polymers e.g. Mirapol® A
- Anionic, zwitterionic, amphoteric and nonionic polymers include, for example, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyllace- tat / butyl maleate / isobomylacrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and their esters, uncrosslinked and polyol-crosslinked polyacrylic acids, acrylamidopropyl trimethylammonium chloride / acrylate copolymers, octylacrylamide / methyl methacrylate / tert.butylaminoethyl methacrylate, poly-hydroxypropyl methacrylate / 2-hydroxypropyl acrylate, Vinyl pyrrolidone / vinyl acetate copolymers, vinyl pyrrolidone / dimethylaminoethyl methacrylate / vinyl caprolactam te
- Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl-modified silicone compounds, which can be both liquid and resinous at room temperature.
- suitable volatile silicones can also be found by Todd et al. in Cosm.Toil. 91, 27 (1976).
- Typical examples of fats are glycerides, waxes include Beeswax, carnauba wax, candelilla wax, montan wax, paraffin wax, hydrogenated castor oils, fatty acid esters or micro waxes solid at room temperature, optionally in combination with hydrophilic waxes, e.g. Cetylstearyl alcohol or partial glycerides in question.
- Metal salts of fatty acids such as e.g. Magnesium, aluminum and / or zinc stearate or ricinoleate are used.
- Biogenic active substances are, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin complexes.
- Deodorants come e.g. Antiperspirants such as aluminum chlorohydates are possible. These are colorless, hygroscopic crystals that easily dissolve in the air and arise when aqueous aluminum chloride solutions are evaporated. Aiuminium chlorohydrate is used for the manufacture of antiperspirant and deodorant preparations and is likely to act by partially occluding the sweat glands through protein and / or polysaccharide precipitation [cf. J.Soc.Cosm.Chem. 24, 281 (1973)]. Under the Locron® brand from Hoechst AG,
- Frankfurt / FRG is aiumium chlorohydrate on the market which corresponds to the formula [Al2 (OH) 5CI] * 2.5 H 2 0 and whose use is particularly preferred [cf. J.Pharm.Pharmacol. 26, 531 (1975)].
- aluminum hydroxyl lactates and acidic aluminum / zirconium salts can also be used.
- Esterase inhibitors can be added as further deodorant active ingredients. These are preferably trialkyl citrates such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and in particular triethyl citrate (Hydagen® CAT, Henkel KGaA, Düsseldorf / FRG).
- the cleavage of the citric acid ester probably releases the free acid, which lowers the pH value on the skin to such an extent that the enzymes are inhibited.
- Other substances which are suitable esterase inhibitors are dicarboxylic acids and esters thereof such as glutaric acid, Glutarklamo- noethylester, diethyl glutarate, adipic acid, adipic acid monoethyl ester, Adipinklatonedie- methyl ester, malonic acid and diethyl malonate, hydroxycarboxylic acids and esters thereof such as citric acid, malic acid, tartaric acid or Tartaric acid diethyl ester.
- Antibacterial agents that influence the bacterial flora and kill sweat-killing bacteria or inhibit their growth can also be contained in the stick preparations.
- Examples include chitosan, phenoxyethanol and chlorhexidine gluconate. 5-Chloro-2- (2,4-dichlorophen-oxy) phenol, which is sold under the Irgasan® brand by
- Climbazole, octopirox and zinc pyrethione can be used as antidandruff agents.
- Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary celulose derivatives, collagen, hyaluronic acid or its salts and similar compounds. Montmorillonites, clay minerals, pemulene and alkyl-modified carbopol types (Goodrich) can serve as swelling agents for aqueous phases. Further suitable polymers or swelling agents can be found in the overview by R. Lochhead in Cosm.Toil. 108, 95 (1993).
- UV light protection factors are understood to mean, for example, organic substances (light protection filters) which are liquid or crystalline at room temperature and which are able to absorb ultraviolet rays and absorb the energy absorbed in the form of longer-wave radiation, e.g. To give off heat again.
- UVB filters can be oil-soluble or water-soluble. As oil-soluble substances e.g. to call:
- 3-benzylidene camphor or 3-benzylidene norcampher and its derivatives e.g. 3- (4-methylbenzylidene) camphor as described in EP 0693471 B1;
- 4-aminobenzoic acid derivatives preferably 2-ethylhexyl 4- (dimethylamino) benzoate, 2-octyl 4- (dimethylamino) benzoate and amyl 4- (dimethylamino) benzoate;
- esters of cinnamic acid preferably 2-ethylhexyl 4-methoxycinnamate, propyl 4-methoxycinnamate, 2-cyano-3,3-phenylcinnamate-2-ethylhexyl ester (octocrylene) 4-methoxycinnamate;
- esters of salicylic acid preferably 2-ethylhexyl saiicylic acid, 4-isopropylbenzyl salicylic acid, homomethyl salicylic acid; • Derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
- esters of benzalmalonic acid preferably di-2-ethylhexyl 4-methoxybenzmalonate
- Triazine derivatives e.g. 2,4,6-trianilino- (p-carbo-2'-ethyl-1'-hexyloxy) -1,3,5-triazine and octyl triazone, as described in EP 0818450 A1;
- Propane-1,3-dione e.g. 1- (4-tert-butylphenyl) -3- (4'methoxyphenyl) propane-1,3-dione;
- Sulfonic acid derivatives of 3-benzylidene camphor e.g. 4- (2-oxo-3-bornylidene methyl) benzenesulfonic acid and 2-methyl-5- (2-oxo-3-bornylidene) sulfonic acid and their salts.
- UV-A filters -4'-methoxy-dibenzoylmethane (Parsol 1789), or 1-phenyl-3- (4'-isopropylphenyl) propane-1,3-dione.
- the UV-A and UV-B filters can of course also be used in mixtures.
- insoluble light protection pigments namely finely dispersed metal oxides or salts, are also suitable for this purpose.
- suitable metal oxides are, in particular, zinc oxide and titanium dioxide and, in addition, oxides of iron, zirconium, silicon, manganese, aluminum and cerium and mixtures thereof.
- Silicates (talc), barium sulfate or zinc stearate can be used as salts.
- the oxides and salts are used in the form of the pigments for skin-care and skin-protecting emulsions and decorative cosmetics.
- the particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm. They can have a spherical shape, but it is also possible to use particles which have an ellipsoidal shape or shape which differs from the spherical shape in some other way. So-called micro- or nanopigments are preferably used in sunscreens. Micronized zinc oxide is preferably used.
- UV light protection filters can be found in the overview by P.Finkel in S ⁇ FW-Journal 122, 543 (1996).
- secondary light stabilizers of the antioxidant type can also be used, which interrupt the photochemical reaction chain which is triggered when UV radiation penetrates the skin.
- amino acids e.g. glycine, histidine, tyrosine, tryptophan
- imidazoles e.g. urocanic acid
- peptides such as D, L-camosine, D-camosine, L-carosin and their derivatives (e.g.
- carotenoids carotenoids
- carotenes eg ⁇ -carotene, ⁇ -carotene, lycopene
- chlorogenic acid and their derivatives lipoic acid and their derivatives (eg dihydroliponic acid)
- aurothioglucose propylthiouracil and other thiols (eg thioredoxin, glutathione, cysteine, Cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, ⁇ -linoleyl, cholesteryl and glyceryl esters) and their salts , Dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleo
- tolerable dosages e.g. pmol to ⁇ mol / kg
- metal chelators e.g. ⁇ -hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin
- ⁇ -hydroxy acids e.g. citric acid, lactic acid, malic acid
- humic acid e.g. citric acid, lactic acid, malic acid
- bile acid bile extracts
- Bilirubin biliverdin
- EDTA EGTA
- unsaturated fatty acids and their derivatives eg ⁇ -linolenic acid, linoleic acid, oleic acid
- folic acid and its derivatives ubiquinone and
- Ubiquinol and its derivatives vitamin C and derivatives (e.g. ascorbyipalmitate, Mg ascorbyiphosphate, ascorbylacetate), tocopherols and derivatives (e.g. vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) as well as coniferyl benzoate of the benzoin resin, rutinic acid and derivatives thereof, ⁇ - rutin, ferulic acid, Furfurylidenglucitol, carnosine, butylhydroxytoluene, butylhydroxyanisole, Nordihydroguajakharzklazklare, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and derivatives thereof, mannose and derivatives thereof, superoxide dismutase, zinc and derivatives thereof (for example ZnO, ZnS0 4) Selenium and its derivatives (eg selenium-methionine), stilbenes and their derivatives (eg stilbene oxide, trans
- Hydrotropes such as ethanol, isopropyl alcohol or polyols can also be used to improve the flow behavior.
- Polyols that come into consideration here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. Typical examples are
- Alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons;
- Methyl compounds such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
- Lower alkyl glucosides in particular those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside;
- Sugar alcohols with 5 to 12 carbon atoms such as sorbitol or mannitol,
- Aminosugars such as glucamine.
- Suitable preservatives are, for example, phenoxyethanol, aldehyde solution, parabens, pentanediol or sorbic acid and the other classes of substances listed in Appendix 6, Parts A and B of the Cosmetics Ordinance.
- insect repellents N, N-diethyl-m-touluamide, 1, 2-pentanediol or insect repellants 3535 are suitable, and dihydroxyacetone is suitable as a self-tanning agent.
- Perfume oils include mixtures of natural and synthetic fragrances. Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, Oranges), roots (mace, angelica, celery, cardamom, costus, iris, calmus), wood (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme), Needles and twigs (spruce, fir, pine, mountain pine), resins and balms (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
- Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are e.g.
- the ethers include, for example, benzyl ethyl ether, the aldehydes e.g.
- the hydrocarbons mainly include the terpenes and balms.
- Essential oils of lower volatility, which are mostly used as aroma components, are also suitable as perfume oils, e.g. Sage oil, chamomile oil, nell
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Abstract
Description
Kosmetische und/oder pharmazeutische ZubereitungenCosmetic and / or pharmaceutical preparations
Gebiet der ErfindungField of the Invention
Die Erfindung betrifft kosmetische und/oder pharmazeutische Zubereitungen mit verbesserten sensorischen Eigenschaften für die Anwendung in der Haut- und Haarpflege, enthaltend Esterquats, Partialglyceride und ausgewählte Tenside in binären bzw. ternären Mischungen.The invention relates to cosmetic and / or pharmaceutical preparations with improved sensory properties for use in skin and hair care, containing esterquats, partial glycerides and selected surfactants in binary or ternary mixtures.
Stand der TechnikState of the art
Esterquats stellen kationische Tenside dar, die wegen ihrer ausgezeichneten ökotoxikologischen Eigenschaften sowohl für den Bereich der Wäscheweichspülmittel als auch für kosmetische und pharmazeutischen Anwendungen zunehmend an Bedeutung gewinnen. Übersichten zu diesem Thema sind beispielsweise von R. Puchta et al. in Tens. Surf. Det., 30, 186 (1993), M. Brock in Tens. Surf. Det. 30, 394 (1993), R. Lagerman et al. in J. Am. Oil. Chem. Soc, 71, 97 (1994) sowie I. Shapiro et al. in Cosm.Toil. 109, 77 (1994) erschienen. In kosmetischen und pharmazeutischen Zubereitungen werden Esterquats, vorzugsweise zusammen mit Fettalkoholen, zur Erzielung eines angenehmen weichen Haut- und Haargefühls eingesetzt. Sie können dabei sowohl in Emulsionen und Lotionen zur Hautpflege wie auch in tensidischen Mitteln wie beispielsweise Shampoos, Duschbädern, Spülungen, Conditionern und dergleichen für die Haarpflege enthalten sein. Nachteilig ist hierbei jedoch, daß der erwünschte weiche Griff der Haut und des Haares gelegentlich als stumpf und trocken empfunden wird, während vom Verbraucher ein weicher, glatter Griff gewünscht wird.Esterquats are cationic surfactants which, due to their excellent ecotoxicological properties, are becoming increasingly important both for the area of fabric softeners and for cosmetic and pharmaceutical applications. Overviews on this topic are, for example, by R. Puchta et al. in tens. Surf. Det., 30, 186 (1993), M. Brock in Tens. Surf. Det. 30, 394 (1993), R. Lagerman et al. in J. Am. Oil. Chem. Soc, 71, 97 (1994) and I. Shapiro et al. in Cosm.Toil. 109, 77 (1994) appeared. In cosmetic and pharmaceutical preparations, esterquats, preferably together with fatty alcohols, are used to achieve a pleasant, soft skin and hair feeling. They can be contained in emulsions and lotions for skin care as well as in surfactants such as shampoos, shower baths, rinses, conditioners and the like for hair care. The disadvantage here, however, is that the desired soft feel of the skin and hair is sometimes felt as dull and dry, while the consumer desires a soft, smooth feel.
Die Aufgabe der vorliegenden Erfindung hat darin bestanden, die Eigenschaften von Esterquats durch Zugabe von Additiven so zu verbessern, so daß niedrigviskose, lagerstabile Konzentrate resultieren, welche die gewünschten sensorischen Eigenschaften aufweisen und in Wasser selbstemulgierend sind. Beschreibung der ErfindungThe object of the present invention was to improve the properties of ester quats by adding additives so that low-viscosity, storage-stable concentrates result which have the desired sensory properties and are self-emulsifying in water. Description of the invention
Gegenstand der Erfindung sind kosmetische und/oder pharmazeutische Zubereitungen, enthaltendThe invention relates to cosmetic and / or pharmaceutical preparations containing
(a) Esterquats und(a) Esterquats and
(b) Partialglyceride,(b) partial glycerides,
(d) Alkoholethoxylate und/oder(d) alcohol ethoxylates and / or
(c2) Alkyl- und/oder Alkenyloligoglykoside und/oder(c2) alkyl and / or alkenyl oligoglycosides and / or
(c3) Polyolpoly-12-hydroxystearate sowie gegebenenfalls(c3) polyol poly-12-hydroxystearates and optionally
(d1) Fettalkohole und/oder(d1) fatty alcohols and / or
(d2) cyclische Carbonate.(d2) cyclic carbonates.
Überraschenderweise wurde gefunden, daß der Zusatz von Stoffen, welche die Komponente (c) bilden, den Weichgriff von Mischungen aus Esterquats und Partialglyceriden sowie deren hautsen- sorischen Eigenschaften signifikant verbessern. Eine weitere Steigerung der Eigenschaften kann erzielt werden, wenn man den Gemischen aus Esterquats und Partialglyceriden mit den Stoffen der Gruppe (c) eine weitere Komponente der Gruppe (d) zusetzt. Die resultierenden Konzentrate sind wasserfrei, niedrigviskos, lagerstabil und beim Eintragen in wäßrige Phasen selbstemulgierend.It has surprisingly been found that the addition of substances which form component (c) significantly improve the softness of mixtures of esterquats and partial glycerides and their skin-sensitive properties. A further increase in the properties can be achieved if a further component of group (d) is added to the mixtures of esterquats and partial glycerides with the substances of group (c). The resulting concentrates are water-free, low-viscosity, stable in storage and self-emulsifying when introduced into aqueous phases.
EsterquatsEsterquats
Unter der Bezeichnung „Esterquats", welche die Komponente (a) bilden, werden im allgemeinen quaternierte Fettsäuretriethanolaminestersalze verstanden. Es handelt sich dabei um bekannte Stoffe, die man nach den einschlägigen Methoden der präparativen organischen Chemie erhalten kann. In diesem Zusammenhang sei auf die Internationale Patentanmeldung WO 91/01295 (Henkel) verwiesen, nach der man Triethanolamin in Gegenwart von unterphosphoriger Säure mit Fettsäuren partiell verestert, Luft durchleitet und anschließend mit Dimethylsulfat oder Ethylenoxid quatemiert. Aus der Deutschen Patentschrift DE 4308794 C1 (Henkel) ist überdies ein Verfahren zur Herstellung fester Esterquats bekannt, bei dem man die Quaternierung von Triethanolaminestern in Gegenwart von geeigneten Dispergatoren, vorzugsweise Fettalkoholen, durchführt. Übersichten zu diesem Thema sind beispielsweise von R.Puchta et al. in Tens.Surf.Det., 30, 186 (1993), M.Brock in Tens.Surf.Det. 30, 394 (1993), R.Lagerman et al. in J.Am.Oil.Chem.Soc, 71, 97 (1994) sowie I.Shapiro in Cosm.Toil. 109, 77 (1994) erschienen. Die quaternierten Fettsäuretriethanoiaminestersalze folgen der Formel (I),The term "esterquats", which form component (a), is generally understood to mean quaternized fatty acid triethanolamine ester salts. These are known substances which can be obtained by the relevant methods of preparative organic chemistry. In this connection, reference is made to the International Reference is made to patent application WO 91/01295 (Henkel), according to which triethanolamine is partially esterified with fatty acids in the presence of hypophosphorous acid, air is passed through and then quaternized with dimethyl sulfate or ethylene oxide. German Patent DE 4308794 C1 (Henkel) also describes a process for the preparation solid ester quats, in which the quaternization of triethanolamine esters is carried out in the presence of suitable dispersants, preferably fatty alcohols. Reviews on this topic are, for example, by R. Puchta et al. in Tens.Surf.Det., 30, 186 (1993), M.Brock in Tens.Surf.Det. 30, 394 (1993), R. Lagerman et al. in J.Am.Oil.Chem.Soc, 71, 97 (1994) and I.Shapiro in Cosm.Toil. 109, 77 (1994) appeared. The quaternized fatty acid triethanoiamine ester salts follow the formula (I)
R4 R 4
II.
[RiCO-(OCH2CH2)mOCH2CH2-N+-CH2CH2θ-(CH2CH20)nR2] X" (I)[RiCO- (OCH 2 CH2) mOCH2CH2-N + -CH2CH2θ- (CH2CH 2 0) nR 2 ] X "(I)
I CH2CH2θ(CH2CH2θ)PR3 I CH 2 CH2θ (CH2CH2θ) P R 3
in der R1CO für einen Acylrest mit 6 bis 22 Kohlenstoffatomen, R2 und R3 unabhängig voneinander für Wasserstoff oder R1CO, R4 für einen Alkylrest mit 1 bis 4 Kohlenstoffatomen oder eine (CH2CH2θ)rH-Gruppe, m, n und p in Summe für 0 oder Zahlen von 1 bis 12, r für Zahlen von 1 bis 12 und X für Halogenid, Alkylsulfat oder Alkylphosphat steht. Typische Beispiele für Esterquats, die im Sinne der Erfindung Verwendung finden können, sind Produkte auf Basis von Capronsäure, Caprylsäure, Caprinsäure, Laurinsäure, Myristinsäure, Palmitinsäure, Isostearinsäure, Stearinsäure, Ölsäure, Elaidinsäure, Arachinsäure, Behensäure und Erucasäure sowie deren technische Mischungen, wie sie beispielsweise bei der Druckspaltung natürlicher Fette und Öle anfallen. Vorzugsweise werden technische Ci2/i8-Kokosfettsäuren und insbesondere teilgehärtete Ci6/18-Talg- bzw. Palmfettsäuren sowie elaidinsäurereiche Ci6/18-Fettsäureschnitte eingesetzt. Zur Herstellung der quaternierten Ester können die Fettsäuren und das Triethanolamin im molaren Verhältnis von 1 ,1 : 1 bis 3 : 1 eingesetzt werden. Im Hinblick auf die anwendungstechnischen Eigenschaften der Esterquats hat sich ein Einsatzverhältnis von 1 ,2 : 1 bis 2,2 : 1 , vorzugsweise 1 ,5 : 1 bis 1 ,9 : 1 als besonders vorteilhaft erwiesen. Die bevorzugten Esterquats stellen technische Mischungen von Mono-, Di- und Triestern mit einem durchschnittlichen Veresterungsgrad von 1 ,5 bis 1 ,9 dar und leiten sich von technischer C16/18- Talg- bzw. Palmfettsäure (lodzahl 0 bis 40) ab. Aus anwendungstechnischer Sicht haben sich quaternierte Fettsäuretriethanolaminestersalze der Formel (I) als besonders vorteilhaft erwiesen, in der R1CO für einen Acylrest mit 16 bis 18 Kohlenstoffatomen, R2 für R1CO, R3 für Wasserstoff, R4 für eine Methylgruppe, m, n und p für 0 und X für Methylsulfat steht.in which R 1 CO represents an acyl radical with 6 to 22 carbon atoms, R 2 and R 3 independently of one another for hydrogen or R 1 CO, R 4 represents an alkyl radical with 1 to 4 carbon atoms or a (CH2CH2θ) r H group, m, n and p in total stand for 0 or numbers from 1 to 12, r for numbers from 1 to 12 and X for halide, alkyl sulfate or alkyl phosphate. Typical examples of ester quats which can be used in the context of the invention are products based on caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, isostearic acid, stearic acid, oleic acid, elaidic acid, arachic acid, behenic acid and erucic acid and their technical mixtures, such as they occur, for example, in the pressure splitting of natural fats and oils. Technical Ci2 / i8 coconut fatty acids and in particular partially hardened Ci6 / 18 tallow or palm fatty acids as well as high elaidic acid Ci6 / 18 fatty acid cuts are preferably used. The fatty acids and the triethanolamine can be used in a molar ratio of 1.1: 1 to 3: 1 to produce the quaternized esters. With regard to the application properties of the ester quats, an application ratio of 1.2: 1 to 2.2: 1, preferably 1.5: 1 to 1.9: 1 has proven to be particularly advantageous. The preferred esterquats are technical mixtures of mono-, di- and triesters with an average degree of esterification of 1.5 to 1.9 and are derived from technical C16 / 18-tallow or palm fatty acid (iodine number 0 to 40). From an application point of view, quaternized fatty acid triethanolamine ester salts of the formula (I) have proven to be particularly advantageous in which R 1 CO for an acyl radical having 16 to 18 carbon atoms, R 2 for R 1 CO, R 3 for hydrogen, R 4 for a methyl group, m , n and p is 0 and X is methyl sulfate.
Neben den quaternierten Fettsäuretriethanolaminestersalzen kommen als Esterquats ferner auch quaternierte Estersalze von Fettsäuren mit Diethanolalkylaminen der Formel (II) in Betracht,In addition to the quaternized fatty acid triethanolamine ester salts, quaternized ester salts of fatty acids with diethanolalkylamines of the formula (II) are also suitable as esterquats,
R4 R 4
II.
[R1CO-(OCH2CH2)mOCH2CH2-N+-CH2CH20-(CH2CH2θ)nR2] X- (II)[R 1 CO- (OCH 2 CH2) mOCH2CH2-N + -CH2CH 2 0- (CH2CH2θ) nR2] X- (II)
II.
R5 in der R1CO für einen Acylrest mit 6 bis 22 Kohlenstoffatomen, R2 für Wasserstoff oder R1CO, R4 und R5 unabhängig voneinander für Alkylreste mit 1 bis 4 Kohlenstoffatomen, m und n in Summe für 0 oder Zahlen von 1 bis 12 und X für Halogenid, Alkylsulfat oder Alkylphosphat steht. Als weitere Gruppe geeigneter Esterquats sind schließlich die quaternierten Estersalze von Fettsäuren mit 1 ,2-Dihydroxypropyldialkylaminen der Formel (III) zu nennen,R 5 in which R 1 CO for an acyl radical with 6 to 22 carbon atoms, R 2 for hydrogen or R 1 CO, R 4 and R 5 independently of one another for alkyl radicals with 1 to 4 carbon atoms, m and n in total for 0 or numbers from 1 to 12 and X represents halide, alkyl sulfate or alkyl phosphate. Finally, a further group of suitable ester quats are the quaternized ester salts of fatty acids with 1,2-dihydroxypropyl dialkylamines of the formula (III),
I II I
[R4-N+-CH2CHCH2θ-(CH2CH2θ)nR2] * (III)[R 4 -N + -CH2CHCH2θ- (CH 2 CH2θ) n R 2 ] * (III)
I R5 IR 5
in der R1CO für einen Acylrest mit 6 bis 22 Kohlenstoffatomen, R2 für Wasserstoff oder R1CO, R4, R5 und R6 unabhängig voneinander für Alkylreste mit 1 bis 4 Kohlenstoffatomen, m und n in Summe für 0 oder Zahlen von 1 bis 12 und X für Halogenid, Alkylsulfat oder Alkylphosphat steht.in which R 1 CO for an acyl radical with 6 to 22 carbon atoms, R 2 for hydrogen or R 1 CO, R 4 , R 5 and R 6 independently of one another for alkyl radicals with 1 to 4 carbon atoms, m and n in total for 0 or numbers from 1 to 12 and X represents halide, alkyl sulfate or alkyl phosphate.
Hinsichtlich der Auswahl der bevorzugten Fettsäuren und des optimalen Veresterungsgrades gelten die für (I) genannten Beispiele auch für die Esterquats der Formeln (II) und (III). Üblicherweise gelangen die Esterquats in Form 50 bis 90 Gew.-%iger alkoholischer Lösungen in den Handel, die bei Bedarf problemlos mit Wasser verdünnt werden können.With regard to the selection of the preferred fatty acids and the optimal degree of esterification, the examples given for (I) also apply to the esterquats of the formulas (II) and (III). The esterquats usually come on the market in the form of 50 to 90% strength by weight alcoholic solutions, which can be diluted with water if required.
PartialglyceridePartial glycerides
Partialglyceride, also Monoglyceride, Diglyceride und deren technische Gemische, welche die Komponente (b) bilden, können herstellungsbedingt noch geringe Mengen Triglyceride enthalten. Die Partialglyceride folgen vorzugsweise der Formel (IV),Partial glycerides, that is, monoglycerides, diglycerides and their technical mixtures, which form component (b), can still contain small amounts of triglycerides due to the production process. The partial glycerides preferably follow the formula (IV)
CH20(CH2CH2θ)xCOR7 CH 2 0 (CH 2 CH2θ) xCOR 7
II.
CHO(CH2CH20)yR8 (IV)CHO (CH 2 CH 2 0) yR8 (IV)
I CH20(CH2CH20)zR9 I CH 2 0 (CH 2 CH 2 0) zR 9
in der R7CO für einen linearen oder verzweigten, gesättigten und/oder ungesättigten Acylrest mit 6 bis 22, vorzugsweise 12 bis 18 Kohlenstoffatomen, R8 und R9 unabhängig voneinander für R7CO oder H und die Summe (x+y+z) für 0 oder Zahlen von 1 bis 100, vorzugsweise 5 bis 25 steht, mit der Maßgabe, daß mindestens einer der beiden Reste R8 und R9 H bedeutet. Typische Beispiele sind Mono- und/oder Diglyceride auf Basis von Capransäure, Caprylsäure, 2-Ethylhexansäure, Caprinsäure, Laurinsäure, Isotridecansäure, Myristinsäure, Palmitinsäure, Palmoleinsäure, Stearinsäure, Isostearinsäure, Ölsäure, Elaidinsäure, Petroselinsäure, Linolsäure, Linolensäure, Elaeo- stearinsäure, Arachinsäure, Gadoleinsäure, Behensaure und Erucasaure sowie deren technische Mischungen. Vorzugsweise werden technische Laurinsäureglyceride, Palmitinsäureglyceride, Stearinsäureglyceride, Isostearinsäureglyceride, Olsaureglyceride, Behensäureglyceride und/oder Erucasäureglyceride eingesetzt, welche einen Monoglyceridanteil im Bereich von 50 bis 95, vorzugsweise 60 bis 90 Gew.-% aufweisen.in which R 7 CO is a linear or branched, saturated and / or unsaturated acyl radical having 6 to 22, preferably 12 to 18 carbon atoms, R 8 and R 9 independently of one another for R 7 CO or H and the sum (x + y + z ) stands for 0 or numbers from 1 to 100, preferably 5 to 25, with with the proviso that at least one of the two radicals R 8 and R 9 is H. Typical examples are mono- and / or diglycerides based on capric acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linoleic acid, linolenic acid, linolenic acid, linolenic acid, linolenic acid, linolenic acid, linolenic acid, linolenic acid, linolenic acid Arachic acid, gadoleic acid, behenic acid and erucic acid and their technical mixtures. Technical lauric acid glycerides, palmitic acid glycerides, stearic acid glycerides, isostearic acid glycerides, oleic acid glycerides, behenic acid glycerides and / or erucic acid glycerides, which have a monoglyceride content in the range from 50 to 95, preferably 60 to 90% by weight, are preferably used.
AlkoholethoxylateAlcohol ethoxylates
Alkoholethoxylate, welche die Komponente (d) bilden, werden herstellungsbedingt als Fettalkoholoder Oxoalkoholethoxylate bezeichnet und folgen vorzugsweise der Formel (V),Alcohol ethoxylates, which form component (d), are referred to as fatty alcohol or oxo alcohol ethoxylates for production reasons and preferably follow the formula (V),
R1°0(CH2CH20)aH (V)R 1 ° 0 (CH 2 CH 2 0) aH (V)
in der R10 für einen linearen oder verzweigten Alkyl- und/oder Alkenylrest mit 6 bis 22 Kohlenstoffatomen und a für Zahlen von 1 bis 50 steht. Typische Beispiele sind die Addukte von durchschnittlich 1 bis 50, vorzugsweise 5 bis 40 und insbesondere 10 bis 25 Mol an Capronalkohol, Ca- prylalkohol, 2-Ethylhexylalkohol, Caprinalkohol, Laurylalkohol, Isotridecylalkohol, Myristylalkohol, Cetylalkohol, Palmoleylalkohol, Stearylalkohol, Isostearylalkohol, Oleylalkohol, Elaidylalkohol, Petroselinylalkohol, Arachylalkohol, Gadoleylalkohol, Behenylalkohol, Erucylaikohol und Brassi- dylalkohol sowie deren technische Mischungen, die z.B. bei der Hochdruckhydrierung von technischen Methylestern auf Basis von Fetten und Ölen oder Aldehyden aus der Roelenschen Oxosynthese sowie als Monomerfraktion bei der Dimerisierung von ungesättigten Fettalkoholen anfallen. Bevorzugt sind Addukte von 10 bis 40 Mol Ethylenoxid an technische Fettalkohole mit 12 bis 18 Kohlenstoffatomen, wie beispielsweise Kokos-, Palm-, Palmkem- oder Taigfettalkohol.in which R 10 represents a linear or branched alkyl and / or alkenyl radical having 6 to 22 carbon atoms and a represents numbers from 1 to 50. Typical examples are the adducts of on average 1 to 50, preferably 5 to 40 and in particular 10 to 25, moles of capron alcohol, capryl alcohol, 2-ethylhexyl alcohol, caprinal alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol Elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyla alcohol and brassidyl alcohol and their technical mixtures, which are used, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as unsaturated monomer alcohol in the dimerization of dimer . Adducts of 10 to 40 moles of ethylene oxide with technical fatty alcohols with 12 to 18 carbon atoms, such as, for example, coconut, palm, palm kernel or tallow fatty alcohol, are preferred.
Alkyl- und/oder AlkenyloliqoqlvkosideAlkyl and / or alkenyl oligonucleotides
Alkyl- und Alkenyloligoglykoside, welche die Komponente (c2) bilden, stellen bekannte nichtionische Tenside dar, die der Formel (VI) folgen,Alkyl and alkenyl oligoglycosides which form component (c2) are known nonionic surfactants which follow the formula (VI)
R110-[G]q (VI) in der R11 für einen Alkyl- und/oder Alkenylrest mit 4 bis 22 Kohlenstoffatomen, G für einen Zuckerrest mit 5 oder 6 Kohlenstoffatomen und q für Zahlen von 1 bis 10 steht. Sie können nach den einschlägigen Verfahren der präparativen organischen Chemie erhalten werden. Stellvertretend für das umfangreiche Schrifttum sei hier auf die Übersichtsarbeit von Biermann et al. in Starch/Stärke 45, 281 (1993), B.Salka in Cosm.Toil. 108, 89 (1993) sowie J.Kahre et al. in SÖFW-Journal Heft 8, 598 (1995) verwiesen.R 11 0- [G] q (VI) in which R 11 represents an alkyl and / or alkenyl radical having 4 to 22 carbon atoms, G represents a sugar radical having 5 or 6 carbon atoms and q represents numbers from 1 to 10. They can be obtained according to the relevant procedures in preparative organic chemistry. Representative of the extensive literature here is the review by Biermann et al. in Starch /force 45, 281 (1993), B.Salka in Cosm.Toil. 108, 89 (1993) and J.Kahre et al. in SÖFW-Journal Issue 8, 598 (1995).
Die Alkyl- und/oder Alkenyloligoglykoside können sich von Aldosen bzw. Ketosen mit 5 oder 6 Kohlenstoffatomen, vorzugsweise der Glucose ableiten. Die bevorzugten Alkyl- und/oder Alkenyloligoglykoside sind somit Alkyl- und/oder Alkenyloligoglucoside. Die Indexzahl q in der allgemeinen Formel (VI) gibt den Oligomerisierungsgrad (DP), d. h. die Verteilung von Mono- und Oligoglykosiden an und steht für eine Zahl zwischen 1 und 10. Während q in einer gegebenen Verbindung stets ganzzahlig sein muß und hier vor allem die Werte q = 1 bis 6 annehmen kann, ist der Wert q für ein bestimmtes Alkyloligoglykosid eine analytisch ermittelte rechnerische Größe, die meistens eine gebrochene Zahl darstellt. Vorzugsweise werden Alkyl- und/oder Alkenyloligoglykoside mit einem mittleren Oligomerisierungsgrad q von 1 ,1 bis 3,0 eingesetzt. Aus anwendungstechnischer Sicht sind solche Alkyl- und/oder Alkenyloligoglykoside bevorzugt, deren Oligomerisierungsgrad kleiner als 1,7 ist und insbesondere zwischen 1,2 und 1,4 liegt. Der Alkyl- bzw. Alkenylrest R11 kann sich von primären Alkoholen mit 4 bis 11 , vorzugsweise 8 bis 10 Kohlenstoffatomen ableiten. Typische Beispiele sind Butanol, Capronalkohol, Caprylalkohol, Caprinal- kohol und Undecylalkohol sowie deren technische Mischungen, wie sie beispielsweise bei der Hydrierung von technischen Fettsäuremethylestern oder im Verlauf der Hydrierung von Aldehyden aus der Roelenschen Oxosynthese erhalten werden. Bevorzugt sind Alkyloiigoglucoside der Kettenlänge Cβ-Cio (DP = 1 bis 3), die als Vorlauf bei der destillativen Auftrennung von technischem C8-Ci8-Kokosfettalkohol anfallen und mit einem Anteil von weniger als 6 Gew.-% Ci2-Alkohol verunreinigt sein können sowie Alkyloiigoglucoside auf Basis technischer Cθ/n-Oxoalkohole (DP = 1 bis 3). Der Alkyl- bzw. Alkenylrest R11 kann sich ferner auch von primären Alkoholen mit 12 bis 22, vorzugsweise 12 bis 14 Kohlenstoffatomen ableiten. Typische Beispiele sind Laurylalkohol, Myristylalkohol, Cetylalkohol, Palmoleylalkohol, Stearylalkohol, Isostearylalkohol, Oleylalkohol, Elaidylalkohol, Petroselinylalkohol, Arachylalkohol, Gadoleylalkohol, Behenylalkohol, Erucylalkohol, Brassidylalkohol sowie deren technische Gemische, die wie oben beschrieben erhalten werden können. Bevorzugt sind Alkyloiigoglucoside auf Basis von gehärtetem Ci2/i4-Kokosalkohol mit einem DP von 1 bis 3. POIVΌIPOIV-12-hydroxystearateThe alkyl and / or alkenyl oligoglycosides can be derived from aldoses or ketoses with 5 or 6 carbon atoms, preferably glucose. The preferred alkyl and / or alkenyl oligoglycosides are thus alkyl and / or alkenyl oligoglucosides. The index number q in the general formula (VI) indicates the degree of oligomerization (DP), ie the distribution of mono- and oligoglycosides, and stands for a number between 1 and 10. While q in a given compound must always be an integer, especially here can assume the values q = 1 to 6, the value q for a certain alkyl oligoglycoside is an analytically determined arithmetic parameter, which usually represents a fractional number. Alkyl and / or alkenyl oligoglycosides with an average degree of oligomerization q of 1.1 to 3.0 are preferably used. From an application point of view, preference is given to those alkyl and / or alkenyl oligoglycosides whose degree of oligomerization is less than 1.7 and in particular between 1.2 and 1.4. The alkyl or alkenyl radical R 11 can be derived from primary alcohols having 4 to 11, preferably 8 to 10, carbon atoms. Typical examples are butanol, capronic alcohol, caprylic alcohol, capric alcohol and undecyl alcohol and their technical mixtures, such as are obtained, for example, in the hydrogenation of technical fatty acid methyl esters or in the course of the hydrogenation of aldehydes from Roelen's oxosynthesis. Alkyl oligoglucosides of chain length Cβ-Cio (DP = 1 to 3) are preferred, which are obtained as a preliminary step in the separation of technical C8-Ci8 coconut fatty alcohol by distillation and can be contaminated with a proportion of less than 6% by weight of Ci2-alcohol and Alkyloiigoglucoside based on technical Cθ / n-oxo alcohols (DP = 1 to 3). The alkyl or alkenyl radical R 11 can also be derived from primary alcohols having 12 to 22, preferably 12 to 14, carbon atoms. Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, arachyl alcohol, gadoleyl alcohol, behenyl alcohol, erucyl alcohol, brassidyl alcohol and their technical mixtures, which can be obtained as described above. Alkyl oligoglucosides based on hydrogenated Ci2 / i4 coconut alcohol with a DP of 1 to 3 are preferred. POIVΌIPOIV-12-hydroxystearate
Bei den Polyolpoly-12-hydroxystearaten, welche die Komponente (c3) bilden, handelt es sich um bekannte Stoffe, die beispielsweise unter den Marken „Dehymuls® PGPH" oder „Eumulgin® VLThe polyol poly-12-hydroxystearates which form component (c3) are known substances which are sold, for example, under the "Dehymuls® PGPH" or "Eumulgin® VL" brands
75" (Abmischung mit Coco Glucosides im Gewichtsverhältnis 1 :1) von der Henkel KGaA, Düssel- dorf/FRG vertrieben werden. In diesem Zusammenhang sei ferner auf die Internationale Patentanmeldung WO 95/34528 (Henkel) verwiesen. Die Polyolkomponente der Emulgatoren kann sich von Stoffen ableiten, die über mindestens zwei, vorzugsweise 3 bis 12 und insbesondere 3 bis 8 Hydroxylgruppen und 2 bis 12 Kohienstoffatome verfügen. Typische Beispiele sind:75 "(mixture with Coco Glucosides in a weight ratio of 1: 1) are sold by Henkel KGaA, Dusseldorf / FRG. In this connection, reference is also made to the international patent application WO 95/34528 (Henkel). The polyol component of the emulsifiers can be derived from substances which have at least two, preferably 3 to 12 and in particular 3 to 8 hydroxyl groups and 2 to 12 carbon atoms, typical examples being:
(a) Glycerin und Polyglycerin;(a) glycerin and polyglycerin;
(b) Alkylenglycole, wie beispielsweise Ethylenglycol, Diethylenglycol, Propylenglycol;(b) alkylene glycols, such as ethylene glycol, diethylene glycol, propylene glycol;
(c) Methyolverbindungen, wie insbesondere Trimethylolethan, Trimethylolpropan, Trimethylol- butan, Pentaerythrit und Dipentaerythrit;(c) methyl compounds, such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
(d) Alkyloiigoglucoside mit 1 bis 22, vorzugsweise 1 bis 8 und insbesondere 1 bis 4 Kohlenstoffen im Alkylrest, wie beispielsweise Methyl- und Butylglucosid;(d) alkyl oligoglucosides with 1 to 22, preferably 1 to 8 and in particular 1 to 4 carbons in the alkyl radical, such as methyl and butyl glucoside;
(e) Zuckeralkohole mit 5 bis 12 Kohlenstoffatomen, wie beispielsweise Sorbit oder Mannit;(e) sugar alcohols having 5 to 12 carbon atoms, such as sorbitol or mannitol;
(f) Zucker mit 5 bis 12 Kohlenstoffatomen, wie beispielsweise Glucose oder Saccharose;(f) sugars with 5 to 12 carbon atoms, such as glucose or sucrose;
(g) Aminozucker, wie beispielsweise Glucamin.(g) aminosugars such as glucamine.
Unter den erfindungsgemäß einzusetzenden Emulgatoren kommt Umsetzungsprodukten auf Basis von Polyglycerin wegen ihrer ausgezeichneten anwendungstechnischen Eigenschaften eine besondere Bedeutung zu. Als besonders vorteilhaft hat sich die Verwendung von ausgewählten Polyglycerinen erwiesen, die die folgende Homologenverteilung aufweisen (in Klammern angegeben sind die bevorzugten Bereiche):Among the emulsifiers to be used according to the invention, reaction products based on polyglycerol are of particular importance because of their excellent performance properties. It has proven particularly advantageous to use selected polyglycerols which have the following homolog distribution (the preferred ranges are given in brackets):
Glycerine: 5 bis 35 (15 bis 30) Gew.-%Glycerins: 5 to 35 (15 to 30)% by weight
Diglycerine: 15 bis 40 (20 bis 32) Gew.-%Diglycerins: 15 to 40 (20 to 32) wt%
Triglycerine: 10 bis 35 (15 bis 25) Gew.-%Triglycerins: 10 to 35 (15 to 25)% by weight
Tetragiycerine: 5 bis 20 (8 bis 15) Gew.-%Tetragiycerins: 5 to 20 (8 to 15)% by weight
Pentaglycerine: 2 bis 10 (3 bis 8) Gew.-%Pentaglycerins: 2 to 10 (3 to 8) wt%
Oligoglycerine: ad 100 Gew.-%Oligoglycerins: ad 100% by weight
FettalkoholeFatty alcohols
Unter Fettalkoholen, welche die Komponente (d1) bilden, sind primäre aliphatische Alkohole der Formel (VII) zu verstehen, R1 0H (VII)Fatty alcohols which form component (d1) are to be understood as primary aliphatic alcohols of the formula (VII) R1 0H (VII)
in der R12 für einen aliphatischen, linearen oder verzweigten Kohlenwasserstoffrest mit 6 bis 22 Kohlenstoffatomen und 0 und/oder 1 , 2 oder 3 Doppelbindungen steht. Typische Beispiele sind Capronalkohol, Caprylalkohol, 2-Ethylhexylalkohol, Caprinalkohol, Laurylalkohol, Isotridecylalkohol, Myristylalkohol, Cetylalkohol, Palmoleylalkohol, Stearylalkohol, Isostearylalkohol, Oleylalkohol, Elaidylalkohol, Petroselinylalkohol, Linolylalkohol, Linolenylalkohol, Elaeostearylalkohol, Arachylalkohol, Gadoleylalkohoi, Behenylalkohol, Erucylalkohol und Brassidylalkohol sowie deren technische Mischungen, die z.B. bei der Hochdruckhydrierung von technischen Methylestern auf Basis von Fetten und Ölen oder Aldehyden aus der Roelenschen Oxosynthese sowie als Monomerfraktion bei der Dimerisierung von ungesättigten Fettalkoholen anfallen. Bevorzugt sind technische Fettalkohole mit 12 bis 18 Kohlenstoffatomen, wie beispielsweise Kokos-, Palm-, Palm- kem- oder Taigfettalkohol.in which R 12 represents an aliphatic, linear or branched hydrocarbon radical having 6 to 22 carbon atoms and 0 and / or 1, 2 or 3 double bonds. Typical examples are capronic alcohol, caprylic alcohol, 2-ethylhexyl alcohol, capric alcohol, lauryl alcohol, isotridecyl alcohol, myristyl alcohol, cetyl alcohol, palmoleyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolenyl alcohol, linolenyl alcohol, linoleyl alcohol Technical mixtures which are obtained, for example, in the high-pressure hydrogenation of technical methyl esters based on fats and oils or aldehydes from Roelen's oxosynthesis and as a monomer fraction in the dimerization of unsaturated fatty alcohols. Technical fatty alcohols with 12 to 18 carbon atoms, such as, for example, coconut, palm, palm kem or tallow fatty alcohol, are preferred.
Cyclische CarbonateCyclic carbonates
Cyclische Carbonate, welche die Komponente (d2) bilden, werden üblicherweise durch Umeste- rung von Dimethylcarbonat oder Diethylcarbonat mit Glycerin oder vicinalen Diolen, vorzugsweise 1 ,2-Diolen hergestellt. Typische Beispiele für geeignete cyclische Carbonate sind die Umeste- rungsprodukte der genannten niederen Dialkylcarbonate mit Ethylenglycol, 1 ,2-Pentandiol, 1 ,2- Hexandiol, 1 ,2-Octandiol, 1 ,2-Decandiol, 1 ,2-Dodecandiol und 1 ,2-Hexadecandiol. Die genannten Diole werden in der Regel durch Ringöffnung der entsprechenden endständigen Olefinepoxide mit Wasser hergestellt; analog können natürlich auch 1 ,2-Diole als Ausgangsstoffe dienen, die auf Basis von innenständigen Olefinepoxiden gewonnen werden. Aus anwendungstechnischer Sicht ist der Einsatz von Glycerincarbonat bevorzugt. Der Anteil der cyclischen Carbonate an den kosmetischen Mitteln kann 0,01 bis 50, vorzugsweise 0,1 bis 30 und insbesondere 5 bis 10 Gew.-% betragen.Cyclic carbonates, which form component (d2), are usually produced by transesterification of dimethyl carbonate or diethyl carbonate with glycerol or vicinal diols, preferably 1, 2-diols. Typical examples of suitable cyclic carbonates are the esterification products of the lower dialkyl carbonates mentioned with ethylene glycol, 1, 2-pentanediol, 1, 2-hexanediol, 1, 2-octanediol, 1, 2-decanediol, 1, 2-dodecanediol and 1, 2-hexadecanediol. The diols mentioned are generally prepared by opening the corresponding terminal olefin epoxides with water; analog, of course, 1, 2-diols can also serve as starting materials, which are obtained on the basis of internal olefin epoxides. From an application point of view, the use of glycerol carbonate is preferred. The proportion of the cyclic carbonates in the cosmetic compositions can be 0.01 to 50, preferably 0.1 to 30 and in particular 5 to 10% by weight.
Gewerbliche AnwendbarkeitIndustrial applicability
Die erfindungsgemäßen pharmazeutischen und kosmetischen Zubereitungen können zur Herstellung von Haut- und Haarbehandlungsmittel eingesetzt werden. Im einfachsten Fall reicht es dazu aus, die Mischungen mit Wasser auf eine Anwendungskonzentration zu verdünnen. Die Mittel, wie beispielsweise Haarshampoos, Haarlotionen, Schaumbäder, Cremes, Gele, Lotionen oder Salben und dergleichen, können aber ferner als weitere Hilfs- und Zusatzstoffe milde Tenside, Ölkörper, Emulgatoren, Überfettungsmittel, Peilglanzwachse, Konsistenzgeber, Verdickungsmittel, Polymere, Siliconverbindungen, Fette, Wachse, Stabilisatoren, biogene Wirkstoffe, Deowirkstoffe, Antischuppenmittel, Filmbildner, Quellmittel, UV-Lichtschutzfaktoren, Antioxidantien, Hydrotrope, Konservierungsmittel, Insektenrepellentien, Selbstbräuner, Solubilisatoren, Parfümöle, Farbstoffe und dergleichen enthalten.The pharmaceutical and cosmetic preparations according to the invention can be used for the production of skin and hair treatment compositions. In the simplest case, it is sufficient to dilute the mixtures with water to an application concentration. The agents, such as, for example, hair shampoos, hair lotions, bubble baths, creams, gels, lotions or ointments and the like, can furthermore, as further auxiliaries and additives, mild surfactants, oil bodies, Emulsifiers, superfatting agents, oil polishing waxes, consistency enhancers, thickening agents, polymers, silicone compounds, fats, waxes, stabilizers, biogenic agents, deodorant agents, anti-dandruff agents, film formers, swelling agents, UV light protection factors, antioxidants, hydrotropes, preservatives, insect repellents, self-tanning agents, perfumes, solubilizers and the like included.
Eine typische erfindungsgemäße Zubereitung weist folgende Zusammensetzung auf:A typical preparation according to the invention has the following composition:
0,5 bis 30, vorzugsweise 1 bis 10 Gew.-% Komponente (a), 0,5 bis 5, vorzugsweise 1 bis 3 Gew.-% Komponente (b), 0,5 bis 10, vorzugsweise 1 bis 5 Gew.-% Komponente (d), 0,5 bis 10, vorzugsweise 1 bis 5 Gew.-% Komponente (c2), 0,5 bis 5, vorzugsweise 1 bis 3 Gew.-% Komponente (c3),0.5 to 30, preferably 1 to 10% by weight of component (a), 0.5 to 5, preferably 1 to 3% by weight of component (b), 0.5 to 10, preferably 1 to 5% by weight. % Component (d), 0.5 to 10, preferably 1 to 5% by weight component (c2), 0.5 to 5, preferably 1 to 3% by weight component (c3),
0 bis 30, vorzugsweise 0,5 bis 10 Gew.-% Komponente (d1),0 to 30, preferably 0.5 to 10% by weight of component (d1),
0 bis 5, vorzugsweise 0,5 bis 2 Gew.-% Komponente (d2).0 to 5, preferably 0.5 to 2% by weight of component (d2).
Typische Beispiele für geeignete milde, d.h. besonders hautverträgliche Tenside sind Fettalkohol- polyglycolethersulfate, Monoglyceridsulfate, Mono- und/oder Dialkylsulfosuccinate, Fettsäure- isethionate, Fettsäuresarcosinate, Fettsäuretauride, Fettsäureglutamate, Ethercarbonsäuren, Alkyloiigoglucoside, Fettsäureglucamide, Alkyiamidobetaine und/oder Proteinfettsäurekondensate, letztere vorzugsweise auf Basis von Weizenproteinen.Typical examples of suitable mild, i.e. particularly skin-compatible surfactants are fatty alcohol polyglycolethersulfate, monoglyceride sulfates, mono- and / or dialkyl sulfosuccinates, fatty acid isethionates, fatty acid sarcosinates, fatty acid taurides, fatty acid glutamates, ether carboxylic acids, Alkyloiigoglucoside, fatty acid glucamides, Alkyiamidobetaine and / or protein fatty acid condensates, the latter preferably based on wheat proteins.
Als Ölkörper kommen beispielsweise Guerbetalkohole auf Basis von Fettalkoholen mit 6 bis 18, vorzugsweise 8 bis 10 Kohlenstoffatomen, Ester von linearen C6-C22-Fettsäuren mit linearen C6- C22-Fettalkoholen, Ester von verzweigten C6-Ci3-Carbonsäuren mit linearen C6-C22-Fettalkoholen, Ester von linearen C6-C22-Fettsäuren mit verzweigten Alkoholen, insbesondere 2-Ethylhexanol, Ester von Hydroxycarbonsäuren mit linearen oder verzweigten C6-C22-Fettalkoholen, insbesondere Dioctyl Malate, Ester von linearen und/oder verzweigten Fettsäuren mit mehrwertigen Alkoholen (wie z.B. Propylenglycol, Dimerdiol oder Trimertriol) und/oder Guerbetalkoholen, Triglyceride auf Basis C6-CiQ-Fettsäuren, flüssige Mono-/Di-/Triglyceridmischungen auf Basis von Cδ-Ciβ- Fettsäuren, Ester von Cε-C∑∑-Fettalkoholen und/oder Guerbetalkoholen mit aromatischen Carbonsäuren, insbesondere Benzoesäure, Ester von C2-Ci2-Dicarbonsäuren mit linearen oder verzweigten Alkoholen mit 1 bis 22 Kohlenstoffatomen oder Polyolen mit 2 bis 10 Kohlenstoffatomen und 2 bis 6 Hydroxylgruppen, pflanzliche Öle, verzweigte primäre Alkohole, substituierte Cyclohexane, lineare und verzweigte C6-C22-Fettalkoholcarbonate, Guerbetcarbonate, Ester der Benzoesäure mit linearen und/oder verzweigten C6-C22-Alkoholen (z.B. Finsolv® TN), lineare oder verzweigte, symmetrische oder unsymmetrische Dialkylether mit 6 bis 22 Kohlenstoffatomen pro Alkylgruppe, Ringöffnungsprodukte von epoxidierten Fettsäureestem mit Polyolen, Siliconöle und/oder aliphatische bzw. naphthenische Kohlenwasserstoffe in Betracht. Als Emulgatoren kommen beispielsweise nichtionogene Tenside aus mindestens einer der folgenden Gruppen in Frage:Guerbet alcohols based on fatty alcohols with 6 to 18, preferably 8 to 10 carbon atoms, esters of linear C6-C22 fatty acids with linear C6-C22 fatty alcohols, esters of branched C6-Ci3-carboxylic acids with linear C6-C22- Fatty alcohols, esters of linear C6-C22 fatty acids with branched alcohols, especially 2-ethylhexanol, esters of hydroxycarboxylic acids with linear or branched C6-C22 fatty alcohols, especially dioctyl malates, esters of linear and / or branched fatty acids with polyhydric alcohols (e.g. Propylene glycol, dimer diol or trimer triol) and / or Guerbet alcohols, triglycerides based on C6-CiQ fatty acids, liquid mono- / di- / triglyceride mixtures based on Cδ-Ciβ fatty acids, esters of Cε-C∑∑ fatty alcohols and / or Guerbet alcohols with aromatic carboxylic acids, especially benzoic acid, esters of C2-Ci2-dicarboxylic acids with linear or branched alcohols with 1 to 22 carbon atoms or of polyols with 2 to 10 carbon atoms and 2 to 6 hydroxyl groups, vegetable oils, branched primary alcohols, substituted cyclohexanes, linear and branched C6-C22 fatty alcohol carbonates, Guerbet carbonates, esters of benzoic acid with linear and / or branched C6-C22 alcohols (e.g. Finsolv® TN), linear or branched, symmetrical or asymmetrical dialkyl ethers with 6 to 22 carbon atoms per Alkyl group, ring opening products of epoxidized fatty acid esters with polyols, silicone oils and / or aliphatic or naphthenic hydrocarbons. Examples of suitable emulsifiers are nonionic surfactants from at least one of the following groups:
(1) Anlagerungsprodukte von 2 bis 30 Mol Ethylenoxid und/ oder 0 bis 5 Mol Propylenoxid an Fettsäuren mit 12 bis 22 C-Atomen und an Aikylphenole mit 8 bis 15 C-Atomen in der Alkylgruppe;(1) adducts of 2 to 30 moles of ethylene oxide and / or 0 to 5 moles of propylene oxide with fatty acids with 12 to 22 C atoms and with aikylphenols with 8 to 15 C atoms in the alkyl group;
(2) Ci2/i8-Fettsäuremono- und -diester von Anlagerungsprodukten von 1 bis 30 Mol Ethylenoxid an Glycerin;(2) Ci2 / i8 fatty acid monoesters and diesters of adducts of 1 to 30 moles of ethylene oxide with glycerol;
(3) Sorbitanmono- und -diester von gesättigten und ungesättigten Fettsäuren mit 6 bis 22 Kohlenstoffatomen und deren Ethylenoxidanlagerungsprodukte;(3) sorbitan mono- and diesters of saturated and unsaturated fatty acids having 6 to 22 carbon atoms and their ethylene oxide addition products;
(4) Anlagerungsprodukte von 15 bis 60 Mol Ethylenoxid an Ricinusöl und/oder gehärtetes Ricinusöl;(4) adducts of 15 to 60 moles of ethylene oxide with castor oil and / or hardened castor oil;
(5) Polyol- und insbesondere Polyglycerinester, wie z.B. Polyglycerinpolyricinoleat, Polyglyce- rinpoly-12-hydroxystearat oder Polyglycerindimeratisostearat. Ebenfalls geeignet sind Gemische von Verbindungen aus mehreren dieser Substanzklassen;(5) polyol and especially polyglycerol esters such as e.g. Polyglycerol polyricinoleate, polyglycerol poly-12-hydroxystearate or polyglycerol dimer isostearate. Mixtures of compounds from several of these classes of substances are also suitable;
(6) Anlagerungsprodukte von 2 bis 15 Mol Ethylenoxid an Ricinusöl und/oder gehärtetes Ricinusöl;(6) adducts of 2 to 15 moles of ethylene oxide with castor oil and / or hardened castor oil;
(7) Partialester auf Basis linearer, verzweigter, ungesättigter bzw. gesättigter C6/22-Fettsäuren, Ricinolsäure sowie 12-Hydroxystearinsäure und Glycerin, Polyglycerin, Pentaerythrit, Di- pentaerythrit, Zuckeralkohole (z.B. Sorbit), Alkylglucoside (z.B. Methylglucosid, Butylgluco- sid, Laurylglucosid) sowie Polyglucoside (z.B. Cellulose);(7) partial esters based on linear, branched, unsaturated or saturated C6 / 22 fatty acids, ricinoleic acid and 12-hydroxystearic acid and glycerol, polyglycerol, pentaerythritol, dipentaerythritol, sugar alcohols (eg sorbitol), alkyl glucosides (eg methyl glucoside, butyl glucoside, butyl glucoside , Lauryl glucoside) and polyglucosides (eg cellulose);
(8) Mono-, Di- und Trialkylphosphate sowie Mono-, Di- und/oder Tri-PEG-alkylphosphate und deren Salze;(8) mono-, di- and trialkyl phosphates as well as mono-, di- and / or tri-PEG-alkyl phosphates and their salts;
(9) Wollwachsalkohole;(9) wool wax alcohols;
(10) Polysiloxan-Polyalkyl-Polyether-Copolymere bzw. entsprechende Derivate;(10) polysiloxane-polyalkyl-polyether copolymers or corresponding derivatives;
(11) Mischester aus Pentaerythrit, Fettsäuren, Citronensäure und Fettalkohol gemäß DE 1165574 PS und/oder Mischester von Fettsäuren mit 6 bis 22 Kohlenstoffatomen, Methyl- glucose und Polyolen, vorzugsweise Glycerin oder Polyglycerin sowie(11) mixed esters of pentaerythritol, fatty acids, citric acid and fatty alcohol according to DE 1165574 PS and / or mixed esters of fatty acids with 6 to 22 carbon atoms, methyl glucose and polyols, preferably glycerol or polyglycerol and
(12) Polyalkylenglycole.(12) Polyalkylene glycols.
Die Anlagerungsprodukte von Ethylenoxid und/oder von Propylenoxid an Fettsäuren, Aikylphenole, Glycerinmono- und -diester sowie Sorbitanmono- und -diester von Fettsäuren oder an Ricinusöl stellen bekannte, im Handel erhältliche Produkte dar. Es handelt sich dabei um Homologengemische, deren mittlerer Alkoxylierungsgrad dem Verhältnis der Stoffmengen von Ethylenoxid und/ oder Propylenoxid und Substrat, mit denen die Anlagerungsreaktion durchgeführt wird, entspricht. Ci2/i8-Fettsäuremono- und -diester von Anlagerungsprodukten von Ethylenoxid an Glycerin sind aus DE 2024051 PS als Rückfettungsmittel für kosmetische Zubereitungen bekannt.The adducts of ethylene oxide and / or of propylene oxide with fatty acids, aikylphenols, glycerol mono- and diesters as well as sorbitan mono- and diesters with fatty acids or with castor oil are known, commercially available products. These are mixtures of homologs, the average degree of alkoxylation of which is Ratio of the amounts of ethylene oxide and / or propylene oxide and substrate with which the addition reaction is carried out corresponds. Ci2 / i8 fatty acid monoesters and diesters of adducts of ethylene oxide with glycerol are known from DE 2024051 PS as refatting agents for cosmetic preparations.
Weiterhin können als Emulgatoren zwitterionische Tenside verwendet werden. Als zwitterionische Tenside werden solche oberflächenaktiven Verbindungen bezeichnet, die im Molekül mindestens eine quartäre Ammoniumgruppe und mindestens eine Carboxylat- und eine Sulfonatgruppe tragen. Besonders geeignete zwitterionische Tenside sind die sogenannten Betaine wie die N-Alkyl-N,N- dimethylammoniumglycinate, beispielsweise das Kokosalkyldimethylammoniumglycinat, N-Acyl- aminopropyl-N,N-dimethylammoniumglycinate, beispielsweise das Kokosacylaminopropyl- dimethylammoniumglycinat, und 2-Alkyl-3-carboxylmethyl-3-hydroxyethylimidazoline mit jeweils 8 bis 18 C-Atomen in der Alkyl- oder Acylgruppe sowie das Kokosacylaminoethylhydroxyethyl- carboxymethylglycinat. Besonders bevorzugt ist das unter der CTFA-Bezeichnung Cocamidopropyl Betaine bekannte Fettsäureamid-Derivat. Ebenfalls geeignete Emulgatoren sind ampholytische Tenside. Unter ampholytischen Tensiden werden solche oberflächenaktiven Verbindungen verstanden, die außer einer Cβ/iβ-Alkyl- oder -Acylgruppe im Molekül mindestens eine freie Aminogruppe und mindestens eine -COOH- oder -SOßH-Gruppe enthalten und zur Ausbildung innerer Salze befähigt sind. Beispiele für geeignete ampholytische Tenside sind N-Alkylglycine, N- Alkylpropionsäuren, N-Alkylaminobuttersäuren, N-Alkyliminodipropionsäuren, N-Hydroxyethyl-N- alkylamidopropylglycine, N-Alkyltaurine, N-Alkylsarcosine, 2-Alkylaminopropionsäuren und Alkylaminoessigsäuren mit jeweils etwa 8 bis 18 C-Atomen in der Alkylgruppe. Besonders bevorzugte ampholytische Tenside sind das N-Kokosalkylaminopropionat, das Kokosacylaminoethylaminopropionat und das Ci∑ -Acylsarcosin. Neben den ampholytischen kommen auch quartäre Emulgatoren in Betracht, wobei solche vom Typ der Esterquats, vorzugsweise methylquaternierte Difettsäuretriethanolaminester-Salze, besonders bevorzugt sind.Zwitterionic surfactants can also be used as emulsifiers. Zwitterionic surfactants are surface-active compounds that contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule. Particularly suitable zwitterionic surfactants are the so-called betaines such as the N-alkyl-N, N-dimethylammonium glycinate, for example the cocoalkyldimethylammonium glycinate, N-acylaminopropyl-N, N-dimethylammonium glycinate, for example the cocoacylaminopropyldimethylammonium glycinate, and 2-alkyl-3-carboxyl -3-hydroxyethylimidazolines each having 8 to 18 carbon atoms in the alkyl or acyl group and the cocoacylaminoethylhydroxyethylcarboxymethylglycinate. The fatty acid amide derivative known under the CTFA name of Cocamidopropyl Betaine is particularly preferred. Suitable emulsifiers are ampholytic surfactants. Ampholytic surfactants are surface-active compounds which, in addition to a Cβ / iβ-alkyl or -acyl group, contain at least one free amino group and at least one -COOH or -SOßH group in the molecule and are capable of forming internal salts. Examples of suitable ampholytic surfactants are N-alkylglycine, N-alkylpropionic acid, N-alkylaminobutyric acid, N-alkyliminodipropionic acid, N-hydroxyethyl-N-alkylamidopropylglycine, N-alkyltaurine, N-alkylsarcosine, 2-alkylaminopropionic acid and alkylaminoacetic acid each with about 8 to 18 C. Atoms in the alkyl group. Particularly preferred ampholytic surfactants are N-coconut alkyl aminopropionate, coconut acylaminoethyl aminopropionate and Ci∑-acyl sarcosine. In addition to the ampholytic emulsifiers, quaternary emulsifiers are also suitable, those of the esterquat type, preferably methylquaternized difatty acid triethanolamine ester salts, being particularly preferred.
Als Überfettungsmittel können Substanzen wie beispielsweise Lanolin und Lecithin sowie polyethoxylierte oder acylierte Lanolin- und Lecithinderivate, Polyolfettsäureester, Monoglyceride und Fettsäurealkanolamide verwendet werden, wobei die letzteren gleichzeitig als Schaumstabilisatoren dienen.Substances such as, for example, lanolin and lecithin and polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides can be used as superfatting agents, the latter simultaneously serving as foam stabilizers.
Als Perlglanzwachse kommen beispielsweise in Frage: Alkylenglycolester, speziell Ethylenglycol- distearat; Fettsäurealkanolamide, speziell Kokosfettsäurediethanolamid; Partialglyceride, speziell Stearinsäuremonoglycerid; Ester von mehrwertigen, gegebenenfalls hydroxysubstituierte Carbonsäuren mit Fettalkoholen mit 6 bis 22 Kohienstoffatomen, speziell langkettige Ester der Weinsäure; Fettstoffe, wie beispielsweise Fettalkohole, Fettketone, Fettaldehyde, Fettether und Fettcarbonate, die in Summe mindestens 24 Kohlenstoffatome aufweisen, speziell Lauron und Distearylether; Fettsäuren wie Stearinsäure, Hydroxystearinsäure oder Behensaure, Ringöffnungsprodukte vonPearlescent waxes, for example, are: alkylene glycol esters, especially ethylene glycol distearate; Fatty acid alkanolamides, especially coconut fatty acid diethanolamide; Partial glycerides, especially stearic acid monoglyceride; Esters of polyvalent, optionally hydroxy-substituted carboxylic acids with fatty alcohols with 6 to 22 carbon atoms, especially long-chain esters of tartaric acid; Fatty substances, such as, for example, fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates, which have a total of at least 24 carbon atoms, especially lauron and distearyl ether; Fatty acids such as stearic acid, hydroxystearic acid or behenic acid, ring opening products from
n Olefinepoxiden mit 12 bis 22 Kohlenstoffatomen mit Fettalkoholen mit 12 bis 22 Kohlenstoffatomen und/oder Polyolen mit 2 bis 15 Kohlenstoffatomen und 2 bis 10 Hydroxylgruppen sowie deren Mischungen.n Olefin epoxides with 12 to 22 carbon atoms with fatty alcohols with 12 to 22 carbon atoms and / or polyols with 2 to 15 carbon atoms and 2 to 10 hydroxyl groups and mixtures thereof.
Als Konsistenzgeber kommen in erster Linie Fettalkohole oder Hydroxyfettalkohole mit 12 bis 22 und vorzugsweise 16 bis 18 Kohlenstoffatomen und daneben Partialglyceride, Fettsäuren oder Hydroxyfettsäuren in Betracht. Bevorzugt ist eine Kombination dieser Stoffe mit Alkyloligoglucosi- den und/oder Fettsäure-N-methylglucamiden gleicher Kettenlänge und/oder Polyglycerinpoly-12- hydroxystearaten.Suitable consistency agents are primarily fatty alcohols or hydroxy fatty alcohols with 12 to 22 and preferably 16 to 18 carbon atoms and, in addition, partial glycerides, fatty acids or hydroxy fatty acids. A combination of these substances with alkyl oligoglucosides and / or fatty acid N-methyl glucamides of the same chain length and / or polyglycerol poly-12-hydroxystearates is preferred.
Geeignete Verdickungsmittel sind beispielsweise Polysaccharide, insbesondere Xanthan-Gum, Guar-Guar, Agar-Agar, Alginate und Tylosen, Carboxymethylcelluiose und Hydroxyethylcellulose, ferner höhermolekulare Polyethylenglycolmono- und -diester von Fettsäuren, Polyacrylate, (z.B. Carbopole® von Goodrich oder Synthalene® von Sigma), Polyacrylamide, Polyvinylalkohol und Polyvinylpyrrolidon, Tenside wie beispielsweise ethoxylierte Fettsäuregiyceride, Ester von Fettsäuren mit Polyolen wie beispielsweise Pentaerythrit oder Trimethylolpropan, Fettalkohol- ethoxylate mit eingeengter Homologenverteiiung oder Alkyloiigoglucoside sowie Elektrolyte wie Kochsalz und Ammoniumchlorid.Suitable thickeners are, for example, polysaccharides, in particular xanthan gum, guar guar, agar agar, alginates and tyloses, carboxymethyl cellulose and hydroxyethyl cellulose, and also higher molecular weight polyethylene glycol mono- and diesters of fatty acids, polyacrylates, (for example Carbopole® from Goodrich or Synthalene® from Sigma ), Polyacrylamides, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as ethoxylated fatty acid glycerides, esters of fatty acids with polyols such as pentaerythritol or trimethylolpropane, fatty alcohol ethoxylates with a restricted homolog distribution or alkyl oligoglucosides as well as electrolytes such as sodium chloride and ammonium chloride.
Geeignete kationische Polymere sind beispielsweise kationische Cellulosederivate, wie z.B. eine quaternierte Hydroxyethylcellulose, die unter der Bezeichnung Polymer JR 400® von Amerchol erhältlich ist, kationische Stärke, Copolymere von Diallylammoniumsalzen und Acrylamiden, quaternierte Vinylpyrrolidon/Vinylimidazol-Polymere, wie z.B. Luviquat® (BASF), Kondensationsprodukte von Polyglycolen und Aminen, quaternierte Kollagenpolypeptide, wie beispielsweise Lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L/Grünau), quaternierte Weizen- polypeptide, Polyethylenimin, kationische Siliconpolymere, wie z.B. Amidomethicone, Copolymere der Adipinsäure und Dimethylaminohydroxypropyldiethylentriamin (Cartaretine®/Sandoz), Copolymere der Acrylsäure mit Dimethyldiallylammoniumchlorid (Merquat® 550/Chemviron), Polya- minopolyamide, wie z.B. beschrieben in der FR 2252840 A sowie deren vernetzte wasserlöslichen Polymere, kationische Chitinderivate wie beispielsweise quaterniertes Chitosan, gegebenenfalls mikrokristallin verteilt, Kondensationsprodukte aus Dihalogenalkylen, wie z.B. Dibrombutan mit Bisdialkylaminen, wie z.B. Bis-Dimethylamino-1 ,3-propan, kationischer Guar-Gum, wie z.B. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 der Firma Celanese, quaternierte Ammoniumsalz- Polymere, wie z.B. Mirapol® A-15, Mirapol® AD-1 , Mirapol® AZ-1 der Firma Miranol.Suitable cationic polymers are, for example, cationic cellulose derivatives, e.g. a quaternized hydroxyethyl cellulose available under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallylammonium salts and acrylamides, quaternized vinylpyrrolidone / vinylimidazole polymers such as e.g. Luviquat® (BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides, such as lauryldimonium hydroxypropyl hydrolyzed collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers, e.g. Amidomethicones, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine (Cartaretine® / Sandoz), copolymers of acrylic acid with dimethyldiallylammonium chloride (Merquat® 550 / Chemviron), polyamino polyamides, e.g. described in FR 2252840 A and its crosslinked water-soluble polymers, cationic chitin derivatives such as quaternized chitosan, optionally microcrystalline, condensation products of dihaloalkylene, such as e.g. Dibromobutane with bisdialkylamines, e.g. Bis-dimethylamino-1, 3-propane, cationic guar gum, e.g. Jaguar® CBS, Jaguar® C-17, Jaguar® C-16 from Celanese, quaternized ammonium salt polymers, e.g. Mirapol® A-15, Mirapol® AD-1, Mirapol® AZ-1 from Miranol.
Als anionische, zwitterionische, amphotere und nichtionische Polymere kommen beispielsweise Vinylacetat/Crotonsäure-Copolymere, Vinylpyrrolidon/Vinylacrylat-Copolymere, Vinylace- tat/Butylmaleat/ Isobomylacrylat-Copolymere, Methylvinylether/Maleinsäureanhydrid-Copolymere und deren Ester, unvemetzte und mit Polyolen vernetzte Polyacrylsäuren, Acrylamidopropyl- trimethylammoniumchlorid/ Acrylat-Copolymere, Octylacrylamid/Methylmethacry- lat/tert.Butylaminoethylmethacrylat/2-Hydroxypropylmethacrylat-Copoiymere, Polyvinylpyrrolidon, Vinylpyrrolidon/Vinylacetat-Copolymere, Vinylpyrrolidon/Dimethylaminoethylmethacrylat/Vinyl- caprolactam-Teφolymere sowie gegebenenfalls derivatisierte Celluloseether und Silicone in Frage.Anionic, zwitterionic, amphoteric and nonionic polymers include, for example, vinyl acetate / crotonic acid copolymers, vinylpyrrolidone / vinyl acrylate copolymers, vinyllace- tat / butyl maleate / isobomylacrylate copolymers, methyl vinyl ether / maleic anhydride copolymers and their esters, uncrosslinked and polyol-crosslinked polyacrylic acids, acrylamidopropyl trimethylammonium chloride / acrylate copolymers, octylacrylamide / methyl methacrylate / tert.butylaminoethyl methacrylate, poly-hydroxypropyl methacrylate / 2-hydroxypropyl acrylate, Vinyl pyrrolidone / vinyl acetate copolymers, vinyl pyrrolidone / dimethylaminoethyl methacrylate / vinyl caprolactam teφolymers and optionally derivatized cellulose ethers and silicones in question.
Geeignete Siliconverbindungen sind beispielsweise Dimethylpolysiloxane, Methylphenylpolysi- loxane, cyclische Silicone sowie amino-, fettsäure-, alkohol-, polyether-, epoxy-, fluor-, glykosid- und/oder alkylmodifizierte Siliconverbindungen, die bei Raumtemperatur sowohl flüssig als auch harzförmig vorliegen können. Eine detaillierte Übersicht über geeignete flüchtige Silicone findet sich zudem von Todd et al. in Cosm.Toil. 91, 27 (1976).Suitable silicone compounds are, for example, dimethylpolysiloxanes, methylphenylpolysiloxanes, cyclic silicones and amino, fatty acid, alcohol, polyether, epoxy, fluorine, glycoside and / or alkyl-modified silicone compounds, which can be both liquid and resinous at room temperature. A detailed overview of suitable volatile silicones can also be found by Todd et al. in Cosm.Toil. 91, 27 (1976).
Typische Beispiele für Fette sind Glyceride, als Wachse kommen u.a. Bienenwachs, Carnauba- wachs, Candelillawachs, Montanwachs, Paraffinwachs, hydriertes Ricinusöle, bei Raumtemperatur feste Fettsäureester oder Mikrowachse gegebenenfalls in Kombination mit hydrophilen Wachsen, z.B. Cetylstearylalkohol oder Partialglyceriden in Frage. Als Stabilisatoren können Metallsalze von Fettsäuren, wie z.B. Magnesium-, Aluminium- und/oder Zinkstearat bzw. -ricinoleat eingesetzt werden.Typical examples of fats are glycerides, waxes include Beeswax, carnauba wax, candelilla wax, montan wax, paraffin wax, hydrogenated castor oils, fatty acid esters or micro waxes solid at room temperature, optionally in combination with hydrophilic waxes, e.g. Cetylstearyl alcohol or partial glycerides in question. Metal salts of fatty acids, such as e.g. Magnesium, aluminum and / or zinc stearate or ricinoleate are used.
Unter biogenen Wirkstoffen sind beispielsweise Tocopherol, Tocopherolacetat, Tocopherolpal- mitat, Ascorbinsäure, Desoxyribonucleinsäure, Retinol, Bisabolol, Allantoin, Phytantriol, Panthenol, AHA-Säuren, Aminosäuren, Ceramide, Pseudoceramide, essentielle Öle, Pflanzenextrakte und Vitaminkomplexe zu verstehen.Biogenic active substances are, for example, tocopherol, tocopherol acetate, tocopherol palmitate, ascorbic acid, deoxyribonucleic acid, retinol, bisabolol, allantoin, phytantriol, panthenol, AHA acids, amino acids, ceramides, pseudoceramides, essential oils, plant extracts and vitamin complexes.
Als Deowirkstoffe kommen z.B. Antiperspirantien wie etwa Aluminiumchlorhydate in Frage. Hierbei handelt es sich um farblose, hygroskopische Kristalle, die an der Luft leicht zerfließen und beim Eindampfen wäßriger Aluminiumchloridlösungen anfallen. Aiuminiumchlorhydrat wird zur Herstellung von schweißhemmenden und desodorierenden Zubereitungen eingesetzt und wirkt wahrscheinlich über den partiellen Verschluß der Schweißdrüsen durch Eiweiß- und/oder Polysaccha- ridfällung [vgl. J.Soc.Cosm.Chem. 24, 281 (1973)]. Unter der Marke Locron® der Hoechst AG,Deodorants come e.g. Antiperspirants such as aluminum chlorohydates are possible. These are colorless, hygroscopic crystals that easily dissolve in the air and arise when aqueous aluminum chloride solutions are evaporated. Aiuminium chlorohydrate is used for the manufacture of antiperspirant and deodorant preparations and is likely to act by partially occluding the sweat glands through protein and / or polysaccharide precipitation [cf. J.Soc.Cosm.Chem. 24, 281 (1973)]. Under the Locron® brand from Hoechst AG,
Frankfurt/FRG, befindet beispielsweise sich ein Aiuminiumchlorhydrat im Handel, das der Formel [Al2(OH)5CI]*2,5 H20 entspricht und dessen Einsatz besonders bevorzugt ist [vgl. J.Pharm.Pharmacol. 26, 531 (1975)]. Neben den Chlorhydraten können auch Aluminiumhy- droxylactate sowie saure Aluminium/Zirkoniumsalze eingesetzt werden. Als weitere Deowirkstoffe können Esteraseinhibitoren zugesetzt werden. Hierbei handelt es sich vorzugsweise um Trialkyl- citrate wie Trimethylcitrat, Tripropylcitrat, Triisopropylcitrat, Tributylcitrat und insbesondere Triethyl- citrat (Hydagen® CAT, Henkel KGaA, Düsseldorf/FRG). Die Stoffe inhibieren die Enzymaktivität und reduzieren dadurch die Geruchsbildung. Wahrscheinlich wird dabei durch die Spaltung des Citronensäureesters die freie Säure freigesetzt, die den pH-Wert auf der Haut soweit absenkt, daß dadurch die Enzyme inhibiert werden. Weitere Stoffe, die als Esteraseinhibitoren in Betracht kommen, sind Dicarbonsäuren und deren Ester, wie beispielsweise Glutarsäure, Glutarsäuremo- noethylester, Glutarsäurediethylester, Adipinsäure, Adipinsäuremonoethylester, Adipinsäuredie- thylester, Malonsäure und Malonsäurediethylester, Hydroxycarbnonsäuren und deren Ester wie beispielsweise Citronensäure, Äpfelsäure, Weinsäure oder Weinsäurediethylester. Antibakterielle Wirkstoffe, die die Keimflora beeinflussen und schweißzersetzende Bakterien abtöten bzw. in ihrem Wachstum hemmen, können ebenfalls in den Stiftzubereitungen enthalten sein. Beispiele hierfür sind Chitosan, Phenoxyethanol und Chlorhexidingluconat. Besonders wirkungsvoll hat sich auch 5-Chlor-2-(2,4-dichlorphen-oxy)-phenol erwiesen, das unter der Marke Irgasan® von derFrankfurt / FRG, for example, is aiumium chlorohydrate on the market which corresponds to the formula [Al2 (OH) 5CI] * 2.5 H 2 0 and whose use is particularly preferred [cf. J.Pharm.Pharmacol. 26, 531 (1975)]. In addition to the chlorohydrates, aluminum hydroxyl lactates and acidic aluminum / zirconium salts can also be used. Esterase inhibitors can be added as further deodorant active ingredients. These are preferably trialkyl citrates such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and in particular triethyl citrate (Hydagen® CAT, Henkel KGaA, Düsseldorf / FRG). The substances inhibit enzyme activity and thereby reduce odor. The cleavage of the citric acid ester probably releases the free acid, which lowers the pH value on the skin to such an extent that the enzymes are inhibited. Other substances which are suitable esterase inhibitors are dicarboxylic acids and esters thereof such as glutaric acid, Glutarsäuremo- noethylester, diethyl glutarate, adipic acid, adipic acid monoethyl ester, Adipinsäuredie- methyl ester, malonic acid and diethyl malonate, hydroxycarboxylic acids and esters thereof such as citric acid, malic acid, tartaric acid or Tartaric acid diethyl ester. Antibacterial agents that influence the bacterial flora and kill sweat-killing bacteria or inhibit their growth can also be contained in the stick preparations. Examples include chitosan, phenoxyethanol and chlorhexidine gluconate. 5-Chloro-2- (2,4-dichlorophen-oxy) phenol, which is sold under the Irgasan® brand by
Ciba-Geigy, Basel/CH vertrieben wird.Ciba-Geigy, Basel / CH.
Als Antischuppenmittel können Climbazol, Octopirox und Zinkpyrethion eingesetzt werden. Gebräuchliche Filmbildner sind beispielsweise Chitosan, mikrokristallines Chitosan, quatemiertes Chitosan, Polyvinylpyrrolidon, Vinylpyrrolidon-Vinylacetat-Copolymerisate, Polymere der Acrylsäurereihe, quaternäre Celiulose-Derivate, Kollagen, Hyaluronsäure bzw. deren Salze und ähnliche Verbindungen. Als Quellmittel für wäßrige Phasen können Montmorillonite, Clay Mineralstoffe, Pemulen sowie alkylmodifizierte Carbopoltypen (Goodrich) dienen. Weitere geeignete Polymere bzw. Quellmittel können der Übersicht von R.Lochhead in Cosm.Toil. 108, 95 (1993) entnommen werden.Climbazole, octopirox and zinc pyrethione can be used as antidandruff agents. Common film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinylpyrrolidone, vinylpyrrolidone-vinyl acetate copolymers, polymers of the acrylic acid series, quaternary celulose derivatives, collagen, hyaluronic acid or its salts and similar compounds. Montmorillonites, clay minerals, pemulene and alkyl-modified carbopol types (Goodrich) can serve as swelling agents for aqueous phases. Further suitable polymers or swelling agents can be found in the overview by R. Lochhead in Cosm.Toil. 108, 95 (1993).
Unter UV-Lichtschutzfaktoren sind beispielsweise bei Raumtemperatur flüssig oder kristallin vorliegende organische Substanzen (Lichtschutzfilter) zu verstehen, die in der Lage sind, ultraviolette Strahlen zu absorbieren und die aufgenommene Energie in Form längerwelliger Strahlung, z.B. Wärme wieder abzugeben. UVB-Filter können öllöslich oder wasserlöslich sein. Als öllösliche Substanzen sind z.B. zu nennen:UV light protection factors are understood to mean, for example, organic substances (light protection filters) which are liquid or crystalline at room temperature and which are able to absorb ultraviolet rays and absorb the energy absorbed in the form of longer-wave radiation, e.g. To give off heat again. UVB filters can be oil-soluble or water-soluble. As oil-soluble substances e.g. to call:
• 3-Benzylidencampher bzw. 3-Benzylidennorcampher und dessen Derivate, z.B. 3-(4-Methyl- benzyliden)campher wie in der EP 0693471 B1 beschrieben;3-benzylidene camphor or 3-benzylidene norcampher and its derivatives, e.g. 3- (4-methylbenzylidene) camphor as described in EP 0693471 B1;
• 4-Aminobenzoesäurederivate, vorzugsweise 4-(Dimethylamino)benzoesäure-2-ethylhexylester, 4-(Dimethylamino)benzoesäure-2-octylester und 4-(Dimethylamino)benzoesäureamylester;4-aminobenzoic acid derivatives, preferably 2-ethylhexyl 4- (dimethylamino) benzoate, 2-octyl 4- (dimethylamino) benzoate and amyl 4- (dimethylamino) benzoate;
• Ester der Zimtsäure, vorzugsweise 4-Methoxyzimtsäure-2-ethylhexylester, 4-Methoxyzimtsäu- repropylester, 4-Methoxyzimtsäureisoamylester 2-Cyano-3,3-phenylzimtsäure-2-ethylhexyles- ter (Octocrylene);• esters of cinnamic acid, preferably 2-ethylhexyl 4-methoxycinnamate, propyl 4-methoxycinnamate, 2-cyano-3,3-phenylcinnamate-2-ethylhexyl ester (octocrylene) 4-methoxycinnamate;
• Ester der Salicylsäure, vorzugsweise Saiicylsäure-2-ethylhexylester, Salicylsäure-4-isopropyl- benzylester, Salicylsäurehomomenthylester; • Derivate des Benzophenons, vorzugsweise 2-Hydroxy-4-methoxybenzophenon, 2-Hydroxy-4- methoxy-4'-methylbenzophenon, 2,2'-Dihydroxy-4-methoxybenzophenon;• esters of salicylic acid, preferably 2-ethylhexyl saiicylic acid, 4-isopropylbenzyl salicylic acid, homomethyl salicylic acid; • Derivatives of benzophenone, preferably 2-hydroxy-4-methoxybenzophenone, 2-hydroxy-4-methoxy-4'-methylbenzophenone, 2,2'-dihydroxy-4-methoxybenzophenone;
• Ester der Benzalmalonsäure, vorzugsweise 4-Methoxybenzmalonsäuredi-2-ethylhexylester;• Esters of benzalmalonic acid, preferably di-2-ethylhexyl 4-methoxybenzmalonate;
• Triazinderivate, wie z.B. 2,4,6-Trianilino-(p-carbo-2'-ethyl-1 '-hexyloxy)-1,3,5-triazin und Octyl Triazon, wie in der EP 0818450 A1 beschrieben;Triazine derivatives, e.g. 2,4,6-trianilino- (p-carbo-2'-ethyl-1'-hexyloxy) -1,3,5-triazine and octyl triazone, as described in EP 0818450 A1;
• Propan-1 ,3-dione, wie z.B. 1-(4-tert.Butylphenyl)-3-(4'methoxyphenyl)propan-1 ,3-dion;Propane-1,3-dione, e.g. 1- (4-tert-butylphenyl) -3- (4'methoxyphenyl) propane-1,3-dione;
• Ketotricyclo(5.2.1.0)decan-Derivate, wie in der EP 0694521 B1 beschrieben.• Ketotricyclo (5.2.1.0) decane derivatives, as described in EP 0694521 B1.
Als wasserlösliche Substanzen kommen in Frage:Possible water-soluble substances are:
• 2-Phenylbenzimidazol-5-sulfonsäure und deren Alkali-, Erdalkali-, Ammonium-, Alkylammo- nium-, Alkanolammonium- und Glucammoniumsalze;• 2-phenylbenzimidazole-5-sulfonic acid and its alkali, alkaline earth, ammonium, alkylammonium, alkanolammonium and glucammonium salts;
• Sulfonsäurederivate von Benzophenonen, vorzugsweise 2-Hydroxy-4-methoxybenzophenon- 5-sulfonsäure und ihre Salze;• sulfonic acid derivatives of benzophenones, preferably 2-hydroxy-4-methoxybenzophenone-5-sulfonic acid and its salts;
• Sulfonsäurederivate des 3-Benzylidencamphers, wie z.B. 4-(2-Oxo-3-bornylidenmethyl)ben- zolsulfonsäure und 2-Methyl-5-(2-oxo-3-bornyliden)sulfonsäure und deren Salze.Sulfonic acid derivatives of 3-benzylidene camphor, e.g. 4- (2-oxo-3-bornylidene methyl) benzenesulfonic acid and 2-methyl-5- (2-oxo-3-bornylidene) sulfonic acid and their salts.
Als typische UV-A-Filter kommen insbesondere Derivate des Benzoylmethans in Frage, wie beispielsweise 1-(4'-tert.Butylphenyl)-3-(4'-methoxyphenyl)propan-1 ,3-dion, 4-tert.-Butyl-4'-methoxy- dibenzoylmethan (Parsol 1789), oder 1-Phenyl-3-(4'-isopropylphenyl)-propan-1 ,3-dion. Die UV-A und UV-B-Filter können selbstverständlich auch in Mischungen eingesetzt werden. Neben den genannten löslichen Stoffen kommen für diesen Zweck auch unlösliche Lichtschutzpigmente, nämlich feindisperse Metalloxide bzw. Salze in Frage. Beispiele für geeignete Metalloxide sind insbesondere Zinkoxid und Titandioxid und daneben Oxide des Eisens, Zirkoniums, Siliciums, Mangans, Aluminiums und Cers sowie deren Gemische. Als Salze können Silicate (Talk), Bariumsulfat oder Zinkstearat eingesetzt werden. Die Oxide und Salze werden in Form der Pigmente für hautpflegende und hautschützende Emulsionen und dekorative Kosmetik verwendet. Die Partikel sollten dabei einen mittleren Durchmesser von weniger als 100 nm, vorzugsweise zwischen 5 und 50 nm und insbesondere zwischen 15 und 30 nm aufweisen. Sie können eine sphärische Form aufweisen, es können jedoch auch solche Partikel zum Einsatz kommen, die eine ellipsoide oder in sonstiger Weise von der sphärischen Gestalt abweichende Form besitzen. In Sonnenschutzmitteln werden bevorzugt sogenannte Mikro- oder Nanopigmente eingesetzt. Vorzugsweise wird mikroni- siertes Zinkoxid verwendet.Derivatives of benzoylmethane, such as 1- (4'-tert-butylphenyl) -3- (4'-methoxyphenyl) propane-1, 3-dione, 4-tert-butyl, are particularly suitable as typical UV-A filters -4'-methoxy-dibenzoylmethane (Parsol 1789), or 1-phenyl-3- (4'-isopropylphenyl) propane-1,3-dione. The UV-A and UV-B filters can of course also be used in mixtures. In addition to the soluble substances mentioned, insoluble light protection pigments, namely finely dispersed metal oxides or salts, are also suitable for this purpose. Examples of suitable metal oxides are, in particular, zinc oxide and titanium dioxide and, in addition, oxides of iron, zirconium, silicon, manganese, aluminum and cerium and mixtures thereof. Silicates (talc), barium sulfate or zinc stearate can be used as salts. The oxides and salts are used in the form of the pigments for skin-care and skin-protecting emulsions and decorative cosmetics. The particles should have an average diameter of less than 100 nm, preferably between 5 and 50 nm and in particular between 15 and 30 nm. They can have a spherical shape, but it is also possible to use particles which have an ellipsoidal shape or shape which differs from the spherical shape in some other way. So-called micro- or nanopigments are preferably used in sunscreens. Micronized zinc oxide is preferably used.
Weitere geeignete UV-Lichtschutzfilter sind der Übersicht von P.Finkel in SÖFW-Journal 122, 543 (1996) zu entnehmen. Neben den beiden vorgenannten Gruppen primärer Lichtschutzstoffe können auch sekundäre Lichtschutzmittel vom Typ der Antioxidantien eingesetzt werden, die die photochemische Reaktionskette unterbrechen, welche ausgelöst wird, wenn UV-Strahlung in die Haut eindringt. Typische Beispiele hierfür sind Aminosäuren (z.B. Glycin, Histidin, Tyrosin, Tryptophan) und deren Derivate, Imidazole (z.B. Urocaninsäure) und deren Derivate, Peptide wie D,L-Camosin, D-Camosin, L-Car- nosin und deren Derivate (z.B. Anserin), Carotinoide, Carotine (z.B. α-Carotin, ß-Carotin, Lycopin) und deren Derivate, Chlorogensäure und deren Derivate, Liponsäure und deren Derivate (z.B. Dihydroliponsäure), Aurothioglucose, Propylthiouracil und andere Thiole (z.B. Thioredoxin, Glutathion, Cystein, Cystin, Cystamin und deren Glycosyl-, N-Acetyl-, Methyl-, Ethyl-, Propyl-, Amyl-, Butyl- und Lauryl-, Palmitoyl-, Oleyl-, γ-Linoleyl-, Cholesteryl- und Glycerylester) sowie deren Salze, Dilaurylthiodipropionat, Distearylthiodipropionat, Thiodipropionsäure und deren Derivate (Ester, Ether, Peptide, Lipide, Nukleotide, Nukleoside und Salze) sowie Sulfoximinverbindungen (z.B. Buthioninsulfoximine, Homocysteinsulfoximin, Butioninsulfone, Penta-, Hexa-, Hep- tathioninsulfoximin) in sehr geringen verträglichen Dosierungen (z.B. pmol bis μmol/kg), ferner (Metall)-Chelatoren (z.B. α-Hydroxyfettsäuren, Palmitinsäure, Phytinsäure, Lactoferrin), α-Hy- droxysäuren (z.B. Citronensäure, Milchsäure, Apfelsäure), Huminsäure, Gallensäure, Gallenextrakte, Bilirubin, Biliverdin, EDTA, EGTA und deren Derivate, ungesättigte Fettsäuren und deren Derivate (z.B. γ-Linolensäure, Linolsäure, Ölsäure), Folsäure und deren Derivate, Ubichinon undFurther suitable UV light protection filters can be found in the overview by P.Finkel in SÖFW-Journal 122, 543 (1996). In addition to the two aforementioned groups of primary light stabilizers, secondary light stabilizers of the antioxidant type can also be used, which interrupt the photochemical reaction chain which is triggered when UV radiation penetrates the skin. Typical examples of this are amino acids (e.g. glycine, histidine, tyrosine, tryptophan) and their derivatives, imidazoles (e.g. urocanic acid) and their derivatives, peptides such as D, L-camosine, D-camosine, L-carosin and their derivatives (e.g. Anserine), carotenoids, carotenes (eg α-carotene, β-carotene, lycopene) and their derivatives, chlorogenic acid and their derivatives, lipoic acid and their derivatives (eg dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (eg thioredoxin, glutathione, cysteine, Cystine, cystamine and their glycosyl, N-acetyl, methyl, ethyl, propyl, amyl, butyl and lauryl, palmitoyl, oleyl, γ-linoleyl, cholesteryl and glyceryl esters) and their salts , Dilauryl thiodipropionate, distearyl thiodipropionate, thiodipropionic acid and their derivatives (esters, ethers, peptides, lipids, nucleotides, nucleosides and salts) as well as sulfoximine compounds (eg buthioninsulfoximines, homocysteine sulfoximines, butioninsulfones, penta-, hexa-, hepatathioninsulfoxins. Low) tolerable dosages (e.g. pmol to μmol / kg), (metal) chelators (e.g. α-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin), α-hydroxy acids (e.g. citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, Bilirubin, biliverdin, EDTA, EGTA and their derivatives, unsaturated fatty acids and their derivatives (eg γ-linolenic acid, linoleic acid, oleic acid), folic acid and its derivatives, ubiquinone and
Ubichinol und deren Derivate, Vitamin C und Derivate (z.B. Ascorbyipalmitat, Mg-Ascorbyiphos- phat, Ascorbylacetat), Tocopherole und Derivate (z.B. Vitamin-E-acetat), Vitamin A und Derivate (Vitamin-A-palmitat) sowie Koniferylbenzoat des Benzoeharzes, Rutinsäure und deren Derivate, α- Glycosylrutin, Ferulasäure, Furfurylidenglucitol, Camosin, Butylhydroxytoluol, Butylhydroxyanisol, Nordihydroguajakharzsäure, Nordihydroguajaretsäure, Trihydroxybutyrophenon, Harnsäure und deren Derivate, Mannose und deren Derivate, Superoxid-Dismutase, Zink und dessen Derivate (z.B. ZnO, ZnS04) Selen und dessen Derivate (z.B. Selen-Methionin), Stilbene und deren Derivate (z.B. Stilbenoxid, trans-Stilbenoxid) und die erfindungsgemäß geeigneten Derivate (Salze, Ester, Ether, Zucker, Nukleotide, Nukleoside, Peptide und Lipide) dieser genannten Wirkstoffe.Ubiquinol and its derivatives, vitamin C and derivatives (e.g. ascorbyipalmitate, Mg ascorbyiphosphate, ascorbylacetate), tocopherols and derivatives (e.g. vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) as well as coniferyl benzoate of the benzoin resin, rutinic acid and derivatives thereof, α- rutin, ferulic acid, Furfurylidenglucitol, carnosine, butylhydroxytoluene, butylhydroxyanisole, Nordihydroguajakharzsäure, nordihydroguaiaretic acid, trihydroxybutyrophenone, uric acid and derivatives thereof, mannose and derivatives thereof, superoxide dismutase, zinc and derivatives thereof (for example ZnO, ZnS0 4) Selenium and its derivatives (eg selenium-methionine), stilbenes and their derivatives (eg stilbene oxide, trans-stilbene oxide) and the derivatives suitable according to the invention (salts, esters, ethers, sugars, nucleotides, nucleosides, peptides and lipids) of these active substances.
Zur Verbesserung des Fließverhaltens können femer Hydrotrope, wie beispielsweise Ethanol, Isopropylalkohol, oder Polyole eingesetzt werden. Polyole, die hier in Betracht kommen, besitzen vorzugsweise 2 bis 15 Kohlenstoffatome und mindestens zwei Hydroxylgruppen. Typische Beispiele sindHydrotropes such as ethanol, isopropyl alcohol or polyols can also be used to improve the flow behavior. Polyols that come into consideration here preferably have 2 to 15 carbon atoms and at least two hydroxyl groups. Typical examples are
• Glycerin;• glycerin;
• Alkylenglycole, wie beispielsweise Ethylenglycol, Diethyienglycol, Propylenglycol, Butylenglycol, Hexylenglycol sowie Polyethylenglycole mit einem durchschnittlichen Molekulargewicht von 100 bis 1.000 Dalton; • technische Oligoglyceringemische mit einem Eigenkondensationsgrad von 1 ,5 bis 10 wie etwa technische Digiyceringemische mit einem Diglyceringehalt von 40 bis 50 Gew.-%;Alkylene glycols, such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1,000 daltons; Technical oligoglycerol mixtures with a degree of self-condensation of 1.5 to 10, such as technical digiycerol mixtures with a diglycerol content of 40 to 50% by weight;
• Methyolverbindungen, wie insbesondere Trimethylolethan, Trimethylolpropan, Trimethylolbutan, Pentaerythrit und Dipentaerythrit;• Methyl compounds, such as in particular trimethylolethane, trimethylolpropane, trimethylolbutane, pentaerythritol and dipentaerythritol;
• Niedrigalkylglucoside, insbesondere solche mit 1 bis 8 Kohlenstoffen im Alkylrest, wie beispielsweise Methyl- und Butylglucosid;• Lower alkyl glucosides, in particular those with 1 to 8 carbons in the alkyl radical, such as methyl and butyl glucoside;
• Zuckeralkohole mit 5 bis 12 Kohlenstoffatomen, wie beispielsweise Sorbit oder Mannit,Sugar alcohols with 5 to 12 carbon atoms, such as sorbitol or mannitol,
• Zucker mit 5 bis 12 Kohlenstoffatomen, wie beispielsweise Glucose oder Saccharose;• Sugar with 5 to 12 carbon atoms, such as glucose or sucrose;
• Aminozucker, wie beispielsweise Glucamin.Aminosugars, such as glucamine.
Als Konservierungsmittel eignen sich beispielsweise Phenoxyethanol, For aldehydlösung, Para- bene, Pentandiol oder Sorbinsäure sowie die in Anlage 6, Teil A und B der Kosmetikverordnung aufgeführten weiteren Stoffklassen. Ais Insekten-Repellentien kommen N,N-Diethyl-m-touluamid, 1 ,2-Pentandiol oder Insekten-Repellent 3535 in Frage, als Selbstbräuner eignet sich Dihydroxyaceton.Suitable preservatives are, for example, phenoxyethanol, aldehyde solution, parabens, pentanediol or sorbic acid and the other classes of substances listed in Appendix 6, Parts A and B of the Cosmetics Ordinance. As insect repellents, N, N-diethyl-m-touluamide, 1, 2-pentanediol or insect repellants 3535 are suitable, and dihydroxyacetone is suitable as a self-tanning agent.
Als Parfümöle seien genannt Gemische aus natürlichen und synthetischen Riechstoffen. Natürliche Riechstoffe sind Extrakte von Blüten (Lilie, Lavendel, Rosen, Jasmin, Neroli, Ylang-Ylang), Stengeln und Blättern (Geranium, Patchouli, Petitgrain), Früchten (Anis, Koriander, Kümmel, Wacholder), Fruchtschalen (Bergamotte, Zitrone, Orangen), Wurzeln (Macis, Angelica, Sellerie, Kardamon, Costus, Iris, Calmus), Hölzern (Pinien-, Sandel-, Guajak-, Zedern-, Rosenholz), Kräutern und Gräsern (Estragon, Lemongras, Salbei, Thymian), Nadeln und Zweigen (Fichte, Tanne, Kiefer, Latschen), Harzen und Balsamen (Galbanum, Elemi, Benzoe, Myrrhe, Olibanum, Opoponax). Weiterhin kommen tierische Rohstoffe in Frage, wie beispielsweise Zibet und Castoreum. Typische synthetische Riechstoffverbindungen sind Produkte vom Typ der Ester, Ether, Aldehyde, Ketone, Alkohole und Kohlenwasserstoffe. Riechstoffverbindungen vom Typ der Ester sind z.B. Benzylacetat, Phenoxyethylisobutyrat, p-tert.-Butylcyclohexylacetat, Linaiylacetat, Dimethylben- zylcarbinylacetat, Phenylethylacetat, ünalylbenzoat, Benzylformiat, Ethylmethylphenylglycinat, Allylcyclohexylpropionat, Styrallylpropionat und Benzylsalicylat. Zu den Ethem zählen beispielsweise Benzylethylether, zu den Aldehyden z.B. die linearen Alkanale mit 8 bis 18 Kohlenstoffatomen, Citral, Citronellal, Citronellyloxyacetaldehyd, Cyclamenaldehyd, Hydroxycitronellal, Lilial und Bourgeonal, zu den Ketonen z.B. die Jonone, oc-lsomethylionon und Methylcedrylketon, zu denPerfume oils include mixtures of natural and synthetic fragrances. Natural fragrances are extracts of flowers (lily, lavender, roses, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (anise, coriander, caraway, juniper), fruit peel (bergamot, lemon, Oranges), roots (mace, angelica, celery, cardamom, costus, iris, calmus), wood (pine, sandal, guaiac, cedar, rosewood), herbs and grasses (tarragon, lemongrass, sage, thyme), Needles and twigs (spruce, fir, pine, mountain pine), resins and balms (galbanum, elemi, benzoin, myrrh, olibanum, opoponax). Animal raw materials, such as civet and castoreum, are also suitable. Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type. Fragrance compounds of the ester type are e.g. Benzyl acetate, phenoxyethyl isobutyrate, p-tert-butylcyclohexyl acetate, linanyl acetate, dimethylbenzylcarbinylacetate, phenylethyl acetate, unalylbenzoate, benzyl formate, ethylmethylphenylglycinate, allylcyclohexylpropionate, styrallyl propalate and benzyl acetate. The ethers include, for example, benzyl ethyl ether, the aldehydes e.g. the linear alkanals with 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamenaldehyde, hydroxycitronellal, lilial and bourgeonal, to the ketones e.g. the Jonone, oc-lsomethylionon and Methylcedrylketon, to the
Alkoholen Anethol, Citronellol, Eugenol, Isoeugenol, Geraniol, Linalool, Phenylethylalkohol und Terpineol, zu den Kohlenwasserstoffen gehören hauptsächlich die Terpene und Balsame. Bevorzugt werden jedoch Mischungen verschiedener Riechstoffe verwendet, die gemeinsam eine ansprechende Duftnote erzeugen. Auch ätherische Öle geringerer Flüchtigkeit, die meist als Aromakomponenten verwendet werden, eignen sich als Parfümöle, z.B. Salbeiöl, Kamillenöl, Nel- Alcohols anethole, citronellol, eugenol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol, the hydrocarbons mainly include the terpenes and balms. However, preference is given to using mixtures of different fragrances which together produce an appealing fragrance. Essential oils of lower volatility, which are mostly used as aroma components, are also suitable as perfume oils, e.g. Sage oil, chamomile oil, nell
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE19851451.4 | 1998-11-09 | ||
DE1998151451 DE19851451A1 (en) | 1998-11-09 | 1998-11-09 | Cosmetic and / or pharmaceutical preparations |
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WO2000027343A2 true WO2000027343A2 (en) | 2000-05-18 |
WO2000027343A3 WO2000027343A3 (en) | 2000-11-16 |
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ID=7887071
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Application Number | Title | Priority Date | Filing Date |
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PCT/EP1999/008287 WO2000027343A2 (en) | 1998-11-09 | 1999-10-30 | Cosmetic and/or pharmaceutical preparations containing quaternary esters and partial glycerides |
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DE (1) | DE19851451A1 (en) |
WO (1) | WO2000027343A2 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001089678A3 (en) * | 2000-05-24 | 2002-07-18 | Cognis Deutschland Gmbh | Emulsifiers |
JP2006518330A (en) * | 2002-11-07 | 2006-08-10 | ロレアル | Cosmetic composition comprising at least one specific cyclic carbonate that may be polymerized |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19919087C2 (en) * | 1999-04-27 | 2003-02-27 | Cognis Deutschland Gmbh | Process for permanent deformation of keratin fibers |
DE19922229A1 (en) * | 1999-05-14 | 2000-11-16 | Cognis Deutschland Gmbh | Cosmetic and / or pharmaceutical preparations |
FR2824732B1 (en) * | 2001-05-15 | 2003-08-22 | Oreal | HAIR CONDITIONING COMPOSITION COMPRISING A MIXTURE OF FATTY ALCOHOLS AND METHOD FOR THE COSMETIC TREATMENT OF HAIR |
FR2846879A1 (en) * | 2002-11-07 | 2004-05-14 | Oreal | COSMETIC COMPOSITION COMPRISING AT LEAST ONE PARTICULAR CYCLIC CARBONATE |
DE10341866B4 (en) * | 2003-05-12 | 2014-12-18 | Johnson Controls Gmbh | Device for an adjustment mechanism, adjustment mechanism and method |
DE10347940A1 (en) | 2003-10-15 | 2005-05-19 | Cognis Deutschland Gmbh & Co. Kg | Self-emulsifying preparations |
EP1752193A1 (en) | 2005-08-13 | 2007-02-14 | Dr. Straetmans Chemische Produkte GmbH | Use of one or more cyclic 1,2-alkylene carbonates as stabilizer and activity enhancer for preservatives, corresponding composition |
DE102007027030A1 (en) | 2007-06-08 | 2008-12-11 | Evonik Goldschmidt Gmbh | Stable, low-viscosity cosmetic compositions containing esterquats and / or dialkyl quats |
CN105050567B (en) | 2013-04-05 | 2018-04-27 | 宝洁公司 | Include the personal care composition of pre-emulsified preparation |
US10806688B2 (en) | 2014-10-03 | 2020-10-20 | The Procter And Gamble Company | Method of achieving improved volume and combability using an anti-dandruff personal care composition comprising a pre-emulsified formulation |
US9993404B2 (en) | 2015-01-15 | 2018-06-12 | The Procter & Gamble Company | Translucent hair conditioning composition |
EP3405168B1 (en) | 2016-01-20 | 2025-01-22 | The Procter & Gamble Company | Hair conditioning composition comprising monoalkyl glyceryl ether |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08510442A (en) * | 1993-01-23 | 1996-11-05 | ヘンケル・コマンディットゲゼルシャフト・アウフ・アクチェン | Detergent mixture with improved conditioning effect |
DE19539876C1 (en) * | 1995-10-26 | 1996-12-05 | Henkel Kgaa | New, biodegradable sorbitol ester-based quaternary cpds. |
DE19541753C2 (en) * | 1995-11-09 | 1998-07-16 | Henkel Kgaa | Cosmetic and / or pharmaceutical emulsions |
DE19623763C2 (en) * | 1996-06-14 | 1999-08-26 | Henkel Kgaa | Cosmetic preparations |
DE19651447C1 (en) * | 1996-12-11 | 1997-10-02 | Henkel Kgaa | Textile or hair conditioners having improved performance |
DE19724868A1 (en) * | 1997-06-12 | 1998-12-24 | Henkel Kgaa | Stable cosmetic or pharmaceutical preparation, e.g. cream |
DE19732015C1 (en) * | 1997-07-25 | 1998-07-23 | Henkel Kgaa | Self-emulsifying formulation useful in production of cosmetics, e.g. hair conditions |
DE19756454C1 (en) * | 1997-12-18 | 1999-06-17 | Henkel Kgaa | Surface-active compositions, especially cosmetics, containing glycerol carbonate as emulsifier |
DE19805703C2 (en) * | 1998-02-06 | 2001-05-03 | Cognis Deutschland Gmbh | Hair care products |
-
1998
- 1998-11-09 DE DE1998151451 patent/DE19851451A1/en not_active Withdrawn
-
1999
- 1999-10-30 WO PCT/EP1999/008287 patent/WO2000027343A2/en active Application Filing
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001089678A3 (en) * | 2000-05-24 | 2002-07-18 | Cognis Deutschland Gmbh | Emulsifiers |
US6927241B2 (en) | 2000-05-24 | 2005-08-09 | Cognis Deutschland Gmbh & Co. Kg | Emulsifiers |
JP2006518330A (en) * | 2002-11-07 | 2006-08-10 | ロレアル | Cosmetic composition comprising at least one specific cyclic carbonate that may be polymerized |
Also Published As
Publication number | Publication date |
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WO2000027343A3 (en) | 2000-11-16 |
DE19851451A1 (en) | 2000-05-11 |
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