DK165364B - Fedtsyreestere, kosmetisk middel indeholdende disse og fremgangsmaade til fremstilling af saadanne estere - Google Patents
Fedtsyreestere, kosmetisk middel indeholdende disse og fremgangsmaade til fremstilling af saadanne estere Download PDFInfo
- Publication number
- DK165364B DK165364B DK533785A DK533785A DK165364B DK 165364 B DK165364 B DK 165364B DK 533785 A DK533785 A DK 533785A DK 533785 A DK533785 A DK 533785A DK 165364 B DK165364 B DK 165364B
- Authority
- DK
- Denmark
- Prior art keywords
- fatty acid
- acid ester
- esters
- ester
- carbon atoms
- Prior art date
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- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 23
- 239000000194 fatty acid Substances 0.000 title claims abstract description 23
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 23
- -1 FATTY ACID ESTERS Chemical class 0.000 title claims abstract description 22
- 150000002148 esters Chemical class 0.000 title claims description 15
- 239000002537 cosmetic Substances 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title description 5
- 238000000034 method Methods 0.000 title description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- KIHBGTRZFAVZRV-UHFFFAOYSA-N 2-Hydroxyoctadecanoic acid Natural products CCCCCCCCCCCCCCCCC(O)C(O)=O KIHBGTRZFAVZRV-UHFFFAOYSA-N 0.000 claims description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 5
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000003906 humectant Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000002562 thickening agent Substances 0.000 claims description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 2
- 125000005645 linoleyl group Chemical group 0.000 claims 4
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000005644 linolenyl group Chemical group 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 10
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 8
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000006071 cream Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 239000002480 mineral oil Substances 0.000 description 6
- 235000010446 mineral oil Nutrition 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- 235000019197 fats Nutrition 0.000 description 5
- 150000004665 fatty acids Chemical group 0.000 description 5
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 5
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 5
- 229960003415 propylparaben Drugs 0.000 description 5
- 229960000541 cetyl alcohol Drugs 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000008278 cosmetic cream Substances 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 4
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 4
- 229960002216 methylparaben Drugs 0.000 description 4
- 239000002304 perfume Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 3
- 229940075529 glyceryl stearate Drugs 0.000 description 3
- 125000002669 linoleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000002895 organic esters Chemical class 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- OCHJVQODRYVDAA-YPKPFQOOSA-N 12-[(9Z)-octadecenoyloxy]octadecanoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC(CCCCCC)CCCCCCCCCCC(O)=O OCHJVQODRYVDAA-YPKPFQOOSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- BQSQIMVFFHIEDR-HNENSFHCSA-N 2-ethylhexyl 12-[(Z)-octadec-9-enoyl]oxyoctadecanoate Chemical compound C(C)C(COC(CCCCCCCCCCC(CCCCCC)OC(CCCCCCC\C=C/CCCCCCCC)=O)=O)CCCC BQSQIMVFFHIEDR-HNENSFHCSA-N 0.000 description 2
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 2
- ICIDSZQHPUZUHC-UHFFFAOYSA-N 2-octadecoxyethanol Chemical compound CCCCCCCCCCCCCCCCCCOCCO ICIDSZQHPUZUHC-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QZKRHPLGUJDVAR-UHFFFAOYSA-K EDTA trisodium salt Chemical compound [Na+].[Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O QZKRHPLGUJDVAR-UHFFFAOYSA-K 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940008099 dimethicone Drugs 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229910001651 emery Inorganic materials 0.000 description 2
- 210000000245 forearm Anatomy 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229940075507 glyceryl monostearate Drugs 0.000 description 2
- 239000008269 hand cream Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 150000004668 long chain fatty acids Chemical class 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229940100459 steareth-20 Drugs 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 1
- IKFIVOAPLOWJFQ-XVTLYKPTSA-N 12-[(9Z,12Z)-octadeca-9,12-dienoyl]oxyoctadecanoic acid Chemical compound C(CCCCCCC\C=C/C\C=C/CCCCC)(=O)OC(CCCCCCCCCCC(=O)O)CCCCCC IKFIVOAPLOWJFQ-XVTLYKPTSA-N 0.000 description 1
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 1
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 description 1
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-UHFFFAOYSA-N 9,12-Octadecadienoic Acid Chemical compound CCCCCC=CCC=CCCCCCCCC(O)=O OYHQOLUKZRVURQ-UHFFFAOYSA-N 0.000 description 1
- 241000282461 Canis lupus Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 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 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 206010042496 Sunburn Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 239000007961 artificial flavoring substance Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008406 cosmetic ingredient Substances 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- 239000003974 emollient agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 229940100242 glycol stearate Drugs 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229920000059 polyethylene glycol stearate Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- UKHVLWKBNNSRRR-TYYBGVCCSA-M quaternium-15 Chemical compound [Cl-].C1N(C2)CN3CN2C[N+]1(C/C=C/Cl)C3 UKHVLWKBNNSRRR-TYYBGVCCSA-M 0.000 description 1
- 229940096792 quaternium-15 Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000002316 solid fats Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229950003429 sorbitan palmitate Drugs 0.000 description 1
- 229950011392 sorbitan stearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000037072 sun protection Effects 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 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
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Saccharide Compounds (AREA)
- Superconductors And Manufacturing Methods Therefor (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Description
i
DK 165364B
Opfindelsen angår højmolekylære diestere, kosmetisk middel indeholdende disse og en fremgangsmåde til fremstilling af sådanne estere.
Organiske estere, som har strukturen R^COOR, hvor R^ og R 5 er identiske eller forskellige carbonhydridkæder, er vidt udbredt i naturen og kan fremstilles ud fra animalske, vegetabilske og mineralske kilder. Sådanne organiske estere foreligger i form af flydende og faste fedtstoffer, voksarter og olier.
Alle naturlige fedtstoffer og olier er blandinger af estere 10 og adskiller sig ved deres smeltepunktsinterval; olierne er flydende ved omgivelsernes temperatur på grund af den høje procentdel af umættede carbonhydrider i deres molekyler; fedtstofferne er faste eller halvfaste. Esterne af fedtstoffer og olier, kaldet triglycerider, er opbygget af glycerol 15 som den alkoholiske del af molekylet, hvor de tre hydrogenatomer af glycerol er erstattet med fedtsyrerester. De syrer, der findes i fedtstoffer og olier, er ligekædede, mættede eller umættede monocarboxylsyrer med 4 til 26 carbonatomer.
Voksarter er også blandinger af estere, men de afviger fra 20 fedtstoffer og olier i den forstand, at de er monoestere af forskellige alkoholer med fedtsyrer. De fleste voksarter er faste stoffer, der indeholder store mængder mættede fedtsyrer.
De organiske estere anvendes i vid udstrækning på det kosmetiske område, i husholdningen, i industrien og til farmaceu-25 tiske præparater. F.eks. anvendes de laveremolekylære estere som opløsningsmidler i lakker og neglelakker, i parfumeriet, til medicin og som kunstige aromastoffer.
Selv om de fleste af esterne kan opnås på basis af naturlige kilder, fremstilles mange laveremolekylære estere og nogle 30 voksarter også syntetisk. De ad syntetisk vej fremstillede
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2 estere anvendes analogt med de estere, der fremstilles ud fra naturlige kilder og har stor kommerciel betydning.
Opfindelsen tilvejebringer fedtsyreestere baseret på hydroxy-stearinsyre samt anvendelsen deraf i kosmetiske midler.
5 Opfindelsen tilvejebringer en fedtsyrediester, der er fremkommet ved, at man først esterificerer en hydroxystearinsyre med en langkædet, umættet fedtsyre til dannelse af er* umættet esterificeret fedtsyre, og at man derpå omsætter den u-mættede esterificerede fedtsyre med en langkædet fedtalkohol 10 til fremstilling af en trifedtsyrediester.
Fedtsyrediesterne ifølge opfindelsen, der er af den i indledningen til krav 1 angivne art, er ejendommelige ved det i den kendetegnende del af krav 1 angivne.
Eksempler på fedtsyrediesterne ifølge opfindelsen omfatter: 15 octyl-oleoyl-oxystearat ethylhexyl-linoleoyl-oxystearat isocetyl-oleoyl-oxystearat isocetyl-linoleoyl-oxystearat isostearyl-oléoyl-oxystearat 20 isostearyl-linoleoyl-oxystearat octyl-linolenoyl-oxystearat isodecyl-linoleoyl-oxystearat isodecyl-oleoyl-oxystearat isodecyl-linolenoyl-oxystearat 25 amyl-oleoyl-oxystearat amyl-linoleoyl-oxystearat octyldodecyl-oleoyl-oxystearat octyldodecyl-linoleoyl-oxystearat
Disse esterprodukter produceres under esterifikationsbetin-30 gelser ved reaktion mellem en hydroxystearinsyre og en fedtsyre med 1-3 dobbeltbindinger. Sådanne betingelser er kendte,
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3 og de følges af esterifikation af den resulterende, frie carboxylsyregruppe af den esterificerede syre. Hvis hydroxy-stearinsyren først esterificeres, er det valgfrie esterifi-kationstrin naturligvis ikke nødvendigt. F.eks. illustreres 5 fremstillingen af fedtsyrediesterne ifølge opfindelsen ved de følgende eksempler: EKSEMPEL 1 2-ethylhexvl-12-oleoyl-oxystearat A) 500 gram af 12-hydroxystearinsyre (Union Camp - Cenwax 10 A), 440 gram oliesyre (Emery - Emersol 233LL) og 7 gram di- butyltinoxid (Aldrich Chem. Co.) blev blandet og opvarmet til 190°C i en 2-liters, 3-halset beholder, indtil esterifi-kationsreaktionen var afsluttet. Vand, der dannedes under denne esterifikationsproces, blev opsamlet i en Dean-Stark fæl-15 de. Ved afslutning af reaktionen blev syretallet bestemt, og det viste sig at ligge mellem 99 og 106, og molekylvægten var 564 for produktet, 12-oleoyl-oxystearinsyre.
B) 300 gram 12-oleoyl-oxystearinsyre fremstillet som under A i det foregående blev blandet med 90 gram 2-ethyl-l-hexa- 20 nol (Aldrich Chem. Co.). Blandingen blev opvarmet til 180°C, og reaktionsvandet blev opsamlet i en Dean-Stark-fælde. Reaktionsproduktet, 2-ethylhexyl-12-oleoyl-oxystearat, blev carbonbehandlet og filtreret gennem en Bilchner-tragt. Det viste sig, at syretallet var 6,5, mens forsæbnings tallet var 25 166 (beregnet) og 164,5 (fundet).
Det bør./bemærkes, at den temperatur, der er anvendt under reaktionen, kan sænkes, og at reaktionstiden, der ligger mellem 2 og 10 timer, kan forkortes ved at anvende en nitrogenstrøm for at drive vand over under esterifikationsreaktionen.
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4 EKSEMPEL 2 2-ethylhexvl-12-linoleoyl-oxystearat
Fremstillingen af den i overskriften angivne forbindelse er analog med fremstillingen af 2-ethylhexyl-12-oleoyl-oxystea-5 rat, med undtagelse af, at man anvendte linolsyre (Emery’s Emersol 315) i stedet for oliesyre.
Ved analyse af den i overskriften angivne forbindelse fremkom der et syretal på 3 og et forsæbningstal på 166.
EKSEMPEL 3 10 Isostearyl-12-linoleoyl-oxystearat
Den i overskriften angivne forbindelse blev fremstillet af 12-linoleoyl-oxystearinsyre og isostearylalkohol (Aldo 66-Sherex Co.) i henhold til den metode, der er beskrevet i eksempel 1.
15 Det viste sig, at syretallet var 7, mens forsæbningstallet var 136.
Det viste sig, at forbindelser ifølge opfindelsen havde en oral toxicitet i rotter, der var større end 15,9 ml/kg, hud-irritationsindex var 0,1, og Draize-prøven viste en minimal 20 ledsagende irritation, der klarede op på dag nr. to.
r
Forbindelserne ifølge opfindelsen kan let formuleres til kosmetiske midler, husholdningsartikler og farmaceutiske produkter.
I almindelighed omfatter en kosmetisk formulering til hud-25 pleje følgende bestanddele på vægtbasis: 1-20% af en fedtsyrediester ifølge opfindelsen eller blandin-
DK 165364B
5 ger deraf; 5-1090 af et fugtighedsbevarende middel, såsom propylengly-col, sorbitol og mineralolie; 0,2-1,0% af et fortykkelsesmiddel, såsom carboxyvinylpoly-5 mere, methylcellulose, hydroxymethylcellulose og hydroxypro- pylcellulose; 0,5-10% af en emulgator, såsom sorbitanstearat, sorbitan-palmitat, glycerylstearat og glycolstearat; og 50-80% vand.
10 Desuden kan man anvende andre bestanddele, der konventionelt anvendes i kosmetiske præparater, såsom konserveringsmidler, farvende midler og parfumer.
Eksempel k, 5, 7 og 8 illustrerer de kosmetiske midler ifølge opfindelsen.
15 EKSEMPEL 4
Kosmetisk creme % w/w octyl-12-oleoyl-oxystearat 8,00 mineralolie 10,00 glycerolmonostearat 10,00 20 ' methyl paraben 0,10 propylparaben 0,15 parfume 0,25 vand 71,50
Man gennemførte en sammenlignende prøvning for at bedømme 25 ønskværdige egenskaber af en kosmetisk creme, der indeholder en diester ifølge opfindelsen. Eksempel 5 viser det middel, hvori der foreligger ethylhexyl-oleoyl-oxystearat ifølge op-
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6 findelsen, mens midlet* i eksempel 6 indeholder en for tiden markedsført ester.
EKSEMPEL 5
Kosmetisk creme 5 % w/w vand 61,25
Carbopol 934 opløsning 5 >00 ethylhexyl-oleoyl-oxy stearat 8,00 propylenglycol . 7 >00 10 methyl par aben 0,30 propylparaben 0,10 glycerylstearat 4,00 cetylalkohol 1,20 stearinsyre 2,40 15 mineralolie 8,00
Steareth 20 1,00 triethanolamin . 1,40 trinatrium EDTA 0,05
Quaternium 15 0,10 20 Dimethicone 0,20 7
Ulv 100004 D
EKSEMPEL 6 ( sammenligningseksempel)
Kosmetisk creme % w/w vand 61,25 5 Carbopol 934 opløsning 5,00 isopropylmyristat 8,00 propylenglycol 7,00 methyl paraben 0,30 propylparaben 0,10 10 glycerylstearat 4,00 cetylalkohol 1,20 stearinsyre 2,40 mineralolie 8,00
Steareth 20 1,00 15 triethanolamin 1,40 trinatrium EDTA 0,05
Quaternium 15 0,10
Dimethicone 0,20
Man gennemførte en for bruger evaluering ved først at rense 20 underarmene og hænderne med elfenbenssæbe og vand og tørre. Produkterne blev skiftevis anvendt i forbindelse med underarmene og hænderne og evalueret for subjektiv følelse, konsistens, udspredningsevne, absorptionsevne og efterfølelse.
De blev også bedømt, hvad angår velegnethed som håndcreme-25 baseret på de ovenfor angivne parametre. Forsøgsresultater er vist i tabel I.
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8 TABEL I .
Parameter Eksempel 6 Eksempel 5 viskositet mere viskos tyndere, strøm mer let 5 konsistens middel let udspredningsevne glider/voksagtig glider/olieagtig absorptionsevne moderat moderat efterfølelse fugtig fugtig · meget blød blød 10 meget silkeagtig silkeagtig
Mens begge produkter er acceptable til anvendelse som håndcremer til tilvejebringelse af fordelagtig befugtningsevne, en glattere og en silkeagtig følelse, medførte anvendelsen af ethylhexyl-oleoyl-oxystearat fra eksempel 5 en olieagtig fø-15 lelse, mens isopropylmyristatet fra eksempel 6 føltes voks-agtigt.
EKSEMPEL 7
En efterfølgende formulering, der tilvejebringer en tykkere håndcreme end eksempel 5, er som følger: 20 % w/w isocetyl-linoleoyl-oxystearat 8,00 cetylalkohol 1,00 mineralolie 10,00 glycerylmonostearat 10,00 25 methylparaben 0,10 propylparaben 0,15 parfume 0,25 vand 70,50 EKSEMPEL 8 30 Dette eksempel illustrerer forligeligheden af diesterne med 9 andre kosmetiske bestanddele: formlen indeholder både et middel til at fremme solbrændthed og et solbeskyttende middel.
% w/v 5 Isocetyl-linoleoyl-oxystearat 4,00 mineraloli e 8,00 glycerylmonostearat SE 8,00 cetylalkohol 0,50
Par sol MCX* 5,00 10 propylparaben 0,10 methylparaben. 0,15
Unipertan P-24** 5,00 parfume 0,25 vand 69,00
Ar 15 Varemærke for Givaudan's 2-ethylhexyl-p- methoxycinnamat jjHt
Varemærke for Induchem*s tyrosin-kompleks
Blandt de kosmetiske midler skal især anføres dem, der præsenteres i form af flydende emulsioner, lotioner, cremer og 20 læbestiftbaser. De kosmetiske midler kan f.eks. være blødgørende mælkepræparater eller cremer til ansigts- og håndpleje, baser til make-up, mælkepræparater eller cremer til solbeskyttelse, mælkepræparater eller cremer til antiperspi-rantmidler og barbercremer.
Claims (11)
1. Fedtsyreester, kendetegnet ved, at den har formlen ' ch3 ( ch2 ) 5ch ( ocor-l ) ( ch2 ) 10coor2 (I) 5 hvor R^ er en carbonhydridgruppe med 17 carbonatomer med 1 til 3 dobbeltbindinger; og R2 er en ligekædet eller forgrenet carbonhydridgruppe med 5 til 22 carbonatomer.
2. Fedtsyreester ifølge krav 1, kendetegnet ved, at R-j^ er oleyl.
3. Fedtsyreester ifølge krav 1, kendetegnet ved, at R^ er linoleyl.
4. Fedtsyreester ifølge krav 1, kendetegnet ved, 15 at R1 er linolenyl.
5. Fedtsyreester ifølge krav 1, kendetegnet ved, at R^ er oleyl, og R2: :er octyl.
6. Fedtsyreester ifølge krav 1, kendetegnet ved, at R^ er linoleyl, og R2 er octyl.
7. Fedtsyreester ifølge krav 1, kendetegnet ved, at R^ er linoleyl, og R2 er isostearyl.
8. Fedtsyreester ifølge krav 1, kendetegnet ved, at R-j^ er oleyl, og R2 er isocetyl. UK Ί6ΰ3ϋ4 tf
9. Fedtsyreester ifølge krav 1, kendetegnet ved, at er linoleyl, og R2 er isocetyl.
10. Kosmetisk middel, kendetegnet ved, at det på vægtbasis omfatter 1-20 % af en fedtsyreester med formlen 5 I ifølge krav 1 ch3(ch2)5ch(ocor1)(ch2)χ0coor2, hvor R·^ er en carbonhydridgruppe med 17 carbonatomer og 1 til 3 dobbeltbindinger; og R2 er en ligekædet eller forgrenet carbonhydridgruppe 10 med 5 til 22 carbonatomer; 5-10 % af et fugtighedsbevarende middel; 0,2-1,0 % af et fortykkelsesmiddel; 0,5-10 % af en emulgator; og 50-80 % vand.
11. Fremgangsmåde til fremstilling af en ester med formlen I ifølge krav 1, kendetegnet ved, at man esteri-ficerer hydroxystearinsyre eller en ester deraf med en umættet fedtsyre med 1-3 dobbeltbindinger, og at man esteri-ficerer det resulterende esterprodukt, når hydroxystearin-20 syre er udgangsforbindelsen.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67330184 | 1984-11-20 | ||
| US06/673,301 US4567037A (en) | 1984-11-20 | 1984-11-20 | Fatty acid diesters |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| DK533785D0 DK533785D0 (da) | 1985-11-19 |
| DK533785A DK533785A (da) | 1986-05-21 |
| DK165364B true DK165364B (da) | 1992-11-16 |
| DK165364C DK165364C (da) | 1993-04-05 |
Family
ID=24702092
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK533785A DK165364C (da) | 1984-11-20 | 1985-11-19 | Fedtsyreestere, kosmetisk middel indeholdende disse og fremgangsmaade til fremstilling af saadanne estere |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4567037A (da) |
| EP (1) | EP0182355B1 (da) |
| JP (1) | JPH0637429B2 (da) |
| KR (1) | KR900006706B1 (da) |
| AT (1) | ATE41767T1 (da) |
| AU (1) | AU591075B2 (da) |
| BR (1) | BR8505793A (da) |
| CA (1) | CA1263664A (da) |
| DE (1) | DE3569105D1 (da) |
| DK (1) | DK165364C (da) |
| ES (1) | ES8900145A1 (da) |
| FI (1) | FI86712C (da) |
| IE (1) | IE59531B1 (da) |
| IL (1) | IL77010A (da) |
| IN (1) | IN164535B (da) |
| MX (1) | MX162948B (da) |
| NO (1) | NO162420C (da) |
| NZ (1) | NZ214245A (da) |
| ZA (1) | ZA858826B (da) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4639369A (en) * | 1986-03-03 | 1987-01-27 | Revlon, Inc. | Higher acyl lower alkyl hydroxystearates useful in cosmetics |
| US4867965A (en) * | 1986-10-02 | 1989-09-19 | Revlon, Inc. | Fatty acid diesters |
| CA2012475A1 (en) * | 1989-03-23 | 1990-09-23 | Hans M. Brand | Diesters and their use in waxes |
| US5490995A (en) * | 1992-10-30 | 1996-02-13 | The Procter & Gamble Company | Solid nondigestible polyol polyesters containing esterified hydroxy fatty acids such as esterified ricinoleic acid |
| WO1999025794A1 (en) * | 1997-11-14 | 1999-05-27 | The United States Of America, As Represented By The Secretary Of Agriculture | Biodegradable oleic estolide ester base stocks and lubricants |
| US6051214A (en) * | 1998-09-25 | 2000-04-18 | The United States Of America, As Represented By The Secretary Of Agriculture | Shampoos and conditioners containing estolides |
| US6316649B1 (en) | 1998-11-13 | 2001-11-13 | The United States Of America As Represented By The Secretary Of Agriculture | Biodegradable oleic estolide ester having saturated fatty acid end group useful as lubricant base stock |
| FR2803513B1 (fr) * | 2000-01-12 | 2003-12-19 | Oreal | Utilisation de la dhea et/ou de ses precurseurs ou derives pour ameliorer l'aspect papyrace de la peau |
| CA2552371A1 (en) * | 2003-12-30 | 2005-07-14 | Council Of Scientific And Industrial Research | Improved process for preparing fatty acid alkylesters using as biodiesel |
| US7276621B2 (en) * | 2005-08-12 | 2007-10-02 | Eastman Chemical Company | Production of di-(2-ethylhexyl) terephthalate |
| US8455412B2 (en) | 2010-08-31 | 2013-06-04 | Biosynthetic Technologies, Llc | Acetic acid-capped estolide base oils and methods of making the same |
| US8236194B1 (en) | 2011-06-17 | 2012-08-07 | Lubrigreen Biosynthetics, Llc | Refrigerating fluid compositions comprising estolide compounds |
| WO2013191750A1 (en) | 2012-06-18 | 2013-12-27 | Biosynthetic Technologies, Llc | Processes of preparing estolide compounds that include removing sulfonate residues |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2256353A (en) * | 1941-09-16 | Oil from hydroxylated fatty acids | ||
| US2452029A (en) * | 1945-06-21 | 1948-10-26 | Rohm & Haas | Addition products from acrylic esters |
| US2500918A (en) * | 1945-08-10 | 1950-03-14 | Goodrich Co B F | Acylation of hydroxylated esters |
| US2652411A (en) * | 1952-07-18 | 1953-09-15 | Howard M Teeter | Alkyl acyloxy stearates |
| US3308140A (en) * | 1963-06-24 | 1967-03-07 | Edward T Roe | Chain substituted higher fatty acids |
| US3906106A (en) * | 1968-10-23 | 1975-09-16 | Kolmar Laboratories | Material for the physiological treatment and refatting of human skin |
| US3792066A (en) * | 1971-04-29 | 1974-02-12 | Secretary | Process for the preparation of acylated unsaturated long-chain compounds |
| FR2290414A1 (fr) * | 1974-11-06 | 1976-06-04 | Dubois Fils Stearinerie | Nouveaux acetoxystearates d'ethyl-2 hexyle, leur procede de preparation et leur application en dermatologie |
| AU486968B2 (en) * | 1975-07-11 | 1977-01-13 | Zoecon Corporation | Esterification process |
| AU546872B2 (en) * | 1982-06-16 | 1985-09-26 | Unilever Plc | Skin treatment compositions containing a fatty acid or ester |
-
1984
- 1984-11-20 US US06/673,301 patent/US4567037A/en not_active Expired - Lifetime
-
1985
- 1985-11-12 IL IL77010A patent/IL77010A/xx not_active IP Right Cessation
- 1985-11-13 AU AU49875/85A patent/AU591075B2/en not_active Ceased
- 1985-11-15 IN IN813/CAL/85A patent/IN164535B/en unknown
- 1985-11-18 ZA ZA858826A patent/ZA858826B/xx unknown
- 1985-11-18 CA CA000495597A patent/CA1263664A/en not_active Expired
- 1985-11-19 NZ NZ214245A patent/NZ214245A/en unknown
- 1985-11-19 EP EP85114697A patent/EP0182355B1/en not_active Expired
- 1985-11-19 DK DK533785A patent/DK165364C/da not_active IP Right Cessation
- 1985-11-19 FI FI854554A patent/FI86712C/fi not_active IP Right Cessation
- 1985-11-19 BR BR8505793A patent/BR8505793A/pt not_active IP Right Cessation
- 1985-11-19 ES ES549029A patent/ES8900145A1/es not_active Expired
- 1985-11-19 DE DE8585114697T patent/DE3569105D1/de not_active Expired
- 1985-11-19 AT AT85114697T patent/ATE41767T1/de not_active IP Right Cessation
- 1985-11-19 MX MX651A patent/MX162948B/es unknown
- 1985-11-19 NO NO854624A patent/NO162420C/no unknown
- 1985-11-19 IE IE289985A patent/IE59531B1/en not_active IP Right Cessation
- 1985-11-20 JP JP60258821A patent/JPH0637429B2/ja not_active Expired - Lifetime
- 1985-11-20 KR KR1019850008662A patent/KR900006706B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0637429B2 (ja) | 1994-05-18 |
| ES8900145A1 (es) | 1989-02-01 |
| IE852899L (en) | 1986-05-20 |
| DK165364C (da) | 1993-04-05 |
| BR8505793A (pt) | 1986-08-12 |
| CA1263664C (en) | 1989-12-05 |
| FI854554A0 (fi) | 1985-11-19 |
| MX162948B (es) | 1991-07-22 |
| US4567037A (en) | 1986-01-28 |
| KR900006706B1 (ko) | 1990-09-17 |
| DK533785D0 (da) | 1985-11-19 |
| ZA858826B (en) | 1986-08-27 |
| KR860004005A (ko) | 1986-06-16 |
| FI86712C (fi) | 1992-10-12 |
| IE59531B1 (en) | 1994-03-09 |
| FI86712B (fi) | 1992-06-30 |
| EP0182355B1 (en) | 1989-03-29 |
| DE3569105D1 (de) | 1989-05-03 |
| NZ214245A (en) | 1988-04-29 |
| DK533785A (da) | 1986-05-21 |
| AU4987585A (en) | 1986-05-29 |
| NO162420C (no) | 1989-12-27 |
| NO854624L (no) | 1986-05-21 |
| CA1263664A (en) | 1989-12-05 |
| NO162420B (no) | 1989-09-18 |
| IN164535B (da) | 1989-04-01 |
| IL77010A0 (en) | 1986-04-29 |
| FI854554L (fi) | 1986-05-21 |
| ATE41767T1 (de) | 1989-04-15 |
| IL77010A (en) | 1989-09-28 |
| EP0182355A3 (en) | 1987-05-06 |
| AU591075B2 (en) | 1989-11-30 |
| EP0182355A2 (en) | 1986-05-28 |
| JPS61129149A (ja) | 1986-06-17 |
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