JPH0397781A - Oil gelling agent - Google Patents
Oil gelling agentInfo
- Publication number
- JPH0397781A JPH0397781A JP1234250A JP23425089A JPH0397781A JP H0397781 A JPH0397781 A JP H0397781A JP 1234250 A JP1234250 A JP 1234250A JP 23425089 A JP23425089 A JP 23425089A JP H0397781 A JPH0397781 A JP H0397781A
- Authority
- JP
- Japan
- Prior art keywords
- oil
- gelling agent
- gel
- cosmetics
- oil gelling
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000003349 gelling agent Substances 0.000 title claims abstract description 13
- -1 12-hydroxyoctadecanoyl Chemical group 0.000 claims abstract description 23
- 150000005690 diesters Chemical class 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 18
- 239000002537 cosmetic Substances 0.000 abstract description 14
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 6
- 239000002674 ointment Substances 0.000 abstract description 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- 230000001588 bifunctional effect Effects 0.000 abstract 3
- 229930195733 hydrocarbon Natural products 0.000 abstract 3
- 239000003921 oil Substances 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000499 gel Substances 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000004375 Dextrin Substances 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- FAUQJFRSOKONGU-UHFFFAOYSA-N ethyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OCC FAUQJFRSOKONGU-UHFFFAOYSA-N 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- NTVDGBKMGBRCKB-UHFFFAOYSA-M sodium;12-hydroxyoctadecanoate Chemical compound [Na+].CCCCCCC(O)CCCCCCCCCCC([O-])=O NTVDGBKMGBRCKB-UHFFFAOYSA-M 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N squalane Chemical compound CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical group CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 230000037365 barrier function of the epidermis Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical group OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 239000010696 ester oil Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- AZXVZUBIFYQWJK-KWRJMZDGSA-N ethyl (z,12r)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(=O)OCC AZXVZUBIFYQWJK-KWRJMZDGSA-N 0.000 description 1
- QOQZSVKKTPUAJM-UHFFFAOYSA-N ethyl 2-hydroxyoctadecanoate Chemical compound CCCCCCCCCCCCCCCCC(O)C(=O)OCC QOQZSVKKTPUAJM-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229940119170 jojoba wax Drugs 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000008164 mustard oil Substances 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Chemical group 0.000 description 1
- 239000011591 potassium Chemical group 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 235000010241 potassium sorbate Nutrition 0.000 description 1
- 239000004302 potassium sorbate Substances 0.000 description 1
- 229940069338 potassium sorbate Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Chemical group 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- MZIXFNCSCKQZLG-UHFFFAOYSA-M sodium;2-hydroxyoctadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCC(O)C([O-])=O MZIXFNCSCKQZLG-UHFFFAOYSA-M 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 239000010913 used oil Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Landscapes
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、液状油のゲル化剤、特に極性油をゲル化する
ためののゲル化剤に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a gelling agent for liquid oils, particularly for gelling polar oils.
［従来の技術］
極性油には、細胞間脂質を初めとして興味深い性質や機
能を有するものが多い。例えばジグリセリルエーテル等
の経皮吸収促進剤、リノール酸等の表皮バリア機能の鍵
或分、ジグリセライド類等の水溶性成分の特異的キャリ
アーとなるものなどが知られている。これら極性油のほ
か、有機溶媒等を含む液状油は、金属セッケン、デキス
トリン脂肪酸エステル、１２−ヒドロキシステアリン酸
等の油ゲル化剤によりゲル化され、化粧料、外用剤等に
配合されている。[Prior Art] Many polar oils have interesting properties and functions, including intercellular lipids. For example, transdermal absorption enhancers such as diglyceryl ether, linoleic acid, which is a key to the epidermal barrier function, and diglycerides, which serve as specific carriers for water-soluble components, are known. In addition to these polar oils, liquid oils containing organic solvents and the like are gelled with oil gelling agents such as metal soaps, dextrin fatty acid esters, and 12-hydroxystearic acid, and are blended into cosmetics, external preparations, and the like.
［発明が解決しようとする課題コ
しかしながら、上記油ゲル化剤のうち金属セツケンは、
液状油に溶解せしめるのに１００℃近くの高温を必要と
するため、化粧料製造時、油剤の品質低下、顔料の変色
等を招くという問題や、経時的に浦の滲み出し、ひび割
れ等を起こして化粧料に発汗等を生じ、その品質を低下
させるという問題がある。また、化粧料用油剤の感触は
、製品のなじみ、のび、つや等の感触等の重要な因子で
あるため、これを低下させないように、油ゲル化剤の添
加量はできるだけ少なくする方がよい（好ましくは１０
重量％以下）が、金属セッケンは少量ではその欠点であ
る経時的な油剤の滲み出し、ひび割れ等が一層大きくな
るという問題もある。更に、金属セッケンは配位結合に
より会合鎖を形戊しているため、極性の高い油剤を使用
すると、カルボン酸と極性浦とが入れ替わり、ゲルを形
成しないという問題もある。この点ではｉ２−ヒドロキ
システアリン酸についても同様な傾向がある。[Problems to be Solved by the Invention] However, among the above oil gelling agents, metal gelatinizers are
Because high temperatures of nearly 100°C are required to dissolve it in liquid oil, there are problems during cosmetic production such as deterioration in the quality of the oil agent and discoloration of pigments, as well as oozing and cracking of the pigment over time. There is a problem in that this causes perspiration in the cosmetics and deteriorates their quality. In addition, the feel of oils for cosmetics is an important factor in the product's fit, spreadability, shine, etc., so it is better to add as little amount of oil gelling agent as possible to avoid deteriorating the feel of the product. (preferably 10
% by weight or less), but when used in small amounts, metal soaps have the disadvantage that oil oozes out over time, cracks, etc. become more serious. Furthermore, since metal soaps form associated chains due to coordination bonds, if a highly polar oil is used, the carboxylic acid and polar ura will replace each other, resulting in the problem that no gel will be formed. In this respect, i2-hydroxystearic acid has a similar tendency.
また、デキストリン脂肪酸エステルは、油剤に充分なゲ
ル強度や保型性を与えることができず、化粧料に配合し
てもゲルによる効果が得られなかった。In addition, dextrin fatty acid esters were unable to impart sufficient gel strength and shape retention to oils, and even when incorporated into cosmetics, no gel effect could be obtained.
従って、油剤の感触を低下させない程度の少量の配合で
、極性の高い油剤においても安定な油保持性及び強固な
保型性を有するゲルを与えることができ、かつ油剤への
溶解温度が通常の乳化温度よりも低い浦ゲル化剤の開発
が望まれていた。Therefore, by adding a small amount that does not reduce the feel of the oil agent, it is possible to provide a gel that has stable oil retention and strong shape retention even in highly polar oil agents, and the dissolution temperature in the oil agent is lower than normal. It has been desired to develop a gelling agent with a temperature lower than the emulsification temperature.
［課題を解決するための手段］
かかる実情において、本発明者らは鋭意研究を行なった
結果、１２−ヒドロキシステアリン酸ジエステルが上記
の条件を具備するものであることを見出し、本発明を完
或した。[Means for Solving the Problems] Under these circumstances, the present inventors conducted intensive research and found that 12-hydroxystearic acid diester satisfies the above conditions, and completed the present invention. did.
すなわち本発明は、次の一般式（１）
Ａ−０−Ｒ−０−Ａ （ １ ）（式中、Ａ
は１２〜ヒドロキシオクタデカノイル基を示し、Ｒは炭
素数２〜ｌ４の２価の炭化水素基を示す）
で表わされるジエステルからなるｈＩ１ゲル化剤を堤供
するものである。That is, the present invention provides the following general formula (1) A-0-R-0-A (1) (wherein A
represents a 12-hydroxyoctadecanoyl group, and R represents a divalent hydrocarbon group having 2 to 14 carbon atoms.
本発明に用いられる１２−ヒドロキシステアリン酸ジエ
ステル（１）としては、例えば以下に示される化合物（
１）、（２）等が好ましいものとして挙げられる。Examples of the 12-hydroxystearic acid diester (1) used in the present invention include the following compounds (
1), (2), etc. are listed as preferred.
（２）
（式中、Ｒ１は炭素数４〜８の飽和または不飽和の２価
の直鎖炭化水素基を、Ｒ２は炭素数１〜４の飽和または
不飽和の２価の直鎖炭化水素基を示す）
また、化合物（Ｉ）は２個の不整炭素原子を有するため
、３種の光学異性体が存在するが、本発明にはこれら及
びその混合物のいずれも使用し得る。(2) (In the formula, R1 is a saturated or unsaturated divalent linear hydrocarbon group having 4 to 8 carbon atoms, and R2 is a saturated or unsaturated divalent linear hydrocarbon group having 1 to 4 carbon atoms. In addition, since compound (I) has two asymmetric carbon atoms, three types of optical isomers exist, and any of these and mixtures thereof can be used in the present invention.
本発明に用いられる化合物（１）は常法（例えば特開昭
５５−５７５０９号公報記載の方法）により製造される
が、高純度の化合物（Ｉ）を得るためには、下記反応式
に従って、１２−ヒドロキシステアリン酸のアルカリ金
属塩（１）とジハライドまたはジスルホネ−１− （Ｔ
ＩＴ）とを反応させることにより製造するのが好ましい
。Compound (1) used in the present invention is produced by a conventional method (for example, the method described in JP-A-55-57509), but in order to obtain highly pure compound (I), according to the following reaction formula, Alkali metal salt of 12-hydroxystearic acid (1) and dihalide or disulfone-1- (T
It is preferable to produce it by reacting with IT).
Ｏ
１１
（１１） （ＩＩＩ）（式中、Ｍは
リチウム、ナトリウムまたはカリウムを示し、Ｘは塩素
、臭素、ヨウ素またはスルポン酸残基を示し、Ｒは前記
した意味を示す）本反応に用いられる化合物（ＩＩ）は
、あらかじめ適当な方法で調製しておいたものを用いて
もよいし、本反応系内で１２−ヒドロキシステアリン酸
に水素化リチウム、水素化ナトリウム、水素化カリウム
、リチウムメトキシド、ナトリウムメトキシド、ナトリ
ウムエトキシド、カリウムターシャリーブトキシド等の
塩基を作用させて調製してもよい。また化合物（ＩＩＩ
）の脱離基Ｘのスルホン酸残基としては、メタンスルホ
ン酸残基、ベンゼンスルホン酸残基、トルエンスルホン
酸残基等が挙げられる。O 11 (11) (III) (wherein M represents lithium, sodium or potassium, X represents chlorine, bromine, iodine or a sulfonic acid residue, and R represents the meaning described above) used in this reaction Compound (II) may be prepared in advance by an appropriate method, or may be prepared by adding lithium hydride, sodium hydride, potassium hydride, or lithium methoxide to 12-hydroxystearic acid in the reaction system. , sodium methoxide, sodium ethoxide, potassium tert-butoxide, and the like. Also, the compound (III
Examples of the sulfonic acid residue of the leaving group X in ) include methanesulfonic acid residue, benzenesulfonic acid residue, toluenesulfonic acid residue, and the like.
本反応に用いられる溶媒としては、反応系において不活
性で、化合物（Ｈ）を溶解できるものであれば特に限定
されないが、ジメチルスルホキシド、ジメチルホルムア
ミド等の非プロトン性極性溶媒：テトラヒド口フラン、
ジオキサン等のエーテル系溶媒；メタノール、エタノー
ル、イソブロビルアルコール等のアルコール系溶媒等が
特に好ましい。また、反応温度は５０〜１８０℃、特に
８０〜１２０℃の範囲が好ましい。The solvent used in this reaction is not particularly limited as long as it is inert in the reaction system and can dissolve compound (H); aprotic polar solvents such as dimethyl sulfoxide and dimethyl formamide; tetrahydrofuran;
Particularly preferred are ether solvents such as dioxane; alcohol solvents such as methanol, ethanol, and isobrobyl alcohol. Further, the reaction temperature is preferably in the range of 50 to 180°C, particularly 80 to 120°C.
かくして得られた化合物（Ｉ）を油ゲル化剤とｌ７て適
用し得る化粧品用または外用剤用の液状浦としては、室
温で液状の油性物質であれば特に限定されないが、例え
ば流動バラフィン、イソパラフィン、スクワラン、シリ
コーン油、高級脂肪酸、高級アルコール、モノグリセリ
ド、ジグリセリド、トリグリセリド、ホホバ油、合或エ
ステル油等が挙げられる。The liquid material for cosmetics or external preparations to which the compound (I) thus obtained can be applied with an oil gelling agent is not particularly limited as long as it is an oily substance that is liquid at room temperature, but examples include liquid paraffin and isoparaffin. , squalane, silicone oil, higher fatty acids, higher alcohols, monoglycerides, diglycerides, triglycerides, jojoba oil, synthetic ester oils, and the like.
液状油をゲル化するに際しては、化合物（Ｔ）は液状油
の０．１−１０重量％、特に０．２〜５重量％配合され
るのが好ましい。配合量がこの範囲を超えると、液状油
の有する良好な性質（のび、つや、なじみ等）が低下し
、この範囲に満たないと本発明の効果が充分に発揮され
ない。When gelling a liquid oil, compound (T) is preferably blended in an amount of 0.1 to 10% by weight, particularly 0.2 to 5% by weight of the liquid oil. If the blending amount exceeds this range, the good properties of the liquid oil (spreadability, gloss, conformability, etc.) will deteriorate, and if the blending amount is below this range, the effects of the present invention will not be fully exhibited.
本発明の油ゲル化剤及び液状油により得られたゲルを用
いて製造できる化粧料または外用剤としては、例えばフ
ァンデーション、口紅等のメイクアップ化粧料；クリー
ム、オイルゲルクレンジング等のスキンケア化許籾；軟
膏等の油性外用剤などが挙げられる。Cosmetics or external preparations that can be produced using the gel obtained from the oil gelling agent and liquid oil of the present invention include, for example, makeup cosmetics such as foundations and lipsticks; skin care products such as creams and oil gel cleansing; Examples include oil-based external preparations such as ointments.
また、このような化粧料または外用剤には、化合物（Ｉ
）及び液状油のほかに、通常使用されるその他の油剤、
精製水、界面活性剤、湿潤剤、防腐剤、酸化防止剤、香
料、粉体等の戊分を適宜配合することができる。In addition, such cosmetics or external preparations include the compound (I
) and other commonly used oils in addition to liquid oils,
Purified water, surfactants, wetting agents, preservatives, antioxidants, fragrances, powders, and other components can be appropriately blended.
その他の油剤としては、高級アルコール、高級脂肪酸、
ワックス類、ロウ類等が挙げられ、これらを配合するこ
とによって化粧料または外用剤のゲル強度、油の保持性
、保型性等を調整することができる。Other oils include higher alcohols, higher fatty acids,
Examples include waxes and waxes, and by blending these, the gel strength, oil retention, shape retention, etc. of cosmetics or external preparations can be adjusted.
また、界面活性剤としては、ポリオキシェチレンアルキ
ルエーテル、ボリオキシエチレン脂肪酸エステル、ボリ
オキシエチレンソルビタン脂肪酸エステル、ソルビタン
脂肪酸エステル、グリセリン脂肪酸エステル、ポリオキ
シエチレン硬化しマシ油、ボリオキシエチレンソルビト
ール脂肪酸エステル等が挙げられ、湿潤剤としては、ソ
ルビトール、グリセリン、プロビレングリコール、１，
３ブチレングリコール、乳酸、乳酸ナトリウム、ポリエ
チレングリコール等が挙げられ、防腐剤としては、パラ
オキシ安息香酸アルキルエステル、安息香酸ナトリウム
、ソルビン酸カリウム、フエノキシエタノール等が挙げ
られ、酸化防止剤としては、トコフエロール、セザモー
ル、セザモリン、レシチン等が挙げられ、粉体としては
、酸化チタン、酸化ｌ■鉛、ＲＴ ’Ｒ ｓ酸化クロム
、酸化鉄、タルク、セリサイト、マイ力、カオリン、雲
母チタン、酸化鉄コーテッド雲母、有機顔料等が挙げら
れる。In addition, as surfactants, polyoxyethylene alkyl ether, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sorbitan fatty acid ester, glycerin fatty acid ester, polyoxyethylene hardened mustard oil, polyoxyethylene sorbitol fatty acid ester Examples of wetting agents include sorbitol, glycerin, propylene glycol, 1,
Examples of antiseptics include 3-butylene glycol, lactic acid, sodium lactate, polyethylene glycol, etc. Preservatives include paraoxybenzoic acid alkyl ester, sodium benzoate, potassium sorbate, phenoxyethanol, etc. Antioxidants include: Examples include tocopherol, sezamol, sezamolin, lecithin, etc., and powders include titanium oxide, l lead oxide, RT'Rs chromium oxide, iron oxide, talc, sericite, kaolin, titanium mica, iron oxide. Examples include coated mica and organic pigments.
本発明の浦ゲル化剤を用いて化粧料または外用剤を調製
する方法としては特に限定されないが、化合物（１）、
液状浦及び任意成分をホモミキサーポモディスバー、三
本ロール等で加熱混合した後、必要により所定の形状に
成型する方法が例示される。The method for preparing cosmetics or external preparations using the ura gelling agent of the present invention is not particularly limited, but compounds (1),
An example of a method is to heat mix the liquid ura and optional ingredients using a homomixer Pomodis bar, three rolls, etc., and then mold the mixture into a predetermined shape if necessary.
［実施例］
以下、実施例を挙げて更に詳細に説明するが、本発明は
これらに限定されるものではない。[Examples] Hereinafter, the present invention will be explained in more detail by giving examples, but the present invention is not limited thereto.
実施例１
である 合 ａ物（Ｉａ） の合 ：（１） １
２−ヒドロキシステアリン酸エチルの合戊″攪拌装置を
備えた１１ステンレス製オートクレープに、リシノール
酸エチル（東京化或■製，純度８７％） ３２６．５ｇ
（ １ ｍｏｌ）、５％パラジウムカーボン３２７ｇ及
びテトラヒドロフラン３００−を仕込み、水素圧ｌＯθ
ｋｇ／ｃｍ’、３０℃で４時間水素添加反応を行なった
。次いで触媒をろ別し、溶媒を留去後、ヘキサンより再
結晶して、１２−ヒドロキシステアリン酸エチル（ Ｇ
ＬＣ純度９８％） ２７２．３ｇを無色針状結晶として
得た（収率８２．９％）。Example 1: Compound a (Ia): (1) 1
Mixing of ethyl 2-hydroxystearate 326.5 g of ethyl ricinoleate (manufactured by Tokyo Kaoru, purity 87%) was placed in a stainless steel autoclave equipped with a stirring device.
(1 mol), 327 g of 5% palladium carbon, and 300 g of tetrahydrofuran, hydrogen pressure lOθ
A hydrogenation reaction was carried out at 30° C. for 4 hours. Next, the catalyst was filtered off, the solvent was distilled off, and recrystallized from hexane to obtain ethyl 12-hydroxystearate (G
LC purity 98%) 272.3 g were obtained as colorless needle crystals (yield 82.9%).
（２） １２−ヒドロキシステアリン酸ナトリウムの合
或
攪拌装置を備えた５００ｍ１２フラスコに、上記（１）
で得た１２−ヒドロキシステアリン酸エチル１３１．４
ｇ（０．４ｍｏ１）、水酸化ナトリウム１２．ＯＯｇ（
０．４ｍｏｌ）及びエタノール８００ｙｎｌｌを仕込み
、８０℃で２時間加熱、攪拌した。次いで反応混合物を
室温まで冷却し、生或した白色固体をろ過した。これを
エタノールで洗浄後、減圧下で乾燥することにより、１
２−ヒドロキシステアリン酸ナトリウム１２３．１４ｇ
を白色固体として得た（収率９５．５％）。(2) Combination of sodium 12-hydroxystearate The above (1) was added to a 500 m12 flask equipped with a stirring device.
Ethyl 12-hydroxystearate obtained in 131.4
g (0.4mol), sodium hydroxide 12. OOg(
0.4 mol) and 800 ynll of ethanol were added, and the mixture was heated and stirred at 80° C. for 2 hours. The reaction mixture was then cooled to room temperature and the white solid formed was filtered. After washing this with ethanol and drying it under reduced pressure, 1
Sodium 2-hydroxystearate 123.14g
was obtained as a white solid (yield 95.5%).
（３）化合物（Ｉａ）の合！戊：
攪拌装置を備えた３００ｍ１２フラスコに、上記（２）
で得た１２−ヒドロキシステアリン酸ナトリウム２ ６
． ７５ｇ（０．０８３ｍｏ１）、１．８−ジブロモ
オクタン１０．８８ｇ（０．０４ｍｏｌ）及びジメチル
スルホキシド１５０ｍｆｌを仕込み、窒素気流下、１０
０℃で１２時間加熱、攪拌した。次いで反応混合物に水
を加えて析出した白色沈殿をろ過した。これをエタノー
ルより再結晶して、標記化合物（Ｉａ） ２４．０４ｇ
を白色結晶として得た（収率７９６％）。(3) Combination of compound (Ia)!戊：Add the above (2) to a 300 m12 flask equipped with a stirring device.
Sodium 12-hydroxystearate obtained in 26
．． 75 g (0.083 mol), 10.88 g (0.04 mol) of 1,8-dibromooctane, and 150 mfl of dimethyl sulfoxide were charged, and the mixture was heated under a nitrogen stream for 10 minutes.
The mixture was heated and stirred at 0°C for 12 hours. Next, water was added to the reaction mixture, and the white precipitate that precipitated was filtered. This was recrystallized from ethanol to obtain 24.04 g of the title compound (Ia).
was obtained as white crystals (yield 796%).
融点：８３９℃
’ Ｈ−ＮＭＲ （ＣＤＣΩ，，δ）
０．８４−０．９４（ｍ，６Ｈ）， １．２０−１．７
０（ｍ，７４Ｈ）．２．２９（ｔ，Ｊ＝７．５Ｈｚ．４
Ｈ）． ３．５７（ｂｓ，２Ｈ）．４．０５（ｔ，Ｊ＝
６．６Ｈｚ，４Ｈ）目Ｃ−ＮＭＲ （ＣＤＣ（ｌ ｓ
，δ）：１４．１， ２２．６， ２５．０， ２５．
７， ２５．９， ２８．７， ２９．１，２９．２，
２９．３， ２９．４， ２９。５， ２９．６，
２９．７， ３１．７，３４４。３７．５， ６４．３
， ７１．９， １７４．０ＴＬＣ （シリカゲル６０
Ｆ−２５４． Ｍｅｒｃｋ社製）：Ｒｆ ＝ ０．４０
（展開溶媒ヘキサン：酢酸エチル＝３＋１），他にスポ
ットは見られない。Melting point: 839°C 'H-NMR (CDCΩ,, δ) 0.84-0.94 (m, 6H), 1.20-1.7
0 (m, 74H). 2.29 (t, J=7.5Hz.4
H). 3.57 (bs, 2H). 4.05(t, J=
6.6Hz, 4H) C-NMR (CDC(l s
, δ): 14.1, 22.6, 25.0, 25.
7, 25.9, 28.7, 29.1, 29.2,
29.3, 29.4, 29.5, 29.6,
29.7, 31.7, 344. 37.5, 64.3
, 71.9, 174.0TLC (silica gel 60
F-254. Merck): Rf = 0.40
(Developing solvent: hexane: ethyl acetate = 3+1), and no other spots were observed.
実施例２
１，８−ジブロモオクタンの代わりに１．４−ジブロモ
ブタンを用いた以外は実施例１と同様にして標記化合物
（ Ｉ ｂ）を得た（収率７８．７％）。Example 2 The title compound (Ib) was obtained in the same manner as in Example 1 except that 1,4-dibromobutane was used instead of 1,8-dibromooctane (yield 78.7%).
融点： ８２．５℃
’ Ｈ−ＮＭＲ （ＣＤ（４ ， ，δ）０．８３−０
．９４（＋ｎ，６Ｈ）， １．２２−１．７３（ｍ，７
０Ｈ），２．３０（ｔ，Ｊ＝７．５１｛ｚ，４Ｈ），
３．５８（ｂｓ，２Ｂ）．４．０５−４．１４（ｍ，４
Ｈ）
ＴＬＣ（シリカゲル６０Ｆ−２５４， Ｍｅｒｃｋ社製
）：Ｒｆ＝０．３５（展開溶媒ヘキサン：酢酸エチル＝
３：１），他にスポットは見られない。Melting point: 82.5°C 'H-NMR (CD(4, , δ) 0.83-0
．． 94 (+n, 6H), 1.22-1.73 (m, 7
0H), 2.30 (t, J=7.51{z, 4H),
3.58 (bs, 2B). 4.05-4.14 (m, 4
H) TLC (silica gel 60F-254, manufactured by Merck): Rf = 0.35 (developing solvent: hexane: ethyl acetate =
3:1), no other spots can be seen.
実施例３
１．４−ビス（１２−ヒドロキシオクタデカノイルオキ
シ）−２−ブテン ー Ｉ）においてＲ＝金』Ｌよ
１．８−ジブ口モオクタンの代わりに１．４−ジクロロ
−２−ブテンを用いた以外は実施例１と同様にして標記
化合物（Ｉｃ）を得た（収率８６，１％）。Example 3 1.4-bis(12-hydroxyoctadecanoyloxy)-2-butene - In I), R=gold, L, 1.4-dichloro-2-butene instead of 1.8-dibutanemooctane The title compound (Ic) was obtained in the same manner as in Example 1, except that 1% was used (yield: 86.1%).
融点： ８６．７℃
’ Ｈ一ＮＭＲ （ＣＤＣ（ｌ ｓ ．δ）０．８２−
０．９４（ｍ，６Ｈ）， １．２０−１．７０（ｍ，６
６Ｈ），２．３１（ｔ，Ｊ＝７．５Ｈｚ，４Ｈ）， ３
．５８（ｂｓ，２Ｈ）４．６８（ｄ，Ｊ＝５．１Ｈｚ，
４Ｈ）， ５．７１−５．７８（ｎｏ，２Ｈ）ＴＬＣ
（シリカゲル６０Ｆ−２５４， Ｍｅｒｃｋ社製）：Ｒ
ｆ＝０．３４（展開溶媒へキサン：酢酸エチル＝３：ｌ
），他にスポットは見られない。Melting point: 86.7°C'H NMR (CDC(ls.δ)0.82-
0.94 (m, 6H), 1.20-1.70 (m, 6
6H), 2.31 (t, J=7.5Hz, 4H), 3
．． 58 (bs, 2H) 4.68 (d, J=5.1Hz,
4H), 5.71-5.78 (no, 2H) TLC
(Silica gel 60F-254, manufactured by Merck): R
f=0.34 (developing solvent hexane:ethyl acetate=3:l
), no other spots can be seen.
実施例４
企韮二
１．８−ジブロモオクタンの代わりにα，α゛−ジクロ
ロキシレンを用いた以外は実施例１と同様にして標記化
合物（Ｉｄ）を得た（収率８３，７％）。Example 4 The title compound (Id) was obtained in the same manner as in Example 1 except that α,α゛-dichloroxylene was used instead of 1,8-dibromooctane (yield 83.7%). .
融点＋ ９１．７℃
’ Ｈ−ＮＭＲ （ＣＤＣＱｓ ，δ）：０．８２−０
．９４（ｍ，６Ｈ）， １．２０−１．７２（１１１．
６６｝１）２．３５（ｔ，Ｊ＝７．５Ｈｚ，４Ｈ），
３．５７（ｂｓ，２Ｈ），５．１１（ｓ，４Ｎ）， ７
．３５（ｓ，４Ｈ）目Ｃ−ＮＭＲ （ＣＤＣＩＩ ，
，δ）：１４．１， ２２．６， ２４．９、２５．７
， ２９．１， ２９．２， ２９．４，２９．５，
２９．６， ２９．７， ３１．７， ３４．３， ３
７．５， ６５．７，７２．０． １２８．４， １３
６．２， １７３．７ＴＬＣ（シリカゲル６０Ｆ−２５
４， Ｍｅｒｃｋ社製）：Ｒｆ＝０．３１（展開溶媒へ
キサン酢酸エチル＝３：１），他にスポットは見られな
い。Melting point + 91.7°C' H-NMR (CDCQs, δ): 0.82-0
．． 94 (m, 6H), 1.20-1.72 (111.
66}1) 2.35 (t, J=7.5Hz, 4H),
3.57 (bs, 2H), 5.11 (s, 4N), 7
．． 35th (s, 4H) C-NMR (CDCII,
, δ): 14.1, 22.6, 24.9, 25.7
, 29.1, 29.2, 29.4, 29.5,
29.6, 29.7, 31.7, 34.3, 3
7.5, 65.7, 72.0. 128.4, 13
6.2, 173.7TLC (silica gel 60F-25
4, manufactured by Merck): Rf=0.31 (developing solvent: hexane-ethyl acetate=3:1), and no other spots were observed.
試験例１ 竺上止血旦よ
種々の液状油に１２−ヒドロキシステアリン酸誘導体を
２％ずつ添加して加熱溶解した後、水浴中で固化してゲ
ルを得た。不動工業社製レオメーターにて直径１０ｍｍ
の円板ブランジャーを用い、２０’Ｃ，上昇速度２ｃｍ
／＋＋＋ｉｎでゲル強度を測定した。この結果を表１に
示す。Test Example 1 12-Hydroxystearic acid derivatives were added to various liquid oils in an amount of 2% to achieve hemostasis, heated and dissolved, and then solidified in a water bath to obtain a gel. Diameter 10mm using a rheometer manufactured by Fudo Kogyo Co., Ltd.
using a disc plunger, 20'C, rising speed 2cm
Gel strength was measured at /+++in. The results are shown in Table 1.
後、室温まで徐冷してゲル化した。Thereafter, it was slowly cooled to room temperature to form a gel.
［発明の効果］
以上のように、本発明の浦ゲル化剤は、極性の高い油剤
、すなわち溶解度パラメータが９以」二であるような油
剤においても、少量の配合で、安定な浦保持性及び強固
な保型性を有するゲルを与えることができ、これを利用
して口紅等の油性固形化粧料、軟膏等の油性外用基剤、
安定性に優れた油中水型乳化化粧料等を製造することが
できる。[Effects of the Invention] As described above, the ura gelling agent of the present invention exhibits stable ura retention even in highly polar oils, that is, oils with a solubility parameter of 9 or more, even when mixed in small amounts. It can provide gels with strong shape-retention properties, and can be used to produce oil-based solid cosmetics such as lipsticks, oil-based external use bases such as ointments,
Water-in-oil emulsion cosmetics and the like with excellent stability can be produced.
以上 ＊高温時、 液々分離that's all *At high temperatures, liquid-liquid separation
Claims (1)
し、Ｒは炭素数２〜１４の２価の炭化水素基を示す） で表わされるジエステルからなる油ゲル化剤。(1) The following general formula (I) A-O-R-O-A (I) (wherein, A represents a 12-hydroxyoctadecanoyl group, and R represents a divalent carbonized group having 2 to 14 carbon atoms) An oil gelling agent consisting of a diester represented by (representing a hydrogen group).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1234250A JPH0397781A (en) | 1989-09-08 | 1989-09-08 | Oil gelling agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1234250A JPH0397781A (en) | 1989-09-08 | 1989-09-08 | Oil gelling agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0397781A true JPH0397781A (en) | 1991-04-23 |
Family
ID=16968026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1234250A Pending JPH0397781A (en) | 1989-09-08 | 1989-09-08 | Oil gelling agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0397781A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5607972A (en) * | 1994-08-08 | 1997-03-04 | The Procter & Gamble Company | Gelling compositions comprising optically enriched gellants |
-
1989
- 1989-09-08 JP JP1234250A patent/JPH0397781A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5607972A (en) * | 1994-08-08 | 1997-03-04 | The Procter & Gamble Company | Gelling compositions comprising optically enriched gellants |
| US5641476A (en) * | 1994-08-08 | 1997-06-24 | The Procter & Gamble Company | Gelling compositions comprising optically enriched gellants |
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