JPH0476082A - Gelling agent - Google Patents
Gelling agentInfo
- Publication number
- JPH0476082A JPH0476082A JP2189761A JP18976190A JPH0476082A JP H0476082 A JPH0476082 A JP H0476082A JP 2189761 A JP2189761 A JP 2189761A JP 18976190 A JP18976190 A JP 18976190A JP H0476082 A JPH0476082 A JP H0476082A
- Authority
- JP
- Japan
- Prior art keywords
- ether
- sugar
- branched aliphatic
- group
- aliphatic
- 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 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 48
- 235000000346 sugar Nutrition 0.000 claims abstract description 29
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 21
- 229930182470 glycoside Natural products 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 239000000126 substance Substances 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 150000002338 glycosides Chemical class 0.000 claims description 2
- -1 aliphatic glycoside Chemical class 0.000 abstract description 55
- 239000000845 maltitol Substances 0.000 abstract description 13
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 abstract description 13
- 235000010449 maltitol Nutrition 0.000 abstract description 13
- 229940035436 maltitol Drugs 0.000 abstract description 13
- LQXBZWFNAKZUNM-UHFFFAOYSA-N 16-methyl-1-(16-methylheptadecoxy)heptadecane Chemical compound CC(C)CCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC(C)C LQXBZWFNAKZUNM-UHFFFAOYSA-N 0.000 abstract description 9
- 239000003814 drug Substances 0.000 abstract description 7
- 239000002537 cosmetic Substances 0.000 abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 13
- 239000008213 purified water Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 229960002920 sorbitol Drugs 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000600 sorbitol Substances 0.000 description 7
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 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 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 235000010356 sorbitol Nutrition 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229920001817 Agar Polymers 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 239000008272 agar Substances 0.000 description 5
- 150000001875 compounds Chemical group 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- DZODYVXOEOUBSM-UHFFFAOYSA-N 18-(18-hydroxyoctadecoxy)octadecan-1-ol Chemical compound OCCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCCO DZODYVXOEOUBSM-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 150000008163 sugars Chemical class 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 125000004079 stearyl 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])([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])C([H])([H])[H] 0.000 description 3
- FMZUHGYZWYNSOA-VVBFYGJXSA-N (1r)-1-[(4r,4ar,8as)-2,6-diphenyl-4,4a,8,8a-tetrahydro-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl]ethane-1,2-diol Chemical compound C([C@@H]1OC(O[C@@H]([C@@H]1O1)[C@H](O)CO)C=2C=CC=CC=2)OC1C1=CC=CC=C1 FMZUHGYZWYNSOA-VVBFYGJXSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- NFQKONHGWOZKOL-UHFFFAOYSA-N 1-bromo-16-methylheptadecane Chemical compound CC(C)CCCCCCCCCCCCCCCBr NFQKONHGWOZKOL-UHFFFAOYSA-N 0.000 description 2
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 2
- QIGJYVCQYDKYDW-UHFFFAOYSA-N 3-O-alpha-D-mannopyranosyl-D-mannopyranose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(CO)OC(O)C1O QIGJYVCQYDKYDW-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- 206010040880 Skin irritation Diseases 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 2
- NLEBIOOXCVAHBD-QKMCSOCLSA-N dodecyl beta-D-maltoside Chemical compound O[C@@H]1[C@@H](O)[C@H](OCCCCCCCCCCCC)O[C@H](CO)[C@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 NLEBIOOXCVAHBD-QKMCSOCLSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 235000015110 jellies Nutrition 0.000 description 2
- 239000008274 jelly Substances 0.000 description 2
- 229940070765 laurate Drugs 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000036556 skin irritation Effects 0.000 description 2
- 231100000475 skin irritation Toxicity 0.000 description 2
- 239000007787 solid 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
- 239000005720 sucrose Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- LGQKSQQRKHFMLI-SJYYZXOBSA-N (2s,3r,4s,5r)-2-[(3r,4r,5r,6r)-4,5,6-trihydroxyoxan-3-yl]oxyoxane-3,4,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)CO[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O)OC1 LGQKSQQRKHFMLI-SJYYZXOBSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KYEACNNYFNZCST-UHFFFAOYSA-N 1-methylpyrrolidine-2,5-dione Chemical compound CN1C(=O)CCC1=O KYEACNNYFNZCST-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- JNAYPSWVMNJOPQ-UHFFFAOYSA-N 2,3-bis(16-methylheptadecanoyloxy)propyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC(C)C)COC(=O)CCCCCCCCCCCCCCC(C)C JNAYPSWVMNJOPQ-UHFFFAOYSA-N 0.000 description 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
- LGQKSQQRKHFMLI-UHFFFAOYSA-N 4-O-beta-D-xylopyranosyl-beta-D-xylopyranose Natural products OC1C(O)C(O)COC1OC1C(O)C(O)C(O)OC1 LGQKSQQRKHFMLI-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 description 1
- WQZGKKKJIJFFOK-IVMDWMLBSA-N D-allopyranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H](O)[C@@H]1O WQZGKKKJIJFFOK-IVMDWMLBSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
- SQNRKWHRVIAKLP-UHFFFAOYSA-N D-xylobiose Natural products O=CC(O)C(O)C(CO)OC1OCC(O)C(O)C1O SQNRKWHRVIAKLP-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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
- AYRXSINWFIIFAE-SCLMCMATSA-N Isomaltose Natural products OC[C@H]1O[C@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)[C@@H](O)[C@@H](O)[C@@H]1O AYRXSINWFIIFAE-SCLMCMATSA-N 0.000 description 1
- 238000006945 Knorr synthesis reaction Methods 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 235000016067 Polianthes tuberosa Nutrition 0.000 description 1
- 244000014047 Polianthes tuberosa Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GCSPRLPXTPMSTL-IBDNADADSA-N [(2s,3r,4s,5s,6r)-2-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[C@@]1([C@]2(CO)[C@H]([C@H](O)[C@@H](CO)O2)O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O GCSPRLPXTPMSTL-IBDNADADSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- SRBFZHDQGSBBOR-STGXQOJASA-N alpha-D-lyxopyranose Chemical compound O[C@@H]1CO[C@H](O)[C@@H](O)[C@H]1O SRBFZHDQGSBBOR-STGXQOJASA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- DLRVVLDZNNYCBX-ZZFZYMBESA-N beta-melibiose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)O1 DLRVVLDZNNYCBX-ZZFZYMBESA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011538 cleaning material Substances 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002951 idosyl group Chemical class C1([C@@H](O)[C@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
- 229960000367 inositol Drugs 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- DLRVVLDZNNYCBX-RTPHMHGBSA-N isomaltose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)C(O)O1 DLRVVLDZNNYCBX-RTPHMHGBSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- QIGJYVCQYDKYDW-LCOYTZNXSA-N laminarabiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1O QIGJYVCQYDKYDW-LCOYTZNXSA-N 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 125000001421 myristyl 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])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JXTPJDDICSTXJX-UHFFFAOYSA-N n-Triacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QIGJYVCQYDKYDW-NSYYTRPSSA-N nigerose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1O QIGJYVCQYDKYDW-NSYYTRPSSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000019488 nut oil Nutrition 0.000 description 1
- 239000010466 nut oil Substances 0.000 description 1
- 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 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Landscapes
- Saccharide Compounds (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、Ｊ２記−形式（Ｉ）で表される糖分岐脂肪族
エーテル及び／または一般式（ＩＴ）で表される分岐脂
肪族グリコシドを含有してなるゲル化剤に関する。更に
詳しくは、化学的に安定で、皮膚や眼に対し極めて低刺
激性であるため、医薬品、医薬部外品及び化粧料に配合
でき、更に、低温でも水によく溶解し、極低濃度水溶液
でもゼリ状になるという特異な性質を持つ、糖分岐脂肪
族エーテル及びまたは分岐脂肪族グリコシドを含有して
なる極めて安全性の高い水溶性ゲル化剤に関する。DETAILED DESCRIPTION OF THE INVENTION "Industrial Application Field" The present invention relates to a branched aliphatic ether represented by J2-Form (I) and/or a branched aliphatic glycoside represented by the general formula (IT). More specifically, it is chemically stable and has extremely low irritation to the skin and eyes, so it can be incorporated into pharmaceuticals, quasi-drugs, and cosmetics, and it can be used even at low temperatures. This invention relates to an extremely safe water-soluble gelling agent containing a sugar-branched aliphatic ether and/or a branched aliphatic glycoside, which has the unique property of being highly soluble in water and becoming gel-like even in an extremely low concentration aqueous solution.
し従来の技術」
従来、多くの皮膚外用剤には、分散等の目的で、非イオ
ン性界面活性剤が使用されている。BACKGROUND OF THE INVENTION Conventionally, nonionic surfactants have been used in many skin preparations for purposes such as dispersion.
これらは、濃度、温度、組成によって、ゲル状、ゼリー
状、溶液状、乳化状等様々な形状を持つため、それぞれ
の目的に応した形状をとることができる。一般に多用さ
れている非イオン性界面活性剤には、グリセリン脂肪酸
エステル、ソルビタン脂肪酸エステル、ソルビトール脂
肪酸エステル、ショ糖脂肪酸エステル、ポリオキシエチ
レンソルビタン脂肪酸エステル、ポリオキシエチレング
リコール脂肪酸エステル、ポリオキシエチレンアルキル
エーテル、ポリオキシエチレンアルキルフェニルエーテ
ル、ポリオキシエチレン硬化ヒマシ油誘導体、マンニト
−ルヒドロキシ脂肪酸エーテル等がある。These have various shapes such as gel, jelly, solution, and emulsion depending on concentration, temperature, and composition, so they can be shaped to suit each purpose. Commonly used nonionic surfactants include glycerin fatty acid ester, sorbitan fatty acid ester, sorbitol fatty acid ester, sucrose fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycol fatty acid ester, and polyoxyethylene alkyl ether. , polyoxyethylene alkylphenyl ether, polyoxyethylene hydrogenated castor oil derivative, mannitol hydroxy fatty acid ether, and the like.
［発明が解決しようとする課題］
従来技術の問題点
を含有する非イオン性界面活性剤には、ＨＬ Ｂ域を広
くかつ任意に調製しうるという長所を持つ反面、一般に
、経時で酸化を受け、低分子量のアルデヒ１くや有機酸
を発生し、変臭や皮膚刺激の原因となったり、ｐ Ｈの
低下を起こすという問題点を有する。また、ソルビタン
脂肪族エステル等の多価アルコール脂肪酸エステルタイ
プの非イオン性界面活性剤は、特に水を含み、ｒ＋Ｈが
中性からしよずれている皮膚外用剤の成分として用いた
場合、エステル結合が分解し易く、経口安定性や安全性
に問題を生じ易い。[Problems to be Solved by the Invention] Nonionic surfactants that contain the problems of the prior art have the advantage of having a wide HLB range and can be arbitrarily adjusted, but are generally susceptible to oxidation over time. However, there are problems in that they generate low molecular weight aldehydes and organic acids, which cause odor and skin irritation, as well as a decrease in pH. In addition, polyhydric alcohol fatty acid ester type nonionic surfactants, such as sorbitan aliphatic ester, contain ester bonds, especially when used as a component of external skin preparations that contain water and have r+H that deviates from neutrality. It is easy to decompose, causing problems with oral stability and safety.
更に、ソルビトールステアリルエーテルや、ｎテトラデ
シルマルトシドなど糖直鎖脂肪族エーテルでは、アルキ
ル鎖が長くなると、低温では、水への溶解性が悪いとい
う問題がある。Furthermore, sugar linear aliphatic ethers such as sorbitol stearyl ether and n-tetradecyl maltoside have a problem of poor solubility in water at low temperatures when the alkyl chain becomes long.
また、一般に広く使われている非イオン系の水溶ゲル化
剤としては、天然物には、寒天、ゼラチン等が知られて
いる。これらの物質は加温、冷却することによって、容
易にゲル化、又は、ゼリ状にすることができるが、手間
がかかる上、できたゲル物質は、不安定で離漿し易く長
期保存ができない。また、溶媒中の有機親水性溶媒（メ
タツル、エタノール、ブタノール、プロパツール等）含
有量が増えたり、ｐＨが３以下になると、ゲルやゼリー
状の形状を示さなくなるという問題かある。これは、そ
のような形状を持つ化粧料や医薬品を処方する上で、し
ばしば処方を制限することとなっている。Furthermore, as nonionic water-soluble gelling agents that are generally widely used, agar, gelatin, and the like are known as natural products. These substances can be easily gelled or made into a jelly by heating and cooling, but it is time-consuming and the resulting gel substance is unstable and easily syneresis, making it impossible to store it for a long period of time. . Furthermore, if the content of organic hydrophilic solvents (metatol, ethanol, butanol, propatool, etc.) in the solvent increases or the pH becomes 3 or less, there is a problem that the gel or jelly-like shape is no longer exhibited. This often limits the formulation of cosmetics and pharmaceuticals that have such a shape.
合成品としては、僅かに、ジヘンジリデンーＤソルビト
−ルか知られている。しかし、このジベンジリデン−〇
−ソルビト−ルは、水に難溶で溶解きせるために沸点近
くまで加温させなければならないため、やはり手間がか
かるという問題がある。As a synthetic product, only dihengylidene-D sorbitol is known. However, this dibenzylidene-0-sorbitol is poorly soluble in water and must be heated to near its boiling point in order to be dissolved, so there is still a problem in that it is time-consuming.
更に、寒天、寒天の誘導体や、ジベンジリデンＤ−ソル
ビトール等の糖誘導体が、ゲルやゼリ状の形状を示すこ
とや、高濃度水溶液では、アルキルグリコシドでもゲル
を形成したり、温度によって、液晶となることは判って
いたが、実際に使用するには制約か多過ぎた。Furthermore, agar, agar derivatives, and sugar derivatives such as dibenzylidene D-sorbitol exhibit a gel or jelly-like shape, and in highly concentrated aqueous solutions, even alkyl glycosides may form gels, and depending on the temperature, they may form liquid crystals. I knew it would happen, but there were too many restrictions to actually use it.
発明の目的
そこで、本発明者らが鋭意検討したところ、糖類に分枝
アルキル基を導入することにより、その性質が向上する
事を発見し、本発明を完成するに到った。ずなオつち、
本発明の糖分岐脂肪族エーテル及び分岐脂肪族グリコシ
ドは、極めて安全性に優れ、極低濃度でも水溶液がゼリ
ー状になり、前述したように、低温でも水によく溶解し
、溶解きせるのに加温の必要がないため、容易にゼリー
状の溶液が調製できて、また、ゼリー状になった溶液の
安定性もよいため、新規の水溶性ゲル化剤及として利用
できることがわかった。Purpose of the Invention The present inventors conducted extensive studies and discovered that introducing a branched alkyl group into a saccharide improves its properties, leading to the completion of the present invention. Zuna Otsuchi,
The sugar-branched aliphatic ether and branched aliphatic glycoside of the present invention are extremely safe, and their aqueous solutions become jelly-like even at extremely low concentrations. Since there is no need for heating, a jelly-like solution can be easily prepared, and the jelly-like solution has good stability, so it has been found that it can be used as a new water-soluble gelling agent.
更に、これらの物質は、界面活性能も有し、界面活性剤
としても、用いることができることがわかった。Furthermore, it has been found that these substances also have surfactant ability and can be used as surfactants.
［課題を解決するための手段］ すなわち、本発明は一般式（■）： Ａ−＋−０−Ｒ） ｎ（Ｉ ） （ただし、式中Ａは糖からｎ個の水酸基を除いた残基。[Means to solve the problem] That is, the present invention is based on the general formula (■): A-+-0-R) n(I) (However, in the formula, A is a residue obtained by removing n hydroxyl groups from a sugar.
Ｒは、エーテル結合１位以上に分岐鎖を持つ脂肪鎖て、
全炭素数８〜３２゜ｎは１以上を表す。）
で、表される糖分岐脂肪族エーテル、及び／または
−形成（ＩＩ）：
Ａ＝Ｏ−Ｒ（ＩＩ）
（ただし、式中Ａは糖から１個の水酸基を除いた残基。R is an aliphatic chain with a branched chain at the 1st position or higher of the ether bond,
The total carbon number of 8 to 32°n represents 1 or more. ) A sugar-branched aliphatic ether represented by, and/or -formation (II): A=O-R(II) (wherein A is a residue obtained by removing one hydroxyl group from a sugar.
Ｒば、グリコシド結合１位以上に分岐鎖を脂肪鎖で、全
炭素数８〜３２ｏ）で、表される分岐脂肪族グリコシド
を含有することを特徴とするゲル化剤に関する。R refers to a gelling agent characterized by containing a branched aliphatic glycoside represented by an aliphatic chain having a branched chain at the first or higher glycosidic bond position and having a total carbon number of 8 to 32 o.
以下、本発明の詳細な説明する。The present invention will be explained in detail below.
まず、本発明においては、糖の１位水酸基と脂肪族炭化
水素基とのエーテル結合物（いわゆるグリコシド結合を
形成している。）を脂肪族グリコシドと呼び、それ以外
の水酸基どのエーテル結合物を糖脂肪族エーテルと呼ぶ
１、
一般式（■）、及び、（１■）において、Ａの糖の具体
例としては、グルコース、ガラクトース、キシロース、
フルクトース、アルドロース、タロス、マンノース、ア
ラビノース、イドース、リキソース、リボース、アロー
ス、等の単糖類及びその混合物、又は、マルト−ス、イ
ソマルト−ス、ラクト−ス、キシロビオース、ケンチオ
ピース、コージオビオース、セロビオース、ツボロース
、ニゲロース、スクロース、メリビオース、ラミナリビ
オース、ルヂノース等の三糖類及びその混合物、更に、
マンニトール、ソルビト−ル、マンニトール、ガラクチ
トール、グルシト−ル、イノシト−ルなどの糖アルコー
ル及びその混合物が挙げられ、更に、それ以上の多糖で
も構わない。First, in the present invention, an ether bond between the 1-position hydroxyl group of a sugar and an aliphatic hydrocarbon group (forming a so-called glycosidic bond) is called an aliphatic glycoside, and other ether bonds of hydroxyl groups are referred to as aliphatic glycosides. In the general formulas (■) and (1■), which are called sugar aliphatic ethers, specific examples of the sugar A include glucose, galactose, xylose,
Monosaccharides and mixtures thereof such as fructose, aldrose, talos, mannose, arabinose, idose, lyxose, ribose, allose, or maltose, isomaltose, lactose, xylobiose, kenthiopiece, cordiobiose, cellobiose, Trisaccharides such as tuberose, nigerose, sucrose, melibiose, laminaribiose, ludinose, and mixtures thereof;
Examples include sugar alcohols such as mannitol, sorbitol, mannitol, galactitol, glucitol, and inositol, and mixtures thereof, and even higher polysaccharides may be used.
Ｒの分岐鎖の具体例どしては、例えばメチル基、エチル
基、イソプロピル基、ペンチル基、ヘキシル基、ヘプチ
ル基、オクチル基、ラウリル基、ミリスチル基、パルミ
ヂル基、ステアリル基、更にそれ以−Ｆの高級脂肪鎖が
挙げられ、分岐の位置は、エーテル結合の１位以上及び
グリコシド結合１位以上の位置であればいずれでもよく
、分岐鎖の数も限定しない。Ｒの具体例どしては、２−
エチルヘキシル基、２−へキシルドデシル基、２−ドデ
シルウンデシル基、２−ウンデシルパルミヂル基、イソ
ステアリル基、テトラヒドロゲラニル基、などが挙げら
れるが、その他分岐脂肪鎖であれば、いずれて・も、太
い。Specific examples of branched chains of R include methyl group, ethyl group, isopropyl group, pentyl group, hexyl group, heptyl group, octyl group, lauryl group, myristyl group, palmidyl group, stearyl group, and more. A higher aliphatic chain of F is mentioned, and the branching position may be any position as long as it is the 1st or higher position of the ether bond or the 1st or higher position of the glycosidic bond, and the number of branched chains is not limited. A specific example of R is 2-
Examples include ethylhexyl group, 2-hexyldodecyl group, 2-dodecylundecyl group, 2-undecylpalmidyl group, isostearyl group, tetrahydrogeranyl group, etc., but any other branched fatty chain can be used. It's also thick.
一般式（Ｉ）または（ＩＩ）で残基Ａは糖で、親水基で
あり、Ｒは、疎水基で、そのバランスと工業性より炭素
数の合計が８〜３２であることが好ましい。Ｒの炭素数
の合計が８〜３２の範囲を外れると、親水性と疎水性の
バランスが崩れ、この特異な性質を示さなくなる。In general formula (I) or (II), residue A is a sugar and is a hydrophilic group, R is a hydrophobic group, and the total number of carbon atoms is preferably 8 to 32 from the viewpoint of balance and industrial efficiency. When the total number of carbon atoms in R is outside the range of 8 to 32, the balance between hydrophilicity and hydrophobicity is lost and this unique property is no longer exhibited.
本発明の分枝脂肪族グリコシドは勿論、糖分岐脂肪族エ
ーテルはゲル化剤としては、■の数は、限定されない。Not only the branched aliphatic glycoside of the present invention but also the sugar branched aliphatic ether can be used as a gelling agent, and the number of ``■'' is not limited.
また本発明の分枝脂肪族グリコシド、及びｎ＝２以下の
糖分岐脂肪族エーテルは界面活性剤として使用すること
も可能である。Furthermore, the branched aliphatic glycosides and sugar branched aliphatic ethers of n=2 or less of the present invention can also be used as surfactants.
本発明の糖分岐脂肪族エーテル及び分岐脂肪族グリコシ
ドの基剤への配合量は側段限定されず、その時の用途に
応じ、あらゆる強度のゲル化能が期待される。The amount of the sugar-branched aliphatic ether and branched aliphatic glycoside of the present invention to be incorporated into the base is not particularly limited, and gelling ability of any strength is expected depending on the application at the time.
−１−記の糖分岐脂肪族エーテル及び分岐脂肪族グリコ
シドは、油状または固体で、例えば洗浄性、分散性、乳
化性、保湿性、コクのある使用感が得られるという機能
を有するうえ、安全性、安定性に極めて優れているため
、医薬品、医薬部外品、化粧料及び洗浄材の成分として
配合されうる。更に、糖直鎖脂肪族エーテルや直鎖グリ
コシドに比べ、アルキル鎖が長くても低温で水によく溶
解し、溶解するのに加温の必要がない。ゼリー状になっ
た溶液の安定性もよく、液晶化剤として利用でき得る。The sugar branched aliphatic ether and branched aliphatic glycoside described in -1- are oily or solid, and have functions such as detergency, dispersibility, emulsifying property, moisturizing property, and providing a rich feeling of use, and are also safe. Because of its excellent properties and stability, it can be incorporated as an ingredient in pharmaceuticals, quasi-drugs, cosmetics, and cleaning materials. Furthermore, compared to sugar straight-chain aliphatic ethers and straight-chain glycosides, even though the alkyl chain is long, it dissolves well in water at low temperatures and does not require heating to dissolve. The jelly-like solution has good stability and can be used as a liquid crystallizing agent.
本発明のうち、糖分岐脂肪族エーテルは、例えば、］コ
バートらの方法（Ｔｅｔｒａｈｅｄｒｏｎ、３５．２１
６９−２１７２（１，９７９））により合成することが
できる。すなわち、糖をジメチルポルムアミド、ジメヂ
ルスルポキシ１り、ジオキサン、ジメチルアセトアミド
チルピロリドン、Ｎ−アセデルモルホリン、Ｎメチルコ
ハク酸イミド等の非水系溶媒に溶がし、これに−形成
％式％（）
］
ただし、式中Ｘはフッ素、塩素、臭素、ヨウ素等のハロ
ゲン基及びトリメチルアンモニウムプロミド塩、水酸基
であり、Ｒは、前記式（Ｉ）に同じで示される化合物を
添加して、触媒の存在下、５０〜１、３００Ｃで撹拌、
反応させることにより得られる。この際、−形式 （Ｔ
ＩＩ）で示される化合物は単独でも、２種以上、併用し
てもよい。Within the present invention, the sugar-branched aliphatic ethers can be prepared, for example, by the method of Covert et al. (Tetrahedron, 35.21).
69-2172 (1,979)). That is, sugar is dissolved in a non-aqueous solvent such as dimethylpolamide, dimethylsulfoxyl, dioxane, dimethylacetamidotylpyrrolidone, N-acedelmorpholine, N-methylsuccinimide, etc., and the -formation% formula % ( ] However, in the formula, X is a halogen group such as fluorine, chlorine, bromine, iodine, trimethylammonium bromide salt, or a hydroxyl group, and R is a compound represented by the same formula as in formula (I) above, which is added to form a catalyst. Stirring at 50-1,300C in the presence of
Obtained by reaction. At this time, -form (T
The compounds represented by II) may be used alone or in combination of two or more.
また、」二重の触媒としては、硫酸等の鉱酸、水酸化リ
チウム、水酸化ナトリウム、水酸化カリウム等のアルカ
リ、ナトリウムエチラート、ナトリウムエチラート等の
ナトリウムアルコラード、Ｎ−メチルベンジルアミン等
のアミン等が挙げられる。In addition, examples of double catalysts include mineral acids such as sulfuric acid, alkalis such as lithium hydroxide, sodium hydroxide, and potassium hydroxide, sodium alcoholates such as sodium ethylate, and N-methylbenzylamine. amines and the like.
この反応に使用される糖と一般式（Ｉ Ｉ Ｉ）で示さ
れる化合物のモル比は、例えばモノエーテルを主生成物
として得ようとする場合１〜３：１で更に好ましくは２
〜３：１である。糖が、多過ぎると糖が多量に残って後
の精製に支障をきたす。The molar ratio of the sugar used in this reaction to the compound represented by the general formula (III) is, for example, 1 to 3:1, more preferably 2:1 when monoether is to be obtained as the main product.
~3:1. If there is too much sugar, a large amount of sugar will remain and cause problems in subsequent purification.
−形式（ＩＩＩ）で示される化合物がすべて消費された
場合、反応系の触媒を中和する目的で酢酸、塩酸、硫酸
、リン酸等の酸、水酸化リチウム、水酸化すＩ・リウム
、水酸化カリウム等のアルカリを加え、反応溶媒を減圧
留去する。- When all the compounds represented by form (III) are consumed, acids such as acetic acid, hydrochloric acid, sulfuric acid, phosphoric acid, lithium hydroxide, sulfur hydroxide, water, etc. are used to neutralize the catalyst in the reaction system. An alkali such as potassium oxide is added, and the reaction solvent is distilled off under reduced pressure.
このようにして得られた反応生成物には、−形式（ Ｉ
）で示される糖分岐脂肪族エーテルのほか、中和時の
塩、糖等が共存している。そのため、例えば糖と塩を除
去する場合、メチルアルコール、エチルアルコール、ブ
ヂルアルコール、イソプロピルアルコール等の糖を溶解
しない溶媒で抽出したり、塩を多量に含む水とメチルエ
ヂルケトン、ｎ−ブタノールで分配し、有機溶媒層を分
取することにより精製できる。また、糖と塩を除去し、
結合した分岐アルキル基の数によって化合物を分離する
場合、反応生成物を水または水とアルコールの混液に懸
濁させ、ハイパーポーラスポリマー（例えば三菱化成工
業株式会社製のハイポーラス樹脂）、オクタデシルシリ
カなどの逆相分配カラムで、始め水で通液し、次にメタ
ノール、エタノールなどのアルコールやアセトニトコノ
ルなどの極性有機溶媒と水の混液で通液し、この液を分
取する１ ］
ことにより精製できる。 前記のように合成した糖分岐
脂肪族エーテルは、抽出溶媒を留去したり、カラムによ
り精製した後層いてもよく、そのまま用いてもよい。
また、−形式（Ｉ Ｉ）で表される分枝脂肪族グリコシ
ドは、例えば特許（公開；６３−８４６３７）の糖類変
性用酸触媒を用いーＣ合成できるほか、一般にグリコジ
ル化に用いられている反応（ケーニッヒ−クノール反応
、ヘルフエライヒ法や、それ以外のエーテル交換法等）
を用いても良い。The reaction product thus obtained has a -form (I
) In addition to the sugar-branched aliphatic ether shown in ), salts, sugars, etc. during neutralization coexist. Therefore, for example, when removing sugars and salts, extraction is performed with a solvent that does not dissolve sugars, such as methyl alcohol, ethyl alcohol, butyl alcohol, or isopropyl alcohol, or water containing a large amount of salt is extracted with methyl edyl ketone or n-butanol. Purification can be achieved by separating the organic solvent layer and separating the organic solvent layer. It also removes sugar and salt,
When separating compounds according to the number of branched alkyl groups bonded, the reaction product is suspended in water or a mixture of water and alcohol, and a hyperporous polymer (for example, Hi-Porous Resin manufactured by Mitsubishi Kasei Corporation), octadecyl silica, etc. It can be purified by first passing water through a reverse-phase partition column, then passing a mixture of water and an alcohol such as methanol or ethanol, or a polar organic solvent such as acetonitkonol, and then separating this liquid1]. . The sugar-branched aliphatic ether synthesized as described above may be layered after the extraction solvent is distilled off or purified using a column, or it may be used as it is.
In addition, the branched aliphatic glycoside represented by the -form (II) can be synthesized using, for example, the acid catalyst for modifying sugars disclosed in the patent (publication; 63-84637), and it can also be synthesized by -C, which is generally used for glycosylation. Reactions (Koenig-Knorr reaction, Helfelreich method, other ether exchange methods, etc.)
You may also use
このようにして得られる糖分枝脂肪族エーテル及び分枝
脂肪族グリコシドは、化学安定性・酸化安定性に優れ、
界面活性能を有する上、分散性・保湿性・ゲル安定性、
更に液晶安定性に優れるという機能を持つ。The sugar branched aliphatic ethers and branched aliphatic glycosides obtained in this way have excellent chemical stability and oxidative stability,
In addition to having surface-active ability, it also has dispersibility, moisture retention, gel stability,
Furthermore, it has the function of excellent liquid crystal stability.
本発明のゲル化剤は、安全性に優れるので、化粧料、医
薬料等に配合できる。また、本発明に加えて通常用いら
れる他の化粧料や医薬料成分を適宜配合することができ
る。例えば、流動パラフィン、スクワラン、ワセリン、
セチルアルコール、イソステアリルアルコール、２−エ
チルヘキザン酸セヂル、２−オクヂルドデシルアルコー
ル、トリイソステアリン酸グリセリン、マカデミアンナ
ッツ油、ラノリン等の各種炭化水素、油脂類、ロウ類等
の油性成分、シリコーン類、他の界面活性剤、増粘剤、
中和剤、防腐剤、殺菌剤、酸化防止剤、粉体成分、色素
、香料、紫外線吸収剤、薬効剤、金属封鎖剤、ｐＨ調製
剤等が挙げられる。Since the gelling agent of the present invention has excellent safety, it can be incorporated into cosmetics, pharmaceuticals, and the like. In addition to the ingredients of the present invention, other commonly used cosmetics and pharmaceutical ingredients may be appropriately blended. For example, liquid paraffin, squalane, petrolatum,
Various hydrocarbons such as cetyl alcohol, isostearyl alcohol, cedyl 2-ethylhexanoate, 2-ocdyldodecyl alcohol, glycerin triisostearate, macadamian nut oil, lanolin, oils and fats, oily components such as waxes, silicones, other surfactants, thickeners,
Examples include neutralizing agents, preservatives, bactericidal agents, antioxidants, powder components, pigments, fragrances, ultraviolet absorbers, medicinal agents, metal sequestrants, pH adjusters, and the like.
［実施例］
以下、実施例を挙げて本発明について具体的に説明する
。[Example] Hereinafter, the present invention will be specifically described with reference to Examples.
尚、本発明はこれに限定されるものではない。Note that the present invention is not limited to this.
玉」ト蝕ニー
４８％臭化水素酸１００ｇに濃硫酸２６ｇを加え、これ
にイソステアリルアルコール３０．０ｇを滴下した。こ
れを昇温し、５時間加熱還流した後、空冷し、４ ０
０ ｍ’ｌ精製水中に性別すると、茶褐色の油層が分離
した。これを、クロロポルム６００ｍｌで抽出し、続い
て１０％炭酸カリウム水溶液３００ ｍ ｌで１回、精
製水５００ ｍ ｌで２回洗浄した後、油層を無水硫酸
マグネシウムで乾燥した。続いて、無水硫酸マグネシウ
ムを濾去した後、減圧濃縮し、得られた淡黄色シロップ
をシリカゲルカラムクロマトグラフ法で、展開溶媒ヘキ
サンにて精製し、臭化イソステアリルを３６゜９ｇ得た
。26 g of concentrated sulfuric acid was added to 100 g of 48% hydrobromic acid, and 30.0 g of isostearyl alcohol was added dropwise thereto. This was heated to reflux for 5 hours, then air cooled to 40
When placed in 0 ml purified water, a brown oil layer was separated. This was extracted with 600 ml of chloroporm, then washed once with 300 ml of 10% aqueous potassium carbonate solution and twice with 500 ml of purified water, and then the oil layer was dried over anhydrous magnesium sulfate. Subsequently, after removing anhydrous magnesium sulfate by filtration, the mixture was concentrated under reduced pressure, and the resulting pale yellow syrup was purified by silica gel column chromatography using hexane as a developing solvent to obtain 36.9 g of isostearyl bromide.
マルチ）・−ル９．２９ｇを予め乾燥きせておいたジメ
チルスルホキシド９０ｍ１に溶解し、８００Ｃ加熱撹拌
１ζ、水酸化ナトリウム０．５９ｇを加え、３０分撹拌
した後、」二重方法にて予め合成した臭化イソステアリ
ル４．ＯＯｇを加え、更にに記温度で３時間加熱撹拌し
た。次に、室温士で冷却し、ＩＮ塩酸で中和した。反応
溶媒を減圧蒸留にて留去し、残留物をハイパーポーラス
ポリマー（三菱化成工業株式会社製のハイポーラス樹脂
）のカラムクロマトグラフ法で展開溶媒として初め精製
水、次にエチルアルコール：精製水＝７：３を用いて分
画すると、精製水の溶出部に食塩、マルチトール及びジ
メチルスルホキシドが認められ、エチルアルコール：精
製水＝７：３溶出部を濃縮し、これをＮ、Ｏ−（ビスト
リメチルシリル）アセトアミド、トリメデルクロロシラ
ン、Ｎ−１−リメチルシリルイミダゾールの等量混合物
でトリメデルシリル化した後、ガスクロマトグラフ法（
カラム充填剤：日本クロマト工業株式会社製、ｊ）ｉａ
ｓｏｌｉｄ ＺＴ内径３ｍｍ、長き５０ｃｍ、昇温速度
： １０００Ｃ−３４０°Ｃ，１００Ｃ／ｍｉｎ、キャ
リアガス及び流量：窒素、５０ｍ１／ｍｉｎ、、検出器
：ＦＴＤ）に７分析したとコロ、保持時間１４．０１分
にマルチトールモノイソステアリルエーテルのピークが
８測された。マルチトールモノイソステアリルエーテル
の収量は２゜００ｇ （収率２７．９％）であった。こ
のようにして得たマルチトールイソスデアリルエーテル
を試料１とした。After dissolving 9.29 g of Multi) in 90 ml of pre-dried dimethyl sulfoxide, stirring at 800C for 1ζ, adding 0.59 g of sodium hydroxide and stirring for 30 minutes, the mixture was pre-synthesized using a double method. Isostearyl bromide 4. OOg was added, and the mixture was further heated and stirred at the specified temperature for 3 hours. Next, it was cooled at room temperature and neutralized with IN hydrochloric acid. The reaction solvent was distilled off under reduced pressure, and the residue was subjected to column chromatography using hyperporous polymer (high porous resin manufactured by Mitsubishi Chemical Industries, Ltd.) using first purified water as the developing solvent, then ethyl alcohol: purified water = When fractionation was performed using 7:3, salt, maltitol, and dimethyl sulfoxide were found in the eluate of purified water, and the eluate of ethyl alcohol:purified water = 7:3 was concentrated, and this was dissolved in N, O-(bis). After trimedelsilylation with an equal mixture of trimethylsilyl)acetamide, trimedelchlorosilane, and N-1-limethylsilylimidazole, gas chromatography (
Column packing material: Nippon Chromato Industries Co., Ltd., j)ia
solid ZT inner diameter 3mm, length 50cm, heating rate: 1000C-340°C, 100C/min, carrier gas and flow rate: nitrogen, 50ml/min, detector: FTD), retention time 14. Eight peaks of maltitol monoisostearyl ether were measured at 01 minutes. The yield of maltitol monoisostearyl ether was 2.00 g (yield 27.9%). The thus obtained maltitol isosudearyl ether was designated as Sample 1.
製造例２
４８％臭化水素酸１５０ｇに濃硫酸３０．０ｇを加え、
これにテトラヒドラゲラニオール３０゜０ ｇを滴下し
・た後、昇温し、加熱還流５．５時間した。反応後、空
冷した後、精製水３００ｍ１中］ ５
に性別すると、茶褐色の油層に分離した。これを、クロ
ロホルム５００ｍ１で抽出し、］○％炭酸カリウム水溶
液３００ｍ１で１回、精製水５００ｍ１で２回洗浄し、
油層を無水硫酸マグネシウムで乾燥した。これを無水硫
酸マグネシウムを濾去したのち、減圧濃縮し得られた淡
黄色オイルをシリカゲルカラムクロマトグラフ法で展開
溶媒ヘキサンにて精製し、臭化テトラヒドロゲラニル４
１゜８ｇ得た。Production Example 2 Add 30.0 g of concentrated sulfuric acid to 150 g of 48% hydrobromic acid,
After 30.0 g of tetrahydra geraniol was added dropwise to this, the temperature was raised and the mixture was heated under reflux for 5.5 hours. After the reaction, the mixture was cooled in air and poured into 300 ml of purified water to separate into a brown oil layer. This was extracted with 500 ml of chloroform, washed once with 300 ml of ○% potassium carbonate aqueous solution and twice with 500 ml of purified water,
The oil layer was dried over anhydrous magnesium sulfate. After filtering off the anhydrous magnesium sulfate, the resulting pale yellow oil was concentrated under reduced pressure and purified by silica gel column chromatography using hexane as a developing solvent.
1°8g was obtained.
次に、マルチトール２０．Ｏｇを予め乾燥させておいた
ジメチルスルホキシド１．９０ｍ１に溶解し、室温にて
、水酸化ナトリウム１．３９４−ｇを加え、３０分撹拌
した後、上記の方法により、予め合成した臭化テトラヒ
ドロゲラニル６．４２４ｇを滴下した。滴下後、４時間
撹拌した後、反応系を室温まで冷却し、ＩＮ塩酸で中和
した。その後、溶媒を減圧留去し、得られた残留物をハ
イパポーラスポリマー（三菱化成工業株式会社製のハイ
ポーラス樹脂）のカラムクロマトグラフ法で展開溶媒と
じて初めに精製水、次にエチルアルコール：精製水＝１
＝１を用いて分画すると、精製水の溶出部に食塩、マル
チトール及びジメチルスルホキシドが認められ、エチル
アルコール：精製水＝１：１溶出部を濃縮し、これをＮ
、Ｏ−（ビストリメデルシリル）アセトアミド、トリメ
デルクロロシラン、Ｎ−トリメデルシリルイミダゾール
の等量混合物でトリメチルシリル化した後、前記と同様
の条件でガスクロマトグラフ法にて分析したところ、保
持時間１１．１．８分にマルチトールモノテトラヒドラ
ゲラニルエーテルのピークか観測された。マルヂト−ル
モノテトラヒドラゲラニルエーテルの収量は８．６ｇ
（収率３０．４７％）であった。そのようにして得たマ
ルヂトールテトラヒドラゲラニルエーテルを試料２とし
た。Next, maltitol 20. Og was dissolved in 1.90 ml of dimethyl sulfoxide that had been dried in advance, and 1.394 g of sodium hydroxide was added at room temperature. After stirring for 30 minutes, the tetrahydrogeranyl bromide synthesized in advance by the above method was dissolved. 6.424g was added dropwise. After the dropwise addition and stirring for 4 hours, the reaction system was cooled to room temperature and neutralized with IN hydrochloric acid. Thereafter, the solvent was distilled off under reduced pressure, and the resulting residue was subjected to column chromatography using a hyperporous polymer (hyporous resin manufactured by Mitsubishi Chemical Industries, Ltd.) as a developing solvent, first with purified water, then with ethyl alcohol. Purified water = 1
When fractionation was performed using ethyl alcohol:purified water = 1, salt, maltitol, and dimethyl sulfoxide were found in the eluted portion of purified water, and the eluted portion of ethyl alcohol:purified water = 1:1 was concentrated, and this was
, O-(bistrimedelsilyl)acetamide, trimedelchlorosilane, and N-trimedelsilylimidazole were trimethylsilylated with a mixture of equal amounts, and then analyzed by gas chromatography under the same conditions as above, the retention time was 11.1. A peak of maltitol monotetrahydrageranyl ether was observed at .8 minutes. The yield of marditolmonotetrahydrageranyl ether is 8.6g.
(yield 30.47%). The thus obtained marditol tetrahydrageranyl ether was designated as Sample 2.
製造例３
日本粘化（株）が持つ特許（公開； ６３−８４６３７
）の方法に準じて合成した。即ち、イソステアリルアル
コール１０ｍ１とオクタアセチルマルトシド１０．９ｇ
とポリモリブドリン酸１４４ｍｇをトルエン２２ｍ ｌ
に溶解し、８５℃油浴中、〕 ８
２時間加熱撹拌した。次に、反応系を室温まで空冷し、
酢酸エチル］、 ＯＯｍ ｌで希釈したのち、飽和食塩
水３０ｍ１で５回洗浄し、無水硫酸マグネシウムにて乾
燥した。これを、無水硫酸マグネシウムを濾去した後、
減圧濃縮し、得られた褐色シロップ１８．４ｇをシリカ
ゲルカラムクロマトグラフ法にて展開溶媒ヘキザン：酢
酸エチル＝４＝１で精製すると、３．３ｇのイソステア
リルマルトシド１・−タルアセタートを得た。これを、
ＩＮナトリウムメチラートに溶解し、室温にて３０分間
撹拌し、脱アセデル化した後、アンバーライトＩＲ］、
２０−Ｂで樹脂中和し、濾過後、減圧濃縮すると、白色
結晶状のイソステアリルマルトシド２．２ｇを得た。こ
れを、シリカゲルカラムクロマトグラフ法にて展開溶媒
メタノール：クロロホルム＝１：３で精製したものを試
料３とした。Production Example 3 Patent held by Nippon Kuka Co., Ltd. (published; 63-84637
) was synthesized according to the method of That is, 10 ml of isostearyl alcohol and 10.9 g of octaacetyl maltoside.
and 144 mg of polymolybdophosphoric acid in 22 ml of toluene.
The mixture was heated and stirred in an 85°C oil bath for 2 hours. Next, the reaction system was air cooled to room temperature,
After diluting with 0ml of ethyl acetate], the mixture was washed five times with 30ml of saturated brine, and dried over anhydrous magnesium sulfate. After filtering off the anhydrous magnesium sulfate,
After concentration under reduced pressure, 18.4 g of the obtained brown syrup was purified by silica gel column chromatography using a developing solvent of hexane:ethyl acetate = 4 = 1 to obtain 3.3 g of isostearyl maltoside 1-talacetate. this,
After dissolving in IN sodium methylate and stirring at room temperature for 30 minutes to deacetylate, Amberlite IR],
The resin was neutralized with 20-B, filtered, and concentrated under reduced pressure to obtain 2.2 g of white crystalline isostearyl maltoside. This was purified by silica gel column chromatography using a developing solvent of methanol:chloroform=1:3, and this was designated as sample 3.
加熱した。冷却後の水溶液の一定量を取り、エチルエー
テルで抽出し、その抽出物のガスクロマトグラムから加
水分解崩を求めた。Heated. A certain amount of the cooled aqueous solution was taken and extracted with ethyl ether, and the hydrolytic breakdown was determined from the gas chromatogram of the extract.
（２）アルデヒド発生試験
製造例１，２を８０°Ｃの容器−Ｌに１００時間放置し
た後、それぞれの試料５ｇを採取した。その後、水５０
０ｍ１及び薄めたリン酸３ｒｎｌを加えてから蒸留し、
留出量が１．９０ｍ１になった時点で蒸留をやめ、水を
くわえて２００ｍ１とし、これを試験溶液として用いた
。(2) Aldehyde generation test After leaving Production Examples 1 and 2 in a container-L at 80°C for 100 hours, 5 g of each sample was collected. After that, water 50
Add 0 ml and 3 rnl of diluted phosphoric acid, then distill;
Distillation was stopped when the distilled volume reached 1.90 ml, water was added to make 200 ml, and this was used as a test solution.
この試験溶液１０ｍ ｌを取り、アセデルアセトン５ｍ
ｌを加えて振り混ぜ、６００Ｃの水浴中で１０分間加熱
した。冷却後、波長４２０ｎｍ付近の極大吸収波長にお
ける吸光度を測定した。Take 10 ml of this test solution and add 5 ml of acedelacetone.
1 was added, shaken, and heated in a 600C water bath for 10 minutes. After cooling, the absorbance at a maximum absorption wavelength around 420 nm was measured.
これらの結果を表−１に示した。These results are shown in Table-1.
（１）加水分解試験
製造例１．２の１％水溶液を９０°Ｃで５時間表−１か
ら判るように製造例１，２のいずれの試料も加水分解は
ほとんど認められなかった。(1) Hydrolysis test The 1% aqueous solution of Production Example 1.2 was heated at 90°C for 5 hours.As can be seen from Table 1, almost no hydrolysis was observed in either of the samples of Production Examples 1 and 2.
一方、市販のショ糖ラウリン酸エステル及びポリエチレ
ングリコール（ＰＥＧ）ラウリン酸エステルでは、表−
１に示すとおり、同一条件でそれぞわ約２０％、約２％
のエステル基の分解が認められ１′二。On the other hand, commercially available sucrose laurate and polyethylene glycol (PEG) laurate have the following properties:
As shown in 1, under the same conditions, approximately 20% and 2%, respectively.
Decomposition of the ester group of 1'2 was observed.
また、実験室的に合成したソルビト−ルヒドロキシステ
アリルエーテルでは、加水分解は、はとんど認められな
かった。Further, in sorbitol hydroxystearyl ether synthesized in a laboratory, hydrolysis was hardly observed.
また、製造例１，２のいずれの試料もアルデヒドの存在
は認められなかっｌ；。Furthermore, the presence of aldehyde was not observed in either of the samples of Production Examples 1 and 2.
一方、ポリエヂレングリコールラウリン酸エステルを同
様に処理して評価すると、アルデヒドの存在が認められ
た。On the other hand, when polyethylene glycol laurate was similarly treated and evaluated, the presence of aldehyde was observed.
なお、ショ糖ラウリン酸エステルとソルビトールヒドロ
キシステアリルエーテルでは、同様に処理しても、アル
デヒドの存在は認められなかった。Incidentally, even when sucrose laurate ester and sorbitol hydroxystearyl ether were treated in the same manner, the presence of aldehyde was not observed.
実施例１
（１）製造例１で得られた １．５％マルヂ
ト−ルイン
ステアリルエーテル
（２）グリセリン ３．０％（３）プ
ロピレングリコール ４．０％（４）オレイル
アルコール ０，１％（５）各種活性剤試料
１．５％（６）エタノール
１０．０％（７）香料
適量（８）エヂルパラベン 適量
（９）イオン交換水 残余実施例と
（１）製造例２で得られた １．５％マルヂ
ト−ルテトラ
ヒトラゲラニルエーテル
（２グリセリン ３．０％（３プロピ
レングリコール ４．０％（４オレイルアルコ
ール ０．１％（５各種活性剤試料
１．５％（６エタノール
１０．０％（７香料 適量（
８エヂルパラベン 適量（９イオン交換
水 残余また、上記実施例１．２は０
０Ｃｚ ５００Ｃに１ケ月放置しても白濁もせず、安定
であり、アルデヒドの存在も認められなかったが、ポリ
エチレングリコール（ＰＥＧ）ラウリン酸エステルを用
いたものでは、５０°Ｃに１ケ月放置すると、アルデヒ
ドの存在が認められた。Example 1 (1) 1.5% malditoline stearyl ether obtained in Production Example 1 (2) Glycerin 3.0% (3) Propylene glycol 4.0% (4) Oleyl alcohol 0.1% (5 ) Various activator samples 1.5% (6) Ethanol
10.0% (7) Fragrance
Appropriate amount (8) Ezylparaben Appropriate amount (9) Ion-exchanged water 1.5% Marditol Tetrahydragelanyl Ether (2) Glycerin 3.0% (3 Propylene Glycol 4) obtained in Remaining Examples and (1) Production Example 2. 0% (4 Oleyl alcohol 0.1% (5 Various activator samples)
1.5% (6 ethanol
10.0% (7 fragrances, appropriate amount)
8 Egilparaben appropriate amount (9 ion-exchanged water remainder, and Example 1.2 above has 0
0Cz Even when left at 500C for one month, it did not become cloudy, was stable, and no aldehyde was observed; The presence of aldehydes was observed.
以上のことから本発明の糖分岐脂肪族エーテル、分岐脂
肪族グリコシドは経時て酸化を受けることなく、低分子
量のアルデヒドや有機酸を発生せず、変臭や皮膚刺激の
原因となったり、ｐＨの低下を起こすという問題点を有
さない。 まｌ：、ｐＨが中性からはずれている皮膚外
用剤の成分として用いた場合にも、エーテル結合は分解
されず、経日安定性や安全性に問題を生しない。From the above, the sugar branched aliphatic ethers and branched aliphatic glycosides of the present invention do not undergo oxidation over time, do not generate low molecular weight aldehydes or organic acids, do not cause odor or skin irritation, and do not have pH It does not have the problem of causing a decrease in 1: Even when used as a component of an external skin preparation whose pH deviates from neutrality, the ether bond will not be decomposed and there will be no problem with stability over time or safety.
実施例３
製造例１のマルチト−ルイソステアリルエーテル、製造
例３のイソステアリルマルトシド、実験室で合成したマ
ルヂトールヒトロキシステアリルエーテル、ラウリルマ
ルトシドを用いてそれぞれ１０％水溶液を調製したとこ
ろ、マルチト−ルイソステアリルエーテルとイソステア
リルマルトシドはゼリー状になったが、マルヂト−ルヒ
ドロキシステアリルエーテルとラウリルマルトシドは、
そのようにならなかった。Example 3 A 10% aqueous solution was prepared using maltitol isostearyl ether of Production Example 1, isostearyl maltoside of Production Example 3, malditol hydroxystearyl ether synthesized in a laboratory, and lauryl maltoside. , malditol isostearyl ether and isostearyl maltoside became jelly-like, but malditol hydroxystearyl ether and lauryl maltoside became jelly-like.
It didn't turn out that way.
実施例４
製造例１のマルチト−ルイソステアリルエーテル、製造
例３のイソステアリルマルトシドと、ステアリルマルト
シド、ジベンジリデン−Ｄ−ソルビトールを用いてそれ
ぞれ５°Ｃにて（溶媒；水）可溶化試験を行ったところ
、マルチトールイソステアリルエーテル、イソステアリ
ルマルトシドは１０％以上溶解したが、ステアリルマル
トシド、ジヘンジリデンーＤ−ソルビト−ルは、殆ど溶
解しなかった。Example 4 Solubilization at 5°C (solvent: water) using maltitol isostearyl ether of Production Example 1, isostearyl maltoside of Production Example 3, stearyl maltoside, and dibenzylidene-D-sorbitol, respectively. When tested, maltitol isostearyl ether and isostearyl maltoside were dissolved by 10% or more, but stearyl maltoside and dihenzylidene-D-sorbitol were hardly dissolved.
実施例５
製造例］のマルチトールイソステアリルエーテル、製造
例３のイソステアリルマルトシド、寒天、及びゼラチン
でそれぞれ１％水溶液を調製し、調製した溶液を２５°
Ｃで１０ケ月間放置後、その外観を観察した結果、マル
チトールイソステアリルエーテル、イソステアリルマル
トシドは分離もなく、安定であったが、寒天とゼラチン
は分離していた。Example 5 A 1% aqueous solution was prepared with maltitol isostearyl ether from Production Example], isostearyl maltoside from Production Example 3, agar, and gelatin, and the prepared solution was heated at 25°C.
After being left at C for 10 months, its appearance was observed. As a result, maltitol isostearyl ether and isostearyl maltoside were stable without separation, but agar and gelatin were separated.
Claims (1)
ル ▲数式、化学式、表等があります▼（ I ） （ただし、式中Ａは糖からｎ個の水酸基を除いた残基。 Ｒは、エーテル結合から１位以上に分岐鎖を持つ脂肪鎖
で、全炭素数８〜３２。ｎは１以上を表す。） 及び／または、一般式（II）で、表される 分岐脂肪族グリコシド。 Ａ−Ｏ−Ｒ（II） （ただし、式中Ａは糖から１個の水酸基を除いた残基。 Ｒは、グリコシド結合から１位以上に分岐鎖を持つ脂肪
鎖で、全炭素数８〜３２。） を用いることを特徴とするゲル化剤。(1) Sugar-branched aliphatic ether represented by the general formula (I) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) (However, in the formula, A is the residue obtained by removing n hydroxyl groups from the sugar. R is an aliphatic chain having a branch at the 1st or higher position from the ether bond, with a total carbon number of 8 to 32; n represents 1 or more) and/or a branched aliphatic group represented by the general formula (II) Glycoside. A-O-R(II) (However, in the formula, A is a residue obtained by removing one hydroxyl group from a sugar. R is an aliphatic chain with a branched chain at the 1st or higher position from the glycosidic bond, and has a total carbon number of 8 to 32.) A gelling agent characterized by using the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2189761A JPH0476082A (en) | 1990-07-18 | 1990-07-18 | Gelling agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2189761A JPH0476082A (en) | 1990-07-18 | 1990-07-18 | Gelling agent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0476082A true JPH0476082A (en) | 1992-03-10 |
Family
ID=16246739
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2189761A Pending JPH0476082A (en) | 1990-07-18 | 1990-07-18 | Gelling agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0476082A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001226215A (en) * | 1999-12-10 | 2001-08-21 | Kanebo Ltd | Cosmetic and method of producing ether derivative of raffinose |
| JP2007262085A (en) * | 1994-09-14 | 2007-10-11 | Stephan Ladisch | Synthetic ganglioside derivatives |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4724532B1 (en) * | 1968-02-07 | 1972-07-06 | ||
| JPS4911206B1 (en) * | 1969-07-24 | 1974-03-15 |
-
1990
- 1990-07-18 JP JP2189761A patent/JPH0476082A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4724532B1 (en) * | 1968-02-07 | 1972-07-06 | ||
| JPS4911206B1 (en) * | 1969-07-24 | 1974-03-15 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007262085A (en) * | 1994-09-14 | 2007-10-11 | Stephan Ladisch | Synthetic ganglioside derivatives |
| JP2001226215A (en) * | 1999-12-10 | 2001-08-21 | Kanebo Ltd | Cosmetic and method of producing ether derivative of raffinose |
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