JP5495255B2 - Liposome-containing composition, and cosmetic for skin comprising the composition - Google Patents
Liposome-containing composition, and cosmetic for skin comprising the composition Download PDFInfo
- Publication number
- JP5495255B2 JP5495255B2 JP2009181282A JP2009181282A JP5495255B2 JP 5495255 B2 JP5495255 B2 JP 5495255B2 JP 2009181282 A JP2009181282 A JP 2009181282A JP 2009181282 A JP2009181282 A JP 2009181282A JP 5495255 B2 JP5495255 B2 JP 5495255B2
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- JP
- Japan
- Prior art keywords
- component
- liposome
- glyceryl
- alcohol
- containing composition
- 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.)
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- 239000002502 liposome Substances 0.000 title claims description 105
- 239000000203 mixture Substances 0.000 title claims description 50
- 239000002537 cosmetic Substances 0.000 title claims description 17
- -1 glyceryl monoalkyl ethers Chemical class 0.000 claims description 39
- 150000003904 phospholipids Chemical class 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 229940106189 ceramide Drugs 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229940031723 1,2-octanediol Drugs 0.000 claims description 4
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 claims description 4
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 claims description 4
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 claims description 4
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 claims description 4
- AEIJTFQOBWATKX-UHFFFAOYSA-N octane-1,2-diol Chemical compound CCCCCCC(O)CO AEIJTFQOBWATKX-UHFFFAOYSA-N 0.000 claims description 4
- 229940015975 1,2-hexanediol Drugs 0.000 claims description 3
- YSRSBDQINUMTIF-UHFFFAOYSA-N decane-1,2-diol Chemical compound CCCCCCCCC(O)CO YSRSBDQINUMTIF-UHFFFAOYSA-N 0.000 claims description 3
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 claims description 3
- 239000012528 membrane Substances 0.000 description 31
- 235000014113 dietary fatty acids Nutrition 0.000 description 22
- 239000000194 fatty acid Substances 0.000 description 22
- 229930195729 fatty acid Natural products 0.000 description 22
- 238000003860 storage Methods 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 239000002202 Polyethylene glycol Substances 0.000 description 10
- 229920001223 polyethylene glycol Polymers 0.000 description 10
- 150000005846 sugar alcohols Polymers 0.000 description 9
- 238000000113 differential scanning calorimetry Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 7
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 230000002708 enhancing effect Effects 0.000 description 5
- 229940099578 hydrogenated soybean lecithin Drugs 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WWUZIQQURGPMPG-UHFFFAOYSA-N (-)-D-erythro-Sphingosine Natural products CCCCCCCCCCCCCC=CC(O)C(N)CO WWUZIQQURGPMPG-UHFFFAOYSA-N 0.000 description 4
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 4
- AERBNCYCJBRYDG-UHFFFAOYSA-N D-ribo-phytosphingosine Natural products CCCCCCCCCCCCCCC(O)C(O)C(N)CO AERBNCYCJBRYDG-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 150000001783 ceramides Chemical class 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 4
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 4
- 229940033329 phytosphingosine Drugs 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- CAYHVMBQBLYQMT-UHFFFAOYSA-N 2-decyltetradecan-1-ol Chemical compound CCCCCCCCCCCCC(CO)CCCCCCCCCC CAYHVMBQBLYQMT-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229930182558 Sterol Natural products 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 229940099417 ceramide 2 Drugs 0.000 description 3
- 239000003240 coconut oil Substances 0.000 description 3
- 235000019864 coconut oil Nutrition 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
- 229940055577 oleyl alcohol Drugs 0.000 description 3
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 3
- AERBNCYCJBRYDG-KSZLIROESA-N phytosphingosine Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](N)CO AERBNCYCJBRYDG-KSZLIROESA-N 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 150000003432 sterols Chemical class 0.000 description 3
- 235000003702 sterols Nutrition 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- JQWAHKMIYCERGA-UHFFFAOYSA-N (2-nonanoyloxy-3-octadeca-9,12-dienoyloxypropoxy)-[2-(trimethylazaniumyl)ethyl]phosphinate Chemical compound CCCCCCCCC(=O)OC(COP([O-])(=O)CC[N+](C)(C)C)COC(=O)CCCCCCCC=CCC=CCCCCC JQWAHKMIYCERGA-UHFFFAOYSA-N 0.000 description 2
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 2
- WNWHHMBRJJOGFJ-UHFFFAOYSA-N 16-methylheptadecan-1-ol Chemical compound CC(C)CCCCCCCCCCCCCCCO WNWHHMBRJJOGFJ-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
- ASKIVFGGGGIGKH-UHFFFAOYSA-N 2,3-dihydroxypropyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(O)CO ASKIVFGGGGIGKH-UHFFFAOYSA-N 0.000 description 2
- JYZLSYFPFQTNNO-UHFFFAOYSA-N 2-octyldecan-1-ol Chemical compound CCCCCCCCC(CO)CCCCCCCC JYZLSYFPFQTNNO-UHFFFAOYSA-N 0.000 description 2
- LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 2
- 239000004166 Lanolin Substances 0.000 description 2
- BBAFBDLICMHBNU-MFZOPHKMSA-N N-(2-hydroxyoctadecanoyl)-4-hydroxysphinganine Chemical compound CCCCCCCCCCCCCCCCC(O)C(=O)N[C@@H](CO)[C@H](O)[C@H](O)CCCCCCCCCCCCCC BBAFBDLICMHBNU-MFZOPHKMSA-N 0.000 description 2
- ATGQXSBKTQANOH-UWVGARPKSA-N N-oleoylphytosphingosine Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@H](CO)NC(=O)CCCCCCC\C=C/CCCCCCCC ATGQXSBKTQANOH-UWVGARPKSA-N 0.000 description 2
- 235000019482 Palm oil Nutrition 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- 239000004147 Sorbitan trioleate Substances 0.000 description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 description 2
- CMPDPBDUZTUXAD-UHFFFAOYSA-N [3-hydroxy-2-(16-methylheptadecanoyloxy)propyl] 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCC(C)C CMPDPBDUZTUXAD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- NOPFSRXAKWQILS-UHFFFAOYSA-N docosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCO NOPFSRXAKWQILS-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000010696 ester oil Substances 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 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 2
- 229940074045 glyceryl distearate Drugs 0.000 description 2
- 229940068939 glyceryl monolaurate Drugs 0.000 description 2
- 229940075507 glyceryl monostearate Drugs 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 125000001165 hydrophobic group Chemical group 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 229940039717 lanolin Drugs 0.000 description 2
- 235000019388 lanolin Nutrition 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- 229940042880 natural phospholipid Drugs 0.000 description 2
- 239000010466 nut oil Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 239000002540 palm oil Substances 0.000 description 2
- 229920001515 polyalkylene glycol Polymers 0.000 description 2
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 235000019337 sorbitan trioleate Nutrition 0.000 description 2
- 229960000391 sorbitan trioleate Drugs 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- CFOQKXQWGLAKSK-KTKRTIGZSA-N (13Z)-docosen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCO CFOQKXQWGLAKSK-KTKRTIGZSA-N 0.000 description 1
- JSPNNZKWADNWHI-PNANGNLXSA-N (2r)-2-hydroxy-n-[(2s,3r,4e,8e)-3-hydroxy-9-methyl-1-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]heptadecanamide Chemical compound CCCCCCCCCCCCCCC[C@@H](O)C(=O)N[C@H]([C@H](O)\C=C\CC\C=C(/C)CCCCCCCCC)CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O JSPNNZKWADNWHI-PNANGNLXSA-N 0.000 description 1
- PAFJZWHXMSQJKV-UQZRNVAESA-N (3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol;octadecanoic acid Chemical compound OC[C@@H](O)C1OC[C@H](O)[C@H]1O.OC[C@@H](O)C1OC[C@H](O)[C@H]1O.OC[C@@H](O)C1OC[C@H](O)[C@H]1O.CCCCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O PAFJZWHXMSQJKV-UQZRNVAESA-N 0.000 description 1
- JXNPEDYJTDQORS-HZJYTTRNSA-N (9Z,12Z)-octadecadien-1-ol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCO JXNPEDYJTDQORS-HZJYTTRNSA-N 0.000 description 1
- IKYKEVDKGZYRMQ-PDBXOOCHSA-N (9Z,12Z,15Z)-octadecatrien-1-ol Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCCO IKYKEVDKGZYRMQ-PDBXOOCHSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- CITHEXJVPOWHKC-UUWRZZSWSA-N 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC CITHEXJVPOWHKC-UUWRZZSWSA-N 0.000 description 1
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 description 1
- IJFVSSZAOYLHEE-SSEXGKCCSA-N 1,2-dilauroyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCC IJFVSSZAOYLHEE-SSEXGKCCSA-N 0.000 description 1
- SNKAWJBJQDLSFF-NVKMUCNASA-N 1,2-dioleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC SNKAWJBJQDLSFF-NVKMUCNASA-N 0.000 description 1
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
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- GBXRUYNQDDTQQS-UHFFFAOYSA-N 1-O-dodecylglycerol Chemical compound CCCCCCCCCCCCOCC(O)CO GBXRUYNQDDTQQS-UHFFFAOYSA-N 0.000 description 1
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- OKMWKBLSFKFYGZ-UHFFFAOYSA-N 1-behenoylglycerol Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(O)CO OKMWKBLSFKFYGZ-UHFFFAOYSA-N 0.000 description 1
- ZXNAIPHYBVMMPY-KTKRTIGZSA-N 1-erucoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OCC(O)CO ZXNAIPHYBVMMPY-KTKRTIGZSA-N 0.000 description 1
- QHZLMUACJMDIAE-SFHVURJKSA-N 1-hexadecanoyl-sn-glycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)CO QHZLMUACJMDIAE-SFHVURJKSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- CFOQKXQWGLAKSK-UHFFFAOYSA-N 13-docosen-1-ol Natural products CCCCCCCCC=CCCCCCCCCCCCCO CFOQKXQWGLAKSK-UHFFFAOYSA-N 0.000 description 1
- DHGBAFGZLVRESL-UHFFFAOYSA-N 14-methylpentadecyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC(C)C DHGBAFGZLVRESL-UHFFFAOYSA-N 0.000 description 1
- FUTGDWNFCMWSJT-UHFFFAOYSA-N 2,3-bis(14-methylpentadecanoyloxy)propyl 14-methylpentadecanoate Chemical compound CC(C)CCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCC(C)C)COC(=O)CCCCCCCCCCCCC(C)C FUTGDWNFCMWSJT-UHFFFAOYSA-N 0.000 description 1
- 239000000263 2,3-dihydroxypropyl (Z)-octadec-9-enoate Substances 0.000 description 1
- XFBOJHLYDJZYSP-UHFFFAOYSA-N 2,8-dioxoadenine Chemical compound N1C(=O)N=C2NC(=O)NC2=C1N XFBOJHLYDJZYSP-UHFFFAOYSA-N 0.000 description 1
- FLPJVCMIKUWSDR-UHFFFAOYSA-N 2-(4-formylphenoxy)acetamide Chemical compound NC(=O)COC1=CC=C(C=O)C=C1 FLPJVCMIKUWSDR-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
- FKOKUHFZNIUSLW-UHFFFAOYSA-N 2-Hydroxypropyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(C)O FKOKUHFZNIUSLW-UHFFFAOYSA-N 0.000 description 1
- ZVUNTIMPQCQCAQ-UHFFFAOYSA-N 2-dodecanoyloxyethyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCOC(=O)CCCCCCCCCCC ZVUNTIMPQCQCAQ-UHFFFAOYSA-N 0.000 description 1
- MUHFRORXWCGZGE-KTKRTIGZSA-N 2-hydroxyethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCO MUHFRORXWCGZGE-KTKRTIGZSA-N 0.000 description 1
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Images
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Description
本発明は、リポソーム含有組成物、並びに該組成物を配合してなる皮膚用化粧料に関する。 The present invention relates to a liposome-containing composition and a cosmetic for skin obtained by blending the composition.
リポソームとは、生体膜の主要構成成分であるリン脂質からなる脂質二重膜で構成された閉鎖小胞体である。従来から、皮膚バリア機能を改善する薬剤などをリポソームに内包させて皮膚用化粧料に配合し、皮膚への経皮吸収性を高める試みがなされている（例えば、特許文献１〜３を参照）。 Liposomes are closed vesicles composed of a lipid bilayer composed of phospholipids, which are the main constituents of biological membranes. 2. Description of the Related Art Conventionally, attempts have been made to increase the transdermal absorbability to the skin by encapsulating drugs that improve the skin barrier function in liposomes and blending them in skin cosmetics (for example, see Patent Documents 1 to 3). .
しかしながら、リポソームは製剤中でリポソーム膜構造が壊れて「リポソームの形状が崩壊する」、「ミセル化する」などの問題があり、非常に不安定なものであることが知られている。そのため、リポソーム自体の保存安定性を高め、リポソームの製剤中での問題点を改善する試みもなされている。例えば、特定の多鎖多親水基型化合物、水を含有するリポソーム（例えば、特許文献４を参照）、リン脂質、ステロール、特定のＨＬＢのポリオキシエチレンステロールエーテル、多価アルコールおよび水を含有するリポソーム（例えば、特許文献５を参照）などが提案されている。 However, liposomes are known to be very unstable due to problems such as “the liposome shape is disrupted” and “micellarization” due to the disruption of the liposome membrane structure in the preparation. For this reason, attempts have been made to improve the storage stability of the liposome itself and to improve the problems in the preparation of the liposome. For example, it contains a specific multi-chain polyhydrophilic group type compound, a liposome containing water (see, for example, Patent Document 4), a phospholipid, a sterol, a specific HLB polyoxyethylene sterol ether, a polyhydric alcohol, and water. Liposomes (see, for example, Patent Document 5) have been proposed.
これら試みに拠って、ある程度、リポソーム自体の保存安定性を高めることができる反面、リポソーム膜が硬くなるために、本来のリポソームの機能、即ち、経皮吸収性を高める効果を十分に発揮させることに劣るといった問題がある。よって、リポソームの機能を十分に発揮させるためには、リポソーム膜を柔軟にして経皮吸収性を高めなければならない。しかしながら、リポソーム膜の柔軟性を高めると、リポソーム自体の保存安定性に劣るといった問題がある。そのため、リポソーム膜が柔軟であるリポソームを製剤中に配合することは困難であった。 Based on these attempts, the storage stability of the liposome itself can be enhanced to some extent, but the liposome membrane becomes hard, so that the function of the original liposome, that is, the effect of enhancing transdermal absorbability can be sufficiently exhibited. There is a problem of being inferior. Therefore, in order to fully exhibit the function of the liposome, the liposome membrane must be made flexible to enhance the transdermal absorbability. However, when the flexibility of the liposome membrane is increased, there is a problem that the storage stability of the liposome itself is poor. For this reason, it has been difficult to incorporate liposomes having a flexible liposome membrane into the preparation.
本発明は、前記従来技術に鑑みてなされたものであり、リポソーム膜の柔軟性を高めることができるとともに、リポソームの保存安定性に優れるリポソーム含有組成物、並びに該組成物を配合してなる皮膚用化粧料を提供することを課題とする。 The present invention has been made in view of the above prior art, and can improve the flexibility of the liposome membrane and has a liposome-containing composition excellent in the storage stability of the liposome, and skin obtained by blending the composition. It is an object to provide cosmetics for use.
即ち、本発明は、
〔１〕皮膚用化粧料に配合される組成物であって、（Ａ）リン脂質、（Ｂ）セラミド類、（Ｃ）炭素数１４〜３０の分岐型アルコール、並びに、（Ｄ）１，２−アルカンジオールおよびグリセリルモノアルキルエーテルの群から選ばれる少なくとも１種を含有し、前記１，２−アルカンジオールは、１，２−ヘキサンジオール、１，２−オクタンジオール、および１，２−デカンジオールの群から選ばれる少なくとも１種であり、（Ａ）成分、（Ｃ）成分および（Ｄ）成分の含有量が、下記含有質量比、
（Ｃ）成分／（Ａ）成分＝０．０１〜１、
（Ｄ）成分／（Ａ）成分＝０．０１〜１
の範囲を満たすことを特徴とするリポソーム含有組成物、
〔２〕（Ａ）成分が、水素添加リン脂質である前記〔１〕に記載のリポソーム含有組成物、
〔３〕（Ｃ）成分が、炭素数２０〜２４の分岐型アルコールである前記〔１〕又は〔２〕に記載のリポソーム含有組成物、
〔４〕（Ａ）成分、（Ｂ）成分および（Ｃ）成分の含有量が、下記含有質量比、
（Ｃ）成分／（（Ａ）成分＋（Ｂ）成分）＝０．０１〜０．７
の範囲を満たすことを特徴とする前記〔１〕〜〔３〕の何れ一つに記載のリポソーム含有組成物、
〔５〕（Ａ）成分、および（Ｂ）成分の含有量が、下記含有質量比、
（Ｂ）成分／（Ａ）成分＝０．０１〜１
の範囲を満たすことを特徴とする前記〔１〕〜〔４〕の何れ一つに記載のリポソーム含有組成物、並びに
〔６〕前記〔１〕〜〔５〕の何れか一つに記載のリポソーム含有組成物を配合してなる皮膚用化粧料
に関する。
That is, the present invention
[1] A composition to be blended in a cosmetic for skin, comprising (A) phospholipid, (B) ceramides, (C) a branched alcohol having 14 to 30 carbon atoms, and (D 1) 1 , 2 -Containing at least one selected from the group of alkanediol and glyceryl monoalkyl ether , wherein the 1,2-alkanediol is 1,2-hexanediol, 1,2-octanediol, and 1,2-decanediol The content of the component (A), the component (C) and the component (D) is at least one selected from the group of:
(C) component / (A) component = 0.01-1
(D) component / (A) component = 0.01-1
A liposome-containing composition characterized by satisfying the range of
[2] The liposome-containing composition according to [1], wherein the component (A) is a hydrogenated phospholipid,
[3] The liposome-containing composition according to [1] or [2], wherein the component (C) is a branched alcohol having 20 to 24 carbon atoms ,
[4 ] The content of the component (A), the component (B) and the component (C) is as follows:
(C) component / ((A) component + (B) component) = 0.01-0.7
The liposome-containing composition according to any one of the above [1] to [ 3 ], which satisfies the following range:
[5] The content of the component (A) and the component (B) is as follows:
(B) component / (A) component = 0.01-1
Said to satisfy the range of [1] to liposome-containing composition according to any one of [4], any one of <br/> in parallel beauty [6] above [1] to [5] The present invention relates to a skin cosmetic comprising the liposome-containing composition described in 1.
本発明のリポソーム含有組成物は、リポソーム膜の柔軟性を高めることができるという効果を奏する。また、リポソーム含有組成物を配合した皮膚用化粧料は、リポソーム膜が柔軟であるにもかかわらず、リポソームの形態が崩壊することなく維持し続けることから、保存安定性に格段に優れた効果を奏する。 The liposome-containing composition of the present invention has an effect that the flexibility of the liposome membrane can be enhanced. In addition, skin cosmetics formulated with a liposome-containing composition have a remarkably excellent effect on storage stability because the liposome membrane continues to be maintained without being disrupted even though the liposome membrane is flexible. Play.
本発明の皮膚用化粧料に配合されるリポソーム含有組成物は、（Ａ）リン脂質、（Ｂ）セラミド類およびステロール類の群から選ばれる少なくとも１種、並びに（Ｃ）分岐型アルコールを含有する。 The liposome-containing composition blended in the skin cosmetic of the present invention contains (A) at least one selected from the group of phospholipids, (B) ceramides and sterols, and (C) a branched alcohol. .
（Ａ）成分のリン脂質とは、リン酸残基を含む複合脂質であって、本発明においてはリポソームを形成する成分である。用いられる（Ａ）成分としては、天然リン脂質、合成リン脂質、天然由来のリン脂質の不飽和炭素鎖を水素により飽和とした水素添加リン脂質などが挙げられる。具体的には、例えば、ホスファチジルコリン、ホスファチジルエタノールアミン、ホスファチジルセリン、ホスファチジルイノシトール、リゾホスファチジルコリン、スフィンゴミエリン、卵黄レシチン、大豆レシチンなどの天然リン脂質；ジラウロイルホスファチジルコリン、ジミリストイルホスファチジルコリン、ジパルミトイルホスファチジルコリン、ジステアロイルホスファチジルコリン、ジオレオイルホスファチジルコリン、パルミトイル・オレオイルホスファチジルコリンなどの合成リン脂質；水素添加大豆レシチン、水素添加卵黄レシチン、水素添加ホスファチジルコリン、水素添加ホスファチジルセリンなどの水素添加リン脂質などを例示することができる。これら（Ａ）成分は、１種を単独で用いてもよく、２種以上を適宜組合せて用いることもできる。好適な（Ａ）成分としては、保存安定性に優れる観点から、水素添加リン脂質を用いることが好ましく、中でも、水素添加大豆レシチンを用いることがより好ましい。 The (A) component phospholipid is a complex lipid containing a phosphate residue, and in the present invention, is a component that forms a liposome. Examples of the component (A) used include natural phospholipids, synthetic phospholipids, and hydrogenated phospholipids in which unsaturated carbon chains of naturally derived phospholipids are saturated with hydrogen. Specifically, for example, natural phospholipids such as phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, phosphatidylinositol, lysophosphatidylcholine, sphingomyelin, egg yolk lecithin, soybean lecithin; dilauroyl phosphatidylcholine, dimyristoylphosphatidylcholine, dipalmitoylphosphatidylcholine, Examples include synthetic phospholipids such as phosphatidylcholine, dioleoylphosphatidylcholine, palmitoyl oleoylphosphatidylcholine; hydrogenated phospholipids such as hydrogenated soybean lecithin, hydrogenated egg yolk lecithin, hydrogenated phosphatidylcholine, and hydrogenated phosphatidylserine. These (A) components may be used individually by 1 type, and can also be used in combination of 2 or more type as appropriate. As a suitable component (A), it is preferable to use hydrogenated phospholipid from the viewpoint of excellent storage stability, and hydrogenated soybean lecithin is more preferable.
尚、（Ａ）成分は、市販品をそのまま用いることもできる。水素添加大豆レシチンの市販品としては、例えば、ＣＯＡＴＳＯＭＥ ＮＣ−６１（商品名，日油社製）、ＮＩＫＫＯＬ レシノールＳ−１０Ｍ（商品名，日光ケミカルズ社製）、ベイシス ＬＳ−６０ＨＲ（商品名，日清オイリオグループ社製）などを例示することができる。 In addition, a commercial item can also be used for (A) component as it is. Commercially available products of hydrogenated soybean lecithin include, for example, COATSOME NC-61 (trade name, manufactured by NOF Corporation), NIKKOL Resinol S-10M (trade name, manufactured by Nikko Chemicals), Basis LS-60HR (trade name, Nippon For example, Kiyo Erio Group).
（Ａ）成分の含有量は、所望の効果が充分に付与されるのであれば特に限定されないが、通常、リポソームを形成する観点から、組成物中、０．１質量％以上が好ましく、より好ましくは０．５質量％以上である。また、保存安定性の観点から、１０質量％以下が好ましく、より好ましくは３質量％以下である。これらの観点から、（Ａ）成分の含有量は、好ましくは０．１〜１０質量％、より好ましくは０．５〜３質量％である。 The content of the component (A) is not particularly limited as long as the desired effect is sufficiently imparted, but usually 0.1% by mass or more is preferable in the composition from the viewpoint of forming liposomes, and more preferably. Is 0.5% by mass or more. Moreover, from a viewpoint of storage stability, 10 mass% or less is preferable, More preferably, it is 3 mass% or less. From these viewpoints, the content of the component (A) is preferably 0.1 to 10% by mass, more preferably 0.5 to 3% by mass.
（Ｂ）成分のセラミド類は、上記（Ａ）成分により形成されるリポソームに内包される成分である。用いられるセラミド類の具体例としては、例えば、スフィンゴシン、フィトスフィンゴシン；スフィンゴシン、フィトスフィンゴシンの長鎖脂肪酸アミドであるセラミド１、セラミド２、セラミド３、セラミド３Ｂ、セラミド４、セラミド５、セラミド６、セラミド６Ｉ、セラミド６ＩＩなどの天然セラミド類；スフィンゴシン、フィトスフィンゴシンのリン脂質誘導体であるスフィンゴミエリン、フィトスフィンゴミエリンなどのスフィンゴリン脂質およびフィトスフィンゴリン脂質；スフィンゴシン、フィトスフィンゴシンの配糖体であるセレブロシド、ガングリオシドなどのスフィンゴ糖脂質およびフィトスフィンゴ糖脂質などを例示することができる。本発明においては、上記したセラミド類の他に化学合成で得られたセラミド類似化合物も好適に用いることができる。これら（Ｂ）成分は、１種を単独で用いてもよく、２種以上を適宜組合せて用いることもできる。 The ceramide component (B) is a component encapsulated in the liposome formed by the component (A). Specific examples of the ceramide used include, for example, sphingosine, phytosphingosine; sphingosine, ceramide 1, ceramide 2, ceramide 3, ceramide 3B, ceramide 4, ceramide 5, ceramide 6, ceramide, which is a long chain fatty acid amide of phytosphingosine Natural ceramides such as 6I and ceramide 6II; sphingosine, phytosphingosine phospholipid derivatives sphingomyelin, phytosphingomyelin and other sphingophospholipids and phytosphingophospholipid; sphingosine, phytosphingosine glycoside cerebroside, ganglioside Examples of the glycosphingolipids and phytosphingoglycolipids can be given. In the present invention, in addition to the ceramides described above, ceramide-like compounds obtained by chemical synthesis can also be suitably used. These (B) components may be used individually by 1 type, and can also be used in combination of 2 or more type as appropriate.
（Ｂ）成分の含有量は、リポソームに内包されて所望の効果が充分に発揮される量であれば特に限定されないが、（Ａ）成分との質量含有比が、（Ｂ）成分／（Ａ）成分＝０．０１〜１の範囲となるように含有させることが好ましく、より好ましくは０．０２〜０．５である。質量含有比が０．０１未満の場合、所望の効果が充分に発揮されないために好ましくない。また、質量含有比が１よりも多い場合、保存安定性に劣るために好ましくない。 The content of the component (B) is not particularly limited as long as the desired effect is sufficiently exhibited when encapsulated in the liposome, but the mass content ratio with the component (A) is (B) component / (A ) It is preferable to contain so that it may become the range of component = 0.01-1. More preferably, it is 0.02-0.5. When the mass content ratio is less than 0.01, the desired effect is not sufficiently exhibited, which is not preferable. Further, when the mass content ratio is more than 1, it is not preferable because the storage stability is poor.
（Ｃ）成分の分岐型アルコールとしては、炭素数１４〜３０の分岐型アルコールが挙げられる。具体的には、例えば、イソステアリルアルコール、ヘキシルデカノール、オクチルデカノール、オクチルドデカノール、デシルテトラデカノールなどを例示することができる。これら（Ｃ）成分は、１種を単独で用いてもよく、２種以上を適宜組合せて用いることもできる。好適な（Ｃ）成分としては、リポソーム膜を柔軟にする観点から、炭素数２０〜２４の分岐型アルコールを用いることが好ましく、中でも、オクチルドデカノール、デシルテトラデカノールを用いることがより好ましい。 (C) As a branched alcohol of a component, C14-30 branched alcohol is mentioned. Specific examples include isostearyl alcohol, hexyl decanol, octyl decanol, octyl decanol, and decyl tetradecanol. These (C) components may be used singly or in appropriate combination of two or more. As a suitable component (C), from the viewpoint of softening the liposome membrane, it is preferable to use a branched alcohol having 20 to 24 carbon atoms, and among them, octyldodecanol and decyltetradecanol are more preferable.
尚、（Ｃ）成分は、市販品をそのまま用いることもできる。オクチルドデカノールの市販品としては、例えば、カルコール２００ＧＤ（商品名，花王社製）などを例示することができる。デシルテトラデカノールの市販品としては、例えば、リソノール ２４ＳＰ（商品名，高級アルコール工業社製）などを例示することができる。 In addition, a commercial item can also be used for (C) component as it is. As a commercial item of octyldodecanol, for example, Calcoal 200GD (trade name, manufactured by Kao Corporation) can be exemplified. As a commercial item of decyltetradecanol, for example, Risonol 24SP (trade name, manufactured by Higher Alcohol Industry Co., Ltd.) can be exemplified.
（Ｃ）成分の含有量は、リポソームに配向されてリポソーム膜が柔軟となる量であれば特に限定されないが、（Ａ）成分との質量含有比が、（Ｃ）成分／（Ａ）成分＝０．０１〜１の範囲となるように含有させることが好ましく、より好ましくは０．０５〜０．５である。質量含有比が０．０１未満の場合、リポソーム膜の柔軟性に劣るために好ましくない。また、質量含有比が１よりも多い場合、リポソームの形態が崩壊するために好ましくない。 The content of the component (C) is not particularly limited as long as it is oriented in the liposome and the liposome membrane becomes flexible, but the mass content ratio with the component (A) is (C) component / (A) component = It is preferable to contain so that it may become the range of 0.01-1, More preferably, it is 0.05-0.5. When the mass content ratio is less than 0.01, the flexibility of the liposome membrane is inferior, which is not preferable. In addition, when the mass content ratio is more than 1, it is not preferable because the form of the liposome is collapsed.
上記（Ａ）〜（Ｃ）成分により形成されるリポソームの平均粒子径は、特に限定されないが、リポソームの保存安定性の観点から、２０〜３００ｎｍの範囲内とすることが好ましく、より好ましくは３０〜２００ｎｍである。尚、本発明のリポソームの平均粒子径とは、ＥＬＳ−８０００（大塚電子社製）を用いて、積算回数１００回で測定したときの値であるが、これら測定条件のみに限定されるものでない。 The average particle size of the liposome formed by the components (A) to (C) is not particularly limited, but is preferably in the range of 20 to 300 nm, more preferably 30 from the viewpoint of the storage stability of the liposome. ~ 200 nm. In addition, although the average particle diameter of the liposome of the present invention is a value measured with ELS-8000 (manufactured by Otsuka Electronics Co., Ltd.) at a total number of 100 times, it is not limited only to these measurement conditions. .
また、上記した（Ａ）成分、（Ｂ）成分および（Ｃ）成分の含有量は、リポソームの保存安定性を高める観点から、下記含有質量比、
（Ｃ）成分／（（Ａ）成分＋（Ｂ）成分）＝０．０１〜０．７
の範囲を満たすことが好ましく、０．０２〜０．５の範囲を満たすことがより好ましい。含有質量比が０．０１未満の場合、リポソーム膜の柔軟性に劣るために好ましくない。また、０．７よりも大きい場合、リポソームの形態が崩壊するために好ましくない。
In addition, the content of the component (A), the component (B), and the component (C) described above is from the viewpoint of enhancing the storage stability of the liposome,
(C) component / ((A) component + (B) component) = 0.01-0.7
It is preferable to satisfy | fill the range of 0.02, and it is more preferable to satisfy | fill the range of 0.02-0.5. When the content ratio is less than 0.01, the flexibility of the liposome membrane is inferior, which is not preferable. Moreover, when larger than 0.7, since the form of a liposome disintegrates, it is unpreferable.
本発明のリポソーム含有組成物には、リポソームの二分子膜に配向させることで更に柔軟性を高める観点から、（Ｄ）不飽和アルコール、１，２−アルカンジオールおよびグリセリルモノアルキルエーテルの群から選ばれる少なくとも１種を含有させることができる。用いられる不飽和アルコールとしては、炭素数１６〜２２の不飽和アルコールが挙げられ、具体的には、例えば、パルミトオレイルアルコール、オレイルアルコール、エライジルアルコール、リノレイルアルコール、リノレニルアルコール、イコセニルアルコール、エルシルアルコールなどを例示することができる。 The liposome-containing composition of the present invention is selected from the group of (D) unsaturated alcohol, 1,2-alkanediol and glyceryl monoalkyl ether from the viewpoint of further enhancing flexibility by orienting the bilayer membrane of the liposome. At least one selected from the group consisting of Examples of the unsaturated alcohol used include unsaturated alcohols having 16 to 22 carbon atoms. Specifically, for example, palmitooleyl alcohol, oleyl alcohol, elaidyl alcohol, linoleyl alcohol, linolenyl alcohol, ico Examples thereof include senyl alcohol and erucyl alcohol.
用いられる１，２−アルカンジオールの具体例としては、例えば、１，２−ヘキサンジオール、１，２−ペンタンジオール、１，２−オクタンジオール、１，２−デカンジオールなどを例示することができる。 Specific examples of the 1,2-alkanediol used include 1,2-hexanediol, 1,2-pentanediol, 1,2-octanediol, 1,2-decanediol, and the like. .
用いられるグリセリルモノアルキルエーテルの具体例としては、例えば、１−ブチルグリセリルエーテル、１−ヘキシルグリセリルエーテル、１−ヘプチルグリセリルエーテル、１−（２−エチルヘキシル）グリセリルエーテル、１−（３，５，５−トリメチルヘキシル）グリセリルエーテル、１−オクチルグリセリルエーテル、１−デシルグリセリルエーテル、１−ドデシルグリセリルエーテルなどを例示することができる。 Specific examples of the glyceryl monoalkyl ether used include, for example, 1-butyl glyceryl ether, 1-hexyl glyceryl ether, 1-heptyl glyceryl ether, 1- (2-ethylhexyl) glyceryl ether, 1- (3, 5, 5 -Trimethylhexyl) glyceryl ether, 1-octyl glyceryl ether, 1-decyl glyceryl ether, 1-dodecyl glyceryl ether and the like can be exemplified.
これら（Ｄ）成分は、１種を単独で用いてもよく、２種以上を適宜組合せて用いることもできる。好適な（Ｄ）成分としては、リポソーム膜の柔軟性を更に高める観点から、オレイルアルコール、１，２−オクタンジオール、１−（２−エチルヘキシル）グリセリルエーテルを用いることが好ましい。 These components (D) may be used alone or in combination of two or more. As a suitable component (D), it is preferable to use oleyl alcohol, 1,2-octanediol, 1- (2-ethylhexyl) glyceryl ether from the viewpoint of further enhancing the flexibility of the liposome membrane.
（Ｄ）成分の含有量は、リポソームに配向されてリポソーム膜の柔軟性を高めることができる量であれば特に限定されないが、（Ａ）成分との質量含有比が、（Ｄ）成分／（Ａ）成分＝０．０１〜１の範囲となるように含有させることが好ましく、より好ましくは０．０５〜０．５である。質量含有比が０．０１未満の場合、リポソーム膜の柔軟性を更に高めることに好ましくない。また、質量含有比が１よりも多い場合、リポソームの形態が崩壊するために好ましくない。 The content of the component (D) is not particularly limited as long as it is an amount that can be oriented in the liposome and increase the flexibility of the liposome membrane, but the mass content ratio with the component (A) is (D) component / ( It is preferable to make it contain so that it may become the range of A) component = 0.01-1, More preferably, it is 0.05-0.5. When the mass content ratio is less than 0.01, it is not preferable for further enhancing the flexibility of the liposome membrane. In addition, when the mass content ratio is more than 1, it is not preferable because the form of the liposome is collapsed.
本発明のリポソームを含有する組成物を調製するためには、溶剤として１，２−アルカンジオール以外の多価アルコールが用いられる。多価アルコールの具体例としては、例えば、エチレングリコール、ジエチレングリコール、トリエチレングリコール、ポリエチレングリコール、プロピレングリコール、ジプロピレングリコール、イソプレングリコール、１，３−ブチレングリコール、グリセリン、濃グリセリン、ジグリセリン、ポリグリセリンなどを例示することができる。これら成分は、１種を単独で用いてもよく、２種以上を適宜組合せて用いることもできる。 In order to prepare the composition containing the liposome of the present invention, a polyhydric alcohol other than 1,2-alkanediol is used as a solvent. Specific examples of the polyhydric alcohol include, for example, ethylene glycol, diethylene glycol, triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, isoprene glycol, 1,3-butylene glycol, glycerin, concentrated glycerin, diglycerin, and polyglycerin. Etc. can be illustrated. These components may be used alone or in combination of two or more.
多価アルコールの含有量は、所望の効果が充分に付与されるのであれば特に限定されないが、通常、リポソーム調製時の溶解性の観点から、組成物中、１質量％以上が好ましく、より好ましくは２質量％以上である。また、保存安定性の観点から、５０質量％以下が好ましく、より好ましくは３０質量％以下である。これらの観点から、多価アルコールの含有量は、好ましくは１〜５０質量％、より好ましくは２〜３０質量％である。 The content of the polyhydric alcohol is not particularly limited as long as the desired effect is sufficiently imparted, but usually 1% by mass or more is preferable in the composition from the viewpoint of solubility during preparation of the liposome, more preferably. Is 2% by mass or more. Moreover, from a viewpoint of storage stability, 50 mass% or less is preferable, More preferably, it is 30 mass% or less. From these viewpoints, the content of the polyhydric alcohol is preferably 1 to 50% by mass, more preferably 2 to 30% by mass.
リポソームを含有する組成物の製造方法は、公知の方法を用いて製造することができれば特に限定されないが、好ましくは以下の製造方法を例示することができる。 Although the manufacturing method of the composition containing a liposome will not be specifically limited if it can manufacture using a well-known method, Preferably the following manufacturing methods can be illustrated.
始めに、多価アルコールに（Ａ）成分を加え、７０〜９０℃の温度範囲で均一溶解して混合物（１）を得る。次いで、多価アルコールに（Ｂ）成分および（Ｃ）成分を加え、７０〜９５℃の温度範囲で均一溶解した混合物（２）を、先に調製した混合物（１）に８０℃以上で加え混合する。均一に混合後、８０℃以上に加温した精製水を加え、ホモミキサー（Ｔ．Ｋ．ロボミックス，特殊機化工業社製）を用いて、６０００ｒｐｍ、５分間攪拌する。このような製造工程により、本発明のリポソームを含有する組成物を調製することができる。尚、（Ｄ）成分を含有させる場合は、混合物（１）を調製時に（Ａ）成分とともに多価アルコールに溶解させれば良い。 First, the component (A) is added to the polyhydric alcohol and uniformly dissolved in a temperature range of 70 to 90 ° C. to obtain a mixture (1). Next, the component (B) and the component (C) are added to the polyhydric alcohol, and the mixture (2) uniformly dissolved in the temperature range of 70 to 95 ° C. is added to the mixture (1) prepared above at 80 ° C. or more and mixed. To do. After uniformly mixing, purified water heated to 80 ° C. or higher is added, and the mixture is stirred at 6000 rpm for 5 minutes using a homomixer (TK Robotics, manufactured by Tokushu Kika Kogyo Co., Ltd.). By such a production process, a composition containing the liposome of the present invention can be prepared. In addition, what is necessary is just to dissolve a mixture (1) in a polyhydric alcohol with (A) component at the time of preparation, when (D) component is contained.
また、本発明においては、より微細なリポソームとするために、高圧ホモジナイザー（（マイクロフルイダイザーＭ−１１０−Ｅ／Ｈ，マイクロフルイディックス社製）又は精密乳化分散機（クレアミックス，エム・テクニック社製）を用いて微細化を施しても良い。 In the present invention, in order to obtain finer liposomes, a high-pressure homogenizer (Microfluidizer M-110-E / H, manufactured by Microfluidics) or a precision emulsifier / disperser (Claremix, M Technique Co., Ltd.) May be used to make finer.
次に、本発明のリポソーム含有組成物が配合される皮膚用化粧料について説明する。皮膚用化粧料を調製する場合、リポソームの保存安定性を損なわない範囲であれば、通常化粧品に用いられる成分、例えば、高級アルコール、脂肪酸、油脂、エステル油、シリコーン油などの油剤、非イオン性界面活性剤、低級アルコール、保湿剤、金属封鎖剤、防腐剤、植物抽出エキス、香料、ｐＨ調整剤、精製水などを目的に応じて適宜配合することができる。 Next, the cosmetic for skin to which the liposome-containing composition of the present invention is blended will be described. When preparing skin cosmetics, as long as the storage stability of the liposome is not impaired, components usually used in cosmetics such as higher alcohols, fatty acids, oils and fats, ester oils, silicone oils and the like, nonionic A surfactant, a lower alcohol, a moisturizer, a metal sequestering agent, an antiseptic, a plant extract, a fragrance, a pH adjuster, purified water, and the like can be appropriately blended depending on the purpose.
用いられる油剤の具体例としては、例えば、ラウリルアルコール、ミリスチルアルコール、セチルアルコール、ステアリルアルコール、オレイルアルコール、ラノリンアルコール、ベヘニルアルコール、セトステアリルアルコールなどの高級アルコール；ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、オレイン酸、ベヘニン酸、ウンデシレン酸、ラノリン酸、イソステアリン酸などの脂肪酸；ヤシ油、パーム油、水素添加パーム油、アボカド油、ゴマ油、オリーブ油、ククイナッツ油、ブドウ粒子油、サフラワー油、アーモンド油、トウモロコシ油、綿実油、ヒマワリ種子油、ブドウ種子油、ヘーゼルナッツ油、マカデミアナッツ油、メドウフォーム油、ローズヒップ油などの油脂；オレイン酸エチル、ミリスチン酸イソプロピル、パルミチン酸イソプロピル、ミリスチン酸ミリスチル、パルミチン酸セチル、オレイン酸オレイル、ミリスチン酸オクチルドデシル、オレイン酸オクチルドデシル、イソステアリン酸エチル、イソステアリン酸イソプロピル、２−エチルヘキサン酸セチル、２−エチルヘキサン酸セトステアリル、トリ２−エチルヘキサン酸グリセリル、トリ（カプリル・カプリン酸）グリセリル、トリイソパルミチン酸グリセリル、テトラ２−エチルヘキサン酸ペンタエリスリトール、オクタン酸イソセチル、オクタン酸イソステアリル、イソステアリン酸イソセチル、イソステアリン酸オクチルドデシル、ジメチルオクタン酸オクチルドデシルなどのエステル油；メチルポリシロキサン、高重合メチルポリシロキサン、メチルフェニルポリシロキサン、オクタメチルトリシロキサン、デカメチルテトラシロキサン、オクタメチルシクロテトラシロキサン、デカメチルシクロペンタシロキサン、ドデカメチルシクロヘキサシロキサン、メチルシクロポリシロキサン、アルコール変性シリコーン、アルキル変性シリコーン、アミノ変性シリコーン、エポキシ変性シリコーンなどのシリコーン油などを例示することができる。これら油剤は、１種を単独で用いてもよく、２種以上を適宜組合せて用いることもできる。 Specific examples of the oil used include higher alcohols such as lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, oleyl alcohol, lanolin alcohol, behenyl alcohol, cetostearyl alcohol; lauric acid, myristic acid, palmitic acid, stearic acid Fatty acids such as oleic acid, behenic acid, undecylenic acid, lanolinic acid, isostearic acid; coconut oil, palm oil, hydrogenated palm oil, avocado oil, sesame oil, olive oil, kukui nut oil, grape particle oil, safflower oil, almond oil Oils such as corn oil, cottonseed oil, sunflower seed oil, grape seed oil, hazelnut oil, macadamia nut oil, meadow foam oil, rosehip oil; ethyl oleate, isopropyl myristate , Isopropyl palmitate, myristyl myristate, cetyl palmitate, oleyl oleate, octyldodecyl myristate, octyldodecyl oleate, ethyl isostearate, isopropyl isostearate, cetyl 2-ethylhexanoate, cetostearyl 2-ethylhexanoate, Glyceryl tri-2-ethylhexanoate, glyceryl tri (capryl / caprate), glyceryl triisopalmitate, pentaerythritol tetra-2-ethylhexanoate, isocetyl octoate, isostearyl octoate, isocetyl isostearate, octyldodecyl isostearate, Ester oil such as octyldodecyl dimethyloctanoate; methylpolysiloxane, highly polymerized methylpolysiloxane, methylphenylpolysiloxane Octamethyltrisiloxane, decamethyltetrasiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, methylcyclopolysiloxane, alcohol-modified silicone, alkyl-modified silicone, amino-modified silicone, epoxy-modified silicone, etc. A silicone oil etc. can be illustrated. These oil agents may be used alone or in combination of two or more.
用いられる非イオン性界面活性剤としては、例えば、グリセリン脂肪酸エステル、グリセリン脂肪酸エステルの酸化エチレン縮合物、ポリアルキレングリコール脂肪酸エステル、ソルビタン脂肪酸エステル、ソルビタン脂肪酸エステルの酸化エチレン縮合物などの脂肪酸エステル型非イオン性界面活性剤の他、ポリオキシアルキレンアルキルエーテル、ポリオキシエチレン硬化ヒマシ油、ポリオキシエチレンヒマシ油、ポリオキシエチレンラノリンなどが挙げられる。これら非イオン性界面活性剤は、１種を単独で用いてもよく、２種以上を適宜組合せて用いることもできる。 Examples of the nonionic surfactant used include fatty acid ester-type non-ionic surfactants such as glycerin fatty acid ester, ethylene oxide condensate of glycerin fatty acid ester, polyalkylene glycol fatty acid ester, sorbitan fatty acid ester, and ethylene oxide condensate of sorbitan fatty acid ester. In addition to ionic surfactants, polyoxyalkylene alkyl ether, polyoxyethylene hydrogenated castor oil, polyoxyethylene castor oil, polyoxyethylene lanolin and the like can be mentioned. One of these nonionic surfactants may be used alone, or two or more thereof may be used in appropriate combination.
グリセリン肪酸エステルとしては、本発明においては、グリセリン脂肪酸エステルおよびポリグリセリン脂肪酸エステルのいずれをも意味し、具体的には、モノカプリル酸グリセリル、モノカプリン酸グリセリル、モノラウリン酸グリセリル、モノミリスチン酸グリセリル、モノパルミチン酸グリセリル、モノステアリン酸グリセリル、モノイソステアリン酸グリセリル、モノベヘン酸グリセリル、モノオレイン酸グリセリル、モノエルカ酸グリセリル、セスキオレイン酸グリセリル、ジステアリン酸グリセリル、ジイソステアリン酸グリセリル、ジアラキン酸グリセリルなどのグリセリン脂肪酸エステル；モノカプリル酸ジグリセリル、モノカプリル酸デカグリセリル、モノカプリン酸ヘキサグリセリル、モノラウリン酸テトラグリセリル、モノラウリン酸ヘキサグリセリル、モノラウリン酸デカグリセリル、モノラウリン酸ポリ（４〜１０）グリセリル、モノミリスチン酸デカグリセリル、モノステアリン酸デカグリセリル、モノイソステアリン酸デカグリセリル、モノステアリン酸ポリ（２〜１０）グリセリル、モノオレイン酸ジグリセリル、モノオレイン酸ヘキサグリセリル、セスキオレイン酸ジグリセリル、ジイソステアリン酸ポリ（２〜１０）グリセリル、ジステアリン酸ポリ（６〜１０）グリセリル、トリイソステアリン酸ジグリセリル、トリステアリン酸ポリ（１０）グリセリルなどの上記したグリセリン脂肪酸エステルの重合度２〜１０のポリグリセリン脂肪酸エステルを例示することができる。また、グリセリン脂肪酸エステルの酸化エチレン縮合物としては、モノステアリン酸ポリオキシエチレングリセリル、モノオレイン酸ポリオキシエチレングリセリルなどを例示することができる。 In the present invention, glycerin fatty acid ester means both glycerin fatty acid ester and polyglycerin fatty acid ester. Specifically, glyceryl monocaprylate, glyceryl monocaprate, glyceryl monolaurate, glyceryl monomyristate Glyceryl fatty acid esters such as glyceryl monopalmitate, glyceryl monostearate, glyceryl monoisostearate, glyceryl monobehenate, glyceryl monooleate, glyceryl monoerucate, glyceryl sesquioleate, glyceryl distearate, glyceryl diisostearate, glyceryl diarachiate ; Diglyceryl monocaprylate, decaglyceryl monocaprylate, hexaglyceryl monocaprate, tetraglyceryl monolaurate Hexaglyceryl monolaurate, decaglyceryl monolaurate, poly (4-10) glyceryl monolaurate, decaglyceryl monomyristate, decaglyceryl monostearate, decaglyceryl monoisostearate, poly (2-10) glyceryl monostearate, mono Diglyceryl oleate, hexaglyceryl monooleate, diglyceryl sesquioleate, poly (2-10) glyceryl diisostearate, poly (6-10) glyceryl distearate, diglyceryl triisostearate, poly (10) tristearate Examples thereof include polyglycerol fatty acid esters having a polymerization degree of 2 to 10 as described above, such as glyceryl. Examples of the ethylene oxide condensate of glycerol fatty acid ester include polyoxyethylene glyceryl monostearate and polyoxyethylene glyceryl monooleate.
ポリアルキレングリコール脂肪酸エステルとしては、例えば、モノラウリン酸ポリエチレングリコール、モノステアリン酸ポリエチレングリコール、モノイソステアリン酸ポリエチレングリコール、モノオレイン酸ポリエチレングリコール、ジラウリン酸ポリエチレングリコール、ジステアリン酸ポリエチレングリコール、ジイソステアリン酸ポリエチレングリコール、ジオレイン酸ポリエチレングリコールなどのポリエチレングリコール脂肪酸エステル；モノステアリン酸プロピレングリコール、モノラウリン酸プロピレングリコール、モノオレイン酸プロピレングリコールなどのプロピレングリコール脂肪酸エステルなどを例示することができる。 Examples of the polyalkylene glycol fatty acid ester include polyethylene glycol monolaurate, polyethylene glycol monostearate, polyethylene glycol monoisostearate, polyethylene glycol monooleate, polyethylene glycol dilaurate, polyethylene glycol distearate, polyethylene glycol diisostearate, and dioleic acid. Examples include polyethylene glycol fatty acid esters such as polyethylene glycol; propylene glycol fatty acid esters such as propylene glycol monostearate, propylene glycol monolaurate, and propylene glycol monooleate.
ソルビタン脂肪酸エステルとしては、例えば、モノオレイン酸ソルビタン、モノステアリン酸ソルビタン、モノイソステアリン酸ソルビタン、モノパルミチン酸ソルビタン、モノラウリン酸ソルビタン、トリオレイン酸ソルビタン、トリステアリン酸ソルビタン、セスキステアリン酸ソルビタン、セスキオレイン酸ソルビタン、セスキイソステアリン酸ソルビタン、ヤシ油脂肪酸ソルビタンなどのソルビタン脂肪酸エステルを例示することができる。また、ソルビタン脂肪酸エステルの酸化エチレン縮合物としては、モノラウリン酸ポリオキシエチレンソルビタン、モノパルミチン酸ポリオキシエチレンソルビタン、モノステアリン酸ポリオキシエチレンソルビタン、モノオレイン酸ポリオキシエチレンソルビタン、モノイソステアリン酸ポリオキシエチレンソルビタン、モノヤシ油脂肪酸ポリオキシエチレンソルビタン、トリステアリン酸ポリオキシエチレンソルビタン、トリオレイン酸ポリオキシエチレンソルビタンなどを例示することができる。 Examples of sorbitan fatty acid esters include sorbitan monooleate, sorbitan monostearate, sorbitan monoisostearate, sorbitan monopalmitate, sorbitan monolaurate, sorbitan trioleate, sorbitan tristearate, sorbitan sesquistearate, sesquioleate Examples include sorbitan fatty acid esters such as sorbitan, sorbitan sesquiisostearate, and coconut oil fatty acid sorbitan. Examples of the ethylene oxide condensate of sorbitan fatty acid ester include polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan monooleate, polyoxyethylene monoisostearate Examples include sorbitan, mono coconut oil fatty acid polyoxyethylene sorbitan, polyoxyethylene sorbitan tristearate, polyoxyethylene sorbitan trioleate, and the like.
ポリオキシアルキレンアルキルエーテルとしては、例えば、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンセチルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンポリオキシプロピレンラウリルエーテル、ポリオキシプロピレンセチルエーテル、ポリオキシプロピレンイソセチルエーテル、ポリオキシプロピレンステアリルエーテル、ポリオキシプロピレンオレイルエーテルなどを例示することができる。 Examples of the polyoxyalkylene alkyl ether include polyoxyethylene lauryl ether, polyoxyethylene cetyl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene polyoxypropylene lauryl ether, polyoxypropylene cetyl ether, Examples thereof include oxypropylene isocetyl ether, polyoxypropylene stearyl ether, and polyoxypropylene oleyl ether.
また、本発明の皮膚用化粧料の形態は、リポソームが安定に配合されるのであれば特に限定されず、液状、乳液状、クリーム状、ジェル状などの種々の形態をとり得ることができる。更に、本発明のリポソーム含有組成物は、リポソーム膜が柔軟であるにもかかわらずリポソームの形態が崩壊することなく維持し続けることから、通常、リポソームの配合が困難である乳液状、クリーム状の形態にも好適に用いることができる。 The form of the cosmetic for skin of the present invention is not particularly limited as long as the liposome is stably blended, and can take various forms such as liquid, emulsion, cream, and gel. Furthermore, since the liposome-containing composition of the present invention continues to maintain the form of the liposome without collapsing despite the fact that the liposome membrane is flexible, it is usually an emulsion or cream that is difficult to mix with the liposome. It can use suitably also for a form.
以下、本発明を実施例に基づいて更に詳細に説明するが、本発明はこれら実施例にのみ限定されるものではない。尚、配合量は、特記しない限り「質量％」を表す。また、評価はすべて、２３℃、湿度６０％の恒温恒湿の一定条件下で実施した。 EXAMPLES Hereinafter, although this invention is demonstrated further in detail based on an Example, this invention is not limited only to these Examples. The blending amount represents “% by mass” unless otherwise specified. Moreover, all evaluation was implemented on the constant conditions of constant temperature and humidity of 23 degreeC and 60% of humidity.
（試料の調製１）
表１および表２に記した組成に従い、処方例１〜１０の各リポソームを常法に準じて調製した。尚、示差走査熱量測定における吸熱ピークの検出限界を考慮して、リポソーム濃度を高くした試料にて下記評価に供した。
(Sample preparation 1)
According to the composition described in Table 1 and Table 2, each liposome of Formulation Examples 1 to 10 was prepared according to a conventional method. In consideration of the detection limit of the endothermic peak in differential scanning calorimetry, the sample was subjected to the following evaluation using a sample with a high liposome concentration.
（試験例１：リポソーム膜の柔軟性試験）
処方例１〜１０の各リポソームをアロジン処理済みアルミニウム製密封容器（エスアイアイ・ナノテクノロジー社製）に適量封入し、示差走査熱量測定（ＤＳＣ；ＥＸＳＴＡＲ６０００：エスアイアイ・ナノテクノロジー社製）を用いて２０℃〜８０℃の範囲で５℃／ｍｉｎの条件にて測定した。結果を表１および表２に併記する。また、示差走査熱量測定結果のチャートを図１および図２に示す。
(Test Example 1: Liposome membrane flexibility test)
Appropriate amounts of each of the liposomes of Formulation Examples 1 to 10 are sealed in an allodin-treated aluminum sealed container (SII NanoTechnology), and differential scanning calorimetry (DSC; EXSTAR6000: SII NanoTechnology) is used. The measurement was performed under the condition of 5 ° C./min in the range of 20 ° C. to 80 ° C. The results are shown in Tables 1 and 2. Moreover, the chart of a differential scanning calorimetry result is shown in FIG. 1 and FIG.
本測定は、セラミド２および膜構成成分である水素添加大豆レシチンの疎水基間相互作用における他因子、具体的には、リポソーム含有組成物の調製時に用いる多価アルコールなどの溶剤の影響を取り除くために、溶剤としてクロロホルム−メタノール溶液（２：１）を用い、薄膜法（バンガム法）にて調製したリポソームの示差走査熱量測定を行った。 This measurement is to remove the influence of other factors in the interaction between hydrophobic groups of ceramide 2 and hydrogenated soybean lecithin, which is a membrane component, specifically, the effects of solvents such as polyhydric alcohols used in preparing liposome-containing compositions. In addition, using a chloroform-methanol solution (2: 1) as a solvent, differential scanning calorimetry of liposomes prepared by a thin film method (Bangham method) was performed.
尚、薄膜法（バンガム法）とは、リポソーム膜構成成分（Ａ）〜（Ｄ）をクロロホルム−メタノール溶液（２：１）に溶解後、ロータリーエバポレーターにて溶媒を留去し、脂質フィルムを作成する。そこへ精製水を加え、８０℃以上に加温後、振とうしてフィルムをはがし、試料を調製する方法である。 The thin film method (Bangham method) is a lipid film prepared by dissolving the liposome membrane components (A) to (D) in a chloroform-methanol solution (2: 1) and then distilling off the solvent with a rotary evaporator. To do. Purified water is added thereto, heated to 80 ° C. or higher, shaken, and the film is peeled off to prepare a sample.
表１および表２、並びに図１および図２に示す通り、示差走査熱量測定結果から、処方例１〜５のリポソームは、処方例６のリポソームと対比して、セラミド２および膜構成成分である水素添加大豆レシチンの疎水基間相互作用を弱め、リポソーム膜の相転移温度（融点）の低下を引き起こし、リポソーム膜を柔らかくする、即ち、リポソーム膜の柔軟性を高めていることが確認された。 As shown in Tables 1 and 2 and FIGS. 1 and 2, from the results of differential scanning calorimetry, the liposomes of Formulation Examples 1 to 5 are ceramide 2 and a membrane constituent, as compared with the liposomes of Formulation Example 6. It was confirmed that the interaction between the hydrophobic groups of hydrogenated soybean lecithin was weakened, the phase transition temperature (melting point) of the liposome membrane was lowered, and the liposome membrane was softened, that is, the flexibility of the liposome membrane was increased.
これに対して、処方例７〜１０のリポソームは、処方例６のリポソームの相転移温度と同等、若しくは相転移温度が上昇していることから、リポソーム膜を硬くする、即ち、リポソーム膜の硬化性を高めていることが確認された。 On the other hand, the liposomes of Formulation Examples 7 to 10 are equivalent to the phase transition temperature of the liposome of Formulation Example 6 or the phase transition temperature is increased, so that the liposome membrane is hardened, that is, the liposome membrane is cured. It was confirmed that the sex was improved.
（試料の調製２）
表３に記した組成に従い、実施例１〜５のリポソーム膜の柔軟性に優れるリポソーム含有組成物を常法に準じて調製した。
(Sample preparation 2)
According to the composition described in Table 3, liposome-containing compositions having excellent flexibility of the liposome membranes of Examples 1 to 5 were prepared according to a conventional method.
（試料の調製３）
表４に記した組成に従い、実施例１〜５の各リポソーム含有組成物を配合した実施例６〜１０の皮膚用化粧料を常法に準じて調製し、下記評価に供した。
(Sample preparation 3)
According to the composition described in Table 4, skin cosmetics of Examples 6 to 10 in which the liposome-containing compositions of Examples 1 to 5 were blended were prepared according to a conventional method and subjected to the following evaluation.
（試験例２：保存安定性の評価）
実施例６〜１０で得られた試料の製造直後のリポソームの形態を透過型電子顕微鏡により観察した。次いで、各試料を５０ｍＬ容の透明ガラス容器にそれぞれ封入し、４０℃の恒温槽に夫々６週間保存した後のリポソームの形態を透過型電子顕微鏡により再度観察し、以下の評価基準に従って評価した。
尚、透過型電子顕微鏡での観察は、ネガティブ染色法で行った。
(Test Example 2: Evaluation of storage stability)
The morphology of the liposomes immediately after production of the samples obtained in Examples 6 to 10 was observed with a transmission electron microscope. Next, each sample was sealed in a 50 mL clear glass container and stored in a constant temperature bath at 40 ° C. for 6 weeks, and the morphology of the liposomes was observed again with a transmission electron microscope and evaluated according to the following evaluation criteria.
The observation with a transmission electron microscope was carried out by a negative staining method.
＜保存安定性の評価基準＞
○：製造直後と全く変化が認められない（リポソームの形態が崩壊していない）
△：リポソームの形態が一部崩壊しミセル化している
×：リポソームの形態が全崩壊しミセル化している
<Evaluation criteria for storage stability>
○: No change is observed immediately after production (the form of the liposome has not collapsed)
Δ: Liposomes partially disintegrated and micelles ×: Liposomes completely disintegrated and micelles
表４に示された結果から、各実施例で得られた皮膚用化粧料は、リポソーム膜が柔軟であるにもかかわらず、リポソームの形態を崩壊させることなく、安定に配合できていることが分かる。即ち、リポソームの保存安定性に格段に優れた効果を奏していることが分かる。 From the results shown in Table 4, the skin cosmetics obtained in each example can be stably blended without disrupting the liposome form even though the liposome membrane is flexible. I understand. That is, it can be seen that the storage stability of the liposome is remarkably excellent.
Claims (6)
前記１，２−アルカンジオールは、１，２−ヘキサンジオール、１，２−オクタンジオール、および１，２−デカンジオールの群から選ばれる少なくとも１種であり、
（Ａ）成分、（Ｃ）成分および（Ｄ）成分の含有量が、下記含有質量比、
（Ｃ）成分／（Ａ）成分＝０．０１〜１、
（Ｄ）成分／（Ａ）成分＝０．０１〜１
の範囲を満たすことを特徴とするリポソーム含有組成物。 A composition blended in a cosmetic for skin, comprising (A) a phospholipid, (B) a ceramide, (C) a branched alcohol having 14 to 30 carbon atoms, and (D ) 1,2-alkanediol And at least one selected from the group of glyceryl monoalkyl ethers ,
The 1,2-alkanediol is at least one selected from the group of 1,2-hexanediol, 1,2-octanediol, and 1,2-decanediol,
The content of the component (A), the component (C) and the component (D) is the following content mass ratio,
(C) component / (A) component = 0.01-1
(D) component / (A) component = 0.01-1
Liposome-containing composition characterized by satisfying the above range .
（Ｃ）成分／（（Ａ）成分＋（Ｂ）成分）＝０．０１〜０．７
の範囲を満たすことを特徴とする請求項１〜３の何れか一項に記載のリポソーム含有組成物。 Content of (A) component, (B) component, and (C) component is the following content mass ratio,
(C) component / ((A) component + (B) component) = 0.01-0.7
The liposome-containing composition according to any one of claims 1 to 3 , wherein the composition satisfies the above range.
（Ｂ）成分／（Ａ）成分＝０．０１〜１ (B) component / (A) component = 0.01-1
の範囲を満たすことを特徴とする請求項１〜４の何れか一項に記載のリポソーム含有組成物。The liposome-containing composition according to any one of claims 1 to 4, wherein the composition satisfies the above range.
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