JP2024021931A - Emulsified compositions and cosmetics - Google Patents
Emulsified compositions and cosmetics Download PDFInfo
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- JP2024021931A JP2024021931A JP2022125138A JP2022125138A JP2024021931A JP 2024021931 A JP2024021931 A JP 2024021931A JP 2022125138 A JP2022125138 A JP 2022125138A JP 2022125138 A JP2022125138 A JP 2022125138A JP 2024021931 A JP2024021931 A JP 2024021931A
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- emulsified composition
- carbon atoms
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- 239000000203 mixture Substances 0.000 title claims abstract description 101
- 239000002537 cosmetic Substances 0.000 title claims description 37
- -1 diester compound Chemical class 0.000 claims abstract description 51
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical class C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 claims abstract description 41
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 24
- 239000004094 surface-active agent Substances 0.000 claims abstract description 21
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 40
- 239000000194 fatty acid Substances 0.000 claims description 40
- 229930195729 fatty acid Natural products 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 235000010445 lecithin Nutrition 0.000 claims description 24
- 239000000787 lecithin Substances 0.000 claims description 24
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 21
- 229940067606 lecithin Drugs 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 claims description 18
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- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 16
- 235000010384 tocopherol Nutrition 0.000 claims description 16
- 229960001295 tocopherol Drugs 0.000 claims description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 150000004665 fatty acids Chemical class 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000004615 ingredient Substances 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
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- 150000003611 tocopherol derivatives Chemical class 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
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- 150000005690 diesters Chemical class 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
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- 150000005846 sugar alcohols Polymers 0.000 description 19
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- 239000005720 sucrose Substances 0.000 description 15
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 14
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- 239000002253 acid Substances 0.000 description 12
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- 239000008346 aqueous phase Substances 0.000 description 11
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- 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 10
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- 238000002835 absorbance Methods 0.000 description 8
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 8
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- 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 8
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 7
- 230000000996 additive effect Effects 0.000 description 7
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 102000008186 Collagen Human genes 0.000 description 6
- 108010035532 Collagen Proteins 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 229920001436 collagen Polymers 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 230000006870 function Effects 0.000 description 6
- 150000002327 glycerophospholipids Chemical class 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
- WNIFXKPDILJURQ-JKPOUOEOSA-N octadecyl (2s,4as,6ar,6as,6br,8ar,10s,12as,14br)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1h-picene-2-carboxylate Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CC[C@@](C(=O)OCCCCCCCCCCCCCCCCCC)(C)C[C@H]5C4=CC(=O)[C@@H]3[C@]21C WNIFXKPDILJURQ-JKPOUOEOSA-N 0.000 description 6
- 239000003002 pH adjusting agent Substances 0.000 description 6
- WOKDXPHSIQRTJF-UHFFFAOYSA-N 3-[3-[3-[3-[3-[3-[3-[3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)COCC(O)CO WOKDXPHSIQRTJF-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 230000001804 emulsifying effect Effects 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- WNIFXKPDILJURQ-UHFFFAOYSA-N stearyl glycyrrhizinate Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(=O)OCCCCCCCCCCCCCCCCCC)(C)CC5C4=CC(=O)C3C21C WNIFXKPDILJURQ-UHFFFAOYSA-N 0.000 description 5
- 229930003802 tocotrienol Natural products 0.000 description 5
- 239000011731 tocotrienol Substances 0.000 description 5
- 235000019148 tocotrienols Nutrition 0.000 description 5
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 4
- ZAKOWWREFLAJOT-CEFNRUSXSA-N D-alpha-tocopherylacetate Chemical compound CC(=O)OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C ZAKOWWREFLAJOT-CEFNRUSXSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 235000010469 Glycine max Nutrition 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- MPDGHEJMBKOTSU-UHFFFAOYSA-N Glycyrrhetinsaeure Natural products C12C(=O)C=C3C4CC(C)(C(O)=O)CCC4(C)CCC3(C)C1(C)CCC1C2(C)CCC(O)C1(C)C MPDGHEJMBKOTSU-UHFFFAOYSA-N 0.000 description 4
- 239000005639 Lauric acid Substances 0.000 description 4
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 235000021355 Stearic acid Nutrition 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 235000010323 ascorbic acid Nutrition 0.000 description 4
- 239000011668 ascorbic acid Substances 0.000 description 4
- 229960005070 ascorbic acid Drugs 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229960003720 enoxolone Drugs 0.000 description 4
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 4
- 150000004676 glycans Chemical class 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 229920001282 polysaccharide Polymers 0.000 description 4
- 239000005017 polysaccharide Substances 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000008117 stearic acid Substances 0.000 description 4
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 4
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical class N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 3
- 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 3
- BJDAUCLANVMIOB-UHFFFAOYSA-N (3-decanoyloxy-2,2-dimethylpropyl) decanoate Chemical compound CCCCCCCCCC(=O)OCC(C)(C)COC(=O)CCCCCCCCC BJDAUCLANVMIOB-UHFFFAOYSA-N 0.000 description 3
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- GJJVAFUKOBZPCB-UHFFFAOYSA-N 2-methyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol Chemical compound OC1=CC=C2OC(CCC=C(C)CCC=C(C)CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-UHFFFAOYSA-N 0.000 description 3
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- 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 3
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- 235000010376 calcium ascorbate Nutrition 0.000 description 1
- 239000011692 calcium ascorbate Substances 0.000 description 1
- 229940047036 calcium ascorbate Drugs 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BLORRZQTHNGFTI-ZZMNMWMASA-L calcium-L-ascorbate Chemical compound [Ca+2].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] BLORRZQTHNGFTI-ZZMNMWMASA-L 0.000 description 1
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- SELHWUUCTWVZOV-UHFFFAOYSA-N dodecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO.CCCCCCCCCCCC(O)=O SELHWUUCTWVZOV-UHFFFAOYSA-N 0.000 description 1
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- 229930195733 hydrocarbon Natural products 0.000 description 1
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- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
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- 239000011148 porous material Substances 0.000 description 1
- 235000019275 potassium ascorbate Nutrition 0.000 description 1
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- CONVKSGEGAVTMB-RXSVEWSESA-M potassium-L-ascorbate Chemical compound [K+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] CONVKSGEGAVTMB-RXSVEWSESA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
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- BFZNCPXNOGIELB-UHFFFAOYSA-N propan-2-yl 10-[5,6-dihexyl-2-(8-oxo-8-propan-2-yloxyoctyl)cyclohex-3-en-1-yl]dec-9-enoate Chemical compound CCCCCCC1C=CC(CCCCCCCC(=O)OC(C)C)C(C=CCCCCCCCC(=O)OC(C)C)C1CCCCCC BFZNCPXNOGIELB-UHFFFAOYSA-N 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
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- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
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- 235000020752 sage extract Nutrition 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
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- 239000000344 soap Substances 0.000 description 1
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- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
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- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 150000003669 ubiquinones Chemical class 0.000 description 1
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Abstract
【課題】グリチルレチン酸誘導体を含有し、透明性及び経時安定性に優れた乳化組成物を提供すること。【解決手段】下記(A)~(C)の成分:(A)下記一般式(1)で表されるグリチルレチン酸誘導体、(B)リン脂質、(C)HLBが12以上の界面活性剤、及び(D)特定のジエステル化合物を含有し、かつ(A)成分に対する(D)成分の量が50質量%~400質量%である乳化組成物。【選択図】なしAn object of the present invention is to provide an emulsion composition containing a glycyrrhetinic acid derivative and having excellent transparency and stability over time. [Solution] Components (A) to (C) below: (A) a glycyrrhetinic acid derivative represented by the following general formula (1), (B) a phospholipid, (C) a surfactant with an HLB of 12 or more, and (D) an emulsified composition containing a specific diester compound and in which the amount of component (D) relative to component (A) is 50% by mass to 400% by mass. [Selection diagram] None
Description
本発明は、乳化組成物及び化粧料に関する。 The present invention relates to emulsified compositions and cosmetics.
グリチルレチン酸ステアリル等のグリチルレチン酸誘導体が、抗炎症効果を有する薬剤として化粧料等に配合されている。グリチルレチン酸誘導体は油溶性薬剤であり、乳化組成物の粒子径を小さくしてナノ乳化することで浸透性が向上して大きな効果が期待できるが、乳化、特に乳化安定性の確保が非常に難しい素材である。 Glycyrrhetinic acid derivatives such as stearyl glycyrrhetinate are blended into cosmetics and the like as drugs having anti-inflammatory effects. Glycyrrhetinic acid derivatives are oil-soluble drugs, and by reducing the particle size of the emulsified composition and creating nano-emulsification, the permeability can be improved and great effects can be expected, but emulsification, especially ensuring emulsion stability, is extremely difficult. It is the material.
特許文献1は、下記(A)~(E)の成分:(A)下記一般式(1)で表されるグリチルレチン酸誘導体、(B)トコフェロール、酢酸トコフェロール及びトコトリエノールから選択される少なくとも1種、(C)リン脂質、(D)HLBが12以上の界面活性剤、及び、(E)トリリノール酸グリセリル、トリリノレン酸グリセリル、トリステアリン酸グリセリル、トリオレイン酸グリセリル、トリイソステアリン酸グリセリル、トリカプリル酸グリセリル、トリカプリン酸グリセリル、及びトリ(カプリル酸/カプリン酸)グリセリルから選択される少なくとも1種を含む脂肪酸グリセリド、を含有し、かつ、一般式(1)で表されるグリチルレチン酸誘導体の含有量が1.0質量%以上5.0質量%以下である乳化組成物について開示している。 Patent Document 1 discloses the following components (A) to (E): (A) a glycyrrhetinic acid derivative represented by the following general formula (1); (B) at least one selected from tocopherol, tocopherol acetate, and tocotrienol; (C) phospholipid, (D) surfactant with HLB of 12 or more, and (E) glyceryl trilinoleate, glyceryl trilinolenate, glyceryl tristearate, glyceryl trioleate, glyceryl triisostearate, tricaprylic acid A fatty acid glyceride containing at least one selected from glyceryl, glyceryl tricaprate, and glyceryl tri(caprylic acid/capric acid), and the content of the glycyrrhetinic acid derivative represented by the general formula (1) is It discloses an emulsified composition in which the content is 1.0% by mass or more and 5.0% by mass or less.
特許文献1では、グリチルレチン酸誘導体に、(B)、(C)、(D)及び(E)成分を配合することで、透明性の高い乳化組成物及び化粧料を提供している。 Patent Document 1 provides highly transparent emulsified compositions and cosmetics by blending components (B), (C), (D), and (E) with a glycyrrhetinic acid derivative.
グリチルレチン酸誘導体を含有し、より優れた透明性及び経時安定性を有する乳化組成物及び化粧料が必要とされている。 There is a need for emulsified compositions and cosmetics that contain glycyrrhetinic acid derivatives and have better transparency and stability over time.
本発明は、以下に記載の実施形態を包含する。 The present invention encompasses the embodiments described below.
項1.下記(A)~(D)の成分:
(A)下記一般式(1)で表されるグリチルレチン酸誘導体、
Item 1. Ingredients (A) to (D) below:
(A) a glycyrrhetinic acid derivative represented by the following general formula (1),
(式(1)中、R1及びR2は、
R1が、-C12H25、-C14H29、-C16H33、-C18H37、又は-C20H41を表し、且つR2が水素原子を表すか、或いは、
R1が水素原子を表し、且つR2が、-(C=O)C11H23、-(C=O)C13H27、-(C=O)C15H31、又は-(C=O)C17H35を表す。)
(B)リン脂質、
(C)HLBが12以上の界面活性剤、及び
(D)下記一般式(2)又は(3)で表される化合物を一種以上、
(In formula (1), R 1 and R 2 are
R 1 represents -C 12 H 25 , -C 14 H 29 , -C 16 H 33 , -C 18 H 37 , or -C 20 H 41 , and R 2 represents a hydrogen atom, or
R 1 represents a hydrogen atom, and R 2 represents -(C=O)C 11 H 23 , -(C=O)C 13 H 27 , -(C=O)C 15 H 31 , or -(C =O) represents C17H35 . )
(B) phospholipid,
(C) a surfactant with an HLB of 12 or more, and (D) one or more compounds represented by the following general formula (2) or (3),
(式(2)中、
R1及びR2が、それぞれ独立して、炭素数2~18の直鎖若しくは分岐アルキル基、又は炭素数2~18の直鎖若しくは分岐アルケニル基であり、
Qが、非置換若しくは置換基を有する炭素数2~40の直鎖若しくは分岐アルキル基、非置換若しくは置換基を有する炭素数2~40の直鎖若しくは分岐アルケニル基、非置換若しくは置換基を有するフェニル基、又は非置換若しくは置換基を有するシクロアルキル基であり、前記直鎖若しくは分岐アルキル基、前記直鎖若しくは分岐アルケニル基、前記フェニル基、及び前記シクロアルキル基の置換基は1又は2個のヒドロキシ基である)
(In formula (2),
R 1 and R 2 are each independently a straight chain or branched alkyl group having 2 to 18 carbon atoms, or a straight chain or branched alkenyl group having 2 to 18 carbon atoms,
Q is an unsubstituted or substituted straight chain or branched alkyl group with 2 to 40 carbon atoms, an unsubstituted or substituted straight chain or branched alkenyl group with 2 to 40 carbon atoms, or an unsubstituted or substituent group. A phenyl group or a cycloalkyl group that is unsubstituted or has a substituent, and the linear or branched alkyl group, the linear or branched alkenyl group, the phenyl group, and the cycloalkyl group have 1 or 2 substituents. hydroxyl group)
(式(3)中、
R3及びR4が、それぞれ独立して、炭素数2~18の直鎖若しくは分岐アルキル基、又は炭素数2~18の直鎖若しくは分岐アルケニル基であり、
Qが、非置換若しくは置換基を有する炭素数2~40の直鎖若しくは分岐アルキル基、非置換若しくは置換基を有する炭素数2~40の直鎖若しくは分岐アルケニル基、非置換若しくは置換基を有するフェニル基、又は非置換若しくは置換基を有するシクロアルキル基であり、前記直鎖若しくは分岐アルキル基、前記直鎖若しくは分岐アルケニル基、前記フェニル基、及び前記シクロアルキル基の置換基は1又は2個のヒドロキシ基である)
を含有し、かつ、(A)成分に対する(D)成分の量が50質量%~400質量%である乳化組成物。
(In formula (3),
R 3 and R 4 are each independently a straight chain or branched alkyl group having 2 to 18 carbon atoms, or a straight chain or branched alkenyl group having 2 to 18 carbon atoms,
Q is an unsubstituted or substituted straight chain or branched alkyl group with 2 to 40 carbon atoms, an unsubstituted or substituted straight chain or branched alkenyl group with 2 to 40 carbon atoms, or an unsubstituted or substituent group. A phenyl group or a cycloalkyl group that is unsubstituted or has a substituent, and the linear or branched alkyl group, the linear or branched alkenyl group, the phenyl group, and the cycloalkyl group have 1 or 2 substituents. hydroxyl group)
and the amount of component (D) relative to component (A) is 50% by mass to 400% by mass.
項2.(D)成分が、炭素鎖2~18の脂肪酸とグリコールのジエステルを含む項1に記載の乳化組成物。 Item 2. Item 2. The emulsified composition according to Item 1, wherein component (D) contains a diester of a fatty acid and a glycol having a carbon chain of 2 to 18.
項3.トコフェロール及びトコフェロール誘導体からなる群より選択される少なくとも一種をさらに含有する項1に記載の乳化組成物。 Item 3. Item 2. The emulsified composition according to Item 1, further comprising at least one selected from the group consisting of tocopherol and tocopherol derivatives.
項4.(B)成分が、レシチンを含む項1~3のいずれか一項に記載の乳化組成物。 Item 4. The emulsified composition according to any one of Items 1 to 3, wherein the component (B) contains lecithin.
項5.(C)成分が、ポリグリセリン脂肪酸エステル及びポリグリセリン脂肪酸エーテルから成る群より選択される少なくとも一つの界面活性剤を含む項1~3のいずれか一項に記載の乳化組成物。 Item 5. 4. The emulsified composition according to any one of Items 1 to 3, wherein component (C) contains at least one surfactant selected from the group consisting of polyglycerol fatty acid ester and polyglycerol fatty acid ether.
項6.項1~5のいずれか一項に記載の乳化組成物を含む化粧料。 Item 6. Item 5. A cosmetic comprising the emulsified composition according to any one of Items 1 to 5.
項7.項1~5のいずれか一項に記載の乳化組成物を含む皮膚外用剤。 Section 7. Item 5. An external skin preparation comprising the emulsified composition according to any one of Items 1 to 5.
本発明によれば、グリチルレチン酸誘導体を含有し、透明性及び経時安定性に優れた乳化組成物及びこれを含有する化粧料が提供される。 According to the present invention, an emulsion composition containing a glycyrrhetinic acid derivative and having excellent transparency and stability over time, and a cosmetic containing the same are provided.
以下、本発明の実施形態について説明する。
乳化組成物
本発明の乳化組成物は、
下記(A)~(D)の成分:
(A)下記一般式(1)で表されるグリチルレチン酸誘導体、
Embodiments of the present invention will be described below.
emulsifying composition
The emulsified composition of the present invention is
Ingredients (A) to (D) below:
(A) a glycyrrhetinic acid derivative represented by the following general formula (1),
式(1)中、R1及びR2は、
R1が、-C12H25、-C14H29、-C16H33、-C18H37、又は-C20H41を表し、且つR2が水素原子を表すか、或いは、
R1が水素原子を表し、且つR2が、-(C=O)C11H23、-(C=O)C13H27、-(C=O)C15H31、又は-(C=O)C17H35を表す
(B)リン脂質、
(C)HLBが12以上の界面活性剤、及び
(D)下記一般式(2)又は(3)で表される化合物を一種以上、
In formula (1), R 1 and R 2 are
R 1 represents -C 12 H 25 , -C 14 H 29 , -C 16 H 33 , -C 18 H 37 , or -C 20 H 41 , and R 2 represents a hydrogen atom, or
R 1 represents a hydrogen atom, and R 2 represents -(C=O)C 11 H 23 , -(C=O)C 13 H 27 , -(C=O)C 15 H 31 , or -(C =O) represents C 17 H 35 (B) phospholipid,
(C) a surfactant with an HLB of 12 or more, and (D) one or more compounds represented by the following general formula (2) or (3),
(式(2)中、
R1及びR2が、それぞれ独立して、炭素数2~18の直鎖若しくは分岐アルキル基、又は炭素数2~18の直鎖若しくは分岐アルケニル基であり、
Qが、非置換若しくは置換基を有する炭素数2~40の直鎖若しくは分岐アルキル基、非置換若しくは置換基を有する炭素数2~40の直鎖若しくは分岐アルケニル基、非置換若しくは置換基を有するフェニル基、又は非置換若しくは置換基を有するシクロアルキル基であり、前記直鎖若しくは分岐アルキル基、前記直鎖若しくは分岐アルケニル基、前記フェニル基、及び前記シクロアルキル基の置換基は1又は2個のヒドロキシ基である)
(In formula (2),
R 1 and R 2 are each independently a straight chain or branched alkyl group having 2 to 18 carbon atoms, or a straight chain or branched alkenyl group having 2 to 18 carbon atoms,
Q is an unsubstituted or substituted straight chain or branched alkyl group with 2 to 40 carbon atoms, an unsubstituted or substituted straight chain or branched alkenyl group with 2 to 40 carbon atoms, or an unsubstituted or substituent group. A phenyl group or a cycloalkyl group that is unsubstituted or has a substituent, and the linear or branched alkyl group, the linear or branched alkenyl group, the phenyl group, and the cycloalkyl group have 1 or 2 substituents. hydroxyl group)
(式(3)中、
R3及びR4が、それぞれ独立して、炭素数2~18の直鎖若しくは分岐アルキル基、又は炭素数2~18の直鎖若しくは分岐アルケニル基であり、
Qが、非置換若しくは置換基を有する炭素数2~40の直鎖若しくは分岐アルキル基、非置換若しくは置換基を有する炭素数2~40の直鎖若しくは分岐アルケニル基、非置換若しくは置換基を有するフェニル基、又は非置換若しくは置換基を有するシクロアルキル基であり、前記直鎖若しくは分岐アルキル基、前記直鎖若しくは分岐アルケニル基、前記フェニル基、及び前記シクロアルキル基の置換基は1又は2個のヒドロキシ基である)
を含有し、かつ、(A)成分に対する(D)成分の量が50質量%~400質量%である。
(In formula (3),
R 3 and R 4 are each independently a straight chain or branched alkyl group having 2 to 18 carbon atoms, or a straight chain or branched alkenyl group having 2 to 18 carbon atoms,
Q is an unsubstituted or substituted straight chain or branched alkyl group with 2 to 40 carbon atoms, an unsubstituted or substituted straight chain or branched alkenyl group with 2 to 40 carbon atoms, or an unsubstituted or substituent group. A phenyl group or a cycloalkyl group that is unsubstituted or has a substituent, and the linear or branched alkyl group, the linear or branched alkenyl group, the phenyl group, and the cycloalkyl group have 1 or 2 substituents. hydroxyl group)
and the amount of component (D) relative to component (A) is 50% by mass to 400% by mass.
(A)グリチルレチン酸誘導体
一般式(1)で表されるグリチルレチン酸誘導体は、グリチルレチン酸誘導体は、油溶性薬剤として作用する。
(A) Glycyrrhetinic acid derivative The glycyrrhetinic acid derivative represented by the general formula (1) acts as an oil-soluble drug.
(A)一般式(1)で表されるグリチルレチン酸誘導体には、i)グリチルレチン酸の3位の水酸基を、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、又はエイコサン酸でエステル化させることより製造されるグリチルレチン酸エステル、及び、ii)グリチルレチン酸の20位のカルボキシル基を、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、又はエイコサノールでエステル化することにより製造されるグリチルレチン酸エステルが包含される。 (A) The glycyrrhetinic acid derivative represented by the general formula (1) is produced by i) esterifying the 3-hydroxyl group of glycyrrhetinic acid with lauric acid, myristic acid, palmitic acid, stearic acid, or eicosanoic acid. Glycyrrhetinic acid ester produced, and ii) glycyrrhetinic acid ester produced by esterifying the carboxyl group at position 20 of glycyrrhetinic acid with lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, or eicosanol. Ru.
一般式(1)中、R1が、-C16H33、-C18H37、又は-C20H41を表し、且つ、R2が水素原子を表すグリチルレチン酸誘導体、或いは、R1が水素原子を表し、且つ、Rが、-(C=O)C15H31、又は-(C=O)C17H35を表すグリチルレチン酸誘導体が好ましい。更には、R1が、-C18H37、且つ、R2が水素原子で表されるグリチルレチン酸ステアリルが最も好ましい。 In general formula (1), a glycyrrhetinic acid derivative in which R 1 represents -C 16 H 33 , -C 18 H 37 , or -C 20 H 41 and R 2 represents a hydrogen atom, or a glycyrrhetinic acid derivative in which R 1 represents a hydrogen atom; Glycyrrhetinic acid derivatives that represent a hydrogen atom and R represents -(C=O)C 15 H 31 or -(C=O)C 17 H 35 are preferred. Most preferred is stearyl glycyrrhetinate in which R 1 is -C 18 H 37 and R 2 is a hydrogen atom.
Qが非置換若しくは置換基を有するシクロアルキル基の場合、シクロアルキル基の炭素数は3~8であることが好ましい。
グリチルレチン酸ステアリルは、CAS番号13832-70-7の化合物であり、脂溶性物質である上に、一般的な油剤に対する相溶性の低い化合物である。グリチルレチン酸ステアリルは、従来、抗炎症、抗アレルギー剤として、石鹸、クリーム、乳液に用いられている。
When Q is an unsubstituted or substituted cycloalkyl group, the cycloalkyl group preferably has 3 to 8 carbon atoms.
Stearyl glycyrrhetinate is a compound with CAS number 13832-70-7, which is a fat-soluble substance and has low compatibility with common oils. Stearyl glycyrrhetinate has conventionally been used in soaps, creams, and milky lotions as an anti-inflammatory and anti-allergic agent.
グリチルレチン酸誘導体は、上記のエステル化反応により合成して得ることもできるし、市販品を利用することもできる。 Glycyrrhetinic acid derivatives can be synthesized by the above-mentioned esterification reaction, or commercially available products can be used.
本発明の乳化組成物におけるグリチルレチン酸誘導体の含有量は、0.5質量%以上10質量%以下であることが好ましい。グリチルレチン酸誘導体に期待される抗炎症作用などの所望の効果を充分に発揮させるためには、下限値は0.9質量%以上が好ましく、1.5質量%以上がより好ましい。乳化組成物中におけるグリチルレチン酸誘導体の含有量の上限は、溶解性の観点から、8質量%以下がより好ましく、7質量%以下が更に好ましい。 The content of the glycyrrhetinic acid derivative in the emulsified composition of the present invention is preferably 0.5% by mass or more and 10% by mass or less. In order to fully exhibit desired effects such as anti-inflammatory action expected of glycyrrhetinic acid derivatives, the lower limit is preferably 0.9% by mass or more, more preferably 1.5% by mass or more. From the viewpoint of solubility, the upper limit of the content of the glycyrrhetinic acid derivative in the emulsified composition is more preferably 8% by mass or less, and even more preferably 7% by mass or less.
本発明の乳化組成物における、グリチルレチン酸誘導体の含有量はさらに好ましくは1.0質量%以上5.0質量%以下であり、最も好ましくは2.0質量%以上4.0質量%以下である。グリチルレチン酸誘導体の含有量が、上記の範囲であることで、グリチルレチン酸誘導体を高濃度に含有しながらも、高い透明性が長期間に亘って安定に維持することができる。また、本発明の透明性の高い乳化組成物を、その好適な用途の一つである化粧料に適用した場合においては、グリチルレチン酸誘導体を高濃度に含有しながらも、優れた経時安定性が得られる。 The content of the glycyrrhetinic acid derivative in the emulsified composition of the present invention is more preferably 1.0% by mass or more and 5.0% by mass or less, most preferably 2.0% by mass or more and 4.0% by mass or less. . When the content of the glycyrrhetinic acid derivative is within the above range, high transparency can be stably maintained over a long period of time even though the glycyrrhetinic acid derivative is contained at a high concentration. In addition, when the highly transparent emulsified composition of the present invention is applied to cosmetics, which is one of its preferred uses, it has excellent stability over time even though it contains a high concentration of glycyrrhetinic acid derivatives. can get.
(B)リン脂質
リン脂質としては、グリセロリン脂質が挙げられる。グリセロリン脂質としては、例えば、ホスファチジン酸、ビスホスアチジン酸、レシチン(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、ホスファチジルメチ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、ホスファチジルグリセリン、ジホスファチジルグリセリン(カルジオリピン)等が挙げられ、これらの任意の混合物も用いることができる。
(B) Phospholipids Examples of phospholipids include glycerophospholipids. Examples of glycerophospholipids include phosphatidic acid, bisphosatidic acid, lecithin (phosphatidylcholine), phosphatidylethanolamine, phosphatidylmethylethanolamine, phosphatidylserine, phosphatidylinositol, phosphatidylglycerin, diphosphatidylglycerin (cardiolipin), etc. Mixtures of can also be used.
乳化組成物の透明性及び経時安定性の点で、リン脂質中のホスファチジルコリンの含有率が50質量%以上であることが好ましい。リン脂質中のホスファチジルコリンの含有率が50質量%以上であると、乳化組成物の透明性及び経時安定性がより向上する。リン脂質中のホスファチジルコリンの含有率は、好ましくは60質量%以上であり、より好ましくは65質量%以上であり、より好ましくは70質量%以上である。リン脂質中のホスファチジルコリンの含有率の上限値は、好ましくは100質量%以下である。 From the viewpoint of transparency and stability over time of the emulsified composition, it is preferable that the content of phosphatidylcholine in the phospholipid is 50% by mass or more. When the content of phosphatidylcholine in the phospholipid is 50% by mass or more, the transparency and stability over time of the emulsion composition are further improved. The content of phosphatidylcholine in the phospholipid is preferably 60% by mass or more, more preferably 65% by mass or more, and even more preferably 70% by mass or more. The upper limit of the content of phosphatidylcholine in phospholipids is preferably 100% by mass or less.
グリセロリン脂質を含む大豆、トウモロコシ、落花生、ナタネ、麦等の植物由来のものや、卵黄、牛等の動物由来のもの及び大腸菌等の微生物等由来の各種レシチンをリン脂質の供給源として使用することができる。 Use lecithins containing glycerophospholipids derived from plants such as soybeans, corn, peanuts, rapeseed, and wheat, those derived from animals such as egg yolk and cows, and various lecithins derived from microorganisms such as Escherichia coli as sources of phospholipids. Can be done.
レシチンは、グリセロリン脂質の一種で、自然界の動植物のすべての細胞中に存在しており、生体膜の主要構成成分である。工業的には、大豆と卵黄を原料として得られた大豆レシチン及び卵黄レシチンが製造及び市販されている。 Lecithin is a type of glycerophospholipid that exists in all cells of animals and plants in nature, and is a major component of biological membranes. Industrially, soybean lecithin and egg yolk lecithin obtained from soybeans and egg yolks are manufactured and marketed.
大豆レシチンは、大豆油精製工程で副生する油滓を乾燥、精製することにより製造される。通常、リン脂質含量が70質量%以下であるペースト状レシチンは、大豆粗油を30質量%程度含むが、安価なため、特に食品分野ではほとんどこのペースト状のレシチンが用いられる。また、近年では、リン脂質自体の生理活性や、より高度な乳化剤へのニーズから、高度精製、分別、酵素分解などの技術が加えられ、性能、機能の異なる種々のレシチン群が作られている。 Soybean lecithin is produced by drying and refining soapstock, a by-product of the soybean oil refining process. Normally, paste-like lecithin with a phospholipid content of 70% by mass or less contains about 30% by mass of soybean crude oil, and because it is inexpensive, this paste-like lecithin is mostly used, especially in the food field. In addition, in recent years, due to the physiological activity of phospholipids themselves and the need for more advanced emulsifiers, technologies such as advanced purification, fractionation, and enzymatic degradation have been added, and various lecithin groups with different performances and functions have been created. .
高度精製レシチンは、上記ペースト状レシチンから、アセトン等の溶媒を用いて脱油し、粉末化したもので、一般にレシチン含量が90質量%以上となっている。この高度精製レシチンの例としては、PHOSPHOLIPON20(リポイド社)、レシオンP(理研ビタミン株式会社)、SLPホワイト(辻製油株式会社)、エマルメティック300(ルーカスマイヤーコスメティックス社)などが市販されている。 Highly purified lecithin is obtained by removing oil from the paste lecithin using a solvent such as acetone and turning it into powder, and generally has a lecithin content of 90% by mass or more. Examples of this highly purified lecithin include PHOSPHOLIPON 20 (Lipoid Co., Ltd.), Resion P (Riken Vitamin Co., Ltd.), SLP White (Tsuji Oil Co., Ltd.), Emulmetic 300 (Lucasmeyer Cosmetics Co., Ltd.), and the like.
分別レシチンは、上記高度精製レシチンに対して、各種溶媒への溶解度差を利用したり、蒸留等の操作を行なうことにより、特定のリン脂質の含有量を高めたものであり、一般には、ホスファチジルコリン含量を高めたものが市販されている。ホスファチジルコリン含量を高めた市販の分別レシチンの例としては、PHOSPHOLIPON50(PC含量:45質量%)、PHOSPHOLIPON85G(PC含量:80質量%)、PHOSPHOLIPON90G(PC含量:94質量%)(以上、リポイド社)、エメルメティック900(PC含量:50質量%)、エメルメティック930(PC含量:95質量%)(以上、ルーカスマイヤーコスメティックス社)、SLP-PC70、SLP-PC90(以上、辻製油株式会社)などが挙げられる。 Fractionated lecithin is the highly purified lecithin mentioned above, which has a higher content of specific phospholipids by utilizing the difference in solubility in various solvents or by performing operations such as distillation. Products with increased content are commercially available. Examples of commercially available fractionated lecithins with increased phosphatidylcholine content include PHOSPHOLIPON 50 (PC content: 45% by mass), PHOSPHOLIPON 85G (PC content: 80% by mass), PHOSPHOLIPON 90G (PC content: 94% by mass) (all manufactured by Lipoid), Emermetic 900 (PC content: 50% by mass), Emermetic 930 (PC content: 95% by mass) (all from Lukasmeyer Cosmetics), SLP-PC70, SLP-PC90 (all from Tsuji Oil Co., Ltd.), etc. can be mentioned.
本発明において、グリセロリン脂質として、酵素分解したグリセロリン脂質を使用することもできる。例えば、前記レシチンを酵素分解したリゾレシチン(酵素分解レシチン)は、酸、又はアルカリ触媒によるレシチンの加水分解により得られる他、ホスホリパーゼA1、又はA2を用いたレシチンの加水分解により得ることもできる。このようなリゾレシチンに代表されるリゾ化合物を化合物名で示すと、リゾホスファチジン酸、リゾホスファチジルグリセリン、リゾホスファチジルイノシトール、リゾホスファチジルエタノールアミン、リゾホスファチジルメチルエタノールアミン、リゾホスファチジルコリン(リゾレシチン)、リゾホスファチジルセリン等が挙げられる。 In the present invention, enzymatically decomposed glycerophospholipids can also be used as the glycerophospholipids. For example, lysolecithin obtained by enzymatically decomposing the lecithin (enzymatically decomposed lecithin) can be obtained not only by hydrolysis of lecithin using an acid or alkali catalyst, but also by hydrolysis of lecithin using phospholipase A1 or A2. Lysophosphatidic acid, lysophosphatidylglycerin, lysophosphatidylinositol, lysophosphatidylethanolamine, lysophosphatidylmethylethanolamine, lysophosphatidylcholine (lysolecithin), lysophosphatidylserine, etc. can be mentioned.
リン脂質は、単独又は複数種の混合物の形態で用いることができる。リン脂質としては、乳化組成物の透明性及び経時安定性の観点から、リゾレシチン以外のリン脂質が好ましく、精製レシチンが好ましく、分別レシチンがより好ましい。これらのレシチンを含有することで、乳化組成物の透明性及び経時安定性がより向上し、乳化組成物を含有する化粧料の透明性及び経時安定性が向上する。 Phospholipids can be used alone or in the form of a mixture of multiple types. As the phospholipid, from the viewpoint of transparency and stability over time of the emulsified composition, phospholipids other than lysolecithin are preferred, purified lecithin is preferred, and fractionated lecithin is more preferred. By containing these lecithins, the transparency and stability over time of the emulsion composition are further improved, and the transparency and stability over time of the cosmetic containing the emulsion composition are further improved.
本発明の乳化組成物におけるリン脂質の含有量は、0.1質量%~10質量%であることが好ましく、0.2質量%~8質量%がより好ましく、1質量%~4質量%がさらに更に好ましい。リン脂質の含有量を0.1質量%以上とすることにより、乳化組成物の乳化安定性がより良好となる傾向がある。また、リン脂質の含有量を10質量%以下とすることにより、過剰なリン脂質が油性成分から離れて水中にリン脂質分散体を形成することなく、乳化組成物の乳化安定性が得られる点から好ましい。 The content of phospholipids in the emulsified composition of the present invention is preferably 0.1% to 10% by mass, more preferably 0.2% to 8% by mass, and 1% to 4% by mass. Even more preferred. By setting the phospholipid content to 0.1% by mass or more, the emulsion stability of the emulsion composition tends to be better. In addition, by setting the phospholipid content to 10% by mass or less, the emulsion stability of the emulsified composition can be obtained without excess phospholipid separating from the oily component and forming a phospholipid dispersion in water. preferred.
また、本発明の乳化組成物中の(B)リン脂質の含有量の(A)グリチルレチン酸誘導体の含有量に対する質量比は、0.1~1.5であることが好ましい。乳化組成物中の、ホスファチジルコリンの量の(A)グリチルレチン酸誘導体の含有量に対する質量比は、0.05~1であることが好ましく、0.01~0.75であることがより好ましい。 Furthermore, the mass ratio of the content of phospholipid (B) to the content of glycyrrhetinic acid derivative (A) in the emulsified composition of the present invention is preferably 0.1 to 1.5. The mass ratio of the amount of phosphatidylcholine to the content of the glycyrrhetinic acid derivative (A) in the emulsified composition is preferably 0.05 to 1, more preferably 0.01 to 0.75.
(C)HLBが12以上の界面活性剤
HLBが12以上の界面活性剤は、乳化組成物中の油相/水相の界面張力を下げ、その結果、乳化組成物の粒子径を細かくするために使用される。HLB値の上限値は、特に限定されないが、一般的には、20以下であり、18以下が好ましい。
(C) Surfactant with HLB of 12 or more Surfactant with HLB of 12 or more lowers the interfacial tension of the oil phase/aqueous phase in the emulsified composition, and as a result, reduces the particle size of the emulsified composition. used for. The upper limit of the HLB value is not particularly limited, but is generally 20 or less, preferably 18 or less.
HLBは、通常界面活性剤の分野で使用される親水性-疎水性のバランスで、通常用いる計算式、例えば川上式等が使用できる。本発明においては、下記の川上式を採用する。 HLB is a hydrophilic-hydrophobic balance commonly used in the field of surfactants, and a commonly used calculation formula such as the Kawakami formula can be used. In the present invention, the following Kawakami formula is adopted.
HLB=7+11.7log(Mw/Mo)
ここで、Mwは親水基の分子量、Moは疎水基の分子量である。
HLB=7+11.7log(Mw/Mo)
Here, Mw is the molecular weight of the hydrophilic group, and Mo is the molecular weight of the hydrophobic group.
また、カタログ等に記載されているHLBの数値を使用してもよい。また、上記の式からも分かるように、HLBの加成性を利用して、任意のHLB値の界面活性剤を得ることができる。 Alternatively, the HLB values listed in catalogs or the like may be used. Further, as can be seen from the above formula, a surfactant having an arbitrary HLB value can be obtained by utilizing the additivity of HLB.
HLBが12以上の界面活性剤としては、カチオン性、アニオン性、両性、非イオン性の各界面活性剤を挙げることができ、特に限定されないが、非イオン性界面活性剤が好ましい。非イオン性界面活性剤の例としては、ポリグリセリン脂肪酸エステル、ポリグリセリン縮合リシノレイン酸エステル、ショ糖脂肪酸エステル、ソルビタン脂肪酸エステル、及びポリオキシエチレンソルビタン脂肪酸エステルなどが挙げられる。 HLBが12以上の界面活性剤は、1種類でもよいし、または2種類以上を組み合わせてもよい。 Examples of the surfactant having an HLB of 12 or more include cationic, anionic, amphoteric, and nonionic surfactants, and are not particularly limited, but nonionic surfactants are preferred. Examples of nonionic surfactants include polyglycerin fatty acid ester, polyglycerin condensed ricinoleic acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester. One type of surfactant having an HLB of 12 or more may be used, or two or more types may be used in combination.
HLBが12以上の界面活性剤として、より好ましくは、ポリグリセリン脂肪酸エステル、ショ糖脂肪酸エステル、ソルビタン脂肪酸エステル、又はポリオキシエチレンソルビタン脂肪酸エステルであり、最も好ましくは、HLBが12以上の界面活性剤は、ポリグリセリン脂肪酸エステルである。 The surfactant having an HLB of 12 or more is more preferably a polyglycerin fatty acid ester, a sucrose fatty acid ester, a sorbitan fatty acid ester, or a polyoxyethylene sorbitan fatty acid ester, and most preferably a surfactant having an HLB of 12 or more. is a polyglycerol fatty acid ester.
ポリグリセリン脂肪酸エステルは、平均重合度が2以上(好ましくは6~15、より好ましくは8~10)のポリグリセリンと、炭素数8~18の脂肪酸(例えばカプリル酸、カプリン酸、ラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、イソステアリン酸、オレイン酸、及びリノール酸から選択される脂肪酸)とのエステルであることが好ましい。 Polyglycerin fatty acid esters include polyglycerin with an average degree of polymerization of 2 or more (preferably 6 to 15, more preferably 8 to 10) and fatty acids having 8 to 18 carbon atoms (for example, caprylic acid, capric acid, lauric acid, myristic acid). Preferably, it is an ester with a fatty acid selected from palmitic acid, stearic acid, isostearic acid, oleic acid, and linoleic acid.
ポリグリセリン脂肪酸エステルの好ましい例としては、ヘキサグリセリンモノオレイン酸エステル、ヘキサグリセリンモノステアリン酸エステル、ヘキサグリセリンモノパルミチン酸エステル、ヘキサグリセリンモノミリスチン酸エステル、ヘキサグリセリンモノラウリン酸エステル、デカグリセリンモノオレイン酸エステル、デカグリセリンモノステアリン酸エステル、デカグリセリンモノイソステアリン酸エステル、デカグリセリンモノパルミチン酸エステル、デカグリセリンモノミリスチン酸エステル、デカグリセリンモノラウリン酸エステル等が挙げられる。これらの中でも、より好ましくは、デカグリセリンモノオレイン酸エステル(HLB=12)、デカグリセリンモノステアリン酸エステル(HLB=12)、デカグリセリンモノパルミチン酸エステル(HLB=13)、デカグリセリンモノミリスチン酸エステル(HLB=14)、デカグリセリンモノラウリン酸エステル(HLB=16)などである。これらのポリグリセリン脂肪酸エステルを、単独又は混合して用いることができる。 Preferred examples of polyglycerin fatty acid esters include hexaglycerin monooleate, hexaglycerin monostearate, hexaglycerin monopalmitate, hexaglycerin monomyristate, hexaglycerin monolaurate, and decaglycerin monooleate. , decaglycerol monostearate, decaglycerol monoisostearate, decaglycerol monopalmitate, decaglycerol monomyristate, decaglycerol monolaurate, and the like. Among these, more preferred are decaglycerin monooleate (HLB=12), decaglycerin monostearate (HLB=12), decaglycerin monopalmitate (HLB=13), and decaglycerin monomyristate. (HLB=14), decaglycerin monolaurate (HLB=16), and the like. These polyglycerol fatty acid esters can be used alone or in combination.
ショ糖脂肪酸エステルとしては、脂肪酸の炭素数が12以上のものが好ましく、12~20のものがより好ましい。ショ糖脂肪酸エステルの好ましい例としては、ショ糖ジオレイン酸エステル、ショ糖ジステアリン酸エステル、ショ糖ジパルミチン酸エステル、ショ糖ジミリスチン酸エステル、ショ糖ジラウリン酸エステル、ショ糖モノオレイン酸エステル、ショ糖モノステアリン酸エステル、ショ糖モノパルミチン酸エステル、ショ糖モノミリスチン酸エステル、ショ糖モノラウリン酸エステル等が挙げられ、これらの中でも、ショ糖モノオレイン酸エステル、ショ糖モノステアリン酸エステル、ショ糖モノパルミチン酸エステル、ショ糖モノミリスチン酸エステル、ショ糖モノラウリン酸エステルがより好ましい。本発明においては、これらのショ糖脂肪酸エステルを、単独又は混合して用いることができる。 The sucrose fatty acid ester preferably has a fatty acid having 12 or more carbon atoms, more preferably 12 to 20 carbon atoms. Preferred examples of the sucrose fatty acid ester include sucrose dioleate, sucrose distearate, sucrose dipalmitate, sucrose dimyristate, sucrose dilaurate, sucrose monooleate, and sucrose monooleate. Examples include sugar monostearate, sucrose monopalmitate, sucrose monomyristate, sucrose monolaurate, etc. Among these, sucrose monooleate, sucrose monostearate, sucrose More preferred are monopalmitate, sucrose monomyristate, and sucrose monolaurate. In the present invention, these sucrose fatty acid esters can be used alone or in combination.
ソルビタン脂肪酸エステルとしては、脂肪酸の炭素数が8以上のものが好ましく、12以上のものがより好ましい。ソルビタン脂肪酸エステルの好ましい例としては、モノカプリル酸ソルビタン、モノラウリン酸ソルビタン、モノステアリン酸ソルビタン、セキステアリン酸ソルビタン、トリステアリン酸ソルビタン、イソステアリン酸ソルビタン、セスキイソステアリン酸ソルビタン、オレイン酸ソルビタン、セスキオレイン酸ソルビタン、トリオレイン酸ソルビタン等が挙げられる。これらのソルビタン脂肪酸エステルを、単独又は混合して用いることができる。 The sorbitan fatty acid ester preferably has fatty acid carbon atoms of 8 or more, more preferably 12 or more. Preferred examples of sorbitan fatty acid esters include sorbitan monocaprylate, sorbitan monolaurate, sorbitan monostearate, sorbitan sextearate, sorbitan tristearate, sorbitan isostearate, sorbitan sesquiisostearate, sorbitan oleate, and sorbitan sesquioleate. , sorbitan trioleate, and the like. These sorbitan fatty acid esters can be used alone or in combination.
ポリオキシエチレンソルビタン脂肪酸エステルとしては、脂肪酸の炭素数が8以上のものが好ましく、12以上のものがより好ましい。またポリオキシエチレンのエチレンオキサイドの長さ(付加モル数)としては、2~100が好ましく、4~50がより好ましい。ポリオキシエチレンソルビタン脂肪酸エステルの好ましい例としては、ポリオキシエチレンモノカプリル酸ソルビタン、ポリオキシエチレンモノラウリン酸ソルビタン、ポリオキシエチレンモノステアリン酸ソルビタン、ポリオキシエチレンセキステアリン酸ソルビタン、ポリオキシエチレントリステアリン酸ソルビタン、ポリオキシエチレンイソステアリン酸ソルビタン、ポリオキシエチレンセスキイソステアリン酸ソルビタン、ポリオキシエチレンオレイン酸ソルビタン、ポリオキシエチレンセスキオレイン酸ソルビタン、ポリオキシエチレントリオレイン酸ソルビタン等が挙げられる。 The polyoxyethylene sorbitan fatty acid ester preferably has fatty acid carbon atoms of 8 or more, more preferably 12 or more. The length (number of moles added) of ethylene oxide in polyoxyethylene is preferably 2 to 100, more preferably 4 to 50. Preferred examples of polyoxyethylene sorbitan fatty acid esters include polyoxyethylene sorbitan monocaprylate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan sextearate, and polyoxyethylene sorbitan tristearate. , polyoxyethylene sorbitan isostearate, polyoxyethylene sorbitan sesquiisostearate, polyoxyethylene sorbitan oleate, polyoxyethylene sorbitan sesquioleate, polyoxyethylene sorbitan trioleate, and the like.
HLBが12以上の界面活性剤は、単独又は混合して用いることができる。 Surfactants having an HLB of 12 or more can be used alone or in combination.
本発明の乳化組成物におけるHLBが12以上の界面活性剤の含有量は、0.5質量%~30質量%が好ましく、1質量%~20質量%がより好ましく、2質量%~15質量%が更に好ましい。HLBが12以上の界面活性剤量を0.5質量%以上含有することは、所定量のグリチルレチン酸誘導体の溶解性を向上させると共に、油相/水相間の界面張力を下げ易い点で好ましい。また、30質量%以下とすることは、界面活性剤を過剰量としない点で好ましい。 The content of the surfactant having an HLB of 12 or more in the emulsion composition of the present invention is preferably 0.5% to 30% by mass, more preferably 1% to 20% by mass, and more preferably 2% to 15% by mass. is even more preferable. It is preferable to contain 0.5% by mass or more of a surfactant having an HLB of 12 or more because it improves the solubility of a predetermined amount of glycyrrhetinic acid derivative and easily lowers the interfacial tension between the oil phase/aqueous phase. Further, it is preferable to set the amount to 30% by mass or less in order to avoid an excessive amount of surfactant.
(D)ジエステル化合物
(1)一般式(2)で表される化合物
本化合物は2価以上4価以下の多価アルコールの2個の水酸基が脂肪酸でエステル化された化合物を表す。
(D) Diester compound (1) Compound represented by general formula (2) This compound represents a compound in which two hydroxyl groups of a polyhydric alcohol having a valence of 2 or more and 4 or less are esterified with a fatty acid.
上記、多価アルコールとしては、エチレングリコール、プロピレングリコ-ル、ブチレングリコール、ペンチレングリコールなどの炭素数2~10のグリコール類、ジエチレングリコール、ジプロピレングリコール、ジプロピレングリコールなどのポリグリコール類も用いることができる。また、グリセリン、ジグリセリンなどのグリセリン類も用いることができる。 As the polyhydric alcohol mentioned above, glycols having 2 to 10 carbon atoms such as ethylene glycol, propylene glycol, butylene glycol, and pentylene glycol, and polyglycols such as diethylene glycol, dipropylene glycol, and dipropylene glycol may also be used. Can be done. Glycerins such as glycerin and diglycerin can also be used.
また、これらの多価アルコールとエステル化する脂肪酸としては、炭素数2~18の直鎖、分岐、あるいは二重結合を有する脂肪酸でも良く、具体的には、カプリン酸、カプロン酸、ラウリン酸、ミリスチン酸、ステアリン酸、オレイン酸、リノール酸などが挙げられる。 In addition, the fatty acids to be esterified with these polyhydric alcohols may be linear, branched, or double-bonded fatty acids having 2 to 18 carbon atoms, and specifically include capric acid, caproic acid, lauric acid, Examples include myristic acid, stearic acid, oleic acid, and linoleic acid.
これらのジエステル化合物の例としては、脂肪族とグリコールのジエステル、脂肪酸グリセリド、グリセリンの2量体がジエステル化された化合物等が挙げられる。 Examples of these diester compounds include diesters of aliphatic and glycol, fatty acid glycerides, and compounds obtained by diesterizing glycerin dimers.
脂肪族とグリコールのジエステルの例としては、ジカプリン酸エチレングリコール、ジカプリン酸プロピレングリコール、ジカプリル酸プロピレングリコール、ジラウリン酸プロピレングリコール、ジミリスチン酸プロピレングリコール、ジラウリン酸ブチレングリコール、ジエチルヘキサン酸ネオペンチレングリコール、ジカプリン酸ネオペンチレングリコール等が挙げられるが、乳化分散性、安定性の観点から、ジカプリン酸プロピレングリコール、ジカプリル酸プロピレングリコール、ジエチルヘキサン酸ネオペンチレングリコール、ジカプリン酸ネオペンチレングリコールが特に好ましい。 Examples of aliphatic and glycol diesters include ethylene glycol dicaprate, propylene glycol dicaprate, propylene glycol dicaprylate, propylene glycol dilaurate, propylene glycol dimyristate, butylene glycol dilaurate, neopentylene glycol diethylhexanoate, Examples include neopentylene glycol dicaprate, and from the viewpoint of emulsification dispersibility and stability, propylene glycol dicaprate, propylene glycol dicaprylate, neopentylene glycol diethylhexanoate, and neopentylene glycol dicaprate are particularly preferred.
脂肪酸グリセリドの例としては、ジカプリル酸グリセリル、ジカプリン酸グリセリル、グリセリル、ジラウリン酸グリセリル、ジミリスチン酸グリセリル、ジパルミトレイン酸グリセリル、ジパルミチン酸グリセリル、ジリノール酸グリセリル、ジリノレン酸グリセリル、ジステアリン酸グリセリル、ジオレイン酸グリセリル、ジイソステアリン酸グリセリルなどが挙げられるが、乳化組成物の安定性の観点から、ジオレイン酸グリセリル、ジイソステアリン酸グリセリル、ジカプリル酸グリセリル、又はジカプリン酸グリセリルがより好ましい。 Examples of fatty acid glycerides include glyceryl dicaprylate, glyceryl dicaprate, glyceryl, glyceryl dilaurate, glyceryl dimyristate, glyceryl dipalmitoleate, glyceryl dipalmitate, glyceryl dilinoleate, glyceryl dilinolenate, glyceryl distearate, dioleic acid. Examples include glyceryl, glyceryl diisostearate, and from the viewpoint of stability of the emulsified composition, glyceryl dioleate, glyceryl diisostearate, glyceryl dicaprylate, and glyceryl dicaprate are more preferred.
またグリセリンの2量体がジエステル化された化合物の例として、ジイソステアリン酸ポリグリセリン(2)、ジステアリン酸ポリグリセリン(2)、ジミリスチン酸ポリグリセリン(2)、ジカプリン酸ポリグリセリン(2)などが挙げられるが、溶解性、乳化安定性の観点から、ジステアリン酸ポリグリセリン(2)、ジミリスチン酸ポリグリセリン(2)が好ましい。 Examples of compounds in which glycerin dimers are diesterified include polyglyceryl diisostearate (2), polyglyceryl distearate (2), polyglyceryl dimyristate (2), and polyglyceryl dicaprate (2). From the viewpoint of solubility and emulsion stability, polyglyceryl distearate (2) and polyglyceryl dimyristate (2) are preferred.
(2)一般式(3)で表される化合物
この化合物は、有機二塩基酸と高級アルコールとのジエステル化合物を表す。
(2) Compound represented by general formula (3) This compound represents a diester compound of an organic dibasic acid and a higher alcohol.
ここで、有機二塩基酸としては、シュウ酸、マロン酸、コハク酸、グルタル酸、セバシン酸、アジピン酸、リンゴ酸、酒石酸、ダイマー酸、ナフタリンジカルボン酸、などが挙げられるが、安全性、入手容易性から、セバシン酸、アジピン酸、リンゴ酸、コハク酸が好ましい。 Here, examples of organic dibasic acids include oxalic acid, malonic acid, succinic acid, glutaric acid, sebacic acid, adipic acid, malic acid, tartaric acid, dimer acid, naphthalene dicarboxylic acid, etc. From the viewpoint of ease, sebacic acid, adipic acid, malic acid, and succinic acid are preferred.
この二塩基酸と高級アルコールのジエステル化合物としては、コハク酸ジエチルヘキシル、リンゴ酸ジイソステアリル、アジピン酸ジイソブチル、ダイマー酸ジイソプロピルが好ましい。 As the diester compound of dibasic acid and higher alcohol, diethylhexyl succinate, diisostearyl malate, diisobutyl adipate, and diisopropyl dimerate are preferable.
油剤である成分(D)及び(E)の合計含油量は、本発明の乳化組成物の濁度を低く抑え、且つ、乳化組成物を化粧料に適用した際に、化粧料使用感を向上させる観点から、乳化組成物の総量に対して、1質量%~35質量%が好ましい。 The total oil content of components (D) and (E), which are oil agents, suppresses the turbidity of the emulsified composition of the present invention to a low level, and improves the feel of the cosmetic when the emulsified composition is applied to the cosmetic. From the viewpoint of increasing the concentration, the amount is preferably 1% by mass to 35% by mass based on the total amount of the emulsified composition.
本発明の乳化組成物において、(A)成分に対する(D)成分の量は、50質量%~400質量%である。(A)成分に対する(D)成分の量が50質量%未満であると、時間経過と共に溶解した成分が析出する事に起因する濁度上昇が起こり、(A)成分に対する(D)成分の量が400質量%を超えると、乳化直後から濁度が大きくなるためである。 In the emulsified composition of the present invention, the amount of component (D) relative to component (A) is 50% by mass to 400% by mass. If the amount of component (D) relative to component (A) is less than 50% by mass, turbidity will increase due to precipitation of dissolved components over time, and the amount of component (D) relative to component (A) will increase over time. This is because if it exceeds 400% by mass, turbidity increases immediately after emulsification.
本発明の乳化組成物における成分(D)の含有量は、1質量%~20質量%が好ましく、2質量%~4質量%がより好ましい。 The content of component (D) in the emulsified composition of the present invention is preferably 1% by mass to 20% by mass, more preferably 2% by mass to 4% by mass.
(E)トコフェロール及びトコフェロールその誘導体からなる群より選ばれる少なくとも一種
本発明の乳化組成物は、トコフェロール及びトコフェロールその誘導体からなる群より選ばれる少なくとも一種をさらに含有してもよい。
(E) At least one selected from the group consisting of tocopherol and tocopherol derivatives The emulsified composition of the present invention may further contain at least one selected from the group consisting of tocopherol and tocopherol derivatives.
グリチルレチン酸誘導体の含有量が1.0質量%以上5.0質量%以下である場合、トコフェロール及びその誘導体を含有することが好ましい。 When the content of the glycyrrhetinic acid derivative is 1.0% by mass or more and 5.0% by mass or less, it is preferable to contain tocopherol and its derivative.
トコフェロール及びその誘導体は、グリチルレチン酸誘導体の溶解性が極めて高い油剤である。 Tocopherol and its derivatives are oil agents in which glycyrrhetinic acid derivatives have extremely high solubility.
本発明におけるトコフェロール及びその誘導体は、トコフェロール及び基本骨格をトコフェロールとした誘導体を指し、具体的には、トコフェロールの異性体であるα、β、γ、及びδトコフェロール、トコフェロールが有するOH基が脂肪酸で修飾された酢酸トコフェロール、基本骨格をトコールとするトコトリエノール等が挙げられる。 Tocopherol and its derivatives in the present invention refer to tocopherol and derivatives having tocopherol as a basic skeleton. Specifically, tocopherol isomers of α, β, γ, and δ tocopherol, and the OH group of tocopherol is a fatty acid. Examples include modified tocopherol acetate and tocotrienols whose basic skeleton is tocol.
トコフェロール及びその誘導体の由来は特に限定されず、具体的には、ひまわり、とうもろこし、オリーブ、菜種、大豆、落花生、アーモンドでもよい。 The origin of tocopherol and its derivatives is not particularly limited, and specifically, they may be derived from sunflowers, corn, olives, rapeseed, soybeans, peanuts, and almonds.
本発明におけるトコフェロール及びその誘導体としては、トコフェロール、酢酸トコフェロール、又はトコトリエノールをより好ましく用いることができる。 As the tocopherol and its derivative in the present invention, tocopherol, tocopherol acetate, or tocotrienol can be more preferably used.
トコフェロール及びその誘導体は、単独でも2種以上を組合せてもよい。 Tocopherol and its derivatives may be used alone or in combination of two or more.
乳化組成物中のグリチルレチン酸誘導体の含有量が、1.0質量%以上5.0質量%以下である場合、成分(E)は、酢酸トコフェロール、トコフェロール及びトコトリエノールから選択される少なくとも1種を含むことが好ましい。 When the content of the glycyrrhetinic acid derivative in the emulsified composition is 1.0% by mass or more and 5.0% by mass or less, component (E) contains at least one selected from tocopherol acetate, tocopherol, and tocotrienol. It is preferable.
本発明の乳化組成物が成分(E)を含有する場合、含有量は、0.5質量%~5質量%が好ましい。 When the emulsified composition of the present invention contains component (E), the content is preferably 0.5% by mass to 5% by mass.
(F)併用可能なオイル類
本発明には(D)で示したジエステル化合物の他に、炭素数10~18の脂肪酸モノエステル類、N-アシルアミノ酸エステル類、トリ脂肪酸グリセリド類を含んでも良い。
(F) Oils that can be used in combination In addition to the diester compounds shown in (D), the present invention may also contain fatty acid monoesters having 10 to 18 carbon atoms, N-acylamino acid esters, and trifatty acid glycerides. .
脂肪酸モノエステル類としては、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、リノール酸、リノレン酸、などが挙げられる。 Examples of fatty acid monoesters include lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, and linolenic acid.
N-アシルアミノ酸エステル類としては、ラウロイルグルタミン酸ジ(コレステリル/オクチルドデシル)、ラウロイルグルタミン酸ジヘキシルデシル、ラウロイルグルタミン酸ジイソステアリル、ラウロイルサルコシンイソプロピルなどが挙げられる。 Examples of the N-acyl amino acid esters include di(cholesteryl/octyldodecyl) lauroylglutamate, dihexyldecyl lauroylglutamate, diisostearyl lauroylglutamate, and isopropyl lauroylsarcosine.
トリ脂肪酸グリセリド類としては、トリ(カプリル酸/カプリン酸)グリセリル、リイソステアリン酸グリセリル、トリカプリル酸グリセリル、トリカプリン酸グリセリル、又はトリトリリノール酸グリセリル、トリリノレン酸グリセリル、トリステアリン酸グリセリル、トリオレイン酸グリセリルなどが挙げられる。 Examples of trifatty acid glycerides include tri(caprylic acid/capric acid) glyceryl, glyceryl diisostearate, glyceryl tricaprylate, glyceryl tricaprate, glyceryl tritrilinoleate, glyceryl trilinolenate, glyceryl tristearate, and glyceryl trioleate. Examples include.
(G)多価アルコール
本発明の乳化組成物は、透明性、経時安定性、及び防腐性の観点から多価アルコールを含有することが好ましい。
(G) Polyhydric alcohol The emulsified composition of the present invention preferably contains a polyhydric alcohol from the viewpoints of transparency, stability over time, and antiseptic properties.
多価アルコールは、保湿機能や粘度調整機能等を有している。また、多価アルコールは、水と油脂成分との界面張力を低下させ、界面を広がりやすくし、微細で、且つ、安定な微粒子を形成しやすくする機能も有している。以上より、乳化組成物が多価アルコールを含有することは、乳化粒子径をより微細化でき、且つ、粒子径が微細な粒子径の状態のまま長期に亘り安定して保持できるとの観点から好ましい。また、多価アルコールの添加により、乳化組成物の水分活性を下げることができ、微生物の繁殖を抑えることができる。 Polyhydric alcohol has a moisturizing function, a viscosity adjusting function, and the like. Polyhydric alcohols also have the function of lowering the interfacial tension between water and oil and fat components, making it easier to spread the interface, and making it easier to form fine and stable particles. From the above, the reason why the emulsified composition contains a polyhydric alcohol is that the emulsion particle size can be made finer and the particle size can be stably maintained in a fine particle size state for a long period of time. preferable. Further, by adding a polyhydric alcohol, the water activity of the emulsified composition can be lowered, and the proliferation of microorganisms can be suppressed.
本発明における多価アルコールとしては、二価以上のアルコールであれば特に限定されず用いることができる。多価アルコールとしては、例えば、グリセリン、ジグリセリン、トリグリセリン、ポリグリセリン、3-メチル-1,3-ブタンジオール、1,3-ブチレングリコール、イソプレングリコール、ポリエチレングリコール、1,2-ペンタンジオール、1,2-ヘキサンジオール、プロピレングリコール、ジプロピレングリコール、エチレングリコール、ジエチレングリコール、ネオペンチルグリコール等が挙げられる。これらの多価アルコールを、単独又は複数種の混合物の形態で用いることができる。 The polyhydric alcohol in the present invention is not particularly limited and can be used as long as it is dihydric or higher alcohol. Examples of polyhydric alcohols include glycerin, diglycerin, triglycerin, polyglycerin, 3-methyl-1,3-butanediol, 1,3-butylene glycol, isoprene glycol, polyethylene glycol, 1,2-pentanediol, Examples include 1,2-hexanediol, propylene glycol, dipropylene glycol, ethylene glycol, diethylene glycol, neopentyl glycol, and the like. These polyhydric alcohols can be used alone or in the form of a mixture of multiple types.
多価アルコールとしては、その1分子中における水酸基の数が、3個以上であるものを用いることが好ましい。これにより、水性媒体と油性成分との界面張力をより効果的に低下させることができ、より微細で、且つ、安定な乳化組成物を形成することができる。その結果、本発明の乳化組成物を化粧料に適用した場合において、経皮吸収性をより高いものとすることができる。 As the polyhydric alcohol, it is preferable to use one having three or more hydroxyl groups in one molecule. Thereby, the interfacial tension between the aqueous medium and the oily component can be lowered more effectively, and a finer and more stable emulsion composition can be formed. As a result, when the emulsified composition of the present invention is applied to cosmetics, transdermal absorption can be made higher.
上述したような条件を満足する多価アルコールの中でも、特に、グリセリンを用いた場合、乳化組成物の粒子径がより小さくなり、且つ、粒子径が小さいまま長期に亘り安定して保持されるため、好ましい。 Among the polyhydric alcohols that satisfy the above-mentioned conditions, when glycerin is used, the particle size of the emulsified composition becomes smaller, and the particle size is stably maintained for a long period of time while remaining small. ,preferable.
多価アルコールの含有量は、乳化組成物が示す透明性、経時安定性、及び防腐性に加えて、乳化組成物の粘度の観点から、組成物の全量に対して10質量%~60質量%が好ましく、20質量%~55質量%がより好ましく、30質量%~50質量%が更に好ましい。 The content of polyhydric alcohol is 10% by mass to 60% by mass based on the total amount of the composition, from the viewpoint of transparency, stability over time, and preservative properties of the emulsified composition, as well as the viscosity of the emulsified composition. is preferable, 20% by weight to 55% by weight is more preferable, and even more preferably 30% to 50% by weight.
多価アルコールの含有量が10質量%以上であると、油性成分の種類や含有量等によっても、十分な保存安定性が得られ易い点で好ましい。一方、多価アルコールの含有量が60質量%以下であると、最大限の効果が得られ、乳化組成物の粘度が高くなるのを抑え易い点で好ましい。 It is preferable that the polyhydric alcohol content is 10% by mass or more, since sufficient storage stability can be easily obtained depending on the type and content of the oily component. On the other hand, it is preferable that the content of the polyhydric alcohol is 60% by mass or less because the maximum effect can be obtained and it is easy to prevent the viscosity of the emulsified composition from increasing.
(H)水
本発明の乳化組成物は、好ましくは水を含有する。水の含油量は、防腐性の観点から組成物全量に対して20質量%~75質量%が好ましく、20質量~50質量%以下がより好ましい。
(H) Water The emulsified composition of the present invention preferably contains water. The oil content of water is preferably 20% to 75% by mass, more preferably 20% to 50% by mass or less, based on the total amount of the composition from the viewpoint of antiseptic properties.
(I)その他の添加成分
本発明の乳化組成物は、上記成分の他、食品、化粧品等の分野において通常用いられる添加成分を、その形態に応じて適宜含有してもよい。
(I) Other additive components In addition to the above-mentioned components, the emulsified composition of the present invention may appropriately contain additive components commonly used in the fields of foods, cosmetics, etc., depending on the form thereof.
例えば、その他の添加成分としては、グルコース、ショ糖、カッパーカラギーナン、ローカストビーンガム、グアーガム、ヒドロキシプロピルグアガム、キサンタンガム、カラヤガム、タマリンド種子多糖、アラビアガム、トラガカントガム、ヒアルロン酸、ヒアルロン酸ナトリウム、コンドロイチン硫酸ナトリウム、デキストリン等の単糖類又は多糖類;ソルビトール、マンニトール、マルチトール、ラクトース、マルトトリイトール、キシリトールなどの糖アルコール;塩化ナトリウム、硫酸ナトリウムなどの無機塩;カゼイン、アルブミン、メチル化コラーゲン、加水分解コラーゲン、水溶性コラーゲン、ゼラチン等の分子量5000超のタンパク質;グリシン、アラニン、バリン、ロイシン、イソロイシン、セリン、スレオニン、アスパラギン酸、グルタミン酸、シスチン、メチオニン、リジン、ヒドロキシリジン、アルギニン、ヒスチジン、フェニルアラニン、チロシン、トリプトファン、プロリン、ヒドロキシプロリン、アセチルヒドロキシプロリン等のアミノ酸及びそれらの誘導体;カルボキシビニルポリマー、ポリアクリル酸ナトリウム、ポリビニルアルコール、ポリエチレングリコール、酸化エチレン・酸化プロピレンブロック共重合体等の合成高分子;ヒドロキシエチルセルロース・メチルセルロース等の水溶性セルロース誘導体;フラボノイド類(カテキン、アントシアニン、フラボン、イソフラボン、フラバン、フラバノン、ルチン)、アスコルビン酸又はその誘導体(アスコルビン酸、アスコルビン酸ナトリウム、アスコルビン酸カリウム、アスコルビン酸カルシウム、L-アスコルビン酸リン酸エステル、リン酸アスコルビルマグネシウム、リン酸アスコルビルナトリウム、硫酸アスコルビル、硫酸アスコルビル2ナトリウム塩、及びアスコルビル-2-グルコシド等)、トコトリエノール及びその誘導体、フェノール酸類(クロロゲン酸、エラグ酸、没食子酸、没食子酸プロピル)、リグナン類、クルクミン類、クマリン類、プテロスチルベン等を含むヒドロキシスチルベン、などを挙げることができる。これらの添加成分は、その機能に基づいて、例えば機能性成分、賦形剤、粘度調整剤、ラジカル捕捉剤などとして含まれてもよい。 For example, other additive ingredients include glucose, sucrose, copper carrageenan, locust bean gum, guar gum, hydroxypropyl guar gum, xanthan gum, karaya gum, tamarind seed polysaccharide, gum arabic, gum tragacanth, hyaluronic acid, sodium hyaluronate, and sodium chondroitin sulfate. , monosaccharides or polysaccharides such as dextrin; sugar alcohols such as sorbitol, mannitol, maltitol, lactose, maltotriitol, xylitol; inorganic salts such as sodium chloride, sodium sulfate; casein, albumin, methylated collagen, hydrolyzed collagen , water-soluble collagen, gelatin, and other proteins with a molecular weight of over 5000; glycine, alanine, valine, leucine, isoleucine, serine, threonine, aspartic acid, glutamic acid, cystine, methionine, lysine, hydroxylysine, arginine, histidine, phenylalanine, tyrosine, Amino acids and their derivatives such as tryptophan, proline, hydroxyproline, acetyl hydroxyproline; Synthetic polymers such as carboxyvinyl polymer, sodium polyacrylate, polyvinyl alcohol, polyethylene glycol, ethylene oxide/propylene oxide block copolymer; hydroxyethyl cellulose・Water-soluble cellulose derivatives such as methylcellulose; flavonoids (catechins, anthocyanins, flavones, isoflavones, flavans, flavanones, rutin), ascorbic acid or its derivatives (ascorbic acid, sodium ascorbate, potassium ascorbate, calcium ascorbate, L- ascorbyl phosphate, ascorbyl magnesium phosphate, sodium ascorbyl phosphate, ascorbyl sulfate, ascorbyl sulfate disodium salt, ascorbyl-2-glucoside, etc.), tocotrienols and their derivatives, phenolic acids (chlorogenic acid, ellagic acid, gallic acid) , propyl gallate), lignans, curcumins, coumarins, hydroxystilbenes including pterostilbene, and the like. These additive components may be included, for example, as functional components, excipients, viscosity modifiers, radical scavengers, etc., based on their functions.
その他、本発明においては、例えば、種々の薬効成分、pH調整剤、pH緩衝剤、紫外線吸収剤、防腐剤、香料、着色剤など、通常、その用途で使用される他の添加物を併用することができる。 In addition, in the present invention, other additives normally used for the purpose, such as various medicinal ingredients, pH adjusters, pH buffers, ultraviolet absorbers, preservatives, fragrances, and colorants, may be used in combination. be able to.
本発明の乳化組成物は、好ましくはγ-オリザノールを含有しない。 The emulsified composition of the present invention preferably does not contain γ-oryzanol.
乳化組成物の製造方法
本発明の乳化組成物の製造方法は、特に限定されず、公知の方法に従い製造することができる。例えば、a)水性媒体に、水溶性成分を溶解させ、レシチンを分散させて水相を得ること、b)油剤、油性成分、HLBが12以上の界面活性剤を混合又は溶解して、油相を得ること、c)攪拌下で水相と油相を混合して、乳化分散を行い、乳化組成物を得ること、を含む製造方法が好ましい。
Method for producing emulsified composition The method for producing the emulsified composition of the present invention is not particularly limited, and can be produced according to known methods. For example, a) a water-soluble component is dissolved in an aqueous medium and lecithin is dispersed to obtain an aqueous phase; b) an oil agent, an oil-based component, and a surfactant with an HLB of 12 or more are mixed or dissolved to form an oil phase. and c) mixing an aqueous phase and an oil phase under stirring to perform emulsification dispersion to obtain an emulsified composition.
乳化分散における油相と水相との比率(質量)は、特に限定されるものではないが、油相/水相比率(質量%)として0.1/99.9~50/50が好ましく、0.5/99.5~30/70がより好ましく、1/99~20/80が更に好ましい。油相/水相比率を0.1/99.9以上とすることにより、有効成分が低くならないため乳化組成物の実用上の問題が生じない傾向となり好ましい。また、油相/水相比率を50/50以下とすることにより、界面活性剤濃度が薄くなることがなく、乳化組成物の経時安定性が保たれるため好ましい。 The ratio (mass) of the oil phase to the aqueous phase in the emulsified dispersion is not particularly limited, but the oil phase/aqueous phase ratio (mass%) is preferably 0.1/99.9 to 50/50. More preferably 0.5/99.5 to 30/70, still more preferably 1/99 to 20/80. It is preferable to set the oil phase/aqueous phase ratio to 0.1/99.9 or more, since the active ingredients will not become low, and therefore problems in practical use of the emulsified composition will not occur. Further, it is preferable to set the oil phase/aqueous phase ratio to 50/50 or less because the surfactant concentration does not become diluted and the stability of the emulsified composition over time is maintained.
乳化分散は、1ステップの乳化操作を行ってもよいが、2ステップ以上の乳化操作を行うことが均一で微細な乳化粒子を得る点から好ましい。具体的には、剪断作用を利用する通常の乳化装置(例えば、スターラーやインペラー攪拌、ホモミキサー、連続流通式剪断装置等)を用いて乳化するという1ステップの乳化操作に加えて、高圧ホモジナイザー、超音波分散機等を通して乳化する等の方法で2種以上の乳化装置を併用するのが特に好ましい。高圧ホモジナイザーを使用することで、乳化物を更に均一な微粒子の液滴に揃えることが出来る。また、更に均一な粒子径の液滴とする目的で複数回行っても良い。 The emulsification and dispersion may be carried out by a one-step emulsification operation, but it is preferable to carry out two or more steps of emulsification operation in order to obtain uniform and fine emulsified particles. Specifically, in addition to the one-step emulsification operation of emulsifying using a normal emulsifying device that uses shearing action (for example, a stirrer, impeller stirring, homomixer, continuous flow shearing device, etc.), a high-pressure homogenizer, It is particularly preferable to use two or more types of emulsifying devices in combination, such as emulsifying through an ultrasonic disperser or the like. By using a high-pressure homogenizer, the emulsion can be made into more uniform fine droplets. Further, the process may be performed multiple times in order to obtain droplets with a more uniform particle size.
本発明の乳化組成物は、適宜pH調整剤を使用することができる。pH調整剤により調整された本発明の乳化組成物のpH値は、4~10の範囲であることが好ましい。 The emulsified composition of the present invention may appropriately contain a pH adjuster. The pH value of the emulsified composition of the present invention adjusted with a pH adjuster is preferably in the range of 4 to 10.
pH調整剤は、乳化組成物を調製する前及び後のいずれに使用してもよい。pHの変動幅を小さくして、より緩和な条件でpHを調整することが可能である点から、pH調整剤は、乳化組成物の調製前に使用することが好ましい。その際には、pH調整剤は、乳化組成物を調製する前の水相組成物、及び油相組成物のいずれに添加してもよい。 The pH adjuster may be used either before or after preparing the emulsified composition. It is preferable to use the pH adjuster before preparing the emulsion composition, since it is possible to reduce the range of pH fluctuation and adjust the pH under milder conditions. In that case, the pH adjuster may be added to either the aqueous phase composition or the oil phase composition before preparing the emulsified composition.
pH調整剤としては、無機酸、有機酸、無機塩基及びそれらの塩を用いてもよく、具体的には、クエン酸、グルコン酸、カルボン酸、酒石酸、コハク酸、酢酸またはフタル酸、トリフルオロ酢酸、モルホリノエタンスルホン酸、2-〔4-(2-ヒドロキシエチル)-1-ピペラジニル〕エタンスルホン酸のような有機酸とその塩;トリス(ヒドロキシメチル)、アミノメタン、アンモニアのような有機塩基;塩酸、過塩素酸、炭酸のような無機酸とその塩;リン酸ナトリウム、リン酸カリウム、水酸化カルシウム、水酸化ナトリウム、水酸化カリウム、水酸化マグネシウムのような無機塩基;リン酸水素ナトリウム、炭酸水素ナトリウムのような無機水素塩が挙げられるが、これらに限定されるものではない。 As the pH adjuster, inorganic acids, organic acids, inorganic bases, and salts thereof may be used, and specifically, citric acid, gluconic acid, carboxylic acid, tartaric acid, succinic acid, acetic acid or phthalic acid, trifluoroacid, etc. Organic acids and their salts such as acetic acid, morpholinoethanesulfonic acid, 2-[4-(2-hydroxyethyl)-1-piperazinyl]ethanesulfonic acid; organic bases such as tris(hydroxymethyl), aminomethane, ammonia ; Inorganic acids and their salts such as hydrochloric acid, perchloric acid, and carbonic acid; Inorganic bases such as sodium phosphate, potassium phosphate, calcium hydroxide, sodium hydroxide, potassium hydroxide, and magnesium hydroxide; Sodium hydrogen phosphate , inorganic hydrogen salts such as sodium hydrogen carbonate, but are not limited to these.
化粧料
本発明の乳化組成物は、化粧料用途などに適用することができる。
Cosmetics The emulsion composition of the present invention can be applied to cosmetics and the like.
本発明の化粧料は、例えば、本発明の乳化組成物及び必要に応じて添加成分を、スターラーやインペラー攪拌、ホモミキサーなどを用いて、混合等して得ることができる。 The cosmetic of the present invention can be obtained, for example, by mixing the emulsified composition of the present invention and optionally additional components using a stirrer, impeller agitation, homomixer, or the like.
上記した各成分以外に任意の他の成分を、必要に応じて含むことができる。 In addition to the above-mentioned components, any other components may be included as necessary.
化粧料は化合物(A)やトコフェロール類の安定性向上という観点から、抗酸化剤を含むことができる。抗酸化剤としては、アスコルビン酸化合物、ジブチルヒドロキシトルエン、カロテノイド類等が挙げられる。安定性を顕著に向上させるという点で、抗酸化剤としては、アスコルビン酸化合物より選択された少なくとも1種がより好ましい。 Cosmetics can contain antioxidants from the viewpoint of improving the stability of compound (A) and tocopherols. Examples of antioxidants include ascorbic acid compounds, dibutylhydroxytoluene, carotenoids, and the like. As the antioxidant, at least one selected from ascorbic acid compounds is more preferable in that it significantly improves stability.
アスコルビン酸化合物としては、例えば、アスコルビン酸、アスコルビン酸ナトリウム、アスコルビン酸マグネシウム、アスコルビン酸硫酸マグネシウム、アスコルビン酸硫酸ナトリウム、アスコルビン酸リン酸マグネシウム、アスコルビン酸リン酸ナトリウム、アスコルビン酸グルコシド、アスコルビン酸パルミテートが挙げられる。 Examples of the ascorbic acid compound include ascorbic acid, sodium ascorbate, magnesium ascorbate, magnesium ascorbate sulfate, sodium ascorbate sulfate, magnesium ascorbyl phosphate, sodium ascorbyl phosphate, ascorbyl glucoside, and ascorbyl palmitate. It will be done.
化粧料は、他の機能性油性成分を含むことができる。機能性油性成分は各種生理活性が期待できる機能性油性成分として既知のものであってもよい。また、機能性油性成分は本発明の乳化時に一緒に添加されても良いが、別に乳化して化粧料製造時に混合されても良い。 The cosmetic may contain other functional oily ingredients. The functional oil component may be a known functional oil component that can be expected to have various physiological activities. Further, the functional oily component may be added together during emulsification of the present invention, but may also be emulsified separately and mixed during cosmetic production.
機能性油性成分の具体例としては、例えば、天然型セラミド類、糖修飾セラミド等のセラミド類;オリーブ油、ツバキ油、マカデミアナッツ油、ヒマシ油、ココナッツ油等の油脂類;コエンザイムQ10等のユビキノン類;EPA、DHA、リノレン酸等のω-3油脂類;流動パラフィン、パラフィン、ワセリン、セレシン、マイクロクリスタリンワックス、スクワラン等の炭化水素;カルナウバロウ、キャンデリラロウ、ミツロウ、ラノリン等のロウ;メチルポリシロキサン、メチルフェニルポリシロキサン等のシリコーン油;;ビタミンA類、ビタミンD類等の脂溶性ビタミン;などを挙げることができる。 Specific examples of functional oil components include ceramides such as natural ceramides and sugar-modified ceramides; fats and oils such as olive oil, camellia oil, macadamia nut oil, castor oil, and coconut oil; ubiquinones such as coenzyme Q10; omega-3 oils and fats such as EPA, DHA, and linolenic acid; hydrocarbons such as liquid paraffin, paraffin, vaseline, ceresin, microcrystalline wax, and squalane; waxes such as carnauba wax, candelilla wax, beeswax, and lanolin; methylpolysiloxane, Examples include silicone oil such as methylphenylpolysiloxane; fat-soluble vitamins such as vitamin A and vitamin D; and the like.
化粧料は、種々の生体機能の発揮が期待される天然物からの各種抽出物を含むことができる。このような各種抽出物としては、例えば、ニンジンエキス、センブリエキス、アロエエキス-1、アルニカエキス、オドリコソウエキス、オランダカラシエキス、桑白皮エキスゴボウエキス、セイヨウキズタエキス、ニンニクエキス、松エキス、ローズマリーエキス、オノニスエキスローマカミツレエキス、アルテアエキス、オノニスエキス、セイヨウノコギリソウエキス、桐葉エキス、セロリエキス、タイムエキス-2、サンショウエキス、フキタンポポエキス、ホップエキス、チンピエキスメリッサエキス、セージエキス、ユーカリエキス、黄杞エキス、オトギリソウエキス、カモミラエキス、スギナエキス、サンショウエキス、シャクヤクエキス、ビワ葉エキス等が挙げられ。 Cosmetics can contain various extracts from natural products that are expected to exhibit various biological functions. Examples of such various extracts include carrot extract, Japanese cabbage extract, aloe extract-1, arnica extract, dead nettle extract, Dutch mustard extract, mulberry bark extract, burdock extract, Ivy extract, garlic extract, pine extract, rose Marie extract, Ononis extract, Roman chamomile extract, Althea extract, Ononis extract, Yarrow extract, Paulownia leaf extract, celery extract, Thyme extract-2, Sansho extract, Coltsfoot extract, Hop extract, Chimpi extract, Melissa extract, Sage extract, Eucalyptus Extracts include yellow perforator extract, hypericum extract, chamomilla extract, horsetail extract, Japanese horsetail extract, peony extract, and loquat leaf extract.
上記成分の他、化粧料、特に頭皮用の皮膚外用剤に通常用いられる添加成分を、本発明の皮膚外用剤に、その形態に応じて適宜含有させてもよい。 In addition to the above-mentioned components, the external skin preparation of the present invention may appropriately contain additive components commonly used in cosmetics, particularly in external skin preparations for the scalp, depending on the form thereof.
その他の添加成分としては、例えば、カッパーカラギーナン、ローカストビーンガム、グアーガム、ヒドロキシプロピルグアガム、キサンタンガム、カラヤガム、タマリンド種子多糖、アラビアガム、トラガカントガム、ヒアルロン酸、ヒアルロン酸ナトリウム、コンドロイチン硫酸ナトリウム、デキストリン等の単糖類又は多糖類;ソルビトール、マンニトール、マルチトール、ラクトース、マルトトリイトール、キシリトールなどの糖アルコール;チアミン等のビタミンB1化合物;リボフラビン等のビタミンB2化合物;ニコチン酸、ニコチン酸アミド等のビタミンB3化合物;ナイアシン、パントテン酸、パントテニルエチルエーテル等のビタミンB5化合物、ピリドキシン等のビタミンB6化合物、ビオチン等のビタミンB7化合物、コバラミン等のビタミンB12化合物、葉酸等のビタミンB群;γ-オリザノール、オロチン酸、グルクロノラクトン、グルクロン酸アミド、ヨクイニンなどの水溶性ビタミン化合物;塩化ナトリウム、硫酸ナトリウムなどの無機塩;カゼイン、アルブミン、メチル化コラーゲン、加水分解コラーゲン、水溶性コラーゲン、ゼラチン等の分子量5000超のタンパク質;グリシン、アラニン、バリン、ロイシン、イソロイシン、セリン、スレオニン、アスパラギン酸、グルタミン酸、シスチン、メチオニン、リジン、ヒドロキシリジン、アルギニン、ヒスチジン、フェニルアラニン、チロシン、トリプトファン、プロリン、ヒドロキシプロリン、アセチルヒドロキシプロリン等のアミノ酸及びそれらの誘導体;カルボキシビニルポリマー、ポリアクリル酸ナトリウム、ポリビニルアルコール、ポリエチレングリコール、酸化エチレン/酸化プロピレンブロック共重合体等の合成高分子;ヒドロキシエチルセルロース/メチルセルロース等の水溶性セルロース誘導体;フラボノイド類(カテキン、アントシアニン、フラボン、イソフラボン、フラバン、フラバノン、ルチン)、フェノール酸化合物(クロロゲン酸、エラグ酸、没食子酸、没食子酸プロピル等)、リグナン化合物、クルクミン化合物、クマリン化合物、プテロスチルベン等を含むヒドロキシスチルベンなどを挙げることができる。皮膚外用剤は、その機能に基づいて、例えば機能性成分、賦形剤、粘度調整剤、ラジカル捕捉剤等として、その他の添加成分を含んでもよい。 Examples of other additive ingredients include copper carrageenan, locust bean gum, guar gum, hydroxypropyl guar gum, xanthan gum, karaya gum, tamarind seed polysaccharide, gum arabic, gum tragacanth, hyaluronic acid, sodium hyaluronate, sodium chondroitin sulfate, and dextrin. Sugars or polysaccharides; sugar alcohols such as sorbitol, mannitol, maltitol, lactose, maltotriitol, xylitol; vitamin B1 compounds such as thiamine; vitamin B2 compounds such as riboflavin; vitamin B3 compounds such as nicotinic acid and nicotinamide; Vitamin B5 compounds such as niacin, pantothenic acid, pantothenylethyl ether, vitamin B6 compounds such as pyridoxine, vitamin B7 compounds such as biotin, vitamin B12 compounds such as cobalamin, vitamin B group such as folic acid; γ-oryzanol, orotic acid, Water-soluble vitamin compounds such as glucuronolactone, glucuronamide, and yokuinin; Inorganic salts such as sodium chloride and sodium sulfate; Proteins with a molecular weight of over 5000 such as casein, albumin, methylated collagen, hydrolyzed collagen, water-soluble collagen, and gelatin. Amino acids such as glycine, alanine, valine, leucine, isoleucine, serine, threonine, aspartic acid, glutamic acid, cystine, methionine, lysine, hydroxylysine, arginine, histidine, phenylalanine, tyrosine, tryptophan, proline, hydroxyproline, acetylhydroxyproline, etc. and their derivatives; synthetic polymers such as carboxyvinyl polymers, sodium polyacrylate, polyvinyl alcohol, polyethylene glycol, ethylene oxide/propylene oxide block copolymers; water-soluble cellulose derivatives such as hydroxyethylcellulose/methylcellulose; flavonoids (catechin, etc.); , anthocyanins, flavones, isoflavones, flavans, flavanones, rutin), phenolic acid compounds (chlorogenic acid, ellagic acid, gallic acid, propyl gallate, etc.), lignan compounds, curcumin compounds, coumarin compounds, hydroxystilbenes including pterostilbene, etc. can be mentioned. The skin external preparation may contain other additive components, such as functional components, excipients, viscosity modifiers, radical scavengers, etc., based on their functions.
その他、本発明においては、例えば、種々の薬効成分、pH調整剤、pH緩衝剤、紫外線吸収剤、香料、着色剤など、通常、その用途で使用される他の添加物を併用することができる。 In addition, in the present invention, other additives normally used for the purpose can be used in combination, such as various medicinal ingredients, pH adjusters, pH buffers, ultraviolet absorbers, fragrances, and colorants. .
化粧料としては、化粧水、美容液、乳液、クリームパック・マスク、パック、洗髪用化粧品、フレグランス化粧品、液体ボディ洗浄料、UVケア化粧品、防臭化粧品、オーラルケア化粧品等(化粧品の場合)などの化粧料が挙げられる。本発明の乳化組成物は、透明性が要求される水性の化粧料に特に好適に適用される。 Cosmetics include lotions, serums, emulsions, cream packs/masks, packs, hair wash cosmetics, fragrance cosmetics, liquid body cleansers, UV care cosmetics, deodorizing cosmetics, oral care cosmetics, etc. (in the case of cosmetics). Examples include cosmetics. The emulsion composition of the present invention is particularly suitably applied to aqueous cosmetics that require transparency.
化粧水、美容液については、一般的に透明性を有することが求められ、その経時変化後も透明で安定していることが要求される。 Lotions and beauty serums are generally required to have transparency, and are required to remain transparent and stable even after changes over time.
本明細書において、「透明性」は濁度を指標として評価される。濁度は、波長650nmの光を用いて、分光光度計を用いて25℃にて測定した吸光度により規定される。 In this specification, "transparency" is evaluated using turbidity as an index. Turbidity is defined by absorbance measured at 25° C. using a spectrophotometer using light with a wavelength of 650 nm.
本明細書において、「経時安定性」は、時間経過前後の濁度の変化率((時間経過後の濁度)/(時間経過前の濁度*100(%))を測定することにより評価することができる。実際には、時間経過前、時間経過後それぞれの乳化組成物を純水で100倍に希釈し、分光光度計を用いて波長650nmの光を用いて測定した吸光度(濁度)から求めることができる。濁度の値は、0.01~0.3であり、より好ましくは0.01~0.2である。 In this specification, "stability over time" is evaluated by measuring the rate of change in turbidity before and after the passage of time ((turbidity after passage of time)/(turbidity before passage of time*100(%)). In fact, each emulsion composition was diluted 100 times with pure water before and after the lapse of time, and the absorbance (turbidity) was measured using a spectrophotometer using light with a wavelength of 650 nm. ) The turbidity value is 0.01 to 0.3, more preferably 0.01 to 0.2.
以下に実施例を挙げて本発明をより具体的に説明するが、本発明はこれらに限定されない。 The present invention will be described in more detail with reference to Examples below, but the present invention is not limited thereto.
実施例1 乳化組成物の調製および評価
(本発明試料1)
1.乳化組成物の調製
下記の成分を、70℃で加熱しながら1時間分散して、水相組成物を得た。
Example 1 Preparation and evaluation of emulsified composition (sample 1 of the present invention)
1. Preparation of emulsified composition The following components were dispersed for 1 hour while heating at 70°C to obtain an aqueous phase composition.
・SLP-PC70 *1 1.5g
・グリセリン 46.8g
・純水 33.7g
また、下記成分を、70℃で加熱しながら1時間溶解して、油相組成物を得た。
・SLP-PC70 *1 1.5g
・Glycerin 46.8g
・Pure water 33.7g
Further, the following components were dissolved for 1 hour while heating at 70°C to obtain an oil phase composition.
・グリチルレチン酸ステアリル 2.0g
・酢酸-DL-トコフェロール 2.0g
・NPDC *2 2.0g
・NIKKOL Decaglyn 1-ISV *3 2.0g
・1,3-ブタンジオール 10.0g
*1 辻製油株式会社 ホスファチジルコリンを70%含有するレシチン
*2 高級アルコール工業株式会社 成分:ジカプリン酸ネオペンチルグリコール
*3 日光ケミカルズ株式会社 モノイソステアリン酸デカグリセリル
・Stearyl glycyrrhetinate 2.0g
・Acetate-DL-tocopherol 2.0g
・NPDC *2 2.0g
・NIKKOL Decaglyn 1-ISV *3 2.0g
・1,3-butanediol 10.0g
*1 Tsuji Oil Co., Ltd. Lecithin containing 70% phosphatidylcholine
*2 Kyukyu Alcohol Industry Co., Ltd. Ingredients: Neopentyl glycol dicaprate
*3 Nikko Chemicals Co., Ltd. Decaglyceryl monoisostearate
水相組成物を攪拌した状態に維持しながら、油相組成物を加えた後、高速攪拌ホモジナイザーを用いて3分間分散することで予備乳化物を得た。 While maintaining the aqueous phase composition in a stirred state, the oil phase composition was added and then dispersed for 3 minutes using a high speed stirring homogenizer to obtain a preliminary emulsion.
続いて、得られた予備乳化物を約60℃まで冷却し、湿式微粒化装置 スターバーストHJP25001(株式会社スギノマシン)を用いて、200MPaの圧力で高圧乳化を行った。 Subsequently, the obtained preliminary emulsion was cooled to about 60° C., and high-pressure emulsification was performed at a pressure of 200 MPa using a wet atomization device Starburst HJP25001 (Sugino Machine Co., Ltd.).
その後、得られた乳化組成物を平均孔径1μmのミクロフィルターでろ過し、80℃で30分加熱滅菌することで実施例1の乳化組成物を調製した。
(本発明試料2)
本発明試料1のNPDCをNDO*4に変えた以外は本発明試料1と同様に作製した。
(本発明試料3)
本発明試料1のNPDCをDADIP*5に変えた以外は本発明試料1と同様に作製した。
(本発明試料4)
本発明試料1のNPDCをDIOS*6に変えた以外は本発明試料1と同様に作製した。
(比較例試料1)
比較例1の乳化組成物は、実施例1のNPDCの代わりに、ココナードMT(花王株式会社、トリ(カプリル・カプリン酸)グリセリル)を用いて調製した(表1)。
(比較例試料2)
本発明試料1のNPDCの量を0.8gとし、全量をグリセリン、水で100gに調整した。
(比較例試料3)
本発明試料1のNPDCの量を10.0gとし、全量をグリセリン、水で100gに調整した。
*4 高級アルコール工業製KAK-NDO 成分:ジエチルヘキシルネオペンチルグリコール
*5 高級アルコール工業製KAK-DADIP 成分:ダイマー酸ジイソプロピル
*6 高級アルコール工業製KAK-DIOS 成分:コハク酸ジエチルヘキシル
Thereafter, the obtained emulsified composition was filtered through a microfilter with an average pore size of 1 μm, and the emulsified composition of Example 1 was prepared by heat sterilizing at 80° C. for 30 minutes.
(Sample 2 of the present invention)
It was produced in the same manner as Inventive Sample 1 except that NPDC in Inventive Sample 1 was changed to NDO *4 .
(Sample 3 of the present invention)
It was produced in the same manner as Inventive Sample 1 except that NPDC in Inventive Sample 1 was changed to DADIP *5 .
(Sample 4 of the present invention)
It was produced in the same manner as Inventive Sample 1 except that NPDC in Inventive Sample 1 was changed to DIOS *6 .
(Comparative example sample 1)
The emulsion composition of Comparative Example 1 was prepared using Coconard MT (Kao Corporation, tri(caprylic/capric) glyceryl) instead of NPDC of Example 1 (Table 1).
(Comparative example sample 2)
The amount of NPDC in Sample 1 of the present invention was 0.8 g, and the total amount was adjusted to 100 g with glycerin and water.
(Comparative example sample 3)
The amount of NPDC in Sample 1 of the present invention was 10.0 g, and the total amount was adjusted to 100 g with glycerin and water.
* 4 KAK-NDO manufactured by Kyokuryuko Kogyo Co., Ltd. Ingredient: Diethylhexyl neopentyl glycol * 5 KAK-DADIP manufactured by Kyokuryuko Kogyo Co., Ltd. Ingredient: diisopropyl dimer acid * 6 KAK-DIOS manufactured by Kyokuryu Alcohol Co., Ltd. Component: Diethylhexyl succinate
2.乳化組成物の評価
上記で得られた各グリチルレチン酸誘導体含有乳化組成物の、濁度、経時安定性を評価した。詳細は以下の通りである。
2. Evaluation of Emulsified Compositions The turbidity and stability over time of each of the glycyrrhetinic acid derivative-containing emulsified compositions obtained above were evaluated. Details are as follows.
2-1.濁度の評価
本発明1~4及び比較例1~3の各グリチルレチン酸誘導体含有乳化組成物 0.1gを、それぞれ、9.9gの純水に添加して、マグネッチックスターラーを用いて、10分間攪拌を行い、水稀釈液を得た。
2-1. Evaluation of turbidity 0.1 g of each glycyrrhetinic acid derivative-containing emulsion composition of Inventions 1 to 4 and Comparative Examples 1 to 3 was added to 9.9 g of pure water, and stirred using a magnetic stirrer for 10 minutes. Stirring was performed for a minute to obtain a diluted solution in water.
得られた各乳化組成物の水希釈液を用い、初期濁度の指標として650nmにおける吸光度を、分光光度計(V-630、株式会社日本分光製)を用いて、25℃にて測定し、下記基準で評価した。また、各乳化組成物の調製から1ヶ月経過後の濁度も測定した。 Using a water diluted solution of each emulsion composition obtained, absorbance at 650 nm was measured as an indicator of initial turbidity using a spectrophotometer (V-630, manufactured by JASCO Corporation) at 25 ° C., Evaluation was made using the following criteria. Moreover, the turbidity was also measured one month after the preparation of each emulsified composition.
評価基準
合格:0.05より大きく0.2以下(○)
不合格:0.2より大きい(×)
Evaluation criteria Pass: greater than 0.05 and less than 0.2 (○)
Fail: Greater than 0.2 (×)
2-2.経時安定性評価
経時安定性の評価(透明性の持続性)は、各グリチルレチン酸誘導体含有乳化組成物を25℃で1ヶ月経時させた後における吸光度変化を濁度変化と見なして測定し、調製直後の吸光度の変化率A(%)を、下記式に基づき求め、下記基準で評価した。
2-2. Evaluation of stability over time Evaluation of stability over time (persistence of transparency) was carried out by measuring the change in absorbance after aging each glycyrrhetinic acid derivative-containing emulsion composition at 25°C for 1 month, treating it as a change in turbidity. The absorbance change rate A (%) immediately after was determined based on the following formula, and evaluated using the following criteria.
変化率A(%)=25℃で1ヶ月間経時させた後の吸光度/調製直後の吸光度×100
変化率A(%)が100%に近い程、乳化組成物は経時安定性に優れることを示す。
Rate of change A (%) = Absorbance after aging at 25°C for 1 month / Absorbance immediately after preparation x 100
The closer the change rate A (%) is to 100%, the more excellent the emulsion composition is in stability over time.
評価基準
合格: 150%未満(〇)
不合格:150%以上(×)
以上の結果を下記表1に示す。各成分の単位はgである。
Evaluation criteria Pass: Less than 150% (〇)
Fail: 150% or more (×)
The above results are shown in Table 1 below. The unit of each component is g.
実施例2.化粧料の調製例
1.化粧料の調製
実施例1の乳化物を用いて表2の組成で化粧料1を作成した。各成分の単位はgである。
Example 2. Cosmetic preparation example 1. Preparation of Cosmetic Composition Cosmetic composition 1 was prepared using the emulsion of Example 1 and having the composition shown in Table 2. The unit of each component is g.
各試薬の製造業者は以下の通りである。
非イオン水溶性ポリマー液 90SH15000 メトローズ(登録商標) ヒドロキシプロピルメチルセルロース 信越化学工業株式会社
Zemea Select Propanediol DuPont Tate & Lyle Bio Products
化粧品用濃グリセリン 花王株式会社
Hydrorite-5 green Symrise
ハイソルブ EPH 東邦化学株式会社
sensiva SC50 JP 成和化成株式会社
レシノール SH50 日光ケミカルズ株式会社
Neosolue-Aqulio 日本精化株式会社
エマノーンHC60 花王株式会社
1,3-ブチレングリコール 株式会社ダイセル
クエン酸 磐田工業株式会社
The manufacturers of each reagent are as follows.
Nonionic water-soluble polymer liquid 90SH15000 Metrose (registered trademark) Hydroxypropyl methylcellulose Shin-Etsu Chemical Co., Ltd.
Zemea Select Propanediol DuPont Tate & Lyle Bio Products
Concentrated glycerin for cosmetics Kao Corporation
Hydrorite-5 green Symrise
High Solv EPH Toho Chemical Co., Ltd.
sensiva SC50 JP Seiwa Kasei Co., Ltd. Resinol SH50 Nikko Chemicals Co., Ltd.
Neosolue-Aqulio Nippon Fine Chemical Co., Ltd. Emanone HC60 Kao Corporation
1,3-Butylene glycol Daicel Citric Acid Co., Ltd. Iwata Industries Co., Ltd.
実施例1におけるのと同じ条件で、化粧料の初期濁度及び25℃で1ヶ月経時させた後における濁度を吸光度で測定したところ、初期濁度の評価、経時安定性の判定はともに〇であった。 Under the same conditions as in Example 1, the initial turbidity of the cosmetic and the turbidity after aging at 25°C for one month were measured by absorbance, and both the evaluation of initial turbidity and the judgment of stability over time were ○. Met.
Claims (7)
(A)下記一般式(1)で表されるグリチルレチン酸誘導体、
R1が、-C12H25、-C14H29、-C16H33、-C18H37、又は-C20H41を表し、且つR2が水素原子を表すか、或いは、
R1が水素原子を表し、且つR2が、-(C=O)C11H23、-(C=O)C13H27、-(C=O)C15H31、又は-(C=O)C17H35を表す。)
(B)リン脂質、
(C)HLBが12以上の界面活性剤、及び
(D)下記一般式(2)又は(3)で表される化合物を一種以上、
R1及びR2が、それぞれ独立して、炭素数2~18の直鎖若しくは分岐アルキル基、又は炭素数2~18の直鎖若しくは分岐アルケニル基であり、
Qが、非置換若しくは置換基を有する炭素数2~40の直鎖若しくは分岐アルキル基、非置換若しくは置換基を有する炭素数2~40の直鎖若しくは分岐アルケニル基、非置換若しくは置換基を有するフェニル基、又は非置換若しくは置換基を有するシクロアルキル基であり、前記直鎖若しくは分岐アルキル基、前記直鎖若しくは分岐アルケニル基、前記フェニル基、及び前記シクロアルキル基の置換基は1又は2個のヒドロキシ基である)
R3及びR4が、それぞれ独立して、炭素数2~18の直鎖若しくは分岐アルキル基、又は炭素数2~18の直鎖若しくは分岐アルケニル基であり、
Qが、非置換若しくは置換基を有する炭素数2~40の直鎖若しくは分岐アルキル基、非置換若しくは置換基を有する炭素数2~40の直鎖若しくは分岐アルケニル基、非置換若しくは置換基を有するフェニル基、又は非置換若しくは置換基を有するシクロアルキル基であり、前記直鎖若しくは分岐アルキル基、前記直鎖若しくは分岐アルケニル基、前記フェニル基、及び前記シクロアルキル基の置換基は1又は2個のヒドロキシ基である)
を含有し、かつ、(A)成分に対する(D)成分の量が50質量%~400質量%である乳化組成物。 Ingredients (A) to (D) below:
(A) a glycyrrhetinic acid derivative represented by the following general formula (1),
R 1 represents -C 12 H 25 , -C 14 H 29 , -C 16 H 33 , -C 18 H 37 , or -C 20 H 41 , and R 2 represents a hydrogen atom, or
R 1 represents a hydrogen atom, and R 2 represents -(C=O)C 11 H 23 , -(C=O)C 13 H 27 , -(C=O)C 15 H 31 , or -(C =O) represents C17H35 . )
(B) phospholipid,
(C) a surfactant with an HLB of 12 or more, and (D) one or more compounds represented by the following general formula (2) or (3),
R 1 and R 2 are each independently a straight chain or branched alkyl group having 2 to 18 carbon atoms, or a straight chain or branched alkenyl group having 2 to 18 carbon atoms,
Q is an unsubstituted or substituted straight chain or branched alkyl group with 2 to 40 carbon atoms, an unsubstituted or substituted straight chain or branched alkenyl group with 2 to 40 carbon atoms, or an unsubstituted or substituent group. A phenyl group or a cycloalkyl group that is unsubstituted or has a substituent, and the linear or branched alkyl group, the linear or branched alkenyl group, the phenyl group, and the cycloalkyl group have 1 or 2 substituents. hydroxyl group)
R 3 and R 4 are each independently a straight chain or branched alkyl group having 2 to 18 carbon atoms, or a straight chain or branched alkenyl group having 2 to 18 carbon atoms,
Q is an unsubstituted or substituted straight chain or branched alkyl group with 2 to 40 carbon atoms, an unsubstituted or substituted straight chain or branched alkenyl group with 2 to 40 carbon atoms, or an unsubstituted or substituent group. A phenyl group or a cycloalkyl group that is unsubstituted or has a substituent, and the linear or branched alkyl group, the linear or branched alkenyl group, the phenyl group, and the cycloalkyl group have 1 or 2 substituents. hydroxyl group)
and the amount of component (D) relative to component (A) is 50% by mass to 400% by mass.
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