JPWO2012093643A1 - 化粧料 - Google Patents
化粧料 Download PDFInfo
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- JPWO2012093643A1 JPWO2012093643A1 JP2012551849A JP2012551849A JPWO2012093643A1 JP WO2012093643 A1 JPWO2012093643 A1 JP WO2012093643A1 JP 2012551849 A JP2012551849 A JP 2012551849A JP 2012551849 A JP2012551849 A JP 2012551849A JP WO2012093643 A1 JPWO2012093643 A1 JP WO2012093643A1
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- 239000002537 cosmetic Substances 0.000 title claims abstract description 60
- -1 alkenyl ammonium Chemical compound 0.000 claims abstract description 42
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 39
- 229940106189 ceramide Drugs 0.000 claims abstract description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000001783 ceramides Chemical class 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 150000007524 organic acids Chemical class 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 12
- 150000001413 amino acids Chemical class 0.000 claims abstract description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 8
- 239000002585 base Substances 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 4
- 125000005210 alkyl ammonium group Chemical group 0.000 claims abstract description 4
- 229930193551 sterin Natural products 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 21
- 238000002156 mixing Methods 0.000 claims description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 238000010438 heat treatment Methods 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 238000002844 melting Methods 0.000 claims description 11
- 230000008018 melting Effects 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 239000003613 bile acid Substances 0.000 claims description 3
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 2
- IRRHHCACCKWUKP-UHFFFAOYSA-N C1=CC=NC=C1.[C+4] Chemical group C1=CC=NC=C1.[C+4] IRRHHCACCKWUKP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 abstract description 2
- 210000000941 bile Anatomy 0.000 abstract 1
- 210000003491 skin Anatomy 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 14
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 14
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 14
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 210000000434 stratum corneum Anatomy 0.000 description 13
- 239000004094 surface-active agent Substances 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 125000004122 cyclic group Chemical group 0.000 description 9
- 229930195734 saturated hydrocarbon Natural products 0.000 description 9
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 9
- 238000005406 washing Methods 0.000 description 8
- 150000002632 lipids Chemical class 0.000 description 7
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 5
- 230000007794 irritation Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 125000004043 oxo group Chemical group O=* 0.000 description 5
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 235000020778 linoleic acid Nutrition 0.000 description 4
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 4
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 4
- 238000010979 pH adjustment Methods 0.000 description 4
- 230000000717 retained effect Effects 0.000 description 4
- 150000004671 saturated fatty acids Chemical class 0.000 description 4
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 4
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 3
- 229930064664 L-arginine Natural products 0.000 description 3
- 235000014852 L-arginine Nutrition 0.000 description 3
- 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 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 229940107161 cholesterol Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 230000035699 permeability Effects 0.000 description 3
- 150000003904 phospholipids Chemical class 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WWUZIQQURGPMPG-UHFFFAOYSA-N (-)-D-erythro-Sphingosine Natural products CCCCCCCCCCCCCC=CC(O)C(N)CO WWUZIQQURGPMPG-UHFFFAOYSA-N 0.000 description 2
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 2
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-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
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 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
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229940099417 ceramide 2 Drugs 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 210000000245 forearm Anatomy 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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- 238000000926 separation method Methods 0.000 description 2
- WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- BQPPJGMMIYJVBR-UHFFFAOYSA-N (10S)-3c-Acetoxy-4.4.10r.13c.14t-pentamethyl-17c-((R)-1.5-dimethyl-hexen-(4)-yl)-(5tH)-Delta8-tetradecahydro-1H-cyclopenta[a]phenanthren Natural products CC12CCC(OC(C)=O)C(C)(C)C1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C BQPPJGMMIYJVBR-UHFFFAOYSA-N 0.000 description 1
- CSVWWLUMXNHWSU-UHFFFAOYSA-N (22E)-(24xi)-24-ethyl-5alpha-cholest-22-en-3beta-ol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(CC)C(C)C)C1(C)CC2 CSVWWLUMXNHWSU-UHFFFAOYSA-N 0.000 description 1
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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
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- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- 229940114072 12-hydroxystearic acid Drugs 0.000 description 1
- XYTLYKGXLMKYMV-UHFFFAOYSA-N 14alpha-methylzymosterol Natural products CC12CCC(O)CC1CCC1=C2CCC2(C)C(C(CCC=C(C)C)C)CCC21C XYTLYKGXLMKYMV-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- ZCOLQXXFCPFSNU-UHFFFAOYSA-N 2-[methyl(tetradecanoyl)amino]ethanesulfonic acid;sodium Chemical compound [Na].CCCCCCCCCCCCCC(=O)N(C)CCS(O)(=O)=O ZCOLQXXFCPFSNU-UHFFFAOYSA-N 0.000 description 1
- IOAOAKDONABGPZ-UHFFFAOYSA-N 2-amino-2-ethylpropane-1,3-diol Chemical compound CCC(N)(CO)CO IOAOAKDONABGPZ-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- KLEXDBGYSOIREE-UHFFFAOYSA-N 24xi-n-propylcholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CCC)C(C)C)C1(C)CC2 KLEXDBGYSOIREE-UHFFFAOYSA-N 0.000 description 1
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
- A61K8/585—Organosilicon compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/63—Steroids; Derivatives thereof
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/68—Sphingolipids, e.g. ceramides, cerebrosides, gangliosides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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Abstract
Description
(A)一般式(1)
で表される有機酸 0.001〜50重量%、
(B)塩基 0.001〜20重量%、
(C)セラミド類 0.0001〜50重量%、
(D)水
を含有し、成分(E)として、成分(A)以外の酸であり、その含有量が、0≦(E)/(A)<0.2であり、組成物としてpH6〜11である化粧料を提供するものである。
一般式(1)において、R1で示される1個の水酸基を有する天然ステリンとしては、例えば、コレステロール、スチグマステロール、シトステロール、カンペステロール、ラノステロール、エルゴステロール等が挙げられ、その中でもコレステロールが好ましい。
成分(A)は、後述する成分(B)との作用で、界面活性剤のような機能を発現することができ、他の界面活性剤を含まなくても、成分(C)のセラミド類を安定に乳化できる。このことにより、成分(C)のセラミド類を乳化するため、他の界面活性剤を含まなくても良い。
有機塩基としては、L−アルギニン、リジン、ヒスチジン等の塩基性アミノ酸;モノエタノールアミン、ジエタノールアミン、トリエタノールアミン、アミノメチルプロパノール、アミノメチルプロパンジオール、アミノエチルプロパンジオール、トリスヒドロキシメチルアミノエタン等のアルカノールアミンから選ばれる1種又は2種以上が好ましい。また、無機塩基としては、水酸化ナトリウム、水酸化カリウムから選ばれる1種又は2種が好ましい。
これらのうち、塩基性アミノ酸、水酸化ナトリウム、水酸化カリウムから選ばれる1種又は2種以上が好ましく、さらに、L−アルギニン、水酸化ナトリウム、水酸化カリウムから選ばれる1種又は2種以上がより好ましい。
成分(B)は、成分(A)を中和して、塩を形成する。このことにより、成分(A)は、界面活性剤のような作用を引き出すことが可能となる。また、組成物全体のpH調整の役割を有する。
(I)一般式(2)で表わされる化合物は、天然由来のセラミド類又は同構造の合成物であっても良い。
これらのセラミドは天然型(D(−)体)の光学活性体を用いても、非天然型(L(+)体)の光学活性体を用いても、更に天然型と非天然型の混合物を用いてもよい。上記化合物の相対立体配置は、天然型の立体配置のものでも、それ以外の非天然型の立体配置のものでも良く、また、これらの混合物によるものでもよい。なかでも、CERAMIDE1、CERAMIDE2、CERAMIDE3、CERAMIDE5、CERAMIDE6IIの化合物(以上、INCI、8th Edition)及び次式で表わされるものから選ばれる1種又は2種以上が好ましい。
このような天然型セラミドの市販のものを用いる場合は、Ceramide I、Ceramide III、Ceramide IIIA、Ceramide IIIB、Ceramide IIIC、Ceramide VI(以上、コスモファーム社)、Ceramide TIC-001(高砂香料社)、CERAMIDE II(Quest International社)、DS-Ceramide VI、DS-CLA-Phytoceramide、C6-Phytoceramide、DS-ceramide Y3S(DOOSAN社)、CERAMIDE2(セダーマ社)から選ばれる1種又は2種以上が好ましい。
有機酸としては、酢酸、プロピオン酸、酪酸等のモノカルボン酸;コハク酸、フタル酸、フマル酸、シュウ酸、マロン酸、グルタル酸等のジカルボン酸;グリコール酸、クエン酸、乳酸、ピルビン酸、リンゴ酸、酒石酸等のオキシカルボン酸;グルタミン酸、アスパラギン酸等のアミノ酸から選ばれる1種又は2種以上が好ましい。
また、無機酸としては、塩酸、硝酸、亜硝酸、硫酸、亜硫酸、リン酸、ホスホン酸、ホスフィン酸から選ばれる1種又は2種以上が好ましい。
これらの中で、有機酸としてはジカルボン酸がより好ましく、無機酸としてはリン酸がより好ましい。
成分(A)との重量割合は、塩析による成分(A)の界面活性能の低下を防止し、皮膚の水分保持量を向上させる点から、0≦(E)/(A)<0.2であり、好ましくは0≦(E)/(A)≦0.1であり、より好ましくは0≦(E)/(A)≦0.08であり、さらに長期の保存安定性と水分保持量の向上の点から、0≦(E)/(A)≦0.05であることが好ましい。
非イオン界面活性剤の含有量は、さらに低刺激にする点及び使用感の向上から、全組成中に1.0重量%以下であるのが好ましく、0.5重量%以下であるのがより好ましく、0.2重量%以下であるのがより好ましい。
アニオン界面活性剤の含有量は、より刺激を低減する点から、全組成中に0.5重量%以下であるのが好ましく、0.2重量%以下であるのがより好ましく、0.1重量%以下であるのがさらに好ましい。
成分(A)、(B)、(C)及び(D)を混合する工程は、成分(A)と成分(B)と成分(D)の一部の水(D1)とを混合し、成分(A)の融点以上に加熱して混合する工程1の後に、成分(C)と他の油性成分を含有する油相を、全ての成分のうち最も高い融点以上に加熱して混合する工程2を備えることが好ましい。なお、前記工程2において、成分(C)を添加した後に、他の油性成分を添加してもよい。
また、成分(A)、(B)、(C)及び(D)を混合する工程は、成分(A)及び(C)を、いずれか高い融点以上に加熱して混合する工程1の後に、成分(B)と成分(D)の一部の水(D1)との混合液を添加して加熱しながら混合する工程2を備えることができる。他の油性成分を添加する工程は、全ての油性成分のうち最も高い融点以上に加熱して混合する工程を、工程2の後に備えることができる。
前記pH調整工程は、工程3において成分(E)を一部の水(D2)に配合することによって、工程3に含めてもよいし、工程3の前又は後に備えることもできる。なお、pHの調整は、成分(B)の含有量によって調整することも可能であるが、前記pH調整工程は、成分(E)と成分(D)の一部の水の添加による工程である。
また、本発明の化粧料の製造方法は、さらに、他の水溶性成分及び成分(D)の一部の水(D3)を含む水相を添加して混合する工程を備えてもよい。なお、成分(D1)、(D2)及び(D3)の含有量の合計が成分(D)の含有量である。
なお、pHは、HORIBA社製、COMPACT pH METER B−212を用い、25℃で、各化粧料を希釈せずに直接測定されるものである。
(A)一般式(1)
で表される有機酸 0.001〜50重量%、
(B)塩基 0.001〜20重量%、
(C)セラミド類 0.0001〜50重量%、
(D)水
を含有し、成分(E)として、成分(A)以外の酸の含有量が、0≦(E)/(A)<0.2であり、pH6〜11である化粧料。
で表わされるものから選ばれる1種又は2種以上である<1>記載の化粧料。
<6>成分(B)を、0.01〜5重量%含有し、好ましくは0.01〜3重量%含有する<1>〜<5>のいずれか1記載の化粧料。
<7>成分(C)を、0.01〜10重量%含有し、好ましくは0.1〜8重量%含有する<1>〜<6>のいずれか1記載の化粧料。
<9>成分(A)及び(E)の重量割合が、0≦(E)/(A)≦0.1であり、好ましくは0≦(E)/(A)≦0.08であり、より好ましくは0≦(E)/(A)≦0.05である<1>〜<8>のいずれか1記載の化粧料。
<11>pHが6〜8である<1>〜<10>のいずれか1記載の化粧料。
<12>pHが7〜9である<1>〜<10>のいずれか1記載の化粧料。
<14>50℃以下に冷却する工程の後にpH6〜11に調整する工程を備える<13>に記載の化粧料の製造方法。
<15>成分(B)の含有量を調整して、pH7以上になるように、成分(A)、(B)、(C)及び(D)を混合し、成分(A)及び(C)のいずれか高い融点以上に加熱して均一に混合する工程の後、50℃以下に冷却する工程を備え、その後、成分(E)を加え、pH6〜11に調整する工程を備える<13>又は<14>に記載の化粧料の製造方法。
<17>成分(A)、(B)、(C)及び(D)を混合し、加熱して均一に混合する工程が、成分(A)及び(C)を加熱して混合する工程1の後に、成分(B)と成分(D)の一部を加熱して混合する工程2を備え、工程2の後に他の油性成分を加熱して混合する工程を備える<13>〜<15>のいずれか1に記載の化粧料の製造方法。
表1及び表2に示す組成の化粧料を製造し、保存安定性を評価した。結果を表1及び表2に併せて示す。
成分(A)及び(C)を80〜90℃で加熱攪拌して均一にし、80℃で均一にした成分(B)と15重量%の成分(D)を、プロペラ450rpmで攪拌しながら徐々に加える。次に、他の油性成分を同様に攪拌しながら加える。さらに攪拌しながら30℃に冷却し、液Iを得た。次に、10重量%の成分(D)にパラオキシ安息香酸メチル、グリセリンを溶解し、液Iに加え、液IIを得た。このときのpHを、成分(E)含む前の各成分(A)〜(D)の溶解均一時のpHとした。次に、成分(E)及びカルボキシビニルポリマーを残りの成分(D)に溶解又は分散し、液IIに加えて均一にした。この後、25℃まで冷却して、化粧料を得た。
各化粧料を、50℃、25℃及び−5℃で、それぞれ1週間保存した後の外観を、肉眼で観察した。更に、光学顕微鏡(400倍)にて観察し、結晶の析出の有無を確認した。結果は、いずれの温度でも、乳化分離や結晶析出が認められず、安定性に優れていたものは「○」、いずれかの温度で、乳化分離又は結晶析出を認め、不安定であるものは「×」で示した。
前記実施例及び比較例の化粧料のうち、表3に示す化粧料について、水分保持量を評価した。結果を表3に併せて示す。
皮膚の水分量の測定は、前腕部の3部位を、各部位の近傍4カ所の合計12カ所を、コルネオメーター(CORNEOMETER CM825、インテグラル社製)で測定することにより行い、水分量としてコルネオメーターに表示された数値を用いた。はじめに、前腕部を洗顔料(ビオレ洗顔フォーム、花王社製)で洗浄し、水分をとってから10分後に測定した水分量を初期値とした。次に、各化粧料を塗布し、6.5時間後に洗浄せずに水分量を測定し、測定値から初期値をひいた数値を水分保持量とした。また、各化粧料を洗浄後の朝、及び入浴後に塗布し、24時間後に洗浄は行わずに水分量を測定し、測定値から初期値をひいた数値を「24時間後、洗浄なし」の水分保持量とした。同様に24時間後に、測定前に洗浄した後に水分量を測定し、測定値から初期値をひいた数値を「24時間後、洗浄あり」の水分保持量とした。
Claims (10)
- 次の成分(A)、(B)、(C)及び(D):
(A)一般式(1)
で表される有機酸 0.001〜50重量%、
(B)塩基 0.001〜20重量%、
(C)セラミド類 0.0001〜50重量%、
(D)水
を含有し、成分(E)として、成分(A)以外の酸の含有量が、0≦(E)/(A)<0.2であり、pH6〜11である化粧料。 - 成分(A)及び(C)の重量割合が、(A)/(C)≧0.001である請求項1記載の化粧料。
- 成分(E)が、ジカルボン酸及びリン酸から選ばれる酸である請求項1又は2記載の化粧料。
- 成分(A)を、0.1〜10重量%含有する請求項1〜3のいずれか1項記載の化粧料。
- 成分(B)を、0.01〜5重量%含有する請求項1〜4のいずれか1項記載の化粧料。
- 成分(C)を、0.01〜10重量%含有する請求項1〜5のいずれか1項記載の化粧料。
- 成分(B)が、塩基性アミノ酸、アルカノールアミン、水酸化ナトリウム及び水酸化カリウムから選ばれる1種又は2種以上である請求項1〜6のいずれか1項記載の化粧料。
- 成分(A)及び(E)の重量割合が、0≦(E)/(A)≦0.1である請求項1〜7のいずれか1項記載の化粧料。
- 成分(A)、(B)、(C)及び(D)を、成分(A)及び(C)のいずれか高い融点以上に加熱して均一に混合する工程の後、50℃以下に冷却する工程を備え、pH6〜11に調整する、請求項1〜8のいずれか1項記載の化粧料の製造方法。
- 成分(B)の含有量を調整して、pH7以上になるよう、成分(A)、(B)、(C)及び(D)を混合し、成分(A)及び(C)のいずれか高い融点以上に加熱して均一に混合する工程の後、50℃以下に冷却する工程を備え、その後、成分(E)を加え、pH6〜11に調整する、請求項1〜8のいずれか1項記載の化粧料の製造方法。
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TWI238068B (en) * | 2001-03-06 | 2005-08-21 | Kao Corp | Composition for external application |
JP4220698B2 (ja) | 2001-12-10 | 2009-02-04 | 花王株式会社 | 皮膚外用剤 |
CN100340227C (zh) | 2001-12-10 | 2007-10-03 | 花王株式会社 | 神经酰胺类乳化物 |
US20070031480A1 (en) * | 2003-03-07 | 2007-02-08 | Lawrence Mayer | Enhanced delivery of sphingolipids |
EP1732577B1 (en) * | 2004-02-23 | 2013-04-10 | Strategic Science & Technologies, LLC | Topical delivery of l-arginine to improve body and skin appearance |
FR2870741B1 (fr) | 2004-05-25 | 2008-03-14 | Coletica Sa | Phase lamellaires hydratees ou liposomes, contenant une monoamine grasse ou un polymere cationique favorisant la penetration intercellulaire, et composition cosmetique ou pharmaceutique la contenant. |
JP5882108B2 (ja) * | 2011-03-31 | 2016-03-09 | 花王株式会社 | ベシクル組成物 |
-
2011
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- 2011-12-28 CN CN201180063868.0A patent/CN103370048B/zh not_active Expired - Fee Related
- 2011-12-28 JP JP2012551849A patent/JP5917414B2/ja active Active
- 2011-12-28 SG SG2013049937A patent/SG191388A1/en unknown
- 2011-12-28 WO PCT/JP2011/080486 patent/WO2012093643A1/ja active Application Filing
- 2011-12-28 US US13/978,148 patent/US9161896B2/en not_active Expired - Fee Related
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2012
- 2012-01-03 TW TW101100204A patent/TWI572365B/zh not_active IP Right Cessation
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SG191388A1 (en) | 2013-08-30 |
CN103370048A (zh) | 2013-10-23 |
WO2012093643A1 (ja) | 2012-07-12 |
TWI572365B (zh) | 2017-03-01 |
JP5917414B2 (ja) | 2016-05-11 |
EP2662071A1 (en) | 2013-11-13 |
TW201231076A (en) | 2012-08-01 |
EP2662071B1 (en) | 2018-06-20 |
US9161896B2 (en) | 2015-10-20 |
EP2662071A4 (en) | 2015-08-26 |
US20130303483A1 (en) | 2013-11-14 |
CN103370048B (zh) | 2016-06-01 |
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