JP6686902B2 - Cosmetic composition containing acyl basic amino acid derivative and basic amino acid - Google Patents
Cosmetic composition containing acyl basic amino acid derivative and basic amino acid Download PDFInfo
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- JP6686902B2 JP6686902B2 JP2016566504A JP2016566504A JP6686902B2 JP 6686902 B2 JP6686902 B2 JP 6686902B2 JP 2016566504 A JP2016566504 A JP 2016566504A JP 2016566504 A JP2016566504 A JP 2016566504A JP 6686902 B2 JP6686902 B2 JP 6686902B2
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- 239000000203 mixture Substances 0.000 title claims description 79
- 239000002537 cosmetic Substances 0.000 title claims description 13
- 150000001413 amino acids Chemical class 0.000 title description 25
- 125000002252 acyl group Chemical group 0.000 title description 18
- 150000003862 amino acid derivatives Chemical class 0.000 title description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 150000003839 salts Chemical class 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- OAHBDANOQZTKQO-LYKKTTPLSA-N (2s)-2,6-diamino-7-oxooctadecanoic acid Chemical compound CCCCCCCCCCCC(=O)C(N)CCC[C@H](N)C(O)=O OAHBDANOQZTKQO-LYKKTTPLSA-N 0.000 claims description 6
- AKGWUHIOEVNNPC-LURJTMIESA-N Arg-OEt Chemical compound CCOC(=O)[C@@H](N)CCCNC(N)=N AKGWUHIOEVNNPC-LURJTMIESA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- XTJKNGLLPGBHHO-HNNXBMFYSA-N (2s)-5-(diaminomethylideneamino)-2-(dodecanoylamino)pentanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCCN=C(N)N XTJKNGLLPGBHHO-HNNXBMFYSA-N 0.000 claims description 3
- ODHCTXKNWHHXJC-VKHMYHEASA-M 5-oxo-L-prolinate Chemical compound [O-]C(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-M 0.000 claims description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 229940071139 pyrrolidone carboxylate Drugs 0.000 claims description 3
- GGCVGFFRMZLQBP-LBPRGKRZSA-N (2s)-6-amino-2-(octanoylamino)hexanoic acid Chemical compound CCCCCCCC(=O)N[C@H](C(O)=O)CCCCN GGCVGFFRMZLQBP-LBPRGKRZSA-N 0.000 claims description 2
- -1 lauroyl amino acid derivative Chemical class 0.000 description 39
- 229940024606 amino acid Drugs 0.000 description 36
- 238000011156 evaluation Methods 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000004472 Lysine Substances 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 229960003646 lysine Drugs 0.000 description 7
- 239000004475 Arginine Substances 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 229960003121 arginine Drugs 0.000 description 6
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 4
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 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 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 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 4
- 125000004442 acylamino group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003240 coconut oil Substances 0.000 description 3
- 235000019864 coconut oil Nutrition 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 210000004209 hair Anatomy 0.000 description 3
- 230000003020 moisturizing effect Effects 0.000 description 3
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229960003104 ornithine Drugs 0.000 description 3
- 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 3
- 239000000843 powder Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 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 3
- 229940058015 1,3-butylene glycol Drugs 0.000 description 2
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 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
- 239000002585 base Substances 0.000 description 2
- 235000019437 butane-1,3-diol Nutrition 0.000 description 2
- WMPOZLHMGVKUEJ-UHFFFAOYSA-N decanedioyl dichloride Chemical compound ClC(=O)CCCCCCCCC(Cl)=O WMPOZLHMGVKUEJ-UHFFFAOYSA-N 0.000 description 2
- 125000003493 decenyl group Chemical group [H]C([*])=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
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 125000005066 dodecenyl group Chemical group C(=CCCCCCCCCCC)* 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
- 229960002885 histidine Drugs 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000400 lauroyl group Chemical group O=C([*])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
- 239000007788 liquid Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 125000002960 margaryl 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])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001419 myristoyl group Chemical group O=C([*])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
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001196 nonadecyl 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])[H] 0.000 description 2
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 2
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000001509 sodium citrate Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000243 solution Substances 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
- 238000003756 stirring Methods 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 230000002123 temporal effect Effects 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000005040 tridecenyl group Chemical group C(=CCCCCCCCCCCC)* 0.000 description 2
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 2
- 229940038773 trisodium citrate Drugs 0.000 description 2
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 2
- 229920003169 water-soluble polymer Polymers 0.000 description 2
- AVBJHQDHVYGQLS-AWEZNQCLSA-N (2s)-2-(dodecanoylamino)pentanedioic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)CCC(O)=O AVBJHQDHVYGQLS-AWEZNQCLSA-N 0.000 description 1
- QZNNVYOVQUKYSC-JEDNCBNOSA-N (2s)-2-amino-3-(1h-imidazol-5-yl)propanoic acid;hydron;chloride Chemical compound Cl.OC(=O)[C@@H](N)CC1=CN=CN1 QZNNVYOVQUKYSC-JEDNCBNOSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- JDTUPLBMGDDPJS-UHFFFAOYSA-N 2-methoxy-2-phenylethanol Chemical compound COC(CO)C1=CC=CC=C1 JDTUPLBMGDDPJS-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 150000001483 arginine derivatives Chemical class 0.000 description 1
- 229960003589 arginine hydrochloride Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- LMHUUGBQXBBNIY-UHFFFAOYSA-N dodecane;dihydrochloride Chemical compound Cl.Cl.CCCCCCCCCCCC LMHUUGBQXBBNIY-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940088598 enzyme Drugs 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZSUZUJSDKZPWHH-UHFFFAOYSA-N ethyl 2-oxopyrrolidine-1-carboxylate Chemical compound CCOC(=O)N1CCCC1=O ZSUZUJSDKZPWHH-UHFFFAOYSA-N 0.000 description 1
- 210000004709 eyebrow Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000000245 forearm Anatomy 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 229940050411 fumarate Drugs 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- LVIMBOHJGMDKEJ-UHFFFAOYSA-N heptanedioyl dichloride Chemical compound ClC(=O)CCCCCC(Cl)=O LVIMBOHJGMDKEJ-UHFFFAOYSA-N 0.000 description 1
- GTABBGRXERZUAH-UHFFFAOYSA-N hexadecan-1-ol;2-methyloxirane;oxirane Chemical compound C1CO1.CC1CO1.CCCCCCCCCCCCCCCCO GTABBGRXERZUAH-UHFFFAOYSA-N 0.000 description 1
- DWMMZQMXUWUJME-UHFFFAOYSA-N hexadecyl octanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCCCCC DWMMZQMXUWUJME-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940071085 lauroyl glutamate Drugs 0.000 description 1
- 125000005645 linoleyl group Chemical group 0.000 description 1
- 229960005337 lysine hydrochloride Drugs 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001402 nonanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- PUIBKAHUQOOLSW-UHFFFAOYSA-N octanedioyl dichloride Chemical compound ClC(=O)CCCCCCC(Cl)=O PUIBKAHUQOOLSW-UHFFFAOYSA-N 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([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 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])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 1
- YVOFTMXWTWHRBH-UHFFFAOYSA-N pentanedioyl dichloride Chemical compound ClC(=O)CCCC(Cl)=O YVOFTMXWTWHRBH-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920001308 poly(aminoacid) Polymers 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000005374 primary esters Chemical group 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- A61K8/40—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Cosmetics (AREA)
Description
本発明は、(A):アシル塩基性アミノ酸誘導体、および(B):塩基性アミノ酸およびその塩、ならびにアシル塩基性アミノ酸低級エステルおよびその塩からなる群から選択される少なくとも一種の成分を含有する、例えば化粧料として使用される組成物に関する。 The present invention contains at least one component selected from the group consisting of (A): acyl basic amino acid derivative, and (B): basic amino acid and its salt, and acyl basic amino acid lower ester and its salt. , For example for compositions used as cosmetics.
下記式: The following formula:
(式中、RaおよびRbは水素原子またはアルキル基であり、nは0から12の整数である。)
で表される化合物またはその塩(以下、「ラウロイルアミノ酸誘導体」ともいう)は、化粧品に配合すると肌へのなじみ感を向上させるほか、保湿能(しっとり感)を発揮することも期待される(特許文献1、非特許文献1および非特許文献2等)。そのため、ラウロイルアミノ酸誘導体を化粧品に配合する検討がなされている。(In the formula, R a and R b are a hydrogen atom or an alkyl group, and n is an integer of 0 to 12.)
The compound represented by or a salt thereof (hereinafter, also referred to as “lauroyl amino acid derivative”) is expected to exhibit a moisturizing effect (moisturizing feeling) in addition to improving familiarity to the skin when blended into cosmetics ( Patent Document 1, Non-Patent Document 1, Non-Patent Document 2, etc.). Therefore, studies are being made to incorporate lauroyl amino acid derivatives into cosmetics.
しかしながら、ラウロイルアミノ酸誘導体を化粧水や乳液等の液状化粧品に配合した場合、ラウロイルアミノ酸誘導体の有するゲル化能により(特許文献1)、低濃度においても経時でゲル化して液状化粧品の流動性が低下し、安定性が悪い。また、ラウロイルアミノ酸誘導体は曳糸性を示すため、使用性がよくないほか、セミウェット時に特有のきしみ感を示すことがある。 However, when the lauroyl amino acid derivative is blended with a liquid cosmetic such as a lotion or an emulsion, due to the gelling ability of the lauroyl amino acid derivative (Patent Document 1), it gels with time even at a low concentration and the fluidity of the liquid cosmetic decreases. And the stability is poor. In addition, since the lauroyl amino acid derivative exhibits spinnability, it is not easy to use and may have a peculiar squeaky feeling during semi-wet.
本発明の目的は、ラウロイルアミノ酸誘導体に代表されるアシル塩基性アミノ酸誘導体の有する肌へのなじみ感やしっとり感を損なうことなく、きしみ感のない良好な使用感を有し、経時安定性および熱安定性に優れ、かつ曳糸性のない良好な使用性を有する組成物を提供することにある。 An object of the present invention is to have a good feeling of use without squeaky feeling, without impairing the familiarity and moisturizing feeling to the skin of the acyl basic amino acid derivative typified by lauroyl amino acid derivative, and stability with time and heat. An object of the present invention is to provide a composition having excellent stability and good usability without spinnability.
本発明者らは、上記目的を達成するため鋭意検討を重ねた結果、成分(A):下記式(1)で示される化合物(以下、「化合物(1)」ともいう)またはその塩に成分(B):塩基性アミノ酸およびその塩、ならびにアシル塩基性アミノ酸低級エステルおよびその塩からなる群から選択される少なくとも一種の成分を配合した組成物が、きしみ感のない良好な使用感を有し、経時安定性および熱安定性に優れ、かつ曳糸性のない良好な使用性を有することを見出し、本発明を完成するに至った。 The present inventors have conducted extensive studies to achieve the above object, and as a result, Component (A): a compound represented by the following formula (1) (hereinafter, also referred to as “compound (1)”) or a salt thereof, (B): A composition containing at least one component selected from the group consisting of a basic amino acid and a salt thereof, and an acyl basic amino acid lower ester and a salt thereof has a good feeling of use without squeaky feeling. The inventors have found that they have excellent aging stability and thermal stability, and have good usability without spinnability, and have completed the present invention.
すなわち、本発明は以下の通りである。
[1]成分(A):式(1)That is, the present invention is as follows.
[1] Component (A): Formula (1)
(式中、
R1およびR2は、各々独立して、炭素原子数5〜21のアルキル基または炭素原子数5〜21のアルケニル基であり、
R3およびR4は、各々独立して、水素原子、炭素原子数1〜22のアルキル基または炭素原子数2〜22のアルケニル基であり、
zは0以上の整数であり、
xおよびyは、各々独立して、2〜4の整数である。)で示される化合物またはその塩;
および
成分(B):塩基性アミノ酸およびその塩、ならびにアシル塩基性アミノ酸低級エステルおよびその塩からなる群から選択される少なくとも一種の成分
を含有する組成物。
[2]成分(A)が、前記式(1)においてzが0〜10の整数である化合物またはその塩である、[1]に記載の組成物。
[3]成分(A)が、前記式(1)においてzが7または8である化合物またはその塩である、[1]または[2]に記載の組成物。
[4]成分(A)が、前記式(1)においてxおよびyが共に4である化合物またはその塩である、[1]〜[3]のいずれかに記載の組成物。
[5]成分(A)が、前記式(1)においてR1およびR2が各々独立して、炭素原子数8〜15の直鎖アルキル基である化合物またはその塩である、[1]〜[4]のいずれかに記載の組成物。
[6]成分(A)が、前記式(1)においてR3およびR4が共に水素原子である化合物またはその塩である、[1]〜[5]のいずれかに記載の組成物。
[7]成分(A)が、前記式(1)においてR1およびR2が、各々独立して、炭素原子数8〜15の直鎖アルキル基であり、R3およびR4が、共に水素原子であり、zが、0〜10の整数であり、xおよびyが、共に4である化合物またはその塩である、[1]〜[5]のいずれかに記載の組成物。
[8]成分(A)が、前記式(1)においてR1およびR2が、共に炭素原子数8〜15の直鎖アルキル基であり、R3およびR4が、共に水素原子であり、zが、7または8であり、xおよびyが、共に4である化合物またはその塩である、[1]〜[5]のいずれかに記載の組成物。
[9]成分(A)が、ビス(Nε-ラウロイル-L-リジン)セバコイルアミドまたはその塩である、[1]〜[5]のいずれかに記載の組成物。
[10]成分(A)が、ビス(Nε-ラウロイル-L-リジン)セバコイルアミド、およびビス(Nε-オクタノイル-L-リジン)セバコイルアミドから選択される化合物またはその塩である、[1]〜[5]のいずれかに記載の組成物。
[11]成分(B)が、アルギニン、リジンまたはヒスチジンである、[1]〜[10]のいずれかに記載の組成物。
[12]成分(B)が、ココイルアルギニンエチルエステルピロリドンカルボン酸塩またはラウロイルアルギニンエチルエステル塩酸塩である、[1]〜[10]のいずれかに記載の組成物。
[13]成分(A)を組成物全量に対して0.005〜20重量%含有する、[1]〜[12]のいずれかに記載の組成物。
[14]成分(B)を組成物全量に対して0.005〜20重量%含有する、[1]〜[13]のいずれかに記載の組成物。
[15][1]〜[14]のいずれかに記載の組成物を含む化粧料。(In the formula,
R 1 and R 2 are each independently an alkyl group having 5 to 21 carbon atoms or an alkenyl group having 5 to 21 carbon atoms,
R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms,
z is an integer of 0 or more,
x and y are each independently an integer of 2 to 4. ) Or a salt thereof;
And component (B): a composition containing a basic amino acid and a salt thereof, and at least one component selected from the group consisting of an acyl basic amino acid lower ester and a salt thereof.
[2] The composition according to [1], wherein the component (A) is a compound in which z is an integer of 0 to 10 in the formula (1) or a salt thereof.
[3] The composition according to [1] or [2], wherein the component (A) is a compound in which z is 7 or 8 in the formula (1) or a salt thereof.
[4] The composition according to any one of [1] to [3], wherein the component (A) is a compound in which x and y are both 4 in the formula (1) or a salt thereof.
[5] The component (A) is a compound or a salt thereof in which R 1 and R 2 are each independently a linear alkyl group having 8 to 15 carbon atoms in the formula (1), [1] to The composition according to any one of [4].
[6] The composition according to any one of [1] to [5], wherein the component (A) is a compound or a salt thereof in which R 3 and R 4 are both hydrogen atoms in the formula (1).
[7] In the component (A), in the formula (1), R 1 and R 2 are each independently a linear alkyl group having 8 to 15 carbon atoms, and R 3 and R 4 are both hydrogen. The composition according to any one of [1] to [5], which is an atom, z is an integer of 0 to 10, and x and y are both 4 or a salt thereof.
[8] In the component (A), in the formula (1), R 1 and R 2 are both linear alkyl groups having 8 to 15 carbon atoms, and R 3 and R 4 are both hydrogen atoms, The composition according to any one of [1] to [5], wherein z is 7 or 8, and x and y are both 4 or a salt thereof.
[9] The composition according to any one of [1] to [5], wherein the component (A) is bis (N ε -lauroyl-L-lysine) sebacoilamide or a salt thereof.
[10] Component (A) is bis - - (octanoyl -L- lysine N epsilon), or a salt thereof selected from Sebacoyl amide, (N epsilon lauroyl -L- lysine) sebacoyl amide, and bis The composition according to any one of [1] to [5].
[11] The composition according to any one of [1] to [10], wherein the component (B) is arginine, lysine or histidine.
[12] The composition according to any one of [1] to [10], wherein the component (B) is cocoyl arginine ethyl ester pyrrolidone carboxylate or lauroyl arginine ethyl ester hydrochloride.
[13] The composition according to any one of [1] to [12], which contains the component (A) in an amount of 0.005 to 20% by weight based on the total amount of the composition.
[14] The composition according to any one of [1] to [13], which contains the component (B) in an amount of 0.005 to 20% by weight based on the total amount of the composition.
[15] A cosmetic containing the composition according to any one of [1] to [14].
本発明によれば、きしみ感のない良好な使用感を示し、経時安定性および熱安定性に優れ、かつ曳糸性のない良好な使用性を有する組成物を提供することができる。 According to the present invention, it is possible to provide a composition having a good usability without squeaky feeling, excellent stability over time and thermal stability, and good usability without spinnability.
本発明の組成物は、成分(A):式(1) The composition of the present invention comprises component (A): formula (1)
(式中、
R1およびR2は、各々独立して、炭素原子数5〜21のアルキル基または炭素原子数5〜21のアルケニル基であり、
R3およびR4は、各々独立して、水素原子、炭素原子数1〜22のアルキル基または炭素原子数2〜22のアルケニル基であり、
zは0以上の整数であり、
xおよびyは、各々独立して、2〜4の整数である。)で示される化合物またはその塩、
および
成分(B):塩基性アミノ酸およびその塩、ならびにアシル塩基性アミノ酸低級エステルおよびその塩からなる群から選択される少なくとも一種の成分
を含有する組成物であることを特徴とする。(In the formula,
R 1 and R 2 are each independently an alkyl group having 5 to 21 carbon atoms or an alkenyl group having 5 to 21 carbon atoms,
R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms,
z is an integer of 0 or more,
x and y are each independently an integer of 2 to 4. ) Or a salt thereof,
And component (B): a composition containing at least one component selected from the group consisting of basic amino acids and salts thereof, and acyl basic amino acid lower esters and salts thereof.
以下に、本発明の実施の形態について詳述する。 Hereinafter, embodiments of the present invention will be described in detail.
1.成分(A):式(1)で示される化合物(化合物(1))またはその塩
R1およびR2は、各々独立して、炭素原子数5〜21のアルキル基または炭素原子数5〜21のアルケニル基である。
炭素原子数5〜21のアルキル基とは、炭素原子数5〜21の直鎖または分岐状のアルキル基を意味し、具体的には、ペンチル基、イソペンチル基、ネオペンチル基、ヘキシル基、イソヘキシル基、ネオヘキシル基、ヘプチル基、イソヘプチル基、ネオヘプチル基、オクチル基、イソオクチル基、ノニル基、イソノニル基、デシル基、イソデシル基、ウンデシル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、オクタデシル基、ノナデシル基、イコシル基等が挙げられる。
炭素原子数5〜21のアルケニル基とは、炭素原子数5〜21の直鎖または分岐状のアルケニル基を意味し、具体的には、ペンテニル基、ヘキセニル基、ヘプテニル基、オクテニル基、ノネニル基、デセニル基、ウンデセニル基、ドデセニル基、トリデセニル基、テトラデセニル基、ペンタデセニル基、ヘキサデセニル基、ヘプタデセニル基、オクタデセニル基、ノナデセニル基、イコセニル基等が挙げられる。
炭素原子数8〜15のアルキル基とは、炭素原子数8〜15の直鎖または分岐状のアルキル基を意味し、具体的には、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基等が挙げられる。
炭素原子数8〜11のアルキル基とは、炭素原子数8〜11の直鎖または分岐状のアルキル基を意味し、具体的には、オクチル基、ノニル基、デシル基、ウンデシル基等が挙げられる。
R1およびR2は、好ましくは各々独立して、炭素原子数8〜15のアルキル基であり、より好ましくは各々独立して、炭素原子数8〜11のアルキル基である。
また、R1およびR2は、直鎖のアルキル基であることが好ましい。さらに、R1およびR2は、同一であることが好ましい。1. Component (A): The compound represented by formula (1) (compound (1)) or a salt thereof R 1 and R 2 are each independently an alkyl group having 5 to 21 carbon atoms or 5 to 21 carbon atoms. Is an alkenyl group.
The alkyl group having 5 to 21 carbon atoms means a linear or branched alkyl group having 5 to 21 carbon atoms, and specifically, a pentyl group, an isopentyl group, a neopentyl group, a hexyl group, an isohexyl group. , Neohexyl group, heptyl group, isoheptyl group, neoheptyl group, octyl group, isooctyl group, nonyl group, isononyl group, decyl group, isodecyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group Group, octadecyl group, nonadecyl group, icosyl group and the like.
The alkenyl group having 5 to 21 carbon atoms means a linear or branched alkenyl group having 5 to 21 carbon atoms, and specifically, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group. , Decenyl group, undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, heptadecenyl group, octadecenyl group, nonadecenyl group, icosenyl group and the like.
The alkyl group having 8 to 15 carbon atoms means a straight-chain or branched alkyl group having 8 to 15 carbon atoms, specifically, octyl group, nonyl group, decyl group, undecyl group, dodecyl group. , Tridecyl group, tetradecyl group, pentadecyl group and the like.
The alkyl group having 8 to 11 carbon atoms means a linear or branched alkyl group having 8 to 11 carbon atoms, and specific examples thereof include an octyl group, a nonyl group, a decyl group, and an undecyl group. To be
R 1 and R 2 are preferably each independently an alkyl group having 8 to 15 carbon atoms, and more preferably each independently being an alkyl group having 8 to 11 carbon atoms.
In addition, R 1 and R 2 are preferably linear alkyl groups. Furthermore, it is preferable that R 1 and R 2 are the same.
R3およびR4は、各々独立して、水素原子、炭素原子数1〜22のアルキル基または炭素原子数2〜22のアルケニル基である。
炭素原子数1〜22のアルキル基とは、炭素原子数1〜22の直鎖または分岐状のアルキル基を意味し、具体的には、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、ペンチル基、イソペンチル基、ネオペンチル基、ヘキシル基、イソヘキシル基、ネオヘキシル基、ヘプチル基、イソヘプチル基、ネオヘプチル基、オクチル基、イソオクチル基、ノニル基、イソノニル基、デシル基、イソデシル基、ウンデシル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、オクタデシル基、ノナデシル基、イコシル基等が挙げられる。
炭素原子数2〜22のアルケニル基とは、炭素原子数2〜22の直鎖または分岐状のアルケニル基を意味し、具体的には、エテニル基、1−プロペニル基、2−プロペニル基、1−ブテニル基、2−ブテニル基、3−ブテニル基、ペンテニル基、ヘキセニル基、ヘプテニル基、オクテニル基、ノネニル基、デセニル基、ウンデセニル基、ドデセニル基、トリデセニル基、テトラデセニル基、ペンタデセニル基、ヘキサデセニル基、ヘプタデセニル基、オクタデセニル基、ノナデセニル基、イコセニル基等が挙げられる。
R3およびR4は、好ましくは共に水素原子である。R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms.
The alkyl group having 1 to 22 carbon atoms means a linear or branched alkyl group having 1 to 22 carbon atoms, specifically, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group. , Isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, neopentyl group, hexyl group, isohexyl group, neohexyl group, heptyl group, isoheptyl group, neoheptyl group, octyl group, isooctyl group, nonyl group, Examples thereof include isononyl group, decyl group, isodecyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group and icosyl group.
The alkenyl group having 2 to 22 carbon atoms means a linear or branched alkenyl group having 2 to 22 carbon atoms, and specifically, an ethenyl group, a 1-propenyl group, a 2-propenyl group, 1 -Butenyl group, 2-butenyl group, 3-butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, tridecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group, Examples thereof include a heptadecenyl group, an octadecenyl group, a nonadecenyl group and an icosenyl group.
R 3 and R 4 are preferably both hydrogen atoms.
zは、0以上の整数である。
zは、好ましくは0〜10の整数であり、より好ましくは7または8である。z is an integer of 0 or more.
z is preferably an integer of 0 to 10, and more preferably 7 or 8.
xおよびyは、各々独立して、2〜4の整数である。
xおよびyは、好ましくは共に4である。x and y are each independently an integer of 2 to 4.
x and y are preferably both 4.
式(1)で示される化合物として、好ましくは、以下の化合物が挙げられる。
(化合物A)
R1およびR2が、各々独立して、炭素原子数8〜15の直鎖アルキル基であり、
R3およびR4が、共に水素原子であり、
zが、0〜10の整数であり、
xおよびyが、共に4である化合物。As the compound represented by the formula (1), the following compounds are preferable.
(Compound A)
R 1 and R 2 are each independently a linear alkyl group having 8 to 15 carbon atoms,
R 3 and R 4 are both hydrogen atoms,
z is an integer of 0 to 10,
A compound in which x and y are both 4.
(化合物B)
R1およびR2が、共に炭素原子数8〜15の直鎖アルキル基であり、
R3およびR4が、共に水素原子であり、
zが、7または8であり、
xおよびyが、共に4である化合物。(Compound B)
R 1 and R 2 are both linear alkyl groups having 8 to 15 carbon atoms,
R 3 and R 4 are both hydrogen atoms,
z is 7 or 8;
A compound in which x and y are both 4.
(化合物C)
R1およびR2が、共に炭素原子数8〜11の直鎖アルキル基であり、
R3およびR4が、共に水素原子であり、
zが、7または8であり、
xおよびyが、共に4である化合物。(Compound C)
R 1 and R 2 are both linear alkyl groups having 8 to 11 carbon atoms,
R 3 and R 4 are both hydrogen atoms,
z is 7 or 8;
A compound in which x and y are both 4.
式(1)で示される化合物の具体例としては、
ビス(Nε-ラウロイル-L-リジン)セバコイルアミド、
またはそれらの塩が挙げられる。Specific examples of the compound represented by the formula (1) include:
Bis (N ε -lauroyl-L-lysine) sebacylamide,
Or the salt thereof is mentioned.
式(1)で示される化合物の塩としては特に限定されず、例えば、ナトリウム塩、カリウム塩等のアルカリ金属塩、カルシウム塩、マグネシウム塩等のアルカリ土類金属塩、アルミニウム塩、亜鉛との塩等の無機塩、あるいはアンモニウム塩、モノエタノールアミン塩、ジエタノールアミン塩、トリエタノールアミン塩等の有機アミン塩や、アルギニン塩、リジン塩等の塩基性アミノ酸塩等の有機塩が挙げられる。これらのうち1種を使用してもよいし、上記群から選ばれる2種以上を混合して使用しても構わない。入手の容易性、取り扱い性等の観点から、アルカリ金属塩、有機アミン塩、塩基性アミノ酸塩が好ましく、ナトリウム塩、カリウム塩が特に好ましい。 The salt of the compound represented by the formula (1) is not particularly limited, and examples thereof include alkali metal salts such as sodium salt and potassium salt, alkaline earth metal salts such as calcium salt and magnesium salt, aluminum salt, and salt with zinc. And the like, organic salts such as ammonium salts, ammonium salts, monoethanolamine salts, diethanolamine salts and triethanolamine salts, and organic salts such as basic amino acid salts such as arginine salts and lysine salts. One of these may be used, or two or more selected from the above group may be mixed and used. From the viewpoint of easy availability, handleability and the like, alkali metal salts, organic amine salts and basic amino acid salts are preferable, and sodium salts and potassium salts are particularly preferable.
化合物(1)は、自体公知の方法またはそれに準じた方法により製造することができる(特開2004−323505号公報、Org. Biomol. Chem., 2003, 1, 4124-4131、New J. Chem., 2005, 29, 1439-1444等)。例えば、下記式に示すように、化合物(1)のうち、対称型の化合物(1’)は、Nω−アシルアミノ酸(2)とジカルボン酸ジクロライド(3)を適切な溶媒中で反応させることにより製造することができる。Compound (1) can be produced by a method known per se or a method analogous thereto (JP 2004-323505 A, Org. Biomol. Chem., 2003, 1, 4124-4131, New J. Chem. , 2005, 29, 1439-1444). For example, as shown in the following formula, among the compounds (1), the symmetrical compound (1 ′) is obtained by reacting the N ω -acyl amino acid (2) with the dicarboxylic acid dichloride (3) in a suitable solvent. Can be manufactured by.
(式中、R1’は炭素原子数5〜21のアルキル基または炭素原子数5〜21のアルケニル基であり、R3’は水素原子、炭素原子数1〜22のアルキル基または炭素原子数2〜22のアルケニル基であり、z’は0以上の整数であり、x’は2〜4の整数である。)(In the formula, R 1 ′ is an alkyl group having 5 to 21 carbon atoms or an alkenyl group having 5 to 21 carbon atoms, and R 3 ′ is a hydrogen atom, an alkyl group having 1 to 22 carbon atoms or the number of carbon atoms. 2 to 22 alkenyl groups, z'is an integer of 0 or more, and x'is an integer of 2 to 4.)
Nω−アシルアミノ酸(2)としては、例えば、Nε−アシルリジン(例:Nε−ヘキサノイル−L−リジン、Nε−オクタノイル−L−リジン等)、Nδ−アシルオルニチン(例:Nδ−ヘキサノイル−L−オルニチン等)、Nγ−アシル−α,γ−ジアミノ酪酸等が挙げられる。
ジカルボン酸ジクロライド(3)としては、例えば、オギザリルクロライド、マロニルクロライド、スクシニルクロライド、グルタリルクロライド、アジポイルクロライド、ピメロイルクロライド、スベロイルクロライド、アゼラオイルクロライド、セバコイルクロライド、ドデカンジオイルクロライド等が挙げられる。ジカルボン酸ジクロライド(3)の使用量は、Nω−アシルアミノ酸(2)に対して通常0.4〜0.6当量である。
溶媒としては、反応に不活性な溶媒であれば特に限定されないが、例えば、ジエチルエーテル、テトラヒドロフラン等のエーテル類が挙げられる。N omega - The acylamino acid (2), for example, N epsilon - acyl-lysine (example: N epsilon - hexanoyl -L- lysine, N epsilon - octanoyl -L- lysine, etc.), N [delta] - acyl-ornithine (eg: N [delta] - hexanoyl -L- ornithine), N gamma - acyl-.alpha., .gamma.-diaminobutyric acid, and the like.
Examples of the dicarboxylic acid dichloride (3) include oxalyl chloride, malonyl chloride, succinyl chloride, glutaryl chloride, adipoyl chloride, pimeloyl chloride, suberoyl chloride, azela oil chloride, sebacyl chloride, dodecane dichloride. Oil chloride and the like can be mentioned. The usage-amount of dicarboxylic acid dichloride (3) is 0.4-0.6 equivalent normally with respect to N ( omega ) -acyl amino acid (2).
The solvent is not particularly limited as long as it is an inert solvent for the reaction, and examples thereof include ethers such as diethyl ether and tetrahydrofuran.
また、化合物(1)のうち、非対称型の化合物(1’’)は下記の通り製造することができる。まず、Nω−アシルアミノ酸(2)とジカルボン酸モノクロライドモノエステル(4)を適切な溶媒中で反応させて化合物(5)を得る(工程1)。続いて、得られた化合物(5)の1級エステル部位を水酸化ナトリウム、水酸化カリウム等の塩基存在下で加水分解した後、チオニルクロライド等のクロロ化剤を用いてカルボン酸部位をクロロ化し、前記工程1で用いたNω−アシルアミノ酸(2)とは異なるNω−アシルアミノ酸(2’)を反応させることにより製造することができる(工程2)。In addition, of the compound (1), the asymmetrical compound (1 ″) can be produced as follows. First, Nω -acyl amino acid (2) and dicarboxylic acid monochloride monoester (4) are reacted in a suitable solvent to obtain compound (5) (step 1). Then, after hydrolyzing the primary ester moiety of the obtained compound (5) in the presence of a base such as sodium hydroxide or potassium hydroxide, the carboxylic acid moiety is chlorinated using a chlorinating agent such as thionyl chloride. , N omega used in the step 1 - different N omega from acylamino acids (2) - can be prepared by reacting the acylamino acid (2 ') (step 2).
(式中、R1’、R3’、z’およびx’は前記定義と同義であり、R2’は炭素原子数5〜21のアルキル基または炭素原子数5〜21のアルケニル基であり、R4’は水素原子、炭素原子数1〜22のアルキル基または炭素原子数2〜22のアルケニル基であり、R5はメチル基、エチル基等のアルキル基であり、y’は2〜4の整数である。)(In the formula, R 1 ′ , R 3 ′ , z ′ and x ′ are as defined above, and R 2 ′ is an alkyl group having 5 to 21 carbon atoms or an alkenyl group having 5 to 21 carbon atoms. , R 4 ′ is a hydrogen atom, an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms, R 5 is an alkyl group such as a methyl group or an ethyl group, and y ′ is 2 to It is an integer of 4.)
Nω−アシルアミノ酸(2)および(2’)は、前記と同様のNω−アシルアミノ酸を用いることができる。
ジカルボン酸モノクロライドモノエステル(4)は、市販されている場合には市販品をそのまま用いることができ、自体公知の方法またはそれに準じた方法にて製造したものを用いることもできる。As the N ω -acyl amino acids (2) and (2 ′), the same N ω -acyl amino acids as described above can be used.
When the dicarboxylic acid monochloride monoester (4) is commercially available, a commercially available product can be used as it is, and a product produced by a method known per se or a method analogous thereto can also be used.
なお、前記方法で得られた化合物(1)を、水酸化ナトリウム、水酸化カリウム等のアルカリ金属水酸化物、水酸化カルシウム等のアルカリ土類金属水酸化物、有機アミン塩基等と反応させることにより、化合物(1)の塩に変換することができる。 The compound (1) obtained by the above method is reacted with an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, an alkaline earth metal hydroxide such as calcium hydroxide, an organic amine base or the like. Can be converted into a salt of compound (1).
本発明の組成物における成分(A):化合物(1)またはその塩の含有量は、組成物全量に対して通常0.005〜20重量%であり、好ましくは0.01〜10重量%であり、より好ましくは0.01〜5.0重量%であり、特に好ましくは0.02〜2.5重量%である。 The content of component (A): compound (1) or a salt thereof in the composition of the present invention is usually 0.005 to 20% by weight, preferably 0.01 to 10% by weight, based on the total amount of the composition. %, More preferably 0.01 to 5.0% by weight, and particularly preferably 0.02 to 2.5% by weight.
2.成分(B):塩基性アミノ酸およびその塩、ならびにアシル塩基性アミノ酸低級エステルおよびその塩からなる群から選択される少なくとも一種の成分
本明細書における「塩基性アミノ酸」、および「アシル塩基性アミノ酸低級エステル」の「塩基性アミノ酸」とは、分子内に一つのアミノ基に加えて、塩基性を示す基(例、アミノ基、イミダゾリル基等)をさらに有するアミノ酸を意味する。「塩基性アミノ酸」の具体例としては、アルギニン、リジン、ヒスチジン、オルニチン等が挙げられる。中でもアルギニン、リジン等が好ましく、アルギニンがより好ましい。2. Component (B): at least one component selected from the group consisting of basic amino acids and salts thereof, and acyl basic amino acid lower esters and salts thereof, "basic amino acid" and "acyl basic amino acid lower" in the present specification. The "basic amino acid" of "ester" means an amino acid having a basic group (eg, amino group, imidazolyl group, etc.) in addition to one amino group in the molecule. Specific examples of the "basic amino acid" include arginine, lysine, histidine, ornithine and the like. Of these, arginine and lysine are preferable, and arginine is more preferable.
本明細書における「アシル塩基性アミノ酸低級エステル」のアシル基としては、炭素原子数8〜22の飽和または不飽和脂肪酸より誘導される、直鎖または分岐鎖のものを使用できる。アシル基の具体例としては、オクタノイル基、ノナノイル基、デカノイル基、ウンデカノイル基、ラウロイル基、ミリストイル基、パルミトイル基、ステアロイル基、オレオイル基、リノレイル基、天然由来の混合脂肪酸(例、ヤシ油脂肪酸、ヒマシ油脂肪酸、オリーブ油脂肪酸、パーム油脂肪酸)より誘導されるアシル基等が挙げられる。好ましくは、ラウロイル基、ミリストイル基、ヤシ油脂肪酸より誘導されるアシル基である。 As the acyl group of the “acyl basic amino acid lower ester” in the present specification, a straight chain or branched chain derivative derived from a saturated or unsaturated fatty acid having 8 to 22 carbon atoms can be used. Specific examples of the acyl group include octanoyl group, nonanoyl group, decanoyl group, undecanoyl group, lauroyl group, myristoyl group, palmitoyl group, stearoyl group, oleoyl group, linoleyl group, naturally occurring mixed fatty acid (eg, coconut oil fatty acid , Castor oil fatty acid, olive oil fatty acid, palm oil fatty acid) and the like. Preferred are lauroyl group, myristoyl group, and acyl group derived from coconut oil fatty acid.
本明細書における「アシル塩基性アミノ酸低級エステル」の低級エステルとしては、炭素原子数1〜6の直鎖または分岐状のアルコールより誘導されるエステルを使用できる。低級エステルの具体例としては、メチルエステル、エチルエステル、プロピルエステル、イソプロピルエステル、ブチルエステル、イソブチルエステル、sec−ブチルエステル、tert−ブチルエステル、ペンチルエステル、ヘキシルエステル等が挙げられ、より好ましくは、エチルエステルである。 As the lower ester of the “acyl basic amino acid lower ester” in the present specification, an ester derived from a linear or branched alcohol having 1 to 6 carbon atoms can be used. Specific examples of the lower ester include methyl ester, ethyl ester, propyl ester, isopropyl ester, butyl ester, isobutyl ester, sec-butyl ester, tert-butyl ester, pentyl ester, and hexyl ester, and more preferably, It is an ethyl ester.
本明細書における「アシル塩基性アミノ酸低級エステル」の具体例としては、ココイルアルギニンエチルエステル、ラウロイルアルギニンエチルエステル等が挙げられる。中でも、ココイルアルギニンエチルエステルが好ましい。
なお、不斉炭素原子を有するアミノ酸に関しては、光学活性体またはラセミ体のいずれでもよい。Specific examples of the “acyl basic amino acid lower ester” in the present specification include cocoyl arginine ethyl ester, lauroyl arginine ethyl ester and the like. Of these, cocoyl arginine ethyl ester is preferable.
The amino acid having an asymmetric carbon atom may be in an optically active form or a racemic form.
塩基性アミノ酸塩およびアシル塩基性アミノ酸低級エステル塩の塩としては特に限定されず、例えば、塩酸塩、臭化水素酸塩、硫酸塩、硝酸塩、リン酸塩等の無機酸との塩、ギ酸塩、酢酸塩、トリフルオロ酢酸塩、シュウ酸塩、コハク酸塩、マレイン酸塩、フマル酸塩、クエン酸塩、酒石酸塩、ピロリドンカルボン酸塩、メタンスルホン酸塩、エタンスルホン酸塩、ベンゼンスルホン酸塩、p−トルエンスルホン酸塩、有機酸との塩等が挙げられる。これらのうち1種を使用してもよいし、上記群から選ばれる2種以上を混合して使用しても構わない。 The salt of the basic amino acid salt and the acyl basic amino acid lower ester salt is not particularly limited, and examples thereof include salts with inorganic acids such as hydrochloride, hydrobromide, sulfate, nitrate and phosphate, and formate salts. , Acetate, trifluoroacetate, oxalate, succinate, maleate, fumarate, citrate, tartrate, pyrrolidonecarboxylate, methanesulfonate, ethanesulfonate, benzenesulfonate Examples thereof include salts, p-toluenesulfonic acid salts, salts with organic acids and the like. One of these may be used, or two or more selected from the above group may be mixed and used.
塩基性アミノ酸塩としては、リジン塩酸塩、アルギニン塩酸塩、ヒスチジン塩酸塩等が好ましく挙げられ、アシル塩基性アミノ酸低級エステル塩としては、ココイルアルギニンエチルPCA(ヤシ油脂肪酸アシルアルギニンエチル・ピロリドンカルボン酸塩)等が好ましく挙げられる。 The basic amino acid salt preferably includes lysine hydrochloride, arginine hydrochloride, histidine hydrochloride and the like, and the acyl basic amino acid lower ester salt includes cocoyl arginine ethyl PCA (coconut oil fatty acid acyl arginine ethyl pyrrolidone carboxylate). ) Etc. are preferably mentioned.
本発明の組成物における成分(B)の含有量は、組成物全量に対して通常0.005〜20重量%であり、好ましくは0.05〜10重量%である。 The content of the component (B) in the composition of the present invention is usually 0.005 to 20% by weight, preferably 0.05 to 10% by weight, based on the total amount of the composition.
本発明の組成物のpHは特に限定されないが、pH5.5〜7.5であるのが好ましい。 The pH of the composition of the present invention is not particularly limited, but it is preferably pH 5.5 to 7.5.
本発明は、また、前記本発明の組成物を含有する化粧料に関する。 The present invention also relates to cosmetics containing the composition of the present invention.
本発明の化粧料としては、具体的には、洗顔料、化粧水、乳液、クリーム、ジェル、美容液、パック、マスク、石鹸、ボディシャンプー、白粉、ファンデーション、口紅、チーク、アイライナー、マスカラ、アイシャドー、眉墨、シャンプー、リンス、ヘアコンディショナー、ヘアスタイリング剤、ヘアトリートメント等が挙げられる。 As the cosmetics of the present invention, specifically, face wash, lotion, emulsion, cream, gel, beauty essence, pack, mask, soap, body shampoo, white powder, foundation, lipstick, cheek, eyeliner, mascara, Eye shadow, eyebrow, shampoo, conditioner, hair conditioner, hair styling agent, hair treatment and the like.
本発明の化粧料は、通常化粧料に添加してもよい成分を本発明の効果を阻害しない範囲で含有してもよい。具体的には、油剤、キレート剤、界面活性剤、粉体、アミノ酸類(例えば、中性アミノ酸、酸性アミノ酸など)、多価アルコール、ポリアミノ酸およびその塩、水溶性高分子、糖アルコールおよびそのアルキレンオキシド付加物、低級アルコール、動植物抽出物、核酸、ビタミン、酵素、抗炎症剤、殺菌剤、防腐剤、抗酸化剤、紫外線吸収剤、制汗剤、顔料、色素、酸化染料、有機および無機粉体、pH調整剤、パール化剤、湿潤剤が挙げられる。 The cosmetic of the present invention may contain components that may be added to the cosmetic in a range that does not impair the effects of the present invention. Specifically, oil agents, chelating agents, surfactants, powders, amino acids (eg, neutral amino acids, acidic amino acids, etc.), polyhydric alcohols, polyamino acids and salts thereof, water-soluble polymers, sugar alcohols and the like. Alkylene oxide adducts, lower alcohols, animal and plant extracts, nucleic acids, vitamins, enzymes, anti-inflammatory agents, bactericides, preservatives, antioxidants, UV absorbers, antiperspirants, pigments, dyes, oxidative dyes, organic and inorganic Examples include powders, pH adjusters, pearling agents, and wetting agents.
本発明の組成物、および該組成物を含む化粧料は、常法に従って製造することができる。 The composition of the present invention and the cosmetic containing the composition can be produced by a conventional method.
次に製造例および実施例により、本発明を具体的に説明する。なお、本発明は以下の製造例および実施例に限定されるものではない。また「%」は特に断りが無い限り「重量%」を示す。 Next, the present invention will be specifically described with reference to manufacturing examples and examples. The present invention is not limited to the following production examples and examples. Further, "%" means "% by weight" unless otherwise specified.
〔製造例1〕ビス(Nε-ラウロイル-L-リジン)セバコイルアミドジナトリウム塩の合成
Nε−ラウロイル−L−リジン8.2g(25mmol)を、水70gおよび25%水酸化ナトリウム水溶液(10g)に溶解させ、ジエチルエーテル80gを加えた。そこへセバコイルクロライド3.3g(14mmol)をエーテル層にゆっくり加えた。この2層溶液を0℃に保持したまま1時間ほど攪拌し、その後室温で23時間攪拌した。次いで、75%硫酸を滴下し、pH2に調整した後、得られた白色沈殿を濾取し、水でよく洗い乾燥した。得られた化合物を水酸化ナトリウム水溶液に溶解させて10%のビス(Nε−ラウロイル−L−リジン)セバコイルアミドジナトリウム塩水溶液を得た。[Production Example 1] Synthesis of bis (N [ epsilon ] -lauroyl-L-lysine) sebacylamide disodium salt N [ epsilon] -lauroyl-L-lysine (8.2 g, 25 mmol) was added to 70 g of water and a 25% aqueous sodium hydroxide solution ( It was dissolved in 10 g) and 80 g of diethyl ether was added. 3.3 g (14 mmol) of sebacoyl chloride was slowly added there to the ether layer. This two-layer solution was stirred for about 1 hour while keeping it at 0 ° C., and then at room temperature for 23 hours. Then, 75% sulfuric acid was added dropwise to adjust the pH to 2, and the obtained white precipitate was collected by filtration, washed well with water and dried. The obtained compound was dissolved in sodium hydroxide aqueous solution of 10% bis (N epsilon - lauroyl -L- lysine) was obtained sebacoyl amide disodium salt solution.
本発明の組成物の経時安定性、熱安定性、使用性(曳糸性のなさ)および使用感(きしみ感のなさ、なじみ感、しっとり感)について評価した。組成物の調製、評価方法および評価基準は下記のとおりである。 The composition of the present invention was evaluated for stability over time, heat stability, usability (no spinnability) and usability (no squeaky feel, familiar feel, moist feel). Preparation of the composition, evaluation method and evaluation criteria are as follows.
実施例1〜7および比較例1〜5の組成物の調製
成分(A)(製造例1で合成した化合物)を、あらかじめ80℃にて水に加熱溶解させた、成分(B)、グルタミン又は尿素、およびクエン酸三ナトリウムの混合物に加えた後、撹拌しながら室温まで冷却し、クエン酸にてpH6.5に調整した。得られた混合物を再び80℃で5分間加熱し、室温まで冷却した。得られた組成物を30mLのガラス瓶に完全密封して25℃にて2週間保管した後、各種評価に供した。Preparation of Compositions of Examples 1 to 7 and Comparative Examples 1 to 5 Component (A) (compound synthesized in Production Example 1) was heated and dissolved in water at 80 ° C. in advance, Component (B), glutamine or After adding to a mixture of urea and trisodium citrate, the mixture was cooled to room temperature with stirring and adjusted to pH 6.5 with citric acid. The resulting mixture was heated again at 80 ° C. for 5 minutes and cooled to room temperature. The obtained composition was completely sealed in a 30 mL glass bottle, stored at 25 ° C. for 2 weeks, and then subjected to various evaluations.
実施例8〜10および比較例6〜7の組成物の調製
成分(A)(製造例1で合成した化合物)、成分(B)、クエン酸三ナトリウムおよび水3gを80℃にて撹拌溶解し、得られた混合物を、あらかじめ80℃にて加熱撹拌させた、ラウロイルグルタミン酸ジ(フィトステリル/オクチルドデシル)、オクタン酸セチル(実施例9および10)、PPG−8セテス−20、PPG−6デシルテトラデセス−30およびグリセリンの混合物に添加した。混合物を40℃まで冷却した後、DPG(ジプロプレングリコール)、BG(1,3‐ブチレングリコール)、防腐剤および残りの水を混合し、クエン酸にてpH6.5に調整した。得られた組成物を30mLのガラス瓶に完全密封して25℃にて2週間保管した後、各種評価に供した。Preparation of compositions of Examples 8 to 10 and Comparative Examples 6 to 7 Component (A) (compound synthesized in Production Example 1), component (B), trisodium citrate and 3 g of water were dissolved by stirring at 80 ° C. The obtained mixture was heated and stirred at 80 ° C. in advance, di (phytosteryl / octyldodecyl) lauroylglutamate, cetyl octanoate (Examples 9 and 10), PPG-8 ceteth-20, PPG-6 decyl tetra. Added to the mixture of Decess-30 and glycerin. After cooling the mixture to 40 ° C., DPG (dipropylene glycol), BG (1,3-butylene glycol), a preservative and the remaining water were mixed, and the pH was adjusted to 6.5 with citric acid. The obtained composition was completely sealed in a 30 mL glass bottle, stored at 25 ° C. for 2 weeks, and then subjected to various evaluations.
評価1:経時安定性
前記のように調製、保管した組成物入りのガラス瓶を20〜30度傾け、目視にて観察し、調製直後の組成物の流動性との違いを下記の基準にて評価した。
◎:組成物の流動性の変化が見られない
△:組成物の流動性の低下が少し確認される
×:組成物の流動性の顕著な低下が確認されるEvaluation 1: Stability over time The glass bottle containing the composition prepared and stored as described above was tilted at 20 to 30 degrees and visually observed, and the difference from the fluidity of the composition immediately after preparation was evaluated according to the following criteria. .
⊚: No change in fluidity of the composition is observed Δ: A slight decrease in fluidity of the composition is confirmed ×: Significant decrease in fluidity of the composition is confirmed
評価2:熱安定性
前記のように調製、保管した組成物を、さらに50℃の恒温槽で2週間保管した後、組成物入りのガラス瓶を20〜30度傾け、目視にて観察し、50℃の恒温槽に入れる直前の組成物の流動性との違いを下記の基準にて評価した。
◎:組成物の流動性の変化が見られない
△:組成物の流動性の低下が少し確認される
×:組成物の流動性の顕著な低下が確認されるEvaluation 2: Heat stability The composition prepared and stored as described above was further stored in a constant temperature bath of 50 ° C. for 2 weeks, and then a glass bottle containing the composition was tilted at 20 to 30 ° and visually observed at 50 ° C. The difference from the fluidity of the composition immediately before being placed in the constant temperature bath was evaluated according to the following criteria.
⊚: No change in fluidity of the composition is observed Δ: A slight decrease in fluidity of the composition is confirmed ×: Significant decrease in fluidity of the composition is confirmed
評価3:使用性(曳糸性のなさ)の評価
前記のように調製、保管した組成物をスポイトにて滴下させた際に、組成物に糸を曳く性質が見られるか否かについて下記の基準にて評価した。なお、下記の基準において、水は◎であり、水溶性高分子であるポリアクリル酸ナトリウムの1%水溶液は×である。
◎:曳糸性が全く認められない
〇:曳糸性がほとんど認められない
△:曳糸性が少し認められる
×:曳糸性が明らかに認められるEvaluation 3: Evaluation of usability (no spinnability) When the composition prepared and stored as described above was dropped using a dropper, whether or not the composition has a thread-stripping property is described below. It was evaluated according to the standard. In the following criteria, water is ⊚, and 1% aqueous solution of sodium polyacrylate, which is a water-soluble polymer, is x.
◎: No spinnability at all 〇: Almost no spinnability △: Little spinnability ×: Clear spinnability
評価4〜6:使用感(きしみ感のなさ、なじみ感、しっとり感)の評価
前記のように調製、保管した組成物(40μL)を、健康な男女5名の前腕内側の皮膚8×2cm以内の範囲に塗布し、塗布中または塗布直後にどのように感じたかを調査し、以下の基準で採点を行った。なお、操作は被験者5人がそれぞれ行い、以下の基準で採点し、その平均点を求め、以下の評価基準で各項目について評価した。Evaluation 4 to 6: Evaluation of feeling of use (non-squeaky feeling, familiarity, moist feeling) The composition (40 μL) prepared and stored as described above was used to measure the skin on the inside of the forearm of 5 healthy men and women within 8 × 2 cm. It was applied to the range of, and how it was felt during or immediately after application was investigated, and the following criteria were used for scoring. In addition, the operation was performed by each of the five test subjects, the scores were scored according to the following criteria, the average score was obtained, and each item was evaluated according to the following criteria.
評価4(きしみ感のなさ)の基準
5点:きしみ感が全くなく、非常にすべすべしている
4点:きしみ感がほとんどなく、すべすべしている
3点:ふつう
2点:きしみ感が少しある
1点:きしみ感が非常に強い5 points for evaluation 4 (no squeaky feeling): No squeaky feeling and very smooth 4 points: Almost no squeaky feeling, smooth 3 points: Normal 2 points: Slightly squeaky feeling 1 point: Very squeaky feeling
評価5(なじみ感)の基準
5点:肌へのなじみが非常に良い
4点:肌へのなじみが良い
3点:ふつう
2点:肌へのなじみが悪い
1点:肌へのなじみが非常に悪いEvaluation 5 (Familiarity) criteria 5 points: Very familiar to the skin 4 points: Good to the skin 3 points: Normal 2 points: Poor to the skin 1 point: Very familiar to the skin Bad for
評価6(しっとり感)の基準
5点:しっとり感が非常に強い
4点:しっとり感がある
3点:ふつう
2点:しっとり感があまりない
1点:しっとり感が全くない5 points for evaluation 6 (moist feeling): Very moist feeling 4 points: Moist feeling 3 points: Normal 2 points: Moist feeling not very much 1 point: No moist feeling at all
評価基準
◎:平均点が4.0以上
○:平均点が3.0以上4.0未満
△:平均点が2.0以上3.0未満
×:平均点が2.0未満Evaluation Criteria ⊚: Average score of 4.0 or more ○: Average score of 3.0 or more and less than 4.0 Δ: Average score of 2.0 or more and less than 3.0 ×: Average score of less than 2.0
結果を表1〜表2に示す。 The results are shown in Tables 1 and 2.
本発明の組成物(実施例1〜10)は、成分(B)を含まない比較例1〜7の組成物と比較して、経時安定性および熱安定性に優れ、曳糸性がなく、使用性が良好であることが示された。また、本発明の組成物(実施例8〜10)は、成分(B)を含まない比較例6および7の組成物と比較して、きしみ感がなく、良好な使用感を有することが示された。 The compositions of the present invention (Examples 1 to 10) are superior in temporal stability and thermal stability, and have no spinnability, as compared with the compositions of Comparative Examples 1 to 7 which do not contain the component (B). It was shown that the usability was good. Further, it is shown that the compositions of the present invention (Examples 8 to 10) have no squeaky feeling and have a good feeling in use, as compared with the compositions of Comparative Examples 6 and 7 containing no component (B). Was done.
本発明は、きしみ感のない良好な使用感を示し、経時安定性および熱安定性に優れ、かつ曳糸性のない良好な使用性を有する組成物を提供することができる。 INDUSTRIAL APPLICABILITY The present invention can provide a composition which exhibits a good feeling of use without squeaky feeling, is excellent in temporal stability and thermal stability, and has good usability without spinnability.
本出願は、日本で出願された特願2014−262164を基礎としており、その内容は本明細書に全て包含されるものである。 This application is based on a patent application No. 2014-262164 filed in Japan, the contents of which are incorporated in full herein.
Claims (14)
(式中、
R1およびR2は、各々独立して、炭素原子数5〜21のアルキル基または炭素原子数5〜21のアルケニル基であり、
R3およびR4は、各々独立して、水素原子、炭素原子数1〜22のアルキル基または炭素原子数2〜22のアルケニル基であり、
zは0以上の整数であり、
xおよびyは、各々独立して、2〜4の整数である。)で示される化合物またはその塩;
および
成分(B):ココイルアルギニンエチルエステルピロリドンカルボン酸塩およびラウロイルアルギニンエチルエステル塩酸塩からなる群から選択される少なくとも一種
を含有する組成物。 Component (A): Formula (1)
(In the formula,
R 1 and R 2 are each independently an alkyl group having 5 to 21 carbon atoms or an alkenyl group having 5 to 21 carbon atoms,
R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 22 carbon atoms or an alkenyl group having 2 to 22 carbon atoms,
z is an integer of 0 or more,
x and y are each independently an integer of 2 to 4. ) Or a salt thereof;
And component (B): a composition containing at least one selected from the group consisting of cocoyl arginine ethyl ester pyrrolidone carboxylate and lauroyl arginine ethyl ester hydrochloride .
Cosmetics containing the composition of any one of Claims 1-13.
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| PCT/JP2015/086211 WO2016104694A1 (en) | 2014-12-25 | 2015-12-25 | Acyl basic amino acid derivative, and cosmetic composition comprising basic amino acid |
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| JP6662093B2 (en) * | 2016-02-24 | 2020-03-11 | 味の素株式会社 | Aid for adjusting hair shape |
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| JP4543692B2 (en) * | 2003-04-28 | 2010-09-15 | 味の素株式会社 | Basic amino acid derivatives |
| JP2006348101A (en) * | 2005-06-14 | 2006-12-28 | Asahi Kasei Chemicals Corp | Detergent composition with improved thickening |
| WO2013118896A1 (en) * | 2012-02-09 | 2013-08-15 | 味の素株式会社 | Basic amino acid derivative |
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| Publication number | Publication date |
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| WO2016104694A8 (en) | 2016-10-06 |
| WO2016104694A1 (en) | 2016-06-30 |
| JPWO2016104694A1 (en) | 2017-10-05 |
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