WO2015064678A1 - N-長鎖アシル酸性アミノ酸および/またはその塩を含む水溶液、並びにその製造方法 - Google Patents
N-長鎖アシル酸性アミノ酸および/またはその塩を含む水溶液、並びにその製造方法 Download PDFInfo
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- WO2015064678A1 WO2015064678A1 PCT/JP2014/078856 JP2014078856W WO2015064678A1 WO 2015064678 A1 WO2015064678 A1 WO 2015064678A1 JP 2014078856 W JP2014078856 W JP 2014078856W WO 2015064678 A1 WO2015064678 A1 WO 2015064678A1
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- WIPO (PCT)
- Prior art keywords
- salt
- aqueous solution
- amino acid
- acidic amino
- acyl
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 114
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 109
- 150000001413 amino acids Chemical class 0.000 title claims abstract description 107
- 230000002378 acidificating effect Effects 0.000 title claims abstract description 104
- 125000002252 acyl group Chemical group 0.000 title claims abstract description 92
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 42
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 103
- 239000000194 fatty acid Substances 0.000 claims abstract description 103
- 229930195729 fatty acid Natural products 0.000 claims abstract description 103
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 72
- 108010016626 Dipeptides Proteins 0.000 claims description 23
- 239000003125 aqueous solvent Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 238000011085 pressure filtration Methods 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 10
- -1 amino acid salt Chemical class 0.000 abstract description 47
- 238000000034 method Methods 0.000 abstract description 6
- 235000002639 sodium chloride Nutrition 0.000 description 116
- 235000001014 amino acid Nutrition 0.000 description 94
- 229940024606 amino acid Drugs 0.000 description 94
- 159000000000 sodium salts Chemical class 0.000 description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 29
- 235000013922 glutamic acid Nutrition 0.000 description 29
- 239000004220 glutamic acid Substances 0.000 description 29
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 25
- 239000003240 coconut oil Substances 0.000 description 21
- 235000019864 coconut oil Nutrition 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000003860 storage Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 235000003704 aspartic acid Nutrition 0.000 description 11
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 11
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 10
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 10
- 239000003760 tallow Substances 0.000 description 10
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 238000005187 foaming Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 235000015278 beef Nutrition 0.000 description 6
- 239000012459 cleaning agent Substances 0.000 description 6
- 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 6
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 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 6
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 6
- 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 6
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical class NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 5
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 5
- 239000005639 Lauric acid Substances 0.000 description 5
- 235000019482 Palm oil Nutrition 0.000 description 5
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 5
- 125000000637 arginyl group Chemical class N[C@@H](CCCNC(N)=N)C(=O)* 0.000 description 5
- 159000000007 calcium salts Chemical class 0.000 description 5
- 239000004359 castor oil Substances 0.000 description 5
- 235000019438 castor oil Nutrition 0.000 description 5
- 239000002385 cottonseed oil Substances 0.000 description 5
- 235000012343 cottonseed oil Nutrition 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- PXEDJBXQKAGXNJ-QTNFYWBSSA-L disodium L-glutamate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CCC([O-])=O PXEDJBXQKAGXNJ-QTNFYWBSSA-L 0.000 description 5
- 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 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 159000000003 magnesium salts Chemical class 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000004006 olive oil Substances 0.000 description 5
- 235000008390 olive oil Nutrition 0.000 description 5
- 239000002540 palm oil Substances 0.000 description 5
- 239000008363 phosphate buffer Substances 0.000 description 5
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 5
- 239000003549 soybean oil Substances 0.000 description 5
- 235000012424 soybean oil Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- UNSAJINGUOTTRA-UHFFFAOYSA-N 3-(3-bromophenyl)prop-2-yn-1-ol Chemical compound OCC#CC1=CC=CC(Br)=C1 UNSAJINGUOTTRA-UHFFFAOYSA-N 0.000 description 4
- 239000004381 Choline salt Substances 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 235000019417 choline salt Nutrition 0.000 description 4
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 description 4
- 235000013923 monosodium glutamate Nutrition 0.000 description 4
- 239000004223 monosodium glutamate Substances 0.000 description 4
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 4
- 239000003346 palm kernel oil Substances 0.000 description 4
- 235000019865 palm kernel oil Nutrition 0.000 description 4
- 150000003248 quinolines Chemical class 0.000 description 4
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 3
- 235000021314 Palmitic acid Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 125000003910 behenoyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 239000002270 dispersing agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 108010055341 glutamyl-glutamic acid Proteins 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 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 3
- 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 3
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 3
- 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 3
- HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 2
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- 230000002421 anti-septic effect Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- WDRWZVWLVBXVOI-QTNFYWBSSA-L dipotassium;(2s)-2-aminopentanedioate Chemical compound [K+].[K+].[O-]C(=O)[C@@H](N)CCC([O-])=O WDRWZVWLVBXVOI-QTNFYWBSSA-L 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004255 ion exchange chromatography Methods 0.000 description 2
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- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- HQEROMHPIOLGCB-DFWYDOINSA-M potassium;(2s)-2-aminopentanedioate;hydron Chemical compound [K+].[O-]C(=O)[C@@H](N)CCC(O)=O HQEROMHPIOLGCB-DFWYDOINSA-M 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
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- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
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- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 1
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- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
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- 108010040443 aspartyl-aspartic acid Proteins 0.000 description 1
- HNGSNSWYGHQTEH-UHFFFAOYSA-N azane;2-[bis(2-hydroxyethyl)amino]ethanol Chemical class N.OCCN(CCO)CCO HNGSNSWYGHQTEH-UHFFFAOYSA-N 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 230000008901 benefit Effects 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
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- 238000005260 corrosion Methods 0.000 description 1
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- 238000007865 diluting Methods 0.000 description 1
- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
- XMXOIHIZTOVVFB-JIZZDEOASA-L disodium;(2s)-2-aminobutanedioate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](N)CC([O-])=O XMXOIHIZTOVVFB-JIZZDEOASA-L 0.000 description 1
- QTHQYNCAWSGBCE-UHFFFAOYSA-N docosanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCCCCCC(Cl)=O QTHQYNCAWSGBCE-UHFFFAOYSA-N 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- NTQYXUJLILNTFH-UHFFFAOYSA-N nonanoyl chloride Chemical compound CCCCCCCCC(Cl)=O NTQYXUJLILNTFH-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- TXXVQZSTAVIHFD-DKWTVANSSA-M potassium;(2s)-2-aminobutanedioate;hydron Chemical compound [K+].[O-]C(=O)[C@@H](N)CC(O)=O TXXVQZSTAVIHFD-DKWTVANSSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229940043131 pyroglutamate Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- WTWSHHITWMVLBX-DKWTVANSSA-M sodium;(2s)-2-aminobutanedioate;hydron Chemical compound [Na+].[O-]C(=O)[C@@H](N)CC(O)=O WTWSHHITWMVLBX-DKWTVANSSA-M 0.000 description 1
- GJBHGUUFMNITCI-QTNFYWBSSA-M sodium;(2s)-2-aminopentanedioate;hydron;hydrate Chemical compound O.[Na+].OC(=O)[C@@H](N)CCC([O-])=O GJBHGUUFMNITCI-QTNFYWBSSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- FJRPWCNFWGBGOF-UHFFFAOYSA-N tridecanoyl chloride Chemical compound CCCCCCCCCCCCC(Cl)=O FJRPWCNFWGBGOF-UHFFFAOYSA-N 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- JUKPJGZUFHCZQI-UHFFFAOYSA-N undecanoyl chloride Chemical compound CCCCCCCCCCC(Cl)=O JUKPJGZUFHCZQI-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
-
- 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
- A61Q19/10—Washing or bathing preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/02—Preparations for cleaning the hair
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/49—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/28—Aminocarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
- C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
- C11D17/04—Detergent materials or soaps characterised by their shape or physical properties combined with or containing other objects
- C11D17/041—Compositions releasably affixed on a substrate or incorporated into a dispensing means
Definitions
- the present invention relates to an aqueous solution containing an N-long chain acyl acidic amino acid (specifically, an NC 8-22 acyl acidic amino acid) and / or a salt thereof, and a method for producing the same.
- an N-long chain acyl acidic amino acid specifically, an NC 8-22 acyl acidic amino acid
- N-long chain acyl acidic amino acid salts are useful as raw materials for detergents, dispersants, emulsifiers, antibacterial agents, preservatives and the like because they have a surface active action, a bactericidal action, a metal corrosion inhibiting action and the like.
- it since it is mild to the hand skin, it is very useful as a raw material for cleaning agents such as shampoos and body shampoos.
- N-long chain acyl acidic amino acid for example, N-long chain acyl glutamic acid
- an acidic amino acid for example, glutamic acid
- a salt thereof and a long chain fatty acid chloride in an aqueous solvent, acetone
- a method of condensing in a mixed solvent of a hydrophilic organic solvent such as t-butanol or propylene glycol and water in the presence of a base is known (Schotten-Baumann reaction, for example, see Patent Document 1).
- Patent Document 1 the obtained N-long chain acyl acidic amino acid is precipitated and recovered as a solid, and the utility value of the aqueous solution itself after the reaction is not evaluated.
- N-long chain acyl acidic amino acid dipeptides are known as substances that improve water resistance and squeaky feeling in detergents containing N-long chain acyl acidic amino acids (Patent Document 2).
- N-long-chain acyl acidic amino acid dipeptides must be obtained by acylating acidic amino acid dipeptides by the Schotten-Baumann reaction or the like, and are expensive and difficult to obtain.
- JP-A-10-81656 Japanese Patent Laid-Open No. 10-121091
- An aqueous reaction solution containing an N-long chain acylamino acid and / or salt thereof obtained after the Schotten-Baumann reaction of an acidic amino acid and / or salt thereof with a long-chain fatty acid chloride can be used as a cleaning agent or its raw material as it is. This makes it possible to simplify the manufacturing process and equipment by omitting the recovery, washing, and drying operations of N-long chain acylamino acids and / or their salts, and achieve a low environmental impact manufacturing process that does not emit any waste liquid. Is done.
- the reaction aqueous solution In order to handle the above-described reaction aqueous solution as it is as a cleaning agent or its raw material, the reaction aqueous solution needs to have high and low temperature stability.
- unreacted acidic amino acids and / or salts thereof for example, glutamic acid and glutamate
- lactam for example, pyroglutamic acid, Pyroglutamate
- N-long chain acyl glutamic acid and / or its salt obtained by the Schotten-Baumann reaction has a problem that the solubility of the reaction aqueous solution is lowered when it is stored at low temperature.
- the present invention has been made paying attention to the above-mentioned circumstances, and an object of the present invention is to provide an aqueous solution containing an N-long chain acylamino acid and / or a salt thereof excellent in high temperature and low temperature stability. is there.
- an acidic amino acid and / or a salt thereof and C 8-22 fatty acid chloride are reacted in an aqueous solvent at a pH of 10 to 13, and then an aqueous reaction solution thereof. It was found that an aqueous solution containing an N—C 8-22 acyl acidic amino acid and / or a salt thereof excellent in low-temperature and high-temperature stability can be obtained by adjusting the pH of the solution to a certain range.
- the present invention based on this finding is as follows.
- the aqueous solution after the second step is 1.0 to 10.0% by weight of acidic amino acid and / or salt thereof, and N—C 8-22 acyl acidic amino acid and / or salt thereof is 10.0 to 30.0.
- the production method according to any one of the above [1] to [11], wherein the aqueous solution after the second step further contains an N—C 8-22 acyl acidic amino acid dipeptide and / or a salt thereof.
- Acidic amino acid and / or salt thereof 1.0 to 10.0% by weight, N—C 8-22 acyl acidic amino acid and / or salt thereof 10.0 to 30.0% by weight, and N—C 8— An aqueous solution containing 0.5 to 5.0% by weight of 22 acyl acidic amino acid dipeptide and / or a salt thereof and having a pH of 8.4 to 9.5.
- the N—C 8-22 acyl acidic amino acid and / or salt thereof is one or more selected from N—C 8-22 acyl glutamic acid, N—C 8-22 acyl aspartic acid, and sodium salts thereof.
- Aqueous solution [23] The aqueous solution according to any one of [17] to [20], wherein the N—C 8-22 acyl acidic amino acid and / or salt thereof is N-cocoylglutamic acid and / or a sodium salt thereof.
- N—C 8-22 acyl acidic amino acid dipeptide and / or a salt thereof is N—C 8-22 acyl glutamyl glutamic acid, N—C 8-22 acyl aspartyl glutamic acid, N—C 8-22 acyl glutamyl asparagine
- N—C 8-22 acyl acidic amino acid tripeptide and / or a salt thereof is N—C 8-22 acyl glutamyl glutamyl glutamic acid, N—C 8-22 acyl aspartyl glutamyl glutamic acid, N—C 8-22 Acyl glutamyl aspartyl glutamic acid, NC 8-22 acyl aspartyl aspartyl glutamic acid, NC 8-22 acyl aspartyl aspartyl aspartic acid, NC 8-22 acyl glutamyl aspartyl aspartic acid, NC 8-22 acyl glutamyl aspartyl aspartic acid, NC 8-22 acyl glutamyl aspartyl aspartic acid, NC 8-22 acyl glutamyl aspartyl aspartic acid, NC 8 The aqueous solution according to the above [27], which is at least one selected from -22 acyl aspartyl glutamyl aspartic acid, N—C 8-22 acyl glutamyl glutamyl aspartic acid, and sodium salt
- the C 8-22 fatty acid and / or salt thereof is one or more selected from octanoic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, coconut oil fatty acid, and sodium salts thereof [31] ].
- the aqueous solution according to [31], wherein the C 8-22 fatty acid and / or salt thereof is at least one selected from lauric acid, coconut oil fatty acid, and sodium salts thereof.
- the aqueous solution according to [31], wherein the C 8-22 fatty acid and / or salt thereof is coconut oil fatty acid and / or a sodium salt thereof.
- an aqueous solution containing an N—C 8-22 acyl acidic amino acid and / or a salt thereof excellent in low temperature and high temperature stability can be obtained.
- an acidic amino acid and / or a salt thereof and C 8-22 fatty acid chloride are reacted in an aqueous solvent at pH 10-13 to form an N—C 8-22 acyl acidic amino acid salt.
- the pH of the aqueous solvent (that is, the reaction system) containing the reaction product in the first step is preferably 10.5 to 12.5, more preferably 11.0 to 12.0.
- the acidic amino acid used in the first step means an amino acid having two or more carboxy groups.
- the acidic amino acid may be optically active or racemic.
- the acidic amino acid is preferably a monoaminodicarboxylic acid, more preferably glutamic acid and / or aspartic acid, and even more preferably glutamic acid. Both glutamic acid and aspartic acid may be L-form or D-form, and preferably L-form.
- Examples of the salt of acidic amino acid include alkali metal salts such as sodium salt and potassium salt; alkaline earth metal salts such as magnesium salt and calcium salt; alkanolamine salts such as triethanolamine salt; ammonium salt; choline salt; And salts with basic amino acids such as lysine salts, ornithine salts, and arginine salts.
- This salt is preferably an alkali metal salt, more preferably a sodium salt. Since acidic amino acids have two or more carboxy groups, in the salts thereof, all carboxy groups may be in the form of salts (-COOM, M is a counter cation), and only some carboxy groups are in the form of salts. There may be.
- the “acidic amino acid and / or salt thereof” used in the first step is preferably one or more selected from glutamic acid, aspartic acid and salts thereof, more preferably glutamic acid, aspartic acid, sodium salts thereof, and One or more selected from these potassium salts (ie glutamic acid, aspartic acid, monosodium glutamate, monopotassium glutamate, monosodium aspartate, monopotassium aspartate, disodium glutamate, dipotassium glutamate, disodium aspartate and aspartic acid One or more selected from dipotassium), and more preferably one or more selected from glutamic acid, its sodium salt, and its potassium salt (ie, glutamic acid, glutamic acid monona).
- the C 8-22 fatty acid chloride used in the first step means a fatty acid chloride having 8 to 22 carbon atoms.
- C 8-22 fatty acid chloride may be saturated or unsaturated.
- fatty acid chloride having a single composition, for example, octanoyl chloride, nonanoyl chloride, decanoyl chloride, undecanoyl chloride, lauroyl chloride, tridecanoyl chloride, myristoyl chloride, stearoyl chloride, palmitoyl Chloride, behenoyl chloride, isostearoyl chloride, oleoyl chloride, etc .; and mixed fatty acid chlorides containing these, such as coconut oil fatty acid chloride, beef tallow fatty acid chloride, hardened tallow fatty acid chloride, soybean oil fatty acid chloride, cottonseed oil fatty acid chloride, castor Oil fatty acid chloride, olive oil fatty acid chloride, palm oil
- the C 8-22 fatty acid chloride is preferably octanoyl chloride, decanoyl chloride, lauroyl chloride, myristoyl chloride, palmitoyl chloride, coconut oil fatty acid chloride, more preferably lauroyl chloride, coconut oil fatty acid chloride, most preferably Coconut oil fatty acid chloride.
- the base used for maintaining the pH of the reaction system in the first step at 10 to 13 is not particularly limited, and examples thereof include sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, ammonia and the like. Of these, sodium hydroxide is preferred.
- the N—C 8-22 acyl acidic amino acid formed in the first step means an acidic amino acid derivative in which the hydrogen atom of the amino group is substituted with an acyl group having 8 to 22 carbon atoms.
- the C 8-22 acyl group is specifically an acyl group corresponding to a portion excluding the chloride of the C 8-22 fatty acid chloride used in the first step.
- the C 8-22 acyl group includes an acyl group having a single composition, for example, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group, lauroyl group, tridecanoyl group, myristoyl group, stearoyl group, palmitoyl group, behenoyl group, isostearoyl group Groups, oleoyl groups, etc .; and mixed fatty acid acyl groups containing these, such as coconut oil fatty acid acyl groups (also referred to as cocoyl groups), beef tallow fatty acid acyl groups, hardened tallow fatty acid acyl groups, soybean oil fatty acid acyl groups, cottonseed oil fatty acid acyls Group, castor oil fatty acid acyl group, olive oil fatty acid acyl group, palm oil fatty acid acyl group, palm kernel oil fatty acid acyl group, and the like.
- the C 8-22 acyl group is preferably an octanoyl group, a decanoyl group, a lauroyl group, a myristoyl group, a palmitoyl group, or a cocoyl group, and more preferably a lauroyl group or a cocoyl group.
- the N—C 8-22 acyl acidic amino acid is preferably N—C 8-22 acyl glutamic acid and / or N—C 8-22 acyl aspartic acid.
- Examples of the salt of N—C 8-22 acyl acidic amino acid include alkali metal salts such as sodium salt and potassium salt; alkaline earth metal salts such as magnesium salt and calcium salt; alkanolamine salts such as triethanolamine salt; And ammonium salts; choline salts; and salts with basic amino acids such as lysine salts, ornithine salts, and arginine salts.
- This salt is preferably an alkali metal salt, more preferably a sodium salt.
- the amount of acidic amino acid and / or salt thereof used is, for example, 0.8 to 1.5 moles per mole of C 8-22 fatty acid chloride.
- the amount used is preferably 1 mol of C 8-22 fatty acid chloride.
- the amount is 0.9 to 1.4 mol, more preferably 1.0 to 1.3 mol.
- a mixed fatty acid chloride such as coconut oil fatty acid chloride
- the molecular weight thereof is octanoyl chloride, decanoyl chloride, lauroyl chloride, myristoyl chloride, which constitutes coconut oil fatty acid chloride, It can be calculated by the weight ratio of palmitoyl chloride.
- the initial concentration of the acidic amino acid and / or salt thereof in the reaction system is preferably 20 to 50% by weight, more preferably 25 to 40% by weight in order to perform an efficient reaction with the acid chloride. is there.
- C 8-22 fatty acid chloride is dropped and reacted while stirring an aqueous solvent containing an acidic amino acid and / or a salt thereof.
- the dropping time of the total amount of C 8-22 fatty acid chloride is preferably 30 to 600 minutes, more preferably 60 to 450 minutes, in order to carry out an efficient reaction with acidic amino acids and / or salts thereof.
- the temperature of the system is preferably 0 to 50 ° C., more preferably 5 to 40 ° C.
- the reaction temperature in the first step after adding all the C 8-22 fatty acid chloride to the reaction system is preferably 10 to 50 ° C., more preferably in order to complete the reaction of the fatty acid chloride with the acidic amino acid and its salt. Is 20 to 40 ° C., and the reaction time of the first step is preferably 10 to 600 minutes, more preferably 30 to 480 minutes.
- the aqueous solvent used in the first step does not substantially contain a hydrophilic organic solvent (for example, acetone, t-butanol, propylene glycol, etc.).
- the aqueous solvent does not substantially contain a hydrophilic organic solvent means that the content of the hydrophilic organic solvent in the aqueous solvent is 5% by weight or less, or the aqueous solvent does not contain the hydrophilic organic solvent. To do.
- the content of the hydrophilic organic solvent in the aqueous solvent is more preferably 4% by weight or less, further preferably 3% by weight or less, and particularly preferably 2% by weight or less.
- An acidic amino acid and / or a salt thereof, an N—C 8-22 acyl acidic amino acid and / or a salt thereof in an aqueous solution obtained by the production method of the present invention because the aqueous solvent does not substantially contain a hydrophilic organic solvent, The effect that the content of N—C 8-22 acyl acidic amino acid dipeptide and / or salt thereof, N—C 8-22 acyl acidic amino acid tripeptide and / or salt thereof is increased, and foaming of aqueous solution and use feeling are improved. Is obtained.
- the N—C 8-22 acyl acidic amino acid dipeptide and the like will be described later.
- the water solvent does not substantially contain a hydrophilic organic solvent, there is an advantage that it is not necessary to consider the influence on the working environment, countermeasures of the Fire Service Act, and the like.
- the production method of the present invention includes a second step of adjusting the pH of the aqueous solution after the first step to 8.4 to 9.5.
- the pH is preferably 8.6 to 9.2.
- the acid used for adjusting the pH of the aqueous solution in the second step is not particularly limited, inorganic acids such as hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid; carboxylic acids (for example, acetic acid, citric acid), Organic acids such as sulfonic acids can be used. Of these, inorganic acids are preferred, and hydrochloric acid is more preferred.
- the temperature of the aqueous solution When adding acid to the aqueous solution in the second step, it is preferable to adjust the temperature of the aqueous solution to 0 to 50 ° C. for safety. This temperature adjustment may be performed, for example, by using a known cooler, or by adding water at normal temperature or cooling water to the aqueous solution.
- the production method of the present invention preferably further includes a step of performing pressure filtration (hereinafter abbreviated as “pressure filtration step”).
- pressure filtration step may be performed either after the first step or after the second step, and may be performed both after the first step and after the second step.
- the temperature of the aqueous solution during filtration is preferably 20 to 90 ° C., more preferably 40 to 80 ° C. in order to increase the working efficiency of pressure filtration.
- a filter aid in the pressure filtration step.
- the filter aid include Celite (registered trademark).
- the amount of filter aid used per 100 g of aqueous solution is preferably 0.05 to 10 g, more preferably 0.1 to 5 g in order to improve the working efficiency of pressure filtration.
- the aqueous solution containing the filter aid After adding the filter aid, it is preferable to stir the aqueous solution containing the filter aid for a certain period of time in order to sufficiently adsorb the impurities to the filter aid.
- the stirring time is preferably 5 to 300 minutes, more preferably 10 to 200 minutes, and the temperature of the aqueous solution is preferably 20 to 90 ° C., more preferably 40 to 80 ° C.
- the pressure for pressure filtration is preferably 0.2 to 10 MPa, more preferably 0.3 to 5 MPa, and the temperature of the aqueous solution at that time is preferably 20 to 90 ° C., more preferably 40 to 80 ° C. .
- This pressure filtration can be performed using a known device such as a stainless steel holder with a tank.
- N—C 8-22 acyl acidic amino acid and / or its salt as well as N which is usually synthesized by acylating acidic amino acid dipeptide and / or its salt.
- a —C 8-22 acyl acidic amino acid dipeptide and / or salt thereof is formed.
- an N—C 8-22 acyl acidic amino acid tripeptide and / or a salt thereof is also formed.
- the N—C 8-22 acyl acidic amino acid dipeptide is a derivative of a dipeptide formed from an acidic amino acid, and means that a hydrogen atom of an amino group is substituted with an acyl group having 8 to 22 carbon atoms.
- N—C 8-22 acyl acidic amino acid tripeptide is a derivative of a tripeptide formed from an acidic amino acid, wherein a hydrogen atom of the amino group is substituted with an acyl group having 8 to 22 carbon atoms. means.
- N-C 8-22 acyl acidic amino acid dipeptide preferably N-C 8-22 acyl -Glu-Glu, N-C 8-22 acyl -Asp-Glu, N-C 8-22 acyl -Glu-Asp and One or more selected from N—C 8-22 acyl-Asp-Asp, more preferably selected from N—C 8-22 acyl-Glu-Glu and N—C 8-22 acyl-Asp-Asp One or more, more preferably N—C 8-22 acyl-Glu-Glu.
- each display is based on a common abbreviation in the peptide field.
- N-C 8-22 acyl -Glu-Glu represents a “N-C 8-22 acyl glutaric Tamil glutamic acid”
- N-C 8-22 acyl -Asp-Asp is "N-C 8-22 “Acyl aspartyl aspartic acid”.
- the C 8-22 acyl group includes an acyl group having a single composition, for example, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group, lauroyl group, tridecanoyl group, myristoyl group, stearoyl group, palmitoyl group, behenoyl group, isostearoyl group Groups, oleoyl groups, etc .; and mixed fatty acid acyl groups containing these, such as coconut oil fatty acid acyl groups (also referred to as cocoyl groups), beef tallow fatty acid acyl groups, hardened tallow fatty acid acyl groups, soybean oil fatty acid acyl groups, cottonseed oil fatty acid acyls Group, castor oil fatty acid acyl group, olive oil fatty acid acyl group, palm oil fatty acid acyl group, palm kernel oil fatty acid acyl group, and the like.
- the C 8-22 acyl group is preferably an octanoyl group, a decanoyl group, a lauroyl group, a myristoyl group, a palmitoyl group, or a cocoyl group, and more preferably a lauroyl group or a cocoyl group.
- Examples of the salt of N—C 8-22 acyl acidic amino acid dipeptide include alkali metal salts such as sodium salt and potassium salt; alkaline earth metal salts such as magnesium salt and calcium salt; alkanolamine salts such as triethanolamine salt Ammonium salts; choline salts; and salts with basic amino acids such as lysine salts, ornithine salts, arginine salts; This salt is preferably an alkali metal salt, more preferably a sodium salt.
- N—C 8-22 acyl acidic amino acid tripeptides are preferably N—C 8-22 acyl-Glu-Glu-Glu, N—C 8-22 acyl-Asp-Glu-Glu, N—C 8-22 acyl.
- the C 8-22 acyl group includes an acyl group having a single composition, for example, octanoyl group, nonanoyl group, decanoyl group, undecanoyl group, lauroyl group, tridecanoyl group, myristoyl group, stearoyl group, palmitoyl group, behenoyl group, isostearoyl group Groups, oleoyl groups, etc .; and mixed fatty acid acyl groups containing these, such as coconut oil fatty acid acyl groups (also referred to as cocoyl groups), beef tallow fatty acid acyl groups, hardened tallow fatty acid acyl groups, soybean oil fatty acid acyl groups, cottonseed oil fatty acid acyls Group, castor oil fatty acid acyl group, olive oil fatty acid acyl group, palm oil fatty acid acyl group, palm kernel oil fatty acid acyl group, and the like.
- the C 8-22 acyl group is preferably an octanoyl group, a decanoyl group, a lauroyl group, a myristoyl group, a palmitoyl group, or a cocoyl group, and more preferably a lauroyl group or a cocoyl group.
- Examples of the salt of the N—C 8-22 acyl acidic amino acid tripeptide include alkali metal salts such as sodium salt and potassium salt; alkaline earth metal salts such as magnesium salt and calcium salt; alkanolamines such as triethanolamine salt Salts; ammonium salts; choline salts; and salts with basic amino acids such as lysine salts, ornithine salts, arginine salts, and the like.
- This salt is preferably an alkali metal salt, more preferably a sodium salt.
- the aqueous solution obtained by the production method of the present invention includes not only the N—C 8-22 acyl acidic amino acid and / or its salt formed by the Schotten-Baumann reaction in the first step, but also the unreacted raw material acidic amino acid and It is preferable to include a salt thereof.
- the presence of the acidic amino acid and / or salt thereof provides the effect of improving foaming and feeling of use.
- the acidic amino acid and / or salt thereof contained in the aqueous solution has the same meaning as described above.
- the aqueous solution obtained by the production method of the present invention preferably contains a C 8-22 fatty acid and / or a salt thereof.
- C 8-22 fatty acids and / or salts thereof provide the effect of improving foaming and feeling of use.
- the C 8-22 fatty acid is derived from the C 8-22 fatty acid chloride used in the first step, and has a single composition such as octanoic acid, nonanoic acid, decanoic acid, undecanoic acid, lauric acid, tridecane.
- Acids myristic acid, stearic acid, palmitic acid, behenic acid, isostearic acid, oleic acid and the like; and mixed fatty acids containing them, such as coconut oil fatty acid, beef tallow fatty acid, hydrogenated beef tallow fatty acid, soybean oil fatty acid, cottonseed oil fatty acid, castor oil Fatty acids, olive oil fatty acids, palm oil fatty acids, palm kernel oil fatty acids and the like.
- the C 8-22 fatty acid is preferably octanoic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, coconut oil fatty acid, more preferably lauric acid, coconut oil fatty acid, most preferably coconut oil fatty acid. .
- salts of C 8-22 fatty acids include alkali metal salts such as sodium salts and potassium salts; alkaline earth metal salts such as magnesium salts and calcium salts; alkanolamine salts such as triethanolamine salts; ammonium salts; And salts with basic amino acids such as lysine salts, ornithine salts, arginine salts, and the like.
- This salt is preferably an alkali metal salt, more preferably a sodium salt.
- the content of acidic amino acid and / or salt thereof is preferably 1.0 to 10.0% by weight, more preferably 2.0 to 8.0% by weight.
- N—C 8-22 acyl acidic amino acid and / or a salt thereof is preferably 10.0 to 30.0% by weight, more preferably 15.0 to 25.0% by weight.
- the content of 8-22 acyl acidic amino acid dipeptide and / or a salt thereof is preferably 0.5 to 5.0% by weight, more preferably 1.0 to 4.0% by weight.
- the manufacturing method of the present invention further includes a step of filling the container with the aqueous solution after the second step.
- the container is not particularly limited, and may be any of bottles, cans, bags, and the like.
- the material of the container is not particularly limited, and may be glass, plastic, metal, or a composite material thereof.
- the present invention provides an acidic amino acid and / or salt thereof of 1.0 to 10.0% by weight, an N—C 8-22 acyl acidic amino acid and / or salt thereof of 10.0 to 30.0% obtained by the above-described method. And an N—C 8-22 acyl acidic amino acid dipeptide and / or salt thereof in an amount of 0.5 to 5.0% by weight and an aqueous solution having a pH of 8.4 to 9.5.
- the aqueous solution of the present invention may further contain an N—C 8-22 acyl acidic amino acid tripeptide and / or a salt thereof.
- the aqueous solution of the present invention may further contain C 8-22 fatty acid and / or a salt thereof.
- the aqueous solution of the present invention is excellent in low temperature and high temperature stability, has good foaming and feeling in use, and is useful as a cleaning agent, a dispersing agent, an emulsifier, an antibacterial agent, an antiseptic, or the like or a raw material thereof.
- Example 1 (Production of aqueous solution containing sodium salt of N-cocoyl glutamic acid) 187 g (1.00 mol) of monosodium L-glutamate monohydrate was suspended in 300 mL of water, and 78 g of 48% aqueous sodium hydroxide solution was added thereto to prepare an aqueous solution having a pH of 12.0. Cooled down. At the same time, 200 g of coconut oil fatty acid chloride (molecular weight 219, 0.91 mol calculated from the weight ratio of the components) and 98 g of 48% sodium hydroxide aqueous solution were maintained at a pH of 12.0 and a temperature of 15 ° C. However, it was dripped over 1 hour.
- G / G 0 is 0.7 or more O: G / G 0 is 0.5 or more and less than 0.7 ⁇ : G / G 0 is 0.3 or more and less than 0.5 ⁇ : G / G 0 is 0. Less than 3
- N-cocoyl glutamic acid prepared by the method described in Patent Document 1 is suspended in water so as to be 0.5% by weight in terms of monosodium salt, and then adjusted to pH 9.0 with 48% aqueous sodium hydroxide solution.
- the foaming test was similarly performed using the prepared aqueous solution. The results are shown in Table 3.
- Example 3 From the results shown in Table 3, it can be seen that the aqueous solution produced in Example 1 is excellent in foaming and usability as a cleaning agent.
- an aqueous solution containing an N—C 8-22 acyl acidic amino acid and / or a salt thereof excellent in low temperature and high temperature stability can be obtained.
- the aqueous solution is useful as a cleaning agent, a dispersing agent, an emulsifier, an antibacterial agent, an antiseptic, or the like or a raw material thereof.
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Abstract
Description
第1工程後の水溶液のpHを8.4~9.5に調整する第2工程
を含む、N-C8-22アシル酸性アミノ酸および/またはその塩を含み、pHが8.4~9.5である水溶液の製造方法。
[2] 第1工程後の水溶液のpHを8.6~9.2に調整する前記[1]に記載の製造方法。
[4] 酸性アミノ酸および/またはその塩が、グルタミン酸および/またはそのナトリウム塩である前記[1]または[2]に記載の製造方法。
[6] C8-22脂肪酸クロライドが、ラウロイルクロライドおよび/またはヤシ油脂肪酸クロライドである前記[1]~[4]のいずれか一つに記載の製造方法。
[7] C8-22脂肪酸クロライドが、ヤシ油脂肪酸クロライドである前記[1]~[4]のいずれか一つに記載の製造方法。
[9] 加圧ろ過を行う工程をさらに含む前記[1]~[8]のいずれか一つに記載の製造方法。
[10] 水溶媒が、実質的に親水性有機溶媒を含まない前記[1]~[9]のいずれか一つに記載の製造方法。
[12] 第2工程後の水溶液が、N-C8-22アシル酸性アミノ酸ジペプチドおよび/またはその塩をさらに含む前記[1]~[11]のいずれか一つに記載の製造方法。
[13] 水溶液中のN-C8-22アシル酸性アミノ酸ジペプチドおよび/またはその塩の含有量が、0.5~5.0重量%である前記[12]に記載の製造方法。
[14] 第2工程後の水溶液が、N-C8-22アシル酸性アミノ酸トリペプチドおよび/またはその塩をさらに含む前記[1]~[13]のいずれか一つに記載の製造方法。
[15] 第2工程後の水溶液が、C8-22脂肪酸および/またはその塩をさらに含む前記[1]~[14]のいずれか一つに記載の製造方法。
[18] pHが8.6~9.2である前記[17]に記載の水溶液。
[20] 酸性アミノ酸および/またはその塩が、グルタミン酸および/またはそのナトリウム塩である前記[17]または[18]に記載の水溶液。
[22] N-C8-22アシル酸性アミノ酸および/またはその塩が、N-C8-22アシルグルタミン酸および/またはそのナトリウム塩である前記[17]~[20]のいずれか一つに記載の水溶液。
[23] N-C8-22アシル酸性アミノ酸および/またはその塩が、N-ココイルグルタミン酸および/またはそのナトリウム塩である前記[17]~[20]のいずれか一つに記載の水溶液。
[25] N-C8-22アシル酸性アミノ酸ジペプチドおよび/またはその塩が、N-C8-22アシルグルタミルグルタミン酸および/またはそのナトリウム塩である前記[17]~[23]のいずれか一つに記載の水溶液。
[26] N-C8-22アシル酸性アミノ酸ジペプチドおよび/またはその塩が、N-ココイルグルタミルグルタミン酸および/またはそのナトリウム塩である前記[17]~[23]のいずれか一つに記載の水溶液。
[28] N-C8-22アシル酸性アミノ酸トリペプチドおよび/またはその塩が、N-C8-22アシルグルタミルグルタミルグルタミン酸、N-C8-22アシルアスパルチルグルタミルグルタミン酸、N-C8-22アシルグルタミルアスパルチルグルタミン酸、N-C8-22アシルアスパルチルアスパルチルグルタミン酸、N-C8-22アシルアスパルチルアスパルチルアスパラギン酸、N-C8-22アシルグルタミルアスパルチルアスパラギン酸、N-C8-22アシルアスパルチルグルタミルアスパラギン酸、N-C8-22アシルグルタミルグルタミルアスパラギン酸、およびこれらのナトリウム塩から選ばれる一つ以上である前記[27]に記載の水溶液。
[29] N-C8-22アシル酸性アミノ酸トリペプチドおよび/またはその塩が、N-C8-22アシルグルタミルグルタミルグルタミン酸および/またはそのナトリウム塩である前記[27]に記載の水溶液。
[30] N-C8-22アシル酸性アミノ酸トリペプチドおよび/またはその塩が、N-ココイルグルタミルグルタミルグルタミン酸および/またはそのナトリウム塩である前記[27]に記載の水溶液。
[32] C8-22脂肪酸および/またはその塩が、オクタン酸、デカン酸、ラウリン酸、ミリスチン酸、パルミチン酸、ヤシ油脂肪酸、およびこれらのナトリウム塩から選ばれる一つ以上である前記[31]に記載の水溶液。
[33] C8-22脂肪酸および/またはその塩が、ラウリン酸、ヤシ油脂肪酸、およびこれらのナトリウム塩から選ばれる一つ以上である前記[31]に記載の水溶液。
[34] C8-22脂肪酸および/またはその塩が、ヤシ油脂肪酸および/またはそのナトリウム塩である前記[31]に記載の水溶液。
また、N-C8-22アシル酸性アミノ酸は、好ましくはN-C8-22アシルグルタミン酸および/またはN-C8-22アシルアスパラギン酸である。
C8-22アシル基としては、単一組成のアシル基、例えば、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、トリデカノイル基、ミリストイル基、ステアロイル基、パルミトイル基、ベヘノイル基、イソステアロイル基、オレオイル基等;並びにこれらを含む混合脂肪酸アシル基、例えば、ヤシ油脂肪酸アシル基(ココイル基ともいう)、牛脂脂肪酸アシル基、硬化牛脂脂肪酸アシル基、大豆油脂肪酸アシル基、綿実油脂肪酸アシル基、ヒマシ油脂肪酸アシル基、オリーブ油脂肪酸アシル基、パーム油脂肪酸アシル基、パーム核油脂肪酸アシル基等;が挙げられる。C8-22アシル基は、好ましくはオクタノイル基、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、ココイル基であり、より好ましくはラウロイル基、ココイル基である。
C8-22脂肪酸の塩としては、例えば、ナトリウム塩、カリウム塩等のアルカリ金属塩;マグネシウム塩、カルシウム塩等のアルカリ土類金属塩;トリエタノールアミン塩等のアルカノールアミン塩;アンモニウム塩;コリン塩;およびリジン塩、オルニチン塩、アルギニン塩等の塩基性のアミノ酸との塩;が挙げられる。この塩は、好ましくはアルカリ金属塩、より好ましくはナトリウム塩である。
なお、以下の実施例における「%」は、特段の記載が無い限り「重量%」を意味する。
L-グルタミン酸モノナトリウム一水和物187g(1.00モル)を水300mLに懸濁させ、これに48%水酸化ナトリウム水溶液78gを添加して、pH12.0の水溶液を調製し、15℃に冷却した。これにヤシ油脂肪酸クロライド200g(成分の重量比から算出した分子量219、0.91モル)と48%水酸化ナトリウム水溶液98gを同時に、反応系のpHを12.0および温度を15℃に維持しながら、1時間かけて滴下した。滴下終了後、反応系の温度を30℃に昇温し、さらに3時間撹拌を続け、反応を完結させた。この反応水溶液に、常温の水320mLと35%塩酸25gを加え、そのpHを9.0に調整した。この水溶液にセライト(登録商標)(Product type: 577LC)6.0gを加え、70℃に加熱した後、この温度で1時間撹拌を行った。アドバンテック社製タンク付ステンレスホルダーを用いて70℃および0.4MPaで、セライトを含む水溶液を加圧ろ過し、N-ココイルグルタミン酸のナトリウム塩を含む水溶液1180gを得た。得られた水溶液の組成を以下の条件のHPLCおよびイオンクロマトグラフィーによって調べた。その結果を表1に示す。
(1)N-ココイルグルタミン酸のナトリウム塩、ヤシ油脂肪酸のナトリウム塩、N-ココイルグルタミルグルタミン酸のナトリウム塩、N-ココイルグルタミルグルタミルグルタミン酸のナトリウム塩の分析
使用機器:島津製作所製CLASS-LC20シリーズ
検出UV:210nm
カラム:(株)ワイエムシィ製YMC-Pack ODS-A 150×6.0mmI.D.、S-5μm、12nm(品番:AA12S05-1506WT)
カラム温度:40℃
溶離液:MeOH/リン酸緩衝液=71.5/28.5(体積比)
(リン酸緩衝液:0.03mol/LのNaH2PO4水溶液にH3PO4を加えてpH3.0に調整したもの)
流量:1.2mL/min
測定時間:90min
注入量:10μL
使用機器:島津製作所製CLASS-LC20シリーズ
検出UV:210nm
カラム:(株)ワイエムシィ製YMC-Pack ODS-A 150×6.0mmI.D.、S-5μm、12nm(品番:AA12S05-1506WT)
カラム温度:40℃
溶離液:MeOH/リン酸緩衝液=5/95(体積比)
(リン酸緩衝液:0.05mol/LのNaH2PO4水溶液にH3PO4を加えてpH2.5に調整した後、オクタンスルホン酸を0.005mol/Lとなるように添加したもの)
流量:1.0mL/min
測定時間:60min
注入量:20μL
塩化ナトリウムの分析
使用機器:DIO NEX社製DX-100
検出:電気伝導度検出
カラム:DIO NEX社製IonPac AS11-HC 2mm(10-32)
カラム温度:40℃
溶離液:0.1Mの水酸化ナトリウム水溶液
流量:1.0mL/min
測定時間:60min
注入量:20μL
実施例1で製造した水溶液に48%水酸化ナトリウム水溶液または35%塩酸を添加して、pHが7.5~10.5の水溶液を製造した。pHが異なる各水溶液を50mLサンプル管に移し入れ、-5℃の保存庫中で14日間保存した。保存後に保存庫から各水溶液を取り出し、目視でその外観を経時的に観察し、以下の基準で評価した。結果を表2に示す。
(評価基準)
◎:澄明
○:薄く白濁、室温に昇温後に澄明
△:強く白濁、室温に昇温後に澄明
×:強く白濁、室温に昇温後も白濁
実施例1で製造した水溶液に48%水酸化ナトリウム水溶液または35%塩酸を添加して、pHが7.5~10.5の水溶液を製造した。高温で保存する前のpHが異なる各水溶液中のグルタミン酸のナトリウム塩の含有量(G0)を以下の条件のHPLCで測定した。
使用機器:島津製作所製CLASS-LC20シリーズ
検出:UV-210nm
カラム:(株)ワイエムシィ製YMC-PackODS-A150×6.0mmI.D.、S-5μm、12nm(品番:AA12S05-1506WT)
カラム温度40℃
溶離液:MeOH/リン酸緩衝液=5/95
(リン酸緩衝液:0.05mol/LのNaH2PO4水溶液にH3PO4を加えてpH2.5に調整した後、オクタンスルホン酸を0.005mol/Lとなるように添加したもの)
流量:1.0mL/min
測定時間:60min
注入量:20μL
(評価基準)
◎:G/G0が0.7以上
○:G/G0が0.5以上0.7未満
△:G/G0が0.3以上0.5未満
×:G/G0が0.3未満
実施例1で製造した水溶液に48%水酸化ナトリウム水溶液または35%塩酸を添加して、pHが7.5~10.5の水溶液を製造した。pHが異なる各水溶液を50mLサンプル管に移し入れ、70℃の保存庫中で14日間保存した。保存後に保存庫から各水溶液を取り出し、日本分光社製の紫外可視分光光度計(N-570)を用いて水溶液の透過率を測定し、以下の基準で評価した。結果を表2に示す。
(評価基準)
◎:透過率97%以上
○:透過率95%以上97%未満
△:透過率93%以上95%未満
×:透過率93%未満
実施例1で製造した水溶液2.0gを水道水で100gに希釈(活性剤濃度0.5%)し、35℃の水浴に5分間浸したのち、ハンドミキサー(貝印社製)を用いて10秒間溶液を泡立て、直後および2分後の泡量を測定した。また、泡のきめ細かさについて目視で判定し、以下の基準で評価した。結果を表3に示す。
(泡質の評価基準)
◎:泡が非常にきめ細かい
○:泡がきめ細かい
△:泡が荒い
×:泡が非常に荒い
Claims (13)
- 酸性アミノ酸および/またはその塩とC8-22脂肪酸クロライドとを水溶媒中pH10~13にて反応させて、N-C8-22アシル酸性アミノ酸および/またはその塩を形成する第1工程、および
第1工程後の水溶液のpHを8.4~9.5に調整する第2工程
を含む、N-C8-22アシル酸性アミノ酸および/またはその塩を含み、pHが8.4~9.5である水溶液の製造方法。 - 加圧ろ過を行う工程をさらに含む請求項1に記載の製造方法。
- 水溶媒が、実質的に親水性有機溶媒を含まない請求項1または2に記載の製造方法。
- 第2工程後の水溶液が、酸性アミノ酸および/またはその塩1.0~10.0重量%、並びにN-C8-22アシル酸性アミノ酸および/またはその塩10.0~30.0重量%を含む請求項1~3のいずれか一項に記載の製造方法。
- 第2工程後の水溶液が、N-C8-22アシル酸性アミノ酸ジペプチドおよび/またはその塩をさらに含む請求項1~4のいずれか一項に記載の製造方法。
- 水溶液中のN-C8-22アシル酸性アミノ酸ジペプチドおよび/またはその塩の含有量が、0.5~5.0重量%である請求項5に記載の製造方法。
- 第2工程後の水溶液が、N-C8-22アシル酸性アミノ酸トリペプチドおよび/またはその塩をさらに含む請求項1~6のいずれか一項に記載の製造方法。
- 第2工程後の水溶液が、C8-22脂肪酸および/またはその塩をさらに含む請求項1~7のいずれか一項に記載の製造方法。
- 第2工程後の水溶液を容器に詰める工程をさらに含む請求項1~8のいずれか一項に記載の製造方法。
- 酸性アミノ酸および/またはその塩1.0~10.0重量%、N-C8-22アシル酸性アミノ酸および/またはその塩10.0~30.0重量%、並びにN-C8-22アシル酸性アミノ酸ジペプチドおよび/またはその塩0.5~5.0重量%を含み、pHが8.4~9.5である水溶液。
- N-C8-22アシル酸性アミノ酸トリペプチドおよび/またはその塩をさらに含む請求項10に記載の水溶液。
- C8-22脂肪酸および/またはその塩をさらに含む請求項10または11に記載の水溶液。
- 容器に詰められた状態である請求項10~12のいずれか一項に記載の水溶液。
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EP14857866.9A EP3064487B1 (en) | 2013-10-31 | 2014-10-30 | Aqueous solution containing n-long-chain acyl acidic amino acid and/or salt thereof, and method for producing same |
CN201480059821.0A CN105683151B (zh) | 2013-10-31 | 2014-10-30 | 包含n-长链酰基酸性氨基酸和/或其盐的水溶液及其制造方法 |
JP2015545288A JP6613896B2 (ja) | 2013-10-31 | 2014-10-30 | N−長鎖アシル酸性アミノ酸および/またはその塩を含む水溶液、並びにその製造方法 |
CN202011063739.9A CN112125821B (zh) | 2013-10-31 | 2014-10-30 | 包含n-长链酰基酸性氨基酸和/或其盐的水溶液及其制造方法 |
US15/139,600 US10220094B2 (en) | 2013-10-31 | 2016-04-27 | Aqueous solution containing N-long-chain acyl acidic amino acid and/or salt thereof, and method for producing same |
US16/177,847 US10780167B2 (en) | 2013-10-31 | 2018-11-01 | Aqueous solution containing n-long-chain acyl acidic amino acid and/or salt thereof, and method for producing same |
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CN105683151B (zh) | 2020-11-03 |
JPWO2015064678A1 (ja) | 2017-03-09 |
JP6613896B2 (ja) | 2019-12-04 |
US20190060460A1 (en) | 2019-02-28 |
CN112125821A (zh) | 2020-12-25 |
CN105683151A (zh) | 2016-06-15 |
CN112125821B (zh) | 2024-02-20 |
US10780167B2 (en) | 2020-09-22 |
JP2020023576A (ja) | 2020-02-13 |
JP7028232B2 (ja) | 2022-03-02 |
US10220094B2 (en) | 2019-03-05 |
EP3064487B1 (en) | 2020-04-29 |
EP3064487A1 (en) | 2016-09-07 |
US20160235850A1 (en) | 2016-08-18 |
EP3064487A4 (en) | 2017-07-26 |
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