CN108779065A - N-酰基-氨基酸的水溶液 - Google Patents
N-酰基-氨基酸的水溶液 Download PDFInfo
- Publication number
- CN108779065A CN108779065A CN201780016333.5A CN201780016333A CN108779065A CN 108779065 A CN108779065 A CN 108779065A CN 201780016333 A CN201780016333 A CN 201780016333A CN 108779065 A CN108779065 A CN 108779065A
- Authority
- CN
- China
- Prior art keywords
- glycine
- acid
- aqueous solution
- solution
- acyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000007864 aqueous solution Substances 0.000 title claims description 23
- -1 N- sulphonyl-amino Chemical group 0.000 claims abstract description 23
- 239000002537 cosmetic Substances 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000000243 solution Substances 0.000 claims description 43
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000004471 Glycine Substances 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 16
- 239000003513 alkali Substances 0.000 claims description 11
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- HEUQYIQQCNOXOG-UHFFFAOYSA-N N-undecanoylglycine Chemical compound CCCCCCCCCCC(=O)NCC(O)=O HEUQYIQQCNOXOG-UHFFFAOYSA-N 0.000 claims description 5
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 5
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000010533 azeotropic distillation Methods 0.000 claims description 3
- 244000005700 microbiome Species 0.000 claims description 3
- 150000008064 anhydrides Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 235000009508 confectionery Nutrition 0.000 claims description 2
- 230000007797 corrosion Effects 0.000 claims description 2
- 238000005260 corrosion Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 239000000356 contaminant Substances 0.000 claims 1
- 230000020477 pH reduction Effects 0.000 claims 1
- 235000011164 potassium chloride Nutrition 0.000 claims 1
- 239000001103 potassium chloride Substances 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 238000001256 steam distillation Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 abstract description 17
- 239000011260 aqueous acid Substances 0.000 abstract description 6
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 5
- 239000012535 impurity Substances 0.000 abstract description 3
- 239000012071 phase Substances 0.000 description 37
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- 229940024606 amino acid Drugs 0.000 description 16
- 229960002449 glycine Drugs 0.000 description 14
- 235000001014 amino acid Nutrition 0.000 description 13
- 150000001413 amino acids Chemical class 0.000 description 11
- 239000003755 preservative agent Substances 0.000 description 11
- 230000002335 preservative effect Effects 0.000 description 11
- 239000000463 material Substances 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000006210 lotion Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000011056 performance test Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000555688 Malassezia furfur Species 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000005191 phase separation Methods 0.000 description 4
- 229920001285 xanthan gum Polymers 0.000 description 4
- 208000001840 Dandruff Diseases 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 125000001931 aliphatic group Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 3
- 239000004519 grease Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- 101100295884 Aedes aegypti SGPRor7 gene Proteins 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000186427 Cutibacterium acnes Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108010008488 Glycylglycine Proteins 0.000 description 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 101150041122 Orco gene Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- 235000004279 alanine Nutrition 0.000 description 2
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 239000002781 deodorant agent Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000002532 enzyme inhibitor Substances 0.000 description 2
- 229940125532 enzyme inhibitor Drugs 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 229940043257 glycylglycine Drugs 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229960004502 levodopa Drugs 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229940055019 propionibacterium acne Drugs 0.000 description 2
- 238000012958 reprocessing Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 229960001295 tocopherol Drugs 0.000 description 2
- 229930003799 tocopherol Natural products 0.000 description 2
- 235000010384 tocopherol Nutrition 0.000 description 2
- 239000011732 tocopherol Substances 0.000 description 2
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- DWNBOPVKNPVNQG-LURJTMIESA-N (2s)-4-hydroxy-2-(propylamino)butanoic acid Chemical compound CCCN[C@H](C(O)=O)CCO DWNBOPVKNPVNQG-LURJTMIESA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical class CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical group CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- NDJKXXJCMXVBJW-UHFFFAOYSA-N Heptadecane Natural products CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- BGHCVCJVXZWKCC-UHFFFAOYSA-N Tetradecane Natural products CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 238000003916 acid precipitation Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- DCAYPVUWAIABOU-UHFFFAOYSA-N alpha-n-hexadecene Natural products CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 1
- RZJRJXONCZWCBN-UHFFFAOYSA-N alpha-octadecene Natural products CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000058 anti acne agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000001166 anti-perspirative effect Effects 0.000 description 1
- 229940124340 antiacne agent Drugs 0.000 description 1
- 239000003213 antiperspirant Substances 0.000 description 1
- 125000001124 arachidoyl 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])[H] 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 229960005261 aspartic acid Drugs 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 229940000635 beta-alanine Drugs 0.000 description 1
- 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 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 229960002433 cysteine Drugs 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 229940075285 dandruff control Drugs 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 229960002743 glutamine Drugs 0.000 description 1
- 235000004554 glutamine Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229960002885 histidine Drugs 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000005644 linolenyl group Chemical group 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 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 1
- GQEZCXVZFLOKMC-UHFFFAOYSA-N n-alpha-hexadecene Natural products CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
- HOWGUJZVBDQJKV-UHFFFAOYSA-N n-propyl-nonadecane Natural products CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 description 1
- 229940038384 octadecane Drugs 0.000 description 1
- 125000000016 octadecenoyl group Chemical group O=C([*])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])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
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 125000001117 oleyl 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])=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
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 125000001236 palmitoleoyl 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])[H] 0.000 description 1
- 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 1
- 235000020232 peanut Nutrition 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- NFIYTPYOYDDLGO-UHFFFAOYSA-N phosphoric acid;sodium Chemical compound [Na].OP(O)(O)=O NFIYTPYOYDDLGO-UHFFFAOYSA-N 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 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 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 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
- 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
- A61K8/442—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof substituted by amido group(s)
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/06—Emulsions
- A61K8/062—Oil-in-water emulsions
-
- 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
- A61Q15/00—Anti-perspirants or body deodorants
-
- 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
-
- 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
- A61Q5/006—Antidandruff preparations
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/524—Preservatives
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dispersion Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Cosmetics (AREA)
Abstract
本发明涉及一种制备N‑酰基‑氨基酸水溶液的方法。该方法不需要分离固体并且提供了具有低杂质含量的溶液。此外,本发明包括相应的N‑酰基‑氨基酸水溶液,以及它们在化妆品和药物制剂中的用途。
Description
本发明涉及一种制备N-酰基-氨基酸水溶液的方法。该方法不需要分离固体并且提供具有低杂质含量的溶液。此外,本发明包括相应的N-酰基-氨基酸水溶液,以及它们在化妆品和药物制剂中的用途。
N-酰基-氨基酸(“脂氨基酸”)被用于化妆品和药品中。这类物质的代表的实例例如为辛酰基甘氨酸(I)和十一碳烯酰基甘氨酸(II)。在此涉及氨基酸甘氨酸的N-酰胺和脂肪酸辛基酸(=辛酸)或十一碳烯酸的N-酰胺。
辛酰基甘氨酸(I)可从MINASOLVE公司以商品名“Caprocine”商购获得。辛酰基甘氨酸显示出对细菌、真菌和酵母菌的广泛的抗微生物作用。该物质可用作防腐剂和除臭剂。此外,辛酰基甘氨酸有效地抑制了决定性地导致痤疮产生的痤疮丙酸杆菌(Propionibacterium Acnes)的生长。同样,该物质抑制了促进在头皮上形成头皮屑的酵母糠秕马拉色菌(Hefepilzes Malassezia Furfur)(卵圆皮屑芽胞菌(Pityrosporumovale))的生长。此外,辛酰基甘氨酸抑制了积极地调节皮肤中油脂的产生的酶5-α还原酶。因此,辛酰基甘氨酸可以减少皮肤中的油脂产生并由此减少形成头皮屑和痤疮的倾向。N-酰基-氨基酸通常具有低的毒性并且是良好亲肤的。因此,它们在化妆品和药品中的用途是令人感兴趣的。
N-酰基-氨基酸通常是在水中仅适度溶解的固体。为了掺入化妆品或药物制剂中,N-酰基-氨基酸因此在碱的帮助下被中和并因此转化成它们的水溶性羧酸盐。在这种情况下,经常使用强腐蚀性的碱性物质,例如氢氧化钠或氢氧化钾。这些强碱与所有在化妆品或药物制剂中使用的原料都不相容。在这种情况下,N-酰基-氨基酸的中和可能需要在单独的搅拌容器中进行。备选地,将N-酰基-氨基酸溶解在热水或另外的亲脂性溶剂中。在这种类型的应用中,游离的N-酰基-氨基酸导致制剂中pH值的降低。同样,这会损害制剂的稳定性。一般而言,固体的处理具有缺陷。通常,必须通过长时间搅拌来确保固体已完全溶解在所选的溶剂中。此外,它可导致粉尘的产生,其例如造成皮肤、眼睛和/或呼吸道的刺激。任选地,它还会导致工作环境的污染。总的来说,固体N-酰基-氨基酸的应用与增加的时间成本、能量消耗、耗材和由此带来的成本相关。
在工业规模上,N-酰基-氨基酸通过氨基酸与羧酸氯化物或酸酐在碱性水溶液中缩合来制备(肖登-包曼(Schotten-Baumann)反应)。这种类型的合成的实例在文献中被描述,尤其是在FR 2771632A(SEPPIC,优先权日:01.12.1997)和WO 2006/010590A1(Sinerga,优先权日:30.07.2004)中。作为化学反应的结果,产生碱性的粗产物溶液,其除了N-酰基-氨基酸盐之外还包含等摩尔量的至少一种无机盐例如氯化钠(NaCl)。原则上,这种未纯化的N-酰基-氨基酸水溶液已经可用作化妆品或药品的原料。然而,缺点是溶液中包含的无机盐可与制剂的其他组分相互作用。例如,这些盐可影响乳液或凝胶的流变性。另一个缺点是粗产物溶液中游离的烷基羧酸的存在。烷基羧酸是肖登-包曼合成的副产物,其由于活化的羧酸的水解而产生。取决于其碳链的长度,烷基羧酸可刺激皮肤并具有特征性的难闻气味。在将未纯化的N-酰基氨基酸溶液直接应用在化妆品中时,另一个缺点是有时发生的染色。
因此,通常对如上所述获得的反应混合物进行再处理。存在于混合物中的N-酰基-氨基酸通过酸化沉淀,并且沉淀的固体必要时借助于合适的有机(共)溶剂结晶。同时,利用该净化步骤还除去有机杂质,例如未反应的游离氨基酸。然而,经纯化的固体的分离和干燥意味着额外的劳动时间和材料消耗,这导致更高的生产成本。
本发明的目的是制备浓缩的N-酰基-氨基酸水溶液,其直接获得并且无需从反应混合物中分离固体。水性浓缩物应含有高纯度的N-酰基-氨基酸,而副产物和废弃产物应以尽可能低的浓度存在。此外,水溶液也应在很宽的温度范围内具有化学和物理稳定性,以及尽可能地无味且较少地着色。
通过下面描述的制备方法令人惊讶地实现了该目的:
●来自肖登-包曼反应的碱性粗产物溶液在有机溶剂的存在下酸化。所述溶剂选自仅能与水有限地混溶但同时与水形成共沸混合物的物质。在酸化过程中,N-酰基-氨基酸转入有机溶剂相。
●通过用水洗涤有机产物溶液除去无机盐和游离的氨基酸。
●用碱的水溶液萃取有机产物溶液。在这种情况下,N-酰基-氨基酸作为水溶性盐再次转入水溶液中。
●在重新进行相分离后,通过共沸蒸馏除去水性的产物溶液中包含的溶剂残余物。通过进一步的水的蒸馏可用水蒸气进一步地除去挥发性的副产物。这些副产物涉及例如在肖登-包曼反应过程中作为水解产物形成的游离的烷基羧酸。为此目的,在蒸馏期间将pH值设定在约6-7的中性范围内。通常,N-酰基-氨基酸是比仅被烷基取代的脂肪酸更强的酸。因此,脂肪酸在中性的pH值下在平衡状态中部分地作为水蒸汽挥发性的游离羧酸存在,而N-酰基-氨基酸优选作为非挥发性的盐存在。
●最终将pH值调节至≥6.5,使N-酰基-氨基酸稳定为水溶液中的羧酸盐。
根据本发明获得的溶液在许多方面优于已知为现有技术的固体或含盐的溶液:它们可以很容易地作为液体被计量添加并掺入液体混合物中。在这种情况下,它们不会产生任何或仅产生轻微的pH值变化。该溶液实际上不含无机盐,因此与盐敏感性物质例如聚合物增稠剂或用盐增稠的表面活性剂凝胶没有任何不利的相互作用。此外,该溶液仅包含少量游离烷基羧酸,这对其气味和其亲肤性具有积极作用。此外,根据本发明获得的溶液的制备是成本低廉的,因为不需要固/液分离。
合成N-酰基-氨基酸的原料可以是任何氨基羧酸(氨基酸)。手性氨基酸可在此用作对映体纯的(enantiomerenreine)或非对映体纯的(diastereomerenreine)化合物,以及不同立体异构体的混合物。氨基酸内存在的任何其他官能团必要时通过合适的保护基团来保护。此外,可使用具有最多达6个氨基酸的短肽。优选地,氨基酸组分选自:丙氨酸、精氨酸、天冬酰胺、天冬氨酸、半胱氨酸、谷氨酰胺、谷氨酸、甘氨酸、甘氨酰基甘氨酸、组氨酸、异亮氨酸、亮氨酸、赖氨酸、蛋氨酸、苯丙氨酸、二羟基苯丙氨酸(DOPA)、脯氨酸、丝氨酸、苏氨酸、色氨酸、酪氨酸、缬氨酸、3-氨基丙酸(β-丙氨酸)和4-氨基丁酸(γ-氨基丁酸,GABA)。特别优选地,氨基酸组分选自甘氨酸和甘氨酰基甘氨酸。
脂肪酸组分选自链长为6至22个碳、优选地6至12个碳的任意脂族脂肪酸。脂肪酸可以是饱和的、单不饱和的或多不饱和的。它可包含一种(个)或两种(个)羧酸官能团。优选地,N-酰基-氨基酸包含至少一个以下基团:己酰基(Caproyl),庚酰基辛酰基(Capryloyl)、壬酰基(Perlagonyl)、癸酰基(Caprinoyl)、十一碳烯酰基、十二烷酰基(月桂基)、十四烷酰基(肉豆蔻基)、十六烷酰基(棕榈酰基)、十七烷酰基(Margarinoyl)、十八烷酰基(硬脂基)、二十烷酰基(花生酰基(Arachinoyl)),二十二烷酰基(山萮酰)、十六碳烯酰基(Hexadecenoyl)(棕榈油酰基)、十八碳烯酰基(油烯基)、二十碳烯酰基(Gadoloyle)、二十二碳烯酰基(Erucyl)、十八碳二烯酰基(亚油酰基)、十八碳三烯酰基(亚麻酰基)、二十碳四烯酰基(花生四烯酰基(Arachidoyl))。特别优选地,N-酰基-氨基酸包含辛酰基(Capryloyl)和十一碳烯酰基基团中的一种。
为了合成N-酰基-氨基酸,羧酸可以作为酰卤作为混合的酸酐或作为对称酸酐被活化。优选地,羧酸作为酰氯被活化。
为了降低粗产物溶液的pH值,可使用其酸度高于合成的N-酰基-氨基酸的酸度的任何酸。优选地使用无机酸和/或其酸盐,例如,盐酸、硫酸、硫酸氢钠、硫酸氢钾、磷酸、磷酸二氢钠、磷酸氢二钠、磷酸二氢钾和/或磷酸氢二钾。所调节的pH值≤7。优选地,pH值在0和5之间,更优选地在0.5和3.0之间。
作为用于N-酰基-氨基酸溶液的水性(含水)再处理的有机溶剂,可使用任何与水不能混溶或不能完全混溶的有机溶剂。可使用单独的溶剂或溶剂混合物。优选地使用酯(例如乙酸乙酯、乙酸丁酯、乙酸异丙酯、乙酸异丁酯)、醚(例如叔丁基甲基醚、二异丙基醚、2-甲基四氢呋喃)、芳族烃(例如甲苯、二甲苯)、脂族烃(例如庚烷、环己烷、甲基环己烷)、酮(例如乙基甲基酮、异丁基甲基酮)、卤代烃(例如二氯甲烷、二氯乙烷、氯仿)和/或醇(例如正丁醇、异丁醇、戊醇)。特别优选地使用乙酸乙酯、甲苯、2-甲基四氢呋喃和/或叔丁基甲基醚。
水性再处理过程中的相分离可在两个相作为液体存在时的任何温度下进行。通常,在-20℃至+100℃的温度下就是这种情况。优选地,相分离在+10℃至+80℃下进行,更优选地在+30℃至+60℃下进行。相分离也可在超压下进行。
可在任何压力下进行共沸蒸馏以除去过量的有机溶剂。蒸馏可在大气压(1013毫巴±50毫巴)和/或真空和/或超压下进行。
作为肖登-包曼反应期间的碱和用于使N-酰基-氨基酸转化为水性的产物溶液的碱,可使用任何碱金属或碱土金属碱。优选地使用氢氧化钠、氢氧化钾、碳酸钠、碳酸钾、碳酸氢钠和/或碳酸氢钾。所用的碱可以固体或水溶液的形式使用。
根据本发明制备的N-酰基-氨基酸溶液的pH值可在pH 5和pH 14之间。优选地,将最终产物溶液调节至pH6.5至pH8.5(包括端点)之间的pH值。
根据本发明制备的溶液中N-酰基-氨基酸的浓度可为1%至90%、优选地10-50%、特别优选地20-40%。给出的值基于游离的N-酰基-氨基酸的质量百分比。在这种情况下,N-酰基-氨基酸主要以与具有用于中和的碱的盐的形式存在。然而,取决于pH,一部分N-酰基-氨基酸可作为游离的羧酸存在。
同样地,根据本发明,通过所述方法制备N-酰基-氨基酸的水溶液。根据本发明的溶液在宽的温度范围内是澄清、稳定和均匀的。很少发生固体组分在低温下的结晶以及组分在较高的温度下的化学分解。优选地,根据本发明的溶液在-20℃至+80℃的温度范围内是物理和化学稳定的。通常,根据本发明的水溶液本身是防腐的(konservierend)并因此对于由微生物造成的定殖或分解是稳定的。因此,通常不需要借助额外的防腐剂来保护本发明的溶液。
如果需要,根据本发明的溶液可包含其他助剂。这些可以是例如防腐剂、化妆品溶剂、表面活性物质(表面活性剂/乳化剂)和/或水溶性多元醇。
根据本发明的溶液可用作化妆品和/或个人护理产品和/或药物制剂中的原料。这种情况下,它们可以实现如下的功能,该功能通常有助于对由年龄引起和/或由环境引起的皮肤或毛发变化产生积极的影响。它们可用作例如防腐剂、除臭剂、抗痤疮剂、去头皮屑剂、皮肤增白剂、酶抑制剂和/或pH调节剂。没有排他性的其他可能的应用包括用作调理剂、泡沫增强剂、(共)乳化剂和/或(共)表面活性剂、酶抑制剂、光和UV保护、以及用于调节油脂产生和/或用于影响流变性或粘度。
通过使用根据本发明的溶液,还可制备含有如上所述的溶液的产品,特别是化妆品和/或药物和/或皮肤科(dermatologischen)产品和/或卫生用品。换句话说,根据本发明的溶液用于化妆品和/或药物和/或皮肤科产品和/或卫生用品中。作为“卫生制剂”或“卫生用品”,特别地理解为家用或清洁产品以及香料制剂。
将根据本发明的溶液添加到化妆品和/或药物和/或皮肤科产品和/或卫生用品中可以在生产过程中的任何时间点进行,例如在水相的生产过程中或在生产过程结束时。
根据本发明的溶液还用于包含根据本发明的溶液的产品,特别地化妆品或皮肤科产品中,其中所述产品包含0.05-10.0重量%的至少一种N-酰基-氨基酸。相应的产品可以任何形式存在,特别地作为:
a.溶液
b.悬浮液
c.乳液
d.凝胶
e.软膏
f.糊剂
g.粉末
h.以碎片或块状物形式呈现的固体
i.泡沫
j.基于微囊化、脂质体或类似的微观结构的配方体系
k.形式a-j的组合。
实施例/实验部分
实施例1-辛酰基甘氨酸水溶液的制备
将甘氨酸(50g)和氢氧化钠(51g)溶解在水(250mL)中。计量加入辛酰氯(87g)。向碱性溶液中加入MTBE(500mL),然后加入36%-浓度的盐酸(50g)。分离各相并用水洗涤有机相。然后将水(600m1)掺入有机相并用氢氧化钠将混合物的pH值调节至pH≥6.5。分离出有机相。从水相中在大气压下蒸馏出过量的有机溶剂和水,直至达到30重量%(基于游离酸)的辛酰基甘氨酸的浓度。最后用碳酸氢钠将水溶液的pH值调节至pH 7.5-8.5。溶液包含<0.1%的氯化钠和<0.5%的辛酸。
30%-浓度的辛酰基甘氨酸水溶液符合根据ISO 11930的防腐剂性能测试的A标准。因此,该溶液被保护免受微生物污染。不需要额外的防腐剂。
实施例2-去屑洗发水
原料供应商:1)Evonik,2)BASF,3)Minasolve,4)Lubrizole,5)SFA,6)Orco
使相A的原料在搅拌下溶解在水中。添加根据本发明的溶液(相B)。在剧烈搅拌下加入增稠剂(相C)。依次加入相D成分,然后加入食盐(相E)。搅拌混合物直至固体完全溶解。最后,调节pH值(相F)。洗发水符合根据ISO 11930的防腐剂性能测试的A标准。
实施例3-面部清洁剂:
原料供应商:1)Dow;2)minasolve;3)Jungbunzlauer;4)BASF;5)Evonik;6)Bell;7)Orco
在搅拌下在室温下将甲基纤维素加入水中。在此,pH值不应超过7.5(相A)。将Pentiol Green+和黄原胶混合(相B)并将混合物加入相A中。搅拌混合物直至均匀。加入根据实施例1的溶液,然后加入少量氢氧化钠溶液(相C)。将混合物搅拌15-20分钟直至完全增稠。按所列顺序在搅拌下加入相D的表面活性剂。随后,按照给定的顺序在搅拌下连续地加入相E的原料。最后,调节pH。该产品符合根据ISO 11930的防腐剂性能测试的A标准。
实施例4-滚搽式止汗剂:
原料供应商:1)Lubrizol,2)Jungbunzlauer,3)Minasolve,4)SFA
将Carbopol分散在水中并搅拌直至完全水合。加入黄原胶并搅拌混合物直至固体完全分散(相A)。加入根据实施例1的本发明的溶液,然后加入少量的氢氧化钠溶液(相B)。在搅拌下加入相C的原料。最后,加入香料,调节pH值并加入缓冲溶液。该产品符合根据ISO11930的防腐剂性能测试的A标准。
实施例5-皮肤保湿O/W乳液:
原料供应商:1)Minasolve,2)Jungbunzlauer,3)BASF,4)AAK,5)Caesar&Loretz
将黄原胶与Pentiol Green+混合,然后在搅拌下加入水中。搅拌混合物直至均匀(相A)。加入根据本发明的溶液(相B)并将混合物加热至75-80℃。在单独的容器中,将相C混合并加热至75-80℃。将相C加入到相A+B中,同时用Ultra-Turrax混合。将乳液以高剪切速率搅拌3分钟,然后用螺旋桨搅拌器再搅拌30分钟。在冷却期间,降低搅拌器速度。在T<40℃时,加入生育酚(相D)。在室温下,调节pH(相E)。该产品符合根据ISO 11930的防腐剂性能测试的A标准。
对比例6-用固体辛酰基甘氨酸制成的皮肤保湿O/W乳液:
原料供应商:1)Minasolve,2)Jungbunzlauer,3)BASF,4)AAK,5)Caesar&Loretz
将黄原胶与Pentiol Green+混合,然后在搅拌下加入水中。搅拌混合物直至均匀(相A)。在单独的槽(Kessel)中,首先加入软化水并用氢氧化钠水溶液处理。随后,在搅拌下加入固体辛酰基甘氨酸。搅拌混合物直至形成澄清溶液(相B)。将相B计量加入相A,然后将混合物加热至75-80℃。在第三个单独的容器中,将相C混合并加热至75-80℃。将相C加入到相A+B中,同时用Ultra-Turrax混合。将乳液以高剪切速率搅拌3分钟,然后用螺旋桨搅拌器再搅拌30分钟。在冷却期间,降低搅拌器速度。在T<40℃时,加入生育酚(相D)。在室温下,调节pH(相E)。该产品符合根据ISO 11930的防腐剂性能测试的A标准。
Claims (11)
1.一种制备辛酰基甘氨酸和/或十一碳烯酰基甘氨酸的碱金属或碱土金属盐的水溶液的方法,包括以下步骤:
(1)将来自1-辛酸(辛酸)和十一碳烯酸的组的活化羧酸以酰卤、混合酸酐或对称酸酐的形式与甘氨酸在水溶液中缩合,得到游离的N-酰基-甘氨酸,
(2)对得到的溶液进行酸化并将游离的N-酰基-甘氨酸萃取到与水不能完全混溶的有机溶剂中,
(3)通过添加碱将N-酰基-甘氨酸转移到水溶液中,和
(4)通过水的共沸蒸馏从水溶液中除去水蒸气挥发性污染物。
2.根据权利要求1所述的方法,其特征在于,使用的有机溶剂与水形成共沸物。
3.根据权利要求1或2所述的方法,其特征在于,将辛酰基甘氨酸或十一碳烯酰基甘氨酸以碱金属或碱土金属盐的形式转移到水溶液中。
4.根据权利要求1至3中至少一项所述的方法,其特征在于,将辛酰基甘氨酸或十一碳烯酰基甘氨酸作为钠盐和/或钾盐转移到水溶液中。
5.根据权利要求1至4中至少一项所述的方法,其特征在于,通过蒸汽蒸馏在pH<8下从辛酰基甘氨酸或十一碳烯酰基甘氨酸水溶液中除去游离的辛酸或十一碳烯酸。
6.根据权利要求1至5中至少一项所述的方法,其特征在于,得到的水溶液包含10-50重量%的辛酰基甘氨酸或十一碳烯酰基甘氨酸的相应的盐。
7.根据权利要求1至6中至少一项所述的方法,其特征在于,得到的水溶液包含不超过2重量%的游离的辛酸或十一碳烯酸。
8.根据权利要求1至7中至少一项所述的方法,其特征在于,得到的水溶液包含不超过1重量%的无机盐。
9.一种根据权利要求6至8中至少一项获得的溶液通过掺入化妆品或皮肤科产品中实现的用途。
10.一种根据权利要求6至8中至少一项获得的溶液用于抑制微生物生长或杀死微生物的用途。
11.一种根据权利要求6至8中至少一项获得的溶液用于化妆品或皮肤科产品的防腐的用途。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102016104205.6 | 2016-03-08 | ||
DE102016104205.6A DE102016104205A1 (de) | 2016-03-08 | 2016-03-08 | Wässrige Lösungen von N-Acyl-Aminosäuren |
PCT/EP2017/053855 WO2017153161A1 (de) | 2016-03-08 | 2017-02-21 | Wässrige lösungen von n-acyl-aminosäuren |
Publications (1)
Publication Number | Publication Date |
---|---|
CN108779065A true CN108779065A (zh) | 2018-11-09 |
Family
ID=58185499
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201780016333.5A Pending CN108779065A (zh) | 2016-03-08 | 2017-02-21 | N-酰基-氨基酸的水溶液 |
Country Status (6)
Country | Link |
---|---|
US (1) | US20190091124A1 (zh) |
EP (1) | EP3426631A1 (zh) |
CN (1) | CN108779065A (zh) |
DE (1) | DE102016104205A1 (zh) |
MA (1) | MA43685A (zh) |
WO (1) | WO2017153161A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109369439A (zh) * | 2018-12-06 | 2019-02-22 | 盐城工学院 | 一种n-酰基氨基酸型表面活性剂的制备方法 |
CN110938023A (zh) * | 2019-12-23 | 2020-03-31 | 张家港格瑞特化学有限公司 | 一种脂肪酰基牛磺酸表面活性剂的制备方法 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR3075197B1 (fr) * | 2017-12-20 | 2019-11-15 | Societe D'exploitation De Produits Pour Les Industries Chimiques Seppic | Nouvelle composition de lipoaminoacides et de diols, le procede pour leur preparation et composition cosmetique ou pharmaceutique en resultant |
FR3130576A1 (fr) * | 2021-12-21 | 2023-06-23 | L'oreal | Composition cosmétique aqueuse comprenant de la vanilline ou l’un de ses dérivés, un tensioactif non ionique, et éventuellement au moins un antimicrobien additionnel |
CN115160169B (zh) * | 2022-07-25 | 2024-04-16 | 湖州欧利生物科技有限公司 | 椰油酰甘氨酸盐表面活性剂的生产工艺 |
CN116172888B (zh) * | 2022-12-21 | 2024-07-02 | 陕西畅想制药有限公司 | 用于调节肌肤微生态的含氨基酸衍生物的组合物 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT490450A (zh) * | 1951-07-19 | |||
US5710295A (en) * | 1995-06-06 | 1998-01-20 | Hampshire Chemical Corp. | Preparation of alkali metal acyl amino acids |
US5762765A (en) * | 1997-04-14 | 1998-06-09 | Berg; Lloyd | Separation of ethanol, isopropanol and water mixtures by azeotropic distillation |
FR2771632B1 (fr) | 1997-12-01 | 2000-03-17 | Seppic Sa | Composition synergique comprenant au moins un lipoaminoacide et au moins un glycol; application en cosmetique |
FR2771633B1 (fr) * | 1997-12-01 | 2000-01-14 | Seppic Sa | Composition synergique comportant au moins un n-octanyl aminoacide et au moins un n-undecylenoyl aminoacide; application en cosmetique |
ITMI20041567A1 (it) | 2004-07-30 | 2004-10-30 | Maycos Italiana Di Comini Miro | "derivati n-acilati di acidi bicarbossilici con amminoacidi e con idrolizzati proteici vegetali e loro applicazione in prodotti cosmetici, dermofarmaceutici e farmaceutici" |
JP2008105945A (ja) * | 2005-02-07 | 2008-05-08 | Ajinomoto Co Inc | アディポネクチンの分泌促進又は誘導作用を有するアシルアミド化合物 |
FR2929275B1 (fr) * | 2008-03-28 | 2011-09-23 | Seppic Sa | Procede de synthese en continu d'un compose n-acyle ; installation pour la mise en oeuvre du procede |
US20130101530A1 (en) * | 2011-10-25 | 2013-04-25 | Galaxy Surfactants Ltd. | Antimicrobial preservative compositions for personal care products |
-
2016
- 2016-03-08 DE DE102016104205.6A patent/DE102016104205A1/de not_active Withdrawn
-
2017
- 2017-02-21 WO PCT/EP2017/053855 patent/WO2017153161A1/de active Application Filing
- 2017-02-21 MA MA043685A patent/MA43685A/fr unknown
- 2017-02-21 CN CN201780016333.5A patent/CN108779065A/zh active Pending
- 2017-02-21 EP EP17707498.6A patent/EP3426631A1/de not_active Withdrawn
- 2017-02-21 US US16/083,436 patent/US20190091124A1/en not_active Abandoned
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109369439A (zh) * | 2018-12-06 | 2019-02-22 | 盐城工学院 | 一种n-酰基氨基酸型表面活性剂的制备方法 |
CN109369439B (zh) * | 2018-12-06 | 2021-04-16 | 盐城工学院 | 一种n-酰基氨基酸型表面活性剂的制备方法 |
CN110938023A (zh) * | 2019-12-23 | 2020-03-31 | 张家港格瑞特化学有限公司 | 一种脂肪酰基牛磺酸表面活性剂的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
EP3426631A1 (de) | 2019-01-16 |
DE102016104205A1 (de) | 2017-09-14 |
US20190091124A1 (en) | 2019-03-28 |
MA43685A (fr) | 2018-11-28 |
WO2017153161A1 (de) | 2017-09-14 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN108779065A (zh) | N-酰基-氨基酸的水溶液 | |
Tripathy et al. | Synthesis, chemistry, physicochemical properties and industrial applications of amino acid surfactants: A review | |
CN106860035B (zh) | 表面活性剂组合物 | |
JP4070768B2 (ja) | 新規アシル基含有組成物 | |
Clendennen et al. | Betaine amphoteric surfactants—Synthesis, properties, and applications | |
JP4644493B2 (ja) | 界面活性剤組成物ならびにそれを用いた洗浄剤組成物および乳化組成物 | |
US20060239952A1 (en) | Cleaning composition and method for preparing the same | |
EP1156033B1 (en) | Process for producing acidic n-(long-chain acyl)amino acid | |
JP4716501B2 (ja) | 洗浄剤組成物 | |
MX2014008050A (es) | Proceso para la sintesis de productos surfactantes cationicos altamente puros. | |
KR20180100665A (ko) | 세정제 조성물 및 그 제조 방법 | |
EP3115104B1 (en) | Method for reducing critical micelle concentration | |
JP4600030B2 (ja) | N−長鎖アシルグルタミン酸及び/又はその塩の結晶 | |
JP2932377B2 (ja) | 液体洗浄剤の増粘方法 | |
JP2003221371A (ja) | N−長鎖アシル中性アミノ酸の製造方法 | |
FR2504389A1 (fr) | Combinaison contre la transpiration contenant un halogenhydrate d'aluminium et un halogenure stannique et composition la contenant | |
JP3434635B2 (ja) | 含水化粧料の変臭・変色防止方法 | |
CA3200640A1 (en) | Blends of n-acyl alaninates and other n-acyl amino acid surfactants and derivatives thereof | |
JPH1112241A (ja) | N−長鎖アシルアミノ酸含有洗浄剤組成物 | |
JP2003192571A (ja) | 身体清浄用化粧料 | |
Nowicki et al. | Synthesis and surfactant properties of triethanolammonium salts of N-acylated N-carboxyethylglycine |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
WD01 | Invention patent application deemed withdrawn after publication | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20181109 |