JPS632962A - Ｎ−長鎖アシルアミノ酸型界面活性剤の製造方法および該活性剤を含有する液体洗浄剤組成物 - Google Patents
Ｎ−長鎖アシルアミノ酸型界面活性剤の製造方法および該活性剤を含有する液体洗浄剤組成物Info
- Publication number
- JPS632962A JPS632962A JP1336386A JP1336386A JPS632962A JP S632962 A JPS632962 A JP S632962A JP 1336386 A JP1336386 A JP 1336386A JP 1336386 A JP1336386 A JP 1336386A JP S632962 A JPS632962 A JP S632962A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- long chain
- fatty acid
- chain acylamino
- alanine
- 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.)
- Granted
Links
- 239000002253 acid Substances 0.000 title claims abstract description 38
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 28
- 239000007788 liquid Substances 0.000 title claims abstract description 26
- 239000000203 mixture Substances 0.000 title claims abstract description 25
- 125000004442 acylamino group Chemical group 0.000 title claims description 32
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- 239000003599 detergent Substances 0.000 title abstract description 20
- 239000013543 active substance Substances 0.000 title 1
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 50
- 229930195729 fatty acid Natural products 0.000 claims abstract description 50
- 239000000194 fatty acid Substances 0.000 claims abstract description 50
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 45
- 235000001014 amino acid Nutrition 0.000 claims abstract description 16
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000001413 amino acids Chemical class 0.000 claims abstract description 13
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims abstract description 11
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims abstract description 11
- 239000003513 alkali Substances 0.000 claims abstract description 10
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229960005261 aspartic acid Drugs 0.000 claims abstract description 8
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims abstract description 7
- 108010077895 Sarcosine Proteins 0.000 claims abstract description 7
- 229940043230 sarcosine Drugs 0.000 claims abstract description 7
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229960002989 glutamic acid Drugs 0.000 claims abstract description 6
- 235000003704 aspartic acid Nutrition 0.000 claims abstract description 5
- 229940000635 beta-alanine Drugs 0.000 claims abstract description 5
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 235000013922 glutamic acid Nutrition 0.000 claims abstract description 5
- 239000004220 glutamic acid Substances 0.000 claims abstract description 5
- VDIPNVCWMXZNFY-UHFFFAOYSA-N N-methyl-beta-alanine Chemical compound CNCCC(O)=O VDIPNVCWMXZNFY-UHFFFAOYSA-N 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 45
- -1 alkali metal salts Chemical class 0.000 claims description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 10
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000004140 cleaning Methods 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 abstract description 15
- 239000002453 shampoo Substances 0.000 abstract description 11
- 238000004821 distillation Methods 0.000 abstract description 9
- 239000002244 precipitate Substances 0.000 abstract description 6
- 238000005562 fading Methods 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000000975 dye Substances 0.000 abstract description 3
- 239000000344 soap Substances 0.000 abstract description 3
- 238000002156 mixing Methods 0.000 abstract description 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 235000019864 coconut oil Nutrition 0.000 description 12
- 239000003240 coconut oil Substances 0.000 description 12
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 11
- 229940024606 amino acid Drugs 0.000 description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 8
- 239000011574 phosphorus Substances 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 8
- 235000021588 free fatty acids Nutrition 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 108700004121 sarkosyl Proteins 0.000 description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 4
- BACYUWVYYTXETD-UHFFFAOYSA-N N-Lauroylsarcosine Chemical compound CCCCCCCCCCCC(=O)N(C)CC(O)=O BACYUWVYYTXETD-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 235000015278 beef Nutrition 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 239000003760 tallow Substances 0.000 description 4
- MLQBTMWHIOYKKC-KTKRTIGZSA-N (z)-octadec-9-enoyl chloride Chemical compound CCCCCCCC\C=C/CCCCCCCC(Cl)=O MLQBTMWHIOYKKC-KTKRTIGZSA-N 0.000 description 3
- VCRXMSMANOGRCM-UHFFFAOYSA-N 2-(dodecanoylamino)butanedioic acid Chemical compound CCCCCCCCCCCC(=O)NC(C(O)=O)CC(O)=O VCRXMSMANOGRCM-UHFFFAOYSA-N 0.000 description 3
- 239000005639 Lauric acid Substances 0.000 description 3
- DIOYAVUHUXAUPX-KHPPLWFESA-N Oleoyl sarcosine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CC(O)=O DIOYAVUHUXAUPX-KHPPLWFESA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- AVBJHQDHVYGQLS-UHFFFAOYSA-N 2-(dodecanoylamino)pentanedioic acid Chemical compound CCCCCCCCCCCC(=O)NC(C(O)=O)CCC(O)=O AVBJHQDHVYGQLS-UHFFFAOYSA-N 0.000 description 2
- ILKFYYOGOCVZRU-UHFFFAOYSA-N 3-(dodecanoylamino)propanoic acid Chemical compound CCCCCCCCCCCC(=O)NCCC(O)=O ILKFYYOGOCVZRU-UHFFFAOYSA-N 0.000 description 2
- UNWFFCPRJXMCNV-UHFFFAOYSA-N 3-[dodecanoyl(methyl)amino]propanoic acid Chemical compound CCCCCCCCCCCC(=O)N(C)CCC(O)=O UNWFFCPRJXMCNV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- VCRXMSMANOGRCM-ZDUSSCGKSA-N (2s)-2-(dodecanoylamino)butanedioic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](C(O)=O)CC(O)=O VCRXMSMANOGRCM-ZDUSSCGKSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- USMCNVFGYLZLGM-UHFFFAOYSA-N 5-amino-2-(dodecanoylamino)-5-oxopentanoic acid Chemical compound CCCCCCCCCCCC(=O)NC(C(O)=O)CCC(N)=O USMCNVFGYLZLGM-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-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
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001294 alanine derivatives Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- PXEDJBXQKAGXNJ-UHFFFAOYSA-L disodium glutamate Chemical compound [Na+].[Na+].[O-]C(=O)C(N)CCC([O-])=O PXEDJBXQKAGXNJ-UHFFFAOYSA-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
- SMVRDGHCVNAOIN-UHFFFAOYSA-L disodium;1-dodecoxydodecane;sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC SMVRDGHCVNAOIN-UHFFFAOYSA-L 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229940049906 glutamate Drugs 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000000774 hypoallergenic effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000007867 post-reaction treatment Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- QKJPFZCCZMBRFB-UHFFFAOYSA-M sodium;3-aminopropanoate Chemical compound [Na+].NCCC([O-])=O QKJPFZCCZMBRFB-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
Landscapes
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1336386A JPS632962A (ja) | 1986-01-24 | 1986-01-24 | Ｎ−長鎖アシルアミノ酸型界面活性剤の製造方法および該活性剤を含有する液体洗浄剤組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1336386A JPS632962A (ja) | 1986-01-24 | 1986-01-24 | Ｎ−長鎖アシルアミノ酸型界面活性剤の製造方法および該活性剤を含有する液体洗浄剤組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS632962A true JPS632962A (ja) | 1988-01-07 |
| JPH0583538B2 JPH0583538B2 (enrdf_load_stackoverflow) | 1993-11-26 |
Family
ID=11831013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1336386A Granted JPS632962A (ja) | 1986-01-24 | 1986-01-24 | Ｎ−長鎖アシルアミノ酸型界面活性剤の製造方法および該活性剤を含有する液体洗浄剤組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS632962A (enrdf_load_stackoverflow) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05156282A (ja) * | 1991-12-04 | 1993-06-22 | Kao Corp | 洗浄剤組成物 |
| JPH05156284A (ja) * | 1991-12-05 | 1993-06-22 | Kao Corp | 洗浄剤組成物 |
| JPH05156285A (ja) * | 1991-12-05 | 1993-06-22 | Kao Corp | 洗浄剤組成物 |
| US5328629A (en) * | 1991-03-18 | 1994-07-12 | Hampshire Chemical Corp. | Process for producing a synthetic detergent soap base from n-acyl sarcosine |
| EP0852577A4 (en) * | 1995-06-06 | 1998-09-02 | Hampshire Chemical Corp | PRODUCTION OF ALKALINE METAL ACYLAMINO ACIDS |
| JP2002167319A (ja) * | 2000-09-22 | 2002-06-11 | Asahi Kasei Corp | 美白化粧料 |
| WO2002057399A1 (de) * | 2001-01-18 | 2002-07-25 | Cognis Deutschland Gmbh & Co. Kg | Tensidgemisch |
| EP0781835B1 (en) * | 1995-07-12 | 2003-12-10 | Kyowa Hakko Kogyo Co., Ltd. | Use of coconut oil fatty acid acyl glutamine in detergent compositions |
| WO2004099121A1 (ja) * | 2003-05-07 | 2004-11-18 | Ajinomoto Co., Inc. | 固体状ｎ-アシルアラニンまたはその塩 |
| WO2005032509A1 (ja) * | 2003-10-02 | 2005-04-14 | Asahi Kasei Chemicals Corporation | 洗浄剤組成物 |
| WO2008140045A1 (ja) | 2007-05-09 | 2008-11-20 | Kyowa Hakko Chemical Co., Ltd. | 油類用添加剤およびこれを含有する潤滑油 |
| EP0826766B2 (en) † | 1996-08-30 | 2011-07-20 | Ajinomoto Co., Inc. | Wash composition |
| JP2016210717A (ja) * | 2015-05-07 | 2016-12-15 | 日油株式会社 | Ｎ−アシルアミノ酸の製造方法 |
| JP2021507916A (ja) * | 2017-12-20 | 2021-02-25 | ソシエテ・デクスプロワタシオン・デ・プロデュイ・プール・レ・アンデュストリー・シミック・セピックＳｏｃｉｅｔｅ Ｄ’Ｅｘｐｌｏｉｔａｔｉｏｎ Ｄｅ Ｐｒｏｄｕｉｔｓ Ｐｏｕｒ Ｌｅｓ Ｉｎｄｕｓｔｒｉｅｓ Ｃｈｉｍｉｑｕｅｓ Ｓｅｐｐｉｃ | リポアミノ酸及びジオールの新規組成物、その調製のための方法、並びにそれから得られる化粧用又は医薬組成物 |
| JP2021507920A (ja) * | 2017-12-20 | 2021-02-25 | ソシエテ・デクスプロワタシオン・デ・プロデュイ・プール・レ・アンデュストリー・シミック・セピックＳｏｃｉｅｔｅ Ｄ’Ｅｘｐｌｏｉｔａｔｉｏｎ Ｄｅ Ｐｒｏｄｕｉｔｓ Ｐｏｕｒ Ｌｅｓ Ｉｎｄｕｓｔｒｉｅｓ Ｃｈｉｍｉｑｕｅｓ Ｓｅｐｐｉｃ | リポアミノ酸及びアルカンジオールの新規組成物、その調製のための方法、並びにそれから得られる化粧用又は医薬組成物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50111006A (enrdf_load_stackoverflow) * | 1974-02-14 | 1975-09-01 |
-
1986
- 1986-01-24 JP JP1336386A patent/JPS632962A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50111006A (enrdf_load_stackoverflow) * | 1974-02-14 | 1975-09-01 |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5328629A (en) * | 1991-03-18 | 1994-07-12 | Hampshire Chemical Corp. | Process for producing a synthetic detergent soap base from n-acyl sarcosine |
| JPH05156282A (ja) * | 1991-12-04 | 1993-06-22 | Kao Corp | 洗浄剤組成物 |
| JPH05156284A (ja) * | 1991-12-05 | 1993-06-22 | Kao Corp | 洗浄剤組成物 |
| JPH05156285A (ja) * | 1991-12-05 | 1993-06-22 | Kao Corp | 洗浄剤組成物 |
| EP0852577A4 (en) * | 1995-06-06 | 1998-09-02 | Hampshire Chemical Corp | PRODUCTION OF ALKALINE METAL ACYLAMINO ACIDS |
| EP0781835B1 (en) * | 1995-07-12 | 2003-12-10 | Kyowa Hakko Kogyo Co., Ltd. | Use of coconut oil fatty acid acyl glutamine in detergent compositions |
| EP0826766B2 (en) † | 1996-08-30 | 2011-07-20 | Ajinomoto Co., Inc. | Wash composition |
| JP2002167319A (ja) * | 2000-09-22 | 2002-06-11 | Asahi Kasei Corp | 美白化粧料 |
| WO2002057399A1 (de) * | 2001-01-18 | 2002-07-25 | Cognis Deutschland Gmbh & Co. Kg | Tensidgemisch |
| WO2004099121A1 (ja) * | 2003-05-07 | 2004-11-18 | Ajinomoto Co., Inc. | 固体状ｎ-アシルアラニンまたはその塩 |
| JPWO2005032509A1 (ja) * | 2003-10-02 | 2007-11-15 | 旭化成ケミカルズ株式会社 | 洗浄剤組成物 |
| JP4716501B2 (ja) * | 2003-10-02 | 2011-07-06 | 旭化成ケミカルズ株式会社 | 洗浄剤組成物 |
| WO2005032509A1 (ja) * | 2003-10-02 | 2005-04-14 | Asahi Kasei Chemicals Corporation | 洗浄剤組成物 |
| US8425889B2 (en) | 2003-10-02 | 2013-04-23 | Asahi Kasei Chemicals Corporation | Cleansing composition |
| WO2008140045A1 (ja) | 2007-05-09 | 2008-11-20 | Kyowa Hakko Chemical Co., Ltd. | 油類用添加剤およびこれを含有する潤滑油 |
| JP2016210717A (ja) * | 2015-05-07 | 2016-12-15 | 日油株式会社 | Ｎ−アシルアミノ酸の製造方法 |
| JP2021507916A (ja) * | 2017-12-20 | 2021-02-25 | ソシエテ・デクスプロワタシオン・デ・プロデュイ・プール・レ・アンデュストリー・シミック・セピックＳｏｃｉｅｔｅ Ｄ’Ｅｘｐｌｏｉｔａｔｉｏｎ Ｄｅ Ｐｒｏｄｕｉｔｓ Ｐｏｕｒ Ｌｅｓ Ｉｎｄｕｓｔｒｉｅｓ Ｃｈｉｍｉｑｕｅｓ Ｓｅｐｐｉｃ | リポアミノ酸及びジオールの新規組成物、その調製のための方法、並びにそれから得られる化粧用又は医薬組成物 |
| JP2021507920A (ja) * | 2017-12-20 | 2021-02-25 | ソシエテ・デクスプロワタシオン・デ・プロデュイ・プール・レ・アンデュストリー・シミック・セピックＳｏｃｉｅｔｅ Ｄ’Ｅｘｐｌｏｉｔａｔｉｏｎ Ｄｅ Ｐｒｏｄｕｉｔｓ Ｐｏｕｒ Ｌｅｓ Ｉｎｄｕｓｔｒｉｅｓ Ｃｈｉｍｉｑｕｅｓ Ｓｅｐｐｉｃ | リポアミノ酸及びアルカンジオールの新規組成物、その調製のための方法、並びにそれから得られる化粧用又は医薬組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0583538B2 (enrdf_load_stackoverflow) | 1993-11-26 |
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