SK119397A3 - Production of polysuccinimide in an organic medium - Google Patents
Production of polysuccinimide in an organic medium Download PDFInfo
- Publication number
- SK119397A3 SK119397A3 SK1193-97A SK119397A SK119397A3 SK 119397 A3 SK119397 A3 SK 119397A3 SK 119397 A SK119397 A SK 119397A SK 119397 A3 SK119397 A3 SK 119397A3
- Authority
- SK
- Slovakia
- Prior art keywords
- acid
- reaction
- catalyst
- medium
- reaction medium
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 5
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims abstract description 29
- 229960005261 aspartic acid Drugs 0.000 claims abstract description 29
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims abstract description 27
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims abstract description 27
- 238000009835 boiling Methods 0.000 claims abstract description 25
- 150000001335 aliphatic alkanes Chemical class 0.000 claims abstract description 22
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229920000642 polymer Polymers 0.000 claims abstract description 19
- 239000003377 acid catalyst Substances 0.000 claims abstract description 13
- PLLBRTOLHQQAQQ-UHFFFAOYSA-N 8-methylnonan-1-ol Chemical compound CC(C)CCCCCCCO PLLBRTOLHQQAQQ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000009833 condensation Methods 0.000 claims abstract description 7
- 230000005494 condensation Effects 0.000 claims abstract description 7
- 125000005233 alkylalcohol group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 238000006482 condensation reaction Methods 0.000 claims abstract description 6
- 239000012430 organic reaction media Substances 0.000 claims abstract description 5
- 229940024606 amino acid Drugs 0.000 claims abstract 6
- 150000001413 amino acids Chemical class 0.000 claims abstract 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 50
- 238000006243 chemical reaction Methods 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 40
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 21
- 239000012429 reaction media Substances 0.000 claims description 21
- 230000035484 reaction time Effects 0.000 claims description 16
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 10
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 6
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- CBFCDTFDPHXCNY-UHFFFAOYSA-N icosane Chemical compound CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 claims description 6
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 claims description 6
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229940038384 octadecane Drugs 0.000 claims description 3
- 230000000977 initiatory effect Effects 0.000 claims 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- SNRUBQQJIBEYMU-NJFSPNSNSA-N dodecane Chemical group CCCCCCCCCCC[14CH3] SNRUBQQJIBEYMU-NJFSPNSNSA-N 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 238000000746 purification Methods 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 22
- 238000005259 measurement Methods 0.000 description 12
- 108010064470 polyaspartate Proteins 0.000 description 9
- 239000007788 liquid Substances 0.000 description 8
- 229920000805 Polyaspartic acid Polymers 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000003599 detergent Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012719 thermal polymerization Methods 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
- 235000003704 aspartic acid Nutrition 0.000 description 2
- 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 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000010612 desalination reaction Methods 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- YCOZIPAWZNQLMR-UHFFFAOYSA-N pentadecane Chemical compound CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000013535 sea water Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- 238000009827 uniform distribution Methods 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-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
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- -1 ferrous metals Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920001308 poly(aminoacid) Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 235000013406 prebiotics Nutrition 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012066 reaction slurry Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000007447 staining method Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/10—Alpha-amino-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1092—Polysuccinimides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Biological Depolymerization Polymers (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/398,323 US5552517A (en) | 1995-03-03 | 1995-03-03 | Production of polysuccinimide in an organic medium |
| PCT/US1996/002672 WO1996027627A1 (en) | 1995-03-03 | 1996-02-27 | Production of polysuccinimide in an organic medium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK119397A3 true SK119397A3 (en) | 1998-03-04 |
Family
ID=23574937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1193-97A SK119397A3 (en) | 1995-03-03 | 1996-02-27 | Production of polysuccinimide in an organic medium |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5552517A (no) |
| EP (1) | EP0813562B1 (no) |
| JP (1) | JPH11501079A (no) |
| KR (1) | KR19980702754A (no) |
| CN (1) | CN1088072C (no) |
| AT (1) | ATE185577T1 (no) |
| AU (1) | AU702811B2 (no) |
| BR (1) | BR9607540A (no) |
| CZ (1) | CZ273897A3 (no) |
| DE (1) | DE69604652T2 (no) |
| ES (1) | ES2140071T3 (no) |
| FI (1) | FI973585A (no) |
| GR (1) | GR3032300T3 (no) |
| HU (1) | HUP9801400A3 (no) |
| NO (1) | NO974029L (no) |
| NZ (1) | NZ304213A (no) |
| PL (1) | PL184405B1 (no) |
| RO (1) | RO118205B1 (no) |
| SK (1) | SK119397A3 (no) |
| WO (1) | WO1996027627A1 (no) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5856427A (en) * | 1996-01-16 | 1999-01-05 | Solutia Inc. | Process for the production of polysuccinimide |
| US5859149A (en) * | 1997-02-07 | 1999-01-12 | Solutia Inc. | Production of solid polyaspartate salt |
| US5889072A (en) * | 1997-02-24 | 1999-03-30 | Solutia Inc. | Process for preparing superabsorbing crosslinked polyaspartate salt |
| US5939517A (en) * | 1997-03-03 | 1999-08-17 | Donlar Corporation | Production of succinimide copolymers in cyclic carbonate solvent |
| US5834568A (en) * | 1997-03-17 | 1998-11-10 | Solutia, Inc. | Forming crosslinked polysuccinimide |
| US5859179A (en) * | 1997-03-17 | 1999-01-12 | Solutia Inc. | Forming superabsorbent polymer |
| US5981691A (en) * | 1997-04-23 | 1999-11-09 | University Of South Alabama | Imide-free and mixed amide/imide thermal synthesis of polyaspartate |
| EP1153958B1 (en) * | 1998-12-25 | 2004-09-29 | Mitsui Chemicals, Inc. | Process for producing polysuccinimide |
| US7101565B2 (en) | 2002-02-05 | 2006-09-05 | Corpak Medsystems, Inc. | Probiotic/prebiotic composition and delivery method |
| US20060099265A1 (en) * | 2003-03-20 | 2006-05-11 | Kazuhisa Shimizu | Micellar preparation containing sparingly water-soluble anticancer agent and novel block copolymer |
| EP1792927B1 (en) | 2004-09-22 | 2013-03-06 | Nippon Kayaku Kabushiki Kaisha | Novel block copolymer, micelle preparation, and anticancer agent containing the same as active ingredient |
| US8323669B2 (en) * | 2006-03-28 | 2012-12-04 | Nippon Kayaku Kabushiki Kaisha | Polymer conjugate of taxane |
| AU2007252678A1 (en) * | 2006-05-18 | 2007-11-29 | Nippon Kayaku Kabushiki Kaisha | Polymer conjugate of podophyllotoxin |
| WO2008041610A1 (fr) * | 2006-10-03 | 2008-04-10 | Nippon Kayaku Kabushiki Kaisha | Mélange d'un dérivé de résorcinol avec un polymère |
| US8334364B2 (en) * | 2006-11-06 | 2012-12-18 | Nipon Kayaku Kabushiki Kaisha | High-molecular weight derivative of nucleic acid antimetabolite |
| EP2206502B1 (en) * | 2007-09-28 | 2018-09-12 | Nippon Kayaku Kabushiki Kaisha | Polymer conjugate of steroid |
| RU2367513C2 (ru) | 2007-11-21 | 2009-09-20 | Учреждение Российской Академии Наук Институт Биохимической Физики Им. Н.М. Эмануэля Ран (Ибхф Ран) | Способ получения полимерного покрытия на поверхности частиц |
| CN101977631A (zh) * | 2008-03-18 | 2011-02-16 | 日本化药株式会社 | 生理活性物质的高分子量偶联物 |
| JP5366940B2 (ja) | 2008-05-08 | 2013-12-11 | 日本化薬株式会社 | 葉酸若しくは葉酸誘導体の高分子結合体 |
| EP2431403B1 (en) | 2009-05-15 | 2016-09-28 | Nipponkayaku Kabushikikaisha | Polymer conjugate of bioactive substance having hydroxy group |
| TW201304805A (zh) | 2010-11-17 | 2013-02-01 | Nippon Kayaku Kk | 新穎之胞核苷系代謝拮抗劑之高分子衍生物 |
| PT2754682T (pt) | 2011-09-11 | 2017-08-29 | Nippon Kayaku Kk | Método para o fabrico de copolímero de bloco |
| BR112017012488B1 (pt) * | 2014-12-12 | 2021-10-19 | Basf Se | Método para produzir ácido poliaspártico por meio de um pré-condensado |
| US10370620B2 (en) | 2015-09-08 | 2019-08-06 | Basf Se | Method for producing polyaspartic acid under reflux cooling |
| CN112080004A (zh) * | 2020-08-03 | 2020-12-15 | 南京艾普拉斯化工有限公司 | 聚琥珀酰亚胺和聚天冬氨酸的制备方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US538044A (en) * | 1895-04-23 | William houghtaling | ||
| US3846380A (en) * | 1972-10-31 | 1974-11-05 | M Teranishi | Polyamino acid derivatives and compositions containing same |
| US4363797A (en) * | 1977-09-14 | 1982-12-14 | Societe Anonyme Dite: L'oreal | Polyaspartic acid derivatives, their preparation and their use in cosmetic composition |
| FR2424293A1 (fr) * | 1978-04-27 | 1979-11-23 | Oreal | Nouveau procede de preparation de l'acide polydehydroaspartique |
| US4333844A (en) * | 1979-11-12 | 1982-06-08 | Lever Brothers Company | Detergent compositions |
| US4428749A (en) * | 1981-01-14 | 1984-01-31 | Lever Brothers Company | Fabric washing process and detergent composition for use therein |
| US4407722A (en) * | 1981-06-18 | 1983-10-04 | Lever Brothers Company | Fabric washing process and detergent composition for use therein |
| US5219986A (en) * | 1989-10-13 | 1993-06-15 | Cygnus Corporation | Polyanhydroaspartic acid and method of dry manufacture of polymers |
| US4971724A (en) * | 1990-02-06 | 1990-11-20 | Monsanto Company | Process for corrosion inhibition of ferrous metals |
| US5057597A (en) * | 1990-07-03 | 1991-10-15 | Koskan Larry P | Process for the manufacture of anhydro polyamino acids and polyamino acids |
| DE4023463C2 (de) * | 1990-07-24 | 1999-05-27 | Roehm Gmbh | Verfahren zur Molekulargewichtserhöhung bei der Herstellung von Polysuccinimid |
| US5221733A (en) * | 1991-02-22 | 1993-06-22 | Donlar Corporation | Manufacture of polyaspartic acids |
| US5315010A (en) * | 1991-02-22 | 1994-05-24 | Donlar Corporation | Polyaspartic acid manufacture |
| US5371179A (en) * | 1992-07-10 | 1994-12-06 | Rohm And Haas Company | Polysuccinimide polymers and process for preparing polysuccinimide polymers |
| US5380817A (en) * | 1992-07-10 | 1995-01-10 | Rohm And Haas Company | Process for preparing polysuccinimides from aspartic acid |
| US5319145A (en) * | 1992-07-10 | 1994-06-07 | Rohm And Haas Company | Method for preparing polysuccinimides with a rotary tray dryer |
| US5266237A (en) * | 1992-07-31 | 1993-11-30 | Rohm And Haas Company | Enhancing detergent performance with polysuccinimide |
| US5380447A (en) * | 1993-07-12 | 1995-01-10 | Rohm And Haas Company | Process and fabric finishing compositions for preventing the deposition of dye in fabric finishing processes |
| DE4327494A1 (de) * | 1993-08-16 | 1995-02-23 | Basf Ag | Verfahren zur Herstellung von Polyasparaginsäureimiden |
| US5484945A (en) * | 1993-08-24 | 1996-01-16 | Mitsui Toatsu Chemicals, Inc. | Preparation process of polysuccinimide |
| DE4342316A1 (de) * | 1993-12-11 | 1995-06-14 | Basf Ag | Verwendung von Polyasparaginsäure in Wasch- und Reinigungsmitteln |
-
1995
- 1995-03-03 US US08/398,323 patent/US5552517A/en not_active Expired - Lifetime
-
1996
- 1996-02-27 NZ NZ304213A patent/NZ304213A/xx unknown
- 1996-02-27 CZ CZ972738A patent/CZ273897A3/cs unknown
- 1996-02-27 EP EP96907901A patent/EP0813562B1/en not_active Expired - Lifetime
- 1996-02-27 PL PL96322086A patent/PL184405B1/pl not_active IP Right Cessation
- 1996-02-27 AU AU51343/96A patent/AU702811B2/en not_active Ceased
- 1996-02-27 BR BR9607540A patent/BR9607540A/pt not_active IP Right Cessation
- 1996-02-27 SK SK1193-97A patent/SK119397A3/sk unknown
- 1996-02-27 ES ES96907901T patent/ES2140071T3/es not_active Expired - Lifetime
- 1996-02-27 CN CN96193470A patent/CN1088072C/zh not_active Expired - Fee Related
- 1996-02-27 RO RO97-01677A patent/RO118205B1/ro unknown
- 1996-02-27 WO PCT/US1996/002672 patent/WO1996027627A1/en not_active Application Discontinuation
- 1996-02-27 KR KR1019970706161A patent/KR19980702754A/ko not_active Application Discontinuation
- 1996-02-27 AT AT96907901T patent/ATE185577T1/de not_active IP Right Cessation
- 1996-02-27 DE DE69604652T patent/DE69604652T2/de not_active Expired - Fee Related
- 1996-02-27 HU HU9801400A patent/HUP9801400A3/hu unknown
- 1996-02-27 JP JP8526915A patent/JPH11501079A/ja active Pending
-
1997
- 1997-09-02 FI FI973585A patent/FI973585A/fi unknown
- 1997-09-02 NO NO974029A patent/NO974029L/no unknown
-
1999
- 1999-12-30 GR GR990403388T patent/GR3032300T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2140071T3 (es) | 2000-02-16 |
| AU5134396A (en) | 1996-09-23 |
| DE69604652D1 (de) | 1999-11-18 |
| CN1088072C (zh) | 2002-07-24 |
| GR3032300T3 (en) | 2000-04-27 |
| HUP9801400A3 (en) | 1999-03-01 |
| NO974029L (no) | 1997-10-31 |
| JPH11501079A (ja) | 1999-01-26 |
| AU702811B2 (en) | 1999-03-04 |
| NZ304213A (en) | 1998-10-28 |
| CN1182441A (zh) | 1998-05-20 |
| RO118205B1 (ro) | 2003-03-28 |
| PL184405B1 (pl) | 2002-10-31 |
| KR19980702754A (ko) | 1998-08-05 |
| ATE185577T1 (de) | 1999-10-15 |
| MX9706683A (es) | 1997-11-29 |
| FI973585A0 (fi) | 1997-09-02 |
| US5552517A (en) | 1996-09-03 |
| BR9607540A (pt) | 1997-12-23 |
| WO1996027627A1 (en) | 1996-09-12 |
| EP0813562A1 (en) | 1997-12-29 |
| DE69604652T2 (de) | 2000-06-08 |
| EP0813562B1 (en) | 1999-10-13 |
| HUP9801400A2 (hu) | 1998-11-30 |
| PL322086A1 (en) | 1998-01-05 |
| CZ273897A3 (cs) | 1998-02-18 |
| NO974029D0 (no) | 1997-09-02 |
| FI973585A (fi) | 1997-10-30 |
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