NZ260338A - Polyanhydroaspartic acid having substantially biodegradable hydrolysates, their preparation and use as detergent builders - Google Patents
Polyanhydroaspartic acid having substantially biodegradable hydrolysates, their preparation and use as detergent buildersInfo
- Publication number
- NZ260338A NZ260338A NZ260338A NZ26033894A NZ260338A NZ 260338 A NZ260338 A NZ 260338A NZ 260338 A NZ260338 A NZ 260338A NZ 26033894 A NZ26033894 A NZ 26033894A NZ 260338 A NZ260338 A NZ 260338A
- Authority
- NZ
- New Zealand
- Prior art keywords
- acid
- polyanhydroaspartic
- hydrolysates
- process according
- boron
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 43
- 239000003599 detergent Substances 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims description 6
- 108010009736 Protein Hydrolysates Proteins 0.000 title description 2
- 150000001638 boron Chemical class 0.000 claims abstract description 23
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims abstract description 11
- 235000003704 aspartic acid Nutrition 0.000 claims abstract description 11
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 230000007062 hydrolysis Effects 0.000 claims abstract description 9
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 9
- 239000002243 precursor Substances 0.000 claims abstract description 7
- 150000003949 imides Chemical group 0.000 claims abstract description 6
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003156 secondary amide group Chemical group 0.000 claims abstract description 5
- 125000001749 primary amide group Chemical group 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 22
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 239000000413 hydrolysate Substances 0.000 claims description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 235000001014 amino acid Nutrition 0.000 claims description 6
- 229940024606 amino acid Drugs 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 6
- 235000010338 boric acid Nutrition 0.000 claims description 6
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 claims description 6
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000004327 boric acid Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000004448 titration Methods 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical class [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- 238000004061 bleaching Methods 0.000 claims description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 3
- 125000005619 boric acid group Chemical class 0.000 claims description 3
- -1 boron halides Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 238000000746 purification Methods 0.000 claims description 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004471 Glycine Substances 0.000 claims description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 2
- 229920002197 Sodium polyaspartate Polymers 0.000 claims description 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims description 2
- 239000004473 Threonine Substances 0.000 claims description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 235000004279 alanine Nutrition 0.000 claims description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 2
- 229910000085 borane Inorganic materials 0.000 claims description 2
- BGECDVWSWDRFSP-UHFFFAOYSA-N borazine Chemical compound B1NBNBN1 BGECDVWSWDRFSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005620 boronic acid group Chemical class 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 235000018417 cysteine Nutrition 0.000 claims description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 235000014304 histidine Nutrition 0.000 claims description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 235000014705 isoleucine Nutrition 0.000 claims description 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 2
- 229960000310 isoleucine Drugs 0.000 claims description 2
- 235000005772 leucine Nutrition 0.000 claims description 2
- 235000018977 lysine Nutrition 0.000 claims description 2
- 238000005259 measurement Methods 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 235000006109 methionine Nutrition 0.000 claims description 2
- 229930182817 methionine Natural products 0.000 claims description 2
- 235000008729 phenylalanine Nutrition 0.000 claims description 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 2
- 235000013930 proline Nutrition 0.000 claims description 2
- 235000004400 serine Nutrition 0.000 claims description 2
- 238000012719 thermal polymerization Methods 0.000 claims description 2
- 235000008521 threonine Nutrition 0.000 claims description 2
- 235000014393 valine Nutrition 0.000 claims description 2
- 239000004474 valine Substances 0.000 claims description 2
- 230000003389 potentiating effect Effects 0.000 claims 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 238000003918 potentiometric titration Methods 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 108010064470 polyaspartate Proteins 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000006065 biodegradation reaction Methods 0.000 description 3
- 238000012505 colouration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920000805 Polyaspartic acid Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UDHXJZHVNHGCEC-UHFFFAOYSA-N Chlorophacinone Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)C(=O)C1C(=O)C2=CC=CC=C2C1=O UDHXJZHVNHGCEC-UHFFFAOYSA-N 0.000 description 1
- ZOMVCLKADSEVSA-UHFFFAOYSA-N ClC1=C(C(=NB1)Cl)Cl Chemical class ClC1=C(C(=NB1)Cl)Cl ZOMVCLKADSEVSA-UHFFFAOYSA-N 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 229920000608 Polyaspartic Polymers 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- UOALEFQKAOQICC-UHFFFAOYSA-N chloroborane Chemical class ClB UOALEFQKAOQICC-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 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
- 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
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3719—Polyamides or polyimides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Polyamides (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Biological Depolymerization Polymers (AREA)
- Detergent Compositions (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9304815 | 1993-04-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ260338A true NZ260338A (en) | 1995-08-28 |
Family
ID=9446373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ260338A NZ260338A (en) | 1993-04-23 | 1994-04-18 | Polyanhydroaspartic acid having substantially biodegradable hydrolysates, their preparation and use as detergent builders |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5536813A (enExample) |
| EP (1) | EP0621300B1 (enExample) |
| JP (1) | JP2696481B2 (enExample) |
| CN (1) | CN1036926C (enExample) |
| AT (1) | ATE171715T1 (enExample) |
| AU (1) | AU677635B2 (enExample) |
| BR (1) | BR9401575A (enExample) |
| CA (1) | CA2121983A1 (enExample) |
| DE (1) | DE69413590D1 (enExample) |
| IL (1) | IL109379A0 (enExample) |
| NO (1) | NO941453L (enExample) |
| NZ (1) | NZ260338A (enExample) |
| TW (1) | TW301672B (enExample) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5714167A (en) | 1992-06-15 | 1998-02-03 | Emisphere Technologies, Inc. | Active agent transport systems |
| US5578323A (en) | 1992-06-15 | 1996-11-26 | Emisphere Technologies, Inc. | Proteinoid carriers and methods for preparation and use thereof |
| US6221367B1 (en) | 1992-06-15 | 2001-04-24 | Emisphere Technologies, Inc. | Active agent transport systems |
| US6331318B1 (en) | 1994-09-30 | 2001-12-18 | Emisphere Technologies Inc. | Carbon-substituted diketopiperazine delivery systems |
| US6099856A (en) | 1992-06-15 | 2000-08-08 | Emisphere Technologies, Inc. | Active agent transport systems |
| US5693338A (en) | 1994-09-29 | 1997-12-02 | Emisphere Technologies, Inc. | Diketopiperazine-based delivery systems |
| US5629020A (en) * | 1994-04-22 | 1997-05-13 | Emisphere Technologies, Inc. | Modified amino acids for drug delivery |
| US5792451A (en) | 1994-03-02 | 1998-08-11 | Emisphere Technologies, Inc. | Oral drug delivery compositions and methods |
| US5811127A (en) | 1992-06-15 | 1998-09-22 | Emisphere Technologies, Inc. | Desferrioxamine oral delivery system |
| US5401516A (en) | 1992-12-21 | 1995-03-28 | Emisphere Technologies, Inc. | Modified hydrolyzed vegetable protein microspheres and methods for preparation and use thereof |
| US6461643B2 (en) * | 1993-04-22 | 2002-10-08 | Emisphere Technologies, Inc. | Oral drug delivery compositions and methods |
| US5958457A (en) | 1993-04-22 | 1999-09-28 | Emisphere Technologies, Inc. | Compositions for the delivery of antigens |
| IL109403A0 (en) | 1993-04-22 | 1994-07-31 | Emisphere Tech Inc | Oral drug delivery compositions and methods |
| US5643957A (en) | 1993-04-22 | 1997-07-01 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| ES2161747T3 (es) * | 1993-11-24 | 2001-12-16 | Rhodia Chimie Sa | Procedimiento de preparacion de poliimidas o de sus hidrolizados polipeptidicos biodegradables. |
| US6090958A (en) | 1995-03-31 | 2000-07-18 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6001347A (en) | 1995-03-31 | 1999-12-14 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| CN1151836C (zh) | 1995-03-31 | 2004-06-02 | 艾米斯菲尔技术有限公司 | 用作传送活性剂的化合物和组合物 |
| US5866536A (en) | 1995-03-31 | 1999-02-02 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5965121A (en) | 1995-03-31 | 1999-10-12 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5989539A (en) | 1995-03-31 | 1999-11-23 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5750147A (en) | 1995-06-07 | 1998-05-12 | Emisphere Technologies, Inc. | Method of solubilizing and encapsulating itraconazole |
| US6051258A (en) | 1995-06-07 | 2000-04-18 | Emisphere Technologies, Inc. | Proteinoid emulsions and methods for preparation and use thereof |
| US5824345A (en) | 1995-06-07 | 1998-10-20 | Emisphere Technologies, Inc. | Fragrances and flavorants |
| WO1997010197A1 (en) | 1995-09-11 | 1997-03-20 | Emisphere Technologies, Inc. | METHOD FOR PREPARING φ-AMINOALKANOIC ACID DERIVATIVES FROM CYCLOALKANONES |
| AU2595697A (en) | 1996-03-29 | 1997-10-22 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| WO1997047288A1 (en) | 1996-06-14 | 1997-12-18 | Emisphere Technologies, Inc. | Microencapsulated fragrances and method for preparation |
| US5776888A (en) * | 1997-02-07 | 1998-07-07 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5879681A (en) | 1997-02-07 | 1999-03-09 | Emisphere Technolgies Inc. | Compounds and compositions for delivering active agents |
| US5876710A (en) | 1997-02-07 | 1999-03-02 | Emisphere Technologies Inc. | Compounds and compositions for delivering active agents |
| US5939381A (en) | 1997-02-07 | 1999-08-17 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6060513A (en) | 1997-02-07 | 2000-05-09 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6358504B1 (en) | 1997-02-07 | 2002-03-19 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5773647A (en) * | 1997-02-07 | 1998-06-30 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6313088B1 (en) | 1997-02-07 | 2001-11-06 | Emisphere Technologies, Inc. | 8-[(2-hydroxy-4-methoxy benzoyl) amino]-octanoic acid compositions for delivering active agents |
| US5804688A (en) | 1997-02-07 | 1998-09-08 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5990166A (en) | 1997-02-07 | 1999-11-23 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US6051561A (en) * | 1997-02-07 | 2000-04-18 | Emisphere Technologies Inc. | Compounds and compositions for delivering active agents |
| US5981691A (en) * | 1997-04-23 | 1999-11-09 | University Of South Alabama | Imide-free and mixed amide/imide thermal synthesis of polyaspartate |
| US5863944A (en) | 1997-04-30 | 1999-01-26 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| US5962710A (en) | 1997-05-09 | 1999-10-05 | Emisphere Technologies, Inc. | Method of preparing salicyloylamino acids |
| US6906191B2 (en) * | 1999-12-27 | 2005-06-14 | Idemitsu Kosan Co., Ltd. | Succinimide compounds and use thereof |
| TWI407907B (zh) | 2010-10-04 | 2013-09-11 | Far Eastern New Century Corp | An antibacterial agent with water solubility and biodegradability |
| CN102450260B (zh) * | 2010-10-14 | 2013-10-16 | 远东新世纪股份有限公司 | 一种具水溶性及生物可分解性的抗菌剂 |
| CN102250353B (zh) * | 2011-05-23 | 2012-10-10 | 黑龙江大学 | 多组分蒸发结晶共聚改性合成聚天冬氨酸衍生物的方法 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4851995A (enExample) * | 1971-11-01 | 1973-07-21 | ||
| DE2626651A1 (de) * | 1976-06-15 | 1977-12-29 | Barmag Barmer Maschf | Kabelfang- und -abschneidevorrichtung |
| US4363797A (en) * | 1977-09-14 | 1982-12-14 | Societe Anonyme Dite: L'oreal | Polyaspartic acid derivatives, their preparation and their use in cosmetic composition |
| JPS61218634A (ja) * | 1985-03-25 | 1986-09-29 | Fuso Kagaku Kogyo Kk | ポリアミノ酸類の製造法 |
| CH667874A5 (fr) * | 1985-12-19 | 1988-11-15 | Battelle Memorial Institute | Polypeptide synthetique biodegradable et son utilisation pour la preparation de medicaments. |
| DD262665A1 (de) * | 1987-06-17 | 1988-12-07 | Akad Wissenschaften Ddr | Verfahren zur herstellung von polyaspartimid |
| US4916204A (en) * | 1987-07-31 | 1990-04-10 | Massachusetts Institute Of Technology | Pure polyanhydride from dicarboxylic acid and coupling agent |
| US4868287A (en) * | 1987-08-24 | 1989-09-19 | University Of South Alabama | Inhibition of mineral deposition by polyanionic/hydrophobic peptides and derivatives thereof having a clustered block copolymer structure |
| JPH01283228A (ja) * | 1988-05-06 | 1989-11-14 | Ajinomoto Co Inc | 生体分解徐放性材料 |
| DE4002736A1 (de) * | 1990-01-31 | 1991-08-01 | Hoechst Ag | Biologisch abbaubare polymere, verfahren zu ihrer herstellung und verwendung derselben fuer depotzubereitungen mit kontrollierter wirkstoffabgabe |
| 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 |
| FR2675153B1 (fr) * | 1991-04-15 | 1994-07-22 | Rhone Poulenc Chimie | Composition detergente contenant un biopolymere polyimide hydrolysable en milieu lessiviel. |
| FI925734A7 (fi) * | 1991-12-20 | 1993-06-21 | Hoechst Ag | Polyaspartamidijohdoksia sappihapon adsorptioaineina, sappihappoja sisältäviä polyaspartamidijohdoksia ja menetelmä niiden valmistamiseksi sekä niiden käyttö lääkkeinä |
| US5319145A (en) * | 1992-07-10 | 1994-06-07 | Rohm And Haas Company | Method for preparing polysuccinimides with a rotary tray dryer |
| US5380817A (en) * | 1992-07-10 | 1995-01-10 | Rohm And Haas Company | Process for preparing polysuccinimides from aspartic acid |
| US5266237A (en) * | 1992-07-31 | 1993-11-30 | Rohm And Haas Company | Enhancing detergent performance with polysuccinimide |
| US5292864A (en) * | 1992-08-07 | 1994-03-08 | Srchem Incorporated | Decolorizing polyaspartic acid polymers |
| DE4307114A1 (de) * | 1993-03-06 | 1994-09-08 | Basf Ag | Verfahren zur Herstellung von Umsetzungsprodukten aus Polyasparaginsäureamid und Aminosäuren und ihre Verwendung |
-
1994
- 1994-04-15 DE DE69413590T patent/DE69413590D1/de not_active Expired - Lifetime
- 1994-04-15 EP EP94400831A patent/EP0621300B1/fr not_active Expired - Lifetime
- 1994-04-15 AT AT94400831T patent/ATE171715T1/de not_active IP Right Cessation
- 1994-04-18 NZ NZ260338A patent/NZ260338A/en unknown
- 1994-04-19 AU AU60581/94A patent/AU677635B2/en not_active Ceased
- 1994-04-21 IL IL10937994A patent/IL109379A0/xx unknown
- 1994-04-21 JP JP6104998A patent/JP2696481B2/ja not_active Expired - Lifetime
- 1994-04-21 NO NO941453A patent/NO941453L/no unknown
- 1994-04-22 CA CA002121983A patent/CA2121983A1/fr not_active Abandoned
- 1994-04-22 BR BR9401575A patent/BR9401575A/pt not_active Application Discontinuation
- 1994-04-23 CN CN94104627A patent/CN1036926C/zh not_active Expired - Fee Related
- 1994-04-25 US US08/231,666 patent/US5536813A/en not_active Expired - Fee Related
- 1994-05-03 TW TW083104005A patent/TW301672B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| JP2696481B2 (ja) | 1998-01-14 |
| IL109379A0 (en) | 1994-07-31 |
| ATE171715T1 (de) | 1998-10-15 |
| TW301672B (enExample) | 1997-04-01 |
| NO941453L (no) | 1994-10-24 |
| EP0621300A3 (fr) | 1995-11-08 |
| AU677635B2 (en) | 1997-05-01 |
| CA2121983A1 (fr) | 1994-10-24 |
| NO941453D0 (no) | 1994-04-21 |
| AU6058194A (en) | 1994-10-27 |
| CN1097429A (zh) | 1995-01-18 |
| JPH073010A (ja) | 1995-01-06 |
| EP0621300B1 (fr) | 1998-09-30 |
| BR9401575A (pt) | 1995-03-07 |
| US5536813A (en) | 1996-07-16 |
| CN1036926C (zh) | 1998-01-07 |
| EP0621300A2 (fr) | 1994-10-26 |
| DE69413590D1 (de) | 1998-11-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5536813A (en) | Detersive polyanhydroaspartic acids and biodegradable hydrolysates thereof | |
| US5639832A (en) | Preparation of products of the reaction of polyaspartimide and amino acids and the use thereof | |
| AU674144B2 (en) | Salts of polyaspartic acid by high temperature reaction | |
| US5442038A (en) | Polymers of maleic acid with amines | |
| AU689812B2 (en) | Amino acid copolymers of maleic acid | |
| JPH07509751A (ja) | ポリアスパラギン酸共重合体 | |
| US20030069153A1 (en) | Polyaspartate derivatives for use in detergent compositions | |
| KR100201264B1 (ko) | 생분해성 폴리이미드 또는 그의 폴리펩티드 가수분해물의 제조방법 | |
| KR20040010587A (ko) | 이미드-함유 폴리아미노산을 제조하기 위한 공단량체 조성물 | |
| EP0745102A1 (en) | Copolymers of polyaspartic acid and polycarboxylic acids and polyamines | |
| NZ272689A (en) | Preparation of polycondensates of amino acids or hydrolysates thereof by bulk thermal polymerisation in pulverulent medium comprising (poly)phosphoric acid or phosphorus pentoxide as catalyst | |
| JP2002509170A (ja) | スクシンイミドコポリマーの製造 | |
| US5936121A (en) | Polymers of aspartic acid with sequestering activity process for their preparation and use thereof | |
| JPH11500167A (ja) | 無水ポリアミノ酸の製造 | |
| US6887971B2 (en) | Synthesis of polysuccinimide and copoly(succinimide-aspartate) in a supercritical fluid | |
| JPH08337769A (ja) | キレート剤 | |
| KR20000068474A (ko) | 반복 숙시닐 단위를 갖는 중합체의 제조 방법 | |
| JPH10168184A (ja) | キレート剤 | |
| JPH11147953A (ja) | 色調の優れたポリアスパラギン酸及びその製造方法 | |
| JPH07196790A (ja) | ポリアミノ酸類の製造方法 |