CA2193198C - Procede de production d'un polysuccinimide et de derives de celui-ci - Google Patents
Procede de production d'un polysuccinimide et de derives de celui-ci Download PDFInfo
- Publication number
- CA2193198C CA2193198C CA002193198A CA2193198A CA2193198C CA 2193198 C CA2193198 C CA 2193198C CA 002193198 A CA002193198 A CA 002193198A CA 2193198 A CA2193198 A CA 2193198A CA 2193198 C CA2193198 C CA 2193198C
- Authority
- CA
- Canada
- Prior art keywords
- precursor
- polysuccinimide
- accordance
- reaction zone
- acid
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 52
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 239000002243 precursor Substances 0.000 claims abstract description 51
- 239000007787 solid Substances 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 23
- 229920000805 Polyaspartic acid Polymers 0.000 claims abstract description 9
- 108010064470 polyaspartate Proteins 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims description 43
- NLVWBYNKMPGKRG-ODZAUARKSA-N azane;(z)-but-2-enedioic acid Chemical compound N.OC(=O)\C=C/C(O)=O NLVWBYNKMPGKRG-ODZAUARKSA-N 0.000 claims description 19
- ZFJLXTJORIDUGY-ODZAUARKSA-N (z)-4-amino-4-oxobut-2-enoic acid;azane Chemical compound [NH4+].NC(=O)\C=C/C([O-])=O ZFJLXTJORIDUGY-ODZAUARKSA-N 0.000 claims description 18
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 18
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 18
- 238000012546 transfer Methods 0.000 claims description 17
- BFXUWDKAQDARCA-DKWTVANSSA-N (2s)-2-aminobutanedioic acid;azane Chemical compound [NH4+].OC(=O)[C@@H](N)CC([O-])=O BFXUWDKAQDARCA-DKWTVANSSA-N 0.000 claims description 14
- 239000001530 fumaric acid Substances 0.000 claims description 10
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 9
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 9
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 9
- CKKXWJDFFQPBQL-UAIGNFCESA-N diazanium;(z)-but-2-enedioate Chemical compound [NH4+].[NH4+].[O-]C(=O)\C=C/C([O-])=O CKKXWJDFFQPBQL-UAIGNFCESA-N 0.000 claims description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 9
- 239000001630 malic acid Substances 0.000 claims description 9
- 235000011090 malic acid Nutrition 0.000 claims description 9
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 9
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 150000003863 ammonium salts Chemical class 0.000 claims description 8
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 7
- 229940018557 citraconic acid Drugs 0.000 claims description 7
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 claims description 6
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- FSQQTNAZHBEJLS-UPHRSURJSA-N maleamic acid Chemical compound NC(=O)\C=C/C(O)=O FSQQTNAZHBEJLS-UPHRSURJSA-N 0.000 claims description 2
- 238000000151 deposition Methods 0.000 claims 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 6
- 239000011976 maleic acid Substances 0.000 claims 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000000376 reactant Substances 0.000 abstract description 12
- 238000012719 thermal polymerization Methods 0.000 abstract description 12
- 239000000543 intermediate Substances 0.000 abstract description 3
- 239000000178 monomer Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 description 29
- 238000010438 heat treatment Methods 0.000 description 20
- 238000011068 loading method Methods 0.000 description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 8
- 239000001099 ammonium carbonate Substances 0.000 description 8
- 229940059913 ammonium carbonate Drugs 0.000 description 8
- 235000012501 ammonium carbonate Nutrition 0.000 description 8
- 150000008064 anhydrides Chemical class 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 7
- 229960001230 asparagine Drugs 0.000 description 7
- 235000009582 asparagine Nutrition 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 230000003247 decreasing effect Effects 0.000 description 6
- 229960002598 fumaric acid Drugs 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 235000011087 fumaric acid Nutrition 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 229940099690 malic acid Drugs 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- NLVWBYNKMPGKRG-TYYBGVCCSA-N azanium;(e)-4-hydroxy-4-oxobut-2-enoate Chemical compound [NH4+].OC(=O)\C=C\C([O-])=O NLVWBYNKMPGKRG-TYYBGVCCSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- -1 itaconic anhydride-and monoammonium Chemical compound 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001542 size-exclusion chromatography Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 235000019297 ammonium fumarate Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000012611 container material Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 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
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000002023 wood Substances 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
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)
- Polyamides (AREA)
Abstract
Selon l'invention, on produit un polysuccinimide par polymérisation thermique d'un précurseur ou d'un mélange de réactifs comprenant un composé insaturé, dans un réacteur à plaques (14), à des températures suffisantes pour amorcer la polymérisation et former un solide cassant. Le polysuccinimide ainsi obtenu peut être transformé par hydrolyse en acide polyaspartique ou en un sel d'acide polyaspartique, si désiré. Le précurseur susmentionné peut être un monomère ou un mélange de réactifs formant des intermédiaires polymérisables.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/267,445 US5681920A (en) | 1994-06-28 | 1994-06-28 | Process for production of a polysuccinimide and derivatives thereof |
| US267,445 | 1994-06-28 | ||
| PCT/US1995/008365 WO1996000744A1 (fr) | 1994-06-28 | 1995-06-28 | Procede de production d'un polysuccinimide et de derives de celui-ci |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2193198A1 CA2193198A1 (fr) | 1996-01-11 |
| CA2193198C true CA2193198C (fr) | 2007-04-03 |
Family
ID=37951702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002193198A Expired - Lifetime CA2193198C (fr) | 1994-06-28 | 1995-06-28 | Procede de production d'un polysuccinimide et de derives de celui-ci |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2193198C (fr) |
-
1995
- 1995-06-28 CA CA002193198A patent/CA2193198C/fr not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2193198A1 (fr) | 1996-01-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5508434A (en) | Production of a polysuccinimide and derivatives thereof in the presence of a sulfur-containing dehydrating agent | |
| MXPA97002236A (en) | Production of polisuccinimide and derivatives from the same in the presence of a dehydrating agent containing azu | |
| US5681920A (en) | Process for production of a polysuccinimide and derivatives thereof | |
| CA2193198C (fr) | Procede de production d'un polysuccinimide et de derives de celui-ci | |
| EP0759948B1 (fr) | Production de polysuccinimide | |
| EP0336374A2 (fr) | Traitement de compositions de précurseur de polyimide | |
| CA2277305C (fr) | Production d'un sel de polyaspartate solide | |
| EP0741701B1 (fr) | Production de polysuccinimide | |
| CN114867710B (zh) | 2-氟代丙烯酸烷基酯的一步合成 | |
| US4281114A (en) | Method for preparing difurfurylideneacetone oligomer | |
| IE921284A1 (en) | PROCESS FOR THE CONTINUOUS PREPARATION OF AMINOARYL OR¹AMINOALKYL ß-SULFATOETHYL SULFONES | |
| JPH0579241B2 (fr) | ||
| CA1080871B (fr) | Resines catalysees par le calcium | |
| SU636893A1 (ru) | Способ получени фурановой смолы | |
| SU1014838A1 (ru) | Способ получени полимеров пропаргилового спирта | |
| Ardaud et al. | Process for the Preparation of Polymers Containing Boron and Nitrogen as Precursors of Boron Nitride, and Products Obtained | |
| JPS63225348A (ja) | イソフタロジニトリルの連続製法 | |
| MXPA96005591A (en) | Production of polisuccinim | |
| JPH02247213A (ja) | 自硬化性固形フェノール樹脂の製造方法 | |
| JPS61108517A (ja) | ナイロン樹脂反応成形装置 | |
| FR2466440A1 (fr) | Procede pour preparer des articles moules en mousse de verre | |
| HK1103234A1 (zh) | 烟酸的制造方法 | |
| JPS584935B2 (ja) | 尼素−ｃ↓４飽和脂肪族アルデヒド縮合物の製造方法 | |
| JPH0931193A (ja) | ポリアスパラギン酸アルカリ金属塩およびその誘導体の製造方法 | |
| JPS585922B2 (ja) | スイヨウセイレゾ−ルジユシノセイホウ |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20150629 |