DE2751535A1 - Verfahren zur polymerisation von pyrrolidon - Google Patents
Verfahren zur polymerisation von pyrrolidonInfo
- Publication number
- DE2751535A1 DE2751535A1 DE19772751535 DE2751535A DE2751535A1 DE 2751535 A1 DE2751535 A1 DE 2751535A1 DE 19772751535 DE19772751535 DE 19772751535 DE 2751535 A DE2751535 A DE 2751535A DE 2751535 A1 DE2751535 A1 DE 2751535A1
- Authority
- DE
- Germany
- Prior art keywords
- pyrrolidone
- acid
- mixture
- aqueous
- solution
- 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.)
- Withdrawn
Links
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 title claims description 184
- 238000006116 polymerization reaction Methods 0.000 title claims description 101
- 238000000034 method Methods 0.000 title claims description 62
- 239000000203 mixture Substances 0.000 claims description 96
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 73
- 239000000243 solution Substances 0.000 claims description 59
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 58
- 239000002253 acid Substances 0.000 claims description 45
- 239000000047 product Substances 0.000 claims description 42
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 38
- 239000002002 slurry Substances 0.000 claims description 38
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 33
- 238000001704 evaporation Methods 0.000 claims description 31
- 230000008020 evaporation Effects 0.000 claims description 31
- 239000000539 dimer Substances 0.000 claims description 30
- 239000001569 carbon dioxide Substances 0.000 claims description 29
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 238000005406 washing Methods 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 17
- 239000011541 reaction mixture Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 10
- 239000012190 activator Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000003247 decreasing effect Effects 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 239000003643 water by type Substances 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 2
- 239000011260 aqueous acid Substances 0.000 claims 1
- 238000009834 vaporization Methods 0.000 claims 1
- 230000008016 vaporization Effects 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 29
- 239000000178 monomer Substances 0.000 description 18
- 238000011084 recovery Methods 0.000 description 15
- 230000007062 hydrolysis Effects 0.000 description 14
- 238000006460 hydrolysis reaction Methods 0.000 description 14
- YGVFJBWDKIVBSX-UHFFFAOYSA-N 1-(2,3-dihydropyrrol-1-yl)pyrrolidin-2-one Chemical compound O=C1CCCN1N1C=CCC1 YGVFJBWDKIVBSX-UHFFFAOYSA-N 0.000 description 10
- 229920001007 Nylon 4 Polymers 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 8
- 229910052939 potassium sulfate Inorganic materials 0.000 description 8
- 235000011151 potassium sulphates Nutrition 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000003999 initiator Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- -1 hexane or heptane Chemical class 0.000 description 6
- 238000006386 neutralization reaction Methods 0.000 description 6
- 239000006072 paste Substances 0.000 description 6
- 238000005054 agglomeration Methods 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 235000005985 organic acids Nutrition 0.000 description 5
- DQAKJEWZWDQURW-UHFFFAOYSA-N pyrrolidonecarboxylic acid Chemical class OC(=O)N1CCCC1=O DQAKJEWZWDQURW-UHFFFAOYSA-N 0.000 description 5
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000012667 polymer degradation Methods 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 150000004040 pyrrolidinones Chemical class 0.000 description 3
- 150000003953 γ-lactams Chemical class 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- MEXQWQLMJYIYPG-UHFFFAOYSA-M potassium;2-oxopyrrolidine-1-carboxylate Chemical compound [K+].[O-]C(=O)N1CCCC1=O MEXQWQLMJYIYPG-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
- YLHUPYSUKYAIBW-UHFFFAOYSA-N 1-acetylpyrrolidin-2-one Chemical compound CC(=O)N1CCCC1=O YLHUPYSUKYAIBW-UHFFFAOYSA-N 0.000 description 1
- YRKRGYRYEQYTOH-UHFFFAOYSA-N 4-methylpyrrolidin-2-one Chemical compound CC1CNC(=O)C1 YRKRGYRYEQYTOH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000010945 base-catalyzed hydrolysis reactiony Methods 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000012674 dispersion polymerization Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 238000009428 plumbing Methods 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000001120 potassium sulphate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
- B01D3/34—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping with one or more auxiliary substances
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
- C07D201/16—Separation or purification
-
- 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
- C08G69/14—Lactams
- C08G69/24—Pyrrolidones or piperidones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyamides (AREA)
- Pyrrole Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/745,501 US4050994A (en) | 1976-11-26 | 1976-11-26 | Recovery of 2-pyrrolidone from dilute alkaline solutions |
| US05/792,421 US4139696A (en) | 1977-04-29 | 1977-04-29 | Continuous polymerization of 2-pyrrolidone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2751535A1 true DE2751535A1 (de) | 1978-06-01 |
Family
ID=27114468
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772751535 Withdrawn DE2751535A1 (de) | 1976-11-26 | 1977-11-18 | Verfahren zur polymerisation von pyrrolidon |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5367798A (enrdf_load_stackoverflow) |
| DE (1) | DE2751535A1 (enrdf_load_stackoverflow) |
| ES (1) | ES464485A1 (enrdf_load_stackoverflow) |
| FR (2) | FR2382471A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1592178A (enrdf_load_stackoverflow) |
| IT (1) | IT1087943B (enrdf_load_stackoverflow) |
| MX (1) | MX4979E (enrdf_load_stackoverflow) |
| NL (1) | NL7713024A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8157870B2 (en) | 2004-02-20 | 2012-04-17 | Synthes Usa, Llc | Prosthesis for replacing the surface in the area of the ball of ball-and-socket joints |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101568908B1 (ko) * | 2013-12-02 | 2015-11-12 | 지에스칼텍스 주식회사 | 입자상 폴리아미드 수지의 연속 제조장치 및 방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3681293A (en) * | 1970-09-03 | 1972-08-01 | Radiation Res Corp | Continuous polymerization of 2-pyrrolidone with carbon dioxide as activator |
-
1977
- 1977-11-18 FR FR7734795A patent/FR2382471A1/fr active Granted
- 1977-11-18 DE DE19772751535 patent/DE2751535A1/de not_active Withdrawn
- 1977-11-24 MX MX657877U patent/MX4979E/es unknown
- 1977-11-25 IT IT3006577A patent/IT1087943B/it active
- 1977-11-25 JP JP14080177A patent/JPS5367798A/ja active Granted
- 1977-11-25 GB GB4925777A patent/GB1592178A/en not_active Expired
- 1977-11-25 NL NL7713024A patent/NL7713024A/xx not_active Application Discontinuation
- 1977-11-25 ES ES464485A patent/ES464485A1/es not_active Expired
-
1978
- 1978-05-16 FR FR7814465A patent/FR2382442A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8157870B2 (en) | 2004-02-20 | 2012-04-17 | Synthes Usa, Llc | Prosthesis for replacing the surface in the area of the ball of ball-and-socket joints |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2382442B1 (enrdf_load_stackoverflow) | 1981-01-16 |
| FR2382471A1 (fr) | 1978-09-29 |
| GB1592178A (en) | 1981-07-01 |
| IT1087943B (it) | 1985-06-04 |
| MX4979E (es) | 1983-01-28 |
| ES464485A1 (es) | 1979-01-01 |
| JPS5731742B2 (enrdf_load_stackoverflow) | 1982-07-06 |
| FR2382471B1 (enrdf_load_stackoverflow) | 1981-01-02 |
| NL7713024A (nl) | 1978-05-30 |
| JPS5367798A (en) | 1978-06-16 |
| FR2382442A1 (fr) | 1978-09-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0566974B1 (de) | Reinigung von fluorierten Carbonsäuren | |
| DE2501348C3 (de) | Kontinuierliches Verfahren zur Herstellung von Polyamiden aus epsilon-Caprolactam | |
| EP0632009B1 (de) | Verfahren zur Rückgewinnung von fluorierten Carbonsäuren | |
| DE69105144T2 (de) | Katalytische herstellung von lactid direkt aus milchsäure. | |
| DE68902934T2 (de) | Verfahren zur herstellung von waessrigen loesungen von 2-hydroxy-4-methylthio-buttersaeure. | |
| EP0093317B1 (de) | Verfahren zur Herstellung von Calciumpropionat | |
| DE69316545T2 (de) | Verfahren zur Rückgewinnung von Alkalimetall- oder Erdalkalimetallterephthalat und Alkylenglykol aus Alkylenpolyterephthalaten | |
| DE2501614C3 (de) | Verfahren zur Herstellung von Propylenhomo- oder -copolymerisaten | |
| DE69203343T2 (de) | Polymerisation von Tetrahydrofuran zur Herstellung von Polytetramethylenetherglycol, mit einem Katalysator aus einem modifizierten Sulfonsäuregruppen enthaltenden fluorierten Harz. | |
| DE69222285T2 (de) | Verfahren zur Herstellung von Terephthalsäure | |
| DE10008161A1 (de) | Verfahren zur Herstellung eines wasserfreien Alkalimetallsulfids und einer Alkalimetallsulfidlösung | |
| DE69503476T2 (de) | Verfahren zur entfernung von umesterungskatalysatoren aus polyethenpolyolen | |
| DE2751535A1 (de) | Verfahren zur polymerisation von pyrrolidon | |
| DE2760272C2 (de) | Verfahren zur Herstellung von Poly-(tetramethylenether)-glykol durch Alkoholyse eines Ester-Endgruppen aufweisenden Poly-(tetramethylenether)-glykols | |
| DE2657190C2 (de) | Verfahren zur Reinigung von Naßverfahrensphosphorsäure | |
| DE2259796B2 (de) | Verfahren zur Gewinnung einer konzentrierten wäßrigen Acrylamidlösung oder kristallinen Acrylamide | |
| DE2642270C2 (de) | Verfahren zur Herstellung von Äthylvanadat | |
| DE69927593T2 (de) | Verfahren zur abtrennung von hydroxymethylthiobuttersäure | |
| DE2714564C2 (de) | Verfahren zur Herstellung von cyclischen Diestern der Undecandisäure | |
| DE3789007T2 (de) | Verfahren zur Herstellung von 3,5-Dichloro-2,4,6-trifluoropyridin. | |
| DE2524299C2 (de) | Verfahren zur Herstellung von Toluoyl-1-methyl-pyrrol-2-acetonitrilen | |
| DE69716203T2 (de) | Verfahren zur Herstellung von hochreinem 1,3-Dialkyl-2-imidazolidinon | |
| DE1099172B (de) | Verfahren zur Herstellung trocknender polymerer Kohlenwasserstoffoele | |
| DE2002377C3 (de) | Verfahren zur Extraktion von Zein aus Getreide-Gluten | |
| DE3722289C2 (de) | Verfahren zur Herstellung eines Polyactons einer Poly-Alpha-Hydroxyacrylsäure |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8128 | New person/name/address of the agent |
Representative=s name: DEUFEL, P., DIPL.-WIRTSCH.-ING. DR.RER.NAT. SCHOEN |
|
| 8130 | Withdrawal |