DE2602350A1 - Loesungspolymerisation von vernetzungsfaehigen acrylnitrilpolymerisaten - Google Patents
Loesungspolymerisation von vernetzungsfaehigen acrylnitrilpolymerisatenInfo
- Publication number
- DE2602350A1 DE2602350A1 DE19762602350 DE2602350A DE2602350A1 DE 2602350 A1 DE2602350 A1 DE 2602350A1 DE 19762602350 DE19762602350 DE 19762602350 DE 2602350 A DE2602350 A DE 2602350A DE 2602350 A1 DE2602350 A1 DE 2602350A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- polymerization
- acrylonitrile
- volume
- 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.)
- Pending
Links
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title claims description 19
- 238000010528 free radical solution polymerization reaction Methods 0.000 title claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 9
- 125000005385 peroxodisulfate group Chemical group 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 4
- 239000003495 polar organic solvent Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 21
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical group CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000004132 cross linking Methods 0.000 description 11
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 10
- 239000000835 fiber Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000000178 monomer Substances 0.000 description 8
- ULYOZOPEFCQZHH-UHFFFAOYSA-N n-(methoxymethyl)prop-2-enamide Chemical compound COCNC(=O)C=C ULYOZOPEFCQZHH-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229940113088 dimethylacetamide Drugs 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- -1 methylol alkyl ethers Chemical class 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CVBUKMMMRLOKQR-UHFFFAOYSA-N 1-phenylbutane-1,3-dione Chemical compound CC(=O)CC(=O)C1=CC=CC=C1 CVBUKMMMRLOKQR-UHFFFAOYSA-N 0.000 description 1
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- XEEYSDHEOQHCDA-UHFFFAOYSA-N 2-methylprop-2-ene-1-sulfonic acid Chemical compound CC(=C)CS(O)(=O)=O XEEYSDHEOQHCDA-UHFFFAOYSA-N 0.000 description 1
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005011 alkyl ether group Chemical group 0.000 description 1
- 239000012935 ammoniumperoxodisulfate Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- NZZIMKJIVMHWJC-UHFFFAOYSA-N dibenzoylmethane Chemical compound C=1C=CC=CC=1C(=O)CC(=O)C1=CC=CC=C1 NZZIMKJIVMHWJC-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical group CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000006855 networking Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- SZHIIIPPJJXYRY-UHFFFAOYSA-M sodium;2-methylprop-2-ene-1-sulfonate Chemical compound [Na+].CC(=C)CS([O-])(=O)=O SZHIIIPPJJXYRY-UHFFFAOYSA-M 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/42—Nitriles
- C08F220/44—Acrylonitrile
- C08F220/48—Acrylonitrile with nitrogen-containing monomers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/42—Nitriles
- C08F220/44—Acrylonitrile
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
- Artificial Filaments (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762602350 DE2602350A1 (de) | 1976-01-22 | 1976-01-22 | Loesungspolymerisation von vernetzungsfaehigen acrylnitrilpolymerisaten |
| GB1302/77A GB1531392A (en) | 1976-01-22 | 1977-01-13 | Production of crosslinkable acrylonitrile polymers by solution polymerisation |
| US05/760,705 US4059556A (en) | 1976-01-22 | 1977-01-19 | Spinnable solutions containing crosslinkable copolymers of acrylonitrile and N-methylol alkyl ether acrylamides |
| BE174227A BE850562A (fr) | 1976-01-22 | 1977-01-20 | Polymerisation en solution de polymeres d'acrylonitrile reticulables |
| DD7700197022A DD129655A5 (de) | 1976-01-22 | 1977-01-20 | Loesungspolymerisation von vernetzungsfaehigen acrylnitrilpolymerisaten |
| JP503877A JPS5291090A (en) | 1976-01-22 | 1977-01-21 | Solution polymerization of curable acrylonitrile polymer |
| FR7701794A FR2338955A1 (fr) | 1976-01-22 | 1977-01-21 | Polymerisation en solution de polymeres d'acrylonitrile reticulables |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762602350 DE2602350A1 (de) | 1976-01-22 | 1976-01-22 | Loesungspolymerisation von vernetzungsfaehigen acrylnitrilpolymerisaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2602350A1 true DE2602350A1 (de) | 1977-07-28 |
Family
ID=5968024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762602350 Pending DE2602350A1 (de) | 1976-01-22 | 1976-01-22 | Loesungspolymerisation von vernetzungsfaehigen acrylnitrilpolymerisaten |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4059556A (enExample) |
| JP (1) | JPS5291090A (enExample) |
| BE (1) | BE850562A (enExample) |
| DD (1) | DD129655A5 (enExample) |
| DE (1) | DE2602350A1 (enExample) |
| FR (1) | FR2338955A1 (enExample) |
| GB (1) | GB1531392A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4326049A (en) * | 1979-09-18 | 1982-04-20 | Minnesota Mining And Manufacturing Company | Phase transfer free-radical polymerization |
| US4536582A (en) * | 1983-01-21 | 1985-08-20 | Eagle-Picher Industries, Inc. | Heat curable solventless liquid prepolymer and novel monomer prepared from N-(2-hydroxyalkyl)phthalimide |
| US4629796A (en) * | 1983-01-21 | 1986-12-16 | Eagle-Picher Industries, Inc. | N-[[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-Z-yl)ethoxy]methyl]-Z-propenamide |
| US4933390A (en) * | 1985-06-28 | 1990-06-12 | Shmuel Dabi | In situ crosslinking of polyelectrolytes |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH470426A (de) * | 1965-06-23 | 1969-03-31 | Bayer Ag | Verfahren zur Herstellung von verspinnbaren Lösungen von Polyacrylnitril oder Acrylnitrilcopolymerisaten |
| NL126039C (enExample) * | 1965-07-14 | |||
| CH463794A (fr) * | 1967-05-25 | 1968-10-15 | Lonza Ag | Procédé d'obtention de polymères réticulés |
| US3803073A (en) * | 1968-07-31 | 1974-04-09 | B Goltsin | Process for preparing fiber-forming solutions on the base of acrylonitrile |
| US3925293A (en) * | 1970-09-14 | 1975-12-09 | Goodrich Co B F | Low-temperature curable latices of vinyl and acrylic monomers |
| US3917776A (en) * | 1970-12-12 | 1975-11-04 | Mitsubishi Rayon Co | Process for producing carbon fiber |
| JPS4943387B1 (enExample) * | 1971-03-03 | 1974-11-20 |
-
1976
- 1976-01-22 DE DE19762602350 patent/DE2602350A1/de active Pending
-
1977
- 1977-01-13 GB GB1302/77A patent/GB1531392A/en not_active Expired
- 1977-01-19 US US05/760,705 patent/US4059556A/en not_active Expired - Lifetime
- 1977-01-20 BE BE174227A patent/BE850562A/xx unknown
- 1977-01-20 DD DD7700197022A patent/DD129655A5/xx unknown
- 1977-01-21 JP JP503877A patent/JPS5291090A/ja active Pending
- 1977-01-21 FR FR7701794A patent/FR2338955A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| GB1531392A (en) | 1978-11-08 |
| US4059556A (en) | 1977-11-22 |
| BE850562A (fr) | 1977-07-20 |
| DD129655A5 (de) | 1978-02-01 |
| FR2338955B3 (enExample) | 1979-09-21 |
| JPS5291090A (en) | 1977-08-01 |
| FR2338955A1 (fr) | 1977-08-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |