DE2507777A1 - Loesungspolymerisation von acrylnitrilpolymerisaten - Google Patents
Loesungspolymerisation von acrylnitrilpolymerisatenInfo
- Publication number
- DE2507777A1 DE2507777A1 DE19752507777 DE2507777A DE2507777A1 DE 2507777 A1 DE2507777 A1 DE 2507777A1 DE 19752507777 DE19752507777 DE 19752507777 DE 2507777 A DE2507777 A DE 2507777A DE 2507777 A1 DE2507777 A1 DE 2507777A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- parts
- polymerization
- volume
- diketone
- 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- Withdrawn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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title claims description 21
- 238000010528 free radical solution polymerization reaction Methods 0.000 title claims description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 63
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 34
- 238000006116 polymerization reaction Methods 0.000 claims description 31
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 24
- 239000000178 monomer Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 125000005385 peroxodisulfate group Chemical group 0.000 claims description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 5
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical group [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000012935 ammoniumperoxodisulfate Substances 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 5
- XEEYSDHEOQHCDA-UHFFFAOYSA-N 2-methylprop-2-ene-1-sulfonic acid Chemical compound CC(=C)CS(O)(=O)=O XEEYSDHEOQHCDA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- IQOJIHIRSVQTJJ-UHFFFAOYSA-N 3-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(Cl)=C1 IQOJIHIRSVQTJJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- WRUAHXANJKHFIL-UHFFFAOYSA-N benzene-1,3-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC(S(O)(=O)=O)=C1 WRUAHXANJKHFIL-UHFFFAOYSA-N 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000002904 solvent Substances 0.000 description 5
- 238000009987 spinning Methods 0.000 description 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 150000002978 peroxides Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229910015900 BF3 Inorganic materials 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- VLUWLNIMIAFOSY-UHFFFAOYSA-N 2-methylbenzenesulfinic acid Chemical compound CC1=CC=CC=C1S(O)=O VLUWLNIMIAFOSY-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
- NYYSPVRERVXMLJ-UHFFFAOYSA-N 4,4-difluorocyclohexan-1-one Chemical compound FC1(F)CCC(=O)CC1 NYYSPVRERVXMLJ-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- OXWNNNGSAYHDQH-UHFFFAOYSA-N [N].C(C=C)(=O)OC Chemical compound [N].C(C=C)(=O)OC OXWNNNGSAYHDQH-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- -1 dirnethylacetamide Chemical compound 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- NMAAELNWXDXUDB-UHFFFAOYSA-N n,n-dimethylformamide;prop-2-enenitrile Chemical compound C=CC#N.CN(C)C=O NMAAELNWXDXUDB-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UIIIBRHUICCMAI-UHFFFAOYSA-N prop-2-ene-1-sulfonic acid Chemical compound OS(=O)(=O)CC=C UIIIBRHUICCMAI-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000002166 wet spinning Methods 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
- C08F20/00—Homopolymers and 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
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/42—Nitriles
- C08F20/44—Acrylonitrile
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752507777 DE2507777A1 (de) | 1975-02-22 | 1975-02-22 | Loesungspolymerisation von acrylnitrilpolymerisaten |
| GB44907/75A GB1512398A (en) | 1975-02-22 | 1975-10-30 | Solution polymerisation or copolymerisation of acrylonitrile |
| US05/658,904 US4052355A (en) | 1975-02-22 | 1976-02-18 | Acrylonitrile polymer solutions |
| NL7601698A NL7601698A (nl) | 1975-02-22 | 1976-02-19 | Werkwijze voor het polymeriseren in oplossing van acrylonitrilepolymeren. |
| JP1715276A JPS5711321B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-02-22 | 1976-02-20 | |
| DK70776*#A DK70776A (da) | 1975-02-22 | 1976-02-20 | Fremgangsmade til fremstilling spindelige oplosninger af acrylonitrilpolymerisater |
| DD191375A DD125490A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-02-22 | 1976-02-20 | |
| CA246,200A CA1054286A (en) | 1975-02-22 | 1976-02-20 | Solution polymerisation of acrylonitrile polymers |
| IT20426/76A IT1055415B (it) | 1975-02-22 | 1976-02-20 | Polimerizzazione in soluzione di polimeri di acrilonitrile |
| IE338/76A IE42484B1 (en) | 1975-02-22 | 1976-02-20 | Solution polymerisation or copolymerisation of acrylonitrile |
| LU74394A LU74394A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-02-22 | 1976-02-20 | |
| FR7604794A FR2301540A1 (fr) | 1975-02-22 | 1976-02-20 | Procede perfectionne pour la polymerisation en solution de l'acrylonitrile |
| BE164502A BE838784A (fr) | 1975-02-22 | 1976-02-20 | Procede perfectionne pour la polymerisation en solution de l'acrylonitrile |
| ES445369A ES445369A1 (es) | 1975-02-22 | 1976-02-20 | Procedimiento para la obtencion de soluciones hilables de polimeros de acrilonitrilo. |
| AT121876A AT346584B (de) | 1975-02-22 | 1976-02-20 | Verfahren zur herstellung von verspinnbaren loesungen des polyacrylnitrils und seiner mischpolymerisate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752507777 DE2507777A1 (de) | 1975-02-22 | 1975-02-22 | Loesungspolymerisation von acrylnitrilpolymerisaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2507777A1 true DE2507777A1 (de) | 1976-09-02 |
Family
ID=5939606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752507777 Withdrawn DE2507777A1 (de) | 1975-02-22 | 1975-02-22 | Loesungspolymerisation von acrylnitrilpolymerisaten |
Country Status (15)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2833143A1 (de) * | 1978-07-28 | 1980-02-07 | Bayer Ag | Acrylnitril enthaltende polymere und verfahren zu deren herstellung |
| US4216301A (en) * | 1979-06-18 | 1980-08-05 | Mobil Oil Corporation | Process for solution polymerization of acrylonitrile |
| US5057584A (en) * | 1981-11-05 | 1991-10-15 | Union Oil Company Of California | Sulfuric acid adduct-catalyzed polymerization |
| US5105040A (en) * | 1985-08-30 | 1992-04-14 | Union Oil Company Of California | Acid catalyzed oxidative reactions |
| US5003021A (en) * | 1988-03-22 | 1991-03-26 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for producing an aromatic vinyl compound-vinyl cyanide compound copolymer |
| IE980775A1 (en) * | 1998-09-17 | 2000-03-22 | Loctite R & D Ltd | Auto-oxidation systems for air-activatable polymerisable compositions |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3025278A (en) * | 1955-12-29 | 1962-03-13 | Du Pont | Method of controlling the dyeability of acrylonitrile polymers |
| DE1645330A1 (de) * | 1966-02-07 | 1970-06-04 | Snia Viscosa Societa Naz Ind A | Verfahren und Vorrichtung zur industriellen Herstellung von spinnbaren Polymeren auf der Basis von Acrylnitril |
| US3634370A (en) * | 1969-07-14 | 1972-01-11 | Gaetano F D Alelio | Acrylonitrile polymerization in the presence of sulfuric acid followed by a neutralization step |
| DE2032548A1 (de) * | 1970-07-01 | 1972-01-20 | Bayer | Acrylnitrilpolymerisate mit hohem Molekulargewicht, hohen kristallinen Anteilen und enger Molekulargewichtsverteilung und Verfahren zu ihrer Herstellung |
-
1975
- 1975-02-22 DE DE19752507777 patent/DE2507777A1/de not_active Withdrawn
- 1975-10-30 GB GB44907/75A patent/GB1512398A/en not_active Expired
-
1976
- 1976-02-18 US US05/658,904 patent/US4052355A/en not_active Expired - Lifetime
- 1976-02-19 NL NL7601698A patent/NL7601698A/xx not_active Application Discontinuation
- 1976-02-20 LU LU74394A patent/LU74394A1/xx unknown
- 1976-02-20 ES ES445369A patent/ES445369A1/es not_active Expired
- 1976-02-20 CA CA246,200A patent/CA1054286A/en not_active Expired
- 1976-02-20 DD DD191375A patent/DD125490A5/xx unknown
- 1976-02-20 IT IT20426/76A patent/IT1055415B/it active
- 1976-02-20 FR FR7604794A patent/FR2301540A1/fr active Granted
- 1976-02-20 IE IE338/76A patent/IE42484B1/en unknown
- 1976-02-20 AT AT121876A patent/AT346584B/de not_active IP Right Cessation
- 1976-02-20 JP JP1715276A patent/JPS5711321B2/ja not_active Expired
- 1976-02-20 BE BE164502A patent/BE838784A/xx unknown
- 1976-02-20 DK DK70776*#A patent/DK70776A/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE838784A (fr) | 1976-08-20 |
| IE42484L (en) | 1976-08-22 |
| AT346584B (de) | 1978-11-10 |
| IE42484B1 (en) | 1980-08-13 |
| JPS5711321B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-03-03 |
| NL7601698A (nl) | 1976-08-24 |
| LU74394A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-01-06 |
| US4052355A (en) | 1977-10-04 |
| IT1055415B (it) | 1981-12-21 |
| JPS51107386A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-09-22 |
| ES445369A1 (es) | 1977-07-01 |
| FR2301540B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-11-21 |
| DK70776A (da) | 1976-08-23 |
| GB1512398A (en) | 1978-06-01 |
| FR2301540A1 (fr) | 1976-09-17 |
| DD125490A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-04-20 |
| ATA121876A (de) | 1978-03-15 |
| CA1054286A (en) | 1979-05-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8125 | Change of the main classification |
Ipc: C08F220/44 |
|
| 8130 | Withdrawal |