IE42484B1 - Solution polymerisation or copolymerisation of acrylonitrile - Google Patents
Solution polymerisation or copolymerisation of acrylonitrileInfo
- Publication number
- IE42484B1 IE42484B1 IE338/76A IE33876A IE42484B1 IE 42484 B1 IE42484 B1 IE 42484B1 IE 338/76 A IE338/76 A IE 338/76A IE 33876 A IE33876 A IE 33876A IE 42484 B1 IE42484 B1 IE 42484B1
- Authority
- IE
- Ireland
- Prior art keywords
- acid
- parts
- acrylonitrile
- weight
- monomer
- Prior art date
Links
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 title claims abstract description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 66
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims abstract description 36
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000000178 monomer Substances 0.000 claims abstract description 29
- 239000002253 acid Substances 0.000 claims abstract description 17
- 229920000642 polymer Polymers 0.000 claims abstract description 15
- 125000005385 peroxodisulfate group Chemical group 0.000 claims abstract description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 31
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 239000001117 sulphuric acid Substances 0.000 claims description 8
- 235000011149 sulphuric acid Nutrition 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 4
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- -1 methallyl sulphonic acid Chemical compound 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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 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
- 229940113088 dimethylacetamide Drugs 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 235000006408 oxalic acid Nutrition 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 abstract description 5
- 159000000000 sodium salts Chemical class 0.000 abstract description 4
- AGBXYHCHUYARJY-UHFFFAOYSA-N 2-phenylethenesulfonic acid Chemical compound OS(=O)(=O)C=CC1=CC=CC=C1 AGBXYHCHUYARJY-UHFFFAOYSA-N 0.000 abstract description 2
- 125000005594 diketone group Chemical group 0.000 abstract description 2
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 1
- 125000005394 methallyl group Chemical group 0.000 abstract 1
- 230000000379 polymerizing effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 4
- 230000002349 favourable effect Effects 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
- 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
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- 239000004753 textile Substances 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
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- NVSONFIVLCXXDH-UHFFFAOYSA-N benzylsulfinic acid Chemical compound O[S@@](=O)CC1=CC=CC=C1 NVSONFIVLCXXDH-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- NDOGLIPWGGRQCO-UHFFFAOYSA-N hexane-2,4-dione Chemical compound CCC(=O)CC(C)=O NDOGLIPWGGRQCO-UHFFFAOYSA-N 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003495 polar organic solvent Substances 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
- 238000009987 spinning Methods 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752507777 DE2507777A1 (de) | 1975-02-22 | 1975-02-22 | Loesungspolymerisation von acrylnitrilpolymerisaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE42484L IE42484L (en) | 1976-08-22 |
| IE42484B1 true IE42484B1 (en) | 1980-08-13 |
Family
ID=5939606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE338/76A IE42484B1 (en) | 1975-02-22 | 1976-02-20 | Solution polymerisation or copolymerisation of acrylonitrile |
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 |
| DE2507777A1 (de) | 1976-09-02 |
| AT346584B (de) | 1978-11-10 |
| 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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