DE2504593C3 - - Google Patents
Info
- Publication number
- DE2504593C3 DE2504593C3 DE19752504593 DE2504593A DE2504593C3 DE 2504593 C3 DE2504593 C3 DE 2504593C3 DE 19752504593 DE19752504593 DE 19752504593 DE 2504593 A DE2504593 A DE 2504593A DE 2504593 C3 DE2504593 C3 DE 2504593C3
- Authority
- DE
- Germany
- Prior art keywords
- fibers
- acrylonitrile copolymer
- mol
- acrylonitrile
- carboxyl groups
- 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
Links
- 239000000835 fiber Substances 0.000 claims description 68
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 39
- 229920001577 copolymer Polymers 0.000 claims description 39
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 27
- 239000004917 carbon fiber Substances 0.000 claims description 27
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 12
- -1 alkali metal cation Chemical class 0.000 claims description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 7
- 230000001590 oxidative Effects 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 238000002166 wet spinning Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000010000 carbonizing Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000004429 atoms Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 239000011260 aqueous acid Substances 0.000 claims 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M isothiocyanate Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- 238000011105 stabilization Methods 0.000 description 8
- 238000009987 spinning Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000011734 sodium Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000007363 ring formation reaction Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- VGTPCRGMBIAPIM-UHFFFAOYSA-M Sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 102000014961 Protein Precursors Human genes 0.000 description 2
- 108010078762 Protein Precursors Proteins 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000003763 carbonization Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000005087 graphitization Methods 0.000 description 2
- 239000003779 heat-resistant material Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- 230000000737 periodic Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-Vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N 2-cyanopropene-1 Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N 2-methyl-2-propenoic acid methyl ester Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N Acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N Itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinylpyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L Zinc chloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium(0) Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000001771 impaired Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- 229920005594 polymer fiber Polymers 0.000 description 1
- HWDDJFFLFNQAFQ-UHFFFAOYSA-M potassium;4-ethenylbenzenesulfonate Chemical compound [K+].[O-]S(=O)(=O)C1=CC=C(C=C)C=C1 HWDDJFFLFNQAFQ-UHFFFAOYSA-M 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000003014 reinforcing Effects 0.000 description 1
- 238000004904 shortening Methods 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
- 239000007858 starting material Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- MLVWCBYTEFCFSG-UHFFFAOYSA-L zinc;dithiocyanate Chemical compound [Zn+2].[S-]C#N.[S-]C#N MLVWCBYTEFCFSG-UHFFFAOYSA-L 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1420974 | 1974-02-04 | ||
| JP49014209A JPS5133211B2 (US20080293856A1-20081127-C00127.png) | 1974-02-04 | 1974-02-04 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2504593A1 DE2504593A1 (de) | 1975-08-07 |
| DE2504593B2 DE2504593B2 (de) | 1976-09-23 |
| DE2504593C3 true DE2504593C3 (US20080293856A1-20081127-C00127.png) | 1977-05-05 |
Family
ID=11854702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752504593 Granted DE2504593B2 (de) | 1974-02-04 | 1975-02-04 | Verfahren zur herstellung von kohlenstoffasern |
Country Status (6)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5231124A (en) * | 1975-09-01 | 1977-03-09 | Japan Exlan Co Ltd | Improved preparation of carbon fiber |
| JPS5920004B2 (ja) * | 1977-03-23 | 1984-05-10 | 日本エクスラン工業株式会社 | 炭素繊維の製造方法 |
| JPS5848643B2 (ja) * | 1977-04-05 | 1983-10-29 | 東レ株式会社 | 高純度アクリル系炭素繊維 |
| IT1112296B (it) * | 1978-07-28 | 1986-01-13 | Snia Viscosa | Polimeri acrilici ad alta resistenza alla fiamma,filati costituiti da tali polimeri,e processo di fabbricazione di tali polimeri e di tali filati |
| US4336022A (en) * | 1979-08-01 | 1982-06-22 | E. I. Du Pont De Nemours And Company | Acrylic precursor fibers suitable for preparing carbon or graphite fibers |
| JPS5982421A (ja) * | 1982-11-04 | 1984-05-12 | Mitsubishi Rayon Co Ltd | 炭素繊維の製法 |
| US4603041A (en) * | 1984-07-19 | 1986-07-29 | E. I. Du Pont De Nemours And Company | Cyclization of acrylic fiber |
| US5066433A (en) * | 1988-02-16 | 1991-11-19 | Hercules Incorporated | Method of manufacturing carbon fiber using preliminary stretch |
| ATE495202T1 (de) | 1998-10-27 | 2011-01-15 | Westlake Longview Corp | Verfahren zur olefinpolymerisation, polyethylene und daraus hergestellte folien und artikel |
| US6323148B1 (en) | 1998-12-04 | 2001-11-27 | Equistar Chemicals, Lp | Ethylene polymerization catalyst and catalyst system |
| US6171993B1 (en) | 1998-12-04 | 2001-01-09 | Equistar Chemicals, Lp | Enhanced-impact LLDPE with a shear modifiable network structure |
| CA2446603A1 (en) * | 2001-05-07 | 2002-11-14 | Exxonmobil Chemical Patents Inc. | Polyethylene resins |
| FR2842192B1 (fr) * | 2002-07-12 | 2004-10-01 | Snecma Propulsion Solide | Procede et installation pour l'obtention de produits en carbone a partir de produits en precurseur de carbone |
| EP2147776A1 (de) * | 2008-07-23 | 2010-01-27 | SGL Carbon SE | Verfahren zur Herstellung eines Fasergelege-verstärkten Verbundwerkstoffs, sowie Fasergelege-verstärkte Verbundwerkstoffe und deren Verwendung |
| DE102009047514A1 (de) | 2009-12-04 | 2011-07-07 | Sgl Carbon Se, 65203 | Fasern zur Herstellung von Verbundwerkstoffen |
| DE102009047491A1 (de) | 2009-12-04 | 2011-06-09 | Sgl Carbon Se | Herstellung einer 3D-Textilstruktur und Faserhalbzeug aus Faserverbundstoffen |
| US10407802B2 (en) | 2015-12-31 | 2019-09-10 | Ut-Battelle Llc | Method of producing carbon fibers from multipurpose commercial fibers |
| US11299824B2 (en) | 2019-08-21 | 2022-04-12 | Hexcel Corporation | Selective control of oxidation atmospheres in carbon fiber production |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3027222A (en) * | 1957-09-03 | 1962-03-27 | Du Pont | Fireproof acrylonitrile copolymers |
| US3491179A (en) * | 1967-01-03 | 1970-01-20 | American Cyanamid Co | Preparation of acrylonitrile polymer fibers |
| US3635675A (en) * | 1968-05-28 | 1972-01-18 | Us Air Force | Preparation of graphite yarns |
| US3592595A (en) * | 1968-11-21 | 1971-07-13 | Celanese Corp | Stabilization and carbonization of acrylic fibrous material |
| GB1288563A (US20080293856A1-20081127-C00127.png) * | 1969-01-20 | 1972-09-13 | ||
| US3841079A (en) * | 1970-04-14 | 1974-10-15 | Celanese Corp | Carbon filaments capable of substantial crack diversion during fracture |
| US3817700A (en) * | 1970-09-14 | 1974-06-18 | Monsanto Co | Process for treating acrylic fibers to obtain carbonizable and graphitizable substrates |
| US3791840A (en) * | 1970-10-21 | 1974-02-12 | Union Carbide Corp | Treatment of carbon fibers to improve shear strength in composites |
| US3746560A (en) * | 1971-03-25 | 1973-07-17 | Great Lakes Carbon Corp | Oxidized carbon fibers |
| JPS4724185U (US20080293856A1-20081127-C00127.png) * | 1971-04-09 | 1972-11-17 | ||
| US3764662A (en) * | 1971-04-21 | 1973-10-09 | Gen Electric | Process for making carbon fiber |
| US3776829A (en) * | 1971-10-26 | 1973-12-04 | Great Lakes Carbon Corp | Aminated carbon fibers |
| US3954947A (en) * | 1972-11-17 | 1976-05-04 | Union Carbide Corporation | Rapid stabilization of polyacrylonitrile fibers prior to carbonization |
-
1974
- 1974-02-04 JP JP49014209A patent/JPS5133211B2/ja not_active Expired
-
1975
- 1975-01-20 US US05/543,008 patent/US4001382A/en not_active Expired - Lifetime
- 1975-01-27 GB GB3521/75A patent/GB1481893A/en not_active Expired
- 1975-02-03 FR FR7503308A patent/FR2259924B1/fr not_active Expired
- 1975-02-04 CA CA219,386A patent/CA1040370A/en not_active Expired
- 1975-02-04 DE DE19752504593 patent/DE2504593B2/de active Granted
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