GB2321215A - Cross-linked acrylonitrile precursors for carbon fibres - Google Patents
Cross-linked acrylonitrile precursors for carbon fibres Download PDFInfo
- Publication number
- GB2321215A GB2321215A GB9700946A GB9700946A GB2321215A GB 2321215 A GB2321215 A GB 2321215A GB 9700946 A GB9700946 A GB 9700946A GB 9700946 A GB9700946 A GB 9700946A GB 2321215 A GB2321215 A GB 2321215A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cross
- elongate member
- acrylonitrile
- polymer
- melt
- 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- Withdrawn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 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title description 5
- 229910052799 carbon Inorganic materials 0.000 title description 5
- 239000002243 precursor Substances 0.000 title description 2
- 229920002239 polyacrylonitrile Polymers 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 13
- 238000004132 cross linking Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000009877 rendering Methods 0.000 claims description 2
- 238000001125 extrusion Methods 0.000 abstract description 13
- 239000000835 fiber Substances 0.000 abstract description 4
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 238000000197 pyrolysis Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000000578 dry spinning Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- PGYJSURPYAAOMM-UHFFFAOYSA-N 2-ethenoxy-2-methylpropane Chemical compound CC(C)(C)OC=C PGYJSURPYAAOMM-UHFFFAOYSA-N 0.000 description 1
- 229920002972 Acrylic fiber Polymers 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 229920002821 Modacrylic Polymers 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- -1 hydroxymethylene groups Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F9/00—Artificial filaments or the like of other substances; Manufacture thereof; Apparatus specially adapted for the manufacture of carbon filaments
- D01F9/08—Artificial filaments or the like of other substances; Manufacture thereof; Apparatus specially adapted for the manufacture of carbon filaments of inorganic material
- D01F9/12—Carbon filaments; Apparatus specially adapted for the manufacture thereof
- D01F9/14—Carbon filaments; Apparatus specially adapted for the manufacture thereof by decomposition of organic filaments
- D01F9/20—Carbon filaments; Apparatus specially adapted for the manufacture thereof by decomposition of organic filaments from polyaddition, polycondensation or polymerisation products
- D01F9/21—Carbon filaments; Apparatus specially adapted for the manufacture thereof by decomposition of organic filaments from polyaddition, polycondensation or polymerisation products from macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D01F9/22—Carbon filaments; Apparatus specially adapted for the manufacture thereof by decomposition of organic filaments from polyaddition, polycondensation or polymerisation products from macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds from polyacrylonitriles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F11/00—Chemical after-treatment of artificial filaments or the like during manufacture
- D01F11/04—Chemical after-treatment of artificial filaments or the like during manufacture of synthetic polymers
- D01F11/08—Chemical after-treatment of artificial filaments or the like during manufacture of synthetic polymers of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/02—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D01F6/18—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds from polymers of unsaturated nitriles, e.g. polyacrylonitrile, polyvinylidene cyanide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2333/00—Characterised by the use of homopolymers or 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 of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
- C08J2333/18—Homopolymers or copolymers of nitriles
- C08J2333/20—Homopolymers or copolymers of acrylonitrile
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Toxicology (AREA)
- Inorganic Fibers (AREA)
- Artificial Filaments (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
A melt-extruded article, e.g. a fibre or film, a fusible acrylonitrile polymer is cross-linked to render it infusible. The thusly cross-linked article can be oxidised and subsequently carbonised or graphitised in similar manner to articles made by wet- or dry-extrusion of infusible acrylonitrile polymers.
Description
MANUFACTURE OF ELONGATE MEMBERS
This invention relates to the manufacture of elongate members based on acrylonitrile polymers and to their oxidation, carbonisation and graphitisation.
Acrylonitrile polymers are well-known and are described for example in articles in Encyclopaedia of Polymer Science and Engineering, Volume 1 (Wiley-Interscience, 1985) entitled "Acrylonitrile Polymers", at page 426, and "Acrylic
Fibers", at page 334. Acrylic polymers are defined as polymers which contain at least 85% by weight acrylonitrile monomer units. Modacrylic polymers are defined as polymers which contain 40 to 85% by weight acrylonitrile monomer units. Many acrylonitrile polymers, including a large proportion of acrylic polymers, are infusible and decompose without melting when they are heated. Processes are known by which such polymers can be processed into elongate members, for example fibres, using wet- or dry-extrusion techniques.
These involve the extrusion of a solution of the polymer in a suitable solvent into a coagulating bath or an evaporative atmosphere, respectively. Processes are also known whereby elongate members can be manufactured by extrusion of a plasticised acrylonitrile polymer under dry-spinning conditions, followed by removal of the plasticiser. Fusible acrylonitrile polymers are also known and are described for example in US-A-5,106,925 and US-A-5,286,828 (both Curatolo et al.), the contents of which are incorporated herein by way of reference. Such fusible acrylonitrile polymers can be melt-extruded to form an elongate member at temperatures below the temperature at which they decompose. In general, such polymers may alternatively be extruded by wet- and dry-spinning techniques.
Carbon fibres are well-known and are described for example in an article in Encyclopaedia of Polymer Science and Engineering, Volume 2 (Wiley-Interscience, 1S85) entitled "Carbon Fibers", at page 640. Carbon fibres are made by controlled pyrolysis of an organic precursor, for example an acrylonitrile polymer, in fibrous form. Pyrolysis of acrylonitrile polymers typically involves a number of pyrolysis steps. The first step, which may be called the stabilisation step or the oxidation, pre-oxidation or thermosetting step, is carried out at relatively low temperatures, typically in the range 200-450 C, usually in air. The oxidised fibre may then be converted to carbon fibre (carbonised) by heating in an inert atmosphere at 1000-2000'C, or it may be graphitised by heating in an inert atmosphere at temperatures in excess of 2500 C.
Melt-extrusion techniques have certain advantages over dry- and wet-extrusion techniques for the manufacture of elongate members, notably in the relative simplicity of the apparatus required. Furthermore, it is known that melt-extrusion often lends itself more readily to the production of extruded members of modified cross-section by extrusion though a die of modified cross-section than do wet- and dry-extrusion techniques. However, it will readily be appreciated that melt-extruded fusible acrylonitrile polymers cannot readily be pyrolysed to form oxidised, carbonised or graphitised articles. Such polymers melt below the temperature at which they can be oxidised.
The present invention provides a method for manufacturing an elongate member comprising the steps of (1) melt-extruding a fusible acrylonitrile polymer to
produce an elongate member, and as characterising step (2) cross-linking said polymer in said elongate member,
thereby rendering it infusible.
The elongate member may take the form of a film or preferably a fibre.
Suitable fusible acrylonitrile polymers for use in the invention and methods for their manufacture and melt-extrusion are described for example in US-A-5,106,925 and US-A-5,286,828. The fusible acrylonitrile polymer generally contains at least 50 percent by weight acrylonitrile monomer units.
The cross-linking step (2) may be effected in a variety of ways. For example, the extruded elongate member may be exposed to ionising radiation so as to induce cross-linking.
Alternatively, the elongate member may be treated with a chemical reagent which serves to induce cross-linking in acrylonitrile polymers, for example ammonia, hydrazine or a primary or secondary amine. Further alternatively, the fusible acrylonitrile polymer may comprise monomer units which possess a cross-linkable group other than the nitrile group, for example olefinic or hydroxyl groups.
Cross-linking may in such cases be induced in the melt-extruded elongate member by subjecting it to conditions which cause reaction of the cross-linkable group, for example in the case of an olefinic group exposure to W radiation or in the case of a hydroxyl group etherification or reaction with a bifunctional reagent. Care should be taken to avoid excessive cross-linking before and during the melt-extrusion step, because this may adversely affect the physical properties of the melt-extruded member. The cross-linkable group should accordingly possess sufficient thermal stability to resist excessive cross-linking during melt-extrusion. Further alternatively, the acrylonitrile polymer may comprise latent cross-linkable groups. For example, it may comprise t-butyl vinyl ether monomer units serving to provide latent cross-linkable groups, whereby the ether groups can be hydrolysed after melt-extrusion to yield hydroxymethylene groups as cross-linkable groups.
The cross-linked infusible polymer is preferably one which does not show any tendency to melt below about 300 C.
This permits the cross-linked polymer to be oxidised and subsequently pyrolysed using techniques generally known for acrylonitrile elongate members, including fibres. The invention further provides a method which further includes the step of (3) pyrolysing the cross-linked elongate member under oxidising conditions, thereby producing an oxidised acrylonitrile elongate member. The invention yet further provides a method which in addition to step (3) further includes the step of (4) pyrolysing said oxidised elongate member under anaerobic conditions, thereby producing a carbonised or a graphitised elongate member.
Cross-linked elongate members produced by the method of the invention in the form of fibres are suited to the manufacture of carbon fibres, for example for use in fire-retardant materials and in battery separators.
Claims (3)
1. A method for manufacturing an elongate member comprising the steps of (1) melt-extruding a fusible acrylonitrile polymer to produce an elongate member, and as characterising step (2) cross-linking said polymer in said elongate member, thereby rendering it infusible.
2. The method according to claim 1, further including the step (3) of pyrolysing said elongate member after crosslinking said polymer, said pyrolysing being carried out under oxidising conditions, thereby producing an oxidised elongate member.
3. The method according to claim 2, further including the step of (4) pyrolysing said oxidised elongate member under anaerobic conditions, thereby producing a carbonised or graphitised elongate member.
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9700946A GB2321215A (en) | 1997-01-17 | 1997-01-17 | Cross-linked acrylonitrile precursors for carbon fibres |
| JP53393998A JP2001508842A (en) | 1997-01-17 | 1998-01-15 | Manufacturing method of extension member |
| CN98801838A CN1091809C (en) | 1997-01-17 | 1998-01-15 | Manufacture of extensions |
| EA199900666A EA001275B1 (en) | 1997-01-17 | 1998-01-15 | Manufacture of elongate members |
| EP98900898A EP0953071A1 (en) | 1997-01-17 | 1998-01-15 | Manufacture of elongate members |
| CA002278484A CA2278484A1 (en) | 1997-01-17 | 1998-01-15 | Manufacture of elongate members |
| AU56708/98A AU5670898A (en) | 1997-01-17 | 1998-01-15 | Manufacture of elongate members |
| KR1019997005821A KR20000069731A (en) | 1997-01-17 | 1998-01-15 | Manufacture of elongate members |
| IL13067098A IL130670A0 (en) | 1997-01-17 | 1998-01-15 | Manufacture of elongate members |
| PCT/GB1998/000124 WO1998031852A1 (en) | 1997-01-17 | 1998-01-15 | Manufacture of elongate members |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9700946A GB2321215A (en) | 1997-01-17 | 1997-01-17 | Cross-linked acrylonitrile precursors for carbon fibres |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB9700946D0 GB9700946D0 (en) | 1997-03-05 |
| GB2321215A true GB2321215A (en) | 1998-07-22 |
Family
ID=10806159
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9700946A Withdrawn GB2321215A (en) | 1997-01-17 | 1997-01-17 | Cross-linked acrylonitrile precursors for carbon fibres |
Country Status (10)
| Country | Link |
|---|---|
| EP (1) | EP0953071A1 (en) |
| JP (1) | JP2001508842A (en) |
| KR (1) | KR20000069731A (en) |
| CN (1) | CN1091809C (en) |
| AU (1) | AU5670898A (en) |
| CA (1) | CA2278484A1 (en) |
| EA (1) | EA001275B1 (en) |
| GB (1) | GB2321215A (en) |
| IL (1) | IL130670A0 (en) |
| WO (1) | WO1998031852A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000050675A1 (en) * | 1999-02-22 | 2000-08-31 | The Standard Oil Company | Carbon fibers or sheets made from copolymers of acrylonitrile |
| US6630555B2 (en) | 2001-11-06 | 2003-10-07 | Lord Corporation | Internally blocked organoborate initiators and adhesives therefrom |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101798392B (en) * | 2009-12-11 | 2012-01-04 | 中国科学院上海应用物理研究所 | Method for modifying polyacrylonitrile by using gamma ray irradiation |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1033141A (en) * | 1962-04-17 | 1966-06-15 | Courtaulds Ltd | Process for modifying synthetic fibres |
| GB1054137A (en) * | 1963-04-09 | 1967-01-04 | Toyo Rayon Co Ltd | Process for cross linking polymers |
| GB1260449A (en) * | 1969-06-12 | 1972-01-19 | Sigri Elektrographit Gmbh | Improvements in or relating to the production of carbonfibres |
| GB1264763A (en) * | 1970-04-07 | 1972-02-23 | Sigri Elektrographit Gmbh | Improvements in or relating to the production of carbon fibres |
| GB2285009A (en) * | 1993-11-30 | 1995-06-28 | Japan Exlan Co Ltd | Porous acrylonitrile fibres |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1283714A (en) * | 1969-07-09 | 1972-08-02 | Ici Ltd | Process for the production of carbon fibres |
| US3917776A (en) * | 1970-12-12 | 1975-11-04 | Mitsubishi Rayon Co | Process for producing carbon fiber |
| GB1580529A (en) * | 1975-10-24 | 1980-12-03 | Nat Res Dev | Polymers useful for producing carbon fibres |
| US4473372A (en) * | 1983-05-12 | 1984-09-25 | Celanese Corporation | Process for the stabilization of acrylic fibers |
| JPS62149918A (en) * | 1985-12-25 | 1987-07-03 | Mitsubishi Rayon Co Ltd | Manufacturing method of heat-resistant acrylonitrile fiber |
| US4921656A (en) * | 1988-08-25 | 1990-05-01 | Basf Aktiengesellschaft | Formation of melt-spun acrylic fibers which are particularly suited for thermal conversion to high strength carbon fibers |
| US5509986A (en) * | 1994-08-22 | 1996-04-23 | The Dow Chemical Company | Process for preparing an ignition resistant carbonaceous material comprising a melt blowing or spunbonding step, a radiation step and a carbonizing step |
-
1997
- 1997-01-17 GB GB9700946A patent/GB2321215A/en not_active Withdrawn
-
1998
- 1998-01-15 JP JP53393998A patent/JP2001508842A/en active Pending
- 1998-01-15 EP EP98900898A patent/EP0953071A1/en not_active Withdrawn
- 1998-01-15 IL IL13067098A patent/IL130670A0/en unknown
- 1998-01-15 AU AU56708/98A patent/AU5670898A/en not_active Abandoned
- 1998-01-15 CA CA002278484A patent/CA2278484A1/en not_active Abandoned
- 1998-01-15 WO PCT/GB1998/000124 patent/WO1998031852A1/en not_active Ceased
- 1998-01-15 CN CN98801838A patent/CN1091809C/en not_active Expired - Fee Related
- 1998-01-15 EA EA199900666A patent/EA001275B1/en not_active IP Right Cessation
- 1998-01-15 KR KR1019997005821A patent/KR20000069731A/en not_active Withdrawn
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1033141A (en) * | 1962-04-17 | 1966-06-15 | Courtaulds Ltd | Process for modifying synthetic fibres |
| GB1054137A (en) * | 1963-04-09 | 1967-01-04 | Toyo Rayon Co Ltd | Process for cross linking polymers |
| GB1260449A (en) * | 1969-06-12 | 1972-01-19 | Sigri Elektrographit Gmbh | Improvements in or relating to the production of carbonfibres |
| GB1264763A (en) * | 1970-04-07 | 1972-02-23 | Sigri Elektrographit Gmbh | Improvements in or relating to the production of carbon fibres |
| GB2285009A (en) * | 1993-11-30 | 1995-06-28 | Japan Exlan Co Ltd | Porous acrylonitrile fibres |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000050675A1 (en) * | 1999-02-22 | 2000-08-31 | The Standard Oil Company | Carbon fibers or sheets made from copolymers of acrylonitrile |
| US6630555B2 (en) | 2001-11-06 | 2003-10-07 | Lord Corporation | Internally blocked organoborate initiators and adhesives therefrom |
| US6841635B2 (en) | 2001-11-06 | 2005-01-11 | Lord Corporation | Internally blocked organoborate initiators and adhesives therefrom |
Also Published As
| Publication number | Publication date |
|---|---|
| EA199900666A1 (en) | 2000-02-28 |
| CA2278484A1 (en) | 1998-07-23 |
| CN1091809C (en) | 2002-10-02 |
| AU5670898A (en) | 1998-08-07 |
| CN1243554A (en) | 2000-02-02 |
| IL130670A0 (en) | 2000-06-01 |
| EA001275B1 (en) | 2000-12-25 |
| WO1998031852A1 (en) | 1998-07-23 |
| GB9700946D0 (en) | 1997-03-05 |
| KR20000069731A (en) | 2000-11-25 |
| JP2001508842A (en) | 2001-07-03 |
| EP0953071A1 (en) | 1999-11-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |