CA2656671A1 - Polyarenazole microfilaments and process for making same - Google Patents
Polyarenazole microfilaments and process for making same Download PDFInfo
- Publication number
- CA2656671A1 CA2656671A1 CA 2656671 CA2656671A CA2656671A1 CA 2656671 A1 CA2656671 A1 CA 2656671A1 CA 2656671 CA2656671 CA 2656671 CA 2656671 A CA2656671 A CA 2656671A CA 2656671 A1 CA2656671 A1 CA 2656671A1
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- filament
- applied voltage
- polypyridazole
- pbo
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims description 28
- 210000003632 microfilament Anatomy 0.000 title description 3
- 229920000642 polymer Polymers 0.000 claims abstract description 73
- 239000004744 fabric Substances 0.000 claims abstract description 7
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 17
- 229920002577 polybenzoxazole Polymers 0.000 claims description 12
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- 239000000835 fiber Substances 0.000 description 32
- 239000000203 mixture Substances 0.000 description 17
- 238000009987 spinning Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 229920001410 Microfiber Polymers 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 7
- 239000003658 microfiber Substances 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- 239000004693 Polybenzimidazole Substances 0.000 description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- OYFRNYNHAZOYNF-UHFFFAOYSA-N 2,5-dihydroxyterephthalic acid Chemical compound OC(=O)C1=CC(O)=C(C(O)=O)C=C1O OYFRNYNHAZOYNF-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 229920002480 polybenzimidazole Polymers 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 229920012306 M5 Rigid-Rod Polymer Fiber Polymers 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000002121 nanofiber Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- -1 polypropylene Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000003252 repetitive effect Effects 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229920006376 polybenzimidazole fiber Polymers 0.000 description 2
- IAYUQKZZQKUOFL-UHFFFAOYSA-N pyridine-2,3,5,6-tetramine Chemical compound NC1=CC(N)=C(N)N=C1N IAYUQKZZQKUOFL-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229920003252 rigid-rod polymer Polymers 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- RLXBOUUYEFOFSW-UHFFFAOYSA-N 2,5-diaminobenzene-1,4-diol Chemical compound NC1=CC(O)=C(N)C=C1O RLXBOUUYEFOFSW-UHFFFAOYSA-N 0.000 description 1
- DPYROBMRMXHROQ-UHFFFAOYSA-N 4,6-diaminobenzene-1,3-diol Chemical compound NC1=CC(N)=C(O)C=C1O DPYROBMRMXHROQ-UHFFFAOYSA-N 0.000 description 1
- KSFAWAYSJUPRED-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetramine Chemical group NC1=C(N)C(N)=CC(C=2C=CC=CC=2)=C1N KSFAWAYSJUPRED-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229920001096 M5 fiber Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- FHESUNXRPBHDQM-UHFFFAOYSA-N diphenyl benzene-1,3-dicarboxylate Chemical compound C=1C=CC(C(=O)OC=2C=CC=CC=2)=CC=1C(=O)OC1=CC=CC=C1 FHESUNXRPBHDQM-UHFFFAOYSA-N 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000001523 electrospinning Methods 0.000 description 1
- 238000010041 electrostatic spinning Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- CYVYLVVUKPNYKL-UHFFFAOYSA-N quinoline-2,6-dicarboxylic acid Chemical compound N1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 CYVYLVVUKPNYKL-UHFFFAOYSA-N 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/22—Polybenzoxazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/18—Polybenzimidazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D5/00—Formation of filaments, threads, or the like
- D01D5/0007—Electro-spinning
- D01D5/0015—Electro-spinning characterised by the initial state of the material
- D01D5/003—Electro-spinning characterised by the initial state of the material the material being a polymer solution or dispersion
- D01D5/0038—Electro-spinning characterised by the initial state of the material the material being a polymer solution or dispersion the fibre formed by solvent evaporation, i.e. dry electro-spinning
-
- 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
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/74—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polycondensates of cyclic compounds, e.g. polyimides, polybenzimidazoles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/298—Physical dimension
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/60—Nonwoven fabric [i.e., nonwoven strand or fiber material]
- Y10T442/608—Including strand or fiber material which is of specific structural definition
- Y10T442/614—Strand or fiber material specified as having microdimensions [i.e., microfiber]
- Y10T442/626—Microfiber is synthetic polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Mechanical Engineering (AREA)
- Artificial Filaments (AREA)
- Spinning Methods And Devices For Manufacturing Artificial Fibers (AREA)
- Woven Fabrics (AREA)
- Nonwoven Fabrics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83442606P | 2006-07-31 | 2006-07-31 | |
| US60/834,426 | 2006-07-31 | ||
| PCT/US2007/074465 WO2008016825A1 (en) | 2006-07-31 | 2007-07-26 | Polyarenazole microfilaments and process for making same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2656671A1 true CA2656671A1 (en) | 2008-02-07 |
Family
ID=38664076
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2656671 Abandoned CA2656671A1 (en) | 2006-07-31 | 2007-07-26 | Polyarenazole microfilaments and process for making same |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20090311935A1 (enExample) |
| EP (1) | EP2046864B1 (enExample) |
| JP (1) | JP5235880B2 (enExample) |
| KR (1) | KR101474574B1 (enExample) |
| CN (1) | CN101568571B (enExample) |
| BR (1) | BRPI0714084A2 (enExample) |
| CA (1) | CA2656671A1 (enExample) |
| DE (1) | DE602007003379D1 (enExample) |
| MX (1) | MX2009001101A (enExample) |
| WO (1) | WO2008016825A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104862826B (zh) * | 2015-05-28 | 2017-01-25 | 中蓝晨光化工研究设计院有限公司 | 一种pipd/pbo混纺纤维的制备方法 |
| CN109943906A (zh) * | 2017-12-21 | 2019-06-28 | 中蓝晨光化工有限公司 | 一种高伸长率聚对苯撑苯并二噁唑纤维及其制备方法 |
| EP3847299B1 (en) * | 2018-09-12 | 2024-11-06 | Gharda Chemicals Limited | Spun abpbi fibers and process for preparing the same |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US26065A (en) * | 1859-11-08 | Improvement in cotton-gins | ||
| US3441640A (en) * | 1964-12-07 | 1969-04-29 | Celanese Corp | Process for wet-spinning polybenzimidazoles |
| US4263245A (en) * | 1979-04-23 | 1981-04-21 | Celanese Corporation | Process for producing high-strength, ultralow denier polybenzimidazole (PBI) filaments |
| US5142021A (en) * | 1990-10-19 | 1992-08-25 | The Dow Chemical Company | Use of reducing agents in polybenzazole synthesis |
| US5273703A (en) * | 1992-08-13 | 1993-12-28 | The Dow Chemical Company | Process for post-spin finishing of polybenzoxazole fibers |
| KR100306676B1 (ko) * | 1993-04-28 | 2001-11-30 | 샬크비즈크 피이터 코르넬리스; 페트귄터 | 피리도비스이미다졸성분의강성막대형중합체 |
| US5417915A (en) * | 1993-12-03 | 1995-05-23 | The Dow Chemical Company | Process for post-spin finishing of polybenzoxazole fibers |
| JP3613719B2 (ja) * | 1994-12-23 | 2005-01-26 | 東洋紡績株式会社 | ポリベンザゾール繊維の製造方法 |
| US6315806B1 (en) * | 1997-09-23 | 2001-11-13 | Leonard Torobin | Method and apparatus for producing high efficiency fibrous media incorporating discontinuous sub-micron diameter fibers, and web media formed thereby |
| KR100549140B1 (ko) * | 2002-03-26 | 2006-02-03 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 일렉트로-브로운 방사법에 의한 초극세 나노섬유 웹제조방법 |
| KR100543489B1 (ko) * | 2002-11-07 | 2006-01-23 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 일렉트로-브로운 방사법에 의한 초극세 나노섬유 제조장치및 제조방법 |
| US20050026526A1 (en) * | 2003-07-30 | 2005-02-03 | Verdegan Barry M. | High performance filter media with internal nanofiber structure and manufacturing methodology |
| US20050048274A1 (en) * | 2003-08-26 | 2005-03-03 | Rabolt John F. | Production of nanowebs by an electrostatic spinning apparatus and method |
| JP2006069141A (ja) * | 2004-09-06 | 2006-03-16 | Teijin Techno Products Ltd | 複合繊維構造体およびその製造方法 |
| US20060110597A1 (en) * | 2004-11-23 | 2006-05-25 | Koralek Alan S | Highly cut-resistant yarn and protective articles made therefrom |
| JP2006152479A (ja) * | 2004-11-29 | 2006-06-15 | Toray Ind Inc | 極細繊維の製造装置およびそれを用いた製造方法 |
| US20060137317A1 (en) * | 2004-12-28 | 2006-06-29 | Bryner Michael A | Filtration media for filtering particulate material from gas streams |
| JP2006188797A (ja) * | 2005-01-07 | 2006-07-20 | Teijin Ltd | 剛直系複素環高分子からなる繊維 |
| KR101324822B1 (ko) * | 2005-03-28 | 2013-11-01 | 마젤란 시스템즈 인터내셔날, 엘엘시 | 높은 고유 점도 중합체 및 그로부터의 섬유 |
| JP5036700B2 (ja) * | 2005-03-28 | 2012-09-26 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | ポリアレーンアゾール重合体の製造方法 |
| WO2006105230A1 (en) * | 2005-03-28 | 2006-10-05 | E. I. Du Pont De Nemours And Company | Process for the production of polyareneazole polymer |
-
2007
- 2007-07-26 KR KR1020097004253A patent/KR101474574B1/ko active Active
- 2007-07-26 JP JP2009522959A patent/JP5235880B2/ja active Active
- 2007-07-26 CA CA 2656671 patent/CA2656671A1/en not_active Abandoned
- 2007-07-26 MX MX2009001101A patent/MX2009001101A/es active IP Right Grant
- 2007-07-26 BR BRPI0714084-3A patent/BRPI0714084A2/pt not_active IP Right Cessation
- 2007-07-26 EP EP20070799848 patent/EP2046864B1/en active Active
- 2007-07-26 DE DE200760003379 patent/DE602007003379D1/de active Active
- 2007-07-26 US US12/375,535 patent/US20090311935A1/en not_active Abandoned
- 2007-07-26 WO PCT/US2007/074465 patent/WO2008016825A1/en not_active Ceased
- 2007-07-26 CN CN2007800284389A patent/CN101568571B/zh active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2046864B1 (en) | 2009-11-18 |
| DE602007003379D1 (de) | 2009-12-31 |
| CN101568571B (zh) | 2013-08-21 |
| EP2046864A1 (en) | 2009-04-15 |
| WO2008016825A1 (en) | 2008-02-07 |
| JP2009545684A (ja) | 2009-12-24 |
| KR101474574B1 (ko) | 2014-12-18 |
| KR20090040904A (ko) | 2009-04-27 |
| US20090311935A1 (en) | 2009-12-17 |
| MX2009001101A (es) | 2009-02-10 |
| CN101568571A (zh) | 2009-10-28 |
| BRPI0714084A2 (pt) | 2012-12-18 |
| JP5235880B2 (ja) | 2013-07-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |
Effective date: 20150213 |