US20090311935A1 - Polyarenazole microfilaments and process for making same - Google Patents
Polyarenazole microfilaments and process for making same Download PDFInfo
- Publication number
- US20090311935A1 US20090311935A1 US12/375,535 US37553507A US2009311935A1 US 20090311935 A1 US20090311935 A1 US 20090311935A1 US 37553507 A US37553507 A US 37553507A US 2009311935 A1 US2009311935 A1 US 2009311935A1
- Authority
- US
- United States
- Prior art keywords
- polymer
- filament
- polyarenazole
- applied voltage
- average diameter
- 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
- JPQPSYBZKIPGTI-UHFFFAOYSA-N CC.CC.CC1=CC=C(C2=NC3=C(C=C4N=C(C)SC4=C3)S2)C=C1.CC1=CC=C(C2=NC3=C(C=C4NC(C)OC4=C3)O2)C=C1.CC1=CC=C(C2=NC3=C(C=C4OC(C)=NC4=C3)O2)C=C1.CC1=CC=C(C2=NC3=C(C=C4SC(C)=NC4=C3)S2)C=C1.CC1=NC2=C(C=CC=C2)O1.CC1=NC2=C(C=CC=C2)S1 Chemical compound CC.CC.CC1=CC=C(C2=NC3=C(C=C4N=C(C)SC4=C3)S2)C=C1.CC1=CC=C(C2=NC3=C(C=C4NC(C)OC4=C3)O2)C=C1.CC1=CC=C(C2=NC3=C(C=C4OC(C)=NC4=C3)O2)C=C1.CC1=CC=C(C2=NC3=C(C=C4SC(C)=NC4=C3)S2)C=C1.CC1=NC2=C(C=CC=C2)O1.CC1=NC2=C(C=CC=C2)S1 JPQPSYBZKIPGTI-UHFFFAOYSA-N 0.000 description 1
- HALTVDHZQDFPAA-UHFFFAOYSA-N [H]N1C(C)=NC2=CC3=C(N=C21)N=C(C1=C(O)C=C(C)C(O)=C1)N3[H] Chemical compound [H]N1C(C)=NC2=CC3=C(N=C21)N=C(C1=C(O)C=C(C)C(O)=C1)N3[H] HALTVDHZQDFPAA-UHFFFAOYSA-N 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
Definitions
- the present invention concerns polyarenazole microfilaments and processes for making such filaments.
- Certain low denier fibers have been shown to be useful in a variety of end uses such as filtration media, cell & tissue cultures, drug delivery systems, and specialty textiles.
- U.S. Pat. No. No. 4,263,245 describes certain low denier, high-strength polybibenzimidazole filaments that are 20 to 200 microns in diameter.
- Filtration mediums, fine particle wipe mediums and absorbent mediums containing a mixture of submicron and greater than submicron fibers are disclosed in U.S. Pat. No. 6,315,806.
- Preferred fibers are said to be made from polypropylene polymer.
- Published U.S. Application No. 20050026526 discloses filter media having a mixture of course fibers and fine fibers of diameter less than 1 ⁇ m.
- PCT Patent Application No. WO 03/080905 discloses the preparation of a nanofiber web by an electro-blown spinning process.
- PCT Patent Application No. WO 05/026398 describes production of nanofibers by reactive electrospinning.
- a method for producing a webbed fibrillar material is disclosed in published U.S. Application No. 20050048274.
- the process injects polymer through an electric field towards an electrically charged target.
- a polymer filament having an average diameter of about 20 to 5000 nm, the filament comprising a polyarenazole polymer having an inherent viscosity of greater than about 20 g/dl.
- the average diameter is in the range of about 20 to 1000 nm. In certain embodiments, the average diameter is in the range of about 20 to 800 nm. In yet other embodiments, the average diameter is in the range of about 100 to 500 nm.
- the yarn comprising filaments described herein.
- the yarn has a filament tenacity of greater than about 10 g/denier.
- the invention also concerns fabrics and garments comprising the filaments and/or yarns described herein.
- the invention also provides a polyarenazole polymer filament comprising:
- the solution comprising polyarenazole polymer comprises polyphosphoric acid as a solvent.
- the first applied voltage is in the range of ⁇ 1 kV to ⁇ 300 kV.
- the second applied voltage is opposite in polarity to the first applied voltage and in the range of 0 to ⁇ 10 kV.
- a polymer filament having an average diameter of about 20 to 5000 nm, the filament comprising a polyarenazole polymer having an inherent viscosity of greater than about 20 g/dl.
- yarns comprising such filaments. Additional aspects concern fabrics and garments comprising such filaments and/or yarns.
- the filaments and yarns of the instant invention utilize polyarenazole microfibers.
- Polyareneazole polymer may be made by reacting a mix of dry ingredients with a polyphosphoric acid (PPA) solution.
- the dry ingredients may comprise azole-forming monomers and metal powders. Accurately weighed batches of these dry ingredients can be obtained through employment of at least some of the preferred embodiments of the present invention.
- Exemplary azole-forming monomers include 2,5-dimercapto-p-phenylene diamine, terephthalic acid, bis-(4-benzoic acid), oxy-bis-(4-benzoic acid), 2,5-dihydroxyterephthalic acid, isophthalic acid, 2,5-pyridodicarboxylic acid, 2,6-napthalenedicarboxylic acid, 2,6-quinolinedicarboxylic acid, 2,6-bis(4-carboxyphenyl) pyridobisimidazole, 2,3,5,6-tetraaminopyridine, 4,6-diaminoresorcinol, 2,5-diaminohydroquinone, 1,4-diamino-2,5-dithiobenzene, or any combination thereof.
- the azole forming monomers include 2,3,5,6-tetraaminopyridine and 2,5-dihydroxyterephthalic acid.
- it is preferred that that the azole-forming monomers are phosphorylated.
- phosphorylated azole-forming monomers are polymerized in the presence of polyphosphoric acid and a metal catalyst.
- Polybenzoxazole (PBO) and polybenzothiazole (PBZ) two suitable polymers. These polymers are described in PCT Application No. WO 93/20400.
- Polybenzoxazole and polybenzothiazole are preferably made up of repetitive units of the following structures:
- the polybenzimidazole (PBI) fiber comprises polybibenzimidazole polymer.
- One useful polybibenzimidazole polymer is poly(2,2′-(m-phenylene)-5,5′-bibenzimidazole) polymer.
- One commercial PBI polymer is prepared from tetra-aminobiphenyl and diphenyl isophthalate.
- aromatic groups shown joined to the nitrogen atoms may be heterocyclic, they are preferably carbocyclic; and while they may be fused or unfused polycyclic systems, they are preferably single six-membered rings.
- group shown in the main chain of the bis-azoles is the preferred para-phenylene group, that group may be replaced by any divalent organic group which doesn't interfere with preparation of the polymer, or no group at all. For example, that group may be aliphatic up to twelve carbon atoms, tolylene, biphenylene, bis-phenylene ether, and the like.
- the polybenzoxazole and polybenzothiazole used to make fibers of this invention should have at least 25 and preferably at least 100 repetitive units. Preparation of the polymers and spinning of those polymers is disclosed in the aforementioned PCT application WO 93/20400.
- Polypyridoimidazole polymer may be made by reacting a mix of dry ingredients with a polyphosphoric acid (PPA) solution.
- the dry ingredients may comprise pyridobisimidazole-forming monomers and metal powders.
- the polypyridobisimidazole polymer used to make the rigid rod fibers used in the fabrics of this invention should have at least 25 and preferably at least 100 repetitive units.
- the relative molecular weights of the polypyridoimidazole polymers are suitably characterized by diluting the polymer products with a suitable solvent, such as methane sulfonic acid, to a polymer concentration of 0.05 g/dl, and measuring one or more dilute solution viscosity values at 30° C.
- Molecular weight development of polypyridoimidazole polymers of the present invention is suitably monitored by, and correlated to, one or more dilute solution viscosity measurements.
- V inh In ( V rel )/ C
- the polypyridoimidazole polymers are produced that are characterized as providing a polymer solution having an inherent viscosity of at least about 20 dl/g at 30° C. at a polymer concentration of 0.05 g/dl in methane sulfonic acid.
- ultra-fine fibers can be prepared by flash spinning, electrostatic spinning, and melt-blown spinning.
- Ultra-fine fibers, such as microfibers, and nonwoven webs can be produced by a process that utilizes an electro-blown spinning process. In such a process, a polymer solution is discharged through a spinning nozzle to which a high voltage has been applied. The fiber spun from the nozzle is collected on a grounded suction collector. Typically, compressed air is injected at the lower end of the spinning nozzle.
- Such a processes for making microfibers and webs containing such fibers can be found in PCT Patent Application WO03/080905, the disclosure of which is incorporated herein in its entirety.
- fiber is defined as a relatively flexible, macroscopically homogeneous body having a high ratio of length to width across its cross-sectional area perpendicular to its length.
- the fiber cross section can be any shape, but is typically round.
- filament or “continuous filament” is used interchangeably with the term “fiber.”
- Basis weight cam be determined by ASTM D-3776, which is hereby incorporated by reference and reported in g/m 2 .
- fiber diameter can be determined as follows. Ten scanning electron microscope (SEM) images at 5,000 ⁇ magnification were taken of each microfiber layer sample. The diameter of eleven (11) clearly distinguishable microfibers were measured from each SEM image and recorded. Defects were not included (i.e., lumps of microfibers, polymer drops, intersections of microfibers). The average fiber diameter for each sample was calculated.
- tenacity and tensile strength refer to the strength of a fiber, yarn or fabric (ISO 5081) as measured using ASTM D638. Tensile properties of the nonwoven web are being determined by (ISO 1924) “Paper and Board—Determination of Tensile Properties”.
- the 1 atmosphere (absolute) pressure in the mixer is equalized to the 1 atmosphere pressure in the N 2 -blanketed weigh chamber.
- the monomer complex, tin, and benzoic acid are transferred to the 10CV mixer, and then the transfer valve is closed.
- the mixer blades are started and their speed is ramped to 40 rpm.
- Water cooling is restarted when the agitator starts, and the monomer complex, tin, and benzoic acid are blended into the PPA mixture for 10 minutes after the mixer blades have reached the 40 rpm rate. Then a vacuum is slowly applied to degas the mixture as the blending continues. Water cooling is controlled to maintain the contents of the mixer at 75 (+/ ⁇ 5)° C.
- the pressure in the mixer is reduced to 50 mm Hg pressure and mixing is continued for 10 minutes. Then the mixer blade speed is reduced to 12 rpm and water cooling is reduced to allow the temperature of the contents in the mixer to rise to 85 (+/ ⁇ 5)° C. The mixer blades are then stopped, N 2 is admitted to bring the pressure up to 1 atmosphere, and the contents of the mixer are then transferred to a feed tank having two agitators (a DIT 10SC mixer).
- the reactant mixture in the feed tank is maintained at a temperature of 110° C. and a pressure of 50 mm Hg absolute. Both agitators are run at 40 rpm.
- the reactant mixture is pumped from the tank at an average rate of 10,050 grams/hour through a heat exchanger, to increase the temperature of the mixture to 137° C., and into a series of three static mixer reactors, allowing a 3-hour hold-up time for oligomer formation.
- superphosphoric acid (SPA) (76% P 2 O 5 ) is injected into the oligomer mixture at an average rate of 1079 grams/hour.
- the oligomer mixture with SPA is then well blended through a static mixer and transferred to a stirred surge tank any volatiles are removed by a vacuum.
- the stirred surge tank is a DIT 5SC mixer, having a temperature maintained at 137° C. Average hold-up time in the surge tank is 11 ⁇ 4 hr.
- the oligomer mixture is then further polymerized to the desired molecular weight at a temperature of 180° C.
- the oligomer mixture is first pumped through a heat exchanger to raise the temperature of the mixture to 180 C. and then through a reactor system of static mixers and a rotating Couette-type-shearing reactor imparting 5 sec ⁇ 1 shear rate to the polymerizing solution.
- the reactor system is maintained at 180° C. (+/ ⁇ 5 degrees) and the hold-up time in the reactor system is 4 hours.
- a solution containing a polymer having an inherent viscosity of 25 dl/g is obtained.
- a 20 weight percent solution of 25 IV polymer in PPA (having a strength of equivalent of 81.5 percent P205 is forwarded to a spinnerette pack having electrically charged spinning nozzles.
- the spinning nozzles have a diameter of about 0.25 mm, an L/d ratio of about 10, DCD of 300 mm, a spinning pressure of about 6 kg/cm 2 , and an applied voltage of about 50 kV.
- the number of spinning nozzles in the spinnerette pack is 51.
- Surrounding the spinning nozzles are air nozzles that provide high pressure air for the electro-blowing process.
- the air velocity is about 3000 meters/minute and the air temperature is about 100 degrees Celsius.
- the spun filaments are collected on a moving belt by suction to form a web.
- the distance between the spinnerette nozzle and suction collection belt is 30 cm.
- the web is sprayed with water at 40 degrees Celsius for 20 seconds.
- the web is then passed through an oven operating at a temperature of 300° C. for a residence time of 60 seconds.
- the web is then washed with a water spray.
- the water temperature is 40° C.
- the web is then dried by passing the web through an oven operating at 150° C. for a residence time of 40 seconds.
- This example illustrates the optional heat treatment of the web made in the previous examples.
- the process of a preceding example is repeated, except after drying, a volatile antistatic finish is applied to the web instead of a textile finish, and the web is immediately conveyed to an oven instead of being wound on a bobbin.
- the dried web is conveyed to an electrically heated belt, which raises the temperature of the web to 400° C.
- the web is then conveyed into a N 2 -blanketed tube oven which raises the temperature of the yarn to 500° C.
- the web Before exiting the N 2 atmosphere, the web is cooled in a room temperature N 2 atmosphere for 2 seconds, and a finish is applied. The web is then collected.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Mechanical Engineering (AREA)
- Artificial Filaments (AREA)
- Nonwoven Fabrics (AREA)
- Spinning Methods And Devices For Manufacturing Artificial Fibers (AREA)
- Woven Fabrics (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/375,535 US20090311935A1 (en) | 2006-07-31 | 2007-07-26 | Polyarenazole microfilaments and process for making same |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US83442606P | 2006-07-31 | 2006-07-31 | |
PCT/US2007/074465 WO2008016825A1 (en) | 2006-07-31 | 2007-07-26 | Polyarenazole microfilaments and process for making same |
US12/375,535 US20090311935A1 (en) | 2006-07-31 | 2007-07-26 | Polyarenazole microfilaments and process for making same |
Publications (1)
Publication Number | Publication Date |
---|---|
US20090311935A1 true US20090311935A1 (en) | 2009-12-17 |
Family
ID=38664076
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/375,535 Abandoned US20090311935A1 (en) | 2006-07-31 | 2007-07-26 | Polyarenazole microfilaments and process for making same |
Country Status (10)
Country | Link |
---|---|
US (1) | US20090311935A1 (ko) |
EP (1) | EP2046864B1 (ko) |
JP (1) | JP5235880B2 (ko) |
KR (1) | KR101474574B1 (ko) |
CN (1) | CN101568571B (ko) |
BR (1) | BRPI0714084A2 (ko) |
CA (1) | CA2656671A1 (ko) |
DE (1) | DE602007003379D1 (ko) |
MX (1) | MX2009001101A (ko) |
WO (1) | WO2008016825A1 (ko) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104862826A (zh) * | 2015-05-28 | 2015-08-26 | 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 |
WO2020053803A1 (en) * | 2018-09-12 | 2020-03-19 | Gharda Chemicals Limited | Spun abpbi fibers and process for preparing the same |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
Citations (14)
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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 |
US5417915A (en) * | 1993-12-03 | 1995-05-23 | The Dow Chemical Company | Process for post-spin finishing of polybenzoxazole fibers |
US5674969A (en) * | 1993-04-28 | 1997-10-07 | Akzo Nobel Nv | Rigid rod polymer based on pyridobisimidazole |
US5976447A (en) * | 1994-12-23 | 1999-11-02 | Toyobo Co., Ltd. | Process for the preparation of polybenzoxazole and polybenzothiazole filaments and fibers |
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 |
KR20040040692A (ko) * | 2002-11-07 | 2004-05-13 | 주식회사 나노테크닉스 | 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 |
US20060280937A1 (en) * | 2005-03-28 | 2006-12-14 | E.I. Du Pont De Nemours And Company | High inherent viscosity polymers and fibers therefrom |
US20060287475A1 (en) * | 2005-03-28 | 2006-12-21 | Allen Steven R | Process for the production of polyarenazole polymer |
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KR100549140B1 (ko) * | 2002-03-26 | 2006-02-03 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 일렉트로-브로운 방사법에 의한 초극세 나노섬유 웹제조방법 |
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 |
US8092566B2 (en) * | 2004-12-28 | 2012-01-10 | E.I. Du Pont De Nemours And Company | 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 |
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 MX MX2009001101A patent/MX2009001101A/es active IP Right Grant
- 2007-07-26 CA CA 2656671 patent/CA2656671A1/en not_active Abandoned
- 2007-07-26 CN CN2007800284389A patent/CN101568571B/zh active Active
- 2007-07-26 KR KR1020097004253A patent/KR101474574B1/ko active IP Right Grant
- 2007-07-26 JP JP2009522959A patent/JP5235880B2/ja active Active
- 2007-07-26 WO PCT/US2007/074465 patent/WO2008016825A1/en active Application Filing
- 2007-07-26 DE DE200760003379 patent/DE602007003379D1/de active Active
- 2007-07-26 EP EP20070799848 patent/EP2046864B1/en active Active
- 2007-07-26 BR BRPI0714084-3A patent/BRPI0714084A2/pt not_active IP Right Cessation
- 2007-07-26 US US12/375,535 patent/US20090311935A1/en not_active Abandoned
Patent Citations (14)
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 |
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Cited By (3)
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CN104862826A (zh) * | 2015-05-28 | 2015-08-26 | 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 |
WO2020053803A1 (en) * | 2018-09-12 | 2020-03-19 | Gharda Chemicals Limited | Spun abpbi fibers and process for preparing the same |
US11993867B2 (en) | 2018-09-12 | 2024-05-28 | Gharda Chemicals Limited | Spun ABPBI fibers and process for preparing the same |
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WO2008016825A1 (en) | 2008-02-07 |
JP2009545684A (ja) | 2009-12-24 |
CN101568571A (zh) | 2009-10-28 |
MX2009001101A (es) | 2009-02-10 |
KR20090040904A (ko) | 2009-04-27 |
DE602007003379D1 (de) | 2009-12-31 |
JP5235880B2 (ja) | 2013-07-10 |
CA2656671A1 (en) | 2008-02-07 |
CN101568571B (zh) | 2013-08-21 |
EP2046864A1 (en) | 2009-04-15 |
EP2046864B1 (en) | 2009-11-18 |
KR101474574B1 (ko) | 2014-12-18 |
BRPI0714084A2 (pt) | 2012-12-18 |
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