CA2571384C - Process for preparing polybenzazole fibers by removing polyphosphoric acid - Google Patents
Process for preparing polybenzazole fibers by removing polyphosphoric acid Download PDFInfo
- Publication number
- CA2571384C CA2571384C CA2571384A CA2571384A CA2571384C CA 2571384 C CA2571384 C CA 2571384C CA 2571384 A CA2571384 A CA 2571384A CA 2571384 A CA2571384 A CA 2571384A CA 2571384 C CA2571384 C CA 2571384C
- Authority
- CA
- Canada
- Prior art keywords
- filament
- polyphosphoric acid
- dope
- acid
- base
- 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 - Fee Related
Links
- 229920000137 polyphosphoric acid Polymers 0.000 title claims abstract description 61
- 239000000835 fiber Substances 0.000 title abstract description 59
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 34
- 238000005406 washing Methods 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- 229910001868 water Inorganic materials 0.000 claims description 32
- 239000002585 base Substances 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 229920002577 polybenzoxazole Polymers 0.000 claims description 17
- 238000006386 neutralization reaction Methods 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 150000001768 cations Chemical class 0.000 claims description 8
- 229920002480 polybenzimidazole Polymers 0.000 claims description 7
- 239000004693 Polybenzimidazole Substances 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 claims description 4
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- ODINCKMPIJJUCX-UHFFFAOYSA-N Calcium oxide Chemical compound [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 2
- 102000009097 Phosphorylases Human genes 0.000 claims description 2
- 108010073135 Phosphorylases Proteins 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 235000010216 calcium carbonate Nutrition 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- 235000011116 calcium hydroxide Nutrition 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 claims description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 2
- 239000000347 magnesium hydroxide Substances 0.000 claims description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 2
- 235000012254 magnesium hydroxide Nutrition 0.000 claims description 2
- 239000011736 potassium bicarbonate Substances 0.000 claims description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 2
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 235000017550 sodium carbonate Nutrition 0.000 claims description 2
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 claims description 2
- 229910001866 strontium hydroxide Inorganic materials 0.000 claims description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004744 fabric Substances 0.000 abstract description 11
- 239000000243 solution Substances 0.000 description 31
- 238000005345 coagulation Methods 0.000 description 29
- 230000015271 coagulation Effects 0.000 description 29
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 13
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 9
- 229910052698 phosphorus Inorganic materials 0.000 description 9
- 239000011574 phosphorus Substances 0.000 description 9
- 239000003570 air Substances 0.000 description 8
- 238000010924 continuous production Methods 0.000 description 8
- 239000012634 fragment Substances 0.000 description 8
- 239000012530 fluid Substances 0.000 description 7
- -1 poly(benzimidazole) Polymers 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 241000894007 species Species 0.000 description 5
- 238000009825 accumulation Methods 0.000 description 4
- 238000010923 batch production Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000009616 inductively coupled plasma Methods 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 230000002535 lyotropic effect Effects 0.000 description 2
- 239000012860 organic pigment Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- 235000009967 Erodium cicutarium Nutrition 0.000 description 1
- 240000003759 Erodium cicutarium Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920000106 Liquid crystal polymer Polymers 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000009998 heat setting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003253 poly(benzobisoxazole) Polymers 0.000 description 1
- 229920003254 poly(benzobisthiazole) Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
- Woven Fabrics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/896,790 | 2004-07-22 | ||
| US10/896,790 US7189346B2 (en) | 2004-07-22 | 2004-07-22 | Polybenzazole fibers and processes for their preparation |
| PCT/US2005/025717 WO2006014718A1 (en) | 2004-07-22 | 2005-07-20 | Process for preparing polybenzazole fibers by removing polyphosphoric acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2571384A1 CA2571384A1 (en) | 2006-02-09 |
| CA2571384C true CA2571384C (en) | 2012-10-02 |
Family
ID=35219462
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2571384A Expired - Fee Related CA2571384C (en) | 2004-07-22 | 2005-07-20 | Process for preparing polybenzazole fibers by removing polyphosphoric acid |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7189346B2 (https=) |
| EP (1) | EP1769109B1 (https=) |
| JP (1) | JP4695644B2 (https=) |
| KR (1) | KR101261067B1 (https=) |
| CN (1) | CN100540762C (https=) |
| BR (1) | BRPI0513606A (https=) |
| CA (1) | CA2571384C (https=) |
| MX (1) | MX2007000642A (https=) |
| WO (1) | WO2006014718A1 (https=) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20050013241A (ko) * | 2002-06-26 | 2005-02-03 | 토요 보세키 가부시기가이샤 | 폴리벤즈아졸 섬유 및 그의 용도 |
| WO2006105076A2 (en) * | 2005-03-28 | 2006-10-05 | E.I. Du Pont De Nemours And Company | Processes for preparing monomer complexes |
| US7754846B2 (en) | 2005-03-28 | 2010-07-13 | E. I. Du Pont De Nemours And Company | Thermal processes for increasing polyareneazole inherent viscosities |
| ATE417951T1 (de) | 2005-03-28 | 2009-01-15 | Du Pont | Verfahren zur herstellung von polyarenazolgarn |
| US7906613B2 (en) | 2005-03-28 | 2011-03-15 | Magellan Systems International, Llc | Process for removing cations from polyareneazole fiber |
| KR101327612B1 (ko) * | 2005-03-28 | 2013-11-12 | 마젤란 시스템즈 인터내셔날, 엘엘시 | 방사된 멀티필라멘트사 중의 폴리인산의 무-융합 가수분해 |
| DE602006004037D1 (de) | 2005-03-28 | 2009-01-15 | Du Pont | Verfahren zur herstellung von polyarenazolen mit höher inhärenter viskosität unter verwendung von metallpulvern |
| WO2006105080A1 (en) | 2005-03-28 | 2006-10-05 | E.I. Du Pont De Nemours And Company | Processes for increasing polymer inherent viscosity |
| DE602006019564D1 (de) * | 2005-03-28 | 2011-02-24 | Du Pont | Verfahren zur entfernung von phosphor von einer faser oder einem garn |
| KR101327632B1 (ko) | 2005-03-28 | 2013-11-12 | 마젤란 시스템즈 인터내셔날, 엘엘시 | 폴리아렌아졸 필라멘트 중 폴리인산의 가수분해 방법 |
| US7683157B2 (en) * | 2005-03-28 | 2010-03-23 | E.I. Du Pont De Nemours And Company | Process for the production of polyarenazole polymer |
| US7906615B2 (en) | 2005-03-28 | 2011-03-15 | Magellan Systems International, Llc | Process for hydrolyzing polyphosphoric acid in a spun yarn |
| CN101213329B (zh) * | 2005-03-28 | 2011-01-19 | 纳幕尔杜邦公司 | 具有羟基侧基和阳离子的聚芳烃唑聚合物纤维 |
| CN101203547A (zh) * | 2005-03-28 | 2008-06-18 | 纳幕尔杜邦公司 | 高特性粘度聚合物和由其制成的纤维 |
| US7977453B2 (en) * | 2005-03-28 | 2011-07-12 | E. I. Du Pont De Nemours And Company | Processes for hydrolyzing polyphosphoric acid in shaped articles |
| US7968030B2 (en) | 2005-03-28 | 2011-06-28 | E.I. Du Pont De Nemours And Company | Hot surface hydrolysis of polyphosphoric acid in spun yarns |
| US7888457B2 (en) | 2005-04-01 | 2011-02-15 | E. I. Du Pont De Nemours And Company | Process for removing phosphorous from a fiber or yarn |
| US20100227984A1 (en) * | 2009-03-05 | 2010-09-09 | Dang Thuy | HYDROLYSIS-RESISTANT POLY (p-PHENYLENEBENZOBISOXAZOLE) (PBO) FIBERS |
| CN103314142B (zh) * | 2011-01-13 | 2017-03-01 | 纳幕尔杜邦公司 | 共聚物纤维的制备和干燥 |
| US9365952B2 (en) * | 2011-01-13 | 2016-06-14 | E I Du Pont De Nemours And Company | Copolymer fibers and processes for making same |
| EP2663676B1 (en) * | 2011-01-13 | 2015-12-16 | E. I. du Pont de Nemours and Company | Copolymer fibers and yarns and processes for making same |
| WO2013105949A1 (en) * | 2012-01-11 | 2013-07-18 | E. I. Du Pont De Nemours And Company | Process for preparing yarn derived from aramid copolymer fiber having low residual sulfur |
| US9469922B2 (en) * | 2012-01-11 | 2016-10-18 | E I Du Pont De Nemours And Company | Method for removing sulfur from fiber using a weak base |
| WO2013105938A1 (en) * | 2012-01-11 | 2013-07-18 | E. I. Du Pont De Nemours And Company | Method for removing sulfur from fiber using monovalent salt ion exchange |
| BR112014016856A8 (pt) * | 2012-01-11 | 2017-07-04 | Du Pont | método de remoção de enxofre de uma fibra feita de um polímero |
| BR112014017066A2 (pt) * | 2012-01-11 | 2018-05-22 | Du Pont | processo para produzir um fio |
| RU2014132856A (ru) * | 2012-01-11 | 2016-03-10 | Е.И.Дюпон Де Немур Энд Компани | Способ удаления серы из волокна с применением водного раствора кислоты |
| US20170152612A1 (en) * | 2014-05-08 | 2017-06-01 | National Institute Of Advanced Industrial Science And Technology | Polybenzimidazole carbon fiber and method for manufacturing same |
| WO2025217022A1 (en) * | 2024-04-08 | 2025-10-16 | The Regents Of The University Of Colorado, A Body Corporate | Continuous fiber reinforced photo sensitive polymer 3d printing |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4533693A (en) * | 1982-09-17 | 1985-08-06 | Sri International | Liquid crystalline polymer compositions, process, and products |
| US4772678A (en) * | 1983-09-15 | 1988-09-20 | Commtech International Management Corporation | Liquid crystalline polymer compositions, process, and products |
| US4703103A (en) * | 1984-03-16 | 1987-10-27 | Commtech International | Liquid crystalline polymer compositions, process and products |
| US4847350A (en) * | 1986-05-27 | 1989-07-11 | The Dow Chemical Company | Preparation of aromatic heterocyclic polymers |
| US5089591A (en) * | 1990-10-19 | 1992-02-18 | The Dow Chemical Company | Rapid advancement of molecular weight in polybenzazole oligomer dopes |
| US5276128A (en) * | 1991-10-22 | 1994-01-04 | The Dow Chemical Company | Salts of polybenzazole monomers and their use |
| US5393478A (en) | 1993-08-20 | 1995-02-28 | The Dow Chemical Company | Process for coagulation and washing of polybenzazole fibers |
| CN1155305A (zh) * | 1994-08-05 | 1997-07-23 | 陶氏化学公司 | 聚苯并噁唑或聚苯并噻唑纤维的制法 |
| EP0783603B1 (en) | 1994-09-30 | 1999-12-08 | Toyobo Co., Ltd. | Process for the preparation of polybenzazole filaments and fibres |
| US5525638A (en) * | 1994-09-30 | 1996-06-11 | The Dow Chemical Company | Process for the preparation of polybenzazole filaments and fibers |
| US6335419B2 (en) | 1999-12-06 | 2002-01-01 | Toyo Boseki Kabushiki Kaisha | Polybenzazole and fiber thereof |
| CN1665886A (zh) | 2002-06-26 | 2005-09-07 | 东洋纺织株式会社 | 高耐久性聚吲哚组合物、纤维以及薄膜 |
| JP2004076213A (ja) | 2002-08-20 | 2004-03-11 | Toyobo Co Ltd | 耐久性に優れる高強度繊維ロープ |
| KR20050013241A (ko) | 2002-06-26 | 2005-02-03 | 토요 보세키 가부시기가이샤 | 폴리벤즈아졸 섬유 및 그의 용도 |
| JP2004076214A (ja) | 2002-08-20 | 2004-03-11 | Toyobo Co Ltd | 耐久性に優れる高強度繊維ロープ |
-
2004
- 2004-07-22 US US10/896,790 patent/US7189346B2/en not_active Expired - Lifetime
-
2005
- 2005-07-20 KR KR1020077001359A patent/KR101261067B1/ko not_active Expired - Fee Related
- 2005-07-20 CA CA2571384A patent/CA2571384C/en not_active Expired - Fee Related
- 2005-07-20 WO PCT/US2005/025717 patent/WO2006014718A1/en not_active Ceased
- 2005-07-20 EP EP05774755A patent/EP1769109B1/en not_active Ceased
- 2005-07-20 CN CNB2005800248114A patent/CN100540762C/zh not_active Expired - Fee Related
- 2005-07-20 BR BRPI0513606-7A patent/BRPI0513606A/pt not_active Application Discontinuation
- 2005-07-20 MX MX2007000642A patent/MX2007000642A/es active IP Right Grant
- 2005-07-20 JP JP2007522690A patent/JP4695644B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| MX2007000642A (es) | 2007-03-07 |
| KR101261067B1 (ko) | 2013-05-06 |
| JP4695644B2 (ja) | 2011-06-08 |
| US7189346B2 (en) | 2007-03-13 |
| WO2006014718A1 (en) | 2006-02-09 |
| BRPI0513606A (pt) | 2008-05-13 |
| EP1769109B1 (en) | 2012-02-29 |
| JP2008507637A (ja) | 2008-03-13 |
| CN100540762C (zh) | 2009-09-16 |
| KR20070033001A (ko) | 2007-03-23 |
| EP1769109A1 (en) | 2007-04-04 |
| CN101001984A (zh) | 2007-07-18 |
| CA2571384A1 (en) | 2006-02-09 |
| US20060019094A1 (en) | 2006-01-26 |
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| EEER | Examination request | ||
| MKLA | Lapsed |
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| MKLA | Lapsed |
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