CA2662239C - Polymers and fibers formed therefrom - Google Patents
Polymers and fibers formed therefrom Download PDFInfo
- Publication number
- CA2662239C CA2662239C CA2662239A CA2662239A CA2662239C CA 2662239 C CA2662239 C CA 2662239C CA 2662239 A CA2662239 A CA 2662239A CA 2662239 A CA2662239 A CA 2662239A CA 2662239 C CA2662239 C CA 2662239C
- Authority
- CA
- Canada
- Prior art keywords
- fiber
- polymer
- polyoxadiazole
- polymers
- value
- 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
- 229920000642 polymer Polymers 0.000 title claims abstract description 33
- 239000000835 fiber Substances 0.000 title claims description 38
- 229920001577 copolymer Polymers 0.000 claims description 11
- 150000001768 cations Chemical class 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 20
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 19
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 18
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 239000012493 hydrazine sulfate Substances 0.000 description 6
- 229910000377 hydrazine sulfate Inorganic materials 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- WMAVHUWINYPPKT-UHFFFAOYSA-M (e)-3-methyl-n-[(e)-(1-methyl-2-phenylindol-1-ium-3-ylidene)amino]-1,3-thiazol-2-imine;chloride Chemical compound [Cl-].C12=CC=CC=C2N(C)C(C=2C=CC=CC=2)=C1N=NC=1SC=C[N+]=1C WMAVHUWINYPPKT-UHFFFAOYSA-M 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 238000004043 dyeing Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- AHYFYYVVAXRMKB-UHFFFAOYSA-N 3-(1h-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C=1NC2=CC=CC=C2C=1CC(C(=O)O)NC(=O)OCC1=CC=CC=C1 AHYFYYVVAXRMKB-UHFFFAOYSA-N 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000000981 basic dye Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 235000004879 dioscorea Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 231100000584 environmental toxicity Toxicity 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- UYPYRKYUKCHHIB-UHFFFAOYSA-N trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004804 winding 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- 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
- C08G73/08—Polyhydrazides; Polytriazoles; Polyaminotriazoles; Polyoxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- 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
- Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
- Y10T428/269—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension including synthetic resin or polymer layer or component
-
- 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
- Y10T428/2933—Coated or with bond, impregnation or core
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Artificial Filaments (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyesters Or Polycarbonates (AREA)
- Coloring (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/544,118 US7528217B2 (en) | 2006-10-06 | 2006-10-06 | Polymers and fibers formed therefrom |
| US11/544,118 | 2006-10-06 | ||
| PCT/US2007/020335 WO2008042115A1 (en) | 2006-10-06 | 2007-09-19 | Polymers and fibers formed therefrom |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2662239A1 CA2662239A1 (en) | 2008-04-10 |
| CA2662239C true CA2662239C (en) | 2014-12-30 |
Family
ID=38805640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2662239A Expired - Fee Related CA2662239C (en) | 2006-10-06 | 2007-09-19 | Polymers and fibers formed therefrom |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7528217B2 (enExample) |
| EP (1) | EP2094763B1 (enExample) |
| JP (1) | JP2010505997A (enExample) |
| KR (1) | KR101386825B1 (enExample) |
| CN (1) | CN101595161B (enExample) |
| BR (1) | BRPI0715300A2 (enExample) |
| CA (1) | CA2662239C (enExample) |
| WO (1) | WO2008042115A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101735455B (zh) * | 2008-11-14 | 2012-07-11 | 无锡华东创新材料研究院 | 一种专用的芳香族聚噁二唑及其阻燃耐高温聚噁二唑纤维的制备方法 |
| DE102010017679A1 (de) | 2010-07-01 | 2012-01-05 | Contitech Schlauch Gmbh | Artikel, insbesondere Schlauch, insbesondere wiederum Ladeluftschlauch, mit einem eingebetteten Festigkeitsträger auf der Basis eines Polyoxadiazols |
| PL2422966T3 (pl) | 2010-08-30 | 2015-11-30 | Contitech Schlauch Gmbh | Sposób wytwarzania przewodów powietrza doładowującego |
| CN103261275A (zh) * | 2010-12-16 | 2013-08-21 | 纳幕尔杜邦公司 | 磺化的聚噁二唑聚合物的制备 |
| WO2012082434A1 (en) | 2010-12-16 | 2012-06-21 | E. I. Du Pont De Nemours And Company | Flame resistant spun staple yarns made from blends of fibers derived from sulfonated polyoxadiazole polymers |
| CN103261274A (zh) * | 2010-12-16 | 2013-08-21 | 纳幕尔杜邦公司 | 磺化聚噁二唑聚合物制品 |
| US8695319B2 (en) * | 2011-12-05 | 2014-04-15 | E I Du Pont De Nemours And Company | Yarns of polyoxadiazole and modacrylic fibers and fabrics and garments made therefrom and methods for making same |
| JP6112683B2 (ja) * | 2012-06-15 | 2017-04-12 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | スルホン化ナフタレンポリオキサジアゾールポリマーより得られる繊維のブレンドから製造された難燃性紡績短繊維ヤーン |
| WO2013188328A1 (en) | 2012-06-15 | 2013-12-19 | E. I. Du Pont De Nemours And Company | Sulfonated polyoxadiazole polymers articles |
| CN104508007B (zh) * | 2012-06-15 | 2019-07-23 | 纳幕尔杜邦公司 | 磺化萘聚噁二唑聚合物 |
| US9150693B2 (en) | 2012-06-15 | 2015-10-06 | E I Du Pont De Nemours And Company | Preparation of sulfonated naphthalene polyoxadiazoles polymers |
| DE102012112581A1 (de) | 2012-12-18 | 2014-06-18 | Contitech Elastomer-Beschichtungen Gmbh | Mehrschichtiger Artikel, insbesondere Faltenbalg, enthaltend wenigstens ein schwer entflammbares textiles Flächengebilde |
| KR102070137B1 (ko) * | 2013-12-30 | 2020-01-28 | 코오롱인더스트리 주식회사 | 공중합 아라미드 원착사 및 그의 제조방법 |
| CN119264424A (zh) * | 2023-07-05 | 2025-01-07 | 华为技术有限公司 | Pod树脂材料、pod树脂薄膜及其制备方法、石墨膜和电子设备 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4087409A (en) | 1966-11-07 | 1978-05-02 | Monsanto Company | Ordered heterocyclic copolymers |
| US3886251A (en) | 1967-04-11 | 1975-05-27 | Furukawa Electric Co Ltd | Method for forming polyoxadiazole series resin solution into shaped articles |
| US4177347A (en) * | 1974-06-12 | 1979-12-04 | Ciba-Geigy Corporation | Distilbenyl-oxdiazoles |
| US4298565A (en) | 1980-02-12 | 1981-11-03 | E. I. Du Pont De Nemours And Company | Spinning process |
| US4340559A (en) | 1980-10-31 | 1982-07-20 | E. I. Du Pont De Nemours And Company | Spinning process |
| US4965033A (en) | 1990-03-26 | 1990-10-23 | E. I. Du Pont De Nemours And Company | Process for spinning high-strength, high-modulus aromatic polyamides |
| US7332530B2 (en) * | 2002-08-02 | 2008-02-19 | Celanese Ventures Gmbh | Proton-conducting polymer membrane comprising a polymer with sulphonic acid groups and use thereof in fuel cells |
| US7582721B2 (en) | 2006-05-01 | 2009-09-01 | E.I. Du Pont De Nemours And Company | Two step preparation of random polyoxadiazole copolymer and articles resulting therefrom |
| US7528216B2 (en) | 2006-05-01 | 2009-05-05 | E.I. Du Pont De Nemours And Company | Two step preparation of random polyoxadiazole copolymer and articles resulting therefrom |
| US20080014440A1 (en) | 2006-07-13 | 2008-01-17 | Kiu-Seung Lee | Polyoxadiazole composite fibers |
-
2006
- 2006-10-06 US US11/544,118 patent/US7528217B2/en active Active
-
2007
- 2007-09-19 KR KR1020097008692A patent/KR101386825B1/ko active Active
- 2007-09-19 EP EP07838531A patent/EP2094763B1/en active Active
- 2007-09-19 JP JP2009531386A patent/JP2010505997A/ja active Pending
- 2007-09-19 CN CN2007800372182A patent/CN101595161B/zh active Active
- 2007-09-19 CA CA2662239A patent/CA2662239C/en not_active Expired - Fee Related
- 2007-09-19 WO PCT/US2007/020335 patent/WO2008042115A1/en not_active Ceased
- 2007-09-19 BR BRPI0715300-7A2A patent/BRPI0715300A2/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR101386825B1 (ko) | 2014-04-17 |
| KR20090060456A (ko) | 2009-06-12 |
| EP2094763B1 (en) | 2013-03-27 |
| CA2662239A1 (en) | 2008-04-10 |
| EP2094763A1 (en) | 2009-09-02 |
| US7528217B2 (en) | 2009-05-05 |
| CN101595161A (zh) | 2009-12-02 |
| WO2008042115A1 (en) | 2008-04-10 |
| CN101595161B (zh) | 2012-02-29 |
| BRPI0715300A2 (pt) | 2013-06-11 |
| US20080085992A1 (en) | 2008-04-10 |
| JP2010505997A (ja) | 2010-02-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20170919 |