CA2120765A1 - Salts of polybenzazole monomers and their use - Google Patents
Salts of polybenzazole monomers and their useInfo
- Publication number
- CA2120765A1 CA2120765A1 CA002120765A CA2120765A CA2120765A1 CA 2120765 A1 CA2120765 A1 CA 2120765A1 CA 002120765 A CA002120765 A CA 002120765A CA 2120765 A CA2120765 A CA 2120765A CA 2120765 A1 CA2120765 A1 CA 2120765A1
- Authority
- CA
- Canada
- Prior art keywords
- monomer
- salt
- pbz
- pbz monomer
- acid
- 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
- 239000000178 monomer Substances 0.000 title claims abstract description 98
- 150000003839 salts Chemical class 0.000 title claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000007864 aqueous solution Substances 0.000 claims abstract description 11
- 229920000642 polymer Polymers 0.000 claims abstract description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- -1 halide ion Chemical class 0.000 claims description 9
- DPYROBMRMXHROQ-UHFFFAOYSA-N 4,6-diaminobenzene-1,3-diol Chemical compound NC1=CC(N)=C(O)C=C1O DPYROBMRMXHROQ-UHFFFAOYSA-N 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000002244 precipitate Substances 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 4
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 229920000106 Liquid crystal polymer Polymers 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- RLXBOUUYEFOFSW-UHFFFAOYSA-N 2,5-diaminobenzene-1,4-diol Chemical compound NC1=CC(O)=C(N)C=C1O RLXBOUUYEFOFSW-UHFFFAOYSA-N 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 230000002535 lyotropic effect Effects 0.000 claims 1
- 150000002500 ions Chemical class 0.000 abstract description 12
- 239000000243 solution Substances 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229920000137 polyphosphoric acid Polymers 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 229920002577 polybenzoxazole Polymers 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 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 description 3
- 239000002585 base Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000002950 deficient Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 150000003141 primary amines Chemical group 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CBQYNPHHHJTCJS-UHFFFAOYSA-N Alline Chemical compound C1=CC=C2C3(O)CCN(C)C3NC2=C1 CBQYNPHHHJTCJS-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 229910000039 hydrogen halide Chemical class 0.000 description 2
- 239000012433 hydrogen halide Chemical class 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- UOFDVLCOMURSTA-UHFFFAOYSA-N 2-(2-carboxyphenoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1C(O)=O UOFDVLCOMURSTA-UHFFFAOYSA-N 0.000 description 1
- CSLLVEYGNGXUDV-UHFFFAOYSA-N 2-(3-aminothiophen-2-yl)benzoic acid Chemical class NC1=C(SC=C1)C1=CC=CC=C1C(=O)O CSLLVEYGNGXUDV-UHFFFAOYSA-N 0.000 description 1
- FOLUJWPWRXHMLF-UHFFFAOYSA-N 2-[2-(2-carboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=CC=C1C(O)=O FOLUJWPWRXHMLF-UHFFFAOYSA-N 0.000 description 1
- GITURYUSYHZMFR-UHFFFAOYSA-N 2-amino-3-(2-amino-3-hydroxyphenyl)sulfonylphenol Chemical compound NC1=C(O)C=CC=C1S(=O)(=O)C1=CC=CC(O)=C1N GITURYUSYHZMFR-UHFFFAOYSA-N 0.000 description 1
- IQGMRVWUTCYCST-UHFFFAOYSA-N 3-Aminosalicylic acid Chemical class NC1=CC=CC(C(O)=O)=C1O IQGMRVWUTCYCST-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N ortho-hydroxyaniline Natural products NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- WHALSQRTWNBBCV-UHFFFAOYSA-N s-aminosulfanylthiohydroxylamine Chemical group NSSN WHALSQRTWNBBCV-UHFFFAOYSA-N 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/33—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
- C07C323/34—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a mercapto group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/76—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring
- C07C215/80—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton of the same non-condensed six-membered aromatic ring containing at least two amino groups bound to the carbon skeleton
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/32—Polythiazoles; Polythiadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/780,493 US5276128A (en) | 1991-10-22 | 1991-10-22 | Salts of polybenzazole monomers and their use |
| US07/780,493 | 1991-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2120765A1 true CA2120765A1 (en) | 1993-04-29 |
Family
ID=25119742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002120765A Abandoned CA2120765A1 (en) | 1991-10-22 | 1992-08-27 | Salts of polybenzazole monomers and their use |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5276128A (enExample) |
| EP (1) | EP0612311A1 (enExample) |
| JP (1) | JP3263946B2 (enExample) |
| CA (1) | CA2120765A1 (enExample) |
| TW (1) | TW245727B (enExample) |
| WO (1) | WO1993008156A1 (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09296041A (ja) * | 1996-04-30 | 1997-11-18 | Toyobo Co Ltd | ポリベンズアゾールの製造方法 |
| US6430225B1 (en) | 1996-07-19 | 2002-08-06 | Sony Corporation | Apparatus and method for digital data transmission |
| DE69807990T2 (de) * | 1997-06-10 | 2003-04-30 | Toyo Boseki K.K., Osaka | Verfahren zur Stabilisierung von 4,6-Diaminoresorcin und dessen Salzen |
| JPH11181093A (ja) * | 1997-12-24 | 1999-07-06 | Toyobo Co Ltd | ポリベンズアゾールの製造方法 |
| JP2001172238A (ja) | 1999-12-17 | 2001-06-26 | Toyobo Co Ltd | 芳香族ジアミン／芳香族ジカルボン酸塩およびその製造方法 |
| US7189346B2 (en) * | 2004-07-22 | 2007-03-13 | E. I. Du Pont De Nemours And Company | Polybenzazole fibers and processes for their preparation |
| JP5063583B2 (ja) * | 2005-03-28 | 2012-10-31 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 高い固有粘度をもつポリマーおよびそれから得られる繊維 |
| WO2006105080A1 (en) * | 2005-03-28 | 2006-10-05 | E.I. Du Pont De Nemours And Company | Processes for increasing polymer inherent viscosity |
| KR101333853B1 (ko) * | 2005-03-28 | 2013-11-27 | 마젤란 시스템즈 인터내셔날, 엘엘시 | 금속 분말을 사용한 높은 고유 점도 폴리아렌아졸의 제조방법 |
| WO2006105076A2 (en) * | 2005-03-28 | 2006-10-05 | E.I. Du Pont De Nemours And Company | Processes for preparing monomer complexes |
| KR101327714B1 (ko) | 2005-03-28 | 2013-11-11 | 마젤란 시스템즈 인터내셔날, 엘엘시 | 폴리아렌아졸 실의 제조 방법 |
| WO2006105226A1 (en) | 2005-03-28 | 2006-10-05 | E. I. Du Pont De Nemours And Company | Process for hydrolyzing polyphosphoric acid in a spun yarn |
| WO2006105311A1 (en) * | 2005-03-28 | 2006-10-05 | E.I. Du Pont De Nemours And Company | Fusion-free hydrolysis of polyphosphoric acid in spun multifilament yarns |
| DE602006019562D1 (de) | 2005-03-28 | 2011-02-24 | Du Pont | Verfahren zur hydrolyse von polyphosphorsäure in polyareneazolfasern |
| DE602006019572D1 (de) * | 2005-03-28 | 2011-02-24 | Du Pont | Heisse oberflächen-hydrolyse von polyphosphorsäure in spun-garnen |
| WO2006105227A1 (en) * | 2005-03-28 | 2006-10-05 | E. I. Du Pont De Nemours And Company | Thermal processes for increasing polyareneazole inherent viscosities |
| US7683157B2 (en) * | 2005-03-28 | 2010-03-23 | E.I. Du Pont De Nemours And Company | Process for the production of polyarenazole polymer |
| JP5090336B2 (ja) | 2005-03-28 | 2012-12-05 | 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繊維からカチオンを除去する方法 |
| EP1877602B1 (en) * | 2005-03-28 | 2009-08-26 | E.I. Du Pont De Nemours And Company | Processes for hydrolyzing polyphosphoric acid in shaped articles |
| 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 |
| 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 |
| CN101310159A (zh) | 2005-08-10 | 2008-11-19 | 纳幕尔杜邦公司 | 可挠曲耐穿透物品 |
| US7638193B1 (en) * | 2006-10-10 | 2009-12-29 | E. I. Du Pont De Nemours And Company | Cut-resistant yarns and method of manufacture |
| US7700191B2 (en) * | 2007-08-22 | 2010-04-20 | E.I. Du Pont De Nemours And Company | Flame resistant spun staple yarns made from blends of fibers derived from diamino diphenyl sulfone and high modulus fibers and fabrics and garments made therefrom and methods for making same |
| US7700190B2 (en) * | 2007-08-22 | 2010-04-20 | E.I. Du Pont De Nemours And Company | Flame resistant spun staple yarns made from blends of fibers derived from diamino diphenyl sulfone and textile fibers and fabrics and garments made therefrom and methods for making same |
| US8166743B2 (en) * | 2007-08-22 | 2012-05-01 | E.I. Du Pont De Nemours And Company | Spun staple yarns made from blends of rigid-rod fibers and fibers derived from diamino diphenyl sulfone and fabrics and garments made therefrom and methods for making same |
| US8015617B1 (en) | 2008-05-14 | 2011-09-13 | E. I. Du Pont De Nemours And Company | Ballistic resistant body armor articles |
| US7665149B2 (en) * | 2008-05-14 | 2010-02-23 | E.I. Du Pont De Nemours And Company | Ballistic resistant body armor articles |
| BRPI1006279A2 (pt) * | 2009-03-20 | 2019-09-24 | Du Pont | " bloco da banda de rodagem do pneu, método de diminuição de ressonância e progresso para a produção de um pneu " |
| US20110146862A1 (en) * | 2009-12-18 | 2011-06-23 | E. I. Du Pont De Nemours And Company | Low noise tire |
| US20120102632A1 (en) | 2010-10-28 | 2012-05-03 | E.I. Du Pont De Nemours And Company | Arc resistant garment containing a multilayer fabric laminate and processes for making same |
| WO2012082435A1 (en) | 2010-12-16 | 2012-06-21 | E. I. Du Pont De Nemours And Company | Sulfonated polyoxadiazole polymers |
| US20130217854A1 (en) | 2010-12-16 | 2013-08-22 | E I Du Pont De Nemours And Company | Preparation of sulfonated polyoxadiazole polymers |
| US20130210306A1 (en) | 2010-12-16 | 2013-08-15 | E I Du Pont De Nemours And Company | Flame resistant spun staple yarns made from blends of fibers derived from sulfonated polyoxadiazole polymers |
| US9291433B2 (en) | 2012-02-22 | 2016-03-22 | Cryovac, Inc. | Ballistic-resistant composite assembly |
| CN104603180B (zh) | 2012-06-15 | 2018-05-15 | 纳幕尔杜邦公司 | 磺化聚噁二唑聚合物制品 |
| US9150693B2 (en) | 2012-06-15 | 2015-10-06 | E I Du Pont De Nemours And Company | Preparation of sulfonated naphthalene polyoxadiazoles polymers |
| WO2014007948A2 (en) | 2012-06-15 | 2014-01-09 | E. I. Du Pont De Nemours And Company | Flame resistant spun staple yarns made from blends of fibers derived from sulfonated naphthalene polyoxadiazole polymers |
| 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 |
| US20140082808A1 (en) | 2012-09-21 | 2014-03-27 | E I Du Pont De Nemours And Company | Ballistic resistant body armor articles |
| CN104837649A (zh) | 2012-12-04 | 2015-08-12 | 纳幕尔杜邦公司 | 包含短纤纱的加强结构 |
| JP6335193B2 (ja) | 2013-01-09 | 2018-05-30 | 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 | タイヤオーバーレイ組成物 |
| US9074321B2 (en) | 2013-09-24 | 2015-07-07 | E I Du Pont De Nemours And Company | Fibrous pulp and use thereof in a composite |
| US20160362525A1 (en) | 2014-02-27 | 2016-12-15 | E. I. Du Pont De Nemours And Company | Micropulp-elastomer masterbatches and compounds |
| CN104119534B (zh) * | 2014-07-10 | 2017-07-14 | 金宁人 | 一类聚羟基对亚苯基苯并二噁唑聚合物及其制备与应用 |
| KR102433523B1 (ko) * | 2016-09-14 | 2022-08-17 | 바스프 에스이 | 폴리벤즈아졸 중합체(p)의 제조 방법 |
| CN118201769A (zh) | 2021-11-10 | 2024-06-14 | 杜邦安全与建筑公司 | 由不含非织造纤维的机械缠结的织造织物制成的防弹材料及其制造方法 |
Family Cites Families (12)
| 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 |
| US4806688A (en) * | 1986-05-16 | 1989-02-21 | The Dow Chemical Company | Preparation of diamino- and dialkylaminobenzenediols |
| US4766244A (en) * | 1986-10-30 | 1988-08-23 | The Dow Chemical Company | High purity process for the preparation of 4,6-diamino-1,3-benzenediol |
| US4982001A (en) * | 1987-10-19 | 1991-01-01 | The Dow Chemical Company | Process for the preparation of amino-1,3-benzenediol |
| US4912246A (en) * | 1987-10-19 | 1990-03-27 | The Dow Chemical Company | 1,3-bis(alkylcarbonato)-nitrobenzenes |
| JPH01256534A (ja) * | 1988-04-06 | 1989-10-13 | Res Inst For Prod Dev | ポリ（ｐ−フェニレンベンゾオキサゾール）の製造法 |
| JPH068351B2 (ja) * | 1988-06-03 | 1994-02-02 | 本田技研工業株式会社 | 芳香族ポリチアゾールの前駆物質の製造方法 |
| JPH01311127A (ja) * | 1988-06-08 | 1989-12-15 | Honda Motor Co Ltd | 芳香族ポリチアゾールの前駆物質の製造方法 |
| JPH04502168A (ja) * | 1988-12-22 | 1992-04-16 | ザ ダウ ケミカル カンパニー | 複素環式ポリマーの改良合成方法 |
| US5138020A (en) * | 1989-04-21 | 1992-08-11 | The Dow Chemical Company | Phosphate salts of monomers for pbz and their use in preparing pbz polymers |
| US5001265A (en) * | 1989-07-28 | 1991-03-19 | The Dow Chemical Company | Aqueous reduction process for halo-nitro-phenols |
| US5089591A (en) * | 1990-10-19 | 1992-02-18 | The Dow Chemical Company | Rapid advancement of molecular weight in polybenzazole oligomer dopes |
-
1991
- 1991-10-22 US US07/780,493 patent/US5276128A/en not_active Expired - Lifetime
-
1992
- 1992-08-27 JP JP50766793A patent/JP3263946B2/ja not_active Expired - Fee Related
- 1992-08-27 EP EP92919948A patent/EP0612311A1/en not_active Withdrawn
- 1992-08-27 WO PCT/US1992/007281 patent/WO1993008156A1/en not_active Ceased
- 1992-08-27 CA CA002120765A patent/CA2120765A1/en not_active Abandoned
- 1992-10-21 TW TW081108393A patent/TW245727B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US5276128A (en) | 1994-01-04 |
| JPH07500592A (ja) | 1995-01-19 |
| JP3263946B2 (ja) | 2002-03-11 |
| TW245727B (enExample) | 1995-04-21 |
| WO1993008156A1 (en) | 1993-04-29 |
| EP0612311A1 (en) | 1994-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5276128A (en) | Salts of polybenzazole monomers and their use | |
| US5089591A (en) | Rapid advancement of molecular weight in polybenzazole oligomer dopes | |
| US4312976A (en) | Single-stage melt polymerization process for the production of high molecular weight polybenzimidazole | |
| AU597279B2 (en) | A process for the production of a liquid crystalline extendedchain polymer composition | |
| US5312895A (en) | Benzobisazole copolymer system soluble in aprotic solvents | |
| US5344896A (en) | Water soluble rigid-rod polymers | |
| US5166313A (en) | Diamantane modified rigid-rod poly benzazole and method of manufacture | |
| US9656982B2 (en) | Acid dianhydride, method for preparing same, and polyimide prepared therefrom | |
| Abed et al. | Synthesis and characterization of new phosphorus and other heteroatom containing aryl cyanate ester monomers and networks | |
| US5194568A (en) | Staged polymerization of polybenzazole polymers | |
| CA2053757A1 (en) | Staged polymerization of polybenzazole polymers | |
| KR970011638B1 (ko) | 폴리아미드 음이온 용액의 제조방법 | |
| US4868249A (en) | Cyanoethylation of hydroxyethylated polybenzimidazole polymers | |
| US5138020A (en) | Phosphate salts of monomers for pbz and their use in preparing pbz polymers | |
| US5021580A (en) | Polybenzoxazoles having pendant methyl groups | |
| US3575933A (en) | Process for preparing benzamide polymers | |
| US5006636A (en) | Process for the production of SiO2 containing polybenzamides | |
| US5151490A (en) | Polybenzoxazoles having pendant methyl groups | |
| US5422416A (en) | Process for the synthesis of polybenzazole polymers | |
| US5068384A (en) | Phosphate salts of AB-polybenzoxazole monomer | |
| US9676739B2 (en) | Acid dianhydride, method for preparing same, and polyimide prepared therefrom | |
| CA2006369A1 (en) | Process for synthesis of heterocyclic polymers | |
| Bottino et al. | Synthesis and properties of new poly (ether sulfone) amides | |
| Bottino et al. | Synthesis and Properties of Aromatic Poly (Ether Sulfone) s and Poly (Etherketone) s Containing Naphthalene or Quinoline Units, and Methyl-Substituted Biphenyl-4, 4′-Diols | |
| US5233014A (en) | Rapid advancement of molecular weight in polybenzazole oligomer dopes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |