CA2614967C - Method for making polybenzobisoxazole containing polymer - Google Patents
Method for making polybenzobisoxazole containing polymer Download PDFInfo
- Publication number
- CA2614967C CA2614967C CA2614967A CA2614967A CA2614967C CA 2614967 C CA2614967 C CA 2614967C CA 2614967 A CA2614967 A CA 2614967A CA 2614967 A CA2614967 A CA 2614967A CA 2614967 C CA2614967 C CA 2614967C
- Authority
- CA
- Canada
- Prior art keywords
- polymer
- acid
- solution
- ppd
- forming
- 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 69
- 229920002577 polybenzoxazole Polymers 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims description 22
- 238000010438 heat treatment Methods 0.000 claims abstract description 13
- 238000006798 ring closing metathesis reaction Methods 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
- -1 alkyl carboxylic acid Chemical class 0.000 claims description 9
- 239000007800 oxidant agent Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- YNGRGHODNDCZCC-UHFFFAOYSA-N nitro hydrogen sulfate Chemical group OS(=O)(=O)O[N+]([O-])=O YNGRGHODNDCZCC-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 235000010344 sodium nitrate Nutrition 0.000 claims description 2
- 239000004317 sodium nitrate Substances 0.000 claims description 2
- 230000000640 hydroxylating effect Effects 0.000 abstract description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000000835 fiber Substances 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000010408 film Substances 0.000 description 7
- 238000005805 hydroxylation reaction Methods 0.000 description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000033444 hydroxylation Effects 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 5
- 229920000137 polyphosphoric acid Polymers 0.000 description 5
- 238000009987 spinning Methods 0.000 description 5
- RXQNKKRGJJRMKD-UHFFFAOYSA-N 5-bromo-2-methylaniline Chemical compound CC1=CC=C(Br)C=C1N RXQNKKRGJJRMKD-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004760 aramid Substances 0.000 description 3
- 229920003235 aromatic polyamide Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000003419 tautomerization reaction Methods 0.000 description 2
- ZFCNECLRCWFTLI-UHFFFAOYSA-N 3-(3-carboxyphenoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=C(C=CC=2)C(O)=O)=C1 ZFCNECLRCWFTLI-UHFFFAOYSA-N 0.000 description 1
- CULWHZJWAKFHMK-UHFFFAOYSA-N 3-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=CC(C(O)=O)=C1 CULWHZJWAKFHMK-UHFFFAOYSA-N 0.000 description 1
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- SQJQLYOMPSJVQS-UHFFFAOYSA-N 4-(4-carboxyphenyl)sulfonylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C=C1 SQJQLYOMPSJVQS-UHFFFAOYSA-N 0.000 description 1
- WRDNCFQZLUCIRH-UHFFFAOYSA-N 4-(7-azabicyclo[2.2.1]hepta-1,3,5-triene-7-carbonyl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C(=O)N1C2=CC=C1C=C2 WRDNCFQZLUCIRH-UHFFFAOYSA-N 0.000 description 1
- XRASRVJYOMVDNP-UHFFFAOYSA-N 4-(7-azabicyclo[4.1.0]hepta-1,3,5-triene-7-carbonyl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C(=O)N1C2=CC=CC=C21 XRASRVJYOMVDNP-UHFFFAOYSA-N 0.000 description 1
- 102100034460 Cytosolic iron-sulfur assembly component 3 Human genes 0.000 description 1
- 101000710266 Homo sapiens Cytosolic iron-sulfur assembly component 3 Proteins 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- PNZVFASWDSMJER-UHFFFAOYSA-N acetic acid;lead Chemical compound [Pb].CC(O)=O PNZVFASWDSMJER-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000009841 combustion method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001523 electrospinning Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical group OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 1
- 229910052756 noble gas Inorganic materials 0.000 description 1
- 150000002835 noble gases Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920000052 poly(p-xylylene) Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000002166 wet spinning Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/180,234 | 2005-07-13 | ||
| US11/180,234 US7465781B2 (en) | 2005-07-13 | 2005-07-13 | Method for making polybenzobisoxazole containing polymer |
| PCT/US2006/026872 WO2007008887A1 (en) | 2005-07-13 | 2006-07-12 | Method for making polybenzobisoxazole containing polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2614967A1 CA2614967A1 (en) | 2007-01-18 |
| CA2614967C true CA2614967C (en) | 2013-04-02 |
Family
ID=37192448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2614967A Expired - Fee Related CA2614967C (en) | 2005-07-13 | 2006-07-12 | Method for making polybenzobisoxazole containing polymer |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7465781B2 (https=) |
| EP (1) | EP1907447B1 (https=) |
| JP (1) | JP4938775B2 (https=) |
| KR (1) | KR101236661B1 (https=) |
| CN (1) | CN101223212B (https=) |
| BR (1) | BRPI0613292A2 (https=) |
| CA (1) | CA2614967C (https=) |
| DE (1) | DE602006003439D1 (https=) |
| MX (1) | MX2008000399A (https=) |
| WO (1) | WO2007008887A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10464639B2 (en) * | 2013-12-31 | 2019-11-05 | Grady-White Boats, Inc. | Seat and seat back assembly |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3819587A (en) | 1969-05-23 | 1974-06-25 | Du Pont | Wholly aromatic carbocyclic polycarbonamide fiber having orientation angle of less than about 45{20 |
| US3869430A (en) | 1971-08-17 | 1975-03-04 | Du Pont | High modulus, high tenacity poly(p-phenylene terephthalamide) fiber |
| US3869429A (en) | 1971-08-17 | 1975-03-04 | Du Pont | High strength polyamide fibers and films |
| US3767756A (en) | 1972-06-30 | 1973-10-23 | Du Pont | Dry jet wet spinning process |
| US4423202A (en) | 1981-05-05 | 1983-12-27 | Celanese Corporation | Process for the production of high molecular weight para ordered aromatic heterocyclic polymer |
| KR100215541B1 (ko) | 1996-04-19 | 1999-08-16 | 박원훈 | 벤족사졸계 비선형 광학 유도체 및 이들로부터 얻어진고분자 |
| CN1233696C (zh) * | 2003-01-17 | 2005-12-28 | 北京大学 | 一种聚（苯撑苯并噁唑）及其预聚物与它们的制备方法 |
| US7465782B2 (en) * | 2005-07-13 | 2008-12-16 | E.I Du Pont De Nemours & Company | Method for making polybenzobisoxazole containing fiber |
-
2005
- 2005-07-13 US US11/180,234 patent/US7465781B2/en not_active Expired - Fee Related
-
2006
- 2006-07-12 BR BRPI0613292-8A patent/BRPI0613292A2/pt active Search and Examination
- 2006-07-12 MX MX2008000399A patent/MX2008000399A/es active IP Right Grant
- 2006-07-12 DE DE602006003439T patent/DE602006003439D1/de active Active
- 2006-07-12 CN CN2006800257936A patent/CN101223212B/zh not_active Expired - Fee Related
- 2006-07-12 JP JP2008521521A patent/JP4938775B2/ja not_active Expired - Fee Related
- 2006-07-12 EP EP06786886A patent/EP1907447B1/en not_active Not-in-force
- 2006-07-12 WO PCT/US2006/026872 patent/WO2007008887A1/en not_active Ceased
- 2006-07-12 CA CA2614967A patent/CA2614967C/en not_active Expired - Fee Related
- 2006-07-12 KR KR1020087003426A patent/KR101236661B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0613292A2 (pt) | 2010-12-28 |
| CA2614967A1 (en) | 2007-01-18 |
| WO2007008887A1 (en) | 2007-01-18 |
| CN101223212A (zh) | 2008-07-16 |
| EP1907447B1 (en) | 2008-10-29 |
| DE602006003439D1 (de) | 2008-12-11 |
| CN101223212B (zh) | 2010-12-08 |
| KR101236661B1 (ko) | 2013-02-22 |
| MX2008000399A (es) | 2008-03-07 |
| JP2009501269A (ja) | 2009-01-15 |
| KR20080031403A (ko) | 2008-04-08 |
| US7465781B2 (en) | 2008-12-16 |
| JP4938775B2 (ja) | 2012-05-23 |
| EP1907447A1 (en) | 2008-04-09 |
| US20070015898A1 (en) | 2007-01-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20170712 |