JPS62283127A - ポリベンズオキサゾ−ル樹脂の製造方法 - Google Patents
ポリベンズオキサゾ−ル樹脂の製造方法Info
- Publication number
- JPS62283127A JPS62283127A JP12515486A JP12515486A JPS62283127A JP S62283127 A JPS62283127 A JP S62283127A JP 12515486 A JP12515486 A JP 12515486A JP 12515486 A JP12515486 A JP 12515486A JP S62283127 A JPS62283127 A JP S62283127A
- Authority
- JP
- Japan
- Prior art keywords
- aromatic
- formula
- resin
- group
- polyamide resin
- 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.)
- Granted
Links
- 239000011347 resin Substances 0.000 title claims abstract description 41
- 229920005989 resin Polymers 0.000 title claims abstract description 41
- 229920002577 polybenzoxazole Polymers 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000004984 aromatic diamines Chemical class 0.000 claims abstract description 6
- 125000000962 organic group Chemical group 0.000 claims abstract description 6
- 239000004760 aramid Substances 0.000 claims abstract description 5
- 229920003235 aromatic polyamide Polymers 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 6
- 238000010438 heat treatment Methods 0.000 abstract description 4
- 239000000835 fiber Substances 0.000 abstract description 3
- 239000012528 membrane Substances 0.000 abstract description 2
- 238000007363 ring formation reaction Methods 0.000 abstract 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229920001296 polysiloxane Polymers 0.000 abstract 1
- 229920006122 polyamide resin Polymers 0.000 description 25
- -1 diamine compound Chemical class 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 5
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006210 cyclodehydration reaction Methods 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 1
- PGJDKGMYQNFEDQ-UHFFFAOYSA-N 3-n-trimethylsilyl-1-n-[3-(trimethylsilylamino)-4-trimethylsilyloxyphenyl]-4-trimethylsilyloxybenzene-1,3-diamine Chemical compound C1=C(O[Si](C)(C)C)C(N[Si](C)(C)C)=CC(NC=2C=C(N[Si](C)(C)C)C(O[Si](C)(C)C)=CC=2)=C1 PGJDKGMYQNFEDQ-UHFFFAOYSA-N 0.000 description 1
- AXBVYKSPLWLLPG-UHFFFAOYSA-N 4-(4-carbonochloridoyl-2,3,5-trifluorophenyl)-2,3,6-trifluoro-5-propan-2-ylidenecyclohexa-1,3-diene-1-carbonyl chloride Chemical compound CC(C)=C1C(F)C(C(Cl)=O)=C(F)C(F)=C1C1=CC(F)=C(C(Cl)=O)C(F)=C1F AXBVYKSPLWLLPG-UHFFFAOYSA-N 0.000 description 1
- QDBOAKPEXMMQFO-UHFFFAOYSA-N 4-(4-carbonochloridoylphenyl)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=C(C(Cl)=O)C=C1 QDBOAKPEXMMQFO-UHFFFAOYSA-N 0.000 description 1
- SJVGFKBLUYAEOK-SFHVURJKSA-N 6-[4-[(3S)-3-(3,5-difluorophenyl)-3,4-dihydropyrazole-2-carbonyl]piperidin-1-yl]pyrimidine-4-carbonitrile Chemical compound FC=1C=C(C=C(C=1)F)[C@@H]1CC=NN1C(=O)C1CCN(CC1)C1=CC(=NC=N1)C#N SJVGFKBLUYAEOK-SFHVURJKSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- MWHHJYUHCZWSLS-UHFFFAOYSA-N FC=1C=C(C=CC1C1=C2CNC(C2=C(C=C1)C=1NC(=CN1)C)=O)NC(=O)NC1=C(C=C(C=C1F)F)F Chemical compound FC=1C=C(C=CC1C1=C2CNC(C2=C(C=C1)C=1NC(=CN1)C)=O)NC(=O)NC1=C(C=C(C=C1F)F)F MWHHJYUHCZWSLS-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- JKBBCAVZVYJPNA-UHFFFAOYSA-N n-trimethylsilyl-5-[3-(trimethylsilylamino)-4-trimethylsilyloxyphenoxy]-2-trimethylsilyloxyaniline Chemical compound C1=C(O[Si](C)(C)C)C(N[Si](C)(C)C)=CC(OC=2C=C(N[Si](C)(C)C)C(O[Si](C)(C)C)=CC=2)=C1 JKBBCAVZVYJPNA-UHFFFAOYSA-N 0.000 description 1
- ZLKIYYJJEWJVIT-UHFFFAOYSA-N n-trimethylsilyl-5-[3-(trimethylsilylamino)-4-trimethylsilyloxyphenyl]sulfonyl-2-trimethylsilyloxyaniline Chemical compound C1=C(O[Si](C)(C)C)C(N[Si](C)(C)C)=CC(S(=O)(=O)C=2C=C(N[Si](C)(C)C)C(O[Si](C)(C)C)=CC=2)=C1 ZLKIYYJJEWJVIT-UHFFFAOYSA-N 0.000 description 1
- NCMXVLJIZACJIH-UHFFFAOYSA-N n-trimethylsilyl-5-[[3-(trimethylsilylamino)-4-trimethylsilyloxyphenyl]methyl]-2-trimethylsilyloxyaniline Chemical compound C1=C(O[Si](C)(C)C)C(N[Si](C)(C)C)=CC(CC=2C=C(N[Si](C)(C)C)C(O[Si](C)(C)C)=CC=2)=C1 NCMXVLJIZACJIH-UHFFFAOYSA-N 0.000 description 1
- 239000011356 non-aqueous organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- KMIOJWCYOHBUJS-HAKPAVFJSA-N vorolanib Chemical compound C1N(C(=O)N(C)C)CC[C@@H]1NC(=O)C1=C(C)NC(\C=C/2C3=CC(F)=CC=C3NC\2=O)=C1C KMIOJWCYOHBUJS-HAKPAVFJSA-N 0.000 description 1
Landscapes
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12515486A JPS62283127A (ja) | 1986-05-30 | 1986-05-30 | ポリベンズオキサゾ−ル樹脂の製造方法 |
| GB08712400A GB2191496A (en) | 1986-05-30 | 1987-05-27 | Method of preparing aromatic polyamides and polybenzoxazoles |
| US07/054,965 US4820793A (en) | 1986-05-30 | 1987-05-28 | Method of preparing aromatic polyamides and polybenzoxazoles |
| DE19873718212 DE3718212A1 (de) | 1986-05-30 | 1987-05-29 | Verfahren zur herstellung von aromatischen polyamiden und polybenzoxazolen |
| IT20732/87A IT1205115B (it) | 1986-05-30 | 1987-05-29 | Metodo per preparare poliammidi aromatiche e polibenzossazoli |
| FR878707596A FR2599370B1 (fr) | 1986-05-30 | 1987-05-29 | Procede de preparation de polyamides aromatiques et de polybenzoxazoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12515486A JPS62283127A (ja) | 1986-05-30 | 1986-05-30 | ポリベンズオキサゾ−ル樹脂の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62283127A true JPS62283127A (ja) | 1987-12-09 |
| JPH0458808B2 JPH0458808B2 (enrdf_load_stackoverflow) | 1992-09-18 |
Family
ID=14903208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12515486A Granted JPS62283127A (ja) | 1986-05-30 | 1986-05-30 | ポリベンズオキサゾ−ル樹脂の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62283127A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63305130A (ja) * | 1987-05-18 | 1988-12-13 | シーメンス、アクチエンゲゼルシヤフト | 耐高熱性誘電体の製造方法 |
| JPH01292034A (ja) * | 1988-05-19 | 1989-11-24 | Cosmo Oil Co Ltd | ポリ（アミドベンゾオキサゾール）樹脂の製造方法 |
| JPH02247225A (ja) * | 1989-03-20 | 1990-10-03 | Honda Motor Co Ltd | ポリベンゾビスオキサゾール前駆物質の製造方法 |
| JP2007262158A (ja) * | 2006-03-27 | 2007-10-11 | Osaka Prefecture | ポリオキサゾール又はその前駆体の微粒子及びその製造方法 |
-
1986
- 1986-05-30 JP JP12515486A patent/JPS62283127A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63305130A (ja) * | 1987-05-18 | 1988-12-13 | シーメンス、アクチエンゲゼルシヤフト | 耐高熱性誘電体の製造方法 |
| JPH01292034A (ja) * | 1988-05-19 | 1989-11-24 | Cosmo Oil Co Ltd | ポリ（アミドベンゾオキサゾール）樹脂の製造方法 |
| JPH02247225A (ja) * | 1989-03-20 | 1990-10-03 | Honda Motor Co Ltd | ポリベンゾビスオキサゾール前駆物質の製造方法 |
| JP2007262158A (ja) * | 2006-03-27 | 2007-10-11 | Osaka Prefecture | ポリオキサゾール又はその前駆体の微粒子及びその製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0458808B2 (enrdf_load_stackoverflow) | 1992-09-18 |
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