JPS62521A - 縮合多環多核芳香族樹脂の製造方法及びその製造に用いる熱硬化性組成物 - Google Patents
縮合多環多核芳香族樹脂の製造方法及びその製造に用いる熱硬化性組成物Info
- Publication number
- JPS62521A JPS62521A JP3332686A JP3332686A JPS62521A JP S62521 A JPS62521 A JP S62521A JP 3332686 A JP3332686 A JP 3332686A JP 3332686 A JP3332686 A JP 3332686A JP S62521 A JPS62521 A JP S62521A
- Authority
- JP
- Japan
- Prior art keywords
- crosslinking agent
- raw material
- molecular weight
- aromatic compound
- mixture
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 80
- 229920005989 resin Polymers 0.000 title claims abstract description 54
- 239000011347 resin Substances 0.000 title claims abstract description 54
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 15
- 125000003367 polycyclic group Chemical group 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 68
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 54
- -1 polycyclic aromatic compound Chemical class 0.000 claims abstract description 40
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 32
- 125000004970 halomethyl group Chemical group 0.000 claims abstract description 22
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 22
- 239000003377 acid catalyst Substances 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims description 81
- 239000000047 product Substances 0.000 claims description 78
- 238000010438 heat treatment Methods 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 24
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 18
- 239000007795 chemical reaction product Substances 0.000 claims description 16
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 16
- 238000006482 condensation reaction Methods 0.000 claims description 15
- 239000011295 pitch Substances 0.000 claims description 13
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 10
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 6
- XMUZQOKACOLCSS-UHFFFAOYSA-N [2-(hydroxymethyl)phenyl]methanol Chemical group OCC1=CC=CC=C1CO XMUZQOKACOLCSS-UHFFFAOYSA-N 0.000 claims description 5
- 239000011300 coal pitch Substances 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000011417 postcuring Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000011301 petroleum pitch Substances 0.000 claims description 2
- 239000011847 coal-based material Substances 0.000 claims 1
- 239000011846 petroleum-based material Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 abstract description 5
- 239000007859 condensation product Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 61
- 238000001723 curing Methods 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 239000000463 material Substances 0.000 description 12
- 230000004580 weight loss Effects 0.000 description 11
- 230000009257 reactivity Effects 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 239000011294 coal tar pitch Substances 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000004917 carbon fiber Substances 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 239000011280 coal tar Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 229920000049 Carbon (fiber) Polymers 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004971 Cross linker Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229920006272 aromatic hydrocarbon resin Polymers 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 239000003245 coal Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 229920006015 heat resistant resin Polymers 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 239000000615 nonconductor Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000002411 thermogravimetry Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
- 239000000805 composite resin Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- GBROPGWFBFCKAG-UHFFFAOYSA-N picene Chemical compound C1=CC2=C3C=CC=CC3=CC=C2C2=C1C1=CC=CC=C1C=C2 GBROPGWFBFCKAG-UHFFFAOYSA-N 0.000 description 2
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 2
- 238000006561 solvent free reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- HETNNUSMWLIANA-UHFFFAOYSA-N [1-(hydroxymethyl)naphthalen-2-yl]methanol Chemical compound C1=CC=CC2=C(CO)C(CO)=CC=C21 HETNNUSMWLIANA-UHFFFAOYSA-N 0.000 description 1
- DQJJXEZXOYPSNJ-UHFFFAOYSA-N [2,3-bis(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC(CO)=C1CO DQJJXEZXOYPSNJ-UHFFFAOYSA-N 0.000 description 1
- CKYOUYSBIZYHNU-UHFFFAOYSA-N [2-(hydroxymethyl)-3,4-dimethylphenyl]methanol Chemical group CC1=CC=C(CO)C(CO)=C1C CKYOUYSBIZYHNU-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- JDPBLCQVGZLACA-UHFFFAOYSA-N benzo[a]perylene Chemical class C1=CC(C=2C3=CC=CC=C3C=C3C=2C2=CC=C3)=C3C2=CC=CC3=C1 JDPBLCQVGZLACA-UHFFFAOYSA-N 0.000 description 1
- TXVHTIQJNYSSKO-UHFFFAOYSA-N benzo[e]pyrene Chemical class C1=CC=C2C3=CC=CC=C3C3=CC=CC4=CC=C1C2=C34 TXVHTIQJNYSSKO-UHFFFAOYSA-N 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000007833 carbon precursor Substances 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000007731 hot pressing Methods 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000006839 xylylene group Chemical group 0.000 description 1
Landscapes
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60-30055 | 1985-02-18 | ||
| JP60-30056 | 1985-02-18 | ||
| JP3005585 | 1985-02-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62521A true JPS62521A (ja) | 1987-01-06 |
| JPH0579093B2 JPH0579093B2 (enExample) | 1993-11-01 |
Family
ID=12293137
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3332686A Granted JPS62521A (ja) | 1985-02-18 | 1986-02-18 | 縮合多環多核芳香族樹脂の製造方法及びその製造に用いる熱硬化性組成物 |
| JP3332786A Granted JPS62522A (ja) | 1985-02-18 | 1986-02-18 | 芳香族樹脂の製造方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3332786A Granted JPS62522A (ja) | 1985-02-18 | 1986-02-18 | 芳香族樹脂の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (2) | JPS62521A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62127350A (ja) * | 1985-11-28 | 1987-06-09 | Ibiden Co Ltd | 熱硬化性樹脂をマトリツクスとする複合材料及びその製造方法 |
| US5514475A (en) * | 1993-01-22 | 1996-05-07 | Sumitomo Metal Industries, Ltd. | Heat-resistant electrical insulating layer |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01124628A (ja) * | 1987-11-10 | 1989-05-17 | Sugiro Otani | 縮合多環多核芳香族繊維の製造方法 |
| US5117742A (en) * | 1989-04-28 | 1992-06-02 | Iwata Air Compressor Mfg. Co. Ltd. | Piston of composite material with c-shaped ring groove |
| JP2551166B2 (ja) * | 1989-09-13 | 1996-11-06 | 横河電機株式会社 | プロセス制御装置 |
| JP2757039B2 (ja) * | 1989-09-26 | 1998-05-25 | 横河電機株式会社 | セルフチューニング調節計 |
| US5780571A (en) * | 1993-03-22 | 1998-07-14 | Nippon Kayaku Kabushiki Kaisha | Naphthalene ring-containing resins, resin compositions and cured products thereof |
| JP3132610B2 (ja) * | 1993-03-22 | 2001-02-05 | 日本化薬株式会社 | ナフタレン環含有樹脂、樹脂組成物及びその硬化物 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3565832A (en) * | 1967-09-05 | 1971-02-23 | Hughes Aircraft Co | Polymerization of aromatic monomers in presence of lewis acid catalyst and oxygen |
| US3677976A (en) * | 1970-04-09 | 1972-07-18 | Hughes Aircraft Co | Commercially useful polyphenylene polymers and method of production thereof |
| JPS5188947A (ja) * | 1975-02-01 | 1976-08-04 | Horiariirenmechirennoseizoho |
-
1986
- 1986-02-18 JP JP3332686A patent/JPS62521A/ja active Granted
- 1986-02-18 JP JP3332786A patent/JPS62522A/ja active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3565832A (en) * | 1967-09-05 | 1971-02-23 | Hughes Aircraft Co | Polymerization of aromatic monomers in presence of lewis acid catalyst and oxygen |
| US3677976A (en) * | 1970-04-09 | 1972-07-18 | Hughes Aircraft Co | Commercially useful polyphenylene polymers and method of production thereof |
| JPS5188947A (ja) * | 1975-02-01 | 1976-08-04 | Horiariirenmechirennoseizoho |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62127350A (ja) * | 1985-11-28 | 1987-06-09 | Ibiden Co Ltd | 熱硬化性樹脂をマトリツクスとする複合材料及びその製造方法 |
| US5514475A (en) * | 1993-01-22 | 1996-05-07 | Sumitomo Metal Industries, Ltd. | Heat-resistant electrical insulating layer |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0579094B2 (enExample) | 1993-11-01 |
| JPH0579093B2 (enExample) | 1993-11-01 |
| JPS62522A (ja) | 1987-01-06 |
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