JPH058932B2 - - Google Patents

Info

Publication number: JPH058932B2
Authority: JP; Japan
Prior art keywords: group; polyphenylene ether; hydrogen; general formula; polymerization
Prior art date: 1987-10-27
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

Application number

JP26945987A

Other languages

English (en)

Japanese (ja)

Other versions

JPH01113425A (ja

Inventor

Teruo Katayose

Hiroharu Oda

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Asahi Chemical Industry Co Ltd

Original Assignee

Asahi Chemical Industry Co Ltd

Priority date (The priority date 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 date listed.)

1987-10-27

Filing date

1987-10-27

Publication date

1993-02-03

1987-10-27 Application filed by Asahi Chemical Industry Co Ltd filed Critical Asahi Chemical Industry Co Ltd

1987-10-27 Priority to JP26945987A priority Critical patent/JPH01113425A/ja

1988-09-08 Priority to CA000576794A priority patent/CA1336526C/fr

1988-09-08 Priority to EP88201949A priority patent/EP0309025B1/fr

1988-09-08 Priority to DE3853801T priority patent/DE3853801T2/de

1988-09-09 Priority to US07/242,234 priority patent/US4923932A/en

1989-05-02 Publication of JPH01113425A publication Critical patent/JPH01113425A/ja

1993-02-03 Publication of JPH058932B2 publication Critical patent/JPH058932B2/ja

Status Granted legal-status Critical Current

Links

229920001955 polyphenylene ether Polymers 0.000 claims description 74
238000006467 substitution reaction Methods 0.000 claims description 48
125000000304 alkynyl group Chemical group 0.000 claims description 41
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 28
229910052739 hydrogen Inorganic materials 0.000 claims description 28
-1 phenol compound Chemical class 0.000 claims description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 22
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
238000004519 manufacturing process Methods 0.000 claims description 18
125000003342 alkenyl group Chemical group 0.000 claims description 17
238000006116 polymerization reaction Methods 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000001033 ether group Chemical group 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
229910052794 bromium Inorganic materials 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 29
238000006243 chemical reaction Methods 0.000 description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 19
238000000034 method Methods 0.000 description 18
229920000642 polymer Polymers 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
229910052751 metal Inorganic materials 0.000 description 12
239000002184 metal Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
230000000704 physical effect Effects 0.000 description 12
239000000126 substance Substances 0.000 description 12
238000005160 1H NMR spectroscopy Methods 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 8
150000001408 amides Chemical class 0.000 description 7
238000009835 boiling Methods 0.000 description 7
238000004132 cross linking Methods 0.000 description 7
239000011521 glass Substances 0.000 description 7
239000012299 nitrogen atmosphere Substances 0.000 description 7
NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 6
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
230000000052 comparative effect Effects 0.000 description 6
238000007710 freezing Methods 0.000 description 6
230000008014 freezing Effects 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
238000001723 curing Methods 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
238000002955 isolation Methods 0.000 description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 4
XLYOGWXIKVUXCL-UHFFFAOYSA-N 4-bromobut-1-yne Chemical compound BrCCC#C XLYOGWXIKVUXCL-UHFFFAOYSA-N 0.000 description 4
125000006043 5-hexenyl group Chemical group 0.000 description 4
238000007259 addition reaction Methods 0.000 description 4
150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
230000007423 decrease Effects 0.000 description 4
238000006704 dehydrohalogenation reaction Methods 0.000 description 4
239000000835 fiber Substances 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
239000000463 material Substances 0.000 description 4
230000001590 oxidative effect Effects 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
229920005989 resin Polymers 0.000 description 4
239000011347 resin Substances 0.000 description 4
BIXFMRXHWVNDBA-UHFFFAOYSA-N 1-iodopent-2-yne Chemical compound CCC#CCI BIXFMRXHWVNDBA-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000000950 dibromo group Chemical group Br* 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
230000009477 glass transition Effects 0.000 description 3
239000000843 powder Substances 0.000 description 3
229920001187 thermosetting polymer Polymers 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
DMAYBPBPEUFIHJ-UHFFFAOYSA-N 4-bromobut-1-ene Chemical compound BrCCC=C DMAYBPBPEUFIHJ-UHFFFAOYSA-N 0.000 description 2
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
XXTLMXOGRBXMQF-UHFFFAOYSA-N 5-bromopent-2-yne Chemical compound CC#CCCBr XXTLMXOGRBXMQF-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000005370 alkoxysilyl group Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
238000005905 alkynylation reaction Methods 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
238000001816 cooling Methods 0.000 description 2
HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
239000000945 filler Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000006872 improvement Effects 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 2
238000006263 metalation reaction Methods 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
239000011259 mixed solution Substances 0.000 description 2
238000000465 moulding Methods 0.000 description 2
125000002524 organometallic group Chemical group 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
230000008569 process Effects 0.000 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
238000001028 reflection method Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
238000004611 spectroscopical analysis Methods 0.000 description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
LNNXOEHOXSYWLD-UHFFFAOYSA-N 1-bromobut-2-yne Chemical compound CC#CCBr LNNXOEHOXSYWLD-UHFFFAOYSA-N 0.000 description 1
VKRJVJZWDJDJBX-UHFFFAOYSA-N 1-chloro-4-(chloromethoxy)butane Chemical compound ClCCCCOCCl VKRJVJZWDJDJBX-UHFFFAOYSA-N 0.000 description 1
BKZDYWLQNSCDLY-UHFFFAOYSA-N 1-iodohex-3-yne Chemical compound CCC#CCCI BKZDYWLQNSCDLY-UHFFFAOYSA-N 0.000 description 1
QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000006024 2-pentenyl group Chemical group 0.000 description 1
125000006041 3-hexenyl group Chemical group 0.000 description 1
YGYPMFPGZQPETF-UHFFFAOYSA-N 4-(4-hydroxy-3,5-dimethylphenyl)-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C=2C=C(C)C(O)=C(C)C=2)=C1 YGYPMFPGZQPETF-UHFFFAOYSA-N 0.000 description 1
ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
LPNANKDXVBMDKE-UHFFFAOYSA-N 5-bromopent-1-ene Chemical compound BrCCCC=C LPNANKDXVBMDKE-UHFFFAOYSA-N 0.000 description 1
KEKBNXAJNJSILY-UHFFFAOYSA-N 5-bromopent-1-yne Chemical compound BrCCCC#C KEKBNXAJNJSILY-UHFFFAOYSA-N 0.000 description 1
RIMXEJYJXDBLIE-UHFFFAOYSA-N 6-bromohex-1-ene Chemical compound BrCCCCC=C RIMXEJYJXDBLIE-UHFFFAOYSA-N 0.000 description 1
WDNFOERVYIUQPG-UHFFFAOYSA-N 6-bromohex-1-yne Chemical compound BrCCCCC#C WDNFOERVYIUQPG-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
229920000049 Carbon (fiber) Polymers 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000002216 antistatic agent Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000010425 asbestos Substances 0.000 description 1
239000011324 bead Substances 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
239000004917 carbon fiber Substances 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
239000011889 copper foil Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
239000003989 dielectric material Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
238000010894 electron beam technology Methods 0.000 description 1
229920006351 engineering plastic Polymers 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
239000004210 ether based solvent Substances 0.000 description 1
239000010408 film Substances 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
125000004970 halomethyl group Chemical group 0.000 description 1
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
229920006015 heat resistant resin Polymers 0.000 description 1
239000012760 heat stabilizer Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
238000005259 measurement Methods 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000000178 monomer Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000647 polyepoxide Polymers 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052895 riebeckite Inorganic materials 0.000 description 1
SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000679 solder Inorganic materials 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000000930 thermomechanical effect Effects 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1

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JP26945987A 1987-09-09 1987-10-27 三重結合を含む硬化性ポリフェニレンエーテルおよびその製造法 Granted JPH01113425A (ja)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
JP26945987A JPH01113425A (ja)	1987-10-27	1987-10-27	三重結合を含む硬化性ポリフェニレンエーテルおよびその製造法
CA000576794A CA1336526C (fr)	1987-09-09	1988-09-08	Resine de poly(oxyde de phenylene) reticule et resine de poly(oxyde de phenylene) reticulable
EP88201949A EP0309025B1 (fr)	1987-09-09	1988-09-08	Une résine de poly(éther de phénylène) durcie et une résine de poly(éther de phénylène) durcissable
DE3853801T DE3853801T2 (de)	1987-09-09	1988-09-08	Ein gehärtetes Polyphenylenetherharz und ein härtbares Polyphenylenetherharz.
US07/242,234 US4923932A (en)	1987-09-09	1988-09-09	Polyphenylene ether resin comprising chloroform extractable/nonextractable polyphenylene ether resin

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP26945987A JPH01113425A (ja)	1987-10-27	1987-10-27	三重結合を含む硬化性ポリフェニレンエーテルおよびその製造法

Publications (2)

Publication Number	Publication Date
JPH01113425A JPH01113425A (ja)	1989-05-02
JPH058932B2 true JPH058932B2 (fr)	1993-02-03

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ID=17472731

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP26945987A Granted JPH01113425A (ja)	1987-09-09	1987-10-27	三重結合を含む硬化性ポリフェニレンエーテルおよびその製造法

Country Status (1)

Country	Link
JP (1)	JPH01113425A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7291692B2 (en)	2003-09-25	2007-11-06	Sumitomo Chemical Company, Limited	Polyarylene oxide and method of producing the same
WO2014104224A1 (fr)	2012-12-26	2014-07-03	Nakajima Toshihiro	RÉGULATEUR DE FONCTION DE LA PROTÉINE PGC-1β, RÉGULATEUR DE FONCTION MITOCHONDRIALE, AGENT ANTI-OBÉSITÉ ET MÉTHODE DE CRIBLAGE ASSOCIÉE

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0678482B2 (ja) *	1988-10-29	1994-10-05	旭化成工業株式会社	硬化性ポリフェニレンエーテル樹脂組成物及びその硬化体のシート又はフィルム並びにその用途
WO1999000435A1 (fr)	1997-06-30	1999-01-07	Sanyo Chemical Industries, Ltd.	Resine polymerisable, resines durcies, isolants, composants d'appareils electriques et appareils electriques fabriques au moyen de ces derniers
US6716955B2 (en) *	2002-01-14	2004-04-06	Air Products And Chemicals, Inc.	Poly(arylene ether) polymer with low temperature crosslinking grafts and adhesive comprising the same

1987
- 1987-10-27 JP JP26945987A patent/JPH01113425A/ja active Granted

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7291692B2 (en)	2003-09-25	2007-11-06	Sumitomo Chemical Company, Limited	Polyarylene oxide and method of producing the same
WO2014104224A1 (fr)	2012-12-26	2014-07-03	Nakajima Toshihiro	RÉGULATEUR DE FONCTION DE LA PROTÉINE PGC-1β, RÉGULATEUR DE FONCTION MITOCHONDRIALE, AGENT ANTI-OBÉSITÉ ET MÉTHODE DE CRIBLAGE ASSOCIÉE

Also Published As

Publication number	Publication date
JPH01113425A (ja)	1989-05-02

Legal Events

Date	Code	Title	Description
2006-02-03	LAPS	Cancellation because of no payment of annual fees

Publication	Publication Date	Title
EP0309025B1 (fr)	1995-05-17	Une résine de poly(éther de phénylène) durcie et une résine de poly(éther de phénylène) durcissable
JP6976981B2 (ja)	2021-12-08	ジシクロペンタジエンを有する官能化ポリ（２，６−ジメチルフェニレンオキシド）オリゴマー及びその製造方法、並びにその用途
WO2018181842A1 (fr)	2018-10-04	Copolymère aromatique vinylique polyfonctionnel soluble, son procédé de production, composition de résine durcissable et produit durci à base de celui-ci
JP7550381B2 (ja)	2024-09-13	プリプレグ、金属張積層板、及び配線板
EP2880079A1 (fr)	2015-06-10	Synthèse de phtalonitriles et additifs durcissants pour phtalonitriles
EP3636692B1 (fr)	2026-04-29	Copolymère de poly (arylène éther)
JPS6235404B2 (fr)	1987-08-01
JPH058930B2 (fr)	1993-02-03
JP2646701B2 (ja)	1997-08-27	ポリアルケニルフエノール化合物
JPH02269716A (ja)	1990-11-05	芳香族ビスマレイミドに基づいた硬化性組成物
JPH01113426A (ja)	1989-05-02	二重結合を含む硬化性ポリフェニレンエーテルおよびその製造法
JPH058932B2 (fr)	1993-02-03
JPH058931B2 (fr)	1993-02-03
JP4288473B2 (ja)	2009-07-01	新規ポリエステルおよびフィルムおよび積層体
JPH0726013B2 (ja)	1995-03-22	硬化性ポリフェニレンエーテル樹脂組成物並びにこれを用いた複合材料および積層体
JP2966867B2 (ja)	1999-10-25	フェノール−ジシクロペンタジエン付加物の縮合生成物の熱硬化性樹脂としてのエーテルの製造法
KR100268521B1 (ko)	2000-10-16	경화성수지조성물,수지경화물및전기저항체
US4515938A (en)	1985-05-07	Hydroxystyrylazapolymers
JPH02233723A (ja)	1990-09-17	新規な官能化ポリフェニレンエーテル樹脂組成物
JPH02120357A (ja)	1990-05-08	硬化ポリフェニレンエーテル樹脂
JPS61235413A (ja)	1986-10-20	フエノ−ル変性芳香族炭化水素ホルムアルデヒド樹脂の製造方法
US5723573A (en)	1998-03-03	Thermosetting polyquinolines
TWI877482B (zh)	2025-03-21	用於改善對基材之附著力的雙官能上膠劑
AU592989B2 (en)	1990-02-01	Thermostable compounds prepared from monohydroxy aromatic aldehydes and methylated pyridines or pyrazines
EP0410547B1 (fr)	1996-01-03	Polymères d'éthers de propargyles aromatiques

JPH058932B2 - - Google Patents

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Priority Applications (5)

Applications Claiming Priority (1)

Publications (2)

Family

ID=17472731

Family Applications (1)

Country Status (1)

Cited By (2)

Families Citing this family (3)

Cited By (2)

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