CA2013937A1 - Compositions durcissables dielectriques ether polyphenylenique-polyepoxyde - Google Patents

Compositions durcissables dielectriques ether polyphenylenique-polyepoxyde

Info

Publication number: CA2013937A1
Authority: CA; Canada
Prior art keywords: composition according; composition; component; amount; curable
Prior art date: 1989-08-03
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

Application number

CA 2013937

Other languages

English (en)

Inventor

Robert E. Colborn

James R. Presley

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.)

General Electric Co

Original Assignee

General Electric Co

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.)

1989-08-03

Filing date

1990-04-05

Publication date

1991-02-03

1990-04-05 Application filed by General Electric Co filed Critical General Electric Co

1990-04-05 Priority to CA 2013937 priority Critical patent/CA2013937A1/fr

1991-02-03 Publication of CA2013937A1 publication Critical patent/CA2013937A1/fr

Status Abandoned legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 148
229920000647 polyepoxide Polymers 0.000 title claims abstract description 37
-1 POLYPHENYLENE Polymers 0.000 claims abstract description 55
229920000265 Polyparaphenylene Polymers 0.000 claims abstract description 13
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims abstract description 8
229920001955 polyphenylene ether Polymers 0.000 claims description 37
239000003153 chemical reaction reagent Substances 0.000 claims description 32
229920003986 novolac Polymers 0.000 claims description 32
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 30
239000002904 solvent Substances 0.000 claims description 30
150000001875 compounds Chemical class 0.000 claims description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 22
229930185605 Bisphenol Natural products 0.000 claims description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
229910052794 bromium Inorganic materials 0.000 claims description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 12
229920000768 polyamine Polymers 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 claims description 9
ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 8
125000001931 aliphatic group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 8
229910052751 metal Inorganic materials 0.000 claims description 8
239000002184 metal Substances 0.000 claims description 8
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 6
239000007795 chemical reaction product Substances 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
229910052725 zinc Inorganic materials 0.000 claims description 6
239000011701 zinc Substances 0.000 claims description 6
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
229910052782 aluminium Inorganic materials 0.000 claims description 5
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
229910052802 copper Inorganic materials 0.000 claims description 5
239000010949 copper Substances 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
239000000758 substrate Substances 0.000 claims description 5
229910000410 antimony oxide Inorganic materials 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
230000003197 catalytic effect Effects 0.000 claims description 3
239000003365 glass fiber Substances 0.000 claims description 3
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
239000007983 Tris buffer Substances 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000002950 monocyclic group Chemical group 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 claims description 2
NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 claims description 2
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 2
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 2
150000001491 aromatic compounds Chemical class 0.000 claims 1
239000003054 catalyst Substances 0.000 abstract description 18
238000002360 preparation method Methods 0.000 abstract description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 41
235000013350 formula milk Nutrition 0.000 description 20
229920005989 resin Polymers 0.000 description 19
239000011347 resin Substances 0.000 description 19
239000000463 material Substances 0.000 description 18
229920000642 polymer Polymers 0.000 description 16
150000002460 imidazoles Chemical class 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
239000004593 Epoxy Substances 0.000 description 11
239000003822 epoxy resin Substances 0.000 description 10
239000004744 fabric Substances 0.000 description 10
238000000034 method Methods 0.000 description 10
150000003254 radicals Chemical class 0.000 description 10
238000004519 manufacturing process Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 6
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 6
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 6
LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 6
239000011521 glass Substances 0.000 description 6
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 5
239000004721 Polyphenylene oxide Substances 0.000 description 5
239000000470 constituent Substances 0.000 description 5
238000004090 dissolution Methods 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
238000011068 loading method Methods 0.000 description 5
229910052748 manganese Inorganic materials 0.000 description 5
239000011572 manganese Substances 0.000 description 5
235000002908 manganese Nutrition 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
229920006380 polyphenylene oxide Polymers 0.000 description 5
239000000243 solution Substances 0.000 description 5
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 4
DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
238000005691 oxidative coupling reaction Methods 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
239000007822 coupling agent Substances 0.000 description 3
238000000113 differential scanning calorimetry Methods 0.000 description 3
238000005530 etching Methods 0.000 description 3
239000003063 flame retardant Substances 0.000 description 3
230000009477 glass transition Effects 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
229920001519 homopolymer Polymers 0.000 description 3
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 3
229910000679 solder Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
230000004580 weight loss Effects 0.000 description 3
GIWQSPITLQVMSG-UHFFFAOYSA-N 1,2-dimethylimidazole Chemical compound CC1=NC=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-N 0.000 description 2
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 2
NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 description 2
PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 2
ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical class C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
229940099408 Oxidizing agent Drugs 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000013019 agitation Methods 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
229960003328 benzoyl peroxide Drugs 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
238000005253 cladding Methods 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
238000007906 compression Methods 0.000 description 2
230000006835 compression Effects 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
230000001186 cumulative effect Effects 0.000 description 2
125000005265 dialkylamine group Chemical group 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
125000005594 diketone group Chemical class 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
150000002357 guanidines Chemical class 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
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 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
125000004464 hydroxyphenyl group Chemical group 0.000 description 2
238000007654 immersion Methods 0.000 description 2
230000006872 improvement Effects 0.000 description 2
238000003475 lamination Methods 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
239000004848 polyfunctional curative Substances 0.000 description 2
238000012545 processing Methods 0.000 description 2
229920005604 random copolymer Polymers 0.000 description 2
239000000725 suspension 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
POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
OPNUROKCUBTKLF-UHFFFAOYSA-N 1,2-bis(2-methylphenyl)guanidine Chemical group CC1=CC=CC=C1N\C(N)=N\C1=CC=CC=C1C OPNUROKCUBTKLF-UHFFFAOYSA-N 0.000 description 1
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 description 1
150000005000 2,6-diaminotoluenes Chemical class 0.000 description 1
STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
LBBOQIHGWMYDPM-UHFFFAOYSA-N 2-tert-butylphenol;formaldehyde Chemical compound O=C.CC(C)(C)C1=CC=CC=C1O LBBOQIHGWMYDPM-UHFFFAOYSA-N 0.000 description 1
GVLZQVREHWQBJN-UHFFFAOYSA-N 3,5-dimethyl-7-oxabicyclo[2.2.1]hepta-1,3,5-triene Chemical group CC1=C(O2)C(C)=CC2=C1 GVLZQVREHWQBJN-UHFFFAOYSA-N 0.000 description 1
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
YSWBFLWKAIRHEI-UHFFFAOYSA-N 4,5-dimethyl-1h-imidazole Chemical compound CC=1N=CNC=1C YSWBFLWKAIRHEI-UHFFFAOYSA-N 0.000 description 1
QDRFIDSUGRGGAY-UHFFFAOYSA-N 4-(3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)-2,6-dimethylcyclohexa-2,5-dien-1-one Chemical compound C1=C(C)C(=O)C(C)=CC1=C1C=C(C)C(=O)C(C)=C1 QDRFIDSUGRGGAY-UHFFFAOYSA-N 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
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MERIEQHLDYSVSR-UHFFFAOYSA-N n-[[2-[[bis(oxiran-2-ylmethyl)amino]methyl]phenyl]methyl]-1-(oxiran-2-yl)-n-(oxiran-2-ylmethyl)methanamine Chemical compound C1OC1CN(CC=1C(=CC=CC=1)CN(CC1OC1)CC1OC1)CC1CO1 MERIEQHLDYSVSR-UHFFFAOYSA-N 0.000 description 1
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
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RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
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NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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WATYAKBWIQTPDE-UHFFFAOYSA-N pentane-2,4-dione;zinc Chemical compound [Zn].CC(=O)CC(C)=O WATYAKBWIQTPDE-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
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150000002989 phenols Chemical class 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
150000004291 polyenes Chemical class 0.000 description 1
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239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
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239000001294 propane Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
150000004053 quinones Chemical class 0.000 description 1
239000012779 reinforcing material Substances 0.000 description 1
239000011342 resin composition Substances 0.000 description 1
239000012260 resinous material Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000646 scanning calorimetry Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
101150111745 sucA gene Proteins 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 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
239000003017 thermal stabilizer Substances 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
230000007704 transition Effects 0.000 description 1
239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1
150000003752 zinc compounds Chemical class 0.000 description 1

Landscapes

Epoxy Resins (AREA)

CA 2013937 1989-08-03 1990-04-05 Compositions durcissables dielectriques ether polyphenylenique-polyepoxyde Abandoned CA2013937A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 2013937 CA2013937A1 (fr)	1989-08-03	1990-04-05	Compositions durcissables dielectriques ether polyphenylenique-polyepoxyde

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US389,215		1989-08-03
CA 2013937 CA2013937A1 (fr)	1989-08-03	1990-04-05	Compositions durcissables dielectriques ether polyphenylenique-polyepoxyde

Publications (1)

Publication Number	Publication Date
CA2013937A1 true CA2013937A1 (fr)	1991-02-03

Family

ID=4144686

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2013937 Abandoned CA2013937A1 (fr)	1989-08-03	1990-04-05	Compositions durcissables dielectriques ether polyphenylenique-polyepoxyde

Country Status (1)

Country	Link
CA (1)	CA2013937A1 (fr)

1990
- 1990-04-05 CA CA 2013937 patent/CA2013937A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
1997-04-07	FZDE	Dead

Publication	Publication Date	Title
US5213886A (en)	1993-05-25	Curable dielectric polyphenylene ether-polyepoxide compositions
US4853423A (en)	1989-08-01	Curable polyphenylene ether-polyepoxide compositions useful in printed circuit board production
US5162450A (en)	1992-11-10	Curable dielectric polyphenylene ether-polyepoxide compositions
US5834565A (en)	1998-11-10	Curable polyphenylene ether-thermosetting resin composition and process
US5043367A (en)	1991-08-27	Curable dielectric polyphenylene ether-polyepoxide compositions useful in printed circuit board production
US5001010A (en)	1991-03-19	Curable polyphenylene ether-polyepoxide compositions from melt processed polyphenylene ethers, and laminates prepared therefrom
US4975319A (en)	1990-12-04	Printed circuit board from fibers impregnated with epoxy resin mixture, halogenated bisphenol and polyphenylene ether
US5089343A (en)	1992-02-18	Curable dielectric polyphenylene ether-polyepoxide compositions
US5141791A (en)	1992-08-25	Curable polyphenylene ether-polyepoxide compositions from melt processed polyphenylene ethers, and laminates prepared therefrom
US5262491A (en)	1993-11-16	High performance curable PPO/monomeric epoxy compositions with tin metal salt compatibilizing agent
WO1991005015A1 (fr)	1991-04-18	Composition a base de resines pour stratifies electriques
US5108842A (en)	1992-04-28	Curable dielectric polyphenylene ether-polyepoxide compositions useful in printed circuit board production
US5073605A (en)	1991-12-17	Bromine-bisphenol reacted bisphenol and novolak epoxy resins with polyphenylene ether
EP0436212A2 (fr)	1991-07-10	Compositions à base de poly(éther de phénylène) et de polyépoxyde qui durcissent rapidement pour obtenir des matériaux retardant la flamme et soudables
CA2102484C (fr)	2004-09-07	Resine a base d'ether de polyphenylene/polyepoxyde pour fabriquer des stratifies de qualite electrique
US5096771A (en)	1992-03-17	Fibers impregnated with epoxy resin mixture, brominated bisphenol and polyphenylene ether
CA1336464C (fr)	1995-07-25	Compositions ether-polyepoxyde, utiles pour la production de circuits imprimes
KR940002283B1 (ko)	1994-03-21	인쇄 회로기판 제조에 유용한 경화가능한 절연성 폴리페닐렌 에테르-폴리에폭시드 조성물
EP0400948A2 (fr)	1990-12-05	Composition de résine époxy résistant à la chaleur et ignifugées