CA1336464C - Compositions ether-polyepoxyde, utiles pour la production de circuits imprimes - Google Patents

Compositions ether-polyepoxyde, utiles pour la production de circuits imprimes

Info

Publication number: CA1336464C
Authority: CA; Canada
Prior art keywords: blend according; component; halogen; reagent; polyphenylene ether
Prior art date: 1988-07-14
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

CA000602222A

Other languages

English (en)

Inventor

John Edward Hallgren

Victoria Jean Eddy

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.)

1988-07-14

Filing date

1989-06-08

Publication date

1995-07-25

1989-06-08 Application filed by General Electric Co filed Critical General Electric Co

1995-07-25 Application granted granted Critical

1995-07-25 Publication of CA1336464C publication Critical patent/CA1336464C/fr

2012-07-25 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 92
-1 polyphenylene Polymers 0.000 title claims description 26
229920000647 polyepoxide Polymers 0.000 title description 11
238000004519 manufacturing process Methods 0.000 title description 9
229920000265 Polyparaphenylene Polymers 0.000 title description 5
229920001955 polyphenylene ether Polymers 0.000 claims abstract description 25
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 abstract description 19
229920003986 novolac Polymers 0.000 claims abstract description 19
229930185605 Bisphenol Natural products 0.000 claims abstract description 8
239000003153 chemical reaction reagent Substances 0.000 claims description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
229910052794 bromium Inorganic materials 0.000 claims description 19
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 17
150000001875 compounds Chemical class 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
101000623895 Bos taurus Mucin-15 Proteins 0.000 claims description 8
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 6
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000007795 chemical reaction product Substances 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 3
125000001188 haloalkyl group Chemical group 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims 1
239000003054 catalyst Substances 0.000 abstract description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 10
238000006243 chemical reaction Methods 0.000 abstract description 10
238000002360 preparation method Methods 0.000 abstract description 10
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 16
239000000463 material Substances 0.000 description 13
LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 12
229920000642 polymer Polymers 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
229960005419 nitrogen Drugs 0.000 description 9
229910052725 zinc Inorganic materials 0.000 description 9
239000011701 zinc Substances 0.000 description 9
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
229920000768 polyamine Polymers 0.000 description 7
238000000034 method Methods 0.000 description 6
239000002966 varnish Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000004593 Epoxy Substances 0.000 description 5
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
229910052748 manganese Inorganic materials 0.000 description 5
239000011572 manganese Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
239000004744 fabric Substances 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
150000002460 imidazoles Chemical class 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
239000000047 product Substances 0.000 description 4
150000003751 zinc Chemical class 0.000 description 4
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 description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
125000000732 arylene group Chemical group 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
239000002131 composite material Substances 0.000 description 3
239000007822 coupling agent Substances 0.000 description 3
125000005594 diketone group Chemical group 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000011521 glass Substances 0.000 description 3
229920001519 homopolymer Polymers 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
238000005691 oxidative coupling reaction Methods 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
229910000679 solder Inorganic materials 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
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 3
XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
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
YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
238000013019 agitation Methods 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
229910052787 antimony Inorganic materials 0.000 description 2
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
239000003795 chemical substances by application Substances 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
238000001246 colloidal dispersion Methods 0.000 description 2
238000000748 compression moulding Methods 0.000 description 2
239000000470 constituent Substances 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
230000001186 cumulative effect Effects 0.000 description 2
230000007812 deficiency 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
239000003989 dielectric material Substances 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000011152 fibreglass Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000005470 impregnation Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
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 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
239000004848 polyfunctional curative Substances 0.000 description 2
239000001294 propane Substances 0.000 description 2
229920005604 random copolymer Polymers 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000012260 resinous material Substances 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
238000010998 test method Methods 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
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
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical compound NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 description 1
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 1
KPTMGJRRIXXKKW-UHFFFAOYSA-N 2,3,5-trimethyl-7-oxabicyclo[2.2.1]hepta-1,3,5-triene Chemical group O1C2=C(C)C(C)=C1C=C2C KPTMGJRRIXXKKW-UHFFFAOYSA-N 0.000 description 1
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 1
UNMUYUJQFADDAM-UHFFFAOYSA-N 2-N,2-N-diethyl-1-N-methylbenzene-1,2-diamine Chemical class C(C)N(C1=C(C=CC=C1)NC)CC UNMUYUJQFADDAM-UHFFFAOYSA-N 0.000 description 1
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-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
WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-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
BVYPJEBKDLFIDL-UHFFFAOYSA-N 3-(2-phenylimidazol-1-yl)propanenitrile Chemical compound N#CCCN1C=CN=C1C1=CC=CC=C1 BVYPJEBKDLFIDL-UHFFFAOYSA-N 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
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 1
229920002972 Acrylic fiber Polymers 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
BSDSAXHIDUGPNJ-UHFFFAOYSA-N C=C=C=CC1CCCCC1 Chemical group C=C=C=CC1CCCCC1 BSDSAXHIDUGPNJ-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229920003043 Cellulose fiber Polymers 0.000 description 1
239000005749 Copper compound Substances 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
YXLXNENXOJSQEI-UHFFFAOYSA-L Oxine-copper Chemical compound [Cu+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 YXLXNENXOJSQEI-UHFFFAOYSA-L 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000005263 alkylenediamine group Chemical group 0.000 description 1
125000001118 alkylidene group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000002216 antistatic agent Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000008901 benefit Effects 0.000 description 1
YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
239000002738 chelating agent Substances 0.000 description 1
238000005253 cladding Methods 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910052570 clay Inorganic materials 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
150000001869 cobalt compounds Chemical class 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
150000001880 copper compounds Chemical class 0.000 description 1
239000011889 copper foil Substances 0.000 description 1
229930003836 cresol Natural products 0.000 description 1
230000002950 deficient Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
239000003822 epoxy resin Substances 0.000 description 1
230000003628 erosive effect Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
230000009477 glass transition Effects 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
229910001385 heavy metal Inorganic materials 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
238000007654 immersion Methods 0.000 description 1
230000006872 improvement Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229940018564 m-phenylenediamine Drugs 0.000 description 1
150000004988 m-phenylenediamines Chemical class 0.000 description 1
150000002697 manganese compounds Chemical class 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
239000000178 monomer Substances 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229910017464 nitrogen compound Inorganic materials 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
150000004989 p-phenylenediamines Chemical class 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
238000013031 physical testing Methods 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
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor 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
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 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
239000007787 solid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000012360 testing method Methods 0.000 description 1
239000003017 thermal stabilizer Substances 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 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
230000002087 whitening effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
- C08L71/123—Polyphenylene oxides not modified by chemical after-treatment
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0326—Organic insulating material consisting of one material containing O

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Epoxy Resins (AREA)
Reinforced Plastic Materials (AREA)
Laminated Bodies (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA000602222A 1988-07-14 1989-06-08 Compositions ether-polyepoxyde, utiles pour la production de circuits imprimes Expired - Fee Related CA1336464C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US21910288A	1988-07-14	1988-07-14
US219,102		1988-07-14

Publications (1)

Publication Number	Publication Date
CA1336464C true CA1336464C (fr)	1995-07-25

Family

ID=22817886

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000602222A Expired - Fee Related CA1336464C (fr)	1988-07-14	1989-06-08	Compositions ether-polyepoxyde, utiles pour la production de circuits imprimes

Country Status (5)

Country	Link
JP (1)	JPH0689121B2 (fr)
KR (1)	KR940001718B1 (fr)
CA (1)	CA1336464C (fr)
DE (1)	DE3922741C2 (fr)
SE (1)	SE504344C2 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN1036402C (zh) *	1991-01-11	1997-11-12	旭化成工业株式会社	可固化的聚苯氧树脂组合物及由它制成的薄膜
KR100612302B1 (ko) *	2004-07-16	2006-08-11	삼성에스디아이 주식회사	고체 고분자형 연료전지용 접착제 조성물 및 이로부터제조되는 연료전지
JP4146408B2 (ja) *	2004-09-10	2008-09-10	三菱電機株式会社	ステアリング制御装置

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1643309U (de) *	1952-02-11	1952-09-04	Loewe Opta Ag	Schallplattengeraet mit mitteln zur inbetriebnahme von schallplatten verschiedener laufgeschwindigkeit.
US4895755A (en) *	1986-09-15	1990-01-23	The Dow Chemical Company	Halogenated advanced epoxy resins
JPS63125516A (ja) *	1986-11-15	1988-05-28	Matsushita Electric Works Ltd	エポキシ樹脂の製造方法

1989
- 1989-06-08 CA CA000602222A patent/CA1336464C/fr not_active Expired - Fee Related
- 1989-07-10 SE SE8902491A patent/SE504344C2/sv not_active IP Right Cessation
- 1989-07-11 DE DE3922741A patent/DE3922741C2/de not_active Expired - Fee Related
- 1989-07-14 KR KR1019890010023A patent/KR940001718B1/ko not_active Expired - Fee Related
- 1989-07-14 JP JP1180692A patent/JPH0689121B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE3922741A1 (de)	1990-01-18
KR940001718B1 (ko)	1994-03-05
SE504344C2 (sv)	1997-01-20
SE8902491L (sv)	1990-01-15
JPH0255722A (ja)	1990-02-26
DE3922741C2 (de)	1994-09-08
KR900001789A (ko)	1990-02-27
SE8902491D0 (sv)	1989-07-10
JPH0689121B2 (ja)	1994-11-09

Legal Events

Date	Code	Title	Description
2006-07-25	MKLA	Lapsed

Publication	Publication Date	Title
EP0350696B1 (fr)	1995-01-18	Composition durcissable de poly(éther de phénylène)/polyépoxyde utilisable pour la production de plaquettes à circuits imprimés
US5213886A (en)	1993-05-25	Curable dielectric polyphenylene ether-polyepoxide compositions
US5043367A (en)	1991-08-27	Curable dielectric polyphenylene ether-polyepoxide compositions useful in printed circuit board production
US4912172A (en)	1990-03-27	Compositions comprising polyphenylene ethers, polyepoxides and aluminum or zinc diketone salt
EP0383178B1 (fr)	1999-11-10	Compositions d'éther de phénylène-polyepoxide durcissables diélectriques
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
US5141791A (en)	1992-08-25	Curable polyphenylene ether-polyepoxide compositions from melt processed polyphenylene ethers, and laminates prepared therefrom
US5089343A (en)	1992-02-18	Curable dielectric polyphenylene ether-polyepoxide compositions
EP0506366B1 (fr)	1997-12-29	Compositions durcissables à haute performance à base de poly(oxyde de phénylène) et de composés époxydes contenant un sel d'étain comme agent de compatibilisation
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
EP0592145B1 (fr)	1998-05-20	Compositions de résines polyphénylène éther-polyépoxyde
US5096771A (en)	1992-03-17	Fibers impregnated with epoxy resin mixture, brominated bisphenol and polyphenylene ether
KR940001718B1 (ko)	1994-03-05	인쇄회로판 제조에 유용한 폴리에폭사이드 및 폴리페닐렌 에테르-폴리에폭사이드 조성물을 함유하는 수지상 배합물
KR940002283B1 (ko)	1994-03-21	인쇄 회로기판 제조에 유용한 경화가능한 절연성 폴리페닐렌 에테르-폴리에폭시드 조성물
CA1336845C (fr)	1995-08-29	Compositions durcissables de polymeres comportant des ethers de polypropylene et des polyepoxydes
CA2013937A1 (fr)	1991-02-03	Compositions durcissables dielectriques ether polyphenylenique-polyepoxyde