WO2012099713A1 - High performance thermoset useful for electrical laminate, high density interconnect and interconnect substrate applications - Google Patents
High performance thermoset useful for electrical laminate, high density interconnect and interconnect substrate applications Download PDFInfo
- Publication number
- WO2012099713A1 WO2012099713A1 PCT/US2012/020129 US2012020129W WO2012099713A1 WO 2012099713 A1 WO2012099713 A1 WO 2012099713A1 US 2012020129 W US2012020129 W US 2012020129W WO 2012099713 A1 WO2012099713 A1 WO 2012099713A1
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- WIPO (PCT)
- Prior art keywords
- composition
- grams
- maleimide
- varnish
- epoxy resin
- Prior art date
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- 229920001187 thermosetting polymer Polymers 0.000 title description 27
- 239000000758 substrate Substances 0.000 title description 21
- 239000000203 mixture Substances 0.000 claims abstract description 99
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000003822 epoxy resin Substances 0.000 claims abstract description 21
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 21
- 239000002131 composite material Substances 0.000 claims abstract description 17
- 239000004643 cyanate ester Substances 0.000 claims abstract description 17
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000576 coating method Methods 0.000 claims description 17
- 239000011248 coating agent Substances 0.000 claims description 11
- 239000002966 varnish Substances 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000853 adhesive Substances 0.000 claims description 6
- 230000001070 adhesive effect Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000005266 casting Methods 0.000 claims description 3
- LKPRJIJQUNSELI-UHFFFAOYSA-N cyanic acid triazine Chemical compound OC#N.C1=CN=NN=C1 LKPRJIJQUNSELI-UHFFFAOYSA-N 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 12
- 239000000243 solution Substances 0.000 description 41
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- 239000000178 monomer Substances 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 17
- 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 class 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 16
- 239000003063 flame retardant Substances 0.000 description 15
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- -1 acid anhydride compounds Chemical class 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
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- 229920003986 novolac Polymers 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 229920003002 synthetic resin Polymers 0.000 description 7
- 239000000057 synthetic resin Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 6
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- 239000000126 substance Substances 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
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- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
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- 238000002411 thermogravimetry Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 239000000843 powder Substances 0.000 description 3
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- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- UUQQGGWZVKUCBD-UHFFFAOYSA-N [4-(hydroxymethyl)-2-phenyl-1h-imidazol-5-yl]methanol Chemical compound N1C(CO)=C(CO)N=C1C1=CC=CC=C1 UUQQGGWZVKUCBD-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000003733 fiber-reinforced composite Substances 0.000 description 2
- 238000009730 filament winding Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000001746 injection moulding Methods 0.000 description 2
- 239000012796 inorganic flame retardant Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 2
- 150000001282 organosilanes Chemical class 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- PKJOUIVGCFHFTK-UHFFFAOYSA-L zinc;hexanoate Chemical compound [Zn+2].CCCCCC([O-])=O.CCCCCC([O-])=O PKJOUIVGCFHFTK-UHFFFAOYSA-L 0.000 description 2
- ZMAMKNPVAMKIIC-UHFFFAOYSA-N (5-benzyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC=1N=C(C=2C=CC=CC=2)NC=1CC1=CC=CC=C1 ZMAMKNPVAMKIIC-UHFFFAOYSA-N 0.000 description 1
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 1
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- KMRIWYPVRWEWRG-UHFFFAOYSA-N 2-(6-oxobenzo[c][2,1]benzoxaphosphinin-6-yl)benzene-1,4-diol Chemical compound OC1=CC=C(O)C(P2(=O)C3=CC=CC=C3C3=CC=CC=C3O2)=C1 KMRIWYPVRWEWRG-UHFFFAOYSA-N 0.000 description 1
- MXCKINYQRLLOAU-UHFFFAOYSA-N 2-[(2-hydroxyphenyl)-phenylphosphoryl]phenol Chemical compound OC1=CC=CC=C1P(=O)(C=1C(=CC=CC=1)O)C1=CC=CC=C1 MXCKINYQRLLOAU-UHFFFAOYSA-N 0.000 description 1
- PJPSSNXBPSVLIQ-UHFFFAOYSA-N 2-bis(2-hydroxy-5-methylphenyl)phosphoryl-4-methylphenol Chemical compound CC1=CC=C(O)C(P(=O)(C=2C(=CC=C(C)C=2)O)C=2C(=CC=C(C)C=2)O)=C1 PJPSSNXBPSVLIQ-UHFFFAOYSA-N 0.000 description 1
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 1
- QFZKVFCEJRXRBD-UHFFFAOYSA-N 2-ethyl-4-[(2-ethyl-5-methyl-1h-imidazol-4-yl)methyl]-5-methyl-1h-imidazole Chemical compound N1C(CC)=NC(CC2=C(NC(CC)=N2)C)=C1C QFZKVFCEJRXRBD-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
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
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- 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
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- RJIQELZAIWFNTQ-UHFFFAOYSA-N 2-phenyl-1h-imidazole;1,3,5-triazinane-2,4,6-trione Chemical compound O=C1NC(=O)NC(=O)N1.C1=CNC(C=2C=CC=CC=2)=N1 RJIQELZAIWFNTQ-UHFFFAOYSA-N 0.000 description 1
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- IZDNNHOZVXRIGA-UHFFFAOYSA-N 2h-1,2-benzoxazin-3-amine Chemical class C1=CC=C2ONC(N)=CC2=C1 IZDNNHOZVXRIGA-UHFFFAOYSA-N 0.000 description 1
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical group C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
- IYMZEPRSPLASMS-UHFFFAOYSA-N 3-phenylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(C=2C=CC=CC=2)=C1 IYMZEPRSPLASMS-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- YGYPMFPGZQPETF-UHFFFAOYSA-N 4-(4-hydroxy-3,5-dimethylphenyl)-2,6-dimethylphenol Chemical group CC1=C(O)C(C)=CC(C=2C=C(C)C(O)=C(C)C=2)=C1 YGYPMFPGZQPETF-UHFFFAOYSA-N 0.000 description 1
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- AHNGUGDMAGMLGV-UHFFFAOYSA-N 5-benzyl-3-methyl-2-phenylimidazol-4-ol Chemical compound N1=C(C=2C=CC=CC=2)N(C)C(O)=C1CC1=CC=CC=C1 AHNGUGDMAGMLGV-UHFFFAOYSA-N 0.000 description 1
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 1
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- DBSOGOMUOXHURW-UHFFFAOYSA-N bis(4-aminophenyl) phenyl phosphate Chemical compound C1=CC(N)=CC=C1OP(=O)(OC=1C=CC(N)=CC=1)OC1=CC=CC=C1 DBSOGOMUOXHURW-UHFFFAOYSA-N 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- KTLIMPGQZDZPSB-UHFFFAOYSA-N diethylphosphinic acid Chemical compound CCP(O)(=O)CC KTLIMPGQZDZPSB-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- CZHYKKAKFWLGJO-UHFFFAOYSA-N dimethyl phosphite Chemical compound COP([O-])OC CZHYKKAKFWLGJO-UHFFFAOYSA-N 0.000 description 1
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- NXHKQBCTZHECQF-UHFFFAOYSA-N ethyl(methyl)phosphinic acid Chemical compound CCP(C)(O)=O NXHKQBCTZHECQF-UHFFFAOYSA-N 0.000 description 1
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 150000002357 guanidines Chemical class 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
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000011229 interlayer Substances 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
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004761 kevlar Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- QJQYPZZUKLQGGT-UHFFFAOYSA-N methyl hypobromite Chemical compound COBr QJQYPZZUKLQGGT-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002071 nanotube Substances 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012811 non-conductive material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000013021 overheating Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical group [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229920006303 teflon fiber Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WPZJSWWEEJJSIZ-UHFFFAOYSA-N tetrabromobisphenol-F Natural products C1=C(Br)C(O)=C(Br)C=C1CC1=CC(Br)=C(O)C(Br)=C1 WPZJSWWEEJJSIZ-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- NNKSCESTDPOUKU-UHFFFAOYSA-N trioxidanylbenzene Chemical compound OOOC1=CC=CC=C1 NNKSCESTDPOUKU-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 238000007666 vacuum forming Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical compound OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 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
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/40—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes 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
- C08G59/02—Polycondensates containing more than one epoxy group per molecule
- C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
- C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
-
- 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
- C08G59/3218—Carbocyclic 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
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4042—Imines; Imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
Definitions
- the present invention relates generally to polyphenolic compounds and epoxy resins which comprise cycloaliphatic moieties, to processes for the production thereof, and to thermoset products which are made from these resins.
- Synthetic resins are widely used in both industrial and consumer electronics because of, among other things, their chemical resistance, mechanical strength and electrical properties.
- synthetic resins can be used in electronics as protective films, adhesive materials and/or insulating materials, such as interlayer insulating films.
- the synthetic resins need to provide ease of handling and certain necessary physical, thermal, electrical insulation and moisture resistance properties.
- synthetic resins having a low dielectric constant, a high solubility and a low moisture uptake as well as a high glass transition temperature (Tg) can be desirable combination of properties for electrical applications.
- synthetic resins in electronic applications can also influence the electrical signals generated in the electronics. Increases in electrical signal frequency in an electronic system (e.g., a computer system) allows for data to be processed at a higher rate. Synthetic resins in the vicinity of such electrical signals, however, can exert a large influence on transmission loss of such electrical signals in a high frequency circuit. To minimize this influence, synthetic resins having a low dielectric constant and a low dissipation factor, in addition to the other properties discussed above, are desired.
- composition comprising, consisting of, or consisting essentially of: a) tetraphenolic epoxy resin;
- composition comprising, consisting of, or consisting essentially of: a) a tetraphenolic epoxy resin; b) a maleimide; and c) a triazine and/or a cyanate ester.
- the multifunctional epoxy resin composition of the present invention may include a composition having the following chemical structure (I):
- R in Structure (I) may be a cycloaliphatic diradical such as:
- Rj and R2 may be independently hydrogen, methyl, ethyl, i-propyl, n-propyl, n-butyl, i-butyl, t-butyl, methoxy, bromine, chlorine, fluorine, trifluoromethyl, methoxy, and ethoxy.
- the tetraphenolic epoxy resin is the tetraglycidyl ether of
- eCHTP cyclohexanedimethyltetraphenol
- the tetraglycidylether of dicyclopentadienedimethyltetraphenol may be used.
- the tetraphenolic epoxy resin is present in an amount in the range of from about 5 weight percent to about 95 weight percent, based on the total weight of the composition. In an embodiment, the epoxy resin is present in an amount in the range of from about 35 weight percent to about 65 weight percent, based on the total weight of the composition. Ranges outside of these would result in significantly decreased performance.
- the composition of the present disclosure further includes a maleimide resin.
- suitable maleimide resins include, but are not limited to, those maleimide resins having at least one maleimide group per molecule. Additional examples include, but are not limited to, toluenebismaleimide, phenylmaleimide, 4,4'- bismaleimidodiphenylmethane and combinations thereof.
- the range of maleimide concentration (expressed as the weight of the maleimide-containing monomer vs the weight of the other organic components excluding solvent) is from about 0 weight percent to about 50 weight percent. In another embodiment, the range is from about 10 weight percent to about 40 weight percent, and in yet another
- the composition of the present disclosure also includes a cyanate ester.
- suitable cyanate esters include, but are not limited to, a partially trimerized cyanate ester, and a triazine cyanate ester (e.g., cyanate ester partially trimerized into a triazine ring structure).
- Suitable cyanate esters are the dicyanates (or polycyanates) of the following bisphenols and polyphenols: bisphenol A, bisphenol F (4,4'- bis(hydroxyphenyl)methane, bisphenol S (4,4'-bis(hydroxyphenyl)sulfone, dicyclopentadiene bisphenol, naphthalene diol, 4,4'-dihydroxybiphenyl, 4,4'-dihydroxy-3,3',5,5'- tetramethylbiphenyl, phenol novolac, cresol novolac, naphthol novolac, and combinations thereof.
- the partially trimerized cyanate ester and/or the triazine cyanate ester are soluble in the aprotic solvent (e.g., ketones such as methyl ethyl ketone, methyl isobutyl ketone and combinations thereof) used with the phosphorous-containing compound of the composition.
- aprotic solvent e.g., ketones such as methyl ethyl ketone, methyl isobutyl ketone and combinations thereof
- Commercially available cyanates include Primaset ® BA-200, Primaset ® BA- 230s, Primaset ® PT-30, Primaset ® PT-30s, Primaset ® LECY, Primaset ® PT-60, and Primaset ® PT-60s all available from Lonza Ltd. Basel, Switzerland.
- the preferred range of cyanate concentration (expressed as the weight of the cyanate monomer vs the weight of the other organic components excluding solvent) is 5 wt to 75 wt , more preferred 10 wt to 50 wt , and most preferred 15 wt to 40 wt . Ranges outside of these would result in significantly decreased performance.
- Catalysts can include, but are not limited to, imidazole compounds including compounds having one imidazole ring per molecule, such as imidazole, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2- undecylimidazole, 2-heptadecylimidazole, 2-phenylimidazole, 2-phenyl-4-methylimidazole, 1- benzyl-2-methylimidazole, 2-ethylimidazole, 2-isopropylimidazole, 2-phenyl-4-benzylimidazole, l-cyanoethyl-2-methylimidazole, l-cyanoethyl-2-ethyl-4-methylimidazole, l-cyanoethyl-2- undecylimidazole, l-cyanoethyl-2-isopropylimidazole, l-cyanoe
- the composition can also contain metal catalysts conventionally used to cure cyanates: zinc naphthenate, zinc octoate, zinc ethylhexoate, zinc hexoate, as well as the manganese, copper, and other transition element (Groups 4-13) of these same anions.
- the halogenated flame retardant may include brominated flame retardants.
- brominated additives include brominated polyphenols such as tetrabromobisphenol A (TBBA) and tetrabromobisphenol F and materials derived therefrom: TBBA-diglycidyl ether, reaction products of bisphenol A or TBBA with TBBA-diglycidyl ether, and reaction products of bisphenol A diglycidyl ether with TBBA. Mixtures of one or more of the above described flame retardant additives can also be used.
- the composition also contains a non-halogen flame retardant.
- the non- halogen flame retardant can be a phosphorus-containing compound.
- the phosphorus-containing compound can contain some reactive groups such as a phenolic group, an acid group, an amino group, an acid anhydride group, a phosphate group, or a phosphinate group which can react with the epoxy resin or hardener of the composition.
- the phosphorus-containing compound can contain on average one or more than one functionality capable of reacting with epoxy groups. Such phosphorus-containing compound generally contains on average 0.8 to 5 functionalities. In an embodiment, the phosphorus- containing compound contains in the range of from 0.9 to 4 functionalities, and in another embodiment, it contains in the range of 1 to 3 functionalities capable of reacting with an epoxy resin.
- the phosphorus-containing compound useful in the present invention include for example one or more of the following compounds: P-H functional compounds such as for example HCA, dimethylphosphite, diphenylphosphite, ethylphosphonic acid, diethylphosphinic acid, methyl ethylphosphinic acid, phenyl phosphonic acid, vinyl phosphonic acid, phenolic (HCA-HQ); tris(4-hydroxyphenyl)phosphine oxide, bis(2-hydroxyphenyl)phenylphosphine oxide, bis(2- hydroxyphenyl)phenylphosphinate, tris(2-hydroxy-5-methylphenyl)phosphine oxide, acid anhydride compounds such as M-acid-AH, and amino functional compounds such as for example bis(4-aminophenyl)phenylphosphate, and mixtures thereof.
- P-H functional compounds such as for example HCA, dimethylphosphite, diphenylphosphite,
- a phosphonate compound can be used.
- Phosphonates that also contain groups capable of reacting with the epoxy resin or the hardener such as polyglycidyl ethers or polyphenols with covalently-bound tricyclic phosphonates are useful.
- Examples include but are not limited to the various materials derived from DOP (9,10-dihydro-9-oxa-10- phosphaphenanthrene 10-oxide) such as DOP-hydroquinone (10-(2',5'-dihydroxyphenyl)-9,10- dihydro-9-oxa-10-phosphaphenanthrene 10-oxide), condensation products of DOP with glycidylether derivatives of novolacs, and inorganic flame retardants such as aluminum trihydrate, aluminum hydroxide (Boehmite) and aluminum phosphinite. If inorganic flame retardant fillers are used, silane treated grades are preferred.
- DOP 9,10-dihydro-9-oxa-10- phosphaphenanthrene 10-oxide
- DOP-hydroquinone (10-(2',5'-dihydroxyphenyl)-9,10- dihydro-9-oxa-10-phosphaphenanthrene 10-oxide
- Mixtures of one or more of the above described flame retardancy enhancing compounds may also be used.
- Embodiments of the present disclosure can also include the use of at least one maleimide resin with the thermosetting monomers of the present disclosure.
- suitable maleimide resins include, but are not limited to, those having two maleimide groups derived from maleic anhydride and diamines or polyamines.
- Suitable maleimide resins include bismaleimides such as 4,4'-diaminodiphenylmethane, among others.
- Embodiments of the present disclosure also provide for a composition that includes the thermosetting monomer of the present disclosure and at least one thermoplastic polymer.
- Typical thermoplastic polymers include, but are not limited to, polymers produced from vinyl aromatic monomers and hydrogenated versions thereof, including both diene and aromatic hydrogenated versions, including aromatic hydrogenation, such as styrene-butadiene block copolymers, polystyrene (including high impact polystyrene), acrylonitrile-butadiene-styrene (ABS) copolymers, and styrene-acrylonitrile copolymers (SAN); polycarbonate (PC), ABS/PC compositions, polyethylene, polyethylene terephthalate, polypropylene, polyphenylenoxides (PPO), hydroxy phenoxy ether polymers (PHE), ethylene vinyl alcohol copolymers, ethylene acrylic acid copolymers, polyolefin carbon monoxide interpolymers, chlorinated polyethylene, polyphenylene
- the composition of the present disclosure can include the thermosetting monomer of the present disclosure and at least one reactive and/or non-reactive thermoplastic resin.
- thermoplastic resins include, but are not limited to, polyphenylsulfones, polysulfones, poly ethersulf ones, polyvinylidene fluoride, polyetherimide, polyp thalimide, polybenzimidiazole, acyrlics, phenoxy, and combinations or blends thereof.
- thermosetting monomer of the present disclosure can be blended with the thermoplastic resin to form a hybrid crosslink network.
- Preparation of the compositions of the present disclosure can be accomplished by suitable mixing means known in the art, including dry blending the individual components and subsequently melt mixing, either directly in the extruder used to make the finished article or pre-mixing in a separate extruder. Dry blends of the compositions can also be directly injection molded without pre-melt mixing.
- the composition of the thermosetting monomers of the present disclosure and the thermoplastic resin can be formed or molded using conventional techniques such as compression molding, injection molding, gas assisted injection molding, calendaring, vacuum forming, thermoforming, extrusion and/or blow molding, alone or in combination.
- the composition of the thermosetting monomers of the present disclosure and the thermoplastic resin may also be formed, spun, or drawn into films, fibers, multi-layer laminates or extruded sheets, or can be compounded with one or more organic or inorganic substances.
- Embodiments of the present disclosure also provide for a composition that includes the thermosetting monomer of the present disclosure and at least one of a polyurethane, a polyisocyanate, a benzoxazine ring-containing compound, an unsaturated resin system containing double or triple bonds, and combinations thereof.
- compositions of the present disclosure described above may also optionally make use of at least one catalyst.
- suitable curing catalysts include amines, dicyandiamides, substituted guanidines, phenolics, amino, benzoxazines, anhydrides, amido amines, polyamides, phosphines, ammonium, phosphonium, arsonium, sulfonium moieties or mixtures thereof.
- thermosetting monomer and/or compositions that include the thermosetting monomer may be useful in the preparation of various articles of manufacture.
- the disclosure also includes prepregs of the above composition as well as shaped articles, reinforced compositions, laminates, electrical laminates, coatings, molded articles, adhesives, composite products as hereinafter described from cured or partially cured thermosetting monomer or compositions that include the thermosetting monomer of the disclosure.
- the compositions of the disclosure can be used for various purposes in the form of a dried powder, pellets, a homogeneous mass, impregnated products or/or compounds. A variety of additional additives may be added to the composition of the present disclosure.
- fibrous reinforcement examples include fibrous reinforcement, fillers, pigments, dyestuffs, thickening agents, wetting agents, lubricants, flame-retardants and the like.
- Suitable fibrous and/or particulate reinforcing materials include silica, alumina trihydrate, aluminum oxide, aluminum hydroxide oxide, metal oxides, nano tubes, glass fibers, quartz fibers, carbon fibers, boron fibers, Kevlar fibers and Teflon fibers, among others.
- a size range for the fibrous and/or particulate reinforcing materials can include 0.5 nm to 100 ⁇ .
- the fibrous reinforcing materials can come in the form of a mat, cloth or continuous fibers.
- the fibrous or reinforcing material is present in the composition in an amount effective to impart increased strength to the composition for the intended purpose, generally from 10 to 70 wt , usually from 30 to 65 wt , based on the weight of the total composition.
- the laminates of the disclosure can optionally include one or more layers of a different material and in electrical laminates this can include one or more layers of a conductive material such as copper or the like.
- the curing is desirably effected under pressure.
- the fibrous reinforcement impregnated with the composition of the present disclosure can be subjected to a relatively mild heat treatment ("B-staged ”) to form a "prepreg.”
- B-staged relatively mild heat treatment
- the prepreg can then subjected to elevated temperature and pressure so as to more completely cure the composition to a hard, inflexible state.
- a plurality of prepregs can be layered and cured to form a laminate having utility in circuit boards.
- Embodiments of the compositions may also include at least one of a synergist to help improve the flame extinguishing ability of the cured composition.
- a synergist include, but are not limited to, magnesium hydroxide, zinc borate, metallocenes and
- compositions may also include adhesion promoters, such as modified organosilanes (epoxidized, methacryl, amino), acytlacetonates, sulfur containing molecules and combinations thereof.
- adhesion promoters such as modified organosilanes (epoxidized, methacryl, amino), acytlacetonates, sulfur containing molecules and combinations thereof.
- Other additives can include, but are not limited to, wetting and dispersing aids such as modified organosilanes, Byk® 900 series and W 9010 (Byk-Chemie GmbH), modified fluorocarbons and combinations thereof; air release additives such as Byk® A530, Byk® A525, Byk® A555, and Byk® A 560 (Byk-Chemie
- a process for the manufacture of the varnish comprises the following steps:
- the tetraphenolic epoxy resin is added to an appropriate vessel equipped with a mechanical stirrer, a heat source, and a nitrogen inlet.
- the resin is heated to 100 to 160 °C to melt the resin.
- the maleimide(s) are added while stirring to dissolve the maleimide.
- the temperature of the blend is maintained between 100 to 160 ° for 15 minutes to 6 hours. Once the mixture is homogenous, the heat source is removed and solvent is added dropwise to the vessel to dilute the epoxy - maleimide blend.
- the viscosity of the curable composition is low enough to flow and sufficiently wet glass bundles.
- Typical reactivities for a laminate varnish based on treater conditions are in the range of from about 200 to about 300 seconds.
- Curing of the compositions disclosed herein may require a temperature of at least about 30°C, up to about 250°C, for periods of minutes up to hours, depending on the epoxy resin, hardener, and catalyst, if used. In other embodiments, curing can occur at a temperature of at least 100°C, for periods of minutes up to hours. Post-treatments may be used as well, such post- treatments ordinarily being at temperatures between about 100°C and 250°C.
- curing can be staged to prevent large exothermic reactions.
- Staging for example, includes curing for a period of time at a temperature followed by curing for a period of time at a higher temperature.
- Staged curing may include two or more curing stages, and may commence at temperatures below about 180°C in some embodiments, and below about 150°C in other embodiments.
- curing temperatures can range from a lower limit of 30°C, 40°C, 50°C, 60°C, 70°C, 80°C, 90°C, 100°C, 110°C, 120°C, 130°C, 140°C, 150°C, 160°C, 170°C, or 180°C to an upper limit of 250°C, 240°C, 230°C, 220°C, 210°C, 200°C, 190°C, 180°C, 170°C, 160°C, where the range may be from any lower limit to any upper limit.
- a resin sheet can be formed from the thermosetting monomer and/or compositions of the present disclosure.
- a plurality of sheets can be bonded together to form a laminated board, where the sheets comprise at least one of the resin sheet.
- the thermosetting monomer and/or compositions that include the thermosetting monomer can also be used to form a resin clad metal foil.
- a metal foil such as a copper foil, can be coated with the thermosetting monomer and/or compositions that include the thermosetting monomer of the present disclosure.
- the various embodiments also include a multi layer board that can be prepared by coating a laminated substrate with the thermosetting monomer and/or compositions of the present disclosure.
- thermosetting monomers of this disclosure comprise one or more components which can each be used in any desired form such as solid, solution or dispersion. These components are mixed in solvent or in the absence of a solvent to form the compositions of this disclosure.
- the mixing procedure comprises mixing solutions of the thermosetting monomers and one or more of the formulation components or either separately or together in a suitable inert organic solvent, such as for example, ketones such as methyl ethyl ketone, chlorinated hydrocarbons such as methylene chloride, ethers and the like, and homogenizing the resulting mixed solution at room temperature or at an elevated temperature below the boiling point of the solvents to form a composition in the form of a solution.
- thermosetting monomer and/or compositions of the present disclosure can applied to a substrate as a coating or adhesive layer.
- the thermosetting monomer and/or compositions of the present disclosure can be molded or laminated in the form of powder, pellet or as impregnated in a substrate such as a fibrous reinforcement.
- the thermosetting monomer and/or compositions of the present disclosure can then be cured by the application of heat.
- the heat necessary to provide the proper curing conditions can depend on the proportion of components constituting the composition and the nature of the components employed.
- the composition of this disclosure may be cured by heating it at a temperature within the range of 0 °C to 300 °C, preferably 100 °C to 250 °C, although differing according to the presence of a catalyst or curing agent or its amount, or the types of the components in the composition.
- the time required for heating can be 30 seconds to 10 hours, where the exact time will differ according to whether the resin composition is used as a thin coating or as molded articles of relatively large thickness or as laminates or as matrix resins for fiber reinforced composites, particularly for electrical and electronic applications, e.g., when applied to an electrically nonconductive material and subsequently curing the composition.
- composites can be formed by curing the compositions disclosed herein.
- composites may be formed by applying a curable epoxy resin composition to a substrate or a reinforcing material, such as by impregnating or coating the substrate or reinforcing material to form a prepreg, and curing the prepreg under pressure to form the electrical laminate composition.
- a composite may be formed by coating a substrate with a curable composition. Coating may be performed by various procedures, including spray coating, curtain flow coating, coating with a roll coater or a gravure coater, brush coating, and dipping or immersion coating.
- the substrate can be monolayer or multi-layer.
- the substrate may be a composite of two alloys, a multi-layered polymeric article, and a metal-coated polymer, among others, for example.
- one or more layers of the curable composition may be disposed on a substrate.
- Other multi-layer composites, formed by various combinations of substrate layers and electrical laminate composition layers are also envisaged herein.
- the heating of the composition can be localized, such as to avoid overheating of a temperature-sensitive substrate, for example.
- the heating may include heating the substrate and the composition.
- Formulations prepared and cured according to the present invention exhibit significantly higher glass transition temperatures than other polyphenolic resins including phenol novolac and oxaxolidinone modified resins.
- compositions disclosed herein may be useful in composites containing high strength filaments or fibers such as carbon (graphite), glass, boron, and the like.
- Composites can contain from about 30% to about 70%, in some embodiments, and from 40% to 70% in other embodiments, of these fibers based on the total volume of the composite.
- Fiber reinforced composites for example, can be formed by hot melt prepregging.
- the prepregging method is characterized by impregnating bands or fabrics of continuous fiber with a thermosetting composition as described herein in molten form to yield a prepreg, which is laid up and cured to provide a composite of fiber and epoxy resin.
- processing techniques can be used to form electrical laminate composites containing the compositions disclosed herein.
- filament winding, solvent prepregging, and pultrusion are typical processing techniques in which the curable composition may be used.
- fibers in the form of bundles can be coated with the curable composition, laid up as by filament winding, and cured to form a composite.
- compositions and composites described herein may be useful as adhesives, structural and electrical laminates, coatings, marine coatings, composites, powder coatings, adhesives, castings, structures for the aerospace industry, and as circuit boards and the like for the electronics industry.
- the curable compositions and resulting thermoset resins may be used in composites, castings, coatings, adhesives, or sealants that may be disposed on, in, or between various substrates.
- the curable compositions may be applied to a substrate to obtain an epoxy based prepreg.
- the substrates include, for example, glass cloth, a glass fiber, glass paper, paper, and similar substrates of polyethylene and polypropylene.
- the obtained prepreg can be cut into a desired size.
- An electrical conductive layer can be formed on the laminate / prepreg with an electrical conductive material.
- suitable electrical conductive materials include electrical conductive metals such as copper, gold, silver, platinum and aluminum.
- Such electrical laminates may be used, for example, as multi-layer printed circuit boards for electrical or electronics equipment.
- Laminates made from the maleimide-triazine-epoxy polymer blends are especially useful for the production of HDI (high density interconnect) boards.
- HDI boards include those used in cell phones or those used for Interconnect (IC) substrates.
- the glass transition temperature (Tg) was measured by DSC using a TA
- the thermal decomposition (Td) is the temperature at which 5 wt % of the cured laminate is lost to decomposition products as measured at a ramp rate of 10°C/minute Td by TGA (TA Instruments Model Q5000 TGA) following the IPC method IPC TM-650 2.3.40.
- DENTM 438 is a is a multifunctional epoxy novolac with an epoxy equivalent weight of 180 sold by The Dow Chemical Company.
- DERTM 6508 is an oxazolidone modified solid epoxy resin.
- DOP-BN is the reaction product of a butylated resole and DOP.
- Primaset® BA-230s is a prepolymer bisphenol A dicyanate.
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Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201280007687.0A CN103347924B (en) | 2011-01-21 | 2012-01-04 | For electric laminated material, high density interconnection and the high-performance thermosetting material of interconnection substrate application |
KR1020137019010A KR20140007820A (en) | 2011-01-21 | 2012-01-04 | High performance thermoset useful for electrical laminate, high density interconnect and interconnect substrate applications |
EP12702911.4A EP2665761B1 (en) | 2011-01-21 | 2012-01-04 | High performance thermoset useful for electrical laminate, high density interconnect and interconnect substrate applications |
SG2013055561A SG192066A1 (en) | 2011-01-21 | 2012-01-04 | High performance thermoset useful for electrical laminate, high densityinterconnect and interconnect substrate applications |
JP2013550486A JP2014503029A (en) | 2011-01-21 | 2012-01-04 | High performance thermosetting resins useful for electrical laminates, high density interconnects and interconnect substrate applications |
US13/990,841 US20130303659A1 (en) | 2011-01-21 | 2012-01-04 | High performance thermoset useful for electrical laminate, high density interconnect and interconnect substrate applications |
Applications Claiming Priority (2)
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US201161434881P | 2011-01-21 | 2011-01-21 | |
US61/434,881 | 2011-01-21 |
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WO2012099713A1 true WO2012099713A1 (en) | 2012-07-26 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/US2012/020129 WO2012099713A1 (en) | 2011-01-21 | 2012-01-04 | High performance thermoset useful for electrical laminate, high density interconnect and interconnect substrate applications |
Country Status (8)
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US (1) | US20130303659A1 (en) |
EP (1) | EP2665761B1 (en) |
JP (1) | JP2014503029A (en) |
KR (1) | KR20140007820A (en) |
CN (1) | CN103347924B (en) |
SG (1) | SG192066A1 (en) |
TW (1) | TWI548690B (en) |
WO (1) | WO2012099713A1 (en) |
Cited By (1)
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CN103614107A (en) * | 2013-11-21 | 2014-03-05 | 安徽康瑞鑫电子科技有限公司 | Epoxy potting adhesive |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
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US20110247756A1 (en) * | 2008-12-16 | 2011-10-13 | Dow Global Technologies Llc | Homogeneous bismaleimide - triazine - epoxy compositions useful for the manufacture of electrical laminates |
JP7029774B2 (en) * | 2015-07-20 | 2022-03-04 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | Sydnone as a component corresponding to thermosetting resin with excellent heat resistance |
CN105238314B (en) * | 2015-11-13 | 2017-11-07 | 深圳先进技术研究院 | A kind of wet-heat resisting high reliability epoxy conductive silver glue and preparation method and application |
JP6761573B2 (en) * | 2015-12-21 | 2020-09-30 | 三菱瓦斯化学株式会社 | Resin composition, prepreg, metal foil-clad laminate, resin sheet and printed wiring board |
US11359062B1 (en) | 2021-01-20 | 2022-06-14 | Thintronics, Inc. | Polymer compositions and their uses |
US11596066B1 (en) | 2022-03-22 | 2023-02-28 | Thintronics. Inc. | Materials for printed circuit boards |
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WO2001042359A1 (en) * | 1999-12-13 | 2001-06-14 | Dow Global Technologies Inc. | Flame retardant phosphorus element-containing epoxy resin compositions |
WO2009114383A1 (en) * | 2008-03-12 | 2009-09-17 | Dow Global Technologies Inc. | Polyphenolic compounds and epoxy resins comprising cycloaliphatic moieties and process for the production thereof |
WO2010075006A1 (en) * | 2008-12-16 | 2010-07-01 | Dow Global Technologies Inc. | Homogeneous bismaleimide - triazine - epoxy compositions useful for the manufacture of electrical laminates |
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JPS5473900A (en) * | 1977-11-25 | 1979-06-13 | Mitsubishi Gas Chem Co Inc | Curable resin composition |
JPS5477663A (en) * | 1977-12-02 | 1979-06-21 | Mitsubishi Gas Chem Co Inc | Curable resin composition |
JPS58194874A (en) * | 1982-05-10 | 1983-11-12 | Mitsubishi Petrochem Co Ltd | Tetrafunctional epoxy compound |
JPS617331A (en) * | 1984-06-21 | 1986-01-14 | Mitsubishi Gas Chem Co Inc | Flame-retardant curable resin composition |
JPH02286723A (en) * | 1989-04-28 | 1990-11-26 | Matsushita Electric Works Ltd | Laminating resin composition and laminate |
WO2008144252A1 (en) * | 2007-05-16 | 2008-11-27 | Dow Global Technologies Inc. | Flame retardant composition |
JP5024205B2 (en) * | 2007-07-12 | 2012-09-12 | 三菱瓦斯化学株式会社 | Prepreg and laminate |
-
2012
- 2012-01-04 SG SG2013055561A patent/SG192066A1/en unknown
- 2012-01-04 EP EP12702911.4A patent/EP2665761B1/en not_active Not-in-force
- 2012-01-04 CN CN201280007687.0A patent/CN103347924B/en not_active Expired - Fee Related
- 2012-01-04 US US13/990,841 patent/US20130303659A1/en not_active Abandoned
- 2012-01-04 WO PCT/US2012/020129 patent/WO2012099713A1/en active Application Filing
- 2012-01-04 JP JP2013550486A patent/JP2014503029A/en not_active Ceased
- 2012-01-04 KR KR1020137019010A patent/KR20140007820A/en not_active Application Discontinuation
- 2012-01-20 TW TW101102542A patent/TWI548690B/en not_active IP Right Cessation
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WO2001042359A1 (en) * | 1999-12-13 | 2001-06-14 | Dow Global Technologies Inc. | Flame retardant phosphorus element-containing epoxy resin compositions |
EP1268665A1 (en) | 1999-12-13 | 2003-01-02 | Dow Global Technologies Inc. | Flame retardant phosphorus element-containing epoxy resin compositions |
WO2009114383A1 (en) * | 2008-03-12 | 2009-09-17 | Dow Global Technologies Inc. | Polyphenolic compounds and epoxy resins comprising cycloaliphatic moieties and process for the production thereof |
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Cited By (1)
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CN103614107A (en) * | 2013-11-21 | 2014-03-05 | 安徽康瑞鑫电子科技有限公司 | Epoxy potting adhesive |
Also Published As
Publication number | Publication date |
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TWI548690B (en) | 2016-09-11 |
SG192066A1 (en) | 2013-08-30 |
KR20140007820A (en) | 2014-01-20 |
CN103347924A (en) | 2013-10-09 |
EP2665761B1 (en) | 2015-04-08 |
JP2014503029A (en) | 2014-02-06 |
EP2665761A1 (en) | 2013-11-27 |
CN103347924B (en) | 2016-12-28 |
US20130303659A1 (en) | 2013-11-14 |
TW201233727A (en) | 2012-08-16 |
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