CN106810820B - Thermosetting alkyl polyol glycidyl ether resin composition and application thereof - Google Patents
Thermosetting alkyl polyol glycidyl ether resin composition and application thereof Download PDFInfo
- Publication number
- CN106810820B CN106810820B CN201510882430.5A CN201510882430A CN106810820B CN 106810820 B CN106810820 B CN 106810820B CN 201510882430 A CN201510882430 A CN 201510882430A CN 106810820 B CN106810820 B CN 106810820B
- Authority
- CN
- China
- Prior art keywords
- glycidyl ether
- resin composition
- alkyl polyol
- thermosetting
- anhydride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 85
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 title claims abstract description 80
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 70
- 229920005862 polyol Polymers 0.000 title claims abstract description 58
- 150000003077 polyols Chemical class 0.000 title claims abstract description 55
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 54
- 239000003822 epoxy resin Substances 0.000 claims abstract description 71
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 71
- 229920005989 resin Polymers 0.000 claims abstract description 55
- 239000011347 resin Substances 0.000 claims abstract description 55
- 239000000203 mixture Substances 0.000 claims abstract description 51
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims description 37
- -1 alkyl polyol glycidyl ethers Chemical class 0.000 claims description 28
- 239000003795 chemical substances by application Substances 0.000 claims description 26
- 239000011521 glass Substances 0.000 claims description 20
- 239000003063 flame retardant Substances 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 16
- 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 claims description 15
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- 239000000835 fiber Substances 0.000 claims description 12
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 12
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 claims description 11
- 229920000147 Styrene maleic anhydride Polymers 0.000 claims description 11
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 11
- 239000000347 magnesium hydroxide Substances 0.000 claims description 11
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 8
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 7
- 150000008064 anhydrides Chemical class 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- 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 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 6
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims description 6
- OBTARUYASFQRHM-UHFFFAOYSA-N benzene-1,3-diol;diphenoxyphosphoryl diphenyl phosphate Chemical compound OC1=CC=CC(O)=C1.C=1C=CC=CC=1OP(OP(=O)(OC=1C=CC=CC=1)OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 OBTARUYASFQRHM-UHFFFAOYSA-N 0.000 claims description 6
- APOXBWCRUPJDAC-UHFFFAOYSA-N bis(2,6-dimethylphenyl) hydrogen phosphate Chemical compound CC1=CC=CC(C)=C1OP(O)(=O)OC1=C(C)C=CC=C1C APOXBWCRUPJDAC-UHFFFAOYSA-N 0.000 claims description 6
- 229920003986 novolac Polymers 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 claims description 5
- 239000005995 Aluminium silicate Substances 0.000 claims description 5
- BQPNUOYXSVUVMY-UHFFFAOYSA-N [4-[2-(4-diphenoxyphosphoryloxyphenyl)propan-2-yl]phenyl] diphenyl phosphate Chemical compound C=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 BQPNUOYXSVUVMY-UHFFFAOYSA-N 0.000 claims description 5
- 235000012211 aluminium silicate Nutrition 0.000 claims description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 5
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 claims description 5
- RERMPCBBVZEPBS-UHFFFAOYSA-N tris(2,6-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(C)=C1P(C=1C(=CC=CC=1C)C)C1=C(C)C=CC=C1C RERMPCBBVZEPBS-UHFFFAOYSA-N 0.000 claims description 5
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 4
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 150000001491 aromatic compounds Chemical class 0.000 claims description 4
- 229910001593 boehmite Inorganic materials 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 4
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 claims description 4
- 239000012796 inorganic flame retardant Substances 0.000 claims description 4
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004843 novolac epoxy resin Substances 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 4
- 239000000454 talc Substances 0.000 claims description 4
- 229910052623 talc Inorganic materials 0.000 claims description 4
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 3
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 claims description 2
- FBHPRUXJQNWTEW-UHFFFAOYSA-N 1-benzyl-2-methylimidazole Chemical compound CC1=NC=CN1CC1=CC=CC=C1 FBHPRUXJQNWTEW-UHFFFAOYSA-N 0.000 claims description 2
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 claims description 2
- MFGALGYVFGDXIX-UHFFFAOYSA-N 2,3-Dimethylmaleic anhydride Chemical compound CC1=C(C)C(=O)OC1=O MFGALGYVFGDXIX-UHFFFAOYSA-N 0.000 claims description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 2
- LEHNQGSPRXHYRT-UHFFFAOYSA-N 2-dodecyl-1h-imidazole Chemical compound CCCCCCCCCCCCC1=NC=CN1 LEHNQGSPRXHYRT-UHFFFAOYSA-N 0.000 claims description 2
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 claims description 2
- FRWYFWZENXDZMU-UHFFFAOYSA-N 2-iodoquinoline Chemical compound C1=CC=CC2=NC(I)=CC=C21 FRWYFWZENXDZMU-UHFFFAOYSA-N 0.000 claims description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 claims description 2
- FUOZJYASZOSONT-UHFFFAOYSA-N 2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=CN1 FUOZJYASZOSONT-UHFFFAOYSA-N 0.000 claims description 2
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 claims description 2
- SESYNEDUKZDRJL-UHFFFAOYSA-N 3-(2-methylimidazol-1-yl)propanenitrile Chemical compound CC1=NC=CN1CCC#N SESYNEDUKZDRJL-UHFFFAOYSA-N 0.000 claims description 2
- AYKYXWQEBUNJCN-UHFFFAOYSA-N 3-methylfuran-2,5-dione Chemical compound CC1=CC(=O)OC1=O AYKYXWQEBUNJCN-UHFFFAOYSA-N 0.000 claims description 2
- DFATXMYLKPCSCX-UHFFFAOYSA-N 3-methylsuccinic anhydride Chemical compound CC1CC(=O)OC1=O DFATXMYLKPCSCX-UHFFFAOYSA-N 0.000 claims description 2
- QZYCWJVSPFQUQC-UHFFFAOYSA-N 3-phenylfuran-2,5-dione Chemical compound O=C1OC(=O)C(C=2C=CC=CC=2)=C1 QZYCWJVSPFQUQC-UHFFFAOYSA-N 0.000 claims description 2
- HDFKMLFDDYWABF-UHFFFAOYSA-N 3-phenyloxolane-2,5-dione Chemical compound O=C1OC(=O)CC1C1=CC=CC=C1 HDFKMLFDDYWABF-UHFFFAOYSA-N 0.000 claims description 2
- HMMBJOWWRLZEMI-UHFFFAOYSA-N 4,5,6,7-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CCCC2=C1C(=O)OC2=O HMMBJOWWRLZEMI-UHFFFAOYSA-N 0.000 claims description 2
- WWJAZKZLSDRAIV-UHFFFAOYSA-N 4-fluoro-2-benzofuran-1,3-dione Chemical compound FC1=CC=CC2=C1C(=O)OC2=O WWJAZKZLSDRAIV-UHFFFAOYSA-N 0.000 claims description 2
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 claims description 2
- XVMKZAAFVWXIII-UHFFFAOYSA-N 5-fluoro-2-benzofuran-1,3-dione Chemical compound FC1=CC=C2C(=O)OC(=O)C2=C1 XVMKZAAFVWXIII-UHFFFAOYSA-N 0.000 claims description 2
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052582 BN Inorganic materials 0.000 claims description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 2
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 229910052581 Si3N4 Inorganic materials 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- LTPBRCUWZOMYOC-UHFFFAOYSA-N beryllium oxide Inorganic materials O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 claims description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims description 2
- 239000000378 calcium silicate Substances 0.000 claims description 2
- 229910052918 calcium silicate Inorganic materials 0.000 claims description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 claims description 2
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 2
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 claims description 2
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 claims description 2
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 claims description 2
- MUTGBJKUEZFXGO-UHFFFAOYSA-N hexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21 MUTGBJKUEZFXGO-UHFFFAOYSA-N 0.000 claims description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 2
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 2
- 229960001545 hydrotalcite Drugs 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052863 mullite Inorganic materials 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 2
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 239000010703 silicon Substances 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 claims description 2
- 229940014800 succinic anhydride Drugs 0.000 claims description 2
- 239000004408 titanium dioxide Substances 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 229910001928 zirconium oxide Inorganic materials 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 2
- 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 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims 2
- 125000006158 tetracarboxylic acid group Chemical group 0.000 claims 2
- KGSFMPRFQVLGTJ-UHFFFAOYSA-N 1,1,2-triphenylethylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 KGSFMPRFQVLGTJ-UHFFFAOYSA-N 0.000 claims 1
- 239000011324 bead Substances 0.000 claims 1
- 239000003829 resin cement Substances 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 9
- 230000001070 adhesive effect Effects 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 51
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 37
- 239000003292 glue Substances 0.000 description 29
- 239000004744 fabric Substances 0.000 description 21
- 239000000463 material Substances 0.000 description 20
- 239000011889 copper foil Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 239000010949 copper Substances 0.000 description 18
- 229910052802 copper Inorganic materials 0.000 description 18
- 239000002253 acid Substances 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- 238000010030 laminating Methods 0.000 description 15
- 238000003475 lamination Methods 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 15
- 230000000875 corresponding effect Effects 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 10
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- 239000012779 reinforcing material Substances 0.000 description 7
- 239000011888 foil Substances 0.000 description 6
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- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
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- 239000011574 phosphorus Substances 0.000 description 4
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- 238000005979 thermal decomposition reaction Methods 0.000 description 4
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 3
- HDPBBNNDDQOWPJ-UHFFFAOYSA-N 4-[1,2,2-tris(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HDPBBNNDDQOWPJ-UHFFFAOYSA-N 0.000 description 3
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- 239000004593 Epoxy Substances 0.000 description 3
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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 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- 239000004642 Polyimide Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
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- YXTSJMYYIRPSDF-UHFFFAOYSA-N (2-methylphenyl)phosphonic acid Chemical compound CC1=CC=CC=C1P(O)(O)=O YXTSJMYYIRPSDF-UHFFFAOYSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- CYXGBTZYTXLVDN-UHFFFAOYSA-N 1-octoxyphosphonoyloxyoctane Chemical compound CCCCCCCCOP(=O)OCCCCCCCC CYXGBTZYTXLVDN-UHFFFAOYSA-N 0.000 description 1
- PVBGKAMVCZUNFQ-UHFFFAOYSA-N 1-propoxyphosphonoyloxypropane Chemical compound CCCOP(=O)OCCC PVBGKAMVCZUNFQ-UHFFFAOYSA-N 0.000 description 1
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- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- QXWLPGNICGFECG-UHFFFAOYSA-N 2-[2-hydroxyethoxy(oxido)phosphaniumyl]oxyethanol Chemical compound OCCOP(=O)OCCO QXWLPGNICGFECG-UHFFFAOYSA-N 0.000 description 1
- SEHJHHHUIGULEI-UHFFFAOYSA-N 2-hydroxyethylphosphonic acid Chemical compound OCCP(O)(O)=O SEHJHHHUIGULEI-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
- JOJBIXXQYQURIR-UHFFFAOYSA-N 2-methoxyethylphosphonic acid Chemical compound COCCP(O)(O)=O JOJBIXXQYQURIR-UHFFFAOYSA-N 0.000 description 1
- FDFUDZVGGRIXEX-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxyphosphonoyloxy)propane Chemical compound CC(C)COP(=O)OCC(C)C FDFUDZVGGRIXEX-UHFFFAOYSA-N 0.000 description 1
- BWGOLNLROKJSGE-UHFFFAOYSA-N 3-hydroxypropylphosphonic acid Chemical compound OCCCP(O)(O)=O BWGOLNLROKJSGE-UHFFFAOYSA-N 0.000 description 1
- LNYYKKTXWBNIOO-UHFFFAOYSA-N 3-oxabicyclo[3.3.1]nona-1(9),5,7-triene-2,4-dione Chemical compound C1=CC(C(=O)OC2=O)=CC2=C1 LNYYKKTXWBNIOO-UHFFFAOYSA-N 0.000 description 1
- UYRFPODVSLYSCO-UHFFFAOYSA-N 4-phosphonobutanoic acid Chemical compound OC(=O)CCCP(O)(O)=O UYRFPODVSLYSCO-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
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- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- HZCDANOFLILNSA-UHFFFAOYSA-N Dimethyl hydrogen phosphite Chemical compound COP(=O)OC HZCDANOFLILNSA-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XAXWWZSCEBUBFZ-UHFFFAOYSA-N OCOP(=O)OCO Chemical compound OCOP(=O)OCO XAXWWZSCEBUBFZ-UHFFFAOYSA-N 0.000 description 1
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920010524 Syndiotactic polystyrene Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
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- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- BLKXLEPPVDUHBY-UHFFFAOYSA-N bis(propan-2-yl) phosphonate Chemical compound CC(C)OP(=O)OC(C)C BLKXLEPPVDUHBY-UHFFFAOYSA-N 0.000 description 1
- GEBLOQXLELCEEO-UHFFFAOYSA-N bis[(2-methylpropan-2-yl)oxy]-oxophosphanium Chemical compound CC(C)(C)O[P+](=O)OC(C)(C)C GEBLOQXLELCEEO-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- UOKRBSXOBUKDGE-UHFFFAOYSA-N butylphosphonic acid Chemical compound CCCCP(O)(O)=O UOKRBSXOBUKDGE-UHFFFAOYSA-N 0.000 description 1
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- 239000004917 carbon fiber Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
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- 238000013329 compounding Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MJUJXFBTEFXVKU-UHFFFAOYSA-N diethyl phosphonate Chemical compound CCOP(=O)OCC MJUJXFBTEFXVKU-UHFFFAOYSA-N 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000005007 epoxy-phenolic resin Substances 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- SMNZHEHSKZSQLM-UHFFFAOYSA-N ethyl(methoxy)phosphinic acid Chemical compound CCP(O)(=O)OC SMNZHEHSKZSQLM-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- CDXVUROVRIFQMV-UHFFFAOYSA-N oxo(diphenoxy)phosphanium Chemical compound C=1C=CC=CC=1O[P+](=O)OC1=CC=CC=C1 CDXVUROVRIFQMV-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
- C08G59/22—Di-epoxy compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Reinforced Plastic Materials (AREA)
- Epoxy Resins (AREA)
Abstract
The invention provides a thermosetting alkyl polyol glycidyl ether resin composition and application thereof, wherein the resin composition takes epoxy resin as a main resin component, the epoxy resin contains alkyl polyol glycidyl ether, and the mass percentage of the alkyl polyol glycidyl ether in the main resin component is 50-100%. The composition is used for preparing prepregs, laminated boards, printed circuit boards and the like, and the epoxy resin with the alkyl polyhydric alcohol glycidyl ether structure of the molecular structure is used as a main resin component, so that the prepared laminated board has low dielectric property while keeping good thermal property and adhesive property, and is low in preparation cost, simple in method and wide in application prospect.
Description
Technical Field
The invention belongs to an epoxy resin composition, and relates to a thermosetting alkyl polyol glycidyl ether resin composition and application thereof.
Background
With the rapid development of wireless transmission products and the leap forward of high-frequency transmission technologies, higher requirements are put on the dielectric properties of materials, and the materials of the existing epoxy resin and phenolic resin systems cannot meet advanced applications, particularly the requirements of high-frequency printed circuit boards. Fluorine-based resins are used as substrate materials for printed wiring boards with low dielectric loss, but such resins are expensive and difficult to process, and are limited in application to military and aerospace fields. In addition, the polyphenyl ether resin has good mechanical properties and excellent dielectric properties, and is increasingly becoming the first choice resin material of the substrate of the high-frequency printed circuit board, but the polyphenyl ether with double bonds is used for manufacturing the high-frequency high-speed board at present through free radical reaction, special production equipment is required, the storage life of the prepreg is short, the adjustment of production process conditions is difficult, and the cost is high.
CN101684191B proposes that a cured product with low dielectric constant and dielectric loss can be obtained by using benzoxazine, styrene-maleic anhydride and a phosphorus-containing curing agent to compound and cure epoxy resin, but the dielectric property of the material is inevitably reduced by only using the styrene-maleic anhydride, so that many other problems occur, and the influence on the cohesiveness is particularly remarkable, because the polarity of modified matrix resin is reduced by a nonpolar styrene structural unit in a styrene-maleic anhydride (SMA) molecular structure, and the interaction force between the resin and copper foil is weakened; meanwhile, the brittleness of a resin cross-linked network is increased due to a large number of benzene ring structures in the SMA, and the bonding performance under a dynamic condition is adversely affected, so that the bonding strength between the base materials and the copper foil is reduced.
CN100523081C proposes that a cured product with low dielectric constant and dielectric loss can be obtained by curing a phosphorus-containing and halogen-free phosphorus-free epoxy composition by using benzoxazine, styrene-maleic anhydride and other curing agents in a compounding manner, but although the phosphorus-containing epoxy resin is used as a main resin, excellent flame retardance can be achieved, excessive introduction of phosphorus inevitably has a great influence on the water absorption of a base material, which inevitably has a negative influence on many other properties of the plate.
Japanese patent laid-open No. 2003-252958 discloses a biphenyl type epoxy resin and an active ester composition which are excellent in dielectric constant and dielectric loss tangent after curing, but have disadvantages of low glass transition temperature and low heat resistance of a cured product due to the use of a bifunctional biphenyl epoxy resin and the low crosslinking density of the active ester.
CN 102689463A discloses a soft copper-clad plate, which comprises an adhesive layer, a polyimide substrate and a copper foil layer, wherein the adhesive layer comprises the following components in percentage by weight: 30-40 parts of solvent type epoxy resin, 10-20 parts of solvent type epoxy toughening agent, 6-25 parts of halogen-free flame retardant, 1-3 parts of radiation-proof agent, 1-3 parts of additive and 20-40 parts of solvent I, wherein the solvent type epoxy toughening agent can be polypropylene glycol glycidyl ether, but the polypropylene glycol glycidyl ether is only used as the toughening agent and has lower application content.
At present, most researches on improving the performance of thermosetting epoxy resin compositions focus on selecting curing agents or toughening agents to improve the performance of the resin compositions, and few reports are made on improving the performance of the compositions by selecting and modifying main resin components.
Accordingly, it would be desirable in the art to be able to prepare resin compositions through the selection of the host resin ingredients so that panels prepared from the resin compositions have low dielectric constants as well as good thermal and adhesive properties.
Disclosure of Invention
In view of the defects of the prior art, the invention aims to provide a thermosetting alkyl polyol glycidyl ether resin composition and application thereof. The resin composition can effectively reduce the dielectric constant of the board, and simultaneously keeps better thermal property and bonding property.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides a thermosetting alkyl polyol glycidyl ether resin composition, which comprises an epoxy resin as a main resin component, wherein the epoxy resin comprises any one or a combination of at least two of alkyl polyol glycidyl ethers having the following structures:
wherein n is 1-10 (e.g., 2,3,4, 5,6, 7, 8 or 9), m is 1-10 (e.g., 2,3,4, 5,6, 7, 8 or 9), q is 2, 4 or 6, and R is H, CH3-or CH3-CH2-；
The alkyl polyhydric alcohol glycidyl ether accounts for 50-100% of the main resin component by mass percent.
In the present invention, the main resin component refers to a toughening agent, a curing agent, and the like as a resin component in the resin composition, not as a resin component. In the present invention, only the epoxy resin is used as the main resin component, and if other resin than the epoxy resin is contained, the other resin is used as a component other than the main resin component, for example, as a toughening agent, a curing agent, or the like.
The main resin component of the resin composition selects the alkyl polyhydric alcohol glycidyl ether which has an alkane chain segment, so that the resin composition has the advantage of low dielectric property, is low in cost, and can increase the length of a flexible chain between epoxy groups in a network after being cured, so that the flexibility of the resin composition is improved, and compared with fluororesin, the resin composition has lower price and more excellent bonding property; compared with polyphenyl ether resin, the polyphenyl ether resin has more excellent processing performance in the production process, simple and convenient production equipment and production process, and simultaneously has the characteristic of low dielectric property.
Preferably, the alkyl polyol glycidyl ether of the invention is
Any one of the above;
wherein q is 2, 4 or 6.
In the thermosetting alkyl polyol glycidyl ether resin composition of the present invention, the alkyl polyol glycidyl ether accounts for 50 to 100% by mass of the main resin component, for example, 53%, 55%, 58%, 60%, 64%, 68%, 70%, 73%, 75%, 78%, 80%, 84%, 88%, 90%, 93%, 95%, or 98%, preferably 50 to 70%. Too much or too little alkyl polyol glycidyl ether accounts for the main resin component by mass, which affects the dielectric and thermal properties.
In the thermosetting alkyl polyol glycidyl ether resin composition of the present invention, the main resin component further includes an epoxy resin other than the alkyl polyol glycidyl ether, and the alkyl polyol glycidyl ether is the alkyl polyol glycidyl ether according to the first aspect of the present invention.
Preferably, the other epoxy resin is selected from any one of phenol novolac type epoxy resin, methylphenol novolac type epoxy resin, bisphenol a novolac epoxy resin, dicyclopentadiene epoxy resin, biphenyl epoxy resin, naphthalene type epoxy resin, glycidyl ether type epoxy resin, alicyclic epoxy resin, polyethylene glycol type epoxy resin, tetraphenol ethane tetraglycidyl ether resin or triphenol methane type epoxy resin or a mixture of at least two thereof. For example, the mixture may be, but is not limited to, a mixture of a phenol novolac type epoxy resin and a methylphenol novolac type epoxy resin, a mixture of a bisphenol a novolac epoxy resin and a dicyclopentadiene epoxy resin, a mixture of a bisphenol a novolac epoxy resin, a dicyclopentadiene epoxy resin and a biphenyl epoxy resin, a mixture of a biphenyl epoxy resin, a naphthalene type epoxy resin and a glycidyl ether type epoxy resin, a mixture of a glycidyl ether type epoxy resin and an alicyclic type epoxy resin, a composition of an alicyclic type epoxy resin, a polyethylene glycol type epoxy resin and a tetraphenolethane tetraglycidyl ether resin, a composition of a tetraphenolethane tetraglycidyl ether resin and a triphenol methane type epoxy resin.
Preferably, the other epoxy resin may be a phosphorous epoxy resin and/or a silicon-containing epoxy resin.
In the thermosetting alkyl polyol glycidyl ether resin composition of the present invention, the thermosetting resin composition further comprises a curing agent.
Preferably, the curing agent is selected from any one of an anhydride curing agent, an active ester curing agent or a benzoxazine resin or a mixture of at least two thereof.
Preferably, the anhydride curing agent is selected from the group consisting of styrene maleic anhydride, methyl vinyl ether-maleic anhydride copolymer, methyl hexahydrophthalic anhydride, phenylsuccinic anhydride, succinic anhydride, oxa-anhydride, dimethylmaleic anhydride, glutaric anhydride, 2-methylsuccinic anhydride, phthalic anhydride, norbornene dianhydride, pyromellitic anhydride, 1, 2-cyclohexanedicarboxylic anhydride, 4-fluorophthalic anhydride, 3-fluorophthalic anhydride, 2-dimethylsuccinic anhydride, 1-cyclohexylbisanhydride, phenylmaleic anhydride, citraconic anhydride, 1, 8-naphthalic anhydride, 4 '-diphenyl ether dianhydride, 3', 4 '-biphenyltetracarboxylic dianhydride, pyromellitic dianhydride, 3', 4 '-diphenyl ether, 4' - (hexafluoroisopropylene) bisanhydride, isophthalic anhydride, maleic anhydride, 1,2,3, 4-cyclobutanetetracarboxylic dianhydride, 3', 4' -benzophenonetetracarboxylic dianhydride, 1,4,5, 8-benzenetetracarboxylic anhydride, perylene-1, 4,9, 10-tetracarboxylic anhydride, 3,4,5, 6-tetrahydrophthalic anhydride or cis-1, 2,3, 6-tetrahydrophthalic anhydride, or a mixture of at least two thereof.
Preferably, the active ester curing agent is a curing agent obtained by reacting a phenolic compound, a difunctional carboxylic aromatic compound or an acid halide and a monohydroxy compound which are connected through an aliphatic cyclic hydrocarbon structure, wherein the amount of the difunctional carboxylic aromatic compound or the acid halide is 1mol, the amount of the phenolic compound connected through the aliphatic cyclic hydrocarbon structure is 0.05-0.75mol, and the amount of the monohydroxy compound is 0.25-0.95 mol.
Preferably, the structural formula of the active ester curing agent is as follows:
wherein X is phenyl or naphthyl, j is 0 or 1, k is 0 or 1, and n is 0.25-1.25.
Preferably, the thermosetting alkyl polyol glycidyl ether resin composition of the invention further comprises a catalyst.
Preferably, the catalyst is an imidazole or pyridine compound.
Preferably, the imidazole compound is selected from any one or a mixture of at least two of 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-undecylimidazole, 1-benzyl-2-methylimidazole, 2-heptadecylimidazole, 2-isopropylimidazole, 2-phenyl-4-methylimidazole, 2-dodecylimidazole or 1-cyanoethyl-2-methylimidazole.
Preferably, the pyridine compound is 4-dimethylaminopyridine.
The amount of the catalyst used in the present invention depends on the type of the epoxy resin, the type of the curing agent and the type of the catalyst, and one principle of using the catalyst is that the gelation time of the glue solution should not be less than 120 s.
Preferably, the catalyst is used in an amount of 0.001 to 5.0% by mass, for example, 0.002%, 0.005%, 0.01%, 0.015%, 0.02%, 0.04%, 0.06%, 0.08%, 0.1%, 1%, 1.5%, 1.8%, 2%, 2.3%, 2.5%, 2.8%, 3%, 3.3%, 3.5%, 3.8%, 4%, 4.2%, 4.5%, 4.7%, or 4.9%, preferably 0.02 to 4.0%, and more preferably 0.005 to 3.0% by mass of the thermosetting alkyl polyol glycidyl ether resin composition. Too much catalyst (more than 5.0%) will result in a thermosetting composition that is too reactive, will increase the formation of by-products and will adversely affect the uniformity of the conversion of the curing reaction; if the amount of the catalyst in the composition is less than 0.001%, the reactivity is too slow, which is not favorable for the preparation of the prepreg.
Preferably, the resin composition further comprises a flame retardant.
Preferably, the flame retardant is selected from organic flame retardants and/or inorganic flame retardants.
The organic flame retardant of the present invention may be an organophosphorus flame retardant, for example, a substituted or unsubstituted alkylphosphonic acid, such as dialkylphosphonic acid (where the alkyl group is preferably a C1-10 alkyl group), including but not limited to dimethylphosphonic acid, methylethylphosphonic acid, diethylphosphonic acid, ethyl (n-, iso-, or tert-) butylphosphonic acid, di-n-propylphosphonic acid, diisopropylphosphonic acid, di-n-butylphosphonic acid, diisobutylphosphonic acid, di-tert-butylphosphonic acid, dipentylphosphonic acid, dioctylphosphonic acid, and the like; hydroxyl-containing dialkylphosphonic acids such as (hydroxymethyl) methylphosphonic acid, (hydroxyethyl) methylphosphonic acid, bis (hydroxymethyl) phosphonic acid, bis (hydroxyethyl) phosphonic acid, and the like; dialkyl phosphoric acids containing a carboxyl group such as (2-carboxyethyl) methylphosphonic acid and the like; alkoxy group-containing dialkylphosphonic acids such as (methoxymethyl) methylphosphonic acid and the like; aryl phosphonic acids, e.g., C6-10 aryl phosphonic acids (e.g., phenyl phosphonic acid), di-C6-10 aryl phosphonic acids (e.g., diphenyl phosphonic acid), alkylaryl phosphonic acids (e.g., C1-4 alkyl-C6-10 aryl-phosphonic acids, such as methyl phenyl phosphonic acid, etc.), and salts of these organic phosphonic acids.
The organic flame retardant may also be a substituted or unsubstituted alkylene phosphonic acid (preferably C3-8 alkylene phosphonic acid, etc.), such as 1-hydroxy-1H-phosphorane-1-oxide, 2-carboxy-1-hydroxy-1H-phosphorane-1-oxide; substituted or unsubstituted alkenylenephosphonic acids (preferably C3-8 alkenylenephosphonic acid), such as 1-hydroxyphosphine-1-oxide, and the like; cycloalkylenephosphonic acids (preferably C4-10 cycloalkylenephosphonic acids), such as 1, 3-cyclobutylenephosphonic acid, 1, 3-cyclopentylenephosphonic acid, 1, 4-cyclooctylenephosphonic acid, 1, 5-cyclooctylenephosphonic acid, and the like; or a salt thereof.
Preferably, the organic flame retardant is selected from any one of tris (2, 6-dimethylphenyl) phosphine, resorcinol bis [ bis (2, 6-dimethylphenyl) phosphate ], resorcinol tetraphenyl diphosphate, triphenyl phosphate, bisphenol a bis (diphenyl phosphate), a phosphazene flame retardant, 10- (2, 5-dihydroxyphenyl) -10-hydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10- (2, 5-dihydroxynaphthyl) -10-hydro-9-oxa-10-phosphaphenanthrene-10-oxide or a 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide flame retardant or a mixture of at least two thereof. For example, the mixture may be, but not limited to, a mixture of tris (2, 6-dimethylphenyl) phosphine and resorcinol bis [ bis (2, 6-dimethylphenyl) phosphate ], a mixture of tris (2, 6-dimethylphenyl) phosphine, resorcinol bis [ bis (2, 6-dimethylphenyl) phosphate ] and resorcinol tetraphenyl diphosphate, a mixture of resorcinol tetraphenyl diphosphate, triphenyl phosphate and bisphenol A bis (diphenyl phosphate), a phosphazene flame retardant, 10- (2, 5-dihydroxyphenyl) -10-hydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10- (2, 5-dihydroxynaphthyl) -10-hydro-9-oxa-10-phosphaphenanthrene-10-oxide and 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide flame retardant mixtures, tris (2, 6-dimethylphenyl) phosphine, resorcinol bis [ bis (2, 6-dimethylphenyl) phosphate ], resorcinol tetraphenyl diphosphate and a mixture of triphenyl phosphate and bisphenol a bis (diphenyl phosphate), resorcinol bis [ bis (2, 6-dimethylphenyl) phosphate ], resorcinol tetraphenyl diphosphate, triphenyl phosphate, bisphenol a bis (diphenyl phosphate), phosphazene flame retardant and a mixture of 10- (2, 5-dihydroxyphenyl) -10-hydro-9-oxa-10-phosphaphenanthrene-10-oxide.
Preferably, the inorganic flame retardant is selected from any one of red phosphorus, aluminum hydroxide, magnesium hydroxide or antimony trioxide or a mixture of at least two of the same. The mixture may be, but is not limited to, a mixture of red phosphorus and aluminum hydroxide, a mixture of aluminum hydroxide and magnesium hydroxide, a mixture of red phosphorus, aluminum hydroxide and magnesium hydroxide, and a mixture of aluminum hydroxide, magnesium hydroxide and antimony trioxide.
Preferably, the resin composition further comprises a filler.
Preferably, the filler is selected from any one or a mixture of at least two of silica, kaolin, talc powder, magnesium hydroxide, aluminum hydroxide, boehmite, hydrotalcite, titanium oxide, calcium silicate, beryllium oxide, boron nitride, glass powder, zinc borate, aluminum nitride, silicon carbide, magnesium oxide, zirconium oxide, mullite, titanium dioxide, potassium titanate, hollow glass microspheres, polytetrafluoroethylene powder, polystyrene powder, potassium titanate fibers, silicon carbide single crystal fibers, silicon nitride fibers, alumina single crystal fibers or glass short fibers. For example, the mixture may be, but is not limited to, a mixture of silica and kaolin, a mixture of talc, magnesium hydroxide and aluminum hydroxide, a mixture of magnesium hydroxide, aluminum hydroxide and boehmite, a mixture of kaolin, talc, magnesium hydroxide and aluminum hydroxide, a mixture of silica, kaolin, talc, magnesium hydroxide, aluminum hydroxide and boehmite.
The silica of the present invention may be crystalline silica, fused silica, spherical silica, or the like.
Preferably, the resin composition further comprises a curing accelerator. One skilled in the art can select a suitable curing accelerator as desired.
In a preferred embodiment of the present invention, the thermosetting alkyl polyol glycidyl ether resin composition of the present invention comprises the alkyl polyol glycidyl ether having the structure according to the first aspect of the present invention, another epoxy resin, and a curing agent, wherein the alkyl polyol glycidyl ether accounts for 50% by mass or more of the main resin component.
The alkyl polyalcohol glycidyl ether can be matched with other epoxy resin and a curing agent for use, and under the synergistic action, the product has low dielectric property, and the thermal property and the bonding property are ensured.
The term "comprising" as used herein means that it may include, in addition to the components, other components which impart different properties to the epoxy resin composition. In addition, the term "comprising" as used herein may be replaced by "being" or "consisting of … …" as closed. Regardless of the components included in the thermosetting alkyl polyol glycidyl ether resin composition, the sum of the mass percentages of the components of the resin composition except for the solvent is 100%.
In a second aspect, the invention provides a resin adhesive solution, wherein the resin adhesive solution is obtained by dissolving or dispersing the thermosetting alkyl polyhydric alcohol glycidyl ether resin composition in a solvent.
Preferably, the solvent is one or a combination of at least two of ketones, hydrocarbons, ethers, esters or aprotic solvents, preferably one or a mixture of at least two of acetone, methyl ethyl ketone, methyl isobutyl ketone, toluene, xylene, methanol, ethanol, primary alcohols, ethylene glycol monomethyl ether, propylene glycol methyl ether acetate, ethyl acetate, N-dimethylformamide or N, N-diethylformamide. The solvents can be used alone or in combination. The addition amount of the solvent can be determined by those skilled in the art according to the viscosity of the selected resin, so that the viscosity of the obtained thermosetting alkyl polyol glycidyl ether resin composition glue solution is moderate, and the curing is convenient, and the invention is not limited to this.
In a third aspect, the present invention provides a prepreg manufactured using the thermosetting alkyl polyol glycidyl ether resin composition according to the first aspect. The alkyl polyhydric alcohol glycidyl ether resin composition disclosed by the invention is attached to a reinforcing material after impregnation and drying to prepare a prepreg.
The method for producing a prepreg using the alkyl polyol glycidyl ether resin composition of the present invention is exemplified below, but the method for producing a prepreg is not limited thereto. And (2) impregnating the thermosetting alkyl polyhydric alcohol glycidyl ether resin composition glue solution (the viscosity of the glue solution is adjusted by using a solvent) on the reinforcing material, and heating and drying the prepreg impregnated with the resin composition to enable the epoxy resin composition in the prepreg to be in a semi-curing Stage (B-Stage), so that the prepreg can be obtained. The heating temperature of the prepreg sheet is 80-250 deg.C, such as 90 deg.C, 100 deg.C, 110 deg.C, 120 deg.C, 130 deg.C, 140 deg.C, 150 deg.C, 160 deg.C, 170 deg.C, 180 deg.C, 190 deg.C, 200 deg.C, 210 deg.C, 220 deg.C, 230 deg.C or 240 deg.C, for 1-30min, such as 3min, 5min, 7min, 10min, 12min, 15min, 18min, 20min, 22min, 25min, 28min or 29 min. The reinforcing material used therein may be an inorganic or organic material. Examples of the inorganic material include: woven or non-woven fabrics or paper of glass fiber, carbon fiber, boron fiber, metal, etc. The glass fiber cloth or non-woven cloth can be E-glass cloth, Q-type cloth, NE cloth, D-type cloth, S-type cloth, high silica cloth, etc. Organic fibers such as woven or nonwoven fabrics or papers made of polyester, polyamine, polyacrylic acid, polyimide, aramid, polytetrafluoroethylene, syndiotactic polystyrene, etc., however, the reinforcing material is not limited thereto, and other reinforcing materials useful for resin reinforcement can also be used to realize the present invention. The resin content in the prepreg is between 30 and 80 wt%, for example 32%, 35%, 38%, 40%, 45%, 48%, 50%, 53%, 55%, 58%, 60%, 63%, 65%, 68%, 70%, 72%, 75%, 78% or 79%.
In a fourth aspect, the present invention provides a printed circuit laminate comprising one or at least two stacked prepregs according to the third aspect.
The laminated board for the printed circuit comprises one or at least two superimposed prepregs and metal foils positioned on one side or two sides of the superimposed prepregs, wherein each prepreg comprises a reinforcing material and the alkyl polyhydric alcohol glycidyl ether resin composition attached to the reinforcing material after impregnation drying.
The resin composition can also be used for manufacturing resin sheets or prepregs, resin composite metal copper foils, laminated plates and printed wiring boards. Laminated board, copper clad laminated board and printingThe wiring board can be produced using the above resin sheet, resin composite metal foil, and prepreg. The copper clad laminate is taken as an example to illustrate the manufacturing method, but is not limited thereto. When the prepregs are used for manufacturing the copper-clad laminate, one or more prepregs are cut into a certain size to be laminated, then the laminated prepreg or prepregs are sent into laminating equipment to be laminated, meanwhile, the metal foil is placed on one side or two sides of the prepregs, and the prepregs are pressed to form the metal-clad laminate through hot-press molding. As the metal foil, copper, brass, aluminum, nickel, and an alloy or composite metal foil of these metals can be used. As the pressing conditions of the laminate, suitable lamination curing conditions should be selected according to the practical condition of the resin composition of the present invention. If the pressing pressure is too low, voids may exist in the laminate and the electrical properties may be degraded; excessive internal stresses in the laminate, which can lead to a reduction in the dimensional stability of the laminate, are present at excessive lamination pressures, and these require the pressing of the sheet with the appropriate molding pressures to achieve the desired results. The general guideline for conventional pressed laminates is that the lamination temperature is 130 ℃ and 250 ℃, the pressure: 3-50kgf/cm2And hot pressing time: 60-240 min. For example, the hot pressing temperature may be 140 ℃, 150 ℃, 160 ℃, 170 ℃, 180 ℃, 190 ℃, 200 ℃, 210 ℃, 220 ℃, 230 ℃ or 240 ℃. The pressure may be 5kgf/cm2、8kgf/cm2、11kgf/cm2、14kgf/cm2、17kgf/cm2、24kgf/cm2、28kgf/cm2、32kgf/cm2、37kgf/cm2、42kgf/cm2、45kgf/cm2Or 48kgf/cm2. The hot pressing time can be 70min, 90min, 110min, 130min, 150min, 170min, 190min, 210min, 230min or 240 min.
The resin sheet, the resin composite metal foil, the prepreg and the metal-clad laminate are used for manufacturing a printed circuit board or a complex multilayer circuit board by a layer adding method or a layer reducing method.
The thermosetting resin composition can be used for manufacturing resin sheets, resin composite metal copper foils, prepregs, laminated plates, copper clad laminated plates and printed wiring boards, can also be used for manufacturing adhesives, coatings or composite materials, and can also be applied to the fields of building, aviation, ship or automobile industry and the like.
Compared with the prior art, the invention has the following beneficial effects:
in the resin composition, the epoxy resin is used as a main resin component, and the epoxy resin with the alkyl polyalcohol glycidyl ether structure of the molecular structure accounts for 50-100% of the main resin component by mass, so that the resin composition has low dielectric property, low cost and simple preparation method while maintaining good thermal property and adhesive property. The method well overcomes the defects of the prior art, such as low adhesiveness and high price of the fluororesin, difficult production process conditions of the polyphenylene ether resin, and the like. The invention takes alkyl polyhydric alcohol glycidyl ether epoxy resin as a main resin component and takes active ester or acid anhydride as a curing agent, fully exerts the characteristic that the active ester and the acid anhydride curing agent do not generate polar groups when reacting with the epoxy resin, and ensures that a cured product has excellent dielectric constant and dielectric loss factor. The invention uses alkyl polyhydric alcohol glycidyl ether as a main resin component, so that the prepreg, the laminated board and the printed circuit board which are prepared by the resin composition have low dielectric constant (10GHz, less than or equal to 3.64), low dielectric loss factor (10GHz, less than or equal to 0.0083), better glass transition temperature (151.1-165.5 ℃), thermal decomposition temperature (361.5-382.3 ℃) and peeling strength (0.81-0.93N/mm), good processing performance and obvious cost advantage, and have wide application prospect.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Example 1
27 parts of 1, 4-butanediol diglycidyl ether (Kramat reagent) and 73 parts of EF40 (styrene maleic anhydride copolymer, Sadoma, USA) are added into a beaker, 50 parts of MEK (methyl ethyl ketone) or any of the solvents mentioned in the invention are added to dissolve the above compounds, and a proper amount of 2E4MI (2-ethyl-4-methylimidazole, Nippon Sizhou chemical Co., Ltd.) is used as a curing accelerator to prepare a glue solution with a solid content of 60-70%. The glue was soaked with 2116 glass cloth and the solvent was removed in an oven at 155 ℃ to obtain a prepreg sample.
And laminating by using 4 sheets of 2116 prepreg laminates and 0.5 ounce electrolytic copper foils on the upper sheet and the lower sheet respectively through a hot press to obtain the double-sided copper clad laminate. The lamination conditions were as follows: (1) when the material temperature is 80-120 ℃, the heating rate is controlled to be 1.0-3.0 ℃/min; (2) the pressure was set at 20kg/cm2(ii) a (3) The curing temperature was 200 ℃ and this temperature was maintained for 90 minutes. The corresponding properties are shown in Table 1.
Example 2
18 parts of 1, 4-butanediol diglycidyl ether, 18 parts of HP7200H (dicyclopentadiene epoxy resin, Japan DIC) and 64 parts of EF40 are added into a beaker, 50 parts of MEK or any solvent mentioned in the invention is added for dissolution, and a proper amount of 2E4MI is used as a curing accelerator to prepare a glue solution with a solid content of 60-70%. The glue was soaked with 2116 glass cloth and the solvent was removed in an oven at 155 ℃ to obtain a prepreg sample.
And laminating by using 4 sheets of 2116 prepreg laminates and 0.5 ounce electrolytic copper foils on the upper sheet and the lower sheet respectively through a hot press to obtain the double-sided copper clad laminate. The lamination conditions were as follows: (1) when the material temperature is 80-120 ℃, the heating rate is controlled to be 1.0-3.0 ℃/min; (2) the pressure was set at 20kg/cm2(ii) a (3) The curing temperature was 200 ℃ and this temperature was maintained for 90 minutes. The corresponding properties are shown in Table 1.
Example 3
23 parts of 1, 4-butanediol diglycidyl ether, 10 parts of NC3000H (biphenyl epoxy resin, Japan DIC) and 67 parts of EF40 were added to a beaker, 50 parts of MEK or any of the solvents mentioned in the present invention were added to dissolve the above compounds, and an appropriate amount of 2E4MI was used as a curing accelerator to prepare a glue solution having a solid content of 60 to 70%. The glue was soaked with 2116 glass cloth and the solvent was removed in an oven at 155 ℃ to obtain a prepreg sample.
Laminating the copper foil with 4 sheets of 2116 prepregs and 0.5 ounce electrolytic copper foils on the upper and lower sheets respectively by a hot press to obtain the double-sided copper clad laminateAnd (7) pressing a plate. The lamination conditions were as follows: (1) when the material temperature is 80-120 ℃, the heating rate is controlled to be 1.0-3.0 ℃/min; (2) the pressure was set at 20kg/cm2(ii) a (3) The curing temperature was 200 ℃ and this temperature was maintained for 90 minutes. The corresponding properties are shown in Table 1.
Example 4
31 parts of 1, 4-butanediol diglycidyl ether and 69 parts of HPC-8000-65T (active ester crosslinker, Japan DIC) are added into a beaker, 50 parts of MEK or any of the solvents mentioned in the invention are added to dissolve the above compounds, and a proper amount of DMAP (4-dimethylaminopyridine, Guangrong chemical) is used as a curing accelerator to prepare a glue solution with a solid content of 60-70%. The glue was soaked with 2116 glass cloth and the solvent was removed in an oven at 155 ℃ to obtain a prepreg sample.
And laminating by using 4 sheets of 2116 prepreg laminates and 0.5 ounce electrolytic copper foils on the upper sheet and the lower sheet respectively through a hot press to obtain the double-sided copper clad laminate. The lamination conditions were as follows: (1) when the material temperature is 80-120 ℃, the heating rate is controlled to be 1.0-3.0 ℃/min; (2) the pressure was set at 20kg/cm2(ii) a (3) The curing temperature was 200 ℃ and this temperature was maintained for 90 minutes. The corresponding properties are shown in Table 1.
Example 5
30 parts of 1, 6-hexanediol diglycidyl ether (Kramal reagent) and 70 parts of EF40 were added to a beaker, 50 parts of MEK or any of the solvents mentioned in the present invention were added to dissolve the above compounds, and an appropriate amount of 2E4MI was used as a curing accelerator to prepare a cement having a solid content of 60 to 70%. The glue was soaked with 2116 glass cloth and the solvent was removed in an oven at 155 ℃ to obtain a prepreg sample.
And laminating by using 4 sheets of 2116 prepreg laminates and 0.5 ounce electrolytic copper foils on the upper sheet and the lower sheet respectively through a hot press to obtain the double-sided copper clad laminate. The lamination conditions were as follows: (1) when the material temperature is 80-120 ℃, the heating rate is controlled to be 1.0-3.0 ℃/min; (2) the pressure was set at 20kg/cm2(ii) a (3) The curing temperature was 200 ℃ and this temperature was maintained for 90 minutes. The corresponding properties are shown in Table 1.
Example 6
20 parts of 1, 6-hexanediol diglycidyl ether, 20 parts of HP7200H and 58 parts of EF40 are added to a beaker, 60 parts of MEK or any of the solvents mentioned in the invention are added to dissolve the above compounds, and a suitable amount of 2E4MI is used as an accelerator to prepare a glue solution with a solid content of 60-70%. The glue was soaked with 2116 glass cloth and the solvent was removed in an oven at 155 ℃ to obtain a prepreg sample.
And laminating by using 4 sheets of 2116 prepreg laminates and 0.5 ounce electrolytic copper foils on the upper sheet and the lower sheet respectively through a hot press to obtain the double-sided copper clad laminate. The lamination conditions were as follows: (1) when the material temperature is 80-120 ℃, the heating rate is controlled to be 1.0-3.0 ℃/min; (2) the pressure was set at 20kg/cm2(ii) a (3) The curing temperature was 200 ℃ and this temperature was maintained for 90 minutes. The corresponding properties are shown in Table 1.
Example 7
22 parts of 1, 6-hexanediol diglycidyl ether, 15 parts of NC3000H and 63 parts of EF40 are added to a beaker, 50 parts of MEK or any of the solvents mentioned in the invention are added to dissolve the above compounds, and a suitable amount of 2E4MI is used as an accelerator to prepare a glue solution with a solid content of 60-70%. The glue was soaked with 2116 glass cloth and the solvent was removed in an oven at 155 ℃ to obtain a prepreg sample.
And laminating by using 4 sheets of 2116 prepreg laminates and 0.5 ounce electrolytic copper foils on the upper sheet and the lower sheet respectively through a hot press to obtain the double-sided copper clad laminate. The lamination conditions were as follows: (1) when the material temperature is 80-120 ℃, the heating rate is controlled to be 1.0-3.0 ℃/min; (2) the pressure was set at 20kg/cm2(ii) a (3) The curing temperature was 200 ℃ and this temperature was maintained for 90 minutes. The corresponding properties are shown in Table 1.
Example 8
25 parts of ethylene glycol diglycidyl ether (kralmar's reagent) and 75 parts of EF40 (styrene maleic anhydride copolymer, sartomera, usa) are added into a beaker, 50 parts of MEK (methyl ethyl ketone) or any of the solvents mentioned in the invention are added to dissolve the above compounds, and a proper amount of 2E4MI (2-ethyl-4-methylimidazole, Nippon Sizhou chemical industry Co., Ltd.) is used as a curing accelerator to prepare a glue solution with a solid content of 60-70%. The glue was soaked with 2116 glass cloth and the solvent was removed in an oven at 155 ℃ to obtain a prepreg sample.
And laminating by using 4 sheets of 2116 prepreg laminates and 0.5 ounce electrolytic copper foils on the upper sheet and the lower sheet respectively through a hot press to obtain the double-sided copper clad laminate. Laminated stripThe following parts: (1) when the material temperature is 80-120 ℃, the heating rate is controlled to be 1.0-3.0 ℃/min; (2) the pressure was set at 20kg/cm2(ii) a (3) The curing temperature was 200 ℃ and this temperature was maintained for 90 minutes. The corresponding properties are shown in Table 1.
Example 9
43 parts of polyethylene glycol diglycidyl ether (Kramal reagent) and 57 parts of EF40 (styrene maleic anhydride copolymer, Saedoma USA) are added into a beaker, 50 parts of MEK (methyl ethyl ketone) or any solvent mentioned in the invention is added to dissolve the above compounds, and a proper amount of 2E4MI (2-ethyl-4-methylimidazole, Nippon Sikko chemical) is used as a curing accelerator to prepare a glue solution with a solid content of 60-70%. The glue was soaked with 2116 glass cloth and the solvent was removed in an oven at 155 ℃ to obtain a prepreg sample.
And laminating by using 4 sheets of 2116 prepreg laminates and 0.5 ounce electrolytic copper foils on the upper sheet and the lower sheet respectively through a hot press to obtain the double-sided copper clad laminate. The lamination conditions were as follows: (1) when the material temperature is 80-120 ℃, the heating rate is controlled to be 1.0-3.0 ℃/min; (2) the pressure was set at 20kg/cm2(ii) a (3) The curing temperature was 200 ℃ and this temperature was maintained for 90 minutes. The corresponding properties are shown in Table 1.
Comparative example 1
52 parts of HP7200H and 48 parts of EF40 are added into a beaker, 50 parts of MEK or any solvent mentioned in the invention is added to dissolve the above compounds, and a proper amount of 2E4MI is used as a curing accelerator to prepare a glue solution with the solid content of 60-70%. The glue was soaked with 2116 glass cloth and the solvent was removed in an oven at 155 ℃ to obtain a prepreg sample.
And (3) laminating 4 2116 prepregs, laminating the upper and lower electrolytic copper foils with 0.5 ounce respectively, and pressing by a hot press to obtain the double-sided copper clad laminate. The lamination conditions were as follows: (1) when the material temperature is 80-120 ℃, the heating rate is controlled to be 1.0-3.0 ℃/min; (2) the pressure was set at 20kg/cm2(ii) a (3) The curing temperature was 200 ℃ and this temperature was maintained for 90 minutes. The corresponding properties are shown in Table 2.
Comparative example 2
53 parts of NC3000H and 47 parts of EF40 are added to a beaker, 50 parts of MEK or any of the solvents mentioned in the invention are added to dissolve the above compounds, and a proper amount of 2E4MI is used as a curing accelerator to prepare a glue solution with a solid content of 60-70%. The glue was soaked with 2116 glass cloth and the solvent was removed in an oven at 155 ℃ to obtain a prepreg sample.
And laminating by using 4 sheets of 2116 prepreg laminates and 0.5 ounce electrolytic copper foils on the upper sheet and the lower sheet respectively through a hot press to obtain the double-sided copper clad laminate. The lamination conditions were as follows: (1) when the material temperature is 80-120 ℃, the heating rate is controlled to be 1.0-3.0 ℃/min; (2) the pressure was set at 20kg/cm2(ii) a (3) The curing temperature was 200 ℃ and this temperature was maintained for 90 minutes. The corresponding properties are shown in Table 2.
Comparative example 3
56 parts of HP7200H and 44 parts of HPC-8000-65T are added into a beaker, 50 parts of MEK or any of the solvents mentioned in the invention are added to dissolve the above compounds, and a proper amount of DMAP is used as a curing accelerator to prepare a glue solution with a solid content of 60-70%. The glue was soaked with 2116 glass cloth and the solvent was removed in an oven at 155 ℃ to obtain a prepreg sample.
And laminating by using 4 sheets of 2116 prepreg laminates and 0.5 ounce electrolytic copper foils on the upper sheet and the lower sheet respectively through a hot press to obtain the double-sided copper clad laminate. The lamination conditions were as follows: (1) when the material temperature is 80-120 ℃, the heating rate is controlled to be 1.0-3.0 ℃/min; (2) the pressure was set at 20kg/cm2(ii) a (3) The curing temperature was 200 ℃ and this temperature was maintained for 90 minutes. The corresponding properties are shown in Table 2.
Comparative example 4
12 parts of 1, 4-butanediol diglycidyl ether, 30 parts of HP7200H (dicyclopentadiene epoxy resin, Japan DIC) and 58 parts of EF40 are added into a beaker, 50 parts of MEK or any solvent mentioned in the invention is added for dissolution, and a proper amount of 2E4MI is used as a curing accelerator to prepare a glue solution with a solid content of 60-70%. The glue was soaked with 2116 glass cloth and the solvent was removed in an oven at 155 ℃ to obtain a prepreg sample.
And laminating by using 4 sheets of 2116 prepreg laminates and 0.5 ounce electrolytic copper foils on the upper sheet and the lower sheet respectively through a hot press to obtain the double-sided copper clad laminate. The lamination conditions were as follows: (1) when the material temperature is 80-120 ℃, the heating rate is controlled to be 1.0-3.0 ℃/min; (2) the pressure was set at 20kg/cm2(ii) a (3) Curing at 200 deg.C and maintainingThis temperature was 90 minutes. The corresponding properties are shown in Table 2.
The criteria or methods for detecting the parameters referred to in table 1 are as follows:
(1) glass transition temperature (Tg): the measurement was carried out by using DSC measurement in accordance with the DSC measurement method specified by IPC-TM-6502.4.25.
(2) Dielectric constant and dielectric dissipation factor: the test was carried out according to the method of IPC-TM-6502.5.5.13, and the test frequency was 10 GHz.
(3) Evaluation of solder dip resistance: and (3) immersing the copper clad laminate in a tin furnace at the temperature of 288 ℃ until the board foams in a layering mode, and recording the time for the board to foam in a layering mode, wherein the time is the limit of the dip soldering resistance of the board.
(4) Peel strength (N/mm): the test was carried out according to the IPC-TM-6502.4.8 method.
(5) Thermal decomposition temperature (Td): the measurement was carried out by the TGA method defined in IPC-TM-6502.4.24 according to the thermogravimetric analysis (TGA).
TABLE 1
TABLE 2
As can be seen from Table 1, the resin compositions of examples 1 to 7 of the present invention have low dielectric constants and low dielectric dissipation factors, excellent low dielectric properties, and good glass transition temperature Tg and thermal decomposition temperature Td and peel strength. Example 1 can ensure that the laminated board prepared by the resin composition has dielectric constant and low dielectric dissipation factor without adding other epoxy resin, and simultaneously keeps better glass transition temperature and thermal decomposition temperature, and compared with comparative example 1, example 2 or example 3 is compared with comparative example 2, the dielectric constant and the dielectric dissipation factor of the thermosetting resin composition are greatly reduced after alkyl polyhydric alcohol glycidyl ether is added into the system, and simultaneously better thermal property and adhesiveness are kept. As can be seen from comparison of examples 1,2,3 and 4 with examples 5,6, 7 and 8, respectively, the longer the alkyl segment of the alkyl polyol, the better the dielectric properties. As can be seen from the comparison of examples 1,2,3 and 4 with comparative example 4, the present invention utilizes alkyl polyol glycidyl ether as the main resin component and controls the content of the glycidyl ether within the range of 50-100% of the main resin component, which can effectively reduce the dielectric constant and the dielectric loss factor of the thermosetting resin composition and maintain better thermal property and adhesion property, but if the content is below 50%, the dielectric property, thermal property and adhesion property of the resin composition are far inferior to those of the resin composition at the content of 50-100%.
The applicant states that the present invention is illustrated by the above examples of the thermosetting alkyl polyol glycidyl ether resin composition and the application thereof, but the present invention is not limited to the above examples, i.e. it is not meant that the present invention is necessarily dependent on the above examples for implementation. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (28)
1. A thermosetting alkyl polyol glycidyl ether resin composition for a laminate, characterized in that the resin composition comprises an epoxy resin as a main resin component, wherein the epoxy resin contains any one or a combination of at least two of alkyl polyol glycidyl ethers having the following structures:
wherein n is 1-10, m is 1-10, q is 2, 4 or 6;
the alkyl polyhydric alcohol glycidyl ether accounts for 53-100% of the main resin component by mass percent;
the thermosetting resin composition also comprises a curing agent, wherein the curing agent is selected from any one or a mixture of at least two of an anhydride curing agent, an active ester curing agent or a benzoxazine resin;
the dielectric constant of the laminated board made of the resin composition is less than or equal to 3.64 under 10GHz, and the dielectric loss factor is less than or equal to 0.0083.
2. The thermosetting alkylpolyol glycidyl ether resin composition according to claim 1 wherein the alkylpolyol glycidyl ether is
Wherein q is 2, 4 or 6.
3. The thermosetting alkyl polyol glycidyl ether resin composition according to claim 1, wherein the alkyl polyol glycidyl ether is contained in the main resin component in an amount of 53 to 70% by mass.
4. The thermosetting alkyl polyol glycidyl ether resin composition according to claim 1, wherein the main resin component further comprises an epoxy resin other than alkyl polyol glycidyl ether.
5. The thermosetting alkyl polyol glycidyl ether resin composition according to claim 4, wherein the other epoxy resin is selected from any one of phenol novolac type epoxy resin, methyl phenol novolac type epoxy resin, bisphenol A novolac epoxy resin, dicyclopentadiene epoxy resin, biphenyl epoxy resin, naphthalene type epoxy resin, glycidyl ether type epoxy resin, alicyclic epoxy resin, polyethylene glycol type epoxy resin, tetraphenylethane tetraglycidyl ether resin, or triphenol methane type epoxy resin, or a mixture of at least two thereof.
6. The thermosetting alkylpolyol glycidyl ether resin composition according to claim 4 wherein the other epoxy resin is a phosphorous epoxy resin and/or a silicon epoxy resin.
7. The thermosetting alkyl polyol glycidyl ether resin composition according to claim 1, wherein the anhydride curing agent is selected from the group consisting of styrene maleic anhydride, methyl vinyl ether-maleic anhydride copolymer, methyl hexahydrophthalic anhydride, phenylsuccinic anhydride, succinic anhydride, oxa-anhydride, dimethyl maleic anhydride, glutaric anhydride, 2-methylsuccinic anhydride, phthalic anhydride, norbornene dianhydride, pyromellitic anhydride, 1, 2-cyclohexane dicarboxylic anhydride, 4-fluorophthalic anhydride, 3-fluorophthalic anhydride, 2-dimethylsuccinic anhydride, 1-cyclohexyl diacetic anhydride, phenylmaleic anhydride, citraconic anhydride, 1, 8-naphthalic anhydride, 4 '-diphenyl ether dianhydride, 3', 4 '-diphenyl tetracarboxylic dianhydride, 3' -diphenyl tetracarboxylic dianhydride, One or a mixture of at least two of pyromellitic dianhydride, 3', 4' -dianhydride diphenyl ether, 4' - (hexafluoroisopropylene) diphthalic anhydride, 1,2,3, 4-cyclobutanetetracarboxylic dianhydride, 3', 4' -benzophenonetetracarboxylic dianhydride, 3,4,5, 6-tetrahydrophthalic anhydride or cis-1, 2,3, 6-tetrahydrophthalic anhydride.
8. The thermosetting alkyl polyol glycidyl ether resin composition according to claim 1, wherein the active ester curing agent is obtained by reacting a phenolic compound, a di-functional carboxylic aromatic compound or an acidic halide, which are bonded to each other via an aliphatic cyclic hydrocarbon structure, with a monohydroxy compound, wherein the amount of the di-functional carboxylic aromatic compound or the acidic halide is 1mol, the amount of the phenolic compound, which is bonded to each other via an aliphatic cyclic hydrocarbon structure, is 0.05 to 0.75mol, and the amount of the monohydroxy compound is 0.25 to 0.95 mol.
9. The thermosetting alkyl polyol glycidyl ether resin composition according to claim 1, wherein the structural formula of the active ester curing agent is as follows:
wherein X is phenyl or naphthyl, j is 0 or 1, k is 0 or 1, and n is 0.25-1.25.
10. The thermosetting alkyl polyol glycidyl ether resin composition according to any of claims 1 to 9 wherein the resin composition further comprises a catalyst.
11. The thermosetting alkylpolyol glycidyl ether resin composition as claimed in claim 10, wherein the catalyst is imidazole or pyridine compound.
12. The thermosetting alkyl polyol glycidyl ether resin composition according to claim 11, wherein the imidazole based compound is selected from any one or a mixture of at least two of 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 2-undecylimidazole, 1-benzyl-2-methylimidazole, 2-heptadecylimidazole, 2-isopropylimidazole, 2-phenyl-4-methylimidazole, 2-dodecylimidazole or 1-cyanoethyl-2-methylimidazole.
13. The thermosetting alkylpolyol glycidyl ether resin composition according to claim 11 wherein the pyridine compound is 4-dimethylaminopyridine.
14. The thermosetting alkyl polyol glycidyl ether resin composition according to claim 10, wherein the catalyst is used in an amount of 0.001 to 5.0% by mass based on the thermosetting alkyl polyol glycidyl ether resin composition.
15. The thermosetting alkyl polyol glycidyl ether resin composition according to claim 14, wherein the catalyst is used in an amount of 0.02 to 4.0% by mass based on the thermosetting alkyl polyol glycidyl ether resin composition.
16. The thermosetting alkyl polyol glycidyl ether resin composition according to claim 15, wherein the catalyst is used in an amount of 0.005 to 3.0% by mass based on the thermosetting alkyl polyol glycidyl ether resin composition.
17. The thermosetting alkyl polyol glycidyl ether resin composition according to any of claims 1 to 9, wherein the resin composition further comprises a flame retardant.
18. The thermosetting alkyl polyol glycidyl ether resin composition according to claim 17, wherein the flame retardant is selected from organic flame retardants and/or inorganic flame retardants.
19. The thermosetting alkyl polyol glycidyl ether resin composition according to claim 18, characterized in that the organic flame retardant is any one or a mixture of at least two of tris (2, 6-dimethylphenyl) phosphine, resorcinol bis [ bis (2, 6-dimethylphenyl) phosphate ], resorcinol tetraphenyl diphosphate, triphenyl phosphate, bisphenol A bis (diphenyl phosphate), a phosphazene flame retardant, 10- (2, 5-dihydroxyphenyl) -10-hydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10- (2, 5-dihydroxynaphthyl) -10-hydro-9-oxa-10-phosphaphenanthrene-10-oxide flame retardants.
20. The thermosetting alkyl polyol glycidyl ether resin composition according to claim 18, wherein the inorganic flame retardant is selected from red phosphorus, aluminum hydroxide, magnesium hydroxide or antimony trioxide, or a mixture of at least two thereof.
21. The thermosetting alkyl polyol glycidyl ether resin composition according to claims 1 to 9 wherein the resin composition further comprises a filler.
22. The thermosetting alkyl polyol glycidyl ether resin composition according to claim 21, wherein the filler is selected from the group consisting of silica, kaolin, talc, magnesium hydroxide, aluminum hydroxide, boehmite, hydrotalcite, titanium oxide, calcium silicate, beryllium oxide, boron nitride, glass powder, zinc borate, aluminum nitride, silicon carbide, magnesium oxide, zirconium oxide, mullite, titanium dioxide, potassium titanate, hollow glass beads, polytetrafluoroethylene powder, polystyrene powder, potassium titanate fiber, silicon carbide single crystal fiber, silicon nitride fiber, alumina single crystal fiber, or a mixture of at least two of glass short fibers.
23. The thermosetting alkyl polyol glycidyl ether resin composition according to any of claims 1 to 9, wherein the resin composition further comprises a curing accelerator.
24. A resin cement obtained by dissolving or dispersing the thermosetting alkyl polyol glycidyl ether resin composition according to any one of claims 1 to 23 in a solvent.
25. A prepreg made using the thermosetting alkyl polyol glycidyl ether resin composition according to any one of claims 1 to 23.
26. A laminate for printed circuits comprising one or at least two superimposed prepregs according to claim 25, wherein the laminate for printed circuits has a dielectric constant of 3.64 or less and a dielectric dissipation factor of 0.0083 or less at 10 GHz.
27. A printed circuit board comprising one or at least two superimposed prepregs according to claim 25.
28. Use of a thermosetting alkyl polyol glycidyl ether resin composition according to any one of claims 1 to 9 for reducing the dielectric constant of a laminate.
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| PCT/CN2016/098478 WO2017092471A1 (en) | 2015-12-02 | 2016-09-08 | Thermosetting alkyl polyol glycidyl ether resin composition and application thereof |
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| EP3560978A1 (en) * | 2018-04-26 | 2019-10-30 | SABIC Global Technologies B.V. | High heat thermoset epoxy compositions |
| WO2020180973A1 (en) * | 2019-03-04 | 2020-09-10 | Sabic Global Technologies B.V. | Metal-clad laminate including thermoset epoxy composition |
| CN113121940B (en) * | 2019-12-31 | 2022-12-30 | 广东生益科技股份有限公司 | Thermosetting resin composition, and prepreg, laminated board and printed wiring board using thermosetting resin composition |
| CN111875781A (en) * | 2020-07-23 | 2020-11-03 | 南开大学 | Composition for preparing glass-like polymer, glass-like polymer and preparation method and application thereof |
| CN112778948B (en) * | 2020-12-23 | 2022-06-24 | 北京康美特科技股份有限公司 | Conductive silver adhesive and preparation method and application thereof |
| CN112745480A (en) * | 2020-12-25 | 2021-05-04 | 天津晶东化学复合材料有限公司 | Curing agent for ultrahigh molecular weight epoxy resin |
| CN113388092B (en) * | 2021-05-26 | 2023-01-03 | 济南大学 | Preparation and application of fluorine-containing benzoxazine epoxy resin copolymer with low dielectric constant |
| CN113322716B (en) * | 2021-06-11 | 2022-09-09 | 广州再森科技股份有限公司 | Environment-friendly coating for paper-plastic composite material and paper-plastic composite material |
| CN113844039A (en) * | 2021-09-27 | 2021-12-28 | 山东金宝电子股份有限公司 | Preparation method of novel low-dielectric-constant copper-clad plate glue solution |
| CN114953646A (en) * | 2022-06-09 | 2022-08-30 | 山东金宝电子股份有限公司 | Preparation method of copper-clad plate for mini LED backboard and copper-clad plate |
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| US20080039555A1 (en) * | 2006-08-10 | 2008-02-14 | Michel Ruyters | Thermally conductive material |
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