CN117417637A - Resin composition and application thereof - Google Patents
Resin composition and application thereof Download PDFInfo
- Publication number
- CN117417637A CN117417637A CN202311560494.4A CN202311560494A CN117417637A CN 117417637 A CN117417637 A CN 117417637A CN 202311560494 A CN202311560494 A CN 202311560494A CN 117417637 A CN117417637 A CN 117417637A
- Authority
- CN
- China
- Prior art keywords
- parts
- resin
- polyphenyl ether
- prepolymer
- ether
- 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.)
- Pending
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 43
- 229920005989 resin Polymers 0.000 claims abstract description 91
- 239000011347 resin Substances 0.000 claims abstract description 91
- 229920013636 polyphenyl ether polymer Polymers 0.000 claims abstract description 49
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 19
- 229920001955 polyphenylene ether Polymers 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 229920013638 modified polyphenyl ether Polymers 0.000 claims abstract description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 5
- 239000000314 lubricant Substances 0.000 claims abstract description 3
- 239000003822 epoxy resin Substances 0.000 claims description 29
- 229920000647 polyepoxide Polymers 0.000 claims description 29
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 14
- 239000005011 phenolic resin Substances 0.000 claims description 14
- 229920001568 phenolic resin Polymers 0.000 claims description 14
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims description 13
- XENMLDGAMXHYMH-UHFFFAOYSA-N 2-[(2-prop-2-enylphenoxy)methyl]oxirane Chemical compound C=CCC1=CC=CC=C1OCC1OC1 XENMLDGAMXHYMH-UHFFFAOYSA-N 0.000 claims description 12
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000011256 inorganic filler Substances 0.000 claims description 7
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000004643 cyanate ester Substances 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
- 229920013822 aminosilicone Polymers 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
- -1 allyl phenyl glycidyl ether Chemical compound 0.000 abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 12
- 238000010521 absorption reaction Methods 0.000 abstract description 9
- 239000004593 Epoxy Substances 0.000 abstract description 4
- 238000012545 processing Methods 0.000 abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- 239000004744 fabric Substances 0.000 description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 13
- 239000000377 silicon dioxide Substances 0.000 description 12
- 239000003365 glass fiber Substances 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000011888 foil Substances 0.000 description 9
- 235000012239 silicon dioxide Nutrition 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- 239000012779 reinforcing material Substances 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 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 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 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 4
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000003292 glue Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920003192 poly(bis maleimide) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 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 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- KTRQRAQRHBLCSQ-UHFFFAOYSA-N 1,2,4-tris(ethenyl)cyclohexane Chemical compound C=CC1CCC(C=C)C(C=C)C1 KTRQRAQRHBLCSQ-UHFFFAOYSA-N 0.000 description 1
- OLZONBZGRPJZKD-UHFFFAOYSA-N 1-ethenyl-2-[2-(2-ethenylphenyl)ethyl]benzene Chemical compound C=CC1=CC=CC=C1CCC1=CC=CC=C1C=C OLZONBZGRPJZKD-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- ZYMOKRVQKMAIBA-UHFFFAOYSA-N 3-(3-phenylpenta-1,4-dien-3-yloxy)penta-1,4-dien-3-ylbenzene Chemical compound C=1C=CC=CC=1C(C=C)(C=C)OC(C=C)(C=C)C1=CC=CC=C1 ZYMOKRVQKMAIBA-UHFFFAOYSA-N 0.000 description 1
- PVFQHGDIOXNKIC-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenol Chemical compound C=1C=CC(C(C)(C)C=2C=CC(O)=CC=2)=CC=1C(C)(C)C1=CC=C(O)C=C1 PVFQHGDIOXNKIC-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000378 calcium silicate Substances 0.000 description 1
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical group C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 108091081474 miR-5000 stem-loop Proteins 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000011191 terminal modification Methods 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene 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
- 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
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention provides a resin composition and application thereof, comprising the following components in parts by weight: (a) maleimide resin and prepolymer thereof: 100 parts; (B) polyphenylene ether resin: 10-200 parts of a lubricant; (C) a crosslinking agent: 5-80 parts; the polyphenyl ether resin contains terminal hydroxyl modified polyphenyl ether resin; the crosslinking agent contains a compound shown in a structural formula (1). The invention improves the compatibility and the processing problem between the maleimide resin and the polyphenyl ether by adding the allyl phenyl glycidyl ether containing two reactive groups; meanwhile, allyl in allyl phenyl glycidyl ether reacts with maleimide to form ether bond, epoxy reacts with hydroxyl in polyphenyl ether to form multidimensional reticular crosslinked cured product, so that the whole crosslinked network structure is more compact, and finally high heat resistance, low water absorption, high peel strength and low dielectric property are obtained.
Description
Technical Field
The invention relates to the technical field of electronic materials, in particular to a resin composition and application thereof.
Background
With the development and scale of 5G, PCB substrate materials are required to have a low dielectric constant and dielectric loss tangent to reduce delay, distortion and loss of signals and interference between signals at high speed transmission. Accordingly, it is desirable to provide a thermosetting resin composition which can exhibit a sufficiently low dielectric constant and low dielectric loss tangent (i.e., the lower and the better the dielectric constant and the dielectric loss tangent) during signal transmission at higher speeds and higher frequencies, and which places higher demands on the performance of the package substrate material: it has low planar thermal expansion coefficient and low dielectric loss tangent.
The main chain of the polyphenyl ether resin contains a large amount of phenyl ether groups, has good physical and mechanical properties, and lower dielectric constant and dielectric loss tangent, and is one of the key materials in the ideal high-frequency high-speed substrate. However, the polyphenylene ether resin has a high melting point, poor flowability and poor processability, and thus the prepreg comprising the polyphenylene ether resin has a high melt viscosity, and it is difficult to meet the process requirements of multilayer printed wiring boards. In the prior art, the melting temperature can be effectively reduced and the fluidity can be improved by reducing the molecular weight of the polyphenyl ether resin, but the low molecular weight can lead to the reduction of the heat resistance of the polyphenyl ether resin, and is not beneficial to the processing and the application of a printed circuit board. Therefore, in order to meet the requirements of actual production and processing, polyphenylene ether needs to be modified by blending or chemical grafting, and common modification methods are directed to terminal modification such as methacrylate modification or styrene modification.
The bismaleimide resin condensate has excellent performances of high temperature resistance, damp heat resistance, high modulus, low CTE, high strength and the like, and is particularly suitable for being used as matrix resin of IC packaging carrier boards and carrier-like boards. However, the disadvantages of high brittleness, poor processability and the like are also present, which limits the large-scale application thereof.
The prior art CN102850766a discloses a halogen-free resin composition, which comprises an epoxy modified polyphenylene ether resin, an allyl modified bismaleimide resin, an epoxy resin, a phosphorus-containing flame retardant, a curing accelerator, a curing agent and an inorganic filler; the resin composition has good compatibility, wettability and processability, but the copper-clad plate containing the resin composition has high dielectric loss tangent, high water absorption and insufficient heat resistance, and is difficult to meet the performance requirements of a high-frequency printed circuit board. In the prior art CN111386313, a resin composition is disclosed which comprises a maleimide compound containing a biphenyl structure and a polyphenylene ether resin containing a carbon-carbon unsaturated double bond, wherein the peel strength, heat resistance, water absorption and dielectric properties are further improved by the maleimide resin containing a biphenyl structure; but it has a technical disadvantage of poor workability.
Therefore, development of a resin composition and application thereof, which can improve compatibility and processability between maleimide resin and polyphenylene ether, and which can obtain high heat resistance, low water absorption, high peel strength and low dielectric properties, is clearly of positive practical significance.
Disclosure of Invention
The invention aims to provide a resin composition and application thereof, which are characterized in that the compatibility and processability problems between maleimide resin and polyphenyl ether are improved by adding allyl phenyl glycidyl ether containing two reactive groups, meanwhile, allyl groups in the allyl phenyl glycidyl ether react with maleimide groups to form ether bonds, epoxy groups react with hydroxyl groups in the polyphenyl ether to form a multidimensional reticular crosslinked cured product, so that the whole crosslinked network structure is more compact, and finally, high heat resistance, low water absorption, high peel strength and low dielectric property are obtained.
In order to achieve the above purpose, the present invention provides the following technical solutions:
a resin composition comprising, in parts by weight:
(A) Maleimide resin and prepolymer thereof: 100 parts;
(B) Polyphenylene ether resin: 10-200 parts of a lubricant;
(C) Crosslinking agent: 5-80 parts;
the polyphenyl ether resin contains terminal hydroxyl modified polyphenyl ether resin;
the crosslinking agent contains a compound shown in a structural formula (1):
preferably, the polyphenyl ether resin contains carbon-carbon double bond modified polyphenyl ether resin.
Preferably, the polyphenylene ether resin is a mixture of a polyphenylene ether represented by the structural formula (2) and a modified polyphenylene ether represented by the structural formula (3) or the structural formula (4);
wherein R1, R2, R3, R4, R5, R6, R7, R8, R10 are hydrogen or C1-C5 alkyl, Y is a direct connection, -O-, methylene, ethylene,One of them.
Preferably, in the structural formula (2) and the structural formula (3), R1, R2, R5 and R6 are methyl, and R3, R4, R7 and R8 are hydrogen; in the structural formula (4), R1, R2, R5, R6 and R8 are methyl, and R3, R4 and R7 are hydrogen.
Preferably, in formula (3) terminal R10 is methyl.
Preferably, the polyphenylene ether resin represented by the formula (2) contains 10 to 80 parts by weight based on 100 parts by weight of the polyphenylene ether resin.
Preferably, the polyphenyl ether resin shown in the structural formula (2) can be SA90 or SA9000 manufactured by Sabyk, and OPE-2St manufactured by Mitsubishi.
Preferably, the cross-linking agent comprises one of o-allylphenyl glycidyl ether, m-allylphenyl glycidyl ether or p-allylphenyl glycidyl ether;
the o-allylphenyl glycidyl ether is shown as a structural formula (5):
preferably, the cross-linking agent is o-allylphenyl glycidyl ether shown in the structural formula (5).
Preferably, the o-allylphenyl glycidyl ether represented by the structural formula (5) is available from four-day synthetic company.
Preferably, the crosslinking agent further contains any one or a combination of at least two of divinylbenzene, bis-vinylbenzyl ether, 1, 2-bis (vinylphenyl) ethane, triallyl isocyanurate (TAIC) or prepolymer thereof, dicyclopentadiene Dimethacrylate (DCP), triallyl cyanurate, 1,2, 4-trivinylcyclohexane, tricyclodecane dimethanol dimethacrylate, trimethylol propane trimethacrylate or polyolefin resin containing butadiene structure, and the content thereof is 1 to 80 percent based on 100 percent by weight of the crosslinking agent.
Preferably, the prepolymer of the maleimide resin is at least one of an allyl compound-modified prepolymer, an aromatic amine compound-modified prepolymer, an aliphatic amine compound-modified prepolymer, an amino silicone resin-modified prepolymer, a cyanate ester-modified prepolymer, or a benzoxazine-modified prepolymer.
Preferably, the bismaleimide compound in the maleimide resin or modified bismaleimide prepolymer is selected from at least one of the following structures:
r2 is hydrogen, methyl or ethyl, R1 is methylene, ethylene or +.>n is an integer of 1 to 10;
n is an integer of 1 to 10;
n is an integer of 1 to 10;
n is an integer of 1 to 10;
r is hydrogen, methyl or ethyl, and n is an integer of 1 to 10.
Preferably, the maleimide resin is selected from any one or more of the following brands of materials: BMI-1000, BMI-1000H, BMI-1100, BMI-1100H, BMI-2000, BMI-2300, BMI-3000H, BMI-4000H, BMI-5000, BMI-5100, BMI-7000, and BMI-7000H manufactured by Dahe chemical Co., ltd; BMI, BMI-70, BMI-80 manufactured by KI chemical Co., ltd; MIR-3000, MIR-5000 manufactured by Japanese chemical pharmaceutical Co., ltd; x9-450, X9-470 manufactured by DIC corporation of Japan; d936, D937, D939, D950, manufactured by Sichuan Dong Corp.
Preferably, the inorganic filler is also included, and the content of the inorganic filler is 30-200 parts.
Preferably, the inorganic filler is at least one selected from fused silica, crystalline silica, spherical silica, hollow silica, aluminum hydroxide, aluminum oxide, talc, aluminum nitride, boron nitride, silicon carbide, barium sulfate, barium titanate, strontium titanate, calcium carbonate, calcium silicate, mica, and glass fiber powder.
Preferably, the inorganic filler is silica, more preferably spherical silica.
Preferably, the inorganic filler is surface treated with a silane coupling agent selected from one or more of KBM-573, KBM-6883, KBONING chemical, KBM-1003, KBM-1403.
Preferably, at least one of epoxy resin, cyanate resin, benzoxazine resin or phenolic resin is also included.
The epoxy resin is selected from one or more of bisphenol A epoxy resin, bisphenol F epoxy resin, tetraphenyl ethane epoxy resin, triphenylmethane epoxy resin, biphenyl epoxy resin, naphthalene ring type epoxy resin, dicyclopentadiene type epoxy resin, isocyanate type epoxy resin, aralkyl novolac epoxy resin, bisphenol A novolac type epoxy resin, polyphenyl ether modified epoxy resin, alicyclic epoxy resin, glycidylamine type epoxy resin, glycidylester type epoxy resin, phosphorus-containing epoxy resin, nitrogen-containing epoxy resin and multifunctional epoxy resin, and the content of the epoxy resin is 1-70 parts by weight.
Further preferably, the epoxy resin is naphthalene type epoxy resin or biphenyl type epoxy resin.
The cyanate is a compound containing at least one cyanate group, which may be a monomer, a polymer, a prepolymer, or a combination thereof.
Preferably, the cyanate ester compound is a prepolymer, or a combination of a prepolymer and a monomer, or a combination of a prepolymer and a polymer.
As an alternative, the cyanate ester compound is at least one selected from bisphenol a type cyanate, bisphenol F type cyanate, bisphenol E type cyanate, bisphenol M type cyanate, DCPD type cyanate, naphthalene type cyanate, and diphenyl cyanate, and the content thereof is 1-50 parts by weight.
The benzoxazine resin is selected from bisphenol A type benzoxazine resin, biphenyl type benzoxazine resin, naphthalene type benzoxazine resin, bisphenol F type benzoxazine resin, dicyclopentadiene type benzoxazine resin or double bond-containing benzoxazine resin, and the content of the benzoxazine resin is 1-60 parts by weight.
The phenolic resin is selected from bisphenol A type phenolic resin, biphenyl type phenolic resin, naphthalene type phenolic resin, triazinyl-containing phenolic resin, bisphenol F type phenolic resin or dicyclopentadiene type phenolic resin, and the content of the phenolic resin is 1-20 parts by weight.
Further preferably, the resin composition comprises: 100 parts of maleimide resin and prepolymer thereof, 10-100 parts of double bond-containing polyphenyl ether resin, 10-100 parts of hydroxyl-containing polyphenyl ether resin and a crosslinking agent: 5-80 parts of epoxy resin and 1-70 parts of epoxy resin.
Further preferably, the resin composition comprises: 100 parts of maleimide resin and prepolymer thereof, 10-100 parts of double bond-containing polyphenyl ether resin, 10-100 parts of hydroxyl-containing polyphenyl ether resin and a crosslinking agent: 5-80 parts of cyanate ester and 1-50 parts of cyanate ester.
Further preferably, the resin composition comprises: 100 parts of maleimide resin and prepolymer thereof, 10-100 parts of double bond-containing polyphenyl ether resin, 10-100 parts of hydroxyl-containing polyphenyl ether resin and a crosslinking agent: 5-80 parts of epoxy resin, 1-50 parts of phenolic resin and 1-20 parts of phenolic resin.
Further preferably, the resin composition comprises: 100 parts of maleimide resin and prepolymer thereof, 10-100 parts of double bond-containing polyphenyl ether resin, 10-100 parts of hydroxyl-containing polyphenyl ether resin and a crosslinking agent: 5-80 parts of epoxy resin, 1-70 parts of benzoxazine resin and 1-40 parts of benzoxazine resin.
Preferably, the resin composition further contains 0.01 to 5 parts of a catalyst. The catalyst is at least one of imidazole catalyst, pyridine catalyst and organic metal salt catalyst.
Preferably, the catalyst is at least one of 4-dimethylaminopyridine, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, modified imidazole and zinc octoate.
The application also claims the use of a resin composition as described above in cured sheets, laminates, insulating sheets, insulating films, circuit substrates and electrical devices.
Specifically, the prepreg comprises a reinforcing material, and the above-described resin composition attached to the surface of the reinforcing material.
Preferably, the reinforcing material is at least one selected from the group consisting of natural fibers, organic synthetic fibers, organic fabrics, and inorganic fabrics. Preferably, the reinforcing material is a glass fiber cloth, and a split cloth or a flat cloth is preferably used in the glass fiber cloth, more preferably, the glass fiber cloth is an E glass fiber cloth, an S glass fiber cloth, a T glass fiber cloth or a Q glass fiber cloth.
In addition, when the reinforcing material is a glass fiber cloth, the glass fiber cloth generally needs to be chemically treated to improve the bonding between the resin composition and the interface of the glass fiber cloth. The main method of the chemical treatment is a coupling agent treatment, and the coupling agent is preferably an epoxy silane coupling agent or an amino silane coupling agent or the like, so as to provide good water resistance and heat resistance.
Preferably, the preparation method of the prepreg comprises the following steps:
dissolving the resin composition with a solvent to prepare a resin composition glue solution;
and (3) dipping the reinforcing material in the resin composition glue solution, and taking out, heating and drying the dipped reinforcing material to obtain the prepreg.
In one embodiment, the impregnated reinforcing material is baked for 1min to 15min at the temperature of 100 ℃ to 180 ℃ and dried to obtain the prepreg.
Specifically, the solvent may be one or a combination of any several of acetone, butanone, toluene, methyl isobutyl ketone, N, N-dimethylformamide, N, N-dimethylacetamide, ethylene glycol methyl ether, propylene glycol methyl ether, benzene, toluene, xylene and cyclohexane.
The amount of the solvent to be used in the present invention is not particularly limited. The amount of the solvent to be added is selected by one skilled in the art according to his own experience, as long as the resulting resin composition dope can be brought to a viscosity suitable for use.
Preferably, the laminated board comprises at least one prepreg and a metal foil formed on at least one surface of the prepreg.
In an embodiment in which the laminate comprises at least two prepregs as described above, the at least two prepregs are stacked and bonded together by heating and pressurizing, and then a metal foil is bonded on one or both sides of the bonded prepregs by heating and pressurizing to form the laminate.
Specifically, the laminate was prepared as follows: and coating metal foil on one side or two sides of one prepreg, or coating metal foil on one side or two sides of at least 2 prepregs after superposing, and performing hot press forming to obtain the laminated board.
The pressing conditions of the laminated board are as follows: pressing for 2-4 hours under the pressure of 0.2-2 MPa and the temperature of 150-250 ℃.
In particular, the number of prepregs may be determined according to the thickness of the laminate as desired, and one or more prepregs may be used.
Preferably, the metal foil may be copper foil or aluminum foil, and the material of the metal foil is not limited; the thickness of the metal foil is also not particularly limited, and may be, for example, 5 μm, 8 μm, 12 μm, 18 μm, 35 μm or 70 μm.
Preferably, the printed wiring board comprises at least one prepreg as described above, or the printed wiring board comprises at least one laminate as described above.
Preferably, the preparation method of the printed circuit board is a conventional technical means in the field, and will not be described herein.
Due to the application of the technical scheme, compared with the prior art, the invention has the following advantages:
(1) The invention improves the compatibility and the processing problem between the maleimide resin and the polyphenyl ether by adding the allyl phenyl glycidyl ether containing two reactive groups;
(2) According to the invention, allyl in allyl phenyl glycidyl ether reacts with maleimide to form ether bond, epoxy reacts with hydroxyl in polyphenyl ether to form multidimensional reticular crosslinked cured product, so that the whole crosslinked network structure is more compact, and finally high heat resistance, low water absorption, high peel strength and low dielectric property are obtained.
Detailed Description
The following description of the embodiments of the present invention will clearly and fully describe the technical solutions of the embodiments of the present invention in conjunction with the specific contents of the present invention, and it is apparent that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to fall within the scope of the invention.
Synthesis example 1: preparation of allyl Compound modified maleimide resin (prepolymer A)
50g of an allylbisphenol A compound, 100g of a maleimide resin (BMI-2300, manufactured by Dagher chemical reaction), 1.8g of p-aminophenol and an appropriate amount of a butanone solvent were added to a beaker, and reacted at 110℃for 90 minutes to obtain an allylbisphenol A modified maleimide resin.
Synthesis example 2: preparation of aromatic diamine Compound modified maleimide resin (prepolymer B)
50g of a4, 4' -diaminodiphenylmethane compound, 100g of a maleimide resin (manufactured by KI formation, KI-80), 2.4g of p-aminophenol and an appropriate amount of a butanone solvent were added to a beaker, and reacted at 125℃for 110 minutes to obtain an aromatic diamine compound-modified maleimide resin.
Example 1
The present embodiment is a resin composition comprising, in parts by weight: 100 parts of prepolymer A, 30 parts of polyphenyl ether A, 50 parts of polyphenyl ether B, 50 parts of o-allylphenyl glycidyl ether, 150 parts of silicon dioxide and 0.5 part of 2-methylimidazole.
Example 2
The present embodiment is a resin composition comprising, in parts by weight: 100 parts of prepolymer B, 40 parts of polyphenyl ether A, 30 parts of polyphenyl ether C, 50 parts of o-allylphenyl glycidyl ether, 150 parts of silicon dioxide and 0.5 part of 2-methylimidazole.
Example 3
The present embodiment is a resin composition comprising, in parts by weight: 100 parts of maleimide resin, 20 parts of polyphenyl ether A, 30 parts of polyphenyl ether B, 10 parts of TAIC, 50 parts of o-allylphenyl glycidyl ether, 150 parts of silicon dioxide and 0.5 part of 2-methylimidazole.
Example 4
The present embodiment is a resin composition comprising, in parts by weight: 100 parts of prepolymer A, 30 parts of polyphenyl ether A, 50 parts of polyphenyl ether B, 50 parts of o-allylphenyl glycidyl ether, 30 parts of epoxy resin, 5 parts of phenolic resin, 150 parts of silicon dioxide and 0.5 part of 2-methylimidazole.
Example 5
The present embodiment is a resin composition comprising, in parts by weight: 100 parts of prepolymer B, 40 parts of polyphenyl ether A, 30 parts of polyphenyl ether C, 50 parts of o-allylphenyl glycidyl ether, 20 parts of cyanate resin, 150 parts of silicon dioxide and 0.5 part of 2-methylimidazole.
Example 6
The present embodiment is a resin composition comprising, in parts by weight: 100 parts of maleimide resin, 50 parts of polyphenyl ether A, 10 parts of TAIC, 50 parts of o-allylphenyl glycidyl ether, 150 parts of silicon dioxide and 0.5 part of 2-methylimidazole.
Comparative example 1
The present embodiment is a resin composition comprising, in parts by weight: 100 parts of prepolymer A, 30 parts of polyphenyl ether A, 50 parts of polyphenyl ether B, 50 parts of TAIC, 150 parts of silicon dioxide and 0.5 part of 2-methylimidazole.
Comparative example 2
The present embodiment is a resin composition comprising, in parts by weight: 100 parts of maleimide resin, 20 parts of polyphenyl ether A, 30 parts of polyphenyl ether B, 60 parts of TAIC, 150 parts of silicon dioxide and 0.5 part of 2-methylimidazole.
The components and addition amounts of examples 1 to 6 and comparative examples 1 to 2 are shown in Table 1 below.
TABLE 1
The raw material manufacturers and models of the respective components used in examples 1 to 6 and comparative examples 1 to 2 are shown in Table 2 below.
TABLE 2
Performance tests were conducted on the above examples 1 to 6 and comparative examples 1 to 2, respectively, and the test results are shown in Table 3 below.
TABLE 3 Table 3
Example 1 | Example 2 | EXAMPLE 3 | EXAMPLE 4 | EXAMPLE 5 | EXAMPLE 6 | Comparative 1 | Comparative example 2 | |
Glass transition temperature (DMA/. Degree.C) | 246 | 248 | 253 | 240 | 259 | 256 | 240 | 242 |
PCT water absorption rate | 0.19 | 0.20 | 0.23 | 0.22 | 0.21 | 0.25 | 0.22 | 0.29 |
Coefficient of thermal expansion (ppm/. Degree.C.) in the face | 12 | 12 | 10 | 13 | 10 | 10 | 12 | 13 |
Dielectric constant (10 GHz) | 3.2 | 3.15 | 3.35 | 3.45 | 3.20 | 3.39 | 3.36 | 3.46 |
Dielectric loss (10 GHz) | 0.003 | 0.003 | 0.004 | 0.004 | 0.003 | 0.004 | 0.004 | 0.006 |
Peel strength (N/mm) | 0.78 | 0.75 | 0.82 | 0.91 | 0.80 | 0.87 | 0.61 | 0.63 |
Compatibility of | O | O | Δ | O | O | O | Δ | Ⅹ |
The performance test methods for all of the above examples 1 to 6 and comparative examples 1 to 2 were as follows:
1) Glass transition temperature (Tg): a dynamic mechanical property tester (TA DMA Q800, USA) is adopted, the heating rate is 10 ℃/min, and the atmosphere is nitrogen;
2) Dk and Df: the measurement was carried out at 10GHz according to IPC-TM-6502.5.5.9 by the plate method;
3) Surface Coefficient of Thermal Expansion (CTE) determination: TMA (thermo mechanical analysis) is adopted, the heating rate is 10 ℃/min, and the test temperature is 30-100 ℃;
rheology of the aminophenols of example 3 and comparative example 2:
4) PCT water absorption: taking 3 samples with the thickness of 10cm multiplied by 10cm and the thickness of 0.80mm and with metal foils removed from two sides, drying at 120 ℃ for 2 hours, then treating for 7 hours at 121 ℃ under 2 atmospheres by using an autoclave stewing test (Pressure Cooker test) machine, drying water surface free water, putting into a dryer for cooling, weighing, and calculating the water absorption rate of the plate according to the front and rear weights;
5) Peel Strength (PS): testing the peel strength of the metal cap layer with laminate a according to the "post thermal stress" experimental conditions in the IPC-TM-650 method;
6) Compatibility: after stirring the glue for 10min, the transparency was observed, for example, as clear and transparent as O, slightly cloudy as delta, and frosted as x.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (10)
1. A resin composition is characterized by comprising the following components in parts by weight:
(A) Maleimide resin and prepolymer thereof: 100 parts;
(B) Polyphenylene ether resin: 10-200 parts of a lubricant;
(C) Crosslinking agent: 5-80 parts;
the polyphenyl ether resin contains terminal hydroxyl modified polyphenyl ether resin;
the crosslinking agent contains a compound shown in a structural formula (1):
2. a resin composition according to claim 1, characterized in that: the polyphenyl ether resin contains carbon-carbon double bond modified polyphenyl ether resin.
3. A resin composition according to claim 1, characterized in that: the polyphenyl ether resin is a mixture of polyphenyl ether shown in a structural formula (2) and modified polyphenyl ether shown in a structural formula (3) or a structural formula (4);
wherein R1, R2, R3, R4, R5, R6, R7, R8, R10 are hydrogen or C1-C5 alkyl, Y is a direct connection, -O-, methylene, ethylene,-S-or->One of them.
4. A resin composition according to claim 3, characterized in that: in the structural formula (2) and the structural formula (3), R1, R2, R5 and R6 are methyl, and R3, R4, R7 and R8 are hydrogen; in the structural formula (4), R1, R2, R5, R6 and R8 are methyl, and R3, R4 and R7 are hydrogen.
5. A resin composition according to claim 3, characterized in that: the polyphenylene ether resin represented by the structural formula (2) contains 10 to 80 parts by weight based on 100 parts by weight of the polyphenylene ether resin.
6. A resin composition according to claim 1, wherein the crosslinking agent comprises one of o-allylphenyl glycidyl ether, m-allylphenyl glycidyl ether or p-allylphenyl glycidyl ether;
the o-allylphenyl glycidyl ether is shown as a structural formula (5):
7. the resin composition according to claim 1, wherein the prepolymer of the maleimide resin is at least one of an allyl compound-modified prepolymer, an aromatic amine compound-modified prepolymer, an aliphatic amine compound-modified prepolymer, an amino silicone resin-modified prepolymer, a cyanate ester-modified prepolymer, or a benzoxazine-modified prepolymer.
8. A resin composition according to claim 1, further comprising an inorganic filler in an amount of 30 to 200 parts.
9. A resin composition according to claim 1, comprising: 100 parts of maleimide resin and prepolymer thereof, 10-100 parts of double bond-containing polyphenyl ether resin, 10-100 parts of hydroxyl-containing polyphenyl ether resin and a crosslinking agent: 5-80 parts by weight of epoxy resin and 1-70 parts by weight of a resin;
or comprises: 100 parts of maleimide resin and prepolymer thereof, 10-100 parts of double bond-containing polyphenyl ether resin, 10-100 parts of hydroxyl-containing polyphenyl ether resin and a crosslinking agent: 5-80 parts of cyanate ester and 1-50 parts of ethylene oxide;
or comprises: 100 parts of maleimide resin and prepolymer thereof, 10-100 parts of double bond-containing polyphenyl ether resin, 10-100 parts of hydroxyl-containing polyphenyl ether resin and a crosslinking agent: 5-80 parts of epoxy resin, 1-50 parts of phenolic resin and 1-20 parts of phenolic resin;
or comprises: 100 parts of maleimide resin and prepolymer thereof, 10-100 parts of double bond-containing polyphenyl ether resin, 10-100 parts of hydroxyl-containing polyphenyl ether resin and a crosslinking agent: 5-80 parts of epoxy resin, 1-70 parts of benzoxazine resin and 1-40 parts of benzoxazine resin.
10. Use of a resin composition characterized in that: use of the resin composition according to any one of claims 1 to 9 in cured sheets, laminates, insulating sheets, insulating films, circuit substrates and electrical devices.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202311560494.4A CN117417637A (en) | 2023-11-22 | 2023-11-22 | Resin composition and application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202311560494.4A CN117417637A (en) | 2023-11-22 | 2023-11-22 | Resin composition and application thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
CN117417637A true CN117417637A (en) | 2024-01-19 |
Family
ID=89524878
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202311560494.4A Pending CN117417637A (en) | 2023-11-22 | 2023-11-22 | Resin composition and application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN117417637A (en) |
-
2023
- 2023-11-22 CN CN202311560494.4A patent/CN117417637A/en active Pending
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN108219371B (en) | Epoxy resin composition, prepreg, laminate, and printed wiring board | |
CN112080102A (en) | Resin composition, prepreg, insulating film, metal-clad laminate, and printed wiring board provided with same | |
CN115850710B (en) | Modified bismaleimide prepolymer, resin composition and application of resin composition | |
TWI804796B (en) | A kind of modified maleimide compound and its preparation method and application | |
CN116003687B (en) | Maleimide resin prepolymer, preparation method thereof, resin composition and application | |
CN114957156A (en) | Compound containing benzoxazine structure, resin composition, prepreg and electric copper clad laminate, and preparation method and application thereof | |
CN115433330A (en) | Modified bismaleimide prepolymer, resin composition and application of resin composition | |
CN109971175B (en) | Modified maleimide resin composition, prepreg and laminated board prepared from same | |
CN116239777A (en) | Modified bismaleimide prepolymer, resin composition and application of resin composition | |
CN116120560B (en) | Preparation method of modified bismaleimide prepolymer, resin composition and application of resin composition | |
CN111849122B (en) | Resin composition and application thereof | |
CN108219134B (en) | Prepolymer and resin composition of modified composite bismaleimide resin, and prepreg and laminated board manufactured by using prepolymer and resin composition | |
CN114149659B (en) | Resin composition and use thereof | |
CN117417637A (en) | Resin composition and application thereof | |
KR20200055795A (en) | Epoxy resin composition, prepreg, laminated board and printed circuit board | |
CN116970169B (en) | Amine compound modified maleimide prepolymer, resin composition and application thereof | |
CN117447842A (en) | Maleimide resin composition and application thereof | |
CN114230794B (en) | Modified bismaleimide prepolymer, resin composition and application | |
CN116004007B (en) | Thermosetting resin composition and application thereof | |
CN115819766B (en) | Modified maleimide prepolymer, resin composition and application of resin composition | |
CN115819765B (en) | Epoxy compound modified maleimide prepolymer, resin composition and application of resin composition | |
CN115449039B (en) | Modified bismaleimide prepolymer, resin composition and application of resin composition | |
CN114262437B (en) | Modified bismaleimide prepolymer, resin composition thereof, prepreg, laminated board and metal foil laminated board | |
CN111849123B (en) | Epoxy resin composition and application thereof | |
CN116425937A (en) | Resin composition and application thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination |