CN114316567B - Resin composition, prepreg and application - Google Patents
Resin composition, prepreg and application Download PDFInfo
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- CN114316567B CN114316567B CN202111670701.2A CN202111670701A CN114316567B CN 114316567 B CN114316567 B CN 114316567B CN 202111670701 A CN202111670701 A CN 202111670701A CN 114316567 B CN114316567 B CN 114316567B
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- 239000011342 resin composition Substances 0.000 title claims abstract description 43
- 239000011347 resin Substances 0.000 claims abstract description 69
- 229920005989 resin Polymers 0.000 claims abstract description 68
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 claims abstract description 21
- 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 claims abstract description 15
- 229920003192 poly(bis maleimide) Polymers 0.000 claims abstract description 15
- 229920013638 modified polyphenyl ether Polymers 0.000 claims abstract description 10
- 239000011256 inorganic filler Substances 0.000 claims abstract description 9
- 229910003475 inorganic filler Inorganic materials 0.000 claims abstract description 9
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 7
- -1 3-methylcyclohexyl Chemical group 0.000 claims description 27
- 239000000463 material Substances 0.000 claims description 16
- 239000000835 fiber Substances 0.000 claims description 15
- 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 9
- 239000003063 flame retardant Substances 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 8
- 239000003365 glass fiber Substances 0.000 claims description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 6
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 6
- 108091081474 miR-5000 stem-loop Proteins 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- BZQKBFHEWDPQHD-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-[2-(2,3,4,5,6-pentabromophenyl)ethyl]benzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1CCC1=C(Br)C(Br)=C(Br)C(Br)=C1Br BZQKBFHEWDPQHD-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- LLVVSBBXENOOQY-UHFFFAOYSA-N 1,2,3,4,5-pentabromobenzene Chemical compound BrC1=CC(Br)=C(Br)C(Br)=C1Br LLVVSBBXENOOQY-UHFFFAOYSA-N 0.000 claims description 3
- DEKVAWHRMRNKMI-UHFFFAOYSA-N 1,2-bis(tert-butylperoxy)-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(OOC(C)(C)C)=C1OOC(C)(C)C DEKVAWHRMRNKMI-UHFFFAOYSA-N 0.000 claims description 3
- ODBCKCWTWALFKM-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhex-3-yne Chemical compound CC(C)(C)OOC(C)(C)C#CC(C)(C)OOC(C)(C)C ODBCKCWTWALFKM-UHFFFAOYSA-N 0.000 claims description 3
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 claims description 3
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 3
- BQARUDWASOOSRH-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-yl hydrogen carbonate Chemical compound CC(C)(C)OOC(C)(C)OC(O)=O BQARUDWASOOSRH-UHFFFAOYSA-N 0.000 claims description 3
- DYIZJUDNMOIZQO-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-[2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione Chemical compound O=C1C(C(=C(Br)C(Br)=C2Br)Br)=C2C(=O)N1CCN1C(=O)C2=C(Br)C(Br)=C(Br)C(Br)=C2C1=O DYIZJUDNMOIZQO-UHFFFAOYSA-N 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- 239000004677 Nylon Substances 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 239000004642 Polyimide Substances 0.000 claims description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- OJMOMXZKOWKUTA-UHFFFAOYSA-N aluminum;borate Chemical compound [Al+3].[O-]B([O-])[O-] OJMOMXZKOWKUTA-UHFFFAOYSA-N 0.000 claims description 3
- 229920006231 aramid fiber Polymers 0.000 claims description 3
- 239000010425 asbestos Substances 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 3
- 239000004917 carbon fiber Substances 0.000 claims description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 claims description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 3
- 239000000347 magnesium hydroxide Substances 0.000 claims description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 3
- 239000010445 mica Substances 0.000 claims description 3
- 229910052618 mica group Inorganic materials 0.000 claims description 3
- 229920001778 nylon Polymers 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 229920001721 polyimide Polymers 0.000 claims description 3
- 229910052895 riebeckite Inorganic materials 0.000 claims description 3
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 3
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 3
- 239000000454 talc Substances 0.000 claims description 3
- 229910052623 talc Inorganic materials 0.000 claims description 3
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 claims description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 239000004760 aramid Substances 0.000 claims 1
- 210000000538 tail Anatomy 0.000 claims 1
- 229920001955 polyphenylene ether Polymers 0.000 abstract description 17
- 239000002994 raw material Substances 0.000 abstract description 6
- 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 abstract description 5
- 238000013329 compounding Methods 0.000 abstract description 3
- 230000015556 catabolic process Effects 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 11
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 230000009477 glass transition Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000004744 fabric Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000032683 aging Effects 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YNSSPVZNXLACMW-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)-3-ethyl-5-methylphenyl]methyl]-2-ethyl-6-methylphenyl]pyrrole-2,5-dione Chemical compound C=1C(C)=C(N2C(C=CC2=O)=O)C(CC)=CC=1CC(C=C1CC)=CC(C)=C1N1C(=O)C=CC1=O YNSSPVZNXLACMW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 239000011889 copper foil Substances 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- BKJGGRPIMFLKFK-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC=CC=C1.C1(C=CC(N1)=O)=O.C1(C=CC(N1)=O)=O Chemical compound C1(=CC=CC=C1)C1=CC=CC=C1.C1(C=CC(N1)=O)=O.C1(C=CC(N1)=O)=O BKJGGRPIMFLKFK-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 238000004806 packaging method and process Methods 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- 229920002725 thermoplastic elastomer Polymers 0.000 description 2
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- PMAAOHONJPSASX-UHFFFAOYSA-N 2-butylperoxypropan-2-ylbenzene Chemical compound CCCCOOC(C)(C)C1=CC=CC=C1 PMAAOHONJPSASX-UHFFFAOYSA-N 0.000 description 1
- FWWXYLGCHHIKNY-UHFFFAOYSA-N 2-ethoxyethyl prop-2-enoate Chemical compound CCOCCOC(=O)C=C FWWXYLGCHHIKNY-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-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
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 108091063785 miR-3000 stem-loop Proteins 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
The invention relates to a resin composition, a prepreg and application, wherein the resin composition comprises the following components in parts by weight: 50-150 parts of modified polyphenyl ether resin, 40-150 parts of first resin, 0.5-140 parts of auxiliary agent and 50-180 parts of inorganic filler; wherein the structural formula of the modified polyphenyl ether resin is (1-1), the number average molecular weight is 800-6000,
Description
Technical Field
The invention relates to the field of high polymer materials, in particular to a resin composition, a prepreg and application.
Background
In recent years, with the increase in information processing amount, mounting technologies such as higher integration of mounted semiconductor devices, higher density of wiring, and multilayering have been rapidly developed for various electronic devices. In order to increase the transmission speed of signals and reduce the loss during signal transmission, the dielectric constant and dielectric loss tangent of the base materials used for forming wiring boards and the like used in various electronic devices are low.
Conventionally, in order to reduce the dielectric constant and dielectric loss tangent, a thermoplastic elastomer having an unsaturated bond in the structure is used as a raw material of a resin composition in a laminate or a wiring board, but the unsaturated bond in the thermoplastic elastomer cannot be completely initiated, which causes the wiring board or laminate containing the resin composition to continue to react at a high temperature during use, thereby causing deterioration of dielectric characteristics thereof.
Disclosure of Invention
Based on this, the main object of the present invention is to provide a resin composition with high glass transition temperature, small dielectric loss and high heat resistance, and a prepreg and application.
The invention provides a resin composition which comprises the following components in parts by weight:
wherein the structural formula of the modified polyphenyl ether resin is (1-1), M and N are positive integers, M+N=50, the number average molecular weight of the modified polyphenyl ether resin is 800-6000, R is cyclopentyl, cyclohexyl, cycloheptyl, 3-methylcyclohexyl, 3-methylcycloheptyl, 3, 5-dimethylcyclohexyl, methylethyl, methylpropyl, ethylpropyl, methylbutyl or ethylbutyl;
the first resin is at least one selected from triallyl isocyanurate, 2' -diallyl bisphenol A, styrene-butadiene-styrene block copolymer and bismaleimide resin.
In one embodiment, the number average molecular weight of the styrene-butadiene-styrene block copolymer is 1000-20000, the styrene content in the styrene-butadiene-styrene block copolymer is 5-90%, and the butadiene content is 5-90%.
In one embodiment, the bismaleimide resin is selected from at least one of biphenyl type bismaleimide resin, polyphenylenemaleimide, and bis (3-ethyl-5-methyl-4-maleimidophenyl) methane.
In one embodiment, the inorganic filler is selected from at least one of silica, alumina, titania, mica, aluminum hydroxide, magnesium hydroxide, talc, aluminum borate, barium sulfate, and calcium carbonate.
In one embodiment, the auxiliary agent includes 0.1 to 15 parts of an initiator and 20 to 80 parts of a flame retardant in the resin composition.
In one embodiment, the flame retardant is selected from at least one of ethane-1, 2-bis (pentabromobenzene), ethylene bis-tetrabromophthalimide, decabromodiphenyl ether, decabromodiphenyl ethane, and tetradecbromodiphenoxybenzene.
In one embodiment, the initiator is selected from at least one of bis-t-butylperoxyisopropyl benzene, dicumyl peroxide, 2, 5-dimethyl-2, 5-di (t-butylperoxy) hexane, di-t-butyl peroxide, 2, 5-dimethyl-2, 5-di (t-butylperoxy) -3-hexyne, benzoyl peroxide, tetrachlorobenzoquinone, t-butylperoxyisopropyl monocarbonate, and azobisisobutyronitrile.
The invention further provides a prepreg which comprises a base material and a resin material loaded on the base material, wherein the resin material is the resin composition.
In one embodiment, the substrate is selected from at least one of glass fiber, carbon fiber, silicon carbide fiber, asbestos fiber, nylon, polyethylene fiber, aramid fiber, polyimide fiber, polyester fiber, and cotton fiber.
Furthermore, the invention also provides application of the prepreg in preparation of a laminated board, a copper-clad plate or a wiring board.
The resin composition is obtained by compounding a modified polyphenylene ether resin and a first resin containing an unsaturated double bond, wherein the modified polyphenylene ether resin sufficiently induces a double bond structure contained in the first resin and effectively crosslinks resin raw materials, and further, the raw materials are compounded with an auxiliary agent and an inorganic filler to obtain a resin composition excellent in dielectric characteristics and suppressing thermal deterioration of dielectric characteristics. The prepreg prepared by the resin composition has high glass transition temperature and small dielectric loss, and can be widely used in vehicle millimeter wave radar and 5G base station antennas.
Detailed Description
The present invention will be described more fully hereinafter in order to facilitate an understanding of the present invention. Preferred embodiments of the present invention are presented. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Furthermore, the terms "first," "second," and the like, are used for descriptive purposes only and are not to be construed as indicating or implying a relative importance or implicitly indicating the number of technical features indicated. Thus, a feature defining "a first" or "a second" may explicitly or implicitly include at least one such feature. In the description of the invention, the meaning of "plurality" means at least two, for example, two, three, etc., unless specifically defined otherwise. In the description of the present invention, the meaning of "several" means at least one, such as one, two, etc., unless specifically defined otherwise.
The words "preferably," "more preferably," and the like in the present invention refer to embodiments of the invention that may provide certain benefits in some instances. However, other embodiments may be preferred under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, nor is it intended to exclude other embodiments from the scope of the invention.
When a range of values is disclosed herein, the range is considered to be continuous and includes both the minimum and maximum values for the range, as well as each value between such minimum and maximum values. Further, when a range refers to an integer, each integer between the minimum and maximum values of the range is included. Further, when multiple range description features or characteristics are provided, the ranges may be combined. In other words, unless otherwise indicated, all ranges disclosed herein are to be understood to include any and all subranges subsumed therein.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and/or" as used herein includes any and all combinations of one or more of the associated listed items.
The invention provides a resin composition which comprises the following components in parts by weight:
wherein the structural formula of the modified polyphenyl ether resin is (1-1), M and N are positive integers, M+N=50, the number average molecular weight of the modified polyphenyl ether resin is 800-6000, R is cyclopentyl, cyclohexyl, cycloheptyl, 3-methylcyclohexyl, 3-methylcycloheptyl, 3, 5-dimethylcyclohexyl, methylethyl, methylpropyl, ethylpropyl, methylbutyl or ethylbutyl;
preferably, the modified polyphenylene ether resin has a number average molecular weight of 1000 to 3000.
Specifically, the modified polyphenylene ether resin is methacrylic acid modified polyphenylene ether resin, and is manufactured by Sabic company, and has the brand of SA9000 and the number average molecular weight of 2300.
It is to be understood that the number average molecular weight may be any value obtained by measuring by a usual molecular weight measurement method, and may be, but is not limited to, a value obtained by Gel Permeation Chromatography (GPC).
Further, the first resin is selected from at least one of triallyl isocyanurate, 2' -diallyl bisphenol a, styrene-butadiene-styrene block copolymer, and bismaleimide resin.
In a specific example, the number average molecular weight of the styrene-butadiene-styrene block copolymer is 1000 to 20000, the styrene content in the styrene-butadiene-styrene block copolymer is 5 to 90%, and the butadiene content is 5 to 90%.
Preferably, the number average molecular weight of the styrene-butadiene-styrene block copolymer is 2000-6000, the content of styrene in the styrene-butadiene-styrene block copolymer is 10% -40%, and the content of butadiene is 60% -90%.
Further, the proportion of 1, 2-vinyl groups in the styrene-butadiene-styrene block copolymer is 25% to 95%, and the proportion of intramolecular c=c is 5% to 55%.
It will be appreciated that the structural formula of the styrene-butadiene-styrene block copolymer is as follows:
in a specific example, the bismaleimide resin is selected from at least one of biphenyl-type bismaleimide resin, polyphenylenemaleimide, and bis (3-ethyl-5-methyl-4-maleimidophenyl) methane.
Preferably, the bismaleimide resin has the preferred structural formula:
and +.>At least one compound of (a) and (b).
Preferably, the firstThe resin is styrene-butadiene-styrene block copolymer and modified biphenyl type bismaleimide resinThe weight ratio of the two is (1-3) 1-3.
Further, the relative molecular mass of the styrene-butadiene-styrene block copolymer is 4000 to 5000.
In a specific example, the inorganic filler is selected from at least one of silica, alumina, titanium oxide, mica, aluminum hydroxide, magnesium hydroxide, talc, aluminum borate, barium sulfate, and calcium carbonate.
In one specific example, the auxiliary agent includes 0.1 to 15 parts of an initiator and 20 to 80 parts of a flame retardant in the resin composition.
In a specific example, the flame retardant is selected from at least one of ethane-1, 2-bis (pentabromobenzene), ethylene bis tetrabromophthalimide, decabromodiphenyl ether, decabromodiphenyl ethane, and tetradecbromodiphenoxybenzene.
In a specific example, the initiator is selected from at least one of bis-t-butylperoxyisopropyl benzene, dicumyl peroxide, 2, 5-dimethyl-2, 5-di (t-butylperoxy) hexane, di-t-butyl peroxide, 2, 5-dimethyl-2, 5-di (t-butylperoxy) -3-hexyne, benzoyl peroxide, tetrachlorobenzoquinone, t-butylperoxyisopropyl monocarbonate, and azobisisobutyronitrile.
Preferably, the resin composition comprises the following components in parts by weight:
the resin composition is obtained by compounding a modified polyphenylene ether resin and a first resin containing an unsaturated double bond, wherein the modified polyphenylene ether resin sufficiently induces a double bond structure contained in the first resin and effectively crosslinks resin raw materials, and further, the raw materials are compounded with an auxiliary agent and an inorganic filler to obtain a resin composition excellent in dielectric characteristics and suppressing thermal deterioration of dielectric characteristics. The prepreg prepared by the resin composition has high glass transition temperature and small dielectric loss, and can be widely used in vehicle millimeter wave radar and 5G base station antennas.
It is understood that the above-mentioned method for preparing the resin composition includes the following steps S10 to S20.
Step S10: the modified polyphenylene ether resin is mixed with a solvent to prepare a premix.
It is understood that the above steps are to thoroughly mix the modified polyphenylene ether resin with the solvent, and the modified polyphenylene ether resin may be heated at a temperature of 40℃to 80 ℃.
Step S20: a first resin, an auxiliary agent, an inorganic filler, and a solvent are added to the premix.
Further, the solvent is at least one selected from methanol, ethanol, ethylene glycol monomethyl ether, acetone, butanone, methyl isobutyl ketone, cyclohexanone, toluene, xylene, 2-methoxyethyl acetate, 2-ethoxyethyl acrylate, ethyl acetate, dimethylformamide, dimethylacetamide and propylene glycol methyl ether. Preferably, the solvent is toluene.
The invention further provides a prepreg, which comprises a base material and a resin material loaded on the base material, wherein the resin material is the resin composition.
And loading the resin composition into a base material, and heating to semi-solidification to obtain the prepreg. It is to be understood that the method of loading the resin composition onto the substrate may be at least one of impregnation, roll, die, coating, bar coating, and spraying, but is not limited thereto.
The loading step may be repeated as many times as necessary, or a plurality of thermosetting resin compositions having different compositions and different solid contents may be repeatedly loaded to adjust the final desired composition and resin content.
It is understood that the heating condition is heating at 80 to 200 ℃ for 1 to 20 minutes, and a prepreg in a semi-cured state, i.e., a prepreg, can be obtained.
The heating condition is preferably that the heating temperature is 110-190 ℃ and the heating time is 2-10 min.
In a specific example, the substrate is selected from at least one of glass fiber, carbon fiber, silicon carbide fiber, asbestos fiber, nylon, polyethylene fiber, aramid fiber, polyimide fiber, polyester fiber, and cotton fiber.
The base material is preferably a glass fiber cloth, and the type of glass fiber cloth is not limited to E, NE, D, S or T-type, and a laminate excellent in mechanical strength can be obtained, and particularly preferably a glass cloth subjected to a flattening treatment. As the flattening process, the yarn may be compressed into a flattening process by continuously pressing the glass fiber cloth with a press roller at an appropriate pressure.
Furthermore, the invention also provides application of the prepreg in preparation of a laminated board, a copper-clad plate or a wiring board.
It will be appreciated that the method of making the laminate described above comprises the steps of: laminating at least one of the prepregs described above.
Further, the lamination process parameters were: at a temperature of 170 ℃ to 250 ℃ and a pressure of 10 kgf/cm 2 ～30kgf/cm 2 And hot-press forming for 60-120 min under the condition that the vacuum degree is less than 2 kPa.
It should be noted that, in the lamination, a metal-clad laminate may be obtained by laminating a plurality of prepregs, that is, one or both sides of the laminate, with metal-clad copper foil.
The thickness of the metal copper foil is 3-70 μm.
It will be appreciated that the laminate has a high glass transition temperature and extremely low dielectric properties and can be widely used in vehicle-mounted millimeter wave radar and 5G base station antennas.
Specific examples are provided below to illustrate the resin composition of the present invention and the method for preparing the same in further detail. In the following examples, all materials are commercially available unless otherwise specified.
Wherein, modified polyphenylene ether resin: SA9000, a methacrylic acid-modified polyphenylene ether resin, manufactured by Sabic company; OPE-1200-2st, styrene-modified polyphenylene ether resin, mitsubishi company.
Triallyl isocyanurate: TAIC, manufactured by Japanese chemical Co., ltd.
Styrene-butadiene-styrene block copolymer: r181, gram Lei Weili company; r100, gram Lei Weili company; nisso-SBS manufactured by Caesada.
| Single product | Manufacturer' s | Mn | Styrene content | Butadiene content | 1, 2-vinyl ratio |
| R181 | Gram Lei Weili | 3200 | 28％ | 72％ | 30％ |
| R100 | Gram Lei Weili | 4500 | 23％ | 77％ | 70％ |
| Nisso-SBS | Cao Da | 4585 | 20％ | 80％ | 90％ |
Bismaleimide resin: MIR-3000, biphenyl bismaleimide resin manufactured by Japanese chemical Co., ltd; MIR-5000, modified biphenyl bismaleimide resin manufactured by Japanese chemical Co., ltd; BMI-50P, polyphenylenemaleimide, manufactured by KI corporation, japan; BMI-70, bis (3-ethyl-5-methyl-4-maleimidophenyl) methane, manufactured by KI corporation, japan.
Flame retardant: 8010, decabromodiphenylethane, manufactured by yabao corporation.
Inorganic filler: SC2300-SVJ, double bond treated spherical silica manufactured by Admatechs.
And (3) an initiator: PERBUTYL P,1, 3-bis (butylperoxyisopropyl) benzene, manufactured by Japanese day oil Co.
The compositions of the resin compositions provided in the examples and comparative examples are as follows:
the preparation methods of the resin compositions of the above examples and comparative examples are as follows:
firstly, mixing the modified polyphenyl ether resin with toluene serving as a solvent, heating the premix to 60 ℃ and fully stirring to fully dissolve the modified polyphenyl ether resin in the toluene, thereby obtaining a toluene solution with a solid content of 50% in mass ratio. The first resin was then added thereto in proportion and stirred for 2 hours to be sufficiently dissolved. Finally, a flame retardant, an inorganic filler, an initiator and an appropriate amount of toluene are further added, and sufficiently dispersed by a bead mill, thereby obtaining a resin composition.
The preparation method of the prepreg carrying the resin compositions of the above examples and comparative examples is as follows:
the resin compositions prepared in each of examples and comparative examples were immersed in glass fiber cloth (2116 cloth produced by macro and company), and dried by heating at 150℃for about 3 minutes, to prepare prepregs. At this time, the solid content of the resin composition may be adjusted to obtain a prepreg having a mass ratio of 50%.
The preparation method of the copper-clad plate comprises the following steps:
8 prepregs corresponding to each example and comparative example were stacked, and 35um copper foil was placed on both sides, and the temperature was 200℃and the pressure was 25kgf/cm 2 And (3) heating, pressurizing and pressing for 2 hours, thereby obtaining the copper-clad plate with the thickness of about 0.9 mm.
Performance testing
1. Peel strength: the test method is carried out according to IPC-TM-650.2.4.8 by using a universal tensile machine.
2. Glass transition temperature (Tg): glass transition temperature (Tg) was measured using a dynamic mechanical analyzer (dynamic mechanical analyzer, DMA) (DMA 850 manufactured by TA Instruments) at a heating rate of 3 ℃/min. The glass transition temperature test specification uses methods of electronic circuit interconnect and packaging society (TheInstitute for Interconnecting and Packaging Electronic Circuits, IPC) IPC-TM-650.4.25C and 24C.
3. Dielectric constant and dielectric loss measurements: the dielectric constants (dielectric constant, dk) and dielectric losses (dissipation factor, df) were measured at an operating frequency of 10 megahertz (GHz) according to the IPC-TM-650.5.5.13 specification by a network analyzer of Agilent company model E5071C.
4. Solder resistance and heat resistance test at 288 ℃: immersing the test piece steamed for 2 hours by a PCT pressure cooker in a 288 ℃ soldering tin furnace for 6 minutes, and recording whether the test piece explodes.
5. Thermal expansion coefficient test and Z-axis expansion rate: the thermal expansion coefficient and the expansion rate of the sample in the Z axis direction are measured by a thermal expansion analyzer of TA instrument model TA Q800, wherein the measurement temperature is 50-260 ℃, the heating rate is 10 ℃/min.
6. Flame retardant test: referring to UL-94 specifications, the self-extinguishing time after burning of the samples was tested using a bunsen burner, methane gas and a marform, and the rating was determined based on this time.
The performance of the copper-clad plate provided by the above examples and comparative examples is as follows:
the performance of the copper-clad plate provided by the above examples and comparative examples can be seen as follows: comparative example 1 is compared with example 1, and mainly shows that the electrical property aging rate of the methacrylic acid-modified polyphenylene ether resin SA9000 is better than OPE-1200-2st in the modified polyphenylene ether resin. Comparative example 2 is compared with example 6 and mainly shows that the electrical property aging rate of the styrene-butadiene-styrene block copolymer R181 is inferior to that of the bismaleimide resin MIR-5000, and the smaller the c=c ratio in the structure of the styrene-butadiene-styrene block copolymer is, the smaller the dielectric property aging rate is. Comparative example 3 is compared with example 11 and mainly shows that in the bismaleimide resin, the electrical property aging rate of MIR-5000 is better than that of BMI-50P. Comparative example 4 was compared with example 11 and mainly shows that in the bismaleimide resin, the electrical aging rate of MIR-5000 was better than that of BMI-3000.
The technical features of the foregoing embodiments may be arbitrarily combined, and for brevity, all of the possible combinations of the technical features of the foregoing embodiments are not described, however, all of the combinations of the technical features should be considered as being within the scope of the disclosure.
The above examples merely represent a few embodiments of the present invention, which facilitate a specific and detailed understanding of the technical solutions of the present invention, but are not to be construed as limiting the scope of the invention. It should be noted that it will be apparent to those skilled in the art that several variations and modifications can be made without departing from the spirit of the invention, which are all within the scope of the invention. It should be understood that those skilled in the art, based on the technical solutions provided by the present invention, can obtain technical solutions through logical analysis, reasoning or limited experiments, all fall within the protection scope of the appended claims. The scope of the patent of the invention should therefore be determined with reference to the appended claims, which are to be construed as in accordance with the doctrines of claim interpretation.
Claims (10)
1. The resin composition is characterized by comprising the following components in parts by weight:
wherein the structural formula of the modified polyphenyl ether resin is (1-1), M and N are positive integers, M+N=50, the number average molecular weight of the modified polyphenyl ether resin is 800-6000, R is cyclopentyl, cyclohexyl, cycloheptyl, 3-methylcyclohexyl, 3-methylcycloheptyl, 3, 5-dimethylcyclohexyl, methylethyl, methylpropyl, ethylpropyl, methylbutyl or ethylbutyl;
the first resin is at least one selected from a styrene-butadiene-styrene block copolymer and a MIR-5000 bismaleimide resin of Japanese chemical Co., ltd, wherein the proportion of 1, 2-vinyl in the styrene-butadiene-styrene block copolymer is 90%.
2. The resin composition according to claim 1, wherein the first resin is a MIR-5000 bismaleimide resin of the Nisso-SBS styrene-butadiene-styrene block copolymer of Cauda company and the Japanese chemical Co., ltd in a weight ratio of (1-3).
3. The resin composition according to claim 1, wherein the inorganic filler is at least one selected from the group consisting of silica, alumina, titanium oxide, mica, aluminum hydroxide, magnesium hydroxide, talc, aluminum borate, barium sulfate, and calcium carbonate.
4. A resin composition according to any one of claims 1 to 3, wherein the auxiliary agent comprises 0.1 to 15 parts of an initiator and 20 to 80 parts of a flame retardant in the resin composition.
5. The resin composition according to claim 4, which comprises the following components in parts by weight:
6. the resin composition of claim 4, wherein the flame retardant is selected from at least one of ethane-1, 2-bis (pentabromobenzene), ethylene bis-tetrabromophthalimide, decabromodiphenyl ether, decabromodiphenyl ethane, and tetradecbromodiphenoxybenzene.
7. The resin composition of claim 4, wherein the initiator is at least one selected from the group consisting of bis-t-butylperoxyisopropyl benzene, dicumyl peroxide, 2, 5-dimethyl-2, 5-di (t-butylperoxy) hexane, di-t-butyl peroxide, 2, 5-dimethyl-2, 5-di (t-butylperoxy) -3-hexyne, benzoyl peroxide, tetrachlorobenzoquinone, t-butylperoxyisopropyl monocarbonate, and azobisisobutyronitrile.
8. A prepreg comprising a base material and a resin material supported on the base material, wherein the resin material is the resin composition according to any one of claims 1 to 7.
9. The prepreg of claim 8, wherein the substrate is selected from at least one of glass fibers, carbon fibers, silicon carbide fibers, asbestos fibers, nylon, polyethylene fibers, aramid fibers, polyimide fibers, polyester fibers, and cotton fibers.
10. Use of the prepreg according to claim 8 or 9 for the preparation of laminates, copper-clad plates or wiring boards.
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| CN102807658A (en) * | 2012-08-09 | 2012-12-05 | 广东生益科技股份有限公司 | Polyphenyl ether resin composite and prepreg and copper clad laminate made of polyphenyl ether resin composite |
| CN112062914A (en) * | 2020-09-22 | 2020-12-11 | 常熟生益科技有限公司 | Resin composition, and prepreg and laminated board manufactured by using same |
| CN112724640A (en) * | 2020-12-25 | 2021-04-30 | 广东生益科技股份有限公司 | Thermosetting resin composition, prepreg using same and copper-clad laminate |
| CN113121999A (en) * | 2019-12-31 | 2021-07-16 | 广东生益科技股份有限公司 | Resin composition, and prepreg, laminated board and printed circuit board using same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102807658A (en) * | 2012-08-09 | 2012-12-05 | 广东生益科技股份有限公司 | Polyphenyl ether resin composite and prepreg and copper clad laminate made of polyphenyl ether resin composite |
| CN113121999A (en) * | 2019-12-31 | 2021-07-16 | 广东生益科技股份有限公司 | Resin composition, and prepreg, laminated board and printed circuit board using same |
| CN112062914A (en) * | 2020-09-22 | 2020-12-11 | 常熟生益科技有限公司 | Resin composition, and prepreg and laminated board manufactured by using same |
| CN112724640A (en) * | 2020-12-25 | 2021-04-30 | 广东生益科技股份有限公司 | Thermosetting resin composition, prepreg using same and copper-clad laminate |
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