CN117586599A - Resin composition and use of the same - Google Patents
Resin composition and use of the same Download PDFInfo
- Publication number
- CN117586599A CN117586599A CN202311661976.9A CN202311661976A CN117586599A CN 117586599 A CN117586599 A CN 117586599A CN 202311661976 A CN202311661976 A CN 202311661976A CN 117586599 A CN117586599 A CN 117586599A
- Authority
- CN
- China
- Prior art keywords
- resin
- resin composition
- weight
- maleimide resin
- modified maleimide
- 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
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- 239000011342 resin composition Substances 0.000 title claims abstract description 62
- 229920005989 resin Polymers 0.000 claims abstract description 144
- 239000011347 resin Substances 0.000 claims abstract description 144
- 229920001400 block copolymer Polymers 0.000 claims abstract description 40
- 150000003923 2,5-pyrrolediones Chemical class 0.000 claims abstract description 35
- 238000004132 cross linking Methods 0.000 claims abstract description 25
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 7
- -1 dicyclopentadienyl methacrylate Chemical compound 0.000 claims description 56
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 46
- 239000003822 epoxy resin Substances 0.000 claims description 46
- 229920000647 polyepoxide Polymers 0.000 claims description 46
- 239000000178 monomer Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 11
- 239000004643 cyanate ester Substances 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 229920001296 polysiloxane Polymers 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 5
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 claims description 5
- 229920001955 polyphenylene ether Polymers 0.000 claims description 5
- 239000013032 Hydrocarbon resin Substances 0.000 claims description 4
- 229920013822 aminosilicone Polymers 0.000 claims description 4
- 229920006270 hydrocarbon resin Polymers 0.000 claims description 4
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 3
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 3
- 150000002148 esters Chemical group 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 abstract description 22
- 125000004185 ester group Chemical group 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000004744 fabric Substances 0.000 description 36
- 239000003365 glass fiber Substances 0.000 description 29
- 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 27
- 239000003063 flame retardant Substances 0.000 description 23
- 239000006087 Silane Coupling Agent Substances 0.000 description 19
- 229910052751 metal Inorganic materials 0.000 description 18
- 239000002184 metal Substances 0.000 description 18
- 239000012779 reinforcing material Substances 0.000 description 16
- 239000003054 catalyst Substances 0.000 description 15
- 239000011888 foil Substances 0.000 description 15
- 239000003999 initiator Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 12
- 239000007822 coupling agent Substances 0.000 description 11
- 239000011256 inorganic filler Substances 0.000 description 11
- 229910003475 inorganic filler Inorganic materials 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 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 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000011574 phosphorus Substances 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 229920003192 poly(bis maleimide) Polymers 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 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 6
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 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
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 239000003292 glue Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000011889 copper foil Substances 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 150000003961 organosilicon compounds Chemical class 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 5
- 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 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 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 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- 239000005062 Polybutadiene Substances 0.000 description 4
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 4
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 239000012796 inorganic flame retardant Substances 0.000 description 4
- GLTDLAUASUFHNK-UHFFFAOYSA-N n-silylaniline Chemical compound [SiH3]NC1=CC=CC=C1 GLTDLAUASUFHNK-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000004843 novolac epoxy resin Substances 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 229920001195 polyisoprene Polymers 0.000 description 4
- 238000003825 pressing Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QRFDGBAUUBFCEQ-UHFFFAOYSA-N 1,1'-biphenyl cyanic acid Chemical compound OC#N.C1=CC=CC=C1C1=CC=CC=C1 QRFDGBAUUBFCEQ-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 3
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 150000004984 aromatic diamines Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000007731 hot pressing Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 108091063785 miR-3000 stem-loop Proteins 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 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 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- INZDTEICWPZYJM-UHFFFAOYSA-N 1-(chloromethyl)-4-[4-(chloromethyl)phenyl]benzene Chemical group C1=CC(CCl)=CC=C1C1=CC=C(CCl)C=C1 INZDTEICWPZYJM-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- QGSRBNGFFJZCQF-UHFFFAOYSA-N 2,3,3-trimethylbutan-2-yl hydrogen carbonate Chemical compound CC(C)(C)C(C)(C)OC(O)=O QGSRBNGFFJZCQF-UHFFFAOYSA-N 0.000 description 2
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- KMRIWYPVRWEWRG-UHFFFAOYSA-N 2-(6-oxobenzo[c][2,1]benzoxaphosphinin-6-yl)benzene-1,4-diol Chemical compound OC1=CC=C(O)C(P2(=O)C3=CC=CC=C3C3=CC=CC=C3O2)=C1 KMRIWYPVRWEWRG-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- XIRDTMSOGDWMOX-UHFFFAOYSA-N 3,4,5,6-tetrabromophthalic acid Chemical compound OC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(O)=O XIRDTMSOGDWMOX-UHFFFAOYSA-N 0.000 description 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- GXIPHHIBYMWSMN-UHFFFAOYSA-N 6-phenylbenzo[c][2,1]benzoxaphosphinine 6-oxide Chemical compound O1C2=CC=CC=C2C2=CC=CC=C2P1(=O)C1=CC=CC=C1 GXIPHHIBYMWSMN-UHFFFAOYSA-N 0.000 description 2
- 229910052582 BN Inorganic materials 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical class N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 229910002113 barium titanate Inorganic materials 0.000 description 2
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 2
- 150000007973 cyanuric acids Chemical class 0.000 description 2
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical group BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical group [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
- VOOLKNUJNPZAHE-UHFFFAOYSA-N formaldehyde;2-methylphenol Chemical compound O=C.CC1=CC=CC=C1O VOOLKNUJNPZAHE-UHFFFAOYSA-N 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 238000010030 laminating Methods 0.000 description 2
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 2
- 239000000347 magnesium hydroxide Substances 0.000 description 2
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- 229920002545 silicone oil Polymers 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 229920002379 silicone rubber Polymers 0.000 description 2
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 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 2
- RERMPCBBVZEPBS-UHFFFAOYSA-N tris(2,6-dimethylphenyl)phosphane Chemical compound CC1=CC=CC(C)=C1P(C=1C(=CC=CC=1C)C)C1=C(C)C=CC=C1C RERMPCBBVZEPBS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229930000257 animal secondary metabolite Natural products 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012776 electronic material Substances 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
- DATWNUNJGBZECY-UHFFFAOYSA-N formaldehyde;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol;phenol Chemical compound O=C.OC1=CC=CC=C1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 DATWNUNJGBZECY-UHFFFAOYSA-N 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 108091081474 miR-5000 stem-loop Proteins 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 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
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical class [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000000538 tail Anatomy 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/14—Layered products comprising a layer of metal next to a fibrous or filamentary layer
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/06—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the heating method
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/10—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by the pressing technique, e.g. using action of vacuum or fluid pressure
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B38/00—Ancillary operations in connection with laminating processes
- B32B38/08—Impregnating
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B38/00—Ancillary operations in connection with laminating processes
- B32B38/16—Drying; Softening; Cleaning
- B32B38/164—Drying
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/248—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using pre-treated fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L53/02—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers of vinyl-aromatic monomers and conjugated dienes
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- 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
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/036—Multilayers with layers of different types
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2250/00—Layers arrangement
- B32B2250/40—Symmetrical or sandwich layers, e.g. ABA, ABCBA, ABCCBA
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/02—Composition of the impregnated, bonded or embedded layer
- B32B2260/021—Fibrous or filamentary layer
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
- B32B2260/04—Impregnation, embedding, or binder material
- B32B2260/046—Synthetic resin
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/10—Inorganic fibres
- B32B2262/101—Glass fibres
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/30—Properties of the layers or laminate having particular thermal properties
- B32B2307/306—Resistant to heat
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2457/00—Electrical equipment
- B32B2457/08—PCBs, i.e. printed circuit boards
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2353/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
- C08J2353/02—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers of vinyl aromatic monomers and conjugated dienes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use 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 C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—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
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2447/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2453/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
- C08J2453/02—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers of vinyl aromatic monomers and conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2479/00—Characterised by the use 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 C08J2461/00 - C08J2477/00
- C08J2479/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
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- Materials Engineering (AREA)
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Abstract
The invention discloses a resin composition and application of the resin composition, wherein the resin composition comprises 10-100 parts by weight of maleimide resin or modified maleimide resin, 10-150 parts by weight of block copolymer and 1-50 parts by weight of crosslinking auxiliary agent; and the structural formula of the block copolymer is defined. Compared with the prior art, the invention can effectively reduce the dielectric constant and dielectric loss of the resin composition and effectively inhibit the problem of the decrease of heat resistance and peeling strength of a cured product by adding the segmented copolymer containing ester groups into the maleimide resin or the modified maleimide resin and controlling the content of the segmented copolymer and the modified maleimide resin, and can improve the compatibility between the segmented copolymer and the maleimide resin and the production process, so that the modified maleimide resin has high heat resistance, high modulus, low dielectric constant and dielectric loss, high peeling strength and excellent rheological property.
Description
Technical Field
The invention belongs to the technical field of electronic materials, and relates to a resin composition and application of the resin composition in prepregs, laminated boards, circuit substrates and electronic devices.
Background
In recent years, with the development of the electronic information industry, the information processing speed and throughput have been remarkably increased, and terminals, base stations, and the like typified by 5G communication have been required to have a faster signal transmission speed and lower signal loss, so that higher demands have been made on the performance, particularly the electrical performance, of laminates, and higher demands have been made on matrix resins.
The conventional matrix resin generally adopts bismaleimide resin, however, the curing product of the bismaleimide resin has the problem of poor dielectric property, and the application of the curing product in the field of high-frequency high-speed packaging substrates is limited. In order to solve the problem of poor dielectric properties of bismaleimide resins, polyphenylene ether resins are generally introduced into the bismaleimide resins in the prior art, so that the dielectric constant of the bismaleimide resin cured product is reduced to a certain extent, but the polyphenylene ether resins have the characteristics of thermoplastic resins, have poor compatibility with the bismaleimide resins, are difficult to obtain very homogeneous glue solution complexes, and have poor production process and rheological properties.
Disclosure of Invention
The application provides a resin composition, and a prepreg, a laminated board, a circuit substrate and an electronic device which are prepared by the resin composition, so as to solve the problems that the existing resin composition is poor in dielectric property and cannot have excellent heat resistance, high peel strength and excellent rheological property.
To achieve the above object, an embodiment of the present invention provides a resin composition comprising, by weight:
10-100 parts by weight of maleimide resin or modified maleimide resin;
10-150 parts by weight of a block copolymer;
1-50 parts by weight of a crosslinking auxiliary agent;
wherein the structural formula of the block copolymer is
PB isx and y are integers, x is more than or equal to 1, y is more than or equal to 1,
q is H, C-C20 straight-chain alkyl, C1-C20 branched-chain alkyl,
R is H, C-C10 straight-chain alkyl or C1-C10 branched-chain alkyl,
n, m and p are integers, n is more than or equal to 1, m is more than or equal to 0, and p is more than or equal to 1.
Preferably, at least one of the block copolymersQ in (2) is->
Preferably, in the block copolymer, at least one PB isAnd x: y is (1-30): (50-120).
Preferably, in the block copolymer, n: m: p is (30-100): (0-30): (10-55); more preferably, n: m: p is (50-90): (1-20): (20-55).
Preferably, in the block copolymer, R is H, methyl, ethyl or tert-butyl.
As an alternative, the crosslinking assistant is selected from at least one of triallyl isocyanate monomer, triallyl isocyanate monomer prepolymer, butadiene monomer, styrene monomer, pentadiene monomer, methacrylate monomer, dicyclopentadienyl methacrylate monomer, norbornene monomer, P' -divinyl-1, 2-diphenylethane, cyclopentadiene monomer.
As an alternative, the modified maleimide resin is at least one selected from the group consisting of allyl compound modified maleimide resins, aromatic diamine modified maleimide resins, monoaminophenol modified maleimide resins, aliphatic diamine modified maleimide resins, amino silicone modified maleimide resins, double bond silicone modified maleimide resins, cyanate ester modified maleimide resins, benzoxazine modified maleimide resins, mercapto modified maleimide resins, polyphenylene ether modified maleimide resins.
Preferably, the allyl compound adopted by the allyl compound modified maleimide resin is at least one of diallyl bisphenol A, diallyl bisphenol S and diallyl diphenyl ether.
Preferably, the aromatic diamine used in the aromatic diamine-modified maleimide resin is at least one of 4,4 '-diaminodiphenylmethane, 4' -diaminobiphenyl, 3 '-diaminodiphenylmethane, reactants of 4,4' -bis (chloromethyl) biphenyl and aniline, 4 '-diaminodiphenyl ether, and 4,4' -methylenebis (2-methyl-6-diethylaniline).
Preferably, the amino organosilicon modified maleimide resin adopts amino organosilicon with the structural formula of
Wherein R is 1 、R 2 、R 3 、R 4 Identical or different, each independently selected from C1-C5 alkyl, R 5 、R 6 The same or different are independently selected from C1-C6 alkylene, and n is an integer of 1-20.
Preferably, the monoaminophenol used in the monoaminophenol modified maleimide resin is para-aminophenol, ortho-aminophenol or meta-aminophenol.
Preferably, the aliphatic diamine compound used in the aliphatic diamine modified maleimide resin is a diamine compound of a polydiamine C36 or C3-C20.
Preferably, the double-bond organosilicon compound used in the double-bond organosilicon modified maleimide resin is an organosilicon compound containing a styryl group or a methacrylate group at the molecular terminal.
Preferably, the cyanate used in the cyanate ester modified maleimide resin is at least one of bisphenol A type cyanate, bisphenol F type cyanate, bisphenol E type cyanate, bisphenol M type cyanate, DCPD type cyanate, naphthalene type cyanate, phenolic type cyanate, and biphenyl type cyanate.
As an alternative, the maleimide resin is selected from at least one of the following structures:
wherein R is 1 Is methylene, ethylene or +.>R 2 Is hydrogen, methyl or ethyl, 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, 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 and m are integers of 1 to 10, respectively.
As a further improvement of an embodiment of the present invention, the resin composition further comprises 0.1 to 50 parts by weight of an ester group-free hydrocarbon resin.
Preferably, the hydrocarbon resin without ester groups is selected from at least one of polybutadiene, modified polybutadiene, polypentadiene, modified polypentadiene, polyisoprene, modified polyisoprene, polystyrene, butadiene-styrene copolymer, styrene-butadiene-styrene copolymer, hydrogenated diene-butadiene-styrene copolymer, maleated diene-butadiene-styrene copolymer, styrene-isoprene-styrene copolymer, styrene-butadiene-divinylbenzene copolymer, maleated styrene-butadiene copolymer, cyclopentadiene, modified cyclopentadiene, dicyclopentadiene, modified dicyclopentadiene, styrene-pentadiene copolymer, styrene-polypentadiene copolymer, butadiene-cyclopentadiene copolymer, ethylene-cyclopentadiene copolymer, norbornene polymer.
As a further improvement of an embodiment of the present invention, the resin composition further comprises, by weight:
1-30 parts by weight of epoxy resin;
and/or, 1-35 parts by weight of cyanate resin.
As an alternative, the epoxy resin is preferably at least one selected from bisphenol a type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol E type epoxy resin, phosphorus containing epoxy resin, o-cresol formaldehyde epoxy resin, bisphenol a novolac epoxy resin, phenol novolac epoxy resin, cresol novolac epoxy resin, triphenylmethane epoxy resin, tetraphenylethane epoxy resin, biphenyl type epoxy resin, naphthalene ring type epoxy resin, dicyclopentadiene type epoxy resin, isocyanate type epoxy resin, aralkyl novolac epoxy resin, alicyclic type epoxy resin, glycidylamine type epoxy resin, glycidylether type epoxy resin, glycidylester type epoxy resin.
Preferably, the cyanate resin contains at least one cyanate group in its molecular structure, which may be a monomer, a polymer, a prepolymer, or a combination thereof. The cyanate ester resin is more preferably a prepolymer, a combination of a prepolymer and a monomer, or a combination of a prepolymer and a polymer.
As an alternative, the cyanate resin is selected from at least one of bisphenol a type cyanate resin, bisphenol F type cyanate resin, bisphenol E type cyanate resin, bisphenol M type cyanate resin, DCPD type cyanate resin, naphthalene type cyanate resin, phenolic type cyanate resin, biphenyl cyanate resin.
As a further improvement of an embodiment of the present invention, the resin composition further comprises an inorganic filler; the inorganic filler is 30 to 250 parts by weight based on100 parts by weight of the total of the resin, the block copolymer and the crosslinking assistant.
As an alternative, the inorganic filler is preferably at least one selected from the group consisting of spherical silica, aluminum hydroxide, alumina, talc, aluminum nitride, boron nitride, silicon carbide, barium sulfate, barium titanate, strontium titanate, calcium carbonate, calcium silicate, mica, glass fiber powder, and more preferably spherical silica.
Preferably, the filler is subjected to surface treatment by using a silane coupling agent, wherein the silane coupling agent is at least one of an aminosilane coupling agent, a silane coupling agent containing carbon-carbon double bonds and an epoxy silane coupling agent.
More preferably, the filler is spherical silica surface-treated with an anilino silane coupling agent, wherein the anilino silane coupling agent has a structural formula:
wherein R is a C1-C6 linear alkylene group and X is methoxy or ethoxy.
As a further improvement of an embodiment of the present invention, the resin composition further includes an initiator; the initiator is 0.001 to 5 parts by weight based on100 parts by weight of the total of the resin, the block copolymer and the crosslinking assistant.
As an alternative, the initiator is selected from at least one of peroxide initiators and azo initiators.
Preferably, the peroxide initiator is selected from at least one of alpha, alpha' -di (tert-butyl-m-isopropyl peroxybenzene, 2, 5-dimethyl-2, 5-di (tert-butyl-peroxy) -3-hexyne, benzoyl peroxide, tert-butyl-isopropyl monocarbonate.
Preferably, the azo initiator is at least one selected from azobisisobutyronitrile, azoison Ding Qingji formamide, azobisisoheptonitrile, dimethyl azobisisobutyrate and the like.
As a further improvement of an embodiment of the present invention, the resin composition further includes a dispersant and a coupling agent; the dispersant is 0.001 to 5 parts by weight and the coupling agent is 0.001 to 10 parts by weight based on100 parts by weight of the total of the resin, the block copolymer and the crosslinking assistant.
As a further improvement of an embodiment of the present invention, the resin composition further includes a flame retardant; the flame retardant is 1 to 60 parts by weight based on100 parts by weight of the total of the resin, the block copolymer and the crosslinking assistant.
As an alternative, the flame retardant is at least one of a brominated flame retardant, a phosphorus flame retardant, a nitrogen flame retardant, a silicone flame retardant, an organometallic flame retardant, and an inorganic flame retardant.
As an alternative, the brominated flame retardant is selected from decabromodiphenyl ether, decabromodiphenyl ethane, brominated styrene, or tetrabromophthalic acid amide.
As an alternative, the phosphorus-based flame retardant is selected from inorganic phosphorus,Condensed phosphate compound, phosphoric acid compound, hypophosphorous acid compound, phosphorus oxide compound, 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO), 10- (2, 5-dihydroxyphenyl) -9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO-HQ), 10-phenyl-9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, tris (2, 6-dimethylphenyl) phosphorus,(m is an integer of 1 to 5),
Phosphazenes.
As an alternative, the nitrogen-based flame retardant is selected from triazine compounds, cyanuric acid compounds, isocyanic acid compounds, phenothiazine.
As an alternative, the silicone flame retardant is selected from silicone oils, silicone rubbers, silicone resins.
As an alternative, the organometallic flame retardant is selected from ferrocene, acetylacetonate metal complexes, organometallic carbonyls.
As an alternative, the inorganic flame retardant is selected from aluminum hydroxide, magnesium hydroxide, aluminum oxide, barium oxide.
As a further improvement of an embodiment of the present invention, the resin composition further includes a catalyst; the catalyst is 0.01 to 5 parts by weight based on100 parts by weight of the total of the resin, the block copolymer and the crosslinking assistant.
As an alternative, the catalyst is at least one of imidazole-type catalyst, pyridine-type catalyst and organic metal salt-type catalyst.
As an alternative, the catalyst is preferably at least one of 4-dimethylaminopyridine, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, modified imidazole and zinc octoate.
The invention also provides application of the resin composition in prepregs, laminated boards, circuit substrates and electronic devices, and the application is specifically described as follows:
the invention also provides a prepreg which comprises a reinforcing material and the resin composition; the resin composition is wrapped on the reinforcing material.
The preparation method of the prepreg comprises the following steps: dissolving the resin composition with a solvent to prepare a glue solution, coating the glue solution on the reinforcing material by an impregnation method, taking out the impregnated reinforcing material, and baking for 1-15 min at the temperature of 100-180 ℃; and drying to obtain the prepreg.
As an alternative, the solvent is at least one selected from the group consisting of acetone, butanone, methyl isobutyl ketone, N-dimethylformamide, N-dimethylacetamide, ethylene glycol methyl ether, propylene glycol methyl ether, benzene, toluene, xylene, and cyclohexane.
As an alternative, the reinforcing material is selected from at least one of natural fibers, organic synthetic fibers, organic fabrics, and inorganic fabrics.
Preferably, the reinforcing material is glass fiber cloth. The glass fiber cloth is preferably a split cloth or a flat cloth. More preferably, the glass fiber cloth is E glass fiber cloth, S glass fiber cloth, T glass fiber cloth, or Q glass fiber cloth.
In addition, when the reinforcing material is a glass fiber cloth, the glass fiber cloth is chemically treated in advance with a coupling agent to improve interface bonding between the resin composition and the glass fiber cloth. The coupling agent herein preferably employs an epoxy silane coupling agent or an amino silane coupling agent to provide good water resistance and heat resistance.
The invention also provides a laminated board which comprises a piece of the prepreg and a metal foil arranged on at least one side surface of the prepreg; or comprises a combination sheet formed by mutually overlapping a plurality of prepregs, and a metal foil arranged on at least one side surface of the combination sheet.
By adopting the technical scheme, the laminated board has the advantages of low thermal expansion coefficient, high glass transition temperature, low dielectric constant and dielectric loss value, and excellent processability.
The preparation method of the laminated board comprises the following steps: and coating metal foil on one side or two side surfaces of one prepreg, or laminating at least two prepregs to form a combined sheet, coating metal foil on one side or two side surfaces of the combined sheet, and performing hot press forming to obtain the metal foil laminated plate. Wherein, the pressing conditions of hot pressing are: the pressure is 0.2-2 MPa, the temperature is 150-250 ℃, and the pressing time is 2-4 h.
Preferably, the metal foil is selected from copper foil or aluminum foil. The thickness of the metal foil is 5 μm, 8 μm, 12 μm, 18 μm, 35 μm or 70 μm.
The invention also provides a circuit substrate which comprises at least one of the prepreg and the laminated board.
The invention also provides an electronic device, which comprises the circuit substrate.
Due to the application of the technical scheme, compared with the prior art, the invention has the following advantages:
the addition of the block copolymer containing ester groups to the maleimide resin or the modified maleimide resin and the control of the content of the block copolymer and the modified maleimide resin can effectively reduce the dielectric constant and dielectric loss of the resin composition and effectively inhibit the problems of heat resistance and peeling strength of a cured product, and the addition of the crosslinking auxiliary agent and the control of the content thereof can improve the compatibility between the block copolymer and the maleimide resin and the production process, so that the resin composition has high heat resistance, high modulus, low dielectric constant and dielectric loss, high peeling strength and excellent rheological property.
Detailed Description
The following examples are merely illustrative, not limiting, and are not intended to limit the scope of the present application.
An embodiment of the present invention provides a resin composition and the use of the resin composition in prepregs, laminates, circuit substrates and electronic devices.
The invention provides a resin composition, which comprises the following components in parts by weight:
10-100 parts by weight of maleimide resin or modified maleimide resin;
10-150 parts by weight of a block copolymer;
1-50 parts of cross-linking auxiliary agent.
Wherein the structural formula of the block copolymer is
PB isx and y are integers, x is more than or equal to 1, y is more than or equal to 1,
q is H, C-C20 straight-chain alkyl, C1-C20 branched-chain alkyl,* Represents the position where Q is attached to the O atom,
r is H, C-C10 straight-chain alkyl or C1-C10 branched-chain alkyl,
n, m and p are integers, n is more than or equal to 1, m is more than or equal to 0, and p is more than or equal to 1.
The addition of the block copolymer containing ester groups to the maleimide resin or the modified maleimide resin and the control of the content of the block copolymer and the modified maleimide resin can effectively reduce the dielectric constant and dielectric loss of the resin composition and effectively inhibit the problems of heat resistance and peeling strength of a cured product, and the addition of the crosslinking auxiliary agent and the control of the content thereof can improve the compatibility between the block copolymer and the maleimide resin and the production process, so that the resin composition has high heat resistance, high modulus, low dielectric constant and dielectric loss, high peeling strength and excellent rheological property.
Preferably, at least one of the block copolymersQ in (2) is->
When the alicyclic group is contained in the block copolymer, not only the dielectric properties can be further reduced and the decrease in heat resistance of the cured product can be effectively suppressed, but also the toughness of the cured product can be improved and the coefficient of thermal expansion can be reduced.
Preferably, in the block copolymer, at least one PB isx is an integer of 1 to 80, and y is an integer of 20 to 120.
Further preferably, x: y is (1-30): (50-120).
Preferably, in the block copolymer, n: m: p is (30-100): (0-30): (10-55); more preferably, n: m: p is (50-90): (1-20): (20-55).
Preferably, in the block copolymer, R is H, methyl, ethyl or tert-butyl.
Specifically, the block copolymer is selected from BM-1035 manufactured by Cauda.
Preferably, the crosslinking assistant is selected from at least one of triallyl isocyanate monomer (TAIC), triallyl isocyanate monomer prepolymer, butadiene monomer, styrene monomer, pentadiene monomer, methacrylate monomer, dicyclopentadienyl methacrylate monomer (DCP), norbornene monomer, P' -divinyl-1, 2-diphenylethane, cyclopentadiene monomer.
Specifically, the crosslinking auxiliary agent can be selected from TAIC manufactured by Yingchuang or Sigma Aldrich, T-500 manufactured by Jinyi chemical, and TAIC manufactured by Mitsubishi chemical TM A-DCP manufactured by Xinzhongcun chemical, DCP-A manufactured by Zoo chemical, ODV-XET manufactured by Xin Nile iron.
Preferably, the modified maleimide resin is at least one selected from the group consisting of an allyl compound modified maleimide resin, an aromatic diamine modified maleimide resin, a monoaminophenol modified maleimide resin, an aliphatic diamine modified maleimide resin, an amino silicone modified maleimide resin, a double bond silicone modified maleimide resin, a cyanate ester modified maleimide resin (BT resin), a benzoxazine modified maleimide resin, a mercapto modified maleimide resin, and a polyphenylene ether modified maleimide resin.
Further, the allyl compound adopted by the allyl compound modified maleimide resin is at least one of diallyl bisphenol A, diallyl bisphenol S and diallyl diphenyl ether.
Further, the aromatic diamine used in the aromatic diamine modified maleimide resin is at least one of 4,4 '-diaminodiphenyl methane, 4' -diaminodiphenyl, 3 '-diaminodiphenyl methane, reactants of 4,4' -bis (chloromethyl) diphenyl and aniline, 4 '-diaminodiphenyl ether and 4,4' -methylenebis (2-methyl-6-diethylaniline).
Further, the amino organosilicon modified maleimide resin adopts amino organosilicon with the structural formula of
Wherein R is 1 、R 2 、R 3 、R 4 Identical or different, each independently selected from C1-C5 alkyl, R 5 、R 6 The same or different are independently selected from C1-C6 alkylene, and n is an integer of 1-20.
Further, the monoaminophenol adopted by the monoaminophenol modified maleimide resin is para-aminophenol, ortho-aminophenol or meta-aminophenol.
Further, the aliphatic diamine compound adopted by the aliphatic diamine modified maleimide resin is a diamine compound of poly (C36) or C3-C20.
Further, the double-bond organosilicon compound adopted by the double-bond organosilicon modified maleimide resin is an organosilicon compound containing a styryl group or a methacrylate group at the molecular terminal.
Further, the cyanate used in the cyanate ester modified maleimide resin is at least one of bisphenol A type cyanate, bisphenol F type cyanate, bisphenol E type cyanate, bisphenol M type cyanate, DCPD type cyanate, naphthalene type cyanate, phenolic type cyanate and biphenyl cyanate.
The preparation method of the modified maleimide resin comprises the following steps: the maleimide resin and the modifier are uniformly mixed in an organic solvent and react for a certain time at a certain temperature to prepare the modified polyimide resin.
The reaction temperature is 50-150 ℃, the reaction time is 0.1-10 h, and the specific reaction temperature and reaction time are set according to the modifier.
The modifier is allyl compound, aromatic diamine, monoaminophenol, aliphatic diamine compound, amino organosilicon compound, double bond organosilicon compound, cyanate, benzoxazine, mercapto compound and polyphenyl ether.
Preferably, the maleimide resin is selected from at least one of the following structures:
wherein R is 1 Is methylene, ethylene or +.>R 2 Is hydrogen, methyl or ethyl, 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, 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 and m are integers of 1 to 10, respectively.
Specifically, the maleimide resin may be selected from 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 Daihou chemical company, BMI-70, BMI-80, MIR-3000 and MIR-5000 manufactured by Japanese chemical company, X9-450 and X9-470 manufactured by Japanese DIC, D936, D937, D939 and D950 manufactured by Sichuan Dong, respectively.
More preferably, the maleimide resin is BMI-2300 manufactured by Daikovia chemical Co., ltd., BMI-70 manufactured by Japanese KI chemical Co., ltd., BMI-80 manufactured by Japanese Kagaku chemical Co., ltd., MIR-3000 manufactured by Japanese Kagaku chemical Co., ltd.
Further, the resin composition further comprises, by weight: 0.1 to 50 parts by weight of hydrocarbon resin without ester groups.
The hydrocarbon-based resin having no ester group is preferably at least one selected from the group consisting of polybutadiene, modified polybutadiene, polypentadiene, modified polypentadiene, polyisoprene, modified polyisoprene, polystyrene, butadiene-styrene copolymer, styrene-butadiene-styrene copolymer, hydrogenated diene-butadiene-styrene copolymer, maleated diene-butadiene-styrene copolymer, styrene-isoprene-styrene copolymer, styrene-butadiene-divinylbenzene copolymer, maleated styrene-butadiene copolymer, cyclopentadiene, modified cyclopentadiene, dicyclopentadiene, modified dicyclopentadiene, styrene-pentadiene copolymer, styrene-polypentadiene copolymer, butadiene-cyclopentadiene copolymer, ethylene-cyclopentadiene copolymer, and norbornene polymer.
Further, the resin composition further comprises, by weight:
1-30 parts of epoxy resin;
and/or 1-35 parts by weight of a cyanate resin.
That is, in one embodiment, the resin composition further includes 1 to 30 parts by weight of an epoxy resin.
In another embodiment, the resin composition further includes 1 to 35 parts by weight of a cyanate resin.
In still another embodiment, the resin composition further includes 1 to 30 parts by weight of an epoxy resin, and 1 to 35 parts by weight of a cyanate resin.
The epoxy resin is preferably at least one selected from bisphenol a type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol E type epoxy resin, phosphorus containing epoxy resin, o-cresol formaldehyde epoxy resin, bisphenol a phenol formaldehyde epoxy resin, cresol formaldehyde epoxy resin, triphenylmethane epoxy resin, tetraphenylethane epoxy resin, biphenyl type epoxy resin, naphthalene ring type epoxy resin, dicyclopentadiene type epoxy resin, isocyanate type epoxy resin, aralkyl type phenol formaldehyde epoxy resin, alicyclic type epoxy resin, glycidol amine type epoxy resin, glycidol ether type epoxy resin, and glycidol ester type epoxy resin.
The cyanate ester resin contains at least one cyanate ester group in the molecular structure, and can be a monomer, a polymer, a prepolymer or a combination thereof. The cyanate resin is preferably a prepolymer, a combination of a prepolymer and a monomer, or a combination of a prepolymer and a polymer.
Preferably, the cyanate resin is at least one selected from bisphenol a type cyanate resin, bisphenol F type cyanate resin, bisphenol E type cyanate resin, bisphenol M type cyanate resin, DCPD type cyanate resin, naphthalene type cyanate resin, phenolic type cyanate resin, biphenyl cyanate resin.
Further, the resin composition further comprises an inorganic filler; the inorganic filler is 30 to 250 parts by weight based on100 parts by weight of the total of the resin, the block copolymer and the crosslinking assistant.
Wherein the resin is the general term for different kinds of resins in the resin composition. For example, when the resin composition includes a maleimide resin, a block copolymer, a crosslinking assistant and an inorganic filler, the inorganic filler is 30 to 250 parts by weight based on100 parts by weight of the total of the maleimide resin, the block copolymer and the crosslinking assistant. For another example, when the resin composition includes a maleimide resin, a block copolymer, a crosslinking assistant, an epoxy resin, and an inorganic filler, the inorganic filler is 30 to 250 parts by weight based on100 parts by weight of the total of the maleimide resin, the block copolymer, the crosslinking assistant, and the epoxy resin.
The inorganic filler is preferably at least one selected from spherical silica, aluminum hydroxide, alumina, talc, aluminum nitride, boron nitride, silicon carbide, barium sulfate, barium titanate, strontium titanate, calcium carbonate, calcium silicate, mica, and glass fiber powder, and more preferably spherical silica.
Further, the filler is subjected to surface treatment by using a silane coupling agent, wherein the silane coupling agent is at least one of an amino silane coupling agent, a silane coupling agent containing carbon-carbon double bonds and an epoxy silane coupling agent.
More preferably, the filler is spherical silica surface-treated with an anilino silane coupling agent, wherein the anilino silane coupling agent has a structural formula:
wherein R is a C1-C6 linear alkylene group and X is methoxy or ethoxy.
Further, the resin composition further includes an initiator; the initiator is 0.001 to 5 parts by weight based on100 parts by weight of the total of the resin, the block copolymer and the crosslinking assistant.
The initiator is at least one selected from peroxide initiator and azo initiator.
Preferably, the peroxide initiator is selected from at least one of alpha, alpha' -di (tert-butyl-m-isopropyl peroxybenzene, 2, 5-dimethyl-2, 5-di (tert-butyl-peroxy) -3-hexyne, benzoyl peroxide, tert-butyl-isopropyl monocarbonate.
Preferably, the azo initiator is at least one selected from azobisisobutyronitrile, azoison Ding Qingji formamide, azobisisoheptonitrile, dimethyl azobisisobutyrate and the like.
Further, the resin composition further comprises a dispersant and a coupling agent; the dispersant is 0.001 to 5 parts by weight and the coupling agent is 0.001 to 10 parts by weight based on100 parts by weight of the total of the resin, the block copolymer and the crosslinking assistant.
The dispersant is preferably BYK-161 and/or BYK-111 manufactured by Pick corporation; the coupling agent is preferably KBM-402, KBM-403, KBM-502, KBE-503, KBM-603, KBM-903, KBM-573, KBM-602, KBM-1003 from the chemical company.
Further, the resin composition further includes a flame retardant; the flame retardant is 1 to 60 parts by weight based on100 parts by weight of the total of the resin, the block copolymer and the crosslinking assistant.
Optionally, the flame retardant is at least one of a brominated flame retardant, a phosphorus flame retardant, a nitrogen flame retardant, an organosilicon flame retardant, an organic metal flame retardant and an inorganic flame retardant.
Optionally, the brominated flame retardant is selected from decabromodiphenyl ether, decabromodiphenyl ethane, brominated styrene, or tetrabromophthalic acid amide.
Optionally, the phosphorus-based flame retardant is selected from inorganic phosphorus, condensed phosphate compounds, phosphoric acid compounds, hypophosphorous acid compounds, phosphorus oxide compounds, 9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO), 10- (2, 5-dihydroxyphenyl) -9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO-HQ), 10-phenyl-9, 10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, tris (2, 6-dimethylphenyl) phosphorus,
(m is an integer of 1 to 5),>phosphazenes.
Optionally, the nitrogen-based flame retardant is selected from triazine compounds, cyanuric acid compounds, isocyanic acid compounds, phenothiazine.
Optionally, the silicone flame retardant is selected from silicone oil, silicone rubber, silicone resin.
Optionally, the organometallic flame retardant is selected from ferrocene, acetylacetonate metal complexes, and organometallic carbonyls.
As an alternative, the inorganic flame retardant is selected from aluminum hydroxide, magnesium hydroxide, aluminum oxide, barium oxide.
The flame retardant is preferably SPB-100, FP-300B or FP-390, PX-200, PX-201 or PX-202, OP-935 or OP-930, SAYTEX8010, HP-7010 or BT-93W, FRX OL3001 or OL5000, respectively.
Further, the resin composition further comprises a catalyst; the catalyst is 0.01 to 5 parts by weight based on100 parts by weight of the total of the resin, the block copolymer and the crosslinking assistant.
Optionally, the catalyst is at least one of imidazole catalyst, pyridine catalyst and organic metal salt catalyst.
The catalyst is preferably at least one of 4-dimethylaminopyridine, 2-methylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, modified imidazole and zinc octoate.
The invention also provides a prepreg which comprises a reinforcing material and the resin composition, wherein the resin composition is wrapped on the reinforcing material.
The preparation method of the prepreg comprises the following steps: dissolving the resin composition with a solvent to prepare a glue solution, coating the glue solution on the reinforcing material by an impregnation method, taking out the impregnated reinforcing material, and baking for 1-15 min at the temperature of 100-180 ℃; and drying to obtain the prepreg.
The solvent is at least one selected from acetone, butanone, methyl isobutyl ketone, N-dimethylformamide, N-dimethylacetamide, ethylene glycol methyl ether, propylene glycol methyl ether, benzene, toluene, xylene, and cyclohexane.
The reinforcing material may be at least one selected from natural fibers, organic synthetic fibers, organic fabrics, and inorganic fabrics, preferably glass fiber cloth, more preferably E glass fiber cloth, S glass fiber cloth, T glass fiber cloth, or Q glass fiber cloth. The glass fiber cloth is preferably a split cloth or a flat cloth.
In addition, when the reinforcing material is a glass fiber cloth, the glass fiber cloth is chemically treated in advance with a coupling agent to improve interface bonding between the resin composition and the glass fiber cloth. The coupling agent is preferably an epoxy silane coupling agent or an amino silane coupling agent so that the reinforcing material has good water resistance and heat resistance.
The invention also provides a laminated board, which comprises a metal foil and the prepreg; the metal foil is arranged on at least one side surface of the prepreg or the prepreg combination.
The laminate may be prepared by the following method: and coating metal foil on one side or two side surfaces of one prepreg, or laminating at least two prepregs to form a combined sheet, coating metal foil on one side or two side surfaces of the combined sheet, and performing hot press forming to obtain the metal foil laminated plate. Wherein, the pressing conditions of hot pressing are: the pressure is 0.2-2 MPa, the temperature is 150-250 ℃, and the pressing time is 2-4 h. The metal foil is selected from copper foil or aluminum foil, and has a thickness of 5 μm, 8 μm, 12 μm, 18 μm, 35 μm or 70 μm.
The invention also provides a circuit substrate which comprises at least one of the prepregs and the laminated boards.
The invention also provides an electronic device, which comprises the circuit substrate.
The technical solutions of the present application will be further described below with reference to specific synthesis examples, examples and comparative examples. Of course, these examples are only some, but not all, of the many variations encompassed by the present embodiments.
Synthesis example 1
The synthesis example discloses a preparation method of an allyl compound modified maleimide resin, which comprises the following steps:
100g of 4, 4-diphenylmethane bismaleimide resin and 50g of diallyl bisphenol A are added into a reaction bottle, stirred and mixed uniformly, and reacted for 60min at 130-150 ℃ to obtain allyl compound modified maleimide resin A.
Synthesis example 2
The synthesis example discloses a preparation method of amino organosilicon modified maleimide resin, which comprises the following steps:
to the reaction flask were added 500g of bismaleimide resin (MIR-3000 manufactured by Nippon chemical Co., ltd.), 50g of amino silicone resin (X-22-161A manufactured by Xinyue chemical Co., ltd.) and 500ml of propylene glycol methyl ether, and the mixture was reacted under reflux for 5 hours to obtain amino silicone-modified maleimide resin B.
Synthesis example 3
The synthesis example discloses a preparation method of cyanate modified maleimide resin, which comprises the following steps:
100g of bismaleimide resin (BMI-2300 produced by Dahe chemical Co., ltd.), 60g of cyanate resin and 40g of cyanate monomer were added to a reaction flask, and the mixture was melted at 130 to 170℃for 3 hours to obtain a cyanate-modified maleimide resin C.
Examples
The chemical components and the contents of the resin compositions of examples 1 to 6 and comparative examples 1 to 4 are shown in Table 1.
Wherein the maleimide resin is BMI-2300 prepared by large neutralization; the block copolymer A is BM-1035 of Caoda, its structural formula is structural formula (1) and Q isThe block copolymer B is butadiene-styrene copolymer, specifically Ricon100 made by gram Lei Weili is selected; the crosslinking aid was TAIC manufactured by Sigma Aldrich; the epoxy resin is biphenyl type epoxy resin, and NC3000H manufactured by chemical drugs is selected; the cyanate resin is bisphenol A type cyanate resin, and C01P0 manufactured by Tianzhui is selected; the initiator is alpha, alpha' -di (tertiary butyl peroxy m-isopropyl) benzene; the catalyst is 2-ethyl-4 methylimidazole prepared by four kingdoms; the inorganic filler is spherical silica subjected to surface treatment by an aminosilane coupling agent, and SC-2050MB manufactured by Admatechs is adopted.
The present embodiment also discloses a prepreg comprising a glass fiber cloth as a reinforcing material and a resin composition coated on the glass fiber cloth by a dipping method. Wherein the glass fiber cloth is a fiber opening cloth which is pretreated by adopting an epoxy silane coupling agent in advance.
Specifically, the resin compositions of examples 1 to 6 and comparative examples 1 to 4 were each diluted with N, N-dimethylacetamide to give a dope having a solid content of 60% by weight; and (3) pre-treating the T glass fiber cloth serving as a reinforcing material by adopting an epoxy silane coupling agent, immersing the T glass fiber cloth in the glue solution, taking out the T glass fiber cloth after immersing, placing the T glass fiber cloth in a blast drying oven at 160 ℃, and baking the T glass fiber cloth for 3-6 min to obtain the prepreg.
The embodiment also discloses a laminated board, which is prepared by the following method:
cutting the prepreg to 300X 300mm, respectively placing a piece of low-coarsening electrolytic copper foil with the thickness of 18 mu m at two sides of the prepreg, stacking to form a certain stacking structure, placing the stacking structure in a vacuum hot press, and hot-pressing for 4 hours under the conditions of the pressure of 1.5MPa and the temperature of 200 ℃ to obtain the copper-clad laminated board with the thickness of 1 mm.
The embodiment also discloses a circuit substrate, which comprises the prepreg, and is prepared by adopting a conventional preparation method in the prior art, and the description is omitted herein.
The copper-clad laminates obtained in examples 1 to 6 and comparative examples 1 to 4 were subjected to performance test, and the test results are shown in Table 2. The performance test method comprises the following steps:
(1) Glass transition temperature (Tg): the test was performed by the method specified by IPC-TM-6502.4.25 using the DMA (thermal mechanical analysis) method, with a heating rate of 10℃per minute.
(2) Coefficient of Thermal Expansion (CTE) in the X/Y axis: the temperature rise rate is 10 ℃/min and the test temperature range is 30-100 ℃ by adopting a TMA method and adopting an IPC-TM-650 method for measurement.
(3) Dk and Df: the dielectric constant Dk and the dielectric loss Df at 1GHz were measured according to IPC-TM-650.2.5.5.9 using the flat panel method.
(4) Peel Strength (PS): the laminate was tested for peel strength of the copper foil layer according to the "post thermal stress" test conditions in the IPC-TM-650.4.8 method.
(5) Plate thickness accuracy: and testing the thickness difference delta d of the middle part and the edge part of the test plate after the copper-clad plate is etched for 3 times, and calculating the average value.
TABLE 2
Referring to table 2, compared with the comparative example, the resin composition of the embodiment of the present invention further prepared a copper clad laminate, not only has excellent heat resistance and excellent rheological properties, lower dielectric constant and dielectric loss, but also has high modulus, and significantly improves the peel strength of the copper foil.
It should be understood that although the present disclosure describes embodiments, not every embodiment is provided with a separate embodiment, and that this description is for clarity only, and that the skilled artisan should recognize that the embodiments may be combined as appropriate to form other embodiments that will be understood by those skilled in the art.
The above detailed description is merely illustrative of possible embodiments of the present invention, which should not be construed as limiting the scope of the invention, and all equivalent embodiments or modifications that do not depart from the spirit of the invention are intended to be included in the scope of the invention.
Claims (10)
1. A resin composition comprising, by weight:
10-100 parts by weight of maleimide resin or modified maleimide resin;
10-150 parts by weight of a block copolymer;
1-50 parts by weight of a crosslinking auxiliary agent;
wherein the structural formula of the block copolymer is
PB isx and y are integers, x is more than or equal to 1, y is more than or equal to 1,
q is H, C-C20 straight-chain alkyl, C1-C20 branched-chain alkyl,
R is H, C-C10 straight-chain alkyl or C1-C10 branched-chain alkyl,
n, m and p are integers, n is more than or equal to 1, m is more than or equal to 0, and p is more than or equal to 1.
2. The resin composition according to claim 1, wherein at least one of the block copolymersQ in (2) is->
3. The resin composition according to claim 1, wherein at least one PB in the block copolymer isAnd x: y is (1-30): (50-120).
4. The resin composition according to claim 1, wherein in the block copolymer, n: m: p is (30-100): (0-30): (10-55).
5. The resin composition according to claim 1, wherein the crosslinking assistant is at least one selected from the group consisting of triallyl isocyanate monomer, triallyl isocyanate monomer prepolymer, butadiene monomer, styrene monomer, pentadiene monomer, methacrylate monomer, dicyclopentadienyl methacrylate monomer, norbornene monomer, P' -divinyl-1, 2-diphenylethane, cyclopentadiene monomer.
6. The resin composition according to claim 1, wherein the modified maleimide resin is at least one selected from the group consisting of an allylic compound modified maleimide resin, an aromatic diamine modified maleimide resin, a monoaminophenol modified maleimide resin, an aliphatic diamine modified maleimide resin, an amino silicone modified maleimide resin, a double bond silicone modified maleimide resin, a cyanate ester modified maleimide resin, a benzoxazine modified maleimide resin, a mercapto modified maleimide resin, and a polyphenylene ether modified maleimide resin.
7. The resin composition of claim 1, wherein the maleimide resin is selected from at least one of the following structures:
wherein R is 1 Is methylene, ethylene or +.>R 2 Is hydrogen, methyl or ethyl, 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, 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 and m are integers of 1 to 10, respectively.
8. The resin composition according to claim 1, further comprising 0.1 to 50 parts by weight of an ester group-free hydrocarbon resin.
9. The resin composition of claim 1, further comprising, by weight:
1-30 parts by weight of epoxy resin;
and/or, 1-35 parts by weight of cyanate resin.
10. Use of the resin composition according to any one of claims 1 to 9 in prepregs, laminates, circuit substrates and electronic devices.
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| CN202311661976.9A CN117586599A (en) | 2023-12-06 | 2023-12-06 | Resin composition and use of the same |
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