TW202126726A - Modified maleimide compound, preparation method therefor and use thereof - Google Patents
Modified maleimide compound, preparation method therefor and use thereof Download PDFInfo
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- TW202126726A TW202126726A TW109114940A TW109114940A TW202126726A TW 202126726 A TW202126726 A TW 202126726A TW 109114940 A TW109114940 A TW 109114940A TW 109114940 A TW109114940 A TW 109114940A TW 202126726 A TW202126726 A TW 202126726A
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- -1 Modified maleimide compound Chemical class 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 239000011342 resin composition Substances 0.000 claims abstract description 14
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 12
- 239000012779 reinforcing material Substances 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 238000010438 heat treatment Methods 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000011888 foil Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 229920005989 resin Polymers 0.000 abstract description 44
- 239000011347 resin Substances 0.000 abstract description 44
- 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 abstract description 19
- 229910000077 silane Inorganic materials 0.000 abstract description 13
- 229920003192 poly(bis maleimide) Polymers 0.000 abstract description 12
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 8
- 239000002131 composite material Substances 0.000 abstract description 4
- 238000001035 drying Methods 0.000 abstract description 4
- 239000000853 adhesive Substances 0.000 abstract description 3
- 230000001070 adhesive effect Effects 0.000 abstract description 3
- 230000009257 reactivity Effects 0.000 abstract description 3
- 239000006087 Silane Coupling Agent Substances 0.000 abstract description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 239000003292 glue Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 239000003365 glass fiber Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 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 4
- 239000003063 flame retardant Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 3
- 0 Cc(c(*)c1)c(*)cc1Oc(c(*)c1)c(*)cc1-c(cc1*)cc(*)c1Oc1cc(*)c(C)c(*)c1 Chemical compound Cc(c(*)c1)c(*)cc1Oc(c(*)c1)c(*)cc1-c(cc1*)cc(*)c1Oc1cc(*)c(C)c(*)c1 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- 239000004643 cyanate ester Substances 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical class C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical class O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 230000008646 thermal stress Effects 0.000 description 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- IMYCVFRTNVMHAD-UHFFFAOYSA-N 1,1-bis(2-methylbutan-2-ylperoxy)cyclohexane Chemical class CCC(C)(C)OOC1(OOC(C)(C)CC)CCCCC1 IMYCVFRTNVMHAD-UHFFFAOYSA-N 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene;hydrogen peroxide Chemical class OO.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-N 0.000 description 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- KRDXTHSSNCTAGY-UHFFFAOYSA-N 2-cyclohexylpyrrolidine Chemical compound C1CCNC1C1CCCCC1 KRDXTHSSNCTAGY-UHFFFAOYSA-N 0.000 description 1
- FYLALDOHAAJNFY-UHFFFAOYSA-N 2-tert-butylperoxy-2-methylpropane;propan-2-yl hydrogen carbonate Chemical compound CC(C)OC(O)=O.CC(C)(C)OOC(C)(C)C FYLALDOHAAJNFY-UHFFFAOYSA-N 0.000 description 1
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical class CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 description 1
- QMFJIJFIHIDENY-UHFFFAOYSA-N CC1=CC=CCC1 Chemical compound CC1=CC=CCC1 QMFJIJFIHIDENY-UHFFFAOYSA-N 0.000 description 1
- MHKULDOVKTXUSE-UHFFFAOYSA-N Cc(cc1)ccc1S(c(cc1)ccc1NC)(=O)=O Chemical compound Cc(cc1)ccc1S(c(cc1)ccc1NC)(=O)=O MHKULDOVKTXUSE-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 229920002633 Kraton (polymer) Polymers 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
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- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- PXFGTSMDPJUNFI-UHFFFAOYSA-N bicyclo[4.2.0]octa-2,4-dien-1-amine Chemical compound NC12C(CC1)C=CC=C2 PXFGTSMDPJUNFI-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- UFXYMLGIRKSLGL-UHFFFAOYSA-N dimethoxy-methyl-[4-(oxiran-2-ylmethoxy)butoxy]silane Chemical compound C(C1CO1)OCCCCO[Si](OC)(OC)C UFXYMLGIRKSLGL-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
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- 239000007789 gas Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
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- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229930004008 p-menthane Natural products 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 102220043159 rs587780996 Human genes 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- CFJYNSNXFXLKNS-UHFFFAOYSA-N trans-p-menthane Natural products CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- QLNOVKKVHFRGMA-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical group [CH2]CC[Si](OC)(OC)OC QLNOVKKVHFRGMA-UHFFFAOYSA-N 0.000 description 1
- 238000004017 vitrification Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
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- 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
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L47/00—Compositions 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; Compositions of derivatives of such polymers
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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
- 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
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
- C08L71/10—Polyethers derived from hydroxy compounds or from their metallic derivatives from phenols
- C08L71/12—Polyphenylene oxides
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
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- 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
- C08J2347/00—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
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Abstract
Description
本發明涉及印刷電路技術領域,尤其涉及一種改性馬來醯亞胺化合物及其製備方法及應用。 The invention relates to the technical field of printed circuits, in particular to a modified maleimide compound and a preparation method and application thereof.
隨著電子電氣行業的進步和終端電子的迅猛發展,電子線路基板的發展方向為輕薄化、高性能化、高可靠性以及環保等。馬來醯亞胺樹脂作為一種熱固性聚醯亞胺樹脂,在力學性能、電性能、耐熱性和耐溶劑性能方面均有著卓越的表現。在電子電路基板中,雙馬來醯亞胺樹脂或多馬來醯亞胺樹脂目前已在封裝基板領域有了大量的應用。但目前存在的問題之一為馬來醯亞胺樹脂在黏合力方面一直表現不足,因此,一般將其與黏結性較好的環氧樹脂、酚醛樹脂和氰酸酯樹脂進行組合使用,但是將雙馬來醯亞胺與極性較低樹脂進行組合時,其黏結性表現仍很差。 With the progress of the electrical and electronic industry and the rapid development of terminal electronics, the development direction of electronic circuit substrates is light and thin, high performance, high reliability, and environmental protection. As a thermosetting polyimide resin, maleimide resin has outstanding performance in mechanical properties, electrical properties, heat resistance and solvent resistance. Among electronic circuit substrates, bismaleimide resin or polymaleimide resin has been widely used in the field of packaging substrates. However, one of the current problems is that the maleimide resin has been insufficient in adhesion. Therefore, it is generally used in combination with epoxy resins, phenolic resins and cyanate ester resins with better adhesion. When bismaleimide is combined with a lower polar resin, its adhesion performance is still very poor.
CN106700549A公開了一種改性雙馬來醯亞胺樹脂、增強層壓板及其製備方法,雙馬來醯亞胺樹脂經氰酸酯樹脂、橡膠、雙氰胺、二氧化矽改性得到改性雙馬來醯亞胺樹脂,以改性雙馬來醯亞胺樹脂為膠黏劑,以玻璃纖維為基材,經過浸塗上膠、膠布乾燥、層壓製備得到增強層壓板。該發明的優點是,提供了一種能夠滿足工業生產要求的改性雙馬 來醯亞胺樹脂以這種改性雙馬來醯亞胺樹脂與玻璃纖維製備的增強層壓板,不僅具有良好的耐熱性能,其力學性能也得到了顯著的提高,綜合性能優良,可應用於電氣絕緣、航空航天等領域。但是該發明中,得到的層壓板仍會存在介電常數和介電損耗較高的問題。 CN106700549A discloses a modified bismaleimide resin, a reinforced laminate and a preparation method thereof. The bismaleimide resin is modified by cyanate ester resin, rubber, dicyandiamide, and silicon dioxide to obtain a modified double The maleimide resin, the modified bismaleimide resin as the adhesive, the glass fiber as the base material, and the reinforced laminate is prepared by dipping and coating, drying the adhesive tape, and laminating. The advantage of this invention is that it provides a modified double horse which can meet the requirements of industrial production. Reinforced laminates prepared by using this modified bismaleimide resin and glass fiber not only have good heat resistance, but also their mechanical properties have also been significantly improved. The comprehensive performance is excellent, and it can be applied to Electrical insulation, aerospace and other fields. However, in this invention, the obtained laminate still has the problem of high dielectric constant and dielectric loss.
CN105295048A公開了一種高耐熱性液體改性雙馬來醯亞胺樹脂及其製備方法,將3-胺基苯並環丁烯與雙馬來醯亞胺單體經邁克爾加成熔融共聚形成預聚體,降溫後添加活性稀釋劑保溫,冷卻後加入溶有催化劑的溶液,混合均勻,真空蒸除溶解催化劑的溶劑,得到高耐熱性液態改性雙馬來醯亞胺樹脂。該發明提供的樹脂體系常溫下呈現流動液態,是雙馬樹脂領域不多見的品種,表現出良好的加工工藝性,適合目前多種複合材料成型工藝,不僅可用作高級覆銅板的基礎樹脂,而且還可以用於航空航天、交通運輸等領域的先進複合材料或耐高溫膠黏劑等。但是該發明的雙馬來醯亞胺樹脂與低極性樹脂組成的組成物與銅箔、玻璃纖維布等材料的黏結性較差,製備得到的層壓板的剝離強度低。 CN105295048A discloses a high heat resistance liquid modified bismaleimide resin and a preparation method thereof. 3-aminobenzocyclobutene and bismaleimide monomer are melted and copolymerized by Michael addition to form a prepolymer After cooling, add an active diluent to keep warm, add a solution with a catalyst after cooling, mix uniformly, and vacuum-evaporate the solvent to dissolve the catalyst to obtain a liquid modified bismaleimide resin with high heat resistance. The resin system provided by the invention presents a fluid liquid at room temperature. It is a rare species in the field of double-horse resins. It exhibits good processing technology and is suitable for many current composite material molding processes. It can not only be used as the basic resin for advanced copper clad laminates, but also It can also be used in advanced composite materials or high-temperature adhesives in aerospace, transportation and other fields. However, the composition composed of the bismaleimide resin and the low-polarity resin of the present invention has poor adhesion to materials such as copper foil, glass fiber cloth, and the like, and the prepared laminate has low peel strength.
CN101824148A公開了一種含八乙烯基籠型倍半矽氧烷的雙馬來醯亞胺-三嗪樹脂及其製備方法。按重量計,在120~140℃下,將100份雙馬來醯亞胺緩慢加入到O,O'-二烯丙基雙酚A中,得到預聚體I;緩慢地將1894份八乙烯基籠型倍半矽氧烷加入到120~140℃的預聚體I中,得到預聚體II;稱取215~280份的氰酸酯,緩慢加入到預聚體II中,升溫至140~160℃,再保溫攪拌1~2小時,得到一種含八乙烯基籠型倍半矽氧烷的雙馬來醯亞胺-三嗪樹脂。製得的樹脂可作為電子訊息領域製備高性能覆銅板等的基礎材料。但是該樹脂的黏結性較差,製備得到的覆銅板 的剝離強度較低。 CN101824148A discloses a bismaleimide-triazine resin containing octavinyl cage silsesquioxane and a preparation method thereof. By weight, 100 parts of bismaleimide are slowly added to O,O'-diallylbisphenol A at 120~140°C to obtain prepolymer I; slowly 1894 parts of octaethylene Base cage silsesquioxane is added to prepolymer I at 120~140℃ to obtain prepolymer II; weigh 215~280 parts of cyanate ester, slowly add it to prepolymer II, and heat up to 140 ~160°C, and then heat and stir for 1~2 hours to obtain a bismaleimide-triazine resin containing octavinyl cage silsesquioxane. The prepared resin can be used as a basic material for preparing high-performance copper clad laminates in the field of electronic information. But the resin has poor adhesion, and the prepared copper clad laminate The peel strength is low.
因此,本領域亟待開發一種新型的馬來醯亞胺化合物,改善與低極性樹脂組合的黏結性能,且得到低介電和高耐熱的層壓板。 Therefore, there is an urgent need in the art to develop a new type of maleimide compound to improve the bonding performance of the combination with a low-polar resin, and to obtain a laminate with low dielectric and high heat resistance.
本發明的目的之一在於提供改性馬來醯亞胺化合物,改善與低極性樹脂組合的黏結性能,進而製備得到高剝離強度、低介電和高耐熱性的層壓板。 One of the objectives of the present invention is to provide a modified maleimide compound to improve the bonding performance of the combination with a low-polar resin, thereby preparing a laminate with high peel strength, low dielectric and high heat resistance.
為達此目的,本發明採用以下技術手段: To achieve this goal, the present invention adopts the following technical means:
本發明提供一種改性馬來醯亞胺化合物,所述改性馬來醯亞胺化合物由化合物(A)或者含胺基矽烷的有機金屬鹽,以及含有至少兩個馬來醯亞胺基團的化合物(B)製備,所述化合物(A)的分子結構如下: The present invention provides a modified maleimine compound which is composed of compound (A) or an organometallic salt containing aminosilane, and containing at least two maleimine groups The compound (B) is prepared, and the molecular structure of the compound (A) is as follows:
所述R1、R2和R3各自獨立地選自C1~C6(例如C1、C2、C3、C4、C5或C6)烷基; The R 1 , R 2 and R 3 are each independently selected from C1 to C6 (e.g. C1, C2, C3, C4, C5 or C6) alkyl groups;
所述Y的結構為-Y1-Y2-或; The structure of Y is -Y 1 -Y 2 -or ;
所述Y1和Y2各自獨立地選自-CH2-、-C2H4-、-C3H6-、-C4H8-、-C5H10-、-C3H6-N-、-C2H4-N-、、、、
所述Y3選自-H、-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C8H17、-C15H31、,或中的任意一種; The Y 3 is selected from -H, -CH 3 , -C 2 H 5 , -C 3 H 7 , -C 4 H 9 , -C 5 H 11 , -C 8 H 17 , -C 15 H 31 , , or Any of
所述m為0或1。 The m is 0 or 1.
本發明將含有至少兩個馬來醯亞胺基團的化合物(B)與含胺基的矽烷化合物(A)或者含胺基矽烷的有機金屬鹽進行加熱反應,得到一種含矽烷的改性馬來醯亞胺化合物。將其用於複合材料的樹脂組成物時,其具有與低極性樹脂更好的相容性,並在半固化片的烘乾過程中避免矽烷偶聯劑的揮發,並能降低雙馬來醯亞胺與其他樹脂之間反應性,使樹脂組成物的固化應力降低,增加樹脂組成物對增強材料或導電層之間的黏合力,並保持低介電損耗和高耐熱性。 In the present invention, a compound (B) containing at least two maleimine groups is heated to react with an amino-containing silane compound (A) or an organometallic salt of amino-containing silane to obtain a modified horse containing silane Leimine compounds. When it is used in the resin composition of composite materials, it has better compatibility with low-polarity resins, avoids the volatilization of the silane coupling agent during the drying process of the prepreg, and can reduce the bismaleimide Reactivity with other resins reduces the curing stress of the resin composition, increases the adhesion of the resin composition to the reinforcing material or the conductive layer, and maintains low dielectric loss and high heat resistance.
本發明中,化合物(A)或者胺基矽烷的有機金屬鹽的N原子與化合物(B)中羰基鄰位連接,示例性地可以形成如下結構的改性馬來醯亞胺化合物: In the present invention, the N atom of the compound (A) or the organometallic salt of aminosilane is connected to the ortho position of the carbonyl group in the compound (B), which can exemplarily form a modified maleimide compound with the following structure:
上述結構僅為了表述化合物(A)或胺基矽烷的有機金屬鹽和化合物(B)反應後的連接方式,並不限於上述結構,根據原料結構的不同,得到的改性馬來醯亞胺化合物的結構也會有所不同。 The above structure only expresses the connection mode of compound (A) or organometallic salt of aminosilane and compound (B) after the reaction, and is not limited to the above structure. Depending on the structure of the raw material, the obtained modified maleimide compound The structure will also be different.
理想地,所述化合物(A)具有如下式I至式III所示的結構中的任意一種: Ideally, the compound (A) has any one of the following structures shown in formula I to formula III:
所述R1、R2、R3、Y1、Y2和Y3均具有與前文相同的選擇範圍。 The R 1 , R 2 , R 3 , Y 1 , Y 2 and Y 3 all have the same selection range as above.
理想地,所述R1、R2和R3各自獨立地選自CH3、C2H5或C3H7中的任意一種。 Ideally, the R 1 , R 2 and R 3 are each independently selected from any one of CH 3 , C 2 H 5 or C 3 H 7.
理想地,所述Y1和Y2各自獨立地選自 Ideally, the Y 1 and Y 2 are each independently selected from
本發明理想化合物(A)中包含上述連接基團,這些連接基團能夠延長鏈長度,避免樹脂固化後的交聯結構對矽氧烷的影響,能夠進一步提升樹脂的黏結性能,另外這些結構的主鏈具有更高的剛性,有利於高耐熱性。 The ideal compound (A) of the present invention contains the above-mentioned linking groups. These linking groups can extend the chain length, avoid the influence of the cross-linked structure of the resin after curing on the silicone, and can further improve the bonding performance of the resin. The main chain has higher rigidity, which is conducive to high heat resistance.
理想地,所述化合物(B)具有如下式IV或式V所示的結構: Ideally, the compound (B) has a structure shown in the following formula IV or formula V:
所述X選自-CH2-、-C2H4-、-C3H6-、-C4H8-、-C5H10-、、
所述R、R4~R11各自獨立地選自-H、C1~C15(例如C1、C2、C3、C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14等)烷基、、或中的任意一種,理想-H、-CH3、-C2H5、- C3H7、-C4H9、-C5H11、-C8H17、-C15H31、、或中的任意一種; The R, R 4 to R 11 are each independently selected from -H, C1 to C15 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, etc. )alkyl, , or Any one of the ideal -H, -CH 3 , -C 2 H 5 , -C 3 H 7 , -C 4 H 9 , -C 5 H 11 , -C 8 H 17 , -C 15 H 31 , , or Any of
所述n為1~10的整數,例如2、3、4、5、6、7、8、9等。 The n is an integer of 1-10, such as 2, 3, 4, 5, 6, 7, 8, 9, etc.
本發明的目的之二在於提供一種目的之一所述的改性馬來醯亞胺化合物的製備方法,所述製備方法包括:化合物(A)或者含胺基矽烷的有機金屬鹽與含有至少兩個馬來醯亞胺基團的化合物(B)進行加熱反應,得到所述改性馬來醯亞胺化合物。 The second object of the present invention is to provide a method for preparing the modified maleimide compound described in the first object. The preparation method comprises: compound (A) or an organometallic salt containing aminosilane and containing at least two The compound (B) with one maleimine group undergoes a heating reaction to obtain the modified maleimine compound.
理想地,所述加熱反應的溫度為100~200℃,理想110℃、120℃、130℃、136℃、141℃、145℃、151℃、156℃、160℃、165℃和170℃。 Ideally, the temperature of the heating reaction is 100-200°C, ideally 110°C, 120°C, 130°C, 136°C, 141°C, 145°C, 151°C, 156°C, 160°C, 165°C and 170°C.
理想地,所述加熱反應的時間為1~30小時,理想2小時、3小時、4小時、5小時、6小時、7小時、8小時、10小時、12小時、16小時、21小時、28小時。 Ideally, the heating reaction time is 1-30 hours, ideally 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, 10 hours, 12 hours, 16 hours, 21 hours, 28 hours. Hour.
理想地,所述加熱反應在冷凝回流的條件下進行。 Ideally, the heating reaction is carried out under the condition of condensation and reflux.
理想地,所述加熱反應在攪拌下進行。 Ideally, the heating reaction is carried out under stirring.
理想地,所述化合物(A)或者含胺基矽烷的有機金屬鹽與化合物(B)的莫耳比為10:90~80:20,例如10:90、15:85、20:80、24:76、30:70、40:60、50:50、60:40、70:30、80:20等。為了使化合物(A)與化合物(B)能夠充分的發生反應,進一步理想地,莫耳比為30:70~50:50,例如30:70、35:65、38:62、40:60、45:55、50:50等。 Ideally, the molar ratio of the compound (A) or the organometallic salt containing aminosilane to the compound (B) is 10:90~80:20, such as 10:90, 15:85, 20:80, 24 : 76, 30: 70, 40: 60, 50: 50, 60: 40, 70: 30, 80: 20, etc. In order to allow the compound (A) to react with the compound (B) sufficiently, it is further desirable that the molar ratio is 30:70-50:50, such as 30:70, 35:65, 38:62, 40:60, 45:55, 50:50, etc.
理想地,所述加熱反應中加入促進劑。 Ideally, an accelerator is added to the heating reaction.
理想地,所述促進劑的用量為化合物(B)質量的0.01~10%,例如0.1%、0.5%、1%、1.5%、2%、2.5%、3%、3.5%、4%、4.5%、5%、5.5%、6%、6.5%、7%、7.5%、8%、8.5%、9%、9.5%等。 Ideally, the amount of the accelerator is 0.01-10% of the mass of compound (B), such as 0.1%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5 %, 5%, 5.5%, 6%, 6.5%, 7%, 7.5%, 8%, 8.5%, 9%, 9.5%, etc.
理想地,所述促進劑包括過氧化二枯基、叔丁基過氧化枯基、過氧化二叔丁基、過氧化異丙基碳酸叔丁酯、2,5-二甲基-2,5-二叔丁基枯基過氧基己炔-3、2,5-二甲基2,5-二叔丁基過氧化己烷、過氧化對孟烷、1,1-雙(叔戊基過氧)環己烷、過氧化氫二異丙基苯、過氧化苯甲醯、過氧化苯甲醯衍生物、乙醯丙酮的金屬鹽、環烷酸的金屬鹽、五氧化釩、胺類化合物、季銨鹽、咪唑、三苯基膦或三苯基膦衍生物中的任意一種或至少兩種組合。 Ideally, the accelerator includes dicumyl peroxide, tert-butyl cumyl peroxide, di-tert-butyl peroxide, tert-butyl peroxide isopropyl carbonate, 2,5-dimethyl-2,5 -Di-tert-butylcumylperoxyhexyne-3, 2,5-dimethyl 2,5-di-tert-butylperoxyhexane, p-menthane peroxide, 1,1-bis(tert-pentyl Peroxy) cyclohexane, diisopropylbenzene hydrogen peroxide, benzyl peroxide, benzyl peroxide derivatives, metal salts of acetone, metal salts of naphthenic acid, vanadium pentoxide, amines Any one or a combination of at least two of the compound, quaternary ammonium salt, imidazole, triphenylphosphine, or triphenylphosphine derivative.
理想地,所述加熱反應中加入溶劑。 Ideally, a solvent is added during the heating reaction.
理想地,所述溶劑的用量為化合物(B)質量的10~500%,例如50%、100%、150%、200%、250%、300%、350%、400%、450%、480%等,理想50~400%; Ideally, the amount of the solvent is 10~500% of the mass of the compound (B), such as 50%, 100%, 150%, 200%, 250%, 300%, 350%, 400%, 450%, 480% Etc., ideally 50~400%;
理想地,所述溶劑包括甲苯、二甲苯、環己烷、四氫呋喃、N,N-二甲基甲醯胺(DMF)或丁酮中的任意一種或至少兩種組合。 Ideally, the solvent includes any one or a combination of at least two of toluene, xylene, cyclohexane, tetrahydrofuran, N,N-dimethylformamide (DMF) or methyl ethyl ketone.
本發明的目的之三在於提供一種樹脂組成物,所述樹脂組成物中含有目的之一所述的改性馬來醯亞胺化合物。 The third object of the present invention is to provide a resin composition containing the modified maleimide compound described in one of the objects.
本發明的目的之四在於提供一種預浸片,所述預浸片包括增強材料及通過含浸乾燥後附著其上的目的之三所述的樹脂組成物。 The fourth object of the present invention is to provide a prepreg sheet comprising a reinforcing material and the resin composition of the third object attached to it after being impregnated and dried.
理想地,所述增強材料包括玻璃纖維布。 Ideally, the reinforcing material includes glass fiber cloth.
本發明的目的之五在於提供一種絕緣板,所述絕緣板包括至少一張目的之四所述的預浸片。 The fifth object of the present invention is to provide an insulating board comprising at least one prepreg sheet according to the fourth object.
本發明的目的之六在於提供一種覆金屬箔層壓板,所述覆金屬箔層壓板包括至少一張目的之四所述的預浸片以及覆於疊合後的預浸片一側或兩側的金屬箔。 The sixth object of the present invention is to provide a metal-clad laminate, the metal-clad laminate comprising at least one prepreg sheet according to the fourth object and on one or both sides of the laminated prepreg Metal foil.
本發明的目的之七在於提供一種印刷電路板,所述印刷電路板包括至少一張目的之四所述的預浸片,或至少一張目的之五所述的絕緣板,或至少一張目的之六所述的覆金屬箔層壓板。 The seventh object of the present invention is to provide a printed circuit board comprising at least one prepreg according to object four, or at least one insulating board according to object five, or at least one object The sixth metal-clad laminate.
相對於先前技術,本發明具有以下功效: Compared with the prior art, the present invention has the following effects:
本發明將含有至少兩個馬來醯亞胺基團的化合物(B)與含胺基的矽烷化合物(A)或者含胺基矽烷的有機金屬鹽進行加熱反應,得到一種含矽烷的改性馬來醯亞胺化合物。將其用於複合材料的樹脂組成物時,其具有與低極性樹脂更好的相容性,並在半固化片的烘乾過程中避免矽烷偶聯 劑的揮發,並能降低雙馬來醯亞胺與其他樹脂之間反應性,使樹脂組成物的固化應力降低,增加樹脂組成物對增強材料或導電層之間的黏合力,並保持低介電損耗和高耐熱性。 In the present invention, a compound (B) containing at least two maleimine groups is heated to react with an amino-containing silane compound (A) or an organometallic salt of amino-containing silane to obtain a modified horse containing silane Leimine compounds. When it is used in the resin composition of composite materials, it has better compatibility with low-polarity resins, and avoids silane coupling during the drying process of the prepreg The volatilization of the agent can reduce the reactivity between the bismaleimide and other resins, reduce the curing stress of the resin composition, increase the adhesion of the resin composition to the reinforcing material or the conductive layer, and maintain a low dielectric Electrical loss and high heat resistance.
下面通過具體實施方式來進一步說明本發明的技術手段。所屬技術領域中具有通常知識者應該明瞭,所述實施例僅僅是幫助理解本發明,不應視為對本發明的具體限制。 The technical means of the present invention will be further explained below through specific implementations. Those with ordinary knowledge in the technical field should understand that the embodiments are only to help understand the present invention and should not be regarded as specific limitations to the present invention.
下文所涉及到的化合物的詳細訊息如下: The detailed information of the compounds involved in the following is as follows:
KBM-602:N-2-(β-胺乙基)-3-γ-胺丙基甲基二甲氧基矽烷,日本信越; KBM-602: N-2-(β-aminoethyl)-3-γ-aminopropylmethyldimethoxysilane, Shin-Etsu;
KBM-603:N-2-(胺乙基)-3-胺丙基三甲氧基矽烷,日本信越; KBM-603: N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, Shin-Etsu Japan;
KBM-903:3-胺丙基三甲氧基矽烷,日本信越; KBM-903: 3-Aminopropyltrimethoxysilane, Shin-Etsu Japan;
KBE-903:3-胺丙基三乙氧基矽烷,日本信越; KBE-903: 3-Aminopropyltriethoxysilane, Shin-Etsu Japan;
1,2-乙二胺,N,N'-雙苄基-N-[3-(三甲氧基矽烷)丙基]-鹽酸鹽,CAS:145151-33-3,試劑,市售; 1,2-Ethylenediamine, N,N' -bisbenzyl-N-[3-(trimethoxysilyl)propyl]-hydrochloride, CAS: 145151-33-3, reagent, commercially available;
KBM-403:3-縮水基甘油醚氧基丙基甲基三甲氧基矽烷,日本信越; KBM-403: 3-Glycidyloxypropylmethyltrimethoxysilane, Shin-Etsu;
DDM:二胺基二苯甲烷,印度阿圖; DDM: Diaminodiphenylmethane, Attu, India;
DDS:二胺基二苯碸,印度阿圖; DDS: Diaminodiphenyl sulfide, Atu, India;
CAS:92-87-5,4,4'-二胺基聯苯,試劑,市售; CAS: 92-87-5, 4,4'-diaminobiphenyl, reagent, commercially available;
BMI-50P:多官能馬來醯亞胺樹脂,日本KI; BMI-50P: Multifunctional maleimide resin, Japan KI;
BMI-70:雙(3-乙基-5-甲基-4-馬來醯亞胺基苯)甲烷,日本KI; BMI-70: Bis (3-ethyl-5-methyl-4-maleiminobenzene) methane, Japan KI;
BMI-80:2,2-二(4-(4-馬來醯亞胺苯氧基)苯基)丙烷,日本KI。 BMI-80: 2,2-bis(4-(4-maleiminophenoxy)phenyl)propane, Japan KI.
合成例1~6 Synthesis example 1~6
合成例1~6提供種改性馬來醯亞胺化合物,製備步驟如下: Synthesis examples 1 to 6 provide a modified maleimide compound, and the preparation steps are as follows:
將含胺基的矽烷化合物(KBM-602,KBM-603,KBM-903,KBE-903)、含有至少兩個馬來醯亞胺基團的化合物(BMI-70,BMI-80,BMI-50P)、促進劑和溶劑加入具有冷凝回流、攪拌和加熱的反應容器中,加熱攪拌回流後,蒸出反應物中的溶劑,冷卻至常溫,得到改性馬來醯亞胺化合物P1~P6。 Amino-containing silane compounds (KBM-602, KBM-603, KBM-903, KBE-903), compounds containing at least two maleimine groups (BMI-70, BMI-80, BMI-50P) ), the accelerator and the solvent are added to the reaction vessel with reflux, stirring and heating, heating and stirring to reflux, the solvent in the reactant is distilled off and cooled to normal temperature to obtain modified maleimide compounds P1 to P6.
合成例1~6的原料組成、反應時間和反應溫度詳見表1。 The raw material composition, reaction time and reaction temperature of Synthesis Examples 1 to 6 are shown in Table 1.
表1
表1中,──代表不添加對應物質。 In Table 1, ── means that no corresponding substances are added.
合成例7~10 Synthesis example 7~10
本合成例提供一種改性馬來醯亞胺化合物P7~P10,其製備方法如下: This synthesis example provides a modified maleimide compound P7~P10, and the preparation method is as follows:
將KBM-403、二胺化合物(DDM、DDS或4,4'-二胺基聯苯)和DMF加入具有冷凝回流,攪拌和加熱的反應容器中,加熱至160℃攪拌回流2小時,然後加入含有兩個以上馬來醯亞胺基團的化合物(BMI-70或BMI-50P),加熱攪拌回流後,蒸出反應物中的溶劑,冷卻至常溫,得到改性馬來醯亞胺化合物P7~10。 Add KBM-403, diamine compound (DDM, DDS or 4,4'-diaminobiphenyl) and DMF into a reaction vessel with reflux, stirring and heating, heating to 160℃, stirring and refluxing for 2 hours, and then adding Compounds containing two or more maleimine groups (BMI-70 or BMI-50P), after heating, stirring and refluxing, the solvent in the reactant is evaporated, and cooled to room temperature to obtain the modified maleimide compound P7 ~10.
合成例7~10的原料組成、反應時間和反應溫度詳見表2。 The raw material composition, reaction time and reaction temperature of Synthesis Examples 7-10 are shown in Table 2.
表2
表2中,──代表不添加對應物質。 In Table 2, ── means no corresponding substances are added.
對比合成例1 Comparative Synthesis Example 1
按照專利申請CN101775139A的實施例1製備得到的改性雙馬來醯亞胺樹脂(D1),具體步驟如下: The modified bismaleimide resin (D1) prepared according to Example 1 of patent application CN101775139A, the specific steps are as follows:
將100份雙馬來醯亞胺、50份二烯丙基苯基化合物、12份γ胺丙基三乙氧基矽烷及0.50~1.50份水在室溫下混合在溫度為40℃的條件下反應 60分鐘;再升溫至150 C,預聚反應120分鐘後,得到一種改性雙馬來醯亞胺樹脂D1。 Mix 100 parts of bismaleimide, 50 parts of diallyl phenyl compound, 12 parts of γ-aminopropyl triethoxysilane and 0.50~1.50 parts of water at room temperature under the condition of 40°C reaction 60 minutes; then the temperature is raised to 150 C, after 120 minutes of pre-polymerization reaction, a modified bismaleimide resin D1 is obtained.
實施例1~10、對比例1~2 Examples 1~10, Comparative Examples 1~2
實施例1~10、對比例1~2分別提供一種樹脂膠液及層壓板,具體製備過程如下: Examples 1 to 10 and Comparative Examples 1 to 2 respectively provide a resin glue and laminate. The specific preparation process is as follows:
(1)樹脂膠液的製備: (1) Preparation of resin glue:
先將改性馬來醯亞胺化合物(P1~P10、D1中的一種)或未改性的馬來醯亞胺化合物在DMF中溶解,然後與配方中的其他組分混合均勻,即得到樹脂膠液;具體配方詳見表3; First dissolve the modified maleimide compound (one of P1~P10, D1) or unmodified maleimide compound in DMF, and then mix it with the other components in the formula to obtain the resin Glue; see Table 3 for the specific formula;
(2)層壓板的製備: (2) Preparation of laminate:
取型號為2116的玻璃纖維布均勻浸漬上述樹脂膠液,在鼓風烘箱中於155℃烘烤5min製得預浸片,將6張上述預浸片重疊,上下覆35μm反轉銅箔,於真空熱壓機中在3MPa壓力和220℃溫度下壓製90min得到層壓板。 Take a glass fiber cloth of model 2116 and evenly impregnate the above resin glue solution, and bake in a blast oven at 155°C for 5 minutes to prepare a prepreg sheet. Overlap 6 of the above prepreg sheets, and cover the top and bottom with 35μm inverted copper foil. The laminate was obtained by pressing in a vacuum hot press at a pressure of 3 MPa and a temperature of 220° C. for 90 min.
性能測試: Performance Testing:
(1)玻璃化轉變溫度Tg:使用動態熱機械分析(DMA)測試,參考IPC-TM-6502.4.24所規定的DMA測試方法。 (1) Glass transition temperature Tg: use dynamic thermomechanical analysis (DMA) test, refer to the DMA test method specified in IPC-TM-6502.4.24.
(2)熱分解溫度(Td):使用熱失重分析(TGA)測試,參考標準IPC-TM-650 2.4.24.6。 (2) Thermal decomposition temperature (Td): Use thermal weight loss analysis (TGA) test, refer to standard IPC-TM-650 2.4.24.6.
(3)剝離強度(PS):指在室溫下將每毫米銅箔剝離覆銅板所需的拉力。 (3) Peel strength (PS): refers to the tensile force required to peel off the copper clad laminate per millimeter of copper foil at room temperature.
(4)介電常數(Dk)和介電損耗因數(Df):使用平板電 容法測定,參考標準IPC-TM-650 2.4.24。 (4) Dielectric constant (Dk) and dielectric loss factor (Df): use a flat panel Determination by volumetric method, refer to standard IPC-TM-650 2.4.24.
(5)阻燃:按照UL94“50W(20mm)垂直燃燒試驗:V-0、V-1和V-2”測試方法測試,認定V-0為阻燃。 (5) Flame retardant: According to UL94 "50W (20mm) vertical burning test: V-0, V-1 and V-2" test method, V-0 is recognized as flame retardant.
(6)熱膨脹係數和50~260℃熱膨脹比例:測試採用靜態熱分析儀(TMA)測試,測試參考標準IPC-TM-650 2.4.24。 (6) Coefficient of thermal expansion and ratio of thermal expansion at 50~260℃: The test adopts a static thermal analyzer (TMA) test, and the test refers to the standard IPC-TM-650 2.4.24.
(7)熱應力:將帶銅的層壓板漂浮在熔融狀態的錫液表面,溫度288℃,以分層或氣泡的時間作為測試結果。 (7) Thermal stress: Float the laminate with copper on the surface of molten tin at a temperature of 288°C, and use the time of delamination or bubbles as the test result.
上述測試結果詳見表3。 The above test results are shown in Table 3.
表3
表3中各組分的詳細訊息如下: The detailed information of each component in Table 3 is as follows:
OPE-2St:三菱瓦斯,雙端烯烴官能化聚苯醚; OPE-2St: Mitsubishi Gas, double-end olefin functionalized polyphenylene ether;
B-1000:日本曹達,聚丁二烯樹脂; B-1000: Japan Soda, polybutadiene resin;
Ricon257:美國克雷威勒,丁二烯-苯乙烯-二乙烯基苯枝化三元共聚物; Ricon257: American Kreweller, butadiene-styrene-divinylbenzene branched terpolymer;
A1536:美國科騰,SEBS樹脂; A1536: American Kraton, SEBS resin;
NQ1025J:無機填料NQ1025J球型熔融二氧化矽,D50=3.0μm,江蘇聯瑞新材料股份有限公司; NQ1025J: Inorganic filler NQ1025J spherical fused silica, D50=3.0μm, Jiangsu Lianrui New Materials Co., Ltd.;
Bt-93W:美國雅寶,十溴二苯乙撐,阻燃劑; Bt-93W: American Albemarle, decabromodiphenyl ethylene, flame retardant;
OP935:美國克萊恩,含磷阻燃劑; OP935: American Klein, phosphorus-containing flame retardant;
DCP:過氧化二異丙苯,引發劑。 DCP: Dicumyl peroxide, initiator.
──代表不添加對應物質。 ──Means that no corresponding substances are added.
由表3可知,本發明提供的改性馬來醯亞胺化合物與低極性樹脂組合後,具有較強的黏結性能,製備得到的層壓板具有較高的剝離強度,同時具有良好的介電性能和耐熱性能,其中,剝離強度為大於0.8N/mm,1GHz介電常數小於3.8,1GHz介電損耗因數小於0.002,玻璃化 轉變溫度大於190℃,熱分解溫度大於400℃,50~260℃熱膨脹比例小於2%,熱應力均大於60min。 It can be seen from Table 3 that after the modified maleimide compound provided by the present invention is combined with a low-polarity resin, it has strong bonding performance, and the prepared laminate has high peel strength and good dielectric properties. And heat resistance. Among them, the peel strength is greater than 0.8N/mm, the dielectric constant of 1GHz is less than 3.8, the dielectric loss factor of 1GHz is less than 0.002, and the vitrification The transition temperature is greater than 190°C, the thermal decomposition temperature is greater than 400°C, the thermal expansion ratio of 50~260°C is less than 2%, and the thermal stress is greater than 60min.
對比例1沒有將含有胺基的矽烷化合物與馬來醯亞胺進行預聚,而是分別加入至樹脂膠液中,最終得到的層壓板的剝離強度較高,Tg和Td較低,Dk和Df較高,熱膨脹係數和膨脹比例較大,耐熱性能明顯下降。這是由於,在膠液固化的過程中,含有胺基的矽烷化合物快速揮發,而且雙馬來醯亞胺與烯烴樹脂的固化反應較快,進而使上述性能降低。 Comparative Example 1 did not prepolymerize the silane compound containing amine groups and maleimide, but added them to the resin glue solution separately. The finally obtained laminate has higher peel strength, lower Tg and Td, and Dk and The Df is higher, the thermal expansion coefficient and expansion ratio are larger, and the heat resistance performance is obviously reduced. This is because during the curing process of the glue liquid, the silane compound containing the amine group volatilizes quickly, and the curing reaction between the bismaleimide and the olefin resin is faster, thereby reducing the above-mentioned performance.
對比例2中所使用的改性馬來醯亞胺化合物的製備原料中還包括二烯丙基苯基化合物,與實施例相比,其介電性能明顯降低,介電常數和介電損耗明顯偏高,這是由於二烯丙基苯基化合物與雙馬來醯亞胺的反應比較複雜,對介電性能造成了不利影響。 The modified maleimide compound used in Comparative Example 2 also includes diallyl phenyl compound as the raw material. Compared with the examples, its dielectric properties are significantly reduced, and the dielectric constant and dielectric loss are obvious. High, this is because the reaction of diallyl phenyl compound and bismaleimide is more complicated, which has an adverse effect on the dielectric properties.
本發明通過上述實施例來說明本發明的詳細方法,但本發明並不局限於上述詳細方法,即不意味著本發明必須依賴上述詳細方法才能實施。所屬技術領域中具有通常知識者應該明瞭,對本發明的任何改進,對本發明產品各原料的均等替換及輔助成分的添加、具體方式的選擇等,均落在本發明的保護範圍和公開範圍之內。 The present invention uses the above-mentioned embodiments to illustrate the detailed methods of the present invention, but the present invention is not limited to the above-mentioned detailed methods, which does not mean that the present invention must rely on the above-mentioned detailed methods to be implemented. Those with ordinary knowledge in the technical field should understand that any improvement of the present invention, the equal replacement of the raw materials of the product of the present invention, the addition of auxiliary components, the selection of specific methods, etc., fall within the scope of protection and disclosure of the present invention. .
Claims (14)
Applications Claiming Priority (2)
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CN116120560A (en) * | 2022-10-11 | 2023-05-16 | 苏州生益科技有限公司 | Preparation method of modified bismaleimide prepolymer, resin composition and application of resin composition |
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CN113512057B (en) * | 2021-07-20 | 2022-09-20 | 山东阳谷华泰化工股份有限公司 | Bismaleimide propyl diethoxysilane, and preparation method and application thereof |
CN114015046B (en) * | 2021-12-07 | 2023-11-10 | 苏州生益科技有限公司 | Modified bismaleimide prepolymer, composition prepared from modified bismaleimide prepolymer, prepreg and laminated board of modified bismaleimide prepolymer |
CN114561101A (en) * | 2022-04-01 | 2022-05-31 | 焦作市天益科技有限公司 | Diallyl bisphenol A modified bismaleimide resin capable of prolonging shelf life and preparation method thereof |
CN114605825A (en) * | 2022-04-11 | 2022-06-10 | 焦作市天益科技有限公司 | Photosensitive antistatic composite material and preparation method thereof |
KR20240052716A (en) * | 2022-10-11 | 2024-04-23 | 셍기 테크놀로지 (쑤저우) 컴퍼니 리미티드 | Modified bismaleimide prepolymer, resin composition and uses of the resin composition |
CN117024659B (en) * | 2023-09-11 | 2024-05-31 | 河南大树实业有限公司 | Preparation method of large-particle-size high-solid-content styrene-butadiene latex |
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EP2468759A1 (en) * | 2010-12-17 | 2012-06-27 | Sika Technology AG | Secondary Aminosilanes |
CN102584886A (en) * | 2012-01-17 | 2012-07-18 | 华南理工大学 | Silane coupling agent and preparation method thereof |
CN102775605A (en) * | 2012-08-14 | 2012-11-14 | 西北工业大学 | Modified bismaleimide resin and preparation method thereof |
CN104845363B (en) * | 2014-02-14 | 2017-04-05 | 广东生益科技股份有限公司 | A kind of halogen-free resin composition and application thereof |
CN106916418B (en) * | 2015-12-25 | 2020-07-07 | 广东生益科技股份有限公司 | Thermosetting resin composition, prepreg, metal foil-clad laminate and printed circuit board |
CN109879903A (en) * | 2019-01-09 | 2019-06-14 | 青岛科技大学 | One kind is novel to prevent old silane coupling agent and preparation method thereof |
CN110218415B (en) * | 2019-05-31 | 2021-07-06 | 广东生益科技股份有限公司 | Resin composition, prepreg, laminate, metal-clad laminate, and printed wiring board |
CN110317541B (en) * | 2019-06-19 | 2021-07-13 | 南亚新材料科技股份有限公司 | Bonding sheet and preparation method of high-speed copper-clad plate |
CN113088061B (en) * | 2019-12-23 | 2022-11-29 | 广东生益科技股份有限公司 | Thermosetting resin composition, and prepreg, laminated board and metal foil-clad laminated board using same |
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CN116120560A (en) * | 2022-10-11 | 2023-05-16 | 苏州生益科技有限公司 | Preparation method of modified bismaleimide prepolymer, resin composition and application of resin composition |
CN116120560B (en) * | 2022-10-11 | 2024-04-12 | 苏州生益科技有限公司 | Preparation method of modified bismaleimide prepolymer, resin composition and application of resin composition |
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