TWI792365B - 熱固性樹脂組成物以及預浸漬片 - Google Patents
熱固性樹脂組成物以及預浸漬片 Download PDFInfo
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- TWI792365B TWI792365B TW110123037A TW110123037A TWI792365B TW I792365 B TWI792365 B TW I792365B TW 110123037 A TW110123037 A TW 110123037A TW 110123037 A TW110123037 A TW 110123037A TW I792365 B TWI792365 B TW I792365B
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- Taiwan
- Prior art keywords
- resin composition
- resin
- thermosetting resin
- cyanate
- bismaleimide
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 33
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 26
- 229920005989 resin Polymers 0.000 claims abstract description 66
- 239000011347 resin Substances 0.000 claims abstract description 66
- 239000003431 cross linking reagent Substances 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 24
- -1 silane-modified diallyl bisphenol compound Chemical class 0.000 claims abstract description 14
- 229930185605 Bisphenol Natural products 0.000 claims abstract description 10
- 125000000524 functional group Chemical group 0.000 claims abstract description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 4
- 239000004643 cyanate ester Substances 0.000 claims abstract description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 35
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 7
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 6
- 239000004744 fabric Substances 0.000 claims 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 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 claims description 3
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- GTYRFVGHYNRSKT-UHFFFAOYSA-N 3-benzylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(CC=2C=CC=CC=2)=C1 GTYRFVGHYNRSKT-UHFFFAOYSA-N 0.000 claims description 3
- NAKOELLGRBLZOF-UHFFFAOYSA-N phenoxybenzene;pyrrole-2,5-dione Chemical compound O=C1NC(=O)C=C1.O=C1NC(=O)C=C1.C=1C=CC=CC=1OC1=CC=CC=C1 NAKOELLGRBLZOF-UHFFFAOYSA-N 0.000 claims description 3
- MOSSLXZUUKTULI-UHFFFAOYSA-N 3-[3-(2,5-dioxopyrrol-3-yl)-4-methylphenyl]pyrrole-2,5-dione Chemical compound CC1=CC=C(C=2C(NC(=O)C=2)=O)C=C1C1=CC(=O)NC1=O MOSSLXZUUKTULI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- RWHRFHQRVDUPIK-UHFFFAOYSA-N 50867-57-7 Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O RWHRFHQRVDUPIK-UHFFFAOYSA-N 0.000 claims 1
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 claims 1
- ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical compound OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 229910000077 silane Inorganic materials 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 11
- 239000000758 substrate Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 239000000945 filler Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 239000011889 copper foil Substances 0.000 description 5
- 239000003365 glass fiber Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- NOBYOEQUFMGXBP-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOC(=O)OC1CCC(C(C)(C)C)CC1 NOBYOEQUFMGXBP-UHFFFAOYSA-N 0.000 description 1
- RIPYNJLMMFGZSX-UHFFFAOYSA-N (5-benzoylperoxy-2,5-dimethylhexan-2-yl) benzenecarboperoxoate Chemical compound C=1C=CC=CC=1C(=O)OOC(C)(C)CCC(C)(C)OOC(=O)C1=CC=CC=C1 RIPYNJLMMFGZSX-UHFFFAOYSA-N 0.000 description 1
- KDPXFEUKJUOWON-UHFFFAOYSA-N 1,2-dibutyl-3-propan-2-ylbenzene Chemical compound CCCCC1=CC=CC(C(C)C)=C1CCCC KDPXFEUKJUOWON-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
- JPOUDZAPLMMUES-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)octane Chemical compound CCCCCCC(C)(OOC(C)(C)C)OOC(C)(C)C JPOUDZAPLMMUES-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- YKTNISGZEGZHIS-UHFFFAOYSA-N 2-$l^{1}-oxidanyloxy-2-methylpropane Chemical group CC(C)(C)O[O] YKTNISGZEGZHIS-UHFFFAOYSA-N 0.000 description 1
- AXWJKQDGIVWVEW-UHFFFAOYSA-N 2-(dimethylamino)butanedioic acid Chemical compound CN(C)C(C(O)=O)CC(O)=O AXWJKQDGIVWVEW-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000106 Liquid crystal polymer Polymers 0.000 description 1
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- CSDREXVUYHZDNP-UHFFFAOYSA-N alumanylidynesilicon Chemical compound [Al].[Si] CSDREXVUYHZDNP-UHFFFAOYSA-N 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- AJTNUOLFTQRAKF-UHFFFAOYSA-N bis[(2-methylpropan-2-yl)oxy] benzene-1,3-dicarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC(C(=O)OOOC(C)(C)C)=C1 AJTNUOLFTQRAKF-UHFFFAOYSA-N 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical group [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 238000011161 development Methods 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
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910021392 nanocarbon Inorganic materials 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000004017 vitrification Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/04—Epoxynovolacs
-
- 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
- C08L79/085—Unsaturated polyimide precursors
-
- 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
- C08G73/126—Unsaturated polyimide precursors the unsaturated precursors being wholly aromatic
-
- 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
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
- C08G64/12—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing nitrogen
-
- 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
-
- 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
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
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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
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C08L61/14—Modified phenol-aldehyde condensates
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08L79/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
- C08J2363/02—Polyglycidyl ethers of bis-phenols
-
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Abstract
本發明提供一種熱固性樹脂組成物以及預浸漬片。熱固性樹脂組成物包括馬來醯亞胺樹脂、氰酸酯樹脂以及交聯劑。交聯劑為矽烷改質二烯丙基雙酚化合物，其結構由式（1）表示：
Description
本發明是有關於一種樹脂組成物以及預浸漬片，且特別是有關於一種熱固性樹脂組成物以及預浸漬片。
近年來，隨著通訊技術的高速發展，電子產品在輕量化與高密度化方面的需求與日俱增。電子產品在使用的過程中的消耗功率將產生大量熱能，導致電子產品溫度升高，不停地熱脹冷縮，使基板容易損毀，因此，對於電子產品的尺寸安定性也愈加嚴苛。對於尺寸安定性之優化，習知手段為提高填料的含量，但此方法會使膠水黏度大幅提升，導致施工難度提升且成品外觀不良。另一方法為提高樹脂之交聯密度，能夠提高尺寸安定性的同時也提高耐熱性。
基於上述，開發出一種熱固性樹脂組合物，以達到優良的尺寸安定性且擁有高Tg（玻璃化轉變溫度）及高耐熱性，並可應用在銅箔基板與印刷電路板當中，為本領域技術人員亟欲發展的目標。
本發明提供一種熱固性樹脂組合物，其中的交聯劑可達到優良的尺寸安定性且擁有高Tg（玻璃化轉變溫度）及高耐熱性，並可應用在銅箔基板與印刷電路板當中。
本發明的熱固性樹脂組成物，包括馬來醯亞胺樹脂、氰酸酯樹脂以及交聯劑。交聯劑為矽烷改質二烯丙基雙酚化合物，其結構由式（1）表示：
式（1）
在式（1）中，X為直鏈或支鏈的C1至C6烷基、環烷基或磺醯基，R1為直鏈或支鏈的C1至C6烷基或芳基，R2為C1至C6的烷基，R3為帶有可交聯雙鍵的官能基，n+m為1至8的正整數。
在本發明的一實施例中，帶有可交聯雙鍵的官能基包括丙烯基（allyl）、乙烯基（vinyl）、丙烯酸基（acrylate）或甲基丙烯酸基（methacrylate）。
在本發明的一實施例中，n+m為2或3。
在本發明的一實施例中，以馬來醯亞胺樹脂的含量為100 phr計，氰酸酯樹脂的含量為30 phr至210 phr，交聯劑的含量為15 phr至150 phr。
在本發明的一實施例中，馬來醯亞胺樹脂與氰酸酯樹脂的反應基當量比例為1：1至3：1。
在本發明的一實施例中，氰酸酯樹脂包括雙酚A型氰酸酯樹脂、雙環戊二烯型（DCPD）氰酸酯樹脂、雙酚F型氰酸酯樹脂、酚醛型氰酸酯樹脂或其組合。
在本發明的一實施例中，馬來醯亞胺樹脂包括4, 4’-二苯甲烷雙馬來醯亞胺、苯甲烷馬來醯亞胺寡聚物、間-亞苯基雙馬來醯亞胺、雙酚A二苯基醚雙馬來醯亞胺、3, 3’-二甲基-5, 5’-二乙基-4, 4’-二苯基甲烷雙馬來醯亞胺、4-甲基-1, 3-亞苯基雙馬來醯亞胺、1, 6-雙馬來醯亞胺-(2, 2, 4-三甲基)己烷或其組合。
本發明的預浸漬片由上述熱固性樹脂組成物所製成，其中通過將基材含浸或塗佈熱固性樹脂組成物，並乾燥經含浸或塗佈的基材而製成。
基於上述，本發明的熱固性樹脂組合物含有矽烷改質二烯丙基雙酚化合物作為交聯劑，因此，可藉由提高樹脂交聯密度進而達到優良的尺寸安定性且擁有高Tg（玻璃化轉變溫度）及高耐熱性，並可應用在銅箔基板與印刷電路板當中。
以下，將詳細描述本發明的實施例。然而，這些實施例為例示性，且本發明揭露不限於此。
在本文中，由「一數值至另一數值」表示的範圍，是一種避免在說明書中一一列舉該範圍中的所有數值的概要性表示方式。因此，某一特定數值範圍的記載，涵蓋該數值範圍內的任意數值以及由該數值範圍內的任意數值界定出的較小數值範圍，如同在說明書中說明文寫出該任意數值和該較小數值範圍一樣。
本發明提出一種熱固型樹脂組成物，包括馬來醯亞胺樹脂、氰酸酯樹脂、交聯劑、填料、催化劑以及溶劑。以下，將對上述各種組分進行詳細說明。
＜ 馬來醯亞胺樹脂 ＞
本發明的馬來醯亞胺樹脂可包括4, 4’-二苯甲烷雙馬來醯亞胺、苯甲烷馬來醯亞胺寡聚物、間-亞苯基雙馬來醯亞胺、雙酚A二苯基醚雙馬來醯亞胺、3, 3’-二甲基-5, 5’-二乙基-4, 4’-二苯基甲烷雙馬來醯亞胺、4-甲基-1, 3-亞苯基雙馬來醯亞胺、1, 6-雙馬來醯亞胺-(2, 2, 4-三甲基)己烷或其組合。
＜ 氰酸酯樹脂 ＞
本發明的氰酸酯樹脂可包括雙酚A型氰酸酯樹脂、雙環戊二烯型（DCPD）氰酸酯樹脂、雙酚F型氰酸酯樹脂、酚醛型氰酸酯樹脂或其組合。在本實施例中，馬來醯亞胺樹脂與氰酸酯樹脂的反應基當量比例為約1：1至3：1。以馬來醯亞胺樹脂的含量為100 phr計，氰酸酯樹脂的含量例如是30 phr至210 phr。
＜ 交聯劑 ＞
本發明的交聯劑為矽烷改質二烯丙基雙酚化合物，其結構由式（1）表示：
式（1）
在式（1）中，X為直鏈或支鏈的C1至C6烷基、環烷基或磺醯基，R1為直鏈或支鏈的C1至C6烷基或芳基，R2為C1至C6的烷基，R3為帶有可交聯雙鍵的官能基，n+m為1至8的正整數，n+m較佳為2或3。
以馬來醯亞胺樹脂的含量為100 phr計，交聯劑的含量例如是15 phr至150 phr。
更詳細而言，在式（1）中，R3為帶有可交聯雙鍵的官能基，帶有可交聯雙鍵的官能基可包括丙烯基（allyl）、乙烯基（vinyl）、丙烯酸基（acrylate）或甲基丙烯酸基（methacrylate），但本發明並不以此為限。此外，必須說明的是，在式（1）中，R3可以是含有氧原子或不含有氧原子的。若R3含有氧原子，例如可以是先接上一個氧原子，再接上帶有可交聯雙鍵的官能基。
＜ 填料 ＞
本發明的填料可包括二氧化矽、氧化鋁、氧化鎂、氫氧化鎂、碳酸鈣、滑石、黏土、氮化鋁、氮化硼、氫氧化鋁、碳化鋁矽、碳化矽、碳酸鈉、二氧化鈦、氧化鋅、氧化鋯、石英、鑽石、類鑽石、石墨、鍛燒高嶺土、白嶺土、雲母、水滑石、中空二氧化矽、聚四氟乙烯（polytetrafluoroethylene，PTFE）粉末、玻璃珠、奈米碳管、奈米級無機粉體或其組合，優選為乙烯基（vinyl）改質之二氧化矽。以馬來醯亞胺樹脂的含量為100 phr計，填料的含量例如是150 phr至400 phr。
＜ 催化劑 ＞
催化劑的種類並無特殊限制，只要能促進官能基反應、並降低樹脂組成物的固化反應溫度即可。具體而言，催化劑可包括過氧化二苯甲醯、過氧化二異丙苯、2,5-二甲基-2,5-二(叔丁基過氧基)己烷、2,5-二甲基-2,5-二(叔丁基過氧基)-3-己炔、過氧化二叔丁基、二(叔丁基過氧化異丙基)苯、二(叔丁基過氧基)鄰苯二甲酸酯、二(叔丁基過氧基)間苯二甲酸酯、過氧苯甲酸叔丁酯、2,2-雙(叔丁基過氧基)丁烷、2,2-雙(叔丁基過氧基)辛烷、2,5-二甲基-2,5-二(苯甲醯基過氧基)己烷、過氧化月桂醯、過氧化新戊酸叔己酯、雙丁基過氧化異丙基苯、雙(4-叔丁基環己基)過氧化二碳酸酯或其至少兩種的組合。以馬來醯亞胺樹脂的含量為100 phr計，催化劑的含量例如是2 phr至6 phr。
＜ 溶劑 ＞
溶劑的種類並無特殊限制，只要其能使樹脂組合物的黏度適中，便於操作、固化即可。更具體而言，溶劑可以是二甲基乙醯胺，但本發明並不以此為限。
本發明也提供一種預浸漬片，由上述熱固性樹脂組成物所製成，其中通過將基材含浸或塗佈熱固性樹脂組成物，並乾燥經含浸或塗佈的基材而製成。更詳細而言，基材可包括玻璃纖維補強材料(玻璃纖維織物或不織物、玻璃紙、玻璃氈等)、牛皮紙、短絨棉紙、天然纖維布、有機纖維布、液晶高分子纖維氈等。在本實施例中，例如可使用2116玻璃纖維布作為補強材(基材)，並在溫度130℃至200℃下加熱乾燥2分鐘至10分鐘，從而製得半固化的預含浸片。取數片半固化的預含浸片堆疊於熱壓機中進行高溫固化，固化條件例如是在溫度210℃至280℃下固化1小時至4小時。
以下，藉由實驗例來詳細說明上述本發明所提出的熱固性樹脂組成物。然而，下述實驗例並非用以限制本發明。
實驗例
為了證明本發明所提出的熱固性樹脂組成物具有優良的熱性質與尺寸安定性，以下特別作此實驗例。
依據以下表1所列出的組成比例，製備實例1至實例5以及比較例1至比較例5的樹脂組成物。使用2116玻璃纖維布作為基材，將基材含浸或塗佈樹脂組成物，並在溫度130℃至200℃下加熱乾燥2分鐘至10分鐘，從而製得半固化的預含浸片。取數片半固化的預含浸片堆疊於熱壓機中進行高溫固化，固化條件例如是在溫度210℃至280℃下固化1小時至4小時。之後，測試試片的各項性質，並將測試結果列於以下表1中。
在以下表1中，氰酸酯樹脂為雙酚A型氰酸酯樹脂，馬來醯亞胺樹脂為3, 3’-二甲基-5, 5’-二乙基-4, 4’-二苯基甲烷雙馬來醯亞胺，填料為二氧化矽，催化劑為過氧化二異丙苯，溶劑為二甲基乙醯胺，交聯劑為由式（1）表示的矽烷改質二烯丙基雙酚化合物。
表 1
（單位：phr）
| 實例1 | 實例2 | 實例3 | 實例4 | 實例5 | 比較例1 | 比較例2 | 比較例3 | 比較例4 | 比較例5 | |
| 馬來醯亞胺樹脂 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 |
| 氰酸酯樹脂 | 57 | 125 | 38 | 76 | 208 | 114 | 0 | 23 | 275 | 251 |
| 交聯劑 | 26 | 127 | 35 | 18 | 29 | 0 | 52 | 21 | 57 | 190 |
| 填料 | 185 | 360 | 176 | 197 | 345 | 215 | 158 | 149 | 440 | 550 |
| 催化劑 | 2 | 4 | 2 | 2 | 2 | 2 | 2 | 2 | 5 | 6 |
| 溶劑 | 適量 | 適量 | 適量 | 適量 | 適量 | 適量 | 適量 | 適量 | 適量 | 適量 |
| Tg (DMA, ℃) | 210 | 206 | 203 | 206 | 220 | 196 | 201 | 193 | 242 | 194 |
| Td (5wt% loss, ℃) | 474 | 453 | 476 | 447 | 423 | 420 | 589 | 496 | 435 | 431 |
| CTE (Alpha 1, ppm/℃) | 22 | 11 | 23 | 9.7 | 11 | -55 | 32 | -19 | 14 | -28 |
| 剝離強度(lb/in) | 2.45 | 2.37 | 1.82 | 2.15 | 1.94 | 1.73 | 0.98 | 1.97 | 2.81 | 2.72 |
| 錫爐爆板測試(Solder dip) | OK | OK | OK | OK | OK | NG | OK | OK | NG | OK |
| Dk (10GHz) | 4.10 | 4.23 | 4.32 | 4.19 | 4.07 | 3.75 | 4.14 | 4.11 | 4.19 | 4.20 |
| Df (10GHz) | 0.0064 | 0.0076 | 0.0070 | 0.0071 | 0.0073 | 0.0059 | 0.0075 | 0.0069 | 0.0073 | 0.0077 |
如表1所示，實例1至實例5顯示，當熱固性樹脂組成物中馬來醯亞胺樹脂、氰酸酯樹脂以及交聯劑符合本發明所提出的含量範圍時（以馬來醯亞胺樹脂的含量為100 phr計，氰酸酯樹脂的含量為30 phr至210 phr，交聯劑的含量為15 phr至150 phr），固化後的樹脂組合物具有優良的熱性質與尺寸安定性。相較之下，比較例1顯示，當樹脂組合物未添加本發明的交聯劑（由式（1）表示的矽烷改質二烯丙基雙酚化合物），其尺寸安定性差、熱性質不良。比較例2顯示，未添加氰酸酯樹脂的情況下，CTE數值偏高且銅箔剝離力異常降低。比較例3顯示，氰酸酯樹脂添加量不足時，Tg低於200℃且CTE為負值。比較例4顯示，氰酸酯樹脂添加過量時，無法通過錫爐爆板測試。比較例5顯示，氰酸酯樹脂與本發明的交聯劑（由式（1）表示的矽烷改質二烯丙基雙酚化合物）添加過量時，Tg低於200℃且CTE為負值。
綜上所述，本發明的熱固性樹脂組合物包括馬來醯亞胺樹脂、氰酸酯樹脂以及交聯劑，交聯劑為由式（1）表示的矽烷改質二烯丙基雙酚化合物。當本發明的熱固性樹脂組成物中馬來醯亞胺樹脂、氰酸酯樹脂以及交聯劑符合所提出的含量範圍時（以馬來醯亞胺樹脂的含量為100 phr計，氰酸酯樹脂的含量為30 phr至210 phr，交聯劑的含量為15 phr至150 phr），藉由添加交聯劑從而提高樹脂交聯密度的方式，可達到優良的尺寸安定性且擁有高Tg（玻璃化轉變溫度）及高耐熱性，並可應用在銅箔基板與印刷電路板當中。
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Claims (7)
- 一種熱固性樹脂組成物，包括：馬來醯亞胺樹脂；氰酸酯樹脂；以及交聯劑，所述交聯劑為矽烷改質二烯丙基雙酚化合物，其結構由式(1)表示：
- 如請求項1所述的熱固性樹脂組成物，其中所述帶有可交聯雙鍵的官能基包括丙烯基(allyl)、乙烯基(vinyl)、丙烯酸基(acrylate)或甲基丙烯酸基(methacrylate)。
- 如請求項1所述的熱固性樹脂組成物，其中n+m為2或3。
- 如請求項1所述的熱固性樹脂組成物，其中所述馬來醯亞胺樹脂與所述氰酸酯樹脂的反應基當量比例為1：1至3：1。
- 如請求項1所述的熱固性樹脂組成物，其中所述氰酸酯樹脂包括雙酚A型氰酸酯樹脂、雙環戊二烯型(DCPD)氰酸酯樹脂、雙酚F型氰酸酯樹脂、酚醛型氰酸酯樹脂或其組合。
- 如請求項1所述的熱固性樹脂組成物，其中所述馬來醯亞胺樹脂包括4,4’-二苯甲烷雙馬來醯亞胺、苯甲烷馬來醯亞胺寡聚物、間-亞苯基雙馬來醯亞胺、雙酚A二苯基醚雙馬來醯亞胺、3,3’-二甲基-5,5’-二乙基-4,4’-二苯基甲烷雙馬來醯亞胺、4-甲基-1,3-亞苯基雙馬來醯亞胺、1,6-雙馬來醯亞胺-(2,2,4-三甲基)己烷或其組合。
- 一種預浸漬片，由請求項1至請求項6中任一項所述的熱固性樹脂組成物所製成，其中通過將基材含浸或塗佈所述熱固性樹脂組成物，並乾燥經含浸或塗佈的所述基材而製成。
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| CN202110981883.9A CN115521614B (zh) | 2021-06-24 | 2021-08-25 | 热固性树脂组成物以及预浸渍片 |
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| CN110099975A (zh) * | 2016-12-23 | 2019-08-06 | 莫门蒂夫性能材料股份有限公司 | 能加成-固化的硅橡胶组合物 |
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