WO2014190529A1 - 氰酸酯树脂组合物及其用途 - Google Patents
氰酸酯树脂组合物及其用途 Download PDFInfo
- Publication number
- WO2014190529A1 WO2014190529A1 PCT/CN2013/076512 CN2013076512W WO2014190529A1 WO 2014190529 A1 WO2014190529 A1 WO 2014190529A1 CN 2013076512 W CN2013076512 W CN 2013076512W WO 2014190529 A1 WO2014190529 A1 WO 2014190529A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- cyanate ester
- prepolymer
- ester resin
- type cyanate
- weight
- Prior art date
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 44
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 title abstract description 121
- 229920005989 resin Polymers 0.000 claims abstract description 107
- 239000011347 resin Substances 0.000 claims abstract description 107
- -1 maleimide compound Chemical class 0.000 claims abstract description 84
- 239000003822 epoxy resin Substances 0.000 claims abstract description 81
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 81
- 229910052751 metal Inorganic materials 0.000 claims abstract description 28
- 239000002184 metal Substances 0.000 claims abstract description 28
- 239000011888 foil Substances 0.000 claims abstract description 10
- 239000000463 material Substances 0.000 claims abstract description 9
- 239000004643 cyanate ester Substances 0.000 claims description 68
- 239000000203 mixture Substances 0.000 claims description 52
- 239000011521 glass Substances 0.000 claims description 49
- 239000000843 powder Substances 0.000 claims description 47
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 42
- 229920003986 novolac Polymers 0.000 claims description 34
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims description 25
- 125000001624 naphthyl group Chemical group 0.000 claims description 23
- 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 20
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 19
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 239000011256 inorganic filler Substances 0.000 claims description 12
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 12
- 229920001296 polysiloxane Polymers 0.000 claims 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 claims description 10
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 10
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 10
- 229910001593 boehmite Inorganic materials 0.000 claims description 10
- 239000005350 fused silica glass Substances 0.000 claims description 10
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 claims description 10
- 239000000377 silicon dioxide Substances 0.000 claims description 10
- 229910002113 barium titanate Inorganic materials 0.000 claims description 8
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 claims description 8
- 239000012766 organic filler Substances 0.000 claims description 8
- 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 claims description 7
- VMDQUQBEIFMAIC-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC(C)=C1N1C(=O)C=CC1=O VMDQUQBEIFMAIC-UHFFFAOYSA-N 0.000 claims description 7
- 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 claims description 7
- 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 claims description 7
- 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 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000011258 core-shell material Substances 0.000 claims description 7
- 229930003836 cresol Natural products 0.000 claims description 7
- 239000005060 rubber Substances 0.000 claims description 7
- QYOJZFBQEAZNEW-UHFFFAOYSA-N 1-(2-methylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC=C1N1C(=O)C=CC1=O QYOJZFBQEAZNEW-UHFFFAOYSA-N 0.000 claims description 6
- KCFXNGDHQPMIAQ-UHFFFAOYSA-N 1-(4-methylphenyl)pyrrole-2,5-dione Chemical compound C1=CC(C)=CC=C1N1C(=O)C=CC1=O KCFXNGDHQPMIAQ-UHFFFAOYSA-N 0.000 claims description 6
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 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 6
- GIXXQTYGFOHYPT-UHFFFAOYSA-N Bisphenol P Chemical compound C=1C=C(C(C)(C)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 GIXXQTYGFOHYPT-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003365 glass fiber Substances 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 6
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 239000005995 Aluminium silicate Substances 0.000 claims description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 5
- 235000012211 aluminium silicate Nutrition 0.000 claims description 5
- 239000004927 clay Substances 0.000 claims description 5
- 239000002131 composite material Substances 0.000 claims description 5
- 229920001971 elastomer Polymers 0.000 claims description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000010445 mica Substances 0.000 claims description 5
- 229910052618 mica group Inorganic materials 0.000 claims description 5
- 229910000476 molybdenum oxide Inorganic materials 0.000 claims description 5
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 5
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 5
- 239000000454 talc Substances 0.000 claims description 5
- 229910052623 talc Inorganic materials 0.000 claims description 5
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 5
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 claims description 5
- 239000011787 zinc oxide Substances 0.000 claims description 5
- XAEWLETZEZXLHR-UHFFFAOYSA-N zinc;dioxido(dioxo)molybdenum Chemical compound [Zn+2].[O-][Mo]([O-])(=O)=O XAEWLETZEZXLHR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052582 BN Inorganic materials 0.000 claims description 4
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 4
- 229920000106 Liquid crystal polymer Polymers 0.000 claims description 4
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 claims description 4
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 claims description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 claims description 4
- 229930185605 Bisphenol Natural products 0.000 claims description 3
- 239000004305 biphenyl Chemical group 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 229910002026 crystalline silica Inorganic materials 0.000 claims description 3
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 3
- 239000000347 magnesium hydroxide Substances 0.000 claims description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 3
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 3
- 235000012239 silicon dioxide Nutrition 0.000 claims description 3
- 229920005992 thermoplastic resin Polymers 0.000 claims description 3
- 229920001187 thermosetting polymer Polymers 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- YNSSPVZNXLACMW-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)-3-ethyl-5-methylphenyl]methyl]-2-ethyl-6-methylphenyl]pyrrole-2,5-dione Chemical compound C=1C(C)=C(N2C(C=CC2=O)=O)C(CC)=CC=1CC(C=C1CC)=CC(C)=C1N1C(=O)C=CC1=O YNSSPVZNXLACMW-UHFFFAOYSA-N 0.000 claims 3
- XAZPKEBWNIUCKF-UHFFFAOYSA-N 1-[4-[4-[2-[4-[4-(2,5-dioxopyrrol-1-yl)phenoxy]phenyl]propan-2-yl]phenoxy]phenyl]pyrrole-2,5-dione Chemical compound C=1C=C(OC=2C=CC(=CC=2)N2C(C=CC2=O)=O)C=CC=1C(C)(C)C(C=C1)=CC=C1OC(C=C1)=CC=C1N1C(=O)C=CC1=O XAZPKEBWNIUCKF-UHFFFAOYSA-N 0.000 claims 2
- RUORVEVRVBXRIO-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)-3,5-dimethylphenyl]methyl]-2,6-dimethylphenyl]pyrrole-2,5-dione Chemical compound C=1C(C)=C(N2C(C=CC2=O)=O)C(C)=CC=1CC(C=C1C)=CC(C)=C1N1C(=O)C=CC1=O RUORVEVRVBXRIO-UHFFFAOYSA-N 0.000 claims 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- VEALVRVVWBQVSL-UHFFFAOYSA-N strontium titanate Chemical compound [Sr+2].[O-][Ti]([O-])=O VEALVRVVWBQVSL-UHFFFAOYSA-N 0.000 claims 2
- NHWYMYDMYCNUKI-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)-3,5-diethylphenyl]methyl]-2,6-diethylphenyl]pyrrole-2,5-dione Chemical compound C=1C(CC)=C(N2C(C=CC2=O)=O)C(CC)=CC=1CC(C=C1CC)=CC(CC)=C1N1C(=O)C=CC1=O NHWYMYDMYCNUKI-UHFFFAOYSA-N 0.000 claims 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 150000004767 nitrides Chemical class 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- GZCWPZJOEIAXRU-UHFFFAOYSA-N tin zinc Chemical compound [Zn].[Sn] GZCWPZJOEIAXRU-UHFFFAOYSA-N 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 14
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 42
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- 238000003786 synthesis reaction Methods 0.000 description 24
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- 239000007822 coupling agent Substances 0.000 description 16
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
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- 238000004821 distillation Methods 0.000 description 9
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- 239000002904 solvent Substances 0.000 description 9
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
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- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 7
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 7
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- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 7
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- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 2
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
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- H05K2201/0209—Inorganic, non-metallic particles
Definitions
- the present invention relates to a resin composition, and more particularly to a cyanate resin composition and a prepreg, a laminate, a metal foil-clad laminate, and a printed wiring board produced using the same.
- miniaturization With the development of miniaturization, high performance, and high functionality of computer, electronic, and information communication equipment, higher requirements have been placed on printed circuit boards: miniaturization, thinning, high integration, and high reliability.
- the cyanate resin has excellent dielectric properties, heat resistance, mechanical properties and processability, and is a commonly used matrix resin in the production of metal foil-clad laminates for high-end printed wiring boards.
- the cyanate resin has poor heat and humidity resistance after self-curing, it is usually modified by an epoxy resin or the like and then used.
- the currently used bisphenol type epoxy resin has excellent processability, but has disadvantages in heat resistance and moisture resistance; although the novolac type epoxy resin is improved in heat resistance, it is in moisture resistance. There are still deficiencies in the processing and other aspects.
- the resin composition for producing a metal foil-clad laminate is generally required to have flame retardancy, and therefore it is also required to simultaneously use a bromine-containing flame retardant to achieve flame retardancy.
- Phosphorus compounds are currently used as flame retardants, but various intermediates and production processes of phosphorus compounds have certain toxicity. Phosphorus compounds may produce toxic gases (such as methylphosphine) and toxic substances (such as triphenyl) during combustion. Phosphine, etc.), its waste may pose a potential hazard to the aquatic environment. Therefore, it is necessary to develop a halogen compound even without using a halogen compound.
- the laminate also has a flame retardant and high reliability laminate, and therefore requires the resin itself to have more excellent flame retardancy.
- the phenol phenyl aryl fluorenyl type epoxy resin and the phenol naphthyl aryl fluorenyl type epoxy resin have insufficient heat resistance and flame retardancy although they have improved moisture resistance.
- the naphthol biphenyl aryl fluorenyl type naphthol naphthyl aryl fluorenyl type epoxy resin has improved flame retardancy, but the resin melt viscosity is increased and the workability is lowered.
- An object of the present invention is to provide a cyanate resin composition which has good moisture resistance, heat resistance, flame retardancy and reliability while having good processability.
- a cyanate resin composition comprising a cyanate resin (A), an epoxy resin (B) having a structure of the formula (I), and a maleimide compound (C);
- R is an aryl group, and n is an integer of 1 to 20.
- n is, for example, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17-
- the molar ratio of the naphthyl group / (naphthyl group + phenyl group) is, for example, 0.08, 0.12, 0.15, 0.21, 0.26, 0.32- 0.38, 0.45, 0.51, 0.56, 0.62, 0.67, 0.71, 0.76, 0.81, 0.88, 0.92, 0.94.
- n is an integer of 1 to 15, preferably n is an integer of 1 to 10, and when n is in the range of 1 to 10, the epoxy resin (B) having the structure (I) has a wettability to the substrate. it is good.
- the molar ratio of naphthyl / (naphthyl + phenyl) is 0.1 0.8, preferably 0.2 0.7.
- the R is a phenyl group, a naphthyl group or a biphenyl group, and preferably R is a naphthyl group or a biphenyl group.
- the naphthyl group is an ⁇ -naphthyl group or a ⁇ -naphthyl group.
- the epoxy resin (B) having the structure of the formula (I) has a melt viscosity of 1.0 Pa-s at 150 °C.
- the present invention (B) is as follows /",:
- the phenyl group and the naphthyl group are selected, and the molar ratio of the naphthyl group / (naphthyl group + phenyl group) is 0.2 to 0.7, R is an aryl group, and n is an integer of 1 to 10.
- the epoxy resin (B) having the structure (I) has a melt viscosity of 1.0 Pa's at 150 °C.
- the epoxy resin (B) having the structure of the formula (I) can remarkably improve the moist heat resistance, flame retardancy and processability of the cyanate resin composition.
- the cyanate resin (A) according to the present invention is not particularly limited, and is selected from a cyanate resin or a cyanate prepolymer having at least two cyanate groups in a molecular structure, preferably from a bisphenol A type.
- the cyanate resin (A) may be used singly or in combination as needed.
- the amount of the cyanate resin (A) to be used is not particularly limited, and it is preferably from 10 to 90% by weight based on the total weight of the cyanate resin (A) and the epoxy resin (B) having the structure of the formula (I), for example, 12 %, 15%, 21%, 26%, 32%, 36%, 45%, 52%, 58%, 63%, 67%, 72%, 77%, 85%, 88%, further preferred 20 ⁇ 80 %, particularly preferably 30 to 70%.
- the epoxy resin (B) having the structure of the formula (I) may be used singly or in combination of at least two epoxy resins (B) having the structure of the formula (I).
- the amount of the epoxy resin (B) having the structure of the formula (I) is not particularly limited, and it is preferably 10% by weight based on the total weight of the cyanate resin (A) and the epoxy resin (B) having the structure of the formula (I). ⁇ 90%, such as 12%, 15%, 21%, 26%, 32%, 36%, 45%, 52%, 58%, 63%, 67%, 72%, 77%, 85%, 88%, Further, it is preferably 20 to 80%, particularly preferably 30 to 70%.
- an epoxy resin (B) having a structure of the formula (I) can be obtained by: arylene-based phenol resin having a structure represented by the formula ( ⁇ ) in the presence of a basic compound The epoxy chloropropene is reacted in an inert organic solvent to obtain an epoxy resin (B) having the structure of the formula (I).
- the phenyl group and the naphthyl group are selected, and the molar ratio of the naphthyl group / (naphthyl group + phenyl group) is 0.05 0.95, R is an aryl group, and n is an integer of 1 to 20.
- the maleimide compound (C) is not particularly limited, and is selected from a compound having at least one maleimide group in a molecular structure, and preferably contains at least two maleimides in a molecular structure.
- a compound of the group further preferably selected from N-phenylmaleimide, N-(2-methylphenyl)maleimide, N- (4-methylphenyl)maleimide , N-(2,6-dimethylphenyl)maleimide, bis(4-maleimidophenyl) formamidine, 2,2-bis(4-(4-maleyl) Iminophenoxy)-phenyl)propanoid, bis(3,5-dimethyl-4-maleimidophenyl) formamidine, bis(3-ethyl-5-methyl- 4-maleimidophenyl) formamidine, bis(3,5-diethyl-4-maleimidophenyl) formamidine, polyphenylformamidine bismaleimide ( Polyphenyl)maleimi
- the maleimide compound (C) can be used singly or in combination of plural kinds as needed.
- the amount of the maleimide compound (C) to be used is not particularly limited, and it is preferably from 5 to 80% by weight based on the total weight of the cyanate resin (A) and the maleimide compound (C), for example, 7%. 12%, 18%, 25%, 32%, 38%, 44%, 48%, 54%, 60%, 64%, 69%, 75%, 78%, further preferably 10 to 70%.
- the cyanate resin composition further includes an inorganic filler (D).
- an inorganic filler (D) By adding the inorganic filler (D) to the cyanate resin composition, a halogen-free flame-retardant resin composition having more excellent flame retardancy can be obtained.
- the inorganic filler (D) according to the present invention is not particularly limited and is selected from the group consisting of silica, metal hydrate, molybdenum oxide, zinc molybdate, titanium oxide, zinc oxide, barium titanate, barium titanate, barium sulfate, and nitrogen.
- the average particle diameter (d50) of the inorganic filler (D) is not particularly limited, but from the viewpoint of dispersibility, the average particle diameter (d50) is preferably 0.1 to 10 ⁇ m, for example, 0.2 ⁇ m, 0.8 ⁇ m, 1.5 ⁇ m, 2.1 ⁇ m, 2.6 microns, 3.5 microns, 4.5 microns, 5.2 microns, 5.5 microns, 6 microns, 6.5 microns, 7 microns, 7.5 microns, 8 microns, 8.5 microns, 9 microns, 9.5 microns, more preferably 0.2-5 microns.
- the inorganic filler (D) of different types, different particle size distributions or different average particle diameters may be used singly or in combination as needed.
- the amount of the inorganic filler (D) to be used in the invention is not particularly limited, and is preferably a cyanate resin (A), an epoxy resin (B) having a structure of the formula (I), and a maleimide compound (C).
- the inorganic filler (D) is used in an amount of 10 to 300 parts by weight, for example, 20 parts by weight, 40 parts by weight, 60 parts by weight, 80 parts by weight, 100 parts by weight, 120 parts by weight, based on 100 parts by weight.
- Parts by weight 160 parts by weight, 180 parts by weight, 200 parts by weight, 220 parts by weight, 240 parts by weight, 260 parts by weight, 280 parts by weight, 290 parts by weight, preferably 30 to 200 parts by weight, further preferably 50 to 150 parts by weight Parts by weight.
- the inorganic filler (D) may be combined with a surface treating agent or a wetting agent or a dispersing agent.
- the surface treatment agent is not particularly limited and is selected from surface treatment agents commonly used for inorganic surface treatment. Specific examples thereof include a tetraethyl orthosilicate compound, an organic acid compound, an aluminate compound, a titanate compound, a silicone oligomer, a macromolecular treatment agent, and a silicon germanium coupling agent.
- the silicon germanium coupling agent is not particularly limited, and is selected from silicon germanium coupling agents commonly used for surface treatment of inorganic materials, and is specifically an aminosilicone coupling agent, an epoxy silicon germanium coupling agent, and a vinyl silicon germanium coupling agent.
- the wetting agent and the dispersing agent are not particularly limited, and are selected from the group consisting of a wetting agent and a dispersing agent which are commonly used for coatings.
- the present invention may be used alone or in appropriate combination with different types of surface treating agents or wetting agents and dispersing agents as needed.
- the cyanate resin composition of the present invention may further comprise an organic filler (E).
- the organic filler (E) is not particularly limited and is selected from the group consisting of silicone, liquid crystal polymer, thermosetting resin, thermoplastic resin, rubber or core-shell rubber, or a mixture of at least two, preferably a silicone powder or / and core shell rubber.
- the organic filler (E) may be a powder or a granule. Among them, the silicone powder has good flame retardant properties, and the core-shell rubber has a good toughening effect, so it is preferred.
- the amount of the organic filler (E) to be used in the present invention is not particularly limited, and is preferably a cyanate resin (A), an epoxy resin (B) having a structure of the formula (I), and a maleimide compound (C).
- the total weight is 100 parts by weight, and the amount of the organic filler (E) is 1 to 30 parts by weight, for example, 2 parts by weight, 5 parts by weight, 7 parts by weight, 9 parts by weight, 12 parts by weight, 15 parts by weight, 18 parts by weight, 21 parts by weight, 24 parts by weight, 27 parts by weight, 29 parts by weight, preferably 3 to 25 parts by weight, more preferably 5 to 20 parts by weight.
- the cyanate resin composition of the present invention may also be used in combination with an epoxy resin other than the epoxy resin (B) having the structure of the formula (I) as long as it does not impair the inherent properties of the cyanate resin composition.
- an epoxy resin other than the epoxy resin (B) having the structure of the formula (I) may be selected from bisphenol A epoxy resin, bisphenol F epoxy resin, novolac epoxy resin, cresol novolac epoxy resin, bisphenol A phenolic epoxy resin, tetramethyl bisphenol F type Epoxy resin, bisphenol M type epoxy resin, bisphenol S type epoxy resin, bisphenol E type epoxy resin, bisphenol P type epoxy resin, trifunctional phenol type epoxy resin, tetrafunctional phenol type epoxy Resin, naphthalene epoxy resin, naphthol epoxy resin, naphthol novolac epoxy resin, fluorene epoxy resin, phenoxy epoxy resin, norbornene epoxy resin, diamond ⁇ epoxy Resin, bismuth epoxy resin, biphenyl type epoxy resin, dicyclopentadiene type epoxy
- the cyanate resin composition of the present invention can also be used in combination with various high polymers as long as it does not impair the inherent properties of the cyanate resin composition.
- it may be a liquid crystal polymer, a thermosetting resin, a thermoplastic resin, a different flame retardant compound or an additive or the like. They can be used alone or in combination of multiple types as needed.
- the cyanate resin composition of the present invention can also be used in combination with a curing accelerator as needed to control the curing reaction rate.
- the curing accelerator is not particularly limited, and may be selected from curing accelerators commonly used for promoting curing of cyanate resins, epoxy resins, maleimide compounds, specifically copper, zinc, cobalt, nickel, manganese.
- An organic salt of a metal such as tin, an imidazole and a derivative thereof, a tertiary amine, an organic peroxide, an azo compound, a phenol, an inorganic metal salt or the like.
- the cyanate resin composition may further contain various additives, and specific examples thereof include an antioxidant, a heat stabilizer, an antistatic agent, an ultraviolet absorber, a pigment, a colorant, and a lubricant.
- a method for preparing one of the inventive resin compositions can be carried out by a known method, stirred, and The epoxy resin (B) having the structure (I), the cyanate resin (A), the maleimide compound (C), and the like are mixed and prepared.
- Another object of the present invention is to provide a prepreg, a laminate, a metal foil-clad laminate, and a printed wiring board prepared using the above cyanate resin composition, a laminate prepared using the prepreg, and a metal foil coated
- the laminate has good moisture resistance, heat resistance, flame retardancy and reliability, and has good processability, and is suitable for use in a substrate material for preparing a high-density printed wiring board.
- the present invention provides a prepreg prepared by using the above cyanate resin composition, the prepreg comprising a substrate and a cyanate resin composition as described above adhered to the substrate by impregnation and drying.
- the substrate of the present invention is not particularly limited and may be selected from known substrates for producing various printed wiring boards. Specifically, it is inorganic fiber (for example, E glass, D glass, L glass, M glass, S glass, T glass, NE glass, quartz glass fiber, etc.), organic fiber (such as polyimide, polyamide, polyester, polystyrene). Ether, liquid crystal polymer, etc.).
- the form of the substrate is usually a woven fabric, a nonwoven fabric, a roving, a staple fiber, a fiber paper or the like.
- the substrate of the present invention is preferably a glass cloth.
- the preparation method of the prepreg of the present invention is not particularly limited as long as it is a method of preparing a prepreg by combining the cyanate resin composition of the present invention with a substrate.
- the organic solvent may be used as needed in the above-mentioned cyanate resin composition for preparing a prepreg, and the organic solvent is not particularly limited as long as it is an epoxy resin (B) having a structure of the formula (I), a cyanate resin.
- a solvent compatible with a mixture of the maleimide compound (C), and specific examples of the solvent include alcohols such as methanol, ethanol, and butanol, ethyl cellosolve, and butyl cellosolve.
- ethers such as ethylene glycol-methyl ether, diethylene glycol diethyl ether, diethylene glycol butyl ether, ketones such as acetone, methyl ethyl ketone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.
- An aromatic hydrocarbon such as toluene, xylene or mesitylene, an ester such as ethoxyethyl acetate or ethyl acetate, hydrazine, hydrazine-dimethylformamide, hydrazine, hydrazine-dimethylacetamide, ⁇ _methyl_ 2 _pyrrolidone and other nitrogen-containing solvents.
- the above solvents may be used singly or as needed Mix two or more types.
- the present invention also provides a laminate and a metal foil-clad laminate prepared using the above prepreg.
- the laminate comprises at least one prepreg as described above, and the laminated prepreg is laminated and cured to obtain a laminate.
- the metal foil-clad laminate comprises at least one prepreg as described above and a metal foil coated on one or both sides of the prepreg. A metal foil is coated on one or both sides of the laminated prepreg, and the laminate is cured to obtain a metal foil-clad laminate.
- Laminates and metal foil-clad laminates prepared using the prepreg have good moisture resistance, heat resistance, flame retardancy and reliability, and have good processability, and are therefore suitable for preparing high-density printed wiring boards. Substrate material.
- the preparation method of the laminate of the present invention can be prepared by a known method, for example: placing one of the above prepregs or stacking two or more prepregs, as needed, in a prepreg or stacking A metal foil is placed on one or both sides of the prepreg and laminated to obtain a laminate or a metal foil laminate.
- the metal foil is not particularly limited and may be selected from metal foils for printed wiring board materials.
- the lamination conditions can be selected from the general lamination conditions of laminates and multilayer boards for printed wiring boards.
- the present invention also provides a printed wiring board comprising at least one prepreg as described above.
- the method for producing the printed wiring board according to the present invention is not particularly limited and can be produced by a known method.
- the cyanate resin composition provided by the present invention has good moisture resistance, heat resistance, flame retardancy and reliability, and has good processability.
- Prepregs, laminates and metal foil-clad laminates prepared using the cyanate resin composition also have good moisture resistance, heat resistance, flame retardancy and reliability, and have good processability.
- the metal foil-clad laminate prepared by the cyanate resin composition of the present invention is tested for Tg, immersion resistance, moist heat resistance and flame retardancy, and the test results are further described in the following examples. description.
- Synthesis Example 4 Synthesis of naphthyl aryl fluorenyl phenolic epoxy resin 100 g of the naphthylaryl fluorenyl phenol resin obtained in Synthesis Example 1 was dissolved in 307 g of epichlorohydrin and 48 g of diethylene glycol dimethyl ether, and 48% was added dropwise at 60 ° C for 4 hours under reduced pressure. 40g o aqueous sodium hydroxide solution during which the generated water by azeotropic embankment with epichlorohydrin is removed outside the system, the epichlorohydrin was distilled off embankment returned to the system. After the completion of the dropwise addition, the reaction was continued for another hour.
- the prepreg was prepared by dipping the above glue with an E glass cloth having a thickness of 0.1 mm, and then drying the solvent to remove the solvent. 4 sheets and 8 sheets of the above prepregs were respectively laminated, and 18 ⁇ m thick electrolytic copper foil was pressed on both sides thereof, and cured in a press for 2 hours, and the curing pressure was 45 Kg/cm 2 , and solidified. The temperature was 220 ° C, and a copper clad laminate having a thickness of 0.4 and 0.8 mm was obtained.
- Type phenolic epoxy resin 0.02 parts by weight of zinc octoate dissolved in DMF, butanone and uniformly mixed, followed by adding 110 parts by weight of spherical fused silica (SC2050, supplied by Admatechs), and 5 parts by weight of core-shell structured silicone powder ( KMP-605, supplied by Shin-Etsu Chemical), 1 part by weight of epoxysilicone coupling agent (Z-6040, supplied by Dow Corning), adjusted to the proper viscosity with methyl ethyl ketone, stirred and mixed Evenly, the glue is made. According to the same manufacturing process as in Example 1, a copper-clad laminate having a thickness of 0.4 and 0.8 mm was obtained.
- a novolac type cyanate resin (PT-30, supplied by LONZA), 28 parts by weight of an ⁇ -naphthol aryl fluorenyl type cyanate resin (a-naphthol aryl fluorenyl group supplied by Nippon Steel) Resin SN485 is reacted with cyanogen chloride), 22 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl) formamidine ( ⁇ -70, by KI Chemical Industry Co.
- a novolac type cyanate resin PT-30, supplied by LONZA
- an ⁇ -naphthol aryl fluorenyl type cyanate resin a-naphthol aryl fluorenyl group supplied by Nippon Steel
- Resin SN485 is reacted with cyanogen chloride
- 22 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl) formamidine ( ⁇ -70
- ⁇ -naphthol aryl fluorenyl type cyanate resin made by reacting ⁇ -naphthol aryl sulfonyl resin SN485 supplied by Nippon Steel with cyanogen chloride
- 15 parts by weight of di(3-ethyl) 5-5-methyl-4-maleimidophenyl) formamidine BMI-70, supplied by KI Chemical Industry Co., Ltd.
- Type phenolic epoxy resin 10 parts by weight of naphthyl ether type naphthol epoxy resin (EXA-7311, supplied by DIC Corporation), 0.02 parts by weight of zinc octoate dissolved in DMF, butanone and mixed uniformly, then added 60 weight Boehmite (APYRALAOH 30, supplied by Nabaltec), 20 parts by weight of silicone powder (KMP-590, supplied by Shin-Etsu Chemical), 1 part by weight of epoxysilicone coupling agent (Z-6040, supplied by Dow Corning), 1 part by weight of dispersant (BYK-W903, supplied by BYK), adjusted to a suitable viscosity with methyl ethyl ketone, stirred and mixed uniformly to obtain a glue.
- a copper clad laminate having a thickness of 0.4 and 0.8 mm was obtained.
- a novolac type cyanate resin (PT-30, supplied by LONZA), 5 parts by weight of bis(3-ethyl-5-methyl-4-maleimidophenyl)formamidine ( BMI-70, supplied by KI Chemical Industry Co., Ltd., 40 parts by weight of the naphthylarylfluorenyl novolac epoxy resin obtained in Synthesis Example 6, and 30 parts by weight of the naphthylarylfluorenyl group obtained in Synthesis Example 4.
- Type phenolic epoxy resin 0.02 parts by weight of zinc octoate dissolved in DMF, butanone and mixed uniformly, then added 220 parts by weight of spherical fused silica (SC2050, supplied by Admatechs), 2.0 parts by weight of epoxy siloxane coupling agent (Z-6040, supplied by Dow Corning), 1 part by weight of dispersant (BYK-W903, supplied by BYK), adjusted to the proper viscosity with methyl ethyl ketone, stirred Mix well and make a glue. According to the same manufacturing process as in Example 1, a copper clad laminate having a thickness of 0.4 and 0.8 mm was obtained.
- a-naphthol aryl fluorenyl type cyanate resin made by reacting a-naphthol aryl sulfonyl resin SN485 supplied by Nippon Steel with cyanogen chloride
- 15 parts by weight of di(3-ethyl) 5-5-methyl-4-maleimidophenyl) formamidine ⁇ -70, supplied by KI Chemical Industry Co., Ltd.
- Type phenolic epoxy resin 0.02 parts by weight of zinc octoate dissolved in DMF, butanone and mixed uniformly, followed by adding 15 parts by weight of spherical fused silica (SC2050, supplied by Admatechs), 30 parts by weight of silicone powder (KMP-590, Provided by Shin-Etsu Chemical), 1 part by weight of an epoxysilicone coupling agent (Z-6040, supplied by Dow Corning), 1 part by weight of a dispersing agent (BYK-W903, supplied by BYK), and adjusted to a suitable viscosity with methyl ethyl ketone, Stir well and mix well to make a glue. According to the same manufacturing process as in Example 1, a copper-clad laminate having a thickness of 0.4 and 0.8 mm was obtained.
- Example 1 70 parts by weight of a bisphenol A type epoxy resin (EPICLON® 1055, supplied by DIC Corporation) was used instead of 70 parts by weight of a naphthylarylfluorenyl type novolac epoxy resin used in Example 1, and the others were the same as in Example 1.
- the method obtained a copper clad laminate having a thickness of 0.4 and 0.8 mm.
- Example 2 50 parts by weight of a phenol phenyl fluorenyl type epoxy resin (NC-2000, supplied by Nippon Kayaku Co., Ltd.) was used instead of 50 parts by weight of a naphthylaryl fluorenyl type phenolic epoxy resin used in Example 2, and others were used.
- a copper clad laminate having a thickness of 0.4 and 0.8 mm was obtained in the same manner as in Example 2.
- Example 7 25 parts by weight of bisphenol A type epoxy resin (EPICLON® 1055, supplied by DIC Corporation) was used instead of 25 parts by weight of naphthylaryl fluorenyl type phenolic epoxy resin used in Example 7, and other implementations were carried out.
- a copper clad laminate having a thickness of 0.4 and 0.8 mm was obtained in the same manner as in Example 7.
- Tg Test equipment and conditions: DMA, heating rate 5 °C/min, test sample size: etched away copper foil, 0.8 mm.
- Dip resistance Immerse the 50 X 50 mm sample in a 288 ° C tin oven and observe the stratified foaming and record the corresponding time.
- Test sample specifications Unetched copper foil, 0.4 mm.
- Test sample specifications Etched to copper foil, 0.4 mm.
- Moisture and heat resistance A 50 X 50 mm sample was dried at 105 °C for 2 hours. Then, the sample was treated with a high pressure cooking tester at 121 ° C and two atmospheres for 3 hours, and then the sample was immersed in a tin furnace at 260 ° C for 60 seconds to observe whether the sample was stratified (stratified sample number / test) Number of samples).
- Test sample specifications Etched to copper foil, 0.4 mm.
- Examples 1 to 7 of the present invention were superior to those of Comparative Example 1 and Comparative Example 3 using bisphenol A type epoxy resin, as compared with the comparative examples.
- the heat resistance and flame retardancy of Examples 1 to 6 of the present invention were superior to those of Comparative Example 2 using a phenol phenyl fluorenyl type epoxy resin.
- the cyanate resin composition of the present invention and the prepreg, laminate and metal foil-clad laminate obtained therefrom have good moisture resistance, heat resistance, flame retardancy and reliability. Suitable for making substrate materials for high density printed wiring boards.
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Abstract
Description
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KR1020157035057A KR101738292B1 (ko) | 2013-05-30 | 2013-05-30 | 시아네이트 수지 조성물 및 그 용도 |
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EP3733746A4 (en) * | 2017-12-27 | 2021-12-15 | Mitsubishi Gas Chemical Company, Inc. | RESIN COMPOSITION, PREPREG, LAMINATE, METAL FOIL LAMINATE, CIRCUIT BOARD AND MULTI-LAYER CIRCUIT BOARD |
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CN101128501A (zh) * | 2005-02-25 | 2008-02-20 | 日本化药株式会社 | 环氧树脂,含环氧树脂的可固化树脂组合物及其用途 |
CN101343412A (zh) * | 2007-07-12 | 2009-01-14 | 三菱瓦斯化学株式会社 | 预浸料和层压板 |
US20110049426A1 (en) * | 2008-05-14 | 2011-03-03 | Hexcel Composites, Ltd. | Moulding processes |
Cited By (1)
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CN112266740A (zh) * | 2020-10-28 | 2021-01-26 | 黑龙江省科学院石油化学研究院 | 一种耐高低温改性氰酸酯结构胶膜及其制备方法与应用 |
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KR101738292B1 (ko) | 2017-05-29 |
US20160108230A1 (en) | 2016-04-21 |
KR20160007600A (ko) | 2016-01-20 |
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