TW201815872A - 苯酚酚醛清漆樹脂、硬化性樹脂組成物及其硬化物 - Google Patents
苯酚酚醛清漆樹脂、硬化性樹脂組成物及其硬化物 Download PDFInfo
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- TW201815872A TW201815872A TW106118790A TW106118790A TW201815872A TW 201815872 A TW201815872 A TW 201815872A TW 106118790 A TW106118790 A TW 106118790A TW 106118790 A TW106118790 A TW 106118790A TW 201815872 A TW201815872 A TW 201815872A
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- Prior art keywords
- resin
- resin composition
- phenol
- phenol novolak
- novolak resin
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 166
- 229920005989 resin Polymers 0.000 title claims abstract description 156
- 239000011347 resin Substances 0.000 title claims abstract description 156
- 229920003986 novolac Polymers 0.000 title claims abstract description 93
- 239000011342 resin composition Substances 0.000 title claims description 81
- 238000005259 measurement Methods 0.000 claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 3
- 239000003822 epoxy resin Substances 0.000 claims description 34
- 229920000647 polyepoxide Polymers 0.000 claims description 34
- 239000000463 material Substances 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 239000004065 semiconductor Substances 0.000 claims description 19
- 239000012783 reinforcing fiber Substances 0.000 claims description 14
- 239000003566 sealing material Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 8
- 239000003733 fiber-reinforced composite Substances 0.000 claims description 8
- 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 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 239000011256 inorganic filler Substances 0.000 claims description 7
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 239000011889 copper foil Substances 0.000 claims description 5
- 239000004848 polyfunctional curative Substances 0.000 claims description 5
- 230000003014 reinforcing effect Effects 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 4
- 238000005481 NMR spectroscopy Methods 0.000 claims 1
- -1 alkyl phenol Chemical compound 0.000 abstract description 77
- 239000000203 mixture Substances 0.000 abstract description 19
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 abstract description 18
- 238000010438 heat treatment Methods 0.000 abstract description 10
- 238000000465 moulding Methods 0.000 abstract description 10
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 47
- 238000000034 method Methods 0.000 description 38
- 150000001875 compounds Chemical class 0.000 description 32
- 239000003063 flame retardant Substances 0.000 description 30
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 29
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 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 20
- 239000000758 substrate Substances 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 17
- 239000005011 phenolic resin Substances 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 16
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 15
- 238000002156 mixing Methods 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 12
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 11
- 238000001723 curing Methods 0.000 description 11
- 150000002989 phenols Chemical class 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229920000877 Melamine resin Polymers 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000004305 biphenyl Substances 0.000 description 10
- 235000010290 biphenyl Nutrition 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 229910052698 phosphorus Inorganic materials 0.000 description 10
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 9
- 239000011574 phosphorus Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 238000003475 lamination Methods 0.000 description 7
- 239000002966 varnish Substances 0.000 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 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 6
- 229930003836 cresol Natural products 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 239000005350 fused silica glass Substances 0.000 description 6
- 238000013007 heat curing Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 6
- 230000001681 protective effect Effects 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 229930185605 Bisphenol Natural products 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 5
- 125000005605 benzo group Chemical group 0.000 description 5
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 5
- 239000000347 magnesium hydroxide Substances 0.000 description 5
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000004843 novolac epoxy resin Substances 0.000 description 5
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 229920000049 Carbon (fiber) Polymers 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
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- 239000012796 inorganic flame retardant Substances 0.000 description 4
- 229910010272 inorganic material Inorganic materials 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 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 description 4
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- 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 4
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- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- GSKNLOOGBYYDHV-UHFFFAOYSA-N 2-methylphenol;naphthalen-1-ol Chemical compound CC1=CC=CC=C1O.C1=CC=C2C(O)=CC=CC2=C1 GSKNLOOGBYYDHV-UHFFFAOYSA-N 0.000 description 3
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229910015900 BF3 Inorganic materials 0.000 description 3
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- YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 description 3
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- 150000001299 aldehydes Chemical class 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
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- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
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- 229910000000 metal hydroxide Inorganic materials 0.000 description 3
- 150000004692 metal hydroxides Chemical class 0.000 description 3
- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
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- 229910021511 zinc hydroxide Inorganic materials 0.000 description 3
- 229940007718 zinc hydroxide Drugs 0.000 description 3
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- WBODDOZXDKQEFS-UHFFFAOYSA-N 1,2,3,4-tetramethyl-5-phenylbenzene Chemical group CC1=C(C)C(C)=CC(C=2C=CC=CC=2)=C1C WBODDOZXDKQEFS-UHFFFAOYSA-N 0.000 description 2
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- CZAVRNDQSIORTH-UHFFFAOYSA-N 1-ethenoxy-2,2-bis(ethenoxymethyl)butane Chemical compound C=COCC(CC)(COC=C)COC=C CZAVRNDQSIORTH-UHFFFAOYSA-N 0.000 description 2
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- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
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Abstract
本發明提供一種於含有苯酚酚醛清漆樹脂之組成物的加熱硬化時之成形收縮率、熱時彈性模數之平衡性優異的苯酚酚醛清漆樹脂、組成物、其製造方法、及其硬化物。本發明係一種苯酚酚醛清漆樹脂、使用其之硬化性樹脂組成物、及其硬化物,該苯酚酚醛清漆樹脂之特徵在於:其係具有碳數4~8之烷基作為芳香環上之取代基的烷基苯酚(I)經由亞甲基連結而成之烷基苯酚酚醛清漆樹脂,且13C-NMR測定中之146~148ppm之積分值(a)與146~153ppm之積分值(b)的比(a)/(b)為0.05~0.30之範圍,並且GPC測定中之烷基苯酚(I)之面積比為0.01~3.0%之範圍。
Description
本發明係關於一種流動性、加熱硬化時之高收縮率、低彈性模數之平衡性優異且能夠較佳地用於半導體密封材料等之苯酚酚醛清漆樹脂、及含有該苯酚酚醛清漆樹脂之硬化性樹脂組成物與其硬化物。
苯酚酚醛清漆樹脂係例如與環氧樹脂之硬化劑組合而製成硬化性樹脂組成物,用於接著劑、成形材料、塗料、光阻劑材料、顯色材料等,此外,就所獲得之硬化物的優異之耐熱性或耐濕性等方面而言,被廣泛用於半導體密封材料或印刷配線板用絕緣材料等電氣、電子領域。
於該等各種用途中,電氣、電子領域對薄型化、輕量化之要求較高,作為應對該等要求之構裝技術之一,有晶圓級封裝技術。晶圓級封裝技術係藉由於晶圓之狀態下進行樹脂密封或再配線、電極形成且藉由切割進行單片化,而製造半導體封裝之構裝技術。由於利用密封樹脂進行一次密封,故而因樹脂硬化時之收縮、及起因於晶片之線膨脹係數與密封樹脂之線膨脹係數的收縮量差而產生翹曲。因該翹曲使封裝體之可靠性顯著降低,故而以抑制翹曲為目的,對密封樹脂要求低黏度化、低收縮化、 低彈性模數化。
作為可較佳地用作電子材料用途、尤其是耐濕、耐焊性優異之積層板用途中之環氧樹脂用硬化劑的苯酚酚醛清漆樹脂,例如提供如下苯酚酚醛清漆樹脂,其係含有25質量%以上之3官能性化合物者,其特徵在於:於構成該樹脂之至少1個苯酚之芳香環上具有取代基(例如參照專利文獻1)。或者亦已知較佳地使用含有萘醚骨架之環氧樹脂作為半導體密封材料(例如參照專利文獻2)。
如上所述,雖然藉由使用以芳香環上具有取代基之酚類作為原料之硬化性樹脂組成物,可於所獲得之硬化物之強度或耐濕性之方面獲得一定效果,但並不能夠充分滿足近年來所要求之樹脂組成物之黏度、加熱硬化時之成形收縮率、彈性模數之平衡等級,從而要求進一步之改良。
[專利文獻1]日本特開平7-10967號公報
[專利文獻2]日本特開2016-89096號公報
因此,本發明所欲解決之課題在於提供一種含有苯酚酚醛清漆樹脂之組成物於加熱硬化時之成形收縮率、彈性模數之平衡性優異的苯酚酚醛清漆樹脂、組成物、及其硬化物。
本發明人等為解決上述問題經過努力研究,結果發現,若於具有碳數4~8之烷基作為芳香環上之取代基的烷基苯酚之酚醛清漆樹脂中,使用含有原料烷基苯酚且13C-NMR測定中之146~148ppm之積分值(a)與146~153ppm之積分值(b)的比為特定範圍者,則於加熱硬化時之成形收縮率、彈性模數之平衡性優異,從而完成了本發明。
即,本發明提供一種苯酚酚醛清漆樹脂、及含有其之硬化性樹脂組成物與其硬化物,該苯酚酚醛清漆樹脂之特徵在於:其係具有碳數4~8之烷基作為芳香環上之取代基的烷基苯酚(I)經由亞甲基連結而成之烷基苯酚酚醛清漆樹脂,且13C-NMR測定中之146~148ppm之積分值(a)與146~153ppm之積分值(b)的比(a)/(b)為0.05~0.30之範圍,並且GPC測定中之烷基苯酚(I)之面積比為0.01~3.0%之範圍。
根據本發明,可提供於樹脂組成物之加熱硬化時之成形收縮率、彈性模數之平衡性優異且可較佳地用於半導體密封材料等之苯酚酚醛清漆樹脂、硬化性樹脂組成物、兼備上述性能之硬化物、半導體密封材料、半導體裝置、預浸體、電路基板、增層膜、增層基板、纖維強化複合材料、及纖維強化成形品。
圖1係於合成例1中合成之苯酚酚醛清漆樹脂(A-1)之 13C-NMR圖。
圖2係於合成例1中合成之苯酚酚醛清漆樹脂(A-1)之GPC圖。
圖3係於合成例3中合成之苯酚酚醛清漆樹脂(A-3)之13C-NMR圖。
圖4係於合成例3中合成之苯酚酚醛清漆樹脂(A-3)之GPC圖。
圖5係於比較合成例1中合成之苯酚酚醛清漆樹脂(A'-1)之13C-NMR圖。
圖6係於比較合成例1中合成之苯酚酚醛清漆樹脂(A'-1)之GPC圖。
圖7係於比較合成例2中合成之苯酚酚醛清漆樹脂(A'-2)之13C-NMR圖。
圖8係於比較合成例2中合成之苯酚酚醛清漆樹脂(A'-2)之GPC圖。
圖9係於比較合成例3中合成之苯酚酚醛清漆樹脂(A'-3)之13C-NMR圖。
圖10係於比較合成例3中合成之苯酚酚醛清漆樹脂(A'-3)之GPC圖。
<苯酚酚醛清漆樹脂>
以下,對本發明進行詳細說明。
本發明之苯酚酚醛清漆樹脂係將具有碳數4~8之烷基作為芳香環上之 取代基的烷基苯酚(I)作為原料者,其特徵在於:13C-NMR測定中之146~148ppm之積分值(a)與146~153ppm之積分值(b)的比即(a)/(b)為0.05~0.35之範圍,並且GPC測定中之烷基苯酚(I)之面積比為0.01~3.0%之範圍。
於13C-NMR測定中,在146~148ppm、146~153ppm之各範圍內檢測出之峰值為於構成該苯酚酚醛清漆樹脂之芳香環中來自與羥基鍵結之碳原子的峰值,146~148ppm歸屬於1分子中之存在於末端以外之芳香環,146~153ppm歸屬於1分子中之與羥基鍵結之芳香環之全部碳原子。
於本發明中,發現若使用該峰值之比(a)/(b)在一定範圍內、具體而言在0.05~0.30之範圍內之樹脂作為硬化性樹脂組成物之1成分,則藉由具有碳數4~8之烷基作為芳香環上之取代基,而於加熱硬化時之成形收縮率、彈性模數之平衡性優異。若該比(a)/(b)未達0.05,則硬化物之交聯密度不足,因而耐熱性不足且成形收縮率變大。又,若超過0.30,則熔融黏度對於密封材料而言不適合,此外苯酚酚醛清漆樹脂中之內部之羥基濃度變高,而且體積大之取代基成為位阻,因此無助於硬化反應之羥基變得容易殘存,硬化時之成形收縮率變高,且硬化物之耐熱性降低,故而不實用。
再者,本發明中之13C-NMR係藉由下述測定方法進行。
裝置:日本電子股份有限公司製造AL-400
測定模式:帶反向閘極之去耦
溶劑:氘氯仿
脈衝角度:30°脈衝
試樣濃度:30wt%
累計次數:4000次
進而,於本發明之苯酚酚醛清漆樹脂中以GPC測定中之面積比計為0.01~3.0%之範圍含有用作原料之烷基苯酚(I)。藉由於該範圍內含有烷基苯酚(I),而硬化物中之交聯密度成為適宜之範圍,從而成為耐熱性與成形收縮率之平衡性優異者。
本發明之苯酚酚醛清漆樹脂可例示下述通式(1)
[式(1)中,R1、R2、R3分別獨立地為氫原子或碳數4~8之烷基,至少任一者為碳數4~8之烷基,n為0~5之整數]
所表示者。即,就硬化反應良好地進行之觀點、原料於工業上容易獲得之觀點、加熱硬化時之成形收縮率、彈性模數之平衡性更優異之觀點而言,芳香環上之取代基較佳為相對於苯酚之羥基為鄰位、對位。進而,作為重複數之平均值,更佳為0.01~2之範圍。
尤其是於與後述之其他樹脂組合而製成硬化性樹脂組成物 時,就硬化物之交聯密度容易設為更適當之範圍之觀點而言,芳香環上之取代基較佳為第三丁基、第三辛基等具有分支結構之烷基,尤其最佳為第三丁基。
又,就硬化物之耐熱性、成形收縮率、彈性模數、樹脂之熔融黏度的平衡性優異之方面而言,較佳為上述通式(1)中之R1、R2、R3之任一者或兩者為第三丁基,進一步較佳為R1為第三丁基且R2、R3為氫原子。
再者,本發明中之上述通式(1)中之n可藉由下述條件之GPC測定而求出。
<GPC測定條件>
測定裝置:Tosoh股份有限公司製造「HLC-8320 GPC」
管柱:Tosoh股份有限公司製造Guard Column「HXL-L」
+Tosoh股份有限公司製造「TSK-GEL G2000HXL」
+Tosoh股份有限公司製造「TSK-GEL G2000HXL」
+Tosoh股份有限公司製造「TSK-GEL G3000HXL」
+Tosoh股份有限公司製造「TSK-GEL G4000HXL」
檢測器:RI(示差折射計)
資料處理:Tosoh股份有限公司製造之「GPC工作站EcoSEC-WorkStation」
測定條件:管柱溫度40℃
展開溶劑 四氫呋喃
流速 1.0ml/分
標準:依據上述「GPC工作站EcoSEC-WorkStation」之測定指南,使用分子量已知之下述單分散聚苯乙烯。
(使用聚苯乙烯)
Tosoh股份有限公司製造之「A-500」
Tosoh股份有限公司製造之「A-1000」
Tosoh股份有限公司製造之「A-2500」
Tosoh股份有限公司製造之「A-5000」
Tosoh股份有限公司製造之「F-1」
Tosoh股份有限公司製造之「F-2」
Tosoh股份有限公司製造之「F-4」
Tosoh股份有限公司製造之「F-10」
Tosoh股份有限公司製造之「F-20」
Tosoh股份有限公司製造之「F-40」
Tosoh股份有限公司製造之「F-80」
Tosoh股份有限公司製造之「F-128」
試樣:利用微量過濾器對以樹脂固形物成分換算計為1.0質量%之四氫呋喃溶液進行過濾而得者(50μl)。
<苯酚酚醛清漆樹脂之製造方法>
如上所述,本發明之苯酚酚醛清漆樹脂如上所述般提供特定之13C-NMR圖。作為獲得此種苯酚酚醛清漆樹脂之方法,可列舉使用具有碳數4~8之烷基作為芳香環上之取代基的烷基苯酚(I),於醛類及酸性觸媒下且於50~180℃之條件下使之反應之方法。
作為上述具有碳數4~8之烷基作為芳香環上之取代基的烷基苯酚(I),例如可列舉第三丁基苯酚、二(第三丁基)苯酚、第三辛基苯酚等,可為僅由1種所構成者,亦可混合2種以上使用。該等之中,就使用所獲得之苯酚酚醛清漆樹脂的硬化性樹脂組成物之加熱收縮率之觀點而言,較佳為具有更大體積之結構之烷基者,進而就原料之獲得容易性、所獲得之樹脂組成物之硬化時的特性之觀點而言,較佳為使用對第三丁基苯酚、鄰第三丁基苯酚、2,4-二(第三丁基)苯酚、對第三辛基苯酚,最佳為使用對第三丁基苯酚。
作為上述醛類,只要為能夠與上述烷基苯酚(I)發生縮合反應而形成酚醛清漆型樹脂者即可,例如可列舉:甲醛、三烷、乙醛、丙醛、四甲醛、聚甲醛、三氯乙醛、六亞甲基四胺等。該等可分別單獨使用,亦可併用2種以上。其中,就反應性優異之方面而言,較佳為使用甲醛。甲醛可以為水溶液狀態之福馬林之形式使用,亦可以為固形物狀態之對甲醛之形式使用。
又,上述酸性觸媒例如可列舉:鹽酸、硫酸、磷酸等無機酸;甲磺酸、對甲苯磺酸、草酸等有機酸;三氟化硼、無水氯化鋁、氯化鋅等路易斯酸等。該等可分別單獨使用,亦可併用2種以上。
作為效率良好地獲得本發明之苯酚酚醛清漆樹脂之方法,例如可列舉相對於烷基苯酚(I)中之羥基1莫耳,於0.05~0.40莫耳之範圍內使用上述醛類,並在上述酸性觸媒之存在下且在50~180℃之溫度條件下進行反應之方法。
上述烷基苯酚(I)與上述醛類之反應亦可視需要於溶劑中進 行。此處所用之溶劑例如可列舉:水;甲醇、乙醇、丙醇、乳酸乙酯、乙二醇、1,2-丙二醇、1,3-丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,7-庚二醇、1,8-辛二醇、1,9-壬二醇、三亞甲基二醇、二乙二醇、聚乙二醇、甘油、2-乙氧基乙醇、乙二醇單甲醚、乙二醇單乙醚、乙二醇單丙醚、乙二醇單丁醚、乙二醇單戊醚、乙二醇二甲醚、乙二醇甲乙醚、乙二醇單苯醚、二乙二醇甲乙醚、丙二醇單甲醚、1,3-二烷、1,4-二烷、四氫呋喃、乙二醇乙酸酯、丙酮、甲基乙基酮、甲基異丁基酮、環己酮、N-甲基吡咯啶酮、二甲基甲醯胺、二甲基亞碸等。該等溶劑可分別單獨使用,亦可作為2種以上之混合溶劑而使用。
反應結束後亦進行如下步驟等:可視需要將未反應原料或溶劑等蒸餾去除;藉由水洗或再沈澱等進行純化。
<硬化性樹脂組成物>
本發明之苯酚酚醛清漆樹脂藉由併用具有與羥基反應之官能基之其他化合物,可製成硬化性樹脂組成物。硬化性樹脂組成物可較佳地用於接著劑或塗料、光阻劑、印刷配線基板、半導體密封材料等各種電氣、電子構件用途。
本發明中所用之具有與羥基反應之官能基的其他化合物例如可列舉:經選自羥甲基、烷氧基甲基、醯氧基甲基中之至少一個基取代之三聚氰胺化合物、胍胺化合物、乙炔脲化合物、脲化合物、可溶酚醛樹脂、環氧樹脂、異氰酸酯化合物、疊氮化合物、含有烯基醚基等雙鍵之化合物、酸酐、唑啉化合物等。
上述三聚氰胺化合物例如可列舉:六羥甲基三聚氰胺、六甲 氧基甲基三聚氰胺、六羥甲基三聚氰胺之1~6個羥甲基經甲氧基甲基化之化合物;六甲氧基乙基三聚氰胺、六醯氧基甲基三聚氰胺、六羥甲基三聚氰胺之羥甲基之1~6個經醯氧基甲基化之化合物等。
上述胍胺化合物例如可列舉:四羥甲基胍胺、四甲氧基甲基胍胺、四甲氧基甲基苯胍胺、四羥甲基胍胺之1~4個羥甲基經甲氧基甲基化之化合物;四甲氧基乙基胍胺、四醯氧基胍胺、四羥甲基胍胺之1~4個羥甲基經醯氧基甲基化之化合物等。
上述乙炔脲化合物例如可列舉:1,3,4,6-四(甲氧基甲基)乙炔脲、1,3,4,6-四(丁氧基甲基)乙炔脲、1,3,4,6-四(羥基甲基)乙炔脲等。
上述脲化合物例如可列舉:1,3-雙(羥基甲基)脲、1,1,3,3-四(丁氧基甲基)脲及1,1,3,3-四(甲氧基甲基)脲等。
上述可溶酚醛樹脂例如可列舉:使苯酚、甲酚或二甲苯酚等烷基苯酚、苯基苯酚、間苯二酚、聯苯、雙酚A或雙酚F等雙酚、萘酚、二羥基萘等含酚性羥基化合物與醛化合物於鹼性觸媒條件下反應而獲得之聚合物。
上述環氧樹脂例如可列舉:雙酚A型環氧樹脂、雙酚F型環氧樹脂、聯苯型環氧樹脂、四甲基聯苯型環氧樹脂、多羥基萘型環氧樹脂、苯酚酚醛清漆型環氧樹脂、甲酚酚醛清漆型環氧樹脂、三苯基甲烷型環氧樹脂、四苯基乙烷型環氧樹脂、二環戊二烯-苯酚加成反應型環氧樹脂、苯酚芳烷基型環氧樹脂、萘酚酚醛清漆型環氧樹脂、二縮水甘油氧基萘、萘酚芳烷基型環氧樹脂、萘酚-苯酚共縮酚醛清漆型環氧樹脂、萘酚 -甲酚共縮酚醛清漆型環氧樹脂、芳香族烴甲醛樹脂改質苯酚樹脂型環氧樹脂、聯苯改質酚醛清漆型環氧樹脂、1,1-雙(2,7-二縮水甘油氧基-1-萘基)烷烴、萘醚型環氧樹脂、三苯基甲烷型環氧樹脂、含磷原子環氧樹脂、含酚性羥基化合物與含烷氧基芳香族化合物之共縮合物的聚縮水甘油醚等。該等環氧樹脂中,尤其就可獲得難燃性優異之硬化物之方面而言,較佳為使用四甲基聯苯酚型環氧樹脂、聯苯芳烷基型環氧樹脂、多羥基萘型環氧樹脂、酚醛清漆型環氧樹脂,就可獲得介電特性優異之硬化物之方面而言,較佳為二環戊二烯-苯酚加成反應型環氧樹脂。
上述異氰酸酯化合物例如可列舉:甲苯二異氰酸酯、二苯基甲烷二異氰酸酯、六亞甲基二異氰酸酯、環己烷二異氰酸酯等。
上述疊氮化物例如可列舉:1,1'-聯苯-4,4'-雙疊氮、4,4'-亞甲基雙疊氮、4,4'-氧基雙疊氮等。
上述含有烯基醚基等雙鍵之化合物例如可列舉:乙二醇二乙烯醚、三乙二醇二乙烯醚、1,2-丙二醇二乙烯醚、1,4-丁二醇二乙烯醚、四亞甲基乙二醇二乙烯醚、新戊二醇二乙烯醚、三羥甲基丙烷三乙烯醚、己二醇二乙烯醚、1,4-環己二醇二乙烯醚、新戊四醇三乙烯醚、新戊四醇四乙烯醚、山梨糖醇四乙烯醚、山梨糖醇五乙烯醚、三羥甲基丙烷三乙烯醚等。
上述酸酐例如可列舉:鄰苯二甲酸酐、偏苯三甲酸酐、均苯四甲酸二酐、3,3',4,4'-二苯甲酮四羧酸二酐、聯苯四羧酸二酐、4,4'-(亞異丙基)雙鄰苯二甲酸酐、4,4'-(六氟亞異丙基)雙鄰苯二甲酸酐等芳香族酸酐;四氫鄰苯二甲酸酐、甲基四氫鄰苯二甲酸酐、六氫鄰苯二甲酸酐、 甲基六氫鄰苯二甲酸酐、內亞甲基四氫鄰苯二甲酸酐、十二烯基琥珀酸酐、三烷基四氫鄰苯二甲酸酐等脂環式羧酸酐等。
該等之中,就成為硬化性或硬化物之耐熱性優異之硬化性組成物的方面而言,特佳為環氧樹脂。
進而於使用上述環氧樹脂之情形時,亦可摻合環氧樹脂用硬化劑。
作為此處可使用之硬化劑,例如可列舉:胺系化合物、醯胺系化合物、酸酐系化合物、酚系化合物等各種公知之環氧樹脂用硬化劑。
具體而言,作為胺系化合物,可列舉:二胺基二苯基甲烷、二伸乙基三胺、三伸乙基四胺、二胺基二苯基碸、異佛爾酮二胺、咪唑、BF3-胺錯合物、胍衍生物等,作為醯胺系化合物,可列舉:二氰二胺、由次亞麻油酸之二聚物與乙二胺所合成之聚醯胺樹脂等。作為酸酐系化合物,可列舉:鄰苯二甲酸酐、偏苯三甲酸酐、均苯四甲酸二酐、順丁烯二酸酐、四氫鄰苯二甲酸酐、甲基四氫鄰苯二甲酸酐、甲基耐地酸酐、六氫鄰苯二甲酸酐、甲基六氫鄰苯二甲酸酐等。作為酚系化合物,可列舉:苯酚酚醛清漆樹脂、甲酚酚醛清漆樹脂、芳香族烴甲醛樹脂改質苯酚樹脂、二環戊二烯苯酚加成型樹脂、苯酚芳烷基樹脂(ZYLOCK樹脂)、萘酚芳烷基樹脂、三酚基甲烷樹脂、四酚基乙烷樹脂、萘酚酚醛清漆樹脂、萘酚-苯酚共縮酚醛清漆樹脂、萘酚-甲酚共縮酚醛清漆樹脂、聯苯改質苯酚樹脂(苯酚核經雙亞甲基連結而得之含多酚性羥基化合物)、聯苯改質萘酚樹脂(苯酚核經雙亞甲基連結而得之多元萘酚化合物)、胺基三改質苯酚樹脂(苯酚核經三聚氰胺、苯胍胺等連結而得之含多酚性羥基化合物)或含 烷氧基芳香環改質酚醛清漆樹脂(苯酚核及含烷氧基芳香環經甲醛連結而得之含多酚性羥基化合物)等含多酚性羥基化合物。
又,本發明之硬化性樹脂組成物亦可併用其他熱硬化性樹脂。
作為其他熱硬化性樹脂,例如可列舉:氰酸酯樹脂、具有苯并結構之樹脂、順丁烯二醯亞胺化合物、活性酯樹脂、乙烯基苄基化合物、丙烯酸化合物、苯乙烯與順丁烯二酸酐之共聚物等。於併用上述其他熱硬化性樹脂之情形時,其使用量只要不阻礙本發明之效果則不受特別限制,較佳為硬化性樹脂組成物100質量份中為1~50質量份之範圍。
作為上述氰酸酯樹脂,例如可列舉:雙酚A型氰酸酯樹脂、雙酚F型氰酸酯樹脂、雙酚E型氰酸酯樹脂、雙酚S型氰酸酯樹脂、雙酚硫醚型氰酸酯樹脂、苯醚型氰酸酯樹脂、萘醚型氰酸酯樹脂、聯苯型氰酸酯樹脂、四甲基聯苯型氰酸酯樹脂、多羥基萘型氰酸酯樹脂、苯酚酚醛清漆型氰酸酯樹脂、甲酚酚醛清漆型氰酸酯樹脂、三苯基甲烷型氰酸酯樹脂、四苯基乙烷型氰酸酯樹脂、二環戊二烯-苯酚加成反應型氰酸酯樹脂、苯酚芳烷基型氰酸酯樹脂、萘酚酚醛清漆型氰酸酯樹脂、萘酚芳烷基型氰酸酯樹脂、萘酚-苯酚共縮酚醛清漆型氰酸酯樹脂、萘酚-甲酚共縮酚醛清漆型氰酸酯樹脂、芳香族烴甲醛樹脂改質苯酚樹脂型氰酸酯樹脂、聯苯改質酚醛清漆型氰酸酯樹脂、蒽型氰酸酯樹脂等。該等可分別單獨使用,亦可併用2種以上。
該等氰酸酯樹脂中,尤其就可獲得耐熱性優異之硬化物之方面而言,較佳為使用雙酚A型氰酸酯樹脂、雙酚F型氰酸酯樹脂、雙酚E 型氰酸酯樹脂、多羥基萘型氰酸酯樹脂、萘醚型氰酸酯樹脂、酚醛清漆型氰酸酯樹脂,就可獲得介電特性優異之硬化物之方面而言,較佳為二環戊二烯-苯酚加成反應型氰酸酯樹脂。
作為具有苯并結構之樹脂,並無特別限制,例如可列舉:雙酚F與福馬林與苯胺之反應生成物(F-a型苯并樹脂)或二胺基二苯基甲烷與福馬林與苯酚之反應生成物(P-d型苯并樹脂)、雙酚A與福馬林與苯胺之反應生成物、二羥基二苯醚與福馬林與苯胺之反應生成物、二胺基二苯醚與福馬林與苯酚之反應生成物、二環戊二烯-苯酚加成型樹脂與福馬林與苯胺之反應生成物、酚酞與福馬林與苯胺之反應生成物、二苯基硫醚與福馬林與苯胺之反應生成物等。該等可分別單獨使用,亦可併用2種以上。
作為上述順丁烯二醯亞胺化合物,例如可列舉下述結構式(i)~(iii)之任一者所表示之各種化合物等。
(式中,R為m價之有機基,α及β分別為氫原子、鹵素原子、烷基、芳基之任一者,s為1以上之整數)
(式中,R為氫原子、烷基、芳基、芳烷基、鹵素原子、羥基、烷氧基之任一者,s為1~3之整數,t以重複單位之平均數計為0~10)
(式中,R為氫原子、烷基、芳基、芳烷基、鹵素原子、羥基、烷氧基之任一者,s為1~3之整數,t以重複單位之平均數計為0~10)該等可分別單獨使用,亦可併用2種以上。
作為上述活性酯樹脂,並無特別限制,通常可較佳地使用苯酚酯類、苯硫酚酯類、N-羥胺酯類、雜環羥基化合物之酯類等1分子中具有2個以上反應活性較高之酯基的化合物。上述活性酯樹脂較佳為由羧酸化合物及/或硫羧酸化合物、與羥基化合物及/或硫醇基化合物之縮合反應而獲得者。尤其就耐熱性提高之觀點而言,較佳為由羧酸化合物或其鹵化物與羥基化合物所獲得之活性酯樹脂,更佳為由羧酸化合物或其鹵化物、與苯酚化合物及/或萘酚化合物所獲得之活性酯樹脂。作為羧酸化合物,例如可列舉:苯甲酸、乙酸、琥珀酸、順丁烯二酸、伊康酸、鄰苯二甲酸、間苯二甲酸、對苯二甲酸、均苯四甲酸等或其鹵化物。作為苯酚化 合物或萘酚化合物,可列舉:對苯二酚、間苯二酚、雙酚A、雙酚F、雙酚S、二羥基二苯醚、酚酞、甲基化雙酚A、甲基化雙酚F、甲基化雙酚S、苯酚、鄰甲酚、間甲酚、對甲酚、鄰苯二酚、α-萘酚、β-萘酚、1,5-二羥基萘、1,6-二羥基萘、2,6-二羥基萘、二羥基二苯甲酮、三羥基二苯甲酮、四羥基二苯甲酮、間苯三酚、苯三醇、二環戊二烯-苯酚加成型樹脂等。
作為活性酯樹脂,具體而言,較佳為含有二環戊二烯-苯酚加成結構之活性酯系樹脂、含有萘結構之活性酯樹脂、作為苯酚酚醛清漆之乙醯化物之活性酯樹脂、作為苯酚酚醛清漆之苯甲醯基化物之活性酯樹脂等,其中,就於剝離強度之提高方面優異之方面而言,更佳為含有二環戊二烯-苯酚加成結構之活性酯樹脂、含有萘結構之活性酯樹脂。作為含有二環戊二烯-苯酚加成結構之活性酯樹脂,更具體而言,可列舉下述通式(iv)所表示之化合物。
其中,式(iv)中,R為苯基或萘基,u表示0或1,n以重複單位之平均數計為0.05~2.5。再者,就降低樹脂組成物之硬化物之介電損耗正切且提高耐熱性之觀點而言,R較佳為萘基,u較佳為0,又,n較佳為0.25~1.5。
進而,亦可併用各種本發明之苯酚酚醛清漆樹脂以外之酚醛 清漆樹脂、二環戊二烯等脂環式二烯化合物與苯酚化合物之加成聚合樹脂、含酚性羥基化合物與含烷氧基芳香族化合物之改質酚醛清漆樹脂、苯酚芳烷基樹脂(ZYLOCK樹脂)、萘酚芳烷基樹脂、三羥甲基甲烷樹脂、四酚基乙烷樹脂、聯苯改質苯酚樹脂、聯苯改質萘酚樹脂、胺基三改質苯酚樹脂、及各種乙烯基聚合物。
更具體而言,上述各種酚醛清漆樹脂可列舉使苯酚、苯基苯酚、間苯二酚、聯苯、雙酚A或雙酚F等雙酚、萘酚、二羥基萘等含酚性羥基化合物與醛化合物於酸觸媒條件下進行反應而獲得之聚合物。
上述各種乙烯基聚合物可列舉聚羥基苯乙烯、聚苯乙烯、聚乙烯基萘、聚乙烯基蒽、聚乙烯基咔唑、聚茚、聚苊、聚降莰烯、聚環癸烯、聚四環十二烯、聚降三環烯、聚(甲基)丙烯酸酯等乙烯系化合物之均聚物或該等之共聚物。
於使用該等其他樹脂之情形時,本發明之苯酚酚醛清漆樹脂與其他樹脂之摻合比率可視用途任意設定,但就更顯著地表現本發明所發揮之加熱硬化時之成形收縮率、熱時彈性模數之平衡性效果之方面而言,較佳為相對於本發明之苯酚酚醛清漆樹脂100質量份,其他樹脂成為0.5~100質量份之比率。
本發明之硬化性樹脂組成物中亦可併用硬化促進劑。作為硬化促進劑,可列舉:咪唑、二甲胺基吡啶等三級胺化合物;三苯基膦等磷系化合物;三氟化硼、三氟化硼單乙胺錯合物等三氟化硼胺錯合物;硫代二丙酸等有機酸化合物;硫代聯苯酚苯并、磺醯基苯并等苯并化合物;磺醯基化合物等。該等可分別單獨使用,亦可併用2種以上。該等 觸媒之添加量較佳為硬化性樹脂組成物100質量份中為0.001~15質量份之範圍。
又,於使用於對本發明之硬化性樹脂組成物要求較高之難燃性的用途之情形時,亦可摻合實質上不含有鹵素原子之非鹵素系難燃劑。
上述非鹵素系難燃劑例如可列舉磷系難燃劑、氮系難燃劑、聚矽氧系難燃劑、無機系難燃劑、有機金屬鹽系難燃劑等,即便於使用該等時,亦無任何限制,可單獨使用,亦可使用同一系之多種難燃劑,又,亦可將不同系之難燃劑組合使用。
上述磷系難燃劑可使用無機系、有機系均可。作為無機系化合物,例如可列舉紅磷、磷酸一銨、磷酸二銨、磷酸三銨、多磷酸銨等磷酸銨類、磷醯胺等無機系含氮磷化合物。
又,上述紅磷較佳為以防止水解等為目的而實施表面處理,作為表面處理方法,例如可列舉如下方法等:(i)藉由氫氧化鎂、氫氧化鋁、氫氧化鋅、氫氧化鈦、氧化鉍、氫氧化鉍、硝酸鉍或該等之混合物等無機化合物進行被覆處理;(ii)藉由氫氧化鎂、氫氧化鋁、氫氧化鋅、氫氧化鈦等無機化合物、及苯酚樹脂等熱硬化性樹脂之混合物進行被覆處理;(iii)於氫氧化鎂、氫氧化鋁、氫氧化鋅、氫氧化鈦等無機化合物之被膜上藉由苯酚樹脂等熱硬化性樹脂進行雙層被覆處理。
上述有機磷系化合物例如除磷酸酯化合物、膦酸化合物、次膦酸化合物、氧化膦化合物、磷烷化合物、有機系含氮磷化合物等通用有機磷系化合物以外,還可列舉:9,10-二氫-9--10-磷雜菲-10-氧化物、10-(2,5-二羥基苯基)-10H-9--10-磷雜菲-10-氧化物、 10-(2,7-二羥基萘基)-10H-9--10-磷雜菲-10-氧化物等環狀有機磷化合物、及使其與環氧樹脂或苯酚樹脂等化合物進行反應而得之衍生物等。
該等磷系難燃劑之摻合量根據磷系難燃劑之種類、樹脂組成物之其他成分、所需難燃性之程度進行適當選擇,但例如在摻合非鹵素系難燃劑及其他填充材料或添加劑等全部而得之樹脂組成物100質量份中,於使用紅磷作為非鹵素系難燃劑之情形時,較佳為以0.1質量份~2.0質量份之範圍進行摻合,於使用有機磷化合物之情形時,同樣地較佳為以0.1質量份~10.0質量份之範圍進行摻合,更佳為以0.5質量份~6.0質量份之範圍進行摻合。
又,於使用上述磷系難燃劑之情形時,亦可於該磷系難燃劑中併用鋁碳酸鎂、氫氧化鎂、硼化合物、氧化鋯、黑色染料、碳酸鈣、沸石、鉬酸鋅、活性碳等。
上述氮系難燃劑例如可列舉:三化合物、三聚氰酸化合物、異三聚氰酸化合物、啡噻等,較佳為三化合物、三聚氰酸化合物、異三聚氰酸化合物。
上述三化合物例如可列舉:三聚氰胺、乙胍、苯胍胺、蜜瓜胺(melon)、蜜白胺、琥珀醯胍胺、伸乙基雙三聚氰胺、多磷酸三聚氰胺、三胍胺等,此外還可列舉例如(1)硫酸胍三聚氰胺、硫酸蜜勒胺、硫酸蜜白胺等硫酸胺基三化合物;(2)苯酚、甲酚、二甲苯酚、丁基苯酚、壬基苯酚等酚類與三聚氰胺、苯胍胺、乙胍、甲胍胺等三聚氰胺類及甲醛之共縮合物;(3)上述(2)之共縮合物與苯酚甲醛縮合物等苯酚樹 脂類之混合物;(4)進而藉由桐油、異構化亞麻仁油等將上述(2)、(3)改質而成者等。
上述三聚氰酸化合物例如可列舉三聚氰酸、三聚氰酸三聚氰胺等。
上述氮系難燃劑之摻合量根據氮系難燃劑之種類、樹脂組成物之其他成分、所需難燃性之程度進行適當選擇,例如較佳為於摻合非鹵素系難燃劑及其他填充材料或添加劑等全部而得之樹脂組成物100質量份中以0.05~10質量份之範圍進行摻合,更佳為以0.1質量份~5質量份之範圍進行摻合。
又,於使用上述氮系難燃劑時,亦可併用金屬氫氧化物、鉬化合物等。
上述聚矽氧系難燃劑只要為含有矽原子之有機化合物,則可無特別限制地使用,例如可列舉聚矽氧油、聚矽氧橡膠、聚矽氧樹脂等。上述聚矽氧系難燃劑之摻合量根據聚矽氧系難燃劑之種類、樹脂組成物之其他成分、所需難燃性之程度進行適當選擇,例如較佳為於摻合非鹵素系難燃劑及其他填充材料或添加劑等全部而得之樹脂組成物100質量份中以0.05~20質量份之範圍進行摻合。又,於使用上述聚矽氧系難燃劑時,亦可併用鉬化合物、氧化鋁等。
上述無機系難燃劑例如可列舉:金屬氫氧化物、金屬氧化物、金屬碳酸鹽化合物、金屬粉、硼化合物、低熔點玻璃等。
上述金屬氫氧化物例如可列舉:氫氧化鋁、氫氧化鎂、白雲石、鋁碳酸鎂、氫氧化鈣、氫氧化鋇、氫氧化鋯等。
上述金屬氧化物例如可列舉:鉬酸鋅、三氧化鉬、錫酸鋅、氧化錫、氧化鋁、氧化鐵、氧化鈦、氧化錳、氧化鋯、氧化鋅、氧化鉬、氧化鈷、氧化鉍、氧化鉻、氧化鎳、氧化銅、氧化鎢等。
上述金屬碳酸鹽化合物例如可列舉:碳酸鋅、碳酸鎂、碳酸鈣、碳酸鋇、鹼性碳酸鎂、碳酸鋁、碳酸鐵、碳酸鈷、碳酸鈦等。
上述金屬粉例如可列舉:鋁、鐵、鈦、錳、鋅、鉬、鈷、鉍、鉻、鎳、銅、鎢、錫等。
上述硼化合物例如可列舉:硼酸鋅、偏硼酸鋅、偏硼酸鋇、硼酸、硼砂等。
上述低熔點玻璃例如可列舉Shipuri(Bokusui Brown公司)、水合玻璃SiO2-MgO-H2O、PbO-B2O3系、ZnO-P2O5-MgO系、P2O5-B2O3-PbO-MgO系、P-Sn-O-F系、PbO-V2O5-TeO2系、Al2O3-H2O系、硼矽酸鉛系等玻璃狀化合物。
上述無機系難燃劑之摻合量根據無機系難燃劑之種類、樹脂組成物之其他成分、所需難燃性之程度進行適當選擇,例如較佳為於摻合非鹵素系難燃劑及其他填充材料或添加劑等全部而得之樹脂組成物100質量份中以0.05質量份~20質量份之範圍進行摻合,更佳為以0.5質量份~15質量份之範圍進行摻合。
上述有機金屬鹽系難燃劑例如可列舉:二茂鐵、乙醯丙酮金屬錯合物、有機金屬羰基化合物、有機鈷鹽化合物、有機磺酸金屬鹽、金屬原子與芳香族化合物或雜環化合物經離子鍵結或配位鍵結而成之化合物等。
上述有機金屬鹽系難燃劑之摻合量根據有機金屬鹽系難燃劑之種類、樹脂組成物之其他成分、所需難燃性之程度進行適當選擇,例如較佳為於摻合非鹵素系難燃劑及其他填充材料或添加劑等全部而得之樹脂組成物100質量份中以0.005質量份~10質量份之範圍進行摻合。
本發明之硬化性樹脂組成物可視需要摻合無機填充材料。上述無機填充材料例如可列舉:熔融二氧化矽、結晶二氧化矽、氧化鋁、氮化矽、氫氧化鋁等。於尤其增大上述無機填充材料之摻合量之情形時,較佳為使用熔融二氧化矽。上述熔融二氧化矽可以破碎狀、球狀之任一形狀使用,但為了提高熔融二氧化矽之摻合量且抑制成形材料之熔融黏度之上升,較佳為主要使用球狀者。進而為了提高球狀二氧化矽之摻合量,較佳為適當調整球狀二氧化矽之粒度分佈。考慮到難燃性,其填充率較佳為較高,特佳為相對於環氧樹脂組成物之全部質量為20質量%以上。又,於用於導電膏等用途之情形時,可使用銀粉或銅粉等導電性填充劑。
此外,本發明之硬化性樹脂組成物還可視需要添加矽烷偶合劑、脫模劑、顏料、乳化劑等各種摻合劑。
<硬化性樹脂組成物之用途>
本發明之硬化性樹脂組成物能夠應用於半導體密封材料、半導體裝置、預浸體、印刷電路基板、增層基板、增層膜、纖維強化複合材料、纖維強化樹脂成形品、導電膏等。
1.半導體密封材料
作為由本發明之硬化性樹脂組成物獲得半導體密封材料之方法,可列舉如下方法,即,視需要利用擠出機、捏合機、輥等將上述硬化性樹脂組 成物、及無機填充劑等摻合劑充分地熔融並混合直至變得均勻。此時,作為無機填充劑,通常使用熔融二氧化矽,但於用作功率電晶體、功率IC用高導熱半導體密封材料之情形時,較佳為使用熱導率高於熔融二氧化矽之結晶二氧化矽;氧化鋁、氮化矽等之高填充化;或可使用熔融二氧化矽、結晶二氧化矽、氧化鋁、氮化矽等。其填充率較佳為以相對於硬化性樹脂組成物100質量份為30質量份~95質量份之範圍使用無機填充劑,其中,為了實現難燃性或耐濕性或耐焊裂性之提高、線膨脹係數之降低,更佳為70質量份以上,進而較佳為80質量份以上。
2.半導體裝置
作為由本發明之硬化性樹脂組成物獲得半導體裝置之方法,可列舉如下方法,即,利用澆鑄模具、或轉注成形機、射出成形機等將上述半導體密封材料成形進而以50~200℃加熱2~10小時。
3.預浸體
作為由本發明之硬化性樹脂組成物獲得預浸體之方法,可列舉如下方法,即,藉由將摻合有機溶劑而清漆化之硬化性樹脂組成物含浸於強化基材(紙、玻璃布、玻璃不織布、聚芳醯胺紙、聚芳醯胺布、玻璃氈、玻璃粗紗布等)中後,以與所使用之溶劑種類對應之加熱溫度、較佳為50~170℃進行加熱而獲得。作為此時所用之樹脂組成物與強化基材之質量比率,並無特別限定,通常較佳為以預浸體中之樹脂成分成為20質量%~60質量%之方式進行製備。
作為此處所使用之有機溶劑,可列舉:甲基乙基酮、丙酮、二甲基甲醯胺、甲基異丁基酮、甲氧基丙醇、環己酮、甲基賽珞蘇、乙基 二乙二醇乙酸酯、丙二醇單甲醚乙酸酯等,其的選擇或適當之使用量可根據用途進行適當選擇,例如於如下所述般由預浸體進而製造印刷電路基板之情形時,較佳為使用甲基乙基酮、丙酮、二甲基甲醯胺等沸點為160℃以下之極性溶劑,又,較佳為以不揮發成分成為40質量%~80質量%之比率使用。
4.印刷電路基板
作為由本發明之硬化性樹脂組成物獲得印刷電路基板之方法,可列舉如下方法,即,藉由常規方法積層上述預浸體,適當重疊銅箔,並於1~10MPa之加壓下以170~300℃加熱壓接10分~3小時。
5.增層基板
作為由本發明之硬化性樹脂組成物獲得增層基板之方法,可列舉經由步驟1~3之方法。步驟1中,首先,利用噴塗法、淋幕式塗佈法等將適當摻合有橡膠、填料等之上述硬化性樹脂組成物塗佈於形成有電路之電路基板後,使之硬化。步驟2中,於視需要對塗佈有硬化性樹脂組成物之電路基板進行特定之通孔部等之開孔後,藉由粗化劑進行處理,將其表面熱水洗,藉此使上述基板形成凹凸,對銅等金屬進行鍍覆處理。步驟3中,視需要依序重複步驟1~2之操作,將樹脂絕緣層及特定之電路圖案之導體層交替地增層而形成增層基板。再者,於上述步驟中,通孔部之開孔可於形成最外層之樹脂絕緣層之後進行。又,本發明之增層基板亦可藉由將於銅箔上使該樹脂組成物半硬化後之附樹脂之銅箔在形成有電路之配線基板上以170~300℃進行加熱壓接,而形成粗化面,省略鍍覆處理步驟,製作增層基板。
6.增層膜
作為由本發明之硬化性樹脂組成物獲得增層膜之方法,例如可列舉如下方法,即,於支持膜上塗佈硬化性樹脂組成物後進行乾燥,而於支持膜上形成樹脂組成物層。於將本發明之硬化性樹脂組成物用於增層膜之情形時,該膜以真空層壓法中之層壓之溫度條件(通常為70℃~140℃)進行軟化,並且重要的是顯示在電路基板之層壓之同時能夠於存在於電路基板之導孔或通孔內填充樹脂之流動性(樹脂流動),較佳為以表現此種特性之方式摻合上述各成分。
此處,電路基板之通孔直徑通常為0.1~0.5mm,深度通常為0.1~1.2mm,通常較佳為能夠以此範圍進行樹脂填充。再者,於層壓電路基板之兩面之情形時,較理想為填充通孔之1/2左右。
作為製造上述增層膜之具體方法,可列舉如下方法,即,製備摻合有機溶劑並清漆化而得之樹脂組成物後,於支持膜(Y)之表面塗佈上述組成物,進而藉由加熱、或熱風吹送等乾燥有機溶劑而形成樹脂組成物之層(X)。
作為此處所使用之有機溶劑,例如較佳為使用丙酮、甲基乙基酮、環己酮等酮類;乙酸乙酯、乙酸丁酯、乙酸賽珞蘇、丙二醇單甲醚乙酸酯、卡必醇乙酸酯等乙酸酯類;賽珞蘇;丁基卡必醇等卡必醇類;甲苯、二甲苯等芳香族烴類;二甲基甲醯胺、二甲基乙醯胺、N-甲基吡咯啶酮等,又,較佳為以成為不揮發成分30質量%~60質量%之比率使用。
再者,所形成之上述樹脂組成物之層(X)之厚度通常必須設為導體層之厚度以上。電路基板所具有之導體層之厚度通常為5~70μm 之範圍,故而樹脂組成物層之厚度較佳為具有10~100μm之厚度。再者,本發明中之上述樹脂組成物之層(X)亦可由下述保護膜保護。藉由以保護膜保護,可防止污物等對樹脂組成物層表面之附著或傷痕。
上述支持膜及保護膜可列舉:聚乙烯、聚丙烯、聚氯乙烯等聚烯烴;聚對苯二甲酸乙二酯(以下有時簡稱為「PET」)、聚萘二甲酸乙二酯等聚酯;聚碳酸酯、聚醯亞胺,進而可列舉脫模紙或銅箔、鋁箔等金屬箔等。再者,支持膜及保護膜除泥漿處理、電暈處理以外,亦可實施脫模處理。支持膜之厚度並無特別限定,通常為10~150μm,較佳為以25~50μm之範圍使用。又,保護膜之厚度較佳為設為1~40μm。
上述支持膜(Y)在層壓於電路基板後或藉由進行加熱硬化而形成絕緣層後被剝離。若於構成增層膜之樹脂組成物層經加熱硬化後剝離支持膜(Y),則可防止於硬化步驟中污物等之附著。於在硬化後剝離之情形時,通常對支持膜預先實施脫模處理。
再者,可自以上述方式獲得之增層膜製造多層印刷電路基板。例如於上述樹脂組成物之層(X)由保護膜保護之情形時,在剝離該等後,例如藉由真空層壓法將上述樹脂組成物之層(X)以直接接觸電路基板之方式層壓於電路基板之單面或兩面。層壓之方法可為批次式,亦可為利用輥進行之連續式。又,根據需要,亦可於進行層壓之前視需要預先對增層膜及電路基板進行加熱(預熱)。層壓條件較佳為將壓接溫度(層壓溫度)設為70~140℃,較佳為將壓接壓力設為1~11kgf/cm2(9.8×104~107.9×104N/m2),較佳為於將氣壓設為20mmHg(26.7hPa)以下之減壓下進行層壓。
7.纖維強化複合材料
作為由本發明之樹脂組成物獲得纖維強化複合材料(強化纖維中含浸有樹脂之片狀中間材料)之方法,可列舉如下方法,即,將構成樹脂組成物之各成分均勻地混合而調整清漆,其次,將其含浸於由強化纖維所構成之強化基材後進行聚合反應,藉此來製造。
進行上述聚合反應時之硬化溫度具體而言較佳為50~250℃之溫度範圍,尤佳為於50~100℃進行硬化而製成不黏著狀之硬化物後,進而於120~200℃之溫度條件下進行處理。
此處,強化纖維亦可為有撚紗、解撚紗、或無撚紗等之任一者,但就兼顧纖維強化塑膠製構件之成形性與機械強度之方面而言,較佳為解撚紗或無撚紗。進而,強化纖維之形態可使用纖維方向於一方向上對齊者、或織物。若為織物,則可根據所使用之部位或用途自平紋織物、緞紋織物等中自由選擇。具體而言,就機械強度或耐久性優異之方面而言,可列舉碳纖維、玻璃纖維、聚芳醯胺纖維、硼纖維、氧化鋁纖維、碳化矽纖維等,亦可併用該等之2種以上。該等之中,尤其就成為成形品之強度良好者之方面而言,較佳為碳纖維,該碳纖維可使用聚丙烯腈系、瀝青系、嫘縈系等各者。其中,較佳為可容易獲得高強度之碳纖維之聚丙烯腈系者。此處,將清漆含浸於由強化纖維所構成之強化基材中而製成纖維強化複合材料時的強化纖維之使用量較佳為該纖維強化複合材料中之強化纖維之體積含有率成為40%~85%之範圍之量。
8.纖維強化樹脂成形品
作為由本發明之樹脂組成物獲得纖維強化成形品(強化纖維中含浸有 樹脂之片狀構件經硬化之成形品)之方法,可列舉:於模具鋪設纖維骨材並將上述清漆多重積層之手工塗佈法或噴附法;使由強化纖維所構成之基材一面含浸清漆一面堆積,然後覆蓋能夠使成形、壓力作用於成形物之可撓性模具並將其氣密密封,使用凸模、凹模之任一者對上述氣密密封而成者進行真空(減壓)成型之真空包裝法;將預先將含有強化纖維之清漆製成片狀而得者利用模具進行壓縮成型之SMC加壓法;藉由向充滿纖維之對模注入上述清漆之RTM法等,製造使強化纖維含浸上述清漆而得之預浸體,並利用大型高壓釜將其燒固之方法等。再者,上述獲得之纖維強化樹脂成形品係具有強化纖維與樹脂組成物之硬化物的成形品,具體而言,纖維強化成形品中之強化纖維之量較佳為40質量%~70質量%之範圍,就強度方面而言,特佳為50質量%~70質量%之範圍。
9.導電膏
作為由本發明之樹脂組成物獲得導電膏之方法,例如可列舉使微細導電性粒子分散於該硬化性樹脂組成物中之方法。上述導電膏可根據所使用之微細導電性粒子之種類而製成電路連接用焊膏樹脂組成物或異向性導電接著劑。
其次,藉由實施例、比較例對本發明進行具體說明,但於以下內容中,「份」及「%」只要無特別說明則為質量基準。再者,GPC、13C-NMR光譜係於以下條件下測定。
<GPC測定條件>
測定裝置:Tosoh股份有限公司製造之「HLC-8320 GPC」
管柱:Tosoh股份有限公司製造之Guard Column「HXL-L」
+Tosoh股份有限公司製造之「TSK-GEL G2000HXL」
+Tosoh股份有限公司製造之「TSK-GEL G2000HXL」
+Tosoh股份有限公司製造之「TSK-GEL G3000HXL」
+Tosoh股份有限公司製造之「TSK-GEL G4000HXL」
檢測器:RI(示差折射計)
資料處理:Tosoh股份有限公司製造之「GPC工作站EcoSEC-WorkStation」
測定條件:管柱溫度40℃
展開溶劑 四氫呋喃
流速 1.0ml/分
標準:依據上述「GPC工作站EcoSEC-WorkStation」之測定指南使用分子量已知之下述單分散聚苯乙烯。
(使用聚苯乙烯)
Tosoh股份有限公司製造之「A-500」
Tosoh股份有限公司製造之「A-1000」
Tosoh股份有限公司製造之「A-2500」
Tosoh股份有限公司製造之「A-5000」
Tosoh股份有限公司製造之「F-1」
Tosoh股份有限公司製造之「F-2」
Tosoh股份有限公司製造之「F-4」
Tosoh股份有限公司製造之「F-10」
Tosoh股份有限公司製造之「F-20」
Tosoh股份有限公司製造之「F-40」
Tosoh股份有限公司製造之「F-80」
Tosoh股份有限公司製造之「F-128」
試樣:利用微量過濾器對以樹脂固形物成分換算計為1.0質量%之四氫呋喃溶液進行過濾而得者(50μl)。
<13C-NMR之測定條件>
裝置:日本電子股份有限公司製造AL-400
測定模式:帶反向閘極之去耦
溶劑:氘氯仿
脈衝角度:30°脈衝
試樣濃度:30wt%
累計次數:4000次
合成例1
向安裝有溫度計、滴液漏斗、冷卻管、分餾管、攪拌器之燒瓶中添加對第三丁基苯酚900質量份(6.0莫耳)、草酸18質量份,一面攪拌一面自室溫以45分鐘升溫至98℃。繼而,耗時2小時滴加42質量%福馬林水溶液54質量份(0.75莫耳)。滴加結束後,進而於98℃攪拌1小時,其後以3小時升溫至180℃。反應結束後,於加熱減壓下去除殘留於反應系統內之水分與未反應物而獲得苯酚酚醛清漆樹脂(A-1)。將所獲得之苯酚酚醛清漆樹脂(A-1)之13C-NMR圖示於圖1,且將GPC圖示於圖2。苯酚酚醛清漆樹脂(A-1)之羥基當量為156g/eq,150℃之熔融黏度(ICI)為 0.1dPa‧s,(a)/(b)值為0.07,n=0體之由GPC測得之面積比為0.8%。
合成例2
除將對第三丁基苯酚900質量份(6.0莫耳)變更為對第三丁基苯酚675質量份(4.3莫耳)、鄰第三丁基苯酚225質量份(1.7莫耳)以外,與合成例1同樣地獲得苯酚樹脂(A-2)。所獲得之苯酚酚醛清漆樹脂(A-2)之羥基當量為156g/eq,150℃之熔融黏度(ICI)為0.1dPa‧s,(a)/(b)值為0.07,n=0體之由GPC測得之面積比為0.4%。
合成例3
除將對第三丁基苯酚900質量份(6.0莫耳)變更為對第三丁基苯酚675質量份(4.3莫耳)與2,4-二(第三丁基)苯酚225質量份(1.1莫耳)並將42質量%福馬林水溶液變更為343質量份(4.7莫耳)以外,與合成例1同樣地獲得苯酚樹脂(A-3)。將所獲得之苯酚酚醛清漆樹脂(A-3)之13C-NMR圖示於圖3,且將GPC圖示於圖4。苯酚酚醛清漆樹脂(A-3)之羥基當量為166g/eq,150℃之熔融黏度(ICI)為0.2dPa‧s,(a)/(b)值為0.08,n=0體之由GPC測得之面積比為0.7%。
比較合成例1
除將42質量%福馬林水溶液設為369質量份(5.1莫耳)以外,與合成例1同樣地獲得苯酚樹脂(A'-1)。將所獲得之苯酚酚醛清漆樹脂(A'-1)之13C-NMR圖示於圖5,且將GPC圖示於圖6。所獲得之苯酚酚醛清漆樹脂(A'-1)之羥基當量為157g/eq,(a)/(b)值為0.315,n=0體之面積為0.6%。
比較合成例2
向安裝有溫度計、滴液漏斗、冷卻管、分餾管、攪拌器之燒瓶中添加苯酚酚醛清漆樹脂(A'-1)100質量份、對第三丁基苯酚4質量份,於150℃混合3小時而獲得苯酚酚醛清漆樹脂(A'-2)。將所獲得之苯酚酚醛清漆樹脂(A'-2)之13C-NMR圖示於圖7,且將GPC圖示於圖8。苯酚酚醛清漆樹脂(A'-2)之羥基當量為157g/eq,〔a〕/〔b〕值為0.298,n=0體之面積為4.4%。
比較合成例3
除將對第三丁基苯酚900質量份(6.0莫耳)變更為對第三丁基苯酚675質量份(4.3莫耳)、對第三辛基苯酚225質量份(1.1莫耳)並將42質量%福馬林水溶液變更為343質量份(4.7莫耳)以外,與合成例1同樣地獲得苯酚樹脂(A'-3)。將所獲得之苯酚酚醛清漆樹脂(A'-3)之13C-NMR圖示於圖9,且將GPC圖示於圖10。苯酚酚醛清漆樹脂(A'-3)之羥基當量為168g/eq,150℃之熔融黏度(ICI)為1.9dPa‧s,(a)/(b)值為0.37,n=0體之由GPC測得之面積比為5.1%。
以表1~2中所示之組成摻合下述化合物後,利用2根輥於90℃之溫度下熔融混練5分鐘而製備目標硬化性樹脂組成物。再者,表1~2中之省略符號意指下述化合物。
‧樹脂A-1:合成例1中所獲得之苯酚酚醛清漆樹脂
‧樹脂A-2:合成例2中所獲得之苯酚酚醛清漆樹脂
‧樹脂A-3:合成例3中所獲得之苯酚酚醛清漆樹脂
‧樹脂A'-1:比較合成例1中所獲得之苯酚酚醛清漆樹脂
‧樹脂A'-2:比較合成例2中所獲得之苯酚酚醛清漆樹脂
‧樹脂A'-3:比較合成例3中所獲得之苯酚酚醛清漆樹脂
‧樹脂A'-4:2,2'-亞甲基雙(4-第三丁基苯酚)(羥基當量156g/eq,(a)/(b)值0,n=0體面積0%)
‧環氧樹脂:甲酚酚醛清漆型環氧樹脂「N-655-EXP-S」當量:201g/eq(DIC股份有限公司製造)
‧TPP:三苯基膦
‧熔融二氧化矽:球狀二氧化矽「FB-560」電氣化學股份有限公司製造
‧矽烷偶合劑:γ-縮水甘油氧基三乙氧基矽烷「KBM-403」信越化學工業股份有限公司製造
‧巴西棕櫚蠟:「PEARL WAX No.1-P」電氣化學股份有限公司製造
<流動性之測定>
將上述獲得之硬化性樹脂組成物注入試驗用模具中,於175℃、70kg/cm2、120秒之條件下測定螺旋流動值。將其結果示於表1~2。
其次,利用轉注成形機將粉碎上述獲得之硬化性樹脂組成物而得者於壓力70kg/cm2、溫度175℃、時間180秒下成形為Φ 50mm×3(t)mm之圓板狀,於180℃進而硬化5小時。
<玻璃轉移溫度、彈性模數之測定>
將上述製作之成形物以寬度5mm、長度54mm之尺寸切出厚度0.8mm之硬化物,並將其作為試片1。利用黏彈性測定裝置(DMA:Rheometric公司製造之固體黏彈性測定裝置「RSAII」,矩形張力法:頻率1Hz、升溫速度3℃/分)對該試片1進行測定,將彈性模數變化成為最大(tanδ變化率最大)之溫度作為玻璃轉移溫度、將40℃之儲存模數作為常溫彈性模數、 將260℃之儲存模數作為熱時彈性模數,從而進行測定。
<成形時之收縮率之測定>
利用轉注成形機(Kohtaki Precision Machine Co.,Ltd製造,KTS-15-1.5C),於模具溫度150℃、成形壓力9.8MPa、硬化時間600秒之條件下將樹脂組成物注入成形,而製作長110mm、寬12.7mm、厚1.6mm之試片。其後,將試片於175℃後硬化處理5小時,測定模具模腔之內徑尺寸、及室溫(25℃)下之試片之外徑尺寸,藉由下述式算出收縮率。
收縮率(%)={(模具之內徑尺寸)-(25℃之硬化物之縱向之尺寸)}/(175℃之模具模腔之內徑尺寸)×100(%)
將該等結果示於表1~2。
Claims (15)
- 一種苯酚酚醛清漆樹脂,其係具有碳數4~8之烷基作為芳香環上之取代基的烷基苯酚(I)經由亞甲基連結而成之烷基苯酚酚醛清漆樹脂,且 13C-NMR測定中之146~148ppm之積分值(a)與146~153ppm之積分值(b)的比(a)/(b)為0.05~0.30之範圍,並且GPC測定中之烷基苯酚(I)之面積比為0.01~3.0%之範圍。
- 如申請專利範圍第1項之苯酚酚醛清漆樹脂,其中,上述苯酚酚醛清漆樹脂為下述通式(1)
- 如申請專利範圍第2項之苯酚酚醛清漆樹脂,其中,上述通式(1)中之R 1、R 2、R 3之任一者或兩者為第三丁基,其餘為氫原子。
- 如申請專利範圍第1至3項中任一項之苯酚酚醛清漆樹脂,其中,上述苯酚酚醛清漆樹脂於150℃之ICI黏度為0.01~3.0dPa‧s。
- 一種硬化性樹脂組成物,其係以申請專利範圍第1至3項中任一項之苯酚酚醛清漆樹脂、及具有與羥基反應之官能基之樹脂作為必需成分。
- 如申請專利範圍第5項之硬化性樹脂組成物,其中,上述具有與羥基反應之官能基之樹脂為環氧樹脂。
- 如申請專利範圍第6項之硬化性樹脂組成物,其進而含有上述苯酚酚醛清漆樹脂以外之環氧樹脂用硬化劑。
- 一種硬化物,其係申請專利範圍第5至7項中任一項之硬化性樹脂組成物之硬化物。
- 一種半導體密封材料,其含有申請專利範圍第5至7項中任一項之硬化性樹脂組成物及無機填充材料。
- 一種半導體裝置,其係申請專利範圍第9項之半導體密封材料之硬化物。
- 一種預浸體,其係具有申請專利範圍第5至7項中任一項之硬化性樹脂組成物及補強基材的含浸基材之半硬化物。
- 一種電路基板,其係由申請專利範圍第5至7項中任一項之硬化性樹脂組成物之板狀賦形物及銅箔所構成。
- 一種增層膜,其係由申請專利範圍第5至7項中任一項之硬化性樹脂組成物之硬化物及基材膜所構成。
- 一種纖維強化複合材料,其含有申請專利範圍第5至7項中任一項之硬化性樹脂組成物及強化纖維。
- 一種纖維強化成形品,其係申請專利範圍第14項之纖維強化複合材料之硬化物。
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