TWI475038B - 苯酚樹脂組成物、其硬化物、覆銅積層板用樹脂組成物、覆銅積層板及新穎苯酚樹脂 - Google Patents
苯酚樹脂組成物、其硬化物、覆銅積層板用樹脂組成物、覆銅積層板及新穎苯酚樹脂 Download PDFInfo
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- TWI475038B TWI475038B TW095144077A TW95144077A TWI475038B TW I475038 B TWI475038 B TW I475038B TW 095144077 A TW095144077 A TW 095144077A TW 95144077 A TW95144077 A TW 95144077A TW I475038 B TWI475038 B TW I475038B
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- Prior art keywords
- phenol resin
- resin composition
- group
- compound
- phenol
- Prior art date
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- 239000005011 phenolic resin Substances 0.000 title claims description 145
- 239000000203 mixture Substances 0.000 title claims description 53
- 239000011342 resin composition Substances 0.000 title claims description 25
- -1 cured article Substances 0.000 title claims description 19
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 90
- 150000001875 compounds Chemical class 0.000 claims description 67
- 239000003822 epoxy resin Substances 0.000 claims description 56
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- 229920005989 resin Polymers 0.000 claims description 44
- 239000011347 resin Substances 0.000 claims description 44
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 34
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 23
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000011889 copper foil Substances 0.000 claims description 11
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- 239000004744 fabric Substances 0.000 claims description 8
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- 125000001424 substituent group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
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- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 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 claims description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 4
- 150000001299 aldehydes Chemical class 0.000 description 26
- 238000000034 method Methods 0.000 description 26
- 238000001723 curing Methods 0.000 description 23
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- 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 15
- 238000009826 distribution Methods 0.000 description 14
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- 238000012360 testing method Methods 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 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 7
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- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 6
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- 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 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
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- 238000005530 etching Methods 0.000 description 5
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- 238000002844 melting Methods 0.000 description 5
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 230000003014 reinforcing effect Effects 0.000 description 5
- 229920001187 thermosetting polymer Polymers 0.000 description 5
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
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- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
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- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
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- 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 3
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
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- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 2
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 2
- OENHRRVNRZBNNS-UHFFFAOYSA-N naphthalene-1,8-diol Chemical compound C1=CC(O)=C2C(O)=CC=CC2=C1 OENHRRVNRZBNNS-UHFFFAOYSA-N 0.000 description 2
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 2
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- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- QLORRTLBSJTMSN-UHFFFAOYSA-N tris(2,6-dimethylphenyl) phosphate Chemical compound CC1=CC=CC(C)=C1OP(=O)(OC=1C(=CC=CC=1C)C)OC1=C(C)C=CC=C1C QLORRTLBSJTMSN-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- JOPDZQBPOWAEHC-UHFFFAOYSA-H tristrontium;diphosphate Chemical compound [Sr+2].[Sr+2].[Sr+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O JOPDZQBPOWAEHC-UHFFFAOYSA-H 0.000 description 1
- 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 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
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- C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
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- C08L61/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08L61/04, C08L61/18 and C08L61/20
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- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
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- H05K1/02—Details
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- C08J2361/34—Condensation polymers of aldehydes or ketones with monomers covered by at least two of the groups C08J2361/04, C08J2361/18, and C08J2361/20
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- H05K2203/122—Organic non-polymeric compounds, e.g. oil, wax, thiol
- H05K2203/124—Heterocyclic organic compounds, e.g. azole, furan
Description
本發明係相關於一種使硬化物具備優異的耐熱性及阻燃性且適用於印刷基板用樹脂組成物之苯酚樹脂組成物、其硬化物、印刷基板用樹脂組成物,及兼具優異的耐熱性和阻燃性之覆銅積層板,及使硬化物具備該類性能之新穎苯酚樹脂。
以苯酚樹脂和環氧樹脂為必要成分之硬化性組成物,因可提供具優異的耐熱性、密合性、電絕緣性等之硬化物,故適用於半導體封止材料、印刷基板、塗料、澆鑄材料用途等。該類用途中,電零件、電子零件的技術領域中,樹脂材料需求阻燃性能,例如為使使用為半導體封止材料的樹脂材料具備阻燃性,而摻合溴化環氧樹脂等鹵素系阻燃劑,及使用為阻燃輔劑的三氧化、四氧化、五氧化銻等銻化合物。惟,近年對環境、安全的考量增加,而避免使用會產生戴奧辛的鹵素系阻燃劑和恐引發癌症的銻化合物,因此急需開發一種可取代上述物質且對環境的負荷低之新穎阻燃化方法。
又隨著近年的技術改革,需求兼具高標準的耐熱性、耐濕性、阻燃性、低介電常數、低介電正切、低熱膨脹等之熱硬化性樹脂組成物,因此,組合使用環氧樹脂之苯酚樹脂亦需求附加價值高的耐熱性、耐濕性、阻燃性、低介電常數等性能,特別是急需開發一種無鹵素且具高阻燃性之材料。
為解決上述的問題,提議一種無鹵素且具優異的阻燃性之熱硬化方法,其係一種在環氧樹脂的硬化劑中,使用分子構造內含有三環的酚醛清漆型苯酚樹脂之技術(例如參考下述專利文獻1、2)。
惟,該分子構造內含有三環之酚醛清漆型苯酚樹脂係其硬化物具高度阻燃性,藉由在燃燒時該苯酚樹脂的分子構造被分解並產生惰性氣體之作用,而具有阻燃效果,因此耐熱性差,不易製得耐熱性優異之硬化物。
【專利文獻1】特許第3502042號公報【專利文獻2】特開2001-226464號公報
因此,解決本發明之課題係提供一種可使硬化物具備優異的耐熱性及阻燃性之苯酚樹脂組成物、其硬化物、覆銅積層板用樹脂組成物,及兼具優異的耐熱性和阻燃性之覆銅積層板。
本發明者等為解決上述課題致力研究之結果發現,藉由使用一種在三環上同時含有具羧基的芳香族烴基和胺基的三化合物、使醛類及苯酚類反應而得的縮合物,做為熱硬化性樹脂組成物之主劑,製得的硬化物具有優異的阻燃性,同時發現亦兼具與其相反的性能亦即耐熱性,而完成本發明。
亦即,本發明係相關於一種苯酚樹脂組成物,其特徵係以苯酚樹脂(I)及硬化劑(II)為必要成分,而該苯酚樹脂(I)係在分子結構中含有經以羧基取代的芳香族烴基為鍵結於三環的化學結構(A)(羧基係隔著二價的芳香族烴基而鍵結於三環的化學結構(A))的部分結構。
又,本發明係相關於上述苯酚樹脂組成物中,更加含有有機溶劑為必須成分之覆銅積層板用樹脂組成物。
本發明更相關於一種覆銅積層板,其特徵係使上述覆銅積層板用樹脂組成物含浸於玻璃布(glass cloth)而得聚酯預浸漬物,層積複數的聚酯預浸漬物及銅箔,並使硬化而得。
本發明更相關於一種新穎的苯酚樹脂,其特徵係含有使苯酚類(x1)、以含有含羧基的芳香族烴基及胺基做為三環上的取代基之三化合物(x2)、和醛類(x3)反應而得的分子結構,且該分子結構中含有以下述構造式(1)表示之構造部位,
(式中,R係代表氫原子、碳原子數1~4的脂肪族烴基、芳香族烴基、溴原子或氯原子,虛線係代表與其他分子結構鍵結之鍵,n、m為代表1~4的整數)且於150℃時的ICI熔融黏度為100泊以下。
依據本發明係可提供一種可使硬化物具備優異的耐熱性及阻燃性之苯酚樹脂組成物、其硬化物、新穎苯酚樹脂、覆銅積層板用樹脂組成物,及兼具優異的耐熱性和阻燃性之覆銅積層板。
因此,本發明的苯酚樹脂組成物係特別有助於使用為覆銅積層板用樹脂組成物用途中,因應高密度實裝化和高週波對應化、高速演算化等高性能材料。又,使該組成物熱硬化而成的硬化物,因除具有阻燃性及耐熱性以外,在耐濕性、密合性等亦具有良好的性能,故不僅於電零件、電子零件,亦適用於黏合劑、複合材料等用途。
本發明的苯酚樹脂組成物係如上述般,係以苯酚樹脂(I)及硬化劑(II)為必要成分,而該苯酚樹脂(I)係在分子結構中含有經以羧基取代的芳香族烴基為鍵結於三環的化學結構(A)(羧基係隔著二價的芳香族烴基而鍵結於三環的化學結構(A))的部分結構。因本發明的苯酚樹脂(I)的分子結構中含有三架構,使硬化物暴露於一般燃燒時的300℃高溫環境時,使該三化合物架構分解,釋出惰性氮氣,藉由在模塑物表面形成惰性氣體層,而具有優異的阻燃性。另一方面,使上述苯酚樹脂(I)硬化時,藉由該樹脂中的羧基與硬化劑(II)鍵結,可抑制三架構於高溫環境下過度分解。其結果,分子結構中含有具羧基的三架構(A)之苯酚樹脂(I),係兼具耐熱性和阻燃性的良好平衡性之材料。
上述苯酚樹脂(I)中的經以羧基取代的芳香族烴基鍵結於三環的化學結構(A),係含有羧基和三環乃隔著二價的芳香族烴基而鍵結的結構之部分化學結構。其中二價的芳香族烴基,例如伸苯基、伸萘基、伸聯苯基、及碳原子數1~4的烷基鍵結於其芳香核上之結構者等。具體而言,本發明的化學結構(A)係以下述結構式(1)所示者,惟宜為具有顯著的硬化物的耐熱性之改善效果者。
式中,R係代表氫原子;甲基、乙基、丙基、異丙基、第三丁基等碳原子數1~4的脂肪族烴基;苯基、萘基、聯苯基等芳香族烴基、溴原子或氯原子。虛線係代表與其他分子結構鍵結之鍵,n、m為代表1~4的整數。
結構式(1)中含有下述結構式所示的苯甲酸結構之三結構,因具優異的耐熱性之改善效果故特別理想。
上述在分子結構內含有含羧基的三架構(A)之苯酚樹脂(I),具體而言,係使苯酚類(x1)、以含有含羧基的芳香族烴基及胺基做為三環上的取代基之三化合物(x2)、和醛類(x3)反應而得的分子結構,因硬化物的硬化性及阻燃性良好故特別理想。
其中使用的苯酚類(x1),例如苯酚、鄰-甲苯酚、間-甲苯酚、對-甲苯酚、鄰-乙基苯酚、間-乙基苯酚、對-乙基苯酚、鄰-異丙基苯酚、間-丙基苯酚、對-丙基苯酚、對-第二丁基苯酚、對-第三丁基苯酚、對-環己基苯酚、對氯基苯酚、鄰-溴基苯酚、間-溴基苯酚、對-溴基苯酚等苯酚類、α-萘酚、β-萘酚等萘酚類、2,4-二甲苯酚、2,5-二甲苯酚、2,6-二甲苯酚等二甲苯酚類等一價苯酚類;間苯二酚、兒茶酚、氫酮、2,2-雙(4’-羥苯基)丙烷、1,1’-雙(二羥苯基)甲烷、1,1’-雙(二羥萘基)甲烷、四甲基二苯酚、二苯酚、六甲基二苯酚、1,2-二羥萘、1,3-二羥萘、1,4-二羥萘、1,5-二羥萘、1,6-二羥萘、1,7-二羥萘、1,8-二羥萘、2,3-二羥萘、2,6-二羥萘、2,7-二羥萘等萘二醇類等二價苯酚類;三羥苯基甲烷等三價苯酚類。
其中,宜為苯酚、鄰-甲苯酚、間-甲苯酚、萘酚類、2,2-雙(4’-羥苯基)丙烷、2,6-二甲苯酚、間苯二酚、氫酮、1,5-二羥萘、1,6-二羥萘、2,7-二羥萘,係因容易工業化生產,且可製得硬化性優異的苯酚樹脂(I),尤宜苯酚、鄰-甲苯酚。
以含有含羧基的芳香族烴基及胺基做為三環上的取代基之三化合物(x2),例如羧萘基-1,3,5-三-2,4-二胺;羧苯基-1,3,5-三-2,4-二胺;其他如下述結構式(2)表示之化合物。
其中,尤宜上述結構式(2)表示的化合物,係因具顯著的耐熱性之改善效果。
上述醛類(x3)例如甲醛、仲甲醛、乙醛、巴豆醛等脂肪族醛;苯甲醛、4-甲基苯甲醛、3,4-二甲基苯甲醛、聯苯醛、萘醛等芳香族醛、水楊醛、3-羥苯甲醛、4-羥苯甲醛、2-羥-4-甲基苯甲醛、2-羥-3,4-二甲基苯甲醛、4-羥聯苯醛、2-羥-1-萘醛、5-羥-1-萘醛、6-羥-1-萘醛、7-羥-2-萘醛等羥基取代芳香族醛。其中,因具優異的工業供應安定性、製得的硬化物的耐熱性、阻燃性、介電特性等,宜為甲醛、仲甲醛、苯甲醛、水楊醛,尤宜甲醛、仲甲醛。
上述苯酚樹脂(I)亦可為使苯酚類(x1)、含羧基、胺基及三架構之化合物(x2)及醛類(x3),更加上與含有化合物(x2)之外的含胺基的三架構之化合物(x4)反應而得的結構者。藉由使用該化合物(x4),容易調整硬化物的阻燃性和耐熱性之平衡。
上述含三環之化合物(x4)無特別的限制,例如下述結構式(3)表示之化合物。
上述結構式(3)表示的化合物,具體而言例如三聚氰胺、或甲基胍胺、苯胍胺等胍胺衍生物、三聚氰酸、或甲基三聚氰酸酯、乙基三聚氰酸酯、乙醯基三聚氰酸酯、氯化三聚氰酸等三聚氰酸衍生物等。其中,尤宜R1
、R2
、R3
中任2個或3個為胺基之三聚氰胺、甲基胍胺、苯胍胺等胍胺衍生物,係因容易工業地製得。
使用於本發明的苯酚樹脂(I)係使上述(x1)~(x3)的各成分,或(x1)~(x4)的各成分反應而得,具體而言例如苯酚酚醛清漆樹脂的分子結構中含有下述結構a或結構b者。
其中,結構c中R、m、n、X係與上述結構a或結構b中的同義,p表示為1~5之整數。
又本發明中,上述苯酚樹脂(I)中,含有殘留的未反應苯酚類(x1)之比率宜為3質量%以下。含有未反應苯酚類(x1)之比率為3質量%以下時,使其硬化後的硬化物具優異的耐熱性、耐濕性。
其次,使上述(x1)~(x3)的各成分,或(x1)~(x4)的各成分反應而製造苯酚樹脂(I)之方法,具體而言,係使苯酚類(x1)、化合物(x2)及醛類(x3),更依需求加上與上述化合物(x4)於無催化劑或催化劑存在下反應之方法。此時反應系的pH宜為3.0~9.0的範圍。又,各原料的反應順序亦無特別的限制,首先使苯酚類(x1)、醛類(x3)反應,再與化合物(x2)、依需求更與化合物(x4)反應,亦可相反地使醛類(x3)、化合物(x2)、依需求與化合物(x4)反應,再與苯酚類(x1)反應。或同時間使全部的原料反應。
此時,對苯酚類(x1)醛類(x3)的莫耳比無特別的限制,宜為醛類(x3)/苯酚類(x1)=0.1~1.1(莫耳比),尤宜上述比為0.2~0.8。
對苯酚類(x1)化合物(x2)的莫耳比,考量反應系均勻且反應物亦均勻之觀點、及製得的硬化物之交聯密度適當且具優異的硬化物物性之觀點,係宜為化合物(x2)/苯酚類(x1)=0.05~1.50(莫耳比)的範圍,尤宜化合物(x2)/苯酚類(x1)=0.05~0.50(莫耳比)。
又,使用化合物(x4)時,對苯酚類(x1)化合物(x2)和化合物(x4)的總計量的莫耳比,考量反應系均勻且反應物亦均勻之觀點、及製得的硬化物之交聯密度適當且阻燃效果和耐熱性的平衡優異之觀點,係宜為化合物(x2)和化合物(x4)的總計量/苯酚類(x1)=0.05~1.50(莫耳比),尤宜上述比為0.05~0.50之範圍,且宜為化合物(x2)/化合物(x4)=0.05~9.00(莫耳比)。又,若重視物性平衡、耐熱性時,宜為化合物(x2)/化合物(x4)=0.5~7.0(莫耳比)之範圍,相對於此,重視溶劑溶解性時,宜為化合物(x2)/化合物(x4)=0.1~3.0(莫耳比)之範圍。因此,該範圍的重複範圍即化合物(x2)/化合物(x4)=0.5~3.0之範圍,因可製得耐熱性和溶劑溶解性的平衡良好之苯酚樹脂(I)故特別適當。
又,使用催化劑時,鹼性催化劑例如氫氧化鈉、氫氧化鉀、氫氧化鋇等鹼金屬及鹼土類金屬的氰氧化物、及其氧化物、氨、1~3級胺類、六亞甲基四胺、碳酸鈉等,酸催化劑例如鹽酸、硫酸、磺酸、磷酸等無機酸、草酸、醋酸等有機酸、路易士酸、或醋酸鋅等2價金屬鹽等。使用本發明的苯酚樹脂組成物做為電氣電子材料用樹脂時,因不殘留金屬等無機物而成殘留催化劑之狀況較適當,故鹼性催化劑宜使用胺類,酸性催化劑宜使用有機酸。考量上述觀點,本發明的上述反應尤宜在無催化劑下進行。
又,考量反應控制的觀點,上述反應亦可於各種溶劑的存在下進行。亦可依需求實施中和、水洗以去除鹽類等雜質,無催化劑或使用胺類做為催化劑時,亦可不實施去除雜質的操作。
反應結束後,依據常壓蒸餾、真空蒸餾等一般法去除縮合水、未反應的醛類(x3)、苯酚類(x1)、溶劑等。此時,為要製得不含羥甲基的苯酚樹脂(I)宜實施120℃以上的加熱處理。又若為120℃以上的溫度,經過充分的時間可去除羥甲基,惟為更有效率地去除,宜實施更高溫度宜為150℃以上的加熱處理。於此高溫依據製得酚醛清漆樹脂時的一般法,宜於加熱的同時亦實施蒸餾。
依此製得的苯酚樹脂(I),特別是於150℃時的ICI熔融黏度為100泊以下的本發明之新穎苯酚樹脂,因阻燃性和耐熱性的平衡優異,故特別理想,因此,分子結構中含有下述結構式(1)表示的結構部位,
(式中,R係代表氫原子、碳原子數1~4的脂肪族烴基、芳香族烴基、溴原子或氯原子,虛線係代表與其他分子結構鍵結之鍵,n、m為代表1~4的整數)且尤以於150℃時的ICI熔融黏度為100泊以下的本發明之新穎苯酚樹脂特別適當。
又,上述苯酚樹脂(I)的熔融黏度,尤宜在150℃時的ICI熔融黏度為30~100泊,係因此時樹脂的流動性和硬化物的優異的耐熱性及阻燃性之平衡佳。
又,上述苯酚樹脂(I)的分子結構中氮原子的含有率宜為2~13質量%。亦即如上述般,該樹脂中所含的三架構毫無浪費且有效率地提供阻燃效果,故苯酚樹脂(I)即使氮原子的含量少仍具優異的阻燃效果。因此,與先前的含20質量%氮原子之ATN樹脂(胺基三酚醛樹脂)相比較,即使氮原子含量遠少於上述者,仍具優異的阻燃效果,此乃其特點。如此,因可降低苯酚樹脂(I)中的氮原子含量,苯酚樹脂(I)的熔融黏度低而熔融時的流動性明顯地提昇,藉由印刷基板用途中漆的低黏度化而明顯地提昇作業性。又,苯酚樹脂(I)中的氮原子含量係可由原料成分的總計使用質量、化合物(x2)及化合物(x4)的使用質量與氮原子的質量而算出。
上述苯酚樹脂(I)的分子量分布(Mw/Mn)宜為2~5之範圍。亦即,Mw/Mn為2以上時,溶劑溶解性良好,另一方面,Mw/Mn為5以下時,阻燃效果良好。
又,上述苯酚樹脂(I)為要兼具耐熱性和阻燃性二種相反的性能,宜將該苯酚樹脂(I)中的羧基量調整為適當的範圍,具體而言,羧基的含有率宜符合羧基當量500~1500g/當量的條件。又,苯酚樹脂(I)中的羧基含量可由原料成分的總計使用質量和化合物(x2)的使用質量及羧基的質量而算出。
本發明的苯酚樹脂組成物中的硬化劑(II),例如含有連結伸烷基、聚環氧烷基的2個順丁烯二醯亞胺的結構之脂肪族雙順丁烯二醯亞胺、含有連結伸苯基、伸聯苯基的2個順丁烯二醯亞胺的結構之芳香族雙順丁烯二醯亞胺.順丁烯二醯亞胺基隔著烷基鍵結於苯酚酚醛清漆樹脂的芳香核之多官能順丁烯二醯亞胺化合物、六胺、環氧樹脂。其中於電氣零件、電子零件用途,考量硬化物具優異的低介電常數、低介電正切等電氣特性,且具明顯的耐熱性之改善效果等,宜為環氧樹脂。
用於本發明的環氧樹脂例如雙酚A型環氧樹脂、雙酚F型環氧樹脂、雙酚S型環氧樹脂、雙酚AD型環氧樹脂、間苯二酚型環氧樹脂、氫醌型環氧樹脂、兒茶酚型環氧樹脂、二羥萘型環氧樹脂、聯苯型環氧樹脂、四甲基聯苯型環氧樹脂等由2價苯酚類衍生之環氧樹脂、苯酚酚醛清漆型環氧樹脂、甲苯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、二環戊二烯苯酚改良型環氧樹脂、苯酚芳烷型環氧樹脂、聯苯芳烷型環氧樹脂、萘酚酚醛清漆型環氧樹脂、萘酚芳烷型環氧樹脂、萘酚苯酚共聚酚醛清漆型環氧樹脂、萘酚甲苯酚共聚酚醛清漆型環氧樹脂、芳香族烴甲醛樹脂改性苯酚樹脂型環氧樹脂、二苯改性酚醛清漆型環氧樹脂等由3價以上的苯酚類衍生之環氧樹脂、由有機磷化合物改性之環氧樹脂等。
又,亦可使用使該苯酚樹脂組成物中的苯酚性羥基縮水甘油化而成環氧樹脂者做為硬化劑(II)。
使上述苯酚樹脂(I)縮水甘油化而成環氧樹脂之方法,例如依常法使苯酚樹脂(I)和環氧氯丙烷、環氧溴丙烷、β-甲基環氧氯丙烷等環氧丙烷類反應即可。
又,上述苯酚樹脂(I)和上述環氧樹脂中的環氧基之摻合比率,係該苯酚樹脂(I)中的苯酚性羥基和環氧樹脂中的環氧基之莫耳比(苯酚性羥基/環氧基),考量硬化性及硬化物的耐熱性之觀點,宜為0.8~1.2。
本發明的苯酚樹脂組成物係以上述苯酚樹脂(I)及硬化劑(II)為必須成分,惟亦可依據用途、需求特性而併用苯酚酚醛清漆樹脂、甲苯酚酚醛清漆樹脂、芳香族烴甲醛樹脂改良苯酚樹脂、苯酚芳烷樹脂、甲苯酚芳烷樹脂、萘酚芳烷樹脂、聯苯改性苯酚樹脂、苯酚三羥甲基甲烷樹脂、四苯酚乙烷樹脂、萘酚酚醛清漆型環氧樹脂、萘酚芳烷型環氧樹脂、萘酚酚醛清漆樹脂、萘酚苯酚共聚酚醛清漆樹脂、萘酚甲苯酚共聚酚醛清漆樹脂、聯苯改性苯酚樹脂、胺基三改性苯酚樹脂、雙酚A酚醛清漆樹脂、雙酚F酚醛清漆樹脂等。
又,為要加速上述苯酚樹脂(I)和硬化劑(II)的硬化反應,可適當地使用硬化促進劑。上述硬化促進劑例如磷系化合物、第3級胺、咪唑、有機酸金屬鹽、路易士酸、胺配鹽等。
本發明的苯酚樹脂組成物,係可依需求依據用途添加使用為無機充填劑、改質劑的熱硬化性及熱塑性樹脂、阻燃賦予劑、顏料、矽烷偶合劑、脫模劑等各種摻合劑。
上述無機質充填材料例如熔融二氧化矽、結晶二氧化矽、氧化鋁、氮化矽、氫氧化鋁、氫氧化鎂等。其中尤宜熔融二氧化矽,乃因可提高無機充填材料的充填率。熔融二氧化矽可為任一破碎狀、球狀,為要提高熔融二氧化矽的摻合量且抑制模塑材料的熔融黏度的上升,宜主要使用球狀者。又,為要提高球狀二氧化矽的摻合量,宜適當地調整球狀二氧化矽的粒度分布。
無機充填材料的摻合比率之適當範圍係因應使用用途和預期的特性而異,例如使用於半導體封止材料用途時,鑒於線膨脹係數和阻燃性愈高者愈好,相對於苯酚樹脂組成物總量,宜為65~95質量%的範圍,尤宜85~95質量%的範圍。又,使用於導電漿和導電薄膜等用途時,可使用銀粉和銅粉等導電性充填劑。
上述使用為改質劑的熱硬化性樹脂級熱塑性樹脂,係可使用各種物質,例如苯氧樹脂、聚醯胺樹脂、聚醯亞胺樹脂、聚醚醯亞胺樹脂、聚醚磺樹脂、聚亞苯醚樹脂、聚亞苯硫醚樹脂、聚酯樹脂、聚苯乙烯樹脂、聚對苯二甲酸乙二酯樹脂等。
上述阻燃賦予劑例如鹵化合物、含磷原子化合物、含氮原子化合物和無機系阻燃化合物等。具體而言,四溴雙酚A型環氧樹脂和溴化苯酚酚醛清漆型環氧樹脂等鹵化合物、三甲基磷酸酯、三乙基磷酸酯、三丁基磷酸酯、三-2-乙基己基磷酸酯、三丁氧基乙基磷酸酯、三苯基磷酸酯、三甲酚磷酸酯、三二甲苯磷酸酯、甲酚二苯基磷酸酯、二甲苯二苯基磷酸酯、2-乙基己基二苯基磷酸酯、三(2,6-二甲基苯基)磷酸酯、間苯二酚二苯基磷酸酯等磷酸酯、聚磷酸銨、聚磷酸醯胺、紅磷、磷酸胍、二烷基羥甲基膦酸酯等縮合磷酸酯化合物等含磷原子化合物、三聚氰胺等含氮原子化合物、氫氧化鋁、氫氧化鎂、硼酸鋅、硼酸鈣等無機系阻燃化合物。惟,因本發明的苯酚樹脂組成物,係不僅不使用對環境負荷高的鹵素系阻燃劑且具優異的阻燃效果,使用上述阻燃賦予劑時,宜使用含磷原子化合物或含氮原子化合物或無機系阻燃化合物。
本發明的苯酚樹脂組成物,係可使上述苯酚樹脂(I)和硬化劑(II)及依需求摻合的其他摻合劑均勻地混合而製得。此時,為提昇作業性等目的或因應用塗和加熱硬化條件,亦可調整其黏度。此時可使用的溶劑無特別的限制,例如甲醇、乙醇、異丙醇、甲基溶纖劑、乙基溶纖劑等醇性溶劑、甲苯、二甲苯等芳香族烴性溶劑、丙酮、甲基乙酮、甲基異丁酮、環己酮、二甲基甲醯胺等非醇性極性溶劑等沸點160℃以下的溶劑及N-甲基吡咯烷酮等,宜因應用途及加熱硬化條件等適當地選擇。又,預先將溶劑添加於苯酚樹脂(I)及硬化劑(II)中,之後再混合二者之方法,亦可為將苯酚樹脂組成物和環氧樹脂及依需求摻合的各種摻合劑混合後,添加溶劑以調整黏度使呈均勻之方法。
本發明的苯酚樹脂組成物的熱硬化條件無特別的限制,可以一般使苯酚樹脂硬化的條件實施硬化,若為樹脂成分的軟化溫度以上即可,一般可為120℃以上、200℃以下的溫度。特別是考量其模塑性,宜為130~180℃的溫度範圍。又,為製得耐熱性優異的磨擦材料,宜於模塑後實施燒結。
以上詳述的本發明的苯酚樹脂組成物,除了光阻油墨用樹脂組成物、摩擦材料用黏合劑之外,使用環氧樹脂做為硬化劑(II)時,因製得的硬化物具優異的介電特性,故可使用於覆銅積層板用樹脂組成物、電子零件的封止材料用樹脂組成物、導電漿、樹脂澆鑄材料、膠黏劑、絕緣塗料等塗層材料。
將本發明的苯酚樹脂組成物使用為光阻油墨用樹脂組成物之方法,例如於上述苯酚樹脂(I)及硬化劑(II)中,更添加有機溶劑、顏料、滑石及填料做為光阻油墨用組成物之後,以網版印刷方式塗布於印刷基板上後,做為光阻油墨硬化物之方法等。其中使用的有機溶劑例如甲基溶纖劑、乙基溶纖劑、甲基溶纖劑乙酸酯、乙基溶纖劑乙酸酯、環己酮、二甲亞碸、二甲基甲醯胺、二氧雜環戊烷、四氫呋喃、丙二醇一甲醚乙酸酯、乙基乳酸酯等。
使用本發明的苯酚樹脂組成物做為摩擦材料用黏合劑時,係可使用藉由加熱使六亞甲基四胺、仲甲醛等產生甲醛之物質做為硬化劑(II),摻合其他例如咪唑、及其衍生物、羧酸衍生物、胺類、BF3
、銨化合物等硬化促進劑而製得。使用摩擦材料用黏合劑調節摩擦材料之方法,例如於上述各成分中添加充填劑、添加劑等並使熱硬化之方法、使上述各成分含浸於纖維基材並使熱硬化之方法等。其中使用的充填劑、添加劑例如二氧化矽、硫酸鋇、碳酸鈣、碳化矽、檟如油聚合物、二硫化鉬、氫氧化鋁、滑石、黏土、石墨、石墨、橡膠粒、鋁粉、銅粉、珍珠粉等。
使用於做為摩擦材料用黏合劑時,例如於苯酚樹脂組成物中併用纖維基材和硬化劑,使熱硬化而製造之方法。其中纖維基材例如玻璃纖維、陶瓷纖維、石棉纖維、碳纖維、不銹鋼纖維等無機纖維、棉、麻等天然纖維、聚酯、聚醯胺等合成有機纖維等,纖維基材之形狀例如短纖維、長纖維、紗線、墊子、薄片等。
由本發明的苯酚樹脂組成物製造覆銅積層板用樹脂組成物之方法,具體而言使用上述苯酚樹脂(I)、硬化劑(II)的環氧樹脂及有機溶劑,而使漆化之方法。
其中使用的有機溶劑例如甲醇、乙醇、異丙醇、甲基溶纖劑、乙基溶纖劑、丙二醇一甲醚等醇性溶劑、甲苯、二甲苯等芳香族烴性溶劑、丙酮、甲基乙酮、甲基異丁酮、環己酮、二甲基甲醯胺、N-甲基吡咯烷酮、二甲基乙醯胺等非醇性極性溶劑等溶劑。
其次,由上述覆銅積層板用樹脂組成物製造覆銅積層板之方法,具體而言如以下之方法。
將上述使用上述苯酚樹脂(I)、硬化劑(II)的環氧樹脂及有機溶劑而漆化之組成物,含浸於紙、玻璃布、玻璃不織布、芳香族聚醯胺紙、芳香族聚醯胺布、玻璃墊、玻璃粗紗布等各種補強基材,因應使用的溶劑種類加熱至加熱溫度,宜為50~170℃,藉此製得硬化物即聚酯預浸漬物。此時,使用的苯酚樹脂組成物和補強基材之摻合比率,一般宜調整為聚酯預浸漬物中的樹脂分為20~60質量%。
層積製得的聚酯預浸漬物,更重疊銅箔,於1~10MPa的加壓下,於170~250℃實施10分鐘~3小時的加熱壓黏,藉此可製得目的物覆銅積層板。
又,本發明的覆銅積層板用樹脂組成物更可有效地使用為組合印刷基板的層間絕緣材料。該組合印刷基板的層間絕緣材料,即使上述漆化方法中,特別是可藉由摻合上述苯酚樹脂(I)、硬化劑(II)的環氧樹脂、上述有機溶劑、橡膠、填料之方法而調製。由依此製得的組合基板用層間絕緣材料製造組合基板之方法,具體而嚴厲如下述的方法。
亦即,利用噴霧塗布法、幕簾塗布法等將該組合基板用層間絕緣材料塗布於已形成電路的配線基板後使硬化,其次,依需求於規定的穿孔部位等穿洞後,以粗化劑實施處理,藉由水洗其表面而形成凹凸,實施銅等金屬鍍敷處理。上述鍍敷方法宜為無電解鍍敷、電解鍍敷,又,上述粗化劑例如酸化劑、鹼、有機溶劑等。依需求依序重複該操作,藉由交互地組合形成樹脂絕緣層及規定的電路圖形的導體層,可製得組合基板。惟,穿孔部位的穿洞,宜於最外層的樹脂絕緣層形成之後實施,又,於銅箔上使該樹脂組成物半硬化之含樹脂銅箔,使其以170~250℃加熱壓黏於已形成電路的配線基板上,藉此形成粗化面,省略鍍敷處理之工程,亦可製作組合基板。
使用本發明的苯酚樹脂組成物做為電子零件的封止材料用樹脂組成物時之具體用途,例如半導體封止材料、半導體的膠帶狀封止劑、坩鍋型液狀封止劑、底膜用樹脂、半導體的層間絕緣膜等。
為要將本發明的苯酚樹脂組成物調整為半導體封止材料用,預先混合上述苯酚樹脂(I)、硬化劑(II)的環氧樹脂、依需求摻合的其他偶合劑、脫模劑等添加劑和無機充填材料等,之後使用擠壓機、捏和機、輥等充分地混合至呈均勻狀之方法。
使用為半導體的膠帶狀封止劑時,加熱依上述方法製得的樹脂組成物,製作半硬化薄片,做成封止劑膠帶後,將該封止劑膠帶置於半導體片上,於100~150℃加熱並使軟化以模塑,於170~250℃使完全硬化之方法。
由本發明的苯酚樹脂組成物調製複合材料之方法,例如為將上述苯酚樹脂(I)及硬化劑(II)調製成因應用途之黏度,而使用有機溶劑以漆化,使該漆含浸於補強基材,加熱製得聚酯預浸漬物後,使其逐漸轉變為纖維,實施層積使相近地維持於等方性,之後藉由加熱而硬化模塑之方法。其中使用的有機溶劑例如甲醇、乙醇、異丙醇、甲基溶纖劑、乙基溶纖劑等醇性溶劑、甲苯、二甲苯等芳香族烴性溶劑、丙酮、甲基乙酮、甲基異丁酮、環己酮、二甲基甲醯胺等非醇性極性溶劑等沸點為160℃以下之溶劑。加熱溫度係可依據使用的溶劑的種類而適當地選擇,宜為50~150℃的範圍。又,上述補強基材例如碳纖維、聚酯纖維、聚醯胺纖維、氧化鋁纖維、紙、玻璃布、玻璃不織布、芳香族聚醯胺紙、芳香族聚醯胺布、玻璃墊、玻璃粗紗布等。樹脂分和補強基材的比率無特別的限制,一般宜將聚酯預浸漬物中的樹脂分調整為20~60質量%。
即使於上述各種用途中,本發明的苯酚樹脂組成物係對環境負荷低的無鹵素之硬化系列,因兼具優異的阻燃性和耐熱性,故特別有助於使用為覆銅積層板用樹脂組成物。
本發明的硬化物係使上述的本發明的苯酚樹脂組成物模塑硬化而製得,因應用途可使用為積層物、澆鑄物、黏合劑、塗膜、薄膜等。如上述般,特別有助於做為印刷基板用的覆銅積層板。
為使本發明的苯酚樹脂組成物硬化,因應硬化劑(II)的種類、其他摻合成分、用途等,於適當的溫度條件實施加熱硬化即可,具體而言,宜於25~200℃的溫度條件實施硬化。
其次,以實施例、比較例更具體地說明本發明,惟以下「份」、「%」係質量基準。
使用於以下的實施例之以含有含羧基的芳香族烴基及胺基做為三環上的取代基之三化合物(x2),係下述構造式(4)表示的日生化學工業所(股)製的苯甲酸胍胺(以下簡稱為「BAG」)。
又,依據下述方法測得實施例及比較例製得的苯酚樹脂是否含羥甲基?是否含有未反應苯酚類(x1)、未反應醛類(x3)?及其分子量分布。
<芳香族取代羥甲基及是否含有羥甲基>使用1 3
C-NMR測定樹脂組成物中的羥甲基是否存在。
裝置:日本電子股份公司製「GSX270質子」:270MHz,測定溶劑:重甲醇或重丙酮、重二甲基亞碸,基準物質:四甲基矽烷。在其分析圖型中的55~70ppm處,有明顯區別於干擾之波峰。出現波峰者判定為「有」,若不出現者則為「無」。
<未反應苯酚類(x1)之含有率>管柱:30%矽藻土545卡努那巴蠟2m×3mm,管柱溫度:170℃,注入口溫度:230℃,檢測器:FID,載體氣體:氮氣1.0kg/cm2
,測定法:內部標準法的測定條件中,測定苯酚樹脂(I)中的一官能性苯酚量。
<未反應醛類(x3)是否存在>使用FT-IR測定反應中苯酚樹脂(I)中是否存在未反應醛類。
裝置:日本分光股份公司製FT/IR-500。將反應混合物塗布於KBr板,由測定圖型中1700cm- 1
附近測得的醛基來源之波峰判定。出現波峰者判定為「有」,若不出現者則為「無」。
<分子量分布>依據下述的裝置及測定條件測定分子量分布。
裝置:東曹股份公司製「HLC-8220GPC」,管柱:G2000HXLx2、G3000HXL、G4000HXL7.8mm×300mm,管柱溫度:40℃,檢測器:RI,載體溶劑:四氫呋喃,流速:1.0ml/分。
測定法:以和聚苯乙烯標準法相同的測定條件,測定苯酚樹脂(I)的分子量分布。
<苯酚樹脂中的氮原子含量>由原料成分的總使用質量、化合物(x2)及化合物(x4)的使用質量和氮原子的質量算出。
<羧基當量>由原料成分的總使用質量、化合物(x2)的使用質量及羧基質量算出。
於具備冷凝器和常壓及減壓蒸餾裝置之反應器中,放入940份苯酚、185份BAG、434份41.5%甲醛溶液、及3份三乙基胺,昇溫至115℃使反應2小時。其次,實施常壓蒸餾的同時昇溫至135℃並使反應2小時,再度實施常壓蒸餾的同時昇溫至180℃,於180℃實施減壓蒸餾以去除未反應單體和水等低沸點成分,製得780份軟化點為123℃的樹脂。以下,稱該樹脂為「苯酚樹脂(A-1)」。
又,製得的苯酚樹脂(A-1)中的固形分,不含羥甲基、未反應醛類,而未反應苯酚單體量為0.1質量%。
分子量分布的測定結果如第1圖所示。
又,苯酚樹脂(A-1)的氮原子含量為7.2質量%,羧基當量為975g/當量,於150℃的ICI熔點黏度為55泊,分子量分布(Mw/Mn)為2.46。
實施例2除將使用比改為1080份的鄰-甲苯酚之外,實施和實施例1相同的反應,製得840份之軟化點為116℃的樹脂。以下,稱該樹脂為「苯酚樹脂(A-2)」。又,製得的苯酚樹脂組成物中的固形分,不含羥甲基、未反應醛類,而未反應苯酚單體量為0.2質量%。分子量分布的測定結果如第2圖所示。
又,苯酚樹脂(A-2)的氮原子含量為6.6質量%,羧基當量為1050g/當量,於150℃的ICI熔點黏度為45泊,分子量分布(Mw/Mn)為3.29。
實施例3於具備冷凝器和常壓及減壓蒸餾裝置之反應器中,放入940份苯酚、92份BAG、50份三聚氰胺、434份41.5%甲醛溶液、及3份三乙基胺,昇溫至100℃使反應2小時。其次,實施常壓蒸餾的同時昇溫至135℃並使反應2小時,再度實施常壓蒸餾的同時昇溫至150℃,反應2小時後降溫至95℃。以滴落方式將170份41.5%甲醛溶液添加於反應系中,昇溫至100℃並使反應2小時。其次,實施常壓蒸餾的同時昇溫至135℃並使反應2小時,再度實施常壓蒸餾的同時昇溫至180℃,於180℃實施減壓蒸餾以去除未反應單體和水等低沸點成分,製得730份之軟化點為117℃的樹脂。以下,稱該樹脂為「苯酚樹脂(A-3)」。又,製得的苯酚樹脂(A-3)中的固形分,不含羥甲基、未反應醛類,而未反應苯酚單體量為0.2質量%。分子量分布的測定結果如第3圖所示。
又,苯酚樹脂(A-3)的氮原子含量為8.4質量%,羧基當量為1825g/當量,於150℃的ICI熔點黏度為81泊,分子量分布(Mw/Mn)為2.95。
比較例1於具備冷凝器和常壓及減壓蒸餾裝置之反應器中,放入940份苯酚、151份三聚氰胺及434份41.5%甲醛溶液,昇溫至100℃使進行回流反應2小時。其次,實施常壓蒸餾的同時昇溫至135℃並使進行回流反應2小時,再度實施常壓蒸餾的同時昇溫至180℃,於180℃實施減壓蒸餾以去除未反應單體和水等低沸點成分,製得740份之軟化點為136℃的樹脂。以下,稱該樹脂組成物為(A’-1)。又,製得的苯酚樹脂組成物中的固形分,不含羥甲基、未反應醛類,而未反應苯酚單體量為0.9質量%。分子量分布的測定結果如第4圖所示。
又,苯酚樹脂(A’-1)的氮原子含量為13.6質量%,於150℃的ICI熔點黏度為100泊,分子量分布(Mw/Mn)為2.84。
實施例4~6、比較例2~4依據第1表所示摻合以下述方法調製苯酚樹脂組成物,其次,於下述條件使硬化並試作二面覆銅積層板,實施各種評估。結果如第1表所示。
【環氧樹脂組成物之調整】使上述各實施例及比較例製得的苯酚樹脂(A-1)、苯酚樹脂(A-2)、苯酚樹脂(A-3)、苯酚樹脂(A’-1)、環氧樹脂(B)混合後,調整成最終組成物的不揮發分(N.V.)為55質量%。
【積層板之製作條件】基材:180 μ m;日東紡績股份公司製玻璃薄片「WEA 7628 H258」層數:8聚酯預浸漬物化條件:160℃/2分銅箔:35 μ m;古河紗科特賀爾股份公司製硬化條件:200℃、於40kg/cm2
實施1.5小時模塑後板之厚度:1.6mm,樹脂含量:40%
【物性試驗條件】模塑狀態:實施蝕刻處理並去除銅箔後,以目視進行外觀檢查,若無破損、擦痕、白斑等,且均勻地被模塑者評估為○。
玻璃轉移溫度:實施蝕刻處理並去除銅箔後,以DMA法測定。昇溫速度為3℃/分。
吸濕率:實施蝕刻處理並去除銅箔後,使用壓力鍋試驗機,使試驗片(25mm×50mm)維持於121℃、2.1氣壓、100% RH的條件下2小時後,測定其前後的重量變化。
介電特性:實施蝕刻處理並去除銅箔後,使用介電特性評估器,測定在100MHz、1GHz的周波數之介電率和介電正切(試驗片的尺寸75×25×2mm)。
燃燒試驗:實施蝕刻處理並去除銅箔後,於燃燒試驗用,製作一種漆,其係相對於上述環氧樹脂組成物中固形分,分散、添加30質量%的氫氧化鋁,和上述積層板製作條件相同,製作積層板。試驗方法係依據UL-94垂直試驗。
烘箱耐熱性:使用具備空氣循環裝置的恆溫槽,使試驗片(50mm×50mm)分別於220℃、240℃、260℃條件下處理1小時,試驗片的單面及端面無膨脹、剝落者評估為○。
又,第1表中的各原料及略號如下表示。
「N-673」:甲苯酚酚醛清漆型環氧樹脂(大日本油墨化學工業股份公司製,商品名「EPICLON N-673」,環氧當量為211g/eq.)「N-690」:甲苯酚酚醛清漆型環氧樹脂(大日本油墨化學工業股份公司製,商品名「EPICLON N-690」,環氧當量為216g/eq.)「1121N-80M」:溴化環氧樹脂(大日本油墨化學工業股份公司製,商品名「EPICLON 1121N-80M」,環氧當量為490g/eq.(固形分),不揮發分80%)「MEK」:甲基乙基酮「DMF」:二甲基甲醯胺
第1圖係於實施例1中製得的苯酚樹脂(A-1)的GPC圖。
第2圖係於實施例2中製得的苯酚樹脂(A-2)的GPC圖。
第3圖係於實施例3中製得的苯酚樹脂(A-3)的GPC圖。
第4圖係於比較例1中製得的苯酚樹脂(A’-1)的GPC圖。
Claims (17)
- 一種苯酚樹脂組成物,其特徵係以苯酚樹脂(I)及硬化劑(II)為必要成分,而該苯酚樹脂(I)係在分子結構中含有經以羧基取代的芳香族烴基為鍵結於三環的化學結構(A)的部分結構,且羧基當量為在500~1500g/當量之範圍。
- 如申請專利範圍第1項之苯酚樹脂組成物,其中苯酚樹脂(I)中的化學結構(A)係以下述構造式(1)表示之化合物;
- 如申請專利範圍第1項之苯酚樹脂組成物,其中在分子結構中含有經以羧基取代的芳香族烴基為鍵結於三環的化學結構(A)的部分結構之苯酚樹脂(I),係含有使苯酚類(x1)、以含有含羧基的芳香族烴基及胺基做為三環上的取代基之三化合物(x2)、和醛類(x3)反應而得的分子結構。
- 如申請專利範圍第3項之苯酚樹脂組成物,其中以含有含羧基的芳香族烴基及胺基做為三環上的取代基之三化合物(x2)係下述構造式(2)表示之化合物;
- 如申請專利範圍第3項之苯酚樹脂組成物,其中苯酚樹脂(I)係使苯酚類(x1)、化合物(x2)及醛類(x3),更加上與化合物(x2)之外的含胺基的三化合物(x4)反應而得。
- 如申請專利範圍第5項之苯酚樹脂組成物,其中含胺基的三化合物(x4)係選自三聚氰胺、甲基胍胺及苯并胍胺組成之群組中的1種以上的化合物。
- 如申請專利範圍第1項之苯酚樹脂組成物,其中苯酚樹脂(I)係150℃時的ICI熔融黏度(帝國化學工業熔融黏度)為100泊以下者。
- 如申請專利範圍第1項之苯酚樹脂組成物,其中苯酚樹脂(I)係在分子結構中所含有氮原子之比例為2~13質量%者。
- 如申請專利範圍第1項之苯酚樹脂組成物,其中硬化劑(II)係環氧樹脂。
- 如申請專利範圍第9項之苯酚樹脂組成物,其中苯酚樹脂(I)和環氧樹脂之摻合比例,以該苯酚樹脂(I)中的苯酚性羥基和該環氧樹脂中所含的環氧基之莫耳比(苯酚性羥基/環氧基)計係0.8~1.2。
- 一種苯酚樹脂硬化物,其係使申請專利範圍第1至10項中任一項之苯酚樹脂組成物經熱硬化而成。
- 一種覆銅積層板用樹脂組成物,其係於申請專利範圍第1至10項中任一項之苯酚樹脂組成物中,更含有有機溶劑為必要成分。
- 一種覆銅積層板,其特徵係使申請專利範圍第12項之樹脂組成物含浸於玻璃布(glass cloth)而得聚酯預浸漬物,層積複數的聚酯預浸漬物及銅箔,並使硬化而得。
- 一種新穎苯酚樹脂,其特徵係含有使苯酚類(x1)、以含有含羧基的芳香族烴基及胺基做為三環上的取代基之三化合物(x2),和醛類(x3)反應而得的分子結構,且該分子結構中含有以下述構造式(1)表示之構造部位,
- 如申請專利範圍第14項之新穎苯酚樹脂,其中苯酚樹脂係使苯酚類(x1)、化合物(x2)及醛類(x3),更加上與化合物(x2)之外的含胺基的三化合物(x4)反應而得。
- 如申請專利範圍第14或15項之新穎苯酚樹脂,其中苯酚樹脂係在分子結構中所含有氮原子之比例為2~13質量%者。
- 如申請專利範圍第14或15項之新穎苯酚樹脂,其中苯酚樹脂係該樹脂中所含有的羧基的羧基當量為在500~1500g/當量之範圍者。
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EP (1) | EP1970389B1 (zh) |
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CN (1) | CN101321790B (zh) |
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CN101602275B (zh) * | 2009-05-18 | 2013-05-01 | 孙助海 | 酚醛泡沫双金属面彩钢夹芯板及其连续化生产工艺 |
CN102226033B (zh) * | 2011-05-03 | 2012-10-24 | 广东生益科技股份有限公司 | 环氧树脂组合物及使用其制作的半固化片与覆金属箔层压板 |
CN102731960B (zh) * | 2012-06-18 | 2013-12-04 | 航天材料及工艺研究所 | 一种高韧性阻燃酚醛预浸料复合材料的制备方法 |
CN103343484B (zh) * | 2013-06-10 | 2015-08-19 | 吴昊 | 滤清器滤纸阻燃处理剂及其制备方法与用途 |
JP5700269B1 (ja) * | 2013-07-19 | 2015-04-15 | Dic株式会社 | フェノール性水酸基含有化合物、感光性組成物、レジスト用組成物、レジスト塗膜、硬化性組成物、レジスト下層膜用組成物、及びレジスト下層膜 |
CN103483900B (zh) * | 2013-09-26 | 2015-01-07 | 江苏高博智融科技有限公司 | 一种金属漆填料 |
JP6507506B2 (ja) * | 2014-07-16 | 2019-05-08 | 住友ベークライト株式会社 | 封止用樹脂組成物及び半導体装置 |
SG11201700803VA (en) | 2015-02-03 | 2017-03-30 | Mitsubishi Gas Chemical Co | Resin composition, prepreg, metal foil-clad laminate, resin composite sheet, and printed wiring board |
US20220213248A1 (en) * | 2019-04-19 | 2022-07-07 | Sumitomo Bakelite Co., Ltd. | Resin material and method for producing the same |
CN111070695A (zh) * | 2019-12-30 | 2020-04-28 | 江苏领瑞新材料科技有限公司 | 一种层间混杂纤维复合材料层压板的制备方法 |
CN115073858B (zh) * | 2022-06-15 | 2023-11-14 | 西安天和嘉膜工业材料有限责任公司 | 高频板用双马改性烯烃树脂胶液、胶布及制备方法和应用 |
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JP2001310989A (ja) * | 2000-04-28 | 2001-11-06 | Dainippon Ink & Chem Inc | エポキシ樹脂組成物及び電気積層板 |
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US20100221555A1 (en) | 2010-09-02 |
WO2007063947A1 (ja) | 2007-06-07 |
EP1970389A4 (en) | 2012-10-03 |
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EP1970389A1 (en) | 2008-09-17 |
KR20080080128A (ko) | 2008-09-02 |
KR101014759B1 (ko) | 2011-02-15 |
MY145098A (en) | 2011-12-30 |
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