TW201927897A - 環氧樹脂組成物及其硬化物 - Google Patents
環氧樹脂組成物及其硬化物 Download PDFInfo
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- TW201927897A TW201927897A TW107144541A TW107144541A TW201927897A TW 201927897 A TW201927897 A TW 201927897A TW 107144541 A TW107144541 A TW 107144541A TW 107144541 A TW107144541 A TW 107144541A TW 201927897 A TW201927897 A TW 201927897A
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- Prior art keywords
- epoxy resin
- resin composition
- resin
- biphenylaralkyl
- phosphorus
- Prior art date
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- 239000003822 epoxy resin Substances 0.000 title claims abstract description 133
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 133
- 239000000203 mixture Substances 0.000 title claims abstract description 55
- 239000005011 phenolic resin Substances 0.000 claims abstract description 59
- 238000005227 gel permeation chromatography Methods 0.000 claims abstract description 22
- 238000005259 measurement Methods 0.000 claims abstract description 12
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 40
- 239000011574 phosphorus Substances 0.000 claims description 39
- 229910052698 phosphorus Inorganic materials 0.000 claims description 39
- 239000004848 polyfunctional curative Substances 0.000 claims description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 25
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 43
- 229920005989 resin Polymers 0.000 description 39
- 239000011347 resin Substances 0.000 description 39
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 38
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- 239000000047 product Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 21
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- 239000004305 biphenyl Substances 0.000 description 20
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 16
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 12
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- 238000012360 testing method Methods 0.000 description 9
- 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 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
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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 8
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- 150000001412 amines Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 6
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- 230000000052 comparative effect Effects 0.000 description 5
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- 230000009477 glass transition Effects 0.000 description 5
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- 239000010410 layer Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 4
- 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 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
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- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
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- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
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- H05K1/0366—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement reinforced, e.g. by fibres, fabrics
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- B32B2260/00—Layered product comprising an impregnated, embedded, or bonded layer wherein the layer comprises an impregnation, embedding, or binder material
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- B32B2262/00—Composition or structural features of fibres which form a fibrous or filamentary layer or are present as additives
- B32B2262/10—Inorganic fibres
- B32B2262/101—Glass fibres
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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Abstract
本發明之課題在於提供一種顯現優異的耐熱性、阻燃性、低吸濕性及接著性,尤其在印刷線路板用途賦予優異之硬化物特性之環氧樹脂用組成物。
本發明之環氧樹脂組成物係以環氧樹脂及硬化劑作為必要成分,其中,上述硬化劑之至少一部分為下述通式(1)所示之聯苯基芳烷基型酚樹脂,該聯苯基芳烷基型酚樹脂在凝膠滲透層析測定中,通式(1)中n為0的成分未達15面積%,n為5以上的成分為20面積%以上。
Description
本發明係有關高耐熱性、低吸濕性、阻燃性、接著性等優異之環氧樹脂組成物、其硬化物、預浸物、積層板及印刷線路基板。
環氧樹脂組成物由於接著性、可撓性、耐熱性、耐藥品性、絶緣性、硬化反應性優異,故可遍及塗料、土木接著、鑄造、電氣電子材料、薄膜材料等多種範圍使用。尤其在屬於電氣電子材料之一的印刷線路基板用途中,廣泛實行對環氧樹脂組成物賦予阻燃性。
近年來,隨著資訊裝置的小型化、高性能化的急速發展,對於半導體或電子零件的領域所使用的材料係要求比目前要更高的性能。尤其對於環氧樹脂組成物,從可靠性的觀點要求玻璃轉移溫度為150℃以上的高耐熱性與低吸濕性。
如專利文獻1所示,迄今在積層板的高耐熱化時曾使用二氰二胺(DICY)等胺系硬化劑,但將該硬化劑形成配線基板時,會有基板的吸濕性變高之問題。
因此,曾開發了源自酚結構的高耐熱硬化劑。就作為高耐熱硬化劑的酚硬化劑而言,例如專利文獻2揭示在使用萘酚樹脂作為環氧樹
脂硬化劑時,相較於一般的酚酚醛清漆樹脂,耐熱性得到提升。然而,阻燃性並無法充分滿足。尤其用作為積層板用時,與玻璃布等基材的密著性低,作為積層板時容易產生界面剝離。
又,專利文獻3中使用萘酚酚醛清漆型樹脂作為環氧樹脂用硬化劑,但在高熱條件化下容易分解,無法顯現充分的耐熱性、阻燃性。
專利文獻4揭示使用三苯基甲烷型酚樹脂作為硬化劑,雖然藉由低黏度化而達成作業性提升及高耐熱化,但阻燃性差。
專利文獻5及6揭示使用聯苯酚-聯苯基芳烷基型樹脂作為環氧樹脂的原料酚樹脂,但並未教示作為硬化劑使用之情形。專利文獻7中以比較例揭示使用由4,4-聯苯酚與雙(二羥甲基)聯苯所得之多元羥基化合物作為硬化劑之情形。然而,所揭示之多元羥基化合物的耐熱性並不足。
使用以往的酚系硬化劑之環氧樹脂組成物,並無法充分滿足因應近年來的高功能化之要求性能,不足以在兼具充分的耐熱性與阻燃性的同時確保接著性。
[專利文獻1]日本特開2006-36798號公報
[專利文獻2]日本特開2007-31527號公報
[專利文獻3]日本特開平7-215902號公報
[專利文獻4]日本特開平11-49846號公報
[專利文獻5] WO2011/074517號
[專利文獻6]日本特開2017-095524號公報
[專利文獻7]日本特開2006-248912號公報
本發明所欲解決之課題係提供一種在硬化物中顯現優異的耐熱性、阻燃性、低吸濕性及接著性,尤其在印刷線路板用途賦予優異的硬化物特性之環氧樹脂組成物。
為了解決上述課題,本發明人對於酚樹脂進行深入探討,結果發現,使用由聯苯酚化合物與聯苯基系縮合劑反應而得到且構成成分的比率為特定範圍之聯苯基芳烷基型酚樹脂作為酚硬化劑時,所得之硬化物的耐熱性、阻燃性、低吸濕性及接著性優異,遂完成本發明。
亦即,本發明為一種環氧樹脂組成物,係以環氧樹脂及硬化劑作為必要成分,其中,上述硬化劑之至少一部分為下述通式(1)所示之聯苯基芳烷基型酚樹脂,該聯苯基芳烷基型酚樹脂在凝膠滲透層析測定中,通式(1)中n為0的成分未達15面積%,n為5以上的成分為20面積%以上,
(在此,n為重複單元數且表示0以上的數,其平均值為1.3至20的數,R1、R2及R3分別獨立地表示氫原子或碳數1至8的烴基)。
上述環氧樹脂的一部分或全部較佳為含磷的環氧樹脂。
又,本發明係使上述環氧樹脂組成物硬化而成之硬化物。又,本發明係以使用上述環氧樹脂組成物為特徵之預浸物、積層板或印刷線路基板。
又,本發明為一種聯苯基芳烷基型酚樹脂,係上述通式(1)所示之聯苯基芳烷基型酚樹脂,該聯苯基芳烷基型酚樹脂在凝膠滲透層析測定中,通式(1)中n為0的成分未達15面積%,n為5以上的成分為20面積%以上。
本發明之環氧樹脂組成物由於在其硬化物中顯現優異的耐熱性、阻燃性、低吸濕性及接著性,故可用於印刷線路基板用途。尤其可用作為高可靠性要求較高的車輛用基板。
第1圖係合成例1所得之聯苯基芳烷基型酚樹脂的GPC圖表。
第2圖係合成例2所得之聯苯基芳烷基型酚樹脂的GPC圖表。
第3圖係合成例3所得之聯苯基芳烷基型酚樹脂的GPC圖表。
第4圖係合成例4所得之聯苯基芳烷基型酚樹脂的GPC圖表。
第5圖係合成例5所得之聯苯基芳烷基型酚樹脂的GPC圖表。
第6圖係合成例6所得之聯苯基芳烷基型酚樹脂的GPC圖表。
第7圖係合成例7所得之聯苯基芳烷基型酚樹脂的GPC圖表。
以下詳細說明本發明之實施形態。
本發明之環氧樹脂組成物係以環氧樹脂及硬化劑作為必要成分。硬化劑的至少一部分為上述通式(1)所示之聯苯基芳烷基型酚樹脂。
通式(1)中,R1、R2、及R3分別獨立地表示氫原子或碳數1至8的烴基。碳數1至8的烴基可列舉例如:甲基、乙基、丙基、異丙基、正丁基、第三丁基、己基等碳數1至8的烷基,環己基等碳數5至8的環烷基,苯基、甲苯基、二甲苯基等碳數6至8的芳基,苯甲基、苯乙基、1-苯基乙基等碳數7至8的芳烷基,但並不限定於該等,各個亦可為相同或相異。從取得的容易性及形成硬化物時的耐熱性等物性之觀點來看,較佳的R1、R2、及R3係氫原子、1-苯基乙基、或甲基。
n為重複單元數且表示0以上的數,其平均值(數平均)為1.3至20,較佳為1.5至15,更佳為1.7至10,又更佳為2至6。
n的平均值,若能鑑別上述式(1)的結構,則可由聯苯基芳烷基型酚樹脂的酚性羥基當量計算求得。例如在合成例1的情況,可得到下述式(2)所示之聯苯基芳烷基型酚樹脂。分子量以(186+364×n’)求得,1分子中之酚性羥基的數求得為(2+2×n’)個。由於酚性羥基當量為158g/eq.,故下述計算式158=(186+364×n’)/(2+2×n’)成立,求得n’為2.7。
又,經GPC測定的重量平均分子量(Mw)較佳為1,000至8,000,更佳為2,000至7,000,又更佳為3,000至6,000。
從溶劑溶解性的觀點來看,上述n為0亦即n=0成分的含量,在GPC測定中為未達15面積%,較佳為10面積%以下,更佳為6面積%以下。尤其在積層板用途等中溶解於有機溶劑使用時,較佳為2至5面積%。
從耐熱性提升的觀點來看,n=5成分以上的含量為20面積%以上,較佳為25面積%以上,更佳為27面積%以上。此外,GPC的測定條件係依據實施例所記載之方法。
酚性羥基當量較佳為140至180g/eq.,更佳為145至170g/eq.,又更佳為150至160g/eq.。軟化點較佳為100至160℃,更佳為110至150℃,又更佳為120至140℃。
上述聯苯基芳烷基型酚樹脂可藉由專利文獻5等所揭示之方法而製造。具體而言,該方法係對於聯苯酚化合物與聯苯基系縮合劑,使聯苯酚化合物1莫耳與未達1莫耳的聯苯基系縮合劑反應。
上述聯苯酚化合物可列舉:4,4’-聯苯酚、2,4’-聯苯酚、或2,2’-聯苯酚等,從反應性的觀點來看,較佳為4,4’-聯苯酚。又,該等聯苯酚化合物可在各個芳香環上具有1個碳數1至8的烴基作為取代基。
上述聯苯基系縮合劑可列舉:聯苯基-4,4’-二甲醇、4,4’-雙(氯甲基)聯苯、4,4’-雙(溴甲基)聯苯、4,4’-雙(甲氧基甲基)聯苯、4,4’-雙(乙氧基甲基)聯苯、聯苯基-2,4’-二甲醇、2,4’-雙(氯甲基)聯苯、2,4’-雙(溴甲基)聯苯、2,4’-雙(甲氧基甲基)聯苯、2,4’-雙(乙氧基甲基)聯苯、聯苯基-2,2’-二甲醇、2,2’-雙(氯甲基)聯苯、2,2’-雙(溴甲基)聯苯、2,2’-雙(甲氧基甲基)聯苯、2,2’-雙(乙氧基甲基)聯苯等。從反應性的觀點來看,較佳為聯苯基-4,4’-二甲醇、4,4’-雙(氯甲基)聯苯,從離子性不純物減低的觀點來看,較佳為聯苯基-4,4’-二甲醇、4,4’-雙(甲氧基甲基)聯苯。又,該等聯苯基系縮合劑可在各個芳香環上具有1個或2個碳數1至8的烴基作為取代基。
在聯苯酚化合物與聯苯基系縮合劑的反應,係相對於聯苯基系縮合劑而使用過量的聯苯酚化合物。相對於聯苯酚化合物1莫耳,聯苯基系縮合劑的使用量較佳為0.1至0.55莫耳,更佳為0.3至0.5莫耳。聯苯基系縮合劑的使用量過多時,n=0成分的生成變少,但分子量本身變高,樹脂的軟化點或熔融黏度變高,有對成形性或操作性造成阻礙之疑慮。另一方面,過少時,反應結束後多餘的聯苯酚化合物以外之量變多,對工業上為不佳。
通常該反應係在公知的無機酸、有機酸等酸觸媒的存在下進行。如此之酸觸媒可列舉例如:鹽酸、硫酸、磷酸等無機酸,甲酸、草酸、三氟乙酸、對甲苯磺酸等有機酸,氯化鋅、氯化鋁、氯化鐵、三氟化硼等路易士酸,或活性白土、氧化矽-氧化鋁、沸石等固體酸等。
通常該反應係在10至250℃進行1至20小時。此外,反應時,溶劑較佳係使用例如:甲醇、乙醇、丙醇、丁醇、乙二醇、甲基賽珞蘇、乙基賽珞蘇等醇類,二乙二醇二甲基醚、三乙二醇二甲基醚(triglyme)等醚類,或氯苯、二氯苯等鹵化芳香族化合物等,其中,特佳為乙基賽珞蘇、二乙二醇二甲基醚、三乙二醇二甲基醚等。
以上述方法所得之聯苯基芳烷基型酚樹脂有時含有15面積%以上之n=0成分,故較佳係在反應結束後視需要施以去除n=0成分之步驟。從溶劑溶解性的觀點來看,n=0成分的含有率為未達15面積%,較佳為10面積%以下,更佳為6面積%以下,特佳為3至5面積%。
在將聯苯基芳烷基型酚樹脂之n=0成分的去除步驟中,例如為了不使n=0成分溶解,而使n=1以上的高分子量成分溶解,較佳係使用混合不良溶劑與良溶劑之溶劑,以濾過等方法將n=0成分去除。不良溶劑只要是幾乎不會使n=0成分溶解者即可,並無特別限定,可列舉例如:苯、甲苯、二甲苯等芳香族溶劑。良溶劑可列舉:上述醇類,醚類,鹵化芳香族化合物,或丙酮、甲基乙基酮、甲基異丁基酮、環己酮等酮類。
聯苯基芳烷基型酚樹脂的軟化點雖然可容易地藉由改變屬於樹脂原料的聯苯酚化合物與聯苯基系縮合劑的莫耳比而調整,但是以減少高分子量體成分之方式改變聯苯酚化合物與聯苯基系縮合劑的莫耳比時,會增加必須去除之n=0成分的含量,使操作性劣化且產率大幅降低,因此有其極限。
本發明之環氧樹脂組成物係以上述聯苯基芳烷基型酚樹脂與環氧樹脂作為必要成分。
環氧樹脂可使用於分子中具有2個以上之環氧基的環氧樹脂。舉例之,可列舉:雙酚A型環氧樹脂、雙酚F型環氧樹脂、四甲基雙酚F型環氧樹脂、氫醌型環氧樹脂、聯苯基型環氧樹脂、雙酚茀型環氧樹脂、雙酚S型環氧樹脂、雙硫醚型環氧樹脂、間苯二酚型環氧樹脂、聯苯基芳烷基酚型環氧樹脂、萘二酚型環氧樹脂、酚酚醛清漆型環氧樹脂、苯乙烯化酚酚醛清漆型環氧樹脂、甲酚酚醛清漆型環氧樹脂、烷基酚醛清漆型環氧樹脂、雙酚酚醛清漆型環氧樹脂、萘酚酚醛清漆型環氧樹脂、β-萘酚芳烷基型環氧樹脂、二萘酚芳烷基型環氧樹脂、α-萘酚芳烷基型環氧樹脂、參苯基甲烷型環氧樹脂、參苯基甲烷型環氧樹脂、二環戊二烯型環氧樹脂、烷二醇型環氧樹脂、脂肪族環狀環氧樹脂、二胺基二苯基甲烷四縮水甘油基胺、胺基酚型環氧樹脂、含磷的環氧樹脂、胺基甲酸酯改性環氧樹脂、含唑啶酮環的環氧樹脂、或後述的反應性稀釋劑等,但並不限定於該等。又,該等環氧樹脂可單獨使用,亦可併用2種類以上。積層板用途而言,較佳係使用萘二酚型環氧樹脂、酚酚醛清漆型環氧樹脂、苯乙烯化酚酚醛清漆型環氧樹脂、甲酚酚醛清漆型環氧樹脂、α-萘酚芳烷基型環氧樹脂、二環戊二烯型環氧樹脂、含磷的環氧樹脂、含唑啶酮環的環氧樹脂。
亦可使用上述通式(1)所示之聯苯基芳烷基型酚樹脂作為原料,並使其酚性羥基環氧化而成之環氧樹脂。
該等環氧樹脂的環氧當量(g/eq.)較佳為100至800,更佳為200至780,又更佳為300至760,特佳為400至740。
在要求阻燃性的領域中,較佳係單獨使用或使用2種類以上之含磷的環氧樹脂,此外,亦可併用不含磷的環氧樹脂。含磷的環氧樹脂,
如日本特開平04-11662號公報、日本特開平05-214070號公報、日本特開2000-309624號公報、及日本特開2002-265562號公報等所揭示,特佳係使9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物或二苯基膦氧化物等反應性磷化合物與視需要之1,4-苯醌或1,4-萘醌等醌化合物反應後,再使其與環氧樹脂反應而得者。該等含磷的環氧樹脂之磷含有率較佳為0.5至7質量%,更佳為1至6質量%,又更佳為2至5.5質量%,特佳為3至5質量%。
又,可併用之不含磷的環氧樹脂並無特別限制,可併用上述環氧樹脂,但較佳為酚醛清漆型環氧樹脂等3官能以上的環氧樹脂。併用不含磷的環氧樹脂時,作為含磷的環氧樹脂與不含磷的環氧樹脂之混合環氧樹脂組成物的磷含有率,係以成為含磷的環氧樹脂之較佳的磷含有率之方式,調整含磷的環氧樹脂之磷含有率或含磷的環氧樹脂與不含磷的環氧樹脂的混合量。
含磷的環氧樹脂之具體例可列舉例如:Epotohto FX-305、Epototo FX-289B、Epototo FX-1225、YDFR-1320、TX-1328(以上為新日鐵住金化學股份有限公司製)等,但並不限定於該等。
硬化劑除了上述聯苯基芳烷基型酚樹脂以外,亦可視需要併用1種類或2種類以上之各種酚樹脂類、酸酐類、胺類、醯肼類、酸性聚酯類等一般所使用的環氧樹脂用硬化劑。併用該等硬化劑時,併用的硬化劑在全硬化劑中較佳為70質量%以下,更佳為50質量%以下。併用的硬化劑之比率過多時,會有作為環氧樹脂組成物的耐熱性及阻燃性劣化之疑慮。
環氧樹脂組成物中,相對於全環氧樹脂的環氧基1莫耳,硬化劑的使用量係以硬化劑的活性氫基為0.2至1.5莫耳的範圍為較佳,更佳
為0.3至1.4莫耳,又更佳為0.5至1.3莫耳,特佳為0.8至1.2莫耳。在該範圍外時,硬化變得不完全,會有無法得到良好的硬化物性之疑慮。例如在使用酚系硬化劑或胺系硬化劑時,係相對於環氧基而調配約為等莫耳的活性氫基,在使用酸酐系硬化劑時,係相對於環氧基1莫耳而調配0.5至1.2莫耳的酸酐基、較佳為調配0.6至1.0莫耳的酸酐基。在單獨使用上述酚樹脂時,較佳係相對於環氧樹脂的環氧基1莫耳使用0.9至1.1莫耳的範圍之酚性羥基。
本發明所稱之活性氫基係指具有與環氧基的反應性的活性氫之官能基(包含具有會因水解等而產生活性氫之潜在性活性氫之官能基、或顯示同等的硬化作用之官能基),具體而言,可列舉:酸酐基、羧基、胺基或酚性羥基等。此外,關於活性氫基,1莫耳的羧基或酚性羥基計算為1莫耳,胺基(NH2)則計算為2莫耳。又,活性氫基不明確時,可藉由測定而求得活性氫當量。例如藉由使環氧當量為已知的苯基縮水甘油基醚等單環氧樹脂與活性氫當量為未知的硬化劑反應而測定所消粍的單環氧樹脂的量,可求得所使用的硬化劑之活性氫當量。
可併用之酚樹脂系硬化劑可列舉:雙酚類、二羥基苯類、羥基萘類,含磷的酚硬化劑,屬於酚醛清漆樹脂等酚類與醛類或縮合劑的縮合物之多官能酚化合物,胺基三改性酚樹脂(經三聚氰胺、2,4-二胺基-6-苯基-1,3,5-三(benzoguanamine)等與酚核連結之多官能酚化合物),萜烯酚樹脂、重油改性酚樹脂等,該等多官能酚化合物經烷基、烷氧基、芳基等取代基進行核取代之多官能酚化合物等,但並不限定該等。
雙酚類的具體例可列舉:雙酚A、雙酚F、雙酚C、雙酚K、雙酚Z、雙酚S、四甲基雙酚A、四甲基雙酚F、四甲基雙酚S、四甲基雙酚Z、二羥基二苯基硫醚、4,4’-硫雙(3-甲基-6-第三丁基酚)等。二羥基苯類的具體例可列舉:鄰苯二酚、間苯二酚、甲基間苯二酚、氫醌、單甲基氫醌、二甲基氫醌、三甲基氫醌、單-第三丁基氫醌、二-第三丁基氫醌等。羥基萘類的具體例可列舉:二羥基萘、二羥基甲基萘、二羥基二甲基萘、三羥基萘等。含磷的酚硬化劑的具體例可列舉:LC-950PM60(Shin-AT&C公司製)或EXB9000A(DIC股份有限公司製)等。
酚類與醛類或縮合劑的縮合物之多官能酚化合物,其具體例可列舉:Shonol BRG-555(Aica SDK Phenol股份有限公司製)等酚酚醛清漆樹脂、DC-5(新日鐵住金化學股份有限公司製)等甲酚酚醛清漆樹脂、Resitop TPM-100(群榮化學工業股份有限公司製)等三羥基苯基甲烷型酚醛清漆樹脂、萘酚酚醛清漆樹脂、萘酚-酚共縮合酚醛清漆樹脂、萘酚-甲酚共縮合酚醛清漆樹脂、酚芳烷基樹脂,或SN-160、SN-395、SN-485(新日鐵住金化學股份有限公司製)等萘酚芳烷基樹脂、二環戊二烯酚樹脂、聯苯基改性酚樹脂、聯苯基改性萘酚樹脂等。
此時,酚類可列舉:酚、甲酚、二甲苯酚、丁基酚、戊基酚、壬基酚、丁基甲基酚、三甲基酚、苯基酚、1-萘酚、2-萘酚等單酚化合物,或上述雙酚類、二羥基苯類、羥基萘類。醛類可列舉:甲醛、乙醛、丙醛、丁醛、戊醛、己醛、苯甲醛、氯乙醛、溴醛、乙醛、丙二醛、丁二醛、戊二醛、己二醛、庚二醛(Pimelaldehyde)、癸二醛(sebacaldehyde)、丙烯醛、巴豆醛、水楊醛、鄰苯二甲醛、羥基苯甲醛等。縮合劑可列舉:苯二甲醇、
二甲苯二醇二甲基醚、伸二甲苯二鹵化物(xylylene dihalide),聯苯基系縮合劑,二甲氧基甲基萘、二氯甲基萘,二乙烯基苯、二乙烯基聯苯等二乙烯基化合物,二環戊二烯等環烷基二烯類等。此外,聯苯基系縮合劑可列舉:可作為本發明使用的酚樹脂的製造原料使用之聯苯基系縮合劑。
酸酐系硬化劑具體上可列舉:甲基四氫鄰苯二甲酸酐、六氫鄰苯二甲酸酐、焦蜜石酸酐、鄰苯二甲酸酐、偏苯三甲酸酐、甲基納迪克酸酐(methyl Nadic anhydride)等。
胺系硬化劑具體上可列舉:二伸乙三胺、三伸乙四胺、間二甲苯二胺、異佛酮二胺、二胺基二苯基甲烷、二胺基二苯基碸、二胺基二苯基醚、苯甲基二甲基胺、2,4,6-參(二甲基胺基甲基)酚、二氰二胺、二聚物酸等酸類與多胺類的縮合物之聚醯胺胺等胺系化合物等。
其他硬化劑具體上可列舉:三苯基膦等膦化合物、四苯基鏻溴化物等鏻鹽、2-甲基咪唑、2-苯基咪唑、2-乙基-4-甲基咪唑、2-十一烷基咪唑、1-氰基乙基-2-甲基咪唑等咪唑類,咪唑類與偏苯三甲酸、異三聚氰酸、硼素等的鹽之咪唑鹽類,三甲基銨氯化物等四級銨鹽類、二氮雜雙環化合物,二氮雜雙環化合物與酚類、酚酚醛清漆樹脂類等之鹽類,三氟化硼與胺類、醚化合物等的錯化合物、芳香族鏻、或錪鹽等。
環氧樹脂組成物可視需要使用硬化促進劑。可使用之硬化促進劑之例可列舉:2-甲基咪唑、2-乙基咪唑、2-乙基-4-甲基咪唑等咪唑類,2-(二甲基胺基甲基)酚、1,8-二氮雜-雙環(5,4,0)十一碳-7-烯等三級胺類,三苯基膦、三環己基膦、三苯基膦三苯基硼烷等膦類,辛酸錫等金屬化合物等。相對於本發明之環氧樹脂組成物中的環氧樹脂成分100質量份,較佳
係使用0.02至5質量份的硬化促進劑。藉由使用硬化促進劑,可降低硬化溫度或縮短硬化時間。
環氧樹脂組成物中可將有機溶劑或反應性稀釋劑作為黏度調整使用。
有機溶劑可列舉例如:N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等醯胺類,乙二醇單甲基醚、二甲氧基二乙二醇、乙二醇二乙基醚、二乙二醇二乙基醚、三乙二醇二甲基醚等醚類,丙酮、甲基乙基酮、甲基異丁基酮、環己酮等酮類,甲醇、乙醇、1-甲氧基-2-丙醇、2-乙基-1-己醇、苯甲基醇、乙二醇、丙二醇、丁二醇、松油(pine oil)等醇類,乙酸丁酯、乙酸甲氧基丁酯、甲基賽珞蘇乙酸酯、賽珞蘇乙酸酯、乙基二乙二醇乙酸酯、丙二醇單甲基醚乙酸酯、卡必醇乙酸酯、苯甲基醇乙酸酯等乙酸酯類,苯甲酸甲酯、苯甲酸乙酯等苯甲酸酯類,甲基賽珞蘇、賽珞蘇、丁基賽珞蘇等賽珞蘇類,甲基卡必醇、卡必醇、丁基卡必醇等卡必醇類,苯、甲苯、二甲苯等芳香族烴類,二甲基亞碸、乙腈、N-甲基吡咯烷酮等,但並不限定於該等。
反應性稀釋劑可列舉例如:烯丙基縮水甘油基醚、丁基縮水甘油基醚、2-乙基己基縮水甘油基醚、苯基縮水甘油基醚、三縮水甘油基醚等單官能縮水甘油基醚類,間苯二酚二縮水甘油基醚、新戊二醇二縮水甘油基醚、1,4-丁二醇二縮水甘油基醚、1,6-己二醇二縮水甘油基醚、環己烷二甲醇二縮水甘油基醚、丙二醇二縮水甘油基醚等二官能縮水甘油基醚類,甘油聚縮水甘油基醚、三羥甲基丙烷聚縮水甘油基醚、三羥甲基乙烷聚縮水甘油基醚、新戊四醇聚縮水甘油基醚等多官能縮水甘油基醚類,新
癸酸縮水甘油基酯等縮水甘油基酯類,苯基二縮水甘油基胺、甲苯基二縮水甘油基胺等縮水甘油基胺類,但並不限定於該等。
有機溶劑較佳係使用20至90質量%之由單獨或複數種類混合而成者作為不揮發分,其合適的種類或使用量係因應用途而適當選擇。例如在印刷線路板用途中,較佳為甲基乙基酮、丙酮、1-甲氧基-2-丙醇等沸點為160℃以下的極性溶劑,其使用量以不揮發分計較佳為40至80質量%。又,在接著膜用途中,較佳係使用例如酮類、乙酸酯類、卡必醇類、芳香族烴類、二甲基甲醯胺、二甲基乙醯胺、N-甲基吡咯烷酮等,其使用量以不揮發分計較佳為30至60質量%。
反應性稀釋劑主要為無溶劑系,且使用在減低黏度或調整凝膠時間之情況。該使用量多時,有硬化反應未充分進行而使未反應成分從硬化物滲出或降低機械強度等硬化物物性之疑慮,故以不要過度使用為較佳。因此,在環氧樹脂中,較佳為30質量%以下,更佳為20質量%以下,又更佳為10質量%以下。
環氧樹脂組成物在不損及特性之範圍內可調配其他熱硬化性樹脂、熱塑性樹脂。例如可列舉:酚樹脂、丙烯酸樹脂、石油樹脂、茚樹脂、苯并呋喃-茚樹脂(coumarone-indene resin)、苯氧樹脂、聚胺基甲酸乙酯樹脂、聚酯樹脂、聚醯胺樹脂、聚醯亞胺樹脂、聚醯胺醯亞胺樹脂、聚醚醯亞胺樹脂、聚伸苯醚樹脂、改性聚伸苯醚樹脂、聚醚碸樹脂、聚碸樹脂、聚醚醚酮樹脂、聚苯硫醚樹脂、聚乙烯甲醛樹脂等,但並不限定於該等。
以提升所得之硬化物的阻燃性為目的,環氧樹脂組成物中可使用公知的各種阻燃劑。可使用之阻燃劑可列舉例如:鹵系阻燃劑、磷系阻燃劑、氮系阻燃劑、聚矽氧系阻燃劑、無機系阻燃劑、有機金屬鹽系阻燃劑等。從環境友善之觀點來看,較佳為不含鹵素的阻燃劑,特佳為磷系阻燃劑。該等阻燃劑可單獨使用或併用2種類以上。
磷系阻燃劑可使用無機磷系化合物、有機磷系化合物之任一種。無機磷系化合物可列舉例如:紅磷、磷酸一銨、磷酸二銨、磷酸三銨(Triammonium Phosphate)、多磷酸銨等磷酸銨類、磷醯胺等無機系含氮磷化合物。有機磷系化合物可列舉例如:脂肪族磷酸酯、磷酸酯化合物、縮合磷酸酯類、磺酸化合物、膦酸化合物、膦氧化物化合物、磷烷化合物、有機系含氮的磷化合物等汎用有機磷系化合物,膦酸的金屬鹽以外,9,10-二氫-9-氧雜-10-磷雜菲-10-氧化物、10-(2,5-二羥基苯基)-10H-9-氧雜-10-磷雜菲-10-氧化物、10-(2,7-二羥基萘基)-10H-9-氧雜-10-磷雜菲-10-氧化物等環狀有機磷化合物,該等與環氧樹脂或酚樹脂等化合物反應而得之衍生物之含磷的環氧樹脂或含磷的硬化劑等。
阻燃劑的調配量係因應磷系阻燃劑的種類、環氧樹脂組成物的成分、所期望的阻燃性程度而適當選擇。例如環氧樹脂組成物中之有機成分(不包含有機溶劑)中之磷含量,較佳為0.2質量%以上4質量%以下,更佳為0.4質量%以上3.5質量%以下,又更佳為0.6質量%以上3質量%以下。磷含量少時,會有難以確保阻燃性之疑慮,過多時,會有對耐熱性造成不良影響之疑慮。又,使用磷系阻燃劑時,可併用氫氧化鎂等阻燃助劑。
環氧樹脂組成物可視需要調配填充材。具體上可列舉:熔融氧化矽、結晶氧化矽、氧化鋁、氮化矽、氫氧化鋁、水鋁石、氫氧化鎂、滑石、雲母、碳酸鈣、矽酸鈣、氫氧化鈣、碳酸鎂、碳酸鋇、硫酸鋇、氮化硼、碳、碳纖維、玻璃纖維、氧化鋁纖維、氧化矽氧化鋁纖維、碳化矽纖維、聚酯纖維、纖維素纖維、芳綸纖維、陶瓷纖維、微粒子橡膠、熱塑性彈性體、顏料等。使用填充材的理由可列舉:耐衝撃性的提升效果。又,使用氫氧化鋁、水鋁石、氫氧化鎂等金屬氫氧化物時,會發揮阻燃助劑的作用,有提升阻燃性之效果。相對於填充材除外之環氧樹脂組成物,該等填充材的調配量較佳為1至150質量%,更佳為10至70質量%。調配量多時,有積層板用途所需的接著性降低之疑慮,而且有硬化物變脆、無法得到充分的機械物性之疑慮。又,調配量少時,有硬化物的耐衝撃性提升等填充劑的調配效果未顯現之疑慮。
將環氧樹脂組成物作為板狀基板等時,從其尺寸安定性、彎曲強度等的點來看,可列舉:纖維狀者作為較佳的填充材。更佳可列舉:將玻璃纖維編織成網孔狀之纖維狀基材且使用填充材之玻璃纖維基板。
環氧樹脂組成物可進一步視需要調配矽烷耦合劑、抗氧化劑、離型劑、消泡劑、乳化劑、觸變劑、平滑劑、阻燃劑、顏料等各種添加劑。相對於環氧樹脂組成物,該等添加劑較佳為0.01至20質量%的範圍。
藉由使環氧樹脂組成物含浸於纖維狀基材,可作成印刷線路板等所使用的預浸物。纖維狀基材可使用玻璃等無機纖維,聚酯樹脂等、多胺樹脂、聚丙烯酸樹脂、聚醯亞胺樹脂、芳香族聚醯胺樹脂等有機質纖維的織布或不織布,但並不限定於此。從環氧樹脂組成物製造預浸物之方
法並無特別限定,例如將環氧樹脂組成物浸漬於經溶劑調整黏度所作成之樹脂清漆中進行含浸後,進行加熱乾燥而使樹脂成分半硬化(B stage化)而得,例如可在100至200℃加熱乾燥1至40分鐘。在此,預浸物中之樹脂量較佳係設為樹脂分30至80質量%。
使預浸物硬化時,可採用一般製造印刷線路板時所使用之積層板的硬化方法,但並不限定於此。例如在使用預浸物而形成積層板時,積層一片或複數片的預浸物,於單側或兩側配置金屬箔而構成積層物,並對該積層物加熱/加壓予以積層成一體化。在此,金屬箔可使用銅、鋁、黃銅、鎳等的單獨、合金、複合之金屬箔。而且,藉由對作成的積層物加壓加熱而使預浸物硬化,可得到積層板。此時,較佳係將加熱溫度適當地調整在160至220℃,將加壓壓力適當地調整在50至500N/cm2,將加熱加壓時間適當地調整在40至240分鐘的範圍,可得到所期望的硬化物。加熱溫度低時,硬化反應未充分進行,較高時,會有環氧樹脂組成物開始分解之疑慮。又,加壓壓力較低時,所得之積層板的內部殘留氣泡,會有電氣特性降低之情形,較高時,要硬化前樹脂會流動而有無法得到所望期的厚度之硬化物之疑慮。另外,加熱加壓時間較短時,會有未充分進行硬化反應之疑慮,較長時,會有預浸物中之環氧樹脂組成物產生熱分解之疑慮。
環氧樹脂組成物可藉由與公知的環氧樹脂組成物同樣的方法進行硬化而得到環氧樹脂硬化物。用以得到硬化物之方法,可採用與公知的環氧樹脂組成物同樣的方法,適合使用鑄造、注入、裝填、浸漬、滴塗、輸送成形、壓縮成形等,或以樹脂薄片、附樹脂的銅箔、預浸物等的
形態予以積層並加熱加壓硬化而作成積層板等的方法。此時,硬化溫度通常為100至300℃的範圍,硬化時間通常為1至5小時左右。
本發明之環氧樹脂硬化物可採用積層物、成型物、接著物、塗膜、薄膜等的形態。
製作環氧樹脂組成物並以其作為積層體,進行加熱硬化而形成積層板時之環氧樹脂硬化物之評價結果,該硬化物可成為顯現優異的耐熱性、阻燃性、低吸濕性與接著性,而且在印刷線路板用途銅箔剝離強度及層間密著強度優異者。
列舉實施例及比較例來具體說明本發明,但本發明並不限定於該等。若無特別註明,則「份」表示質量份,「%」表示質量%。又,測定方法分別藉由以下的方法測定。
酚羥基當量:依據JIS K0070規格。
軟化點:依據JIS K7234規格、環球法測定。具體而言,使用自動軟化點裝置(MEITECH股份有限公司製,ASP-MG4)。
GPC測定:使用於本體(Tosoh股份有限公司製,HLC-8220GPC)串聯地具備管柱(Tosoh股份有限公司製,TSKgelG4000HXL、TSKgelG3000HXL、TSKgelG2000HXL)者,管柱溫度設為40℃。又,洗提液係使用四氫呋喃(THF),將流速設為1mL/分鐘,檢測器係使用示差折射率檢測器。測定試料係使用試樣0.1g溶解於10mL的THF並經微過濾器濾過者50μL。數據處理係使用Tosoh股份有限公司製GPC-8020 model II version 6.00。藉由所得之層析圖算出n=0成分量,藉由經標準的單分散聚
苯乙烯(Tosoh股份有限公司製,A-500、A-1000、A-2500、A-5000、F-1、F-2、F-4、F-10、F-20、F-40、F-80、F-128)求得的校準曲線來測定數量平均分子量(Mn)、重量平均分子量(Mw)、分散度(Mw/Mn)。
玻璃轉移溫度(Tg.DSC):係以依據IPC-TM-650 2.4.25.c藉由示差掃描量熱測定裝置(Hitachi High-Tech Science股份有限公司製,EXSTAR6000 DSC6200)以20℃/分鐘的升溫條件進行測定時之DSC.Tgm(相對於玻璃狀態與橡膠狀態的接線為變異曲線的中間溫度)的溫度表示。
玻璃轉移點(Tg.TMA):藉由熱機械測定裝置(SII NanoTechnology股份有限公司製EXSTAR6000TMA/6100)以升溫速度10℃/分鐘的條件而求得Tg。
阻燃性:依據UL94藉由垂直法進行評價。評價記載為V-0、V-1、V-2。但完全燃燒者記載為x。
銅箔剝離強度及層間接著力:依據JIS C6481規格進行測定,層間接著力係在第7層與第8層間進行剝離測定。
吸水率:依據JIS K7209規格。試驗片係使用介電常數及介電損耗正切測定時使用之試樣,並於23℃的水中浸漬24小時而進行測定。
比介電常數及介電損耗正切:依據IPC-TM-650 2.5.5.9使用材料分析裝置(AGILENT Technologies公司製),以容量法求得在頻率1GHz之比介電常數及介電損耗正切。
[環氧樹脂]
(A-1):含磷的環氧樹脂(新日鐵住金化學股份有限公司製,製品名:FX-1225,環氧當量320,磷含有率2.5%)
(A-2):含磷的環氧樹脂(新日鐵住金化學股份有限公司製,製品名:YDFR-1320,環氧當量747,磷含有率5.0%)
(A-3):二環戊二烯型環氧樹脂(DIC股份有限公司製,製品名:HP-7200H,環氧當量280,軟化點82℃)
(A-4):聯苯酚芳烷基型環氧樹脂(依專利文獻6的合成例1所記載之方法合成之樹脂,環氧當量197,熔點125℃)
[硬化劑]
(B-1):合成例1所得之聯苯基芳烷基型酚樹脂
(B-2):合成例2所得之聯苯基芳烷基型酚樹脂
(B-3):合成例3所得之聯苯基芳烷基型酚樹脂
(B-4):合成例4所得之聯苯基芳烷基型酚樹脂
(B-5):合成例5所得之聯苯基芳烷基型酚樹脂
(B-6):合成例6所得之聯苯基芳烷基型酚樹脂
(B-7):合成例7所得之聯苯基芳烷基型酚樹脂
(B-8):含磷的酚硬化劑(Shin-AT&C公司製,製品名:LC-950PM60,酚性羥基當量340,磷含有率9.2%)
(B-9):酚酚醛清漆樹脂(Aica SDK Phenol股份有限公司製,製品名:BRG-557,酚性羥基當量105)
(B-10):酚樹脂(明和化成股份有限公司製,製品名:MEH-7851-3H,酚羥基當量223)
(B-11):酚樹脂(群榮化學工業股份有限公司製,製品名:TPM-100,酚羥基當量98)
(B-12):二氰二胺(Japan Carbide工業股份有限公司製,製品名:DIHARD,活性氫當量21)
[硬化促進劑]
(C-1):2-乙基-4-甲基咪唑(四國化成工業股份有限公司製,製品名:Curezol 2E4MZ)
(C-2):三苯基膦:(北興化學工業股份有限公司製,製品名;Hokko TPP)
合成例1
在具備攪拌機、溫度計、氮氣吹入管及冷卻管的反應裝置添加4,4’-聯苯酚246.2份(1.32莫耳)、二乙二醇二甲基醚379.1份、4,4’-雙氯甲基聯苯132.9份(0.53莫耳),在氮氣流下一邊攪拌一邊升溫至170℃而進行反應2小時。反應後,在減壓下將二乙二醇二甲基醚全量餾除,添加甲苯311份、甲基異丁基酮104份並攪拌混合,冷卻至室溫後,將析出的n=0成分濾除後,將甲苯及甲基異丁基酮餾除,得到聯苯基芳烷基型酚樹脂(B-1)187份。將所得之樹脂的物性呈示於表1,將GPC呈示於第1圖。
合成例2
以與合成例1同樣的操作進行反應後,在減壓下將二乙二醇二甲基醚全量餾除,添加甲苯473份、甲基異丁基酮158份並攪拌混合,冷卻至室溫後,將所析出的n=0成分濾除後,將甲苯及甲基異丁基酮餾除,得到聯苯基芳烷基型樹脂(B-2)203份。將所得之樹脂的物性呈示於表1,將GPC呈示於第2圖。
合成例3
以與合成例1同樣的操作進行反應後,添加甲苯379份並攪拌混合,冷卻至室溫後,將所析出的n=0成分濾除後,將二乙二醇二甲基醚及甲苯餾除,得到聯苯基芳烷基型酚樹脂(B-3)153份。將所得之樹脂的物性呈示於表1,將GPC呈示於第3圖。
合成例4
在與合成例1同樣的裝置添加4,4’-聯苯酚269.9份(1.45莫耳)、二乙二醇二甲基醚379.1份、4,4’-雙氯甲基聯苯109.2份(0.44莫耳),在氮氣流下一邊攪拌一邊升溫至170℃而進行反應2小時。反應後,在減壓下將二乙二醇二甲基醚全量餾除,添加甲苯260份、甲基異丁基酮87份並攪拌混合,冷卻至室溫後,將所析出的n=0成分濾除後,將甲苯及甲基異丁基酮餾除,得到聯苯基芳烷基型酚樹脂(B-4)190份。將所得之樹脂的物性呈示於表1,將GPC呈示於第4圖。
合成例5
在與合成例1同樣的裝置添加4,4’-聯苯酚226.4份(1.22莫耳)、二乙二醇二甲基醚379.1份、4,4’-雙氯甲基聯苯152.7份(0.61莫耳),在氮氣流下一邊攪拌一邊升溫至170℃而進行反應2小時。反應後,在減壓下將二乙二醇二甲基醚全量餾除,添加甲苯250份、甲基異丁基酮83份並攪拌混合,冷卻至室溫後,將所析出的n=0成分濾除後,將甲苯及甲基異丁基酮餾除,得到聯苯基芳烷基型酚樹脂(B-5)183份。將所得之樹脂的物性呈示於表1,將GPC呈示於第5圖。
合成例6
以與合成例1同樣的操作進行反應後,在減壓下將二乙二醇二甲基醚全量餾除,添加甲苯424份、甲基異丁基酮85份並攪拌混合,冷卻至室溫後,將所析出的n=0成分濾除後,將甲苯及甲基異丁基酮餾除,得到聯苯基芳烷基型酚樹脂(B-6)158份。將所得之樹脂的物性呈示於表1,將GPC呈示於第6圖。
合成例7
以與合成例1同樣的操作進行反應後,在減壓下將二乙二醇二甲基醚全量餾除,添加甲基乙基酮339份並攪拌混合,冷卻至室溫後,將所析出的n=0成分濾除後,將甲基乙基酮餾除,得到聯苯基芳烷基型酚樹脂(B-7)208份。將所得之樹脂的物性呈示於表1,將GPC呈示於第7圖。
實施例1
將作為環氧樹脂之(A-4)100份、作為硬化劑之(B-1)80份、及作為硬化促進劑之(C-2)1份混練而得到樹脂組成物。使用所得之環氧樹脂組成物在
175℃進行成形,接著在175℃進行後硬化12小時,得到硬化物。將硬化物的玻璃轉移溫度(Tg.TMA)呈示於表2。
實施例2至4及比較例1至4
除了使用合成例3至7所得之樹脂(B-3)至(B-7)、或酚酚醛清漆樹脂(B-9)、酚樹脂(B-11),並設成表2的調配以外,其餘以與實施例1同樣的方式得到環氧樹脂組成物,並得到硬化物。將進行與實施例1同樣的試驗之結果呈示於表2。此外,表中的「-」表示未使用。
實施例5
將作為含磷的環氧樹脂之(A-1)100份、作為硬化劑之(B-1)50份、作為硬化促進劑之(C-1)0.03份調配,溶解於以MEK、丙二醇單甲基醚、N,N-二甲基甲醯胺調整的混合溶劑而得到環氧樹脂組成物清漆。將所得之環氧樹脂組成物清漆含浸於玻璃布(日東紡織股份有限公司製,WEA 7628 XS13,
0.18mm厚)。將經含浸的玻璃布在150℃的熱風循環烘箱中乾燥9分鐘而得到預浸物。使所得之預浸物8片從上下與銅箔(三井金屬鑛業股份有限公司製,3EC-III,厚度35μm)重疊,在130℃×15分鐘+190℃×80分鐘的溫度條件下進行2MPa的真空擠壓,得到1.6mm厚的積層板。將所得之積層板的銅箔部分浸漬於蝕刻液而去除,並進行洗淨與乾燥後,切出127mm×12.7mm的大小作為阻燃性測定用試驗片。將積層板的銅箔剝離強度、層間接著力、玻璃轉移溫度(Tg.DSC)及阻燃性的結果呈示於表3。
又,將所得之預浸物鬆開,以篩作成通過100網孔的粉狀預浸物粉末。將所得之預浸物粉末置入氟樹脂製的模具,在130℃×15分鐘+190℃×80分鐘的溫度條件下進行2MPa的真空擠壓,得到50mm平方×2mm厚的試驗片。將試驗片的吸水率、比介電常數及介電損耗正切的結果呈示於表3。
實施例6至8及比較例5至8
將作為環氧樹脂之(A-1)、作為硬化劑之(B-1)至(B-2)、(B-4)至(B-5)、(B-9)至(B-12)、作為硬化促進劑之(C-1)依表3的調配量(份)調配,進行與實施例5同樣的操作,得到積層板及試驗片。進行與實施例5同樣的試驗,其結果呈示於表3。
實施例9至12及比較例9至12
將作為環氧樹脂之(A-1)至(A-3)、作為硬化劑之(B-1)、(B-8)至(B-9)、作為硬化促進劑之(C-1)依表4的調配量(份)調配,進行與實施例5同樣的操作,得到積層板及試驗片。進行與實施例5同樣的試驗,其結果呈示於表4。
由該等結果可知,使用聯苯基芳烷基型酚樹脂之環氧樹脂組成物可具有高耐熱性,於低吸水性與接著性亦顯現充分的性能。尤其在使用含磷的環氧樹脂時,可得到兼具更高的阻燃性之環氧樹脂組成物。
Claims (7)
- 一種環氧樹脂組成物,係以環氧樹脂及硬化劑作為必要成分,其中,上述硬化劑之至少一部分為下述通式(1)所示之聯苯基芳烷基型酚樹脂,該聯苯基芳烷基型酚樹脂在凝膠滲透層析測定中,通式(1)中n為0的成分未達15面積%,n為5以上的成分為20面積%以上,
- 如申請專利範圍第1項所述之環氧樹脂組成物,其中,上述環氧樹脂的一部分或全部為含磷的環氧樹脂。
- 一種硬化物,係使申請專利範圍第1或2項所述之環氧樹脂組成物硬化而成者。
- 一種預浸物,係使用申請專利範圍第1或2項所述之環氧樹脂組成物而得者。
- 一種積層板,係使用申請專利範圍第1或2項所述之環氧樹脂組成物而得者。
- 一種印刷線路基板,係使用申請專利範圍第1或2項所述之環氧樹脂組成物而得者。
- 一種聯苯基芳烷基型酚樹脂,為下述通式(1)所示者,該聯苯基芳烷基型酚樹脂在凝膠滲透層析測定中,通式(1)中n為0的成分未達15面積%,n為5以上的成分為20面積%以上,
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JPH07215902A (ja) | 1994-01-31 | 1995-08-15 | Dai Ichi Kogyo Seiyaku Co Ltd | ナフトールアルデヒド縮合物の製造方法 |
JPH1149846A (ja) | 1997-08-01 | 1999-02-23 | Nippon Kayaku Co Ltd | トリフェニルメタン型フェノール樹脂、エポキシ樹脂組成物及びその硬化物 |
JP4036011B2 (ja) * | 2002-02-26 | 2008-01-23 | 日立化成工業株式会社 | 難燃性熱硬化樹脂組成物,それを用いたプリプレグ及び電気配線板用積層板 |
JP4745625B2 (ja) * | 2003-06-19 | 2011-08-10 | 住友化学株式会社 | エポキシ化合物およびエポキシ樹脂硬化物 |
JP4736367B2 (ja) | 2004-07-22 | 2011-07-27 | 住友ベークライト株式会社 | 樹脂組成物、プリプレグおよび積層板 |
JP5002897B2 (ja) | 2005-03-08 | 2012-08-15 | Dic株式会社 | 多価ヒドロキシ化合物、エポキシ樹脂、それらの製造方法、エポキシ樹脂組成物及び硬化物 |
JP2007031527A (ja) | 2005-07-26 | 2007-02-08 | Asahi Organic Chem Ind Co Ltd | ナフトール樹脂及びその製造方法 |
JP2007302746A (ja) * | 2006-05-09 | 2007-11-22 | Toto Kasei Co Ltd | リン含有変性エポキシ樹脂、難燃性マトリックス樹脂組成物、プリプレグ及び複合材料 |
JP5142180B2 (ja) * | 2006-05-17 | 2013-02-13 | 日本化薬株式会社 | エポキシ樹脂組成物、およびその硬化物 |
CN102656204B (zh) | 2009-12-14 | 2014-08-27 | 新日铁住金化学株式会社 | 环氧树脂、其制造方法、使用其的环氧树脂组合物及固化物 |
JP5432791B2 (ja) * | 2010-03-26 | 2014-03-05 | パナソニック株式会社 | エポキシ樹脂組成物、プリプレグ、金属箔付き樹脂シート、樹脂シート、積層板、多層板 |
CN108314774B (zh) * | 2012-06-15 | 2021-02-12 | 日铁化学材料株式会社 | 含磷的环氧树脂和以该环氧树脂作为必须成分的组合物、固化物 |
TWI601755B (zh) * | 2012-09-26 | 2017-10-11 | Dainippon Ink & Chemicals | Epoxy resin, curable resin composition, cured product thereof, and printed circuit board |
JPWO2014065152A1 (ja) * | 2012-10-26 | 2016-09-08 | 新日鉄住金化学株式会社 | エポキシ樹脂組成物、エポキシ樹脂硬化物の製造方法、及び半導体装置 |
JP6139997B2 (ja) * | 2013-06-20 | 2017-05-31 | 新日鉄住金化学株式会社 | エポキシ樹脂、エポキシ樹脂組成物、及びその硬化物 |
JP2017095524A (ja) * | 2014-03-28 | 2017-06-01 | 新日鉄住金化学株式会社 | エポキシ樹脂、エポキシ樹脂組成物、及びその硬化物 |
JP2016180056A (ja) * | 2015-03-24 | 2016-10-13 | 新日鉄住金化学株式会社 | 多価ヒドロキシ樹脂、エポキシ樹脂、それらの製造方法、エポキシ樹脂組成物及びその硬化物 |
JP6808318B2 (ja) * | 2015-12-28 | 2021-01-06 | 日鉄ケミカル&マテリアル株式会社 | 多価ヒドロキシ樹脂及びエポキシ樹脂の製造方法 |
TWI728084B (zh) * | 2016-03-30 | 2021-05-21 | 日商日鐵化學材料股份有限公司 | 多價羥基樹脂、其之製造方法、環氧樹脂、環氧樹脂組成物及其之硬化物 |
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CN110003616B (zh) | 2024-01-09 |
JP7368551B2 (ja) | 2023-10-24 |
JP2022137081A (ja) | 2022-09-21 |
TWI798311B (zh) | 2023-04-11 |
KR20190070282A (ko) | 2019-06-20 |
JP2019104821A (ja) | 2019-06-27 |
CN110003616A (zh) | 2019-07-12 |
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