低分子量聚苯醚的制备及其在低介电损耗覆铜板中的应用
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- 论文作者：彭康 ; 董辉 ; 潘锦平 ; 陈忠红 ; 梁希亭
- 年：2016
- 作者机构：浙江华正新材料股份有限公司;
- 论文关键词：聚苯醚 ; 低分子量 ; 再分配 ; 热固改性 ; 低介电 ; 覆铜板
- 英文论文关键词：Polyphenylene oxide ; low molecular weight ; redistribution ; thermosetting modification ; low dielectric loss ; copper clad laminate
- 会议召开时间：2016-10-13
- 会议录名称：第十七届中国覆铜板技术·市场研讨会论文集
- 语种：中文
- 分类号：TN41
- 学会代码：FTBC
- 会议名称：第十七届中国覆铜板技术·市场研讨会
- 会议地点：中国陕西西安
- 主办单位：中国印制电路行业协会基板材料分会、中国电子材料行业协会覆铜板材料分会
- 学会名称：中国电子材料行业协会覆铜板材料分会
- 页数：8
- 文件大小：258k
- 原文格式：D
- 会议级别：全国
摘要
低分子量聚苯醚作为一种综合性能优异的树脂在高速低损耗覆铜板中具有广阔的应用前景。本文综述了聚苯醚的基本性能,采用再分配或直接合成制备了低分子量聚苯醚并对其热固改性,进一步阐述了其在高速低损耗覆铜板中的应用。
Low molecular weight polyphenylene Oxides, as one of the resin with outstanding overall properties, has broad application prospects in high speed low loss copper clad laminate. This paper reviewed the basic properties of polyphenylene oxide, the preparation of low molecular weight polyphenylene ether by redistribution or one pot synthetic method. Then the low molecular weight PPO was modified by introducing reactive crosslink group and applicated in high speed low dielectric loss in CCl.
Low molecular weight polyphenylene Oxides, as one of the resin with outstanding overall properties, has broad application prospects in high speed low loss copper clad laminate. This paper reviewed the basic properties of polyphenylene oxide, the preparation of low molecular weight polyphenylene ether by redistribution or one pot synthetic method. Then the low molecular weight PPO was modified by introducing reactive crosslink group and applicated in high speed low dielectric loss in CCl.
引文
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[3]Xu Tongwen,Wu Dan,Wu Liang.Poly(2,6-dimethyl-1,4-phenylene oxide)(PPO)—A versatile starting polymer for proton conductive membranes(PCMs)[J].Progress in Polymer Science,2008,33(9):894-915.
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[5]Percec Simona,Li George.Chemical Modification of Poly(2,6-dimethyl-1,4-phenylene oxide)and Properties of the Resulting Polymers[M].Chemical Reactions on Polymers.American Chemical Society.1988:46-59.
[6]Percec Simona.Chemical modification of poly(2,6-dimethyl-1,4-phenylene oxide)by friedel–crafts reactions[J].Journal of Applied Polymer Science,1987,33(1):191-203.
[7]Percec Simona.Chemical modification of poly(2,6-dimethyl-1,4-phenylene oxide)via phase transfer catalysis[J].Journal of Applied Polymer Science,1988,36(2):415-427.
[8]Mahajan Sudhakars,Sarwade Bhimraod,Wadgaonkar Prakashp.Chemical modification of poly(2,6-dimethyl-1,4-phenylene oxide)by electrophitic substitution reaction with isocyanates[J].Polymer Bulletin,1988,20(2):153-160.
[9]Pan Yan,Huang Yuhui,Liao Bing,Cong Guangmin.Synthesis and characterization of aminated poly(2,6-dimethyl-1,4-phenylene oxide)[J].Journal of Applied Polymer Science,1996,61(7):1111-1115.
[10]Bhole Y.S.,Kharul U.K.,Somani S.P.,Kumbharkar S.C.Benzoylation of polyphenylene oxide:Characterization and gas permeability investigations[J].European Polymer Journal,2005,41(10):2461-2471.
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[12]Chowdhury Geeta,Vujosevic Ranka,Matsuura Takeshi,Brendan Laverty.Effects of polymer molecular weight and chemical modification on the gas transport properties of poly(2,6-dimethyl-1,4-phenylene oxide)[J].Journal of Applied Polymer Science,2000,77(5):1137-1143.
[13]Bopp R.C.,Gaur U.,Kambour R.P.,Wunderlich B.Effect of bromination on the thermal properties of poly(2,6-dimethyl-1,4-phenylene oxide)[J].Journal of Thermal Analysis,1982,25(2):243-258.
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[15]Chintapalli Sangamithra,Frech Roger.Ionic association and conductivity in polyethylene oxide)and poly(propylene oxide)metal salt systems[J].Electrochimica Acta,1995,40(13–14):2093-2099.
[16]Chao Herbert S.I.,Whalen Jana M.Poly(2,6-dimethyl-1,4-phenylene ether)(PPO®)capping and its significance in the preparation of PPO®/epoxy laminate[J].Journal of Applied Polymer Science,1996,59(3):473-481.
[17]Jerussi Robert A.,Mccormick Michael R.Aryl end-capping of 2,6-dimethyl-1,4-polyphenylene oxide[J].Journal of Polymer Science Part A-1:Polymer Chemistry,1968,6(11):3167-3169.
[18]Mühlbach Klaus,Percec Virgil.The influence of molecular weight on the reactivity of a vinylbenzyl ether macromonomer of poly(2,6-dimethyl-1,4-phenylene oxide)[J].Journal of Polymer Science Part A:Polymer Chemistry,1987,25(9):2605-2627.
[19]Chan K.P.,Argyropoulos D.S.,White D.M.,Yeager G.W.,Hay A.S.Facile Quantitative Analysis of Hydroxyl End Groups of Poly(2,6-dimethyl-1,4-phenylene oxide)s by 31P NMR Spectroscopy[J].Macromolecules,1994,27(22):6371-6375.
[20]Han Changsun,Kim Sungchul.Preparation and characterization of poly(2,6-dimethyl-1,4-phenylene oxide)and Nylon 6 graft copolymer[J].Polymer Bulletin,1995,35(4):407-413.
[21]Chalk A.J.,Hay A.S.Direct metalation of poly(2,6-dimethyl-1,4-phenylene ether)[J].Journal of Polymer Science Part A-1:Polymer Chemistry,1969,7(2):691-705.
[22]Hay A.S.,Chalk A.J.Metalation of polyphenylene ethers[J].Journal of Polymer Science Part B:Polymer Letters,1968,6(2):105-107.
[23]Nava Hildeberto,Percec Virgil.Functional polymers and sequential copolymers by phase transfer catalysis.18.Synthesis and characterization ofα,ω-bis(2,6-dimethylphenol)–poly(2,6-dimethyl-1,4-phenylene oxide)andα,ω-bis(vinylbenzyl)–poly(2,6-dimethyl-1,4-phenylene oxide)oligomers[J].Journal of Polymer Science Part A:Polymer Chemistry,1986,24(5):965-990.
[24]Percec Virgil,Wang Jamesh.Synthesis ofα,ω-bis(2,6-dimethylphenol)-poly(2,6-dimethyl-1,4-phenylene oxide)by phase transfer catalyzed polymerization of 4-bromo-2,6-dimethylphenol in the presence of2,2-di(4-hydroxy-3,5-dimethylphenyl)propane[J].Polymer Bulletin,1990,24(5):493-500.
[25]Lee Tzung-Jan,Fang Yau-De,Yuan Wei-Ge,Wei Kuo-Min,Liang Mong.Synthesis,structures and thermal properties of new class epoxide-terminated telechelic poly(2,6-dimethyl-1,4-phenylene oxide)s[J].Polymer,2007,48(3):734-742.
[26]Krijgsman J.,Feijen J.,Gaymans R.J.Synthesis and characterisation of telechelic poly(2,6-dimethyl-1,4-phenylene ether)for copolymerisation[J].Polymer,2003,44(23):7055-7065.
[27]Witteler Helmut,Lieser Günter,Dr?scher Michael.Compatibility of poly[oxy(2,6-dimethyl-1,4-phenylene)]and styrene/maleic anhydride copolymers[J].Die Makromolekulare Chemie,Rapid Communications,1993,14(7):401-403.
[28]Van Aert Huub A.M.,Burkard Milko E.M.,Jansen Johan F.G.A.,Van Genderen Marcel H.P.,Meijer E.W.,Oevering Henk,Buning Gerard H.Werumeus.Functional Oligomers,Telechelics,and Graft and Star-Shaped Poly(2,6-dimethyl-1,4-phenylene ether)s Prepared by Redistribution[J].Macromolecules,1995,28(23):7967-7969.
[29]Van Aert Huub A.M.,Van Genderen Marcel H.P.,Van Steenpaal Grègory J.M.L.,Nelissen Laurent,Meijer E.W.,Liska Juraj.Modified Poly(2,6-dimethyl-1,4-phenylene ether)s Prepared by Redistribution[J].Macromolecules,1997,30(20):6056-6066.
[30]Hwang Hann-Jang,Hsu Su-Wen,Chung Chia-Lung,Wang Chun-Shan.Low dielectric epoxy resins from dicyclopentadiene-containing poly(phenylene oxide)novolac cured with dicyclopentadiene containing epoxy[J].Reactive and Functional Polymers,2008,68(8):1185-1193.
[31]Saito K.,Masuyama T.,Oyaizu K.,Nishide H.Depolymerization of poly(2,6-dimethyl-1,4-phenylene oxide)under oxidative conditions[J].Chemistry,2003,9(17):4240-4246.
[32]万勇军.改性聚苯醚在覆铜板中的应用[J].化工新型材料,2000,(06):13-17.
[33]村上贤志门胁利治,菊田学.乙烯基苄基-聚苯醚化合物的制备方法[P]:CN,104072751A.2014-03-18.
[34]齐藤英一郎,古森清孝,伊藤直树.多聚酯合成物(聚苯醚),聚酯胶片,多层板,印刷电路板,以及多层印刷电路板[P]:CN,1458963A.2003-11-26.
[35]Inoue Hiroharu,Saito Eiichiro,Fujiwara Hiroaki.Poly(phenylene ether)resin composition,prepreg,and laminated sheet[P]:US,2004146692A1.2004-07-29.
[36]Hashimoto Shoji Komori Kiyotaka,Watanabe Tatsuya.Polyphenylene ether resin composition,prepreg,and laminated board[P]:JP,2005015613A.2005-01-20.
[37]Itoh Syouichi,Ueno Yoshitaka,Yaginuma Michio.Resin composition,prepreg and resin sheet,and metal foil-clad laminate[P]:WO,2012128313A1.2012-09-27.
[38]Tanigawa Takao Mizuno Yasuyuki,Kamiyama Kenichi.Thermosetting resin composition,and resin varnish,prepreg and metal-clad laminate using the same[P]:JP,2011225639A.2011-11-10.
[39]王荣涛,谢镇宇,田文君,马子倩,吕文峰.低介电树脂组合物及应用其的铜箔基板及印刷电路板[P]:CN,104341766A.2015-02-11.
[40]杨虎,何岳山.一种无卤树脂组合物及其用途[P]:CN,104845363A.2015-08-19.
[2]Zhu Weiming,Weil Edward D.Influence of the molecular weight of PPO resins and char-forming behavior of polymeric additives on the flame retardancy of EPDM formulations[J].Journal of Applied Polymer Science,1998,67(8):1405-1414.
[3]Xu Tongwen,Wu Dan,Wu Liang.Poly(2,6-dimethyl-1,4-phenylene oxide)(PPO)—A versatile starting polymer for proton conductive membranes(PCMs)[J].Progress in Polymer Science,2008,33(9):894-915.
[4]Lí?ka Juraj,Borsig Eberhard.Polymer-Analogous Reactions on Poly(2,6-dimethyl-1,4-phenylene Oxide)[J].Journal of Macromolecular Science,Part C,1995,35(3):517-529.
[5]Percec Simona,Li George.Chemical Modification of Poly(2,6-dimethyl-1,4-phenylene oxide)and Properties of the Resulting Polymers[M].Chemical Reactions on Polymers.American Chemical Society.1988:46-59.
[6]Percec Simona.Chemical modification of poly(2,6-dimethyl-1,4-phenylene oxide)by friedel–crafts reactions[J].Journal of Applied Polymer Science,1987,33(1):191-203.
[7]Percec Simona.Chemical modification of poly(2,6-dimethyl-1,4-phenylene oxide)via phase transfer catalysis[J].Journal of Applied Polymer Science,1988,36(2):415-427.
[8]Mahajan Sudhakars,Sarwade Bhimraod,Wadgaonkar Prakashp.Chemical modification of poly(2,6-dimethyl-1,4-phenylene oxide)by electrophitic substitution reaction with isocyanates[J].Polymer Bulletin,1988,20(2):153-160.
[9]Pan Yan,Huang Yuhui,Liao Bing,Cong Guangmin.Synthesis and characterization of aminated poly(2,6-dimethyl-1,4-phenylene oxide)[J].Journal of Applied Polymer Science,1996,61(7):1111-1115.
[10]Bhole Y.S.,Kharul U.K.,Somani S.P.,Kumbharkar S.C.Benzoylation of polyphenylene oxide:Characterization and gas permeability investigations[J].European Polymer Journal,2005,41(10):2461-2471.
[11]Sisto R.,Bonfanti C.,Valentini C.Structure and gas permeability of alkynylated poly(phenylene oxide)[J].Journal of Membrane Science,1994,95(2):135-146.
[12]Chowdhury Geeta,Vujosevic Ranka,Matsuura Takeshi,Brendan Laverty.Effects of polymer molecular weight and chemical modification on the gas transport properties of poly(2,6-dimethyl-1,4-phenylene oxide)[J].Journal of Applied Polymer Science,2000,77(5):1137-1143.
[13]Bopp R.C.,Gaur U.,Kambour R.P.,Wunderlich B.Effect of bromination on the thermal properties of poly(2,6-dimethyl-1,4-phenylene oxide)[J].Journal of Thermal Analysis,1982,25(2):243-258.
[14]Scoponi Macro,Ghiglione Chiara.Photo-oxidation mechanisms of poly(2,6-dimethyl-1,4-phenylene oxide)[J].Die Angewandte Makromolekulare Chemie,1997,252(1):237-256.
[15]Chintapalli Sangamithra,Frech Roger.Ionic association and conductivity in polyethylene oxide)and poly(propylene oxide)metal salt systems[J].Electrochimica Acta,1995,40(13–14):2093-2099.
[16]Chao Herbert S.I.,Whalen Jana M.Poly(2,6-dimethyl-1,4-phenylene ether)(PPO®)capping and its significance in the preparation of PPO®/epoxy laminate[J].Journal of Applied Polymer Science,1996,59(3):473-481.
[17]Jerussi Robert A.,Mccormick Michael R.Aryl end-capping of 2,6-dimethyl-1,4-polyphenylene oxide[J].Journal of Polymer Science Part A-1:Polymer Chemistry,1968,6(11):3167-3169.
[18]Mühlbach Klaus,Percec Virgil.The influence of molecular weight on the reactivity of a vinylbenzyl ether macromonomer of poly(2,6-dimethyl-1,4-phenylene oxide)[J].Journal of Polymer Science Part A:Polymer Chemistry,1987,25(9):2605-2627.
[19]Chan K.P.,Argyropoulos D.S.,White D.M.,Yeager G.W.,Hay A.S.Facile Quantitative Analysis of Hydroxyl End Groups of Poly(2,6-dimethyl-1,4-phenylene oxide)s by 31P NMR Spectroscopy[J].Macromolecules,1994,27(22):6371-6375.
[20]Han Changsun,Kim Sungchul.Preparation and characterization of poly(2,6-dimethyl-1,4-phenylene oxide)and Nylon 6 graft copolymer[J].Polymer Bulletin,1995,35(4):407-413.
[21]Chalk A.J.,Hay A.S.Direct metalation of poly(2,6-dimethyl-1,4-phenylene ether)[J].Journal of Polymer Science Part A-1:Polymer Chemistry,1969,7(2):691-705.
[22]Hay A.S.,Chalk A.J.Metalation of polyphenylene ethers[J].Journal of Polymer Science Part B:Polymer Letters,1968,6(2):105-107.
[23]Nava Hildeberto,Percec Virgil.Functional polymers and sequential copolymers by phase transfer catalysis.18.Synthesis and characterization ofα,ω-bis(2,6-dimethylphenol)–poly(2,6-dimethyl-1,4-phenylene oxide)andα,ω-bis(vinylbenzyl)–poly(2,6-dimethyl-1,4-phenylene oxide)oligomers[J].Journal of Polymer Science Part A:Polymer Chemistry,1986,24(5):965-990.
[24]Percec Virgil,Wang Jamesh.Synthesis ofα,ω-bis(2,6-dimethylphenol)-poly(2,6-dimethyl-1,4-phenylene oxide)by phase transfer catalyzed polymerization of 4-bromo-2,6-dimethylphenol in the presence of2,2-di(4-hydroxy-3,5-dimethylphenyl)propane[J].Polymer Bulletin,1990,24(5):493-500.
[25]Lee Tzung-Jan,Fang Yau-De,Yuan Wei-Ge,Wei Kuo-Min,Liang Mong.Synthesis,structures and thermal properties of new class epoxide-terminated telechelic poly(2,6-dimethyl-1,4-phenylene oxide)s[J].Polymer,2007,48(3):734-742.
[26]Krijgsman J.,Feijen J.,Gaymans R.J.Synthesis and characterisation of telechelic poly(2,6-dimethyl-1,4-phenylene ether)for copolymerisation[J].Polymer,2003,44(23):7055-7065.
[27]Witteler Helmut,Lieser Günter,Dr?scher Michael.Compatibility of poly[oxy(2,6-dimethyl-1,4-phenylene)]and styrene/maleic anhydride copolymers[J].Die Makromolekulare Chemie,Rapid Communications,1993,14(7):401-403.
[28]Van Aert Huub A.M.,Burkard Milko E.M.,Jansen Johan F.G.A.,Van Genderen Marcel H.P.,Meijer E.W.,Oevering Henk,Buning Gerard H.Werumeus.Functional Oligomers,Telechelics,and Graft and Star-Shaped Poly(2,6-dimethyl-1,4-phenylene ether)s Prepared by Redistribution[J].Macromolecules,1995,28(23):7967-7969.
[29]Van Aert Huub A.M.,Van Genderen Marcel H.P.,Van Steenpaal Grègory J.M.L.,Nelissen Laurent,Meijer E.W.,Liska Juraj.Modified Poly(2,6-dimethyl-1,4-phenylene ether)s Prepared by Redistribution[J].Macromolecules,1997,30(20):6056-6066.
[30]Hwang Hann-Jang,Hsu Su-Wen,Chung Chia-Lung,Wang Chun-Shan.Low dielectric epoxy resins from dicyclopentadiene-containing poly(phenylene oxide)novolac cured with dicyclopentadiene containing epoxy[J].Reactive and Functional Polymers,2008,68(8):1185-1193.
[31]Saito K.,Masuyama T.,Oyaizu K.,Nishide H.Depolymerization of poly(2,6-dimethyl-1,4-phenylene oxide)under oxidative conditions[J].Chemistry,2003,9(17):4240-4246.
[32]万勇军.改性聚苯醚在覆铜板中的应用[J].化工新型材料,2000,(06):13-17.
[33]村上贤志门胁利治,菊田学.乙烯基苄基-聚苯醚化合物的制备方法[P]:CN,104072751A.2014-03-18.
[34]齐藤英一郎,古森清孝,伊藤直树.多聚酯合成物(聚苯醚),聚酯胶片,多层板,印刷电路板,以及多层印刷电路板[P]:CN,1458963A.2003-11-26.
[35]Inoue Hiroharu,Saito Eiichiro,Fujiwara Hiroaki.Poly(phenylene ether)resin composition,prepreg,and laminated sheet[P]:US,2004146692A1.2004-07-29.
[36]Hashimoto Shoji Komori Kiyotaka,Watanabe Tatsuya.Polyphenylene ether resin composition,prepreg,and laminated board[P]:JP,2005015613A.2005-01-20.
[37]Itoh Syouichi,Ueno Yoshitaka,Yaginuma Michio.Resin composition,prepreg and resin sheet,and metal foil-clad laminate[P]:WO,2012128313A1.2012-09-27.
[38]Tanigawa Takao Mizuno Yasuyuki,Kamiyama Kenichi.Thermosetting resin composition,and resin varnish,prepreg and metal-clad laminate using the same[P]:JP,2011225639A.2011-11-10.
[39]王荣涛,谢镇宇,田文君,马子倩,吕文峰.低介电树脂组合物及应用其的铜箔基板及印刷电路板[P]:CN,104341766A.2015-02-11.
[40]杨虎,何岳山.一种无卤树脂组合物及其用途[P]:CN,104845363A.2015-08-19.