生物基苯并噁嗪的来源及性能研究进展
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摘要
苯并噁嗪树脂作为一类新型热固性树脂,具有低收缩率、低介电常数、低吸水性和灵活分子设计性等独特性能,受到学术界和工业上极大关注。在石油资源逐渐枯竭和全球性气候变暖的背景下,以天然可再生原料为基础的生物基苯并噁嗪树脂在原料来源及性能提升等方面的研究均取得较多进展。文章聚焦于生物基苯并噁嗪树脂的酚类来源,以木质素分解酚类、植物提取酚类、以及生物质衍生酚类三个类别归纳分析近年来生物基苯并噁嗪的研究进展,探究各种生物基苯并噁嗪的结构与性能相关规律,并展望今后生物基苯并噁嗪的研发方向。
Benzoxazine resin,as a new type of thermosetting resin,has attracted great academic and industrial attention due to its unique properties such as low shrinkage,low dielectric constant,low water absorption and flexible molecular design.Under the background of gradual depletion of oil resources and global warming,benzoxazine resins based on natural renewable raw materials have made much progress in terms of raw material sources and performance improvement.This paper focused on the phenolic sources of bio-based benzoxazine resins,summarized the research progress of bio-based benzoxazine in recent years by categorizing the lignin decomposition of phenols,plant extracts of phenols,and biomass-derived phenols,explored the relevant laws of structure and properties of various bio-based benzoxazines,and looked forward to the development direction of bio-based benzoxazines in the future.
Benzoxazine resin,as a new type of thermosetting resin,has attracted great academic and industrial attention due to its unique properties such as low shrinkage,low dielectric constant,low water absorption and flexible molecular design.Under the background of gradual depletion of oil resources and global warming,benzoxazine resins based on natural renewable raw materials have made much progress in terms of raw material sources and performance improvement.This paper focused on the phenolic sources of bio-based benzoxazine resins,summarized the research progress of bio-based benzoxazine in recent years by categorizing the lignin decomposition of phenols,plant extracts of phenols,and biomass-derived phenols,explored the relevant laws of structure and properties of various bio-based benzoxazines,and looked forward to the development direction of bio-based benzoxazines in the future.
引文
[1]Nair C P R.Advances in addition-cure phenolic resins[J].Progress in Polymer Science,2004,29(5):401-498.
[2]Ishida H,Allen D J.Physical and mechanical characterization of near-zero shrinkage polybenzoxazines[J].Journal of Polymer Science Part B Polymer Physics,2015,34(6):1019-1030.
[3]Ishida H, Rodriguez Y.Curing kinetics of a new benzoxazine-based phenolic resin by differential scanning calorimetry[J].Polymer,1995,36(16):3151-3158.
[4]Hong Y L,Ishida H.Improved thermal stability of polybenzoxazines by transition metals[J]. Polymer Degradation&Stability,2006,91(4):805-815.
[5]李洪峰,曲春艳,顾继友,等.航空航天用耐高温苯并噁嗪树脂胶粘剂[J].粘接,2017,38(8):31-36.
[6]张建,刘向阳,顾宜.高性能苯并噁嗪模压复合材料的研究[J].塑料工业,2009,37(3):78-81.
[7]Xiang H,Ling H, Wang J,et al.A novel high performance RTM resin based on benzoxazine[J].Polymer Composites,2010,26(5):563-571.
[8]Rimdusit S,Ishida H.Development of new class of electronic packaging materials based on ternary systems of benzoxazine,epoxy,and phenolic resins[J].Polymer,2000,41(22):7941-7949.
[9]翁云宣.2016生物基材料专刊序言[J].生物工程学报,2016,32(6):711-714.
[10]Methot J C,Cholette A.Effect of polymerizing diacetylene groups on the lowering of polymerization temperature of benzoxazine groups in the highly thermally stable,mainchain-typepolybenzoxazines[J]. Macromolecules,2009,42(14):5121-5127.
[11]Ghosh N N,Kiskan B,Yagci Y.PolybenzoxazinesNew high performance thermosetting resins:Synthesis and properties[J].Progress in Polymer Science,2007,32(11):1344-1391.
[12]Agag T,Lin J,Ishida H.A new synthetic approach for difficult benzoxazines:Preparation and polymerization of4, 4’-diaminodiphenylsulfone-basedbenzoxazine monomer[J].Polymer,2009,50(25):5940-5944.
[13]Ishida H.Process for preparation of benzoxazine compounds in solventless systems:US,5,543,516[P].1996-8-6.
[14]崔俊儒,辛嘉英,牛建中,等.甲烷氧化细菌催化二氧化碳生物合成甲醇的研究[J].分子催化,2004,18(3):214-218.
[15]崔玉虎,王奇,苟光俊,等.木质素催化降解液化的研究进展[J].材料导报,2017,31(5):112-116.
[16]董晨.浅谈我国造纸工业的特点及污染防治现状[J].科学中国人,2015(6):152-156.
[17]赵晓梅.造纸废水中木质素的回收利用[J].辽宁大学学报(自然科学版),2012,39(1):44-46.
[18]曾育才,张学先,刘小玲.造纸黑液木质素及其综合利用[J].广东化工,2005,32(10):11-14.
[19]Wang C F,Sun J Q,Liu X D,et al.Synthesis and copolymerization of fully bio-based benzoxazines from guaiacol,furfurylamine and stearylamine[J].Green Chemistry,2012,14(10):2799-2806.
[20]Wang C F,Zhao C H,Sun J Q,et al.Synthesis and thermal properties of a bio-based polybenzoxazine with curing promoter[J].Journal of Polymer Science Part A Polymer Chemistry,2013,51(9):2016-2023.
[21]Sini N K,Bijwe J,Varma I K.Renewable benzoxazine monomer from Vanillin:Synthesis,characterization,and studies on curing behavior[J].Journal of Polymer Science Part A Polymer Chemistry,2014,52(1):7-11.
[22]Van A,Chiou K,Ishida H.Use of renewable resource vanillin for the preparation of benzoxazine resin and reactive monomeric surfactant containing oxazine ring[J].Polymer,2014,55(6):1443-1451.
[23]ComíM,Lligadas G,Ronda J C,et al.Renewable benzoxazine monomers from “lignin-like”naturally occurring phenolic derivatives[J].Journal of Polymer Science Part A Polymer Chemistry,2013,51(22):4894-4903.
[24]Froimowicz P R.Arza C, Han L,et al.Smart,sustainable,and ecofriendly chemical design of fully bio-based thermally stable thermosets based on benzoxazine chemistry[J].Chemsuschem,2016,9(15):1921-1928.
[25]Trejomachin A,Verge P,Puchot L,et al.Phloretic acid as an alternative to the phenolation of aliphatic hydroxyls for the elaboration of polybenzoxazine[J].Green Chemistry,2017,19(21):28-35.
[26]Xu M,Huang Q,Chen Q,et al.Synthesis and characterization of octadecylamine grafted multi-walled carbon nanotubes[J].Chemical Physics Letters,2003,375(5-6):598-604.
[27]宋谋道,朱吉亮,张邦华,等.聚乙二醇改性聚乳酸的研究[J].高分子学报,1998,1(4):454-458.
[28]方维海,方德彩.丙烯酸气相热解机理的理论探讨[J].物理化学学报,1993,9(5):630-634.
[29]Yamauchi Y,Oshima R,Ju K.Configuration of the olefinic bonds in the heteroolefinic side-chains of japanese lacquer urushiol:Separation and identification of components of dimethylurushiol by means of reductive ozonolysis and high-performance liquid chromatography[J].Journal of Chromatography A,1982,243(1):71-84.
[30]Kumanotani J.Urushi(Oriental Lacquer):A Natural Aesthetic Durable and Future-Promising Coating[M].Butterworths:Digestive Physiology and Nutrition of the Ruminant,1995:163-195.
[31]CalòE,Maffezzoli A,Mele G,et al.Synthesis of a novelcardanol-basedbenzoxazinemonomerand environmentally sustainable production of polymers and bio-composites[J].Green Chemistry,2007,9(7):754-759.
[32]Rao B S,Palanisamy A.Synthesis of bio based low temperature curable liquid epoxy,benzoxazine monomer system from cardanol:Thermal and viscoelastic properties[J].European Polymer Journal,2013,49(8):2365-2376.
[33]Xu G,Shi T,Liu J,et al.Preparation of a liquid benzoxazine based on cardanol and the thermal stability of its graphene oxide composites[J].Journal of Applied Polymer Science,2014,131(11):1732-1742.
[34]Zhang C,Zhang Y,Zhou Q,et al.Processability and mechanical properties of bis-benzoxazine modified by the cardanol-based aromatic diamine benzoxazine[J].Journal of Polymer Engineering,2014,34(6):561-568.
[35]Lochab B,Varma I,Bijwe J.Cardanol-based bisbenzoxazines:Effect of structure on thermal behaviour[J].Journal of Thermal Analysis&Calorimetry,2012,107(2):661-668.
[36]Vasapollo G,Pio I, Mele G,et al.Solvent free synthesis of novel mono-and bis-benzoxazines from cashew nut shell liquid components[J].Current Organic Chemistry,2012,16(21):113-121.
[37]Zhang C,Zhang Y,Zhou Q,et al.Processability and mechanical properties of bisbenzoxazine modified by the cardanol-based aromatic diamine benzoxazine[J].Journal of Polymer Engineering,2014,34(6):561-568.
[38]Zhang L,Yang Y,Chen Y,et al.Cardanol-capped main-chain benzoxazine oligomers for resin transfer molding[J].European Polymer Journal,2017(4):140-149.
[39]Patil D M,Phalak G A,Mhaske S T.Synthesis and characterization of bio-based benzoxazine oligomer from cardanol for corrosion resistance application[J].Journal of Coatings Technology&Research,2017(3):1-14.
[40]Ma H X,Xu Z B,Qiu J J,et al.Synthesis of artificial urushi via ring-opening reaction of benzoxazine with renewable cardanol[J].Polymer,2017(6):34-42.
[41]Zeng M,Pang T,Chen J,et al.Facile preparation of thenovelcastoroil-basedbenzoxazine-urethane copolymer with improved high-frequency dielectric properties[J].Journal of Materials Science Materials in Electronics,2018(5):1-10.
[42]王海青,曹万荣,李光旭,等.腰果酚基苯并噁嗪及其高生物质含量复合材料的制备和性能研究[J].浙江理工大学学报,2016,35(1):29-34.
[43]Puchot L,Verge P,Fouquet T,et al.Breaking the symmetry of dibenzoxazines:aparadigm to tailor the design of bio-based thermosets[J].Green Chemistry,2016,18(11):3346-3353.
[44]Dumas L,Bonnaud L,Olivier M,et al.Bio-based high performance thermosets:Stabilization and reinforcement of eugenol-based benzoxazine networks with BMI and CNT[J].European Polymer Journal,2015,6(7):494-502.
[45]Dumas L,Bonnaud L,Olivier M,et al.Eugenol-based benzoxazine:From straight synthesis to taming of the network properties[J].Journal of Materials Chemistry A,2015,3(11):6012-6018.
[46]Dumas L,Bonnaud L,Olivier M,et al.Chavicol benzoxazine:Ultrahigh Tg biobased thermoset with tunable extended network[J].European Polymer Journal,2016,8(1):337-346.
[47]Dumas L,Bonnaud L,Olivier M,et al.Arbutin-based benzoxazine:En route to an intrinsic water soluble biobased resin[J].Green Chemistry,2016,4(8):311-319.
[48]彭林才,林鹿,李辉.生物质转化合成新能源化学品乙酰丙酸酯[J].化学进展,2012,24(5):801-809.
[49]Zú1iga C, Larrechi M S, Lligadas G, et al.Polybenzoxazines from renewable diphenolic acid[J].Journal of Polymer Science Part A Polymer Chemistry,2011,49(5):1219-1227.
[50]Yan H,Li N,Cheng J,et al.Fabrication of flame retardant benzoxazine semi-biocomposites reinforced by ramie fabrics with bio-based flame retardant coating[J].Polymer Composites,2017,52(11):778-786.
[51]Kimura H, Matsumoto A,Sugito H,et al.New thermosetting resin from poly(p-vinylphenol)based benzoxazine and epoxy resin[J].Journal of Applied Polymer Science,2001,79(3):555-565.
[52]Li S,Zou T,Liu X,et al.Synthesis and characterization of benzoxazine monomers from rosin and their thermal polymerization[J].Designed Monomers&Polymers,2014,17(1):40-46.
[2]Ishida H,Allen D J.Physical and mechanical characterization of near-zero shrinkage polybenzoxazines[J].Journal of Polymer Science Part B Polymer Physics,2015,34(6):1019-1030.
[3]Ishida H, Rodriguez Y.Curing kinetics of a new benzoxazine-based phenolic resin by differential scanning calorimetry[J].Polymer,1995,36(16):3151-3158.
[4]Hong Y L,Ishida H.Improved thermal stability of polybenzoxazines by transition metals[J]. Polymer Degradation&Stability,2006,91(4):805-815.
[5]李洪峰,曲春艳,顾继友,等.航空航天用耐高温苯并噁嗪树脂胶粘剂[J].粘接,2017,38(8):31-36.
[6]张建,刘向阳,顾宜.高性能苯并噁嗪模压复合材料的研究[J].塑料工业,2009,37(3):78-81.
[7]Xiang H,Ling H, Wang J,et al.A novel high performance RTM resin based on benzoxazine[J].Polymer Composites,2010,26(5):563-571.
[8]Rimdusit S,Ishida H.Development of new class of electronic packaging materials based on ternary systems of benzoxazine,epoxy,and phenolic resins[J].Polymer,2000,41(22):7941-7949.
[9]翁云宣.2016生物基材料专刊序言[J].生物工程学报,2016,32(6):711-714.
[10]Methot J C,Cholette A.Effect of polymerizing diacetylene groups on the lowering of polymerization temperature of benzoxazine groups in the highly thermally stable,mainchain-typepolybenzoxazines[J]. Macromolecules,2009,42(14):5121-5127.
[11]Ghosh N N,Kiskan B,Yagci Y.PolybenzoxazinesNew high performance thermosetting resins:Synthesis and properties[J].Progress in Polymer Science,2007,32(11):1344-1391.
[12]Agag T,Lin J,Ishida H.A new synthetic approach for difficult benzoxazines:Preparation and polymerization of4, 4’-diaminodiphenylsulfone-basedbenzoxazine monomer[J].Polymer,2009,50(25):5940-5944.
[13]Ishida H.Process for preparation of benzoxazine compounds in solventless systems:US,5,543,516[P].1996-8-6.
[14]崔俊儒,辛嘉英,牛建中,等.甲烷氧化细菌催化二氧化碳生物合成甲醇的研究[J].分子催化,2004,18(3):214-218.
[15]崔玉虎,王奇,苟光俊,等.木质素催化降解液化的研究进展[J].材料导报,2017,31(5):112-116.
[16]董晨.浅谈我国造纸工业的特点及污染防治现状[J].科学中国人,2015(6):152-156.
[17]赵晓梅.造纸废水中木质素的回收利用[J].辽宁大学学报(自然科学版),2012,39(1):44-46.
[18]曾育才,张学先,刘小玲.造纸黑液木质素及其综合利用[J].广东化工,2005,32(10):11-14.
[19]Wang C F,Sun J Q,Liu X D,et al.Synthesis and copolymerization of fully bio-based benzoxazines from guaiacol,furfurylamine and stearylamine[J].Green Chemistry,2012,14(10):2799-2806.
[20]Wang C F,Zhao C H,Sun J Q,et al.Synthesis and thermal properties of a bio-based polybenzoxazine with curing promoter[J].Journal of Polymer Science Part A Polymer Chemistry,2013,51(9):2016-2023.
[21]Sini N K,Bijwe J,Varma I K.Renewable benzoxazine monomer from Vanillin:Synthesis,characterization,and studies on curing behavior[J].Journal of Polymer Science Part A Polymer Chemistry,2014,52(1):7-11.
[22]Van A,Chiou K,Ishida H.Use of renewable resource vanillin for the preparation of benzoxazine resin and reactive monomeric surfactant containing oxazine ring[J].Polymer,2014,55(6):1443-1451.
[23]ComíM,Lligadas G,Ronda J C,et al.Renewable benzoxazine monomers from “lignin-like”naturally occurring phenolic derivatives[J].Journal of Polymer Science Part A Polymer Chemistry,2013,51(22):4894-4903.
[24]Froimowicz P R.Arza C, Han L,et al.Smart,sustainable,and ecofriendly chemical design of fully bio-based thermally stable thermosets based on benzoxazine chemistry[J].Chemsuschem,2016,9(15):1921-1928.
[25]Trejomachin A,Verge P,Puchot L,et al.Phloretic acid as an alternative to the phenolation of aliphatic hydroxyls for the elaboration of polybenzoxazine[J].Green Chemistry,2017,19(21):28-35.
[26]Xu M,Huang Q,Chen Q,et al.Synthesis and characterization of octadecylamine grafted multi-walled carbon nanotubes[J].Chemical Physics Letters,2003,375(5-6):598-604.
[27]宋谋道,朱吉亮,张邦华,等.聚乙二醇改性聚乳酸的研究[J].高分子学报,1998,1(4):454-458.
[28]方维海,方德彩.丙烯酸气相热解机理的理论探讨[J].物理化学学报,1993,9(5):630-634.
[29]Yamauchi Y,Oshima R,Ju K.Configuration of the olefinic bonds in the heteroolefinic side-chains of japanese lacquer urushiol:Separation and identification of components of dimethylurushiol by means of reductive ozonolysis and high-performance liquid chromatography[J].Journal of Chromatography A,1982,243(1):71-84.
[30]Kumanotani J.Urushi(Oriental Lacquer):A Natural Aesthetic Durable and Future-Promising Coating[M].Butterworths:Digestive Physiology and Nutrition of the Ruminant,1995:163-195.
[31]CalòE,Maffezzoli A,Mele G,et al.Synthesis of a novelcardanol-basedbenzoxazinemonomerand environmentally sustainable production of polymers and bio-composites[J].Green Chemistry,2007,9(7):754-759.
[32]Rao B S,Palanisamy A.Synthesis of bio based low temperature curable liquid epoxy,benzoxazine monomer system from cardanol:Thermal and viscoelastic properties[J].European Polymer Journal,2013,49(8):2365-2376.
[33]Xu G,Shi T,Liu J,et al.Preparation of a liquid benzoxazine based on cardanol and the thermal stability of its graphene oxide composites[J].Journal of Applied Polymer Science,2014,131(11):1732-1742.
[34]Zhang C,Zhang Y,Zhou Q,et al.Processability and mechanical properties of bis-benzoxazine modified by the cardanol-based aromatic diamine benzoxazine[J].Journal of Polymer Engineering,2014,34(6):561-568.
[35]Lochab B,Varma I,Bijwe J.Cardanol-based bisbenzoxazines:Effect of structure on thermal behaviour[J].Journal of Thermal Analysis&Calorimetry,2012,107(2):661-668.
[36]Vasapollo G,Pio I, Mele G,et al.Solvent free synthesis of novel mono-and bis-benzoxazines from cashew nut shell liquid components[J].Current Organic Chemistry,2012,16(21):113-121.
[37]Zhang C,Zhang Y,Zhou Q,et al.Processability and mechanical properties of bisbenzoxazine modified by the cardanol-based aromatic diamine benzoxazine[J].Journal of Polymer Engineering,2014,34(6):561-568.
[38]Zhang L,Yang Y,Chen Y,et al.Cardanol-capped main-chain benzoxazine oligomers for resin transfer molding[J].European Polymer Journal,2017(4):140-149.
[39]Patil D M,Phalak G A,Mhaske S T.Synthesis and characterization of bio-based benzoxazine oligomer from cardanol for corrosion resistance application[J].Journal of Coatings Technology&Research,2017(3):1-14.
[40]Ma H X,Xu Z B,Qiu J J,et al.Synthesis of artificial urushi via ring-opening reaction of benzoxazine with renewable cardanol[J].Polymer,2017(6):34-42.
[41]Zeng M,Pang T,Chen J,et al.Facile preparation of thenovelcastoroil-basedbenzoxazine-urethane copolymer with improved high-frequency dielectric properties[J].Journal of Materials Science Materials in Electronics,2018(5):1-10.
[42]王海青,曹万荣,李光旭,等.腰果酚基苯并噁嗪及其高生物质含量复合材料的制备和性能研究[J].浙江理工大学学报,2016,35(1):29-34.
[43]Puchot L,Verge P,Fouquet T,et al.Breaking the symmetry of dibenzoxazines:aparadigm to tailor the design of bio-based thermosets[J].Green Chemistry,2016,18(11):3346-3353.
[44]Dumas L,Bonnaud L,Olivier M,et al.Bio-based high performance thermosets:Stabilization and reinforcement of eugenol-based benzoxazine networks with BMI and CNT[J].European Polymer Journal,2015,6(7):494-502.
[45]Dumas L,Bonnaud L,Olivier M,et al.Eugenol-based benzoxazine:From straight synthesis to taming of the network properties[J].Journal of Materials Chemistry A,2015,3(11):6012-6018.
[46]Dumas L,Bonnaud L,Olivier M,et al.Chavicol benzoxazine:Ultrahigh Tg biobased thermoset with tunable extended network[J].European Polymer Journal,2016,8(1):337-346.
[47]Dumas L,Bonnaud L,Olivier M,et al.Arbutin-based benzoxazine:En route to an intrinsic water soluble biobased resin[J].Green Chemistry,2016,4(8):311-319.
[48]彭林才,林鹿,李辉.生物质转化合成新能源化学品乙酰丙酸酯[J].化学进展,2012,24(5):801-809.
[49]Zú1iga C, Larrechi M S, Lligadas G, et al.Polybenzoxazines from renewable diphenolic acid[J].Journal of Polymer Science Part A Polymer Chemistry,2011,49(5):1219-1227.
[50]Yan H,Li N,Cheng J,et al.Fabrication of flame retardant benzoxazine semi-biocomposites reinforced by ramie fabrics with bio-based flame retardant coating[J].Polymer Composites,2017,52(11):778-786.
[51]Kimura H, Matsumoto A,Sugito H,et al.New thermosetting resin from poly(p-vinylphenol)based benzoxazine and epoxy resin[J].Journal of Applied Polymer Science,2001,79(3):555-565.
[52]Li S,Zou T,Liu X,et al.Synthesis and characterization of benzoxazine monomers from rosin and their thermal polymerization[J].Designed Monomers&Polymers,2014,17(1):40-46.