A Review on the New Development of Benzoxazine Resin: Use in Smart Materials and Energy and Environmental Applications
LI Xiaodan1, HU Xinyu1, LIU Xiaoping1, LIU Xiaoqing1, SHEN Yu2, TANG Ying1, FENG Jiacheng1
1 Chongqing Key Laboratory of Catalysis and New Environmental Materials, Chongqing Technology and Business University, Chongqing 400067, China; 2 National Research Base of Intelligent Manufacturing Service, Chongqing Technology and Business University, Chongqing 400067, China
Abstract: Benzoxazine resin is a kind of high-performance thermosetting resin. Because of its high thermal stability, high char yield, flame retardant, low water absorption, low shrinkage, limited or no by-products during curing, and good mechanical properties, it has become an effective substitute for phenolic resin, bismaleimide resin and other high-performance polymers and been widely used in aerospace, electronic circuit board, blends and alloys industry. Although benzoxazine resins are widely used in several applications, the research of polybenzoxazine mainly focuses on the synthesis of composite materials and the substitution of traditional epoxy resin and phenolic resin. Because polybenzoxazine contains unique molecular structures such as tertiary amines and phenolic hydroxyl groups that can form hydrogen bonds, and has high flexibility in molecular design, its application potential in many emerging fields also deserves attention. In terms of intelligent application, electrochemically active coatings and hydrophobic surfaces can be easily obtained from polybenzoxazine; and self-healing function can be imparted to benzoxazine resin by virtue of the supramolecular structure of polybenzoxazine and its precursors; in addition, shape memory polymer, near infrared (NIR) and polychromatic electrochromic materials can also be constructed based on benzoxazine resin. In the fields of energy and environment, benzoxazine resin can be used to adsorb metal ions in water due to the metal binding ability of N and O atoms or functional groups such as mercaptans and carboxylic acids; moreover, sulfur-containing benzoxazine resin also can be used as positive electrode of lithium-sulfur battery. In this paper, the intelligent application of polybenzoxazine materials and their applications in the energy and environmental fields are reviewed, and the relationship between the properties and structures of polybenzoxazine is discussed.
作者简介: 李晓丹,重庆工商大学材料科学与工程系副教授,硕士研究生导师。2007年6月毕业于四川大学,获工学学士学位。2007年9月进入四川大学高分子科学与工程学院硕博连读,2012年6月获高分子科学与工程专业工学博士学位。2015年10月—2017年12月在四川大学从事博士后研究。长期从事功能高分子材料、纳米复合材料、环境功能材料等领域,特别是高性能苯并噁嗪树脂的理论及应用的研究。近年来,主持国家级项目1项,省部级项目6项,在Polymer Chemistry、Physical Chemistry Chemical Physics等国际学术期刊上发表相关研究论文20余篇,编著专著2部。
引用本文:
李晓丹, 胡心雨, 刘小平, 刘小清, 申渝, 唐莹, 冯佳成. 苯并噁嗪树脂的研究新进展:智能化应用及能源、环境领域应用[J]. 材料导报, 2021, 35(3): 3209-3218.
LI Xiaodan, HU Xinyu, LIU Xiaoping, LIU Xiaoqing, SHEN Yu, TANG Ying, FENG Jiacheng. A Review on the New Development of Benzoxazine Resin: Use in Smart Materials and Energy and Environmental Applications. Materials Reports, 2021, 35(3): 3209-3218.
Nair C P R.Progress in Polymer Science,2004,29(5),401.2 Ghosh N N, Kiskan B,Yagci Y.Progress in Polymer Science,2007,32(11),1344.3 Wirasate S, Dhumrongvaraporn S, Allen D J, et al.Journal Applied of Polymer Science,1998,70(7),1299.4 Kim H D, Ishida H.Macromolecules,2003,36(22),8320.5 Kanchanasopa M, Yanumet N, Hemvichian K, et al.Polymers & Polymer Composites,2001,9(6),367.6 Kim H D, Ishida H.Journal of Applied Polymer Science.2001,79(7),1207.7 Hemvichian K, Laobuthee A, Chirachanchai S, et al.Polymer Degradation and Stability,2002,76(1),1.8 Liu Y L, Chou C I.Journal of Polymer Science Part A: Polymer Chemistry,2005,43(21),5267.9 Lin C H, Cai S X, Leu T S, et al.Journal of Polymer Science Part A: Polymer Chemistry,2006,44(11),3454.10 Liu Y H, Zhang W, Chen Y, et al.Journal Applied of Polymer Scirnce,2006,99(3),927.11 Low H Y, Ishida H.Polymer Degradation and Stability,2006,91(4),805.12 Kiskan B, Yagci Y, Sahmethogilu E, et al.Journal of Polymer Science Part A: Polymer Chemistry,2007,45(6),999.13 Douse E, Kopsidas S, Jesson D, et al.Reactive and Functional Polymers,2016,103,117.14 Ishida H, Allen D J.Journal of Polymer Science Part B: Polymer Physics,1996,34(6),1019.15 Ishida H, Allen D J.Journal Applied of Polymer Scirnce,2001,79(3),406.16 Goward G R, Sebastiani D, Schnell I, et al.Journal of the American Chemical Society,2003,125(19),5792.17 Hamerton I, McNamara L T, Howlin B J, et al.Macromolecules,2013,46(13),5117.18 Cid J A, Wang Y X, Ishida H.Polymers & Polymer Composites,1999,7(6),409.19 Wang Y X, Ishida H.Polymer,1999,40(16),4563.20 Chutayothin P, Ishida H.Macromolecules,2010,43(10),4562.21 Kudoh R, Sudo A, Endo T.Macromolecules,2010,43(3),1185.22 Sudo A, Hirayama S, Endo T.Journal of Polymer Science Part A: Polymer Chemistry,2010,48(2),479.23 Imran M, Kiskan B, Yagci Y.Tetrahedron Letters,2013,54(36),4966.24 Lligadas G, Tuzun A, Ronda J C, et al.Polymer Chemistry,2014,5(23),6636.25 Sini N K, Bijwe J, Varma I K.Journal of Polymer Science Part A: Polymer Chemistry,2014,52(1),7.26 Ishida H, Ohba S.Polymer,2005,46(15),5588.27 Mohamed M G, Hsiao C H, Hsu K C, et al.RSC Advances,2015,5(17),12763.28 Zhang T, Wang J, Feng T, et al.RSC Advances,2015,5(42),33623.29 Mohamed M G, Hsu K C, Kuo S W.Polymer Chemistry,2015,6(13),2423.30 Kiskan B, Yagci Y.Journal of Polymer Science Part A: Polymer Chemistry,2007,45(9),1670.31 Agag T, Takeichi T.Macromolecules,2001,34(21),7257.32 Agag T, Takeichi T.Macromolecules,2003,36(16),6010.33 Sudo A, Du L C, Hirayama S, et al.Journal of Polymer Science Part A: Polymer Chemistry,2010,48(13),2777.34 Kiskan B, Koz B, Yagci Y.Journal of Polymer Science Part A: Polymer Chemistry,2009,47(24),6955.35 Agag T, Geiger S, Alhassan S M, et al.Macromolecules,2010,43(17),7122.36 Baranek A D, Kendrick L L, Narayanan J, et al.Polymer Chemistry,2012,3(10),2892.37 Demir K D, Kiskan B, Aydogan B, et al.Reactive and Functional Polymers,2013,73(2),346.38 Yagci Y, Kiskan B, Ghosh N N.Journal of Polymer Science Part A: Polymer Chemistry,2009,47(21),5565.39 Aydogan B, Sureka D, Kiskan B, et al.Journal of Polymer Science Part A: Polymer Chemistry,2010,48(22),5156.40 Kiskan B, Aydogan B, Yagci Y.Journal of Polymer Science Part A: Polymer Chemistry,2009,47(3),804.41 Chou C I, Liu Y L.Journal of Polymer Science Part A: Polymer Chemistry,2008,46(19),6509.42 Chernykh A, Liu J P, Ishida H.Polymer,2006,47(22),7664.43 Takeichi T, Kano T, Agag T.Polymer,2005,46(26),12172.44 Agag T, Takeichi T.Journal of Polymer Science Part A: Polymer Chemistry,2007,45(10),1878.45 Lin C H, Chang S L, Shen T Y, et al.Polymer Chemistry,2012,3(4),935.46 Demir K D, Kiskan B, Yagci Y.Macromolecules,2011,44(7),1801.47 Demir K D, Kiskan B, Latthe S S, et al.Polymer Chemistry,2013,4(6),2106.48 Nagai A, Kamei Y, Wang X S, et al.Journal of Polymer Science Part A: Polymer Chemistry,2008,46(7),2316.49 Chernykh A, Agag T, Ishida H.Polymer,2009,50(2),382.50 Altinkok C, Kiskan B, Yagci Y.Journal of Polymer Science Part A: Polymer Chemistry,2011,49(11),2445.51 Kiskan B, Yagci Y, Ishida H.Journal of Polymer Science Part A: Polymer Chemistry,2008,46(2),414.52 Zhang K, Liu J, Ishida H.Macromolecules,2014,47(24),8674.53 Agag T, Liu J, Graf R, et al.Macromolecules,2012,45(22),8991.54 Kiskan B, Ghosh N N, Yagci Y.Polybenzoxazine-based composites as high-performance materials,Polymer International,2011,60(2),167.55 Goward G R, Schnell I, Brown S P, et al.Magnetic Resonance in Che-mistry,2001,39,S5.56 Kim H D, Ishida H.The Journal of Physical Chemistry A,2002,106(14),3271.57 Dong H, Xin Z, Lu X, et al.Polymer,2011,52(4),1092.58 Yang P, Wang X, Fan H, et al.Physical Chemistry Chemical Physics,2013,15(37),15333.59 Chirachanchai S, Laobuthee A, Phongtamrug S, et al.Journal of Applied Polymer Science,2000,77(12),2561.60 Kaewvilai A, Rujitanapanich S, Wattanathana W, et al.Macromolecules,2012,17(1),511.61 Wool R P.Soft Matter,2008,4(3),400.62 Sawaryn C, Landfester K, Taden A.Macromolecules,43(21),8933.63 Kiskan B, Yagci Y.Journal of Polymer Science Part A, Polymer Chemistry,2014,52(20),2911.64 Arslan M, Kiskan B, Yagci Y.Macromolecules,2015,48(5),1329.65 Wang B, Yang P, Li Y, et al.Polymer International,2017,66,1159.66 Zhang Y, Broekhuis A A, Picchioni F.Macromolecules,2009,42(6),1906.67 Haberhauer P.In: Polysulfones (PES/PSU), Polysulfone (PES/PSU), Kunststoffe Plast Europe,2004,pp.122.68 Taskin O S, Kiskan B, Yagci Y.Macromolecules,2013,46(22),8773.69 Lendlein A, Kelch S.Angewandte Chemie International Edition,2002,41(12),2034.70 Lendlein A, Jiang H Y, Junger O, et al. Nature,2005,434(7035),879.71 Prima M A D, Lesniewski M, Gall K, et al.Smart Materials and Structures,2007,16(6),2330.72 Kimura H, Matsumoto A, Hasegawa K, et al.Journal of Applied Polymer Science,1998,68(12),1903.73 Rao B S, Reddy K R, Pathak S K, et al.Polymer International,2005,54(10),1371.74 Chang S L, C.H. Lin C H.Journal of Polymer Science Part A, Polymer Chemistry,2010,48(11),2430.75 Sarawut R, Montha L, Kasinee H, et al.Smart Materials and Structures,2013,22(7),075033.76 Kumar A, Stephenson L D, Murray J N.Progress in Organic Coatings,2006,55(3),244.77 Radhakrishnan S, Sonawane N, Siju C R.Progress in Organic Coatings,2009,64(4),383.78 Zhou C, Lu X, Xin Z, et al.Corrosion Science,2013,70,145.79 Lu X, Liu Y, Zhou C, et al.RSC Advances,2016,6(7),5805.80 ASTM, Annual Book of ASTM Standards, D 3359-90, Standard Test Methods for Measuring Adhesion by Tape Test, Test Method B, West Conshohocken,1991.81 DIN 53152, Deutsche Normen, Deutscher Normenausschuss (DNA),1959.82 Tuzun A, Kiskan B, Alemdar N, et al.Journal of Polymer Science Part A, Polymer Chemistry,2010,48(19),4279.83 Aydogan C, Kiskan B, Hacioglu S O, et al.RSC Advances,2014,4(52),27545.84 Zhang X, Shi F, Niu J, et al.Journal of Materials Chemistry,2008,18(6),621.85 Coulson S R, Woodward I, Badyal J P S, et al.The Journal of Physical Chemistry B,2000,104(37),8836.86 Kato K, Uchida E, Kang E T, et al.Progress in Polymer Science,2003,28(2),209.87 Kang E T, Zhang Y.Advanced Materials,2000,12(20),1481.88 Wang C F, Su Y C, Kuo S W, et al.Angewandte Chemie International Edition,2006,45(14),2248.89 Wang C F, Wang Y T, Tung P H, et al.Langmuir,2006,22(20),8289.90 Qu L, Xin Z, et al.Langmuir,2011,27(13),8365.91 Liu J, Lu X, Xin Z, et al.Langmuir,2013,29(1),411.92 Huang M, Si Y, Tang X, et al.Journal of Materials Chemistry A,2013,1(45),14071.93 Dai C, Liu N, Cao Y, et al.Soft Matter,2014,10(40),8116.94 Zhang X, Li Z, Liu K, et al.Advanced Functional Materials,2013,23(22),2881.95 Gao P, Liu Z, Sun D D, et al.Journal of Materials Chemistry A,2014,2(34),14082.96 Zhang L, Zhong Y, Cha D, et al.Scientific Reports,2013,3,2326.97 Gao S J, Shi Z, Zhang W B, et al.ACS Nano,2014,8(6),6344.98 Rathousky J, Kalousek V, Kolá<inline-formula><mml:math xmlns:mml="http://www.w3.org/1998/Math/MathML" id="Mml1-1005-023X-35-3-3209"><mml:mover><mml:mrow><mml:mi mathvariant="normal">r</mml:mi></mml:mrow><mml:mrow><mml:mi>?</mml:mi></mml:mrow></mml:mover></mml:math></inline-formula> M, et al.Catalysis Today,2011,161(1),202.99 Zhang W, Lu X, Xin Z, et al.Nanoscale,2015,7(46),19476.100 Macko J A, Ishida H.Journal of Polymer Science Part B, Polymer Phy-sics,2000,38(20),2687.101 Arslan M, Kiskan B, Yagci Y.Macromolecules,2016,49(14),5026.102 Tasdelen M A, Kiskan B, Yagci Y.Macromolecular Rapid Communications,2006,27(18),1539.103 Han Y J, Lin C Y, Liang M, et al.Macromolecular Rapid Communications,2016,37(10),845.104 Liao C S, Wang C F, Lin H C, et al.Langmuir,2009,25(6),3359.105 Gogoi N, Rastogi D, Jassal M, et al.The Journal of The Textile Institute,2014,105(11),1212.106 Lin L C, Yen H J, Kung Y R, et al.Journal of Materials Chemistry C,2014,2(37),7796.107 Shih H K, Chu Y L, Chang F C, et al.Polymer Chemistry,2015,6(34),6227.108 Gorodisher I.In: Handbook of Benzoxazine Resins, Chapter 11-catalytic opening of lateral benzoxazine rings by thiols, H.I. Agag (Ed.), Amsterdam,2011,pp.211.109 Semerci E, Kiskan B, Yagci Y.European Polymer Journal,2015,69,636.110 Bektas S, Kiskan B, Orakdogen N, et al.Polymer,2015,75,44.111 Musa A, Kiskan B, Yagci Y.Polymer,2014,55(22),5550.112 Beyazkilic Z, Kahveci M U, Aydogan B, et al.Journal of Polymer Science Part A, Polymer Chemistry,2012,50(19),4029.113 Kawaguchi A W, Sudo A, Endo T.Journal of Polymer Science Part A, Polymer Chemistry,2012,50(8),1457.114 Kawaguchi A W, Sudo A, Endo T.ACS Macro Letters,2012,2(1),1.115 Chung W J, Griebel J J, Kim E T, et al.Nature Chemistry,2013,5(6),518.116 Griebel J J, Li G, Glass R S, et al.Journal of Polymer Science Part A, Polymer Chemistry,2015,53(2),173.117 Swager T M, Fennell J F.Synfacts,2016,12(04),363.118 Arslan M, Kiskan B, Yagci Y.Macromolecules,2016,49(3),767.119 Arza C R, Froimowicz P, Ishida H.RSC Advances,2016,6(42),35144.120 Ji X, Lee K T, Nazar L F.Nature Materials,2009,8(6),500.121 Demir-Cakan R, Morcrette M, Nouar F, et al.Journal of the American Chemical Society,2011,133(40),16154.122 Barchasz C, Molton F, Duboc C, et al.Analytical Chemistry,2012,84(9),3973.123 Arslan M, Kiskan B, Cengiz E C, et al.European Polymer Journal,2016,80,70.124 Simmonds A G, Griebel J J, Park J, et al.ACS Macro Letters,2014,3(3),229.125 Shukla S, Ghosh A, Sen U K, et al.Chemistry Select,2016,1(3),594.126 Je S H, Hwang T H, Talapaneni S N, et al.ACS Energy Letters,2016,1(3),566.127 Clarkson T W.Critical Reviews in Clinical Laboratory Sciences,1997,34(4),369.128 Atwood D A.In: Recent Developments in Mercury Science, Mercury removal from water, University of Kentucky, USA,2006,pp.163.