Synthesis, Modification and Application of Polyaspartic Acid/Salt: the State-of-art Technological Advances
YANG Jinhui1, LIU Tai1, CHEN Yanxue1, WANG Man1, WANG Hongyuan2, LIU Hongbin2
1 School of Materials Science and Engineering, Shijiazhuang Tiedao University, Shijiazhuang 050043; 2 Key Laboratory of Nonpoint Source Pollution Control of Ministry of Agriculture, Beijing 100081
Abstract: Polyaspartic acid/salt (PASP), a novel biodegradable and environmental-friendly material, has found wide application in many fields by virtue of its special molecular chain structure and excellent properties, and has attained notable improvement in technological diversification of synthesis & modification, product type & performance, and application range, due to the deep and intensive research endeavors in recent years. This review renders a vivid description upon the synthesis/modification techniques, the industrial/agricultural applications (e.g. scale inhibitor, corrosion inhibitor, fertilizer synergist, water retention agent, and paint), biomedical and other applications. We also sketch out the prospective development tendency of PASP and the relevant derivatives.
杨晋辉,刘泰,陈艳雪,王满,王洪媛,刘宏斌. 聚天门冬氨酸/盐的合成、改性及应用研究进展[J]. 《材料导报》期刊社, 2018, 32(11): 1852-1862.
YANG Jinhui, LIU Tai, CHEN Yanxue, WANG Man, WANG Hongyuan, LIU Hongbin. Synthesis, Modification and Application of Polyaspartic Acid/Salt: the State-of-art Technological Advances. Materials Reports, 2018, 32(11): 1852-1862.
1 Cheng D M, Chen Q, Zhu A P, et al. Progress in research on poly(aspartic acid) and its derivatives[J].Materials Review,2002(7):60(in Chinese). 成大明,陈强,朱爱萍,等.聚天门冬氨酸及其衍生物的研究进展[J].材料导报,2002(7):60. 2 Xiong R C, Dong X L, Wei G. Synthesis and scale inhibition of polyaspartic acid as a green polymer[J].Industrial Water Treatment,2001,1(1):17(in Chinese). 熊蓉春,董雪玲,魏刚.绿色生物高分子聚天门冬氨酸的合成及其阻垢性能研究[J].工业水处理,2001,1(1):17. 3 Kuhnel D, Nickel C. The OECD expert meeting on ecotoxicology and environmental fate—Towards the development of improved OECD guidelines for the testing of nanomaterials[J].Science of the Total Environment,2014,472:347. 4 Xiao F L, Wei M, Zhao J. Advance in research of polyaspartic acid[J].Biomass Chemical Engineering,2014,48(6):50(in Chinese). 肖凤龙,卫民,赵剑.聚天门冬氨酸合成与应用研究进展[J].生物质化学工程,2014,48(6):50. 5 Fang L, Tan T W. Chemical syntheses and application of polyaspartates[J].Chemical Industry and Engineering Progress,2001,20(3):24(in Chinese). 方莉,谭天伟.聚天门冬氨酸的合成及其应用[J].化工进展,2001,20(3):24. 6 Yang Y H, Xie B B, Han W L, et al. Study on the synergistic effect of PASP-ATMP compound scale inhibitors and influencing factors[J].Applied Chemical Industry,2012,41(5):834(in Chinese). 杨耀辉,解蓓蓓,韩文礼,等.复合阻垢剂PASP-ATMP的协同效应及影响因素研究[J].应用化工,2012,41(5):834. 7 Lei W, Ping C X, Wang F H, et al. Synthesis of acrylic acid-acrylamide copolymer containing fluorescent group[J].Petrochemical Technology,2006,35(2):145(in Chinese). 雷武,平春霞,王风贺,等.含荧光基团的丙烯酸-丙烯酰胺共聚物的合成[J].石油化工,2006,35(2):145. 8 Wang Y, Hou Y, Ruan G, et al. Study on the polymerization of aspartic acid catalyzed by phosphoric acid[J].Journal of Macromolecular Science,Part A,2003,40(3):293. 9 Tomida M, Nakato T, Matsunami S, et al. Convenient synthesis of high molecular weight poly(succinimide) by acid-catalysed polycondensation of L-aspartic acid[J].Polymer,1997,38(18):4733. 10 程终发,万振涛,刘全华,等.利用L-天门冬氨酸合成聚天门冬氨酸新工艺:中国,103724625A[P].2014-04-16. 11 谭天伟,方莉,曹辉.聚天门冬氨酸的合成方法:中国,1341676A[P].2002-03-27. 12 杨现斌,底建涛.一种聚天门冬氨酸的制备方法:中国,103819673A[P].2014-05-28. 13 卫民,赵剑,刘军利,等.一种液相介质中聚天门冬氨酸的制备方法:中国,104327267A[P].2015-02-04. 14 杨士林,高倩.一种利用咪唑类离子液体催化合成聚天门冬氨酸的方法:中国,10225035A[P].2011-11-23. 15 Chen S, Zhou Z M, Yu C J. Study on the synthesis of poly-aspartic acid[J].Applied Chemical Industry,2011,40(1):118(in chinese). 陈舜,周志明,于超俊.聚天门冬氨酸的合成研究[J].应用化工,2011,40(1):118. 16 金政坤,李钟禾,徐成德,等.使用马来酸酐制造聚天门冬氨酸的方法:中国,101535376A[P].2009-09-16. 17 Hu Z G, Wang X, Zhang Y L, et al. Latest research development of modified polyaspartic acid[J].Applied Chemical Industry,2014,43(2):360(in chinese). 胡志光,王昕,张玉玲,等.改性聚天门冬氨酸研究最新进展[J].应用化工,2014,43(2):360. 18 杨士林,王博.多组分蒸发结晶共聚改性合成聚天门冬氨酸衍生物的方法:中国,102250353A[P].2011-11-23. 19 Zhang Y L, Hu Z G, Wang J L, et al. Biodegradation of poly(aspartic acid-lysine) copolymers by mixed bacteria from natural water[J].Polymer Degradation and Stability,2016,128:134. 20 Chen J, Xu L, Han J, et al. Synthesis of modified polyaspartic acid and evaluation of its scale inhibition and dispersion capacity[J].Desalination,2015,358:42. 21 Xu Y, Zhao L, Wang L, et al. Synthesis of polyaspartic acid-melamine grafted copolymer and evaluation of its scale inhibition performance and dispersion capacity for ferric oxide[J].Desalination,2012,286:285. 22 Gao Y, Fan L, Ward L, et al. Synthesis of polyaspartic acid derivative and evaluation of its corrosion and scale inhibition performance in seawater utilization[J].Desalination,2015,365:220. 23 柳鑫华,孔毅超,杜蛟,等.改性聚天门冬氨酸阻垢剂的制备及其应用方法:中国,101792504A[P].2010-08-04. 24 黄凯,孔利,傅淑霞.聚天门冬氨酸衍生物及其制备方法和应用:中国,102875808A[P].2013-01-16. 25 邹金娥.一种复合聚天门冬氨酸的改性方法:中国,103819669A[P].2014-05-28. 26 程池.一种改性聚天门冬氨酸阻垢剂的制备方法:中国,104556431A[P].2015-04-29. 27 杨晋辉,陈艳雪,彭玲,等.高分子量有机胺和马来酸酐改性聚天门冬氨酸盐及其制备方法:中国,10654383436A[P].2017-03-29. 28 Gyarmati B, Krisch E, Szilágyi A. In situ oxidation-induced gelation of poly(aspartic acid) thiomers[J].Reactive and Functional Polymers,2014,84:29. 29 Cao H, Ma X, Sun S, et al. A new photocrosslinkable hydrogel based on a derivative of polyaspartic acid for the controlled release of ketoprofen[J].Polymer Bulletin,2009,64(6):623. 30 Zhang B, He C, Wang C, et al. Synergistic corrosion inhibition of environment-friendly inhibitors on the corrosion of carbon steel in soft water[J].Corrosion Science,2015,94:6. 31 何锰.一种聚天门冬氨酸和聚丙烯酸复合阻垢剂的生产方法:中国,105692927A[P].2016-06-22. 32 何猛.聚天门冬氨酸和羟基亚乙基二磷酸复合阻垢剂:中国,105600954A[P].2016-05-25. 33 何猛.一种聚天门冬氨酸和多氨基多醚基甲叉磷酸复配阻垢剂:中国,105692930A[P].2016-06-22. 34 何猛.一种聚天门冬氨酸和二乙烯三胺五亚甲基磷酸复配阻垢剂:中国,105692931A[P].2016-06-22. 35 Nita L, Chiriac A, Bercea M, et al. Synergistic behavior of poly(aspartic acid) and pluronic F127 in aqueous solution as studied by viscometry and dynamic light scattering[J].Colloids and Surfaces B: Biointerfaces,2013,103:544. 36 Nita L, Chiriac A P, Bercea M. Effect of pH and temperature upon self-assembling process between poly(aspartic acid) and pluronic F127[J].Colloids and Surfaces B: Biointerfaces,2014,119:47. 37 Nita L, Chiriac A, Bercea M, et al. Static and dynamic investigations of poly(aspartic acid) and pluronic F127 complex prepared by self-assembling in aqueous solution[J].Applied Surface Science,2015,359:486. 38 Zhu Z L, Liang X M, Hao J Y, et al. Study on the synthesis and scale inhibition of polyaspartic acid[J].Industrial Water Treatment,2004,24(4):30(in chinese). 朱志良,梁晓明,郜俊影,等.聚天门冬氨酸的合成方法及其阻垢性能之间的关系研究[J].工业水处理,2004,24(4):30. 39 王永丽,黄少斌,王旭东.聚天门冬氨酸的阻垢机理[C]∥中国精细化工协会第一届水处理化学品行业年会论文集.延吉,2005:142. 40 Huo Y N, Lu Z. Research on the effect of polyaspartic acid on crystallization of calcium carbonate[J].Fine Chemicals,2004,21(3):206(in Chinese). 霍宇凝,陆柱.环保型阻垢剂聚天门冬氨酸对碳酸钙结晶过程的影响[J].精细化工,2004,21(03):206. 41 Huang J, Xu Q, Ren Z F, et al. Resarch progress of corrosion and scale inhibitors in circulating cooling water[J].Plating & Finishing,2009,31(2):131(in Chinese). 黄娟,徐强,任志峰,等.循环冷却水缓蚀剂和阻垢剂的研究进展[J].电镀与精饰,2009,31(2):131. 42 Silverman D C, Kolota D J, Stover F S. Eeffct of pH on corrosion inhibition of steel by polyaspartic acid[J].Corrosion Science,1995,51(11):818. 43 Kathie B. Mechanisms of calcite dissolution using environmentally benign polyaspartic acid: A rotating disk study[J].Langmuir,2003,19(41):5669. 44 Xu Y J, Yang W Z, Tang Y M, et al. Performance of scale-corrosion inhibition of polyaspartic acid[J].Journal of Nanjing University of Technology (Natural Science Edition),2002,24(1):87(in Chinese). 徐耀军,杨文忠,唐永明,等.聚天门冬氨酸的阻垢缓蚀性能[J].南京工业大学学报(自然科学版),2002,24(1):87. 45 Wu Y J, Zhang L H, Tian C L, et al. Researches on polyaspartic acid-based composite and its scate-and corrosion-inhibition[J].Technology of Water Treatment,2007,33(7):33(in Chinese). 吴运娟,张利辉,田彩莉,等.聚天门冬氨酸复配物及其阻垢缓蚀性能[J].水处理技术,2007,33(7):33. 46 Du Z J, Yang H, Wang S C, et al. Advance of homologous polypeptides polyaspartic acids for agriculture[J].Chinese Journal of Tropical Crops,2011,2(12):2381(in Chinese). 杜中军,杨浩,王树昌,等.农用聚天门冬氨酸同源多肽研究进展[J].热带作物学报,2011,32(12):2381. 47 高进华,陈大印,周丽,等.一种含聚天门冬氨酸的硝硫基烟草专用肥及其制备方法:中国,102674977A[P].2012-09-19. 48 郭卫红,赵鹏程,杨世立,等.甘蔗专用肥及其制备方法:中国,103804092A[P].2014-05-21. 49 孙仁贵.一种板栗专用复合包膜肥料及其制备方法:中国,104058828A[P].2014-09-24. 50 刘佃平,曹振国,曹兴华,等.一种脲醛功能性大蒜专用肥及其制备方法:中国,104045468A[P].2014-09-17. 51 高志华.葡萄专用有机-无机微生物水溶性肥料及其制备方法:中国,104151079A[P].2014-11-19. 52 Hu J C, Pan Z C, Dong F Q, et al. A review on research of biodegradable high water absorbent materials[J].Materials Review,2006(S2):362(in Chinese). 胡军楚,潘湛昌,董奋强,等.可生物降解性高吸水材料的研究状况[J].材料导报,2006(S2):362. 53 Zhang C, Wu S, Qin X. Facile fabrication of novel pH-sensitive poly(aspartic acid) hydrogel by crosslinking nanofibers[J].Materials Letters,2014,132:393. 54 Zhao Y S, Wu Y X, Niu F G, et al. The effect of hydrolysis conditions on the properties of polyaspartic acid superabsorbent resin[J].New Chemical Materials,2010,38(4):63(in Chinese). 赵彦生,吴永新,牛富刚,等.水解条件对聚天门冬氨酸高吸水性树脂的性能影响[J].化工新型材料,2010,38(4):63. 55 Salakhieva D V, Gumerova D R, Akhmadishina R A, et al. Anti-radical and cytotoxic activity of polysuccinimide and polyaspartic acid of different molecular weight[J].Bionano Science,2016,6(4):348. 56 Vega-Chacón J, Arbeláez M A, Jorge J H, et al. pH-responsive poly(aspartic acid) hydrogel-coated magnetite nanoparticles for biomedi-cal applications[J].Materials Science and Engineering:C,2017,77:366. 57 Zrinyi M, Gyenes T, Juriga D, et al. Volume change of double cross-linked poly(aspartic acid) hydrogels induced by cleavage of one of the crosslinks[J].Acta Biomater,2013,9(2):5122. 58 Nam M O, Kyung T O, Yu S Y, et al. Poly(L-aspartic acid) nanogels for lysosome-selective antitumor drug delivery[J].Colloids and Surfaces B: Biointerfaces,2013,101:298. 59 谭天伟,孙绍华,曹辉,等.一种用聚天门冬氨酸衍生物制备可注射原位凝胶的方法:中国,101507833A[P].2009-08-19. 60 马建标,五国琳,逯彩彩,等.一种基于聚天门冬氨酸衍生物的可注射水凝胶的制备方法:中国,102617867[P].2012-08-01. 61 成都市绿科华通科技有限公司.一种生物相容性高分子抗肿瘤药物的制备方法:中国,104415104A[P].2015-03-18. 62 周根陶.一种聚天门冬氨酸的医药用途:中国,103720707A[P].2014-04-16. 63 周四元,宦梦蕾,崔晗,等.一种可逆转肿瘤耐药的线粒体靶向胶束递药系统:中国,104523723A[P].2015-04-22. 64 成都市龙华新科技有限公司.具有双亲性结构的高分子药物制备方法:中国,105126114A[P].2015-12-09. 65 Zheng T, Wang H, Yang X M. Study on synthesis and properties of polyaspartic esters polyureas[J].China Plastics Industry,2014,42(11):14(in Chinese). 郑涛,王洪,杨旭明.聚天门冬氨酸酯聚脲的合成与性能研究[J].塑料工业,2014,42(11):14. 66 He J W, Huang S L, Qing N. Research status of polyaspartic po-lyurea[J].Materials Review,2014(S2):292(in Chinese). 何金文,黄顺礼,卿宁.聚天门冬氨酸酯聚脲的研究现状[J].材料导报,2014(S2):292. 67 Wang C Y, Ren B Y, Tong Z, et al. Progress in studies of biodegradable polyaspartate materials[J].Polymer Bulletin,2002(5):29(in Chinese). 王朝阳,任碧野,童真,等.可生物降解材料聚天门冬氨酸的研究进展[J].高分子通报,2002(5):29. 68 彭瑞,姜鹏波,史立彤,等.景观道具用聚天门冬氨酸酯防护涂料及其制备方法:中国,103805048A[P].2014-05-21. 69 季春波,姜鹏波,史立彤,等.矿山设备用聚天门冬氨酸酯耐磨涂料及其制备方法:中国,103788857A[P].2014-05-14. 70 李根固.一种抗裂墙体保温材料及其制备方法:中国,104261769A[P].2015-01-07. 71 张庆.一种电力设备柜等用多功能电磁屏蔽型涂料及其制备方法:中国,104449346A[P].2015-03-25. 72 宋欢欢,陈小庆,李超宇,等.一种橡胶隔振器用耐油、抗老化防护涂料及其制备方法:中国,104530954A[P].2015-04-22. 73 Sun Bo, Development of polyaspartate materials: Design, synthesis, characterization and applications[D].Tianjin: Tianjin University,2006(in Chinese). 孙波.聚天(门)冬氨酸材料的设计、合成与应用基础研究[D].天津:天津大学,2006. 74 Nagao Y, Imai Y, Matsui J, et al. Proton transport properties of poly(aspartic acid) with different average molecular weights[J].The Journal of Chemical Thermodynamics,2011,43(4):613. 75 Feng J, Gao L, Wen R, et al. Fluorescent polyaspartic acid with an enhanced inhibition performance against calcium phosphate[J].Desalination,2014,345:72. 76 Nemeth C, Gyarmati B, Abdullin T, et al. Poly(aspartic acid) with adjustable pH-dependent solubility[J].Acta Biomaterialia,2017,49:486. 77 Migahed M A, Rashwan S M, Kamel M M, et al. Synthesis, cha-racterization of polyaspartic acid-glycine adduct and evaluation of their performance as scale and corrosion inhibitor in desalination water plants[J].Journal of Molecular Liquids,2016,224:849. 78 Zhang Y L, Zhao C X, Liu X D, et al. Application of poly(aspartic acid-citric acid) copolymer compound inhibitor as an effective and environmental agent against calcium phosphate in cooling water systems[J].Journal of Applied Research and Technology,2016,14(6):425. 79 Zeng D, Chen T, Zhou S. Synthesis of polyaspartic acid/chitosan graft copolymer and evaluation of its scale inhibition and corrosion inhibition performance[J].International Journal of Electrochemical Science,2015,10:9513. 80 Xu Y, Zhang B, Zhao L, et al. Synthesis of polyaspartic acid/5-aminoorotic acid graft copolymer and evaluation of its scale inhibition and corrosion inhibition performance[J].Desalination,2013,311:156. 81 Zhang B, Zhou D, Lv X, et al. Synthesis of polyaspartic acid/3-amino-1H-1, 2,4-triazole-5-carboxylic acid hydrate graft copolymer and evaluation of its corrosion inhibition and scale inhibition performance[J].Desalination,2013,327:32. 82 Song H Q, Dou X B, Li R Q, et al. A general strategy to prepare different types of polysaccharide-graft-poly(aspartic acid) as degra-dable gene carriers[J].Acta Biomaterialia,2015,12:156. 83 Gyarmati B, Meszar E Z, Kiss L, et al. Supermacroporous chemically cross-linked poly(aspartic acid) hydrogels[J].Acta Biomaterialia,2015,22:32.