氨(季铵)基纤维素的合成及应用进展
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摘要
氨(季铵)基纤维素因其不同结构具有不同的性质,可量身定制具有不同性能的氨(季铵)基纤维素,使其工业应用不断增长。本文系统概述了氨(季铵)基纤维素合成的策略。包括纤维素对甲苯磺酸酯亲核取代法、卤化纤维素取代法、纤维素环氧化合物开环法、纤维素酰胺酯胺解法、迈克尔加成反应策略、纤维素碳酸酯胺解法等制备季铵纤维素的合成方法。除了结构和合成方面外,还进一步讨论了氨(季铵)基纤维素在基因载体与酶蛋白的固载、药物传递与缓释、消毒杀菌、催化、重金属的吸附与分离等方面的应用,并对以后的氨(季铵)基纤维素研究方向做了展望。
The properties of ammonia(quaternary ammonium) cellulose vary by different structure. It can be tailored to ammonia(quaternary ammonium) based cellulose with different properties which can promote industrial development. This article reviews the synthetic methods for the preparation of ammonia(quaternary ammonium) cellulose. A variety of synthetic methods are as follows:The nucleophilic substitution method of cellulose p-toluenesulfonate, halogenated cellulose substitution method, cellulose epoxy compound ring-opening method, cellulose amide ester amination method, Michael addition reaction strategy, cellulose carbonate amidation method, etc. Then, the application of ammonia(quaternary ammonium) cellulose in the immobilization of gene carriers and enzyme proteins, drug delivery and sustained release, disinfection and sterilization, catalysis, and adsorption and separation of heavy metals were further discussed. At last, we are looking forward to receiving the future research direction of ammonia(quaternary ammonium) cellulose.
The properties of ammonia(quaternary ammonium) cellulose vary by different structure. It can be tailored to ammonia(quaternary ammonium) based cellulose with different properties which can promote industrial development. This article reviews the synthetic methods for the preparation of ammonia(quaternary ammonium) cellulose. A variety of synthetic methods are as follows:The nucleophilic substitution method of cellulose p-toluenesulfonate, halogenated cellulose substitution method, cellulose epoxy compound ring-opening method, cellulose amide ester amination method, Michael addition reaction strategy, cellulose carbonate amidation method, etc. Then, the application of ammonia(quaternary ammonium) cellulose in the immobilization of gene carriers and enzyme proteins, drug delivery and sustained release, disinfection and sterilization, catalysis, and adsorption and separation of heavy metals were further discussed. At last, we are looking forward to receiving the future research direction of ammonia(quaternary ammonium) cellulose.
引文
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[6]汪森,张蓉蓉,许小娟,等.天然聚多糖的溶解机理及溶液性质[J].高分子学报,2017,9:1426-1443.
[7]张金明,张军.基于纤维素的先进功能材料[J].高分子学报,2010,12:1376-1398.
[8]Matthias Pohl,Nico Michaelis,Frank Meister,et al.Biofunctional surfaces based on dendronized cellulose[J].Biomacromolecules,2009,10(2):382-389.
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[12]Becher J,Liebegott H,Berlin P,et al.Novel xylylene diaminocellulose derivatives for enzyme immobilization[J].Cellulose,2004,11(1):119-126.
[13]Heinze T,Pfeifer A,Koschella A,et al.Solvent-free synthesis of 6-deoxy-6-(ω-aminoalkyl)amino cellulose[J].Journal of Applied Polymer Science,2016,133(39):43987-43993.
[14]Mais U,Knaus S,Binder W,et al.Functionalization of Cellulose[M].2018.
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[16]Xie H,King A,Kilpelainen I,et al.Thorough chemical modification of wood-based lignocellulosic materials in ionic liquids[J].Biomacromolecules,2007,8(12):3740-3748.
[17]Xie H,Cao X,Shan S,et al.Guanidine cellulose for biocompatible nanoparticles phase transfer[J].Chemistry Select,2017,2(32):10555-10558.
[18]Zarth C S P,Koschella A,Pfeifer A,et al.Synthesis and characterization of novel amino cellulose esters[J].Cellulose,2011,18(5):1315-1325.
[19]Pohl M,Michaelis N,Meister F,et al.Biofunctional surfaces based on dendronized cellulose[J].Biomacromolecules,2009,10(2):382-389.
[20]Demircan D,Zhang B.Facile synthesis of novel soluble cellulose-grafted hyperbranched polymers as potential natural antimicrobial materials[J].Carbohydrate Polymers,2017,157:1913-1921.
[21]Zhu S,Wu Y,Chen Q,et al.Dissolution of cellulose with ionic liquids and its application:A mini-review[J].Green Chemistry,2006,8(4):325-327.
[22]Chen Q,Peng C,Xie H,et al.Cellulosic poly(ionic liquid)s:Synthesis,characterization and application in the cycloaddition of CO2 to epoxides[J].Rsc Advances,2015,5(55):44598-44603.
[23]Deng X,Zhi Y,Shan S,et al.Effective and reusable microcrystalline cellulosic Salen complexes for epoxidation of alpha-pinene[J].Cellulose,2018,25(2):1281-1289.
[24]Jolita Aniulyte J B,and Jolanta Liesiene,.Activation of cellulose-based carriers with pentaethylenehexamine[J].Proc Estonian Acad Sci Chem,2006,55(2):61-69.
[25]Xin Y,Xiong Q,Bai Q,et al.A hierarchically porous cellulose monolith:A template-free fabricated,morphology-tunable,and easily functionalizable platform[J].Carbohydrate Polymers,2017,157:429-437.
[26]Sharifi M,Robatjazi S-M,Sadri M,et al.Covalent immobilization of organophosphorus hydrolase enzyme on chemically modified cellulose microfibers:Statistical optimization and characterization[J].Reactive and Functional Polymers,2018,124:162-170.
[27]Cai J,Zhang L,Zhou J,et al.Novel fibers prepared from cellulose in Na OH/urea aqueous solution[J].Macromolecular Rapid Communications,2004,25(17):1558-1562.
[28]Song Y,Sun Y,Zhang X,et al.Homogeneous quaternization of cellulose in Na OH/urea aqueous solutions as gene carriers[J].Biomacromolecules,2008,9(8):2259-2264.
[29]Okamoto Y,Kawashima M,Hatada K.Chromatographic resolution.7.Useful chiral packing materials for high-performance liquid chromatographic resolution of enantiomers:Phenylcarbamates of polysaccharides coated on silica gel[J].Journal of the American Chemical Society,1984,106(18):5357-5359.
[30]Han M,Jin X,Yang H,et al.Controlled synthesis,immobilization and chiral recognition of carboxylic acid functionalized cellulose tris(3,5-dimethylphenylcarbamate)[J].Carbohydrate Polymers,2017,172:223-229.
[31]Alila S,Ferraria A M,Botelho do Rego A M,et al.Controlled surface modification of cellulose fibers by amino derivatives using N,N?-carbonyldiimidazole as activator[J].Carbohydrate Polymers,2009,77(3):553-562.
[32]Vanthuyne N,Roussel C.Cellulose chiral induction during the synthesis of cellulose N-phthaloyl-amino acid esters[J].Cellulose,2013,20(4):2057-2067.
[33]Sirvi?J A,Heiskanen J P.Synthesis of alkaline-soluble cellulose methyl carbamate using a reactive deep eutectic solvent[J].Chem Sus Chem,2017,10(2):455-460.
[34]Elschner T,Bra?i?M,Mohan T,et al.Modification of cellulose thin films with lysine moieties:A promising approach to achieve antifouling performance[J].Cellulose,2017,25(1):537-547.
[35]Hassan M L.Preparation and thermal stability of new cellulose-based poly(propylene imine)and poly(amido amine)hyperbranched derivatives[J].Journal of Applied Polymer Science,2006,101(3):2079-2087.
[36]Pourjavadi A,Seidi F,Afjeh S S,et al.Synthesis of soluble N-functionalized polysaccharide derivatives using phenyl carbonate precursor and their application as catalysts[J].Starch/Staerke,2011,63(12):780-791.
[37]Elschner T,Heinze T.A promising cellulose-based polyzwitterion with p H-sensitive charges[J].Beilstein J Org Chem,2014,10:1549-1556.
[38]Elschner T,Scholz F,Miethe P,et al.Rapid flow through immunoassay for CRP determination based on polyethylene filters modified with omega-aminocellulose carbamate[J].Macromol Biosci,2014,14(11):1539-1546.
[39]Heinze T,Wondraczek H,Elschner T,et al.Process for the functionalization of a surface:WO,2014147168A1[P].2014-9-25.
[40]Elschner T,Doliska A,Bracic M,et al.Film formation ofω-aminoalkylcellulose carbamates-A quartz crystal microbalance(QCM)study[J].Carbohydr Polym,2015,116:111-116.
[41]Elschner T,Heinze T.Cellulose carbonates:A platform for promising biopolymer derivatives with multifunctional capabilities[J].Macromolecular Bioscience,2015,15(6):735-746.
[42]Elschner T,Ludecke C,Kalden D,et al.Zwitterionic cellulose carbamate with regioselective substitution pattern:A coating material possessing antimicrobial activity[J].Macromol Biosci,2016,16(4):522-534.
[43]Salimi H,Aryanasab F,Banazadeh A R,et al.Designing syntheses of cellulose and starch derivatives with basic or cationic N-functions:PartⅠ-cellulose derivatives[J].Polymers for Advanced Technologies,2016,27(1):5-32.
[44]Chang S,Condon B,Edwards J V.Preparation and characterization of aminobenzyl cellulose by two step synthesis from native cellulose[J].Fibers and Polymers,2010,11(8):1101-1105.
[45]Kim H,Park S,Yang Y,et al.Investigation of optimum amino group introduction conditions to microcrystalline cellulose(MCC)surface by silanization[J].Polymer-Korea,2016,40(6):925-932.
[46]Kim H,Yang Y,Hwang K,et al.Preparation and properties of polyethylene composites using microcrystalline cellulose(MCC)with carbon dioxide adsorbable amino groups as filler[J].Polymer-Korea,2017,41(6):1011-1018.
[47]Yang Y,Kim H,Lim K-H,et al.Preparation and characterization of polyurethane composites using amino-functionalized microcrystalline cellulose(MCC)as fillers[J].Polymer-Korea,2018,42(1):147-156.
[48]Liang M,Zhang G,Feng Y,et al.Facile synthesis of silver nanoparticles on amino-modified cellulose paper and their catalytic properties[J].Journal of Materials Science,2018,53(2):1568-1579.
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