摘要
甲壳素和壳聚糖是可再生的大分子生物质资源.由于分子内和分子间的强烈氢键作用,甲壳素和壳聚糖不能溶解在水或常规有机溶剂中,这极大地限制了其在诸多领域中的应用.离子液体作为一种新型绿色溶剂,对甲壳素和壳聚糖具有优良的溶解作用.本文综述了离子液体对甲壳素和壳聚糖的溶解性能和溶解机理,概述了均相溶液体系中纤维、膜、凝胶等材料的制备以及酰化、接枝共聚、交联、降解、希夫碱化等多种衍生化反应,总结了离子液体在甲壳素和壳聚糖化学研究中面临的挑战并对其进行了展望.
Chitin and chitosan are renewable biomass resources with macromolecular structures. Due to the strong intra-and inter-molecular hydrogen bonds, chitin and chitosan cannot be dissolved in water or traditional organic solvents, which tremendously limit their applications in many fields. Ionic liquid, as a novel green solvent, provides excellent solubility to chitin and chitosan. In this paper, the research progress on dissolution performance and dissolution mechanism of chitin and chitosan in ionic liquids is reviewed. Materials including fibers, films and gels created from the homogeneous solutions are summarized; meanwhile, the chemical derivatization of chitin and chitosan in ionic liquids are also discussed. Finally, the challenges and future development of ionic liquids in chitin and chitosan chemistry are proposed.
引文
1 Rinaudo M.Prog Polym Sci,2006,31:603-632
2 Wu Y,Sasaki T,Irie S,Sakurai K.Polymer,2008,49:2321-2327
3 Hu X,Du Y,Tang Y,Wang Q,Feng T,Yang J,Kennedy JF.Carbohydr Polym,2007,70:451-458
4 Einbu A,Naess SN,Elgsaeter A,V?rum KM.Biomacromolecules,2004,5:2048-2054
5 Poirier M,Charlet G.Carbohydr Polym,2002,50:363-370
6 Min BM,Lee SW,Lim JN,You Y,Lee TS,Kang PH,Park WH.Polymer,2004,45:7137-7142
7 Nishi N,Noguchi J,Tokura S,Shiota H.Polym J,1979,11:27-32
8 Tamura H,Nagahama H,Tokura S.Cellulose,2006,13:357-364
9 Zhu HY,Fu YQ,Jiang R,Yao J,Xiao L,Zeng GM.Bioresour Tech,2012,105:24-30
10 Pillai CKS,Paul W,Sharma CP.Prog Polym Sci,2009,34:641-678
11 Duan J,Liang X,Cao Y,Wang S,Zhang L.Macromolecules,2015,48:2706-2714
12 Huang Y,Zhong Z,Duan B,Zhang L,Yang Z,Wang Y,Ye Q.J Mater Chem B,2014,2:3427-3432
13 Duan B,Zheng X,Xia Z,Fan X,Guo L,Liu J,Wang Y,Ye Q,Zhang L.Angew Chem,2015,127:5241-5245
14 Chang C,Chen S,Zhang L.J Mater Chem,2011,21:3865-3871
15 Swatloski RP,Spear SK,Holbrey JD,Rogers RD.J Am Chem Soc,2002,124:4974-4975
16 Zhang S,Liu Y,Nie Y.J Light Ind,2016,31:1-14(in Chinese)[张锁江,刘艳荣,聂毅.轻工学报,2016,31:1-14]
17 Zakrzewska ME,Bogel-?ukasik E,Bogel-?ukasik R.Energy Fuels,2010,24:737-745
18 Silva SS,Duarte ARC,Oliveira JM,Mano JF,Reis RL.J Bioactive Compatible Polym,2013,28:481-491
19 Xie H,Zhang S,Li S.Green Chem,2006,8:630-633
20 Yamazaki S,Takegawa A,Kaneko Y,Kadokawa J,Yamagata M,Ishikawa M.Electrochem Commun,2009,11:68-70
21 Wang WT,Zhu J,Wang XL,Huang Y,Wang YZ.J Macromol Sci Part B,2010,49:528-541
22 Prasad K,Murakami M,Kaneko Y,Takada A,Nakamura Y,Kadokawa J.Int J Biol Macromol,2009,45:221-225
23 Duan Y,Freyburger A,Kunz W,Zollfrank C.Carbohydr Polym,2018,192:159-165
24 Zhou Y,Deng Y,Shang H.Pap Pap Making,2009,28:40-43(in Chinese)[周雅文,邓宇,尚海萍.纸和造纸,2009,28:40-43]
25 Qin Y,Lu X,Sun N,Rogers RD.Green Chem,2010,12:968-971
26 Setoguchi T,Kato T,Yamamoto K,Kadokawa J.Int J Biol Macromol,2012,50:861-864
27 Xiao W,Chen Q,Wu Y,Wu T,Dai L.Carbohydr Polym,2011,83:233-238
28 Sun X,Xue Z,Mu T.Green Chem,2014,16:2102-2106
29 Sun X,Huang C,Xue Z,Mu T.Energy Fuels,2015,29:1923-1930
30 Chen Q,Xu A,Li Z,Wang J,Zhang S.Green Chem,2011,13:3446-3452
31 Liu L,Zhou S,Wang B,Xu F,Sun R.J Appl Polym Sci,2013,129:28-35
32 Duan X,Xu J,He B,Li J,Cheng C.New Chem Mater,2011,39:56-59(in Chinese)[段先泉,徐纪刚,何北海,李军荣,程春祖.化工新型材料,2011,39:56-59]
33 Nunes CS,Rufato KB,Souza PR,de Almeida EAMS,da Silva MJV,Scariot DB,Nakamura CV,Rosa FA,Martins AF,Muniz EC.Carbohydr Polym,2017,170:99-106
34 Cho CW,Jeon YC,Pham TPT,Vijayaraghavan K,Yun YS.Ecotoxicol Environ Safety,2008,71:166-171
35 Sashina ES,Kashirskii DA,Zaborski M,Jankowski S.Russ J Gen Chem,2012,82:1994-1998
36 Taheri N,Abdolmaleki A,Fashandi H.Carbohydr Polym,2018,195:413-419
37 Walther P,Ota A,Müller A,Hermanutz F,G?hr F,Buchmeiser MR.Macromol Mater Eng,2016,301:1337-1344
38 Tolesa LD,Gupta BS,Lee MJ.Int J Biol Macromol,2019,130:818-826
39 Liang S,Ji H,Li l,Yu S,Liu F,Xie C.Polym Mater Sci Eng,2010,26:70-72(in Chinese)[梁升,纪欢欢,李露,于世涛,刘福胜,解从霞.高分子材料科学与工程,2010,26:70-72]
40 Li X,Zhao Q,Liao M,Li H,Zhou G.Food Sci Technol,2015,40:242-247(in Chinese)[李训碧,赵钦,廖明馨,李贺,周桂.食品科技,2015,40:242-247]
41 Tian TC,Xie CX,Li L,Wei QL,Yu ST,Zhang T.Polym Degrad Stab,2016,126:17-21
42 Uto T,Idenoue S,Yamamoto K,Kadokawa JI.Phys Chem Chem Phys,2018,20:20669-20677
43 Li Q,Sun J,Zhuang L,Xu X,Sun Y,Wang G.Carbohydr Polym,2018,195:288-297
44 Barber PS,Griggs CS,Bonner JR,Rogers RD.Green Chem,2013,15:601-607
45 Li L,Yuan B,Liu S,Yu S,Xie C,Liu F,Guo X,Pei L,Zhang B.J Mater Chem,2012,22:8585-8593
46 Mundsinger K,Müller A,Beyer R,Hermanutz F,Buchmeiser MR.Carbohydr Polym,2015,131:34-40
47 Shamshina JL,Zavgorodnya O,Choudhary H,Frye B,Newbury N,Rogers RD.ACS Sustain Chem Eng,2018,6:14713-14722
48 Shamshina JL,Zavgorodnya O,Berton P,Chhotaray PK,Choudhary H,Rogers RD.ACS Sustain Chem Eng,2018,6:10241-10251
49 Shamshina JL,Gurau G,Block LE,Hansen LK,Dingee C,Walters A,Rogers RD.J Mater Chem B,2014,2:3924-3936
50 Park TJ,Jung YJ,Choi SW,Park H,Kim H,Kim E,Lee SH,Kim JH.Macromol Res,2011,19:213-215
51 Ma B,Zhang M,He C,Sun J.Carbohydr Polym,2012,88:347-351
52 Silva SS,Duarte ARC,Carvalho AP,Mano JF,Reis RL.Acta Biomater,2011,7:1166-1172
53 Santos-López G,Argüelles-Monal W,Carvajal-Millan E,López-Franco YL,Recillas-Mota MT,Lizardi-Mendoza J.Polymers,2017,9:722
54 Ren H,Li B,Neckenig M,Wu D,Li Y,Ma Y,Li X,Zhang N.Carbohydrate Polymers,2019,207:737-746
55 Li M,Wang Z,Li B.Desalination Water Treatment,2015,158:1-11
56 Liu Z,Wang H,Liu C,Jiang Y,Yu G,Mu X,Wang X.Chem Commun,2012,48:7350-7352
57 Liu Z,Wang H,Li B,Liu C,Jiang Y,Yu G,Mu X.J Mater Chem,2012,22:15085-15091
58 Silva SS,Santos TC,Cerqueira MT,Marques AP,Reys LL,Silva TH,Caridade SG,Mano JF,Reis RL.Green Chem,2012,14:1463-1470
59 Takegawa A,Murakami M,Kaneko Y,Kadokawa J.Carbohydr Polym,2010,79:85-90
60 Kimura A,Nagasawa N,Taguchi M.Polym Degrad Stab,2019,159:133-138
61 Trivedi TJ,Rao KS,Kumar A.Green Chem,2014,16:320-330
62 King C,Shamshina JL,Gurau G,Berton P,Khan NFAF,Rogers RD.Green Chem,2017,19:117-126
63 Chakravarty J,Rabbi MF,Bach N,Chalivendra V,Yang CL,Brigham CJ.Carbohydr Polym,2018,198:443-451
64 Stefanescu C,Daly WH,Negulescu II.Carbohydr Polym,2012,87:435-443
65 Oh DX,Shin S,Lim C,Hwang DS.Materials,2013,6:3826-3839
66 Tran CD,Mututuvari TM.Langmuir,2015,31:1516-1526
67 Fu R,Ji X,Ren Y,Wang G,Cheng B.Fibers Polym,2017,18:852-858
68 Ma H,Hsiao BS,Chu B.Polymer,2011,52:2594-2599
69 Yang D,Wang Y,He L,Li H.ACS Appl Mater Interfaces,2016,8:19709-19715
70 Silva SS,Mano JF,Reis RL.Green Chem,2016,19:1208-1220
71 Mine S,Izawa H,Kaneko Y,Kadokawa JI.Carbohydr Res,2009,344:2263-2265
72 Hirayama H,Yoshida J,Yamamoto K,Kadokawa JI.Carbohydr Polym,2018,200:567-571
73 Yamamoto K,Yoshida S,Mine S,Kadokawa J.Polym Chem,2013,4:3384-3389
74 Zhang H,Ge L,Yi J,Zhou H,Feng L.Chem Res Appl,2011,23:1595-1598(in Chinese)[张惠欣,葛丽环,尹静,周宏勇,冯磊.化学研究与应用,2011,23:1595-1598]
75 Liang S,Li L,Yu ST,Liu F,Xie C.J Chem Eng Chin Univ,2009,23:901-905(in Chinese)[梁升,李露,于世涛,刘福胜,解从霞.高校化学工程学报,2009,23:901-905]
76 Zhao G,Lang X,Wang F,Li J,Li X.Biochem Eng J,2017,126:24-29
77 Wang Z,Zheng L,Li C,Zhang D,Xiao Y,Guan G,Zhu W.Carbohydr Polym,2015,117:973-979
78 Han X,Cheng C,Zhu Q,Wu C.Polym Mater Sci Eng,2011,27:20-23(in Chinese)[韩小进,程春祖,朱庆松,武长城.高分子材料科学与工程,2011,27:20-23]
79 Ge W,Li D,Chen M,Wang X,Liu S,Sun R.Carbohydr Polym,2015,117:169-176
80 Wang Z,Zheng L,Li C,Zhang D,Xiao Y,Guan G,Zhu W.Carbohydr Polym,2013,94:505-510
81 Yang L,Zhang J,He J,Zhang J,Gan Z.Polym Int,2015,64:1045-1052
82 Liu D,Lin D,Liu M.New Chem Mater,2015,43:169-171(in Chinese)[刘丹慧,林春香,刘明华.化工新型材料,2015,43:169-171]
83 Chen H,Cui S,Zhao Y,Zhang C,Zhang S,Peng X.PLoS ONE,2015,10:e0121817
84 Chen J,Zheng L,Chen X,Wang Z,Li C,Xiao Y,Guan G,Zhu W.Int J Biol Macromol,2015,74:433-438
85 Kimura A,Nagasawa N,Shimada A,Taguchi M.Radiat Phys Chem,2016,124:130-134
86 Guyomard-Lack A,BuchtováN,Humbert B,Le Bideau J.Phys Chem Chem Phys,2015,17:23947-23951
87 Zhou Y,Fan M,Luo X,Huang L,Chen L.Carbohydr Polym,2014,113:108-114
88 Mezzetta A,Guazzelli L,Chiappe C.Green Chem,2017,19:1235-1239
89 Zhang Z,Li C,Wang Q,Zhao ZK.Carbohydr Polym,2009,78:685-689
90 Husson E,Hadad C,Huet G,Laclef S,Lesur D,Lambertyn V,Jamali A,Gottis S,Sarazin C,Nguyen Van Nhien A.Green Chem,2017,19:4122-4131
91 Li J,Huang WC,Gao L,Sun J,Liu Z,Mao X.Carbohydr Polymers,2019,211:329-335
92 Liu K,Li L,Yuan B,Yu S.J Qingdao Univ Sci Technol(Nat Sci Ed),2012,33:352-356(in Chinese)[刘坤,李露,袁冰,于世涛.青岛科技大学学报(自然科学版),2012,33:352-356]
93 Yuan WL,Su CJ,Lei CM,Mou CY.J Appl Polym Sci,2014,131:41152
94 Xing R,Liu S,Yu H,Guo Z,Wang P,Li C,Li Z,Li P.Carbohydr Res,2005,340:2150-2153
95 Chen Q,Xiao W,Zhou L,Wu T,Wu Y.Polym Degrad Stab,2012,97:49-53
96 Shan L,Liu S,Li L,Yu S,Liu F,Xie C.J Chem Eng Chin Univ,2010,24:980-984(in Chinese)[单丽娟,刘仕伟,李露,于世涛,刘福胜,解从霞.高校化学工程学报,2010,24:980-984]
97 Wu C,Zang H,Li D,Zhang M,Yu J,Cheng B.Polym Mater Sci Eng,2014,30:75-79(in Chinese)[吴长春,臧洪俊,李大庆,张明川,于建春,程博闻.高分子材料科学与工程,2014,30:75-79]
98 Hua D,Jiang J,Kuang L,Jiang J,Zheng W,Liang H.Macromolecules,2011,44:1298-1302
99 Liu P,Li K,Zhang S.J Zhengzhou Univ(Eng Sci),2013,34:49-53(in Chinese)[刘蒲,李克让,张帅.郑州大学学报(工学版),2013,34:49-53]
100 00 Li KR,Xu M,Zhang S,Liu P.CIESC J,2013,64:1499-1503(in Chinese)[李克让,徐民,张帅,刘蒲.化工学报,2013,64:1499-1503]