Research progress in adsorption and separation of dyeing wastewater by β⁃cyclodextrin polymer

doi:10.19491/j.issn.1001-9278.2024.05.021

Abstract

Abstract:

This paper introduced the preparation methods of β⁃Cyclodextrin polymer（β⁃CDs）and reviewed the research progress in its adsorption mechanism and application effectiveness in the adsorption and separation of printing and dyeing wastewater pollutants such as anionic dyes， cationic dyes， heavy metal ions， and bisphenol. Meanwhile， the future development trend of β⁃CDs in research and applications was prospected.

Key words: β?cyclodextrin polymer, water treatment, dye, metal ion, bisphenol

CLC Number:

TQ320.79

WU Ruonan, SHI Wenzhao, LU Shaofeng, LIU Jinshu, DONG Jiankun, CUI Junjie, ZHANG Ling. Research progress in adsorption and separation of dyeing wastewater by β⁃cyclodextrin polymer[J]. China Plastics, 2024, 38(5): 120-128.

Figures/Tables 9

Fig.1. Structural diagrams of （a） crosslinked β⁃cyclodextrin polymer，（b） immobilized β⁃cyclodextrin polymer，（c） linear β⁃cyclodextrin polymer，（d） star β⁃cyclodextrin polymer and （e） hyperbranched β⁃cyclodextrin polymer

Fig.2. Synthetic route of （a）CDP⁃CN，（b） CDP⁃DEA and （c） CDP⁃NH2［20］

Fig.3. Synthetic route of CT⁃β⁃CD［21］

Fig.4. Synthetic route of the PBSST⁃g⁃β⁃CDP nanofiber membrane ［31］

Fig.5. Synthetic route of the CD/TPP nanoparticles［35］

Fig. 6. Synthetic route of thermally responsive star polymer ［38］

Fig.7. （a） Adsorption mechanism of β⁃CDP on NR， BF and ST［45］，（b） adsorption mechanism of T⁃β⁃CD and CT⁃β⁃CD on MB［21］，（c） adsorption mechanism of PBSST⁃g⁃β⁃CDP3 nanofibers on MB and MO dyes［31］，（d）binding mechanism of MB dye CA⁃PANI/β⁃CD nanofibers［48］

Fig.8. Adsorption mechanism of anionic dyes on EA⁃CDP ［49］

Fig.9. Mechanism of Cu （II） removal by M⁃β⁃MGO PVDF membrane ［55］

References 62

1	高志亮，南蓓蓓，白阳，等.基于环糊精的高交联密度pH响应性水凝胶的制备与性能研究［J］.高分子通报，2022，282（10）：74⁃86.
	GAO Z L， NAN B B， BAI Y， et al.The Preparation and application of pH⁃responsive B⁃cyclodextrin⁃based hydrogel with high cross⁃linked density［J］. Polymer Bulletin， 2022，282（10）：74⁃86.
2	SEIDI Farzad， SHAMSABDI Ahmad Arabi， AMINI Mojtaba， et al. Functional materials generated by allying cyclodextrin⁃based supramolecular chemistry with living polymerization［J］. Polymer Chemistry， 2019， 10（27）： 3 674⁃3 711.
3	赵传靓，王子婕，闫仪，等.环糊精多孔聚合物对水中染料分子的吸附性能及主客效应［J］.环境科学，2022，43（02）：907⁃919.
	ZHAO C L， WANG Z J， YAN Y， et al.Adsorption properties and host⁃guest effects of porous cyclodextrin polymers for dye molecules in water ［J］.Environmental Science，2022，43（02）：907⁃919.
4	LIU Zongjian， YE Lin，XIJianing， et al. Cyclodextrin polymers： Structure， synthesis， and use as drug carriers［J］. Progress in Polymer Science， 2021， 118： 101408.
5	钟汉毅，高鑫，邱正松，等.环保型β⁃β⁃环糊精聚合物微球高温降滤失作用机理［J］.石油学报，2021，42（08）：1 091⁃1 102+1 112.
	ZHONG H Y， GAO X， QIU Z S， et al. Mechanism of filtration loss reduction of environment⁃friendly B⁃cyclodextrin polymer microspheres under high temperatures［J］. Acta Petrolei Sinica，2021，42（08）：1 091⁃1 102+1 112.
6	龚伟，李美兰，袁浪，等.β⁃环糊精/壳聚糖交联聚合物对水中Pb²⁺的吸附行为［J］.热固性树脂，2019，34（03）：37⁃42
	GONG W， LI M L， YUAN L， et al. Adsorption behavior of β⁃CD/CTS crosslinked polymers for Pb²⁺ in water［J］. Thermosetting Resin，2019，34（03）：37⁃42
7	高陆玺，吕雪川，张弛，等.用于印染废水处理的改性絮凝剂合成及其脱色性能［J］.纺织学报，2022，43（07）：121⁃128.
	GAO L X， LU X C， ZHANG C， et al.Synthesis and decolorizing performance of modified flocculant for treating dyeing wastewater［J］. Journal of Textile Research，2022，43（07）：121⁃128.
8	赵朦，李梅，白毛毛，等.高级氧化技术在印染废水处理中的研究进展［J］.应用化工，2023，52（06）：1 884⁃1 890.
	ZHAO M， LI M， BAI M M， et al. Research progress of advanced oxidation technology in dyeing wastewater treatment［J］. Applied Chemical Industry，2023，52（06）：1 884⁃1 890.
9	FADZLI Julia， HAMID Ku Halim Ku， Nik Raikhan Nik HIM， et al. A critical review on the treatment of reactive dye wastewater［J］. Desalination And Water Treatment， 2022， 257： 185⁃203.
10	CHEN Yan Feng. Polyvinyl chloride centrifugal mother liquid wastewater treatment by electrochemical oxidation process［J］.Industrial Water & Wastewater， 2019.
11	章君，姚杭永，陆佳俊.高级氧化技术在印染废水处理的应用和前景研究［J］.节能与环保，2022， 335（06）：65⁃66.
	ZHANG J， YAO H Y LU J J， et al.Application principle and prospect of advanced oxidation technology in dyeing waste water treatment［J］.Energy Conservation & Environmental Protection，2022， 335（06）：65⁃66.
12	孙理密，赵承军，张德清，等.厌氧脱色技术在印染废水处理中的工程应用［J］.水处理技术，2022，48（07）：145⁃148.
	SUN L M， ZHAO C J， ZHANG D Q， et al. Application of Anaerobic Decolorization Technology in Printing and Dyeing Wastewater Treatment［J］. Technology of Water Treatment，2022，48（07）：145⁃148.
13	宋梦琪，周春江，马鲁铭.水解酸化工艺处理印染废水的机理［J］.环境工程学报，2015，9（01）：102⁃106.
	SONG M Q， ZHOU C J， MA L M， et al.Mechanism of printing and dyeing wastewater treatment by hydrolysis and acidification process［J］. Chinese Journal of Environmental Engineering，2015，9（01）：102⁃106.
14	乔函，张璐，李薇，等.活性炭吸附处理印染废水及再生研究［J］.化工新型材料，2022，50（S1）：422⁃426.
	QIAO H， ZHANG L， LI W， et al. Study on AC adsorption treatment of printing and dyeing wastewater and the regeneration process［J］. New Chemical Materials，2022，50（S1）：422⁃426.
15	孙晓旭，李兴宇，徐进.不同活性炭吸附组合工艺处理印染废水的实验研究［J］.工业水处理，2018，38（07）：78⁃80.
	SUN X X， LI X Y， XU J， et al.Experimental study on the treatment of printing and dyeing wastewater by different activated carbon adsorption combined processes［J］. Industrial Water Treatment，2018，38（07）：78⁃80.
16	郄淑燕，郝莹，刘宗建，等.环糊精聚合物及其生物医学应用的研究进展［J］.化学学报，2020，78（03）：232⁃244.
	QIE S Y， HAO Y， LIU Z J， et al. Advances in cyclodextrin polymers and their applications in biomedicine［J］. Acta Chimica Sinica，2020，78（03）：232⁃244.
17	Yadav M， Thakore S， Jadeja R. A review on remediation technologies using functionalized cyclodextrin［J］. Environmental Science and Pollution Research， 2022， 29（1）： 236⁃250.
18	Xing C， Xu X， Song L， et al. β⁃Cyclodextrin⁃based poly （vinyl alcohol） fibers for sustained release of fragrances［J］. Polymers， 2022， 14（10）： 2002.
19	Martwong E， Chuetor S， Junthip J. Adsorption of paraquat by poly （vinyl alcohol）⁃cyclodextrin nanosponges［J］. Polymers， 2021， 13（23）： 4110.
20	XU MengYa， JIANG HongLiu， XIE ZeWU，et al. Highly efficient selective adsorption of anionic dyes by modified β⁃cyclodextrin polymers［J］. Journal of the Taiwan Institute of Chemical Engineers， 2020， 108： 114⁃128.
21	JIANG Hongliu， LIN Jieci， Wei HAI， et al. A novel crosslinked β⁃cyclodextrin⁃based polymer for removing methylene blue from water with high efficiency［J］. Colloids and Surfaces A： Physicochemical and Engineering Aspects， 2019， 560： 59⁃68.
22	吕启祥，宫红，王锐.β⁃环糊精/环氧氯丙烷聚合物的制备及其对双酚S的吸附特性［J］.环境科学研究，2018，31（11）：1 933⁃1 939.
	LV Q X， GONG H， WANG R， et al. Synthesis of β⁃cyclodextrin/epichlorohydrin polymer and its adsorption properties for bisphenol S［J］. Research of Environmental Sciences，2018，31（11）：1 933⁃1 939.
23	Ogunbadejo B， Al⁃Zuhair S. MOFs as potential matrices in cyclodextrin glycosyltransferase immobilization［J］. Molecules， 2021， 26（3）： 680.
24	聂晓娟，李霞，马红艳.环糊精聚合物的合成及应用研究［J］.精细化工，2019，36（12）：2 364⁃2 370+2 377.
	NIE X J， LI X， MA H Y. Synthesis and application of cyclodextrin polymers［J］. Fine Chemicals，2019，36（12）：2 364⁃2 370+2 377.
25	Healy B， Yu T， da Silva Alves D C， et al. Cyclodextrins as supramolecular recognition systems： Applications in the fabrication of electrochemical sensors［J］. Materials， 2021， 14（7）： 1668.
26	GONG Tao， ZHOU Yehong， SUN Linlin， et al. Effective adsorption of phenolic pollutants from water using β⁃cyclodextrin polymer functionalized Fe₃O₄magnetic nanoparticles［J］. RSC advances， 2016， 6（84）： 80 955⁃80 963.
27	Plesselova S， Garcia⁃Cerezo P， Blanco V， et al. Polyethylenimine–bisphosphonate–cyclodextrin ternary conjugates： supramolecular systems for the delivery of antineoplastic drugs［J］. Journal of Medicinal Chemistry， 2021， 64（16）： 12 245⁃12 260.
28	Wang X， Chen H， Wang J， et al. Silver⁃modified β⁃cyclodextrin polymer for water treatment： a balanced adsorption and antibacterial performance［J］. Water， 2021， 13（21）： 3004.
29	Lin S， Wang F， Hong R. Polyacrylic acid and β⁃cyclodextrin polymer cross⁃linking binders to enhance capacity performance of silicon/carbon composite electrodes in lithium⁃ion batteries［J］. Journal of Colloid and Interface Science， 2022， 613： 857⁃865.
30	Chen H， Zhou Y， Wang J， et al. Polydopamine modified cyclodextrin polymer as efficient adsorbent for removing cationic dyes and Cu²⁺ ［J］. Journal of Hazardous Materials， 2020， 389： 121897.
31	LIU Yinli， JIA Jie， GAO Tingting， et al. Rapid， selective adsorption of methylene blue from aqueous solution by durable nanofibrous membranes［J］. Journal of Chemical & Engineering Data， 2020， 65（8）： 3 998⁃4 008.
32	冯颖，李可心，张宏，等.壳聚糖复合水凝胶的制备方法及在水处理中的应用［J/OL］.工业水处理：1⁃22.［2023⁃09⁃12］.
	FENG Y， LI K X， ZHANG H， et al. Preparation of chitosan composite hydrogel and its application in water treatment［J/OL］. Industrial Water Treatment：1⁃22.［2023⁃09⁃12］.
33	JIANG Yezhou， LIU Bingchuan， XU Jikun， et al. Cross⁃linked chitosan/β⁃cyclodextrin composite for selective removal of methyl orange： Adsorption performance and mechanism［J］. Carbohydrate polymers， 2018， 182： 106⁃114.
34	QU Mengnan， HE Dan， LUO Zhanxia， et al. Facile preparation of a multifunctional superhydrophilic PVDF membrane for highly efficient organic dyes and heavy metal ions adsorption and oil/water emulsions separation［J］. Colloids and Surfaces A： Physicochemical and Engineering Aspects， 2022， 637： 128231.
35	Tian J， Xia L， Wu J， et al. Linear alternating supramolecular photosensitizer for enhanced photodynamic therapy［J］. ACS Applied Materials & Interfaces， 2020， 12（29）： 32 352⁃32 359.
36	李霞，马红艳，聂晓娟，等.星形环糊精聚合物的制备及其应用［J］.化学进展，2020，32（07）：935⁃942.
	XIA L， MA H Y， NIE X J， et al.Preparation of star⁃like polymer based on cyclodextrin and its application ［J］. Progress in Chemistry，2020，32（07）：935⁃942.
37	Pottanam Chali S， Hüwel S， Rentmeister A， et al. Self‐assembled cationic polypeptide supramolecular nanogels for intracellular DNA delivery［J］. Chemistry–A European Journal， 2021， 27（47）： 12 198⁃12 206.
38	Liu Z， Ye L， Xi J， et al. Cyclodextrin polymers： Structure， synthesis， and use as drug carriers［J］. Progress in Polymer Science， 2021， 118： 101408.
39	Vrijsen J H， Van de Reydt E， Junkers T. Tunable thermoresponsive β‐cyclodextrin‐based star polymers［J］. Journal of Polymer Science， 2020， 58（24）： 3 402⁃3 410.
40	邹在平，刘小兵，赵秀丽.超支化环糊精聚合物研究进展［J］.高分子通报，2015（11）：1⁃12.
	ZOU Z P， LIU X B， ZHAO X L， et al. Progress cyclodextrin⁃based hyperbranched polymer［J］. Polymer Bulletin，2015（11）：1⁃12.
41	Wankar J， Kotla N G， Gera S， et al. Recent advances in host–guest self‐assembled cyclodextrin carriers： Implications for responsive drug delivery and biomedical engineering［J］. Advanced Functional Materials， 2020， 30（44）： 1909049.
42	Wan W， Ouyang H， Jiang Z， et al. Synthesis and intracellular drug delivery applications of hyperbranched polymers functionalized β⁃cyclodextrin［J］. Colloid and Interface Science Communications， 2021， 42： 100425.
43	侯淋，李霞，王丽琼.环糊精聚合物吸附剂的制备及其应用研究［J］.化学通报，2023，86（04）：420⁃428.
	HOU L， LI X， WANG L Q.Preparation and applications of cyclodextrin polymer adsorbent［J］. Chemistry，2023，86（04）：420⁃428.
44	洪雪丽，焦芬，刘维.印染废水处理技术综述［J］.中南大学学报（自然科学版），2023，54（04）：1 219⁃1 229.
	HONG X L， JIAO F， LIU W， et al.Review on dyeing wastewater treatment technology［J］. Journal of Central South University（Science and Technology），2023，54（04）：1 219⁃1 229.
45	LI Xia， XIE Long， YANG Xua， et al. Adsorption behavior and mechanism of β⁃cyclodextrin–styrene⁃based polymer for cationic dyes［J］. RSC Advances， 2018， 8（70）： 40 321⁃40 329.
46	陈雯婧，吴远悦，谢知音，等.可再生纤维素/环糊精聚合物对水中亚甲基蓝吸附行为［J］.合成化学，2023，31（01）：52⁃60.
	CHEN W J， WU Y Y， XIE Z Y， et al.Study of adsorption behavior for the removal of methylene blue in water by renewable cellulose/cyclodextrin polymer［J］.Chinese Journal of Synthetic Chemistry，2023，31（01）：52⁃60.
47	NARIYA Pratik， Manita DAS， SHUKLA Falguni， et al. Synthesis of magnetic silver cyclodextrin nanocomposite as catalyst for reduction of nitro aromatics and organic dyes［J］. Journal of Molecular Liquids， 2020， 300： 112279.
48	Ahmed S M ALI， ELl⁃Aassar M R， Hashem F S， et al. Surface modified of cellulose acetate electrospun nanofibers by polyaniline/β⁃cyclodextrin composite for removal of cationic dye from aqueous medium［J］. Fibers and Polymers， 2019， 20： 2 057⁃2 069.
49	JIANG Hongliu， XU Mengya， XIE Zewu， et al. Selective adsorption of anionic dyes from aqueous solution by a novel β⁃cyclodextrin⁃based polymer［J］. Journal of Molecular Structure， 2020， 1203： 127373.
50	XU Mengya， JIANG Hongliu， XIE Zewu， et al. Highly efficient selective adsorption of anionic dyes by modified β⁃cyclodextrin polymers［J］. Journal of the Taiwan Institute of Chemical Engineers， 2020， 108： 114⁃128.
51	QIU Changjing， LI Yuehu， LIU Hongchen， et al. A novel crosslinking strategy on functional cellulose⁃based aerogel for effective and selective removal of dye［J］. Chemical Engineering Journal， 2023， 463： 142404.
52	DUAN Hui⁃Ling， DENG Xu， WANG Jun， et al. Ethanolamine⁃and amine⁃functionalized porous cyclodextrin polymers for efficient removal of anionic dyes from water［J］. European Polymer Journal， 2020， 133： 109762.
53	JUMAH May N Bin， Mohamed Hamdy EID， AL⁃HUQAIL Arwa Abdulkreem， et al. Enhanced remediation of As （V） and Hg （II） ions from aqueous environments using β⁃cyclodextrin/MCM-48 composite： Batch and column studies［J］. Journal of Water Process Engineering， 2021， 42： 102118.
54	XU Weifeng，LIUXiang， TANG Kewen. Adsorption of hydroquinone and Pb （II） from water by β⁃cyclodextrin/polyethy，leneimine bi⁃functional polymer［J］. Carbohydrate Polymers， 2022， 294： 119806.
55	ZHANG Rui， LI Yu， ZHU Xuyang， et al. Application of β⁃cyclodextrin⁃modified/PVDF blend magnetic membranes for direct metal ions removal from wastewater［J］. Journal of Inorganic and Organometallic Polymers and Materials， 2020， 30： 2 692⁃2 707.
56	CHEN Huafeng， ZHOU Yi， WANG Jianyu， et al. Polydopamine modified cyclodextrin polymer as efficient adsorbent for removing cationic dyes and Cu²⁺ ［J］. Journal of Hazardous Materials， 2020， 389： 121897.
57	李晓丽，王崧人，张彦，等.改性环糊精在环境水污染中的研究进展［J］.化工科技，2020，28（01）：76⁃78.
	LI X L， WANG S R， ZHANG Y， et al. Research progress of modified cyclodextrin in water pollution treatment［J］. Science & Technology in Chemical Industry，2020，28（01）：76⁃78.
58	YANG ChangAn， HUANG He， JI Tuo， et al. A cost‐effective crosslinked β‐cyclodextrin polymer for the rapid and efficient removal of micropollutants from wastewater［J］. Polymer International， 2019， 68（4）： 805⁃811.
59	WANG Jianyu， CHENG Guang， LU Jian， et al. PDA⁃cross⁃linked beta⁃cyclodextrin： a novel adsorbent for the removal of BPA and cationic dyes［J］. Water Science and Technology， 2020， 81（11）： 2 337⁃2 350.
60	LI X， ZHOU M， JIA J， et al. Design of a hyper⁃crosslinked β⁃cyclodextrin porous polymer for highly efficient removal toward bisphenol a from water［J］. Separation and Purification Technology， 2018， 195： 130⁃137.
61	WANG Niejun， ZHOU Lilin， GUO Jun， et al. Adsorption of environmental pollutants using magnetic hybrid nanoparticles modified with β⁃cyclodextrin［J］. Applied Surface Science， 2014， 305： 267⁃273.
62	Haydar ALI， MUKHOPADHYAY Soumita， JANA Nikhil R. Selective electrochemical detection of bisphenol A using a molecularly imprinted pol ymer nanocomposite［J］. New Journal of Chemistry， 2019， 43（3）： 1 536⁃1 543.

[1]	CAO Hui, TANG Jing, REN Weitao, ZHOU Qiong. Fabrication of PES/modified UiO⁃66 composite membrane for separation of heavy metal ions [J]. China Plastics, 2024, 38(5): 14-18.
[2]	WANG Xiaohui, DONG Liming, GU Junjie, YAO Bing, CHEN Yan, LI Jing. Synthesis of 2，6⁃monosubstituted bisphenol A isophthalaldehyde phenolic resin and its applications in reversible thermochromic composite NiBR film [J]. China Plastics, 2024, 38(4): 32-39.
[3]	YANG Chen, TANG Xiaodong, LI Jingjing, FENG Xuefeng, CAO Yefei, GAO Zhiqiang. Research progress in synthetic technology of bisphenol⁃A epoxy resin [J]. China Plastics, 2023, 37(2): 106-112.
[4]	SUN Ying, BAI Lin, REN Runhan, SHANG Wei, WENG Yunxuan. Establishment and validation of a method for analyzing bisphenol⁃A in food⁃contact materials [J]. China Plastics, 2023, 37(11): 81-86.
[5]	GU Hainan, YING Jie, QIU Qihao, CHEN Meng, WANG Chenye, TONG Qifeng. Development for applications of bio⁃based polycarbonate [J]. China Plastics, 2023, 37(10): 34-39.
[6]	SONG Danyang, ZHENG Hongjuan, LI Yilong. Research progress in PLA⁃based oil⁃water separation materials [J]. China Plastics, 2022, 36(9): 187-192.
[7]	ZHOU Wenxian, LI Mingquan. Research on the properties of new type high⁃durability dye⁃type polyvinyl alcohol polarizer [J]. China Plastics, 2022, 36(4): 53-59.
[8]	WANG Fang, LI Yan, GUO Xintao, DOU Peng. Synthesis and properties of ternary polysulfone copolymer containing bisphenol fluorene [J]. China Plastics, 2022, 36(11): 24-29.
[9]	SUN Zhengmeng, ZHANG Mingxu, ZHANG Xinning, LIANG Ce, ZHANG Hailiang, LI Yunhui, MA Yuqin. Study on Thermal Stability of Bisphenol⁃A⁃Type Epoxy Matrix Composites Doped with Nano Glass Powders [J]. China Plastics, 2021, 35(9): 15-20.
[10]	WU Jingwen. Feasibility Study on Detection of Metal Elements and Ions in Plastic Infusion Containers by ICP-OES [J]. China Plastics, 2020, 34(9): 73-79.
[11]	. Bismaleimide Resin Toughened by Reactive PFEK with Pendant Propenyl Groups [J]. China Plastics, 2016, 30(06): 18-22 .
[12]	. Preparation and Dyeing of Benzylated Polystyrene/Fir Powder Composites [J]. China Plastics, 2014, 28(10): 29-35 .
[13]	. Synthesis and Application of the Efficient Silicon, Chlorine and Bromine Elements Coordination Flame Retardant [J]. China Plastics, 2014, 28(10): 89-93 .
[14]	ZHU Ya-hui Ke KE Yaqin JI. Preparation and Properties of BMI/DBA/PC Modified Resin [J]. China Plastics, 2013, 27(12): 57-61 .
[15]	. Study on Properties Difference of Homo-polypropylene and Co-polypropylene in Modification [J]. China Plastics, 2013, 27(03): 73-76 .