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Functionalization of cellulose with hyperbranched polyethylenimine for selective dye adsorption and separation

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Abstract

Cationic hyperbranched polyethylenimine (hPEI) was covalently linked onto the backbone of cellulose molecules via forming Schiff base structure between the amino groups of hPEI and the aldehyde groups on the chemically oxidized cellulose surface. The functionalized hPEI-CE possessed available active sites, and its adsorption behavior to anionic dye congo red (CR) and cationic basic yellow 28 (BY28) in aqueous solution was investigated. The hPEI-CE interacted with the two dyes, exhibiting sharp response to solution pH and ionic strength. The adsorption process was well dominated by the pseudo-second-order kinetic model. And the hPEI-CE following the Langmuir isotherm model, had a maximum adsorption capacity of 2100 mg g−1 for CR and 1860 mg g−1 for BY28, respectively. Further, the adsorption performance of six dyes onto the hPEI-CE was studied, which showed high adsorption capacities for CR, BY28, brilliant blue 133 (BB133), and reactive red, but very low adsorption for cationic bright yellow 7GL (7GL) and eosin Y (EY). The different adsorption performances for different dyes indicated the selective adsorption of the hPEI-CE for dyes owing to their different distribution coefficient (K) defining as the partition of dyes between hPEI-CE and water. Based on the unique selective adsorption, the mixtures of dyes, such as BB133-CR, BB133-BY28, BB133-7GL, and CR-7GL, were separated successfully using hPEI-CE.

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References

  • Areti S, Bandaru S, Teotia R, Rao CP (2015) Water-soluble 8-hydroxyquinoline conjugate of amino-glucose as receptor for La3+ in HEPES buffer, on whatman cellulose paper and in living cells. Anal Chem 87:12348–12354

    Article  CAS  Google Scholar 

  • Chakraborti S, Joshi P, Chakravarty D, Shanker V, Ansari ZA, Singh SP, Chakrabarti P (2012) Interaction of polyethyleneimine-functionalized ZnO nanoparticles with bovine serum albumin. Langmuir 28:11142–11152

    Article  CAS  Google Scholar 

  • Chen L, Berry RM, Tam KC (2014) Synthesis of β-cyclodextrin-modified cellulose nanocrystals (CNCs) @ Fe3O4 @ SiO2 superparamagnetic nanorods. ACS Sustain Chem Eng 2:951–958

    Article  CAS  Google Scholar 

  • Cheng C, Wang J, Yang X, Li A, Philippe C (2014) Adsorption of Ni (II) and Cd (II) from water by novel chelating sponge and the effect of alkali-earth metal ions on the adsorption. J Hazard Mater 264:332–341

    Article  CAS  Google Scholar 

  • Dash R, Elder T, Ragauskas AJ (2012) Grafting of model primary amine compounds to cellulose nanowhiskers through periodate oxidation. Cellulose 19:2069–2079

    Article  CAS  Google Scholar 

  • Davis CW, Di Toro DM (2015) Modeling nonlinear adsorption to carbon with a single chemical parameter: a lognormal langmuir isotherm. Environ Sci Technol 49:7810–7817

    Article  CAS  Google Scholar 

  • Donia AM, Atia AA, Abouzayed FI (2012) Preparation and characterization of nano-magnetic cellulose with fast kinetic properties towards the adsorption of some metal ions. Chem Eng J 191:22–30

    Article  CAS  Google Scholar 

  • Dou X, Li P, Zhang D, Feng CL (2012) C2-symmetric benzene-based hydrogels with unique layered structures for controllable organic dye adsorption. Soft Matter 8:3231–3238

    Article  CAS  Google Scholar 

  • Drese JH, Choi S, Lively RP, Koros WJ, Fauth DJ, Gray ML, Jones CW (2009) Synthesis–structure–property relationships for hyperbranched aminosilica CO2 adsorbents. Adv Funct Mater 19:3821–3832

    Article  CAS  Google Scholar 

  • Guendouz S, Khellaf N, Zerdaoui M, Ouchefoun M (2013) Biosorption of synthetic dyes (direct red 89 and reactive green 12) as an ecological refining step in textile effluent treatment. Environ Sci Pollut Res 20:3822–3829

    Article  CAS  Google Scholar 

  • Hadi P, Guo J, Barford JP, McKay G (2016) Multilayer dye adsorption in activated carbons-facile approach to exploit vacant sites and interlayer charge interaction. Environ Sci Technol. doi:10.1021/acs.est.6b00021

    Google Scholar 

  • Haerifar M, Azizian S (2012) Fractal-like adsorption kinetics at the solid/solution interface. J Phys Chem C 116:13111–13119

    Article  CAS  Google Scholar 

  • Hernández-Zamora M, Cristiani-Urbina E, Martínez-Jerónimo F, Perales-Vela HV, Ponce-Noyola T, del Carmen Montes-Horcasitas M, Cañizares-Villanueva RO (2015) Bioremoval of the azo dye congo red by the microalga chlorella vulgaris. Environ Sci Pollut R 22:10811–10823

    Article  Google Scholar 

  • Hinterstoisser B, Salmén L (1999) Two-dimensional step-scan FTIR: a tool to unravel the OH-valency-range of the spectrum of cellulose I. Cellulose 6:251–263

    Article  CAS  Google Scholar 

  • Hokkanen S, Repo E, Sillanpää M (2013) Removal of heavy metals from aqueous solutions by succinic anhydride modified mercerized nanocellulose. Chem Eng J 223:40–47

    Article  CAS  Google Scholar 

  • Hokkanen S, Repo E, Suopajärvi T, Liimatainen H, Niinimaa J, Sillanpää M (2014a) Adsorption of Ni (II), Cu (II) and Cd (II) from aqueous solutions by amino modified nanostructured microfibrillated cellulose. Cellulose 21:1471–1487

    Article  CAS  Google Scholar 

  • Hokkanen S, Repo E, Westholm LJ, Lou S, Sainio T, Sillanpää M (2014b) Adsorption of Ni2+, Cd2+, PO4 3− and NO3 − from aqueous solutions by nanostructured microfibrillated cellulose modified with carbonated hydroxyapatite. Chem Eng J 252:64–74

    Article  CAS  Google Scholar 

  • Ji M, Li P, Sheng N, Liu L, Pan H, Wang C, Ma Y (2016) Sialic acid-targeted nanovectors with phenylboronic acid-grafted polyethylenimine robustly enhance siRNA-based cancer therapy. ACS Appl Mater Interfaces 8:9565–9576

    Article  CAS  Google Scholar 

  • Kim B, Park SW, Kim JY, Yoo K, Lee JA, Lee MW, Han S (2013) Rapid dye adsorption via surface modification of TiO2 photoanodes for dye-sensitized solar cells. ACS Appl Mater Interfaces 5:5201–5207

    Article  CAS  Google Scholar 

  • Li B, Wu L, Li L, Seeger S, Zhang J, Wang A (2014a) Superwetting double-layer polyester materials for effective removal of both insoluble oils and soluble dyes in water. ACS Appl Mater Interfaces 6:11581–11588

    Article  CAS  Google Scholar 

  • Li B, Dong Y, Zou C, Xu Y (2014b) Iron (III)-alginate fiber complex as a highly effective and stable heterogeneous fenton photocatalyst for mineralization of organic dye. Ind Eng Chem Res 53:4199–4206

    Article  CAS  Google Scholar 

  • Li J, Su Z, Xu H, Ma X, Yin J, Jiang X (2015a) Supramolecular networks of hyperbranched poly (ether amine)(hPEA) nanogel/chitosan (CS) for the selective adsorption and separation of guest molecules. Macromolecules 48:2022–2029

    Article  CAS  Google Scholar 

  • Li K, Gao Q, Yadavalli G, Shen X, Lei H, Han B, Zhou C (2015b) Selective adsorption of Gd3+ on a magnetically retrievable imprinted chitosan/carbon nanotube composite with high capacity. ACS Appl Mater Interfaces 7:21047–21055

    Article  CAS  Google Scholar 

  • Li H, Shan C, Zhang Y, Cai J, Zhang W, Pan BC (2016) Arsenate adsorption by hydrous ferric oxide nanoparticles embedded in crosslinked anion exchanger: effect of the host pore structure. ACS Appl Mater Interfaces 8:3012–3020

    Article  CAS  Google Scholar 

  • Lien CF, Lin YF, Lin YS, Chen MT, Lin JL (2005) FTIR study of adsorption and surface reactions of N (CH3)3 on TiO2. J Phys Chem B 109:10962–10968

    Article  CAS  Google Scholar 

  • Lin N, Dufresne A (2013) Supramolecular hydrogels from in situ host-guest inclusion between chemically modified cellulose nanocrystals and cyclodextrin. Biomacromolecules 14:871–880

    Article  CAS  Google Scholar 

  • Liu F, Chung S, Oh G, Seo TS (2012) Three-dimensional graphene oxide nanostructure for fast and efficient water-soluble dye removal. ACS Appl Mater Interfaces 4:922–927

    Article  CAS  Google Scholar 

  • Liu W, Wu ZL, Wang YJ, Zhao YL, Liu WC, Yu Y (2013) Recovery of isoflavones from the soy whey wastewater using two-stage batch foam fractionation. Ind Eng Chem Res 52:13761–13767

    Article  CAS  Google Scholar 

  • Liu L, Gao ZY, Su XP, Chen X, Jiang L, Yao JM (2015) Adsorption removal of dyes from single and binary solutions using a cellulose-based bioadsorbent. ACS Sustainable Chem Eng 3:432–442

    Article  CAS  Google Scholar 

  • Liu L, Xie JP, Li YJ, Zhang Q, Yao JM (2016) Three-dimensional macroporous cellulose-based bioadsorbents for efficient removal of nickel ions from aqueous solution. Cellulose 23:723–736

    Article  CAS  Google Scholar 

  • Monti S, Pastore M, Li C, De Angelis F, Carravetta V (2016) Theoretical investigation of adsorption, dynamics, self-aggregation and spectroscopic properties of the D102 indoline dye on an anatase (101) substrate. J Phys Chem C 120:2787–2796

    Article  CAS  Google Scholar 

  • Park J, Lee J, Kwag J, Baek Y, Kim B, Yoon CJ, Kim S (2015) Quantum dots in an amphiphilic polyethyleneimine derivative platform for cellular labeling, targeting, gene delivery, and ratiometric oxygen sensing. ACS Nano 9:6511–6521

    Article  CAS  Google Scholar 

  • Pelton R, Ren P, Liu J, Mijolovic D (2011) Polyvinylamine-graft-TEMPO adsorbs onto, oxidizes, and covalently bonds to wet cellulose. Biomacromolecules 12:942–948

    Article  CAS  Google Scholar 

  • Shukla NB, Rattan S, Madras G (2012) Swelling and dye-adsorption characteristics of an amphoteric superabsorbent polymer. Ind Eng Chem Res 51:14941–14948

    Article  CAS  Google Scholar 

  • Sirvio J, Hyvakko U, Liimatainen H, Niinimaki J, Hormi O (2011) Periodate oxidation of cellulose at elevated temperatures using metal salts as cellulose activators. Carbohydr Polym 83:1293–1297

    Article  CAS  Google Scholar 

  • Spinella S, Maiorana A, Qian Q, Dawson NJ, Hepworth V, McCallum SA, Gross RA (2016) concurrent cellulose hydrolysis and esterification to prepare surface-modified cellulose nanocrystal decorated with carboxylic acid moieties. ACS Sustain Chem Eng 4:1538–1550

    Article  CAS  Google Scholar 

  • Sun X, Yang L, Li Q, Zhao J, Li X, Wang X, Liu H (2014) Amino-functionalized magnetic cellulose nanocomposite as adsorbent for removal of Cr(VI): synthesis and adsorption studies. Chem Eng J 241:175–183

    Article  CAS  Google Scholar 

  • Tao J, Xiong J, Jiao C, Zhang D, Lin H, Chen Y (2016) Hybrid mesoporous silica based on hyperbranch-substrate nanonetwork as highly efficient adsorbent for water treatment. ACS Sustain Chem Eng 4:60–68

    Article  CAS  Google Scholar 

  • Teotia A, Ikram S, Gupta B (2012) Structural characterization of chitosan and oxidized carboxymethyl cellulose based freeze-dried films. Polym Bull 69:175–188

    Article  CAS  Google Scholar 

  • Unuabonah EI, Gunter C, Weber J, Lubahn S, Taubert A (2013) Hybrid clay: a new highly efficient adsorbent for water treatment. ACS Sustain Chem Eng 1:966–973

    Article  CAS  Google Scholar 

  • Wang R, Yu B, Jiang X, Yin J (2012) Understanding the host–guest interaction between responsive core-crosslinked hybrid nanoparticles of hyperbranched poly (ether amine) and dyes: the selective adsorption and smart separation of dyes in water. Adv Funct Mater 22:2606–2616

    Article  CAS  Google Scholar 

  • Wu X, Cai J, Li S, Zheng F, Lai Z, Zhu L, Chen T (2016) Au @ Cu2O stellated polytope with core-shelled nanostructure for high-performance adsorption and visible-light-driven photodegradation of cationic and anionic dyes. J Colloid Interface Sci 469:138–146

    Article  CAS  Google Scholar 

  • Yadav VSK, Purkait MK (2016) Simultaneous CO2 reduction and dye (crystal violet) removal electrochemically on Sn and Zn electrocatalysts using Co3O4 anode. Energy Fuel 30:3340–3346

    Article  CAS  Google Scholar 

  • Yan SC, Li ZS, Zou ZG (2010) Photodegradation of rhodamine B and methyl orange over boron-doped g-C3N4 under visible light irradiation. Langmuir 26:3894–3901

    Article  CAS  Google Scholar 

  • Yang ST, Chen S, Chang Y, Cao A, Liu Y, Wang H (2011) Removal of methylene blue from aqueous solution by graphene oxide. J Colloid Interface Sci 359:24–29

    Article  CAS  Google Scholar 

  • Yang Z, Tarabara VV, Bruening ML (2015) Adsorption of anionic or cationic surfactants in polyanionic brushes and its effect on brush swelling and fouling resistance during emulsion filtration. Langmuir 31:11790–11799

    Article  CAS  Google Scholar 

  • Zhao J, Lu C, He X, Zhang X, Zhang W, Zhang X (2015) Polyethylenimine-grafted cellulose nanofibril aerogels as versatile vehicles for drug delivery. ACS Appl Mater Interfaces 7:2607–2615

    Article  CAS  Google Scholar 

  • Zhou Y, Zhang M, Hu X, Wang X, Niu J, Ma T (2013) Adsorption of cationic dyes on a cellulose-based multicarboxyl adsorbent. J Chem Eng Data 58:413–421

    Article  CAS  Google Scholar 

  • Zhu H, Zhang Y, Yang X, Liu H, Shao L, Zhang X, Yao J (2015a) One-step green synthesis of non-hazardous dicarboxyl cellulose flocculant and its flocculation activity evaluation. J Hazard Mater 296:1–8

    Article  CAS  Google Scholar 

  • Zhu H, Zhang Y, Yang X, Liu H, Zhang X, Yao J (2015b) An eco-friendly one-step synthesis of dicarboxyl cellulose for potential application in flocculation. Ind Eng Chem Res 54:2825–2829

    Article  CAS  Google Scholar 

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Acknowledgments

The work is financially supported by the National Natural Science Foundation of China (51303159, 51372226), National Science Foundation of Zhejiang Province (LY15E030003), and 521 Talent Project of Zhejiang Sci-Tech University.

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Authors and Affiliations

  1. The Key Laboratory of Advanced Textile Materials and Manufacturing Technology of Ministry of Education, College of Materials and Textiles, Zhejiang Sci-Tech University, Hangzhou, 310018, China

    Wenjing Zhu, Lin Liu, Qian Liao, Xuan Chen, Zhouqi Qian, Junyan Shen, Junlong Liang & Juming Yao

  2. National Engineering Lab of Textile Fiber Materials and Processing Technology, Hangzhou, 310018, China

    Lin Liu & Juming Yao

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  1. Wenjing Zhu
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  2. Lin Liu
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  3. Qian Liao
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  4. Xuan Chen
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  6. Junyan Shen
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  7. Junlong Liang
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  8. Juming Yao
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Correspondence to Juming Yao.

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Zhu, W., Liu, L., Liao, Q. et al. Functionalization of cellulose with hyperbranched polyethylenimine for selective dye adsorption and separation. Cellulose 23, 3785–3797 (2016). https://doi.org/10.1007/s10570-016-1045-4

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  • DOI: https://doi.org/10.1007/s10570-016-1045-4

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