Reversible acetalization of cellulose: A platform for bio-based materials with adjustable properties and biodegradation

被引:10
作者
Peil, Stefan [1 ,2 ]
Gojzewski, Hubert [1 ]
Wurm, Frederik R. [1 ]
机构
[1] Univ Twente, Fac Sci & Technol, MESA Inst Nanotechnol, Dept Mol & Mat,Sustainable Polymer Chem SPC, NL-7500 AE Enschede, Netherlands
[2] Max Planck Inst Polymer Res, Ackermannweg 10, D-55128 Mainz, Germany
关键词
Acetalated; Biodegradable; Bio-based; Soil; -degradable; Compost; Acetal-derivatized; ACETALS; DEPROTECTION; SUBSTITUTION; DEXTRAN; KETALS; ESTERS;
D O I
10.1016/j.cej.2022.139280
中图分类号
X [环境科学、安全科学];
学科分类号
08 ; 0830 ;
摘要
Bio-based and biodegradable polymers are essential for a sustainable society. Cellulose is the most abundant biopolymer on earth; however, derivatization is necessary for its processing, which slows down its biodegrad-ability dramatically, e.g. used cigarette filters made from cellulose acetate are barely biodegradable. We developed the first reversible modification of cellulose, which allows processing and guarantees full biodegra-dation even at high degrees of substitution as the linkers, acetals, can be cleaved first during the degradation process releasing native cellulose that biodegrades in a second step. Acetalization is a versatile platform approach to bio-based and fully degradable cellulose-derivatives, which are characterized by solubility in common organic solvents (alcohols, aromatic and chlorinated solvents), adjustable glass transition temperatures (-48 degrees C < Tg < 80 degrees C), young's modulus (1.9 MPa < E < 58 MPa) and contact angle (86 degrees< & theta; < 124 degrees). In contrast to previously known cellulose modifications, cellulose acetals remain fully degradable as the acetal bond is reversible and undergoes an acidic cleavage under desired conditions, for instance in compost, followed by enzymatic degra-dation of the remaining cellulose backbone. With climate change and plastic pollution, these new and versatile cellulose acetals provide bio-based and biodegradable alternatives to fossil-based and non-degradable polyolefin plastics, leading to a more sustainable future for our planet.
引用
收藏
页数:10
相关论文
共 39 条
  • [1] Acetal-derivatized dextran:: An acid-responsive biodegradable material for therapeutic applications
    Bachelder, Eric M.
    Beaudette, Tristan T.
    Broaders, Kyle E.
    Dashe, Jesse
    Frechet, Jean M. J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (32) : 10494 - +
  • [2] Behr A., 2018, EINFUHRUNG CHEM NACH, DOI DOI 10.1007/978-3-662-55255-1
  • [3] Acetalated dextran is a chemically and biologically tunable material for particulate immunotherapy
    Broaders, Kyle E.
    Cohen, Joel A.
    Beaudette, Tristan T.
    Bachelder, Eric M.
    Frechet, Jean M. J.
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2009, 106 (14) : 5497 - 5502
  • [4] Enzymatic degradation of plant biomass and synthetic polymers
    Chen, Chun-Chi
    Dai, Longhai
    Ma, Lixin
    Guo, Rey-Ting
    [J]. NATURE REVIEWS CHEMISTRY, 2020, 4 (03) : 114 - 126
  • [5] ECHA, 2019, REG RESTR INT OUTC E
  • [6] Sustainable Fatty Acid Modification of Cellulose in a CO2-Based Switchable Solvent and Subsequent Thiol-Ene Modification
    Esen, Eren
    Haedinger, Pauline
    Meier, Michael A. R.
    [J]. BIOMACROMOLECULES, 2021, 22 (02) : 586 - 593
  • [7] Sustainable Functionalization of 2,3-Dialdehyde Cellulose via the Passerini Three-Component Reaction
    Esen, Eren
    Meier, Michael A. R.
    [J]. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2020, 8 (41) : 15755 - 15760
  • [8] Modified Breath Figure Methods for the Pore-Selective Functionalization of Honeycomb-Patterned Porous Polymer Films
    Falak, Shahkar
    Shin, Bokyoung
    Huh, Dosung
    [J]. NANOMATERIALS, 2022, 12 (07)
  • [9] Production, use, and fate of all plastics ever made
    Geyer, Roland
    Jambeck, Jenna R.
    Law, Kara Lavender
    [J]. SCIENCE ADVANCES, 2017, 3 (07):
  • [10] CELLULOSE DERIVATIVES WITH LOW DEGREE OF SUBSTITUTION .3. THE BIODEGRADABILITY OF CELLULOSE ESTERS USING A SIMPLE ENZYME ASSAY
    GLASSER, WG
    MCCARTNEY, BK
    SAMARANAYAKE, G
    [J]. BIOTECHNOLOGY PROGRESS, 1994, 10 (02) : 214 - 219