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. 2023 Mar 9;8(11):9889-9895.
doi: 10.1021/acsomega.2c06811. eCollection 2023 Mar 21.

New Functional Polymer Materials via Click Chemistry-Based Modification of Cellulose Acetate

Maximilian Röhrl  1 , Justus F Ködel  2 , Renee L Timmins  1 , Christoph Callsen  3 , Merve Aksit  3 , Michael F Fink  4 , Sebastian Seibt  5 , Andy Weidinger  2 , Glauco Battagliarin  6 , Holger Ruckdäschel  3 , Rainer Schobert  7 , Josef Breu  1 , Bernhard Biersack  7
Affiliations

New Functional Polymer Materials via Click Chemistry-Based Modification of Cellulose Acetate

Maximilian Röhrl et al. ACS Omega. .

Abstract

Cellulose acetate (CA) was partially acrylated, and the resulting cellulose acetate acrylate (acryl-substitution degree of 0.2) underwent quantitative thio-Michael click reactions with various thiols. A toolbox of functional CA polymers was obtained in this way, and their properties were studied. The modification with fatty alkyl thiols led to hydrophobic materials with large water drop contact angles. Octadecylthio-, butoxycarbonylpropylthio-, and furanylthio-modifications formed highly transparent materials. The new derivative CAASFur disintegrated completely under industrial composting conditions. Films of modified CA polymers were cast and investigated in terms of barrier properties. The nanocomposite of CAAS18 compounded with a synthetic layered silicate (hectorite) of a large aspect ratio showed permeabilities as low as 0.09 g mm m-2 day-1 for water vapor and 0.16 cm3 mm m-2 day-1 atm-1 for oxygen. This portfolio of functional CA polymers opens the door to new applications.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Reagents and Conditions: Thiol (6 equiv), Et3N (3 equiv), DMSO or THF, r.t., 24 h
Figure 1
Figure 1
(A) Contact angles of water drops on plates made from derivatives CAAS12-20 or from the control polymers PS and CA after 1 min (means of the left and right angles). (B) Representative images of water drops on the indicated polymer plates after 1 min.
Figure 2
Figure 2
Time-dependent disintegration (in %) of the new polymer CAASFur under industrial composting conditions according to ISO 20200.
Figure 3
Figure 3
Characterization of the CAAS18/Hec nanocomposite film. (A) XRD pattern of the neat CAAS18 film (black) and CAAS18/Hec nanocomposite film (blue). Top inset sketches the tortuous path theory for an oxygen molecule. Bottom inset shows the transparent CAAS18/Hec nanocomposite film. (B) TEM image of the CAAS18/Hec cross-section indicating segregated domains of CAAS18 slabs (bright) and restacked Hec-only domains (dark).
See this image and copyright information in PMC

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