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

Maximilian Röhrl; Justus F Ködel; Renee L Timmins; Christoph Callsen; Merve Aksit; Michael F Fink; Sebastian Seibt; Andy Weidinger; Glauco Battagliarin; Holger Ruckdäschel; Rainer Schobert; Josef Breu; Bernhard Biersack

doi:10.1021/acsomega.2c06811

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

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

Affiliations

¹ Inorganic Chemistry 1, University of Bayreuth, Universitätsstrasse 30, 95440 Bayreuth, Germany.
² Fachgruppe Chemie, Wirtschaftswissenschaftliches und Naturwissenschaftlich-Technologisches Gymnasium Bayreuth, Am Sportpark 1, 95448 Bayreuth, Germany.
³ Department of Polymer Engineering, Faculty of Engineering Science, University of Bayreuth, Universitätsstrasse 30, 95440 Bayreuth, Germany.
⁴ Chair of Electrochemical Process Engineering, Faculty of Engineering Science, University of Bayreuth, Universitätsstrasse 30, 95447 Bayreuth, Germany.
⁵ Linseis Messgeräte GmbH, Vielitzerstrasse 43, 95100 Selb, Germany.
⁶ Biopolymers and Biodegradability Research, BASF, Carl-Bosch-Str. 38, 67056 Ludwigshafen am Rhein, Germany.
⁷ Organic Chemistry 1, University of Bayreuth, Universitätsstrasse 30, 95440 Bayreuth, Germany.

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.