The preparation and properties of vinyl cellulose

Träskman, B.; Tammela, Viljo

doi:10.1002/app.1986.070310708

Cited by 7 publications

(2 citation statements)

References 12 publications

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“…The absorption band at 1722 cm −1 corresponded to the carbonyl C=O ester stretching vibration and verified the methacrylation of the tosyl cellulose (MATSC). Additionally, new absorption bands arose at 1633 cm −1 and 941 cm −1 , referring to the alkene C=C stretching vibration and the C=CH 2 out-of-plane deformation vibration, respectively [ 12 , 37 ]. Furthermore, in comparing the TSC and MATSC spectra, a decrease in the absorption intensity that originated from the stretching vibration of the hydroxyl groups was observed at around 3487 cm −1 [ 12 , 30 ].…”

Section: Resultsmentioning

confidence: 99%

Photocrosslinkable Cellulose Derivatives for the Manufacturing of All-Cellulose-Based Architectures

Rothammer,

Zollfrank

2023

Polymers

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Replacing petroleum-based polymers with biopolymers such as polysaccharides is essential for protecting our environment by saving fossil resources. A research field that can benefit from the application of more sustainable and renewable materials is photochemistry. Therefore, cellulose-based photoresists that could be photocrosslinked via UV irradiation (λ = 254 nm and λ = 365 nm) were developed. These biogenic polymers enable the manufacturing of sustainable coatings, even with imprinted microstructures, and cellulose-based bulk materials. Thus, herein, cellulose was functionalized with organic compounds containing carbon double bonds to introduce photocrosslinkable side groups directly onto the cellulose backbone. Therefore, unsaturated anhydrides such as methacrylic acid anhydride and unsaturated and polyunsaturated carboxylic acids such as linoleic acid were utilized. Additionally, these cellulose derivatives were modified with acetate or tosylate groups to generate cellulose-based polymers, which are soluble in organic solvents, making them suitable for multiple processing methods, such as casting, printing and coating. The photocurable resist was basically composed of the UV-crosslinkable biopolymer, an appropriate solvent and, if necessary, a photoinitiator. Moreover, these bio-based photoresists were UV-crosslinkable in the liquid and solid states after the removal of the solvent. Further, the manufactured cellulose-based architectures, even the bulk structures, could be entirely regenerated into pure cellulose devices via a sodium methoxide treatment.

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Section: Resultsmentioning

confidence: 99%

Photocrosslinkable Cellulose Derivatives for the Manufacturing of All-Cellulose-Based Architectures

Rothammer,

Zollfrank

2023

Polymers

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“…[13,20] Accordingly, functionalization of the CDA with sorbic acid, led to additional absorption bands at 1644 cm -1 , 1617 cm -1 , 957 cm -1 and 801 cm -1 . These bands correspond to the alkene C=C stretching vibration [21][22][23] and the C=CH out-of-plane deformation [23,24] of the conjugated carboncarbon double bonds. Comparing the spectra of CDA with those of MACA and SORCA at 3485 cm -1 (stretching vibration of the hydroxyl groups), a decrease is noticeable, 12 which is due to the substitution of the hydroxyl groups by unsaturated moieties during the syntheses.…”

Section: Characterization Of the Biocompatible Materialsmentioning

confidence: 99%

Biocompatible, sustainable coatings based on photo-crosslinkable cellulose derivatives

Rothammer

Ströbel²,

Zollfrank

et al. 2023

Preprint

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Materials derived from renewable resources have great potential to replace fossil-based plastics in biomedical applications. In this study, the synthesis of cellulose-based photoresists by esterification with methacrylic acid anhydride and sorbic acid was investigated. These resists polymerize under UV irradiation in the range λ=254 nm to 365 nm, with or even without the use of an additional photoinitiator concerning the sorbic acid derivative. Usability for biomedical applications was demonstrated by investigating the adhesion and viability of a fibrosarcoma cell line (HT-1080). Compared to polystyrene, the material widely used for cell culture dishes, cell adhesion to the biomaterials tested was even stronger, as assessed by a centrifugation assay. This is all the more remarkable since chemical surface modification of cellulose with methacrylate and sorbic acid allows direct attachment of HT-1080 cells without the addition of protein modifiers or ligands. Furthermore, cells on both biomaterials show similar cell viability, not significantly different from polystyrene, indicating no significant impairment or enhancement. This will allow the future use of these cellulose derivatives as support structures for scaffolds or as self-supporting coatings also for cell culture, based solely on renewable and sustainable resources.

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Synthesechemische Modifizierung von Cellulose zur Einführung aktiver funktioneller Gruppen unter heterogenen Reaktionsbedingungen. Fortschrittsbericht

1990

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Herrn Professor D r . habil. Burkart Philipp zum 65. Geburtstag gewidmetDie vorliegende Ubersicht enthalt eine zusammenfassende Darstellung von Untersuchungen zur Einfuhrung reaktiver funktioneller Gruppen in die Cellulose. Unter synthesechemischen Gesichtspunkten werden heterogen verlaufende Reaktionen betrachtet, die sich vor allem durch die Erzielung eines moglichst hohen durchschnittlichen Substitutionsgrades, einen weitgehend selektiven Verlauf oder die Anwendung neuer praparativer Techniken und Reagenzien auszeichnen. X w u u e c x a z Moi3u$uxayuR y e~a r n~z o m e eemepozennb8x ycAosuRx ~J C R eeeaexuu peaxmusnbcx $ynxyuon(Wtbnbtx z p y n n , 0630pOIIACbIBaloTCR ACCJIeHOBaHHR 0 BBeAeHAH PeaKTABHbIX @YHKI(AOHaJIbHbIX FpyIIII B I(eJIJIloJI03y B FeTepOreHHbIX YCJIOBARX PeaKUAA. c TOYKA 3peHAR CMHTeTMSeCKOfi XMMMM PaCCMaTpABaloTCR peaHI(MM, KOTOpbIe AaIoT BOBMOXHOCTb AOCTAFHYTb BbICOKYlo CpeAH€O€O CTeIIeHb 3aMeqeHAR, IIOJIyWfTb CeJIeKTMBHbIfi XOA PeaKqMM MJIA IIpAMeHATb HOBbIe cnoco6b1 nonyqemFi A npenapaTb1. Zntroduction of reactive functional groups into cellulose by chemical modification under heterogeneous conditions. ReviewInvestigations on the introduction of reactive functional groups into cellulose a t heterogeneous conditions of reaction are reviewed. From the organic chemist's point of view the survey considers reactions characterized by yielding a high degree of substitution, a selective course of functionalisation, or the use of modern preparation techniques and new reagents.

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The preparation and properties of vinyl cellulose

Abstract: synopsisThe vinylation of cellulose by acetylene under alkaline conditions was optimized with respect to both DS and DP. Shortening the reaction time reduced the harmful alkaline depolymerization of cellulose during the reaction and gave products with higher DP values.

Cited by 7 publications

References 12 publications

Photocrosslinkable Cellulose Derivatives for the Manufacturing of All-Cellulose-Based Architectures

Photocrosslinkable Cellulose Derivatives for the Manufacturing of All-Cellulose-Based Architectures

Biocompatible, sustainable coatings based on photo-crosslinkable cellulose derivatives

Synthesechemische Modifizierung von Cellulose zur Einführung aktiver funktioneller Gruppen unter heterogenen Reaktionsbedingungen. Fortschrittsbericht

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