The thiol‐ene (click) reaction for the synthesis of plant oil derived polymers

Türünç, Oğuz; Meier, Michael A. R.

doi:10.1002/ejlt.201200148

Cited by 149 publications

(69 citation statements)

References 61 publications

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“…[8,9] In addition, thiol-ene is known as a versatile tool to produce polymers from fully renewable α,ω-diene monomers bearing, for example, ester, ether, or amide functional groups in the backbone chain. [10][11][12] There is a growing interest in developing novel biomaterials aiming for applications in drug delivery systems, tissue engineering, and to address environmental issues. In this context, thiol-ene reactions have been earning attention due to the improved mechanical properties, unique crosslinking structure, clean, and environmentally harmless reaction conditions, and tunable degradability behavior provided by these click reactions.…”

Section: Introductionmentioning

confidence: 99%

Biocompatible Polymeric Nanoparticles From Castor Oil Derivatives via Thiol‐Ene Miniemulsion Polymerization

Cardoso

Machado²,

Feuser³

et al. 2017

Euro J Lipid Sci & Tech

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Biocompatible polymeric nanoparticles are obtained via thiol-ene polymerization of a biobased monomer in miniemulsion. The α,ω-diene-diester monomer is synthesized through esterification reaction of a glycerol derivative, namely 1,3-propanediol, with 10-undecenoic acid, a long-chain diene carboxylic acid. In order to investigate how different monomeric structures behave toward thiolene polymerization in miniemulsion, two types of thiols are investigated: 1,4-butanedithiol and 2-mercaptoethyl ether. Poly(thioether-ester)s with weight average molecular weight up to 15 kDa (M n ) are obtained, depending on initiator concentration and types of surfactant and dithiol employed. Finally, biobased poly(thioether-ester) nanoparticles are submitted to cytotoxicity and hemolysis analyses. High cell viability and no significant changes in cell morphology are observed after the incubation on murine fibroblast (L929) and human cervical cancer cells (HeLa). Last, hemolysis assays revealed blood compatibility and therefore polymeric nanoparticles have been shown to be a potential alternative drug delivery vector for intravenous administration. Practical Applications: There is a great demand for polymeric systems that fulfill a number of requirements, such as biodegradability and biocompatibility, for biomedical applications. In this context, biobased polymers obtained from vegetable oils are a very attractive sustainable alternative to fossil-derived polymeric materials, presenting potential biodegradability and low toxicity. By thiol-ene reactions, polymeric materials containing ester groups in the main chain -which can undergo hydrolysis-can be prepared in miniemulsion, enabling their degradation in physiological environment and, therefore, being interesting for biomedical applications and material disposal. Such novel materials could be used in temporary implants, tissue engineering, and drug delivery systems.

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Section: Introductionmentioning

confidence: 99%

Biocompatible Polymeric Nanoparticles From Castor Oil Derivatives via Thiol‐Ene Miniemulsion Polymerization

Cardoso

Machado²,

Feuser³

et al. 2017

Euro J Lipid Sci & Tech

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“…Plant essential oils contain saturated and unsaturated aromatic compounds, such as terpenes, monoterpenes, thujone, polyphenols, tannins, alkene, flavonoid, cedrol, and phenolic acids (Fernández-Pan et al 2013;Türünç and Meier 2013). Most of these compounds are hydrophobic with a wide range of antimicrobial properties (Seydim and Sarikus 2006).…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial activity of sugar beet lignocellulose films containing tung oil and cedarwood essential oil

Shen

Kamdem

2015

Cellulose

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Several studies have been reported on the use of cellulose, lignocellulose, chitin and other biological macromolecules for food packaging. One of the major drawbacks limiting their wide uses is their limited antimicrobial and water vapor barrier properties. In this study, cedarwood (Thuja occidentalis) essential oil (CWO), known to contain terpenes, polyphenols and tung oil, known to contain fatty acids, were used as additives to improve water vapor barrier, antimicrobial, and physical properties of laboratory cast lignocellulose films. Physicochemical and mechanical properties were tested to evaluate the impact of the addition of oils in the films formulations. The addition of 15 % CWO and tung oils improved water vapor permeability by more than 25 % as also evidenced by the increase of contact angle between water and film by 134 % from 38.98°to 89.36°with 15 % tung oil. FTIR was used to monitor the presence of hydrophobic groups at 1463 and 1741 cm -1 from the oil on the film spectra confirming the improvement of film hydrophobicity from oils interactions. However, the addition of 15 % hydrophobic oils promoted a significant decrease in tensile properties of films (p B 0.05) by 40 % for CWO and 32 % for tung oil, respectively, due to a partial incompatibility between hydrophilic lignocellulose and hydrophobic oils. The use of a tailored coupling agent to reduce the incompatibility and to improve the load charge transfer between hydrophobic and hydrophilic group might reduce the decrease of the tensile properties with the addition of hydrophobic compounds. No significant difference (p [ 0.05) was observed on the thermal stability of films using TGA. The antimicrobial effects of lignocellulose films against bacteria namely Listeria innocua, Escherichia coli, and Salmonella enterica was tested by disk inhibition zone method and showed an improvement with the addition of 5 % CWO in the film. The Microbe Growth Index of the lignocellulose cellulosic films containing 20 % w/w of CWO decreases by 80 %. CWO and tung oil are good candidates to control microbial growth and water vapor permeability in flexible films. Future work will focus on the olfactory and tensile properties for applications in food packaging.

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“…Reaction optimisation produced thiol-bearing dyes to relatively high yields. Although the side reaction of thioester formation was observed, each product obtained possessed both the chromophore and a thiol group, dictating that they can be utilised for colouration of substrates that possess C=C bonds via TEC reactions, thus enhancing the application range of conventional reactive dyes [7]. Furthermore, the thiol-modification method is applicable to other dyes which have aliphatic OH groups in their structures.…”

Section: Discussionmentioning

confidence: 99%

“…The dye with thiol functionality may be readily incorporated into materials containing (C=C) groups by highly effective TEC reactions, enhancing the prospect of efficient dye conjugation to an appropriate substrate. One application example is to incorporate the dyes into plant oils [7], enabling the production of highly durable coating materials.…”

Section: Introductionmentioning

confidence: 99%

The synthesis and characterisation of thiol-bearing C. I. Disperse Red 1

Hayashi

Thornton

2015

Dyes and Pigments

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C. I. Disperse Red 1 (DR1) was chemically modified by a facile, one-step, Steglich esterification to yield the thiol-bearing analogue. The dye produced possesses the appropriate functionality to be readily incorporated into appropriate materials by highly effective thiol-ene 'click' chemistry reactions. This method of dye modification greatly widens the application range of hydroxyl-bearing reactive dyes for various materials, enabling the facile production of coloured materials by using the thiol groups added.

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The thiol‐ene (click) reaction for the synthesis of plant oil derived polymers

Cited by 149 publications

References 61 publications

Biocompatible Polymeric Nanoparticles From Castor Oil Derivatives via Thiol‐Ene Miniemulsion Polymerization

Biocompatible Polymeric Nanoparticles From Castor Oil Derivatives via Thiol‐Ene Miniemulsion Polymerization

Antimicrobial activity of sugar beet lignocellulose films containing tung oil and cedarwood essential oil

The synthesis and characterisation of thiol-bearing C. I. Disperse Red 1

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