Fatty Acid Derived Monomers and Related Polymers <i>Via</i> Thiol‐ene (Click) Additions

Türünç, Oğuz; Meier, Michael A. R.

doi:10.1002/marc.201000291

Cited by 174 publications

(74 citation statements)

References 41 publications

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“…[27] In addition, the polymers exhibited double melting endotherms revealing that the polymers first undergo a melting process causing an increase in chain mobility and leading to a crystallization, which is followed by a second melting. [28,29] FTIR spectra of a dried sample from reaction M3 is presented in Figure 3. It can be noticed that there is no peak correspondent to double bonds at 1640 cm (C5 5C stretch), indicating absence of residual diene monomer.…”

Section: Thiol-ene Polymerizationmentioning

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: Thiol-ene Polymerizationmentioning

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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“…Moreover, a castor oil derivative, 10-undecenoic acid, was widely used to prepare bio-based building blocks via thiol-ene reactions. [9][10][11][12]More recently, Türünç and co-workers reported the use of functional monothiols and dithiols for the functionalization of castor oil-derived 10-undecenoic acid [13]. It was proposed to use the synthesized materials as building blocks in the synthesis of novel polymeric structures.…”

Section: Introductionmentioning

confidence: 99%

Renewable sulfur-containing thermoplastics via AB-type thiol-ene polyaddition

Berg

Dışpınar

Hommez

et al. 2013

European Polymer Journal

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Polythioethers with molar masses up to 40 kDa were prepared by UV-or thermal initiated thiolene polyaddition polymerization of an aliphatic α-olefinic ω-thiol, an AB-type monomer derived from 10-undecenoic acid, which is a bio-sourced building block obtained from castor oil. The low polarity of the starting compound and the stability of the thioether functions formed during polymerization allowed for the synthesis of polymers with similar structures to existing bulk and engineering plastics such as polyethylene. The presence of the thioether functions offered the opportunity to oxidize these polyethylene analogues by hydrogen peroxide into sulfone linkages, resulting in polysulfones, which are valuable as engineering plastic in several application fields.Thermal analysis demonstrated the increased thermal stability and melting temperature (175°C) of these polysulfones.

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“…45 Very recently, Meier et al synthesized the first polyesters from polyols obtained by thiol-ene coupling on derivatives of vegetable oils. 46 Generally, polyols synthesized by thiol-ene coupling are derived from fatty acids. Our study is designed to synthesize new biobased polyols, directly from unsaturated triglycerides by thiol-ene coupling, in order to use them in PUs syntheses.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new polyurethanes from vegetable oil by thiol-ene coupling

et al. 2013

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Soybean vegetable oil was functionalized in a single step by addition of mercaptan with hydroxyl functions by ther-mal thiol-ene coupling. The synthesized biobased polyol was analyzed by nuclear magnetic resonance, titrations, size exclusion chromatography, and mass analyses to precisely determine its average functionality, thus allowing the use of the mixture of products without purification. This polyol was added to a prepolymer of 4, 4'-diisocyanate diphenylmethylene (MDI) with a ratio OH/NCO of 1, to synthesize partially bio-based polyurethane by step growth polymerization. The synthesized polyurethane was compared to polyurethane obtained from a commercial polyether polyol polyester, named desmophen 1150. Mixtures of these polyols were made to optimize the properties of the materials obtained. Polymerization was monitored by rheology. Polyurethanes were characterized by thermogravimetric analysis, differential scanning calorimetry, shore hardness, and tensile tests at different temperatures to determine their thermal and mechanical properties. Different materials present the characteristics of soft and ductile elastomers with thermal stability of polyurethanes.

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Fatty Acid Derived Monomers and Related Polymers Via Thiol‐ene (Click) Additions

Cited by 174 publications

References 41 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

Renewable sulfur-containing thermoplastics via AB-type thiol-ene polyaddition

Synthesis of new polyurethanes from vegetable oil by thiol-ene coupling

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