Terpene-Based Renewable Monomers and Polymers via Thiol–Ene Additions

Firdaus, Maulidan; Espinosa, Lucas Montero de; Meier, Michael A. R.

doi:10.1021/ma201544e

Cited by 203 publications

(195 citation statements)

References 52 publications

(77 reference statements)

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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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“…Currently, polymers are prepared from components, which are derived from petroleum [5,6]. Renewable substances proposed for the synthesis of polymers are, for example, vegetable oils (e.g., linseed oil, sunflower oil, palm oil, cotton oil, soybean oil, tung oil, cashew nut oil [5][6][7][8]), glycerol and its derivatives [9,10], terpenes [11] and rosin [12,13]. The bio-based components, which can be used as a polyols in the synthesis of polyurethanes, are, for example, castor oil [14], polyricinoleate diol [15], hydroxylated soybean oil [6,16], hydroxylated hemp seed oil [17] and polyglycerols [18].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structure and properties of poly(ether-urethane)s synthesized using a tri-functional oxypropylated glycerol as a polyol

Datta

Kosiorek

Włoch

2016

J Therm Anal Calorim

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The main aim of this work was to obtain poly(ether-urethane)s using tri-functional polyoxyalkylene polyol (Rokopol G1000), which introducing the chemical cross-links into the structure of polyurethanes. Poly(etherurethane)s were prepared using two-step method, called prepolymer method, which involves in the first step the reaction of 4,4 0 -diphenylmethane diisocyanate (MDI) and tri-functional polypropylene glycol glycerol triether polyol. In the second step, prepolymer chains were extended by using: 1,6-hexanediol, 1,4-butanediol in the mixture with poly(ethylene glycol) and poly(ethylene glycol). The prepolymer chains extending was realized at three different molar ratios of NCO groups (presented in prepolymer) to OH groups (presented in chain extender), i.e., 0.95, 1.00 or 1.05. The influence of chain extender type on the chemical structure, selected mechanical properties and thermomechanical properties of the obtained poly(ether-urethane)s was investigated. The results showed that applying different types of chain extenders results in obtaining materials with diversified mechanical properties, but very similar thermal stability. The performance of obtained poly(etherurethane)s is mostly affected by the chemical cross-links, which were introduced into soft segments by tri-functional polyetherol.

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“…Works by Firdaus et al 61 and Firdaus and Meier 78 also demonstrate the potential for the elegant and efficient chemical functionalisation of renewable monomers. The functionalisations were carried out at room temperature without the presence of solvents.…”

Section: Limonenementioning

confidence: 95%

“…77 Firdaus et al 61 utilised the high atom efficiency of thiol-ene additions to introduce different functional groups to produce limonene-based homopolymers. Limonene (6) was reacted with both hydroxyl-and methyl esterfunctionalised thiols to produce monomers which would be suitable for polymerisation through polycondensation (Scheme 8).…”

Section: Limonenementioning

confidence: 99%

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Progress in the synthesis of sustainable polymers from terpenes and terpenoids

et al. 2016

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The imminent depletion of resources derived from fossil fuels is a major concern for today's society. 300 Mt of polymers are used every year in the form of plastics, most commonly derived from fossil fuels, hence the necessity to find new materials based on renewable resources. This review explores the utilisation of monoterpenes and terpenoids -a family of abundant and inexpensive natural products -as promising renewable monomers. Terpenes can be directly used in polymerisations or converted into bespoke monomers through organic transformations. The use of terpenes for the production of renewable plastics has been a prevalent topic of research for the past few decades. Early research focused on cationic polymerisation of terpenes by way of their alkene moieties; however, more recently terpenes are being functionalised to incorporate handles for a larger range of polymerisation techniques. Herein an assessment of the future prospects for the use of these small functional molecules to synthesise novel and valuable renewable materials is presented.

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Terpene-Based Renewable Monomers and Polymers via Thiol–Ene Additions

Abstract: ACKNOWLEDGMENT M.F. is thankful for a fellowship from the Indonesian Directorate General of Higher Education. ' DEDICATIONDedicated to Professor Christian Bruneau on the occasion of his 60th birthday.

Cited by 203 publications

References 52 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

Synthesis, structure and properties of poly(ether-urethane)s synthesized using a tri-functional oxypropylated glycerol as a polyol

Progress in the synthesis of sustainable polymers from terpenes and terpenoids

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