A facile and green route to terpene derived acrylate and methacrylate monomers and simple free radical polymerisation to yield new renewable polymers and coatings

Sainz, Marina; Souto, José A.; Regentová, Dominika; Johansson, Mats; Timhagen, Susana Torron; Irvine, Derek J.; Buijsen, Paul; Koning, Cor E.; Stockman, Robert A.; Howdle, Steven M.

doi:10.1039/c6py00357e

Cited by 95 publications

(130 citation statements)

References 21 publications

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“…The polymerization of methacrylates (TEGDMA, TEGDMA/bis‐GMA blend, and EB605) resulted in much lower C than acrylates (Table ). This can be ascribed to the lower reactivity of methacrylates than that of acrylates and the stiffer chain or network formed by methacrylates, which leads to the termination of propagating chain with lower conversion . The conversion (66%) in photopolymerization of TEGDMA/bis‐GMA blend under 410 nm was comparable with that previously achieved under LED@405 nm (64%, ≈110 mW cm −2 ), which demonstrates that the photopolymerization with R‐Cl is quite reproducible …”

Section: Resultssupporting

confidence: 58%

Yellow Triazine as an Efficient Photoinitiator for Polymerization and 3D Printing under LEDs

Lai

Zhu

Xiao

2019

Macro Chemistry & Physics

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The search for new efficient photoinitiators for polymerization under the illumination of visible light is under extensive investigation due to their wide application in 3D printing. 2‐(4‐Methoxystyryl)‐4,6‐bis(trichloromethyl)‐1,3,5‐triazine (yellow triazine, R‐Cl) alone or the R‐Cl/additive systems have been indicated as promising photoinitiating systems in the free radical polymerization at 405 nm in our previous study. Here, further investigation of R‐Cl in the polymerization of a series of difunctional (meth)acrylate monomers is described. The effect of monomers on the polymerization performance is elucidated. The interplay of functional group, double bond concentration, and fluidity determines the polymerization rate and final conversions. Remarkably, R‐Cl shows better photoinitiating ability than well‐known commercial photoinitiator bisacylphosphine oxide in the polymerization of bis‐GMA/TEGDMA blend and EB605 under LED at 400 nm. The optimum concentrations of R‐Cl in the photopolymerization of TetEGDA and DPGDA monomers are revealed, the results of which are used to guide the 3D printing of DPGDA.

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Section: Resultssupporting

confidence: 58%

Yellow Triazine as an Efficient Photoinitiator for Polymerization and 3D Printing under LEDs

Lai

Zhu

Xiao

2019

Macro Chemistry & Physics

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“…A recent publication by Sainz et al 87 has developed simple chemistry to modify terpenes and create new polymers. Cheap and abundant terpenes, such as a-pinene (11), b-pinene (10) and limonene (6), were transformed into monomers by the addition of acrylates and methacrylate functionality to create new monomers that can easily undergo free-radical polymerisation (FRP).…”

Section: Pinenesmentioning

confidence: 99%

“…Sainz et al 87 looked into a more efficient one-step synthesis of the monomers by way of C-H activation, which can be viewed as an efficient way of functionalising alkenes. 87 Methacrylic acid was added to 10 by way of catalytic C-H functionalisation using palladium (II) acetate (Pd(OAc) 2 ) as a catalyst (Scheme 14).…”

Section: Pinenesmentioning

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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“…13,20 Neste sentido, é crescente o interesse de indústrias e pesquisadores no uso dos componentes majoritários dos OEs como reagentes para a produção de novos compostos semissintéticos, visando potencializar suas atividades biológicas e diminuir a volatilidade, tendo como alvo as aplicações farmacológicas, em alimentos ou em cosméticos. 13,20,25 Recentemente, indústrias e pesquisadores estão focados nos componentes majoritários dos OEs para usá-los como solventes verdes bioderivados 13,[26][27] na extração de metabólitos como gorduras, lipídios, carotenoides e polifenóis, para usá-los como monômero na síntese de polímeros renováveis [29][30][31] ou como auxiliares em síntese assimétrica. 13 Entretanto, estas características dos óleos essenciais ainda são pouco exploradas no Brasil, que se destaca como um dos principais produtores mundiais de óleos essenciais.…”

Section: Introductionunclassified

Essential Oils as a Sustainable Raw Material for the Preparation of Products with Higher Value-Added

Jacob

2017

Rev. Virtual Quim.

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Abstract:The use of renewable feedstocks, which may substitute those derived from petroleum, is currently a great challenge in the chemical and pharmaceutical industries. However, plant essential oils (EOs) that have been studied for their biological activities, such as antioxidant, antimicrobial, antifungal and antinociceptive are generally regarded as safe additives maintaining the microbiological stability of foods. EOs are a mixture of natural volatile compounds, that are predominantly formed during the secondary metabolism in plants and commonly concentrated in the leaves, bark or fruits of aromatic plants. They are complex mixtures composed mainly of terpenes (hydrocarbons or oxygenated compounds) and phenylpropanoids, which can be used as a source of raw materials for fine chemicals industry. In recent years, researchers and industries have been focusing on the major compounds of EOs in order to use them as solvents or as bio-based building blocks adding value to this material derived from biomass.Keywords: Essential oil; bio-based compounds; biomass. ResumoO uso de matérias-primas renováveis, que podem substituir os derivados de petróleo, é atualmente um grande desafio para as indústrias químicas e farmacêuticas. No entanto, os óleos essenciais (OEs) de plantas que têm sido estudados pelas suas atividades biológicas, tais como antioxidante, antimicrobiana, antifúngica e antinociceptiva, são geralmente considerados como aditivos seguros para a manutenção da estabilidade microbiológica de alimentos. Os OEs são uma mistura de compostos voláteis naturais, que são formados durante o metabolismo secundário das plantas e geralmente concentrados nas folhas, casca ou frutos de plantas aromáticas. Eles são misturas complexas compostas principalmente de terpenos (hidrocarbonetos ou compostos oxigenados) e fenilpropanoides, que podem ser utilizados como uma fonte de matéria-prima para a indústria de química fina. Nos últimos anos, pesquisadores e indústrias estão focados nos componentes majoritários dos OEs, a fim de usá-los como solventes ou como blocos de construção de base biológica agregando valor a este material derivado de biomassa.

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A facile and green route to terpene derived acrylate and methacrylate monomers and simple free radical polymerisation to yield new renewable polymers and coatings

Cited by 95 publications

References 21 publications

Yellow Triazine as an Efficient Photoinitiator for Polymerization and 3D Printing under LEDs

Yellow Triazine as an Efficient Photoinitiator for Polymerization and 3D Printing under LEDs

Progress in the synthesis of sustainable polymers from terpenes and terpenoids

Essential Oils as a Sustainable Raw Material for the Preparation of Products with Higher Value-Added

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