A Green Step to New Monomers and Their Polymerization

Strehmel, Veronika; Strunk, David; Heinz, Markus; Walther, Sebastian

doi:10.1002/slct.202002526

Cited by 7 publications

(12 citation statements)

References 34 publications

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“…Synthesis of MAPO [27,28] (Scheme 1) and isomer mixture MIMAO comprising methyl 9‐(1H‐imidazol‐1‐yl)‐10‐(methacryloyloxy)‐octadecanoate and methyl 9‐(methacryloyloxy)‐10‐(1H‐imidazol‐1‐yl)‐octadecanoate [12,13] (Scheme 1) are described elsewhere.…”

Section: Methodsmentioning

confidence: 99%

Manufacturing and photocrosslinking of a new bio‐based dimethacrylate resulting in hydrophobic crosslinked films

Sanay

Strehmel

2021

Applied Research

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A new bio‐based dimethacrylate (EMHO) consisting of three isomers, that is (ethane‐1,2‐diyl‐bis(9‐methacryloyloxy‐10‐hydroxy octadecanoate) [EMHO‐i1], ethane‐1,2‐diyl‐9‐hydroxy‐10‐methacryloyloxy‐9′‐methacryloyloxy‐10′‐hydroxy octadecanoate [EMHO‐i2], and ethane‐1,2‐diyl‐bis(9‐hydroxy‐10‐methacryloyloxy octadecanoate [EMHO‐i3]), was made by a three‐step reaction starting from esterification of oleic acid with ethylene glycol followed by epoxidation in a second step, and epoxy ring‐opening reaction with methacrylic acid in a third step. The new dimethacrylate obtained was photocured applying ultra‐violet technology to receive a neat polymer on the one hand and in the presence of a further methacrylate, such as 4‐(4‐methacryloyloxyphenyl)‐butan‐2‐one (MAPO) or methyl 9‐(1H‐imidazol‐1‐yl)‐10‐(methacryloyloxy)‐octadecanoate and methyl 9‐(methacryloyloxy)‐10‐(1H‐imidazol‐1‐yl)‐octadecenoate available as isomer mixture (MIMAO), on the other hand. The photopolymerization kinetic study applying photo‐differential scanning calorimetry technology showed that the addition of MAPO or MIMAO during photocuring resulted in an increase in both polymerization rate and final conversion on monomer in comparison with the homopolymerization of EMHO. As expected, the network density obtained by the study of the elastic modulus of the copolymers was reduced compared to the homopolymer caused by the presence of the methacrylate MAPO or MIMAO comprising only one polymerizable functional group. The crosslinked polymer films contain high gel content. Those films made by using an excess of MAPO showed a glass transition above room temperature caused by the aromatic ring comprising in MAPO. High contact angle values for water indicate the high hydrophobicity of the crosslinked polymer films that is attributed to the long alkyl chains contained in the bio‐based dimethacrylate. The copolymer made from the bio‐based dimethacrylate with MAPO excess may be interesting for application as a water‐repellent coating for surface protection and protection against corrosion.

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Section: Methodsmentioning

confidence: 99%

Manufacturing and photocrosslinking of a new bio‐based dimethacrylate resulting in hydrophobic crosslinked films

Sanay

Strehmel

2021

Applied Research

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“…In addition, the resin formulations based on natural phenolic acrylates containing a structural diacrylate synthesized by a dimerization of eugenol with a dithiol through the radical thiol-ene ''click'' reaction, a mono-methacrylate diluent (guaiacol methacrylate) and a methacrylate cross-linker (vanillyl alcohol methacrylate) have been tested for their use as more environmentally friendly materials for stereolitography 3D printing [34]. Also, the studies on the use of the new methacrylate monomer: eugenyl-2-hydroxypropyl methacrylate for the preparation of copolymers with methyl methacrylate are described [35]. Moreover, terpenes and terpenoids are very interesting group of compounds, due to the large variety of their structures which makes them interesting compounds for the synthesis of the new terpene bio-based polymers.…”

Section: Introductionmentioning

confidence: 99%

TG/DSC/FTIR/QMS analysis of environmentally friendly poly(citronellyl methacrylate)-co-poly(benzyl methacrylate) copolymers

Worzakowska

2023

J Mater Sci

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Polymer materials, not described in the literature so far, were obtained in the process of UV polymerization between methacrylic monomer obtained on the basis of natural, terpene alcohol: citronellyl methacrylate and benzyl methacrylate with different composition. The structures of the novel, environmentally friendly copolymers were confirmed by the FTIR and 13C CPMAS/NMR spectra. The copolymers containing more than 50% mass of citronellyl methacrylate were characterized by a high conversion of the double bonds determined on the basis of the FTIR and NMR spectra (95–96% and 92–94%, respectively). The novel materials were highly resistant to polar and non-polar solvents and the chemical stability. The glass transition temperature was from 15.8 to 19.9 °C which confirms that the obtained materials are elastomers at room temperature. Their thermal stability depended on their composition. It was from 185 to 205 °C (inert conditions) and from 149 to 214 °C (oxidizing conditions). TG/FTIR/QMS studies confirmed that their decomposition took place mainly as a depolymerization process combined with a subsequent breaking of the bonds in the resulting monomer/s at higher temperatures, which led to the formation of the gases with lower molecular masses. The main decomposition products emitted in an inert atmosphere were benzyl methacrylate, citronellyl methacrylate, 2-methylpropenal, citronellal and higher molecular mass compounds formed as a result of radical reactions between intermediate volatile products. In turn, under oxidizing conditions, as volatiles, benzyl methacrylate, citronellyl methacrylate, 2-methylpropenal, citronellal and small amounts of inorganic gases (CO, CO2, H2O) as a result of depolymerization and some combustion processes of the residues were indicated.

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“…Furthermore, several bio-based linear aliphatic, aromatic, and cycloaliphatic compounds have been successfully converted into (meth)acrylates that are interesting monomers for manufacturing of polymers. [7][8][9][10][11][12][13][14] Among these bio-based monomers is a new dimethacrylate synthesized in three steps as shown in Scheme 1. The synthesis starts with esterification of oleic acid with ethylene glycol, it continues with epoxidation of the two double bonds of the ethylene dioleate, and ring opening reaction of the resulting diepoxy compound with methacrylic acid is the final step.…”

Section: Introductionmentioning

confidence: 99%

Crosslinked Polymers Based on Monomers Derived from Renewable Resources and Their Application Potential

Strehmel

2023

Preprint

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Possible structural variation of a bio-based dimethacrylate derived from oleic acid and ethylene glycol is discussed as well as sources to obtain the starting material for manufacturing of this monomer. Furthermore, aspects influencing the transfer of a newly developed product or further scientific result to application are included into the discussion as well focusing to manufacturing processes and development of a new product for the market.

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A Green Step to New Monomers and Their Polymerization

Cited by 7 publications

References 34 publications

Manufacturing and photocrosslinking of a new bio‐based dimethacrylate resulting in hydrophobic crosslinked films

Manufacturing and photocrosslinking of a new bio‐based dimethacrylate resulting in hydrophobic crosslinked films

TG/DSC/FTIR/QMS analysis of environmentally friendly poly(citronellyl methacrylate)-co-poly(benzyl methacrylate) copolymers

Crosslinked Polymers Based on Monomers Derived from Renewable Resources and Their Application Potential

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