Activity of the furfuryl ring in the free radical polymerization of acrylic monomers

Davidenko, Natalia; Zaldívar, Dionisio; Péniche, Carlos; Sastre, R.; Román, Julio San

doi:10.1002/(sici)1099-0518(19960930)34:13<2759::aid-pola21>3.3.co;2-h

Cited by 8 publications

(13 citation statements)

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“…Furfuryl methacrylate (FMA) is an interesting monomer because of the presence of its reactive furfuryl pendant group. FMA is of particular interest in clinical applications, as a biomaterial (bone cement), and in coating and adhesive applications due to its low polymerization shrinkage 5. Perez et al6 reported that methyl methacrylate (MMA) can be substituted with FMA as a traditional monomer in the preparation of biomaterials, because it has a lower volume shrinkage and a lower heat of polymerization than MMA.…”

Section: Introductionmentioning

confidence: 99%

Atom‐Transfer Radical Copolymerization of Furfuryl Methacrylate (FMA) and Methyl Methacrylate (MMA): A Thermally‐Amendable Copolymer

Kavitha

Singha

2007

Macro Chemistry & Physics

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Polymers of furfuryl methacrylate (FMA) are interesting materials because of the presence of the furfuryl group as the reactive diene functionality in the pendent group. Copolymers of FMA and MMA were prepared using atom‐transfer radical polymerization (ATRP) catalyzed by CuCl, in combination with HMTETA as a ligand at 90 °C. It was very difficult to prepare by conventional radical polymerization because of several side reactions involving the reactive diene group. The copolymer composition was calculated using 1H NMR studies. The reactivity ratios of FMA and MMA (r1 and r2) were determined using the Finemann‐Ross and Kelen‐Tudos linearization methods. The reactivity ratios obtained were r1 = 1.56 and r2 = 0.56. Diels‐Alder chemistry was carried out using the reactive diene of the copolymers and a maleimide as the dienophile. Interestingly, the resultant material was observed to be thermo‐reversible as evidenced by FT‐IR spectroscopy and DSC studies.

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Section: Introductionmentioning

confidence: 99%

Atom‐Transfer Radical Copolymerization of Furfuryl Methacrylate (FMA) and Methyl Methacrylate (MMA): A Thermally‐Amendable Copolymer

Kavitha

Singha

2007

Macro Chemistry & Physics

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“…On the other hand, the validity of these constants are corroborated statistically by means of the fit goodness test (Table 3). 32 Values of χ 2 ( χ

_{calc}^{2}

) were calculated using experimental data from ref 33. while the theoretical ones ( χ

_{theo}^{2}

) were extracted from a table of distribution of χ 2 for m − 1 = 16 degrees of freedom with 1 − α f = 0.95 confidence level.…”

Section: Analysis and Discussion Of Numerical Resultsmentioning

confidence: 99%

“…The exotherms obtained by this method allowed the monomer conversion to be estimated at a given point in time. The kinetic curves conversion vs time of FA polymerization at different light intensities were obtained as it is reported in a publication 33…”

Section: Experimental Partmentioning

confidence: 99%

Mathematical Modeling of the Bulk Photopolymerization of Furfuryl Acrylate

Lange

Davidenko

Rieumont

et al. 2004

Macro Theory & Simulations

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Summary: Experimental data for the photopolymerization of furfuryl acrylate (FA) conformed satisfactorily to the kinetics model proposed for the photopolymerization of furfuryl methacrylate (FM). This model allowed the kinetic constants of the basic steps of the studied mechanism, namely propagation, degradative transfer, re‐initiation and cross‐termination, to be determined. The calculated values of these constants were in agreement with the chemical nature of FA. For each of these constants, the confidence intervals were determined, and the statistical dependence between some of them was analyzed using the ellipse error method. The equations of moments of the distribution of molecular sizes of the primary chains in the network with order greater than one were developed to describe different molecular averages, such as weight‐average chain length and size‐average heterogeneity of the primary chains. The results found for the monomer conversion, the cross‐link degree and number‐average length of the primary chains of the network for FA were compared with those obtained for FM, and it was shown that the process of polymerization of the former monomer was more retarded and produced gels with a greater degree of cross‐linking than the latter as expected.

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“…At higher reaction time, there is a possibility of chain transfer reaction that produces oligomers. So, the formation of oligomers predominates due to polymer chain scission, thereby reducing the percent yield of the reaction . As a result, the optimum polymerization condition was set to 20 h reaction time at RT.…”

Section: Resultsmentioning

confidence: 99%

Sustainable self‐healing elastomers with thermoreversible network derived from biomass via emulsion polymerization

Sahu

Bhowmick

2019

J. Polym. Sci. Part A: Polym. Chem.

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Motivated by the growing demand for greener and sustainable polymer systems, self‐healing elastomers were prepared by emulsion polymerization of terpene and furfural‐based monomers. Both the method and the monomers were green and sustainable. The synthesized copolymers showed molecular weights between 59,080 and 84,210 Da and glass‐transition temperature (Tg) between −25 and −40 °C, implying rubbery properties. A set of one‐dimensional (1D) and two‐dimensional (2D) NMR spectroscopy supported the formation of the copolymer and nuclear spin–spin coupling in the copolymer. Reactivity ratios were determined by conventional linear method. A thermoreversible network was achieved for the first time by reacting the furan‐based polymer with bismaleimide (BM) as a crosslinker, via a Diels−Alder (DA) coupling reaction. The reversible nature of the polymer network was evidenced from infrared and NMR spectroscopy. The thermoreversible character of the DA crosslinked adduct was confirmed by applying retro‐DA reaction (observed in differential scanning calorimeter [DSC] analysis) and mechanical recovery was verified by repeated heating and cooling cycles. The network polymers displayed excellent self‐healing ability, triggered by heating at 130 °C for 4–12 h, when their scratched surface was screened by microscopic visualization. The healing efficiency of the crosslinked DA‐adduct was calculated as 78%, using atomic force microscopy. This work provides a green and efficient approach to prepare new green and functional materials. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 738–751

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Activity of the furfuryl ring in the free radical polymerization of acrylic monomers

Cited by 8 publications

References 0 publications

Atom‐Transfer Radical Copolymerization of Furfuryl Methacrylate (FMA) and Methyl Methacrylate (MMA): A Thermally‐Amendable Copolymer

Atom‐Transfer Radical Copolymerization of Furfuryl Methacrylate (FMA) and Methyl Methacrylate (MMA): A Thermally‐Amendable Copolymer

Mathematical Modeling of the Bulk Photopolymerization of Furfuryl Acrylate

Sustainable self‐healing elastomers with thermoreversible network derived from biomass via emulsion polymerization

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