Copolymerization of ethyl ?-(hydroxymethyl)acrylate with maleimide and characterization of the resulting copolymer

Jia, Xinqiao; Pang, Yanwan; Huang, Junlian

doi:10.1002/(sici)1099-0518(199806)36:8<1291::aid-pola12>3.0.co;2-1

Cited by 13 publications

(6 citation statements)

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“…One possible explanation is that the 3‐furoic acid forms a conjugated electron poor vinyl bond, which may be susceptible to nucleophilic attack. It has been well documented that maleimides and vinyl or acrylate species react readily with one another 20, 21…”

Section: Resultsmentioning

confidence: 99%

Kinetic and thermodynamic measurements for the facile property prediction of diels–alder‐conjugated material behavior

et al. 2012

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The Diels–Alder (DA) reaction between maleimide and furan moieties possessing various substitutions was performed as a means for developing predictive capabilities for temperature and conversion‐dependent material properties in networks comprised of DA moieties. Using HNMR spectroscopy, the reactions of maleimide‐ and furan‐containing molecules further functionalized with carboxylic acids were monitored to ascertain the impact that substitutional changes had on the thermodynamic and kinetic behavior of the DA reaction. The reaction rate and equilibrium conversion of the furan and maleimide increased when the carboxylic acid functional group directly connected to the furan ring was moved from the two to the three position. When an aliphatic two‐carbon spacer was used, such that the π‐electrons of the carboxylic acid and furan were no longer conjugated, the reaction rate increased further. We also report the reactivity effect on the distance between the carboxylic acid functional group and the maleimide, which yielded little impact on the reaction rate but exhibited increased equilibrium conversion with increasing distance. Additionally, the impact on the kinetic and thermodynamic properties of coupling the carboxylic acid to another molecule, tert‐butyl glycine, was also determined. When the carboxylic acid was coupled to an amine, the DA reaction between the furan and maleimide was generally found to have similar kinetic and thermodynamic behavior as compared to their uncoupled, carboxylic acid equivalents. Thus, the characterized and tabulated kinetic and thermodynamic data presented herein enables the prediction of a broad set of temperature‐dependent chemical and material properties. Finally, we discuss practical limitations and nuances of the DA reaction, such as the potential for the maleimide to ring‐open in aqueous media via hydrolysis. © 2012 American Institute of Chemical Engineers AIChE J, 2012

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Section: Resultsmentioning

confidence: 99%

Kinetic and thermodynamic measurements for the facile property prediction of diels–alder‐conjugated material behavior

et al. 2012

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“…From thermograms, the temperatures for initial decomposition T i and final decomposition T f for each step is determined by drawing appropriate tangents and taking their point of intersection [13,42]. The viscosity measurement was carried out in DMF at 30…”

Section: Measurementsmentioning

confidence: 99%

Radical polymerization of N-(4-butoxycarbonylphenyl)maleimide, its co-polymerization with methyl methacrylate, styrene and acrylonitrile, and the properties of the resulting polymers

Oswal

Chapaneri

Malek

2007

Designed Monomers and Polymers

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Abstract-Co-polymers were synthesized from free radical co-polymerization of methyl methacrylate (MMA), styrene (ST) and acrylonitrile (AN) with N -(4-butoxycarbonylphenyl)maleimide (BCPM), using benzyl peroxide (BPO) as an initiator and DMF as a solvent at 85 • C. A series of co-polymers of MMA, ST and AN with BCPM was prepared using different feed ratio of comonomers. The thermo-stabilities and physical properties of the polymer samples obtained have been described. The values of monomer reactivity ratios r 1 and r 2 determined by Fineman-Ross and Kelen-Tudos methods are 0.28 and 0.90 in BCPM/MMA, 0.20 and 0.39 in BCPM/ST and 0.51 and 1.23 in BCPM/AN systems. Alfrey-Price Q and e values for BCPM are Q = 1.39 and e = 1.57 in BCPM/MMA, Q = 2.53 and e = 2.15 in BCPM/ST and Q = 1.11 and e = 1.89 in BCPM/AN systems.

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“…Principally, the 1,2‐disubstituted vinyl group of maleimides is sterically hindered towards radical homopolymerization compared with 1‐ or 1,1‐substituted vinyl monomers like (meth)acryl‐derivatives or styrene. Accordingly, electron‐poor N ‐phenyl‐maleimides tend to undergo alternating copolymerization with relatively electron‐rich comonomers like styrene or N ‐vinylpyrrolidone in an organic medium . Copolymers containing N‐substituted maleimides in the main chain are of practical interest in respect to elevated thermostability or glass transition temperatures of polymeric materials …”

Section: Introductionmentioning

confidence: 99%

Influence of β‐Cyclodextrin on the Free‐Radical Copolymerization of N‐(4‐Methylphenyl)maleimide with N‐Vinylpyrrolidone in Water

Schönenberg

Ritter

2013

Macro Chemistry & Physics

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Randomly methylated β -cyclodextrin (me-β -CD) is used to include the hydrophobic monomer N -(4-methylphenyl)maleimide (MPM) ( 1 ) yielding the corresponding water-soluble host-guest structure 1a . Free-radical copolymerization of 1a with N -vinylpyrrolidone (NVP) ( 2 ) is performed and the reactivity ratios r 1 and r 2 are determined: 0.24 ± 0.03 ( r 2 ) and 1.10 ± 0.05 ( r 1a ). This indicates a preferred incorporation of complexed maleimide into the copolymer chain. In contrast to that, the copolymerization of the uncomplexed monomers 1 and 2 is carried out using organic solvent (DMF/H 2 O) showing reactivity ratios corresponding to nearly alternating copolymerization ( r 2 = 0.09 ± 0.02; r 1 = 0.34 ± 0.03).

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Copolymerization of ethyl ?-(hydroxymethyl)acrylate with maleimide and characterization of the resulting copolymer

Cited by 13 publications

References 4 publications

Kinetic and thermodynamic measurements for the facile property prediction of diels–alder‐conjugated material behavior

Kinetic and thermodynamic measurements for the facile property prediction of diels–alder‐conjugated material behavior

Radical polymerization of N-(4-butoxycarbonylphenyl)maleimide, its co-polymerization with methyl methacrylate, styrene and acrylonitrile, and the properties of the resulting polymers

Influence of β‐Cyclodextrin on the Free‐Radical Copolymerization of N‐(4‐Methylphenyl)maleimide with N‐Vinylpyrrolidone in Water

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