New Functional Maleimides and Citraconimides for Amide, Urea or Parabanic Aromatic Bismaleimides

Găină, Constantin; Gaina, Viorica

doi:10.1163/156855508x332478

Cited by 9 publications

(8 citation statements)

References 17 publications

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“…After the furan-grafting reaction, the intermediate products (FGSB0 and FG0) were further reacted with BM using DA chemistry. The presence of BM in the products was verified by the appearance of the peak at an absorption band of 1510 cm −1 , which corresponds to CH = CH of the BM aromatic ring’s stretching vibrations (υCH=CH) as observed in Figure 1 a for FGSB1 and Figure 1 b for FG1 [ 34 ]. The DA adduct (C-O-C, Scheme 1 c), however, is only present in FG1, as shown from the shoulder around the absorption band of 1186 cm −1 (δDAring, Figure 1 a) [ 13 , 18 , 35 ].…”

Section: Resultsmentioning

confidence: 99%

Cross-Linking of Polypropylene via the Diels–Alder Reaction

et al. 2022

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In this work, the possibility of preparing cross-linked polypropylene (PP) via Diels–Alder (DA) chemistry is explored. The overall strategy involves reaction of maleated polypropylene (the starting material), furfuryl amine (FFA), and bismaleimide (BM) as the cross-linking agent. The occurrence of reversible cross-linking was studied by checking the presence of relevant peaks in FTIR spectra, i.e., CH out-of-plane bending vibrations of the furan ring’s peak (γCH) at an absorption band of 730–734 cm−1, CH=CH of the BM aromatic ring’s stretching vibrations (υCH=CH) at an absorption band of 1510 cm−1, and the DA adduct (C-O-C, δDAring) at an absorption band of 1186 cm−1. In agreement with the spectroscopic characterization, the presence of a cross-linked network is also confirmed by rheology, namely the higher storage modulus (G′) compared with loss modulus (G″) value (G′ >> G″), as obtained via temperature sweep. Both the maleic anhydride (MA) content as well as the annealing temperature (50 °C and 120 °C) favor the DA reaction, while only partial de-cross-linking (retro DA) is observed at the higher temperature range of 150–200 °C. In addition, the products show higher mechanical robustness and thermal stability compared to the starting material.

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Section: Resultsmentioning

confidence: 99%

Cross-Linking of Polypropylene via the Diels–Alder Reaction

et al. 2022

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“…MMPI, yield 83%. 1 H NMR (CDCl 3 , TMS), δ (ppm): 7.44–7.40 (t, 1H, J = 8.1, 8.1 Hz, aromatic proton), 7.24–7.22 (m, 1H, aromatic proton), 7.15–7.14 (t, 1H, J = 2.0, 2.0 Hz, aromatic proton), 7.12–7.10 (m, 1H, aromatic proton), 6.88 (s, 2H, ─CH═CH─).…”

Section: Methodsmentioning

confidence: 99%

“…The easy introduction of maleimide moieties in common polymer chains, that is, those easily synthesized or commercially available, would provide powerful scaffolds and building blocks for the rapid construction of macromonomers and block copolymers. For that purpose, we focused our attention on p ‐maleimidophenyl isocyanate ( PMPI ) [Fig. (a)] as a modification agent, which can be used to directly transform the hydroxy groups in polymer chains into reactive maleimide groups via a one‐pot reaction with the reactive isocyanate group.…”

Section: Introductionmentioning

confidence: 99%

Maleimidophenyl isocyanates as postpolymerization modification agents and their applications in the synthesis of block copolymers

Takashima

Kida

Aoki

et al. 2019

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

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The maleimide structure is highly reactive, exemplified by thiol–ene click reactions with thiols and Diels–Alder reactions with furans. Although postpolymerization modifications and macromolecular conjugations involving maleimide units have been widely studied, mostly due to their selectivity and high reactivity, little has been reported on the one‐pot postpolymerization introduction of maleimides in polymer chains. Herein, we report p‐maleimidophenyl isocyanate and its derivatives as modification agents to introduce maleimide moieties by reaction with hydroxy groups into polymer chains. The high reactivity of the resulting modification agents and of the corresponding maleimide structures once inserted in the polymer chains was examined by studying their reaction kinetics. Furthermore, these modification agents were successfully applied to the synthesis of macromonomers for graft polymerization and various block copolymers, with, for example, AB‐type, star‐shaped, and H‐shaped architectures. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 2396–2406

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“…Compounds 1(a-b) were synthesized by the reaction of maleic anhydride with 3-or 4-aminobenzoic acid, then with thionyl chloride, yielding in 3 (4)- (benzoylchloride) maleimide, as presented in literature [16]. Compounds 1(c-d) were obtained starting from 1(a-b) that were treated with sodium azide, resulting in 3(4)-maleimidobenzoic azides which, by Curtius decomposition, lead to 3(4)-maleimidobenzoic isocyanates (Scheme 5).…”

Section: Reagents and Materialsmentioning

confidence: 99%

Synthesis of new polyimides with 1,2,3-triazole units

Găină¹,

Gaina²

2008

E-Polymers

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New polyimides with 1,2,3-triazole units were prepared by click reaction of α,α'-bis(azidosuccinimide)s with bispropargyl monomers or AB-monomers containing azide and propargyl groups. The α,α'-bis(azidosuccinimide)s were obtained by the addition of hydrazoic acid to bismaleimide monomers. The structure of monomers and polymers was confirmed by FTIR and 1 H-NMR spectroscopy and all synthesized compounds were characterized through thermal methods.

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New Functional Maleimides and Citraconimides for Amide, Urea or Parabanic Aromatic Bismaleimides

Cited by 9 publications

References 17 publications

Cross-Linking of Polypropylene via the Diels–Alder Reaction

Cross-Linking of Polypropylene via the Diels–Alder Reaction

Maleimidophenyl isocyanates as postpolymerization modification agents and their applications in the synthesis of block copolymers

Synthesis of new polyimides with 1,2,3-triazole units

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