Complex‐radical terpolymerization of phenanthrene, maleic anhydride, and <i>trans</i>‐stilbene

Baştürkmen, Meray; Rzaev, Zakır M. O.; Akovali, G.; Kisakürek, Duygu

doi:10.1002/pola.1995.080330102

Cited by 9 publications

(4 citation statements)

References 18 publications

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“…According to the literature,31–33 vinyl ether monomers usually exhibit negative values for e parameter, which enhances the electron‐donating character of allyl monomers. Maleic anhydride (MA)34–36 shows positive e value of about 2.3. Furthermore, MA and vinyl ethers show Q values of about 0.2 and 0.1, respectively (0.1 is an average value as the Q value of the vinyl ethers may vary with the substituent).…”

Section: Resultsmentioning

confidence: 99%

Novel dialkyl vinyl ether phosphonate monomers: Their synthesis and alternated radical copolymerizations with electron‐accepting monomers

Iftene

David

Boutevin

et al. 2012

J. Polym. Sci. A Polym. Chem.

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Three new vinyl ether monomers containing phosphonate moieties were synthesized from transetherification reaction. We showed that the yield was dependent on the spacer length between the vinyl oxy group and the phosphonate moieties: when the spacer is a single methylene side reaction may occur, leading to the formation of acetal compounds. Free-radical copolymerizations of phosphonate-containing vinyl ether monomers with maleic anhydride were carried out, leading to alternated copolymers of rather low molecular weights (from 1000 to 7000 g/mol). Both gel permeation chromatography and 31 P NMR analyses enhanced possible intramolecular transfer reactions occurring from the phosphonate moieties. Kinetic investigation showed that the electron-withdrawing character of the phosphonate moieties tends to decrease the rate of copolymerization. Nevertheless, almost complete monomers conversion was reached after 30 min of reaction with dimethyl vinyloxyethylphosphonate (VEC 2 PMe). Then, radical copolymerization of VEC 2 PMe with a series of electron-accepting monomers, that is, dibutyl maleate, dibutylitaconate, itaconic anhydride, butyl maleimide, and methyl maleimide, led to a series of alternated copolymers. From kinetic investigation, we showed that the higher the electron-accepting effect, the faster the vinyl ether consumption and the higher the molecular weights.

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Section: Resultsmentioning

confidence: 99%

Novel dialkyl vinyl ether phosphonate monomers: Their synthesis and alternated radical copolymerizations with electron‐accepting monomers

Iftene

David

Boutevin

et al. 2012

J. Polym. Sci. A Polym. Chem.

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“…The compositions of the copolymers synthesized using various monomer feed ratios were determined by known FTIR [26,27] and NMR [28] methods and were achieved by comparing the absorption bands and the integrals of the methyne and nitrile groups regions in the spectra of VIM and AN units, respectively. Molar fractions of the comonomer units (m 1 and m 2 ) in poly(VIM-co-AN)s using 1 H NMR analysis data were calculated according to Equation (1) and (2).…”

Section: Measurementsmentioning

confidence: 99%

Synthesis and Characterization of Poly(N‐vinylimidazole‐co‐acrylonitrile) and Determination of Monomer Reactivity Ratios

Pekel

Rzaev

Güven

2004

Macro Chemistry & Physics

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Summary: Radical‐initiated solution copolymerization of N‐vinylimidazole (VIM) and acrylonitrile (AN) was carried out with 2,2′‐azobisisobutyronitrile (AIBN) as an initiator in benzene at 70 °C in nitrogen atmosphere. The structure and composition of synthesized copolymers for a wide range of monomer feeds were determined by FTIR, 1H and 13C NMR spectroscopy with the aid of recorded analytical absorption bands for VIM (667 cm−1, CN of imidazole ring) and AN (2 242 cm−1, CN group), as well as by using the areas of proton and carbon atom signals from corresponding functional groups of monomer units. Monomer reactivity ratios for VIM (M1)‐AN (M2) pair were determined by nonlinear regression (NLR), Kelen–Tüdös (KT) and Fineman–Ross (FR) methods. They were found to be r1 = 0.24 and r2 = 0.15 for the NLR method, r1 = 0.22 and r2 = 0.094 for the KT method, and r1 = 0.24 and r2 = 0.12 for the FR method, respectively. The relatively high activity observed of VIM growing macroradical and the results of FTIR and 1H NMR structural analysis of copolymers suggest the formation of complexed linkages between monomers and growing radicals in chain propagation reactions. Similar complexation between monomer–comonomer units in the structure of formed macromolecules showed an increase in isotactic triad fractions in the copolymer.Complex formation between the imidazole ring and nitrile group in both the monomer mixture and chain growing reactions.imageComplex formation between the imidazole ring and nitrile group in both the monomer mixture and chain growing reactions.

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“…In several publications some attention has been focused on the study of monomer charge transfer complexes (CTC) effect in radical terpolymerization by using following donor-acceptor ternary systems: maleic anhydride(MA)-styrene(St)-methacrylates [9], MA-St (or trans-stilbene)-N-phenylmaleimide [10,11], MA-St-citraconic anhydride [12], MA-St-vinylacetate [13], MA-trans-stilbene-phenanthrene [11,14], MAallyl-glycigyl ether-methyl methacrylate [15] and other systems containing MA [5,11]. Similar effects were observed in radical copolymerization of bifunctional monomers (allylcinnamate, monoallylmaleate, Nallylmaleimides, allylmethacrylate and etc.)…”

Section: Introductionmentioning

confidence: 99%

Complex-Radical Terpolymerization of Maleic Anhydride (Styrene), Allyl Propionate and Methyl Methacrylate

et al. 2016

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<p>The radical terpolymerization reactions of the acceptor-donor-acceptor and donor-acceptor-donor systems, maleic anhydride (MA)-allyl propionate (AP)-methyl methacrylate (MMA) and styrene (St)-MMA-AP, had been studied. The terpolymerizations were carried out in methyl ethyl ketone at 60-75 °C in the presence of 2,2’-azoisobutyronitrile (ABIN) used as the initiator. Some kinetic parameters and copolymerization constants - for both, system were determined by dilatometric and Kelen-Tudos or Seiner-Lift methods. The obtained results are discussed in terms of the free monomer and complex chain growth models. It is shown that terpolymerization was carried out at a stage close to binary copolymerization of MA...AP complex with free MMA and St...MMA complex with AP in the both studied system, respectively. These systems are also used as model for interpretation of cyclocopolymerization mechanism in allyl methactylate-MA (or St) system. DTA and TGA analyses indicated the relatively high thermal stability of St-MMA-AP terpolymer. It is shown that this terpolymer decomposes through a one-step reaction at 310 °C, however MA-AP-MMA terpolymer decomposes through a multi-step reactions at 150, 260 and 310 °C.</p>

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Complex‐radical terpolymerization of phenanthrene, maleic anhydride, and trans‐stilbene

Cited by 9 publications

References 18 publications

Novel dialkyl vinyl ether phosphonate monomers: Their synthesis and alternated radical copolymerizations with electron‐accepting monomers

Novel dialkyl vinyl ether phosphonate monomers: Their synthesis and alternated radical copolymerizations with electron‐accepting monomers

Synthesis and Characterization of Poly(N‐vinylimidazole‐co‐acrylonitrile) and Determination of Monomer Reactivity Ratios

Complex-Radical Terpolymerization of Maleic Anhydride (Styrene), Allyl Propionate and Methyl Methacrylate

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