Synthesis and Polymerization of N-Arylitaconimides: Free Radically and Anionic ally

Pyriadi, Thanun M.; Fraih, M.

doi:10.1080/00222338208074415

Cited by 21 publications

(12 citation statements)

References 11 publications

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“…It is interesting to mention here that two isomeric N-substituted citraconamic acids might form from the reaction of primary amines with citracon anhydride. 3 Attempts to separate the two isomers were not made since both isomers after dehydration would give a single isomer. Dehydration of the prepared citraconamic acids to the corresponding imides was performed by fusion of the amic acids.…”

Section: Three Isomeric N-(hydroxyphenyl)citraconamic Acids Namely Omentioning

confidence: 99%

“…Internsic viscosities of the soluble polyacrylates were in the range 0.136 -0.54 dL/g using CHCl 3 or DMF as solvents (Table V). The prepared polyacrylates were cured using two methods, namely, by prolonged heating at 200°C for 3 h in an oven or by addition of the well-known crosslinking agent N,N-p-phenylenedimaleimide 15 and trace amounts of AIBN to the polymer in THF followed by heating the mixture at 80°C for 2 h. In both methods a tough, insoluble, and infusible polymer was obtained.…”

Section: Five Of the N-(hydroxyphenyl)citraconimides Ofmentioning

confidence: 99%

“…3 However, N-substituted citraconimides did not polymerize free radically or anionically. 4 It seems that steric hindrance from the methyl group substituted on the vinyl is retarding the propagation steps of chain formation.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, polymerization, and curing ofN-substituted citraconimidyl acrylate

Pyriadi

Alazawi

1999

J. Polym. Sci. A Polym. Chem.

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Section: Three Isomeric N-(hydroxyphenyl)citraconamic Acids Namely Omentioning

confidence: 99%

Section: Five Of the N-(hydroxyphenyl)citraconimides Ofmentioning

confidence: 99%

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Synthesis, polymerization, and curing ofN-substituted citraconimidyl acrylate

Pyriadi

Alazawi

1999

J. Polym. Sci. A Polym. Chem.

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“…Systematic studies on the reactivity of disubstituted ethylene monomers, especially of five‐membered cyclic imides, ie N ‐substituted maleimides and isomaleimides,1–14 citraconimides15–17 or itaconimides,18–21 in free radical and anionic polymerization have been carried out by a number of research groups. Polymerization takes place by opening of the double bond and head‐to‐tail coupling to obtain polymers of low molecular weight.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and polymerization of anthracene‐based itaconimides

Grigoraş¹,

Colotin²,

Antonoaia³

2004

Polymer International

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Two new anthracene‐based itaconimides, ie N‐(1‐ and 2‐anthryl) itaconimides, were synthesized by the reaction of aromatic amines with itaconic anhydride, followed by itaconamic acid imidization. The same reaction failed in the case of anthracene‐ring substitution at the position 9′. Radical and thermal polymerization of N‐(1‐ and 2‐anthryl) itaconimides led to polymers with anthracene pendant groups. No self‐polymerization by Diels–Alder cycloaddition of the itaconic function (dienophile) and anthracene nucleus (diene) was observed, as is the case for N‐(anthryl) maleimides and citraconimides. Copyright © 2004 Society of Chemical Industry

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“…That is, the MBPI monomer containing two allylic hydrogens can cause chain transfer reaction. 3 There were no olefinic protons in the spectra for poly(MBPI). Thus, ordinary vinylidene polymerizations took place.…”

Section: Mbpimentioning

confidence: 99%

Synthesis and Polymerization of Optically Active N-[4-N′-(α-Methylbenzyl)aminocarbonylphenyl] itaconimide

Oishi

Kawamoto

1994

Polym J

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ABSTRACT:A new type of optically active N-[4-N'-(IX-methylbenzyl)aminocarbonylphenyl]-itaconimide (MBPI) was synthesized from itaconic anhydride, p-aminobenzoic acid, and (R)-1X-methylbenzylamine. The radical homopolymerization of MBPI was performed in tetrahydrofuran (THF) at 60--I 30°C for 22 h to give optically active polymers having [ IX Ji 5 = -46.6 to -51.8°. Anionic polymerizations of MBPI with n-butyllithium in THF and N,N-dimethylformamide were performed. But the yields were quite small. Radical copolymerizations of MBPI (Mi) were performed with styrene (ST, M 2), methyl methacrylate (MMA, M 2 ), or indene (ID, M2) in THF at 70°C. Monomer reactivity ratios (r1, r2) and Alfrey-Price Q-e values were calculated. Chiroptical properties of the polymers and copolymers were also investigated.KEY WORDS Optically Active ltaconimide / Radical Polymerization / Monomer Reactivity Ratio/ Q--e values/ Chiroptical Properties/ Asymmetric Perturbation / There have been some reports on the polymerization and copolymerization of Nsubstituted itaconimides (Ril). 1 -4 However, no studies on polymerization of optically active RII have been made. Thus, polymerization reactivity and chiroptical property of RII including a chiral group were of interest to us. We reported that radical copolymerizations of optical active N-[4-N'-(a-metbylbenzyl)aminocarbonylphenyl]maleimide [(R)-MBPM5 and (S)-MBPM 6 ] were performed with styrene (ST) or methyl methacrylate (MMA). In these systems, relationships between specific rotation of the copolymers and content (wt%) of chiral MBPM monomeric unit indicated great deviation from linearity. This deviation could be attributed to (1) asymmetric induction into the copolymer main chain and/or (2) asymmetric perturbation of chromophore of the chiral side chain.* To whom all correspondence should be addressed. 920In this paper, a novel, optically active N-[ 4-N' -( a-methyl-benzyl)aminocarbonylphenyl]itaconimide (MBPI), is prepared from itaconic anhydride, p-aminobenzoic acid, and (R)-( + )-a-methylbenzylamine. MBPI is polymerized and copolymerized with styrene, methyl methacrylate, and indene (ID) in the presence of radical initiators. From the results, monomer reactivity ratios and Q-e values were determined. Based on specific rotations and molecular ellipticities of the copolymers, asymmetric induction into the copolymer main chain and asymmetric perturbation of chromophore of the chiral side chain are discussed and compared with that of (R)-MBPM 5 containing the same N-substituent as MBPI. MBPI was also polymerized with an anionic initiator.

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Synthesis and Polymerization of N-Arylitaconimides: Free Radically and Anionic ally

Cited by 21 publications

References 11 publications

Synthesis, polymerization, and curing ofN-substituted citraconimidyl acrylate

Synthesis, polymerization, and curing ofN-substituted citraconimidyl acrylate

Synthesis and polymerization of anthracene‐based itaconimides

Synthesis and Polymerization of Optically Active N-[4-N′-(α-Methylbenzyl)aminocarbonylphenyl] itaconimide

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