Studies on the polymerization of bifunctional monomers. XVII. Cyclopolymerization of malealdehyde and the structure of the polymer

Aso, Chuji; Kunitake, Toyoki; Miura, Masanobu; Koyama, Katsuhisa

doi:10.1002/macp.1968.021170113

Cited by 6 publications

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“…(l)] as was the case for some aliphat,ic dialdehydes. [4][5][6] Thus, differences in polymerization behavior which would probably arise between the ortho isomer and the meh and para isomers were of particular interest. The results obtained in the present investigation that copolymers containing more than 50 mole-yo of the o-phthdaldehyde unit were formed in the copolymerization with styrene led us to the finding that o-phthalaldehyde by itself could yield the cyclopolymer.…”

Section: Introductionmentioning

confidence: 99%

Polymerization of aromatic aldehydes. IV. Cationic copolymerization of phthalaldehyde isomers and styrene

Aso

Tagami

Kunitake

1970

J. Polym. Sci. A‐1 Polym. Chem.

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Copolymerizations of three phthalaldehyde isomers (M2) with styrene (M1) were carried out in methylene chloride or in toluene with BF3OEt2 catalyst. The monomer reactivity ratios were r1 = 0.77, r2 = 0 for the meta isomer and r1 = 0.60, r2 = 0 for the para isomer. The second aldehyde group of both isomers did not participate in polymerization and acted simply as the electron‐withdrawing group, thus reducing the cationic reactivity of these monomers. Copolymerization behaviors of the ortho isomer (o‐PhA) were quite different between 0°C and −78°C. At −78°C, o‐PhA preferentially polymerized to yield “living” cyclopolymers, until an equilibrium concentration of o‐PhA monomer was reached. Then, styrene propagated from the living terminal rather slowly. The block structure of the copolymer was confirmed by the chemical and spectroscopic means. In the copolymerization at 0°C, the o‐PhA unit in copolymer consisted both of cyclized and uncyclized units. This copolymer seemed to contain short o‐PhA sequences. The variation of the o‐PhA‐St copolymer structure with the polymerization temperature was explained on the basis of whether the polymerization was carried out above or below the ceiling temperature (−43°C) of the homopolymerization of o‐PhA.

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Section: Introductionmentioning

confidence: 99%

Polymerization of aromatic aldehydes. IV. Cationic copolymerization of phthalaldehyde isomers and styrene

Aso

Tagami

Kunitake

1970

J. Polym. Sci. A‐1 Polym. Chem.

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Titanium(IV) Chloride-Triethylaluminum

Takahashi

Suzuki

2001

Encyclopedia of Reagents for Organic Synthesis

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Polymerization ability of cis‐ and trans‐4,5‐epoxy‐2‐pentenal with ionic and free radical initiators. Cyclopolymerization of the cis isomer

Yokoyama

Hall

1982

J. Polym. Sci. Polym. Chem. Ed.

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SynopsisThe behavior of the readily available cis-(1) and trans-(2) 4,5-epoxy-2-penten& toward classical cationic, anionic, and free radical initiators has been examined. Only the cationic polymerization of 1 gave soluble polymer of moderate molecular weights. This polymer possessed predominantly the cyclopolymerized furanose structure 12. Cationic initiation of 2 and anionic initiation of both 1 and 2 gave only crosslinked materials, and free radical initiators with 1 and 2 gave no polymer. EXPERIMENTALInstrumentation lH-NMR spectra were obtained using a Varian-T6O and a Bruker WM-250Multinuclear FT spectrometer. Infrared spectra were recorded using a Perkin-Elmer 710A spectrophotometer. Elemental analyses were performed by the University of Arizona Analytical Center (Tucson, Arizona). The numberaverage molecular weight of the polymers was determined in dichloromethane at 37OC using a Hewlett-Packard vapor pressure osmometer model 302B. Monomers cis-(I) and trans-4,5-Epoxy-Z-Pentenal.(2)'Commercial (Tridom-Fluka) cisand tram-4,5-epoxy-2-pentenal(90% pure) were purified by using a spinning band distillation column (1 m) of the Perkin-Elmer Manufacturing Corp. The purity of monomer was checked by lH-NMR spectroscopy (>98% for 1 and >99% for 2). bp 59-60°C/6 mm Hg for 1 and 52OC/5 mm Hg for 2; IR (CCk) for 1: 3050 (VC-H, CH2 of epoxy ring, m), 3020 (VC-H, CH of epoxy ring and CH=CH, w), 2780 (w), 2755 (m), and 2735 (m)

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Studies on the polymerization of bifunctional monomers. XVII. Cyclopolymerization of malealdehyde and the structure of the polymer

Cited by 6 publications

References 6 publications

Polymerization of aromatic aldehydes. IV. Cationic copolymerization of phthalaldehyde isomers and styrene

Polymerization of aromatic aldehydes. IV. Cationic copolymerization of phthalaldehyde isomers and styrene

Titanium(IV) Chloride-Triethylaluminum

Polymerization ability of cis‐ and trans‐4,5‐epoxy‐2‐pentenal with ionic and free radical initiators. Cyclopolymerization of the cis isomer

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