The effect of phenol and cresols on the polymerization of styrene

Minoura, Yuji; Yasumoto, Noboru; Ishii, Tatsuya

doi:10.1002/macp.1964.020710111

Cited by 12 publications

(3 citation statements)

References 2 publications

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“…It is possible to give some explanations for the reactions. Minoura et al 15 have shown that phenol and cresols act as weak chain-transfer agents in polymerization of styrene under oxygen-free conditions. Similar tra,nsfer reactions are considered to occur in these monomers as illustrated in eq.…”

Section: 6mentioning

confidence: 99%

Radical polymerization behavior of hydroxystyrenes

Kato¹

1969

J. Polym. Sci. A‐1 Polym. Chem.

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Homopolymerizations of m‐ and p‐hydroxystyrene and their copolymerizations with styrene and methyl methacrylate by use of azobisisobutyronitrile as initiator were investigated, and the results were compared with those obtained previously o‐hydroxystyrene. Intrinsic viscosities of m‐ and p‐hydroxystyrene polymers obtained by bulk and solution polymerizations were ca. 2 to 3 times larger than those of o‐hydroxystyrene polymers obtained by the similar conditions. The structures of the polymers thus produced were investigated by infrared and ultraviolet spectroscopy. These studies suggested that all of the homopolymers consisted mainly of structures of normal vinyl type polymer. Rp was proportional to [I]0.52 for m‐hydroxystyrene and to [I]0.50 for p‐hydroxystyrene, for o‐hydroxystyrene Rp was proportional to [I]0.72. A reasonable chain transfer mechanism for these monomers was postulated. The apparent activation energies of polymerization for m‐ and p‐hydroxystyrene were found to be 20.1, and 18.0 kcal/mole, respectively, compared to the value of 21.5 kcal/mole for o‐hydroxystyrene. Monomer reactivity ratios and Q − e values for m‐ and p‐hydroxystyrene were determined, and the results were also compared with the case of o‐hydroxystyrene. Copolymerization generally gave a polymer with relatively high intrinsic viscosity, even in the case of o‐hydroxystyrene.

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Section: 6mentioning

confidence: 99%

Radical polymerization behavior of hydroxystyrenes

Kato¹

1969

J. Polym. Sci. A‐1 Polym. Chem.

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“…However, the mixtures containing guaiacol later returned to colorless, indicating that the quinone had been consumed, and polymerization could proceed. I n similar experiments made with cresols, Minoura et al 9 proposed that the phenols were rapidly oxidized to the quinone form, that product being the actual inhibitor.…”

Section: I1 IIImentioning

confidence: 96%

The graft copolymerization of styrene and lignin. III. Chain transfer reactions of lignin and lignin model compounds

Phillips

Brown

Stannett

1973

J of Applied Polymer Sci

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SynopsisThe effect of addition of lignin model compounds on the polymerization rate and molecular weight of polymer in the radiation-induced polymerization of styrene was studied. Guaiacol, a model for softwood lignin, reacted slowly with styrene radicals, while 2,6dimethoxyphenol, a hardwood lignin model, was a much more efficient chain transfer agent. Studies with isoeugenol indicate that allylic or phenoxy radical stability in a conjugated system may terminate polymerization quite effectively. The results are discussed in the light of new and previous data with isolated lignins; they are consistent with the previously presented grafting scheme.

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“…CH=CHa or (5) The growing radical M,. attacks either the hydroxyl group or a phenolic nucleus of the monofier molecule to terminate by abstracting a hydrogen atom.…”

Section: Yh=chzmentioning

confidence: 99%

Studies on polymers containing functional groups. VI. Kinetics of the polymerization and copolymerization behaviors of o‐hydroxystyrene

Kato¹,

Kamogawa²

1966

J. Polym. Sci. A‐1 Polym. Chem.

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SynopsisSome kinetic studies were made of the homopolymerization of o-hydroxystyrene and its copolymerization behavior with styrene and methyl methacrylate in tetrahydrofuran using azobisisobutyronitrile as initiator were done. The rate of polymerization experimentally obtained is given by R, = K [ M ] [I]0.7e. Accordingly, it is likely that the growing chain radicals are terminated not only by mutual termination but also by a chaintransfer mechanism, the latter occupying a considerable portion. The latter is mostly attributed to the transfer to monomer, i.e., C, for o-hydroxystyrene was 1.3 x Some transfer mechanism were assumed, although it i s difficult to elucidate the mechanism in detail, owing to its complexity. Effects of solvent on the rate of polymerization were examined, dioxane, methyl ethyl ketone, ethanol, and tetrahydrofuran being used. However, no differences were found among the solvents. The apparent activation energy of polymerization was found to be 21.5 kcal./mole. Monomer reactivity ratios and Alfrey-Price &-e values for o-hydroxystyrene were determined. The Q-e values (& = 1.41, e = -1.13) are rather similar to those of p-methoxystyrene. Thus, the e value for o-hydroxystyrene is more negative than that for styrene.

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The effect of phenol and cresols on the polymerization of styrene

Cited by 12 publications

References 2 publications

Radical polymerization behavior of hydroxystyrenes

Radical polymerization behavior of hydroxystyrenes

The graft copolymerization of styrene and lignin. III. Chain transfer reactions of lignin and lignin model compounds

Studies on polymers containing functional groups. VI. Kinetics of the polymerization and copolymerization behaviors of o‐hydroxystyrene

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