Effect of aggregation of <i>p</i>‐phenylphenol on enzymatic polymer synthesis in dioxane/water mixture

Liu, W.; Ma, Lili; Wang, Jiadong; Jiang, Sixun; Cheng, Y. H.; Li, T. J.

doi:10.1002/pola.1995.080331406

Cited by 12 publications

(11 citation statements)

References 22 publications

(1 reference statement)

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“…This is in good agreement with the spectrometric analysis on the p-phenylphenol aggregation in aqueous 1,4-dioxane. 11 As for the absorption spectra in the aqueous methanol ( Figure 3), only the decrease of the absorption bands around 270-278 (6) and 280-290 nm is observed. According to the mass spectrometric analysis, the m-cresol clusters are formed efficiently even in pure methanol solvent, and their formation is not influenced by the increase of water content except for the increase of the hydration for the m-cresol clusters.…”

Section: Resultsmentioning

confidence: 87%

Self-Association of m-Cresol in Aqueous Organic Solvents: Relation to Enzymatic Polymerization Reaction

et al. 2002

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Oxidative polymerization of phenols using horseradish peroxidase (HRP) in aqueous organic solvents (1,4-dioxane-water and methanol-water), which is an attractive pathway for synthesis of a new class of polyphenols without use of toxic formaldehyde, was remarkably influenced by the water content. The present study is focused on the self-association of m-cresol in such a solvent to understand the effect of solvent on its polymerization. The change of the molecular weight of the polymer with varying the water content was found to be related to the molecular clustering in the solution, observed through the difference UV absorption spectroscopy and the mass spectrometry for clusters. In mixed solvents of 1,4-dioxane and aqueous 0.1 M phosphate buffer (pH 7), number-average molecular weight had a maximum at the aqueous buffer content of 50 vol %, whereas in methanol-aqueous buffer mixtures, the molecular weight had a small maximum at 20 vol % aqueous buffer content and gradually decreased with increase of the aqueous buffer content. As for the m-cresol clustering, the effect of the water content was also in significant contrast between the above aqueous organic solvent systems. The m-cresol clusters were not formed in 1,4-dioxane, but its clustering was remarkably promoted by an increase of the water content. On the other hand, the m-cresol clusters were formed favorably in methanol and were readily hydrated with increase of the water content in the solution. These effects of the water content on the clustering are related to the enzymatic polymerization. The polymer would be obtained in high yields when the m-cresol clusters were formed in the solution; however, the hydration of the m-cresol cluster would restrain the polymerization.

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Section: Resultsmentioning

confidence: 87%

Self-Association of m-Cresol in Aqueous Organic Solvents: Relation to Enzymatic Polymerization Reaction

et al. 2002

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“…It follows a mixed mechanism of step growth and chain growth. In a previous work, it was pointed out that the formation of aggregates of phenolic compound is favorable for the coupling and transferring of phenolic radicals . Inspired by this, we assumed that the aggregates of 4‐methoxyphenol are probably formed in the aqueous 4‐methoxyphenol solution.…”

Section: Resultsmentioning

confidence: 86%

“…The aggregation of 4‐methoxyphenol in water is ascribed to both hydrophilic hydroxy group and lipophilic methoxyl group of 4‐methoxyphenol. Mostly because of the smooth coupling and transferring of 4‐methoxyphenol radicals resulted from the aggregation, peroxidase‐catalyzed polymerization of 4‐methoxyphenol is performed effectively in water …”

Section: Resultsmentioning

confidence: 99%

Facile synthesis of oligo(4‐methoxyphenol) in water and evaluation of its efficiency in stabilization of polypropylene

Jiang

Chai

et al. 2018

Polymers for Advanced Techs

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A hindered polyphenol, oligo(4-methoxyphenol), has been first successfully synthesized via a mild biocatalytic pathway using horseradish peroxidase as catalyst in water without any additive.Then the efficiency of oligo(4-methoxyphenol) in stabilization of polypropylene (PP) was evaluated in terms of thermal analysis and accelerated aging test. It was observed that the apparent activation energy for thermal decomposition of PP/oligo(4-methoxyphenol) calculated by Friedman's method is higher than that of virgin PP. Oligo(4-methoxyphenol)-stabilized PP maintains its tensile strength even after aging at 120°C for 800 hours. Oxidation induction time and onset oxidation temperature of PP/oligo(4-methoxyphenol) are higher than both virgin PP and PP/4-methoxyphenol, as well as PP stabilized with commercially available 6-di-tert-buty-4-methylphenol or 1076. These results indicate that oligo(4-methoxyphenol) can effectively improve the thermo-oxidative resistance of PP. Noting that oligo(4-methoxyphenol) is synthesized via enzymatic polymerization in water under mild condition with a facile procedure, oligo(4-methoxyphenol) is thus proposed as a new efficiency and readily available antioxidant for PP.

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“…The monomer reactivity, molecular weight and its index were simulated for precise control of the polymerization of bisphenol -A. In aqueous 1,4 -dioxane, aggregates from p -phenylphenol were detected by difference UV absorption spectroscopy [40] . Such aggregate formation might elucidate the specifi c solvent effects in the enzymatic polymerization of phenols.…”

Section: Peroxidase -Catalyzed Polymerization Of Phenolicsmentioning

confidence: 99%

Enzymatic Polymerization of Phenolic Monomers

Uyama

2010

Biocatalysis in Polymer Chemistry

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Effect of aggregation of p‐phenylphenol on enzymatic polymer synthesis in dioxane/water mixture

Cited by 12 publications

References 22 publications

Self-Association of m-Cresol in Aqueous Organic Solvents: Relation to Enzymatic Polymerization Reaction

Self-Association of m-Cresol in Aqueous Organic Solvents: Relation to Enzymatic Polymerization Reaction

Facile synthesis of oligo(4‐methoxyphenol) in water and evaluation of its efficiency in stabilization of polypropylene

Enzymatic Polymerization of Phenolic Monomers

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