Chemoselective Polymerization of a Phenol Derivative Having a Methacryl Group by Peroxidase Catalyst

Uyama, Hiroshi; Lohavisavapanich, Chakapan; Ikeda, Rinsei; Kobayashi, Shiro

doi:10.1021/ma971510p

Cited by 99 publications

(61 citation statements)

References 8 publications

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“…Generally, laccases and peroxidases act on the phenol part selectively leading to vinyl-substituted poly(phenols) which then are available for further modification (Figure 26) [68,101,171].…”

Section: Selected Examples For Chemoselective Polymerizationmentioning

confidence: 99%

Enzyme Initiated Radical Polymerizations

2012

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Section: Selected Examples For Chemoselective Polymerizationmentioning

confidence: 99%

Enzyme Initiated Radical Polymerizations

2012

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“…We reported that peroxidase catalysis induced a chemoselective polymerization of 2-(4-hydroxyphenyl)-ethyl methacrylate (1), a phenol derivative, having methacryloyl group, 20 in which only the phenol moiety was polymerized without involving vinyl polymerization of methacryl to give a polymer having the methacryloyl group in the side chain. The resulting polymer was subjected to thermal and photochemical curings.…”

Section: Resultsmentioning

confidence: 99%

“…literture. 20 Laccase solution (4 × 10 4 unit per mL) and 2 were purchased from Koken Co. and Shin-Nakamura Chemical Co., respectively. All the reagents and solvents were used as received.…”

Section: Discussionmentioning

confidence: 99%

Laccase-Catalyzed Curing of Vinyl Polymers Bearing a Phenol Moiety in the Side Chain

Ikeda

Uyama

Kobayashi

2001

Polym J

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KEY WORDSCuring / Laccase / Phenol / Oxidative Coupling / Recently, environmentally benign process of polymer curing has been paid much attention in coating industry, since the conventional industrial method often involves severe curing conditions with a large amount use of energy. 1 Development of new curing methodology under ambient conditions is strongly desired.Polymerizations catalyzed by enzymes (enzymatic polymerizations) have been investigated extensively as new methodology of polymer syntheses. 2-10 Characteristics of enzyme catalysis are expected to provide new polymeric materials, which are difficult to be obtained by conventional methods. Peroxidases induced the oxidative polymerization of phenol derivatives under mild reaction conditions to produce a new class of functional polyphenols in good yields. This process does not use toxic formaldehyde and their synthetic procedure is very facile. The polyphenols enzymatically obtained have structures normally composed of a mixture of phenylene and oxyphenylene units, which are formed by C-C and C-O couplings of phenols, respectively. Recent investigations revealed that the coupling selectivity (regioselectivity) could be controlled by changing the solvent composition, yielding a DMFsoluble polyphenol. 11,12 Very recently, we have created a novel system of enzymatic polymerization, i.e., a laccase-catalyzed crosslinking reaction of new "urushiol analogues" for the preparation of "artificial urushi". [13][14][15] Single-step synthesis of the urushiol analogues was achieved by using lipase as catalyst. These compounds were cured in the presence of laccase catalyst under mild reaction conditions without use of organic solvents to produce the crosslinked polymeric film with high gloss surface and good elastic properties. This multienzymatic processes are highly significant as a fundamental study for † To whom correspondence should be addressed.

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“…Örneğin metakriloil grublu fenolik bir bileşiğin enzimatik polimerizasyonunda, metakriloil grupları polimerleşmeye dahil olmadan sadece fenol grubunun polimerleşmesini enzimlerin kemoseçiciliğinin mümkün kıldığından bahsedilmiştir. Böylece yan zincirinde metakriloil grup olan polifenolü yüksek verimde elde etmişlerdir [7]. Bunun yanında enzimatik polimerizasyonu, iletken polimerleri sentezlemek [8,9] ve atık sudan fenolü çıkarmak için de verimli bir şekilde kullanmışlardır [10][11][12].…”

Section: Introductionunclassified

Enzi̇mati̇k Oksi̇dati̇f Poli̇meri̇zasyon İle Orto-Hi̇drazon-Fonksi̇yonlu Oli̇gofenol Sentezi̇

Turaç¹

2017

Ömer Halisdemir Üniversitesi Mühendislik Bilimleri Dergisi

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Hidrazon fonksiyonlu oligofenol, (E)-2-(1-(2-fenilhidrazon)etil)fenol[FHEF] enzimatik oksidatif polimerizasyon yöntemiyle sentezlenmiştir. Yan zincirinde hidrazon fonksiyonel grubu içeren fenol türevinin enzimatik oksidatif polimerizasyonunda; katalizör olarak Horseradish peroksidaz (HRP) enzimi, yükseltgeyici olarak ise Hidrojen peroksit (H 2 O 2 ) kullanılmıştır. Polimerleşme üzerine reaksiyon sıcaklığı, reaksiyon pH'sı ve çözücü sistemleri gibi değişik parametrelerin etkileri çalışılmıştır. Sentezlenen oligomerin karakterizasyonu nükleer magnetic rezonans ( 1 H ve 13 C NMR), infrared spektroskopisi (FT-IR), jel geçirgenlik kromotoğrafisi (GPC), ultraviyole spektroskopisi (UV-Vis), dönüşümlü voltametri (CV) ve termogravimetrik analiz (TGA/DTA) teknikleri ile yapılmıştır.

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Chemoselective Polymerization of a Phenol Derivative Having a Methacryl Group by Peroxidase Catalyst

Cited by 99 publications

References 8 publications

Enzyme Initiated Radical Polymerizations

Enzyme Initiated Radical Polymerizations

Laccase-Catalyzed Curing of Vinyl Polymers Bearing a Phenol Moiety in the Side Chain

Enzi̇mati̇k Oksi̇dati̇f Poli̇meri̇zasyon İle Orto-Hi̇drazon-Fonksi̇yonlu Oli̇gofenol Sentezi̇

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