Derivatives of 1,4-naphthoquinone as visible-light-absorbing one-component photoinitiators for radical polymerisation / Rafal Strzelczyk in COLORATION TECHNOLOGY, Vol. 131, N° 3 (06/2015)  

[article]  inCOLORATION TECHNOLOGY > Vol. 131, N° 3 (06/2015) . - p. 229-235 Titre : Derivatives of 1,4-naphthoquinone as visible-light-absorbing one-component photoinitiators for radical polymerisation Type de document : texte imprimé Auteurs : Rafal Strzelczyk, Auteur ; Radoslaw Podsiadly, Auteur Année de publication : 2015 Article en page(s) : p. 229-235 Note générale : Bibliogr. Langues : Anglais (eng) Catégories : Caractérisation Colorants -- Synthèse Naphtoquinone Photoamorceurs (chimie) Polyaddition Index. décimale : 667.2 Colorants et pigments Résumé : Bifunctional visible-light photoinitiators for free radical polymerisation based on a 1,4-naphthoquinone skeleton were synthesised and characterised using proton nuclear magnetic resonance spectroscopy and chemical ionisation mass spectrometry. Their basic spectroscopic properties, such as absorption and low-temperature phosphorescence spectra, and their red-ox properties were also measured. These initiators contain an appropriate electron/hydrogen donor group in the skeleton and do not require an additional coinitiator for initiation. During irradiation they act both as a triplet photosensitiser and as a hydrogen/electron donor. The ability of each naphthoquinone to act as a photoinitiator strongly depends on its chemical structure. These studies suggest that initiator radicals are generated from the triplet state in an intermolecular electron/hydrogen transfer reaction. Note de contenu : - EXPERIMENTAL : General - Synthesis - Photochemical experiments - RESULTS AND DISCUSSION : Synthesis and spectroscopic characterisation of dyes - Free radical polymerisation DOI : 10.1111/cote.12144 En ligne : https://onlinelibrary.wiley.com/doi/epdf/10.1111/cote.12144 Format de la ressource électronique : Pdf Permalink : https://e-campus.itech.fr/pmb/opac_css/index.php?lvl=notice_display&id=24125 [article]

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Dyes based on the 6,7-dichloro-5,8-quinolinedione skeleton as new type II photoinitiators for radical polymerisation / Agnieszka Orzel in COLORATION TECHNOLOGY, Vol. 130, N° 3 (06/2014)  

[article]  inCOLORATION TECHNOLOGY > Vol. 130, N° 3 (06/2014) . - p. 185-190 Titre : Dyes based on the 6,7-dichloro-5,8-quinolinedione skeleton as new type II photoinitiators for radical polymerisation Type de document : texte imprimé Auteurs : Agnieszka Orzel, Auteur ; Radoslaw Podsiadly, Auteur ; Karolina Podemska, Auteur ; Rafal Strzelczyk, Auteur ; Jolanta Kolinska, Auteur ; Jolanta Sokolowska, Auteur Année de publication : 2014 Article en page(s) : p. 185-190 Note générale : Bibliogr. Langues : Anglais (eng) Catégories : Caractérisation Colorants -- Synthèse Electrochimie Oxydoréduction Photoamorceurs (chimie) Photochimie Polyaddition Résonance magnétique nucléaire Teinture -- Fibres textiles Index. décimale : 667.3 Teinture et impression des tissus Résumé : Several dyes based on the 6,7-dichloro-5,8-quinolinedione skeleton have been synthesised and characterised by proton nuclear magnetic resonance spectroscopy and electron ionisation mass spectrometry. The spectroscopic and electrochemical properties of these dyes were investigated. Photoredox pairs consisting of the synthesised dyes and commercially available hydrogen donors (2-mercaptobenzoxazole, 2-mercaptobenzothiazole, 2-mercaptobenzimidazole, and 2,5-dimercapto-1,3,4-thiadiazole) were tested for use as effective initiator systems for radical polymerisation of trimethylolpropane triacrylate with visible light. The efficiencies of these initiator systems are discussed in terms of the free energy change for the electron transfer process from the dye to the hydrogen donor. Note de contenu : - General - Synthesis of 6,7-dicholoro-5,8-quinolinedione - Synthesis of 6-(5-methoxyanilino)-7-chloro-5,8-quinolinedione - 6,11-dihydro-3-methoxy-pyrido[2,3-b]phenazine-6,11-dione II - Photochemical experiments DOI : 10.1111/cote.12083 En ligne : https://onlinelibrary.wiley.com/doi/epdf/10.1111/cote.12083 Format de la ressource électronique : Pdf Permalink : https://e-campus.itech.fr/pmb/opac_css/index.php?lvl=notice_display&id=21446 [article]

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Naphthoylenebenzimidazolone dyes as one-component photoinitiators / Rafal Strzelczyk in COLORATION TECHNOLOGY, Vol. 133, N° 2 (04/2017)  

[article]  inCOLORATION TECHNOLOGY > Vol. 133, N° 2 (04/2017) . - p. 178-183 Titre : Naphthoylenebenzimidazolone dyes as one-component photoinitiators Type de document : texte imprimé Auteurs : Rafal Strzelczyk, Auteur ; Radoslaw Podsiadly, Auteur Année de publication : 2017 Article en page(s) : p. 178-183 Note générale : Bibliogr. Langues : Anglais (eng) Catégories : Colorants Oxydoréduction Photoamorceurs (chimie) Photoréticulation Polyaddition Index. décimale : 667.2 Colorants et pigments Résumé : The appropriate substituents have been added to a 7H-benzimidazo[2,1-a]benz[de]isoquinolin-7-one skeleton in order to obtain a one-component initiator system. The absorption, fluorescence, and electrochemical properties of these naphthoylenebenzimidazolone dyes and their usefulness as visible light initiators of free radical polymerisation of trimethylolpropane triacrylate were examined. The initiation efficiency of these dyes was compared with that of the parent 7H-benzimidazo[2,1-a]benz[de]isoquinolin-7-one in the presence of a coinitiator. Results show that these bifunctional dyes are able to initiate polymerisation without an additional coinitiator. Photopolymerisation studies and the relationship between the rate of polymerisation and the free energy change for electron transfer revealed that, depending on the concentration, initiating radicals are generated via intra- and intermolecular electron transfer. DOI : 10.1111/cote.12266 En ligne : https://drive.google.com/file/d/1Ifn7hJnnErImnucwbhKJtz85aq4K5L07/view?usp=drive [...] Format de la ressource électronique : Pdf Permalink : https://e-campus.itech.fr/pmb/opac_css/index.php?lvl=notice_display&id=28232 [article]

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Synthesis and application of dyes derived from benz[cd]indol-2(1H)-one as visible-light-absorbing polymerisation photoinitiators / Rafal Strzelczyk in COLORATION TECHNOLOGY, Vol. 132, N° 4 (08/2016)  

[article]  inCOLORATION TECHNOLOGY > Vol. 132, N° 4 (08/2016) . - p. 320-326 Titre : Synthesis and application of dyes derived from benz[cd]indol-2(1H)-one as visible-light-absorbing polymerisation photoinitiators Type de document : texte imprimé Auteurs : Rafal Strzelczyk, Auteur ; Radoslaw Michalski, Auteur ; Radoslaw Podsiadly, Auteur Année de publication : 2016 Article en page(s) : p. 320-326 Note générale : Bibliogr. Langues : Anglais (eng) Catégories : Colorants -- Synthèse Lumière -- Absorption Photoamorceurs (chimie) Photochimie Polyaddition Index. décimale : 667.3 Teinture et impression des tissus Résumé : Several potential initiators based on benz[cd]indol-2(1H)-one dye have been synthesised and evaluated in the radical polymerisation of a system containing trimethylolpropane triacrylate under visible light. Absorption, fluorescence, and phosphorescence spectra and the electrochemical properties of these novel dyes were determined. Owing to the presence of an appropriate hydrogen donor group in their structure, these photoinitiators do not need an extra coinitiator to initiate the polymerisation process. During photopolymerisation they act both as a triplet sensitiser and as a hydrogen donor. The relationship between the polymerisation rate and the triplet-excited-state reduction potential suggests that initiating radicals are formed from the triplet state via hydrogen transfer. This mechanism is supported by density functional theory calculations. 8-Bromo-6-[(2-sulphanylethyl)sulphanyl]benzo[cd]indol-2(1H)-one and 8-bromo-6-sulphanylbenz[cd]indol-2(1H)-one may be applied as visible-light initiators of free radical polymerisation to obtain a low-molecular-weight polymer. Note de contenu : - General - Synthesis - Photochemical experiments - Quantum chemical calculations DOI : 10.1111/cote.12218 En ligne : https://onlinelibrary.wiley.com/doi/epdf/10.1111/cote.12218 Format de la ressource électronique : Pdf Permalink : https://e-campus.itech.fr/pmb/opac_css/index.php?lvl=notice_display&id=26734 [article]

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