Novel azo dyes derived from phthalimide. Part 1 : Synthesis and spectroscopic properties / Jae-Hong Choi in COLORATION TECHNOLOGY, Vol. 124, N° 2 (2008)  

[article]  inCOLORATION TECHNOLOGY > Vol. 124, N° 2 (2008) . - p. 92-99 Titre : Novel azo dyes derived from phthalimide. Part 1 : Synthesis and spectroscopic properties Type de document : texte imprimé Auteurs : Jae-Hong Choi, Auteur ; Chun Yoon, Auteur ; Andrew D. Towns, Auteur ; Mi-Hyeon Kim, Auteur ; Jeong-Min Jeon, Auteur Année de publication : 2009 Article en page(s) : p. 92-99 Note générale : Bibliogr. Langues : Anglais (eng) Index. décimale : 667.3 Teinture et impression des tissus Résumé : A series of azo dyes has been synthesised based on N-alkylphthalimide diazo components featuring one of three different alkyl groups. An analogous set of dyes was prepared in which the N-alkylphthalimidylazo systems bore an o,o-dibromo-substitution pattern. In these cases, cyanodebromination was performed to give the corresponding dicyano analogues. All the synthesised intermediates and dyes were characterised by mass spectrometry, proton nuclear magnetic resonance spectroscopy and elemental analysis. The absorption maxima of the dyes in dimethylformamide (N,N-dimethyl ~) were observed to be in the range 435–608 nm and found to be consistent with results seen in previous studies of conventional monoazo disperse dyes. Replacement of both halogens in the dibromo-substituted dyes with cyano groups led to large bathochromic shifts (128–141 nm) in absorption maxima. Bathochromism was also observed when acetylamino groups were present on the coupler ring ortho to the azo link. However, variation of the N-alkyl function on the imido ring from n-butyl to sec-butyl and iso-propyl had little effect on absorption maxima, values being similar to that reported for the parent N-unsubstituted analogue. DOI : 10.1111/j.1478-4408.2008.00127.x En ligne : http://onlinelibrary.wiley.com/doi/10.1111/j.1478-4408.2008.00127.x/pdf Format de la ressource électronique : Pdf Permalink : https://e-campus.itech.fr/pmb/opac_css/index.php?lvl=notice_display&id=3148 [article]

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Synthesis and spectroscopic properties of novel azo dyes derived from phthalimide / Jae-Hong Choi in COLORATION TECHNOLOGY, Vol. 123, N° 6 (2007)  

[article]  inCOLORATION TECHNOLOGY > Vol. 123, N° 6 (2007) . - p. 379-386 Titre : Synthesis and spectroscopic properties of novel azo dyes derived from phthalimide Type de document : texte imprimé Auteurs : Jae-Hong Choi, Auteur ; Joon-Soo Park, Auteur ; Mi-Hyeon Kim, Auteur ; Hyun-young Lee, Auteur ; Andrew D. Towns, Auteur Année de publication : 2008 Article en page(s) : p. 379-386 Note générale : Bibliogr. Langues : Anglais (eng) Index. décimale : 667.3 Teinture et impression des tissus Résumé : A set of azo dyes has been synthesised using N-substituted phthalimides as diazo components. 3,5-Dibromo-N-substituted-phthalimidylazo derivatives were cyanated by cyanodehalogenation to give dicyano analogues. All of the synthesised intermediates and dyes have been characterised by mass spectrometry, 1H-NMR or elemental analyses. The gamut of colour of the prepared dyes spanned much of the visible spectrum: absorption maxima of the dyes in formamide were observed in the range 436 to 609 nm. Consistent with results seen in previous studies of non-phthalimido monoazo disperse dyes, replacement of dibromo groups with dicyano functions in the phthalimide-based set led to large bathochromic shifts in absorption maxima, as did the introduction of acetylamino groups onto the coupler ring ortho to the azo link. However, switching an N-propyl function on the imido ring for a benzyl or 3-cyanopropyl substituent had little effect on absorption maxima. Good correlations between the observed absorption maxima of certain dyes and those of model analogues predicted by Pariser–Parr–Pople molecular orbital calculations were observed when steric effects were absent. DOI : 10.1111/j.1478-4408.2007.00112.x En ligne : http://onlinelibrary.wiley.com/doi/10.1111/j.1478-4408.2007.00112.x/pdf Format de la ressource électronique : Pdf Permalink : https://e-campus.itech.fr/pmb/opac_css/index.php?lvl=notice_display&id=6858 [article]

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