Spectrophotometric investigation and PPP-MO calculations of some phenylazophthalimide dyes

Wojciechowski, Krzysztof; Szadowski, J.

doi:10.1016/0143-7208(91)87019-j

Cited by 12 publications

(6 citation statements)

References 29 publications

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“…These dyes provide a good build-up and general fastness properties on polyester fabrics and they remain permanent and do not run or fade easily [16][17][18]. We have previously reported the synthesis and application of some monoazo naphthalimide containing N-alkyl and N-carboxylic acid for dyeing of polyester fabrics [19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Solubility of Two Disperse Dyes Derived from N‐Alkyl and N‐Carboxylic Acid Naphthalimides in the Presence of Gemini Cationic Surfactants

Gharanjig

Sadeghi‐Kiakhani

Tehrani‐Bagha

et al. 2011

J Surfact & Detergents

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The solubility of naphthalimide-based monoazo dyes containing N-ethyl and N-ethanoic acid groups was investigated in the presence of a conventional monomeric counterpart (DTAB) and two cationic gemini surfactants (12-4-12 or 14-4-14) individually. The effective parameters on dye solubility such as temperature, time and concentration of surfactants were investigated by UVVisible spectrophotometry. The results demonstrate that the solubility of both dyes was considerably increased at concentrations above the surfactant CMC. The wavelength for the maximum absorbance of dyes in the aqueous solution shifts toward longer wavelengths with changes in the concentration of the cationic surfactants. A kinetic study of solubilization of dyes in cationic surfactants solution showed that the rate of solubilization follows the pseudo-first-order reactions. Rates of solubilization were in the range of 0.5 9 10 -3 to 6.8 9 10 -3 min -1 for both dyes. The disperse dye containing a carboxylic acid group (dye 2) has a higher solubility rate than the dye containing an alkyl group (dye 1). The type of surfactant has a very low effect on adsorption of dye 1 onto the polyester fibers, whereas changing the surfactant type from DTAB to 12-4-12 or 14-4-14 causes adsorption of dye 2 on polyester to decrease.

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Section: Introductionmentioning

confidence: 99%

Solubility of Two Disperse Dyes Derived from N‐Alkyl and N‐Carboxylic Acid Naphthalimides in the Presence of Gemini Cationic Surfactants

Gharanjig

Sadeghi‐Kiakhani

Tehrani‐Bagha

et al. 2011

J Surfact & Detergents

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“…The method given here for reduction of the three alkylated nitrophthalimides 3 – 5 is based on the procedure for conversion of 4‐nitrophthalimide to 4‐aminophthalimide described by Wojciechowski and Szadowski [15]. N ‐Alkyl‐4‐nitrophthalimide (0.10 mol) was stirred into a solution of stannous chloride (0.44 mol) in hydrochloric acid (37%, 450 ml) and water (150 ml).…”

Section: Methodsmentioning

confidence: 99%

“…While phthalimidylazo dyes feature in at least one commercial range of high wet fastness dyes [14], relatively little has appeared in the academic literature concerning their synthesis and properties. Furthermore, when such information has been reported, it has been restricted to relatively simple derivatives [15,16]. An exception has been our recent paper [17], which discusses the preparation and spectroscopic properties of some novel highly substituted phthalimidylazo dyes that feature various N ‐alkylimido motifs in addition to bathochromically shifted absorption maxima.…”

Section: Introductionmentioning

confidence: 99%

Novel azo dyes derived from phthalimide. Part 1: Synthesis and spectroscopic properties

Choi

Jeon

Kim

et al. 2008

Coloration Technology

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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.

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“…Monoazo disperse dyes containing naphthalimide residue have been found to have acceptable dyeing and fastness properties. [5][6][7][8] They displayed excellent thermal stabilities and good dyeing fastness properties. 9,10 A group of disperse dyes based on N-alkyl, N-alkylglycinates, and N-butyric acid-1,8-naphthalimide were synthesized and their dyeing and fastness properties on polyester fibers were investigated.…”

Section: Introductionmentioning

confidence: 99%

Dyeing and fastness properties of polyamide fabrics using some acid‐based monoazo disperse dyes

Sadeghi‐Kiakhani

Gharanjig

Arami

et al. 2011

J of Applied Polymer Sci

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A series of monoazo disperse dyes derived from naphthalimide containing butyric acid has been applied on polyamide fabrics. The build up and dyeing properties of these dyes such as leveling property, wash, light, perspiration for alkaline and acidic conditions, and rubbing fastnesses on polyamide fabrics have been investigated. The results showed that the applied dyes are capable of producing red to bluish red hues on polyamide fabrics. Because of the presence of both carboxylic acid and hydroxyl groups on the molecular structure of Dye 3, it showed desired and more strength in respect to other used dyes. Comparing the build up of these dyes to commercial dyes such as disperse red 60 and disperse red 73 revealed that most of the used dyes have higher build up in comparison to the commercial ones. Measurement of fastness properties of dyed samples indicated that they have good wash (4-5), rubbing (4), perspiration (4-5), and heat fastnesses (4-5) and they possess less than moderate light fastness (3-4) on polyamide fabrics.

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Spectrophotometric investigation and PPP-MO calculations of some phenylazophthalimide dyes

Cited by 12 publications

References 29 publications

Solubility of Two Disperse Dyes Derived from N‐Alkyl and N‐Carboxylic Acid Naphthalimides in the Presence of Gemini Cationic Surfactants

Solubility of Two Disperse Dyes Derived from N‐Alkyl and N‐Carboxylic Acid Naphthalimides in the Presence of Gemini Cationic Surfactants

Novel azo dyes derived from phthalimide. Part 1: Synthesis and spectroscopic properties

Dyeing and fastness properties of polyamide fabrics using some acid‐based monoazo disperse dyes

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