scholarly journals Synthesis of azo pyridone dyes

2011 ◽  
Vol 65 (5) ◽  
pp. 517-532 ◽  
Author(s):  
Dusan Mijin ◽  
Gordana Uscumlic ◽  
Natasa Valentic ◽  
Aleksandar Marinkovic
Keyword(s):  
Azo Dyes ◽  
Diazo Compound ◽  
Coupling Reaction ◽  
Disperse Dyes ◽  
Transfer Printing ◽  
Substituted Anilines ◽  
Light Fastness ◽  
Synthetic Fibers ◽  
Heterocyclic Derivatives ◽  
Dyes And Pigments

Over 50% of all colorants which are used nowdays are azo dyes and pigments, and among them arylazo pyridone dyes (and pigments) have became of interest in last several decades due to the high molar extinction coefficient, and the medium to high light and wet fastness properties. They find application generally as disperse dyes. The importance of disperse dyes increased in the 1970s and 1980s due to the use of polyester and nylon as the main synthetic fibers. Also, disperse dyes were used rapidly since 1970 in inks for the heat-transfer printing of polyester. The main synthetic route for the preparation of azo dyes is coupling reaction between an aromatic diazo compound and a coupling component. Of all dyes manufactured, about 60% are produced by this reaction. Arylazo pyridone dyes can be prepared from pyridone moiety as a coupling component, where substituent can be on nitrogen, and diazonim salts which can be derived from different substituted anilines or other heterocyclic derivatives. In addition, arylazo dyes containing pyridone ring can be prepared from arylazo diketones or arylazo ketoesters (obtained by coupling ?-diketones or ?-ketoesters with diazonim salts) by condensation with cyanoacetamide. Disazo dyes can be prepared by tetrazotizing a dianiline and coupling it with a pyridone or by diazotizing aniline and coupling it with a dipyridone. Trisazo dyes can be also prepared by diazotizing of aniline and coupling it with a tripyridone or by hexazotizing a trianiline and coupling it with a pyridone. The main goal of this paper is to give a brief review on the synthesis of arylazo pyridone dyes due to the lack of such reviews. In addition, some properties of arylazo pyridone dyes as light fastness and azo-hydrazon tautomerism are disccused.

Selectfluor-induced C(sp2)–O coupling reaction of N-substituted anilines with hydroxylamine derivatives

2018 ◽  
Vol 16 (33) ◽  
pp. 6017-6024 ◽  
Author(s):  
Bin Sun ◽  
Shi Yin ◽  
Xiaohui Zhuang ◽  
Can Jin ◽  
Weike Su
Keyword(s):  
Coupling Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Substituted Anilines ◽  
Metal Free ◽  
Cross Coupling Reactions ◽  
Hydroxylamine Derivatives

We developed a novel metal-free method for the construction of C(sp2)–O bonds via oxidative cross-coupling reactions between various N-substituted anilines and hydroxylamine derivatives just using commercially available Selectfluor as an oxidant.

scholarly journals Preparation and Characterization of Self-Dispersing Phthalocyanine Blue 15:4 Pigment for Dyeing of Wool Textiles

Coatings ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 741
Author(s):  
Lun Nie ◽  
Guangtao Chang ◽  
Ruoxin Li
Keyword(s):  
Sulfonic Acid ◽  
Coupling Reaction ◽  
Acid Dyes ◽  
Light Fastness ◽  
Grade 5 ◽  
Weather Resistance ◽  
Sulfonic Acid Groups ◽  
Positively Charged ◽  
Better Than

A self-dispersing pigment was produced by a diazonium coupling reaction; the pigment reacted with aromatic diazonium salts which were generated by the reaction of p-aminobenzene sulfonic acid and sodium nitrite. The surface of the pigment particles was negatively charged due to sulfonic acid groups on the pigment surface. The pigment particle size and zeta potential were, respectively, 134.5 nm and −45.4 mV at neutral pH. The wool surface was positively charged by adjusting the pH; then the anionic self-dispersing pigment dyed the cationic wool. The results show that self-dispersing pigment can adhere well without a binder, and that the K/S value is closely related to pH, dyeing time, and the amount of pigment. The color fastness of the wool was good and the light fastness of the wool was grade 5, which is better than acid dyes. Self-dispersing pigments are potential candidates for dyeing high-weather-resistance textiles.

Development of Dyeing Process for Sulphatoethylsulphone Reactive-Disperse Dye on Natural and Synthetic Fibers

2020 ◽  
Vol 1005 ◽  
pp. 116-122
Author(s):  
Juthapak Pukngam ◽  
Porntip Tooptompong ◽  
Jantip Setthayanond ◽  
Pimonrat Hansakulwat
Keyword(s):  
Coupling Agent ◽  
Diazonium Salt ◽  
Coupling Reaction ◽  
Disperse Dye ◽  
Color Fastness ◽  
Synthetic Fibers ◽  
Dyeing Process ◽  
Pet Fibers ◽  
Excellent Color ◽  
Natural And Synthetic

Sulphatoethylsulphone reactive-disperse dye was synthesized via diazotization reaction of aminophenyl-4-(β-sulphatoethylsulphone) followed by coupling reaction of the diazonium salt with phenol as a coupling agent. The synthesized dye was well dyeable on both natural and synthetic fibers with providing orange shade on cotton, silk and nylon, while the dyed PLA and PET fibers appeared in yellow shade. The dyeing conditions for cotton and silk could be conducted using 60 g/l Na2SO4 and 20 g/l Na2CO3 at 60°C for 90 minutes whereas dyeing on PLA and PET fibers was optimally done at 110°C for 30 and 45 minutes for PLA and PET, respectively. In case of nylon, it could be dyed at 100°C for 15 minutes. The synthesized reactive-disperse dye could well dye on these 5 fibers with excellent color fastness to washing.

The influence of a polymer substrate on the light fastness and isomerisation of some azo dyes

2008 ◽  
Vol 105 (3) ◽  
pp. 107-111 ◽  
Author(s):  
E Dubini-Paglia ◽  
P L Beltrame ◽  
A Seves ◽  
G Prati
Keyword(s):  
Azo Dyes ◽  
Polymer Substrate ◽  
Light Fastness

scholarly journals Disperse Yellow Dye: An Emerging Professional Sensitizer in Contact Allergy Dermatitis

2012 ◽  
Vol 10 (3) ◽  
pp. 525-526
Author(s):  
A. Tammaro ◽  
C. Abruzzese ◽  
A. Narcisi ◽  
G. Cortesi ◽  
F.R. Grippaudo ◽  
...  
Keyword(s):  
Female Patient ◽  
Textile Industry ◽  
Nursery School ◽  
School Teacher ◽  
Contact Allergy ◽  
Disperse Dyes ◽  
Hair Dyes ◽  
Synthetic Fibers ◽  
Plastic Materials ◽  
Nursery School Teacher

Disperse dyes are well known as common sensitizers in contact allergy dermatitis. Disperse yellow 3 is usually adopted in the textile industry for dying synthetic fibers, but is also used in hair dyes and for colouring plastic materials. We describe three cases of two males and one female patient, respectively a painter, an actor and a nursery-school teacher, who presented contact allergy dermatitis to disperse yellow 3 dye.

Synthesis of 4-hydroxy coumarin dyes and their applications

2016 ◽  
Vol 45 (5) ◽  
pp. 320-329 ◽  
Author(s):  
Hatem Gaffer ◽  
Mounir Salem ◽  
Magda Marzouk
Keyword(s):  
Azo Dyes ◽  
Antioxidant Activities ◽  
Fastness Properties ◽  
Transfer Printing ◽  
Polyester Fabrics ◽  
Content Type ◽  
Colour Strength ◽  
Textile Dyeing ◽  
Hydroxy Coumarin ◽  
Decisive Evidence

Purpose The present study aims to focus on the possibility of developing new eco-friendly azo dyes with good colouristic application properties, exhibiting biological and pharmacological activities. Design/methodology/approach Coupling of 4-hydroxycoumarin with a variety of aromatic diazonium salts of 2-aminothiazole, 2-aminobenzothiazole, 4-aminoantipyrine, 4-aminoacetophenone, adenine sulphate, a-naphthylamine and sulphadimidine to produce novel azo dyes. The compounds were fully characterised using spectroscopic and analytical methods. All of the compounds were tested for their antimicrobial, anticancer and antioxidant activities. The prepared dyestuffs were dyed on polyester fabrics and subsequently their dyeing properties, light, washing, perspiration, rubbing and sublimation fastness were determined. Findings The spectroscopic data of the synthesised compounds have provided decisive evidence that such compounds exist in the solid state as the azo-dike to form C and in solution in equilibrium tautomer forms A, B and D. The prepared dyestuffs are suitable for either heat transfer printing or traditional printing on polyester and nylon 6 fabrics. The prints obtained from the dyes possess high colour strength, as well as good overall fastness properties. Also the synthesised compounds exhibit good biological and pharmacology activity. Research limitations/implications Synthesis of these seven azo dyes for textile dyeing had never been reported previously. Practical implications The dyestuffs derived from 4-hydroxycoumarin are reasonable azo disperse dyestuffs giving good all round fastness properties on polyester fabrics. Social implications Production of less expensive and new eco-friendly dyes exhibit antimicrobial and anticancer activity. Originality/value It provided a potentially simple way to synthesize novel coumarin azo-dyes exhibit good biological and pharmacology activity and also exhibit good overall fastness properties.

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