Azo dyes are widely used to treat textiles, leather articles, and some foods. Some azo dyes, if absorbed by the human body, can undergo reduction decomposition to form carcinogenic amines due to enzymes in the body that have reduction properties. Classifications, properties, recent synthesis and applications of azo. Azo dyes are organic compounds bearing the functional group r. They are a commercially important family of azo compounds, i. Solvent effects on the electronic spectra of some heterocyclic azo dyes pradipta kumar behera, anita xess, and sachita sahu photochemistry research group, school of chemistry, sam balpur university, jyoti vihar, sambalpur 768019, india email. Patel 2 faculty of science, pacific university, udaipur 1bhavans science college, dakor, gujarat, india. Recent trends in synthesis and application of nitrogen heterocyclic azo dyes.
This dye exhibits twophoton absorption activity in the range of 720880 nm, with a 2pa cross section of 1508 at 850 nm. Synthesis of disazo dyes derived from heterocyclic components. Sometime between 1858 and 1859, french chemist francoisemmanuel verguin found that reaction of aniline with stannic chloride gave a fuchsia, or rosecoloured, dye, which he. Synthesis of heterocyclic azo dyes from quinolin8ol ezema. Azo dyes represent the largest production volume of dye chemistry. Aug 01, 2012 read modelling heterocyclic azo dye affinities for cellulose fibres by computational approaches, dyes and pigments on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. Synthesis, characterization, and antimicrobial activity of. From the earliest of times, people admired the beautiful natural colors of the plants and minerals. Nov 02, 2019 azo dye plural azo dyes chemistry any of a large number of mostly yellow to red synthetic dyes that contain an azo or diimide nn functional group. The dyebath ph stability of a disperse dye is a property of great technical importance. Azo dyes are characterised by presence in the molecule of one or more azo groups n n, which form bridges between organic residues, of which at least one is usually an aromatic nucleus. Six derivatives of heterocyclic azo dyes were synthesized by coupling diazotized aniline and 4nitroaniline with quinolin8ol, 5nitrosoquinolin8ol and 5nitroquinolin8ol respectively. Synthesis, properties and applications topics in heterocyclic chemistry 14 strekowski, lucjan on. Physicochemical and nonlinear optical properties of novel.
Tartrazine is a yellow acid azo dye discovered in 1884 and still in common use. Examples of benzidinebased dyes are direct blue 6, direct brown 9, direct black 38, etc. There is a risk of exposure when wearing garments or accessories that contain azo dyes, or when sleeping in such bedclothes. Hydrochloric acid 1 ml was added to a flask with a suspension of 4aminobenzaldehyde or 4aminobenzoic acid 1. Synthesis of heterocyclic azo dyes from quinolin8ol chidimma g. The thiophene ring can also be incorporated into a coupling component for the preparation of heterocyclic azo dyes. Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and applications of these heterocycles. Synthesis of heterocyclic azo dyes from quinolin 8. Photographs of a pmma thin film doped with heterocyclic azo dye 7.
Azoic dyes azo dyes contain at least one azo group nn attached to one or often two aromatic rings. Photoswitching in azo dyes bearing thienylpyrrole and. Since, the organic dyes that harness sunlight are generally considered as the heart of the dye sensitized solar cells dssc, the present study was carried out with the aim to design heterocyclic azo dyes that can be potentially used in dssc application. Structures of the azomethine dyes were confirmed by the elemental analysis, mass spectrometry and several spectroscopic techniques. Diazotation of 4aminobenzaldehyde and 4aminobenzoic acid. Some azo dyes have the potential to release carcinogenic aromatic amines when reductive cleavage occurs. Chemistry and materials research issn 2224 3224 print issn 2225 0956 online vol. Oct, 2014 chemistry and materials research issn 2224 3224 print issn 2225 0956 online vol. Heterocycles are extensively used in disperse dye chemistry either for textile or. Nov 14, 2003 the term azo dyes is applied to those synthetic organic colorants that are characterized by the presence of the chromophoric azo group. Get exclusive access to content from our 1768 first edition with your subscription. Ep0214445a3 ep86110549a ep86110549a ep0214445a3 ep 0214445 a3 ep0214445 a3 ep 0214445a3 ep 86110549 a ep86110549 a ep 86110549a ep 86110549 a ep86110549 a ep 86110549a ep 0214445 a3 ep0214445 a3 ep 0214445a3 authority ep european patent office prior art keywords azo dyes heterocyclic azo heterocyclic dyes prior art date 19850810 legal status the legal status is an assumption and is not a. Azo dyes may also be toxic to aquatic organisms and cause longterm adverse effects in the aquatic environment.
Perkins accidental discovery of mauve as a product of dichromate oxidation of impure aniline motivated chemists to examine oxidations of aniline with an array of reagents. Interest in the design of azo dyes containing heterocyclic moieties stems from their. The acid azo dyes possess affinity for wool and silk and are applied by essentially the same procedure used for the direct class. Heterocyclic azo dyes were synthesized by diazotation of several substituted anilines and coupling with 5n,ndialkylamino2,2.
Azo dyes containing heterocyclic rings lead to brighter and often deeper. This dye was isolated as light orange yellow colour solid with 78% yield, m. Prominent types are 1 acid dyes for polyamide and protein substrates such as nylon, wool, and silk. Experiment 8 synthesis of an azo dye the coupling reaction. New azo dyes, azomethine dyes and heterocyclic schiff bases derivatives.
Pdf six derivatives of heterocyclic azo dyes were synthesized by coupling diazotized aniline and 4nitroaniline with quinolin8ol. Azo dye compounds have many applications in industry including photosensitive, photodynamic therapy, electro photographic and photographic system applications and are predominant organic photoconductive materials. Table 1 yieds, purification details and physical properties of dyes 26. Jcprc5 364 synthesis, characterization and chelating properties of novel heterocyclic azo dyes containing ligand bhavna k.
The films thickness were measured with a digital vernier caliper and found to be between 0. Synthesis of heterocyclic azo dyes from quinolin 8 ol. Some azo dyes with this property and which can revert slowly to the trans isomer in the dark are used in sunglasses and car sunroofs. New heterocyclic azo dyes for printing synthetic fabrics. Due to the interesting biological activities, several studies have been reported based on heterocyclic azo dyes as well as metalii complexes 2, in this article, synthesis of new azo. The substituent effects on the visible absorption spectra of the heterocyclic azo dyes 18 were also evaluated. Photoswitching in azo dyes bearing thienylpyrrole and benzothiozole heterocyclic systems by paulo j. Heterocyclic azo dyes have wide applications as high leveldying. Fast thermal cistrans isomerization of heterocyclic azo. Synthesis and characterization of a new heterocyclic azo pigment. Us4225489a heterocyclic azo dyes and pigments containing 4. It is likely that the arylamines emitted from the azo dye can be absorbed by the skin and accumulate in the body. Pdf synthesis of heterocyclic azo dyes from quinolin8ol. Procedure for the azo coupling of pyrrole precursors 68 with the diazonium salts 9 and 10 to afford heterocyclic azo dyes 15.
Synthesis of heterocyclic azo dyes from quinolin 8 ol by. Synthesis, spectroscopic characterization and pharmacological. Read developments in azo disperse dyes derived from heterocyclic diazo components, dyes and pigments on deepdyve, the largest online rental service for scholarly research with thousands of academic publications available at your fingertips. This divalent group is attached to sp 2 hybridized carbon atoms. Primary amines were condensed with aromatic keton, 2acetyl fluorene in dmf dimethyl. Heterocyclic azo dyes adaptable photochromic switches with. The characteristic feature is the presence in the structures of one or more azo groups, together with hydroxyl groups, amine and substituted amine groups as auxochromes. The pdf file you selected should load here if your web browser has a pdf reader plugin installed for example, a recent version of adobe acrobat reader. Alternatively, you can also download the pdf file directly to your computer, from where it can be opened using a pdf reader. In recent, years heterocyclic based azo dyes, have found great success due to their higher tinctorial strength, brighter dyeing and excellent light, washing and sublimation fastness, and chromophoric strength in relation to diazo dyes based uniquely on azobenzene derivatives 3. To download the pdf, click the download link below. Theoretical designing of novel heterocyclic azo dyes for dye. Synthesis of heterocyclic azo dyes from quinolin 8 ol, length.
Azo dyes make up 6070% of all dyes used and are the most important chemical class of dyes. Dyes are used in almost every commercial product such as food, clothing, pigments and paints, etc. About half of the dyes used in industry are azo dyes. This shortcoming of car bocyclic azo dyes is overcome by heterocyclic azo dyes, as well as other dye.
Abstract a series of schiff bases and their fluorene derivatives have been synthesized. Synthesis of heterocyclic azo dyes from quinolin 8 ol, author. We studied absorbance and fluorescence spectra of the azomethine dyes in various solvents. Many azo dyes, like sudan red and scarlet red, can be used as biological dyes because they are fat soluble and can be absorbed into fat cell tissues on microscope slides. Scribd is the worlds largest social reading and publishing site. Preparation and characterization of some new azo dyes. Synthesis and spectral properties of some azo disperse dyes.
A series of disperse dyes have been synthesized by diazotation of 2 aminothiophene derivative and coupling with various narylmaleimides. Synthesis, characterization, biological activity and. There are many different classes of dyes in which azo dyes are certainly one of the most important classes. The azo dyes constitute the largest chemical class, containing at least 66% of all colorants. The present work describes the synthesis of novel heterocyclic azo dyes by. Azo dyes represent the largest production volume of dye chemistry today, and their relative. Dyes, azo kirkothmer encyclopedia of chemical technology. Novel heterocyclic azomethine dyes were prepared by the reaction of anthracene9carbaldehyde with different heterocyclic amines under microwave irradiation. Developments in azo disperse dyes derived from heterocyclic.