• Bulletin of the Korean Chemical Society
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• v.34 no.3
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• pp.863-867
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• 2013

A series of azo disperse dyes having dicyanovinyl groups was synthesized by the Knoevenagel condensation with malononitrile from carbonyl substituted phenylazo disperse dyes which were prepared by conventional diazo coupling reaction of aniline derivatives as diazo components. A variety of coupling components such as anilines, an indole and a pyridone were used. The azo disperse dyes were evaluated for their spectral properties and dyeing assessment on the polyester fabrics. The azo disperse dyes containing dicyanovinyl groups showed bathochromic shifts and darker colors due to increased electron withdrawing strength in their azo components and extended conjugation by dicyanovinyl groups than their parent carbonyl substituted azo dyes. The dyes containing 2-acetylamino-5-methoxy substituent in the coupling component exhibited higher wavelength of maximum absorbance (${\lambda}_{max}$) and significant negative solvatochromism than those of other dyes due to intramolecular hydrogen bonding.

• Journal of the Korean Chemical Society
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• v.16 no.5
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• pp.320-327
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• 1972

The coupling of aromatic diazonium salts with humic or nitrohumic acid, as a supplemental method of determining the structure and utilization of humic acid, were studied. The following results were obtained. 1) Humic acids have many vacan to-and p-positions in their phenol kernels. 2) Humic acids have not so many benzene kernels in their structure units. 3) When coupled with aromatic diazonium salts (such as aniline, aminonaphthalene and aminoanthraquinone derivatives), various azo-dye were obtained.

• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.26 no.7
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• pp.528-533
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• 2013

We focused on the development of red azo colorants with high thermal stability and good solubility for LCD color filter in this research. For the synthesis of hybrid azo colorants, we used the couplers of aniline, naphthol and benzoimidazol functional group. The synthesized hybrid azo colorants were charaterized by using NMR, UV/visible spectroscopy, FT-IR, EA and TGA. They represented the maximum absorption wavelengths which are longer than 500 nm in UV/visible spectrum. So they were confirmed to be suitable for red colorants of LCD color filter. Azo compound (1a, 1b) with aniline functional group had good solubility in organic solvents such as acetone, methanol, chloroform and PGMEA. Moreover azo compounds (1c, 1d and 1e) with naphthol and benzoimidazolone functional group gave excellent thermal stability higher than $250^{\circ}C$ in TGA thermograms.

• Macromolecular Research
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• v.16 no.6
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• pp.532-538
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• 2008

Epoxy-based azopolymers were synthesized by the reaction of the diglycidyl ether of bisphenol A (DGEBA) or N,N-diglycidyl aniline (DGA) with disperse orange 3 (DO3) to give poly(DGEBA-co-DO3) or poly(DGA-co-DO3), respectively. Aniline-based azopolymers prepared from poly(DGA-co-An) precursors, synthesized by the reaction of DGA with aniline, were produced by the post-azo coupling reaction with diazonium salts containing various substituents. Holographic gratings were carried out to measure the diffractive efficiencies (DE) for the interference patterns of the $Ar^+$ laser from 50 to $300\;mW/cm^2$ intensity. The shorter repeating unit with higher chromophore density induced deeper surface relief gratings (SRG). Large surface gratings were observed for the aniline-based azopolymers with -COOH substituents, as compared with those for epoxy-based azopolymers. The aniline-based azopolymers with dimerized chromophores and various substituents were also synthesized to observe the effect of chromophore substituents and dimerization on the holography. The dimerized chromophores were more sensitively photoisomerized by the $Ar^+$ laser beam, and demonstrated a larger grating than that with one azo bond.

• Proceedings of the Korean Society of Dyers and Finishers Conference
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• 2004.04a
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• pp.199-203
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• 2004

The azo red pigments for textile printing containing amino-N-substituted benzamide derivatives as diazo components and 2-hydroxy-3-naphthoyl derivatives as coupling components were prepared. They have been printed on cotton, and the fastness, such as light, washing, dry cleaning, rubbing and heat stability was estimated. The new azo red pigments were valuable colorants in case of textile printing.

• Bulletin of the Korean Chemical Society
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• v.27 no.2
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• pp.195-196
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• 2006

• Textile Coloration and Finishing
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• v.19 no.5
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• pp.37-40
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• 2007

The electrostatic layer-by-layer technique provides a convenient way to control the construction of ultrathin films at nano-scale ranges and can be easily obtained. It can be also applicable to fiber substrate with dye compounds. We have fabricated multilayer dye films using diazonium resin and three couplers, which are prepared by self-assembly approach. This method is based on layer-by-layer deposition using electrostatic attraction between oppositely charged ions. Beside, the diazo coupling reaction proceeded to form azo dye layer on the PET fibers the same time. The corresponding results of the multilayer films have been discussed on the level of color strength (K/S).

• Analytical Science and Technology
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• v.19 no.1
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• pp.50-57
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• 2006

Well known environmental wastes from dye industry were separated by the micellar electrokinetic capillary chromatography(MECC). These wastes include H-acid modifier and 2-naphthylamine-1,5-disulfonic acid, and are known to be the diazo components of the azo dye. The results of the separation were compared with the result obtained by the HPLC using ion-pairing mechnism. MECC method was also applied to separate a few direct dyes including Direct Blue 2, Direct Blue 6 and Direct Blue 15, and reactive dye such as Reactive Orange 4. Informations about the diazo components of any azo dye could be obtained by comparison of electropherogram of the reduction solution of given dye with those obtained from standard materials such as H-acid, J-acid, ${\gamma}$-acid, orthanilic acid, sulfanilic acid and 2-naphthylamine-1,5-disulfonic acid which are used as diazo components of the typical azo dyes. It has been concluded that MECC and HPLC with ion-pairing mechanism could be successfully applied for the analysis of unknown dyes and their diazo components.

• Applied Chemistry for Engineering
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• v.17 no.4
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• pp.426-431
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• 2006

Acryl and vinyl sulfone functionalized blue and orange azo dyes were prepared by the coupling reaction of 6-bromo-2-cyano-4-nitroaniline and 2,5-dimethoxy-4-(vinylsulfonyl)benzenamine with 3-acrylamido-(N,N-diethylamino)benzene and 3-methyl-(N,N-diethylamino)benzene, respectively, for the coloring of poly(methyl methacrylate) (PMMA). Allyl functionalized dye was also prepared by reacting vinyl sulfone-containing dye with allylamine. Three types of dyeing method were used: the copolymerization of reactive dye with methyl methacrylate (MMA) and dyeing by polymerization of MMA in the presence of polymeric dye and dye 2 without reactive function. The color fastness for the three PMMAs were evaluated by comparing the solubility of dye under various conditions.

• Elastomers and Composites
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• v.12 no.1
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• pp.27-32
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• 1977

The kinetics of azo-coupling reaction of N-acetyl-H-acid (1-acetamino-8-hydroxynaphthalene-3, 6-disulfonic acid) with several heterocyclic diasonium compounds such as diazotiged 3-aminopyridine, 3-aminoquinoline, 8-aminoauinoline and aniline was studied. It was found that reactions proceeded at remarkably different rate. Reaction rate was in increasing order; 3-aminopyridine, 3-aminoquinoline, 8-aminoauinoline and aniline. And the activation energies were 9.62, 10.10, 10.39, 10.70 Kcal/mole, respectively. Especially, the rate constant of 3-aminopyridine was 100 times larger than that of benzene diasonium compound even in strong acidity. Hammett plot was also made of the rate constants obtained against the heterocyclic substituent constants reported in the literature. A good linear relationship was obtained and the reaction constant of N-acetyl H-acid was calculated to be 3.14.