Synthesis and application of an alkali-clearable azo disperse dye containing a fluorosulfonyl group and analysis of its alkali-hydrolysis kinetics

Koh, Joonseok; Greaves, Andrew

doi:10.1016/s0143-7208(01)00028-6

Cited by 105 publications

(75 citation statements)

References 4 publications

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“…Azo compounds have found widespread application in many different areas such as polyester fiber [1], disperse dyes [2], biological reactions, and in analytical chemistry [3]. On the other hand, azo benzene is one of the most representative classes of photochromic molecules with two geometric isomers, trans and cis [4][5][6].…”

Section: Introductionmentioning

confidence: 99%

Crystallographic and conformational analysis of two novel trans-azo benzene compounds

et al. 2009

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The molecular and crystal structure of (E)-2-Acetyl-4-(2-bromophenyldiazenyl)phenol (1) and (E)-2-Methyl-4-(o-tolyldiazenyl)phenol (2) were characterized and determined by single crystal X-ray diffraction method besides spectroscopic means. The periodic organization of 1 is stabilized by C-HÁÁÁO type weak H-bond and BrÁÁÁO type weak halogen bonding and thus, a two dimensional puckered network is established almost parallel to (101) the plane. Molecules of 2 are linked into C(7) chains generated by translation along the [1 0 1] direction with the aid of O-HÁÁÁN type H-bonds, and these chains are strengthened by C-HÁÁÁp interactions involving o-tolylphenol ring. Quantum chemical studies at B3LYP/6-311 ??G(d,p) level reveal that potential barrier of the compounds around Ar-N torsions is of double minimum character unless it is defected by the presence of o-substituent groups in the vicinity of the azo bridge. The results from crystallographic and quantum chemical studies suggest that azo benzene compounds may adapt non-planar geometry apart from the most stable planar conformation, which is located on the secondary minima of double potential barrier regarding rotational motion around Ar-N bonds.

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Section: Introductionmentioning

confidence: 99%

Crystallographic and conformational analysis of two novel trans-azo benzene compounds

et al. 2009

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“…Azo compounds have received much structural interest in chemistry due to their versatile applications in many different areas such as polyester fiber [1], disperse dyes [2], as well as their use in many biological reactions and in analytical chemistry [3]. Furthermore, their application as industrial dyes and in biological systems where some may be used as inhibitor for tumor growth [3] is of great importance.…”

Section: Introductionmentioning

confidence: 99%

Crystallographic and conformational analysis of (E)-2-isopropyl-4-(p-tolyldiazenyl)phenol

et al. 2008

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The molecular and crystal structures of the title compound, C 16 H 18 N 2 O, were characterized and determined by single crystal X-ray diffraction method in addition to spectroscopic means such as IR, UV-VIS and 1 H NMR. The compound crystallizes in orthorhombic space group P bca, with a = 9.3350(5) Å , b = 23.4878(13) Å , c = 26.5871 (12) Å , Z = 16, D calc. = 1.1591(1) g/cm 3 , l (MoK a ) = 0.073 mm -1 . Monomers of the compound in the crystal structure are linked into C(7) and C(8) chains generated by translation along the [1 0 0] direction with the aid of O-HÁÁÁN type H-bonds which serve to the stabilization of periodic organization of the molecules beside major and minor component in the disordered azo fragment. In order to describe conformational flexibility and the crystal packing effects on the molecular conformation, potential barriers regarding the rotation along both Ar-N bonds were calculated by varying the related torsional degrees of freedom in every 10°ranging from -180°to +180°via quantum chemical calculations at DFT/B3LYP level.

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“…Thus, the modified dyes containing diesters, thiophenes, benzodifuranones, phthalimides and fluorosulfonyl group have been designed to improve the wash fastness ( Fig. 8) (Koh & Kim, 1998a, 1998bKoh & Greaves, 2001). The most often patented dyes with enhanced wash fastness and build-up properties were based on heterocyclic amines such as 2-aminothiophene, and 2-aminopyrazole, and were used separately or in combination (Freeman and Sokolowska, 1999).…”

Section: Fastness To Wet Treatmentmentioning

confidence: 99%

“…8). These alkali-clearable disperse dyes obviate the need for sodium hydrosulphite and significantly reduce the cost of effluent treatment (Koh & Greaves, 2001). Recently, these types of dye have become technically important for the coloration of polyester and its cellulosic blends.…”

Section: Recent Requirements In Disperse Dyeing Technologymentioning

confidence: 99%

Dyeing with Disperse Dyes

Koh¹

2011

Textile Dyeing

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Synthesis and application of an alkali-clearable azo disperse dye containing a fluorosulfonyl group and analysis of its alkali-hydrolysis kinetics

Cited by 105 publications

References 4 publications

Crystallographic and conformational analysis of two novel trans-azo benzene compounds

Crystallographic and conformational analysis of two novel trans-azo benzene compounds

Crystallographic and conformational analysis of (E)-2-isopropyl-4-(p-tolyldiazenyl)phenol

Dyeing with Disperse Dyes

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