Abstract
Four new ʻupper rimʼ azocalix[4]resorcinarene have been synthesized by coupling calix[4]resorcinarene with different diazotized aromatic compounds of sulphanilic acid, anthranilic acid,o-aminophenol andp-aminobenzoic acid. The prepared compounds were characterized based on m.p., elemental analysis, FT-IR,1H-NMR. These dyes have been used for the dyeing of textile fibres like cotton and wool. Their fastness properties such as fastness to sunlight, water, washings, and perspiration have also been studied. The synthesized dyes have been employed for computerized colour strength determination through colour matching with known standards. Their L, A*, B*values as well as the colour difference values such as ∆L, ∆A*, ∆B*, ∆C and ∆H have also been reported.
Highlights
Dyes1-3 and pigments are chemical components that are responsible for much of the colour in the natural world and which are added to manufactured goods such as textiles, and foodstuffs to generate a desired colour
Calix[n]arenas have been mostly reported as the coupling component for various diazotized aromatic amines4-6 while amino crown ether has been used as the diazo component7
4 new azo compounds were synthesized by coupling of diazonium salt of sulphanilic acid, anthranilic acid, o-aminophenol, and p-aminobenzoic acid with calix[4]resorcinarene
Summary
Dyes and pigments are chemical components that are responsible for much of the colour in the natural world and which are added to manufactured goods such as textiles, and foodstuffs to generate a desired colour. Calix[4] resorcinarene-anthranilic acid dye II (2-{[11,17,23-tris[(2-carboxyphenyl) diazenyl]4,6,10,12,16,18,22,2 4-octahydroxy-2,8, 14,20-tetramethylpentacyclo [19.3.1.13,7.19,13.115,19] octacosa-1(25),3,5,7(28),9, 11,13(27),15,17,19(26),21,23dodecaene-5-yl] diazenyl}benzoic acid). Reddish brown powder; m.p.> 300 ̊ C; λmax 440 nm in DMF; IR (KBr) 3429.78 (Ar-OH), 1607.38 (-N=N-) cm-1; 1H NMR (DMSO-d6) δ 1.65 ppm (d, 12H, CHCH3), δ 4.88 ppm (q, CHCH3), δ 7.1-8.0 ppm (m, ArH), δ 10.12 ppm (s, 12H OH). Calix [4] resorcinarene-p-aminobenzoicacid dye IV (4-{[11,17,23-tris[(4-carboxy phenyl) diazenyl]4,6,10,12,16,18,22,24-octa hydroxy-2,8,14,20-tetramethyl pentacyclo [19.3.1.13,7.19,13.115,19] octacosa-1 (25),3,5,7(28),9, 11,13(27),15,17, 19(26),21,23-dodecaene-5-yl] diazenyl}benzoic acid). Brown powder; m.p.> 300 ̊ C; λmax 435 nm in DMF; IR (KBr) 3410.49 (Ar-OH), 1517.02 (-N=N-), 1637.27 cm-1; 1H NMR (DMSO-d6) δ 1.65 ppm (d, 12H CHCH3), δ 4.96 ppm (q, 4H, CHCH3), δ 7.8-8.5 ppm (m, ArH), 9.02 ppm (s, 12H, OH). 0.25 g Calix[4]resorcinarene dyes was added in 35 mL water and the solution was heated to 50°C. A chromaticity curve was obtained, and with the help of the computer, their L, A, B values and colour difference values such as ∆L, ∆A, ∆B, ∆C, ∆H, the total colour and the percentage strength were evaluated
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