Alkyl orange dyes

BINDING PARAMETERS OF ALKYL ORANGE DYES TO IMPRINTED GELS ... 

The imprint hypothesis of specific adsorption suggests that compounds which are structurally related to the specific compound will also show enhanced adsorption on a specific adsorbent (relative to the normal adsorbent). Numerous experimental data have been reported [e.g.. Refs. (110,111,113,123-127)] which amply confirm this prediction. Almost invariably, a specific adsorbent will show increased adsorption for all compounds even remotely similar to the specific compound. Presumably, the more closely such compounds resemble the specific compound, the greater their adsorption on the specific adsorbent. Dickey (113) has confirmed this for the various orange dyes adsorbents specific for one alkyl orange dye show greater specificity for adjacent homologs than for... 

Morrison J.L., Worsley M., Shaw D.R. and Hodgson G.W. (1959) The nature of the specificity of adsorption of alkyl orange dyes on silica gels. Can. J Chem. 37, 1986-1995. 

Haldeman R.G. and Emmett P.H. (1955) Specific adsorption of alkyl orange dyes on silica gel, J. Phys. Chem., 59, 1039-1043. 

Introduction of an unsaturated alkyl residue improves the solubility of the dye [100], iV-Methyl- /V-cyanocthylaniline yields an orange dye. The shade is shifted to yellow with a red cast by using iV-cyanoethyl-2-chloroani 1 inc. 

These unexacting requirements make the simplest unsulphonated azo structures, often monoazo types, quite acceptable [80]. Typical of the least polar members of this class are Cl Solvent Yellow 2 (4-68), Cl Solvent Orange 1 (4.69) and Cl Solvent Red 17 (4.70). Simple azo structures carrying sulphonamide, sulphone or carboxylate ester groups are used where a somewhat more polar, less soluble dye is needed. Simple disazo compounds (4-amino-azobenzene— 2-naphthol, for example) are used as red solvent dyes. Probably the only structural feature worthy of note in this class is the occasional adoption of structures carrying long alkyl chains to enhance solubility, as in the case of the disazo dye Cl Solvent Yellow 107 (4.71). 

Sulfur Bake. The yellow, orange, and brown sulfur dyes belong to this group. The dyes are usually made from aromatic amines, diamines, and their acyl and nuclear alkyl derivatives. These may be used in admixture with nitroanilines and nitrophenols or aminophenols to give the desired shade. The color formed is said to be the result of the formation of the thiazole chromophore, evident in dye structure (1). 

Exhaustive alkylation of aminonaphthols, such as 2-amino-7-naphthol, and coupling with diazotized aromatic amines generates yellow, orange, red, and brown cationic azo dyes. Compound 5 dyes human hair and polyacrylonitrile in brown shades [26],... 

Exhaustively alkylated 4-aminodiphenylamine is also suitable as a coupling component. Dyes such as 6 [41025-69-8], obtained by reaction with diazotized nitroanilines, confer fast yellow, orange, and red shades to polyacrylonitrile [27],... 

By exhaustive alkylation of 3-aminophenylpyrazolone compounds, a trimethy-lammonium moiety can be introduced into this coupling component. The disazo dye 7 [86565-98-2] colors paper in orange shades [28],... 

Such dye salts are converted to azo bases by alkali. Alkylating agents attack the nitrogen atom of the azo bond, forming alkylarylhydrazone dyes which dye polyacrylonitrile in lightfast, yellow to orange shades [26],... 

As for PANI/polysaccharide composite, PANI/extracellular composite had successfully apphed for anionic reactive dyes removal, such as reactive brilliant blue R and reactive orange 16 [25]. The electrostatic interactions between dye anions and cationic ammonium in the composite were attributed for the adsorption process with the maximum adsorption capacity of 0.5775 and 0.4748 mmol/g for reactive brilliant blue R and reactive orange 16, respectively. The effect of substituted anihne to adsorption was investigated by synthesizing several alkyl-substituted aniline/chitosan composites... 

Figure 20.3. Solubilization experiments support the notion of a polymer-induced micellization. The amount of a dye, Orange OT, solubilized in mixtures of sodium alkyl sulfates of different chain lengths (C10-C16) and poly(vinyl pyrrolidone) (PVP) is given as a function of the surfactant concentration. (Redrawn from H. Lange, Kolloid-Z. Z. Polym., 243 (1971 101)...

Figure 8 Effect of PVP on the solubilization/concentration plots of sodium alkyl sulfates of different chain lengths and indicated c.m.c. (Cm). Dye is Orange OT. (From Ref. 27.)...

Chapman and co-workers have appended tert-butyloxycarbonyl terminated poly( lysine) dendrimers onto poly(ethylene glycol) chains [74] to produce dendritic block copolymer surfactant systems. The surfactant activity was explored by studies of the solubilisation of the dye Orange-OT in aqueous solutions and the dendritic copolymers were found to be effective surfactants. In a closely related study, Meijer and co-workers have synthesised poly(propylene imine) dendrimers that were modified with long hydrophobic alkyl chains, azabenzene units or adamantane groups (Figure 8.13) [75]. Studies of these PPI dendritic... 

A study by stopped-flow techniques of the rate of solubilization of positively charged acridine (and related) dyes by the micelles of several sodium n-alkyl sulphates was reported by Robinson and co-workers [132]. The solubilization process was relatively slow k = 47.6 s for acridine orange in NaDS) due largely to charge effects and the rate was very dependent on the geometrical shape... 

Borman nitrated PPO to give 11 that has a nitro-substituent on the polymer backbone. This material was then reduced to the amino-substitued polymer 12 that was then converted to the diazonium salt. (Scheme 4) The latter reacted with (3-naphthol to give an orange colored polymeric dye. The amino-substituted polymers 12 were reacted with dianhydrides or diglycidyl ethers to give cross-linked products." Alkylation of 12 with dimethyl sulfate gave the dimethyl derivative. 

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