Triphenylmethane dye

Ishikawa M, Ye J Y, Maruyama Y and Nakatsuka H 1999 Triphenylmethane dyes revealing heterogeneity of their nanoenvironment femtosecond, picosecond, and single-molecule studies J. Chem. Phys. A 103 4319-31... 

Crystal violet is an example of a triphenylmethane dye. Its preparation in the laboratory may be illustrated by the condensation of 4 4 -tetramethyl-diaminobenzophenone (Michler s ketone) and dimethylaiiiliue in the presence of phosphorus oxychloride ... 

Naphthalenesulfonic acids are important chemical precursors for dye intermediates, wetting agents and dispersants, naphthols, and air-entrainment agents for concrete. The production of many intermediates used for making a2o, a2oic, and triphenylmethane dyes (qv) involves naphthalene sulfonation and one or more unit operations, eg, caustic fusion, nitration, reduction, or amination. 

Hydroxy-2-Naphthalenecarboxylic Acid. l-Hydroxy-2-naphthoic acid is made similarly to the isomer (2-hydroxy-1-naphthoic acid) by reaction of dry sodium 1-naphthalenolate with CO2 in an autoclave at ca 125°C. It has been used in making triphenylmethane dyes and metalli able a2o dyes. Alkylamides and arylamides of l-hydroxy-2-naphthalenecarboxyhc acid are cyan couplers, ie, components used in indoaniline dye formation in color films (see Color PHOTOGRAPHY). 

V-hen2y1-/V-ethy1ani1ine CisH N [92-59-1] C5H5N(C2HUCH2C5H5 light yeUow oil 314 triphenylmethane dyes... 

C-alkyl (9-toluidine C HgN [95-53P H3CC3H,NH3 yeUow Hquid 200-20 triphenylmethane dyes ... 

Triphenylmethane dyes comprise one of the oldest classes of synthetic dyes. They are of bdUiant hue, exhibit high tinctorial strength, are relatively inexpensive, and may be appHed to a wide range of substrates. However, they are seriously deficient in fastness properties, especially fastness to light and... 

Nearly all uses and appHcations of benzyl chloride are related to reactions of the active haUde substituent. More than two-thirds of benzyl chloride produced is used in the manufacture of benzyl butyl-phthalate, a plasticizer used extensively in vinyl flooring and other flexible poly(vinyl chloride) uses such as food packaging. Other significant uses are the manufacture of benzyl alcohol [100-51-6] and of benzyl chloride-derived quaternary ammonium compounds, each of which consumes more than 10% of the benzyl chloride produced. Smaller volume uses include the manufacture of benzyl cyanide [140-29-4], benzyl esters such as benzyl acetate [140-11-4], butyrate, cinnamate, and saUcylate, benzylamine [100-46-9], and benzyl dimethyl amine [103-83-8], and -benzylphenol [101-53-1]. In the dye industry benzyl chloride is used as an intermediate in the manufacture of triphenylmethane dyes (qv). First generation derivatives of benzyl chloride are processed further to pharmaceutical, perfume, and flavor products. 

In presence of polyamines the maximum of light absorption of indicated triphenylmethane dyes displaces on 10-30 nm, for azo dyes the shift of the band reaches 50-80 nm. The greatest difference of light absorption of associates and reagents is watched for BKM at pH 5,05, for BPR at pH 4,20, for CPR in an interval pH 5,05-5,45. At these pH dyes are anions, it promotes interaction with a cationic surface-active substance. The ratios between polymer and BKM, BPR, CPR are established by spectroscopy method, its equal 1 20, 1 20 and 1 30 accordingly. 

The mechanism of reaction with steroids has not been elucidated. Various nonquantitative reactions occur simultaneously. Cyclopentenyl cations have been postulated as intermediates which condense with anisaldehyde to yield colored compounds [4]. It is probable that triphenylmethane dyes are also formed with aromatic compounds. 

One of the most typical examples demonstrating the importance of the hydro-phobic contribution may be alkaline-fading reactions of triphenylmethane dyes, which take place between dye cations and hydroxyl ions to form carbinols167. ... 

Primary alcohols can be selectively detected using reagent sequences involving an initial oxidation to yield aldehydes that are then reacted in acid medium with electron-rich aromatics or heteroaromatics, according to the above scheme, to yield intensely colored triphenylmethane dyes. 

Classical examples of this type of reaction are the various dimethylaminobenz-aldehyde reagents (q.v.) and vanillin-acid reagents, of which one, the vanillin-phosphoric acid reagent, is already included in Volume 1 a. The aldol condensation of estrogens is an example for the reaction mechanism (cf. Chapter 2, Table 6). According to Maiowan indole derivatives react in a similar manner [1]. Longo has postulated that catechins yield intensely colored triphenylmethane dyes [2]. 

In the presence of strong acids catechins react with aromatic aldehydes to yield triphenylmethane dyes [14] according to Malowan [15] indole derivatives form the following condensation product ... 

The general aspects of the aldehyde-acid reaction were discussed in Chapter 2. Thus it is readily understood that catechins, for example, can react with aromatic aldehydes in the presence of strong acids to yield colored triphenylmethane dyes [26]. 

Azo dyes Allura Red AC, Amaranth, Azorubine, Brilliant Black BN, Brown FK, Brown HT, Lithol Rubine BK, Ponceau 4R, Red 2G, Sunset Yellow, Tartrazine Triarylmethane (triphenylmethane) dyes Brilliant Blue FCF, Fast green FCF, Green S, Patent Blue V... 

Arylmethane leuco dyes are converted into di- or triarylmethane dyes on oxidation. This class of dye precursors sometimes is referred to as leuco di- or triphenylmethane dyes, or di- or triphenylmethane leuco dyes. The use of the term di- or triarylmethane dyes can be misleading as the central carbon atom is a carbonium ion. Instead, the term di- and triarylmethine dye is recommended for this class as it correlates with the well-known polymethine dyes. Nevertheless, it has not been commonly used. 

Triphenylmethane dyes show inferior lightfastness properties. They are, however, still one of the most important groups of synthetic dyes due to their brilliance, high tinctorial strength, and low cost. Several reviews have appeared on di- and triphenylmethane dyes.1-5 However, the color-forming precursors — leuco dyes — have received less attention in the literature. 

In general, the triarylmethane leuco skeleton can be represented by structures 1-4. Traditional leuco di- and triphenylmethane dyes frequently include compounds of type 1 and 3. The closely related compounds 2 and 4 are derived from 1 and 3. Another closely related type is the lactone or phthalide 5 (see Chapter 4). In all of these leuco dyes, one or more of the phenyl rings can be replaced by a hetaryl ring or by a fused aromatic ring such as a naphthalene. 

Triphenylmethane leuco dyes are far more important than the diphenylmethanes in terms of practical value. Use of triphenylmethane dyes for traditional applications of dyes is limited to dyeing wool, silk, leather, and polyacrylonitrile fibers. The largest portion of the annual production of this class of leuco dyes is consumed in the manufacturing of various copying papers. 

Like most dyes, substituents on di- and triphenylmethane dyes have a significant effect on the absorption spectra. Acetylation of the imino nitrogen of auramine O (32) results in shift to longer wavelength (Eq. 3). A... 

Thermal recording materials consist of a heat-sensitive layer made by dispersing a leuco triphenylmethane dye and a phenol in a binder where the... 

Smith, I. L., Analytical Applications of the Heavy Metal Induced Oxidation of the Leuco Bases of Triphenylmethane Dyes, Ph.D. dissertation, The University of Alabama (1974) Chem. Abs. 83(8), 71097m. 

As a beginning toward understanding and preventing this phenomenon, the effect of selected amines and phenol stabilizers on the pigment-sensitized photooxidation of the leuco triphenylmethane dye I to the blue dye II was determined (Scheme 2). 

The pioneering work Forster and Hoffmann [28] on the viscosity dependence of the fluorescence quantum yield of triphenylmethane dyes (TPM) has set the foundation for several reports in these dyes (Fig. 12). It was found that both an ability to twist around the carbocationic center and the donor-acceptor properties are important [66], Specifically, a strong intramolecular quenching is observed for 34 that is virtually absent (two orders of magnitude slower quenching rate) in the bridged... 

Vogel M, Rettig W (1987) Excited state dynamics of triphenylmethane-dyes used for investigation of microviscosity effects. Ber Bunsenges Phys Chem 91 1241-1247... 

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