XANTHENE DYES


XANTHENE DYES] (Supplement)  [c.1039]

Xanthation Xanthene Xanthene dyes  [c.1075]

Most xanthene dyes are classified as basic dyes by their method of appHcation acid dyes can be produced by introduction of sulfonic acid groups. The fluoresceins, which contain carboxy and hydroxy substituents, are also acid dyes for coloration of silk. Some of the fluoresceins in which the carboxy group has been esterified, are soluble in alcohol or other organic solvents and can be classified as solvent dyes. Mordant dyes can be produced by introducing o-dihydroxy or sahcyhc acid groups (2), which when metallised can have very good lightfastness.  [c.399]

The physical properties of the xanthene type dye stmcture in general have been considered. For example, the aggregation phenomena of xanthene dyes has been reviewed (3), as has then photochemistry (4), electron transfer (5), triplet absorption spectra (6), and photodegradation (7). For the fluoresceins in particular, spectral properties and photochemistry have been reviewed (8), and the photochemistry of rhodamines has been investigated (9).  [c.399]

Recently, there have been many new uses for xanthene dyes reported. These include photo-activated insecticidal activity and pest-control (10,11), as anticancer agents (12), in hydrogen generation during the photolysis of water (13), as nonlinear optical (NLO) materials (14), or charge control agents in electrophotographic toners (laser printers and photocopiers) (15), and many reports as markers or biological stains (16—19). Rhodamines and rosamines in particular have been used in inks for ink-jet printers. There has also been a significant amount of new activity on the use of xanthenes, and in particular rhodamines, as laser dyes (20—22).  [c.399]

Recently, several rhodamines have been used as magentas ia ink-jet printing. These have been chosen primarily for their brilliant magenta shades, but with the disadvantage of very poor light- and waterfastness on ordinary copy papers. On specially coated color ink-jet papers the waterfastness improves, but the lightfastness is stiU much lower than comparable a2o dyes, and, on this media, the difference ia brightness between a2o and xanthene chromophores is also much smaller. Attempts to improve the waterfastness of xanthene dyes for ink-jet have been made as ia (21) (33,34). Improvements ia lightfastness have been claimed by iatroduciag branching and rings ia the alkyl chains on the nitrogens and by usiag a polymeric counterion, (An ), eg, (22) (35).  [c.400]

Table 1. Economic Aspects of Xanthene Dyes Table 1. Economic Aspects of Xanthene Dyes
Table 2. Toxicological Properties of Selected Xanthene Dyes Table 2. Toxicological Properties of Selected Xanthene Dyes
See Analgesics, antipyretics, AND antiinflammatory agents Xanthene dyes.  [c.286]

Xanthene Dyes. This class is best represented by Rhodamine B. It has high fluorescent brilliance but poor light and heat stabihty it may be used in phenohcs. Sulfo Rhodamine is stable and is useflil in nylon-6,6. Other xanthenes used in acryhcs, polystyrene, and rigid poly(vinyl chloride) are Solvent Green 4, Acid Red 52, Basic Red 1, and Solvent Orange 63 (see Xanthene dyes).  [c.464]

A useful classification of sensitizing dyes is the one adopted to describe patents in image technology. In Table 1, the Image Technology Patent Information System (ITPAIS), dye classes and representative patent citations from the ITPAIS file are Hsted as a function of significant dye class. From these citations it is clear that preferred sensitizers for silver haUdes are polymethine dyes (cyanine, merocyanine, etc), whereas other semiconductors have more evenly distributed citations. Zinc oxide, for example, is frequendy sensitized by xanthene dyes (qv) or triarylmethane dyes (see Triphenylmethane and related dyes) as well as cyanines and merocyanines (see Cyanine dyes).  [c.429]

Neady every significant class of dyes and pigments has some members that function as sensitizers. Toxicological data are often included in surveys of dyes (84), reviews of toxic substance identification programs (85), and in material safety data sheets provided by manufacturers of dyes. More specific data about toxicological properties of sensitizing dyes are contained in the Engchpedia under the specific dye classes (see Cyanine dyes Polymethine dyes Xanthene dyes).  [c.438]

The rhodamines described thus far are basic rhodamines. They are used primarily for the dyeing of paper and the preparation of lakes for use as pigments. They are also used in the dyeing of silk and wool where brilliant shades with fluorescent effects are required, but where lightfastness is unimportant. Many new uses for rhodamine dyes have been reported. For example, when vacuum-sublimed onto a video disk, Rhodamine B loses its color to form a clear stable film which becomes permanently colored on exposure to uv light (27). This can be used ia optical recording for computer storage or video recording (28). Fluorescent coloration of rigid or nonplasticized poly(vinyl chloride) (PVC) by the addition of selected rhodamines to the PVC resia before sheet or film formation has been reported (29). The addition of rhodamines to Hquefied bis(hydroxyalkyl)aromatic dicarboxyhc acid esters prior to their condensation to form polyesters to produce tinted polymer sheets is also used (30). Rhodamine 6G can be used ia ink-jet printing where fluorescence under uv conditions is a desired property (31). Selected xanthenes, including fluoresceia, Rhodamine B, and Rhodamine 6G, have been used as laser dyes (32).  [c.400]

Fig. 1. Colorants for food and dmgs fall into several dye types. FD C Blue No. 1 (1) and FD C Green No. 3 (3) are triphenyknethane dyes (qv). FD C Blue No. 2 (2) is an indigoid and FD C Red No. 3 (4) is a xanthene dye (qv). FD C Red No. 40 (5), FD C Yellow No. 6 (7), Citms Red No. 2 (8), and FD C Red No. 4 (10) are azo dyes (qv). FD C Yellow No. 5 (6) and Orange B (9) are pyrazolones (see Pyrazoles,pyrazolines, and pyrazolones). Fig. 1. Colorants for food and dmgs fall into several dye types. FD C Blue No. 1 (1) and FD C Green No. 3 (3) are triphenyknethane dyes (qv). FD C Blue No. 2 (2) is an indigoid and FD C Red No. 3 (4) is a xanthene dye (qv). FD C Red No. 40 (5), FD C Yellow No. 6 (7), Citms Red No. 2 (8), and FD C Red No. 4 (10) are azo dyes (qv). FD C Yellow No. 5 (6) and Orange B (9) are pyrazolones (see Pyrazoles,pyrazolines, and pyrazolones).
Xanthene dyes are those containing the xanthylhim [261-23-4] (la) or diben2o-y-pryan nucleus [92-83-1] (xanthene) (lb) as the chromophore with amino or hydroxy groups meta to the oxygen as the usual auxochromes. They are  [c.398]

For uniformity with the stmctures given in the Colourindex the ammonium radical (9) is used for the amino-substituted xanthenes and the keto form for the hydroxy derivatives. The xanthene dyes may be classified into two main groups diphenylmethane derivatives, called pyronines, and triphenylmethane derivatives (eg, (4)), which are mainly phthaleins made from phthaUc anhydride condensations. A third much smaller group of rosamines (9-phenylxanthenes) is prepared from substituted ben2aldehydes. The phthaleins may be further subdivided into the following fluoresceins (hydroxy-substituted) rhodamines (amino-substituted), eg, (6) and mixed hydroxy/amino-substituted.  [c.399]

Reactive xanthene dyes with P-hydroxyethylsulfonyl groups, as exemplified by stmcture (29), provide brilliant shades and excellent washfastness on cotton (40). The sulfutein derivative (29) is synthesized by condensing 3-aminophenol-P-hydroxyethylsulfone with  [c.402]

A series of water-soluble fiber-reactive xanthene dyes has been prepared from the reaction of ben2oxanthenedicatboxylic acid anhydride disulfonic acid with, for example, 3-aminophenyl-P-hydtoxyethyl sulfone to yield dyes, with high brilliance and good fastness properties for dyeing of or printing on leather, wool, sHk, or ceUulosic fibers (53).  [c.406]

Since 1973, the U.S. International Trade Commission has reported the manufacture and sales of dyes by appHcation class only. During the latter half of the 1970s and all through the 1980s, aimual dye production in the United States, including xanthene dyes, changed very Httle. Statistics for the production of basic dyes include those products Hsted as cationic dyes, eg, cyanines, for dyeing polyacrylonitrile fibers and the classical triaryhnethane dyes, eg, malachite green, for coloring paper and other appHcations. Furthermore, statistics for xanthene dyes ate also hidden in the production figures for acid, solvent, mordant, and food dyes and organic pigments. Between 1975 and 1984, the production of basic dyes in the United States varied from (11—17 million Ihs). However, from 1985—1990, production of basic dyes varied from (11—12.5 million Ihs) with an increase in sales value from 56 to 73 million pet annum. The production figures for xanthenes in 1980 ate reproduced in Table 1.  [c.406]

Xanthene dyes (qv) can be either acidic or basic. Acid xanthenes are known to exist in two tautomeric forms. The phenoHc type, or fluorans, are free-acid stmctures such as D C Orange No. 10 (17b) and D C Red No. 21 (17c). Most have poor water solubHity. In contrast to these, the quinoids or xanthenes are usuaHy the highly water-soluble sodium salt counterparts of the fluorans such as D C Orange No. 11 (18) and D C Red No. 22 (21a). Presendy, there are no certifiable basic xanthene colorants.  [c.443]

Cadmium sulfide can be spectrally sensitized by cyanine, styryl, merocyanine, and xanthene dyes (32,33). In contrast to zinc oxide, which is sensitized by many dyes that desensitize silver haUdes, cadmium sulfide energy levels require dyes that are also good sensitizers for silver haUde. In a comparison of dye energy levels for various photoconductors, vinylogous thiacyanines were noted to sensitize ZnO, AgBr, and CdS, but the silver haUde desensitizer methylene blue sensitized only zinc oxide (33). Tin sulfide, dye-sensitized with oxazine 1 [24796-94-9] is an excellent model semiconductor surface for kinetic studies of spectrally sensitized electron transfer. Erom fluorescence quenching studies, the rate of electron transfer from oxazine 1 into the SnS2 conduction band is 3 x 10, corresponding to an electron-transfer time of 40 fs (34).  [c.433]

SENSORS WITH RESPONSE ON SOME XANTHENE DYES BASED ON MOLECULARLY IMPRINTED ELECTROSYNTHESIZED POLYMERS  [c.322]

In the present work, the synthesis of two MIEPs is described and their application for sensing and separation two xanthene dyes - rhodamine and fluorescein - has been reported.  [c.322]

These acid rhodamines are usually used for sHk and wool because they have level dyeing properties and show good fastness to alkaU however, they have poor lightfastness. An improved process for manufacturing 3,6-diaminosubstituted xanthenes is reaction of the inner salts of  [c.401]

Hydroxyl Derivatives. The building block of most hydroxyl-substituted xanthenes, or fluorones, is fluorescein (2), (3). Fluoresceins can be made by the condensation of resorcinol with phthaUc anhydride. Although fluorescein itself is no longer in general use as a textile dye, its intense green fluorescence, even at extremely high dilutions, makes it ideal for tracing water flows to detect leakage and as sea markers for downed aircraft and missing ships. However, Acid Red 388 is replacing fluorescein in such appHcations. The sodium or potassium salt of fluorescein, commonly called uranine [518 7-8] (Cl45550) (37), is stiU used for dyeing wool and silk brilliant yellow shades.  [c.404]

Figure 4 shows the stmctures of the metallized dye developers used in the first SX-70 film (1972) and in Polacolor 2 (1975). The images formed by these dye developers are characterized by very high light stabiUty (23). The metallized cyan dye developer is based on a copper phthalocyanine pigment (24). Incorporation of developer groups converts the pigment into an alkah-soluble dye developer. A study of the chromium complexes of azo and azomethine dyes led to the design of the magenta and yellow metallized dye developers (25). The latter was derived from the 1 1 chromium complex of an (9,(9 -dihydroxyazomethine dye. A magenta dye developer [78052-95-6] (1) containing a xanthene dye moiety is used in Polacolor ER (extended range) film, as well as in the integral Polaroid films that followed SX-70 (26,27). This dye developer has much less unwanted blue absorption than eadier magenta dye developers and is thus capable of more accurate color rendition (Fig. 5).  [c.488]

Although aot showa ia Table 1, dyes ate also being used ia high technology appHcations, such as ia the medical, electronics, and especially the reprographics industries. For example, they ate used in electrophotography (qv) (photocopying and laser printing) in both the toner and the organic photoconductor, in ink jet printing, and in direct and thermal transfer printing (6). As in traditional appHcations, azo dyes predominate phthalocyanine, anthraquiaone, xanthene, and triph enylm eth an e dyes ate also used. These appHcations ate low volume (tens of kg up to several hundred t pet annum) and high added value (hundreds of doUats to several thousand doUats pet kg), with high growth rates (up to 60%).  [c.271]

Acid Dyes. These water-soluble anionic dyes ate appHed to nylon, wool, sUk, and modified acryHcs. They ate also used to some extent for paper, leather, food, and cosmetics. The original members of this class aU had one or mote sulfonic or catboxyHc acid groups in thein molecules. This characteristic probably gave the class its name. Chemically, the acid dyes consist of azo (including preformed metal complexes), anthraquiaone, and ttiaryHnethane compounds with a few azHie, xanthene, ketone imine, nitro, nitroso, and quHiophthalone compounds.  [c.271]

Di- and Triaryl Garbonium and Related Dyes. The structural interrelationships of the diarylcarbonium dyes (58), triarylcarbonium dyes (59), and thek heterocycHc derivatives are shown in Figure 5. As a class, the dyes are bright and strong, but are generally deficient in lightfastness. Consequendy, they are used in oudets where brightness and cost-effectiveness, rather than permanence, are paramount, for example, the coloration of paper. Many dyes of this class, especially derivatives of pyronines (xanthenes), are among the most duorescent dyes known.  [c.282]

Fig. 5. Stmctural interrelationships among diaryl and triaryl carbonium dyes. Pyronine = xanthene (61), R = CH3 is Bindschedler s Green. Fig. 5. Stmctural interrelationships among diaryl and triaryl carbonium dyes. Pyronine = xanthene (61), R = CH3 is Bindschedler s Green.

See pages that mention the term XANTHENE DYES : [c.1075]    [c.1075]    [c.398]    [c.398]    [c.398]    [c.399]    [c.400]    [c.401]    [c.402]    [c.403]    [c.404]    [c.405]    [c.406]    [c.407]    [c.408]    [c.408]    [c.409]    [c.114]    [c.351]    [c.401]   
See chapters in:

Encyclopedia of chemical technology Supplement  -> XANTHENE DYES