Dyes for Synthetic Fibres

M.V. Kazankov, Dyes for synthetic fibres dyeing. Journal of All-Union chemical society named after D.I. Mendeleev (1974), v. 19, No 1, 64-71 (in Russian). 

There are many references in the patent literature to azo dyes prepared from 4- and 5-aminoisothiazoles, 3-, 5- and 7-amino-1,2-benzisothiazoles, and their quaternized derivatives. These are particularly useful in the dyeing of synthetic fibres. Isothiazole compounds have also been suggested for other industrial purposes, such as corrosion inhibitors, fireproofing agents, additives in rubber vulcanization, photographic chemicals and fluorescent whiteners in detergents. 

A series of dyestuffs have been reported which contain the pyrido[2,3-p]-l,2,4-triazine and pyrido[4,3-e]-1,2,4-triazine nuclei. These compounds have been used to dye a number of fibres fluorescent yellow shades <74GEP(0)2417916>. Another series of polyheterocyclic dyestuffs which contain a pyridotriazine moiety have been patented as fast yellow dyes especially for synthetic fibres <75GEP(0)2355967>. Amongst a number of the compounds prepared as dyestuffs were several 1H-pyrido-l,3,4-thiadiazines. The compounds were used to dye polyester fibres fast shades of yellow <77USP4025510>. 

For known fibres, at least five spectra should be obtained for synthetic fibres and ten spectra for natural fibres, along the fibre length. This is to take into account the natural variation in the fibre due, for example, to differential uptake of the dyes. 

The problem in determining affinities in dyeing is to find suitable expressions for the activities, or effective concentrations, of the dye in the fibre (a and in solution (a). This is difficult, and usually molar concentrations must be substituted. For example, in dyeing a synthetic fibre with a pure non-ionic disperse dye at equilibrium, Eq. 2.10b may be employed ... 

There is a wide diversity of chemical structures of anthraquinone colorants. Many anthraquinone dyes are found in nature, perhaps the best known being alizarin, 1,2-dihydroxyanthraquinone, the principal constituent of madder (see Chapter 1). These natural anthraquinone dyes are no longer of significant commercial importance. Many of the current commercial range of synthetic anthraquinone dyes are simply substituted derivatives of the anthraquinone system. For example, a number of the most important red and blue disperse dyes for application to polyester fibres are simple non-ionic anthraquinone molecules, containing substituents such as amino, hydroxy and methoxy, and a number of sul-fonated derivatives are commonly used as acid dyes for wool. 

In view of the immense commercial importance of phthalocyanines as pigments, it is perhaps surprising that only a few are of importance as textile dyes. This is primarily due to the size of the molecules they are too large to allow penetration into many fibres, especially the synthetic fibres polyester and polyacrylonitrile. An example of a phthalocyanine dye which may be used to dye cellulosic substrates such as cotton and paper is C. I. Direct Blue 86 (96), a disulfonated copper phthalocyanine. In addition, a few blue reactive dyes for cotton incorporate the copper phthalocyanine system as the chromophoric unit (Chapter 8). 

Many other properties have to be considered, especially for apparel fibres, e.g., moisture absorption, ability to dye, drape, texture, weaving characteristics, etc. Many of the properties are influenced by the cross-section profile of the fibre. Thus cotton and some rayons (an artificial synthetic fibre derived from cellulose) are a hollow round fibre silk has a triangular shape giving it a fine lustre and drape. 

These dyes have affinity for one or, usually, more types of hydrophobic fibre and they are normally applied by exhaustion from fine aqueous dispersion. Although pure disperse dyes have extremely low solubility in cold water, such dyes nevertheless do dissolve to a limited extent in aqueous surfactant solutions at typical dyeing temperatures. The fibre is believed to sorb dye from this dilute aqueous solution phase, which is continuously replenished by rapid dissolution of particles from suspension. Alternatively, hydrophobic fibres can absorb disperse dyes from the vapour phase. This mechanism is the basis of many continuous dyeing and printing methods of application of these dyes. The requirements and limitations of disperse dyes on cellulose acetate, triacetate, polyester, nylon and other synthetic fibres will be discussed more fully in Chapter 3. Similar products have been employed in the surface coloration of certain thermoplastics, including cellulose acetate, poly(methyl methacrylate) and polystyrene. 

Many brilliantly coloured and tinctorially strong basic dyes for silk and tannin-mordanted cotton were developed in the early decades of the synthetic dye industry. Most of these belonged to the acridine, azine, oxazine, triarylmethane, xanthene and related chemical classes their molecules are usually characterised by one delocalised positive charge. Thus in crystal violet (1.29) the cationic charge is shared between the three equivalent methylated p-amino nitrogen atoms. A few of these traditional basic dyes are still of some interest in the dyeing of acrylic fibres, notably as components of cheap mixture navies and blacks, but many modified basic dyes were introduced from the 1950s onwards for acrylic and modacrylic fibres, as well as for basic-dyeable variants of nylon and polyester [44] ... 

Derivatives of triphenylmethane were among the earliest synthetic colorants, and are still in demand where bright, intense colours are needed without the necessity for outstanding fastness to light and chemical reagents. Basic dyes of this type, as well as other cationic dyes, are suitable for dyeing conventional acrylic fibres, on which they show better fastness properties than on natural fibres. The photodegradation of triphenylmethane dyes has been reviewed [42]. 

The main use of fluorescent dyes is in the coloration of synthetic fibres, especially polyester, polyamide and acrylics in conjunction with elastane fibres, for fashion, leisure and especially sportswear uses. The fluorescent textiles offer not only high design options but also a large degree of safety in use, for instance increasing the visibility of cyclists and runners in busy urban areas. 

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