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Introduction

Dye is a chemical compound used to produce long lasting colour in materials. Dyes are used in textile, paper and plastic industries, for leather, ink, food, etc. A dye may not be capable of attaching itself to the material to be dyed, but also retain its colour on prolonged exposure to air, sunlight, temperature, soap or water. Presence of certain groups in the molecules of dyes impart colour to them, because the electrons in these compounds get excited, absorbing some colour from the visible region of light and the complementary colour is shown. Examples of such groups are -N=N-(azo) groups, -N=O(nitro) group and NH2(amino) groups. A dye can generally be described as a colored substance that has an affinity to the substrate to which it is being applied. The dye is generally applied in an aqueous solution, and may require amordant to improve the fastness of the dye on the fiber. Both dyes and pigments appear to be colored because they absorb some wavelengths of light preferentially. In contrast with a dye, a pigment generally is insoluble, and has no affinity for the substrate. Some dyes can be precipitated with an inert salt to produce a lake pigment, and based on the salt used they could be aluminum lake, calcium lake or barium lake pigments. Dyed flax fibers have been found in the Republic of Georgia dated back in a prehistoric cave to 36,000 BP. Archaeological evidence shows that, particularly in India and Phoenicia, dyeing has been extensively carried out for over 5000 years. The dyes were obtained from animal, vegetable or mineral origin, with no or very little processing. By far the greatest source of dyes has been from

the plant kingdom, notably roots, berries, bark, leaves and wood, but only a few have ever been used on a commercial scale.

Classification
These dyes have been classified into two categories Classification based on constitution: Depending upon the characteristic structural units the dyes are classified as follows.

Sl. No.

Type of Dye

Structural Unit
O

Examples Martius yellow, Naphthol yellow

1.

Nitro dyes

N O (Nitro group)

2.

Azo dyes Triphenyl methane dyes

N=N (azo group) (C6H5)3C


O C

Orange-I, Orange-II, Congo red Malachite green, Rosaniline

3.

4.

Phthalein dyes
C O (Phthalein group)

Phenolphthalein, Mercurochrome

O C

5.

Anthraquinone dyes

C O (anthraquinone group)

Alizarin

O C

6.

Indigoid dyes
C

Indigo, Tyrian purple

O Indigoid group

Structures
OH NO2 SO3Na
+

N N OH

NO2 (Martius yellow)

(Orange-I)

HO

OH

O OH

C O C O (Phenolphthalein) O (Alizarine) OH

O C C N

H N C C C N (CH 3)2
+

H O (Indigo)

N(CH 3)2 (Malachite green)

Diphenyl Methane Dye


N (H3C) 2 N (CH 3)2
+

C NH2

Auromine - 0

Classification Based on Application A particular dye may be suitable for one kind of fibre and may be unsuitable for the other. For example, a dye suitable for wool and silk may not be applied or used for dyeing cotton or rayon. Thus based on the class, shade and other properties like resistance to acids, alkalies, and fastness to light a classification of dyes is done, as given below: a) c) e) g) a) Acid dyes Direct dyes Fibre reactive dyes Insoluble azodyes b) Basic dyes d) Disperse dyes f) Vat dyes h) Mordant dyes

Acid dyes: These dyes are characterised by the presence of acid group like sulphonic acid ( SO3H), carboxylic acid ( COOH) and phenolic group. The presence of such groups make the dyes more soluble and also serve as the reactive points for fixing the dye to the fibre. Application: These dyes are applied to wool, silk and nylon. These have no affinity for cotton.

Examples: Orange-I and Orange-II can be obtained by the action of sulphonic compounds with naphthols or by coupling sulphonic compounds with naphthols.
HO
+ + -

Na O 3 S

Cl

-naphthol HO

N SO 3 Na
+

Orange-I

HO

SO 3 Na

Cl

-naphthol HO SO 3 Na
+

N N

Orange-II

b)

Basic Dyes: These dyes contain (NH2) group or (NR2) group as chromophore (colour bearing group) or auxochrome (colour enhancing group). In acidic solutions these form water soluble cations. These dyes use the anionic side on the fabric to get themselves attached. Application: This type of dyes is used to dye nylon, polyester, wool, cotton, leather, paper, etc.

Example 1. Aniline yellow


N N NH2

2. Butter yellow

N N N

CH3 CH3

3. Crysodine G

NH2 NH2

c)

Direct Dyes: These dyes also belong to the class of azo dyes and are used to dye the fabrics directly by placing it in aqueous solution of the dye. The direct dyes attack the fibre by means of hydrogen bonding. Application: These are very effective for dying cotton, wool and rayon Example: 1. Martius yellow 2. Congo Red
NH2

N N HO N N

H2N

SO 3 Na

c)

Disperse Dyes: These dyes, as the name signifies, are usually applied in the form of a dispersion of finely divided dye in a soap solution in the presence of phenol, cresol or benzoic acid.

Application: These are mainly used to dye rayon, dacron nylon, synthetic fibres, polysters and poly acrylonitrile. Examples:
O NH2

1. Celliton fast pink B


O HO
O NH CH3

2. Cellition fast blue B


O HN CH3

d)

Fibre Reactive Dyes: These dyes are used to dye fibres like cotton, wool or silk. These are linked to the fibre by virtue of the hydroxy or amino group present on the fibre. These dyes induce fast colour on fibres which is retained for a longer time. Insoluble azo dyes: The dyes belonging to this class are directly synthesised on the fibre. The fabric to be coloured is soaked in an alkaline solution of phenol or naphthol and is than treated with a solution of diazotised amine to produced the azo dye on the surface of the fabric. Application: These dyes can be used to dye cotton silk, polyester, nylon, etc. Example:
O 2N N N HO (Nitroaniline red)

e)

f)

Vat Dyes: Before being introduced on to fabric these dyes are first reduced to colourless leuco compounds in wooden vats by alkaline reducing agent. The fibre is then soaked in the solution of the dye. After proper absorption of the dye, the fibre is then exposed to air or to an oxidising agent. By doing so the dye gets oxidised to yield insoluble coloured dye on the fabric. Example: Indigo dye

g)

Mordant Dyes: A dye which imparts different colours to the fabric in the presence of different metal ions (called mordants) is referred to as mordant dye. Nowadays it is rarely used Application: These dyes are used for dyeing of wool. The method involves the precipitation of certain substances on the fabrics which then combine with the dye with the dye to form an insoluble coloured complex called lake. Depending on the kind of mordant used different colours. For example, Alizarin, a mordant dye, gives red colour with aluminium and tin salts, where as brownish red colour chromium mordant and black violet with iron mordant.

HISTORY:
Dyed flax fibers have been found in the Republic of Georgia dated back in a prehistoric cave to 36,000 BP. Archaeological evidence shows that, particularly in India and Phoenicia, dyeing has been extensively carried out for over 5000 years. The dyes were obtained from animal, vegetable or mineral origin, with no or very little processing.

Earlier, all dyes were made from natural resources like plants and animals. During the Late 1800s and early 1900s, chemists developed synthetic dyes. Synthetic dyes are available with a variety of colour shades, are fast and cheaper in cost.

CHARACTERISTICS OF A DYE

It must have a suitable colour. It must be capable of being fixed to the material. When fixed it must be fast to detergents, soaps, water, dry cleaning solvents, light and dilute acids.

Origin of colour in dyes The colour of dyes is attributed to their ability to absorb some wavelengths of visible region of electromagnetic spectrum (380 nm to 760 nm). The part of the colour which reflected back gives the colour of the dye i.e. complementary to the colour absorbed. The colour of visible light absorbed and the complementary colour reflected are listed in table.

Wave length (nm) 400 435 435 480 480 490 490 500 500 560 560 580 580 595 595 605 605 750

Colour absorbed Violet Blue Greenish Blue Bluish Green Green Yellowish Green Yellow Orange Red

Complementary colour Yellow, Green Yellow Orange Red Purple Violet Blue Greenish Blue Blue, Green

In the earlier days fabrics were coloured by the dyes mainly from Alizarin (red dye) and indigo (blue dye).

Health and safety

Any dyes including acid dyes have the ability to induce sensitization in humans due to their complex molecular structure and the way in which they are metabolised in the body. This is extremely rare nowadays as we have a much greater understanding through experience and knowledge of dyestuffs themselves. Some acid dyes are used to colour food. We wear fabrics every day exposing our skin to dyes. The greatest risk of disease or injury due to dyes is by ingestion or exposure to dye dust. These scenarios are normally confined to textile workers. Whereby the dye itself is normally non toxic, the molecules are metabolised (usually in the liver) where they may be broken back down to the original intermediates used in manufacture. Thus many intermediate chemicals used in dye manufacture have been identified as toxic and their use retricted. For example: the dye CI Acid red 128 was found to metabolise in the body back to ortho-toluidine, one of its chemical intermediates. Many intermediates used in dye manufacture such as o-toluidine, benzidine etc. were found to be carcinogenic.

Experiment

AIM
To prepare fluorescent dye and dye a cotton cloth directly with it.

APPARATUS REQUIRED
Test tubes, weighing balance, burner, conical flask, a piece of cotton cloth, a pair of tongs.

CHEMICALS REQUIRED
Resorcinol - 2g, pthalic anhydride 2g, 5% solution of NaOH, Conc.H2SO4.

PROCEDURE

1. 2g of Resorcinol and 2g of pthalic anhydride were taken in a test tube, and 2ml of conc. H2SO4 was added to it. 2. The contents were heated and till the contents turned black. 3. The contents were cooled and 20ml of 5% NaOH were added to it in a conical flask. 4. The concentration of NaOH and water was varied to get the desired intensity of colour. 5. The cotton cloth was dipped in the boiling solution with the help of tongs, and then washed and dried.

OBSERVATIONS
The dye formed shows properties of fluorescence. It appears green from some angles and orangish-yellow from others. The dye, when put in a large amount of water in the sink turned into a bright-yellow colour. The colour of the cotton cloth was uniform but was not fast on washing, therefore fluorescent dye acts as a mordant dye to cotton.

Bibliography
Wikipedia the free encyclopedia Together with Chemistry Lab Manual www.google.com www.bing.com