Section -I: Introduction - Shodhgangashodhganga.inflibnet.ac.in/bitstream/10603/3032/7/07_chapter...

Section-I: Introduction

Section-I: Introduction 1

Section-I

Introduction

Reactive dyes are colored compounds which contain one or two groups

capable of forming covalent bonds between a carbon or phosphorus atom of the dye

ion or molecule and an oxygen, nitrogen or sulphur atom of a hydroxy, an amino or a

mercapto group, respectively, of the substrate. Such covalent bonds are formed with

the amino, hydroxyl groups of cellulosic fibres, with the amino, hydroxyl and

mercapto groups of protein fibres and with the amino groups of polyamides[1]

. In

general, reactive dyes are the only textile colorants designed to bond covalently with

the substrate on application. They are used for the dyeing and printing of cellulose

and to a lesser extent polyamide fibres. They are valued for their brilliance and variety

of hue, versatility and high wet fastness profiles.

The reason for such a rapid increase in demand is primarily due to the

excellent characteristics of reactive dyes, e.g. their brilliant shades, excellent wet

fastness of dyeing and simple dyeing operations which have increasingly been

accepted within the industry. However, with the growth in the usage of reactive dyes,

additional properties have been demanded by dye works and apparel manufactures[2-5]

in particular high fixation in exhaustion dyeing and high fastness to chlorine

perspiration, light and washing in the presence of peroxides.

The first dye of this group was introduced in 1956 under the name ‘Procion’

by the Dyestuffs Division of Imperial Chemical Industries Ltd. Most of the procion

dyes are water soluble, easily applied and because the reactive group may be attached

to almost any colored molecular system, can be used to produce both very bright and

very dull shades of all colors. Procion dyes are greatly superior to direct cotton dyes,

which have high affinity. Because of their distinctive advantages, the procion dyes,

and fibre reactive dyes generally, have made a greater impact on dyeing technology in

the few years since their introduction than any other class of dyes in so short time.

Close attention has been paid to the fact that the existence of cations results in

some of the coloristic properties of these kinds of dyes[6]

. Reactive dyes are well

known and applied for dyeing of different materials[7]

. Among them triazine

derivatives have an important place.



Reactive dyes are widely used for dyeing and printing protein fibres. The

hydrophilic group of conventional reactive dyes is an anionic group, e.g. sulphonate

or carboxylate but the hydrophilic group of reactive cationic dyes is cationic[8]

.

Reactive dyes, the newest addition of existing dyes are the centre of attraction

in dyestuff research[9,10]

. Several new reactive systems have been introduced from

time to time which covers the subject of innumerable patents and publications[11-13]

.

Hot brand reactive dyes are of major commercial importance in reactive dyeing[14]

.

It is particularly suitable in dyes for printing. On silk these dyes are reported to give

moderate to poor build-up[15, 16]

. Hot brand reactive dyes have been widely considered

due to their higher fixation yield on various fibers[17]

. Reactive dyes are becoming

increasingly popular for dyeing cellulosic fibres because of their wide shade range,

ease of application and excellent wet fastness properties. Improvement in the structure

of reactive chromogens, selection and number of reactive groups led to an increased

use of reactive dyes[18-20]

.

Reactive dyes are now a major group of dyes, though a late entry into the

family of synthetic dyes, have very soon attained a commercial status. There is no

slackening of activity in this field as seen from the large number of patent

specification and several ranges which continue to appear in the market[21-23]

.

Constitution of Reactive Dyes

In principle, a reactive dye should contain a leaving group (X) which can

undergo nucleophilic displacement by hydroxyl group of cellulose in the presence of

aqueous alkali (Dye–X + Cell–OӨ →

Dye–O–Cell + X

Ө ) or an activated –C=C– bond

which is able to add to a hydroxyl group of cellulose.

(–CH=CH2 + Cell–OH → –CH2–CH2–O–Cell).

Reactive dyes are the only textile coloration products designed to furnish

covalent bonds between dye and substrate during dyeing. Although many different

reactions can be used for fixation, two main types are exploited commercially, i.e.

hetero aromatic nucleophilic substitution and addition to an activated alkane[24-27]

.

Thus, the majority of reactive dyes can be distinguished in to two categories

by their reaction modes as:



(i) Nucleophilic addition-elimination dyes:

(ii) Nucleophilic addition dyes:

The general formula of a reactive dye is given as,

a – c – b – R

Where, ‘a’ is water-solubilizing group. Generally, SO3Na and COONa groups

are used as a water-solublizing group. ‘b’ is a bridging group which links together

chromophoric ‘c’ and reactive ‘R’ systems. The commonly used bridging groups are

–NH–, –N(CH3)–, and –CH2O– etc. The bridge unit affects to a great extent, the

reactivity of the dye and the tendency of the corresponding dyeing to hydrolyze.

‘R’ is a reactive group. The dye-fibre compound may have the properties of an

ester or ether; the precise nature and stability of the dye fibre bond will depend on the

reactive group.

Chromophoric system ‘c’ is mainly responsible for the color of the dye.

Various types of shade can be obtained by changing the chromophoric system. From

the large number of suggested chromophoric system azo, antraquinone and

phthalocyanine derivatives have achieved greatest economical importance up to

present date. Dyestuff of these groups forms the hard core of all commercial reactive

dyestuff ranges. The widest range of shades is covered by the azo compounds, which

comprise practically every shade from greenish yellow to black. Brilliant blue and

green shades with high fastness to light are mainly from anthraquinone derivatives,

while sulfonic acids of copper and nickel phthalocyanine are used to produce

turquoise shades and in combination with yellow dyestuff to synthesize bright green

shades.



Classification of Reactive dyes

Reactive dyes can be classified into different groups as follows:

Major commercial types of reactive dyes for cellulose

Structure

Commercial

Name

Firm

Year of

Introduction

Procion

ICI

1956

Procion H

Cibacron

ICI

CIBA

1957

1957

Remazol

Hoechst

1958

Levafix P

Bayer

1966

Primazin P

BASF

1964



Major commercial types of reactive dyes for wool and polyamides

Structure

Commercial

Name

Firm Year of

Introduction

Procilan

ICI

1964

Lanasol CIBA 1966

Verofix

Drimalan F

Bayer

Sandoz

1970

1970

Various Reactive Systems

Reactive systems, in general, can be classified as aliphatic, aromatic and

heterocyclic reactive system as follows.

[A] Aliphatic Carrier Systems of Labile Groups

Substituted Alkane - Mono Carboxylic Acid Amides

The dyeing of cellulosic textiles with dyestuffs containing chloroacetylamino

groups (I) was first described by BASF[28]

, and later also by other firms. The fixation

yields of these chloroacetylamino reactive dyestuffs are also not particularlily high on

cellulosic fibers.



CIBA[29]

described wool-reactive dyes containing β-chloro propionylamino

groups (II) and recognized the suitabilities of β-chloro propionylamino dyestuffs,

which are in most cases freely water-soluble and possess less affinity for the

continuous dyeing and printing of cellulosic fibres[30]

.

In a BASF patent[31]

relating to β-sulphonylpropionamide dyestuffs (III)

sulphonyl group is described and claimed in anthraquinone, azo and phthalocyanine

dyes.

α,β-dihalopropionamides (IV) were developed by CIBA[32]

in cellulose

reactive dyes. The use of dichloro or dibromo propionic acid[33]

is claimed in a

number of new dyes. Among other substituted aliphatic carboxylic acid, amides and

substituted isobutyric acid amides[34]

are claimed as new reactive components.



Substituted Alkane - Monocarboxylates

This new reactive dyestuffs group (V) was discovered by General Aniline and

Film Corporation[35]

. In such dyes saponification of propionic ester, leads to bond

formation resulting in good yield, good fixation and better fastness to washing.

Substituted Cycloalkane Carboxamide

From ethylenetetrafluoride and acrylonitrile or 1-cyano-butadiene or their

derivatives, fluoro cyclobutane carboxamides are obtained (VI) which is useful

reactive dyestuff groups. Farbwerke Hoechst and other firms[36]

have claimed number

of patents related to this group.

Alkene Monocarboxamides

Reactive dyes with β-chloropropionylamide groups containing acrylamide are

fairly slow in their reaction. They are less suitable for the dyeing of cellulosic

materials than for pad dyeing processes and textile printing. The crotonamide group is

even less reactive.

Substituted Aliphatic Ketones

The stability of dyestuffs containing chloromethyl or β-chloroethyl aryl ketone

groups (VII) for the dyeing of cellulose in the presence of alkalies was recognized by

BASF and General Aniline[37]

.



β - Substituted Ethyl Sulphone-Vinyl Sulphones

The following reactive systems are frequently referred to as ‘Vinyl Sulphones’

to simplify matters, though strictly speaking they are Vinyl sulphone intermediates.

For this reason, the majority of papers and patent specifications refer to a

multitude of β-substituents (X), which are quite easy to eliminate, e.g. XӨ=Cl

Ө.

Reacive dyes containing β-haloethyl sulphone groups are recommended by CIBA[38]

for the dyeing of cellulose. Generally β-substituents XӨ = Cl

Ө, (Alkyl)2N

Ө, HO3SS

Ө,

H2O3POӨ, but primarily OSO3H is used. In the case of azo dyes the vinyl sulphone

group is usually substituted directly into the aryl nucleus of the diazo component or

that of the coupling component. In a number of patents, however bridges are included.

e.g. –NH–, –(CH2)n–, –CONR(CH2)n–, –SO2NRAryl–, –CONRAryl– and

–NRSO2Aryl– between the aryl nucleus and the vinylsulphone group. In this

connection references have been made to a large number of patents primarily from

Farbwerke Hoechst, as well Sumitomo and other firms[39,40]

covering this reactive

group (VIII & IX).



In some reviews, attention is focused on the development of vinyl sulphone[41]

dyes and their general fields of applications.

β - Substituted Ethylamine Derivatives

In 1956, dyestuffs containing β-haloethylamines group for dyeing cellulosic

materials was described by BASF[42]

. The N,N-bis-(β-chloro-ethyl)-hydrazide group

(X) claimed by Sandoz is interesting from chemistry point of view. Thus all

ethylamine derivatives, containing a group in the β-position, which is capable of

splitting off together with the bonding electron pair under alkaline medium, have been

mentioned as reactive groups used in reactive dyes for the dyeing of cellulose, nylon

and wool.

β - Substituted Ethylamides of Sulphonic Acids

ICI[43]

recognized that the water-soluble dye (XI) containing N-β-halo ethyl

sulphonamide groups are fixed on cellulosic fibres from aqueous alkaline medium

shades which possess excellent wet-fastness properties.



Epoxide Derivatives and Their Precursors

The group (a) and its precursor (b) are nearly always mentioned together.

Water-soluble reactive dyes of this type give dyeing with very good wet fastness

properties.

[B] Aromatic Carrier Systems

Due to equivalence of the group >N– and ≥C–NO2 with regard to the

activation of halogen atoms in the ortho or para position in hetero aromatic or

aromatic rings, the aromatic carrier systems are rarely used. The virtual absence of

papers on the use of well-known aromatic carrier systems shows that they are of little

practical importance. One of the interesting systems[44]

is given below (XII).

[C] Heterocyclic Carrier Systems

Pyridine Derivatives

Halogen substituents attached to pyridine or quinoline systems are not

sufficiently reactive to form covalent bonds with cellulose under normal dyeing or

printing conditions unless suitably situated electron-attracting groups are also present

in the ring to give enhanced reactivity. By condensation of amino dyestuffs with

3,5-activated 2,6-dichloropyridine[45]

derivatives, easily fixed reactive dyes (XIII) are

obtained.



Pyridazone derivatives

Reacton/ Drimarine

This reactive group, has been achieved technical importance in reaction, the 6-

pyridazone substituted on nitrogen atom 1 is not an aromatic nitrogen heterocyclic; its

4,5-dihalo derivatives react in the 4-position as vinylogous carbonyl halides.

Pyridazine Derivatives

Dyestuffs containing chloropyridazine groups[46]

are suitable for the printing

and continuous dyeing of cellulosic fibres with subsequent fixation in dry heat or in

steam. Tetrachloropyridazine condensed in an aqueous alcoholic medium with

1,3-diamino benzene-4-sulfonic acid, after diazotization and coupling gives the

following dyestuff (XIV).



Pyrimidine Derivatives

Pyrimidine is the most important heterocyclic carrier system.

Reactive Dyes containing a Chloropyrimidine Nucleus

(a) Dichloropyrimidine type

(b) Trichloropyrimidine type

Reacton Drimarene Z

Reactive Dyes Containing a Cyanuric chloride Nucleus

Cyanuric chloride contains three labile chlorine atoms which can be replaced

in succession to an amine salt or a hydroxyl compound. A simple dye containing a

cyanuric chloride can be represented as follows:

(a) Procion H (Cibacron)

Monochlorotriazine reactive dyes



Where X = Aromatic or Aliphatic amine or dye with a free amino group attached to

the chloride or heterocyclic residue.

(b) Procion M

Dichlorotriazine reactive dyes

1,2,4-Triazine Derivatives

Halogen derivatives of not easily available 1,2,4-triazine are suitable as

reactive compounds. Finally powdered 3,5-dichloro-1,2,4-triazine condense with the

appropriate aminoazo dyestuff in aqueous solution at 0-5ºC and pH 4.5-6.0 forming a

reactive dyestuff, the constitution of which (substitutions position on 1, 2, 4-triazine)

is not exactly known.

Phthalazine Derivatives

Dyestuff with 1,4-dichlorophthalazine-6-carbonyl chloride, reactive

components are extremely suitable for textile printing and continuous dyeing.

Bayer[47]

recognized the value of this dyestuffs group under the name Elisiane

dyestuffs.

Elisiane Brilliant Red B

Quinoxaline Derivatives

This technically important reactive principle was developed by Bayer[48]

,

Dupont[49]

, CIBA[50]

and Francolor[51]

. Commercial products on this basis are Levafix

E dyestuffs and the Cavalite dyestuffs.



Levafix Brilliant red E-2B (Cavalite Red Y)

F. Oesterlein and K. Seitz[52]

have synthesized fibre reactive disazo dye having

structure (XV) gave greenish blue dye from cotton.

Where, R = Et, Me.

R1 = H, NH2, SO3H.

CIBA[53]

prepared fibre reactive azonaphtholsulfonic acid dyes (XVI) to give a

reddish brown dye for cotton.

Where, R = Cl, NH2

ICI[54]

discovered the cyanuric bromide is also suitable for the synthesis of

reactive dyestuff (XVII).



ICI[55,56]

patented the dyestuff Procion yellow M-RS (XVIII) as well as

Procion Brilliant Orange M-FS (XIX) in the year 1954.

A. Crabtree[57]

has synthesized diazo component to manufacture reactive dyes

from m-phenylene diamine-4,6-disulfonic acid and cyanuric chloride, which gives

bright red shade of the following structure (XX).



Ciba Geigy[58]

prepared monoazo reactive dye (XXI) for cotton to give golden

yellow shades.

Sumitomo Chemical Co. Ltd[59]

prepared reactive disazo dyes (XXII) of free

acid to give reddish brown shades on cotton. Jarkovsky and Horyna[60]

prepared

brown fibre reactive triazine disazo dye for dyeing cellulosic fibres (XXIII). The

presence of two o-Me groups disturbs the co-planarity of dye molecular and lowers

the substantivity of unbound dye.

Where, R = NHCH2SO3Na, NHCH2CH2SO3Na

Where, R = Cl, NH2, MeO



Jin et al.[61]

have synthesized scarlet dyes for cotton fabrics (XXIV).

Where, R = SO2CH2CH2OSO3H

Ciba-Geigy prepared[62]

a reactive azo dyes for silk, leather, wool, polyamide,

fibers, polyurathanes, rayon, cotton and cellulose of the structure (XXV).

P. M. Mistry and J. A. Taylor[63]

have synthesized navy blue reactive azo dyes

for cotton (XXVI). The compounds are characterized by good strength and ability to

build up exhaust and pad-batch dyeing to heavy depths of shade, producing colored

textiles having good resistance to washing and light.



K. Seitz[64]

prepared disazo reactive dyes for cellulosic fibres based on H-acid,

K-acid, S-acid or J-acid. The synthesized compound show high degree of fixation

when applied by low temperature process and produce fast navy blue dyeing and

printing cotton.

A. Tzikas[65]

has synthesized reactive dyes, which gives fast navy blue shades

on cotton in dyeing and printing.

Herd et al.[66]

have synthesized fibre reactive dyes (XXVII) containing a

halopyrimidinyl anchor group useful for the high color yield dyeing or printing of

hydroxyl or amide group containing fabrics in fast bluish red shade on cotton.

Mitsui Toatsu Chemicals[67]

prepared water soluble reactive anthraquinone

dyes useful for dyeing cellulose fibre. The cotton knitted fabric was dyed in a dye

bath containing water and glauber’s salt heated at 60°C in the presence of Na2CO3 to

give uniformly dyed product with deep color, which showed color fastness to light

grade 5, color fastness to wet and light grade 4-5.

Hardina et al.[68]

have synthesized novel reactive dyes for wool. This type of

reactive dyes can be prepared by diazotization of aromatic amine and subsequent

coupling reaction with secondary components. These dyes contain

–SO2CH2CH2N(CH3)CH2COOH group capable of liberating reactive vinyl group in

the application dye bath. The dye showed acceptable wash fastness and light fastness.

D. Akerman and co-worker [69]

have synthesized azo/hydrazo dyes (XXVIII)

derived from H-acid, with superior resistance to oxidative bleach fading.



Where X = H, Cl, Br.

Y = H, Cl, Br.

SES = Sulfato Ethane Sulfonyl.

Patel et al.[70]

have synthesized hot brand reactive dyes (XXIX) by coupling

tetrazotised 4,4'–diaminodiphenyl sulphonamide with o-Fluoro anilino cyanurated

coupling component, and their dyeing performance on silk, wool and cotton fibres has

been assessed.

Where R= o-fluoro aniline

P. Suwanruji and H. S. Freeman[71]

have synthesized bifunctional bisdichloro

triazine (bis-DCT) and tertafunctional bis monochlorotriazine/bis sulphatoethyl

sulphone [bis-(MCT/SES)] reactive dyes were applied to cotton for good color

fastness & rubbing fastness.

Mokhtari et al.[72]

have synthesized trisazo heterobifunctional reactive dyes

(XXX) which gives variety of shade on cotton.



Where Z =

X = -CH3, -H, -SO3Na.

Y = -CH3, -OCH3, -OC2H5

P. Petrova-Miladinova and T. N. Konstantinova[73]

have synthesized reactive

triazine azodyes (XXXI) containing tertamethyl piperidine (TMP) fragment. The dyes

co-polymerized with acryl amide and acrylonitrile and the co-polymer with an intense

orange color which is stable to solvent extraction.

Where,

A1 = -NH2 -Cl

A2 =

-Cl



Y. W. Ho and W. H. Yao[74]

have synthesized heterocyclic monoazo (XXXII)

dyes by appropriate selection of substituents in the coupling components dyes varying

in hue from yellow to blue can be obtained. The dyes were applied to polyester; their

spectral, fastness properties and color assessment are reported.

Where,

R =

Ar =

D. M. Lewis and A. A. Siddique[75]

have prepared reactive dyes (XXXIII)

based on the bis (N-Carboxyl methyl amino) mono-quaternary-triazine-bis-

ethylsulphone reactive group having following structure gives good application to

cotton fabrics.

Chen et al.[76]

synthesized reactive dyes containing an alkyl-thio-s-triazinyl

reactive group. It is suitable for exhaust dyeing, cold batch up dyeing and continuous

dyeing materials that contain hydroxyl group or N-group fibres.

A. A. Mousa[77]

has synthesized polyfunctional reactive dyes (XXXIV)

containing bis (monochloro triazine/ sulphatoethyl sulphone) reactive system, which



shows good dyeing property on silk. The twinned MCT/SES reactive system confers

relatively high fixation efficiency even at low salt/temp condition.

Where R= SO2CH2CH2OSO3Na

E. L. Gillingham and David M. Lewis[78]

have prepared triazinylamino

alkylphosphonate reactive dyes (XXXV) for cotton fabrics. Which shows very high

dye-fibre fixation value (>90%) by using pad-batch-bake process.

Patel et al.[79]

have been synthesized hot brand reactive dyes (XXXVI) by

coupling tetrazotized 4,4'–methylene bis 2,5–dichloroaniline with various m-toluidino

cyanurated coupling component for silk, wool and cotton fabrics.

Where R=m-toluidine



Ruan and Weixiang[80]

have synthesized tetrazo reactive dyes which are

prepared by reaction between sulfonyl containing compound and amine containing

compound and the diamine. This dye is useful for dyeing or printing of fibres.

Chu and Pingzhong[81]

have synthesized blue reactive dyes (XXXVII). The

product has high color fixation rate and high binding stability.

Where X = F, Cl, NH2CH2CH2SO2CH2CH2OSO3H.

Y = F, Cl, NH2CH2CH2SO2CH2CH2OSO3H.

R1 = H or Sulfonyl.

R2 = Sulfonyl.

Chu and Pingzhong[82]

have synthesized reactive brown dye (XXXVIII).

These dyes give good light fastness, perspiration resistance and soaping resistance,

and can be applied to dip dyeing, pad dyeing, jig dyeing and continuous pad dyeing of

cotton, rayon and hemp textiles.

Where R1 = H, Me, Methoxy or Sulfonic group.

R2 = H, Me, Methoxy.



R3 = H, Sulfonic group or –COOH.

Z = -SO2Y (on the m-position or p-position of amino group).

Y = Vinyl or –CH2CH2U and U can leave under alkali condition.

M = H or alkali metal.

J. Paluszkiewicz and W. Czajkowski [83]

have synthesized bifunctional reactive

dyes (XXXIX) with quinolino-s-triazine groups, and their application properties

during the dyeing of cotton fabrics were determined.

B. M. Patel and S. K. Patel[84]

have synthesized bisazo reactive dyes (XXXX),

which gives a wide range of violet to red shades on cotton fibre.

Mehta et al.[85]

have synthesized cold brand bisazo reactive dyes (XXXXI) for

silk, wool and cotton fibres. Exhaustion, fixation and fastness properties of these dyes

were also reported.



D. N. Wadia and P. M. Patel[86]

have synthesized monofunctional reactive

dyes (XXXXII) using various substituted imidazole-4-one. All the dyes were applied

to wool fabrics using various pH conditions. Wash and light fastness of prepared dyes

were reported.

Where R1= 4-OCH3; 3,4,5-OCH3; 4-OH; 4-Cl; 2-OH, 3-OCH3; 2-OH; 4-N(CH3)2;

H; 4F.

T. Kim and co-worker[87]

have synthesized disazo yellow dyes of following

structure (XXXXIII). The fastness properties and K/S value are also reported.

Where R= Methyl, Ethyl, Propyl, Butyl, Pentyl, Hexyl and Heptyl groups.

H. Z. Shams[88]

has synthesized disazo reactive dyes (XXXXIV) using

pyrazolo[1,2-a]pyrazole fused system as chromophoric moiety. The synthesized dyes



were applied to cotton, wool and silk fabrics under the typical exhaust dyeing

condition and their fastness properties were investigated.

Where

Ar =

D. R. Patel and co-worker [89]

have synthesized hot brand bisazo reactive dyes

(XXXXV). These dyes were applied on silk, wool and cotton fibres. The fastness

properties, exhaustion and fixation data were also been studied.

Where R=m-nitro aniline.

D. R. Patel and co-worker [90]

have synthesized cold brand reactive dyes with

quinazoline moiety (XXXXVI). All these dyes give yellow to purple color shades

with good fastness properties. The exhaustion and fixation data of all the dyes are

very good.



S. H. Ungoren[91]

has synthesized anthraquinone dyes (XXXXVII) from furan-

2,3-diones and their spectroscopic properties in solution and in the solid state are

reported.

F. Karci and co-worker[92]

have synthesized heterocyclic disazo dyes

(XXXXVIII). The antimicrobial activity and absorption characteristics of the dyes

were also reported.

Where X= H; p-OCH3; p-Cl; p-CH3; m-OCH3; m-Cl; m-CH3; o-OCH3; o-Cl; o-CH3

J. Mokhtari and co-worker[93]

have synthesiszed trisazo hetero bifunctional

reactive dyes (XXXXIX) based on J-acid. The dyeing properties have also been

reported.



Where,

Z= SO2CH2CH2OSO3H

X= H H SO3H

Y= H CH3 H

B. Yang and co-worker[94]

have synthesized tetrazine dyes with pyrazole

molecule. the reaction mechanism of formation of the 5-aryl-3-methylpyrazole[3,4e]

[1,2,3,4] tetrazines is discussed and the colors of the aminopyrazoles and pyrazolo-

tetrazine dyes in a range of solvents are also discussed.

D. R. Patel and co-worker[95]

have synthesized bromine containing bisazo

reactive dyes of following structure (L). All the dyes were applied to wool, silk and

cotton fibres with fair to very good light, wash and rubbing fastness properties. All the

dyes showed good exhaustion and fixation data.

Where R=m-toluidine

Patel et al.[96]

have synthesized bisazo reactive dyes (LI) from 4,4'-methylene-

bis-anthranilic acid. These dyes were applied to wool, silk and cotton fibres, which

shows moderate to very good light, wash and rubbing fastness properties.



Where R=m-chloro aniline.

Patel et al.[97]

have synthesized cold brand bisazo reactive dyes (LII) from

4,4'-methylene bis-(2,3-dichloro aniline). The dyed fibres show moderate to very

good fastness to light, washing and rubbing on silk wool and cotton fibres.

Literature on Quinazolinone

Quinazolinones

Quinazolinones[98]

are versatile nitrogen containing heterocyclic compounds.

In 1869 Griess[99]

prepared the first quinazoline derivative, 2-cyano-3, 4-dihydro-4-

oxoquinazolinone, by reaction of cyanogens with anthranilic acid. Griess apparently

recognized the bicyclic nature of the product, which he called bicyanoamidobenzene

and used until 1885 when the structure was known with some certainty[100]

.

Weddige[101]

carried out systematic quinazoline synthesis following the observation

that the formyl and acetyl derivatives of anthranilamide lost water on heating. He

correctly interpreted this as a cyclization reaction and was first to realize the

possibility of tautomerism in the oxoquinazolines. The preparation of parent

quinazoline comes many years later when Bischler and Lang[102]

obtained it by

decarboxylation of the 2-carboxy derivatives. A more satisfactory synthesis of

quinazoline was subsequently devised by Gabriel[103]

who studied its properties and

those of its derivatives in greater detail.



Numbering System of Quinazolinone

The nomenclature of the quinazolinone ring system is as follows.

Quinazolinone is also known as phenmiazine, benzylene-amidine, 1, 3-diaza-

naphthalene or benzo-1, 3-diazine or 5, 6-benzo-pyrimidine. The term phenmiazine

was used by Wildman[104]

. The numbering shown in the structure was suggested by

Paal and Busch[105]

and is one in the current use[106]

. The quinazoline having a

hydroxyl group in 2- or 4- position forms a distinct class and are tautomeric[107]

with

the corresponding ketodihydroxyquinazoline. Various data[108,109]

indicate that

4-hydroxyquinazoline exists as an equilibrium mixture of (a) and (b) in which the

form (a) is the most favoured.

The 4-hydroxyquinazolilne tautomeric with 4-keto-3, 4-dihydro-quinazoline,

is commonly named as 4(3H)-quinazoline is also the familiar name used for the

system. Today the name 4-quinazoline has been universally accepted for 4-keto-3, 4-

dihydroquinazoline.

Synthesis of Quinazolinone

The majority of synthetic route of 4-quinazolinone essentially proceeds from

anthranilic acid or its derivatives. A number of methods may be classified into

different categories according to the type of the components undergoing

condensation.



TYPE – 1

This type includes condensation of

(1) N-acetyl anthranilic acid with aromatic amine in presence of

phosphorus trichloride[110-112]

.

(2) N-acetyl anthranilic acid with acetic anhydride affording 2-methyl-3, 1,

4-benzoxazone that is subsequently allowed to react with an amine[113-119]

.

(3) N-acetyl anthranilic acid with an amine in a sealed tube[120]

.

(4) N-acetyl anthranilic acid with formamide[121]

.

TYPE – 2


(1) Anthranilic acid with acid-amide[122-124]

.

(2) Anthranilic acid with cyanamide[125]

.

(3) Anthranilic acid with a compound containing –N=C-Cl system[126-128]

.

TYPE – 3


(1) Acetanilide with urethane in presence of phosphorus pentoxide[129-131]

.

(2) Benzanilide imidochloride with urethane and subsequent cyclization[132-133]

.

TYPE – 4


(1) Anthranilamide with acid chloride and subsequent cyclization of

N-acylanthranilamide[134-136]

.

(2) Anthranilamide with acetic anhydride[137-138]

.

In addition to this many other reactions are reported which lead to the

synthesis of 4-quinazolinones[139-144]

.

Chromophoric potential of the 4(3H)-quinazolinone

Heterocyclic coloring matters have been known since prehistoric times in the

form of natural products such as indigo and its 6, 6'-dibromo derivative, Tyrian

Purpssle. The first commercial synthetic dye, Mauveine, discovered by Perkin in 1856

was also heterocyclic. Since that time the contribution of heterocyclic derivatives to

color chemistry has been considerable. Dyes based on the quinazoline ring system



have been reported as being useful on natural and synthetic fibres[145]

. Such dyes have

excellent dyeing properties including low sublimation and high thermal stability[146]

.

The quinazoline nucleous is the key component of a number of colored

products. The following literature shows the important role of the 4(3H)-

quinazolinone ring as a chromophore.

Azo disperse dyes such as following (LIII) containing a 4(3H)-quinazolinone

derivative as coupling component have been synthesized by Bhatti[147]

gives yellow to

red shade with good fastness on natural and synthetic fibers.

Where, X = H, NO2; Y = NO2, Cl; Z = H, CN, OCH3

A. Arcoria and G. Scarlata[148]

have synthesized azo dyes (LIV) with excellent

light fastness and saturation on wool, cotton, rayon and nylon.

Where X = H or COOH.

P. S. Patel and co-worker[149]

have synthesized heterocyclic monoazo dyes

(LV) from 4-oxoquinazoline. Dyeing properties of these dyes on wool and silk were

assessed. Fastness properties have also been studied.



Where R= Various coupling component.

H. Jung and W. Kurtz[150]

have synthesized quinazoline azo pigment (LVI)

gives yellow to orange shade and useful in dyeing, printing inks, lacquers and PVC.

A. A. Cavesco[151]

has synthesized fluorescent 4(3H)-quinazolones (LVII)

containing sulphonamide or carboxamidophenyl groups are reportedly used in

luminescent inks for paper.

Where R1 = H, Cl; R

2 = Ph, CH3; Q = SO2, CO.

Desai et al.[152]

have synthesized reactive dyes (LVIII) based on quinazoline

ring system, which gives yellow to red shade with good fastness on natural and

synthetic fibers with different coupling component.



Where R = H, CH3, OCH3, NO2, Cl, Br.

Naik et al.[153]

have synthesized heterocyclic monoazo dyes (LIX) for

application to viscose, silk and polyester. Dyeing and fastness properties of the dyes

were evaluated.

Where R = various coupling component.

Fadda et al.[154]

have synthesized heterocyclic azo styryl dyes (LX) shows

good fastness property and variety of shade on viscose, silk and polyester.

Where R = various coupling component.

Rana et al.[155]

have prepared various acid dyes (LXI) by coupling diazotized

2-Methyl-3-(2’-chlorophenyl)-6-amino-4-oxoquinazoline with various coupling acid

component and their dyeing performance on silk, wool and nylon fibres has been

assessed.



Where R = various coupling component

Patel et al.[156]

have synthesized 4(3H)-quinazolinone based disperse dyes

(LXII), shows good fastness properties on nylon 66 and polyester fibres.

Where R= various mono and di-N-substituted aniline derivatives

Vijay H. Patel[157]

and co-workers have synthesized novel heterocyclic

monoazo dyes (LXIII) by coupling with various naphthols. The dyed fibers shows fair

to good fastness to light and very good to excellent fastness to washing, rubbing,

perspiration and sublimation.

Where R = various Naphthols such as, Naphthol AS,



H. S. Bhatti and S. Seshadri[158]

have synthesized styryl disperse dyes (LXIV)

derived from 6-nitro substituted 3-aryl-2-methyl-4(3H)-quinazolinone. The

application properties of these dyes on polyester and their fastness properties have

been evaluated.

Where R1=CH3, C2H5; R2=CH3, C2H5, CH2C6H5

S. V. Patel and co-worker[159]

have synthesized fluoran compound (LXV)

containing bromo quinazoline molecule. All these colorless fluorans develop a color

in contact with electron accepting compounds.

Where R= CH3 or C6H5, R1=Br, R2=H or Br.

S. V. Patel and co-worker[160]

have synthesized quinazoline substituted fluoran

compound which shows color on contact with electron accepting compounds.

M. F. Abdel-Megeed and co-worker[161]

have synthesized azo disperse dyes

containing quinazoline nucleous (LXVI). These dyes were applied to polyester fabrics

and their fastness properties were evaluated.



Where Ar = α-Naphthol, β-Naphthol, Phenol, Resorcinol

H. D. Navadiya and co-worker[162]

have synthesized mono azo dyes (LXVII)

derived from 2-phenyl-3,1-benzoxazine-4-(4H)-one. All the dyes showed good

fastness properties on nylon and polyester.

Where R= Phenol, o-cresol, m-cresol, p-cresol, o-cl-phenol, m-cl-phenol.

Patel et al.[163]

have synthesized reactive dyes based on 2-phenyl-3-[4′-(4″-

aminophenylsulphonamido)]phenyl-4(3H)-quinazolinone-6-sulphonic acid (LXVIII)

and applied on silk, wool and cotton fibres. These dyes give good fastness properties.

Where R = Various 4-chloro anilino cyanurated coupling components.

D. R. Patel and K. C. Patel[164]

have synthesized monoazo reactive dyes

(LXIX) containing quinazolinone moiety shows good dyeing as well as fastness

properties on silk, wool and cotton fibres.



Where R= various 2-chloro, 4-nitro anilino cyanurated coupling components

J. T. Bilimoria and K. C. Patel

[165] have synthesized monoazo dyes (LXX)

derived from 2-methyl-3-(2'-methylphenyl)-6-arylazo-4-oxoquinazoline for silk, wool

and viscose rayon fibres. All the dyes showed fair to very good light fastness and very

good to excellent washing and rubbing fastness properties.

Where R= various cyanurated coupling components

D. R. Patel and K. C. Patel

[166, 167] have synthesized monoazo reactive dyes

based on 4(3H)-quinazolinone moiety. These dyes gives yellow to purple hues with

fair to very good light fastness and very good to excellent washing and rubbing

fastness properties. Some of the dyes showed good antimicrobial activity.



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166. D. R. Patel, K. C. Patel, J. Serb. Chem. Soc. (2010) (Accepted-In press).

167. D. R. Patel, K. C. Patel, Dyes Pigm. (2010) (Accepted).

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