Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar 388 120

Received 5 September 1984; accepted 3 December 1984

n~ n" •••• _ •• n _

Indian Journal of Textile ResearchVol. 10. June 1985, Pp. 71-74

Azoacid Dyes with 4-Quinazolinone Ring for Dyeing Nylon, Wool, Cotton andViscose Rayon Fibres

J A DESAI, M H PATEL, K K PATEL. (Miss) R G PATEL and V S PATEL

/The dyeing properties of some 6-arylazo-2-methyl-4(3H)-quinazolinone dyes on nylon and wool fibres as acid dyes and on

cotton and viscose rayon fibres as direct dyes were assessed. The percentage dye-bath exhaustion on nylon and wool was goodto excellent; on cotton and viscose rayon it was poor to moderate. A study of the fastness properties of dyed patterns showed

that these were good to very good for nylon and wool, and fair to good for viscose rayon and cotton. _Keywords: Azoacid dyes, Cotton dyeing, Nylon dyeing, 4-Quinazolinone based dyes, Viscose rayon dyeing, Wool dyeing

Simple or 2-methyl-6-arylazo-4-(3H)~quinazolinonedyes with pyrazolone and H-acid as couplingcomponents are reported in the patent literature 1,2 .

These dyes give fast yellow and fast blue to red colouron nylon fibres. Sona et al.3 and Scarlata et at.4 have

also reported that pyrazolone monoazo dyes giveyellow shade on cellulose and nylon.

In this study, 6-arylazo-2-methyl-4(3H)-quina­zolinone dyes were prepared by coupling diazotized 6­amino-2-methyl-4(3H)-quinazolinbne with differentcoupling components to yield monoazo acid dyes.

R = naphthalene intermediates and pyrazolones asshown in Table I

These dyes were characterized by elemental analysisand IR spectra. The I R spectra of 6-arylazo-2-methyl­4(3H)-quinazolinone dyes showed bands at 3300-3450cm -I (bonded OH), 1680-1735 cm -I (amide-I band ofquinazolinone ring), 1520-1540 cm -I (- N = N -),and two strong bands at 1260-1150 cm -1 (\' as of SO 2)

and 1080-1010 cm -I (Vs ofS02) due to sulphonic acid

group.The coupling components, percentage yield,

elemental analysis and percentage exhaustion of aciddyes on nylon, wool, viscose rayon and cotton fibresare given in Table I. The percentage yield varied from78 to 88%. The percentage exhaustion was 70-95% forall dyes except 01 and Os for nylon fibres; for woolfibres the exhaustion observed was excellent (83-98%),

while for viscose rayon and cotton fibres theexhaustion observed was poor. The shades observedfor nylon, wool and viscose rayon were brilliant.

Experimental Procedure

Preparation of 6-amino-2-methyl-4(3H)-quina­zolinone- Title compounds were prepared by themethod described in literatures.6 .

Preparation of 6-arylazo-2-methyl-4-quinazolinonedyes-A well-stirred solution of the base amino­quinazolinone (0.1 mol) in 2N hydrochloric acid (125m!) was cooled in an ice-salt bath and diazotized with

sodium nitrite solution (0.1 mol, 10 ml H20). Themixture was tested for complete diazotization withstarch iodide paper, which gave a weak blue test. If themixture did not give this test, more sodium nitritesolution was added dropwise until a positive test wasobtained and the colour was stable for a few minutes. If

on the other hand, a strong test for nitrite wasobtained, a few drops of a dilute solution of the basehydrochloride were added until the nitrite test wasnearly negative.

The above cold diazonium solution was added

slowly to a well-stirred solution of the couplingcomponent (0.1 mol) in 10% aqueou~ sodiumcarbonate. The mixture was stirred and cooled in an

ice-salt bath by maintaining pH 7.8. The reactionmixture was further stirred for 4 h at pH 7.8. After theaddition of the diazonium solution, the reaction mass

was tested for complete coupling reaction at regular

intervals by the usual test with f3-naphthol. Similarly,the presence of unreacted coupler was determined byusing a diazonium solution.

After the coupling reaction was complete thereaction mixture was stirred at 50°C and sodium

cWo ride was added until the colouring matter nearly

precipitated. The precipitated solid was filtered off anddissolved in a minimum amount of OMF and

precipitated with chloroform. The precipitates werefiltered off and dried at 40-50°C.

71

INDIAN J. TEXT. RES., VOL. 10, JUNE 1985

Table I-Yield, MolecularFormula, ElementalAnalysisand PercentageExhaustion of Different Azo DyesDye Coupling component of

YieldMolecular FormulaI"maxFound (Calc.) % Exhaustion,No.

the dye %(mol.wt.)(omaJ

R

CHNNylon Wool Viscose Cotton

rayonDI

nI-acid 80C'9H'40sNsSzNaz54041.32.412.562881316

(550)

(4.46)(41.5)(2.5)(12.7)

D2

l-acid 86C19H'40sNsSNa 47250.93.015.483961821

(447)

(4.53)(51.0)(3.1)(15.6)D3

~-Phenyl J-acid 88CZSH'90sNsSNa 47657.13.413.186981620

(524)

(4.55)(57.2)(3.6)(13.3)D4

J-acid urea 84C30H J 90,oN6SzNaz48249.12.511.485941619

(733)

(4.48)(49.3)(2.6)(11.5)

D5

Chicago acid 78C'9H'40sNsSzNaz 53241.32.412.56186II13

(550)

(4.45)(41.5)(2.5)(12.7)

06. Gamma acid

86C'9H'40sNsSNa 50650.93.015.483831413

(447)

(4.57)(51.0)(3.1)(15.6)

D7

G-salt 84C'9H '30sN4SzNaz47542.42.310.476881215

(535)

(4.54)(42.6)(2.4)(10.5)08

R-salt 82C'9H130sN6SzNaz50042.42.210.378901012

(535)(4.52)(42.6)(2.4)(10.5)

D93-Methyl-I-(4' -sulpho-84C'9H'SOsN6SNa 42049.13.118.083922528

phenyl)-5-pyrazolone

(462)(4.46)(49.3)(3.2)(18.1)

DIO i3-Carboxy-I-(4'-sulpho-

78C'9H,z07N6SNaz 43244.22.216.195962832

phenyl)-5-pyrazolone

(514)(4.53)(44.3)(2.3)(16.3)

011 3- Methyl-1-(2' ,5' -di-

82C 19H 130S N4SNaCIz42242.7 2.215.182842426

chloro-4' -sulphophenyl)-

(531)(4.51)(42.9)(2.4)(15.3)

-5-pyrazolone D 12 Laurent acid

86C'9H'404NsSNa 48052.73.116.078942224

(431)

(4.57)(52.9)(3.2){I 6.2)D 13 Peri acid

80C19H'404NsSNa 49\152.73.116.071962126

(431)

(4.48)(52.9)(3.2)(16.2)

Dyeing of nylon and woolfibres with 4-quinazolinoneas acid dyes-The nylon fibres were treated at pH4(adjusted with 30% acetic acid) for 30 min at 80°Candthe wool fibres were treated at pH3 for 30 min at 80°C.

The dye was dissolved by pasting up in a minimumamount of cold water and then hot water and 10%glauber salt (4 ml) were added, and dyeing was carriedout at 100°C for I h. The material-to-Iiquor ratio was1:30. Dyeing pH for nylon fibres was 4 and that forwool fibres, 3. The fibres were rinsed with cold wateranq washed for IS min with a hot solution (95°C)containing soda ash (2g/litre) and soap (lg/litre). The

sup,erficially adhering dye was completely removedand the fibres were rinsed with cold water and air­dried.

Dyeing of cotton and viscose rayon fibres with 4­quinazolinone dyes as direct dyes-The cotton andviscose rayon fibres were treated at pH 7-8 (adjustedwith 10% soda ash solution) for 20 min at 80°C.

The dye was dissolved by pasting up in a minimuma~ount of cold water and then hot water and 10%glauber salt (4 m!) were added and dyeing was carriedat 100°C for I h. The material-to-liquor ratio was

72

1:30. Dyeing pH was 7-8. The fibres were rinsed withcold water and washed for 15 min with a hot solution

(70°e) containing soda ash (2g/1itre)and soap (1gflitre).The superficially adhering dye was completelyremoved and the fibres were rinsed with cold water andair-dried.

Fastness to light-The lightfastness test was carriedout using a microseal light fastness tester inconjunction with the straight light mercury lamp(MB/U 400-W) under the standard conditions set outin BS: 1006. The results are given in Tables 2 and 3.Thelightfastness was fairly good to very good for nylonand wool except in the cases of D1 and D9 for woolwhere it was fair to fairly good. For viscose rayon, itwas fair to good and for cotton, poor.

Fastness to washing-Fastness to washing wasassessed by using an automatic Lander-O-meter underthe following conditions: washing solution containingsoap (5gflitre) and soda ash (2gflitre); washingtemperature, 95°C; duration of washing, 30 min; andmaterial-to-liquor ratio, 1:50. After washing, thespecimen was removed and rinsed with hot water(35°e) until the rinsed showed no alkalinity with

OESAI el at.: AZOACID OYES FOR OYEING NYLON, WOOL, COTION & VISCOSE RAYON FIBRES

Table 2-Shades and Fastness of Different Azo Dyes on Nylon and Wool FibresDye

Colour of dyeings Light fastnessWash fastnessRubbing fastness Acid perspirationAlkalineNo.

for NylonperspirationNylon

WoolNylonWoolNylonWool NylonWool

OryWet NylonWool

01

MagentaViolet red43-43333333302

Red Reddish6543-44433-433brown 03

ReddishReddish5-6644-54-544434.brown

brown04

YellowishOrange5633-43-43443-44brown ,- MagentaViolet red 334305 44-533-43 4-5

06YellowishReddish4634-54443-444

brownbrown

D7YellowishYellowish4-54-544-5554434

orangeorange

08OrangeOrange4-55-64455-3-4444

09GoldenBright5-63-453-44444-534

yellowyellow

OlOGoldenGolden6-74-553334333

yellowyellow

OIlGoldenGolden5-6553443434

yellowyellow

012Oark brownBrown4-5633-4334-5344

013Brown Brown5-65-644-5443434

Table 3-Shades and Fastness of Different Azo Dyes on Viscose Rayon and Cotton Fibres

Oye

Colour of dyeingsLight fastnessWash fastnessRubbing fastnessAcidAlkalineNo.

perspirationperspirationViscose

CottonViscoseCottonViscoseCottonViscoseCottonrayon

rayonrayonrayonViscoseCottonViscoseCotton

rayon

rayon

Ory

WetOryWet

01

VioletViolet3-421-22~222 222202

RedOrange431-22321-222222D3

Crimson Light4-5221-22222 31-232red 04

OrangeLight51-221-22232 2323

orange 05Magenta Violet4-51-21-21-23222 3222

06

PinkLight3-41-2223321-223-423red 07

BrownLight41-21-21-22233 23-423brown 08

OrangeOrange4-51-21-21-23232 '"2-332-3".09

YellowYellow4-532-32-33233 2232

OlO

Yellowish Yellow4322-33322 3323

brown OIlYellowYellow3-42-322-32233 3333

012LightBrown4-521-21-21-22333-4433

brown 013BrownLight522-31-22233 2232

brown

73

I INDIAN J. TEXT. RES., VOL. 10, JUNE 1985

phenolphthalein. It was then squeezed and air-dried.The effect on the colour was expressed and defined byreference to the international geometric grey scale. Thewash-fastness for nylon and wool. was good toexcellent and that for viscose rayon and cotton, poor.

Fastness to rubbing-The rubbing fastness test wascarried out by using a Crockmeter of Atlas inaccordance with AA TCC8-l96l standard methods of

testing. The rubbing fastness for nylon was good toexcellent and that for viscose·rayon and cotton, fair togood.

Fastness to acid perspiration-Fastness to acidperspiration was assessed by the standard method 7 .

The composition of the acid perspiration solution (pH5.5) Vlas: sodium chloride (5 g/litre), disodiumhydrogen phosphate (2.5 g/litre)" and histidinemonohydrochioride (0.5 g/litre). The results are givenin Tables 2 and 3. The acid perspiration fastness fornylon and wool was good to very good and that forviscose and cotton, fair to good.

Fastness to alkaline perspiration~Fastness toalkaline perspiration was also assessed by the standard

74

method? The composition of the alkaline per­spiration solution (pH 8) was: sodium chloride (5g/litre), disodium hydrogen phosphate(2.5 g/litre), andhistidine monohydrochloride (0.5 g/litre). The resultsare given in Tables 2 and 3. The alkaline perspirationfastness for nylon and wool was good to very good andthat for viscose and cotton, fair to good.

References

Pfitzner H & Dammert W, Ger Offen 2,044,824 (to BadischeAnilin- und Soda-Fabrik A.-G.), 16 March 1972; ChernAbstr, 77 (1972) 36381d.

2 Pfitzner H & Dammert W, Ger Offen 2,116,559 (to BadischeAnilin- und Soda-Fabrik A.-G.), 12 Oct 1972;Chern Abstr,78 (1973) 73617b.

3 Sona Panusova & Jiri Klicnar, Chern Technol Pardubice, 1 (1961)81.

4 Scarlata & Guiseppe, Tinctoria, 66 (I) (1969) 1.

5 Tomisek A J & Christensen B E, J Arn chernSac, 70 (1948) 2423.

6 Bogert M T & Beal G D, J Am chem Soc, 34 (1912) 516.

7 Standard methods for the determination of the colour fastness oftextiles and leather (The Society of Dyers and Colorists)1978.

)

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