GHTMDD 397 Received: October 30, 2001 Accepted: March 28, 2002

Bulletin of the Chemists and Technologists of Macedonia, Vol. 21, No. 1, pp. 5764 (2002) ISSN 0350 0136 UDC: 677.494.674.027.423 Professional paper

DISPERSE DYES BASED ON 2-AMINOTHIAZOLE DERIVATIVES FOR POLYESTER

Hari Raghav Maradiya1*, Vithal Soma Patel2 V.P. and R.P.T.P. Science College, Vallabh Vidyanagar 388 120, Gujarat State, India, *E-mail: mardiahari@yahoo.com 2 Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar 388 120, Gujarat State, India
Novel monoazo disperse dyes based on 2-amino-4-phenylthiazole were prepared using various N,Ndialkylaniline derivatives as the coupling component. The dyes were characterized by IR spectral studies, visible absorption spectroscopy and elemental analysis. The dyeing performance of these dyes was assessed on the polyester fibre. These dyes were found to give a wide range of colour shades varying from bright red to navy blue with very good depth, brightness and levelness on polyester. The dyed fibre showed fairly good to very good light fastness and very good to excellent fastness to washing, perspiration, rubbing and sublimation. The dyebath exhaustion and fixation on the polyester fibre was found to be very good. Key words: 2-amino-4-phenylthiazole; disperse dyes; dyeing; exhaustion; fixation; fastness; polyester
1

INTRODUCTION The discovery of the fusion reaction between p-toluidine and sulphur to give dehydrothio-ptoluidine in 1887 constitutes the beginning of thiazole dyestuff technology. Colour Index described various basic, direct, vat and disperse dyes wherein thiazole ring occurs [1]. The early interest in heterocyclic diazo components was stimulated by the need for blue disperse dyes with improved dischargeability and gas fastness (nitrogen oxide). Derivatives of 2-aminothiazole have a long history of use as heterocyclic diazo components for disperse dyes [2]. Blue dischargeable monoazo derivatives based on 2-amino5-nitrothiazole caught the attention of dye chemists in 1950, with colourants such as C.I. Disperse Blue 339 [3] having been produced commercially since then [2]. 2-aminothiazole containing nitro groups are prized for their bathochromism and high tinctorial strength relative to their carbocyclic analogues [4]; these properties, which have given the rise to prominence of these dyes as replacement for blue anthraquinone colourants [5], were first reported by Dickey nearly forty years ago [2]. In 1953, they prepared bright blue heterocyclic azo disperse dyes [7] from 2-amino-5-nitrothiazole with adequate light fastness combined with excellent dischargeability, gas fastness and dyeability on cellulose acetate. The commercial success of such bright blue azo disperse dyes for cellulose acetate proved considerable interest in this class of dyes. With the exception of the 5-nitro derivatives for discharge printing of dyeing cellulose acetate fibres, 2thiazolylazo dyes have only secondary importance as bright blue dyes for polyester so far. Greenish blue dyes can be prepared by choosing a coupler containing electron-donating groups such as 5acetamido-2-methoxyaniline derivatives. Additional early work on the 2-thiazolylazo dyes resulted in violet dyes from 2-amino-4-trifluoromethyl-5carbalkoxythiazole [8], 2-amino-4-alkylsulphonylthiazole [8], 2-amino-4-methyl-5-cyanothiazole [9] and even more bathochromic dyes from 2amino-4-alkylsulphonyl-5-nitrothiazole [10]. The commercial success of dyes for cellulose triacetate, which were derived from 2-amini-5-nitrothiazole, resulted in considerable interest in this class of

58

H. Raghav Maradiya, V. Soma Patel

dyes. Early dyes showed moderate light fastness on cellulose triacetate and polyesters, and light fastness on polyamides was very poor. Dyes with increased light fastness and/or sublimation fastness were prepared from aniline type coupling components containing one or more N-alkyl groups substituted with cyano [11], amylcarbonyloxy [12], alkoxy [13], sulphato [14], diphenylamine [15], pyridinium [16] dicarboximide [17], 1-naphthylamine [18] and N-alkyl-1,2,3,4-tetrahydroquinolines [19] were used as coupling components. These coupler types have the advantages of providing dyes, which have a neutral or green cast when exposed to artificial light, whereas the corresponding dyes from N-alkylaniline couplers have an extremely red cast. The improved fastness to light and sublimation provided by 3-acylaminoaniline types coupling components was not overlooked and dyes were patented [2023]. During the last ten years, the level of interest as indicated by the patent literature has grown in

the field of thiazolylazo disperse dyes [2429]. There has been a considerable growth in the volume of data reporting outside of patent literature [3038]. Earlier we had studied the disperse dyes based on 2-aminothiazole derivatives [3942]. The encouraging results prompted to extend the study on thiazole moiety. Hence, a series of monoazo dyes of general formula shown in Fig. 1 were synthesized and tested as disperse dyes for the polyester fibre. In addition to the characterization of the dyes, an evaluation of their technical properties and a colour assessment were performed.
O2N O2N S N N=N R3 1
Fig. 1. General structural formula of dyes

CH2CH2R1 CH2CH2R2

EXPERIMENTAL All chemicals used in the synthesis of dyes 1a-j were of commercial grade and were further purified by crystallization and distillation. All solvents used were either of analytical grade or redistilled commercial grade. Melting points were determined by the open capillary method. The visible absorption spectra were measured in a Carl Zeiss UV/VIS Specord spectrometer. Elemental analyses were carried out on a Carlo Erba Elemental Analyser 1108. Infrared spectra were recorded in KBr pellets, on a Perkin-Elmer model 983 spectrophotometer. Preparation of 2-amino-4-phenylthiazole 2 The title compound was synthesized by the method reported in the literature [44]. Preparation of dye Diazotization of 2-amino-4-phenylthiazole 2 was carried out according to the method reported in the literature [41]. General coupling procedure The N,N-dialkylaniline (0.02 mol) was dissolved in 10 ml glacial acetic acid and 5 ml water together with 5 g sodium acetate. This solution was Dyeing of polyester A convenient laboratory method for dyeing polyester is to employ high temperature (130 135 C) and high pressure (2430 psi). The dyeing was carried out according to the method reported earlier [41]. Colour fastness test The fastness to light, sublimation and perspiration was assessed in accordance with BS:10061978. The rubbing fastness test was carried out by using a crockmeter (Atlas) in accordance with cooled in an ice-bath 0 5 oC and the diazonium solution of 3 previously prepared was added dropwise over 30 min with vigorous stirring. The pH was maintained between 4 and 5 by simultaneous addition of 10 % sodium acetate solution. Stirring was continued for 2 h, allowing the temperature to the rise to the ambient. The dye was then filtered off, washed with warm and cold water until acidfree, dried at 50 oC in an oven to give azo dye 1aj. (Scheme 1) Recrystallized from ethanol provided the pure dye. The characterization data are given in Table 1.

Bull. Chem. Technol. Macedonia, 21, 1, 5764 (2002)

Disperse dyes based on 2-aminothiazole derivatives for polyester

59

AATCC-1961 and the wash fastness test in accordance with IS:765-1979. The details of various fastness tests are mentioned in the literature [41].

Determination of the percentage of exhaustion and fixation (Dissolution method) The dyebath exhaustion percentage (%E) and fixation percentage (%F) of the dyed fibre were determined according to the known method [41].

O 2N O2 N S 2 N R3

N NH2

NaNO2, H2SO4 O2N 0-5C

N O2N S

+ NNHSO4

CH2CH2R1 CH2CH2R2 O2 N O2N S N N=N R3 1

Scheme 1. Synthetic route of dyes

0 - 5C, pH 4-5

CH2CH2R1 CH2CH2R2

Table 1 Characterisation data, % exhaustion and fixation properties of dyes 1aj

Dye no. Substituents Melting point
o

Yield

Absorption maxima (max) in DMF in conc. H2SO4 (nm) 587 475 480 485 470 500 505 505 470 490 (nm) 520 505 690 515 650 515 515 510 520 500

log (DMF)

Exhaustion

Fixation

Rf value (CH3OH : H2O : AcOH; 1 : 2 : 3) 0.86 0.78 0.87 0.94 0.85 0.80 0.85 0.78 0.90 0.87

R1 1a OH 1b OAc 1c OH 1d OH 1e OH 1f OAc

R2 OH OAc OH OH OH OAc Cl CN CN CN

R3 H H CH3 Cl NHAc CH3 H H CH3 Cl

% 81 86 88 74 90 82 82 80 86 84

% 4.47 4.81 4.86 4.52 5.18 4.98 4.26 4.87 4.36 4.76 68 71 78 65 75 80 81 78 74 80

% 84 88 90 86 84 89 89 88 85 90

118120 125127 116118 135136 109110 107108 137138 162163 135137 115116

1g Cl 1h CN 1i 1j CN CN

Glas. hem. tehnol. Makedonija, 21, 1, 5764 (2002)

60

H. Raghav Maradiya, V. Soma Patel

RESULTS AND DISCUSSION Preparation of thiazole dyes 4-substituted thiazoles are prepared by reacting the appropriate ketone with thiourea in the presence of bromine. Acetophenone was reacted overnight on a steam bath with thiourea in the equimolar ratio in the presence of one mole bromine and gave compound 2 [41]. The thiazole derivative was obtained from the reaction mixture agreed in the elemental analysis and physical properties with those reported in the literature [41]. For diazo component 2, an anhydrous diazotization can only be achieved by using nitrosylsulphuric acid obtained from dry solid sodium nitrite and concentrated sulphuric acid. Thus, the thiazole intermediate 2 was diazotized satisfactorily at 05 oC by addition of nitrosylsulphuric acid to a suspension of the amine in a mixture of acetic acid and propionic acid. All products required recrystallization to eliminate contaminants arising from diazo decomposition and/or by-products present in the industrial sourced coupling components used. In addition, removal of undiazotized amine was necessary in dyes. In order to determine the end point of diazotization, it was found useful to check for the presence of unreacted diazo component on TLC by sampling the diazotization mixture and extracting with ethyl acetate. Thus, when unreacted diazo component no longer persisted on TLC, the diazotization was ended. All dyes were purified by recrystallization from ethanol. Purity of the dyes was Table 2 Elemental analysis of dyes 1 a-j
Dye no. 1a 1b 1c 1d 1e 1f 1g 1h 1i 1j Molecular formula C19H20N4O2S C23H24N4O4S C20H22 N4O2S C17H15N4OSCl C21H23N5O3S C24H26N4O4S C19H18N4SCl2 C21H18N6S C22H20N6S C21H17N6SCl Realative molecular mass 368 452 382 358.5 425 466 405 386 400 420.5 w (C) / % Calcd 61.95 61.06 62.82 56.90 59.29 61.80 56.29 65.28 66.00 59.92 Found 61.69 60.88 62.65 56.71 59.06 61.52 56.10 65.09 65.76 59.65 w (H) / % Calcd 5.43 5.30 5.75 4.18 5.41 5.57 4.44 4.86 5.00 4.04 Found 5.23 5.10 5.60 4.01 5.28 5.41 4.20 4.48 4.81 3.80 w (N) / % Calcd 15.21 12.38 14.65 15.62 16.47 12.01 13.82 21.76 21.00 19.97 Found 15.08 12.20 14.50 15.76 16.28 11.72 13.58 21.43 20.76 19.70

confirmed by TLC and the satisfactory elemental analysis (Table 2). The diazonium salt solution 3 was generally used within a few hours since it decomposed on standing, even when cold. Subsequent coupling reactions took place readily on adding the resulting diazonium salt solution 3 continuously to the solution of coupling component in acetic acid. Coupling was usually accompanied by some evidence of decomposition; however, by a careful addition of the diazonium salt solution at 05 oC to a solution 3 of the coupling component in an aqueous acetic acid, high yields (7490 %) of the dye were usually obtained. To complete coupling, particularly for reactions using nitrosylsulphuric acid for the diazotization, the pH of the reaction mixture was eventually adjusted to approximately 45. Thus, an appropriate amount of 10 % sodium acetate solution was slowly added to the solution below 5 oC. Physical properties of dyes All solid dyes are dark brown in colour. The purity of the dyes was checked by TLC using methanol-water-acetic acid (12:3:7) as the solvent system. When adsorbed onto silica chromatography plates, each dye produced a reddish-brown colour sport. All the recrystallized dyes exhibited well-defined melting points characteristic of pure compounds.

Bull. Chem. Technol. Macedonia, 21, 1, 5764 (2002)

Disperse dyes based on 2-aminothiazole derivatives for polyester

61

The electronic absorption spectral properties of dyes The visible absorption spectroscopic properties of dyes 1aj were recorded in DMF and concentrated H2SO4 solution, and are presented in Table 1. The value of the logarithm of the molar extinction coefficient (log ) of the dyes 1aj was in the range of 4.265.18, consistent with their very high intensity of absorption. One cause of the increased intensity might be attributed to the greater planarity of the thiazole dyes, because of the lower steric interaction of a five-membered thiazole ring. The colour of the dyes 1aj is affected by substituents in the coupler constituent. The bathochromism of the dyes is an inherent property of the thiazole system itself; the bathochromism does not derive from the substituent groups. However, the greater polarizability of the thiazole system (relative to the benzene system), in addition to affecting a general bathochromism in dyes. As can be seen from the data in Table 1, additional bathochromic shifts can also be obtained by enhancing the electron donor properties of the coupler ring. The colour properties of the dyeing corresponded with the absorption maxima of the dyes in solution, the positions of which were consistent with expectations. For example, bathochromic shifts were observed on the replacing terminal CN group in the N-alkyl chains with hydroxyl functions, or locating an electron releasing group meta to the terminal amino function. When replacing the Cl and CN groups in dye 1g and 1h by the OH group, the resulting dye 1a is absorbed at 520 nm. The bathochromic shift is due to an increase in the donor strength of the coupler ring. Similarly, introducing a methyl group meta to the terminal amino function in dyes 1c, 1f and 1i produced bathachromic shift of 170 nm and 10 nm compared to the dyes 1a, 1b and 1h respectively. The CN group is a more powerful electron acceptor (dye 1h) than the Cl group (dye 1g) and hypsochromic shift of 5 nm is observed. Curious coupling component substituent effects on absorption maxima are evident; for example, acetylation of terminal OH groups in dyes 1a, typically brings about the modest hypsochromic shift of 15 nm and 175 nm in dyes 1b and 1f respectively. Introducing an acetamido group ortho to the azo group, as in dyes 1e gave shift of 130 nm relative to dye 1a. The acetamido group is a weak electron donor, but more importantly, it can take part in hydrogen bonding with the azo group. This enhances the planarity of the

dye containing the acetamido group. The value of log of the dye 1e is 5.18 indicating the highest intensity of absorption attributed to greater planarity of the dye. The results summarised in Table 1 clearly show that the incorporation of the electron withdrawing group in the coupler ring leads to the red shift, similarly, when the electron donating ability of the coupler is enhanced, the deeper in the colour of the resulting dyes. In order to bring the shift in absorption maxima to longer wavelengths, the negative group strategically placed in the coupler ring which increases in polarisability of the dye molecule resulting from the enhanced electron density movement from the donor groups (coupler) to the acceptor group (diazo ring). The thiazole ring, being more electron deficient, is accordingly a poor electron donor. The bathochromicity of thiazole dyes is not attributable to a contribution of 3d atomic orbital of sulphur atom of the heterocyclic ring [45]. Infrared spectra of dyes The C-H stretching vibrations of the aromatic ring appear at 710805 and 15801595 cm1. The strong absorption bands in the range 15001510 cm1 and 11901210 cm1 are corresponding to CN stretching vibration. The N-H stretching vibration confirmed at 34003450 cm1. The azo and OH group stretching vibration band appear at 1500 1525 cm1 and 35003600 cm1 respectively. The C-H stretching vibration of alkyl group appears at 28952900 cm1. The carbonyl stretching appears at 17151735 cm1. Dyeing properties of dyes The disperse dyes 1aj were applied at 2 % depth on the polyester fibre. Their dyeing properties are given in Table 3. These dyes gave a wide range of attractive colour shades varying from bright red to navy blue shades with good levelness, brightness and depth on the fibre. The variation in the shades of the dyed fibre results from both the nature and position of the substituent present on the coupler ring. For example, the introduction of an acetamido group ortho to the azo linkage in dye 1e results in a significant improvement in the light fastness. This may be due to the intramolecular hydrogen bond formed between the acetamido group and azo group. The light fastness of the dyes

Glas. hem. tehnol. Makedonija, 21, 1, 5764 (2002)

62

H. Raghav Maradiya, V. Soma Patel

is more uniform (see Table 3). The slight differences in the coupling components appear to have little effect: the addition of a CN group onto the end of the alkylamino chain would be expected, have a beneficial effect on the light and sublimation fastness with polyester as the substrate. Light fastness ranges from fairly good (4) to excellent (7). The observed slightly higher fastness (5) of dyes with fairly good (4) can be explained in terms of the reduction of the electron density at the azo group due to the inductive effect excerted by the CN group. Dye 1a has slight poor sublimation fastness,

but incorporation if polar acylamino group (dye 1e) into the coupling component improves this. The fastness to wash fastness and to perspiration are very good to excellent for all dyes. All the dyes show excellent fastness to rubbing on fibre. This may be attributed to good penetration and affinity. The intrinsic conjugation in the thiazole structure ensures very good colour strength. The compactness of the dye structure provides for excellent sublimation fastness.

Table 3 Dyeing and fastness properties of dyes 1aj on polyester fibre

Dye no. 1a 1b 1c 1d 1e 1f 1g 1h 1i 1j Colour hue on polyester Bright maroon Bright red Blackish violet Dark maroon Navy blue Deep red Deep red Dark brown Brown Bright red Light fastness 4 4-5 4 4-5 7-6 4 5-4 5 5 5 Wash fastness 5-4 4-5 5-4 5 5 5-4 5-4 5 5 5 Perspiration fastness Acid Alkaline 4-5 5-4 5-4 5 5 5 5-4 5 5 5 5-4 5 5 5 5-4 5-4 5-4 5 5 5 Sublimation fastness 5 5 5 5 5 5 5 5 5 5 Rubbing fastness 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5 5

CONCLUSION A series of thiazolylazo disperse dyes containing various N,N-dialkylaniline residues have been synthesized by conventional methods and their colour properties examined both insolution and on application to polyester fibre. The dyes provide a wide range of attractive colour which vary from bright red to navy blue fast shades on fibre and offer excellent affinity and intensity of colour. Their synthesis is generally convenient and inexpensive. The small size of thiazolylazo dyes provided better dyeability. The intrinsic conjugation in the thiazolylazo structure results in excellent colour strength. The outstanding property of the thiazolylazo dyes is their high sublimation fastness. The compactness of structure improves sublimation fastness. The nature of the substituent in the coupling components has a great influence on the visible absorption and shade of the dyeing. The introduction of an acetamido group ortho to the azo linkage results in a significant improvement in the light fastness. The heteroatom in the thiazolylazo structure results in bathochromacity and leads to the brightness of shades. The CN substituted dyes, probably because of their poorer migration properties, have generally higher fastness than the hydroxylated analogues. Furthermore these dyes show very good exhaustion, fixation, uniform dyeing and display excellent dischargeability (an additional dyeing property, not exhibited by the carbocyclic azo and anthraquinone disperse dye). These properties, which have aided the rise to prominence of such diazo components as replacement for blue anthraquinone dyes on polyester fibre.

Bull. Chem. Technol. Macedonia, 21, 1, 5764 (2002)

Disperse dyes based on 2-aminothiazole derivatives for polyester

63

The results suggest that the dyeing of polyester fibre with thiazolylazo disperse dyes can be promising for practical uses, chiefly on account of the facility and cheapness of the dyes synthesis, the

case of application and the overall versatility of their use.

Acknowledgements: The authors thank Professor V. S. Patel, Vice-Chancellor of Sardar Patel University, for providing research facilities and valuable guidance.

REFERENCES
[1] Colour Index, Society of Dyers and Colourist, ed. American Association of Textile Chemist and Colourist, Bradford, 1971. [2] L. Shuttleworth, M. A. Weaver, in The Chemistry and Application of Dyes, D. R. Waring and G. Hallas, ed. Plenum Press, New York, 1990, p. 107. [3] J.-Z. Hu, P. Skrabal, H. Zollinger, Dyes Pigm., 8, 189 (1987). [4] M. A. Weaver, L. Shuttleworth, Dyes Pigm, 3, 133 (1982). [5] R. Egli, in The Design and Synthesis of Organic Dyes and Pigments, A. T. Peters, H. S. Freeman, ed. Elsevier, London 1991, p. 1. [6] J. B. Dickey, E. B. Towne, M. S. Bloom, W. H. Moore, H. M. Hill, H. Heynemann, D. G. Hedberg, D. C. Sievers, M. V. Ottis, J. Org. Chem., 24, 187 (1959). [7] J. B. Dickey, E. B. Towne, U. S. Patent 2659719, 1953; Chem. Abstr., 49, 1335f (1955). [8] E. B. Towne, H. M. Hill, U. S. Patent 2746953, 1956; Chem. Abstr., 50, 6058a (1956). [9] E. Merian, U. S. Patent 3007915, 1961; Chem. Abstr., 57, 7421h (1961). [10] R. Egli, U. S. Patent 4395544, 1979; Chem. Abstr., 99, 159949g (1983). [11] E. B. Towne, J. B. Dickey, M. S. Bloom, U. S. Patent 2852504, 1958; Chem. Abstr., 53, 6627c (1958). [12] Gosei Senryo Gijutsu Kenkyu Kumiai, Jpn. Kokai Tokkyo Koho, JP 59215355, 1983; Chem. Abstr., 102, 186655v (1985). [13] Gosei Senryo Gijutsu Kenkyu Kumiai, Jpn. Kokai Tokkyo Koho, JP 59170142, 1983; Chem. Abstr., 102, 26377c (1985). [14] Mitsubishi Chemical Industries Co. Ltd., Jpn. Kokai Tokkyo Koho, 80133458, 1980; Chem. Abstr., 94, 104887b (1981). [15] Sumitomo Chemical Co., Ltd., Jpn. Kokai Tokkyo Koho, JP 57161653, 1982; Chem. Abstr., 98, 73836k (1983). [16] H. Erwin, W. Matthias, R. Helmut, G. Sabine, Ger. Offen DE 4120362, 1991; Chem. Abstr., 118, 256596h (1993). [17] B. Parton, British U. K. Patent 2028856, 1978; Chem. Abstr., 94, 4937z (1981). [18] M. A. Weaver and J. M. Straley, U. S. Patent 3526733, 1970; Chem. Abstr., 73, 131958y (1970). [19] G. Modena, A. Risatsu, Bull. Sci. Fac. Chem. Ind. Borogna, 11, 65 (1953). [20] Gosei Senryo Gijutsu Kenkyu Kumiai, Jpn. Kokai Tokkyo, Koho 5920356, 1984; Chem. Abstr., 100, 211648p (1984). [21] Nippon Kayaku Co. Ltd., Jpn. Kokai Tokkyo Koho 8060558, 1978; Chem. Abstr., 93, 151649q (1980). [22] M. Peter, Ger. Offen 3001945, 1979; Chem. Abstr., 93, 206144d (1980). [23] Mitsubishi Chemical Industries Co. Ltd., Jpn. Kokai Tokkyo Koho 80112266, 1979; Chem. Abstr., 94, 32171p (1981). [24] Gosei Senryo Gijutsu Kenkyu Kumia, Jpn. Kokai Tokkyo Koho JP 5991152, 1982; Chem. Abstr., 101, 173017t (1984). [25] H. Tsien, K.-P. Chu, H. Chang, US Patent 5652344, 1995; Chem. Abstr., 127, 150201w (1997). [26] R. Sens, K.-H. Etzbach, Ger. Offen DE 4426023, 1994; Chem. Abstr., 124, 204936y (1996). [27] S. Beckmann, K.-H. Etzbach, R. Sens, PCT Int. Appl. WO 9529958, 1994; Chem. Abstr., 124, 120121r (1996). [28] Y. Nakamura, J. Murata, Jpn. Kokai Tokkyo Koho JP 05155870, 1993; Chem. Abstr., 119, 18261n (1993). [29] N. Sekar, Colourage, 41, 38 (1994). [30] A. T. Peters, A. Gbadamosi, J. Chem. Tech. Biotechnol., 53, 301 (1992). [31] K. A. Bello, C. M. O. A. Martins and I. K. Adamu, Colourage, 42, 29 (1995). [32] K. R. Desai, B. R. Modi, B. D. Mistry, J. Indian Chem. Soc., 72, 141 (1995). [33] K. A. Bello, Dyes Pigm., 27, 45 (1995). [34] J. Griffihs, C. J. Riepl, Chem. Commun. (Cambridge), 13, 1349 (1998). [35] G. Hallas, J.-H. Choi, Dyes Pigm., 42, 249 (1999). [36] K. H. Chikhalia, K. R. Desai, J. Inst. Chem. (India), 70, 142 (1998). [37] D. V. Rangnekar, V. R. Kanetkar, G. S. Shankarling, J. V. Malanker, J. Indian Counc. Chem., 15, 28 (1998). [38] A. D. Towns, Dyes Pigm., 42, 3 (1999). [39] D. W. Rangnekar, G. J. Malankar, Phosphorus, Sulfur Silicon Relat. Elem., 164, 199 (2000). [40] H. R. Maradiya, V. S. Patel, J. Serb. Chem. Soc., 65, 773 (2000). [41] H. R. Maradiya, V. S. Patel, Bull. Chem. Technol. Macedonia, 20, 51 (2001). [42] H. R. Maradiya, V. S. Patel, J. Braz. Chem. Soc, 12, 710 (2001).

Glas. hem. tehnol. Makedonija, 21, 1, 5764 (2002)

64

H. Raghav Maradiya, V. Soma Patel

[43] H. R. Maradiya, V. S. Patel, Fibers and Polymers, 2, 153 (2001). [44] J. B. Dickey, E. B. Towne, U. S. Patent 2730523, 1956; Chem. Abstr. 50, 7467b (1956)

[45] Y. Kogo, Dyes Pigm., 6, 318 (1985).

Rezime

DISPERZNI BOI NA 2-AMINOTIAZOLNI DERIVATI ZA POLIESTER Hari Raghav Maradiya1, Vithal Soma Patel2
V.P. and R.P.T.P. Science College, Vallabh Vidyanagar 388 120, Gujarat State, India, *E-mail: mardiahari@yahoo.com 2 Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar 388 120, Gujarat State, India
1

Klu~ni zborovi: 2-amino-4-feniltiazol; disperzni boi; boewe; iscrpuvawe; fiksirawe; postojanost; poliester Sintretizirani se novi monoazodisperzi boi na baza na 2-amino-4-feniltiazol so polzuvawe na razli~ni N,N-dialkil anilinski derivati kako komponenti za kupluvawe. Boite se karakterizirani so infracrvena i vidliva spektroskopija, kako i so elementarna analiza. Prosledeni se i performansite na dobienite boi na poliesterskite vlakna. Najdeno e deka boite davaat {iroka paleta na nijansi, od svetlocrvena do temnosina, so jaki i sjajni tonovi i uedna~enost pri boeweto na poliesterot. Oboenite vlakna poka`uvaat dosta dobra do mnogu dobra postojanost na svetlina i mnogu dobra do odli~na postojanost na perewe, potewe, suvo i mokro triewe i sublimacija. Boite poka`uvaat dobra prifatlivost i fiksiranost na poliesterskite vlakna.

Bull. Chem. Technol. Macedonia, 21, 1, 5764 (2002)