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One-bath Dyeing of PET/cotton Blends with Azohydroxypyridone Disperse Dyes Containing a Fluorosulfonyl Group
Joonseok Koh* and Jongseung Park1
Department of Textile Engineering, Konkuk University, Seoul 143-701, Korea Electronic Chemical Materials Group, Cheil Industries Inc., Gyeonggi-do 437-711, Korea (Received August 13, 2007; Revised October 18, 2007; Accepted December 27, 2007)
Abstract: Azohydroxypyridone disperse dyes containing a fluorosulfonyl group were dyed on PET/cotton blends and their dyeing and fastness properties were investigated. Specially, the azohydroxypyridone dyes containing a nitro group in place of the fluorosulfonyl group in the para position to azo group were synthesized in order to compare their dyeing and fastness properties on PET/cotton blends with those of fluorosulfonyl-substituted analogues. As these dyes can be alkali cleared in the same bath, a one-bath dyeing method was used and the results were compared with that of a conventional two-bath dyeing method. In particular, the cross-staining of cotton was studied in order to assess their suitability for the one-bath dyeing of PET/cotton blends. Keywords: Azohydroxypyridone, One-bath dyeing, PET/cotton blends, Fluorosulfonyl group, Disperse dyes, Fastness
The demand for environmentally friendly dyes of high wet fastness on polyester is increasing. In addition, there are rising global legislative pressures to reduce the impact of dyeing processes on the environment through reductions in effluent discharge as well as in the use of energy and materials. Alkali-clearable disperse dyes offers a means of addressing both challenges at once. Alkali-clearable disperse dyes do not require the use of sodium dithionite and this significantly reduces the cost of effluent treatment [1-15]. In addition, by avoiding the need for reduction clearing, significant productivity improvements can be made, including lower usage of water and chemicals and a reduction in effluent volume, this is a key objective in the ‘rapid dyeing’ approach for PET . Alkali clearability is of particular interest in the dyeing of blends of PET with cotton since it allows dyes suitable for each fiber to be applied in one bath using a two-step dyeing technique. Any superficial disperse dye remaining on the PET, or any disperse dye cross-staining the cotton, is hydrolysed by the alkali and can be removed from the PET at the same time as the reactive dye is exhausting on to the cotton. In this way the use of an alkali clearing stage gives better productivity and savings in energy, chemicals, and water . In previous studies, synthesis and application of novel alkali-clearable azo disperse dyes containing the fluorosulfonyl group have been investigated [6-13]. 4-(N,N-diethylamino)4'-fluorosulfonylazobenzene dyes, which have been synthesized in a previous study, cover a whole gamut of colors (red to greenish blue, max 469-620 nm in ethanol) except the yellow shade area . Recently, we have attempted to synthesize yellow disperse dyes which have good spectral properties and dyeing properties . Thus, for the yellow shades,
*Corresponding author: email@example.com 128
hydroxypyridone derivatives were used as coupling components since they provide greenish yellow to orange shades and have significantly high tinctorial strength . The present study describes for the one-bath dyeing of PET/cotton blends using a combination of alkali-clearable disperse dyes based on azohydroxypyridone and hot-type reactive dyes. In this case reduction clearing cannot be used since the conditions are too severe for the reactive dyes. In addition, the color fastness achieved in the one-step process, especially in heavy shades, may be a cause for concern . The objective of the current study was therefore to develop yellow disperse dyes that were both clearable under mildly alkaline conditions, at the same time achieving a level of color fastness comparable to that from the traditional twobath method. The approach adopted was to synthesize a series of new azohydroxypyridone disperse dyes containing a fluorosulfonyl group. Dyeing and fastness properties on PET/cotton blends were studied, in particular the cross staining of cotton, in order to establish their suitability for the one-bath dyeing of these blends. Dyeings from the azohydroxypyridone dyes containing a nitro group in place of the fluorosulfonyl group were also investigated for comparative purpose.
Materials 100 % PET, 100 % cotton fabrics (KS K 0905), and scoured twill woven PET/cotton blends (65 % PET, 35 % cotton) were kindly supplied by Kabool Textiles. The following dispersing agents were used: Diwatex (anionic, Borregaard Lignotech) for milling the synthesized dyes; and Lyocol RDN liquid (anionic, Clariant) for the dyeing of PET. Sandozin NIE (non-ionic, Clariant) was used as the wetting agent and Snogen CS-940N (non-ionic, Daeyoung Chemicals) as the soaping agent. The reactive dye, Procion Crimson H-
and reduction clearing. Vol. The color difference ( E) between the stained fabrics and untreated white fabric was obtained from the distance between their coordinates in CIELAB color space using equation (1) : E= L* 2 + a * 2 + b* 2 (1) Dye F1 F2 F3 N1 N2 N3 X FSO2 FSO2 FSO2 NO2 NO2 NO2 R H CH3 C2H5 H CH3 C2H5 Mol. Color Measurement The reflectance and CIELAB values of the dyed samples were measured using a spectrophotometer (Color-Eye 3000.13]. specular component included) interfaced with a personal computer. separated pieces of PET and cotton were dyed in each dyeing process by the method described above. the PET component of the blend was dyed in the first bath for 30 min at 130 oC. and reduction clearing using 2 g/l sodium hydroxide and 2 g/l of sodium dithionite. each for 20 min at 80 oC. in the second bath the cotton component was dyed for 40 min at 80 oC. . y10. Cross-staining was assessed by measuring the color difference between stained and unstained cottons. . Azohydroxypyridone disperse dyes F1-N3 used in the present study reduction clearing for 20 min at 80 oC. A conventional two-bath dyeing method and a one-bath twostep dyeing method were used.24 313. the disperse dye for PET and the reactive dye for the cotton were introduced together at the start of dyeing (Figure 1).35 299. a* and b* represent the differences in L*. The other reagents were of commercial grade. In the two-bath process. Macbeth. 10 o standard observer. Cross-staining of Cotton The cross-staining of cotton was investigated to assess the suitability of a dye for dyeing PET/cotton blends and the effectiveness of the clearing treatment. D65. In the one-bath two-step dyeing method. and z10. are colour matching functions for the 10 o standard observer at each wavelength (ISO 7724/11984). . Dye Synthesis and Preparation of Dye Dispersion The synthesis of azohydroxypyridone disperse dyes and the preparation of dye dispersion have been described in the previous work [11. One-bath dyeing profile of PET/cotton blends. In order to compare the color yield individually on the PET and cotton component between one-bath and two-bath dyeing. Alkali clearing was conducted using 20 g/l sodium carbonate. Datacolor International) at a dye concentration of 2 %owf and a liquor ratio of 25:1. No. The color strength ( fk) is the sum of the weighted K/S values in the visible region.33 364. followed by Table 1. The PET component was first dyed at 130 oC and thereafter cooling the dyebath to 80 oC. Color Fastness PET/cotton blends were dyed (2 %owf) and heat-set (180 oC. weight 336. The synthesized dyes (F1-F3 and N1-N3) that were used throughout the study were given in Table 1.Azohydroxypyridone Disperse Dyes Fibers and Polymers 2008. a* and b* between the two samples. The color yield of the dyes on PET and cotton was also investigated by measuring the color strength value of dyed fabrics at a given dye concentration. 2.9. was supplied by DyStar for the dyeing of cotton component in the blends. given by equation (2) : 700 fk = = 400 K/S x 10 + y 10 + z 10 (2) where x10. L*. alkali clearing.2 129 EXL [bis(aminochlorotriazine) type]. alkali was added.30 350. 60 s) and assessed for color fastness to washing (ISO 105 Figure 1.0 % owf disperse dye was applied to separate pieces of PET and cotton. In this procedure. Dyeing Fabrics based on PET/cotton blends were dyed in a laboratory dyeing machine (Ahiba.27 327. followed by three different types of treatment: no clearing.30 (EtOH) 420 nm 422 nm 422 nm 436 nm 436 nm 438 nm max Appearance Yellow solid Yellow solid Yellow solid Yellow solid Orange solid Orange solid where.
Figure 4. Color yield of the reactive dyes on cotton. it is seen that the one-bath dyeing method gave lower color yield on cotton than did the twobath method: F1-F3 and N1-N3 dyes yielded 83~94 % and 73~91 % of the depth of shade given by the corresponding two-bath dyeing method. Figure 2. one-bath dyeing of PET/cotton blends using a combination of reactive dyes and alkali-clearable azohydroxypyridone disperse dyes containing the fluorosulfonyl group under hightemperature dyeing conditions is feasible by an appropriate dye selection.2 Joonseok Koh and Jongseung Park CO6:1994/B1M). one-bath and two-bath dyeing produced a Figure 3. by the one-bath and the traditional two-bath dyeing process. It was. the fastness tests were carried out for after both one-bath and two-bath dyeings. The advantages of such a dyeing technique include increased productivity due to savings in total cycle times. The changes in shade and staining were assessed using a gray scale. No. irrespective of dyeing method (Figure 2). considered that satisfactory depth of shade might be obtainable by careful consideration of dye structure and dyeing conditions . water. in the case of dyes F3 and N1. Results and Discussion Color Yield on PET/cotton Blends The advantages of a one-bath dyeing process include savings in time. Color yield of the disperse dyes and reactive dyes on PET/cotton blends. Therefore. rubbing (ISO 105 X12:2001). Results from the one-bath dyeing were compared with those from the traditional two-bath method. one-bath and two-bath dyeing produced a similar level of color yield on PET/cotton blends. however. On the other hand in the case of dyes F3 and N1. However. The lower color strength of F1 on PET is probably because of the low substantivity due to its relatively high polarity and short alkyl chain length. . Figure 4 shows the color yield of PET/cotton blends using the one-bath dyeing method and that using two-bath dyeing method. The synthesized dyes except F1 produced a similar level of color yield on PET. are shown in Figures 2-4. similar level of color yield (94 % and 91 % of the 2-bath dyeing). The decrease in disperse dye uptake on PET/cotton using the one-bath technique is mainly due to the lower reactive dye uptake on cotton component (Figure 3). energy.130 Fibers and Polymers 2008. Color yield of the synthesized disperse dyes on PET. from Figure 3. and labor and a reduction in raw material requirement. Vol. The decrease in reactive dye uptake on cotton using the one-bath technique could have been due to the decomposition of reactive dyes during high temperature dyeing and the agglomeration caused by the dispersing agent present in the dye bath . perspiration (ISO 105 E04:1994).9. The color yield (fk) on the dyed fabric using a combination of azohydroxypyridone disperse dye and bis(aminochlorotriazine) reactive dye. The one-bath dyeing method gave lower color yield on PET/cotton blends than did the two-bath method. Its disadvantage is that dye exhaustion may be poorer than with conventional two-bath dyeing. However. and light (ISO 105 B02:1994).
In the case of dyes N1-N3. A: acetate.Azohydroxypyridone Disperse Dyes Fibers and Polymers 2008. In the case of azohydroxypyridone dyes containing a fluorosulfonyl group (F1-F3). 5 5 5 5 5 5 5 5 4 5 4 4-5 P: PET. Alkali-clearable dyes of this type are therefore readily removed by alkali treatment in one-bath dyeing and exhibit a low level of staining in wash fastness tests. Hydrolysis and ionization of azohydroxypyridone disperse dyes containing a fluorosulfonyl group under alkaline condition. particularly is important where both good fastness to crocking and wash are crucial. It is therefore reasonable to assume that the good clearing properties shown by the azohydroxypyridone dyes containing a fluorosulfonyl group will have a positive effect on their color fastness in addition to their productivity benefits. Cotton staining of the synthesized dyes. Wash Fastness The wash fastness test. although less than that of the untreated samples. the cotton staining of the alkalitreated samples. nylon. Fastness to washinga of the synthesized dyes (ISO 105 C06 B1M) Dye A One-bath C N W D Two-bath C N W Figure 5. This result can be attributed to the good alkali clearing properties of azohydroxypyridone disperse dyes containing the fluorosulfonyl group and supports the hydrolysis mechanism proposed previously (Scheme 1) . without addition of alkali. and that these may generate alkalinity (ca. was intermediate between that of the non-cleared and reduction-cleared samples. was chosen in order to minimize the possible advantageous effect of the alkali-clearability of the azohydroxypyridone dyes containing a fluorosulfonyl group. azohydroxypyridone disperse dyes showed a similar efficiency between alkali clearing and conventional reduction clearing leading to their suitability for use on PET/cotton blends. N: . F1 4 5 5 5 5 5 F2 4 5 5 5 5 5 F3 5 5 5 5 5 5 N1 3-4 4 4 4-5 4-5 5 N2 4 4-5 4 4-5 4 5 N3 4 4-5 4 4-5 4 5 a Multifiber strip consisting of W: wool. The fastness of dyed PET/cotton was assessed in order to determine whether the presence of the fluorosulfonyl group was effective in achieving alkali clearability.5) in the test liquor . pH 9. Dyeings from the 4'-nitro analogues (N1-N3) were also investigated for comparative purposes. These dyes were not expected to be alkali-clearable enough since their nitro functions cannot give water-soluble dyes on hydrolysis although the ionization of hydroxypyridone under alkaline Table 2. both showing a high level of fastness. The fastness of blends dyed using the one-bath. Color Fastness Properties Of major importance for the commercial viability of the one-bath dyeing process is the color fastness of the dyed goods. For conventional two-bath dyeing. Cross-staining on Cotton In order to assess the suitability of azohydroxypyridone dyes containing a fluorosulfonyl group for one-bath dyeing of PET/cotton blends. The results can be accounted for the hydrolysis of a fluorosulfonyl group and the ionization of a hydroxypyridone structure: the flurosulfonyl group of the synthesized dyes is hydrolyzed in alkali to give a water soluble sulfonate group and the hydrozone form of the hydroxypyridone dye is converted to the azo anion form (Scheme 1) . D: diacetate. cross-staining of the cotton was assessed by measuring the color difference between stained and untreated cotton fabrics. two-step process and the conventional two-bath process were compared. it has to be remembered that detergents typically contain 40~50 % of alkali materials such as sodium tripolyphosphate. the fastness of the dyed fabric by the one-bath method was similar to that for the two-bath process. As shown in Figure 5. Nevertheless. The results indicate that azohydroxypyridone disperse dyes containing a fluorosulfonyl group are equally suitable for the one-bath dyeing process as for conventional two-bath dyeing.2 131 the fabric surface. No. ISO 105-C06/B1M. The dyes containing the fluorosulfonyl group showed excellent levels of wash fastness using test method ISO 105-C06/B1M (Table 2).9. C: cotton. a reduction clearing following PET dyeing is effective for the removal of dyes on Scheme 1. Vol.
No.0. The ratings for both the dyeing methods were between 4-5 and 5 for dry rubbing fastness and between 3-4 and 4 for wet rubbing. both showing relatively high levels of fastness.5-1.5-1. Table 5. and both showed high levels of fastness. The ratings of wet rubbing fastness were lower than those of dry rubbing fastness. irrespective of dyes used (Table 5). in the case of N1-N3. Rubbing Fastness The rubbing fastness of fabric dyed by the one-bath and two-bath methods was similar. In the case of F1-F3. An analogous comparison between the fluorosulfonyl-substituted derivatives (F1-F3) and nitro analogues (N1-N3) revealed a gap in alkali-clearability as exemplified by the difference between the one-bath dyeing and two-bath dyeing in wash fastness (Table 2): the ratings of wash fastness of one-bath dyeing were relatively lower than that of two-bath dyeing by up to the ratings of 0. The advantages of such a dyeing technique include productivity increases due to savings in . Fastness to light of the synthesized dyes (ISO 105 B02) Dye One-bath Two-bath F1 6 6 F2 6 6 F3 6 6 N1 6 6 N2 5 5 N3 6 6 Light Fastness The light fastness of the dyed fabrics was in the range 5 to 6 irrespective of the dyeing method and dyes (Table 6). Fastness to acid perspiration of the synthesized dyes (ISO 105 E04) Dye F1 F2 F3 N1 N2 N3 One-bath D 3-4 3 2-3 1-2 3 4 C 4-5 4-5 4 3-4 4-5 5 N 4 4 3-4 1-2 4 4-5 P 5 5 4-5 4 5 5 A 5 5 4-5 4-5 5 5 W 5 5 4-5 3-4 4-5 4-5 D 3-4 3 3 2-3 3 4 C 4-5 4-5 4-5 4-5 4-5 5 Two-bath N 4 4 4 2-3 4 4-5 P 5 5 4-5 4-5 5 5 A 5 5 5 5 5 5 W 5 5 5 4 5 4-5 condition could contribute to the alkali-clearability. the fastness of one-bath dyed fabric was similar to that of two-bath dyed fabric. presumably because the fluorosulfonyl group of the synthesised dyes is hydrolysed in alkali to solubilising sulfonate group as was investigated in previous study (Scheme 1). and PET component of the multifiber adjacent fabric were particularly prone to staining during the perspiration test but loss of color did not occur perceptibly in the sample (Tables 3 and 4).0. Conclusion It has been demonstrated that one-bath dyeing of PET/ cotton blends using a combination of reactive dyes and alkali-clearable azohydroxypyridone disperse dyes containing the fluorosulfonyl group under high-temperature dyeing conditions was feasible. Fastness to rubbing of the synthesized dyes (ISO 105 X12) One-bath Dye F1 F2 F3 N1 N2 N3 Dry 5 5 5 4-5 5 5 Wet 3-4 3-4 3-4 4 4 4 Two-bath Dry Wet 5 4 5 3-4 5 3-4 5 4 5 4 5 4 Table 6. Fastness to alkaline perspiration of the synthesized dyes (ISO 105 E04) Dye F1 F2 F3 N1 N2 N3 One-bath D 4 3 3 2 2-3 3-4 C 4-5 4-5 4-5 3 4-5 4-5 N 4 3-4 3-4 2 3-4 4 P 5 4/5 4/5 4-5 5 5 A 5 5 5 5 5 5 W 4-5 4 4 3-4 4-5 4-5 D 4 3 3 3 3 3-4 C 4-5 4-5 4-5 4 5 5 Two-bath N 4 3-4 3-4 3 4 4-5 P 5 4-5 4-5 5 5 5 A 5 5 5 5 5 5 W 4-5 4 4 4 4-5 4-5 Table 4.2 Joonseok Koh and Jongseung Park Table 3. nylon. Vol. Perspiration Fastness The diacetate.132 Fibers and Polymers 2008. However. one-bath dyeing gave relatively lower perspiration fastness compared with two-bath dyeing by up to the ratings of 0.9.
Dyes Pigments. J. 120. Yang and S. J. Technol. Technol. Greaves. No. H. M. H.0.9. to be hydrolyzed and washed off while reactive dye is exhausted onto the cotton. 15. Dyes Pigments. Kim.39. Lee. 6. 18. Acknowledgements This paper was supported by Konkuk University in 2007. 4. Y. 265 (1998). probably because their alkali-clearable property enables the dyes to be applied in the same bath with cotton reactive dyes for a one-bath dyeing process: alkali clearing probably causes superficial disperse dye on the PET. Berger-schunn. P. J. Colour..D. C. D. Springer-Verlag. a similar depth of shade was obtainable by appropriate dye selection. Bradford. Kim. J. “Practical Color Measurement”. 120. A. 60. Koh. p. Polym. 5. Kim. P. S. M. Therefore. Koh and J. P. 2002. Koh. Kim. Greaves. 28. 38 (2000). S. 37. and J. New York.Azohydroxypyridone Disperse Dyes Fibers and Polymers 2008. 22. H. S. Soc. J. J. 103. A.. London. 3. energy. Although the one-bath method gave lower color yield on PET/cotton blends compared with conventional two-bath dyeing. Koh. Kim. water. Kim. T. Seoul National University. T. Koh. 9. Fibers and Polymers. Shore. J. Soc. Koh and J. J. TCC & ADR. F. 13. Yoo. Krayer. 56. M. 7. Koh. Koh and J. 100 (1987). J. Koh and A. J. Gordon and P. 1998. Kim. chemicals. A. and J. 23 (1996). T. 114. J. 10. An analogous comparison between the fluorosulfonylsubstituted derivatives and nitro analogues revealed a gap in alkali-clearability as exemplified by the difference between the one-bath dyeing and two-bath dyeing in wash fastness (Table 2): the ratings of wash fastness of one-bath dyeing were relatively lower than that of two-bath dyeing by up to the ratings of 0. M. Kleinmeier. John Wiley & Sons Inc. 8. Vol. Thesis. 233 (2006). Li. Dyers. and J.. References 1. Dyeings from the 4'-nitro analogues were also investigated for comparative purposes.. 156 (2004). Dyes Pigments. Fiber.5-1. A. and J. J. 56 (2004). J. we can anticipate the savings of energy. Kim. 69. Azohyddroxypyridone disperse dyes containing the fluorosulfonyl group showed an excellent level of fastness in onebath dyeing of PET/cotton blends. and A. J. Gregory. Dyes Pigments. 56. SDC. P. P. Koh.108. 241 (2004). 17 (2005). These dyes were not expected to be alkali-clearable enough since their nitro functions cannot give water-soluble dyes on hydrolysis although the ionization of hydroxypyridone under alkaline condition could contribute to the alkali-clearability. Brossman. and J. W. in addition to the improved productivity. B. 2. 134 (2004). 21. J. and labor. and water consumption in dyeing of PET/cotton blends. Dyes Pigments. J. 20. A. Dyers.. P. 5. P. J. 50. 155 (2004). 121 (1998). P. T. P. Koh. 19. S. Yang. Colour. Leaver. Color. Koh. Koh. 11. 105.. 117 (2001). 32. 9. D. J. 14. p. “Blends Dyeing”. Park. Kim. S.182. Baumann.. Baldwinson. 1994. Dyes Pigments. J. C. or any dye cross-staining of the cotton. P. J. 120. . Fibers and Polymers.. and H. by incorporation of an alkali clearing stage. Oh.. P. Kim. Y. Groebel. 12. Koh. Kim. Koh and J. Color. Oesch. 1982. The results demonstrate that azohydroxypyridone disperse dyes containing a fluorosulfonyl group are equally suitable for the one-bath dyeing process as for conventional two-bath dyeing. Dyes Pigments. J. “Organic Chemistry in Colour”. Colour. H. R. Seo. N. 269 (1989). and J. Dyers. 8. 69 (2003). Cunningham. Greaves. J. Technol. pp. 601 (2007). 17 (2003). Color. 101 (2008) 16. 64.2 133 time. Soc. J. Kim. Ph. 17.
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