Research Article pubs.acs.org/journal/ascecg
Carrier-Free and Low-Temperature Ultradeep Dyeing of Poly(ethylene terephthalate) Copolyester Modified with Sodium-5sulfo-bis(hydroxyethyl)-isophthalate and 2‑Methyl-1,3-propanediol Jun Wang,† Xiaoyan Li,† Fengyan Ge,† Zaisheng Cai,*,† and Lixia Gu‡ †
Key Laboratory of Science & Technology of Eco-Textile, Ministry of Education, Donghua University, North Renmin Road 2999, Shanghai 201620, China ‡ State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Material Science and Engineering, Donghua University, North Renmin Road 2999, Shanghai 201620, China S Supporting Information *
ABSTRACT: To obtain sufficient dyeability, dyeing of poly(ethylene terephthalate) fabrics must be performed at high temperature and high pressure or by using a noeco-friendly carrier at atmospheric pressure, which implies large energy consumption and environmental contamination. In order to improve the sustainability of the dyeing process, a carrier-free and low-temperature dyeing procedure was developed for the poly(ethylene terephthalate) copolyester (MCDP) incorporated with sodium-5-sulfo-bis(hydroxyethyl)-isophthalate (SIP) and 2-methyl-1,3-propanediol (MPD). The results obtained from cationic dyeing at optimized conditions show an outstanding dye utilization (99.0%) with MCDP, which is much higher than that of the conventional SIP-modified copolyester. Meanwhile, the introduction of SIP and MPD contents ensures the large adsorption and fast diffusion of dye molecules into the amorphous region of fibers, allowing an efficient and deep disperse dyeing of polyester fabrics under atmosphere in the absence of carriers. The environmental benefits arising from high quality dyed MCDP fabrics with ultradeep dyeing performance and excellent color fastness through a facile and clean dyeing process are highlighted with the economic ones. KEYWORDS: Copolyester, Low-temperature, Carrier-free, Ultradeep dyeing
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INTRODUCTION Of all synthetic fibers, poly(ethylene terephthalate) (PET) fibers have been widely used in the textile industry due to their unique physical and mechanical properties. However, dyeing of PET fabrics with various dyes is an intricate matter and presents considerable difficulties because of their high crystallinity, tight structure, and lack of reactive groups.1 To obtain sufficient dyeability, general dyeing conditions used for PET fabrics require high temperatures (around 130 °C) and high pressures, which imply large energy consumption and potential risk caused by pressurized vessels.1,2 Carrier dyeing of polyester has been intensively studied as a means of improving dye uptake and lowering disperse dyeing temperature.3,4 The presence of carrier can make the fiber undergo some structural transformations which facilitated the dye adsorption and diffusion.5,6 Nevertheless, most of the carriers (phenols, amines, etc.) have significant problems with toxicity and environmental contamination; thus, much effort is required to develop new eco-friendly and low-temperature dyeing of PET without the need for carriers.7−9 Easy cationic dyeable copolyester (ECDP)10−13 is known for a modified PET copolyester dyeing at boiling temperature under atmospheric pressure without carriers. It has been produced by incorporating sodium-5-sulfo-bis(hydroxyethyl)© XXXX American Chemical Society
isophthalate (SIP) and poly(ethylene glycol) (PEG) into regular polyester. Compared to the normal SIP-incorporated copolyester13−16 (known as cationic dyeable copolyester, CDP), ECDP shows improved boiling dyeability and enhanced hygroscopicity thanks to the increase of ether bond and hydroxyl value from PEG units. However, the further application of ECDP as PET replacement has been limited by the undesired properties, such as poor spinnability, low light fastness, and poor pile-on property in the boiling dyeing processes.15,17 Recently, a 2-methyl-1,3-propanediol (MPD) modified copolyester (MCDP) was developed in our laboratory to overcome the drawbacks of ECDP and further enhance its dyeability at boiling temperature.18,19 MCDP fiber was synthesized and prepared using SIP and MPD as the third and fourth comonomers by a melting and drawing process. The newly produced copolyester displayed high quality properties of soft handle, antipilling property, and excellent spinnability and drawability. Most importantly, the introduction of MPD substantially reduced the regularity of SIP-modified PET and Received: February 17, 2016 Revised: May 4, 2016
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DOI: 10.1021/acssuschemeng.6b00338 ACS Sustainable Chem. Eng. XXXX, XXX, XXX−XXX
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Dyeing Procedures. For cationic dyeing, CDP, ECDP, and MCDP fabrics weighing 1.0 g were dyed in a dyeing machine (Rapid; Taiwan) with Basic Red 46 at various pH values (3−8) and dye concentrations (1−8% o.w.f). The liquor ratio was kept at 20:1. Dyeing temperature was raised from 40 to 70 °C by 1 °C/min and held for 10 min, and then was up to 100 °C for a fixed time. After dyeing, the fabrics were washed at 40 °C for 30 min and dried under ambient conditions. For disperse dyeing, MCDP fabric samples weighing 1.0 g were dyed with three disperse dyes at various dyebath conditions (pH, time, temperature and dye concentration). The liquor ratio was kept at 20:1, the temperature was set at 40 °C, and then raised to a fixed temperature by 1 °C/min and dyeing operations continued for a fixed time. After dyeing, the dyed fabrics were washed twice and air-dried. The alkaline pretreatment and conventional disperse dyeing of PET fabrics was carried out under high temperature and high pressure (HTHP) conditions as described before.20 Measurements. The detailed procedures for dye uptake, color yield, color fastness, and tensile strength test are provided in the Supporting Information. Differential Scanning Calorimetry (DSC). The thermal property of the CDP, ECDP, and MCDP fabric was measured using Thermal Analyzer 204F1 (Netzsch, German) under nitrogen atmosphere. The following conditions were used: temperature range, 30−290 °C; scan rate, 10 °C/min; differential thermal compensation range, 120 mW; and sampling temperature, 50−270 °C. X-ray Diffraction (XRD). The XRD analysis were performed on Xray diffractometer D/Max 2500PC (Rigaku, Japan). The diffracted intensity of Cu Kα radiation (0.154 nm, 40 kV, and 200 mA) was measured in the 2θ range between 5° and 60° at the scanning rate of 5 °C/min.
increased the accessibility for the dye molecule, offering the possibility for ultradeep dyeing under atmospheric conditions without carriers. In the present work, a carrier-free and low-temperature dyeing procedure for MCDP was developed. The influence of dyeing conditions (pH, temperature, time, and dye concentration) on cationic and disperse dyeability of MCDP fabrics was elucidated. The dye performance including color strength (K/S value), tensile strength, and the color fastness of MCDP was measured and compared with regulator PET and SIPmodified PET fabrics. Moreover, the structure and thermal property of the MCDP fabric was also evaluated to analyze the dyeing mechanism and dyeability of the fabric with cationic and disperse dyes.
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MATERIALS AND METHODS
Materials. The preparation of CDP, ECDP, and MCDP copolyester containing identical SIP content was mentioned in the previous work.18,19 PET, CDP, ECDP, and MCDP woven fabrics investigated (plain weave, 110 g/cm3) were supplied by Shanghai Lianji Synthetic Fiber Co., Ltd. (China). All fabrics were soaped at 60 °C for 30 min and air-dried at room temperature. Four commercial cationic and disperse dyes were supplied by Runtu Co., Ltd. (China) with the chemical structures shown in Figure 1. Chemical reagents
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RESULTS AND DISCUSSION Thermal and Structural Property. DSC heating curves for CDP, ECDP, and MCDP fabrics in Figure 2a distinctly exhibit the region of glass transition and peaks corresponding to cold crystallization and melting behavior. It can be observed that the glass transition temperature (Tg) decreased in the order of CDP, ECDP, and MCDP. This manifests that the branched methyl groups in the MPD unit enhanced flexibility and the irregularity of molecular chains, meaning that MCDP has more free volume and larger fraction of amorphous regions which allowed more dye molecules to penetrate. Accordingly, the lower Tg these samples have, the better were the dyeability and soft handling with which they were endowed. Meanwhile, the incorporation of feed MPD as the fourth component in the PET structure result in random copolyester with considerable enhancement in chain flexibility. This
Figure 1. Chemical structure of used cationic and disperse dyes. including acetic acid, sodium acetate, sodium dihydrogen phosphate, sodium hydrogen phosphate, citric acid, sodium carbonate, and sodium hydrosulfite were of analytical grade and were used as received from Sinopharm Chemical Reagent Co. Ltd. (China).
Figure 2. DSC thermograms and WRD diffractograms of all SIP-modified copolyesters. B
DOI: 10.1021/acssuschemeng.6b00338 ACS Sustainable Chem. Eng. XXXX, XXX, XXX−XXX
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Figure 3. Effects of (a) pH (b) temperature, (c) time, and (d) dye concentration on the cationic dyeability of all SIP-modified copolyesters. Dyeing conditions: (a) 5% o.w.f, 100 °C, 130 min; (b) pH 4−5, 5% o.w.f, 130 min; (c) pH 4−5, 5% o.w.f, 100 °C; and (d) pH 4−5, 100 °C, 130 min.
peaks24 were 48.6, 43.9, and 39.1%, respectively. As mentioned earlier, the crystallinity of MCDP is the lowest due to the steric hindrance effect of the MPD groups destroying the regularity of the polymer chain molecules and leading to a looser crystal structure. Cationic Dyeability. The presence of SIP content increased anionic dye sites for cationic dye−fiber interaction, imparting the PET copolyester with cationic dyeability. Our first objective is to evaluate the cationic dyeability of MCDP fiber for all cationic dyeable copolyesters with identical SIP content. Therefore, the dyeing behavior of cationic dye on CDP, ECDP, and MCDP fabrics was investigated with respect to pH, time, temperature, and dye dosage. pH. Figure 3a presents the effect of pH on dye uptakes of all SIP-modified PET fabrics. Irrespective of the type of copolyesters, the dye uptakes of Basic Red 46 (BR46) increased as pH increased and reached a maximum in the region of pH 4−5. This result can be attributed to the hydrolytic stability of the dye structure and the surface charge of copolyester fiber at a certain pH.25 The dye uptake at maximum can be explained by the increased probability of interactions between the ionized sulfonic groups on fiber and protonated dye molecules, as well as the stability of cationic dye at the appropriate pH.26 Temperature. Generally, the dye uptake in synthetic fiber was correlated with the quantity and structure of the amorphous region. It can be found from Figure 3b that the dye exhaustion increased markedly when holding temperature exceeded the Tg of three copolyester fiber. This trend could be
enhanced the capability of molecular chains crowding into crystal lattices, leading to a reduction of cold crystallization temperature (Tcc) of MCDP compared with other SIP-modified PET.11,21 Another reason for this phenomenon is that sodium compounds could nucleate the crystallization of PET. The addition of the MPD unit made more ionic species available to the reaction with the ester linkage of PET, creating sodium carboxylate chain ends, which were concluded to be the effective nucleating species.22 Another thermal parameter, the melting temperature (Tm), was found to decrease in the order of MCDP, CDP, and ECDP, accompanying with the gradually widening melting peak. As reported elsewhere,11,17,23 the presence of unstable ether bonds in PEG segments led to the poor thermal stability of ECDP. However, MCDP with higher thermal stability is due to the adverse effect of the methyl side groups on chain segment motion, resulting in the improved thermal stability to some degree. The X-ray diffraction pattern of a polymer reflects its crystalline structure. In Figure 2b, there is no obvious positional changes except for the diffraction intensities of the characteristic diffraction peaks in the XRD spectra, indicating that the added MPD and PEG units were in the noncrystalline state as minor components in these copolyesters. This can be proven by the almost unchanged diffracting angles of (010), (110), and (100) reflecting planes, which are 17.5°, 22.5°, and 25.8° for all testing samples. In addition, the crystallinities of the CDP, ECDP, and MCDP calculated by the method of dividing C
DOI: 10.1021/acssuschemeng.6b00338 ACS Sustainable Chem. Eng. XXXX, XXX, XXX−XXX
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Scheme 1. Illustration for the Penetration of MCDP Copolyester and Possible Interactions between the Copolyester and Cationic/Disperse Dye Molecules
explained by the increased molecular movements of the fiber segment at temperatures higher than Tg, and the consequent generation of more free volume allowed dyes to penetrate (Scheme 1). The highest color yield of MCDP shows that the decreased crystallinity of the copolyester is caused by the introduction of flexible branched diol into the macromolecular chain. With decreasing crystallinity, the amorphous regions and the accessibility into them increased. Accordingly, the dye uptake capacity of the MPD-modified copolyester improved because of trapping more dye molecules within them. Time. The dyeing rate curve in Figure 3c reveals that a marked increase in the percent exhaustion of all dyed samples occurred at a temperature about 10 °C higher than their Tgs (ca. 50 min). This can be explained in terms of the promoted rate of dye diffusion as a consequence of the formation of amorphous region transformed from partial crystalline. In comparison with other copolyester, MCDP exhibited the shorter balance time (ca. 100 min) and higher dyeing capacity due to its larger quantity of available dyeing sites. That is to say, for MCDP, a smaller amount of dyestuff is needed for the same shade depth. Dye Concentration. Figure 3d shows that the extent of dye exhaustion decreased progressively, regardless of fiber type, with increasing dye concentration in the dyebath. This trend is due to the increased adsorption of dye cations on negatively charged fiber surface which weaken the electrostatic dye−fiber interaction and prevent dye sorption.27 Furthermore, the available dye sites on fiber were gradually occupied, and the competitive hydrolysis of dye molecules increased at higher dye concentrations, resulting in a decrease of dye uptake.28
To further investigate the dye adsorption capacity of MCDP, dye saturation value, which corresponds to the ability of anionic synthetic fiber to absorb cationic dye, was calculated by a threepoint fitting method (Figure S1−S3 of the Supporting Information).29 Interestingly, the MCDP fiber (2.84%) showed much higher value for dye saturation compared to that of CDP (0.49%) and ECDP (1.96%) fibers with identical feed SIP contents. The higher dye saturation value of the MCDP can be explained by its relatively more open structure and increased accessibility of the sulfonic groups in the fiber. Disperse Dyeability. One of our attempts in this study was to evaluate the quality of dyed MCDP fabrics with disperse dyes at boiling temperature under atmospheric conditions without carriers. Dyeing experiments with three disperse dyestuffs might contribute to the exploration of the dyeability of MCDP under these dyeing conditions. pH. It is shown in Figure 4a that the color strength of the MCDP fabrics improved when the pH values increased from 3 to 6 but started to gradually decline with further increase. Similar to cationic dye, the effect of disperse dyebath pH can be attributed to the correlation between the intention of hydrolysis and reduction of disperse dyes and the quantity and structure of amorphous regions for the MCDP fiber structure.30 Results of the experiment indicate an optimal dye yield at pH 5−6. Temperature. It can be observed in Figure 4b that the color strength of dyed MCDP increases at first and then decreases with increasing temperature. Generally, a higher temperature could could promote the thermal movement of the dye molecules by breaking the bonds (van der Waals forces, Dipole−dipole bond and hydrogen bond) between polymer chains above Tg.31 Higher color yield obtained with the formation of larger, more accessible voids through which the D
DOI: 10.1021/acssuschemeng.6b00338 ACS Sustainable Chem. Eng. XXXX, XXX, XXX−XXX
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Figure 4. Effects of (a) pH, (b) temperature, (c) time, and (d) dye concentration on dye uptake of three different azo disperse dyes on MCDP copolyesters. Dyeing conditions: (a) 4% o.w.f, 100 °C, 90 min; (b) pH 5−6, 4% o.w.f, 90 min; (c) pH 5−6, 4% o.w.f, 100 °C; and (d) pH 5−6, 100 °C, 90 min.
disperse dye molecules can diffuse more readily. However, as temperature was increased successively, the tendency of the dye molecules to go from the fiber into the dyebath was also enhanced. Time and Dye Concentration. Figure 4c shows that there is almost no dye adsorption below 65 °C. A holding time of 30 min at 100 °C should be sufficient based on the equilibrium point detected. This behavior is a consequence of the balance in the amounts of dyestuff that diffused into the fibers and escaped from fibers at equilibrium. The dye uptake of BR46 was plotted as a function of dye concentrations in Figure 2d. It was seen that the dye uptake changed little when the dye concentration up to 5% o.w.f. This trend may be caused by the crash and coagulation of dyestuff molecules at high concentration, which reduce the adsorption and fixation of disperse dye on MCDP fabrics.30 Comparison of Conventional Dyeing Process. The color strength data above indicated that MCDP fabric could be successfully dyed with disperse dyes in the absence of a carrier. To further evaluate the possibility of the replacement of HTHP dyeing of PET, the K/S values of three disperse dyes on all SIPmodified copolyesters at boiling temperature and conventional dyed PET were measured in Figure 5. As expected, for all disperse dyes, it can be seen MCDP fabrics yield the highest K/S values in modified copolyester, which corresponded well to their cationic dyeability. Therefore, it seemed that changes in the amorphous structure caused by the additional MPD content played a great role not only in cationic dye adsorption but also in disperse dye diffusion.
Figure 5. Comparison of color strength between HTHP-dyed PET fabrics and SIP-modified copolyester fabrics dyed at 100 °C with 5% o.w.f disperse dyes.
Compared to conventional dyeing of PET, the K/S values of the MCDP copolyester was 19.6−35.5% higher than that of dyed PET. Especially, the low-temperature dyeing method produced ultradeep dyed products without the alkali pretreatment of PET and the addition of carrier. This is very important because the use of alkali pretreatment and carrier would result in the difficulty of effluent treatment. E
DOI: 10.1021/acssuschemeng.6b00338 ACS Sustainable Chem. Eng. XXXX, XXX, XXX−XXX
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ACS Sustainable Chemistry & Engineering Table 1. Tensile Strength of Three SIP-Modified Copolyester Dyed Samples with BR46 tensile strength (N) samples CDP
original dyeda original dyeda original dyeda
ECDP MCDP a
elongation at break (%)
weft
warp
weft
warp
weft
645.6 614.4 633.8 618.6 575.1 559.8
565.5 538.2 534.2 509.9 455.4 443.7
35.41 33.23 36.22 35.77 40.49 37.49
32.70 32.25 35.66 34.24 40.33 39.99
4.83
4.83
2.40
4.56
2.66
2.56
Dyeing conditions: 5% o.w.f; pH 4−5; 100 °C, 130 min.
methyl-1,3-propanediol (MPD). The cationic and disperse dyeability of MCDP fabrics at different dyeing conditions were evaluated. The results at optimized conditions show an outstanding cationic dye utilization (99.0%) and deep disperse color yield (19.6−35.5% higher than HTHP-dyed PET) of dyed MCDP, which can be explained by the lower glass transition temperature and crystalline degree observed from DSC and XRD analysis. Meanwhile, high quality dyed MCDP fabrics were obtained with excellent tensile strength and color fastness. An advantage of our method is that sufficient dyeing of polyester fabrics can be accomplished with a reduced temperature without using high pressure or carrier, which indicates the use of less energy and safer processing conditions compared with those of conventional processes. Another advantage is that the ultradeep color of dyed MCDP samples was achieved using this method in contrast to HTHP-dyed PET dyeing before alkali pretreatment. This fact indicates that the process can be operated using less dyestuff to get the same depth and requires less and safer chemicals than the usual processes. That is to say that the eco-friendly and low-cost dyeing of MCDP in this work signicantly contributes to the increase the sustainability of conventional PET dyeing processes.
The ultradeep color yield can be interpreted by the dyeing mechanism of MCDP shown in Scheme 1. In this work, Disperse Yellow 163 (DY163), Disperse Red 167 (DR167), and Disperse Blue 79 (DB79) are azo dyes and can be adsorbed on the surface of MCDP fibers by van der Waals force and hydrogen bonding. Similar to the dyeing mechanism of PET, initial adsorption is rapid because of the high affinity polyester has for disperse dyes, but diffusion within the fiber is the key stage of whole dyeing as it is at the slowest rate. For the dyeing of MCDP, the segmental mobility of molecular chains, which is the major influence of diffusion rate, can be tremendously increased under the same thermal energy due to the lower Tg and larger amorphous regions compared with PET. Additionally, the lower temperature dyeing method can be performed without a carrier because MCDP fiber itself will probably have the same role of enhanced segmental mobility as carriers do. Tensile Strength and Color Fastness. The values of the tensile strength of three dyed SIP-modified copolyester fabrics with cationic dye were summarized in Table 1. The tensile strength in the warp and weft direction of all the dyed samples decreased, and the loss of MCDP was lower than 3%. The similar result of MCDP dyed with three disperse dyes can be observed from Table S1. This indirectly proved that the damage of both the cationic and disperse dyeing process to the MCDP fiber was so limited that it would not affect industrial use. From Table 2 and Table S2, all cationic and disperse dyed fabrics exhibited good fastness properties in washing and
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washing
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acssuschemeng.6b00338. Measurements for dye uptake, color yield, color fastness, and breaking strength test; three-point fitting of SIPmodified copolyester dyeing rate curves; tensile strength and color fastness of HTHP-dyed PET and boil-dyed SIP-modified copolyester fabrics with disperse dyes (PDF)
rubbing
samples
K/S value
light
cotton
PET
dry
wet
CDP ECDP MCDP
15.877 19.212 21.523
4 4 5
4/5 5 5
4 4/5 5
5 4 5
4/5 4 4
ASSOCIATED CONTENT
S Supporting Information *
Table 2. Color Fastness of Three SIP-Modified Copolyester Dyed Samples with BR46a
a
loss of strength (%)
warp
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Dyeing conditions: 5% o.w.f; pH 4−5; 100 °C, 130 min.
AUTHOR INFORMATION
Corresponding Author
rubbing fastness. For cationic dyeing, it is due to the strong electrovalent bond linkage between the cationic dye and more accessible acidic group on MCDP. Meanwhile, MCDP fibers were found to have excellent fastness with disperse dyes due to the effective trap of dye molecules within the amorphous region of the fiber.
*Tel: +86-021-67792609. Fax: +86-021-67792608. E-mail:
[email protected]. Notes
The authors declare no competing financial interest.
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ACKNOWLEDGMENTS This work was supported by Program for Specialized Research Fund for the Doctoral Program of Higher Education in China (No.20130075130002) and the National Natural Science Foundation of China (Grant No. 51203018).
CONCLUSIONS The present work developed a carrier-free and low-temperature dyeing procedure for MCDP copolyester incorporated with sodium-5-sulfo-bis(hydroxyethyl)-isophthalate (SIP) and 2F
DOI: 10.1021/acssuschemeng.6b00338 ACS Sustainable Chem. Eng. XXXX, XXX, XXX−XXX
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(23) Li, X.; Wang, J.; Wang, H.; Cai, Z. Alkaline hydrolysis and pretreatment of trilobal high dimethyl 5-sulfoisophthalate sodium cationic dyeable polyester. J. Text. Inst. 2015, 1−11. (24) Hsiao, K.-J.; Kuo, J.-L.; Tang, J.-W.; Chen, L.-T. Physics and kinetics of alkaline hydrolysis of cationic dyeable poly(ethylene terephthalate) (CDPET) and polyethylene glycol (PEG)−modified CDPET polymers: Effects of dimethyl 5-sulfoisophthalate sodium salt/ PEG content and the number-average molecular weight of the PEG. J. Appl. Polym. Sci. 2005, 98 (2), 550−556. (25) Aspland, J. R. Chapter 12: The Application of Basic Dye Cations to Anionic Fibers: Dyeing Acrylic and Other Fibers with Basic Dyes. Text. Chem. Color. 1993, 25 (6), 21−26. (26) Wang, J.; Li, X.; Cai, Z.; Gu, L. Absorption kinetics and thermodynamics of cationic dyeing on easily dyeable copolyester modified by 2-methyl-1,3-propanediol. Fibers Polym. 2015, 16 (11), 2384−2390. (27) Teli, M. D.; Prasad, N. M.; Vyas, U. V. Electrokinetic properties of modified polyester fibers. J. Appl. Polym. Sci. 1993, 50 (3), 449−457. (28) Harwood, R. J.; McGregor, R.; Peters, R. H. Adsorption of Cationic Dyes by Acrylic Films II-Kinetics of Dyeing. J. Soc. Dyers Colour. 1972, 88 (8), 288−292. (29) Li, X.; Wang, H.; Cai, Z.; Yu, J. Cationic dyeing properties of trilobal high dimethyl 5-sulfoisophthalate sodium salt (SIP) content cationic dyeable polyester (THCDP) fabrics. J. Text. Inst. 2015, 106 (8), 835−844. (30) Aspland, J. R. Chapter 9: The Structure and Properties of Disperse Dyes And Related Topics. Text. Chem. Color. 1993, 25 (1), 21−25. (31) Silkstone, K. The Influence of Polymer Morphology on the Dyeing Properties of Synthetic Fibres. Rev. Prog. Color. Relat. Top. 1982, 12 (1), 22−30.
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