Journal of Textile Research ›› 2024, Vol. 45 ›› Issue (01): 120-127.doi: 10.13475/j.fzxb.20230300101

• Dyeing and Finishing Engineering • Previous Articles     Next Articles

Application of methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate in supercritical carbon dioxide fluid dyeing with disperse dyes

GE Huaifu1,2, WU Wei1,2(), WANG Jian3, XU Hong1,2,4, MAO Zhiping1,2,4,5   

  1. 1. Key Laboratory of Science and Technology of Eco-Textile, Ministry of Education, Donghua University, Shanghai 201620, China
    2. College of Chemistry and Chemical Engineering, Donghua University, Shanghai 201620, China
    3. Jifa Group Co., Ltd.,Qingdao, Shandong 266000, China
    4. Innovation Center for Textile Science and Technology, Donghua University, Shanghai 201620, China
    5. National Engineering Research Center for Dyeing and Finishing of Textiles, Donghua University, Shanghai 201620, China
  • Received:2023-03-01 Revised:2023-05-06 Online:2024-01-15 Published:2024-03-14

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Abstract:

Objective Supercritical carbon dioxide fluid (ScCO2) dyeing of disperse dyes with low energy consumption and no effluent discharge in the dyeing process is an advanced industrial technology in line with sustainable development. However, some problems associated with the disperse dyes in this process, such as low dye uptake and incomplete dye chromatography caused by low solubility, greatly limit their further development. In view of these problems, this paper proposed to add appropriate cosolvent to the ScCO2 to improve its solubility, so as to reduce the impact of these problems on the dyeing process.

Method Based on the interaction forces between disperse dye molecules and cosolvent molecules, a green cosolvent (methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate) with high solubility for disperse dyes, high boiling point and non-volatile and non-toxic was selected as a dyeing auxiliary. Disperse yellow 163 and Disperse Blue 60 were selected as experimental dyes. The dyeing rates and K/S values of disperse dye filter cakes and disperse dye filter cakes with cosolvent blends were tested under different process conditions to evaluate their dyeing effects. The mechanical properties and color fastness of the dyed yarns were characterized to assess the effect of the cosolvent addition on the yarn properties.

Results The influence of cosolvent on the fabric was studied through the reflectance curve of the dyed fabric. The results showed that the selected cosolvent has a significant influence on the brightness of the fabric, but it will not change the color and saturation of the fabric. With the addition of cosolvent, the K/S value of fabric dyed by Disperse Yellow 163 increased from 4.5 to 12.0, and that of fabric dyed by Disperse Blue 60 increased from 5.9 to 12.2, indicating that this cosolvent could be used in supercritical carbon dioxide fluid dyeing with disperse dyes. By changing the mass ratio of disperse dyes to liquid cosolvent, dyeing temperature and pressure, the influence of process conditions on the dye uptake of disperse dyes was investigated. The dye uptake of disperse dyes increased significantly after adding the cosolvent. When the mass ratio of dye and cosolvent was 1∶20, the dyeing rate of Disperse Yellow 163 and Disperse Blue 60 reached 57.62% and 70.97%, respectively. With the increase of temperature, the dye uptake increased first and then decreased after adding cosolvent, reaching the maximum at 130 ℃. With the increase of pressure, the dye uptake of disperse dyes increased slightly. The dye uptake did not change significantly with the dyeing pressure above 27 MPa, and the optimum dyeing pressure was 27 MPa. The mechanical properties and color fastness of four different yarns were characterized. The breaking strength and the elongation at break did not change significantly, and the breaking strength of yarns is all about 250 cN and elongation at break is all about 20%. Color fastness to rubbing, color fastness to sunlight and color fastness to soaping of the yarn were all above 4 levels. Properties of yarns dyed with cosolvent met the production requirements.

Conclusion In this study, methyl-5-(dimethylamino)-2-methyl-5-oxopentanoate was used as a dyeing cosolvent to effectively improve the dyeing rate of Disperse Yellow 163 and Disperse Blue 60 in the supercritical CO2 fluid dyeing process from a practical production problem. Meanwhile, the addition of the cosolvent only affected the brightness of the dyed yarn, and had no significant effect on the color phase and saturation. A suitable dyeing process was determined by the subsequent experiment conditions, i.e., the mass ratio of dye to co-solvent was 1:20, the dyeing temperature was 130 ℃, and the dyeing pressure was 27 MPa. After the addition of cosolvent, the resulting fabric with increased color depth, no significant loss of mechanical properties, and excellent color fastness performance met the requirements of national standards. In summary, the addition of cosolvent caused no significant effect on yarn properties while improving the dyeing rate of disperse dyes with good application prospects in the field of ScCO2dyeing.

Key words: disperse dye, supercritical carbon dioxide fluid, cosolvent, dye-uptake, polyester yarn

CLC Number: 

  • TS193.1

Fig.1

Structure formula for methyl-5-(dimethylamino)-2-methyl-5-oxopentanoate"

Fig.2

Spectral reflectance curves of different dyeing systems. (a) Y163 and Y163+cosolvent; (b) B60 and B60+cosolvent"

Fig.3

Standard absorbance curves for disperse dyes. (a) Disperse Yellow 163; (b) Disperse Blue 60"

Fig.4

Dye uptake of yarn dyed by disperse dyes with different cosolvent dosages"

Tab.1

K/S values of yarn dyed by dyeing systems with different dosages of co-solvents"

助溶剂
用量/g		 K/S值
分散黄163 分散蓝60
0 4.5 5.9
5 6.1 9.0
10 9.8 11.0
15 11.1 12.1
20 12.0 12.2

Fig.5

Influence of temperature on dye uptake of different dyeing systems"

Tab.2

K/S values of yarns dyed with four dyeing systems at different temperatures"

温度/
℃		 K/S值
Y163 Y163+助溶剂 B60 B60+助溶剂
90 3.8 8.3 4.7 7.3
100 4.1 9.6 5.2 8.8
110 4.2 10.7 5.7 10.1
120 4.4 11.1 5.8 11.6
130 4.5 12.0 5.9 12.2
140 4.6 12.0 6.0 12.2

Fig.6

Influence of pressure on dye uptake of different dyeing systems"

Tab.3

K/S values of yarns dyed with four dye systems under different pressures"

压力/
MPa		 K/S值
Y163 Y163+助溶剂 B60 B60+助溶剂
22 3.8 11.4 5.4 11.0
24 4.2 11.5 5.7 11.4
26 4.5 11.8 5.8 12.0
27 4.5 12.0 5.9 12.2

Tab.4

Mechanical property of yarn"

染料 断裂强力/
cN		 断裂强力
CV值/%		 断裂伸长
率/%		 断裂伸长率
CV值/%
Y163 250.23 1.55 20.81 3.26
Y163+助溶剂 248.36 2.24 19.42 3.36
B60 252.04 2.13 21.08 3.61
B60+助溶剂 256.18 1.76 21.13 3.28

Tab.5

"

染料 耐日晒色
牢度		 耐摩擦色牢度 耐皂洗色牢度
原样变色 不同材质贴衬沾色
湿摩 干摩
丝 漂白棉 涤纶 聚丙烯腈 毛 聚酰胺
Y163 ≥4 5 5 4~5 4~5 4~5 4~5 4~5 5 4~5
Y163+助溶剂 ≥4 4~5 4~5 4~5 4~5 4~5 4~5 4~5 5 4~5
B60 ≥4 5 5 4~5 4~5 4~5 4~5 4~5 5 4~5
B60+助溶剂 ≥4 4~5 4~5 4~5 4~5 4~5 4~5 4~5 5 4~5
[1] 陈何卿, 陈旭, 管永银, 等. 涤纶分散染料低共熔溶剂染色[J]. 染整技术, 2022, 44(2): 12-15,48.
CHEN Heqing, CHEN Xu, GUAN Yongyin, et al. Deep eutectic solvent dyeing of polyester with disperse dyes[J]. Textile Dyeing and Finishing Journal, 2022, 44(2): 12-15,48.
[2] 程文青. 硅基非水介质中分散染料对涤纶纤维的上染特性研究[D]. 杭州: 浙江理工大学, 2021:6-7.
CHENG Wenqing. Study on the dyeing characteristics of disperse dyes to polyester fiber in silicon-based non-aqueous medium[D]. Hangzhou: Zhejiang Sci-Tech University, 2021:6-7.
[3] 费良, 殷允杰, 王潮霞. 新型泡沫染整概述[J]. 印染助剂, 2020, 37(8): 1-5.
FEI Liang, YIN Yunjie, WANG Chaoxia. Overview of novel foam dyeing and finishing[J]. Textile Auxiliaries, 2020, 37(8):1-5.
[4] TANG A Y L, LEE C H, WANG Y M, et al. Polyethylene glycol (PEG) non-ionic surfactant-based reverse micellar dyeing of cotton fabric with hot type trichloropyrimidine (TCP)-based reactive dyes[J]. Journal of Natural Fibers, 2023, 20(1): 2131689.
doi: 10.1080/15440478.2022.2131689
[5] 万伟, 刘今强, 李莎, 等. D5反胶束体系的制备及其增溶特性的研究[J]. 应用化工, 2009, 38(10): 14, 17-20,36.
WAN Wei, LIU Jinqiang, LI sha, et al. Study on the preparation and solubilization properties of D5 reverse micelle system[J]. Applied Chemical Industry, 2009, 38(10): 14, 17-20,36.
[6] BANCHERO M. Recent advances in supercritical fluid dyeing[J]. Coloration Technology, 2020, 136(4): 317-335.
doi: 10.1111/cote.v136.4
[7] 裴刘军, 施文华, 张红娟. 非水介质活性染料染色关键技术体系及其产业化研究进展[J]. 纺织学报, 2022, 43(1):122-130.
PEI Liujun, SHI Wenhua, ZHANG Hongjuan, et al. Technology progress and application prospect of non-aqueous medium dyeing systems[J]. Journal of Textile Research, 2022, 43(1):122-130.
[8] 郑环达, 郑来久. 超临界流体染整技术研究进展[J]. 纺织学报, 2015, 36(9):141-148.
ZHENG Huanda, ZHENG Laijiu. Research development of supercritical fluid dyeing and finishing technology[J]. Journal of Textile Research, 2015, 36(9):141-148.
[9] 《“十四五”工业绿色发展规划》发布绿色低碳转型方向[J]. 印染, 2022, 48(1): 84-85.
The "14th Five-Year Plan" for Industrial Green Development released the direction of green and low-carbon transformation[J]. China Dyeing & Finishing, 2022, 48(1): 84-85.
[10] TSAI C C, LIN H M, LEE M J. Solubility of 1,5-Di-aminobromo-4,8-dihydroxyanthraquinone in supercritical carbon dioxide with or without cosolvent[J]. Journal of Chemical & Engineering Data, 2008, 54(5): 1442-1446.
doi: 10.1021/je800646h
[11] TSAI C C, LIN H M, LEE M J. Solubility of C.I. Disperse Violet 1 in supercritical carbon dioxide with or without cosolvent[J]. Journal of Chemical & Engineering Data, 2008, 53(9): 2163-2169.
doi: 10.1021/je8003673
[12] BANCHERO M, FERRI A, MANNA L, et al. Solubility of disperse dyes in supercritical carbon dioxide and ethanol[J]. Fluid Phase Equilibria, 2006, 243(1/2): 107-114.
doi: 10.1016/j.fluid.2006.02.010
[13] CAMPANA F, MASSACCESI B M, SANTORO S, et al. Polarclean/water as a safe and recoverable medium for selective C2-arylation of indoles catalyzed by Pd/C[J]. ACS sustainable chemistry & engineering, 2020, 8(44): 16441-16450.
[14] RANDOVÁ A, BARTOVSKÁ L, MORÁVEK P, et al. A fundamental study of the physicochemical properties of Rhodiasolv Polarclean: a promising alternative to common and hazardous solvents[J]. Journal of Molecular Liquids, 2016, 224: 1163-1171.
doi: 10.1016/j.molliq.2016.10.085
[15] WANG H H, JUNG J T, KIM J F, et al. A novel green solvent alternative for polymeric membrane preparation via nonsolvent-induced phase separation (NIPS)[J]. Journal of Membrane Science, 2019, 574: 44-54.
doi: 10.1016/j.memsci.2018.12.051
[16] 袁理, 王丹书, 谷迁. 基于光谱泛相似测度的色纺纱线与织物间呈色规律[J]. 纺织学报, 2019, 40(2):30-37.
YUAN Li, WANG Danshu, GU Qian. et al. Coloration rules between colored spun yarns and its fabricsbased on spectral pan-similarity measure[J]. Journal of Textile Research, 2019, 40(2):30-37.
[17] ZHENG Jinhua, XV Mingxian, LU Xueyan. Measurement and correlation of solubilities of C.I. Disperse Red 73, C.I. Disperse Blue 183 and their mixture in supercritical carbon dioxide[J]. Chinese Journal of Chemical Engineering, 2010, 18(4):648-653.
[18] FERRI A, BANCHERO M, MANNA L, et al. Dye uptake and partition ratio of disperse dyes between a PET yarn and supercritical carbon dioxide[J]. The Journal of Supercritical Fluids, 2006, 37(1): 107-114.
doi: 10.1016/j.supflu.2005.07.001
[19] MONTERO G A, SMITH C B, HENDRIX W A, et al. Supercritical fluid technology in textile processing: an overview[J]. Industrial & Engineering Chemistry Research, 2000, 39(12): 4806-4812.
doi: 10.1021/ie0002475
[20] 汪孟艳. 超临界CO2体系溶解度参数的分子动力学模拟研究[D]. 天津: 天津大学, 2007:27-31.
WANG Mengyan. Study on solubility parameter of supercritical carbon dioxide by molecular dynamics simulation[D]. Tianjin: Tianjin University, 2007:27-31.
[21] 黄钢. 超临界流体染色产业化关键技术的研究[D]. 上海: 东华大学, 2010:55-57.
HUANG Gang. The study of key technologies on the dyeing of textiles in supercritical fluid on industrial scale[D]. Shanghai: Donghua University, 2010:55-57.
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