Journal of Textile Research ›› 2025, Vol. 46 ›› Issue (10): 143-151.doi: 10.13475/j.fzxb.20250204701

• Dyeing and Finishing Engineering • Previous Articles     Next Articles

Synthesis of new ethylene sulfone acetate reactive disperse dyes and its dyeing performance for polyamide 66 fabrics

LI Jian'ge1, WU Wei1, HAN Weipeng2, JI Bolin1,3, XU Hong1, MAO Zhiping1,3,4()   

  1. 1. College of Chemistry and Chemical Engineering, Donghua University, Shanghai 201620, China
    2. Anoky Group Co., Ltd., Shanghai 201703, China
    3. National Engineering Research Center for Dyeing and Finishing of Textiles, Donghua University, Shanghai 201620, China
    4. National Innovation Center for Advanced Dyeing and Finishing Technology, Taian, Shandong 271000, China
  • Received:2025-02-21 Revised:2025-06-13 Online:2025-10-15 Published:2025-10-15
  • Contact: MAO Zhiping E-mail:zhpmao@dhu.edu.cn

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Abstract:

Objective Polyamide 66 fiber has high crystalline degree, dense structure, and less active amino content at the end of the molecular chain, and it is difficult to achieve deep dyeing of polyamide 66 with acidic dyes or disperse dyes or reactive dyes. To achieve deep dyeing, it is necessary to use acidic dyes containing heavy metal complexes, which causes a certain pressure on environmental protection. It is of great significance to synthesize special dyes for polyamide 66.

Method Small molecular disperse dyes were synthesized by diazotization and coupling reaction with 2-[(3-aminophenyl) sulfonyl] ethanol as diazo component and N, N-diethylaniline as the coupling component. The synthesized small molecular disperse dyes were then modified by acetic anhydride to prepare small molecular hydrophobic active disperse dyes with better affinity for polyamide 66. The structure of the dyes was characterized by fourier transform infrared spectroscopy and proton nuclear magnetic resonance spectroscopy, and the spectral properties of the dyes were analyzed by ultraviolet-visible spectroscopy. The dyeing process conditions of the polyamide 66 fabric were optimized by single factor experiment with K/S value of the dyed fabric as the index. The kinetics and thermodynamics of reactive disperse dyes for dyeing polyamide 66 were analyzed through the constant temperature dyeing rate curve and the adsorption isotherm. The color fastness test of the dyed fabrics was conducted to examine the color fastness of polyamide 66 fabrics dyed with reactive disperse dyes in various aspects, and the penetration property analysis was carried out.

Results The structure of the dye was confirmed to be correct by infrared spectroscopy and hydrogen nuclear magnetic resonance spectroscopy. The dye had a maximum absorption wavelength at 450 nm, the color light was yellow, and the molar extinction coefficient reached 14 104 L/(mol·cm). The optimal dyeing of nylon 66 fabric was processed at dyeing temperature 100 ℃, pH 7, and dyeing time 30 min. When 2%(o.w.f) dye was added into the dyeing bath, the K/S value of the dyed fabric was 27. The fastness of polyamide 66 fabric dyed by reactive disperse dyes was good, with the fastness to soap washing, sublimation and dry/wet friction reaching 4-5. The fastness to sunlight was 4 and achieved dye penetration. The adsorption dyeing kinetics equation of reactive disperse dyes on polyamide 66 conforms to the quasi-second-order kinetics equation, and the adsorption isotherm conforms to the Nernst thermodynamic adsorption model. The reactive disperse dyes demonstrated good dye penetration for polyamide 66.

Conclusion Due to its low polarity, the developed reactive disperse dyes show good affinity for polyamide 66 fibers. During the dyeing process, the saturated dyeing amount is at a relatively high level, solving the problem of poor depth of polyamide 66 fabrics. Each color fastness is excellent and meet the production requirements and consumption needs short process flow, high efficiency and energy saving.

Key words: reactive disperse dye, vinyl sulfone acetate, dye modification, polyamide 66, dye depth, dynamics, thermodynamics

CLC Number: 

  • O647.9

Fig.1

Dye synthesis route.(a)Diazo-reaction;(b)Coupled reaction;(c)Acetylation"

Fig.2

Ultraviolet-visible light absorption spectrum of dyes"

Fig.3

Infrared spectrum of reactive disperse dyes"

Fig.4

Molecular structure diagram of reactive disperse dyes"

Fig.5

Mechanism of reaction between reactive disperse dyes and polyamide fibers"

Fig.6

Influence of dyeing pH values on dye uptake rate(a)and K/S value(b)of dyed polyamide 66 fabrics"

Fig.7

Influence of dyeing temperatures on dye uptake rate(a)and K/S value(b)of dyed polyamide 66 fabrics"

Fig.8

Temperature-rising dyeing rate curve of reactive disperse dyes on polyamide 66"

Fig.9

Curve of dyeing enhancement of reactive disperse dyes on polyamide 66"

Fig.10

Constant-temperature dyeing rate curve of reactive disperse dyes on polyamide 66"

Fig.11

Kinetic equation fitting for adsorption of reactive disperse dyes on polyamide 66.(a)Quasi-first-order dynamic fitting;(b)Quasi-second-order dynamic fitting"

Tab.1

Kinetic fitting parameters for adsorption of reactive disperse dyes on polyamide 66"

模型 温度/
℃		 K1/K2 [D]f.e
预测值		 R2 [D]f.e
实验值
准一级 90 0.033 09 0.001 207 0.993 02 0.001 754
98 0.037 24 0.001 011 0.981 39 0.001 794
准二级 90 58.835 7 0.001 847 0.999 79 0.001 754
98 81.942 0 0.001 873 0.999 75 0.001 794

Fig.12

Adsorption isotherm of reactive disperse dyes on polyamide 66"

Fig.13

Nernst type fitting curve"

Tab.2

Nernst type fitting parameters"

温度/ ℃ 吸附常数Kn 拟合公式 拟合系数R2
90 3.652 85 y=3.652 85x+1.273 6 0.994 93
98 4.294 83 y=4.294 83x+2.133 7 0.999 20

Tab.3

Thermodynamic parameters for dyeing of polyamide 66 with reactive disperse dyes"

温度/
℃		 亲和力-Δμ°/
(kJ·mol-1)		 染色热ΔH°/
(kJ·mol-1)		 染色熵ΔS°/
(J·(K·mol)-1)
90 24.77 22.44 130
98 25.81

Fig.14

High-resolution image of cross-section of polyamide 66 dyed with reactive disperse dyes"

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