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TEXTILE RESEARCH JOURNAL · 2023 · IF 2.3

Excellent fixation and color fastness of nylon fibers dyed with low-water-soluble reactive dyes based on the reactivity and stability of vinyl sulfone

Dexiang Li,Wei Ma,Bingtao Tang,Shufen Zhang

Reactive dyes in nylon dyeing have been associated with utilization inefficiencies despite their high color fastness. A potential solution to this issue involves combining the benefits of reactive dyes and milling acid dyes to obtain low-water-soluble reactive dyes (LWSRDs), which can stain and fix to nylon fibers under neutral conditions. To identify a suitable functional group for LWSRDs, six model dyes comprising one vinyl sulfone and five monochloro-s-triazines were prepared and reacted with glycine or hydrolyzed to simulate the fixation progress on nylon fibers. The results show that vinyl sulfone exhibited sufficient reactivity with glycine, and ∼3% hydrolysis over 90 min. Consequently, vinyl sulfone was considered a superior functional group for LWSRDs. Based on these results, four LWSRDs with monofunctional groups were synthesized and used for dyeing nylon 6 microfibers. Notably, these dyes exhibited fixation of >91% and demonstrated exceptional color fastness against washing and rubbing, exceeding grade 4. These results underscore the potential of LWSRDs as highly efficient and effective dyes for nylon, offering a solution to the limitations associated with conventional dyeing techniques.

研究领域: 化学工程 · 纺织科学 · 染料技术
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DYES AND PIGMENTS · 2022 · IF 5.122

Fabrication and characterization of corrosion resistant vinyl sulfone reactive dye-encapsulated colored aluminum pigment composites

Zhenchao Luan,Yezhen Chen,Yifei Liu,Xianger Xia,Kunkai Ma,Junzhi Lin,Bing Geng,Hui Li

A novel waterborne aluminum pigment with bright color and excellent corrosion resistance was prepared. The aluminum pigment encapsulation carries out by vinyl sulfone reactive dye after introducing a vinyl-modified layer on the surface. As a typical vinyl sulfone reactive dye, C.I. Reactive Blue 19 (RB-19) can wrap flake aluminum powder and make its surface rich in hydrophilic groups . And the sulfonic acid group of RB-19 also makes it have favorable dispersibility in water. Furthermore, the coating layer composed of vinyl trimethoxysilane (VTMS) and vinyl sulfone reactive dyes can eliminate the hydrogen evolution phenomenon when they are immersed in strongly alkaline solution (5 wt %). This study provides a new strategy for the research of color aluminum pigment.

CAS / MDL: 78-67-1
研究领域: 材料科学 · 化学工程
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ACS Sustainable Chemistry & Engineering · 2019 · IF 6.97

New Strategy for Functionalization of Silica Materials via Catalytic Oxa-Michael Reaction of Surface Silanol Groups with Vinyl Sulfones

Fang Cheng,Hanqi Wang,Wei He,Bingbing Sun,Jing Zhao,Jingping Qu,Qing Wang

This article demonstrates the catalytic oxa-Michael reaction of inorganic silanol groups with vinyl sulfones, which facilitates an efficient strategy for functionalization of the silica surface. The strategy was applied on materials ranging from nanoscale to macroscale silica, and the surface functionalization was achieved in hours using organo-catalysts at mild temperature. The formation of Si–O–C bonds on the surface was characterized by solid-state 13C cross polarization-magic angle spinning nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and X-ray photoelectron spectroscopy. Our strategy showed several advantages over traditional methods, and the resulting Si–O–C bond exhibited distinct behaviors toward different solvents. Organic solvents would stabilize the functionalized silica materials, while aqueous solutions would result in degradation affected by both solution and surface factors. With use of divinyl sulfone as a cross-linker, a variety of molecules can be immobilized and sequentially released in a controllable manner, which would benefit a broad range of applications from sensing to drug and catalyst carriers.

研究领域: 材料科学 · 化学工程 · 生物医学工程
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JOURNAL OF MOLECULAR LIQUIDS · 2022 · IF 6.633

High-performance inkjet printing ink: Properties and application effects of vinyl sulfone reactive dye-based inks

Yun Li,Chuangui Cao,Fan Feng,Kuanjun Fang,Mengyue Wang,Ruyi Xie,Zhihui Zhao,Weichao Chen

Benefiting its high reactivity with natural fabrics, vinyl sulfone reactive dyes have the advantage of obtaining good color fixation and high exhaustion rates under medium or low temperatures. Although these dyes were widely applied in traditional dyeing processes, little research has been conducted on vinyl sulfone dye-based inks for digital inkjet printing. Hence, we explore an efficient and environmental-friendly ink system for inkjet printing on natural fabrics. In this work, three vinyl sulfone reactive dyes including reactive orange 131 (O-131), reactive red AS (R-AS), and reactive blue 203 (B-203) were selected to simulate the stable structure of the dye molecules in aqueous solution by GAUSSIAN 09 package based on density functional theory (DFT). On this basis, the physicochemical properties of the inks were studied, and the color fastness and apparent color depth values of cotton, linen, and silk inkjet printed fabrics were tested. As a result, compared to O-131 and B-203, the monomer molecular content of R-AS dye solutions was significantly reduced and displayed a strong tendency to aggregate. The surface tensions of three inks decreased with increasing concentrations and the degree of molecular aggregation. The rheological properties of the dye solutions were correlated with concentration and molecular weight. At the same concentrations, B-203 had the largest molecular weight and the solution exhibited the largest viscosity. The printed fabrics all possessed good color quality and color fastness, and printed silk fabric displayed higher color depth than cotton and linen fabrics. This work provided a cleaner and cost-effective ink for inkjet printing on natural fabrics by exploring the properties of vinyl sulfone reactive dye-based inks.

CAS / MDL: 9004-62-0
研究领域: 材料科学 · 纺织工程 · 化学工程
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COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS · 2025 · IF 5.4

Vinyl sulfonamide/PEG co-immobilized on the surface of magnetic beads for the chemiluminescent immunoassay

Shihong Zhu,Daohang Du,Shuli Yu,Ting Tao,Xianfeng Chu,Yunhua Jiang,Jia Yang,Jiefu Li,Zhifei Wang

Chemiluminescent immunoassays utilizing magnetic nanoparticles exhibit critical importance in in vitro diagnostics, attributed to their remarkable superparamagnetic properties, high specificity, and uniform monodispersity. Current surface functionalization strategies for antibody conjugation predominantly rely on carboxyl or amino groups, requiring pre-activation steps for both amino- and carboxyl-modified nanoparticles prior to antibody labeling. However, the complex activation protocols and persistent challenges in developing efficient chemiluminescent detection methods highlight significant technical obstacles. To address these limitations, we developed vinyl sulfone-functionalized magnetic beads (VSF-GMP), enabling rapid antibody conjugation via specific reactions between vinyl sulfone groups and lysine residues exposed on the surface of creatine kinase MB isoenzyme antibodies (CK-MB). This approach facilitates highly efficient chemiluminescent immunoassays. The engineered VSF-GMP magnetic beads demonstrated molecular weight-dependent adsorption profiles, achieving maximal binding capacity (86.32 μg/mg) for mouse IgG (150 kDa) compared to β-lactoglobulin (18.2 kDa) and bovine serum albumin (66.4 kDa). Moreover, compared with the protein coupling method using EDC/NHS-activated carboxylated magnetic beads, our VSF-GMP beads exhibited superior coupling efficiency. Additionally, bis-functionalized poly(ethylene glycol) (NH 2 -PEG-NH 2 ) was employed as a blocking agent to optimize the reactivity and stability of antibody conjugation, reducing non-specific protein labeling on the magnetic beads by 97.8 %. The analytical performance of the proposed chemiluminescent immunoassay (CLIA) was rigorously evaluated. Finally, the practical utility of VSF-GMP magnetic beads for CK-MB determination in plasma samples was investigated. These engineered magnetic beads showcase exceptional analytical sensitivity, specificity, and operational simplicity, establishing a robust platform for advanced chemiluminescent diagnostics with enhanced throughput capabilities.

研究领域: 生物医学工程 · 分析化学 · 免疫学
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Polymers · 2018 ·Vol. 10 ·期 10 ·1158 · IF 2.935

Influence of Ethylene Oxide Content in Nonionic Surfactant to the Hydrolysis of Reactive Dye in Silicone Non-Aqueous Dyeing System

Jiping Wang,Yongbo Zhang,Huashu Dou,Liujun Pei

Silicone reverse dyeing technology provides an important means of saving water and salts-free in the textile dyeing industry. The interactions between dyes and surfactants may influence the hydrolysis of dye during dyeing. In this investigation, the effect of ethylene oxide content in nonionic surfactant on the hydrolytic reaction of reactive dye was firstly investigated in a siloxane reverse emulsion dyeing system. Compared with no surfactants, the hydrolytic reaction of vinyl sulfone reactive dye was a slowdown when some nonionic surfactants were used during dyeing. Usually, the hydrophobic groups in nonionic surfactants were dodecyl chains but their polar head groups were different. The hydrolytic reaction of vinyl sulfone dye showed that the longer of EO (ethylene oxide) chains, the faster the hydrolytic reaction of vinyl sulfone dye. From the absorption spectrum of dye, it could be concluded that more of dyes would be solubilized into the formed micelles, and dye-surfactant complexes were adhered to the surface of micelles if the molecular structure of surfactant had a shorter EO chains. Furthermore, the intramolecular or intermolecular hydrogen bond could be formed between dye and surfactant, which would further influence the hydrolytic reaction of vinyl sulfone dye. However, the solubility of surfactant in siloxane non-aqueous media would decrease with the increase of EO chains. Meanwhile, the dispersion of dye was enhanced as well as the hydrolytic reaction of dye. From this investigation, some surfactant can be used to improve the fixation of reactive dye during dyeing. Furthermore, washing times after dyeing and the ecological problems can be decreased.Keywords:hydrolysis;dye-surfactant interaction;siloxane non-aqueous reverse emulsion dyeing;EO chains;vinyl sulfone reactive dye

研究领域: 纺织化学 · 表面化学
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Biointerphases · 2018 ·Vol. 13 ·期 6 · IF 2.455

Controllable functionalization of hydroxyl-terminated self-assembled monolayers via catalytic oxa-Michael reaction

Cheng Fang,Li Mingyang,Zhao Xuguang,Wang Hanqi,He Wei,Hua Xin,Wang Qing,Qu Jingping

Traditional strategies for the functionalization of materials displaying hydroxyl groups either require active esterification reagents or involve the nucleophilic attack of the hydroxyl group toward electrophilic groups. The former tends to hydrolyze in aqueous solutions while the latter occurs under harsh conditions. Herein, the authors reported a new method for the functionalization of hydroxyl groups on the surface via catalytic oxa-Michael addition with vinyl sulfones. Using hydroxyl group terminated self-assembled monolayers as a model surface, a series of organocatalysts were screened and triphenylphosphine stood out for the best catalytic activity. The catalytic reaction on the surface was characterized by x-ray photoelectron spectroscopy. The information of reaction kinetics was obtained using static water contact angle measurements. Once conjugated with ligands onto the functionalized surfaces, the multivalence binding of proteins was investigated by quartz crystal microbalance experiments. By varying the reaction conditions, e.g., catalyst types and reaction times, ligands can be anchored with a controllable density, which would be helpful to establish the relationships between ligand density and bioactivity.

研究领域: 材料科学 · 表面化学 · 催化 · 生物化学
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LANGMUIR · 2021 · IF 3.882

Versatile, Oxygen-Insensitive Surface-Initiated Anionic Polymerization to Prepare Functional Polymer Brushes in Aqueous Solutions

Chong Liu,Fang Cheng,Bo Liu,Dongdong Gao,Gang Cheng,Chunmei Li,Huanan Wang,Wei He

Surface-initiated polymerization is an attractive approach to achieve desired interfacial compositions and properties on a wide range of substrates and surfaces. Due to mild reaction conditions, multiple surface-initiated polymerization methods, such as atom-transfer radical polymerization (ATRP), reversible addition–fragmentation chain-transfer polymerization, and so forth, have been developed and studied in academia and industry. However, the current methods require the combination of metal catalysts, special initiators, and oxygen removal. Herein, we developed a surface-initiated carbanion-mediated anionic polymerization (SI-CMAP), which can be conducted in aqueous solutions in the presence of oxygen without the need for metal catalysts. Zwitterionic 2-(N-3-sulfopropyl-N,N-dimethyl ammonium)ethyl methacrylate (SBMA) was selected as a model monomer to develop and demonstrate this strategy. The vinyl sulfone (VS) groups displayed on substrate surfaces reacted with N-methylimidazole (NMIM), which was used as the in situ initiator. The polymerization mechanism was extensively studied from many aspects at room temperature, including the changes in reaction conditions, factors affecting the polymerization extent, and substrate surfaces. We also demonstrated the compatibility of this method with a broad spectrum of monomers ranging from SBMA to other acrylates and acrylamides by using glycine betaine as a reaction additive. This method was also evaluated for the preparation of polymer-coated nanoparticles. For polymer-coated silica nanoparticles, their hydrodynamic diameter, copper contamination, and effects of salt and protein concentrations were compared with SI-ATRP in parallel. SI-CMAP in aqueous solutions in air and the absence of metal catalysts make this method sustainable and cost-effective. We believe that SI-CMAP can be readily adapted to the industrial surface coating and large-scale nanoparticle preparation under mild conditions.

CAS / MDL: 80-62-6 3637-26-1
研究领域: 聚合物化学 · 材料科学 · 表面科学 · 纳米技术
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