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Solvatochromic, computational chemical and E/Z geometrical isomerism studies on some aryl-hydrazones synthesised by reacting of aryldiazonium chlorides with 6-butyl-4-hydroxyquinolin-2(1H)-one 通过芳基偶氮氯化物与 6-丁基-4-羟基喹啉-2(1H)-酮反应合成的一些芳基肼酮的溶色、计算化学和 E/Z 几何异构研究
IF 2 4区 工程技术 Q3 CHEMISTRY, APPLIED Pub Date : 2024-08-01 DOI: 10.1111/cote.12781
Enayatollah Moradi Rufchahi, Fatemeh Ashuri Mirsadeghi

A series of 3-(2-aryl-hydrazone)-quinolin-2,4-diones were synthesised by the reaction of aryldiazonium chlorides with 6-butyl-4-hydroxyquinolin-2(1H)-one dissolved in water containing equimolar amount of sodium hydroxide. All the reactions were carried out at 0–5°C and the corresponding hydrazones were obtained in satisfactory yields and purified easily by recrystallisation from hot dimethylformamide. According to proton nuclear magnetic resonance (1H NMR) and ultraviolet-visible (UV-visible) results, there are two kinds of intramolecular hydrogen bonds in these synthesised aryl-hydrazones which enables the compounds to be rotated about the hydrazone C=N bond and through that leads to a reversible isomerisation between their E and Z configurations. The isomers populations and the rotation phenomenon can be controlled by changing the polarity of the solvents. The E/Z ratio of each synthesised compound was studied in deuterated dimethyl sulfoxide (DMSO-d6) and, if soluble in deuterated chloroform (CDCl3) and compared. The results reveal that a decrease in solvent polarity (upon changing the solvent from DMSO-d6 to CDCl3) shifts the isomeric balance to Z-geometrical form and substantially increase the E/Z ratio. A density functional theory (DFT) analysis regarding highest occupied molecular orbital (HOMO), HOMO −1, lowest unoccupied molecular orbital (LUMO), and LUMO +1 has been conducted and discussed. The results obtained from DFT calculations at B3LYP/6-31G(d) level of theory, demonstrated that the hydrazone tautomeric forms are more stable with the lowest total energy and showed a good agreement with the experimental findings in both gas and solution states. As it is expectable, DFT calculation in CDCl3 and DMSO-d6 indicate that the dipole moments of the Z configurations are significantly higher than those of the E structures.

通过芳基偶氮氯化物与溶于含等摩尔量氢氧化钠水中的 6-丁基-4-羟基喹啉-2(1H)-酮的反应,合成了一系列 3-(2-芳基-腙)-喹啉-2,4-二酮。所有反应均在 0-5°C 温度下进行,并以令人满意的产率获得了相应的肼酮,而且很容易从热二甲基甲酰胺中重结晶提纯。根据质子核磁共振(1H NMR)和紫外可见光(UV-visible)结果,在这些合成的芳基肼中存在两种分子内氢键,这使得化合物能够围绕腙的 C=N 键旋转,并通过旋转导致其 E 和 Z 构型之间的可逆异构化。可以通过改变溶剂的极性来控制异构体的数量和旋转现象。我们在氚代二甲基亚砜(DMSO-d6)中研究了每种合成化合物的 E/Z 比值,并对其在氚代氯仿(CDCl3)中的溶解性进行了比较。研究结果表明,溶剂极性的降低(当溶剂从 DMSO-d6 变为 CDCl3 时)会使异构体平衡转向 Z-几何形式,并大幅提高 E/Z 比值。对最高占有分子轨道(HOMO)、HOMO-1、最低未占有分子轨道(LUMO)和 LUMO +1 进行了密度泛函理论(DFT)分析和讨论。在 B3LYP/6-31G(d) 理论水平上进行的 DFT 计算得出的结果表明,腙的同分异构形式更加稳定,总能量最低,并且与气态和溶液态的实验结果显示出良好的一致性。在 CDCl3 和 DMSO-d6 中进行的 DFT 计算表明,Z 构型的偶极矩明显高于 E 结构。
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引用次数: 0
Enzymatic coloration of wool fabrics and its comparison with conventional dyeing 羊毛织物的酶法染色及其与传统染色的比较
IF 2 4区 工程技术 Q3 CHEMISTRY, APPLIED Pub Date : 2024-07-31 DOI: 10.1111/cote.12783
Rıza Atav, Gökmen Karagöz, Uğur Ergünay

The search for a more ecological alternative to dyeing processes, which is the most polluting textile process, has become one of the most studied topics today. In this respect, enzymatic colouring with the use of laccases offer important opportunities, but studies on enzymatic colouring are still very limited. However, in order for enzymatic dyeing to find industrial-scale use, the colour variety must be wide. Within the scope of this study, it is an important output that this study has brought to the literature, that the variety of colours that have been obtained in the literature in enzymatic dyeing has been increased so far by working with a wide variety of precursors and their mixtures, including those that have not been tested on wool before. At the same time, the reaction mechanism of the enzymatic dye synthesis and the chemical structures of the dyes were elucidated by Fourier-transform infrared spectroscopy. Beyond that, as it is known, when a new dyeing process is developed, its technical, economic and ecological advantages and disadvantages compared to the currently accepted conventional dyeing should be revealed. In this study, the colours obtained by enzymatic dyeing were matched with 1:2 metal complex dyes and then two fabrics dyed with the same colour, one enzymatic and the other with conventional method, were compared in terms of technical (colour, fastness), economic (water, energy and chemical consumption) and ecological (biological oxygen demand of wastewater, chemical oxygen demand, etc.) aspects.

染色工艺是污染最严重的纺织工艺,寻找一种更生态的染色工艺替代品已成为当今最热门的研究课题之一。在这方面,使用漆酶的酶法染色提供了重要的机会,但有关酶法染色的研究仍然非常有限。然而,要使酶法染色在工业上得到大规模应用,颜色种类必须丰富。在本研究范围内,本研究为文献带来了一项重要成果,即通过使用多种前体及其混合物,包括以前未在羊毛上测试过的前体,迄今为止,文献中的酶法染色所获得的颜色种类有所增加。同时,还通过傅立叶变换红外光谱法阐明了酶法染料合成的反应机理和染料的化学结构。除此以外,众所周知,当一种新的染色工艺被开发出来时,它在技术、经济和生态方面与目前公认的传统染色工艺相比的优缺点也应被揭示出来。本研究将酶法染色得到的颜色与 1:2 金属络合染料进行配比,然后从技术(颜色、牢度)、经济(水、能源和化学品消耗)和生态(废水的生物需氧量、化学需氧量等)方面对酶法和传统方法染成相同颜色的两种织物进行比较。
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引用次数: 0
Colour difference detection algorithm for warp-knitted fabric based on image colour appearance model 基于图像色彩外观模型的经编织物色差检测算法
IF 2 4区 工程技术 Q3 CHEMISTRY, APPLIED Pub Date : 2024-07-09 DOI: 10.1111/cote.12779
Guosheng Xie, Yang Xu, Xiaowei Sheng, Yike Jin, Yize Sun

Detecting colour differences in warp-knitting fabric is essential to ensure its quality. Machine vision algorithms are commonly used for automatic colour difference detection. However, the current algorithm directly extracts RGB (red, green, blue) colour stimulus values from the image without considering the image's colour attributes, leading to a significant error in colour difference detection. To solve this issue, a colour appearance model is introduced into the field of colour difference detection for warp-knitted fabric. Initially, a colour appearance model based on CAM16 is established, and the critical parameters are calculated to obtain the colour appearance attribute of the fabric. The colour difference calculation formula is then constructed in the uniform colour space of CAM16-UCS. A template selection algorithm based on principal component analysis was designed to select warp-knitted cloth images with standard colours. Subsequently, a cloth colour difference detection algorithm was developed using the cloth colour profile model. The performance of the colour difference formula based on the colour profile model was evaluated using the PF/3 method. To compare the CIELab, CMC(2:1), and CIEDE2000 colour difference formulas, standardised residual sum of squares was used. The results indicated that the colour difference formula based on the colour-appearance model is about 5.32% different from the visual colour difference perceived by the human eye. However, it can perform as well as the CMC(2:1) colour difference formula, which is widely used in the textile industry.

检测经编织物的色差对确保其质量至关重要。机器视觉算法通常用于自动色差检测。然而,目前的算法直接从图像中提取 RGB(红、绿、蓝)色彩刺激值,而不考虑图像的色彩属性,导致色差检测存在很大误差。为解决这一问题,经编面料色差检测领域引入了色彩外观模型。首先,建立基于 CAM16 的色彩外观模型,并计算关键参数以获得织物的色彩外观属性。然后在 CAM16-UCS 统一色彩空间中构建色差计算公式。设计了一种基于主成分分析的模板选择算法,用于选择具有标准色彩的经编布图像。随后,利用布匹色彩轮廓模型开发了布匹色差检测算法。使用 PF/3 方法评估了基于色彩轮廓模型的色差公式的性能。为了比较 CIELab、CMC(2:1) 和 CIEDE2000 色差公式,使用了标准化残差平方和。结果表明,基于色彩外观模型的色差公式与人眼感知的视觉色差相差约 5.32%。不过,它的性能不亚于在纺织行业广泛使用的 CMC(2:1)色差公式。
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引用次数: 0
Towards structurally new cyanine dyes—investigating the photophysical and potential antifungal properties of linear substituted heptamethine dyes 开发结构新颖的氰基染料--研究线性取代庚胺染料的光物理特性和潜在的抗真菌特性
IF 2 4区 工程技术 Q3 CHEMISTRY, APPLIED Pub Date : 2024-07-04 DOI: 10.1111/cote.12780
Okoh Adeyi Okoh, Clare L. Lawrence, Roger H. Bisby, Sarah L. Brennan, Robert B. Smith

The synthesis of a range of new linear substituted heptamethine dyes has been designed and described. The photophysical properties of all the dyes were investigated, with many exhibiting improved fluorescent quantum yields when compared with indocyanine green. Finally, growth inhibition studies were performed in the fission yeast Saccharomyces pombe, which suggests potential antifungals activity in the μM range.

我们设计并描述了一系列新的线性取代庚胺染料的合成。对所有染料的光物理特性进行了研究,与吲哚菁绿相比,许多染料的荧光量子产率都有所提高。最后,还在裂殖酵母中进行了生长抑制研究,结果表明这些染料在 μM 范围内具有潜在的抗真菌活性。
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引用次数: 0
FP-Flow: Feature pyramid flow model for fabric defect detection FP-Flow:用于织物疵点检测的特征金字塔流模型
IF 2 4区 工程技术 Q3 CHEMISTRY, APPLIED Pub Date : 2024-07-01 DOI: 10.1111/cote.12768
Yuanfei Wang, Yang Xu, Zhiqi Yu, Xiaowei Sheng

Fabric defect detection is a crucial aspect of fabric production. At present, deep learning detection methods mostly rely on supervised learning. To tackle this issue, this study proposes an unsupervised fabric defect detection approach based-on normalising flow. The method only needs to train the mapping of the feature probability distribution of defect-free samples to a Gaussian distribution. In the inference process, the location of defects can be determined by testing the distance between the probability distribution of image features and the estimated distribution. To adapt to the complex background and various minor defects of the fabric, a feature pyramid structure is adopted. Moreover, considering the gradient vanishing and network degradation caused by deep layers during training, a residual structure is incorporated into the model. Experimental results demonstrate that the feature pyramid flow model outperforms other methods in defect detection across multiple datasets, with an average score rate of 98.7% and 100% for pixel-level area under the curve (AUC) receiver operating characteristic and image-level AUC, respectively, compared to an average score rate of 91.1% and 85.4% for other methods.

织物疵点检测是织物生产的一个关键环节。目前,深度学习检测方法大多依赖于监督学习。针对这一问题,本研究提出了一种基于归一化流量的无监督织物疵点检测方法。该方法只需训练无缺陷样本的特征概率分布与高斯分布的映射。在推理过程中,可通过测试图像特征概率分布与估计分布之间的距离来确定疵点位置。为了适应复杂的背景和织物的各种微小疵点,采用了特征金字塔结构。此外,考虑到训练过程中深层造成的梯度消失和网络退化,在模型中加入了残差结构。实验结果表明,在多个数据集上,特征金字塔流模型在疵点检测方面优于其他方法,在像素级曲线下面积(AUC)接收操作特征和图像级AUC方面的平均得分率分别为98.7%和100%,而其他方法的平均得分率分别为91.1%和85.4%。
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引用次数: 0
The mathematical model for colour preference in Chinese painting within museum lighting environments 博物馆照明环境下中国画色彩偏好的数学模型
IF 2 4区 工程技术 Q3 CHEMISTRY, APPLIED Pub Date : 2024-06-15 DOI: 10.1111/cote.12778
Rui Dang, Shuning Wang, Xingcan Sun, Ming Tang, Di Yang

Colour in a Chinese painting not only conveys cultural, historical, and philosophical concepts but also carries specific symbolic meanings and emotions, possessing a high level of artistic value. However, the sensitivity of Chinese paintings to light results in exhibition environments being characterised by low illuminance and low colour temperature. Therefore, accurately assessing colour preferences in Chinese paintings under such conditions is an issue that needs to be addressed. This study conducted simulated experiments in real museum exhibition halls, with 36 participants providing subjective evaluations of Chinese paintings, to explore the effects of various lighting parameters on colour preferences. Through statistical analysis and multiple linear regression, the relationship between lighting parameters and colour preferences in a Chinese painting was determined, and an evaluation model was established. This research outcome provides important mathematical tools for selecting appropriate lighting and developing dedicated lighting for Chinese paintings, ensuring the artistic inheritance of Chinese painting colours.

中国画中的色彩不仅传达着文化、历史和哲学概念,还承载着特定的象征意义和情感,具有极高的艺术价值。然而,中国画对光线的敏感性导致展览环境具有低照度和低色温的特点。因此,在这种条件下准确评估中国画的色彩偏好是一个亟待解决的问题。本研究在真实的博物馆展厅中进行了模拟实验,由 36 名参与者对中国画进行主观评价,以探讨各种照明参数对色彩偏好的影响。通过统计分析和多元线性回归,确定了中国画照明参数与色彩偏好之间的关系,并建立了评价模型。这一研究成果为选择合适的照明和开发中国画专用照明提供了重要的数学工具,确保了中国画色彩的艺术传承。
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引用次数: 0
Fast prediction of optimal reaction conditions and dyeing effects of natural dyes on silk fabrics by lightweight integrated learning (XGBoost) models 利用轻量级集成学习(XGBoost)模型快速预测丝织物上天然染料的最佳反应条件和染色效果
IF 2 4区 工程技术 Q3 CHEMISTRY, APPLIED Pub Date : 2024-06-10 DOI: 10.1111/cote.12777
Jie Chen, Yuyang Lin, Ying Liu

There is a lot of repetitive work involved in exploring the dyeing performance of natural dyes. To improve the experimental efficiency, save material, reduce time costs and shorten the research cycle, this study collects and analyses the literature data of 350 natural dye experiments to construct the Natural Dyes Dataset, and achieves rapid prediction of the optimal reaction conditions and dyeing effects of natural dyes using a lightweight integrated learning model. The size of the trained XGBoost model is only 562 KB; only the name of the dye and its approximate chemical composition need to be input to predict the results of the reaction environment pH, colour fastness to washing (CFW) and colour fastness to rubbing (CFR) of the natural dye on silk fabrics with the highest K/S in a very short time of 52 ms. The prediction accuracies for pH, CFW and CFR in the validation set are as high as 94.12%, 93.75% and 100%, respectively, and 77.78%, 91.67% and 83.33% for the real test set, with both validity and transferability. The integrated learning approach provides valuable guidance for exploring the dyeing performance of natural dyes with very small deployment costs and a very short inference time, expanding the possibilities of cross-application of the disciplines of machine learning and textile dyeing.

天然染料的染色性能探索涉及大量重复性工作。为了提高实验效率、节省材料、降低时间成本、缩短研究周期,本研究收集并分析了 350 个天然染料实验的文献数据,构建了天然染料数据集,并利用轻量级集成学习模型实现了对天然染料最佳反应条件和染色效果的快速预测。训练好的 XGBoost 模型大小仅为 562 KB,只需输入染料名称及其大致化学成分,即可在 52 ms 的极短时间内预测出 K/S 最高的天然染料在丝织物上的反应环境 pH 值、水洗色牢度(CFW)和摩擦色牢度(CFR)的结果。验证集的 pH 值、CFW 值和 CFR 值的预测准确率分别高达 94.12%、93.75% 和 100%,实际测试集的预测准确率分别为 77.78%、91.67% 和 83.33%,具有有效性和可移植性。该集成学习方法以极小的部署成本和极短的推理时间为天然染料染色性能的探索提供了宝贵的指导,拓展了机器学习与纺织品染色学科交叉应用的可能性。
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引用次数: 0
Sustainable scouring of cotton using extracts from wood ash and soapnut and its optimisation by response surface methodology 使用木灰和皂角提取物对棉花进行可持续冲洗,并通过响应面方法对其进行优化
IF 2 4区 工程技术 Q3 CHEMISTRY, APPLIED Pub Date : 2024-06-09 DOI: 10.1111/cote.12776
Harshal Patil, Ashok Athalye

The non-cellulosic impurities like oil, wax, and pectins present in the cotton fibre adversely impact wetting. Consequently, these impurities must be removed during the pretreatment process to prevent unevenness of subsequent coloration. Generally, an alkaline treatment with petroleum-based synthetic surfactants is done, which is called scouring. This study attempts to develop an environmentally safe alternative using alkali from wood ash extract (WAE) and surfactant from soapnut extract (SE). The factors of WAE (10%–30%), SE (5–15 g/L), temperature (75–95°C), and time (20–60 min) were optimised using response surface methodology. A concentration of 20% WAE and 10 g/L SE at 90°C for 30 min was found to be adequate to remove impurities. The statistically optimised method showed good hydrophilicity, indicated by an average wetting time of 15 s, and 2.7% weight loss. The scoured fabric was subsequently dyed with natural dye extracted from marigold flowers and reactive dye. The scoured cotton was evaluated by weight loss, wettability, tensile strength, whiteness index, and colour value (K/S) and showed comparable results to conventional scouring.

棉纤维中存在的油、蜡和果胶等非纤维素杂质会对润湿产生不利影响。因此,必须在预处理过程中去除这些杂质,以防止随后的着色不均匀。一般情况下,使用石油基合成表面活性剂进行碱性处理,即所谓的冲洗。本研究试图利用木灰提取物(WAE)中的碱和皂角提取物(SE)中的表面活性剂开发一种环境安全的替代方法。采用响应面方法对 WAE(10%-30%)、SE(5-15 g/L)、温度(75-95°C)和时间(20-60 分钟)等因素进行了优化。结果发现,浓度为 20% 的 WAE 和 10 g/L 的 SE 在 90°C 下 30 分钟足以去除杂质。统计优化方法显示出良好的亲水性,平均润湿时间为 15 秒,重量损失为 2.7%。随后,用从金盏花中提取的天然染料和活性染料对洗净的织物进行染色。通过失重、润湿性、拉伸强度、白度指数和色值(K/S)对洗净的棉布进行了评估,结果与传统的洗净方法相当。
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引用次数: 0
Post-modification of azo dyes using an α-phenyl diazo ester for improving the colour fixation properties of polyurethane fibre 使用α-苯基重氮酯对偶氮染料进行后改性,以改善聚氨酯纤维的固色性能
IF 2 4区 工程技术 Q3 CHEMISTRY, APPLIED Pub Date : 2024-06-04 DOI: 10.1111/cote.12769
Hua Jiang, Lulu Shi, Xiaokang Xie, Ye Wang

Colour fastness of polyurethane fibre dyed with conventional disperse dyes is always poor owing to the insufficient affinity between fibres and dyes. Thus, three novel azo dyes containing an α-phenyl diazo ester moiety were designed in this study. The dyes were synthesised through two-step post-modification of a hydroxylated azo benzene chromophore. All three dyes were characterised using proton and carbon nuclear magnetic resonance, high-resolution mass spectrometry and infrared spectrometry. The ultraviolet-visible absorption and thermal properties of the dyes were also studied. Fixation properties of these dyes on polyurethane fibre were examined using samples dyed using a non-aqueous dyeing method. Practicality of these dyes, that is colour depth, fixation value, colour fastness and dye migration degree, was further verified on fibre dyed via an aqueous dyeing method. Finally, the mechanical properties of the dyed polyurethane fibre were explored.

由于纤维与染料之间的亲和力不足,用传统分散染料染色的聚氨酯纤维的色牢度总是很差。因此,本研究设计了三种含有 α-苯基重氮酯分子的新型偶氮染料。这些染料是通过对羟基偶氮苯发色团进行两步后修饰合成的。使用质子和碳核磁共振、高分辨率质谱法和红外光谱法对这三种染料进行了表征。此外,还研究了这些染料的紫外可见吸收和热特性。使用非水性染色法染色的样品检验了这些染料在聚氨酯纤维上的固着特性。在采用水性染色法染色的纤维上,进一步验证了这些染料的实用性,即色深、固着值、色牢度和染料迁移程度。最后,还探讨了染色聚氨酯纤维的机械性能。
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引用次数: 0
Redox kinetics of methylene green: Titanium trichloride as a novel photo redox agent 亚甲基绿的氧化还原动力学:作为新型光氧化还原剂的三氯化钛
IF 2 4区 工程技术 Q3 CHEMISTRY, APPLIED Pub Date : 2024-05-30 DOI: 10.1111/cote.12753
Syed Muhammad Saqib Nadeem, Rehana Saeed

The kinetics of the redox reaction of methylene green (MG) and the novel photo-redox agent titanium trichloride (TiCl3) in water were investigated by real-time spectrophotometric analysis of the change in absorbance of the reaction mixture at 655 nm. The novelty of this redox reaction is that the TiCl3 is an inorganic compound in contrast to the previously studied organic redox couples. The redox reaction was analysed in depth and the effects of the concentration of the TiCl3, MG, pH, dielectric constant, ionic strength, metal ions, and temperature on the reaction kinetics were observed. The rate of reaction had a direct relationship with the pH, dielectric constant, and ionic strength of the reaction medium, while an increase in temperature decreased the rate of reaction. The activation energy (Ea) was calculated by the Arrhenius relation, and the other thermodynamic parameters, such as enthalpy change of activation (∆H*), free energy change of activation (∆G*), and entropy change of activation (∆S*) were also evaluated to support the findings of the kinetic measurements. The presence of any reaction intermediate other than the species in the reaction mechanism was ruled out by the spectroscopic analysis of the reaction mixture and Michaelis–Menten plot while the absence of any free radicals was confirmed by the negative polyacrylamide test. A reaction mechanism for the redox reaction of MG+ and TiCl3 was proposed based on the different excited states of the MG+ involved in the reaction and the results of the product analysis. The decolourisation of MG by the TiCl3 is overall a second-order reaction and is significantly affected by the pH of the reaction medium. The overall rate law for the redox reaction of MG and TiCl3 is as follows.

通过对反应混合物在 655 纳米波长处的吸光度变化进行实时分光光度分析,研究了亚甲基绿(MG)和新型光氧化还原剂三氯化钛(TiCl3)在水中的氧化还原反应动力学。这种氧化还原反应的新颖之处在于 TiCl3 是一种无机化合物,与之前研究的有机氧化还原偶联物不同。对氧化还原反应进行了深入分析,观察了 TiCl3 浓度、MG、pH 值、介电常数、离子强度、金属离子和温度对反应动力学的影响。反应速率与反应介质的 pH 值、介电常数和离子强度有直接关系,而温度升高则会降低反应速率。活化能(Ea)由阿伦尼乌斯关系式计算得出,其他热力学参数,如活化焓变化(∆H*)、活化自由能变化(∆G*)和活化熵变化(∆S*)也得到了评估,以支持动力学测量的结果。反应混合物的光谱分析和迈克尔斯-门顿图排除了反应机理中物种以外的任何反应中间体的存在,而聚丙烯酰胺阴性试验则证实了不存在任何自由基。根据参与反应的 MG+ 的不同激发态和产物分析结果,提出了 MG+ 和 TiCl3 氧化还原反应的反应机理。TiCl3 对 MG 的脱色反应总体上属于二阶反应,受反应介质 pH 值的影响很大。MG 与 TiCl3 的氧化还原反应的总速率规律如下。
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引用次数: 0
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Coloration Technology
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