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Studies on synthesis of dyes having fluoroalkyl groups and water-repellent dying

含氟烷基染料的合成及拒水染色研究

基本信息

批准号：
10680121
负责人：
KAWASE Tokuzo
金额：
$ 2.11万
依托单位：
Osaka City University
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (C)
财政年份：
1998
资助国家：
日本
起止时间：
1998 至 1999
项目状态：
已结题

来源：
https://kaken.nii.ac.jp/grant/KAKENHI-PROJECT-10680121/
关键词：
Fluoroalkyl groups acid dye nylon water repellency dyeing surface free energy ESCA surface analysis

项目摘要

Dyes having fluoroalkyl groups to function as water- and oil repellent agents have hardly reported owing to the difficulties of syntheses. In this work, novel fluoroalkylated anilines were synthesized by (1) the reaction of perfluoroalkanoyl peroxides with acetoanilide, or (2) the coupling of perfluoroalkyl iodide and iodoaniline. By the diazo-coupling reaction, acid and direct dyes having fluoroalkyl group on the aromatic ring were easily prepared.I selected the acid dyes, applied to the dyeing of nylon, and basically studied the novel water-repellent dying system from the viewpoint of surface free energies, contact angles, and ESCA surface analysis.At the same amount of dye exhaustion, water contact angles increased in the order of RィイD2fィエD2 = CFィイD23ィエD2 < CィイD23ィエD2FィイD27ィエD2 << CィイD26ィエD2FィイD213ィエD2 【approximately equal】 CィイD28ィエD2FィイD217ィエD2, in the latter two cases, nylon surface could be changed apparently to water-repelled. Based on the ESCA measurements, the peak area ratio on FィイD21sィエD2 to NィイD2lsィエD2 was taken as a new measure of fluorine concentration at the surface. Those FィイD21sィエD2/NィイD21sィエD2 peak ratios were highly correlated to the water contact angles. The difference that was observed depending on RィイD2fィエD2 could be interpreted in terms of the diffusion of dyes into the bulk.

由于合成困难，具有氟代烷基的染料用作防水剂和防油剂几乎没有报道。本文通过全氟烷酰基过氧化物与乙酰苯胺反应，或全氟烷基碘与碘苯胺偶联，合成了新型氟烷基苯胺。通过重氮偶联反应，合成了芳环上含氟烷基的酸性染料和直接染料，并将其应用于尼龙的染色，从表面自由能、接触角和ESCA表面分析等方面对新型拒水染色体系进行了初步研究，在相同上染量下，水接触角按以下顺序增加：RイD2 f D2 = CFイD23 D2 < CイD23 D2 FイD27 D2 << CイD26 D2 FイD213 D2 [大约等于] CイD28 D2 FイD217 D2，在后两种情况下，尼龙表面可明显改变为拒水。在ESCA测量的基础上，将F_（21）S_（21）D_（22）与N_（21）S_（21）D_（21）D_（22）的峰面积比作为表面氟浓度的新量度。这些F β D21 s β D2/N β D21 s β D2峰比率与水接触角高度相关。观察到的差异取决于R λ D2 f λ D2，可以解释为染料扩散到本体中。