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Organic solvent soluble metal complex azo dyes

一种有机溶剂、染料的技术，应用在偶氮染料、有机染料、偶氮染料的配合金属化合物等方向，能够解决没有溶解性等问题

Inactive Publication Date: 2006-12-20
UNITED COLOR MFG INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to their ionic character, most of these dyes have limited solubility in lower alcohols, glycol ethers, ketones and esters, and similar materials, and often have no significant solubility in aromatic or even more aliphatic hydrocarbons

Method used

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  • Organic solvent soluble metal complex azo dyes
  • Organic solvent soluble metal complex azo dyes
  • Organic solvent soluble metal complex azo dyes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]To a solution of 15 g of sodium nitrite in 60 ml of water was added 28 g of technical grade (0.2 mole) 4-nitroaniline and stirred until a homogeneous slurry was obtained. The slurry was then added over about 5 minutes to 60 g of 32% hydrochloric acid which had been cooled to -5°C by adding ice. Additional ice was provided to the ligand system to prevent the temperature from rising above 5°C during slurry addition. The mixture is then stirred for about 15 minutes until it becomes as clear as possible. At this point, a small amount of filter aid was added to filter 4-nitrobenzenediazonium chloride while still keeping its temperature below 5°C. The filtered solution is then transferred to a stirred beaker or flask and any remaining nitrite ions are reduced with sulfamic acid. Next, 32 g of 2,5-dimethoxyaniline dissolved in 200 ml of water and 25 g of 32% hydrochloric acid were added over 15 minutes via the dropping funnel. The azo coupling started immediately and a visco...

Embodiment 2

[0041] Into a 5 liter flask surrounded by an ice bath was added 300 g of ice and 50 g of water. The mixture was stirred and 130 g of 96% sulfuric acid was added, followed by 100 g of aniline, forming a white dispersion of aniline sulfate. The mixture was then cooled to -5°C by adding ice and diazotized below 3°C by adding 190 g of 40% aqueous sodium nitrite solution. The mixture was stirred until all white particles of aniline sulfate had dissolved to form a clear solution. After approximately 5 minutes of agitation, unreacted nitrite ions were removed by adding a small amount of sulfamic acid. 140 g of 2-methoxy-5-methylaniline was added to the diazo compound while raising the temperature to 5-10°C. After stirring for 15 minutes, sufficient 30% aqueous sodium acetate was added to raise the pH of the reaction to 3.5. The reaction was stirred at 10-12°C for 4 hours to substantially complete the azo coupling. Next, 600 g of xylene was added, followed by 110 g of concentrated...

Embodiment 3

[0044] The synthesis of Example 2 was repeated except that 165 g of diethylene glycol-3-aminopropyl ether was replaced by 220 g of 1-propylamine-3,3'-[oxybis(2,1-ethanedyloxy)]bis. The resulting dye had very similar properties to Example 2, except that it was significantly bluer in the shade.

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PUM

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Abstract

The present invention relates to organic solvent soluble dyes. In particular, the invention relates to an organic solvent soluble metal complex azo dyes containing chelated metal atoms.

Description

[0001] Cross References to Related Applications [0002] This application is related to and claims the earlier filing date benefit and priority of Application Serial No. 60 / 504,984, filed September 23, 2003, which is hereby incorporated by reference in its entirety. technical field [0003] The present invention relates to dyes soluble in organic solvents. In particular, the present invention relates to organic solvent-soluble metal complex azo dyes containing chelated copper or nickel atoms. Background technique [0004] Metal complex azo compounds have been used as organic solvent soluble dyes for many years. A survey of the "Color Index" lists, published by the American Association of Textile Chemists and the Society of Dyers and Colourists (UK), revealed that, with one exception, all dyes were chromium and to a lesser extent cobalt and iron. Chelates. The only exception seems to be C.I.Solvent Black 49, a non-ionic copper complex. As these aforementioned metals are i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B45/08C09B45/12C09BC09B45/00
CPCC09B69/00C09B45/28C09D11/328
Inventor 迈克尔·J.·史密斯
Owner UNITED COLOR MFG INC
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