Reactive dye compounds

A reactive dye and high-efficiency technology, applied in the direction of reactive dyes, azo dyes, organic dyes, etc., can solve the problems of dye retention, achieve high color intensity, improve affinity, and simplify the effect of soaping process

Inactive Publication Date: 2001-07-11
THE PROCTER & GAMBNE CO
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AI-Extracted Technical Summary

Problems solved by technology

However, an urgent problem still faced by the fabric dye industry at present is the l...
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Abstract

Reactive dye having a Fixation Value (F) on cellulosic substrates of 95% or greater as measured by the Fixation Value Technical Test Method (at 2:1 standard depth). In addition, the compounds herein have high Exhaustion Values (E), high Efficiency Values (T) and show significant improvements in terms of reducing spent dyestuff in effluent, increasing dye affinity to the substrate, increasing the dye-substrate covalent bonding, increasing the ability to dye substrates at room temperature, decreasing the amount of dye that is removed during the post dyeing ''soaping off process'' and therefore simplifying the post dyeing ''soaping off process'' traditionally associated with dyeing cotton with fibre reactive dyes and reduction of staining of adjacent white fabrics. In addition, the compounds prepared above provide more intense dyeings and require less levels of salt for dyeing cotton substrates.

Application Domain

Technology Topic

Examples

  • Experimental program(17)
  • Effect test(1)

Example

[0140] Examples Example 1 Synthesis of monothioglycolato-nicotinic acid triazine dye using Procion (RTM) dye as a starting material
[0141] The synthesis route as described in Reaction Scheme 1 is used to prepare monothioglycolato-nicotinic acid triazine dye.
[0142] The synthesis method consists of two parts, namely the first part for preparing monochloromonothioglycolato triazine and the second part for preparing monothioglycolato mononicotinic triazine as shown in the following reaction mechanism.
[0143] In this reaction route, D is a chromophore and varies according to the starting dye used. In this example, various Procion (RTM) dyes commercially available from BASF were used as starting materials, particularly Procion Red MX-8B, Procion Yellow MX-8G, and Procion Blue MX-2G. Synthesis of monochloromonothioglycolato triazine dye
[0144] The first part of the synthesis method is to obtain monochloro-monothioglycolato triazine. Prepare purified Procion (RTM) dichlorotriazine dye aqueous solution (0.1mol/100ml, pH 7.5). 0.1 mol of thioglycolic acid was slowly added dropwise to the solution at a temperature of 0-5°C. After adding thioglycolic acid, the pH of the system was adjusted to 8 using sodium carbonate and HCl. The reaction is then allowed to proceed for 5-8 hours at 0-5°C and pH 8. For each different dye, the required reaction time is different (7-8 hours for Procion Red MX-8B, about 6 hours for Procion Yellow MX-8G, and about 5 hours for Procion Blue MX-2G hour). During the synthesis process, a rapid decrease in pH was observed, and a neutralizer was used to restore the pH to 8. The end of this part of the reaction is indicated by the pH of the reaction system remaining constant for more than 5 minutes. At this time, the dye monochloro-monothioglycolato triazine is obtained. At the end of the synthesis, the pH of the system was lowered below pH2. After precipitation and filtration, a solid monochloromonothioglycolato triazine dye compound is obtained. Synthesis of monothioglycolato-nicotinic acid triazine dye
[0145] In the second part of the synthesis method, the monochloromonothioglycolatotriazine synthesized from the first part is reacted with niacin. A stoichiometric excess of the aqueous solution of niacin (pH value of 5-5.5) is added to the aqueous solution of the monochloromonothioglycolato triazine dye solution. Then the temperature of the reaction system is increased to 50-55°C, and the pH value is adjusted to 5-5.5. The reaction is allowed to proceed for a period of time under these conditions. It was observed that the pH value of the synthesis system dropped rapidly. The end of the reaction is indicated by the stability of the pH value for more than 5 minutes. For each different dye, the required reaction time is different (4-5 hours for Procion Red MX-8B, about 3 hours for Procion Yellow MX-8G, and about 2 hours for Procion Blue MX-2G. 2.5 hours). At this time, the monothioglycolato-nicotinic acid triazine dye is obtained.
[0146] At the end of the synthesis, the reaction system was immediately cooled to below 5°C and the pH value was lowered below 2 to prevent the hydrolysis of the monothioglycolatonicotinic acid triazine dye. After precipitation and filtration, a solid monothioglycolatomononicotinic triazine dye is obtained.
[0147] Rinse the resulting solid monothioglycolato-nicotinic acid triazine dyes 4-5 times with acetone to ensure they are free of water, and then store at 0-5°C.

Example Embodiment

[0148] Example 2 Synthesis of monothioglycolato-isonicotinyl triazine dye
[0149] The synthesis route described in Reaction Scheme 2 was used to prepare monothioglycolato-isonicotinyl triazine dye.
[0150] Reaction route 2
[0151] In this reaction route, D is a chromophore and varies according to the starting dye used. In this example, Procion (RTM) Red MX-8B was used as the starting material. The Procion(RTM) Red MX-8B in this embodiment can be replaced by other dichlorotriazine dyes such as Procion Yellow MX-8G or Procion Blue MX-2G.
[0152] The synthesis method consists of two parts, the first part of preparing monochloromonothioglycolato triazine dye and the second part of preparing monothioglycolato-isonicotinyl triazine dye. Synthesis of monochloromonothioglycolato triazine dye
[0153] The monochloromonothioglycolato triazine dye was prepared in the same manner as described in Example 1 above and using the same Procion starting dye. Synthesis of Monothioglycolato-isonicotinyl Triazine Dyes
[0154] In the second part of the synthesis step, the monochloromonothioglycolatotriazine synthesized in the first part is reacted with isonicotinic acid. Add 0.01 mol of monochloromonothioglycolato triazine dye synthesized from the first part and 0.04 mol of isonicotinic acid in distilled water into the flask. Then the temperature of the reaction system was increased to 55°C, and the pH value was adjusted to 5.5. The reaction was allowed to proceed for 30 minutes under these conditions. It was observed that the pH value of the synthesis system dropped rapidly and was raised again with a buffer. The pH value is stable for more than 5 minutes to indicate the end of the reaction. The conditions of precipitation, filtration and acetone washing are the same as those of the compound prepared in Example 1. The yield exceeds 85%.

Example Embodiment

[0155] Example 3 Synthesis of monothioglycolato-(diazabicyclooctane) triazine dye
[0156] The synthesis route described in Reaction Scheme 3 was used to prepare monothioglycolato-(diazabicyclooctane) triazine dye.
[0157] Reaction route 3
[0158] In this reaction route, D is a chromophore and varies according to the starting dye used. In this example, Procion (RTM) Red MX-8B was used as the starting material.
[0159] The synthesis method consists of two parts, the first part of preparing monochloromonothioglycolato triazine dye and the second part of preparing monothioglycolato-DABCO triazine dye. The monochlorothioglycolatotriazine was prepared in the same manner as in Example 1 above.
[0160] In the second part of the synthesis method, the monochloromonothioglycolato triazine dye synthesized from the first part is reacted with diazabicyclooctane (DABCO). 0.01 mol of monochloromonothioglycolato triazine dye was added to the flask along with 0.03 mol of DABCO in distilled water. The temperature of the resulting solution was then increased to 55°C and the pH value was adjusted to 5.5. The reaction was allowed to proceed for 15 minutes under these conditions. The rapid decrease of the pH value of the synthesis system was observed again, which was raised to pH 5.5 again by the buffer. The pH value is stable for more than 5 minutes to indicate the end of the reaction. The conditions of precipitation, filtration and acetone washing are the same as in Example 1 above. The yield exceeds 85%.
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