Reactive dye compounds

A technology of reactive dyes and compounds, applied in the direction of reactive dyes, organic dyes, azo dyes, etc., can solve the problems of dye retention, etc., achieve the effects of high color intensity, increased covalent reaction efficiency, and improved affinity

Inactive Publication Date: 2002-05-29
THE UNIV OF NORTH CAROLINA AT CHAPEL HILL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, a critical problem still faced by the fabric dye industry is that a large am

Method used

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Examples

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preparation example Construction

[0082] The invention also relates to a process for the preparation of the dyes of the invention. In general, dye compounds of formula (I) can be prepared by reacting suitable precursors of dyes of formula (I), at least one of which contains the group D-L-Z, wherein D, L and Z are as defined above, and wherein At least one contains a Y group (where Y is as defined above) and at least one of them contains an X group. Those of ordinary skill in the art will appreciate that where X is a halogen, the halogen is part of the Z group in a starting material such as dichlorotriazine.

[0083] For example, a dye compound of the invention having formula (I) wherein Z is a triazine heterocycle can be prepared by combining one mole of a dichlorotriazine dye such as those commercially available from BASF under the tradename Procion MX (RTM) with a It is prepared by reacting one mole of a suitable reactant containing a Y group and then reacting the resulting intermediate dye compound with on...

Embodiment 1

[0102] Synthesis of monochloromonocitrate triazine dyes using Procion (RTM) dyes as raw materials (Procion Red MX-8B / CA)

[0103] Monochloromonocitrate-based triazine dyes were prepared using the synthetic route shown in Scheme 1.

[0104] The synthetic method consists of a one-step reaction of dichlorotriazine dye and citric acid, and the reaction mechanism is shown below.

[0105] Reaction scheme 1

[0106] In this reaction scheme, D is a chromophore and varies according to the starting dye used. In this example, various Procion MX (RTM) dyes commercially available from BASF were used as starting materials, in particular Procion Red MX-8B, Procion Yellow MX-3R, Procion Blue MX-2G and Procion Turquoise Blue MX -G. In the above reaction mechanism, CA represents -O(C=O)R derived from citric acid in the above formula (I) * group, namely, -C(OH)(CH 2 COOH) 2 or -CH 2 C(OH)(COOH)CH 2 COOH. It should be noted that the citric acid moiety is bonded to...

Embodiment 2

[0109] Synthesis of Monocitrate Mononicotinyl Triazine Dye (Compound 2) (Procion Red MX-8B / CA / NA)

[0110] Monocitrate mononicotinyl triazine dyes were prepared using the synthetic route shown in Scheme 2.

[0111] In this reaction scheme, D is a chromophore and varies according to the starting dye used. In this example, Procion (RTM) Red MX-8B was used as starting material. In this example, Procion Red MX-8B can be replaced with other dichlorotriazine dyes such as Procion Yellow MX-3R, Procion Blue MX-2G or Procion Turquoise Blue MX-G. The definition of CA is the same as in Example 1.

[0112] The synthesis method consists of two parts, the first part is to prepare monochloromonocitrate triazine dye (see Example 1), and the second part is to prepare monocitrate mononicotinate triazine dye.

[0113] The monochloromonocitrate triazine dye was prepared using the same method and the same Procion MX starting dye as described in Example 1 above.

[0114] In the second part of...

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Abstract

A reactive dye compound comprising: (a) at least one chromophore moiety, (b) at least one nitrogen-containing heterocycle, (c) a linking group to link each chromophore moiety to each nitrogen-containing heterocycle; characterised in that at least one nitrogen-containing heterocycle is substituted with at least one oxy- or thio-carbonyl derivative wherein the oxy- or thio-carbonyl derivative is selected from Y wherein Y is -A(CO)R* wherein A is selected from O or S and wherein R* is an organic residue which comprises at least one nucleophilic group, and salts thereof. 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 the 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.

Description

technical field [0001] This invention relates to reactive dye compounds. In particular, the present invention relates to reactive dye compounds having improved dyebath exhaustion (Exhaustion, E) and improved dye-fiber covalent fixation (Fixation, F). Background of the invention [0002] Reactive dye compounds are known in the art for dyeing various substrates. Such matrices include, for example, proteinaceous materials such as keratin, which is found, for example, in hair, skin and nails and various animal body parts such as horns, hooves and feathers, and other naturally proteinaceous substances such as silk and sugar-derived substances such as Those obtained from cellulose or cellulose derivatives, such as natural products such as cotton, and synthetic fibers such as polyamide. [0003] Examples of such reactive dyes known in the art include mono- or dichloro- or fluoro-1,3,5-triazinyl, trichloro- or mono- or difluoro-pyrimidinyl, β-halo-propiony...

Claims

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Application Information

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IPC IPC(8): C07D251/16A61K8/49A61Q5/06C07D239/42C07D241/44C07D251/42C07D251/46C07D251/48C07D251/50C07D401/04C07D401/14C09B43/16C09B62/02C09B62/085C09B62/245C09B62/32C09B62/80C09B62/825C09B67/26D06P1/38D06P1/382D06P3/10D06P3/14D06P3/24D06P3/66
CPCA61K2800/57A61Q5/065A61K2800/43A61K8/494A61K8/4966C09B62/02C09B43/16
Inventor 戴维·M·刘易斯何卫东塔尔·I·尤萨夫吉勒斯·Y·M·F·吉奈恩
Owner THE UNIV OF NORTH CAROLINA AT CHAPEL HILL
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