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Reactive dyes, their preparation and their use

A technology of reactive dyes and metal complex dyes, applied in the field of new reactive dyes, can solve the problems of unstable dyeing and unsatisfactory dyes

Inactive Publication Date: 2011-11-23
HUNTSMAN ADVANCED MATERIALS (SWITZERLAND) GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Known dyes do not meet those needs in all properties
[0004] So far, highly pigmented dyeings on polyamides have only been possible with acid dyes, but the dyeings are not fast when wet at elevated temperatures

Method used

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  • Reactive dyes, their preparation and their use
  • Reactive dyes, their preparation and their use
  • Reactive dyes, their preparation and their use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0135] (a) 26.4 parts of the free acid form are correspondingly compounds of the following structural formula

[0136]

[0137] Stir in 100 parts of water. The resulting slurry was cooled to 0°C by adding about 50 parts of ice and adjusted to pH 4 with aqueous sodium hydroxide solution, keeping its temperature at 0°C with ice. The resulting solution was slowly added to 18.2 parts of cyanuric chloride containing 20 parts of water, about 80 parts of ice and 0.2 parts of Na 2 HPO 4 12H 2 In the slurry in O, the pH was maintained at 3 by the addition of aqueous sodium hydroxide and the temperature was maintained at 0 °C by the addition of ice. A suspension is obtained comprising the free acid form of the compound of formula

[0138]

[0139] (b) 42 parts of free acid forms are correspondingly compounds of the following structural formula

[0140]

[0141] Slurry with 550 parts water, 15 parts formic acid and 6.8 parts chromium(III) acetate and heat in an autoclave at...

Embodiment 2

[0152] The dye according to example 1 was treated with sodium hydroxide at pH 11 for about 2 hours at room temperature. The resulting solution was freed from salt by dialysis and concentrated to dryness by evaporation. The dyestuff that obtains is free acid form and is correspondingly the compound of following structural formula and coordination isomer (λ 最大 =550nm)

[0153]

[0154] The dyes of formula (102) dye amino-containing fibers in Bordeaux shades with good permanent wet fastness properties even without postfixation, especially when the dyeing process described in EP-A 1687478 is used.

Embodiment 3-9

[0156] Dyes with the following structural formula

[0157]

[0158] (λ 最大 =480nm)

[0159]

[0160] (λ 最大 =499nm)

[0161]

[0162] (λ 最大 =462nm)

[0163]

[0164] (λ 最大 =459nm)

[0165]

[0166] (λ 最大 =461nm)

[0167]

[0168] (λ 最大 =574nm)

[0169]

[0170] (λ 最大 =570nm)

[0171]

[0172] (λ 最大 =573nm)

[0173]

[0174] (λ 最大 =570nm)

[0175]

[0176] (λ 最大 =577nm)

[0177]

[0178] (λ 最大 =459nm)

[0179]

[0180] (λ 最大 =552nm)

[0181]

[0182] (λ 最大 =552nm)

[0183]

[0184] (λ 最大 =588nm)

[0185]

[0186] (λ 最大 =606nm)

[0187]

[0188] (λ 最大 =568nm)

[0189]

[0190] (λ 最大 =570nm)

[0191]

[0192] (λ 最大 =584nm)

[0193]

[0194] (λ 最大 =464nm)

[0195]

[0196] (λ 最大 =572nm)

[0197] and the corresponding acrylate and vinyl ester forms, which can be prepared in a manner similar to that described in Examples 1 and 2 (except for the dyes of formulas (103) to (109) disclosed in ...

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Abstract

Reactive dyes of formula (1), wherein R1 is hydrogen or unsubstituted or substituted C1-C4alkyl, (R2)s denotes s identical or different substituents from the group halogen, nitro, unsubstituted or halo-substituted C1-C4alkyl, C2-C4alkanoylamino, C1-C4alkylsulfonyl, carbamoyl, sulfamoyl and sulfo, Me is chromium, cobalt or iron, E is a bivalent radical of formulae (1a), (1b) or (1c), wherein X denotes chlorine or fluorine, T is a fibre-reactive radical of formula (2a): -NH-(CH2)2-3-SO2-Z, formula (2b): -NH-(CH2)2-3-O-(CH2)2-3-SO2-Z, formulae (2c), (2d), (2e) or (2f), (R3)0-2 denotes from 0 to 2 identical or different substituents from the group halogen, C1-C4alkyl, C1-C4alkoxy and sulfo, Z is vinyl or a -CH2-CH2-U radical and U is a group that is removable under alkaline conditions, Q is a -CH(HaI)-CH2-HaI or -C(HaI)=CH2 group, s is the number 0, 1, 2 or 3, q is the number 0 or 1, A denotes a bivalent radical of formulae (3a), (3b), (3c) or (3d), wherein R1, R2, X, T, m, n, q and s are as defined above, R4 and R7 denote hydrogen or C1-C4alkyl, R5 and R6 represent, each independently of the other, identical or different substituents from the group hydroxyl, halogen, nitro, unsubstituted or halo-substituted C1-C4alkyl, C1-C4alkoxy, C2-C4alkanoylamino, C1-C4alkylsulfonyl, carbamoyl, sulfamoyl and sulfo, and t and u are each independently of the other the number 0, 1, 2 or 3, are especially suitable for dyeing synthetic polyamide fibre materials and yield dyeings or prints having good wet-fastness properties.

Description

technical field [0001] The present invention relates to novel reactive dyes, to a process for their preparation and to their use in the dyeing or printing of textile fiber materials. Background technique [0002] The recent use of reactive dyes for dyeing has led to higher demands on the quality of the dyeings and the economic efficiency of the dyeing process. Therefore, there is still a need for new reactive dyes with improved properties, especially with regard to their applications. [0003] Dyeing currently requires reactive dyes that are sufficiently substantive and at the same time have good properties for easy washing of unfixed dye. They should also have good color yields and high activity, the purpose of which is in particular to provide dyeings with a high level of fixity. Known dyes do not satisfy those requirements in all properties. [0004] To date, highly pigmented dyeings on polyamides have only been possible by using acid dyes, but the dyeings are not fast...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B62/44C09D11/00
CPCC09B45/16C09D11/328C09B62/4416C09B62/44C09D5/035C09D11/30D06P1/38D06P5/30
Inventor 莱纳·希尔德布兰德亚历山大·缪勒库尔特·普拉特纳桑德拉·达席瓦尔萨拉伊娃达米安·舍尔
Owner HUNTSMAN ADVANCED MATERIALS (SWITZERLAND) GMBH
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