Thiol derivative dyes

A compound, alkyl technology, applied in the direction of sulfur dyes, azo dyes, organic dyes, etc., can solve the problem of unsatisfactory washing fastness

Inactive Publication Date: 2009-09-09
CIBA SPECIALTY CHEM HLDG INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is that their fast

Method used

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  • Thiol derivative dyes
  • Thiol derivative dyes
  • Thiol derivative dyes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment A-1

[0379] Example A-1: Preparation of compound of formula (101)

[0380]

[0381] A-1.1 Monoazo (monoazo)

[0382] At 295K, 62 g of 4-fluoroaniline was added to a stirred solution of 125 ml of water and 12 ml of 32% hydrochloric acid. Then, the reaction mixture was cooled to 273K and 95 ml of 36% sodium nitrite solution was added dropwise to control the dropping rate so that the temperature of the mixture was maintained at 273 to 276K. After adding the sodium nitrite solution, the mixture was stirred for one hour. If no remaining nitrite is detected within one hour (use potassium iodide test paper for detection), then add a certain amount of sodium nitrite solution. After this hour, the remaining excess nitrite was reduced with sulfamic acid. Then, the obtained diazo-solution was added dropwise to a 273K cold solution of 38 g of imidazole in 30 ml of water, thereby maintaining the pH of the solution in the range of pH 10 to 11 by adding 36% sodium hydroxide solution. After the a...

Embodiment A-2

[0397] Example A-2: Preparation of the compound of formula (102)

[0398]

[0399] A-2.1 Alkylation

[0400] One equivalent (6.0 g) of thiourea was dissolved in 30 g of the aforementioned alkylating dye solution in absolute ethanol. The temperature was raised to reflux and the temperature was maintained at 80°C for the next 48 hours.

[0401] A-2.2 Hydrolysis

[0402] One equivalent (4.0 g) of sodium hydroxide was dissolved in the absolute ethanol solution of the aforementioned substances. The temperature was maintained at 80°C for the next 4 hours. Under stirring, the product was crystallized by cooling to room temperature, and then separated by filtration, washed and dried in a vacuum dryer.

[0403] Use the following data to characterize the product:

[0404] In deuterated chloroform 1 H-NMR data (128 scans) / 360MHz

[0405] 8.003 d 6.7 2.00 Phenyl

[0406] 7.576 s 2.01 imidazolyl

[0407] 7.000 d 6.9 2.01 phenyl

[0408] 4.060 s 6.00 methyl

[0409] 4.002 t 6 2.03 ethyl...

Embodiment A-3

[0412] Example A-3: Preparation of the compound of formula (103)

[0413]

[0414] A-3.1 Alkylation

[0415] One equivalent (10.0 g) of potassium thioacetate was dissolved in a solution of 30 g of the aforementioned alkylated dye in 75 ml of ethanol. The temperature was raised to reflux and the temperature was maintained at 80°C for the next 4 hours.

[0416] Use the following data to characterize the product:

[0417] In deuterated chloroform 1 H-NMR data (128 scans) / 360MHz

[0418] 8.003 d 6.7 2.00 Phenyl

[0419] 7.578 s 2.01 imidazolyl

[0420] 7.060 d 6.9 2.01 phenyl

[0421] 4.074 s 6.00 methyl

[0422] 3.352 t 6 2.03 ethylene

[0423] 3.085 t 6 2.05 ethylene

[0424] 2.289 s 3.087 acetate

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Abstract

Disclosed are thiol dyes of formula (1 ) wherein L1 is hydrogen; C1-C12 alkyl; or phenyl-C1-C4alkyl; X is C1-C12 alkylene, C2-C12 alkenylene, C5-C10 cycloalkylene, C5-C10 arylene, or C5-C10 arylene-C1-C10 alkylene, which may by interrupted by -O-, -NH-, -S-, -CO-, or -SO2-; Y is the residue of an organic dye; Z is a group of formula (1b) or -carbon-nitrogen triple bond; wherein A is O; S; or N-L2; B is L3; -OL3; -NL3L4; or -SL3; and L2, L3 and L4, indepently from other are are hydrogen; C1-C12 alkyl; C5-C12 aryl-C1-C12 alkyl. The compounds are useful for the dyeing of organic materials, such as keratin fibers, preferably human hair.

Description

Technical field [0001] The present invention relates to new thiol derivative dyes and compositions comprising the dyes, their preparation methods and their use for dyeing organic substances, wherein the organic substances such as keratin fibers (keratin fibers) fibers), wool, leather, silk, cellulose or polyamide, especially keratin-containing fibers, cotton or nylon, preferably hair, more preferably human hair. Background technique [0002] For example, it is known from WO 95 / 01772 that cationic dyes can be used for dyeing organic substances, such as keratin, silk, cellulose or cellulose derivatives, and also synthetic fibers, such as polyamides. Cationic dyes exhibit very bright shades. The disadvantage is that their fastness to washing is not satisfactory. Summary of the invention [0003] The technical problem of the present invention is to provide a dye that is characterized by good washing resistance, light resistance, shampoo resistance and abrasion resistance and deep dy...

Claims

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Application Information

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IPC IPC(8): C09B44/16C09B55/00C09B56/18C09B49/00C09B29/36A61Q5/06A61Q5/10
CPCC09B44/16C09B49/00A61Q5/065A61K8/4946C09B55/003C09B56/18A61Q5/10C09B55/00
Inventor 维克托·埃利尤比特·弗罗林多米尼克·考夫曼
Owner CIBA SPECIALTY CHEM HLDG INC
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