Disperse azo dyes
09938411 ยท 2018-04-10
Assignee
Inventors
Cpc classification
International classification
Abstract
The present invention relates to disperse azo dyes based on diazo components having at least one fluorine-containing substituent and an 2,6-diaminosubstituted pyridine coupling component, to a process for the preparation of such dyes and to their use in the dyeing or printing of semi-synthetic and, especially, synthetic hydrophobic fiber materials, more especially textile materials.
Claims
1. A dye of formula ##STR00067## wherein R.sub.1 is trifluoromethyl, R.sub.2 denotes nitro, R.sub.3 represents hydrogen, R.sub.4 is phenyl and R.sub.5 is hydrogen.
2. A process for the preparation of an azo dye of formula (1) according to claim 1, wherein a compound of formula ##STR00068## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined in claim 1, is diazotised and then coupled to a coupling component of formula ##STR00069## wherein R.sub.4 and R.sub.5 are as defined in claim 1.
3. A dye mixture comprising a dye of formula (1a) according to claim 1 and a dye of formula (1b) ##STR00070## wherein R.sub.1 is trifluoromethyl, R.sub.2 denotes nitro, R.sub.3 represents hydrogen, R.sub.4 is hydrogen and R.sub.5 is phenyl.
4. A process for the dyeing or printing of a semi-synthetic or synthetic hydrophobic fibre material, wherein a dye of formula (1a) according to claim 1 is applied to the said material or is incorporated into that material.
5. A process for the dyeing or printing of a sung-synthetic or synthetic hydrophobic fibre material, wherein a dye mixture according to claim 3 is applied to the said material or is incorporated into that material.
Description
I. PREPARATION EXAMPLES
Example I.1
(1) A. Diazotisation
(2) 10.67 g of 1M-nitrosylsulfuric acid are placed in a laboratory reaction apparatus. At 15-20 C., 3.2 g of 2,4-dibromo-6-trifluoromethylaniline are introduced. After being stirred for 2 hours at 15-20 C., the mixture is poured into 80 g of ice-water and stirred for a further 10 min. The excess nitrite is destroyed by addition of sulfamic acid.
(3) B. Coupling
(4) 2.3 g of a mixture of 2-phenylamino-3-cyano-4-methyl-6-aminopyridine and 2-amino-3-cyano-4-methyl-6-phenylaminopyridine in 40 ml of 80% acetic acid are placed in a laboratory reaction apparatus and 2 drops of Surfynol 104 E (2,4,7,9-tetramethyl-5-decyne-4,7-diol) are added thereto. After addition of 30 g of ice, the solution of the diazonium salt prepared under A is slowly added dropwise so that the internal temperature is <15 C. The mixture is stirred for 1 hour, while the temperature is kept <15 C. by addition of ice and pH is adjusted to 3.0 to 3.5 by addition of 30% NaOH. After heating to 50 C., the mixture is stirred for 30 min and afterwards the solid is filtered off with suction, washed with deionised water and dried. 4.8 g (8.6 mmol, 86% yield) of a mixture of golden yellow dyes of formulae (101a) and (101b) is obtained.
(5) ##STR00005##
Example 1.2
(6) A. Diazotation
(7) 3.2 g of 2-chloro-5-trifluoromethylaniline are dissolved in 20 g of 50% sulfuric acid at room temperature. 0.1 g of ice and 5.55 g of 1M-nitrosylsulfuric acid are added under stirring. After being stirred for 5 hours at 15-20 C., the mixture is poured into 65 ml of acetic acid and stirred for a further 10 min. The excess nitrite is destroyed by addition of 0.5 g of sulfamic acid.
(8) B. Coupling
(9) 3.58 g of a mixture of 2-phenylamino-3-cyano-4-methyl-6-aminopyridine and 2-amino-3-cyano-4-methyl-6-phenylaminopyridine are added to at 5 C. to a solution of 0.5 g of Surfynol 104 E (2,4,7,9-tetramethyl-5-decyne-4,7-diol) and 0.5 g of Baykanol (dispersing agent, supplied by Lanxess) in 65 ml of 80% acetic acid. The solution of the diazonium salt prepared under A is slowly added dropwise under cooling so that the internal temperature is 0-5 C. Subsequently, the mixture is stirred until the internal temperature is about room temperature and afterwards the solid is filtered off with suction, washed with deionised water and dried. 6.1 g (14 mmol, 88% yield) of a mixture of dyes of formulae (102a) and (102b) is obtained.
(10) ##STR00006##
(11) The dyes (102)-(106) listed in Table 1 are prepared analogously to the process described in Example I.1.
(12) TABLE-US-00001
II. APPLICATION EXAMPLES
Example II. 1
(13) Samples of a polyester fabric are dyed in a high-temperature exhaust process at 135 C. in a dyebath containing 1% of one of the dyes (101)-(105). The resulting dyeings exhibit values in respect of light fastness of 6.