Method for improving alkali resistance and oxidation resistance of benzothiazole disperse dye

Abstract

The disclosure relates to a method for improving the alkali resistance and oxidation resistance of a benzothiazole disperse dye, and belongs to the field of disperse dyes. In the disclosure, 4 kinds of diazo components and 8 kinds of coupling components are used in designing and synthesizing 28 thiazole heterocyclic azo disperse dyes, and the alkali resistance and oxidation resistance of the disperse dyes are improved. Structure confirmation is performed on the synthetic disperse dyes, and the alkali resistance, oxidation resistance and other dyeing properties of the disperse dyes are tested. According to the method for improving the alkali resistance and oxidation resistance of the benzothiazole disperse dye provided in the disclosure, a relationship between a dye structure and the alkali resistance and oxidation resistance is determined, the disperse dyes with excellent alkali resistance and oxidation resistance are obtained, and the dyeing performance is stable under a dyeing condition of 10 g/L of sodium hydroxide or 5 g/L of hydrogen peroxide. This kind of dyes can be applied to a one bath for bleaching and dyeing of polyester and cotton and a one bath for deweighting and dyeing of polyester, dyeing and finishing in a short process are achieved, and great ecological and economic benefits are obtained.

Claims

1. A benzothiazole disperse dye having the following structural formula: ##STR00083##

Description

BRIEF DESCRIPTION OF FIGURES

(1) FIG. 1 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 1.

(2) FIG. 2 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 2.

(3) FIG. 3 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 3.

(4) FIG. 4 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 4.

(5) FIG. 5 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 5.

(6) FIG. 6 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 6.

(7) FIG. 7 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 7.

(8) FIG. 8 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 8.

(9) FIG. 9 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 10.

(10) FIG. 10 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 12.

(11) FIG. 11 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 14.

(12) FIG. 12 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 16.

(13) FIG. 13 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 18.

(14) FIG. 14 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 20.

(15) FIG. 15 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 24.

(16) FIG. 16 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 25.

(17) FIG. 17 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 26.

(18) FIG. 18 is a hydrogen nuclear magnetic resonance spectrum of a benzothiazole disperse dye obtained in Example 28.

DETAILED DESCRIPTION

(19) It should be understood that descriptions of the following preferred examples of the disclosure are used to better explain the disclosure, but not intended to limit the disclosure.

Performance Test Methods

(20) An alkali resistance test of a dye including a stability test under different pH values and a stability test under different NaOH concentrations and an oxidation resistance test of the dye are involved. Specific test steps include: (1) preparing a dyeing solution at room temperature, wherein the use amount of a dye in the dyeing solution is 2% of the weight of a polyester knitted fabric, the use amount of an alkali-resistant levelling agent is 1 g/L, the weight ratio of the dyeing solution to the polyester knitted fabric is 30:1, a high-temperature and high-pressure dyeing method is used, and reduction clearing is performed on the polyester knitted fabric after dyeing to obtain a dyed polyester knitted fabric; (2) testing the stability of a dye under different pH values, wherein a dye bath with a pH=3-13 is prepared, dyeing and reduction clearing after dyeing are performed on a polyester knitted fabric under different pH values according to a dyeing and reduction clearing process formula and a process flow in step (1), the stability of the dye under different pH values is tested, and the highest pH value when the color and luster of the dye are not changed is taken as the highest pH resistant value of the dye; (3) testing the stability of a dye under different NaOH concentrations, wherein a test on high alkali resistance of a benzothiazole disperse dye is performed when the pH is stable and 10, a dye bath with a NaOH concentration of 0-10 g/L is prepared, dyeing and reduction clearing after dyeing are performed on a polyester knitted fabric under different NaOH concentrations according to a dyeing and reduction clearing process formula and a process flow in step (1), the stability of the dye under different NaOH concentrations is tested, and the highest NaOH concentration when the color and luster of the dye are not changed is taken as the highest NaOH resistant concentration of the dye; (4) testing the stability of a dye under different hydrogen peroxide concentrations, wherein since the optimal pH value of hydrogen peroxide for bleaching a cotton fabric is 10-11, the stability of the dye under different hydrogen peroxide concentrations is tested when the pH is 10, a dye bath with a hydrogen peroxide concentration of 0-5 g/L is prepared, dyeing and reduction clearing after dyeing are performed on a polyester knitted fabric under different hydrogen peroxide concentrations according to a dyeing and reduction clearing process formula and a process flow in step (1) under the condition that the concentration of a hydrogen peroxide stabilizer (stabilizer DM1403) is 2 g/L, the stability of the dye under different hydrogen peroxide concentrations is tested, and the highest hydrogen peroxide concentration when the color and luster of the dye are not changed is taken as the highest hydrogen peroxide resistant concentration of the dye.

Example 1

(21) A benzothiazole disperse dye with a structural formula shown below is provided,

(22) ##STR00027##

(23) A synthetic route is:

(24) ##STR00028##

(25) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction: adding 2-amino-5,6-dichlorobenzothiazole (0.04 mol) into a single-neck flask, adding 20.00 ml of water and 15.6 g of a 98% sulfuric acid solution, reducing the temperature to 0 C., adding an appropriate amount (12.7 g) of nitrosyl sulfuric acid under stirring (300-500 rpm), performing uniform stirring and detection with a starch-potassium iodide test paper until the color is blue to ensure that nitrosyl sulfuric acid is excessive, performing a reaction continuously for 3 h, adding 3.88 g of sulfamic acid to remove excessive nitrosyl sulfuric acid after the reaction is completed, and performing stirring at 0 C. for 15 min to obtain a diazo solution; (2) performing a coupling reaction: adding 60 mL of water, 2 mL of H.sub.2SO.sub.4 and a coupling component (N-ethyl-N-p-methylphenylaniline (0.1 mol)) into a double-neck flask, and reducing the temperature to 8 C. to obtain a coupling solution; slowly adding the diazo solution obtained in step (1) dropwise into the coupling solution under stirring for performing a reaction continuously at 8 C. for 2 h, increasing the temperature to 12 C. for performing a reaction continuously for 4 h, and after the reaction is completed, adding sodium hydroxide to adjust the pH to neutral to obtain a product; performing suction filtration, washing and drying on the obtained product to obtain a filter cake; (3) dissolving the filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(26) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 1) of hydrogen nuclear magnetic resonance spectrum are:

(27) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.11 (s, 1H, ArH, 1), 7.96-7.93 (dd, 2H, ArH, 3, 3), 7.89 (s, 1H, ArH, 2), 7.26 (solvent peak), 7.17-7.08 (dd, 4H, ArH, 8, 9, 10, 11), 6.81-6.78 (dd, 2H, ArH, 4, 4), 4.66 (s, 2H, CH.sub.2, 7), 3.64-3.59 (q, 2H, CH.sub.2, 5), 2.34 (s, 3H, CH.sub.3, 12), 1.56 (water peak), 1.33-1.29 (t, 3H, CH.sub.3, 6).

Example 2

(28) A benzothiazole disperse dye with a structural formula shown below is provided,

(29) ##STR00029##

(30) A synthetic route is:

(31) ##STR00030##

(32) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein 2-amino-5,6-dichlorobenzothiazole in step (1) in Example 1 was changed into 2-amino-6-chlorobenzothiazole, and other conditions were the same as those in step (1) in Example 1; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 1; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(33) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 2) of hydrogen nuclear magnetic resonance spectrum are:

(34) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.11 (s, 1H, ArH, 1), 7.96-7.93 (dd, 2H, ArH, 3, 3), 7.89 (s, 1H, ArH, 2), 7.26 (solvent peak), 7.17-7.08 (dd, 4H, ArH, 8, 9, 10, 11), 6.81-6.78 (dd, 2H, ArH, 4, 4), 4.66 (s, 2H, CH.sub.2, 7), 3.64-3.59 (q, 2H, CH.sub.2, 5), 2.34 (s, 3H, CH.sub.3, 12), 1.56 (water peak), 1.33-1.29 (t, 3H, CH.sub.3, 6).

Example 3

(35) A benzothiazole disperse dye with a structural formula shown below is provided,

(36) ##STR00031##

(37) A synthetic route is:

(38) ##STR00032##

(39) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein 2-amino-5,6-dichlorobenzothiazole in step (1) in Example 1 was changed into 2-amino-6-nitrobenzothiazole, and other conditions were the same as those in step (1) in Example 1; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 1; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(40) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 3) of hydrogen nuclear magnetic resonance spectrum are:

(41) .sup.1H NMR (500 MHz, CDCl.sub.3) 8.08-7.99 (d, 1H, ArH, 1), 7.96-7.85 (d, 1H, ArH, 2) 7.85-7.49 (dd, 1H, ArH, 3), 7.26 (solvent peak), 7.17-7.07 (dd, 4H, ArH, 10, 11, 12, 13), 6.65-6.62 (dd, 1H, ArH, 4), 6.61-6.60 (t, 1H, ArH, 5), 4.65 (s, 2H, CH.sub.2, 9), 3.61-3.56 (s, 2H, CH.sub.2, 7), 2.66-2.63 (d, 3H, CH.sub.3, 6), 2.35 (s, 3H, CH.sub.3, 14), 1.57 (water peak), 1.31-1.28 (t, 3H, CH.sub.3, 8).

Example 4

(42) A benzothiazole disperse dye with a structural formula shown below is provided,

(43) ##STR00033##

(44) A synthetic route is:

(45) ##STR00034##

(46) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein 2-amino-5,6-dichlorobenzothiazole in step (1) in Example 1 was changed into 2-aminobenzothiazole, and other conditions were the same as those in step (1) in Example 1; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 1; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(47) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 4) of hydrogen nuclear magnetic resonance spectrum are:

(48) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.14, 7.89 (d, 1H, ArH, 2), 8.00-7.97 (d, 1H, ArH, 3), 7.90, 7.88, 7.55, 7.53 (dd, 1H, ArH, 1), 7.39-7.32 (m, 3H, ArH, 10, 12, 14), 7.26 (solvent peak), 7.20-7.18 (d, 2H, ArH, 11, 13), 6.69-6.67 (d, 1H, ArH, 4), 6.67-6.65 (d, 1H, ArH, 5), 4.81 (s, 2H, CH.sub.2, 9), 3.91-3.88 (t, 2H, CH.sub.2, 7), 2.76-2.72 (m, 2H, CH.sub.2, 8), 2.70-2.68 (d, 3H, CH.sub.3, 6), 1.56 (water peak).

Example 5

(49) A benzothiazole disperse dye with a structural formula shown below is provided,

(50) ##STR00035##

(51) A synthetic route is:

(52) ##STR00036##

(53) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 1; (2) performing a coupling reaction, wherein N-ethyl-N-p-methylphenylaniline in step (2) in Example 1 was changed into N-ethyl-N-p-methylphenyl-m-methylaniline, and other conditions were the same as those in step (2) in Example 1; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(54) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 5) of hydrogen nuclear magnetic resonance spectrum are:

(55) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.09, 7.85 (d, H, ArH, 2), 7.99-7.97 (d, 1H, ArH, 3), 7.83-7.49 (dd, 1H, ArH, 1), 7.37-7.26 (m, 3H, ArH, 10, 14, 12), 7.26 (solvent peak), 7.21-7.19 (d, 2H, ArH, 11, 13), 6.66-6.63 (dd, 1H, ArH, 4), 6.62-6.60 (t, 1H, ArH, 5), 4.69 (s, 2H, CH.sub.2, 9), 3.63-3.58 (q, 2H, CH.sub.2, 7), 2.66-2.64 (d, 3H, CH.sub.3, 6), 1.59 (water peak), 1.32-1.29 (t, 3H, CH.sub.3, 8).

Example 6

(56) A benzothiazole disperse dye with a structural formula shown below is provided,

(57) ##STR00037##

(58) A synthetic route is:

(59) ##STR00038##

(60) A preparation method of the benzothiazole disperse dye includes the following steps:

(61) (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 2; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 5; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(62) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 6) of hydrogen nuclear magnetic resonance spectrum are:

(63) hydrogen spectrum: .sup.1H NMR (400 MHz, CDCl.sub.3) 8.11, 7.89 (d, 1H, ArH, 2), 7.97-7.94 (dd, 2H, ArH, 3, 3), 7.88-7.51 (dd, 1H, ArH, 1), 7.38-7.29 (m, 3H, ArH, 8, 10, 12), 7.26 (solvent peak), 7.21-7.20 (d, 2H, ArH, 9, 11), 6.82-6.79 (dd, 2H, ArH, 4, 4), 4.71 (s, 2H, CH.sub.2, 7), 3.63 (q, 2H, CH.sub.2, 5), 1.57 (water peak), 1.32 (t, 3H, CH.sub.3, 6).

Example 7

(64) A benzothiazole disperse dye with a structural formula shown below is provided,

(65) ##STR00039##

(66) A synthetic route is:

(67) ##STR00040##

(68) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 3; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 5; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(69) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 7) of hydrogen nuclear magnetic resonance spectrum are:

(70) hydrogen spectrum: .sup.1H NMR (400 MHz, CDCl.sub.3) 8.10, 7.89 (d, 1H, ArH, 2), 7.98-7.95 (dd, 2H, ArH, 3, 3), 7.87-7.50 (dd, 1H, ArH, 1), 7.26 (solvent peak), 6.77-6.74 (dd, 2H, ArH, 4, 4), 3.55-3.50 (q, 4H, CH.sub.2, 5, 5), 1.57 (water peak), 1.30-1.27 (t, 6H, CH.sub.3, 6, 6)

Example 8

(71) A benzothiazole disperse dye with a structural formula shown below is provided,

(72) ##STR00041##

(73) A synthetic route is:

(74) ##STR00042##

(75) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 4; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 5; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(76) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 8) of hydrogen nuclear magnetic resonance spectrum are:

(77) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.12, 7.91 (d, 1H, ArH, 2), 7.99-7.96 (dd, 2H, ArH, 3, 3), 7.88-7.52 (dd, 1H, ArH, 1), 7.26 (solvent peak), 6.84-6.81 (dd, 2H, ArH, 4, 4), 3.95-3.91 (q, 2H, CH.sub.2, 7), 3.68-3.65 (t, 2H, CH.sub.2, 8), 3.64-3.58 (q, 2H, CH.sub.2, 5), 1.67-1.64 (t, 1H, OH, 9), 1.56 (water peak), 1.31-1.27 (t, 3H, CH.sub.3, 6).

Example 9

(78) A benzothiazole disperse dye with a structural formula shown below is provided,

(79) ##STR00043##

(80) A synthetic route is:

(81) ##STR00044##

(82) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 1; (2) performing a coupling reaction, wherein N-ethyl-N-p-methylphenylaniline in step (2) in Example 1 was changed into N-propylcyano-N-phenylaniline, and other conditions were the same as those in step (2) in Example 1; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(83) Structural characterization is performed on the obtained benzothiazole disperse dye, and results of hydrogen nuclear magnetic resonance spectrum are:

(84) .sup.1H NMR (400 MHz, CDCl.sub.3) 7.97 (s, 1H, ArH, 1), 7.96-7.95 (d, 2H, ArH, 4, 4), 7.80 (d, 1H, ArH, 2), 7.42-7.40 (dd, 1H, ArH, 3), 7.26 (solvent peak), 7.17-7.08 (dd, 4H, ArH, 9, 10, 11, 12), 6.79 (d, 2H, ArH, 5, 5), 4.66 (s, 2H, CH.sub.2, 8), 3.61 (q, 2H, CH.sub.2, 6), 2.34 (s, 3H, CH.sub.3, 13), 1.55 (water peak), 1.30 (t, 3H, CH.sub.3, 7).

Example 10

(85) A benzothiazole disperse dye with a structural formula shown below is provided,

(86) ##STR00045##

(87) A synthetic route is:

(88) ##STR00046##

(89) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 2; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 9; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(90) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 9) of hydrogen nuclear magnetic resonance spectrum are:

(91) .sup.1H NMR (400 MHz, CDCl.sub.3) 7.98-7.96 (d, 1H, ArH, 1), 7.95-7.92 (d, 1H, ArH, 4), 7.76 (d, 1H, ArH, 2), 7.41-7.38 (dd, 1H, ArH, 3), 7.26 (solvent peak), 7.17-7.08 (dd, 4H, ArH, 11, 12, 13, 14), 6.65-6.62 (dd, 1H, ArH, 5), 6.60 (d, 1H, ArH, 6), 4.64 (s, 2H, CH.sub.2, 10), 3.61-3.55 (q, 2H, CH.sub.2, 8), 2.64 (s, 3H, CH.sub.3, 7), 2.34 (s, 3H, CH.sub.3, 15), 1.55 (water peak), 1.31-1.27 (t, 3H, CH.sub.3, 9)

Example 11

(92) A benzothiazole disperse dye with a structural formula shown below is provided,

(93) ##STR00047##

(94) A synthetic route is:

(95) ##STR00048##

(96) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 1; (2) performing a coupling reaction, wherein N-ethyl-N-p-methylphenylaniline in step (2) in Example 1 was changed into N-propylcyano-N-phenyl-m-toluidine, and other conditions were the same as those in step (2) in Example 1; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(97) Structural characterization is performed on the obtained benzothiazole disperse dye, and results of hydrogen nuclear magnetic resonance spectrum are:

(98) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.01-7.82 (dd, 1H, ArH, 1), 7.46-7.35 (dd, 1H, ArH, 3), 7.34-7.28, 7.24-7.19 (m, 7H, ArH, 4,4,9, 10, 11, 12, 13), 7.26 (solvent peak), 6.86-6.79 (dd, 1H, ArH, 2), 6.77-6.74 (t, 2H, ArH, 5, 5), 4.61 (s, 2H, CH.sub.2, 8), 3.78-3.75 (t, 2H, CH.sub.2, 6), 3.75-3.70 (q, ethanol-CH.sub.2), 2.63-2.60 (t, 2H, CH.sub.2, 7), 1.60 (water peak), 1.26-1.23 (t, ethanol-CH.sub.3)

Example 12

(99) A benzothiazole disperse dye with a structural formula shown below is provided,

(100) ##STR00049##

(101) A synthetic route is:

(102) ##STR00050##

(103) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 10; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 11; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(104) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 10) of hydrogen nuclear magnetic resonance spectrum are:

(105) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.01-7.89 (d, 1H, ArH, 1), 7.96 (s, 1H, ArH, 4), 7.81-7.78 (dd, 1H, ArH, 2), 7.43-7.41 (dd, 1H, ArH, 3), 7.38-7.31, 7.20-7.18 (m, 5H, ArH, 11, 12, 13, 14, 15), 7.26 (solvent peak), 6.67-6.58 (m, 2H, ArH, 5, 6), 4.79 (s, 2H, CH.sub.2, 10), 3.94-3.87 (dt, 2H, CH.sub.2, 8), 3.75-3.69 (q, ethanol-CH.sub.2), 2.75-2.72 (t, 2H, CH.sub.2, 9), 2.70-2.68 (ds, 3H, CH.sub.3, 7), 1.65 (water peak), 1.26-1.22 (t, ethanol-CH.sub.3)

Example 13

(106) A benzothiazole disperse dye with a structural formula shown below is provided,

(107) ##STR00051##

(108) A synthetic route is:

(109) ##STR00052##

(110) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 1; (2) performing a coupling reaction, wherein N-ethyl-N-p-methylphenylaniline in step (2) in Example 1 was changed into N-ethyl-N-benzyl-m-toluidine, and other conditions were the same as those in step (2) in Example 1; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(111) Structural characterization is performed on the obtained benzothiazole disperse dye, and results of hydrogen nuclear magnetic resonance spectrum are:

(112) .sup.1H NMR (400 MHz, CDCl.sub.3) 7.98-7.92 (dd, 2H, ArH, 1, 4,), 7.76-7.75 (d, 1H, ArH, 2), 7.40-7.38 (dd, 1H, ArH, 3), 7.37-7.28, 7.21-7.19 (m, 5H, ArH, 11, 12, 13, 14, 15), 7.26 (solvent peak), 6.65-6.62 (dd, 1H, ArH, 5), 6.60-6.59 (d, 1H, ArH, 6), 4.67 (s, 2H, CH.sub.2, 10), 3.62-3.56 (q, 2H, CH.sub.2, 8), 2.64 (s, 3H, CH.sub.3, 7), 1.64 (water peak), 1.31-1.24 (t, 3H, CH.sub.3, 9).

Example 14

(113) A benzothiazole disperse dye with a structural formula shown below is provided,

(114) ##STR00053##

(115) A synthetic route is:

(116) ##STR00054##

(117) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 2; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 13; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(118) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 11) of hydrogen nuclear magnetic resonance spectrum are:

(119) hydrogen spectrum: .sup.1H NMR (400 MHz, CDCl.sub.3) 7.97-7.93 (m, 3H, ArH, 1, 4, 4), 7.80-7.79 (d, 1H, ArH, 2), 7.42-7.40 (dd, 1H, ArH, 3), 7.37-7.29, 7.21-7.20 (m, 5H, ArH, 9, 10, 11, 12, 13) 7.26 (solvent peak), 6.80-6.78 (d, 2H, ArH, 5, 5), 4.69 (s, 2H, CH.sub.2, 8), 3.65-3.59 (q, 4H, CH.sub.2, 6), 1.61 (water peak), 1.33-1.29 (t, 3H, CH.sub.3, 7).

Example 15

(120) A benzothiazole disperse dye with a structural formula shown below is provided,

(121) ##STR00055##

(122) A synthetic route is:

(123) ##STR00056##

(124) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 3; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 13; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(125) Structural characterization is performed on the obtained benzothiazole disperse dye, and results of hydrogen nuclear magnetic resonance spectrum are:

(126) .sup.1H NMR (400 MHz, CDCl.sub.3) 7.96-7.93 (m, 3H, ArH, 1, 4, 4), 7.79-7.78 (d, 1H, ArH, 2), 7.41-7.38 (dd, 1H, ArH, 3), 7.26 (solvent peak), 6.74-6.72 (d, 2H, ArH, 5, 5), 3.52-3.47 (q, 4H, CH.sub.2, 6, 6), 1.67 (water peak), 1.28-1.24 (t, 6H, CH.sub.3, 7, 7).

Example 16

(127) A benzothiazole disperse dye with a structural formula shown below is provided,

(128) ##STR00057##

(129) A synthetic route is:

(130) ##STR00058##

(131) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 4; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 13; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(132) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 12) of hydrogen nuclear magnetic resonance spectrum are:

(133) .sup.1H NMR (400 MHz, CDCl.sub.3) 7.97-7.94 (m, 3H, ArH, 1, 4, 4), 7.81-7.80 (d, 1H, ArH, 2), 7.43-7.40 (dd, 1H, ArH, 3), 7.26 (solvent peak), 6.82-6.79 (d, 2H, ArH, 5, 5), 3.94-3.91 (t, 2H, CH.sub.2, 8), 3.67-3.64 (t, 2H, CH.sub.2, 9), 3.61-3.56 (q, 2H, CH.sub.2, 6), 1.56 (water peak), 1.29-1.25 (t, 3H, CH.sub.3, 7).

Example 17

(134) A benzothiazole disperse dye with a structural formula shown below is provided,

(135) ##STR00059##

(136) A synthetic route is:

(137) ##STR00060##

(138) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 1; (2) performing a coupling reaction, wherein N-ethyl-N-p-methylphenylaniline in step (2) in Example 1 was changed into N-ethyl-N-benzylaniline, and other conditions were the same as those in step (2) in Example 1; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(139) Structural characterization is performed on the obtained benzothiazole disperse dye, and results of hydrogen nuclear magnetic resonance spectrum are:

(140) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.75-8.74 (d, 1H, ArH, 1), 8.33-8-31 (dd, 1H, ArH, 2), 8.11-8.09 (d, 1H, ArH, 3), 8.00-7.97 (d, 2H, ArH, 4), 7.26 (solvent peak), 7.18-7.08 (dd, 4H, ArH, 9, 10, 11, 12), 6.83-6.81 (d, 2H, ArH, 5), 4.69 (s, 2H, CH.sub.2, 8), 3.67-3.61 (q, 2H, CH.sub.2, 6), 2.35 (s, 3H, CH.sub.3, 13), 1.54 (water peak), 1.34-1.31 (t, 3H, CH.sub.3, 7).

Example 18

(141) A benzothiazole disperse dye with a structural formula shown below is provided,

(142) ##STR00061##

(143) A synthetic route is:

(144) ##STR00062##

(145) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 2; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 17; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(146) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 13) of hydrogen nuclear magnetic resonance spectrum are:

(147) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.71-8.70 (d, 1H, ArH, 1), 8.32-8.29 (dd, 1H, ArH, 3), 8.08-8.06 (d, 1H, ArH, 2), 8.04-8.01 (d, 1H, ArH, 4), 7.26 (solvent peak), 7.18-7.07 (dd, 4H, ArH, 11, 12, 13, 14), 6.68-6.65 (dd, 1H, ArH, 5), 6.63 (d, 1H, ArH, 6), 4.67 (s, 2H, CH.sub.2, 10), 3.64-3.58 (q, 2H, CH.sub.2, 8), 2.66 (s, 3H, CH.sub.3, 7), 2.35 (s, 3H, CH.sub.3, 15), 1.55 (water peak), 1.33-1.29 (t, 3H, CH.sub.3, 9).

Example 19

(148) A benzothiazole disperse dye with a structural formula shown below is provided,

(149) ##STR00063##

(150) A synthetic route is:

(151) ##STR00064##

(152) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 3; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 17; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(153) Structural characterization is performed on the obtained benzothiazole disperse dye, and results of hydrogen nuclear magnetic resonance spectrum are:

(154) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.69 (d, 1H, ArH, 1), 8.30-8.27 (dd, 1H, ArH, 3), 8.07-8.05 (d, 1H, ArH, 2), 8.02-8.00 (d, 1H, ArH, 4) 7.38-7.28, 7.21-7.19 (m, 5H, ArH, 11, 12, 1314, 15), 7.26 (solvent peak), 6.68-6.65 (dd, 1H, ArH, 5), 6.63-6.62 (d, 1H, ArH, 6), 4.71 (s, 2H, CH.sub.2, 10), 3.65-3.60 (q, 2H, CH.sub.2, 8), 2.65 (s, 3H, CH.sub.3, 7) 1.60 (water peak), 1.34-1.30 (t, 3H, CH.sub.3, 9).

Example 20

(155) A benzothiazole disperse dye with a structural formula shown below is provided,

(156) ##STR00065##

(157) A synthetic route is:

(158) ##STR00066##

(159) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 3; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 17; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(160) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 14) of hydrogen nuclear magnetic resonance spectrum are:

(161) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.73 (d, 1H, ArH, 1), 8.32-8.29 (dd, 1H, ArH, 3), 8.11-8.08 (d, 1H, ArH, 2), 7.99-7.96 (d, 2H, ArH, 4, 4) 7.38-7.28, 7.21-7.19 (m, 5H, ArH, 9, 10, 11, 12, 13), 7.26 (solvent peak), 6.83-6.81 (d, 2H, ArH, 5, 5), 4.73 (s, 2H, CH.sub.2, 8), 3.68-3.62 (q, 2H, CH.sub.2, 6), 1.60 (water peak), 1.35-1.32 (t, 3H, CH.sub.3, 7).

Example 21

(162) A benzothiazole disperse dye with a structural formula shown below is provided,

(163) ##STR00067##

(164) A synthetic route is:

(165) ##STR00068##

(166) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 1; (2) performing a coupling reaction, wherein N-ethyl-N-p-methylphenylaniline in step (2) in Example 1 was changed into N,N-diethylaniline, and other conditions were the same as those in step (2) in Example 1; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(167) Structural characterization is performed on the obtained benzothiazole disperse dye, and results of hydrogen nuclear magnetic resonance spectrum are:

(168) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.71-8.71 (d, 1H, ArH, 1), 8.30-8.27 (dd, 1H, ArH, 3), 8.08-8.06 (d, 1H, ArH, 2), 7.98-7.96 (d, 2H, ArH, 4, 4), 7.26 (solvent peak), 6.67-6.74 (d, 2H, ArH, 5, 5), 3.56-3.51 (q, 4H, CH.sub.2, 6, 6), 1.64 (water peak), 1.31-1.28 (t, 3H, CH.sub.3, 7, 7).

Example 22

(169) A benzothiazole disperse dye with a structural formula shown below is provided,

(170) ##STR00069##

(171) A synthetic route is:

(172) ##STR00070##

(173) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 2; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 21; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(174) Structural characterization is performed on the obtained benzothiazole disperse dye, and results of hydrogen nuclear magnetic resonance spectrum are:

(175) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.72-8.72 (d, 1H, ArH, 1), 8.31-8.29 (dd, 1H, ArH, 3), 8.10-8.07 (d, 1H, ArH, 2), 7.96-7.94 (d, 2H, ArH, 4, 4), 7.26 (solvent peak), 6.83-6.80 (d, 2H, ArH, 5, 5), 3.96-3.93 (t, 2H, CH.sub.2, 8), 3.70-3.67 (t, 2H, CH.sub.2, 9), 3.64-3.59 (q, 2H, CH.sub.2, 6), 1.61 (water peak), 1.31-1.27 (t, 3H, CH.sub.3, 7).

Example 23

(176) A benzothiazole disperse dye with a structural formula shown below is provided,

(177) ##STR00071##

(178) A synthetic route is:

(179) ##STR00072##

(180) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 3; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 21; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(181) Structural characterization is performed on the obtained benzothiazole disperse dye, and results of hydrogen nuclear magnetic resonance spectrum are:

(182) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.08-8.06 (d, 1H, ArH, 1), 7.97-7.95 (d, 2H, ArH, 3, 3), 7.84-7.82 (d, 1H, ArH, 2), 7.51-7.33 (m, 2H, ArH, 4, 4), 7.26 (solvent peak), 7.17-7.09 (dd, 4H, ArH, 9, 10, 11, 12), 6.80-6.78 (d, 2H, ArH, 5, 5), 4.65 (s, 2H, CH.sub.2, 8), 3.63-3.58 (q, 2H, CH.sub.2, 6), 2.34 (s, 3H, CH.sub.3, 13), 1.54 (water peak), 1.32-1.28 (t, 3H, CH.sub.3, 7).

Example 24

(183) A benzothiazole disperse dye with a structural formula shown below is provided,

(184) ##STR00073##

(185) A synthetic route is:

(186) ##STR00074##

(187) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 4; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 21; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(188) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 15) of hydrogen nuclear magnetic resonance spectrum are:

(189) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.06-8.04 (d, 1H, ArH, 2), 7.99-7.97 (d, 1H, ArH, 1), 7.81-7.79 (d, 1H, ArH, 4), 7.50-7.31 (m, 2H, ArH, 3, 3), 7.26 (solvent peak), 7.16-7.08 (dd, 4H, ArH, 11, 12, 13, 14), 6.65-6.62 (dd, 1H, ArH, 5), 6.60 (d, 1H, ArH, 6), 4.63 (s, 2H, CH.sub.2, 10), 3.60-3.55 (q, 2H, CH.sub.2, 8), 2.66 (s, 3H, CH.sub.3, 7), 2.34 (s, 3H, CH.sub.3, 15), 1.56 (water peak), 1.30-1.27 (t, 3H, CH.sub.3, 9).

Example 25

(190) A benzothiazole disperse dye with a structural formula shown below is provided,

(191) ##STR00075##

(192) A synthetic route is:

(193) ##STR00076##

(194) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 1; (2) performing a coupling reaction, wherein N-ethyl-N-p-methylphenylaniline in step (2) in Example 1 was changed into N-ethyl-N-hydroxyethylaniline, and other conditions were the same as those in step (2) in Example 1; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(195) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 16) of hydrogen nuclear magnetic resonance spectrum are:

(196) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.06-8.04 (d, 1H, ArH, 2), 8.00-7.97 (d, 1H, ArH, 1), 7.81-7.79 (d, 1H, ArH, 4), 7.46-7.28 (m, 5H, ArH, 11, 12, 13, 14, 15), 7.26 (solvent peak), 7.21-7.19 (d, 2H, ArH, 3, 3), 6.65-6.62 (dd, 1H, ArH, 5), 6.60-6.59 (d, 1H, ArH, 6), 4.67 (s, 2H, CH.sub.2, 10), 3.61-3.56 (q, 2H, CH.sub.2, 8), 2.66 (s, 3H, CH.sub.3, 7), 1.69 (water peak), 1.31-1.28 (t, 3H, CH.sub.3, 9).

Example 26

(197) A benzothiazole disperse dye with a structural formula shown below is provided,

(198) ##STR00077##

(199) A synthetic route is:

(200) ##STR00078##

(201) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 2; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 25; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(202) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 17) of hydrogen nuclear magnetic resonance spectrum are:

(203) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.08-8.06 (d, 1H, ArH, 2), 7.97-7.95 (d, 2H, ArH, 4, 4), 7.84-7.82 (d, 1H, ArH, 1), 7.48-7.28 (m, 5H, ArH, 9, 10, 11, 12, 13), 7.26 (solvent peak), 7.22-7.20 (d, 2H, ArH, 3, 3), 6.80-6.78 (d, 2H, ArH, 5, 5), 4.69 (s, 2H, CH.sub.2, 8), 2.64-3.59 (q, 3H, CH.sub.2, 6), 1.73 (water peak), 1.33-1.29 (t, 3H, CH.sub.3, 7).

Example 27

(204) A benzothiazole disperse dye with a structural formula shown below is provided,

(205) ##STR00079##

(206) A synthetic route is:

(207) ##STR00080##

(208) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 3; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 25; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(209) Structural characterization is performed on the obtained benzothiazole disperse dye, and results of hydrogen nuclear magnetic resonance spectrum are:

(210) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.07-8.05 (d, 1H, ArH, 2), 7.98-7.96 (d, 2H, ArH, 4, 4), 7.84-7.82 (d, 1H, ArH, 1), 7.47-7.35 (dt, 2H, ArH, 3, 3), 7.26 (solvent peak), 6.74-6.72 (d, 2H, ArH, 5, 5), 3.52-3.46 (q, 4H, CH.sub.2, 6, 6), 1.65 (water peak), 1.27-1.24 (t, 6H, CH.sub.3, 7, 7).

Example 28

(211) A benzothiazole disperse dye with a structural formula shown below is provided,

(212) ##STR00081##

(213) A synthetic route is:

(214) ##STR00082##

(215) A preparation method of the benzothiazole disperse dye includes the following steps: (1) performing a diazo reaction, wherein conditions were the same as those in step (1) in Example 4; (2) performing a coupling reaction, wherein conditions were the same as those in step (2) in Example 25; (3) dissolving a filter cake obtained in step (2) in a 95% ethanol solution (the filter cake can be dissolved in the ethanol solution), and performing reflux at 70 C. for 2 h, cooling, recrystallization, filtration and drying to obtain a benzothiazole disperse dye.

(216) Structural characterization is performed on the obtained benzothiazole disperse dye, and results (FIG. 18) of hydrogen nuclear magnetic resonance spectrum are:

(217) .sup.1H NMR (400 MHz, CDCl.sub.3) 8.08-8.06 (d, 1H, ArH, 2), 7.96-7.94 (d, 2H, ArH, 4, 4), 7.85-7.83 (d, 1H, ArH, 1), 7.49-7.37 (dt, 2H, ArH, 3, 3), 7.26 (solvent peak), 6.81-6.78 (d, 2H, ArH, 5, 5), 3.94-3.91 (t, 2H, CH.sub.2, 8), 3.66-3.63 (t, 2H, CH.sub.2, 9), 3.60-3.54 (q, 2H, CH.sub.2, 6), 1.58 (water peak), 1.28-1.24 (t, 3H, CH.sub.3, 7).

Comparative Example 1

(218) The alkali resistance, oxidation resistance, washing resistance, rubbing resistance, sunlight resistance and color fastness to sublimation of conventional monoazo disperse dyes (disperse red 2B, disperse yellow BRL and disperse blue BBLS) are shown in Table 1:

(219) TABLE-US-00001 TABLE 1 Related properties of dyes Alkali resistance Oxidation Highest resistance hydrogen Highest Highest NaOH peroxide Dye pH resistant resistant number resistant concentration concentration Washing Rubbing Sunlight Sublimation or name value (g/L) (g/L) resistance resistance resistance resistance Example 1 12 1 5 4-5 4-5 4-5 3-4 2 9 0 0 4 4-5 5 5 3 9 0 0 4-5 4 4-5 4-5 4 9 0 0 4 4-5 4-5 4-5 5 12 3 5 4-5 4-5 6 5 6 12 3 5 4-5 5 7 5 7 9 0 0 4 4-5 6-7 5 8 13 10 5 5 4-5 6 4-5 9 13 10 5 5 5 6-7 4 10 13 10 5 4-5 5 7 4-5 11 13 10 5 5 5 6-7 5 12 12 1 5 4-5 4-5 2-3 4 13 12 1 5 5 4-5 5-6 4 14 12 1 5 4 4 7 4 15 13 1 5 4-5 4-5 3 4 16 13 10 5 4 4 5 4 17 13 1 5 4 4 5 4 18 13 1 5 4 4 5 4 19 9 1 5 4 4 5-6 4-5 20 12 10 5 4 4 5-6 4-5 21 13 10 0 4 4 6 4-5 22 13 10 0 5 5 6 5 23 12 10 0 5 5 6 4-5 24 13 8 5 5 5 3-4 4-5 25 12 8 5 4-5 4-5 3-4 5 26 12 10 5 4-5 4-5 4 4-5 27 12 1 5 4-5 4-5 4 5 28 12 1 5 4-5 4-5 5 5 Comparative Disperse 6 0 0 5 5 7 5 Example red 2B Disperse 6 0 0 4-5 5 4-5 4-5 yellow BRL Disperse 6 0 0 4-5 4-5 6 4-5 blue BBLS Note: A test of color fastness to rubbing, a test of color fastness to washing a test of color fastness to sunlight and a test of color fastness to sublimation are performed based on relevant regulations of GB/T3920.2008 Textiles-Color Fastness Test-Color Fastness to Rubbing, AATCC TM 61-2009 Corlorfastness to Laundering: Accelerated A2, GB/T8427.2008 Textiles-Test for Color Fastness-Color Fastness to Artificial Light: Xenon Arc Fading Lamp Test and GB/T6152-1997 Textiles-Tests for Color Fastness-Color Fastness to Hot Pressing respectively.

(220) By comparing Examples 1-28 and the comparative example in Table 1, it can be seen that among benzothiazole disperse dyes designed and synthesized in Examples 1-28, the color and luster of the disperse dye with the lowest alkali resistance in a dye bath when the pH is 9 are still stable, and the alkali resistance is higher than that of conventional disperse dyes; among the benzothiazole disperse dyes designed and synthesized in Examples 1-28, the oxidation resistance of the benzothiazole disperse dye with the highest pH resistant value greater than or equal to 10 when the pH=10 is higher than that of conventional disperse dyes, and the highest hydrogen peroxide resistant concentration can reach 5 g/L. In addition, various kinds of fastness of the benzothiazole disperse dyes designed and synthesized in Examples 1-28 are excellent.

(221) The benzothiazole heterocyclic azo disperse dyes designed and synthesized in Examples 1-28 have high brightness, bright color, stable luster and other spectral properties; azo alkali-resistant disperse dyes with 2-amino-benzothiazole and derivatives as the diazo component and aniline derivatives as the coupling component are synthesized based on structural design of the dyes, the alkali resistance and oxygen bleaching resistance of the heterocyclic azo disperse dyes can be improved by introducing different groups to the coupling component, an alkali resistance sequence and an oxidation resistance sequence of the disperse dyes after different substituents are introduced are determined, and structural characteristics of the benzothiazole disperse dyes with high alkali resistance and high oxidation resistance are obtained; a reference is provided for structural design of disperse dyes with alkali resistance and oxidation resistance, and disperse dyes capable of meeting requirements of a one-bath process for cotton bleaching and disperse dyeing of a polyester-cotton blended fabric or a one-bath process for alkali deweighting and disperse dyeing of polyester fabrics are determined; besides, according to the method for improving the alkali resistance and oxidation resistance of benzothiazole disperse dyes provided in the examples, compared with conventional dyes, the alkali resistance and oxidation resistance of the disperse dyes are higher; under a dyeing condition of 10 g/L of sodium hydroxide or 5 g/L of hydrogen peroxide, a K/S value of a polyester knitted fabric dyed with these disperse dyes is still stable, and requirements of the one-bath process for cotton bleaching and disperse dyeing of a polyester-cotton blended fabric or the one-bath process for alkali deweighting and disperse dyeing of polyester fabrics for the disperse dyes can be met; a dyeing and finishing process flow of a polyester-cotton blended fabric and a polyester fabric is simplified, requirements of energy saving and emission reduction in the textile industry are met, and good social and economic benefits can be obtained.

(222) Unless otherwise specified, solvents of solutions in the examples are all water.