CN111500084A - Nitrobenzoisothiazole-pyridone dye and preparation method thereof - Google Patents
Nitrobenzoisothiazole-pyridone dye and preparation method thereof Download PDFInfo
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- CN111500084A CN111500084A CN202010342474.XA CN202010342474A CN111500084A CN 111500084 A CN111500084 A CN 111500084A CN 202010342474 A CN202010342474 A CN 202010342474A CN 111500084 A CN111500084 A CN 111500084A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
- C09B29/0074—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms
- C09B29/0077—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing nitrogen and sulfur as heteroatoms containing a five-membered heterocyclic ring with one nitrogen and one sulfur as heteroatoms
- C09B29/0085—Thiazoles or condensed thiazoles
- C09B29/0088—Benzothiazoles
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3639—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more amino groups
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
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- Textile Engineering (AREA)
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Abstract
The invention discloses a nitrobenzoisothiazole-pyridone dye and a preparation method thereof, belonging to the technical field of heterocyclic dye synthesis. The invention provides a synthesis strategy through functional group conversion, which adopts alkaline methoxypropylamine to replace the hydroxyl of pyridone, thereby removing active hydroxyl protons in the pyridone and solving the problem of poor stability of the nitrobenzoisothiazole-pyridone heterocyclic dye under the acidic condition. Research shows that the nitrobenzoisothiazole-pyridone dye has strong acid resistance, and the UV-Vis spectrum of the dye can keep good stability under the acidic condition without red shift or blue shift.
Description
Technical Field
The invention relates to a nitrobenzoisothiazole-pyridone dye and a preparation method thereof, belonging to the technical field of heterocyclic dye synthesis.
Background
Compared with the traditional benzene ring azo disperse dye, the heterocyclic disperse dye has more bright color and higher color development intensity. They have a wide range of applications not only in the textile industry for dye colorants but also play an important role in the electronics industry, such as non-linear optics, visual sensors and dye-sensitized cells. Wherein, the heterocyclic dye synthesized by taking the pyridine-2, 6-diketone and the derivative thereof as the coupling component has very bright color and excellent various fastness properties.
The study shows that nitro-benzisothiazole-pyridone heterocyclic Dyes synthesized by using 3-amino-5-nitro-benzisothiazole as a diazo component and pyridine-2, 6-dione as a coupling component have azo-hydrazone tautomerism due to the migration of active protons under the induction of an acidic environment, and are converted into hydrazone structures under the acidic condition, the azo-hydrazone tautomerism is caused to present bright yellow, red and blue under the induction of solvents with different polarities, however, when the Dyes are used for dyeing fibers, the Dyes usually have an acidic condition, which means that the dyeing stability is reduced due to the azo-hydrazone tautomerism of the Dyes in the dyeing process, the most probable reason for the phenomenon is that the active hydroxyl protons exist in the coupling component pyridine-2, 6-dione, which can generate the reversible migration of azo moieties and pyridone rings under the acidic condition (as shown in the following reaction formula), the dye forms a complex with the dye in a mode of a transition metal, Buckoo, Bu.
Disclosure of Invention
Aiming at the problems, the invention provides a nitrobenzoisothiazole-pyridone dye and a preparation method thereof, the invention realizes that the acidic hydroxyl of pyridine-2, 6-diketone is replaced by basic amino by a functional group conversion mode, and the method can improve the acid stability of the pyridone heterocyclic dye by removing active protons, thereby eliminating the problem of unstable dyeing caused by tautomerism.
The invention provides a nitrobenzoisothiazole-pyridinone dye, the molecular structural formula of which is shown in formula I:
in the formula, R1Is- [ CH ]2]n-O-CH3N is 3 to 8; r2Selected from hydrogen, C1～8Alkyl, hydroxyalkyl, alkoxyalkyl, phenyl.
A second object of the present invention is to provide a process for preparing the above-mentioned nitrobenzoisothiazole-pyridone dye, which proceeds by the following reaction scheme:
in the formula, R1Is- [ CH ]2]n-O-CH3N is 3 to 8; r2Selected from hydrogen, C1～8Alkyl, hydroxyalkyl, alkoxyalkyl, phenyl.
In one embodiment of the present invention, the method for preparing the above nitrobenzoisothiazole-pyridone dye comprises the following steps:
(1) 1-N-R2Dissolving 3-cyano-4-methyl-6-hydroxy-2-pyridone in phosphorus oxychloride, heating, washing a reaction product after the reaction is finished, dissolving the product by using dichloromethane, separating, drying and filtering the organic phase obtained by separation, collecting the filtrate, removing the solvent, and finally purifying to obtain a compound (i);
(2) Dissolving the compound (i) in absolute ethanol, adding NH2-(CH2)n-O-CH3(n is 3-8) and heating, removing the solvent in the reaction product after the reaction is finished, and finally purifying to obtain a compound (ii);
(3) dissolving 3-amino-5-nitro-2, 1-benzisothiazole in concentrated sulfuric acid and glacial acetic acid to obtain a mixed solution, dissolving sodium nitrite in water, adding the mixed solution, and stirring to obtain diazonium salt; dissolving the compound (ii) in a methanol-water mixed solution to obtain a compound (ii) mixed solution;
(4) adding the obtained diazonium salt into the mixed solution of the compound (ii) and stirring, heating and aging reaction mother liquor after the reaction is finished, then filtering, and washing with water to obtain a crude product;
(5) and dissolving the crude product by using an organic solvent, heating and refluxing, and cooling to room temperature to precipitate crystals to obtain a final product.
In one embodiment of the present invention, the 1-N-R in step (1)2-3-cyano-4-methyl-6-hydroxy-2-pyridone with the phosphorus oxychloride in a molar ratio of 1: 2-1: 2.2, the heating temperature is 80-100 ℃.
In one embodiment of the present invention, the washing in step (1) is washing of the reaction product with an ice-water mixture.
In one embodiment of the invention, the separation in step (1) is carried out by transferring to a separatory funnel for extraction.
In one embodiment of the present invention, the drying in step (1) is drying with anhydrous sodium sulfate and standing for 5 to 10 minutes, and the solvent is removed by a rotary evaporator.
In one embodiment of the present invention, said compound (i) and said NH in step (2)2-(CH2)n-O-CH3In a molar ratio of 1: 2-1: 2.2, the heating temperature is 80-100 ℃.
In one embodiment of the invention, the molar ratio of the 3-amino-5-nitro-2, 1-benzisothiazole to the sodium nitrite to the compound (ii) in step (3) is 1: 1.1: 1.
in one embodiment of the invention, the volume ratio of the glacial acetic acid to the concentrated sulfuric acid in the step (3) is 1: 1-1: 1.5, the stirring time is 20-40 minutes, and the volume ratio of methanol to water in the methanol-water mixed solvent is 2: 1.
In one embodiment of the present invention, the diazonium salt and the compound (ii) are mixed in step (4) in a molar ratio of 1: 1-1: 1.2.
in one embodiment of the present invention, the heating temperature in the step (4) is 45 to 65 ℃ and the aging time is 10 to 20 minutes.
In one embodiment of the present invention, the organic solvent in step (5) is any one of a chloroform-ethanol mixed solvent, a chloroform-methanol mixed solvent, and a dichloromethane-ethanol mixed solvent.
In an embodiment of the present invention, a volume ratio of chloroform to ethanol in the chloroform-ethanol mixed solvent is 1:1, a volume ratio of chloroform to methanol in the chloroform-methanol mixed solvent is 1:1, and a volume ratio of dichloromethane to ethanol in the dichloromethane-ethanol mixed solvent is 1: 1.
In one embodiment of the present invention, the heating temperature in step (5) is 50 to 70 ℃ and the reflux time is 30 to 60 minutes.
In one embodiment of the present invention, the purification in step (1) and step (2) is performed by using a chromatographic column.
In one embodiment of the present invention, the column chromatography in step (1) uses silica gel filler as stationary phase and ethyl acetate-petroleum ether eluent as mobile phase to perform column chromatography purification, wherein the volume ratio of ethyl acetate to petroleum ether is 1: 1; and (3) performing column chromatography purification by using the column chromatography in the step (2) by using a silica gel filler as a stationary phase and using a dichloromethane-methanol eluent as a mobile phase, wherein the volume ratio of dichloromethane to methanol is 80: 1.
A third object of the present invention is to provide a dye colorant in the textile industry, which dye colorant comprises the above-mentioned nitrobenzoisothiazole-pyridone dye.
A fourth object of the present invention is to provide the use of the above-mentioned nitrobenzoisothiazole-pyridone dye in nonlinear optical devices, visual sensors and dye-sensitized cells.
The invention has the beneficial effects that:
(1) according to the invention, alkaline amine groups are adopted to modify the hydroxyl groups of the pyridone in a functional group conversion mode, then the modified pyridone is taken as a coupling component, and 3-amino-5-nitro-2, 1-benzisothiazole is taken as a diazo component, so that the bis-heterocyclic azo dye stable to an acidic environment is synthesized. Under the induction of different acid environments, the dye molecules synthesized by functional group conversion do not have azo-hydrazone tautomerism due to the absence of active hydroxyl protons, and have good acid stability.
(2) The invention has the advantages of easily controlled reaction conditions, convenient operation and high product yield.
Drawings
FIG. 1 is a nuclear magnetic hydrogen spectrum of Compound I-1 prepared in example 1.
FIG. 2 is a mass spectrum of Compound I-1 prepared in example 1.
FIG. 3 is a graph of UV-Vis absorption spectra of compound I-1 prepared in example 1 under different acidic environments.
FIG. 4 is a nuclear magnetic hydrogen spectrum of Compound I-2 prepared in example 2.
FIG. 5 is a mass spectrum of Compound I-2 prepared in example 2.
FIG. 6 is a graph of UV-Vis absorption spectra of compound I-2 prepared in example 2 under different acidic environments.
Detailed Description
The present invention will be described in further detail with reference to the following examples.
Example 1
Preparation of Compound I-1:
(1) dissolving 10.00mmol of 1-N-ethyl-3-cyano-4-methyl-6-hydroxy-2-pyridone in 21.60mmol of phosphorus oxychloride, heating at 80 ℃, monitoring reaction by T L C, washing a reaction product with an ice water mixture, fully dissolving the reaction product with dichloromethane, transferring the obtained product into a separating funnel for extraction, drying an organic phase obtained by separation for 5 minutes by using anhydrous sodium sulfate, filtering, collecting filtrate, removing a solvent by using a rotary evaporator to obtain a red crude product, using 60.00g of silica gel filler as a stationary phase, using 500.00ml of ethyl acetate-petroleum ether (wherein the volume ratio of ethyl acetate to petroleum ether is 1:1) eluent as a mobile phase, and performing column chromatography on the crude product to obtain a compound (i-1) with the yield of 84%;
(2) dissolving 5.00mmol of compound (i-1) in 25.00ml of absolute ethanol, adding 11.00mmol of 3-methoxypropylamine and heating at 90 ℃, monitoring the completion of the reaction by T L C, removing the solvent from the product by a rotary evaporator to obtain a crude product, and purifying the crude product by column chromatography using 40.00g of silica gel filler as a stationary phase and 300.00ml of dichloromethane-methanol (wherein the volume ratio of dichloromethane to methanol is 80:1) eluent as a mobile phase to obtain compound (ii-1) in 78% yield;
(3) dissolving 10.00mmol of 3-amino-5-nitro-2, 1-benzisothiazole with 5.00ml of 98% concentrated sulfuric acid and 5.00ml of glacial acetic acid to obtain a mixed solution, dissolving 11.00mmol of sodium nitrite with 5.00ml of deionized water, adding the dissolved solution into the mixed solution, and stirring for 30 minutes to obtain diazonium salt; dissolving 10.00mmol of compound (ii-1) in 60.00ml of a mixed solvent of methanol and water (wherein the volume ratio of methanol to water is 2:1) to obtain a mixed solution of compound (ii-1);
(4) adding all the obtained diazonium salts into the mixed solution of the compound (ii-1), stirring, monitoring the completion of the reaction through T L C, heating and aging the reaction mother liquor at 55 ℃ for 10 minutes, filtering, and washing with water to obtain a crude product;
(5) dissolving the crude product with 20.00ml of chloroform-ethanol (wherein the volume ratio of chloroform to ethanol is 1:1), heating and refluxing at 60 ℃ for 45 minutes, cooling to room temperature to precipitate crystals, and obtaining the compound I-1 with the yield of 82%.
The preparation process comprises the following steps:
the nuclear magnetic resonance spectroscopy of the compound prepared in this example was carried out, and FIG. 1 is a nuclear magnetic hydrogen spectrum of the compound I-1 prepared in example 1, from which it can be confirmed that the final product was obtained.
1H NMR(300MHz,CDCl3，ppm)：＝12.55(s,1H),8.96(s,1H),8.21(d,J＝9.7Hz,1H),7.76(d,J＝9.7Hz,1H),4.39-4.27(m,2H),4.06-3.95(m,2H),3.70(t,J＝5.3Hz,2H),3.33(s,3H),2.73(s,3H),2.28(dd,J＝11.2,5.6Hz,2H),1.46(t,J＝7.0Hz,3H).NegativeESI–MS in methanol:(m/z)＝454.15(100％),[M-H]-。
FIG. 2 is an ESI-MS diagram of Compound I-1 prepared in this example, and from FIG. 2 it can be seen that the molecular ion peak of the compound appears at 100% abundance using the negative ion mode in the methanol solvent, indicating that this method is effective in analyzing the molecular structure of the heterocyclic pyridone dye.
Acid stability test:
the prepared concentration is 3.0 × 10-5Firstly, testing the UV-Vis absorption spectrum (pH is equal to the absorption line of 6.77) of a methanol solution of the compound I-1, then dropwise adding a methanol solution of 0.1 mol/L acetic acid into a methanol solution of the compound I-1, and testing the pH value and the UV-Vis absorption spectrum (pH is equal to the absorption line of 1.35,3.47 and 6.77), as shown in figure 3, and as can be seen from figure 3, the maximum absorption wavelength of the compound I-1 synthesized by the functional group conversion mode is 549nm and does not change along with the change of the external acid environment, the dye is proved to have high acid stability.
Example 2
Preparation of Compound I-2:
(1) dissolving 10.00mmol of 1-N-isopropoxypropyl-3-cyano-4-methyl-6-hydroxy-2-pyridone in 21.60mmol of phosphorus oxychloride, heating at 80 ℃, monitoring reaction by T L C, washing a reaction product with an ice water mixture, fully dissolving the reaction product with dichloromethane, transferring the obtained product into a separating funnel for extraction, drying an organic phase obtained by separation for 5 minutes by using anhydrous sodium sulfate, filtering, collecting filtrate, removing a solvent by using a rotary evaporator to obtain a red crude product, using 60.00g of a silica gel filler as a stationary phase, using 500.00ml of ethyl acetate-petroleum ether (wherein the volume ratio of ethyl acetate to petroleum ether is 1:1) eluent as a mobile phase, and performing column chromatography on the crude product to obtain a compound (i-2) with the yield of 90%;
(2) dissolving 5.00mmol of the compound (i-2) in 25.00ml of absolute ethanol, adding 11.00mmol of 3-methoxypropylamine and heating at 90 ℃, after monitoring the reaction by T L C, removing the solvent from the product by a rotary evaporator to obtain a crude product, and purifying the crude product by column chromatography using 40.00g of silica gel filler as a stationary phase and 300.00ml of dichloromethane-methanol (wherein the volume ratio of dichloromethane to methanol is 80:1) eluent as a mobile phase to obtain the compound (ii-2) with a yield of 80%;
(3) dissolving 10.00mmol of 3-amino-5-nitro-2, 1-benzisothiazole with 5.00ml of 98% concentrated sulfuric acid and 5.00ml of glacial acetic acid to obtain a mixed solution, dissolving 11.00mmol of sodium nitrite with 5.00ml of deionized water, adding the dissolved solution into the mixed solution, and stirring for 30 minutes to obtain diazonium salt; dissolving 10.00mmol of compound (ii-2) in 60.00ml of a mixed solvent of methanol and water (wherein the volume ratio of methanol to water is 2:1) to obtain a mixed solution of compound (ii-2);
(4) adding all the obtained diazonium salts into the mixed solution of the compound (ii-2), stirring, monitoring the completion of the reaction through T L C, heating and aging the reaction mother liquor at 55 ℃ for 10 minutes, filtering, and washing with water to obtain a crude product;
(5) dissolving the crude product with 20.00ml of chloroform-ethanol (wherein the volume ratio of chloroform to ethanol is 1:1), heating and refluxing at 60 ℃ for 45 minutes, cooling to room temperature to precipitate crystals, and obtaining the compound I-2 with the yield of 85%.
The preparation process comprises the following steps:
the nuclear magnetic resonance spectrum of the compound prepared in this example was subjected to nuclear magnetic resonance testing, and FIG. 4 is a nuclear magnetic hydrogen spectrum of the compound I-2 prepared in example 2, from which it could be confirmed that the final product was obtained.
1H NMR(400MHz,CDCl3，ppm)：＝12.69(s,1H),8.98(d,J＝1.7Hz,1H),8.20(dd,J＝9.7,2.3Hz,1H),7.77-7.73(m,1H),4.44-4.37(m,2H),4.06(dd,J＝11.2,6.5Hz,2H),3.69-3.64(m,2H),3.58-3.47(m,3H),3.30(s,3H),2.71(s,3H),2.24(dd,J＝11.6,6.0Hz,2H),2.03(dd,J＝13.1,7.4Hz,2H),1.14(d,J＝6.1Hz,6H).Negative ESI–MS inmethanol:(m/z)＝526.25(100％),[M-H]-。
FIG. 5 is an ESI-MS graph of Compound I-2 prepared in this example, and from FIG. 5 it can be seen that the molecular ion peak of the compound appears at 100% abundance using the negative ion mode in the methanol solvent, indicating that this method is effective in analyzing the molecular structure of the heterocyclic pyridone dye.
Acid stability test:
the prepared concentration is 3.0 × 10-5Firstly, testing the UV-Vis absorption spectrum (pH 7.01 absorption line) of the methanol solution of the compound I-2, then dropwise adding the methanol solution of 0.1 mol/L acetic acid into the methanol solution of the compound I-2, and testing the pH value and the UV-Vis absorption spectrum (pH 1.25,4.52,7.01 absorption line), as shown in figure 6. from figure 6, the compound I-2 synthesized by the functional group conversion mode has the maximum absorption wavelength at 555nm and does not change along with the change of the external acid environment, and the dye is proved to have high acid stability.
Although the present invention has been described with reference to the preferred embodiments, it should be understood that various changes and modifications can be made therein by those skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (10)
1. The nitrobenzoisothiazole-pyridone dye is characterized in that the molecular structural formula of the nitrobenzoisothiazole-pyridone dye is shown as a formula I:
in the formula, R1Is- [ CH ]2]n-O-CH3N is 3 to 8; r2Selected from hydrogen, C1～8Alkyl, hydroxyalkyl, alkoxyalkyl, phenyl.
2. A process for preparing a nitrobenzoisothiazole-pyridone dye according to claim 1, by the reaction:
in the formula, R1Is- [ CH ]2]n-O-CH3N is 3 to 8; r2Selected from hydrogen, C1～8Alkyl, hydroxyalkyl, alkoxyalkyl, phenyl.
3. The method of claim 2, wherein the method of preparing the nitrobenzothiazole-pyridone dye comprises the steps of:
(1) 1-N-R2Dissolving 3-cyano-4-methyl-6-hydroxy-2-pyridone in phosphorus oxychloride, heating, washing a reaction product after the reaction is finished, dissolving the product by using dichloromethane, separating, drying and filtering the organic phase obtained by separation, collecting the filtrate, removing the solvent, and finally purifying to obtain a compound i;
(2) dissolving compound i in absolute ethyl alcohol, adding NH2-(CH2)n-O-CH3N is 3-8, heating, removing the solvent in the reaction product after the reaction is finished, and finally purifying to obtain a compound ii;
(3) dissolving 3-amino-5-nitro-2, 1-benzisothiazole in concentrated sulfuric acid and glacial acetic acid to obtain a mixed solution, dissolving sodium nitrite in water, adding the mixed solution, and stirring to obtain diazonium salt; dissolving a compound ii in a methanol-water mixed solution to obtain a compound ii mixed solution;
(4) adding the obtained diazonium salt into the mixed solution of the compound ii, stirring, heating, aging after the reaction is finished, filtering, and washing with water to obtain a crude product;
(5) and dissolving the crude product by using an organic solvent, heating and refluxing, and cooling to room temperature to precipitate crystals to obtain a final product.
4. The method according to claim 3, wherein the 1-N-R in the step (1)2-3-cyano-4-methyl-6-hydroxy-2-pyridone with the phosphorus oxychloride in a molar ratio of 1: 2-1: 2.2, the heating temperature is 80-100 ℃.
5. The method according to claim 3, wherein the compound i and the NH in step (2)2-(CH2)n-O-CH3In a molar ratio of 1: 2-1: 2.2, the heating temperature is 80-100 ℃.
6. The production method according to claim 3, wherein the molar ratio of the 3-amino-5-nitro-2, 1-benzisothiazole to the sodium nitrite to the compound ii in step (3) is 1: 1.1: 1.
7. the method according to claim 3, wherein the diazonium salt and the compound ii are mixed in the step (4) at a molar ratio of 1: 1-1: 1.2.
8. the production method according to claim 3, wherein the organic solvent in step (5) is any one of a chloroform-ethanol mixed solvent, a chloroform-methanol mixed solvent, and a dichloromethane-ethanol mixed solvent.
9. A dye colorant in the textile industry, characterized in that it contains the nitrobenzoisothiazole-pyridone dye according to claim 1.
10. Use of a nitrobenzoisothiazole-pyridone dye as claimed in claim 1 in non-linear optics, visual sensors and dye-sensitized cells.
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