CN112442283A - Azo type disperse dye compound suitable for dyeing in acid-alkaline bath, preparation method, composition and application thereof - Google Patents
Azo type disperse dye compound suitable for dyeing in acid-alkaline bath, preparation method, composition and application thereof Download PDFInfo
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- CN112442283A CN112442283A CN201910801402.4A CN201910801402A CN112442283A CN 112442283 A CN112442283 A CN 112442283A CN 201910801402 A CN201910801402 A CN 201910801402A CN 112442283 A CN112442283 A CN 112442283A
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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
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
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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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0079—Azoic dyestuff preparations
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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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/008—Preparations of disperse dyes or solvent dyes
-
- 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
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/36—Material containing ester groups using dispersed dyestuffs
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/82—Textiles which contain different kinds of fibres
- D06P3/8204—Textiles which contain different kinds of fibres fibres of different chemical nature
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Coloring (AREA)
Abstract
An azo-type disperse dye compound suitable for dyeing in an acid-alkaline bath, characterized by having a structure represented by the following formula (I):
in the formula (I), A is selected from 5-nitro-2, 1-benzisothiazolyl, 2, 6-dibromo-4-nitrophenyl, 2, 4-dinitro-6-bromophenyl or2-chloro-4-nitrophenyl; r1、R2Each independently selected from H, C1‑C6Linear or branched alkyl. The disperse dye compound provided by the invention is simple in production process, wide in pH application range, suitable for dyeing in an alkaline dye bath, and has the advantages of higher dye uptake, good lifting performance, excellent perspiration fastness, light fastness and the like.
Description
Technical Field
The invention relates to an azo type disperse dye compound suitable for dyeing in an acid-alkaline bath, a preparation method, a composition and application thereof.
Background
Generally, disperse dyes are mainly used for dyeing polyester fibers, but most disperse dyes can be dyed only in an acid dye bath. At present, the environmental protection situation at home and abroad is very severe, and the dyeing under the alkaline condition can greatly reduce the sewage discharge quantity, reduce the printing and dyeing process and shorten the printing and dyeing time. For example, the pretreatment of textiles requires alkali reduction, and if the alkali reduction and dyeing are carried out simultaneously, on one hand, one process can be saved, the labor cost is saved, and on the other hand, the sewage discharge amount during washing and neutralization is greatly reduced, so that the advantage of alkali dyeing is very obvious.
Disclosure of Invention
The invention aims to provide an azo type disperse dye compound suitable for dyeing in an acid-alkaline bath, which has the advantages of simple production process, wide pH application range, high dye uptake, good lifting performance, excellent perspiration fastness, light fastness and the like, and is suitable for dyeing in an alkaline dye bath.
The technical scheme adopted by the invention is as follows:
an azo-type disperse dye compound suitable for dyeing in an acid-alkaline bath, characterized by having a structure represented by the following formula (I):
in the formula (I), A is selected from 5-nitro-2, 1-benzisothiazolyl, 2, 6-dibromo-4-nitrophenyl, 2, 4-dinitro-6-bromophenyl or 2-chloro-4-nitrophenyl;
R1、R2each independently selected from H, C1-C6Linear or branched alkyl.
Alternatively, R1、R2Each independently selected from the group consisting of H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, isopentyl, 1-ethylpropyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, isohexyl, 1-dimethylbutyl, 2-dimethylbutyl, 3-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 2-methylhexyl, 3-methylhexyl, 2-dimethylpentyl, 3-dimethylpentyl, 2-dimethylpentyl, 3-dimethylpentyl, 2-dimethylpenty, 2, 4-dimethylpentyl, 3-ethylpentyl or 2,2, 3-trimethylbutyl; alternatively, R1、R2Each independently selected from methyl, ethyl, propyl, isopropyl, butyl or isobutyl.
Alternatively, the dye compound represented by formula (I) is selected from the following compounds:
alternatively, the above-mentioned method for preparing an azo-type disperse dye compound suitable for dyeing in an acid-alkaline bath comprises the steps of: diazotizing a diazo component shown in a formula (X) to prepare a diazo liquid, performing coupling reaction on the diazo liquid and a coupling component shown in a formula (Y), stirring until the coupling reaction is finished, filtering, washing with water to be neutral, and drying to obtain a compound shown in a formula (I);
A-NH3(X)
wherein in the formula (X), A is as defined above, and in the formula (Y), R1、R2As described above.
Optionally, in the preparation method, the diazotization reaction temperature is-5-35 ℃, and the reaction time is 3-5 h.
Optionally, in the preparation method, the coupling reaction temperature is 0-10 ℃.
Optionally, the method further comprises a treatment step of slowly heating the reaction solution after the coupling reaction to 60-90 ℃, and preserving heat for 2-5 hours.
Alternatively, the azo type disperse dye compound suitable for dyeing in an acid-alkaline bath according to the present invention may be prepared by:
firstly, adding a certain amount of sulfuric acid (98 percent) and nitrosyl sulfuric acid, optionally adding phosphoric acid or propionic acid when the diazo component is 3-amino-5-nitro-2, 1-benzisothiazole, cooling, slowly adding the diazo component shown in the formula (X), and reacting for 3-5 hours at the temperature of-5-35 ℃ to prepare a diazo liquid; taking a certain amount of ice water, concentrated sulfuric acid (98%), TX-10-2, a coupling component shown in a formula (Y) and sulfamic acid, pulping and dissolving completely, adding crushed ice, cooling to below 0 ℃, then slowly dropping heavy nitrogen liquid at 0-10 ℃, stirring until the coupling reaction is finished, continuing stirring for 2 hours, slowly heating to 60-90 ℃, preserving heat for 2-5 hours, filtering, washing with water to be neutral, and drying.
In another aspect of the present invention, there is provided a disperse dye composition comprising a compound of formula (I) as defined above and optionally an auxiliary.
Optionally, the auxiliary agent is one or more of a dispersing agent and a dispersing agent;
optionally, the auxiliary agent is one or more of a dispersing agent NNO, a dispersing agent CNF, a dispersing agent MF or sodium lignosulfonate.
The preparation method of the disperse dye composition comprises the following steps: and (3) uniformly mixing the compound and the auxiliary agent according to the weight ratio of 1: 0.2-4.5 in the presence of water, grinding, and then performing spray drying to obtain the catalyst.
The auxiliary agent is one or more of a dispersing agent and a dispersing agent.
The auxiliary agent is one or more of a diffusant NNO, a dispersant CNF, a dispersant MF or sodium lignosulfonate.
In another aspect of the present invention, there is provided a use of the above compound of formula (I) or the above disperse dye composition for dyeing polyester fibers or their woven or blended fabrics.
Advantageous effects
The disperse dye provided by the invention obviously improves the dyeing property of polyester fiber, and has the advantages of wide pH value application range, good improvement performance, excellent perspiration fastness, light fastness and the like. Therefore, the disperse dye has high dye-uptake and good reproducibility, and particularly can obtain deep concentration effect and the same dyeing result when dyeing polyester fibers in an acid-to-alkaline dye bath with the pH value of 3.0-11.0. While the common polyester fiber dyed by the disperse dye is only suitable for dyeing in a weak acid bath, and most of the disperse dyes cannot dye deep color.
Detailed Description
Example 1:
adding 180g of sulfuric acid (98%), 40g of phosphoric acid (85%) and 96g of nitrosyl sulfuric acid (28%) into a 250mL flask, adding 40g of 3-amino-5-nitro-2, 1-benzisothiazole (0.205mol) at the temperature of below 5 ℃, and carrying out heat preservation reaction for 4 hours at the temperature of 0-5 ℃ to obtain a diazo solution for later use;
adding 250g of ice water, 20g of 98 g of acid, 2g of TX-10-2 and 43g of 99% N-ethyl-N-chloroethyl m-toluidine (0.205mol) and 1g of sulfamic acid into a 2000mL beaker, pulping, dissolving completely, adding crushed ice, cooling to below 0 ℃, then slowly dropping heavy nitrogen liquid into the coupling component at 0-5 ℃, stirring for 2 hours after the coupling reaction is finished, slowly heating to 60 ℃, preserving heat for 2 hours, filtering, washing with water to neutrality, and drying. The dye compound (I-1) was obtained in a yield of 88.5% in a dry cake of 73.3g, HPLC: 97.34 percent.
Example 2:
adding 30g of sulfuric acid and 39g of nitrosyl sulfuric acid into a 250mL flask, stirring, cooling to 20 ℃, slowly adding 25g of 2, 6-dibromo-4-nitroaniline, and keeping the temperature for 2 hours at 30-35 ℃ after the addition is finished for later use.
Adding 200g of ice water into a 1000mL beaker, starting stirring, slowly adding 20g of 98 acid, 1g of sulfamic acid, 1gTX-10-2, 13.5g of 99% N-ethyl-N-chloroethyl m-toluidine, pulping, dissolving completely, adding crushed ice, cooling to below 0 ℃, then slowly dripping heavy nitrogen liquid into a coupling component at 0-5 ℃, stirring for 2 hours after the coupling reaction is finished, slowly heating to 90 ℃, preserving heat, carrying out crystal transformation for 2 hours, filtering, washing with water to be neutral, preparing a dye monomer (I-2), drying 32.35g of a filter cake, obtaining a yield of 94.92%, and performing HPLC: 98.86 percent.
Example 3:
adding 21g of sulfuric acid and 43.8g of nitrosyl sulfuric acid into a 250mL flask, stirring, cooling to 20 ℃, slowly adding 25g of 2, 4-dinitro-6-bromoaniline, and keeping the temperature at 25-30 ℃ for 2 hours for later use.
Adding 500g of ice water, 20g of 98% acid, 1.5gTX-10-2, 19g of 99% N-ethyl-N-chloroethyl m-toluidine and 1g of sulfamic acid into a 2000mL beaker, pulping and fully dissolving, adding crushed ice, cooling to below 0 ℃, then slowly dripping diazo into a coupling component at the temperature of-5 ℃, stirring for 2 hours after the coupling reaction is finished, slowly heating to 60 ℃, preserving the temperature for 2 hours, filtering, washing with water to be neutral to obtain a dye monomer (I-3), drying 40.85g of a filter cake, obtaining the yield of 90.99%, and HPLC (high performance liquid chromatography) 94.76%
Example 4:
adding 8g of water into a 250mL flask, stirring, adding 21g of sulfuric acid and 53.5g of liquid, keeping the temperature between 20 and 30 ℃, slowly adding 20g of 2-chloro-4-nitroaniline, and preserving the temperature for 2 hours for later use after the adding is finished.
Adding 500g of ice water, 20g of 98 acid, 2gTX-10-2, 23g of 99% N-ethyl-N-chloroethyl m-toluidine and 1g of sulfamic acid into a 2000mL beaker, pulping, fully dissolving, adding crushed ice, cooling to below 0 ℃, then slowly dripping diazo into a coupling component at 0-5 ℃, stirring for 2 hours after the coupling reaction is finished, slowly heating to 60 ℃, preserving heat for 2 hours, filtering, and washing with water to be neutral to obtain the dye monomer (I-4). 42.0g of filter cake is dried, the yield is 95.11 percent, and the HPLC is 96.17 percent
The dye monomers (I-1), (I-2), (I-3) and (I-4) of the above examples 1-4 were tested for their physicochemical properties, and the specific test results are shown in Table 1.
TABLE 1
Dyeing application:
example 5:
50g of dried dye monomer (I-1) from example 1, 70 g of a methylnaphthalenesulfonic acid condensate (dispersant MF) and 70 g of sodium lignosulfonate 85A were mixed, 285 g of water was added, and the mixture was sanded in a sand mill and spray-dried to obtain a dye product 1.
Example 6:
50g of dried dye monomer (I-2) of example 2 were mixed with 70 g of naphthalenesulfonic acid formaldehyde condensate (dispersant NNO) and 70 g of sodium lignosulfonate 85A, 285 g of water was added, and the mixture was subjected to sand milling and spray drying to obtain dye product 2.
Example 7:
50g of dried dye monomer (I-4) from example 4 were mixed with 70 g of naphthalenesulfonic acid formaldehyde condensate (dispersant NNO) and 70 g of sodium lignosulfonate 85A, 285 g of water was added, and the mixture was subjected to sand milling and spray drying to obtain dye product 3.
Example 8:
50g of the dried dye monomer (I-3) from example 3, 70 g of a benzyl naphthalene sulfonic acid formaldehyde condensate (dispersant CNF) and 70 g of sodium lignosulfonate 83A were mixed, 285 g of water was added, and the mixture was sanded in a sand mill and spray-dried to obtain a dye product 4.
Comparative example 1:
prepared according to the method of example 5, except that the dye monomer (I-1) was replaced with the dye monomer (I-5), to prepare a dye preparation 5:
the dye preparations obtained in example 5 and comparative example 1 were subjected to a performance test.
The specific test method is as follows:
0.5 g of dye preparation 1 of example 5 and dye preparation 4 of comparative example 1 were weighed out separately in 500ml of water to prepare a disperse dye suspension. 20ml of disperse dye suspension is sucked and mixed with 80ml of water, the pH value of a dye bath is adjusted to 5 by using acetic acid-sodium acetate buffer solution, then the temperature is raised to 60 ℃, 2g of polyester fiber is respectively added for high-temperature high-pressure dyeing, the temperature is raised to 125 ℃ within 35 minutes, the temperature is kept for 50 minutes, and the sample is taken after the temperature is cooled to 80 ℃.
The applicable range of pH value and the light fastness of the dye products prepared in the example 5 and the comparative example 1 are respectively determined according to the methods of GB/T2403-2014 and GB/T8427-2008, and the test results are shown in Table 2.
TABLE 2 (Unit: grade)
| Name (R) | pH value application range | Color fastness to sunlight |
| Example 5 | 3-11 | 6-7 |
| Comparative example 1 | 3-10 | 5-6 |
Comparative example 2:
prepared according to the method of example 7, except that the dye monomer (I-4) was replaced with the dye monomer (I-6), to prepare a dye preparation 6:
the dye preparations obtained in examples 6 and 7 and comparative example 2 were subjected to a performance test.
The specific test method is as follows:
1.0 g of the dye preparation 2 of example 6, the dye preparation 3 of example 7 and the dye preparation 6 of comparative example 2 were weighed out in 500ml of water, respectively, to prepare a disperse dye suspension. 70ml of disperse dye suspension is sucked and mixed with 30ml of water, the pH value of a dye bath is adjusted to 5 by using acetic acid-sodium acetate buffer solution, then the temperature is raised to 60 ℃, 2g of polyester fiber is respectively added for high-temperature high-pressure dyeing, the temperature is raised to 130 ℃ within 35 minutes, the temperature is kept for 50 minutes, and the sample is taken after the temperature is cooled to 80 ℃.
The pH value application range and the perspiration fastness of the dye products prepared in the examples 6 to 7 and the comparative example 2 are respectively measured according to the methods of GB/T2403-2014 and GB/T3922-2013, and the test results are shown in Table 3.
TABLE 3 (Unit: grade)
| Name (R) | pH value application range | Fastness to perspiration |
| Example 6 | 3-11 | 5 |
| Example 7 | 3-11 | 4-5 |
| Comparative example 2 | 3-10 | 4 |
Comparative example 3:
prepared according to the method of example 8, except that the dye monomer (I-3) was replaced with the dye monomer (I-7), to prepare a dye preparation 7:
the dye preparations obtained in example 8 and comparative example 3 were subjected to a performance test.
The specific test method is as follows:
1.0 g of dye preparation 4 of example 8 and dye preparation 7 of comparative example 3 were weighed out separately in 500ml of water to prepare a disperse dye suspension. 70ml of disperse dye suspension is sucked and mixed with 30ml of water, the pH value of a dye bath is adjusted to 5 by using acetic acid-sodium acetate buffer solution, then the temperature is raised to 60 ℃, 2g of polyester fiber is respectively added for high-temperature high-pressure dyeing, the temperature is raised to 130 ℃ within 35 minutes, the temperature is kept for 50 minutes, and the sample is taken after the temperature is cooled to 80 ℃.
The pH application range and the perspiration fastness of the dye products prepared in the example 8 and the comparative example 3 are respectively determined according to the methods of GB/T2403-2014 and GB/T3922-2013, and the test results are shown in Table 4.
TABLE 4 (Unit: grade)
| Name (R) | pH value application range | Fastness to perspiration |
| Example 8 | 3-10 | 5 |
| Comparative example 3 | 3-9 | 4 |
In conclusion, the disperse dye compound provided by the invention is simple in production process, wide in pH application range, suitable for dyeing in an alkaline dye bath, and has the advantages of high dye uptake, good lifting performance, excellent perspiration fastness, light fastness and the like.
Claims (10)
1. An azo-type disperse dye compound suitable for dyeing in an acid-alkaline bath, characterized by having a structure represented by the following formula (I):
in the formula (I), A is selected from 5-nitro-2, 1-benzisothiazolyl, 2, 6-dibromo-4-nitrophenyl, 2, 4-dinitro-6-bromophenyl or 2-chloro-4-nitrophenyl;
R1、R2each independently selected from H, C1-C6Linear or branched alkyl.
2. Azo-type disperse dyes suitable for dyeing in acid-alkaline baths according to claim 1, characterized in that R1、R2Each independently selected from H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, sec-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, isopentyl, 1-ethylpropyl, neopentylN-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, isohexyl, 1-dimethylbutyl, 2-dimethylbutyl, 3-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 2-methylhexyl, 3-methylhexyl, 2-dimethylpentyl, 3-dimethylpentyl, 2, 4-dimethylpentyl, 3-ethylpentyl or 2,2, 3-trimethylbutyl; alternatively, selected from methyl, ethyl, propyl, isopropyl, butyl or isobutyl.
3. Azo-type disperse dyes suitable for dyeing in acid-alkaline baths according to claim 1, characterized in that the dye compounds of formula (I) are selected from the following compounds:
4. a method for preparing the azo type disperse dye compound suitable for dyeing in an acid-alkaline bath according to claims 1 to 3, comprising the steps of: diazotizing a diazo component shown in a formula (X) to prepare a diazo liquid, performing coupling reaction on the diazo liquid and a coupling component shown in a formula (Y), stirring until the coupling reaction is finished, filtering, washing with water to be neutral, and drying to obtain a compound shown in a formula (I);
A-NH3(X)
wherein in formula (X), A is as defined in any one of claims 1 to 3, and in formula (Y), R1、R2The method according to any one of claims 1 to 3.
5. The preparation method according to claim 4, wherein the diazotization reaction temperature is-5-35 ℃, and the reaction time is 3-5 h.
6. The method according to claim 4 or 5, wherein the coupling reaction temperature is 0 to 10 ℃.
7. The preparation method according to any one of claims 4 to 6, further comprising a treatment step of slowly raising the temperature of the reaction solution after the coupling reaction to 60 to 90 ℃ and maintaining the temperature for 2 to 5 hours.
8. A disperse dye composition, comprising a compound of the formula (I) as claimed in any of claims 1 to 3 and optionally auxiliaries.
9. A disperse dye composition according to claim 8, wherein: the auxiliary agent is one or more of a dispersing agent and a dispersing agent;
optionally, the auxiliary agent is one or more of a dispersing agent NNO, a dispersing agent CNF, a dispersing agent MF or sodium lignosulfonate.
10. Use of a compound of formula (I) according to any one of claims 1 to 3 or a disperse dye composition according to claim 8 for dyeing polyester fibers or their woven or blended fabrics.
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