CN111849194A - Benzisothiazole dye monomer compound, preparation method and application in hydrophobic fiber material dyeing - Google Patents
Benzisothiazole dye monomer compound, preparation method and application in hydrophobic fiber material dyeing Download PDFInfo
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- CN111849194A CN111849194A CN202010730761.8A CN202010730761A CN111849194A CN 111849194 A CN111849194 A CN 111849194A CN 202010730761 A CN202010730761 A CN 202010730761A CN 111849194 A CN111849194 A CN 111849194A
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- monomer compound
- dye monomer
- benzisothiazole
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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
- C09B29/0081—Isothiazoles or condensed isothiazoles
-
- 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
- C09B29/095—Amino naphthalenes
- C09B29/0955—Amino naphthalenes containing water solubilizing groups
-
- 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
-
- 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
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
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- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The invention provides a benzisothiazole dye monomer compound, a preparation method and application in hydrophobic fiber material dyeing, wherein the structure of the benzisothiazole dye monomer compound is shown as a formula (I), and a disperse dye prepared from the benzisothiazole compound. Benzisothiazole dye monomer compound which can be used for dyeing hydrophobic fiber materials and disperse dye prepared from the benzisothiazole compound. The disperse dye provided by the invention has the advantages that the dyeing performance of polyester fiber is obviously improved, the dyeing pH range is wide, the deep dyeing property is good, the rubbing fastness is good, the washing fastness is good, the light fastness is good, and the sublimation fastness is good.
Description
Technical Field
The invention relates to the field of hydrophobic fiber material dyeing, in particular to a benzisothiazole dye monomer compound, a preparation method and application thereof in hydrophobic fiber material dyeing.
Background
Polyester fibers, commonly known as "dacron". The PET fiber is a synthetic fiber obtained by spinning polyester formed by polycondensation of organic dibasic acid and dihydric alcohol, is called PET fiber for short, and belongs to a high molecular compound. The polyester fiber has the advantages of good crease resistance and shape retention, high strength and elastic recovery capability, firmness and durability, crease resistance, no ironing and no hair sticking.
Spandex is a short for polyurethane fiber and is an elastic fiber. The spandex is excellent in elasticity. And the strength is 2-3 times higher than that of the latex yarn, the linear density is thinner, and the latex yarn is more resistant to chemical degradation. The spandex has better acid and alkali resistance, sweat resistance, seawater resistance, dry cleaning resistance and wear resistance.
Polyester and spandex are introduced on a large scale in the market due to their excellent properties. With the development of polyester/spandex blend fibers, the requirements on dyeing of polyester and spandex materials are higher and higher in recent years, and at present, the existing products have some defects from the market situation. Therefore, the development of a class of economic compound dyes with excellent dyeing performance is a main subject of the current dye industry.
Disclosure of Invention
The invention aims to provide a benzisothiazole dye monomer compound and application thereof in dyeing of hydrophobic fiber materials.
A benzisothiazole dye monomer compound has a structure shown as a formula (I):
in formula (I): r1、R2Each independently is C1-4Alkyl, cyanoethyl or cyanoethoxyethyl;
preferably, R1Is C1-2Alkyl groups of (a);
more preferably, the benzisothiazole dye monomer compound is one of the following compounds:
the azo disperse dye can be prepared by adopting a conventional method in the industry, such as:
firstly diazotizing 3-amino-5-nitrobenzothiazole to obtain diazonium salt, and then coupling the diazonium salt with a coupling component shown as a formula (II) to prepare a target product (benzisothiazole dye monomer compound).
Diazotization of 3-amino-5-nitrobenzoisothiazole is carried out according to known methods, for example, diazotization is carried out by slowly adding 3-amino-5-nitrobenzoisothiazole at-10 ℃ to 10 ℃ in a mixed solution of nitrosylsulfuric acid and sulfuric acid to prepare a diazonium salt.
The same coupling process can be carried out according to a known method, the diazonium salt is slowly added into ice water containing the coupling component shown in the formula (II), the reaction is suitably carried out in an acid medium, the temperature range is-10 ℃, after the coupling is finished, the temperature is increased for crystal transformation, and the disperse dye filter cake is obtained by filtering and washing.
When the disperse dye of the present invention is used for dyeing, it is possible to obtain a commercial dye by mixing with one or more of additives such as a naphthalenesulfonic acid-formaldehyde condensate, a lignosulfonate, an alkylnaphthalenesulfonic acid-formaldehyde condensate (e.g., a methylnaphthalenesulfonic acid-formaldehyde condensate (dispersant MF)), a naphthalenesulfonic acid-formaldehyde condensate (dispersant NNO), a benzylnaphthalenesulfonic acid-formaldehyde condensate (dispersant CNF), and sodium lignosulfonates (lignin 85A and lignin 83A), followed by sanding and drying. The mass ratio of the dye monomer compound to the auxiliary agent is preferably 1: 0.5-5.
The benzisothiazole dye monomer compound is mixed with an auxiliary agent and used for dyeing hydrophobic fiber materials. The hydrophobic fiber material is terylene (polyester fiber) and spandex. The mass ratio of the benzisothiazole dye monomer compound to the auxiliary agent is 1: 0.5-5.
A process for the preparation of a dye for dyeing hydrophobic fibre materials, comprising:
adding 100 g of sulfuric acid and 65.8 g of nitrosyl sulfuric acid with the mass percent of 40% into a flask, cooling to 0-5 ℃, adding 39 g of 3-amino-5-nitrobenzothiazole, controlling the temperature to 0-5 ℃ when adding, and keeping the temperature at 0-5 ℃ for 4 hours after adding to obtain a diazo liquid; adding 61.5 g of N-cyanoethyl-N-cyanoethoxyethyl-1-naphthylamine, 24 g of sulfuric acid, peregal and urea into ice water, stirring and pulping for half an hour to form a solution containing a coupling component, dripping diazo liquid into the solution containing the coupling component, controlling the temperature to be 0 ℃ and keeping the coupling component excessive in the process of dripping the diazo liquid, heating to 70 ℃ after the reaction is finished, preserving the temperature for 1 hour, filtering and washing to be neutral to obtain a dye filter cake containing the compound shown in the formula (I-2), then adding 21 g of a dispersing agent, 85A21 g of lignin, water, grinding and dispersing, and spray drying to obtain the dye for dyeing the hydrophobic fiber material;
the finished dye product containing the I-2 dye monomer compound prepared by the method has better washing fastness, light fastness and sublimation fastness.
Compared with the prior art, the invention has the following advantages:
when the benzisothiazole dye monomer compound provided by the invention is applied to dyeing of hydrophobic fiber materials, the benzisothiazole dye monomer compound has the characteristics of wide pH range of separate dyeing, good deep dyeing property, good washing fastness, good light fastness, good sublimation fastness and the like.
Detailed Description
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
example 1
Adding 100 g of sulfuric acid and 65.8 g of nitrosyl sulfuric acid (mass percentage is 40%) into a flask, cooling to below 5 ℃, slowly adding 39 g of 3-amino-5-nitrobenzothiazole, controlling the temperature to be lower than 5 ℃ when adding, and keeping the temperature at 0-5 ℃ for reaction for 4 hours after adding to obtain a diazo liquid; adding 55 g (in hundred weight, formula II structure, R) of N-ethyl-N-cyanoethoxyethyl-1-naphthylamine into a certain amount of ice water1Is ethyl, R2Is cyanoethoxyethyl, i.e.
) 24 g of sulfuric acid, a proper amount of peregal and urea, stirring and pulping for half an hour, dripping the diazo liquid into the coupling component, controlling the temperature to be about 0 ℃ in the process of dripping the diazo liquid and keeping the coupling component excessive,after the reaction is finished, heating to 70 ℃, preserving heat for 1 hour, filtering and washing to be neutral to obtain a dye filter cake of the formula (I-2), then adding an auxiliary agent (dispersing agent MF 20 g, lignin 85A20 g) and water, grinding and dispersing, and spray drying to obtain a finished product.
Example 2
Adding 100 g of sulfuric acid and 65.8 g of nitrosyl sulfuric acid (40%) into a flask, cooling to below 5 ℃, slowly adding 39 g of 3-amino-5-nitrobenzothiazole, controlling the temperature to be lower than 5 ℃ when adding, and keeping the temperature at 0-5 ℃ for reaction for 4 hours after adding to obtain a diazo liquid; adding 52.4 g (in hundred weight) of N-methyl-N-cyanoethoxyethyl-1-naphthylamine, 24 g of sulfuric acid, a proper amount of peregal and urea into a certain amount of ice water, stirring and pulping for half an hour, then dropwise adding diazo liquid into a coupling component, controlling the temperature to be about 0 ℃ in the process of dropwise adding the diazo liquid and keeping the coupling component excessive, heating to 70 ℃ after the reaction is finished, preserving the temperature for 1 hour, filtering and washing to be neutral to obtain a dye filter cake of a formula (I-2), then adding an auxiliary agent (20 g of a dispersing agent MF and 85A20 g of lignin), grinding and dispersing with water, and spray drying to obtain a finished product.
Example 3
Adding 100 g of sulfuric acid and 65.8 g of nitrosyl sulfuric acid (40%) into a flask, cooling to 0-5 ℃, slowly adding 39 g of 3-amino-5-nitrobenzothiazole, controlling the temperature to 0-5 ℃ when adding, and keeping the temperature at 0-5 ℃ for 4 hours after adding to obtain a diazo liquid; adding 61.5 g (in hundred weight) of N-cyanoethyl-N-cyanoethoxyethyl-1-naphthylamine, 24 g of sulfuric acid, a proper amount of peregal and urea into a certain amount of ice water, stirring and pulping for half an hour, then dropwise adding diazo liquid into a coupling component, controlling the temperature to be about 0 ℃ in the process of dropwise adding the diazo liquid, keeping the coupling component excessive, heating to 70 ℃ after the reaction is finished, preserving the temperature for 1 hour, filtering and washing to be neutral to obtain a dye filter cake of a formula (I-2), then adding an auxiliary agent (MF 21 g of a dispersing agent, 85A21 g of lignin), grinding and dispersing water, and spray drying to obtain a finished product.
Example 4
Coupling component (R) with the structure of formula II1Is methyl, R2Cyanoethoxyethyl) instead of the coupling component of the structure of the formula II in example 1, the rest being as in example 1, to give a composition containingThe dye monomer compound of (I-1) is a dye product.
Example 5
Coupling component (R) with the structure of formula II1Is cyanoethyl, R2Cyanoethoxyethyl) was substituted for the coupling component of the structure of the formula II in example 1, and the rest of the procedure was conducted in the same manner as in example 1 to obtain a dye product containing the dye monomer compound of (I-3).
Dyeing application
The commercial dyes prepared in examples 1-5 were used to dye polyester fabrics using a high temperature high pressure process: 0.5 g of the commercial dye is dispersed in 500 ml of water, 20 ml of the commercial dye is absorbed and then mixed with 80 ml of water, the pH value of the dye bath is adjusted to 5 by acetic acid, then the temperature is raised to 70 ℃, 2 g of polyester fiber is added at the same time, the temperature is raised from 70 ℃ to 130 ℃ within 30 minutes, the temperature is kept for 40 minutes, and the commercial dye is taken out after the temperature is lowered.
The dyes prepared in examples 1-3 are respectively tested for rubbing fastness, washing fastness, light fastness and sublimation fastness by using national standards GB/T3920-1997, GB/T3921-2008, GB/T8427-2008 and GB/T5718-1997. The test results are shown in Table 1.
TABLE 1
The data in the table 1 show that the disperse dye has wide pH value application range, good washing fastness, good light fastness and good sublimation fastness, wherein the finished dye product containing the I-2 dye monomer compound has better washing fastness, light fastness and sublimation fastness.
The preferred embodiments of the present invention have been described in detail, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are within the protective scope of the present invention.
Claims (9)
1. A benzisothiazole dye monomer compound is characterized in that the structure is shown as formula (I):
in formula (I): r1、R2Each independently is C1-4Alkyl, cyanoethyl or cyanoethoxyethyl.
2. The benzisothiazole dye monomer compound of claim 1, wherein R is R1Is C1-2Alkyl group of (1).
3. The benzisothiazole dye monomer compound of claim 1, which is one of:
4. the method for preparing a benzisothiazole dye monomer compound according to any one of claims 1 to 3, comprising the steps of:
firstly diazotizing 3-amino-5-nitrobenzothiazole to obtain diazonium salt, and then coupling the diazonium salt with a coupling component shown as a formula (II) to prepare a benzisothiazole dye monomer compound;
wherein R in the formula II1、R2And R in formula (I)1、R2Have the same meaning.
5. The process according to claim 4, wherein the diazotization of 3-amino-5-nitrobenzothiazole comprises:
in the mixed solution of nitrosyl sulfuric acid and sulfuric acid, 3-amino-5-nitrobenzothiazole is added at-10 ℃ for diazotization to prepare diazonium salt.
6. The method of claim 4, wherein the coupling is carried out under reaction conditions selected from the group consisting of: in an acid medium, the temperature is in the range of-10 ℃ to 10 ℃.
7. Use of the benzisothiazole dye monomer compound according to any one of claims 1 to 3 for dyeing hydrophobic fiber materials.
8. The application according to claim 7, comprising in particular: the benzisothiazole dye monomer compound is mixed with an auxiliary agent and used for dyeing hydrophobic fiber materials.
9. The use according to claim 7, wherein the auxiliary agent is at least one of a naphthalene sulfonic acid formaldehyde condensate, a lignosulfonate, an alkyl naphthalene sulfonic acid formaldehyde condensate, a benzyl naphthalene sulfonic acid formaldehyde condensate, and sodium lignosulfonate.
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| CN202010730761.8A CN111849194B (en) | 2020-07-27 | 2020-07-27 | Benzisothiazole dye monomer compound, preparation method and application in hydrophobic fiber material dyeing |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114773289A (en) * | 2022-05-11 | 2022-07-22 | 辽宁庸信达染料化工有限公司 | Nitrobenzoisothiazole azo compound and application thereof |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1425426A (en) * | 1972-06-06 | 1976-02-18 | Eastman Kodak Co | Monoazo compounds and textile materials dyed therewith |
| US3943121A (en) * | 1972-06-06 | 1976-03-09 | Eastman Kodak Company | Monoazo compounds from 3-aminobenzisothiazoles and substituted α-naphthylamine couplers |
| GB1448778A (en) * | 1973-03-19 | 1976-09-08 | Du Pont | Monoazo acid dye for nylon |
| GB1457127A (en) * | 1973-08-22 | 1976-12-01 | Ici Ltd | Disperse monoazo dyestuffs |
| JPS53126034A (en) * | 1977-04-09 | 1978-11-02 | Basf Ag | Acid azo dye |
| DE2805304A1 (en) * | 1978-02-08 | 1979-08-09 | Basf Ag | Azo dyes contg. benzisothiazole di:sulphonic acid gp. - give fast red to green-blue tints on polyamide(s), pelts etc. |
| DE3041838A1 (en) * | 1980-11-06 | 1982-07-01 | Basf Ag, 6700 Ludwigshafen | Dyeing paper with 2,1-benzoisothiazole sulphonic acid azo dyestuff - giving brilliant light-fast dyeing |
| DE3428458A1 (en) * | 1984-08-02 | 1986-02-13 | Basf Ag, 6700 Ludwigshafen | Optical recording medium |
| CN104592782A (en) * | 2014-12-22 | 2015-05-06 | 浙江闰土研究院有限公司 | Azoic disperse dye suitable for dyeing in acidic-alkaline bath as well preparation method and application thereof |
| CN105111775A (en) * | 2015-09-30 | 2015-12-02 | 上海安诺其集团股份有限公司 | Application of azo compound |
-
2020
- 2020-07-27 CN CN202010730761.8A patent/CN111849194B/en active Active
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|---|---|---|---|---|
| GB1425426A (en) * | 1972-06-06 | 1976-02-18 | Eastman Kodak Co | Monoazo compounds and textile materials dyed therewith |
| US3943121A (en) * | 1972-06-06 | 1976-03-09 | Eastman Kodak Company | Monoazo compounds from 3-aminobenzisothiazoles and substituted α-naphthylamine couplers |
| GB1448778A (en) * | 1973-03-19 | 1976-09-08 | Du Pont | Monoazo acid dye for nylon |
| GB1457127A (en) * | 1973-08-22 | 1976-12-01 | Ici Ltd | Disperse monoazo dyestuffs |
| JPS53126034A (en) * | 1977-04-09 | 1978-11-02 | Basf Ag | Acid azo dye |
| DE2805304A1 (en) * | 1978-02-08 | 1979-08-09 | Basf Ag | Azo dyes contg. benzisothiazole di:sulphonic acid gp. - give fast red to green-blue tints on polyamide(s), pelts etc. |
| DE3041838A1 (en) * | 1980-11-06 | 1982-07-01 | Basf Ag, 6700 Ludwigshafen | Dyeing paper with 2,1-benzoisothiazole sulphonic acid azo dyestuff - giving brilliant light-fast dyeing |
| DE3428458A1 (en) * | 1984-08-02 | 1986-02-13 | Basf Ag, 6700 Ludwigshafen | Optical recording medium |
| CN104592782A (en) * | 2014-12-22 | 2015-05-06 | 浙江闰土研究院有限公司 | Azoic disperse dye suitable for dyeing in acidic-alkaline bath as well preparation method and application thereof |
| CN105111775A (en) * | 2015-09-30 | 2015-12-02 | 上海安诺其集团股份有限公司 | Application of azo compound |
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| Title |
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| HIGASHINO, KATSUJI等: "《Effects of substituent groups on photocurrent and photovoltaic power in azo compounds》", 《SENRYO TO YAKUHIN》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114773289A (en) * | 2022-05-11 | 2022-07-22 | 辽宁庸信达染料化工有限公司 | Nitrobenzoisothiazole azo compound and application thereof |
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