CN111040466B - Trisazo red acid dye and preparation method thereof - Google Patents
Trisazo red acid dye and preparation method thereof Download PDFInfo
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- CN111040466B CN111040466B CN201911362874.0A CN201911362874A CN111040466B CN 111040466 B CN111040466 B CN 111040466B CN 201911362874 A CN201911362874 A CN 201911362874A CN 111040466 B CN111040466 B CN 111040466B
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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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/35—Trisazo dyes in which the tetrazo component is a diamino-azo-aryl compound
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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
- D06P1/39—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 acid dyes
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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
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/06—Material containing basic nitrogen containing amide groups using acid dyes
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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
- 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid dyes
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Abstract
The invention discloses a trisazo red acid dye and a preparation method thereof, wherein the preparation method comprises the following steps: reacting diaminoazobenzene, hydrochloric acid and a sodium nitrite solution in water, and eliminating residual nitrous acid after reaction to obtain a diazonium salt solution; reacting the reaction raw materials with a diazonium salt solution to finally obtain the corresponding trisazo red acid dye; the reaction raw materials are N-ethyl-N-benzylaniline-3 '-sulfonic acid and N-ethyl-N-benzyl m-toluidine-3' -sulfonic acid. The trisazo red acid dye does not contain carcinogenic dye and heavy metal dye, and belongs to safe and environment-friendly dye. The dye has good water solubility, can be smoothly dyed in a dyeing system, has good level dyeing property, can be efficiently combined with protein and polyamide fibers, has high dye-uptake, has excellent color fastness after being dyed, and is an ideal substitute of metal complex dyes.
Description
Technical Field
The invention belongs to the field of chemical industry; in particular to a novel red acid dye (trisazo red acid dye) and a preparation method and application thereof.
Background
The acid dye is also called anion dye, which contains acid groups in dye molecules, can be combined with amino groups in protein fibers and polyamide molecules by ionic bonds and is suitable for acidic, weak acid or neutral conditions. The acid dye is a main dye for printing and dyeing wool and polyamide fibers, occupies about 95 percent of China, is widely used in the fields of daily chemicals, ink, wood, leather and the like, and is an important dye with wide application range.
Along with the improvement of living standard of people, the quality requirement of the fabric is more and more strict, one of the quality indexes is color fastness, and the color fastness of the dyed fabric directly reflects the grade of the fabric to determine the price and the sale of the fabric. The color fastness of the fabric is mainly determined by two aspects, namely the color fastness of the dye for dyeing and the dyeing process during dyeing. The traditional high-fastness dye mostly adopts metal complex dye, so that the production process faces huge pollution of heavy metal, huge waste water containing heavy metal is generated in the printing and dyeing process, and the residual heavy metal of the printed and dyed fabric can also cause unpredictable damage to human bodies. Therefore, dyes containing no heavy metal and having good color fastness and good dyeing degree are very popular, and especially in developed countries such as europe and the united states, the demand for such dyes is continuously increasing. Develops a novel high-fastness acid dye, and accords with the industry development trend.
The date red is an important variety in red, provides dark blue light red tone, and has the following characteristics:
acid jujube red MB (c.i. acid violet 90):
neutral purplish red GRL (c.i. acid red 213):
acid red SB (c.i. acid red 405):
the three jujube red acid dyes are all metal complex dyes, have excellent color fastness and very wide application, and are not environment-friendly and have a lot of application limitations because the three jujube red acid dyes are metal complex dyes.
Disclosure of Invention
The invention aims to provide a novel red acid dye, namely a trisazo red acid dye and a preparation method thereof.
In order to solve the technical problems, the invention provides a trisazo red acid dye, which has a structural general formula as follows:
r1 and R2 are-C2H5A group;
r3 and R4 are H or-CH3A group;
m is H or an alkali metal cation.
The structural formula of the improved trisazo red acid dye is any one of the following:
dye I-1:
r1 is-C2H5Group, R2 is-C2H5Group, R3 is a H group, R4 is a H group, M is H or an alkali metal cation.
Dye I-2:
r1 is-C2H5Group, R2 is-C2H5Group, R3 is-CH3Group, R4 is-CH3The radical, M is H or an alkali metal cation.
The invention also provides a preparation method of the trisazo red acid dye, which comprises the following steps:
1) adding p-diaminoazobenzene (CAS NO. 538-41-0) into water, uniformly stirring, adding hydrochloric acid (mass fraction is 31%) and uniformly stirring, cooling to 0-5 ℃, dropwise adding a sodium nitrite solution (mass fraction is 30%) to form a reaction system I, controlling the temperature of the reaction system I not to exceed 5 ℃ in the dropwise adding process, stirring and reacting at 0-5 ℃ for 2 +/-0.2 hours after dropwise adding is finished, and then eliminating residual nitrous acid after reaction to obtain a diazonium salt solution;
p-diaminoazobenzene: hydrochloric acid 1: a molar ratio of 5.0;
p-diaminoazobenzene: sodium nitrite 1: a molar ratio of 2.05;
description of the drawings: in the reaction process, detecting that no color is developed as a reaction end point by using an Ehrlich reagent;
using sulfamic acid to destroy redundant nitrous acid, and taking starch potassium iodide test paper as a standard that the starch potassium iodide test paper does not turn blue;
2) adding reaction raw materials into water, uniformly stirring, adjusting the pH value to 7.0-8.0 (the pH value can be adjusted by using soda ash), cooling to 0-5 ℃, dropwise adding the diazonium salt solution obtained in the step 1) to form a reaction system II, controlling the temperature of the reaction system II to be not more than 10 ℃ in the dropwise adding process, always adjusting the pH value of the reaction system II to 7.0-8.0 in the dropwise adding process, and reacting at 5-10 ℃ for 3 +/-0.3 hours after the dropwise adding is finished; reaction raw materials: the diaminoazobenzene in step 1) is 2 to 2.1:1.0 (preferably 2.02: 1.0) of the molar ratio;
after the reaction is finished, adding sodium chloride to generate a precipitate, filtering, and drying a filter cake to obtain a product;
when the reaction raw material is N-ethyl-N-benzylaniline-3' -sulfonic acid (CAS No. 101-11-1), the obtained product is dye I-1;
when the reaction raw material is N-ethyl-N-benzyl m-toluidine-3' -sulfonic acid, the obtained product is the dye I-2.
As an improvement of the preparation method of the trisazo red acid dye of the present invention:
in the step 1), 200. + -.50 g of water is used per 0.1mol of p-diaminoazobenzene.
As a further improvement of the preparation process of the trisazo red acid dye of the present invention:
in the step 2) of the said step,
300-400 g of water is matched with every 2-2.1 mol of reaction raw materials;
drying for 24 hours at the temperature of 80-90 ℃.
The trisazo red acid dye obtained by the invention is judged as a red dye according to a Panton international standard color card as a reference basis.
Based on a large number of experiments, the inventor surprisingly found that the trisazo red acid dye of the invention has excellent color fastness, does not contain heavy metal structures and carcinogenic structures, and can replace the three jujube red acid dyes in the prior art.
In conclusion, the trisazo red acid dye does not contain carcinogenic dye and heavy metal dye, and belongs to safe and environment-friendly dye. The dye has good water solubility, can be smoothly dyed in a dyeing system, has good level dyeing property, can be efficiently combined with protein and polyamide fibers, has high dye-uptake, has excellent color fastness after being dyed, and is an ideal substitute of metal complex dyes.
Detailed Description
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
in the following case, the stirring speed is 30 to 200 rpm.
Example 1, a process for the preparation of a trisazo red acid dye i-1, successively following steps:
1) starting stirring in a reactor provided with a stirring device, adding 200g of water, adding 0.1mol (about 21.23g) of p-diaminoazobenzene, adding 0.5mol of hydrochloric acid (31% by mass), adding ice, cooling to 0-5 ℃, dropwise adding a sodium nitrite solution (30% by mass) containing 0.205mol of sodium nitrite, controlling the temperature of the reaction system to be not more than 5 ℃ in the dropwise adding process, turning the starch potassium iodide test paper to blue, reacting for 2 hours at 0-5 ℃ (using an ehrlichia reagent to detect no color as an end point), and then using sulfamic acid to destroy the residual nitrous acid after reaction (taking the starch potassium iodide test paper not to turn blue, and using amount of sulfamic acid is about 0.5 g); to give a diazonium salt solution (all used directly in the next step).
2) Stirring is started in a reactor provided with a stirring device, 300g of water is added, 0.202mol of N-ethyl-N-benzylaniline-3 '-sulfonic acid is added, soda is added to adjust the pH value to 7.0-8.0, and the mixture is stirred until the N-ethyl-N-benzylaniline-3' -sulfonic acid is dissolved.
And (2) adding ice to cool to 0-5 ℃, slowly dropwise adding all the products (diazonium salt solution) obtained in the step 1), controlling the temperature of a reaction system to be not more than 10 ℃ in the dropwise adding process, adjusting the pH value to be 7.0-8.0 by using sodium carbonate in the dropwise adding process, reacting at 5-10 ℃ for 3 hours after the dropwise adding is finished, adding sodium chloride (about 60g) to separate out the dye, performing suction filtration to obtain a filter cake, and drying the filter cake at 80-90 ℃ for 24 hours to obtain about 110g of dye I-1.
The dye I-1 is as follows:
1H NMR(400MHz,DMSO-d6)：δ8.47(d,2H),8.33(s,2H),8.05(d,2H),7.93(d,4H),7.72(d,4H),7.58(d,4H),7.20(t,2H),6.78(d,4H),4.67(s,4H),3.62(q,4H),1.23(t,6H)；ESI MS(m/z,％):815.3([M-H]-,100)。
example 2, a process for the preparation of a trisazo red acid dye i-2, sequentially carrying out the following steps:
1) same as in step 1) of example 1;
2) stirring is started in a reactor with stirring, 400g of water is added, 0.202mol of N-ethyl-N-benzyl-m-toluidine-3 '-sulfonic acid is added, the pH is adjusted to 7.0 to 8.0 by adding soda ash, and the mixture is stirred until the N-ethyl-N-benzyl-m-toluidine-3' -sulfonic acid is dissolved.
Adding ice to cool to 0-5 ℃, slowly dropwise adding all the products (diazonium salt solution) obtained in the step 1), controlling the temperature of a reaction system to be not more than 10 ℃ in the dropwise adding process, adjusting the pH value to be 7.0-8.0 by using sodium carbonate in the dropwise adding process, reacting for 3 hours at the temperature of 5-10 ℃, adding sodium chloride (about 65g) to separate out the dye, performing suction filtration to obtain a filter cake, and drying the filter cake for 24 hours at the temperature of 80-90 ℃ to obtain about 116g of dye I-2.
The dye I-2 is as follows:
1H NMR(400MHz,DMSO-d6)：δ8.45(d,2H),8.37(d,2H),7.95(m,4H),7.74(m,2H),7.55(m,6H),7.33(t,2H),7.20(m,2H),6.78(m,2H),4.76(s,4H),3.62(q,4H),2.66(s,6H),1.23(t,6H)；ESI MS(m/z,％):843.3([M-H]-,100)。
the application example and the performance of the embodiment were tested according to the following test methods:
(1) solubility was tested according to GB/T3671.1-1996;
(2) the color fastness was determined as follows:
soaping fastness test method the test was carried out according to ISO 105-C10.
Perspiration (alkali) fastness test method the test was carried out according to ISO 105-E04.
100g of maltodextrin was added to 100g of the dye I to 1110 g obtained in example 1, and the mixture was standardized to a commercial dye and dyed to obtain a dyed fabric sample:
fabric: polyamide fiber, dyeing depth: 2% (weight ratio of commercial dye to fabric), bath ratio: 1:25, acetic acid: 1%, heating rate: heating to 95 ℃ at the temperature of 1 ℃/min, preserving heat for 30 minutes, cooling to 60 ℃, washing with water, and drying at 60 ℃.
Description of the drawings: the bulking agent used in the standardization may be sodium sulfate, sodium chloride, soluble starch, sodium lignosulfonate, ammonium lignosulfonate, or glucose instead of maltodextrin.
The dye I-2 obtained in example 2 was also used to obtain a dyed cloth sample by the same standardization and dyeing method as described above.
Soaping fastness test method on polyamide fibres the results are given in the following Table 1, according to ISO 105-C10:
TABLE 1
Perspiration (alkali) fastness on polyamide fibres is tested according to ISO105-E04, with the results given in Table 2 below:
TABLE 2
The standardized dyes I-1 and I-2 were subjected to solubility measurement, and the results are shown in Table 3 below:
TABLE 3
| Dye material | Solubility (g/L) |
| Ⅰ-1 | 120 |
| Ⅰ-2 | 100 |
(3) And carrying out performance measurement on the standardized dye I-1 and the standardized dye I-2 in the dyeing process:
fabric: polyamide fiber, dyeing depth: 1%, bath ratio: 1:50, acetic acid: 0.2g/L, leveling agent: 0.2g/L, heating rate: heating to 95 ℃ at the temperature of 1 ℃/min, keeping the temperature for 45 minutes, taking out the fabric at different times in the heating process, washing the fabric with water, and drying the fabric at the temperature of 60 ℃. And (3) adding the residual liquid after the fabric is taken out into blank fabric with the same weight, continuously heating and dyeing, cooling to 60 ℃ after heat preservation, washing with water, drying at 60 ℃, and taking out the dyed fabric at different times, wherein K/S values are shown in the following table 4:
TABLE 4
After the fabric is taken out at different temperatures and put into an equal-weight blank fabric for continuous dyeing, the K/S value of the fabric is shown in the following table 5:
TABLE 5
In conclusion: the dye I-1 and the dye I-2 have very gentle dye-uptake, good level-dyeing property and high dyeing degree.
Finally, it is also noted that the above-mentioned lists merely illustrate a few specific embodiments of the invention. It is obvious that the invention is not limited to the above embodiments, but that many variations are possible. All modifications which can be derived or suggested by a person skilled in the art from the disclosure of the present invention are to be considered within the scope of the invention.
Claims (5)
1. The trisazo red acid dye is characterized by having a structural general formula as follows:
R1and R2is-C2H5A group;
R3and R4Is H or-CH3A group;
m is H or an alkali metal cation.
2. Trisazo red acid dye according to claim 1, characterized by the structural formula being any of:
dye I-1:
dye I-2:
3. the process for preparing a trisazo red acid dye according to claim 1 or 2, which comprises the steps of:
1) adding diaminoazobenzene into water, uniformly stirring, adding hydrochloric acid, uniformly stirring, cooling to 0-5 ℃, dropwise adding a sodium nitrite solution to form a reaction system I, controlling the temperature of the reaction system I not to exceed 5 ℃ in the dropwise adding process, stirring and reacting at 0-5 ℃ for 2 +/-0.2 hours after the dropwise adding is finished, and then removing the residual nitrous acid after the reaction to obtain a diazonium salt solution;
p-diaminoazobenzene: hydrochloric acid 1: a molar ratio of 5.0;
p-diaminoazobenzene: sodium nitrite 1: a molar ratio of 2.05;
2) adding reaction raw materials into water, uniformly stirring, adjusting the pH value to 7.0-8.0, cooling to 0-5 ℃, dropwise adding the diazonium salt solution obtained in the step 1) to form a reaction system II, controlling the temperature of the reaction system II to be not more than 10 ℃ in the dropwise adding process, always adjusting the pH value of the reaction system II to 7.0-8.0 in the dropwise adding process, and reacting at 5-10 ℃ for 3 +/-0.3 hours after the dropwise adding is finished; reaction raw materials: the molar ratio of p-diaminoazobenzene in the step 1) is 2-2.1: 1.0;
after the reaction is finished, adding sodium chloride to generate a precipitate, filtering, and drying a filter cake to obtain a product;
when the reaction raw material is N-ethyl-N-benzylaniline-3' -sulfonic acid, the obtained product is dye I-1;
when the reaction raw material is N-ethyl-N-benzyl m-toluidine-3' -sulfonic acid, the obtained product is the dye I-2.
4. The method for preparing a trisazo red acid dye according to claim 3, wherein:
in the step 1), 200 +/-50 g of water is used for every 0.1mol of p-diaminoazobenzene.
5. The method for preparing a trisazo red acid dye according to claim 4, wherein:
in the step 2) of the said step,
300-400 g of water is matched with every 2-2.1 mol of reaction raw materials;
drying for 24 hours at the temperature of 80-90 ℃.
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| CN114958026B (en) * | 2022-05-30 | 2023-05-23 | 金华双宏化工有限公司 | Improved trisazo red acid dye and preparation method thereof |
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