CN114958026A - Improved trisazo red acid dye and preparation method thereof - Google Patents
Improved trisazo red acid dye and preparation method thereof Download PDFInfo
- Publication number
- CN114958026A CN114958026A CN202210595467.XA CN202210595467A CN114958026A CN 114958026 A CN114958026 A CN 114958026A CN 202210595467 A CN202210595467 A CN 202210595467A CN 114958026 A CN114958026 A CN 114958026A
- Authority
- CN
- China
- Prior art keywords
- dye
- trisazo
- improved
- acid
- red
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Images
Classifications
-
- 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
-
- 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
-
- 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
- D06P3/14—Wool
- D06P3/16—Wool using acid 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
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/24—Polyamides; Polyurethanes
- D06P3/241—Polyamides; Polyurethanes using acid dyes
Abstract
The invention discloses an improved trisazo red acid dye, which has a structural general formula as follows:
r1 and R2 are-C 2 H 5 A group; r3 and R4 are H or-CH 3 A group; m is H or an alkali metal cation. The invention also provides a preparation method of the composition. The improved trisazo red acid dye does not contain carcinogenic dye and heavy metal dye, and belongs to safe and environment-friendly dye. Has good water solubility, smooth dye-uptake and good level-dyeing property in a dyeing system, can be efficiently combined with protein and polyamide fiber, has high dye-uptake rate, and can be dyedThe fiber has excellent color fastness and is an ideal substitute for 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, 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. Acid dyes are the main dyes used in the printing of wool and polyamide fibres.
The date red is an important variety in red, provides dark blue light red tone, and the most date red acid dyes used in the market at present are: acid purplish red MB (c.i. acid violet 90), neutral purplish red GRL (c.i. acid red 213), and acid red SB (c.i. acid red 405). Because it is a metal complex dye, it is not environment-friendly and has many application limitations.
Patent CN201911362874.0 "trisazo red acid dye and its preparation method" has mentioned a new red acid dye, but because its color light is dark, it is difficult to blend some bright formulas in many color matching applications, and more often blend some dark hues, so the application is greatly limited.
Disclosure of Invention
The invention aims to provide a novel red acid dye-improved trisazo red acid dye and a preparation method and application thereof.
In order to solve the technical problems, the invention provides an improved trisazo red acid dye, which has a structural general formula as follows:
r1 and R2 are-C 2 H 5 A group;
r3 and R4 are H or-CH 3 A 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 formulas:
dye II-1:
the dye II-1 has a structural formula as follows:
r1 is-C 2 H 5 Group, R2 is-C 2 H 5 Group, R3 is a H group, R4 is a H group, M is H or an alkali metal cation.
Dye II-2:
the dye II-2 has a structural formula as follows:
r1 is-C 2 H 5 Group, R2 is-C 2 H 5 Group, R3 is-CH 3 Group, R4 is-CH 3 The group, M is H or an alkali metal cation.
The dye II-1 is specifically as follows:
the dye II-2 is specifically as follows:
the invention also provides a preparation method of the improved trisazo red acid dye, which comprises the following steps:
1) adding hydrochloric acid (mass fraction is 31%) and paranitroaniline into water, 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 1-2 hours after the dropwise adding is finished, and then eliminating the residual nitrous acid after the reaction to obtain a diazonium salt solution;
p-nitroaniline: hydrochloric acid 1: 3.7 molar ratio;
p-nitroaniline: sodium nitrite 1: a molar ratio of 1.05;
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 ratio of p-nitroaniline in step 1) is 1-1.05: 1.0 (preferably 1.02: 1.0) of the molar ratio;
the reaction raw materials are N-ethyl-N-benzylaniline-3 '-sulfonic acid (CAS No.:101-11-1) and N-ethyl-N-benzyl m-toluidine-3' -sulfonic acid.
3) Adding liquid alkali into the product obtained in the step 2) to adjust the pH value to 11.0-13.0, heating to 75-80 ℃, adding saccharides, and then keeping the temperature at 75-85 ℃ for 2 hours;
the saccharides are glucose, maltose and beta-cyclodextrin;
the saccharide is: a molar ratio of reactants (calculated as glucose monomers) of 1 to 1.5:1.0 (preferably 1.2 to 1.4: 1.0);
4) adding sodium chloride into the reaction product obtained in the step 3) 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 II-1;
when the reaction raw material is N-ethyl-N-benzyl m-toluidine-3' -sulfonic acid, the obtained product is the dye II-2.
The improvement of the preparation method of the improved trisazo red acid dye of the invention comprises the following steps:
in the step 1), 60 +/-10 g of water is added for every 0.1mol of p-nitroaniline.
The preparation method of the improved trisazo red acid dye is further improved as follows:
in the step 2), 150-200 g of water is added for every 0.1-0.105 mol of reaction raw materials;
in the step 4), drying is carried out for 24 hours at the temperature of 80-90 ℃.
The improved 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 finds that the trisazo red acid dye has more excellent color fastness, does not contain a heavy metal structure and a carcinogenic structure, can replace the red acid dye in the prior art, and simultaneously compensates the condition of light bias of the dye in the patent CN 201911362874.0.
In conclusion, the improved 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 dyed smoothly 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. Compared with the dye in CN201911362874.0, the dye has brighter color tone, and has wider application range when being applied to brighter products.
Drawings
The following describes embodiments of the present invention in further detail with reference to the accompanying drawings.
FIG. 1 is a graph comparing the dye uptake curves of the dye II-1 of the present invention and the corresponding dye I-1 of CN 201911362874.0;
FIG. 2 is a graph showing the dye uptake curves of the dye II-2 of the present invention and the corresponding dye I-2 of CN 201911362874.0.
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 50 to 300 rpm.
Example 1, a method for preparing a trisazo red acid dye ii-1, sequentially carrying out the following steps:
1) starting stirring in a reactor with a stirrer, adding 60g of water, adding 0.1mol (about 13.8g) of p-nitroaniline, adding 0.37mol of hydrochloric acid (31 mass percent of hydrochloric acid), cooling to 0-5 ℃, dropwise adding a sodium nitrite solution (30 mass percent of sodium nitrite solution) containing 0.105mol of sodium nitrite, controlling the temperature of a reaction system to be not more than 5 ℃ in the dropwise adding process, turning the starch potassium iodide test paper to blue at the moment, reacting for 2 hours at 0-5 ℃ (using an Ehrlich reagent to detect no color development as an end point), and then destroying the residual nitrous acid after the reaction by sulfamic acid (taking the starch potassium iodide test paper as the standard of not turning the starch potassium iodide test paper to blue); to give a diazonium salt solution (all used directly in the next step).
2) Stirring is started in a reactor with stirring, 150g of water is added, 0.102mol of N-ethyl-N-benzylaniline-3 '-sulfonic acid is added, the pH value is adjusted to 7.0-8.0 by adding soda ash, and the mixture is stirred until the N-ethyl-N-benzylaniline-3' -sulfonic acid is dissolved.
Cooling to 0-5 ℃, slowly dripping 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 dripping process, adjusting the pH value to be 7.0-8.0 by using sodium carbonate in the dripping process, and reacting for 3 hours at 5-10 ℃ after the dripping is finished.
3) Adding liquid alkali into the product obtained in the step 2) to adjust the pH value to 12.0 (the amount of the liquid alkali is about 90g), heating to 75-80 ℃, adding 25g (about 0.135mol) of industrial glucose, and preserving heat for 2 hours at 75-85 ℃ after the addition is finished;
4) and adding sodium chloride (about 30g) into the reaction product obtained in the step 3) to separate out the dye, performing suction filtration to obtain a filter cake, and drying the filter cake at the temperature of 80-90 ℃ for 24h to obtain about 52g of the dye II-1.
The dye II-1 is:
1 H NMR(400MHz,DMSO-d6)：δ9.16(d,2H),8.41(d,4H),7.93-7.70(m,10H),7.59(d,2H), 7.44(d,2H),6.95(d,4H),4.81(s,4H),3.42(q,4H),1.12(t,6H)；ESI MS(m/z,％):853.3([M-Na] - , 100)。
example 2, a method for preparing a trisazo red acid dye ii-2, sequentially comprising the steps of:
1) same as in step 1) of example 1;
2) stirring is started in a reactor with stirring, 200g of water is added, 0.102mol of N-ethyl-N-benzyl m-toluidine-3 '-sulfonic acid is added, the pH value is adjusted to 7.0-8.0 by adding soda ash, and the mixture is stirred until the N-ethyl-N-benzyl m-toluidine-3' -sulfonic acid is dissolved.
Cooling to 0-5 ℃, slowly dripping 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 dripping process, adjusting the pH value to be 7.0-8.0 by using sodium carbonate in the dripping process, and reacting for 3 hours at the temperature of 5-10 ℃.
3) Adding liquid alkali into the product obtained in the step 2) to adjust the pH value to 12.0, heating to 75-80 ℃, adding 25g of glucose, and keeping the temperature at 75-85 ℃ for 2 hours after the addition.
4) Adding sodium chloride (about 20g) into the reaction product obtained in the step 3) to separate out the dye, performing suction filtration to obtain a filter cake, and drying the filter cake at the temperature of 80-90 ℃ for 24h to obtain about 59g of the dye II-2.
The dye II-2 is:
1 H NMR(400MHz,DMSO-d6)：δ9.15(d,2H),8.03(d,2H),7.91-7.70(m,10H),7.66-7.59 (m,4H),7.44(d,2H),6.88(d,2H),4.80(s,4H),3.41(q,4H),2.12(s,6H),1.12(t,6H)；ESI MS(m/z,％):881.2([M-Na] - ,100)。
the application embodiment and each performance of the embodiment are detected according to the method of CN 201911362874.0;
60g of maltodextrin was added to 60g of the dye II to 152 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 II-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 tested according to ISO105-C10, the results are given in Table 1 below:
TABLE 1
Perspiration (alkali) fastness on polyamide fibres is tested according to ISO105-E04, with the results given in Table 2 below:
TABLE 2
As can be seen from the data in tables 1 and 2, the dyes II-1 and II-2 have excellent color fastness performance, and compared with the corresponding dyes in CN201911362874.0, the color fastness of the original cloth is slightly improved.
The standardized dyes II-1 and II-2 were subjected to solubility measurement (GB/T3671.1, 90 ℃ C.), and the results are shown in Table 3 below:
TABLE 3
| Dye material | Solubility (g/L) |
| Ⅱ-1 | 120 |
| Ⅱ-2 | 100 |
The solubility of the dye obtained by the invention is the same as CN 201911362874.0.
(3) And performing performance measurement on the standardized dye II-1 and the standardized dye II-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
The dye uptake curves of the dyes of the invention were calculated from the fabric K/S values/total K/S (Table 4+ Table 5K/S values for the corresponding conditions) in combination with the data of tables 4 and 5 as shown in Table 6:
TABLE 6
The basic dye uptake curve data for the corresponding dyes I-1 and I-2 of CN201911362874.0 were calculated in the same manner as shown in Table 7.
TABLE 7
The dyes II-1 and II-2 of the present invention were compared with the dye I-1 and I-2 of CN201911362874.0, respectively, and the results are shown in FIG. 1 and FIG. 2.
In conclusion: the dye II-1 and the dye II-2 also have very gentle dye-uptake curves, good level-dyeing property and high dyeing degree. Compared with CN201911362874.0, the invention has the following advantages: the dye uptake curve is more gentle.
Color difference data of the dye II-1 of the present invention with respect to the CN201911362874.0 dye I-1 were examined.
The detection process is as follows: polyamide fiber, dyeing depth: 0.5%, 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, washing the fabric, drying the fabric at the temperature of 60 ℃, taking out the fabric for cooling again, detecting the fabric sample by using a Datacolor 850 color measuring instrument manufactured by the American Deta company so as to respectively obtain a Lab value of II-1 and a Lab value of I-1 in CN201911362874.0, and then automatically calculating DC and DH values by software carried by a color measuring instrument system according to a CIE color difference calculation formula as shown in the following table 8.
TABLE 8
| Dye material | CIE L | CIE a | CIE b |
| Ⅱ-1 | 41.58 | 42.56 | 6.60 |
| CN201911362874.0-Ⅰ-1 | 40.02 | 38.76 | 3.00 |
The data of II-1 are shown in Table 9, using CN 201911362874.0-I-1 as a standard.
TABLE 9
| CIE DL | CIE Da | CIE Db | CIE DC | CIE DH |
| 1.56 | 3.80 | 3.60 | 4.12 | 1.78 |
From table 9, it can be seen that: the color light of the detection dye II-1 is reddish, yellowish and gorgeous relative to the color light of I-1 in CN 201911362874.0.
Color difference data of the dye II-2 of the present invention with respect to the CN201911362874.0 dye I-2 were examined.
The detection process is the same as the above, so that the Lab value of II-2 and the Lab value of I-2 in CN201911362874.0 are respectively obtained, and then the DC value and the DH value are obtained by the same calculation formula; the method comprises the following specific steps:
watch 10
| Dye material | CIE L | CIE a | CIE b |
| Ⅱ-2 | 37.71 | 37.82 | -5.65 |
| CN201911362874.0-Ⅰ-2 | 35.75 | 33.24 | -9.65 |
The data of II-2 are shown in Table 11, based on CN 201911362874.0-I-2.
TABLE 11
| CIE DL | CIE Da | CIE Db | CIE DC | CIE DH |
| 1.96 | 4.58 | 4.00 | 4.26 | 1.95 |
From table 11, it can be seen that: the color light of the detection dye II-2 is reddish, yellowish and gorgeous relative to the color light of I-2 in CN 201911362874.0.
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 (7)
1. The improved trisazo red acid dye is characterized by having a structural general formula as follows:
r1 and R2 are-C 2 H 5 A group;
r3 and R4 are H or-CH 3 A group;
m is H or an alkali metal cation.
2. An improved trisazo red acid dye according to claim 1, wherein: dye II-1, dye II-2:
dye II-1:
dye II-2:
3. an improved trisazo red acid dye according to claim 2, wherein the dye ii-1 is:
4. an improved trisazo red acid dye according to claim 2, wherein the dye ii-2 is:
5. the process for preparing an improved trisazo red acid dye according to any one of claims 1 to 4, comprising the steps of:
1) adding hydrochloric acid and paranitroaniline into water, 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 1-2 hours after the dropwise adding is finished, and then eliminating the residual nitrous acid after the reaction to obtain a diazonium salt solution;
p-nitroaniline: hydrochloric acid 1: 3.7 molar ratio;
p-nitroaniline: sodium nitrite 1: a molar ratio of 1.05;
2) adding reaction raw materials into water, uniformly stirring, then 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 not to exceed 10 ℃ in the dropwise adding process, constantly 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-nitroaniline in the step 1) is 1-1.05: 1.0;
the reaction raw materials are N-ethyl-N-benzylaniline-3 '-sulfonic acid and N-ethyl-N-benzyl m-toluidine-3' -sulfonic acid;
3) adding liquid alkali into the product obtained in the step 2) to adjust the pH value to 11.0-13.0, heating to 75-80 ℃, adding saccharides, and then keeping the temperature at 75-85 ℃ for 2 hours;
the saccharides are glucose, maltose and beta-cyclodextrin;
the saccharide is: the molar ratio of reactants is 1-1.5: 1.0;
4) adding sodium chloride into the reaction product obtained in the step 3) 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 II-1;
when the reaction raw material is N-ethyl-N-benzyl m-toluidine-3' -sulfonic acid, the obtained product is the dye II-2.
6. The process for the preparation of improved trisazo red acid dyes according to claim 5, wherein:
in the step 1), 60 +/-10 g of water is added for every 0.1mol of p-nitroaniline.
7. The process for the preparation of an improved trisazo red acid dye according to claim 6, wherein:
in the step 2), 150-200 g of water is added for every 0.1-0.105 mol of reaction raw materials;
in the step 4), drying is carried out for 24 hours at the temperature of 80-90 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210595467.XA CN114958026B (en) | 2022-05-30 | 2022-05-30 | Improved trisazo red acid dye and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210595467.XA CN114958026B (en) | 2022-05-30 | 2022-05-30 | Improved trisazo red acid dye and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114958026A true CN114958026A (en) | 2022-08-30 |
| CN114958026B CN114958026B (en) | 2023-05-23 |
Family
ID=82957681
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202210595467.XA Active CN114958026B (en) | 2022-05-30 | 2022-05-30 | Improved trisazo red acid dye and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114958026B (en) |
Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR754798A (en) * | 1932-04-28 | 1933-11-14 | Ste Ind Chim Bale | Production of new azo dyestuffs |
| GB414483A (en) * | 1932-05-15 | 1934-08-09 | Chem Ind Basel | Manufacture of new azo-dyestuffs |
| GB557842A (en) * | 1942-05-06 | 1943-12-08 | Arthur Howard Knight | New disazo dyestuffs |
| EP0031508A2 (en) * | 1979-12-19 | 1981-07-08 | Hoechst Aktiengesellschaft | Water-soluble azo compounds and their copper complexes, process for their preparation and their use as dyestuffs |
| CN1421492A (en) * | 2002-12-06 | 2003-06-04 | 华东理工大学 | Monoazo acid blue dye without carcinogenicity and its application |
| CN1954034A (en) * | 2004-05-19 | 2007-04-25 | 克莱里安特财务(Bvi)有限公司 | Bridged monoazo dyes |
| CN101415781A (en) * | 2006-04-07 | 2009-04-22 | 克莱里安特财务(Bvi)有限公司 | Acid dyes |
| CN101705013A (en) * | 2009-11-16 | 2010-05-12 | 天津德凯化工股份有限公司 | Dark blue dye for dyeing nylon and preparation method thereof |
| US20100233443A1 (en) * | 2006-06-25 | 2010-09-16 | Clariant Finance (Bvi) Limited | Acid dyes |
| CN102660134A (en) * | 2012-05-10 | 2012-09-12 | 金华恒利康化工有限公司 | Acidic green-light black dye and preparation method thereof |
| CN104011143A (en) * | 2011-10-22 | 2014-08-27 | 克拉瑞特国际有限公司 | Trisazo acid dyes |
| CN107721887A (en) * | 2017-10-18 | 2018-02-23 | 恒升化工有限公司 | A kind of preparation method of highly acid blue dyes |
| CN108289968A (en) * | 2015-11-27 | 2018-07-17 | 株式会社D.西医疗法研究所 | Triarylmethane composition and colouring compositions for dyeing eye mask |
| CN111040466A (en) * | 2019-12-26 | 2020-04-21 | 金华双宏化工有限公司 | Trisazo red acid dye and preparation method thereof |
| JP2021024798A (en) * | 2019-08-02 | 2021-02-22 | 株式会社デ・ウエスタン・セラピテクス研究所 | Method for producing ethyl anilino toluene sulfonic acid derivative |
-
2022
- 2022-05-30 CN CN202210595467.XA patent/CN114958026B/en active Active
Patent Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR754798A (en) * | 1932-04-28 | 1933-11-14 | Ste Ind Chim Bale | Production of new azo dyestuffs |
| GB414483A (en) * | 1932-05-15 | 1934-08-09 | Chem Ind Basel | Manufacture of new azo-dyestuffs |
| GB557842A (en) * | 1942-05-06 | 1943-12-08 | Arthur Howard Knight | New disazo dyestuffs |
| EP0031508A2 (en) * | 1979-12-19 | 1981-07-08 | Hoechst Aktiengesellschaft | Water-soluble azo compounds and their copper complexes, process for their preparation and their use as dyestuffs |
| CN1421492A (en) * | 2002-12-06 | 2003-06-04 | 华东理工大学 | Monoazo acid blue dye without carcinogenicity and its application |
| CN1954034A (en) * | 2004-05-19 | 2007-04-25 | 克莱里安特财务(Bvi)有限公司 | Bridged monoazo dyes |
| CN101415781A (en) * | 2006-04-07 | 2009-04-22 | 克莱里安特财务(Bvi)有限公司 | Acid dyes |
| US20100233443A1 (en) * | 2006-06-25 | 2010-09-16 | Clariant Finance (Bvi) Limited | Acid dyes |
| CN101705013A (en) * | 2009-11-16 | 2010-05-12 | 天津德凯化工股份有限公司 | Dark blue dye for dyeing nylon and preparation method thereof |
| CN104011143A (en) * | 2011-10-22 | 2014-08-27 | 克拉瑞特国际有限公司 | Trisazo acid dyes |
| CN102660134A (en) * | 2012-05-10 | 2012-09-12 | 金华恒利康化工有限公司 | Acidic green-light black dye and preparation method thereof |
| CN108289968A (en) * | 2015-11-27 | 2018-07-17 | 株式会社D.西医疗法研究所 | Triarylmethane composition and colouring compositions for dyeing eye mask |
| CN107721887A (en) * | 2017-10-18 | 2018-02-23 | 恒升化工有限公司 | A kind of preparation method of highly acid blue dyes |
| JP2021024798A (en) * | 2019-08-02 | 2021-02-22 | 株式会社デ・ウエスタン・セラピテクス研究所 | Method for producing ethyl anilino toluene sulfonic acid derivative |
| CN111040466A (en) * | 2019-12-26 | 2020-04-21 | 金华双宏化工有限公司 | Trisazo red acid dye and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 潘国光: "二氧化锰氧化法合成酸性翠蓝AE", 染料与染色 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114958026B (en) | 2023-05-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR850001475B1 (en) | Manufacturing method of azodyes for cellulose fibers | |
| EP0021351A1 (en) | Formazan reactive blue dyes, a process for their preparation and a process for dyeing cellulose fibers therewith | |
| CN111040466B (en) | Trisazo red acid dye and preparation method thereof | |
| US5075428A (en) | 2,4-diamino-6-fluorotriazine disazo reactive dyestuffs | |
| CN110938039A (en) | Purple reactive dye based on trisazo multichromosome and preparation and application thereof | |
| CN113683903B (en) | Thiazole heterocycle azo type reactive dye and preparation method thereof | |
| US4150021A (en) | Esters of cellulose with phosphonic acid dyes having a sulfonamide bridge | |
| CN112662199B (en) | Black dye compound and preparation method and dyeing application thereof | |
| CN111303654B (en) | Biaryl primary amine acid dye containing beta-naphthylamine structure and preparation method thereof | |
| CN114958026A (en) | Improved trisazo red acid dye and preparation method thereof | |
| EP1760117B1 (en) | Reactive dyestuff compositions and their use | |
| US4322372A (en) | Condensation products containing sulphonic acid groups | |
| Akhtar et al. | Application of Acid Dyes on Silk Fabric and Fastness Properties Part II. | |
| HU182574B (en) | Process for producing 1:2 metal complexes of bis-diazo-compounds | |
| US3413077A (en) | Process of dyeing cellulose and polyamide fabrics with reactive dyestuffs | |
| CN109651839B (en) | Preparation method of orange reactive printing dye | |
| US4248773A (en) | Acetoacetamide diazo dyestuffs | |
| CN110066527B (en) | Red reactive dye and preparation method thereof | |
| CN110903679A (en) | Green reactive dye based on monoazo structure of mono H acid and preparation and application thereof | |
| CN115505281B (en) | Improved orange acid dye and preparation method thereof | |
| US4113719A (en) | 1:2-Cobalt-complex azo dyestuffs having an acetoacetylamino diphenylamino coupler | |
| CA1049001A (en) | Chromium complex dyes, their manufacture and use | |
| JPH0798910B2 (en) | Water-soluble disazo compound, method for producing the same and method of using the compound as a dye | |
| US4472308A (en) | Azo dyestuffs containing an amino or acylated amino naphthol monosulfonic acid radical and at least one reactive phosphoric or phosphonic acid group | |
| US1841636A (en) | Amino and nitro derivatives of ortho-hydroxy-carboxy-diphenyl sulphides, and process of preparing same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |