CN115838538A - Disperse orange capable of replacing disperse yellow 54#, and synthesis method and application thereof - Google Patents
Disperse orange capable of replacing disperse yellow 54#, and synthesis method and application thereof Download PDFInfo
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- CN115838538A CN115838538A CN202211609305.3A CN202211609305A CN115838538A CN 115838538 A CN115838538 A CN 115838538A CN 202211609305 A CN202211609305 A CN 202211609305A CN 115838538 A CN115838538 A CN 115838538A
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Abstract
The invention discloses a disperse orange capable of replacing disperse yellow 54#, a synthetic method and application thereof. The synthesis method comprises the following steps: (1) Putting p-nitroaniline into nitrosyl sulfuric acid, controlling the temperature below 30 ℃ after the material is put, and adding ice water after stirring to obtain a diluent; keeping the temperature of the diluent below 0 ℃; (2) Adding N-cyanoethyl o-chloroaniline into hydrochloric acid solution containing an emulsifier for pulping, controlling the temperature not to exceed 25 ℃, and adding the diluent in the step (1); (3) Gradually heating and preserving heat, wherein the heating rate is 0.5-5 ℃/h, the temperature per liter is 2-5 ℃, the heat preservation is 1-4h, the temperature is finally heated to 44-50 ℃, the reaction time is 30-60h, and the disperse orange is obtained after the reaction is finished. The disperse orange can replace disperse yellow 54# to be used for dyeing products such as terylene and the like.
Description
Technical Field
The invention relates to the technical field of production of disperse dyes, in particular to a disperse orange capable of replacing disperse yellow 54#, a synthetic method and application thereof.
Background
Disperse yellow 54# is an important disperse dye, is mainly used for dyeing polyester fibers, has good level dyeing performance and high light fastness, can be used for dyeing single color, and can be spliced with blue to dye bright fruit green. The dye synthesis is mainly carried out by reacting 2-methyl-3-hydroxyquinoline or 2-methyl-3-hydroxyquinoline-4-carboxylic acid with phthalic anhydride.
Patent specification with publication number CN105669545A discloses a preparation process of disperse yellow 54#, which comprises the steps of carrying out heat preservation reaction on 2-methyl-3-hydroxyquinoline or 2-methyl-3-hydroxyquinoline-4-carboxylic acid and phthalic anhydride at 200 +/-20 ℃, putting the obtained product into hot water for dilution when the product is hot, and carrying out colloid grinding after the product is cooled.
Patent specification CN109021607A discloses a method for producing disperse yellow 54#, which is obtained by reacting 3-hydroxyquinoline-4-carboxylic acid with phthalic anhydride in a mixed medium of dimethylformamide or trichlorobenzene and phenol at 180 ℃.
The method realizes the synthesis of disperse yellow 54#, but the reaction process is harsh, the reaction needs to be carried out under the condition of high temperature or toxic solvent, and the production cost and the safety risk are high.
The invention provides a dye which has performance similar to that of disperse yellow 54# and can replace disperse yellow 54#, a synthetic method and application thereof, and production under mild conditions can be realized.
Disclosure of Invention
The invention provides a disperse orange dye which has performance similar to that of disperse yellow 54# and can replace disperse yellow 54#, and the disperse orange dye can be produced under mild conditions. Compared with disperse yellow 54#, the dye has basically consistent light fastness, rubbing fastness and compatibility, and slightly excellent level dyeing performance and dye strength.
The specific technical scheme is as follows:
a disperse orange capable of replacing disperse yellow 54#, which has a structure shown as the following formula (I):
the invention also provides a synthesis method of the dispersed orange, which comprises the following steps:
(1) Putting p-nitroaniline into nitrosyl sulfuric acid, controlling the temperature below 30 ℃ after the material is put, and adding ice water after stirring to obtain a diluent; keeping the temperature of the diluent below 0 ℃;
(2) Adding N-cyanoethyl o-chloroaniline into hydrochloric acid solution containing an emulsifier for pulping, controlling the temperature not to exceed 25 ℃, and adding the diluent in the step (1);
(3) Gradually heating and preserving heat, wherein the heating rate is 0.5-5 ℃/h, the temperature per liter is 2-5 ℃, the heat preservation is 1-4h (preferably 1-2 h), the temperature is finally heated to 44-50 ℃, the reaction time is 30-60h, and the disperse orange is obtained after the reaction is finished.
In order to further improve the product purity and yield of the dispersed orange, the following technical scheme can be optimized:
in a preferred embodiment, in the method for synthesizing dispersed orange, in step (1), the molar ratio of the p-nitroaniline to the nitrosyl sulfuric acid is preferably 1.01 to 1.09, and more preferably 1.02 to 1.05. Within the range, the p-nitroaniline can be completely reacted, and the dosage of nitrosyl sulfuric acid can be reduced to the minimum.
In a preferred embodiment, in the step (1), the stirring time is 3-8h.
In a preferred embodiment, in the method for synthesizing dispersed oranges, in step (1), the mass fraction of the ice water in the diluent is preferably 40% to 60%, and more preferably 50% to 55%.
In a preferred embodiment, in the method for synthesizing dispersed orange, in the step (2), the mass fraction of HCl in the hydrochloric acid solution is preferably 24% to 35%, and more preferably 24% to 28%, which facilitates practical operation.
In a preferred embodiment, in the method for synthesizing dispersed orange, in step (2), the mass fraction of the emulsifier in the hydrochloric acid solution is preferably 0.05% to 0.5%, and more preferably 0.05% to 0.2%, which can achieve the desired effects of product purity and yield, and can reduce the amount of the emulsifier.
In a preferred embodiment, in the step (2), the mass ratio of the cyanoethyl o-chloroaniline to the hydrochloric acid solution is 1:3-5.
In a preferred embodiment, in the method for synthesizing dispersed oranges, in the step (2), the beating time is preferably 0.1 to 2 hours, and more preferably 0.5 to 1 hour.
In a preferred embodiment, in the step (2), the diluent added in the step (1) is used for preferably 0.5 to 4 hours, and more preferably 0.5 to 1.5 hours.
In a preferred embodiment, in the step (2), the diluent is added according to a molar ratio of the p-nitroaniline in the step (1) to the N-cyanoethyl-o-chloroaniline in the step (2) of 1.05-1.3.
The invention also provides application of the dispersed orange. The disperse orange can be used for dyeing terylene.
The invention also provides application of the disperse orange in dyeing instead of the disperse yellow 54#.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides a novel disperse orange which has excellent level dyeing performance, light fastness, rubbing fastness, compatibility and dyeing intensity and can be used for replacing disperse yellow 54#.
The synthesis conditions of the disperse orange are mild, the overall reaction temperature is-1-50 ℃, the equipment requirement is low, the method is suitable for large-scale production, the product purity is more than 91%, and the yield is more than 89%.
Drawings
FIG. 1 is a schematic diagram of a process for synthesizing dispersed orange according to the present invention.
Detailed Description
The invention is further described with reference to the following drawings and specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention.
The following examples are conducted under conditions not specified, usually according to conventional conditions, or according to conditions recommended by the manufacturer.
As shown in fig. 1, the method for synthesizing dispersed orange of the present invention comprises the steps of:
(1) Putting p-nitroaniline into nitrosyl sulfuric acid, controlling the temperature below 30 ℃ after the material is put, and adding ice water after stirring to obtain a diluent;
(2) Adding N-cyanoethyl o-chloroaniline into hydrochloric acid solution containing an emulsifier for pulping, controlling the temperature not to exceed 25 ℃, and adding the diluent in the step (1);
(3) Gradually heating and preserving heat, wherein the heating rate is 0.5-5 ℃/h, the temperature per liter is 2-5 ℃, the heat preservation is 1-4h (preferably 1-2 h), the temperature is finally heated to 44-50 ℃, the reaction time is 30-60h, and the disperse orange is obtained after the reaction is finished.
Example 1
27.3g of p-nitroaniline is added into 92.4g of nitrosyl sulfuric acid, the molar ratio of the two is 1.03, the temperature is controlled at 25 ℃, the mixture is stirred for 4 hours, 120g of ice water is added to obtain a diluent, and the temperature is kept at 0 ℃;
42g N-cyanoethyl o-chloroaniline is added into 186g hydrochloric acid solution (hydrochloric acid concentration 25 wt%) containing 0.05wt% peregal to be pulped, the temperature is controlled at 24 ℃, and the pulping time is 0.5h; after pulping, adding the diluent into pulping liquid for 1h; controlling the temperature to 20 ℃;
gradually heating up, heating up at a speed of 1 ℃/h, keeping the temperature at 2 ℃ per liter for 2h, heating up to 48 ℃, keeping the total time at 56h, obtaining the dispersed orange after the reaction is finished, wherein the purity is 92.0%, the yield is 63.1g, and the yield is 89.1%.
Example 2
Adding 14g of p-nitroaniline into 47.8g of nitrosyl sulfuric acid, controlling the molar ratio of the p-nitroaniline to the nitrosyl sulfuric acid to be 1.04, controlling the temperature to be 25 ℃, stirring for 4 hours, adding 70g of ice water to obtain a diluent, and keeping the temperature at-1 ℃;
20.1g N-cyanoethyl o-chloroaniline is added into 82.4g hydrochloric acid solution (hydrochloric acid concentration 27 wt%) containing 0.1wt% peregal to be pulped, the temperature is controlled at 25 ℃, and the pulping time is 0.5h; after pulping, adding the diluent into pulping liquid for 0.5h; controlling the temperature to 15 ℃;
gradually heating up, heating up at 5 ℃/h, keeping the temperature for 2h at the temperature of 2 ℃/h, heating up to 50 ℃, keeping the temperature for 2h, and obtaining the dispersed orange with the purity of 92.5 percent, the yield of 32.3g and the yield of 89.4 percent after the reaction is finished, wherein the total time is 42 h.
Example 3
270g of p-nitroaniline is added into 932g of nitrosyl sulfuric acid, the molar ratio of the two is 1.05, the temperature is controlled at 28 ℃, stirring is carried out for 8 hours, 1469g of ice water is added to obtain a diluent, and the temperature is kept at-1 ℃;
459g N-cyanoethyl o-chloroaniline is added into 1955g hydrochloric acid solution (hydrochloric acid concentration is 26 wt%) containing 0.4wt% peregal to be pulped, the temperature is controlled at 26 ℃, and the pulping time is 2 hours; after pulping, adding the diluent into pulping liquid for 3 hours; controlling the temperature to 23 ℃;
gradually heating up, heating up at a speed of 0.5 ℃/h, keeping the temperature at 5 ℃ per liter for 1h, heating up to 47 ℃, keeping the total time at 55h, obtaining the dispersed orange after the reaction is finished, wherein the purity is 91.5%, the yield is 650.0g, and the yield is 92.3%.
Example 4
100g of p-nitroaniline is put into 338.5g of nitrosyl sulfuric acid, the molar ratio of the two is 1.03, the temperature is controlled at 27 ℃, the mixture is stirred for 6 hours, 495g of ice water is added to obtain a diluent, and the temperature is kept at-1 ℃;
150g N-cyanoethyl o-chloroaniline is added into 615g hydrochloric acid solution (hydrochloric acid concentration 27 wt%) containing 0.2wt% peregal to be pulped, the temperature is controlled at 27 ℃, and the pulping time is 1h; after pulping, adding the diluent into pulping liquid for 2 hours; controlling the temperature to 20 ℃;
gradually heating up, heating up at a rate of 1 ℃/h, keeping the temperature for 1h at a temperature of 3 ℃ per liter, heating up to 48 ℃, keeping the temperature for a total time of 37h, obtaining the disperse orange after the reaction is finished, wherein the purity is 91.8%, the yield is 235.0g, and the yield is 90.4%.
Example 5
27.3g of p-nitroaniline is added into 91.5g of nitrosyl sulfuric acid, the molar ratio of the p-nitroaniline to the nitrosyl sulfuric acid is 1.02, the temperature is controlled at 28 ℃, the mixture is stirred for 3 hours, 120g of ice water is added to obtain a diluent, and the temperature is kept at-1 ℃;
40g N-cyanoethyl o-chloroaniline is added into 186g hydrochloric acid solution (hydrochloric acid concentration 24 wt%) containing 0.1wt% peregal to be pulped, the temperature is controlled at 25 ℃, and the pulping time is 0.5h; after pulping, adding the diluent into pulping liquid for 1.5h; controlling the temperature to 20 ℃;
gradually heating up, heating up at a speed of 1 ℃/h, keeping the temperature at 2 ℃ per liter for 1h, heating up to 47 ℃, keeping the temperature for total time of 41h, obtaining the disperse orange after the reaction is finished, wherein the purity is 91.7%, the yield is 63.7g, and the yield is 89.6%.
The purity of the dispersed orange compound prepared in each example was tested by liquid chromatography, and the structure was identified by LC-MS.
The results of the performance tests of the novel dispersed orange and the dispersed yellow 54# prepared in each example are shown in the following tables 1-3.
TABLE 1 fastness test
| Color fastness to sunlight | Fastness to dry rubbing | Fastness to wet rubbing | Degree of migration | |
| Novel dispersing orange | Grade 3-4 | 4-5 stages | 4 stage | 98.13 |
| Disperse yellow 54# | Grade 3-4 | 4-5 stages | 4 stage | 96.51 |
Note: the color fastness to sunlight, the time is 20h, AARCC 1-2004, the temperature is 180 ℃ multiplied by 30s, the concentration of a cloth sample is 0.2 percent, and the cloth is made of a terylene material;
rubbing fastness is ISO 105-X12, time is 20h,180 ℃ multiplied by 30s, concentration of a cloth sample is 4.0%, and the cloth is made of polyester material;
the dye transfer degree is GB/T10663-200, the concentration of a cloth sample is 1.0%, and the cloth is made of a terylene material.
TABLE 2 dyeing Strength test
TABLE 3 compatibility test
Note: compatibility with English color Huihong E-FB and English color Huihong E-BL; controlling the temperature to be normal temperature, starting heating up at the heating rate of 1 ℃/min, and preserving heat after the temperature reaches 130 ℃; the D65 strength is marked by using stock solution at 130 ℃ for 50min, a color measurement data formula CMC2:1, and the cloth is made of terylene.
As can be seen from tables 1, 2 and 3, the novel disperse orange of the invention has basically the same performance with disperse yellow 54# in light fastness, rubbing fastness, compatibility with red and blue dyes, and slightly excellent dye transfer degree (level dyeing performance) and dyeing strength, and can be used for replacing disperse yellow 54#.
Comparative example
27.3g of p-nitroaniline is put into 91.5g of nitrosyl sulfuric acid, the molar ratio of the p-nitroaniline to the nitrosyl sulfuric acid is 1.02, the temperature is controlled at 28 ℃, and the mixture is stirred for 3 hours to obtain a diazo liquid.
40g N-cyanoethyl o-chloroaniline is added into 186g hydrochloric acid solution (hydrochloric acid concentration 24 wt%) containing 0.1wt% peregal to carry out pulping, the temperature is controlled at 30 ℃, and the pulping time is 0.5h; after pulping, adding the diluent into pulping liquid for 3.5 hours; controlling the temperature to be 30 ℃; after the addition, stirring was continued for 50 hours, and at the end of the reaction, dispersed orange was obtained with a purity of 88.2% and a yield of 59.7g. The yield was 80.8%.
It can be seen that, in the comparative example, no ice water is added for dilution after the reaction of the paranitroaniline and the nitrosyl sulfuric acid, the temperature is controlled to be 30 ℃ when the paranitroaniline and the cyanoethyl o-chloroaniline are coupled, the low-temperature pulping below 25 ℃ is not needed, and the heating reaction is not needed, so that the diazo is easy to decompose, the coupling effect is poor, the product purity is low, and the yield is low.
The synthesis method adopted by the invention reduces the diazo decomposition degree caused by heat release in the diazo dropping process by diluting the diazo liquid of paranitroaniline at low temperature, and simultaneously promotes the coupling reaction by using a step-by-step heating mode, thereby realizing high conversion rate and high selectivity. Compared with the dispersed oranges prepared in the comparative example, the purity and yield of the dispersed oranges in the example are remarkably improved.
Furthermore, it should be understood that various changes and modifications can be made by one skilled in the art after reading the above description of the present invention, and equivalents also fall within the scope of the invention as defined by the appended claims.
Claims (9)
1. A disperse orange capable of replacing disperse yellow 54#, which is characterized by having a structure shown as the following formula (I):
2. the method for synthesizing dispersed oranges according to claim 1, characterized by comprising the steps of:
(1) Putting p-nitroaniline into nitrosyl sulfuric acid, controlling the temperature below 30 ℃ after the material is put, and adding ice water after stirring to obtain a diluent; keeping the temperature of the diluent below 0 ℃;
(2) Adding N-cyanoethyl o-chloroaniline into hydrochloric acid solution containing an emulsifier for pulping, controlling the temperature not to exceed 25 ℃, and adding the diluent in the step (1);
(3) Gradually heating and preserving heat, wherein the heating rate is 0.5-5 ℃/h, the temperature per liter is 2-5 ℃, the heat preservation is 1-4h, the temperature is finally heated to 44-50 ℃, the reaction time is 30-60h, and the disperse orange is obtained after the reaction is finished.
3. The synthesis method according to claim 2, wherein in the step (1), the molar ratio of the p-nitroaniline to the nitrosyl sulfuric acid is 1.01-1.09.
4. The synthesis method according to claim 2, wherein in step (1):
the stirring time is 3-8h;
the mass fraction of the ice water in the diluent is 40-60%.
5. The method of synthesis according to claim 2, wherein in step (2):
the mass fraction of HCl in the hydrochloric acid solution is 24-35%;
the mass fraction of the emulsifier in the hydrochloric acid solution is 0.05-0.5%;
the mass ratio of the N-cyanoethyl o-chloroaniline to the hydrochloric acid solution is 1:3-5.
6. The synthesis method according to claim 2, wherein in the step (2), the beating time is 0.1-2h.
7. The method of synthesis according to claim 2, wherein in step (2):
the time for adding the diluent in the step (1) is 0.5-4h;
and (3) adding the diluent according to the molar ratio of the p-nitroaniline in the step (1) to the N-cyanoethyl-o-chloroaniline in the step (2) of 1.05-1.3.
8. The use of dispersed oranges according to claim 1, characterized in that the dispersed oranges are used for dyeing terylene.
9. Use of the disperse orange of claim 1 for dyeing in place of disperse yellow 54#.
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2022
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