CN112480708B - Reactive dye red and preparation method and application thereof - Google Patents
Reactive dye red and preparation method and application thereof Download PDFInfo
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- CN112480708B CN112480708B CN202011152683.4A CN202011152683A CN112480708B CN 112480708 B CN112480708 B CN 112480708B CN 202011152683 A CN202011152683 A CN 202011152683A CN 112480708 B CN112480708 B CN 112480708B
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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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/513—Disazo or polyazo dyes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
- C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
- C09B62/08—Azo dyes
- C09B62/09—Disazo or polyazo 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
- 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
- D06P1/38—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 reactive dyes
- D06P1/382—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 reactive dyes reactive group directly attached to heterocyclic group
-
- 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
- D06P1/38—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 reactive dyes
- D06P1/384—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 reactive dyes reactive group not directly attached to heterocyclic group
-
- 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
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
- D06P3/663—Natural or regenerated cellulose using reactive dyes reactive group directly attached to heterocyclic group
-
- 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
- D06P3/58—Material containing hydroxyl groups
- D06P3/60—Natural or regenerated cellulose
- D06P3/66—Natural or regenerated cellulose using reactive dyes
- D06P3/666—Natural or regenerated cellulose using reactive dyes reactive group not directly attached to heterocyclic group
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- Engineering & Computer Science (AREA)
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Abstract
The invention relates to a reactive dye red and a preparation method and application thereof, wherein the structure of the reactive dye red is shown as a general formula (I):
Description
Technical Field
The invention belongs to the technical field of dyes, and particularly relates to a reactive dye red as well as a preparation method and application thereof.
Background
When the polyester-cotton blended fabric on the market is dyed, a common dyeing method is a two-bath method, namely, the fabric is dyed and washed by disperse dye, and then dyed and washed by reactive dye. Although the homochromatism is good and the fastness is high, the process is long, the energy consumption is excessive, the energy conservation and emission reduction and the clean production of printing and dyeing enterprises are not facilitated, and the problems of color splash and cylinder difference can be generated in the production along with the prolonging of the processing time, so that the product quality and the efficiency are influenced.
In order to solve the problems, many factories search for one-bath one-step dyeing of polyester cotton, but the existing reactive dye red still has poor high temperature resistance, can only dye at about 50 ℃, and is not suitable for one-bath one-step dyeing by matching with disperse dyes.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide an improved reactive dye red and a preparation method thereof.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a reactive dye red has a compound structure shown as a general formula (I):
in the formula:
R 1 、R 2 、R 3 、R 4 each independently selected from H or an alkali metal cation;
M 1 、M 2 、M 3 、M 4 are respectively and independently selected from X and SO 3 X is alkyl with 1-5 carbon atoms or alkoxy with 1-5 carbon atoms, and X is H or alkali metal cation;
F 1 、F 2 are respectively and independently selected from Y and SO 3 Y、
Y is H or alkali metal cation, m and n are respectively and independently selected from integers between 1 and 5;
A 1 、A 2 each independently selected from H or an alkali metal cation.
According to some embodiments of the invention, the alkali metal cation is Na, K or Li.
According to some implementation aspects of the invention, the M 1 、M 2 、M 3 、M 4 Are respectively and independently selected from H and SO 3 H、SO 3 Na、SO 3 K、SO 3 Li、CH 3 O or CH 3 。
According to some of the implementation aspects of the invention, said F 1 、F 2 Are respectively and independently selected from H and SO 3 H、SO 3 Na、SO 3 K、SO 3 Li、SO 2 C 2 H 5 、SO 2 C 2 H 4 Na、SO 2 C 2 H 4 K、SO 2 C 2 H4Li、SO 2 C 2 H 4 OSO 3 H、SO 2 C 2 H 4 OSO 3 Na、SO 2 C 2 H 4 OSO 3 K or SO 2 C 2 H 4 OSO 3 Li。
According to some embodiments of the invention, in the formula I, the two NH groups on the phenyl ring in the intermediate position are located in the para-position or meta-position, respectively, of the phenyl ring.
According to some embodiments of aspects of the invention, in the general formula I, the COOA 1 、COOA 2 Respectively at ortho, meta or para positions of the N group on the ring. Preferably, the COOA 1 、COOA 2 Each being meta to the N group on the ring.
According to some embodiment aspects of the invention, the compound of formula I is one of the compounds represented by the following structural formula:
the invention adopts another technical scheme that: a preparation method of reactive dye red comprises the following steps:
(1) Carrying out primary condensation reaction on a compound shown as a formula II and a compound shown as a formula III to obtain a condensate;
(2) Carrying out diazo reaction on a compound shown as a formula IV under the action of nitrous acid to obtain a first intermediate;
(3) Carrying out coupling reaction on the first condensate and the first intermediate to obtain a second intermediate;
(4) Carrying out secondary condensation reaction on the second intermediate and a compound shown as a formula V to obtain a secondary condensate;
(5) Carrying out tertiary condensation reaction on the secondary condensate and a compound shown in a formula VI to obtain reactive dye red;
M 1 、M 2 are each independently selected from X 1 、SO 3 X 1 An alkyl group having 1 to 5 carbon atoms or an alkoxy group having 1 to 5 carbon atoms, wherein X is 1 Is H or an alkali metal cation;
f is selected from Y 1 、SO 3 Y 1 、
Said Y is 1 Is H or alkali metal cation, m and n are respectively and independently selected from integers between 1 and 5;
R 1 、R 2 are independently selected from H or alkali metal cation;
a is selected from H or an alkali metal cation.
According to some embodiment aspects of the invention, the M 1 、M 2 Are respectively and independently selected from H and SO 3 H、SO 3 Na、SO 3 K、SO 3 Li、CH 3 O or CH 3 。
According to some embodiment aspects of the invention, F is selected from H, SO 3 H、SO 3 Na、SO 3 K、SO 3 Li、SO 2 C 2 H 5 、SO 2 C 2 H 4 Na、SO 2 C 2 H 4 K、SO 2 C 2 H 4 Li、SO 2 C 2 H 4 OSO 3 H、SO 2 C 2 H 4 OSO 3 Na、SO 2 C 2 H 4 OSO 3 K or SO 2 C 2 H 4 OSO 3 Li。
According to some embodiment aspects of the invention, the R is 1 、R 2 Each independently selected from H, na, K or Li. Preferably, said R is 1 、R 2 Are respectively and independently selected from H or Na, and are not simultaneously Na.
According to some embodiments of an aspect of the invention, in the formula V, di is on the benzene ringNH 2 2 The groups are located in the para or meta position, respectively, of the phenyl ring.
According to some embodiment aspects of the invention, a is selected from H, na, K or Li.
According to some embodiment aspects of the invention, in formula VI, COOA is ortho, meta or para to the N group on the ring. Preferably, in said formula VI, COOA is meta to the N group on the ring.
According to some embodiments of the present invention, step (1) is performed by: mixing the compound shown in the formula II and the compound shown in the formula III with water, and stirring at the pH value of 1.5-3.0 and the temperature of 0-15 ℃ for reaction to prepare the monoacid condensate, wherein the feeding molar ratio of the compound shown in the formula II to the compound shown in the formula III is 1.97-1.02.
According to some implementation aspects of the invention, the step (2) is implemented as follows: mixing the compound shown in the formula IV, hydrochloric acid, nitrite and water, and stirring for reaction at 0-15 ℃ to obtain the first intermediate, wherein the feeding molar ratio of the compound shown in the formula IV, HCl and nitrite ions is 1 (1-2.5) to 1-1.1.
According to some embodiments of the present invention, in the step (3), the first condensate and the first intermediate are fed according to a feeding molar ratio of the compound represented by the formula III to the compound represented by the formula IV of 1.97-1.01, and the coupling reaction is performed at a pH of 4.5-7.0 and a temperature of 10-20 ℃.
According to some embodiments of the invention, in the step (4), the feeding molar ratio of the compound represented by the formula V to the compound represented by the formula II is 1.0-2.1, and the secondary condensation reaction is performed at a pH value of 4.5-6.0 and a temperature of 30-45 ℃.
According to some embodiments of the invention, in step (5), the molar ratio of the compound of formula II to the compound of formula VI is 1.0-3.5, and the three-time condensation reaction is performed at a pH of 5.0-7.0 and a temperature of 75-90 ℃.
According to some embodiment aspects of the invention, the method of making is embodied by the steps of:
(1) Mixing the compound shown in the formula II and the compound shown in the formula III with ice water, adding weak base to adjust the pH value to 1.5-3.0, and then stirring and reacting for 2-4 h at 0-15 ℃ to obtain a first reaction solution, wherein the weak base is one or more of sodium bicarbonate, potassium bicarbonate and lithium bicarbonate;
(2) Mixing the compound shown in the formula IV, hydrochloric acid, sodium nitrite and ice water, and stirring and reacting for 1-3 hours at the temperature of 0-15 ℃ to obtain a second reaction solution;
(3) Mixing the first reaction solution and the second reaction solution, adding weak base to adjust the pH value to 4.5-7.0, and reacting for 4-6 h at 10-20 ℃ to obtain a third reaction solution, wherein the weak base is one or more of sodium bicarbonate, potassium bicarbonate and lithium bicarbonate;
(4) Adding the compound shown in the formula V into the third reaction liquid, adding weak base to adjust the pH value to 4.5-6.0, and reacting for 2-5 h at 30-45 ℃ to obtain a fourth reaction liquid, wherein the weak base is one or more of sodium bicarbonate, potassium bicarbonate and lithium bicarbonate;
(5) Adding the compound shown in the formula VI into the fourth reaction liquid, adding strong base to adjust the pH value to be 5.0-7.0, and reacting for 6-9 h at 75-90 ℃ to obtain a fifth reaction liquid, wherein the strong base is one or more of sodium carbonate, lithium carbonate and potassium carbonate;
(6) And drying the fifth reaction solution to obtain the reactive dye red.
According to yet another technical scheme adopted by the invention, the reactive dye red is applied to pure cotton, rayon, T/R or T/C blended fabrics.
When the reactive dye red is used for dyeing pure cotton (or rayon), the reactive dye red and anhydrous sodium sulphate are dissolved in water, the temperature is raised to 100-130 ℃, and the pure cotton (or rayon) is subjected to heat preservation dyeing, cooling, water washing and soaping.
The addition amount of the reactive dye red and the anhydrous sodium sulphate can be added according to the existing addition amount of the reactive dye and the anhydrous sodium sulphate, and the heat preservation is usually 20-60 min. Such as about 40 min.
Due to the application of the technical scheme, compared with the prior art, the invention has the following advantages:
the reactive dye has higher reactivity, good color fixing capability and good dyeing capability, and the reactive dye does not need to be added with soda for color fixing during dyeing, so that the use of the soda is avoided. Meanwhile, the reactive dye also has high temperature resistance, can be used in cooperation with a disperse dye, and can simultaneously dye T/R or T/C blended products at a temperature higher than 100 ℃, so that a one-bath dyeing process is realized, the dyeing process is simplified, the dyeing time is shortened, the discharge capacity is greatly reduced, and the labor cost and the energy consumption are reduced.
Detailed Description
In order to make the objects, technical solutions and effects of the present invention clearer and clearer, the present invention is described in further detail below. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The raw materials in the following examples are commercially available. The hydrochloric acid used is 30% strength hydrochloric acid.
Example 1
The reactive dye red provided in this example is prepared by the following method:
(1) Will be provided with
Adding into crushed ice and water, stirring, and adding
Then adding sodium bicarbonate to adjust the pH value to 2.0-2.5, reacting for 3.5h at the temperature of 5-10 ℃ to obtain a first mixed solution, wherein,
and with
The feeding molar ratio of (1);
(2) Will be provided with
Adding the mixture into water and crushed ice, stirring, keeping the temperature at 0-5 ℃, adding hydrochloric acid, then adding sodium nitrite, reacting for 1.5 hours to obtain a second mixed solution, wherein,
the feeding molar ratio of HCl to sodium nitrite is 1.0;
(3) Adding the second mixed solution obtained in the step (2) into the first mixed solution obtained in the step (1), adding sodium bicarbonate to adjust the pH value to 5.5-6.0, and reacting at 10-15 ℃ for 5.5h to obtain a third mixed solution, wherein the feeding of the first mixed solution and the second mixed solution is carried out according to the proportion
And
the feeding molar ratio of (1);
(4) Will be provided with
Adding the third mixed solution obtained in the step (3), adding sodium bicarbonate to adjust the pH value to 5.5-6.0, reacting for 2.5h at the temperature of 30-35 ℃ to obtain a fourth mixed solution, wherein,
and with
The feeding molar ratio of (1);
(5) Will be provided with
Adding the mixture into the fourth mixed solution obtained in the step (4), adding sodium carbonate to adjust the pH value to 5.5-6.0, reacting for 6.5h at the temperature of 75-80 ℃ to obtain a fifth mixed solution, wherein,
and
the feeding molar ratio of (1);
(6) And (6) drying the fifth mixed solution obtained in the step (5) to obtain the product, namely the reactive dye red.
The structural formula of the product is as follows:
example 2
The reactive dye red provided in this example is prepared by the following method:
(1) Will be provided with
Adding into crushed ice and water, stirring
Adding sodium bicarbonate to regulate pH value to 2.0-2.5, reacting at 5-10 deg.c for 3 hr to obtain the first mixed solution,
and
the feeding molar ratio of (1);
(2) Will be provided with
Adding the mixture into water and crushed ice, stirring, keeping the temperature at 5-8 ℃, adding hydrochloric acid, and then adding sodium nitrite to react for 1.5 hours to obtain a second mixed solution, wherein
The feeding molar ratio of HCl to sodium nitrite is 1.0;
(3) Adding the second mixed solution obtained in the step (2) into the second mixed solution obtained in the step (1)Adding sodium bicarbonate into the first mixed solution to adjust the pH value to 5.5-6.0, and reacting for 5 hours at the temperature of 10-15 ℃ to obtain a third mixed solution, wherein the feeding of the first mixed solution and the second mixed solution is carried out according to the proportion
And with
The feeding molar ratio of (1);
(4) Will be provided with
Adding the third mixed solution obtained in the step (3), adding sodium bicarbonate to adjust the pH value to 5.5-6.0, reacting for 3 hours at the temperature of 30-35 ℃ to obtain a fourth mixed solution, wherein,
and
the feeding molar ratio of (1);
(5) Will be provided with
Adding the mixture into the fourth mixed solution obtained in the step (4), adding sodium carbonate to adjust the pH value to 5.5-6.0, reacting for 6 hours at the temperature of 75-80 ℃ to obtain a fifth mixed solution, wherein,
and
the feeding molar ratio of (1);
(6) And (6) drying the fifth mixed solution obtained in the step (5) to obtain the product, namely the reactive dye red.
The structural formula of the product is as follows:
example 3
The reactive dye red provided in this example is prepared by the following method:
(1) Will be provided with
Adding into crushed ice and water, stirring, and adding
Adding sodium bicarbonate to adjust the pH value to 2.0-2.5, reacting for 4 hours at the temperature of 5-10 ℃ to obtain a first mixed solution, wherein,
and with
The feeding molar ratio of (1);
(2) Will be provided with
Adding the mixture into water and crushed ice, stirring, keeping the temperature at 0-5 ℃, adding hydrochloric acid, adding sodium nitrite, reacting for 1.5 hours to obtain a second mixed solution, wherein,
the feeding molar ratio of HCl to sodium nitrite is 1.0;
(3) Adding the second mixed solution obtained in the step (2) into the first mixed solution obtained in the step (1), adding sodium bicarbonate to adjust the pH value to 5.5-6.0, and reacting at 10-15 ℃ for 6h to obtain a third mixed solution, wherein the feeding of the first mixed solution and the second mixed solution is carried out according to the proportion
And
the feeding molar ratio of (1)Feeding the materials in rows;
(4) Will be provided with
Adding the third mixed solution obtained in the step (3), adding sodium bicarbonate to adjust the pH value to 5.5-6.0, reacting for 3 hours at the temperature of 40-45 ℃ to obtain a fourth mixed solution, wherein,
and
the feeding molar ratio of (1);
(5) Will be provided with
Adding the mixture into the fourth mixed solution obtained in the step (4), adding sodium carbonate to adjust the pH value to 5.5-6.0, reacting for 6 hours at the temperature of 75-80 ℃ to obtain a fifth mixed solution, wherein,
and with
The feeding molar ratio of (1);
(6) And (5) drying the fifth mixed solution obtained in the step (5) to obtain the product, namely the reactive dye red.
The structural formula of the product is as follows:
example 4
The reactive dye red provided in this example is prepared by the following method:
(1) Will be provided with
Adding into crushed ice and water, stirring, and adding
Adding sodium bicarbonate to adjust the pH value to 2.0-2.5, reacting for 4 hours at the temperature of 5-10 ℃ to obtain a first mixed solution, wherein,
and
the feeding molar ratio of (1);
(2) Will be provided with
Adding the mixture into water and crushed ice, stirring, keeping the temperature at 0-5 ℃, adding hydrochloric acid, adding sodium nitrite, reacting for 1.5 hours to obtain a second mixed solution, wherein,
the feeding molar ratio of HCl to sodium nitrite is 1.0;
(3) Adding the second mixed solution obtained in the step (2) into the first mixed solution obtained in the step (1), adding sodium bicarbonate to adjust the pH value to 5.5-6.0, and reacting at 10-15 ℃ for 5h to obtain a third mixed solution, wherein the feeding of the first mixed solution and the second mixed solution is carried out according to the proportion
And with
The feeding molar ratio of (1);
(4) Will be provided with
Adding the third mixed solution obtained in the step (3), adding sodium bicarbonate to adjust the pH value to 5.5-6.0, reacting for 3 hours at the temperature of 30-35 ℃ to obtain a fourth mixed solution, wherein,
and with
The feeding molar ratio of (1);
(5) Will be provided with
Adding the mixture into the fourth mixed solution obtained in the step (4), adding sodium carbonate to adjust the pH value to 5.5-6.0, reacting for 7 hours at the temperature of 75-80 ℃ to obtain a fifth mixed solution, wherein,
and
the feeding molar ratio of (1);
(6) And (6) drying the fifth mixed solution obtained in the step (5) to obtain the product, namely the reactive dye red.
The structural formula of the product is as follows:
comparative example 1
Commercially available reactive dye red has the following structural formula:
performance testing
1. Preparation of dyeing liquor
The reactive dyes of examples 1 to 4 and comparative example 1 were each weighed 2% by dyeing depth, 60g/l by anhydrous sodium sulphate, bath ratio 1:10, preparing each dyeing solution for later use.
2. Dyeing process (pure cotton)
The dyeing process using the dyeing liquids of examples 1 to 4: the dyeing liquid prepared by the reactive dyes of the examples 1 to 4 is heated, and pure cotton is dyed, washed and soaped, so that the dyeing is finished.
Dyeing process using the dyeing liquor of comparative example 1: the dyeing liquid prepared by the reactive dye of the comparative example 1 is heated, and the sodium carbonate (the dosage is 20 g/l) is added to dye, wash and soap the pure cotton, thus completing the dyeing.
3. Optimal coloring temperature determination
The dyeing solutions prepared by using the reactive dyes of example 1 and comparative example 1 were used to dye 12 cotton pieces of the same color at 60 ℃, 80 ℃, 100 ℃, 110 ℃, 120 ℃ and 130 ℃ respectively according to the above dyeing process, the color yields of the 12 dyed cotton pieces were measured respectively, and the relative color yields of the cotton pieces at 60 ℃, 80 ℃, 100 ℃, 110 ℃ and 120 ℃ were calculated respectively using the color yields at 130 ℃ as a reference standard, and the results are shown in table 1.
Table 1 shows the optimum coloring temperatures of the reactive dye of example 1 compared with that of comparative example 1
As can be seen from Table 1, the optimum coloring temperature of the reactive dye of example 1 is 100-130 ℃.
The dyeing solutions prepared from the reactive dyes of examples 2 to 4 were used to dye different pure cotton of the same color at 60 ℃, 80 ℃, 100 ℃, 110 ℃, 120 ℃ and 130 ℃, respectively, and the optimal coloring temperature was also 100 to 130 ℃.
As can be seen from the above, the reactive dyes of examples 1 to 4 of the present invention are preferably used at a dyeing temperature of 100 to 130 ℃ and the same dyeing temperature as that of the disperse dye (110 to 130 ℃), and can be mixed with the disperse dye to carry out one-bath dyeing. In addition, the reactive dyes of the embodiments 1 to 4 of the invention do not need to be added with soda for color fixation when being dyed.
The best coloring temperature of the existing common reactive dye is about 60 ℃, the dye cannot be simultaneously dyed with the disperse dye in one bath, and sodium carbonate is added for fixation during dyeing, so that the dyeing cost is increased, and the sewage and sludge treatment cost is also increased.
4. Testing of light resistance, wash resistance, perspiration resistance, friction resistance, hot press resistance, solubility
1) The dyeing liquid prepared by the reactive dyes of the examples 1 to 4 is heated to 100 ℃, and pure cotton is dyed after being kept warm for 40min, cooled, washed and soaped, thus completing dyeing.
2) The dyeing liquid prepared by the reactive dye of the comparative example 1 is heated to 60 ℃, pure cotton is dyed, sodium carbonate (20 g/l) is added for fixation, the temperature is kept for 40min, and the dyeing is finished after cooling, washing and soaping.
The dyed pure cotton cloth was subjected to performance test, and the results are shown in table 2.
Table 2 shows the performance tests of the reactive dye reds of examples 1 to 4 and comparative example 1
As can be seen from Table 2, the reactive dyes of examples 1 to 4 of the present invention, when dyed at a high temperature of 100 ℃, have a fastness comparable to or superior to that of the conventional reactive dyes at 60 ℃. As is clear from the above Table 1, the dyeing properties of the conventional reactive dyes are poor when the dyes are dyed at a high temperature of 100 ℃.
The above performance tests were performed using the following criteria:
1) Color fastness to rubbing: GB/T3920-2008
2) Color fastness to perspiration: GB/T3922-2013
3) Color fastness to light: GB/T8427-2008. Method 3
4) Color fastness to washing: GB/T3921-2008. Method 3
5) Heat resistance at 200 ℃: GB/T6152-1997.
6) Solubility: GB/T21879-2015.
5. Polyester cotton one-bath dyeing
The reactive dye of example 1 was mixed at room temperature in a dyeing depth of 2% o.w.f, a commercially available disperse dye red T-2B (wujiang peach-derived dye) in a dyeing depth of 0.96o.w.f, anhydrous sodium sulphate 60g/l, a bath ratio of 1:10 to prepare a staining solution. And heating the dyeing liquid to 110-130 ℃, performing heat preservation dyeing on the cotton-polyester blended fabric for 40min, cooling, washing with water, and soaping to finish dyeing.
The result shows that the cloth surface is full in color when the disperse dye red T-2B is used for dyeing in one bath in the embodiment 1, and the dyeing effect of the two-bath method can be achieved because the polyester and cotton are dyed without color difference.
The above embodiments are merely illustrative of the technical ideas and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and these ranges or values should be understood to encompass values close to these ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
Claims (4)
1. The application of reactive dye red and disperse dye to one-bath dyeing of T/R or T/C blended products is characterized in that: the reactive dye red has the following compounds:
2. the use according to claim 1, characterized in that the process for the preparation of the reactive dye red comprises the following steps:
(1) Make it
And
carrying out primary condensation reaction to obtain a condensate;
(2) Make it
Carrying out diazo reaction under the action of nitrous acid to obtain a first intermediate;
(3) Carrying out coupling reaction on the first condensate and the first intermediate to obtain a second intermediate;
(4) Reacting said second intermediate with
Carrying out secondary condensation reaction to obtain a secondary condensate;
(5) Making the two-condensed material and
carrying out condensation reaction for three times to obtain the reactive dye red.
3. Use according to claim 2, characterized in that: the specific implementation process of the step (1) is as follows: will be described in
Mixing with water, stirring and reacting at the pH of 1.5-3.0 and the temperature of 0-15 ℃ to obtain the polycondensate, wherein the polycondensate is prepared
And
the feeding molar ratio of (1);
the specific implementation process of the step (2) is as follows: will be described in
Mixing hydrochloric acid, nitrite and water, and stirring and reacting at 0-15 ℃ to prepare the first intermediate, wherein the first intermediate is prepared
The feeding molar ratio of HCl to nitrite ions is 1 (1-2.5) to 1-1.1;
in the step (3), the first condensate and the first intermediate are fed according to the proportion
And
the feeding molar ratio of (1) is 1.97-1.01, and the coupling reaction is carried out at a pH value of 4.5-7.0 and a temperature of 10-20 ℃;
in the step (4), the
And with
The feeding molar ratio of (A) is 1.0-2.1, and the secondary condensation reaction is carried out at a pH value of 4.5-6.0 and a temperature of 30-45 ℃;
in the step (5), the
And
the feeding molar ratio of (A) is 1.0-3.5, and the third condensation reaction is carried out at a pH value of 5.0-7.0 and a temperature of 75-90 ℃.
4. Use according to claim 2 or 3, characterized in that the implementation of the preparation method comprises the following steps:
(1) Will be described in
Mixing with ice water, adding weak base to regulate pH value to 1.5-3.0, stirring at 0-15 deg.c to react for 2-4 hr to obtain the first reactionThe weak base is one or more of sodium bicarbonate, potassium bicarbonate and lithium bicarbonate;
(2) Will be described in
Mixing hydrochloric acid, sodium nitrite and ice water, and stirring and reacting for 1-3 h at 0-15 ℃ to obtain a second reaction solution;
(3) Mixing the first reaction solution and the second reaction solution, adding weak base to adjust the pH value to 4.5-7.0, and reacting for 4-6 h at 10-20 ℃ to obtain a third reaction solution, wherein the weak base is one or more of sodium bicarbonate, potassium bicarbonate and lithium bicarbonate;
(4) Will be described in
Adding the mixture into the third reaction solution, adding weak base to adjust the pH value to be 4.5-6.0, and reacting for 2-5 h at the temperature of 30-45 ℃ to obtain a fourth reaction solution, wherein the weak base is one or more of sodium bicarbonate, potassium bicarbonate and lithium bicarbonate;
(5) Will be described in
Adding the mixture into the fourth reaction liquid, adding strong base to adjust the pH value to 5.0-7.0, and reacting for 6-9 hours at 75-90 ℃ to obtain fifth reaction liquid, wherein the strong base is one or more of sodium carbonate, lithium carbonate and potassium carbonate;
(6) And drying the fifth reaction solution to obtain the reactive dye red.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS58186682A (en) * | 1982-04-27 | 1983-10-31 | 日本化薬株式会社 | Dyeing of cellulose or cellulose containing fiber material |
| JPH0723586B2 (en) * | 1984-02-20 | 1995-03-15 | 住友化学工業株式会社 | Dyeing method for cellulose fiber materials |
| JPS60208368A (en) * | 1984-04-02 | 1985-10-19 | Sumitomo Chem Co Ltd | Reactive dye composition |
| JPS60208366A (en) * | 1984-04-02 | 1985-10-19 | Sumitomo Chem Co Ltd | Triazine compound and dyeing or printing of fibrous material using the same |
| JPS6155275A (en) * | 1984-08-20 | 1986-03-19 | 日本化薬株式会社 | Fastness dyeing of natural leather |
| JPH0655906B2 (en) * | 1985-03-29 | 1994-07-27 | 日本化薬株式会社 | Reactive dye composition |
| DE3636398A1 (en) * | 1986-10-25 | 1988-05-05 | Hoechst Ag | WATER-SOLUBLE DISAZO COMPOUNDS, METHOD FOR THEIR PRODUCTION AND THEIR USE AS DYES |
| JPH10315612A (en) * | 1997-05-19 | 1998-12-02 | Sony Corp | Recording method |
| JP2000044830A (en) * | 1998-05-22 | 2000-02-15 | Sumitomo Chem Co Ltd | Reactive dye composition and its application |
| JP2001214087A (en) * | 2000-02-04 | 2001-08-07 | Sumitomo Chem Co Ltd | Reactive dye composition and dyeing method using the same |
| CN104371357A (en) * | 2014-09-29 | 2015-02-25 | 浙江亿得化工有限公司 | Low-alkali or alkali-free active bright-red dye and preparation method thereof |
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