CN112852185B - Blue fluorine-containing reactive dye with high fixation rate and preparation method thereof - Google Patents
Blue fluorine-containing reactive dye with high fixation rate and preparation method thereof Download PDFInfo
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- CN112852185B CN112852185B CN202011624230.7A CN202011624230A CN112852185B CN 112852185 B CN112852185 B CN 112852185B CN 202011624230 A CN202011624230 A CN 202011624230A CN 112852185 B CN112852185 B CN 112852185B
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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
- C09B62/505—Anthracene dyes
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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
- C09B62/78—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 with other reactive groups
- C09B62/80—Anthracene dyes
Abstract
The application relates to the field of reactive dyes, and particularly discloses a blue fluorine-containing reactive dye with high fixation rate. The preparation method of the blue fluorine-containing reactive dye with high fixation rate comprises the following steps: a. carrying out Ullmann reaction; b. refining; c. carrying out secondary condensation reaction; d. and (3) carrying out tertiary condensation reaction. The product has the advantages of higher color fixing rate, bright color, high light fastness, washing fastness, high rubbing fastness and the like.
Description
Technical Field
The application relates to the field of reactive dyes, in particular to a blue fluorine-containing reactive dye with high fixation rate and a preparation method thereof.
Background
The reactive dye is a dye with the widest application range of cellulose fiber textiles, the application range and the requirement of the reactive dye have great proportion in the dye, and the reactive dye has the tendency of replacing reduction, vulcanization and insoluble azo dyes. However, the utilization rate of the existing reactive dye is not high, generally 70-80%, and the reactive dye is easy to discolor and migrate during heat treatment in processing after dyeing. A large amount of colored sewage is generated after dyeing, and great pollution is brought to the environment. Furthermore, unfixed hydrolysed dye is not always completely washable, which in turn affects the fastness properties of the dyeings.
Therefore, the inventor believes that aiming at the problems of low fixation rate, easy color change and easy migration of the existing reactive dyes, the development of the reactive dyes is urgently needed, and aims to solve the problems.
Disclosure of Invention
In order to solve the problems of low fixation rate, easy color change and easy migration of the existing reactive dye, the application provides a blue fluorine-containing reactive dye with high fixation rate and a preparation method thereof.
In a first aspect, the application provides a blue fluorine-containing reactive dye with high fixation rate, which adopts the following technical scheme:
a blue fluorine-containing reactive dye with high fixation rate has a structural general formula as shown in formula (I):
wherein R is 1 、R 2 is-H;
R 3 is one of the following formulas:
-NHCH 2 CH 2 OCH 2 CH 2 SO 2 CH 2 CH 2 Cl；
m is an alkali metal.
By adopting the technical scheme, experimental data show that the reactive dye with the structural formula (I) has good effects of high color fixing rate and high fastness.
Optionally, M is selected from one of Na or K.
Optionally, M is Na.
Alternatively, R3 is-NHCH 2 CH 2 OCH 2 CH 2 SO 2 CH 2 CH 2 Cl。
By adopting the technical scheme, NHCH is preferentially adopted 2 CH 2 OCH 2 CH 2 SO 2 CH 2 CH 2 Cl is condensed three times because of-NHCH 2 CH 2 OCH 2 CH 2 SO 2 CH 2 CH 2 Cl is a linear active group, the color fixing rate of the synthesized dye after dyeing is relatively higher, and good effects of high color fixing rate and high fastness can be obtained.
In a second aspect, the present application provides a preparation method of a blue fluorine-containing reactive dye with high fixation rate, which adopts the following technical scheme:
a preparation method of blue fluorine-containing reactive dye with high fixation rate comprises the following steps:
a. ullmann reaction: pulping bromamine acid and water, adding p-biphenyldiamine-2, 5-disulfonic acid sodium solution and catalyst, heating to 90-95 ℃, and reacting to obtain the product with the structural formula
The primary condensate of (a);
b. refining: adding active carbon into the primary condensation compound obtained in the step a for adsorption, and filtering twice to obtain a secondary refined filter cake;
c. secondary condensation reaction: b, pulping the secondary refined filter cake obtained in the step b by using water, adding the cyanuric fluoride, and reacting to obtain the compound with the structural formula
A secondary condensate of (a);
d. and (3) tertiary condensation reaction: adding NHCH to the secondary condensate obtained in the step c 2 CH 2 OCH 2 CH 2 SO 2 CH 2 CH 2 Cl、
One of the three raw materials reacts to obtain a tertiary condensate, and the structural formula of the tertiary condensate is one of the following formulas:
e. product treatment: and d, filtering the tertiary condensation compound obtained in the step d, retaining insoluble substances, and performing spray drying to obtain the finished dye.
Optionally, in the step a, the added catalyst comprises the following components in parts by weight: 100 parts of cuprous chloride, 5 parts of copper sulfate and 2 parts of copper powder.
By adopting the technical scheme, the catalyst with the composition and the proportion can play a good role in promoting the Ullmann reaction and reduce the generation of byproducts.
Optionally, in the step b, the primary condensation compound is cooled to 50 ℃, and then activated carbon is added for adsorption, and a primary refined solution is obtained through filtration; adjusting pH of the primary refined solution to 1.0-1.5 with hydrochloric acid, adding sodium chloride solution, standing for 2 hr, and filtering again.
By adopting the technical scheme, the primary condensation compound is subjected to the filtering steps, so that the refining and purifying efficiency can be improved, and the purifying effect is better.
Optionally, in the step c, after the secondary refined filter cake is pulped with water, the pH of the secondary refined filter cake is adjusted to 5.0-6.0 with liquid alkali, and the temperature is reduced to 0-5 ℃.
By adopting the technical scheme, the secondary refined filter cake can be dissolved and clarified at the pH value of 5.0-6.0 and the temperature of 0-5 ℃, so that better conversion rate of the secondary condensation reaction is obtained.
Optionally, in the step c, the cyanuric fluoride is added and the temperature is maintained at 0-5 ℃ for reaction for 1.5h, and a secondary condensation compound is obtained after the reaction.
By adopting the technical scheme, after the melamine is added, the reaction is maintained at the low temperature of 0-5 ℃, so that the hydrolysis of the melamine can be reduced, and the secondary condensation yield is improved.
Optionally, in the step d, after the raw material of R3 is added, the pH is adjusted to 5.0 to 6.0, the temperature is raised to 30 to 35 ℃, then the pH is maintained at 5.0 to 6.0, the reaction is carried out for 0.5h, and then the pH is adjusted to 5.5 to 6.5 with hydrochloric acid, so as to obtain a tertiary condensate.
In summary, the present application has the following beneficial effects:
1. the reactive dye prepared by the method has good color fixing rate, bright color, high light fastness, washing fastness, high rubbing fastness and other excellent performances, and is an energy-saving emission-reducing green environment-friendly reactive dye.
2. Preference is given to using-NHCH in the present application 2 CH 2 OCH 2 CH 2 SO 2 CH 2 CH 2 The Cl raw material obtains excellent effects of high color fixing rate and high fastness due to the characteristics of linear active groups.
3. According to the method, the low-temperature condensation method is adopted, so that the cyanuric fluoride is not easy to hydrolyze in the secondary condensation reaction, and the effect of high conversion rate is achieved.
Detailed Description
The present application is further described in detail with reference to the following examples, which are intended to illustrate: the following examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer, and all the starting materials in the following examples were obtained from the ordinary commercial sources except for the specific conditions.
Examples
Example 1
The blue fluorine-containing reactive dye with high fixation rate has a structure shown as a formula (IV) -1:
the embodiment also provides a preparation method of the blue fluorine-containing reactive dye with high fixation rate, which comprises the following steps:
a. ullmann reaction: pulping 1mol of bromamine acid with 100ml of water, heating to 50 ℃ for dispersion, adding 200ml of p-phenylenediamine-2, 5-disulfonic acid sodium solution with the molar concentration of 1.05mol/L, adding 0.1mol of cuprous chloride, 0.05mol of copper sulfate and 0.02mol of copper powder, heating to 90 ℃ for reaction for 6 hours to obtain a primary condensation compound, and performing chromatographic detection on an end point to obtain a primary condensation compound with the main purity of HPLC being more than 97 percent, wherein the structural formula of the primary condensation compound is shown in the specification
b. Refining: cooling the primary condensation compound solution obtained in the step a to 50 ℃, adding 0.03mol of activated carbon for adsorption, and filtering to obtain a primary refined solution; adjusting the pH value of the primary refined solution to 1.0 by using hydrochloric acid, adding solid sodium chloride accounting for 15% of the volume of the primary refined solution, maintaining for 2 hours, separating out a sample application material, and performing filter pressing to obtain a secondary refined filter cake;
c. secondary condensation reaction: b, pulping the secondary refined filter cake obtained in the step b by using water, adjusting the pH value to 5.0 by using liquid alkali, reducing the temperature to 0 ℃, adding 1.2mol of cyanuric fluoride, simultaneously adjusting the pH value to 5.0 by using liquid alkali, controlling the temperature to 0 ℃, completely maintaining the pH value and the temperature for 0.5h, adjusting the pH value to 8.0 by using liquid alkali, maintaining for 1h, and reacting to obtain the compound with the structural formula of
A secondary condensate of (a);
d. and (3) tertiary condensation reaction: adding 1.1mol of-NHCH to the secondary condensate obtained in the step c 2 CH 2 OCH 2 CH 2 SO 2 CH 2 CH 2 Adjusting the pH value to 5.0 by Cl and liquid alkali, heating to 30 ℃, maintaining for half an hour, and adjusting the pH value to 5.0 by hydrochloric acid. Reacting to obtain a compound with a structural formula
The tertiary condensate of (4);
e. product treatment: and d, passing the tertiary condensate obtained in the step d through insoluble substances, and spray drying to obtain the product. Example 2
The blue fluorine-containing reactive dye with high fixation rate has a structure shown in a formula (I) -2:
the embodiment also provides a preparation method of the blue fluorine-containing reactive dye with high fixation rate, which comprises the following steps:
a. ullmann reaction: pulping 1mol of bromamine acid with 100ml of water, heating to 50 ℃ for dispersion, adding 200ml of p-phenylenediamine-2, 5-disulfonic acid sodium solution with the molar concentration of 1.08mol/L, adding 0.1mol of cuprous chloride, 0.05mol of copper sulfate and 0.02mol of copper powder, heating to 93 ℃ for reaction for 6 hours to obtain a primary condensation compound, and performing chromatographic detection on an end point to obtain a primary condensation compound with the main purity of HPLC being more than 97 percent, wherein the structural formula of the primary condensation compound is shown in the specification
b. Refining: cooling the primary condensation compound solution obtained in the step a to 50 ℃, adding 0.03mol of activated carbon for adsorption, and filtering to obtain a primary refined solution; adjusting the pH value of the primary refined solution to 1.2 by using hydrochloric acid, adding solid sodium chloride with the volume of 15% of the liquid volume, maintaining for 2 hours, separating out a sample application material, and performing filter pressing to obtain a secondary refined filter cake;
c. secondary condensation reaction: b, pulping the secondary refined filter cake obtained in the step b by using water, adjusting the pH value to 5.5 by using liquid alkali, reducing the temperature to 2 ℃, adding 1.3mol of cyanuric fluoride, simultaneously maintaining the pH value to 5.5 by using the liquid alkali, maintaining the temperature to 2 ℃, completely maintaining the pH value and the temperature for 0.5h, adjusting the pH value to 8.3 by using the liquid alkali, maintaining for 1h, and reacting to obtain the compound with the structural formula of
A secondary condensate of (a);
d. and (3) tertiary condensation reaction: adding 1.2mol of the secondary condensate obtained in the step c
Adjusting pH to 5.5 with liquid alkali, heating to 32 deg.C, and maintaining at half of the temperatureAfter hours, the pH was adjusted back to 5.5 with hydrochloric acid. Reacting to obtain a compound with a structural formula
The tertiary condensate of (2);
e. product treatment: and d, passing the tertiary condensate obtained in the step d through insoluble substances, and spray drying to obtain the product.
Example 3
The blue fluorine-containing reactive dye with high fixation rate has a structure shown in a formula (I) -3:
the embodiment also provides a preparation method of the blue fluorine-containing reactive dye with high fixation rate, which comprises the following steps:
a. ullmann reaction: pulping 1mol of bromamine acid with 100ml of water, heating to 50 ℃ for dispersion, adding 200ml of p-phenylenediamine-2, 5-disulfonic acid sodium solution with the molar concentration of 1.1mol/L, adding 0.1mol of cuprous chloride, 0.05mol of copper sulfate and 0.02mol of copper powder, heating to 95 ℃ for reaction for 6 hours to obtain a primary condensation compound, and performing chromatographic detection on an end point to obtain a primary condensation compound with the main purity of HPLC being more than 97 percent, wherein the structural formula of the primary condensation compound is shown in the specification
b. Refining: cooling the primary condensation compound solution obtained in the step a to 50 ℃, adding 0.03mol of activated carbon for adsorption, and filtering to obtain a primary refined solution; adjusting the pH value of the primary refined solution to 1.5 by using hydrochloric acid, adding solid sodium chloride accounting for 15% of the volume of the primary refined solution, maintaining for 2 hours, separating out a sample application material, and performing filter pressing to obtain a secondary refined filter cake;
c. secondary condensation reaction: b, pulping the secondary refined filter cake obtained in the step b by using water, adjusting the pH value to 6.0 by using liquid alkali, reducing the temperature to 5 ℃, adding 1.4mol of cyanuric fluoride, simultaneously maintaining the pH value to be adjusted to 0 by using the liquid alkali, maintaining the temperature to be 5 ℃, completely maintaining the pH value and the temperature for 0.5h, adjusting the pH value to 8.5 by using the liquid alkali, maintaining for 1h, and reacting to obtain the compound with the structural formula of
A secondary condensate of (a);
d. and (3) tertiary condensation reaction: adding 1.3mol of the secondary condensate obtained in the step c
Adjusting pH to 6.0 with liquid alkali, heating to 35 deg.C, maintaining for half an hour, and adjusting pH to 6.0 with hydrochloric acid. Reacting to obtain a compound with a structural formula
The tertiary condensate of (4);
e. product treatment: and d, passing the tertiary condensate obtained in the step d through insoluble substances, and spray drying to obtain the product.
Performance test
Dyeing and sample preparation: 4g each of the dyes prepared in examples 1 to 3 were dissolved in water and then brought to a volume of 500 ml. Sucking 10ml of dye liquor, mixing with 50ml of water, adding 4g of cotton cloth and 1g of sodium sulfate, raising the temperature to 60 ℃ at the heating rate of 1 ℃/min, keeping the temperature for 30 minutes, adding 0.5g of sodium carbonate, keeping the temperature for 60 ℃ for dyeing for 30 minutes, taking out the dyed cotton cloth, boiling and soaping the dyed cotton cloth for 15 minutes by using a non-ionic detergent, cleaning the dyed cotton cloth by using water at the temperature of 60 ℃, and drying the dyed cotton cloth at the temperature of about 70 ℃ to obtain bright blue fabric with bright color and good leveling property.
The brilliant blue fabrics dyed with the dyes of examples 1 to 3 were tested according to the GB/T2391, ISO205C04, ISO105B02, ISO102-X12 test standards, respectively, and the results are shown in the following table.
As can be seen from the data in the table above, the reactive dye prepared by the method has the color fixing rate of over 90 percent, and has good light fastness, washing fastness and rubbing fastness. The fixation rate and the various color fastnesses of example 1 were optimized.
The present embodiment is only for explaining the present application, and it is not limited to the present application, and those skilled in the art can make modifications of the present embodiment without inventive contribution as needed after reading the present specification, but all of them are protected by patent law within the scope of the claims of the present application.
Claims (9)
1. A blue fluorine-containing reactive dye with high fixation rate is characterized by having a structural general formula as shown in formula (I):
wherein R is 1 、R 2 is-H;
R 3 is NHCH 2 CH 2 OCH 2 CH 2 SO 2 CH 2 CH 2 Cl；
M is an alkali metal.
2. The blue fluorine-containing reactive dye with high fixation rate according to claim 1, wherein M is selected from one of Na and K.
3. The blue fluorine-containing reactive dye with high fixation rate according to claim 1, wherein M is Na.
4. A method for preparing the blue fluorine-containing reactive dye with high fixation rate according to claim 1, which comprises the following steps:
a. ullmann reaction: pulping bromamine acid and water, adding p-biphenyldiamine-2, 5-disulfonic acid sodium solution and catalyst, heating to 90-95 ℃, and reacting to obtain the product with the structural formula
The primary condensate of (a);
b. refining: adding active carbon into the primary condensation compound obtained in the step a for adsorption, and filtering twice to obtain a secondary refined filter cake;
c. secondary condensation reaction:b, pulping the secondary refined filter cake obtained in the step b by using water, adding the cyanuric fluoride, and reacting to obtain the compound with the structural formula
A secondary condensate of (a);
d. and (3) tertiary condensation reaction: adding NHCH to the secondary condensate obtained in the step c 2 CH 2 OCH 2 CH 2 SO 2 CH 2 CH 2 A starting material for Cl,
reacting to obtain a third condensation compound, wherein the structural formula of the third condensation compound is as follows:
e. product treatment: and d, filtering the tertiary condensation compound obtained in the step d, retaining insoluble substances, and performing spray drying to obtain the finished dye.
5. The preparation method of the blue fluorine-containing reactive dye with high fixation rate according to claim 4, wherein the catalyst added in the step a comprises the following components in parts by weight: 100 parts of cuprous chloride, 5 parts of copper sulfate and 2 parts of copper powder.
6. The preparation method of the blue fluorine-containing reactive dye with high fixation rate according to claim 4, wherein in the step b, the primary condensation compound is cooled to 50 ℃, then activated carbon is added for adsorption, and a primary refined solution is obtained by filtration; adjusting pH of the primary refined solution to 1.0-1.5 with hydrochloric acid, adding sodium chloride solution, standing for 2 hr, and filtering again.
7. The method for preparing blue fluorine-containing reactive dye with high fixation rate according to claim 4, wherein in the step c, the pH of the secondary refined filter cake is adjusted to 5.0-6.0 by liquid alkali after the secondary refined filter cake is pulped by water, and the temperature is reduced to 0-5 ℃.
8. The method for preparing blue fluorine-containing reactive dye with high fixation rate according to claim 4, wherein in the step c, the cyanuric fluoride is added and the temperature is maintained at 0-5 ℃ for reaction for 1.5h, and a secondary condensation compound is obtained after the reaction.
9. The method for preparing blue fluorine-containing reactive dye with high fixation rate according to claim 4, wherein in the step d, R is added 3 After the raw material is adjusted to pH 5.0-6.0, the temperature is raised to 30-35 ℃, then the pH 5.0-6.0 is maintained for reaction for 0.5h, and then the pH 5.5-6.5 is adjusted by hydrochloric acid, thus obtaining a tertiary condensation compound.
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| CH378442A (en) * | 1959-12-11 | 1964-06-15 | Geigy Ag J R | Process for the preparation of aminoanthraquinonyl monoazo dyes |
| NL278003A (en) * | 1960-10-28 | |||
| JPS59217766A (en) * | 1983-05-25 | 1984-12-07 | Sumitomo Chem Co Ltd | Anthraquinone compound and dyeing and printing method using the same |
| GB8517779D0 (en) * | 1985-07-15 | 1985-08-21 | Ici Plc | Anthraquinone derivatives |
| ES2115097T3 (en) * | 1993-05-18 | 1998-06-16 | Dystar Textilfarben Gmbh & Co | REACTIVE DYES WITH FIBERS, SOLUBLE IN WATER, PROCEDURE FOR ITS PREPARATION AND USE. |
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