CN112876875B - Disazo reactive yellow dye and preparation method and application thereof - Google Patents
Disazo reactive yellow dye and preparation method and application thereof Download PDFInfo
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- CN112876875B CN112876875B CN202011630798.XA CN202011630798A CN112876875B CN 112876875 B CN112876875 B CN 112876875B CN 202011630798 A CN202011630798 A CN 202011630798A CN 112876875 B CN112876875 B CN 112876875B
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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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- 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
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/58—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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Abstract
The application relates to the field of reactive dyes, and particularly discloses a disazo reactive yellow dye and a preparation method and application thereof. The preparation method of the disazo reactive yellow dye comprises the following steps: a. preparing a sodium m-diaminobenzene sulfonate solution, b, performing acylation reaction on sodium m-diaminobenzene sulfonate and chlorosulfonyl benzoyl chloride to obtain a m-diacylate; and c, performing diazotization reaction on the para-ester and sodium nitrite to obtain para-ester diazonium salt, and performing coupling reaction on the meta-diacylated compound and the para-ester diazonium salt to obtain the disazo reactive yellow dye. The composition/product can be used for dip dyeing, continuous dyeing and cold batch, printing and wet short steaming processes of cellulose fibers, has high color fixing rate and perspiration fastness, has good light fastness and washing fastness, and is green and environment-friendly.
Description
Technical Field
The application relates to the field of reactive dyes, in particular to a disazo reactive yellow dye, and a preparation method and application thereof.
Background
The reactive orange 107 is a common vinyl sulfone golden yellow dye, can be used for conventional dyeing and printing of cellulose fibers, can also be used for cold batch dyeing, dye-resist printing and discharge dyeing, has wider application range, and is a relatively economic common vinyl sulfone golden yellow dye.
However, the reactive orange 107 is a mono-vinyl sulfone type reactive group and mono-azo structure, so that the substantivity is low, the color fixing rate is low, and the commercial reactive orange 107 dye generates high-COD and high-chroma wastewater containing a large amount of inorganic salts in the dyeing and printing processes, so that the three-waste treatment difficulty is high, and the environment friendliness is not facilitated.
Disclosure of Invention
In order to solve the problems of high pollution and environmental pollution in the current printing and dyeing industry, the application provides a disazo reactive yellow dye and a preparation method and application thereof.
In a first aspect, the present application provides a disazo reactive yellow dye, which adopts the following technical scheme:
a disazo reactive yellow dye has a general structural formula shown as a formula (I):
by adopting the technical scheme, the component of the disazo reactive yellow dye with the formula (I) contains more aqueous solution groups, so that the disazo reactive yellow dye has high solubility which can reach 300g/l of 250-one. The disazo reactive yellow dye is a monomer or component dye with similar structure, the sensitivity to dyeing and printing conditions is basically consistent, and the individual difference on the molecular structure causes the difference of the polarity, so that when the disazo reactive yellow dye dyes or prints fabrics, the opportunity of the reaction of the dye and fibers is improved by utilizing the synergistic effect of polarity complementation, thereby having high fixation rate. The structure of the disazo reactive yellow dye does not contain heavy metal and carcinogenic aromatic amine, can avoid the heavy metal and carcinogenic aromatic amine of the printed fabric from exceeding the standard, and belongs to an environment-friendly safe dye.
In a second aspect, the present application provides a preparation method of a disazo reactive yellow dye, which adopts the following technical scheme:
a preparation method of a disazo reactive yellow dye comprises the following steps:
a. preparing sodium m-diaminobenzenesulfonate, water and sodium chloride into a solution, and heating to dissolve the solution into a solution;
b. c, adding chlorosulfonyl benzoyl chloride into the solution obtained in the step a for acylation reaction, then adding sodium chloride, stirring for reaction, filtering and drying the product to obtain a meta-diacylate; adding crushed ice and water into the para-ester dry powder, pulping, and adding hydrochloric acid and sodium nitrite solution to react to prepare para-ester diazonium salt;
c. b, adding a meta-diacylate into the para-ester diazonium salt obtained in the step b for reaction to obtain a coupling reaction solution with a structural general formula (I);
d. and c, filtering, drying, and blending the coupling reaction solution obtained in the step c in a dry or wet mode to obtain the finished product of the disazo reactive yellow dye.
By adopting the technical scheme, the novel m-diacylate is synthesized firstly to replace the acetyl-m-bis and then coupled with the para-ester diazonium salt to obtain the reactive yellow dye with the bisazo and the bisvinyl sulfone active groups, and compared with the reactive orange 107, the reactive yellow dye has higher color development effect and reaction activity and higher color fixation rate. The benzene rings are introduced into the two reactive yellow 201 structures, so that the dye substantivity is improved compared with reactive orange 107, the affinity of the dye to fibers is increased, the use of inorganic salt is reduced, and the reactive dye with the structure is more beneficial to printing and dyeing dark colors.
Optionally, in the acylation reaction in the step b, the molar ratio of the m-diaminobenzene sodium sulfonate to the chlorosulfonyl benzoyl chloride is 2: 1.0-1.1.
Optionally, in the acylation reaction in the step b, the molar ratio of the m-diaminobenzene sodium sulfonate to the chlorosulfonyl benzoyl chloride is 2: 1.05.
Optionally, in the step b, the temperature of the reaction liquid system is controlled to be 35-50 ℃ when the acylation reaction is carried out.
Optionally, in the step b, the temperature of the reaction liquid system is controlled to be 37-42 ℃ when the acylation reaction is carried out.
Optionally, in the step b, after the acylation reaction and before the addition of sodium chloride, the pH of the reaction solution system is adjusted to 11.5-12.5 and stirred for 0.5 h.
Optionally, in the step b, after the acylation reaction and before the addition of sodium chloride, the reaction liquid system is adjusted to pH 11.5 to 12.5 and stirred for 0.5h, and then the temperature of the reaction liquid system is reduced to 20 to 25 ℃ and the pH is adjusted to 1.5.
Optionally, in the step c, when the p-ester diazonium salt reacts with the m-diacylate, the system pH is kept at 6.0 to 6.5, and the system temperature is kept at 5 to 10 ℃.
In a third aspect, the present application provides an application of a disazo reactive yellow dye, which adopts the following technical scheme:
the application of disazo reactive yellow dye in dip dyeing, continuous dyeing and cold stacking, printing and wet short steaming process of cellulose fiber.
In summary, the present application has the following beneficial effects:
1. the active yellow dye in the application contains more aqueous solution groups, so that the active yellow dye has high solubility which can reach 250-300 g/l;
2. in the application, the disazo reactive yellow dye is a monomer or a component dye with a similar structure, so that the sensitivity to dyeing and printing conditions is basically consistent, and the individual difference in the molecular structure causes the difference in polarity, so that when the disazo reactive yellow dye is used for dyeing or printing fabrics, the opportunity of the reaction of the dye and fibers is improved by utilizing the synergistic effect of polarity complementation, and the disazo reactive yellow dye has high color fixing rate which can reach 80%;
3. the dye structure does not contain heavy metal and carcinogenic aromatic amine, so that the heavy metal and carcinogenic aromatic amine of the printed fabric can be prevented from exceeding the standard, and the dye belongs to an environment-friendly safe dye;
4. according to the method, a novel m-diacylate is synthesized firstly to replace an acetyl-m-bis and then coupled with a para-ester diazonium salt to obtain the reactive yellow dye with the bisazo and bisvinyl sulfone active groups, and compared with reactive orange 107, the reactive yellow dye has higher color development effect and reaction activity and higher color fixation rate; the benzene rings are introduced into the two reactive yellow 201 structures, so that the dye substantivity is improved compared with reactive orange 107, the affinity of the dye to fibers is increased, the use of inorganic salt is reduced, and the reactive dye with the structure is more beneficial to printing and dyeing dark colors.
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
A disazo reactive yellow dye of the formula (i) -1:
the disazo reactive yellow dye is detected by using domestic reactive golden yellow RNL as a standard, has reddish and gorgeous color and 215% strength, and is suitable for dip dyeing, continuous dyeing and printing of cellulose fibers.
The embodiment also provides a preparation method of the disazo reactive yellow dye, which comprises the following steps:
a. adding 80% purity sodium m-diaminobenzenesulfonate 126.12g in weight percentage into 1000ml of water, heating to 35 deg.C under stirring, adding 100g sodium chloride, keeping pH at 7.2, and stirring for 30min until the solid is dissolved to obtain clear solution;
b. c, controlling the temperature to be 35 ℃, adding 76g of m-chlorosulfonyl benzoyl chloride with a folding weight into the clear solution obtained in the step a at a constant speed within 2h, carrying out acylation reaction for 3h, and separating out a product in the reaction solution; adding 50g of sodium chloride into the reaction solution, filtering to obtain a filter cake, and drying to obtain a meta-diacylate; tests show that the analytical content of the m-diacylate is not less than 68.8%, the HPLC purity is not less than 95.2%, the m-bis is not more than 0.81%, the bis between diacylates is not more than 1.8%, and the others are not more than 2.1%;
wherein the diacylated meta-bis is a mixture of 5 structures in the following formula:
mixing 100ml of water, 150g of crushed ice and 56.26g of para-ester (the purity is 100 percent), stirring and pulping, wherein the stirring speed is 55 revolutions per minute, the stirring time is 60 minutes, uniform suspension is formed, and 24.34g of industrial hydrochloric acid with the mass fraction of 30 percent is added into the suspension;
dissolving 14.22g of industrial sodium nitrite (with the purity of 98%) with water to prepare a solution with the mass fraction of 30%, and dripping the solution into the suspension liquid at a constant speed within 30min, wherein the process always keeps the test of microscopic blue by a KI test paper and the test of blue by a Congo red test paper; after the sodium nitrite solution is added, stirring for 60min at the speed of 55 revolutions per minute at the temperature of 10-15 ℃, testing the colorless spot ring-wetting by using an ehrlichia reagent as a reaction end point, balancing the excessive nitrous acid by using a sulfamic acid solution until the excessive nitrous acid is not developed by using a starch KI test paper, and obtaining the para-ester diazonium salt;
c. adding 58.65g (in hundredth) of the m-diacyl filter cake obtained in the step b into the para-ester diazonium salt obtained in the step b, slowly adjusting the pH value of a reaction liquid system to 7.0 by using 20% of soda ash, controlling the system temperature at 15 ℃, stirring until the diazonium disappears (the diazo does not appear red when a salting-out ring is wetted and is tested by using 1% of alkaline H acid), filtering and drying the product to obtain the disazo reactive yellow dye with the structural formula (I) -1;
example 2
A disazo reactive yellow dye of the formula (i) -1:
this example also provides a process for preparing the disazo reactive yellow dye, which is different from example 1 in that the temperature is controlled to be 37 ℃ during the acylation reaction in step b.
Through testing, the content of the m-diacylate obtained in the process of preparing the disazo reactive yellow dye in the embodiment is equal to or greater than 69.1%, the HPLC purity is equal to or greater than 95.5%, the m-bis is equal to or less than 0.76%, the bis-acylated m-bis is equal to or less than 1.75%, and the other is equal to or less than 2%.
Example 3
A disazo reactive yellow dye of the formula (i) -1:
this example also provides a process for preparing the disazo reactive yellow dye, which is different from example 1 in that the temperature is controlled to be 40 ℃ during the acylation reaction in step b.
Through testing, the content of the m-diacylate obtained in the process of preparing the disazo reactive yellow dye in the embodiment is equal to or greater than 69.3%, the HPLC purity is equal to or greater than 95.1%, the m-bis is equal to or less than 0.74%, the bis-acylated m-bis is equal to or less than 1.78%, and the other is equal to or less than 1.95%.
Example 4
A disazo reactive yellow dye of the formula (i) -1:
this example also provides a process for preparing the disazo reactive yellow dye, which is different from example 1 in that the temperature is controlled to be 42 ℃ during the acylation reaction in step b.
Through testing, the content of the m-diacylate obtained in the process of preparing the disazo reactive yellow dye in the embodiment is equal to or greater than 69.3%, the HPLC purity is equal to or greater than 95.5%, the m-bis is equal to or less than 0.75%, the bis-acylated m-bis is equal to or less than 1.82%, and the other is equal to or less than 2%.
Example 5
A disazo reactive yellow dye of the formula (i) -1:
this example also provides a process for preparing the disazo reactive yellow dye, which is different from example 1 in that the temperature is controlled to be 50 ℃ during the acylation reaction in step b.
Through testing, the content of the m-diacylate obtained in the process of preparing the disazo reactive yellow dye in the embodiment is equal to or greater than 69.5%, the HPLC purity is equal to or greater than 95.8%, the m-bis is equal to or less than 0.78%, the bis-acylated m-bis is equal to or less than 1.85%, and the other is equal to or less than 1.96%.
Example 6
A disazo reactive yellow dye of the formula (i) -1:
this example also provides a process for preparing the disazo reactive yellow dye, which is different from example 3 in that in step b, after the acylation reaction and before the addition of sodium chloride, the pH of the reaction solution system is slowly adjusted to 11.5 with 30% by weight of alkali solution, and the reaction solution is stirred for 0.5h until the reaction solution is clear and the pH is stable.
Through testing, the content of the m-diacylate obtained in the process of preparing the disazo reactive yellow dye in the embodiment is equal to or greater than 69.2%, the HPLC purity is equal to or greater than 95.4%, the m-bis is equal to or less than 0.81%, the bis-acylated m-bis is equal to or less than 1.86%, and the other is equal to or less than 1.98%.
Wherein the diacylated meta-bis is a mixture of 5 structures in the following formula:
example 7
A disazo reactive yellow dye of the formula (i) -1:
this example also provides a process for preparing the disazo reactive yellow dye, which is different from example 3 in that in step b, after the acylation reaction and before the addition of sodium chloride, the pH of the reaction solution system is slowly adjusted to 12.0 with 30% by weight of alkali solution, and the reaction solution is stirred for 0.5h until the reaction solution is clear and the pH is stable.
Through testing, the content of the m-diacylate obtained in the process of preparing the disazo reactive yellow dye in the embodiment is equal to or greater than 69.3%, the HPLC purity is equal to or greater than 95.5%, the m-bis is equal to or less than 0.75%, the bis-acylated m-bis is equal to or less than 1.88%, and the other is equal to or less than 2%.
Wherein the diacylated meta-bis is a mixture of 5 structures in the following formula:
example 8
A disazo reactive yellow dye of the formula (i) -1:
this example also provides a process for preparing the disazo reactive yellow dye, which is different from example 3 in that in step b, after the acylation reaction and before the addition of sodium chloride, the pH of the reaction solution system is slowly adjusted to 12.5 with 30% by weight of alkali solution, and the reaction solution is stirred for 0.5h until the reaction solution is clear and the pH is stable.
Through testing, the content of the m-diacylate obtained in the process of preparing the disazo reactive yellow dye in the embodiment is equal to or greater than 69.5%, the HPLC purity is equal to or greater than 95.8%, the m-bis is equal to or less than 0.78%, the bis-acylated m-bis is equal to or less than 1.85%, and the other is equal to or less than 1.96%.
Wherein the diacylated meta-bis is a mixture of 5 structures in the following formula:
example 9
A disazo reactive yellow dye of the formula (i) -1:
this example also provides a process for preparing a disazo yellow dye, which is different from example 7 in that in step b, after the acylation reaction and before the addition of sodium chloride, the pH of the reaction liquid system is slowly adjusted to 12.0 with 30% by mass of an alkali solution, the reaction liquid system is stirred for 0.5h until the reaction liquid is clear and the pH is stabilized, and then the reaction liquid system is cooled to 25 ℃ and the pH of the reaction liquid is adjusted to 1.5 with industrial hydrochloric acid.
Through testing, the content of the m-diacylate obtained in the process of preparing the disazo reactive yellow dye in the embodiment is not less than 70.7%, the HPLC purity is not less than 95.3%, the m-bis is not more than 0.75%, the bis-acylated m-bis is not more than 1.55%, and the other is not more than 2%.
Wherein the diacylated meta-bis is a mixture of 5 structures in the following formula:
example 10
A disazo reactive yellow dye of the formula (i) -1:
this example also provides a process for preparing a disazo reactive yellow dye, which is different from example 7 in that in step b, after the acylation reaction and before the addition of sodium chloride, the pH of the reaction liquid system is slowly adjusted to 12.0 with 30% by mass of an alkali solution, the reaction liquid system is stirred for 0.5h until the reaction liquid is clear and the pH is stabilized, and then the reaction liquid system is cooled to 22 ℃ and the pH of the reaction liquid is adjusted to 1.5 with industrial hydrochloric acid.
Through testing, the content of the m-diacylate obtained in the process of preparing the disazo reactive yellow dye in the embodiment is not less than 70.6%, the HPLC purity is not less than 95.6%, the m-bis is not more than 0.62%, the bis-acylated m-bis is not more than 1.55%, and the other is not more than 1.95%.
Wherein the diacylated meta-bis is a mixture of 5 structures in the following formula:
example 11
A disazo reactive yellow dye of the formula (i) -1:
this example also provides a process for preparing a disazo yellow dye, which is different from example 7 in that in step b, after the acylation reaction and before the addition of sodium chloride, the pH of the reaction liquid system is slowly adjusted to 12.0 with 30% by mass of an alkali solution, the reaction liquid system is stirred for 0.5h until the reaction liquid is clear and the pH is stabilized, and then the reaction liquid system is cooled to 20 ℃ and the pH of the reaction liquid is adjusted to 1.5 with industrial hydrochloric acid.
Through testing, the content of the m-diacylate obtained in the process of preparing the disazo reactive yellow dye in the embodiment is not less than 70.5%, the HPLC purity is not less than 95.7%, the m-bis is not more than 0.71%, the bis-acylated m-bis is not more than 1.68%, and the other is not more than 1.95%.
Wherein the diacylated meta-bis is a mixture of 5 structures in the following formula:
example 12
A disazo reactive yellow dye of the formula (i) -1:
this example also provides a process for producing a disazo reactive yellow dye, which is different from example 11 in that in the reaction of the para-ester diazonium salt with the meta-diacylate, the pH of the reaction solution system is slowly adjusted to 6.5 with 20% by mass of soda ash, and the temperature of the system is controlled at 5 ℃.
Through testing, the content of the m-diacylate obtained in the process of preparing the disazo reactive yellow dye in the embodiment is not less than 70.2%, the HPLC purity is not less than 96.3%, the m-bis is not more than 0.68%, the bis-acylated m-bis is not more than 1.74%, and the other is not more than 2%.
Wherein the diacylated meta-bis is a mixture of 5 structures in the following formula:
example 13
A disazo reactive yellow dye of the formula (i) -1:
this example also provides a process for producing a disazo reactive yellow dye, which is different from example 11 in that in the reaction of the para-ester diazonium salt with the meta-diacylate, the pH of the reaction solution system was slowly adjusted to 6.2 with 20% by mass of soda ash, and the temperature of the system was controlled at 7 ℃.
Through testing, the content of the m-diacylate obtained in the process of preparing the disazo reactive yellow dye in the embodiment is not less than 70.5%, the HPLC purity is not less than 96%, the m-bis is not more than 0.55%, the bis-acylated is not more than 1.45%, and the others are not more than 2%.
Wherein the diacylated meta-bis is a mixture of 5 structures in the following formula:
example 14
A disazo reactive yellow dye of the formula (i) -1:
this example also provides a process for producing a disazo reactive yellow dye, which is different from example 11 in that in the reaction of the para-ester diazonium salt with the meta-diacylate, the pH of the reaction solution system is slowly adjusted to 6.0 with 20% by mass of soda ash, and the temperature of the system is controlled to 10 ℃.
Through testing, the content of the m-diacylate obtained in the process of preparing the disazo reactive yellow dye in the embodiment is not less than 70.5%, the HPLC purity is not less than 96%, the m-bis is not more than 0.55%, the bis-acylated is not more than 1.45%, and the others are not more than 2%.
Wherein the diacylated meta-bis is a mixture of 5 structures in the following formula:
example 15
A disazo reactive yellow dye of the formula (i) -2:
the disazo reactive yellow dye is detected by using domestic reactive golden yellow RNL as a standard, has reddish and brilliant color and 208% strength, and is suitable for dip dyeing and continuous dyeing of cellulose fibers.
The embodiment also provides a preparation method of the disazo reactive yellow dye, which comprises the following steps:
a. adding 80% purity sodium m-diaminobenzenesulfonate 126.12g in weight percentage into 1000ml of water, heating to 40 deg.C under stirring, adding 100g sodium chloride, keeping pH at 7.2, and stirring for 30min until the solid is dissolved to obtain clear solution;
b. c, controlling the temperature to be 40 ℃, adding 76g of parachlorosulfonyl benzoyl chloride with a weight of one hundred percent into the clear solution obtained in the step a at a constant speed within 2.5h, carrying out acylation reaction for 6h, slowly adjusting the pH value of a reaction liquid system to be 12.0 by using 30% alkali liquor, stirring for 0.5h until the reaction liquid is clear and stable, cooling the reaction liquid system to 20 ℃, adjusting the pH value of the reaction liquid to be 1.5 by using industrial hydrochloric acid, and separating out a product in the reaction liquid; adding 50g of sodium chloride into the reaction solution, filtering to obtain a filter cake, and drying to obtain a meta-diacylate; the analysis content of the m-diacylate is equal to or more than 73 percent, the HPLC purity is equal to or more than 96.5 percent, the m-bis is equal to or less than 0.78 percent, the bis between diacylation is equal to or less than 1.3 percent, and the others are equal to or less than 1.92 percent through testing;
wherein the diacylated meta-bis is a mixture of 4 structures of the following formula:
mixing 100ml of water, 150g of crushed ice and 56.26g of para-ester (the purity is 100 percent), stirring and pulping, wherein the stirring speed is 60 revolutions per minute, the stirring time is 60 minutes, uniform suspension is formed, and 24.34g of industrial hydrochloric acid with the mass fraction of 30 percent is added into the suspension;
dissolving 14.22g of industrial sodium nitrite (with the purity of 98%) with water to prepare a solution with the mass fraction of 30%, and dripping the solution into the suspension liquid at a constant speed within 30min, wherein the process always keeps the test of microscopic blue by a KI test paper and the test of blue by a Congo red test paper; after the sodium nitrite solution is added, stirring for 60min at the speed of 60 revolutions per minute at the temperature of 10-15 ℃, using an ehrlichia reagent to test colorless spot ring wetting as a reaction end point, and balancing excess nitrous acid by using a sulfamic acid solution to obtain para-ester diazonium salt;
c. adding 58.65g (in hundredth) of the m-diacyl filter cake obtained in the step b into the para-ester diazonium salt obtained in the step b, slowly adjusting the pH value of a reaction liquid system to 6.0 by using 20% of soda ash, controlling the system temperature at 10 ℃, stirring until the diazonium disappears (the diazo does not appear red when a salting-out ring is wetted and is tested by using 1% of alkaline H acid), filtering and drying the product to obtain the disazo reactive yellow dye with the structural formula (I) -2;
example 16
A disazo reactive yellow dye of the formula (I) -1 and (I) -2:
the disazo reactive yellow dye is detected by using domestic reactive golden yellow RNL as standard, has reddish and brilliant color and 211% strength, and is suitable for dip dyeing, continuous dyeing, cold batch and wet short steaming processes of cellulose fibers.
The embodiment also provides a preparation method of the disazo reactive yellow dye, which comprises the following steps:
a. adding 80% purity sodium m-diaminobenzenesulfonate 126.12g in terms of percentage weight into 1000ml of water, heating to 45 ℃ under stirring, adding 100g of sodium chloride, keeping pH at 7.2, and stirring for 30min until the solid is dissolved to obtain a clear solution;
b. c, controlling the temperature to be 45 ℃, adding 40g of m-chlorosulfonyl benzoyl chloride and 40g of p-chlorosulfonyl benzoyl chloride into the clear solution obtained in the step a at a constant speed within 3h, stirring for acylation reaction for 4h, slowly adjusting the pH of a reaction liquid system to 12.0 by using alkali liquor with the mass fraction of 30%, stirring for 0.5h until the reaction liquid is clear and stable, cooling the reaction liquid system to 20 ℃, adjusting the pH of the reaction liquid to 1.5 by using industrial hydrochloric acid, and separating out a product in the reaction liquid; adding 50g of sodium chloride into the reaction solution, filtering to obtain a filter cake, and drying to obtain a meta-diacylate; tests show that the analytical content of the m-diacylate is not less than 74.5%, the HPLC purity is not less than 95.5%, the m-bis is not more than 0.75%, the bis between the diacylates is not more than 1.85%, and the others are not more than 1.9%;
wherein, the diacylation m-bis is a mixture of the following 9 structures:
mixing 100ml of water, 150g of crushed ice and 56.26g of para-ester (with the purity of 100%), stirring and pulping, wherein the stirring speed is 60 revolutions per minute, the stirring time is 60 minutes, so as to form uniform suspension, and then adding 24.34g of industrial hydrochloric acid with the mass fraction of 30% into the suspension;
dissolving 14.22g of industrial sodium nitrite (with the purity of 98%) with water to prepare a solution with the mass fraction of 30%, and dripping the solution into the suspension liquid at a constant speed within 30min, wherein the process always keeps the test of microscopic blue by a KI test paper and the test of blue by a Congo red test paper; after the sodium nitrite solution is added, stirring for 60min at the speed of 60 revolutions per minute at the temperature of 10-15 ℃, using an ehrlichia reagent to test colorless spot ring wetting as a reaction end point, and balancing excess nitrous acid by using a sulfamic acid solution to obtain para-ester diazonium salt;
c. adding 58.65g (in hundredth) of the m-diacyl filter cake obtained in the step b into the para-ester diazonium salt obtained in the step b, slowly adjusting the pH value of a reaction liquid system to 6.5 by using 20% of soda ash, controlling the system temperature to be 5 ℃, stirring until the diazonium disappears (the diazo does not appear red when a salting-out ring is wetted and is tested by using 1% of alkaline H acid), filtering and drying the product to obtain the disazo reactive yellow dye with the compound structural formula of (I) -1 and (I) -2;
example 17
A disazo reactive yellow dye, which is prepared by compounding the dyes prepared in the embodiments 14 and 15 according to the weight percentage of 55: 45.
The disazo reactive yellow dye is detected by using domestic reactive golden yellow RNL as standard, has reddish and brilliant color and 216% strength, and is suitable for dip dyeing, continuous dyeing, cold batch and wet short steaming processes of cellulose fibers.
Example 18
A disazo reactive yellow dye, this example differs from example 16 in that in step b, the acylation temperature is adjusted to 50 ℃, the percentage weight of m-chlorosulfonylbenzoyl chloride is 50g, the percentage weight of p-chlorosulfonylbenzoyl chloride is 30g, the acylation reaction time is 4h, and the other conditions are not changed.
Through testing, the content of the m-diacylate obtained in the process of preparing the disazo reactive yellow dye in the embodiment is not less than 74.8%, the HPLC purity is not less than 96.2%, the m-bis is not more than 0.72%, the bis-acylated m-bis is not more than 1.53%, and the other is not more than 1.91%.
The disazo reactive yellow dye is detected by using domestic reactive golden yellow RNL as standard, has reddish and brilliant color and 211% strength, and is suitable for dip dyeing, continuous dyeing, cold batch and wet short steaming processes of cellulose fibers.
Dyeing property test
The dyeing properties of the disazo reactive yellow dyes prepared in domestic reactive golden yellow RNL and examples 1 to 18 were measured according to GB/T2391, ISO205C04, ISO105B02, ISO105E04 and ISO102-X12, respectively, and the results are shown in Table 1.
TABLE 1 dyeing Properties test Table for examples 1-18 and domestic reactive golden yellow RNL
As can be seen from table 1, the disazo reactive yellow dye provided by the application has high color fixing rate and high perspiration fastness, the color fixing rate of the disazo reactive yellow dye can reach 80%, and the disazo reactive yellow dye has good light fastness and washing fastness and excellent performance.
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 (10)
1. A disazo reactive yellow dye is characterized by having a general structural formula shown as a formula (I):
2. a process for the preparation of disazo reactive yellow dye according to claim 1, comprising the steps of:
a. preparing sodium m-diaminobenzenesulfonate, water and sodium chloride into a solution, and heating to dissolve the solution into a solution;
b. c, adding chlorosulfonyl benzoyl chloride into the solution obtained in the step a for acylation reaction, then adding sodium chloride, stirring for reaction, filtering and drying the product to obtain a meta-diacylate; adding crushed ice and water into the para-ester dry powder, pulping, and adding hydrochloric acid and sodium nitrite solution to react to prepare para-ester diazonium salt;
c. b, adding a meta-diacylate into the para-ester diazonium salt obtained in the step b for reaction to obtain a coupling reaction solution with a structural general formula (I);
d. and c, filtering, drying, and blending the coupling reaction solution obtained in the step c in a dry or wet mode to obtain the finished product of the disazo reactive yellow dye.
3. The method for preparing disazo reactive yellow dye according to claim 2, wherein in the acylation reaction in the step b, the molar ratio of the sodium m-diaminobenzenesulfonate to the chlorosulfonyl benzoyl chloride is 2: 1.0-1.1.
4. The process for preparing disazo reactive yellow dye according to claim 3, wherein in the acylation reaction in the step b, the molar ratio of the sodium m-diaminobenzenesulfonate to the chlorosulfonyl benzoyl chloride is 2: 1.05.
5. The process for preparing a disazo reactive yellow dye according to any one of claims 2-4, wherein in the step b, the temperature of the reaction liquid system is controlled to be 35-50 ℃ when the acylation reaction is carried out.
6. The process according to claim 5, wherein in the step b, the temperature of the reaction solution system is controlled to be 37 to 42 ℃ when the acylation reaction is carried out.
7. The process according to claim 6, wherein in step b, after the acylation reaction and before the addition of sodium chloride, the pH of the reaction solution system is adjusted to 11.5-12.5 and the reaction solution is stirred for 0.5 h.
8. The process according to claim 7, wherein in the step b, after the acylation reaction and before the addition of sodium chloride, the reaction liquid system is stirred for 0.5h at a pH of 11.5 to 12.5, and then the temperature of the reaction liquid system is lowered to 20 to 25 ℃ and the pH is adjusted to 1.5.
9. The process according to claim 8, wherein in the step c, the reaction between the p-ester diazonium salt and the m-diacylate is carried out while maintaining the system pH at 6.0-6.5 and the system temperature at 5-10 ℃.
10. Use of a disazo reactive yellow dye according to claim 1 for exhaust dyeing, continuous dyeing and cold mass, printing and wet short steaming of cellulose fibres.
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| US3932381A (en) * | 1973-02-12 | 1976-01-13 | Eastman Kodak Company | Magenta image-providing phenylazo-naphthyl dyes |
| GB1543173A (en) * | 1975-04-04 | 1979-03-28 | Hoechst Ag | Water-soluble disazo dyestuffs process for their preparation and their use |
| CN1121097A (en) * | 1994-07-06 | 1996-04-24 | 拜尔公司 | Azo dyes having a fiber-reactive group |
| CN101250332A (en) * | 2008-04-08 | 2008-08-27 | 赵卫国 | Reactive golden yellow RNL diazo dyes and preparation method thereof |
| CN107033628A (en) * | 2016-12-31 | 2017-08-11 | 浙江龙盛化工研究有限公司 | A kind of reactive yellow dye compounds and its preparation method and application |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101307190B (en) * | 2007-05-18 | 2011-05-25 | 明德国际仓储贸易(上海)有限公司 | Yellow chemically-reactive dye combinations |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932381A (en) * | 1973-02-12 | 1976-01-13 | Eastman Kodak Company | Magenta image-providing phenylazo-naphthyl dyes |
| GB1543173A (en) * | 1975-04-04 | 1979-03-28 | Hoechst Ag | Water-soluble disazo dyestuffs process for their preparation and their use |
| CN1121097A (en) * | 1994-07-06 | 1996-04-24 | 拜尔公司 | Azo dyes having a fiber-reactive group |
| CN101250332A (en) * | 2008-04-08 | 2008-08-27 | 赵卫国 | Reactive golden yellow RNL diazo dyes and preparation method thereof |
| CN107033628A (en) * | 2016-12-31 | 2017-08-11 | 浙江龙盛化工研究有限公司 | A kind of reactive yellow dye compounds and its preparation method and application |
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