CN111592775A - Monoazo compound and preparation method and application thereof - Google Patents
Monoazo compound and preparation method and application thereof Download PDFInfo
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- CN111592775A CN111592775A CN202010407865.5A CN202010407865A CN111592775A CN 111592775 A CN111592775 A CN 111592775A CN 202010407865 A CN202010407865 A CN 202010407865A CN 111592775 A CN111592775 A CN 111592775A
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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
- C09B62/02—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
- C09B62/085—Monoazo dyes
-
- 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
-
- 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
- C09B62/095—Metal complex azo dyes
-
- 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
- C09B68/00—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology
- C09B68/20—Organic pigments surface-modified by grafting, e.g. by establishing covalent or complex bonds, in order to improve the pigment properties, e.g. dispersibility or rheology characterised by the process features
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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
- 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
Abstract
The invention discloses a monoazo compound, which is shown as a formula 1. The invention also discloses a preparation method and application of the reactive dye in preparation of the reactive printing dye with high fixation rate. The monoazo compound of the invention has the advantages of high color fixing rate, good white background staining, high solubility and the like, and is suitable for printing on cellulose fibers such as cotton, hemp and the like or protein fibers such as wool, silk and the like. The preparation method is simple, the raw materials are cheap, and great economic and environmental benefits are achieved.
Description
Technical Field
The invention relates to the field of reactive printing dyes, in particular to a monoazo compound and a preparation method and application thereof.
Background
The active dyes used for printing in the current market mainly comprise P type dyes of Huntsman company, PN type dyes of DyStar company and domestic K type dyes, the active groups of the dyes are mainly monochlorotriazine type dyes, and vinyl sulfone type active dyes are also used for printing, but the active dyes have high activity, are sensitive to process conditions and are not easy to control, so the active dyes are rarely applied to printing. Two monochlorotriazine dyes are also used for printing, namely domestic KE dyes, but because the substantivity of the dyes is too high, the wet treatment fastness of the dyes is poor, and the white bottom staining is also serious, the dyes are basically not used for printing process under general conditions.
As for the monochlorotriazine reactive dye, the monochlorotriazine reactive dye is rapidly developed and applied due to the advantages of complete chromatogram, excellent fastness indexes, good white background staining, high solubility and the like, and basically meets the requirements of the market.
However, they also have the fatal disadvantage of low fixation rate, generally 60% more, and a few 70%, so that 30-40% of dye is wasted in the printing process, which is not favorable for environmental protection, increases the difficulty of waste water treatment, and increases the printing cost. Does not conform to the national policy of energy conservation and emission reduction.
At present, no report in the aspect is found at home and abroad. The call is very loud in the market. Therefore, the art needs a reactive printing dye with high fixation rate and good white background staining.
Disclosure of Invention
In order to overcome the defect of low fixation rate of the reactive printing dye in the prior art, the invention aims to provide a monoazo compound which is used for preparing the reactive printing dye with high fixation rate.
The second object of the present invention is to provide a method for producing the monoazo compound.
The invention also aims to provide the application of the monoazo compound in preparing the reactive printing dye with high fixation rate.
In order to realize one of the purposes of the invention, the adopted technical scheme is as follows:
a monoazo compound shown as a formula 1,
wherein D is a dye parent substance, and comprises any one parent substance of monoazo, disazo, anthraquinone or formazan ;
a is any one or more of a group shown in a formula 2 or a group shown in a formula 3;
and R is any one or more of amino, N-ethylanilino, m-aminobenzene sulfonic acid, p-aminobenzene sulfonic acid or diglycol amino.
In a preferred embodiment of the present invention, the structure of D specifically includes any one of formulas I-1 to I-10:
wherein, among said I-1 to I-10, said R1is-CONH2or-CH2SO3Any one or more of H; r2Is any one or more of methyl or carboxyl; r3Is any one or more of hydrogen or methyl; the sulfonic acid group of the formula (I-9) is in the 6-or 7-position.
In order to realize the second purpose of the invention, the adopted technical scheme is as follows:
a preparation method of a monoazo compound comprises the following steps:
condensing a compound shown as a formula 4 with the substituent R to obtain a monoazo compound shown as a formula 1;
in a preferred embodiment of the present invention, the compound represented by formula 4 is specifically derived from a condensation reaction of a compound represented by formula 5 and cyanuric chloride, wherein the ratio of the compound represented by formula 5 to the cyanuric chloride is 1:1-1.5, preferably 1: 1-1.2. Obtaining the compound shown in the formula 4;
a preparation method of a monoazo compound comprises the following steps:
condensing the compound shown as the formula 6 and the compound shown as the formula 7 to obtain a monoazo compound shown as the formula 1;
in order to realize the third purpose of the invention, the adopted technical scheme is as follows:
the application of the monoazo compound is application in preparing a reactive printing dye with a high fixation rate, wherein the monoazo compound is particularly applied to the field of printing of cellulose materials containing hydroxyl or amino.
In a preferred embodiment of the present invention, the cellulose material containing hydroxyl or amino groups is any one or more of cotton, viscose, hemp or silk.
In a preferred embodiment of the present invention, the specific steps of the application include: and (3) preparing a proper amount of the monoazo compound, sodium bicarbonate, urea, dye-resistant salt and sodium alginate into printing paste for printing, prebaking, steaming, washing with water, and then soaping, washing with hot water, washing with cold water and ironing to dry to obtain the product.
The positive progress effects of the invention are as follows:
the monoazo compound of the invention has the advantages of high color fixing rate, good white background staining, high solubility and the like, and is suitable for printing on cellulose fibers such as cotton, hemp and the like or protein fibers such as wool, silk and the like. The preparation method is simple, the raw materials are cheap, and great economic and environmental benefits are achieved.
Detailed Description
The invention is further illustrated by the following examples, which are not intended to limit the scope of the invention. The experimental methods without specifying specific conditions in the following examples were selected according to the conventional methods and conditions, or according to the commercial instructions.
Unless otherwise indicated, temperatures are degrees Celsius, parts and percentages are parts by weight and percentages by weight, and the relationship between parts by weight and parts by volume is consistent with the relationship between kilograms and liters.
Example 1
18.8 parts of cyanuric chloride, 70 parts of ice, 50 parts of water and 0.1 part of peregal O25 are pulped in an ice bath for 45-60min, 54.6 parts of compound 8 (dissolved in 220 parts of water in advance) synthesized by a conventional method are added for primary condensation, and the reaction is carried out at 0-5 ℃.
Adjusting pH to 6.5-7.0 with 10% sodium carbonate solution, reacting for 3.0-4.0h, and ending when no compound 8 is present. Compound 9 of the following formula is obtained.
Then adding 10.4 parts of hydroxyethyl ethylenediamine into the first condensate, heating to 40 ℃, carrying out secondary condensation at 40-45 ℃, adjusting the pH of the medium to 6.0-6.5 by using 10% sodium carbonate solution, reacting for 3.0-5.0h, and obtaining a mixed compound shown in the following formula 10 or 11 when no compound 6 exists.
Its molecular weight was 761, according to its structure, as measured by HPLC-MS.
Pulping 18.8 parts of cyanuric chloride, 70 parts of ice, 50 parts of water and 0.1 part of peregal O25 in an ice bath for 45-60min, then adding the obtained mixed compound 7, performing triple condensation, reacting at 0-5 ℃, adjusting the pH to 6.5-7.0 by using 10% sodium hydroxide solution, and reacting for 5.0 h.
The end point is obtained when the compound 1-3 is not mixed. To obtain the mixed compounds shown in the formulas 12 and 13.
After the end point is reached, 17.3 parts of m-aminobenzene sulfonic acid (dissolved in 200 parts of water in advance) is added for tetra-condensation, the reaction is carried out at the temperature of 40-45 ℃, the pH value is adjusted to 6.5-7.0 by 10% sodium carbonate solution, the reaction is carried out for 7.0-8.0h, and the end point is obtained when no compound 9 exists. The mixed compound dyes 14 and 15 with the following formulas are obtained. Its molecular weight was 1046 by HPLC-MS, consistent with its structure.
Example 2
Pulping 18.8 parts of cyanuric chloride, 70 parts of ice, 50 parts of water and 0.1 part of peregal O25 in an ice bath for 45-60min, then adding 17.3 parts of m-aminobenzene sulfonic acid (dissolved in 200 parts of water in advance), carrying out condensation, reacting at 0-5 ℃, adjusting the pH to 6.5-7.0 by using 10% sodium carbonate solution, reacting for 3.0h, and taking the end point when no m-aminobenzene sulfonic acid exists. Compound 16 of the following formula is obtained.
Example 3
The compound 10 obtained in example 2 is added to the mixed compound 7 obtained in example 1, condensation reaction is carried out at 40-55 ℃, the pH of the medium is adjusted to 6.5-7.5 by 10% sodium carbonate solution, reaction is carried out for 4.0-5.0h, and the mixed compound dye of the following formula 17, 18 is obtained when no mixed compound 7 exists. Its molecular weight was 1046 by HPLC-MS, consistent with its structure.
Example 4
In the synthesis of 78.2 parts of the compound of formula 19 by conventional methods, 7.4 parts of 1, 2-propanediamine are added, the temperature is raised to 40 ℃, the di-condensation is carried out at 40-45 ℃, and the pH of the medium is adjusted to 6.0-6.5 with 10% sodium carbonate solution.
Reacting for 3.0-5.0h, and obtaining a mixed compound 21 shown in the following formula, wherein the end point is obtained when the compound 20 is absent. Its molecular weight was 818 as determined by HPLC-MS, consistent with its structure.
The compound 16 obtained in example 2 is added to the mixed compound formula 21 obtained above, condensation reaction is carried out at 40-55 ℃, the pH of the medium is adjusted to 6.5-7.5 by 10% sodium carbonate solution, the reaction lasts for 5.0-6.0h, and the mixed compound formula 21 is not used, namely the end point, and the mixed compound dye formula 22 or 23 shown in the following formula is obtained.
Its molecular weight was 1102, as determined by HPLC-MS, consistent with its structure.
Example 5
In the synthesis of 59.4 parts of the compound of formula 24 according to the usual method, 10.4 parts of hydroxyethylethylenediamine are added, the temperature is raised to 40 ℃ and the di-condensation is carried out at 40-45 ℃ with the medium pH being adjusted to 6.0-6.5 with 10% sodium carbonate solution.
Reacting for 3.0-5.0h, and obtaining a mixed compound shown as the following formula 26, wherein the end point is the time when the compound shown as the formula 25 is absent. Its molecular weight was 761, according to its structure, as measured by HPLC-MS.
The compound 16 obtained in example 2 is added to the mixed compound 25 or 26 obtained above, condensation reaction is carried out at 40-55 ℃, the pH of the medium is adjusted to 6.5-7.5 by 10% sodium carbonate solution, the reaction lasts for 5.0-6.0h, and the mixed compound dye of the following formula 27 or 28 is obtained when the mixed compound 21 is not available. Its molecular weight was measured by HPLC-MS to be 947, consistent with its structure.
Example 6
Adding 10.4 parts of hydroxyethyl ethylenediamine into 65.1 parts of compound 29 synthesized by a common method, heating to 40 ℃, carrying out secondary condensation at 40-45 ℃, adjusting the pH of a medium to 6.0-6.5 by using 10% sodium carbonate solution, reacting for 3.0-5.0h, and obtaining the end point when no compound 29 exists.
To obtain mixed compound 30 or 31 of the formula. Its molecular weight was 718, consistent with its structure, as measured by HPLC-MS.
The compound 16 obtained in example 2 is added to the mixed compound 30 or 31 obtained above, condensation reaction is carried out at 40-55 ℃, the pH of the medium is adjusted to 6.5-7.5 by 10% sodium carbonate solution, the reaction lasts for 5.0-6.0h, and the mixed compound dye formula 32 or 33 shown in the following formula is obtained when the mixed compound 30 or 31 is not available. The molecular weight was 1004 as determined by HPLC-MS, consistent with its structure.
Example 7
Adding 10.4 parts of hydroxyethyl ethylenediamine into 71.6 parts of compound formula 34 synthesized by a common method, heating to 40 ℃, carrying out secondary condensation at 40-45 ℃, adjusting the pH of a medium to 6.0-6.5 by using 10% sodium carbonate solution, reacting for 3.0-5.0h, and obtaining mixed compounds of the following formulae 35 and 36 when no compound 34 exists. Its molecular weight was 714 as determined by HPLC-MS, in accordance with its structure.
The compound 16 obtained in example 2 was added to the mixed compound 35 or 36 obtained above, and condensation reaction was carried out at 40-55 ℃ with the medium pH adjusted to 6.5-7.5 with 10% sodium carbonate solution for 5.0-6.0 h.
The end point is obtained in the absence of the mixed compound 18, giving the mixed compound dyes of the formulae 37, 38. Its molecular weight was 1066 as determined by HPLC-MS, consistent with its structure.
Example 8
Adding 10.4 parts of hydroxyethyl ethylenediamine into 87.0 parts of compound 39 synthesized by a common method, heating to 40 ℃, carrying out secondary condensation at 40-45 ℃, adjusting the pH of a medium to 6.0-6.5 by using 10% sodium carbonate solution, reacting for 3.0-5.0h, and obtaining the end point when no compound 39 exists.
To obtain mixed compound 40 or 41 of the formula. Its molecular weight was 936 by HPLC-MS, consistent with its structure.
The compound 16 obtained in example 2 is added to the mixed compound formula 40 or 41 obtained above, condensation reaction is carried out at 40-55 ℃, the pH of the medium is adjusted to 6.5-7.5 by 10% sodium carbonate solution, the reaction lasts for 5.0-6.0h, and the end point is obtained when the mixed compound 40 or 41 is not available, thus obtaining the mixed compound dye formula 42 or 43 shown in the following formula.
Its molecular weight was 1222 as determined by HPLC-MS, consistent with its structure.
Example 9
74.5 parts of compound 44 synthesized by a conventional method is added with 10.4 parts of hydroxyethyl ethylenediamine, heated to 40 ℃, and subjected to a secondary condensation at 40 to 45 ℃, and the pH of the medium is adjusted to 6.0 to 6.5 with 10% sodium carbonate solution, and the reaction is carried out for 3.0 to 5.0 hours.
The end point is obtained in the absence of compound 44, giving a mixed compound 45 or 46 of the formula. Its molecular weight was 811 by HPLC-MS, consistent with its structure.
The compound 16 obtained in example 2 was added to the mixed compound 45 or 46 obtained above, condensation reaction was carried out at 40-55 ℃, the medium ph was adjusted to 6.5-7.5 with 10% sodium carbonate solution, reaction was carried out for 5.0-6.0h, and the end point was reached when there was no mixed compound 45 or 46.
To give a mixed compound of the formula dye formula 47 or 48. Its molecular weight was 1095 by HPLC-MS, in accordance with its structure.
Example 10
Adding 10.4 parts of hydroxyethyl ethylenediamine into 93.1 parts of compound formula 49 synthesized by a common method, heating to 40 ℃, carrying out secondary condensation at 40-45 ℃, adjusting the pH of a medium to 6.0-6.5 by using 10% sodium carbonate solution, reacting for 3.0-5.0h, and obtaining the end point when no compound 49 exists.
To obtain a mixed compound of the formula 50 or 51. Its molecular weight was 997 by HPLC-MS, consistent with its structure.
The compound 16 obtained in example 2 is added to the mixed compound formula 50 or 51 obtained above, condensation reaction is carried out at 40-55 ℃, the pH of the medium is adjusted to 6.5-7.5 by 10% sodium carbonate solution, the reaction lasts for 5.0-6.0h, and the mixed compound formula 52 or 53 is obtained when the mixed compound formula 50 or 51 is not available. Its molecular weight was 1281, according to HPLC-MS, in accordance with its structure.
Application example 1
5 parts of the dye 101 compound synthesized in example 4 are taken, 2 parts of baking soda, 10 parts of urea, 1 part of dye-resistant salt, 70 parts of sodium alginate paste and water are added to prepare 5% of printing paste, and the printing paste is subjected to conventional printing and dyeing by using pure cotton fabrics and then subjected to steaming, washing, soaping and drying to obtain bright golden yellow fabrics.
Application example 2
5 parts of the dye synthesized in the example 4 are taken, 2 parts of baking soda, 10 parts of urea, 1 part of dye-resistant salt, 70 parts of sodium alginate paste and water are added to prepare 5% of printing paste, and the pure cotton fabric is subjected to conventional printing and dyeing, and is steamed, washed, soaped and dried to obtain bright red fabric.
Application example 3
5 parts of the dye synthesized in the example 7 are taken, 2 parts of baking soda, 10 parts of urea, 1 part of dye-resistant salt, 70 parts of sodium alginate paste and water are added to prepare 5% of printing paste, the pure cotton fabric is subjected to conventional printing and dyeing, and the bright orange fabric is obtained through steaming, washing, soaping and drying.
Through tests, the fixation rate of the dye and the fixation rate data of the comparative existing reactive dye are shown in the following table 1 (GB/T2391-:
as can be seen from table 1, the fixation ratio of the reactive dye of the example of the present invention is much higher than that of the existing reactive dye.
Table 2 shows (determination of the fastness to washing, perspiration, rubbing and of the ISO 105X 12 dyes, ISO 105C 10C (3), ISO 105E 04C (3), ISO 105X 12 and determination of the solubility):
it can be seen that the data of the reactive dyes prepared according to the invention can meet the requirements.
Claims (8)
1. A monoazo compound is characterized in that as shown in formula 1,
wherein D is a dye parent substance, and comprises any one parent substance of monoazo, disazo, anthraquinone or formazan ;
a is any one or more of a group shown in a formula 2 or a group shown in a formula 3;
and R is any one or more of amino, N-ethylanilino, m-aminobenzene sulfonic acid, p-aminobenzene sulfonic acid or diglycol amino.
2. A monoazo compound according to claim 1 wherein D has a structure which comprises any one of formulae i-1 to i-10:
wherein, among said I-1 to I-10, said R1is-CONH2or-CH2SO3Any one or more of H; r2Is any one or more of methyl or carboxyl; r3Is any one or more of hydrogen or methyl; the sulfonic acid group of the formula (I-9) is in the 6-or 7-position.
3. A process for the preparation of a monoazo compound according to claim 1 or 2, comprising the steps of:
condensing a compound shown as a formula 4 with the substituent R to obtain a monoazo compound shown as a formula 1;
4. the method for preparing monoazo compound according to claim 3, wherein the compound represented by formula 4 is obtained by condensation reaction of a compound represented by formula 5 with cyanuric chloride, wherein the ratio of the compound represented by formula 5 to the cyanuric chloride is 1:1-1.5, and the compound represented by formula 4 is obtained;
5. a process for the preparation of a monoazo compound according to claim 1 or 2, comprising the steps of:
condensing the compound shown as the formula 6 and the compound shown as the formula 7 to obtain a monoazo compound shown as the formula 1;
6. the use of a monoazo compound according to claim 1 or 2 in the preparation of reactive printing dyes having a high degree of fixation, wherein the monoazo compound is particularly useful in the field of printing of hydroxy-or amino-containing cellulose materials.
7. The use of a monoazo compound according to claim 6 wherein the cellulose material containing hydroxyl or amino groups is any one or more of cotton, viscose, hemp or silk.
8. The use of a monoazo compound according to claim 6, wherein the use comprises the steps of: and (3) preparing a proper amount of the monoazo compound, sodium bicarbonate, urea, dye-resistant salt and sodium alginate into printing paste for printing, prebaking, steaming, washing with water, and then soaping, washing with hot water, washing with cold water and ironing to dry to obtain the product.
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| CN106833012A (en) * | 2016-12-05 | 2017-06-13 | 泰兴锦云染料有限公司 | A kind of Yellow reactive dyes and its preparation and application |
| CN107964258A (en) * | 2017-12-05 | 2018-04-27 | 湖北丽源科技股份有限公司 | A kind of Yellow fluorine-containing reactive dye mixture and its preparation method and application |
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