CN109825108B - Red reactive dye and method for dyeing cotton fibers in non-aqueous medium by using same - Google Patents
Red reactive dye and method for dyeing cotton fibers in non-aqueous medium by using same Download PDFInfo
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Abstract
The invention discloses a red reactive dye, which has a structure shown in a formula I:
wherein R is1、R2Each independently selected from hydrogen, substituted or unsubstituted C1‑C4An alkyl group; x is F, Cl or Br; r3、R4Each independently selected from C1‑C4Alkoxy, halogen, hydroxy, sulfonic acid; d1、D2Each independently selected from substituted phenyl; the red reactive dye has higher solubility in a non-aqueous medium and higher affinity to cotton fibers, and can be dyed on the cotton fibers at higher dye-uptake; meanwhile, the hydrolytic dye of which the corresponding part is not fixed on the fiber is very easy to clean.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering, and relates to a red reactive dye, a preparation method thereof and a method for dyeing cotton fibers in a non-aqueous medium.
Background
The reactive dye is the first choice dye for dyeing cotton fiber and has excellent fastness. The existing commercial reactive dyes dye cotton fibers in water, so that a large amount of colored wastewater is generated after dyeing is finished, and the protection of the water environment is not favorable. China is a printing and dyeing big country, and the total amount of printing and dyeing wastewater generated by dyeing accounts for 1/4 of the total amount of industrial wastewater every year. The existing commercial reactive dye can not be completely adapted to the dyeing condition of a non-aqueous medium, and mainly shows that the dye uptake is not high, so that a large amount of reactive dye stays in the dyeing medium.
In view of the above, there is a need to develop a reactive dye capable of dyeing cotton fibers in a non-aqueous medium.
Disclosure of Invention
The first purpose of the invention is to provide a red reactive dye.
The second purpose of the invention is to provide a preparation method of the red reactive dye.
The third purpose of the invention is to provide a method for dyeing cotton fiber by the red reactive dye in a non-aqueous medium.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
the first aspect of the invention provides a red reactive dye, which has a structure shown in formula I:
wherein R is1、R2Each independently selected from hydrogen, substituted or unsubstituted C1-C4An alkyl group;
x is F, Cl or Br;
R3、R4each independently selected from C1-C4Alkoxy, halogen, hydroxy, sulfonic acid;
D1、D2each independently selected from substituted phenyl;
the compound shown in the formula I at least contains 2 sulfonic acid groups, preferably 3-8 sulfonic acid groups, each sulfonic acid group is independent from each other and is in a free acid form or (preferably) a sulfonate form.
Preferred compounds of the invention are, of the formula I, D1、D2Each independently selected from one of the following substituents:
the most preferred compound of the present invention is one of the following structures:
the second aspect of the present invention provides a preparation method of the red reactive dye, comprising the following steps:
the first step is as follows: dissolving para-anisidine-3-sulfonic acid in water, dropwise adding 30% hydrochloric acid to adjust the pH to be less than 3, controlling the temperature of an ice salt bath to be 0-5 ℃, slowly dropwise adding excessive sodium nitrite into the para-anisidine-3-sulfonic acid solution to prepare a 30% aqueous solution, after dropwise adding is completed, keeping the temperature to be 0-5 ℃ and the pH to be less than 3 for reaction, adding sulfamic acid, and obtaining a product which is a compound 1, namely the water suspension of the diazo para-anisidine-3-sulfonic acid;
the second step is that: dissolving J acid in water, wherein the molar ratio of the J acid to the p-anisidine-3-sulfonic acid is 1:1, adjusting the pH value to 5-6 by using 30% hydrochloric acid, controlling the reaction temperature to 0-5 ℃ by using an ice salt bath, slowly dropwise adding the compound 1, namely the water suspension of the p-anisidine-3-sulfonic acid diazonium salt, and reacting at the temperature of 0-5 ℃ and the pH value of 5-6 to generate a product, namely an aqueous solution of a compound 2;
the third step: dissolving cyanuric chloride in water, wherein the molar ratio of the cyanuric chloride to p-anisidine-3-sulfonic acid is 1:1, cooling to 0-5 ℃, dropwise adding an aqueous solution of a compound 2 into the cyanuric chloride solution, controlling the pH of the solution to be 5-6, and keeping the temperature to be 0-5 ℃ and the pH to be 5-6 for reaction to obtain an aqueous solution of a compound 3;
the fourth step: dissolving H acid in water, wherein the molar ratio of the H acid to p-anisidine-3-sulfonic acid is 1:1, adjusting the pH to 7 by using a 10% NaOH aqueous solution, dropwise adding the solution into the compound 3 aqueous solution, controlling the reaction temperature to be 30-35 ℃, continuously dropwise adding a 5% NaOH aqueous solution to control the pH of a reactant to be 5-6, and keeping the temperature to be 30-35 ℃ and the pH to be 5-6 for reaction to obtain a product, namely a compound 4 aqueous solution;
the fifth step: dissolving 2, 4-diaminobenzene sulfonic acid in water, dripping equimolar 2, 3-dibromo propionyl chloride, continuously dripping a sodium bicarbonate solution with the concentration of 10% in the process, adjusting the pH to be 5-6, and keeping the pH to be 5-6 for reaction after dripping to obtain a product, namely an aqueous solution of a compound 5;
and a sixth step: cooling the water solution of the compound 5 to 0-5 ℃, adjusting the pH value to be less than 3 by using hydrochloric acid with the concentration of 30%, slowly dripping excessive sodium nitrite water solution, keeping the temperature for reaction after dripping, and adding sulfamic acid to generate a product which is the water suspension of the compound 6;
the seventh step: dropwise adding the aqueous suspension of the compound 6 prepared in the sixth step into the aqueous solution of the compound 4 prepared in the fourth step at room temperature, adjusting the pH to 4-6 with 5% NaOH, stirring and reacting to obtain the product, namely, the aqueous solution of the compound I-1, and obtaining a solid powder by freeze-drying.
The second aspect of the present invention provides a preparation method of the red reactive dye, comprising the following steps:
dissolving cyanuric chloride in water, cooling to 0-5 ℃, and adjusting the pH value to 5-6 by using NaOH with the concentration of 5%; dissolving H acid with equal molar ratio in water, adding NaOH with concentration of 10% to dissolve the H acid to pH <7, slowly dripping the H acid solution into the aqueous suspension of the cyanuric chloride at the temperature of 0-5 ℃, continuously dripping NaOH with concentration of 5% to adjust the pH to 5-6, and carrying out heat preservation reaction to obtain a product, namely an aqueous solution of a compound 7;
secondly, slowly dripping the water suspension of the compound 1, namely the diazo p-anisidine-3-sulfonic acid salt into the water solution of the compound 7 at the temperature of 0-5 ℃, continuously dripping 5 percent NaOH to adjust the pH value to be 5-6, and carrying out heat preservation reaction to obtain a product, namely the water solution of the compound 8;
dissolving gamma acid in water, adding 10% NaOH dropwise to dissolve the gamma acid and H acid in an equimolar ratio to ensure that the pH value is less than 7, heating the solution to 30-35 ℃, slowly adding the gamma acid solution dropwise into the aqueous solution of the compound 8, continuously adding 5% NaOH dropwise to adjust the pH value to be 4-6 during the process, and carrying out heat preservation reaction to obtain a product, namely the aqueous solution of the compound 9;
fourthly, dropwise adding the aqueous suspension of the compound 6 into the aqueous solution of the compound 9 at the temperature of 30-35 ℃, continuously dropwise adding 5% NaOH to adjust the pH value to 4-6, keeping the temperature for reaction, and obtaining the product, namely the aqueous solution of the compound I-2, and obtaining solid powder in a freeze drying mode.
The second aspect of the present invention provides a preparation method of the red reactive dye, comprising the following steps:
dissolving meta-ester-4-sulfonic acid in water, dropwise adding 30% hydrochloric acid to adjust the pH value to be less than 3, cooling to 0-5 ℃, dropwise adding excessive sodium nitrite to perform heat preservation reaction, and adding sulfamic acid to generate a product which is the aqueous suspension of a compound 10;
and a second step of adding dropwise the aqueous suspension of compound 10 to the aqueous solution of compound 9 at room temperature, while continuously adding dropwise 5% NaOH to adjust the pH to 4-6, and maintaining the temperature to react, thereby obtaining an aqueous solution of compound I-3 as a product, and freeze-drying the resulting product to obtain a solid powder.
The second aspect of the present invention provides a preparation method of the red reactive dye, comprising the following steps:
dissolving J acid in water, dropwise adding 30% hydrochloric acid to adjust the pH value to 5-6, heating the aqueous solution of the compound 8 to 30-35 ℃, slowly dropwise adding the J acid solution, continuously dropwise adding 5% NaOH to adjust the pH value to 5-6, and carrying out heat preservation reaction to obtain a product, namely an aqueous solution of a compound 11;
and a second step of slowly adding dropwise an aqueous suspension of compound 10 to the aqueous solution of compound 11 at room temperature while continuously adding dropwise 5% NaOH to adjust the pH to 5-6, and maintaining the temperature to give an aqueous solution of compound I-4 as a product, which is then lyophilized to obtain a solid powder.
The third aspect of the invention provides a method for dyeing cotton fibers by the red reactive dye in a non-aqueous medium, which comprises the following steps:
dissolving the pretreated cotton fabric in a non-aqueous medium containing the red reactive dye, fully dissolving, heating to 50-60 ℃, preserving heat, adding a solvent B, heating to 90-100 ℃, preserving heat, cooling to room temperature, taking out the cotton fabric, and squeezing to obtain dyed cotton fibers;
the non-aqueous medium refers to a mixture of binary organic solvents (solvent M), one component of which is an organic solvent with higher polarity, namely solvent A, capable of dissolving the red reactive dye, and the other component of which is an organic solvent with lower polarity, namely solvent B, incapable of dissolving the red reactive dye; the solvent A and the solvent B are mutually soluble, and the two solvents can be mutually soluble in any proportion. In the mixed solvent, the solvent B is used for reducing the solubility of the solvent A to the red reactive dye;
the mass ratio of the cotton fabric to the red reactive dye is (25-40): 1.
The bath ratio of the cotton fabric to the solvent A to the solvent B is 1: 5-25.
The mass ratio of the cotton fabric to the red reactive dye is 33.3: 1.
The cotton fabric refers to pure cotton fabrics with various organizational structures, pure cotton mercerized fabrics and cotton blended fabrics blended with other fibers.
The solvent A is at least one of DMF, DMSO and N-methylpyrrolidone.
The solvent B is at least one of petroleum ether, tetrachloroethylene (PCE) and carbon tetrachloride.
The treatment method of the pretreated cotton fabric comprises the following steps:
soaking cotton fabric in Na2CO3And (3) putting the swollen cotton fabric into a centrifuge tube provided with a steel mesh for supporting a sample, centrifuging, accurately weighing the centrifuged cotton fabric, and drying until the water content of the cotton fabric is less than 2%.
Due to the adoption of the technical scheme, the invention has the following advantages and beneficial effects:
the structure of the red reactive dye of the invention consists of a parent dye, a linking group and a reactive group. Unlike existing reactive dyes, a) the type and number of reactive groups in the dye molecule; b) the number of sulfonic acid groups in the dye molecule is more than that of the existing reactive dye. The reactive dye with the characteristics, namely the red reactive dye has higher solubility in a non-aqueous medium and higher affinity to cotton fibers, and can be dyed on the cotton fibers at higher dye-uptake; meanwhile, the hydrolytic dye which is not fixed on the fiber is easy to clean.
It is emphasized that all intermediates and chemicals required for the production of the individual dyes of the present invention are readily available in the domestic and foreign markets without the need for special customization, the equipment required for the manufacture of these dyes is also standard equipment common to dye manufacturing companies, and the various reactions involved in the synthesis of these dyes are the unit reactions commonly used in the production of azo dyes. The dye disclosed by the invention has a relatively large number of sulfonic acid groups in the structure, so that the dye has great affinity to water, does not have high dye uptake when used for dyeing cotton fibers in water, is only suitable for dyeing the cotton fibers in a non-aqueous medium, and has the dye uptake of 92% or more.
Detailed Description
In order to more clearly illustrate the invention, the invention is further described below in connection with preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
All the raw materials used in the examples of the invention are industrial products, and some raw materials are filter cakes containing water.
Example 1
The first step is as follows: diazotization of p-anisidine-3-sulfonic acid
P-anisidine-3-sulfonic acid (20.3g, 0.1mol, 99.22% from Zhejiang Longsheng dye chemical Co., Ltd.) was dissolved in 200mL of water, 30% hydrochloric acid was added dropwise to adjust the pH to 3, and the temperature of the ice salt bath was controlled at 0-5 ℃. Sodium nitrite (8.3g, 0.12mol, 99.5% of Jinan Kunfeng chemical Co., Ltd.) is prepared into 30% aqueous solution, the aqueous solution is slowly dripped into the p-anisidine-3-sulfonic acid solution, after the dropwise addition is completed, the temperature is kept between 0 and 5 ℃ and the pH value is kept less than 3, and the reaction is carried out for 15 to 30 min. Excess nitrous acid was destroyed with sulfamic acid (99.5% from Shandong Ming Daichemical science and technology Co., Ltd.) and sulfamic acid was added to produce a product as an aqueous suspension of diazo p-anisidine-3-sulfonate, having the structure shown in Compound 1.
The second step is that: coupling of para-anisidine-3-sulfonic acid diazonium salt with J acid
J acid (2-amino-5-naphthol-7-sulfonic acid) (23.9g, 0.1mol, 90.76% solid content, wet cake, from zhejiang cheng dyestuffs chemical limited) was dissolved in 250mL of water, pH was adjusted to 5-6 with 30% hydrochloric acid, reaction temperature was controlled to 0-5 ℃ in an ice salt bath, and the above compound 1, i.e., an aqueous suspension of p-anisidine-3-sulfonic acid diazonium salt was slowly added dropwise while maintaining the temperature at 0-5 ℃ and pH at 5-6, and reacted for 2 hours to give an aqueous solution of compound 2.
The third step: condensation of Compound 2 with Cyanuric chloride
Cyanuric chloride (18.8g, 0.1mol, 98% from Zhejiang Longsheng dye chemical Co., Ltd.) was thoroughly mixed with 200mL of water (containing 1% of emulsifier TX-100, 98% from Nantong Yongle chemical Co., Ltd.), and cooled to 0-5 ℃. Dropwise adding the aqueous solution of the compound 2 obtained in the second step into the solution, controlling the pH of the solution to be 5-6, keeping the temperature to be 0-5 ℃ and the pH to be 5-6, and reacting for 2h to obtain the product, namely the aqueous solution of the compound 3.
The fourth step: condensation of Compound 3 with H acid
H acid (1-amino-8-naphthol-3, 6-disulfonic acid) (32.0g, 0.1mol, chejiang dragon dye chemical ltd, wet cake, solid content 85.48%) was dissolved in 300mL of water, pH 7 was adjusted with 10% aqueous NaOH, at which time the H acid was completely dissolved, the solution was added dropwise to the aqueous solution of compound 3 obtained in the third step, while controlling the reaction temperature at 30 to 35 ℃, and aqueous 5% NaOH was continuously added dropwise to control the pH of the reactant at 5 to 6, the temperature was maintained at 30 to 35 ℃ and the pH at 5 to 6, and the reaction was carried out for 2 hours to give an aqueous solution of compound 4.
The fifth step: condensation of 2, 4-diaminobenzenesulphonic acid and 2, 3-dibromopropionyl chloride
2, 4-diaminobenzenesulfonic acid (18.8g, 0.1mol, 82.13% solid content, wet cake, from Zhejiang Longsheng dyestuff chemical Co., Ltd.) was dissolved in 200ml of water, and 2, 3-dibromopropionyl chloride (25.0g, 0.1mol, 98% from carbofuran science Co., Ltd.) was added dropwise to the solution, while a 10% sodium bicarbonate solution was continuously added dropwise, the pH was adjusted to 5-6, and the reaction was carried out for 2-3 hours while maintaining the pH at 5-6, to give an aqueous solution of Compound 5.
And a sixth step: diazotization of Compound 5
Cooling the aqueous solution of compound 5 obtained in the fifth step to 0-5 ℃, adjusting the pH to be less than 3 by using 30% hydrochloric acid, slowly dropwise adding an aqueous solution of sodium nitrite (8.3g, 0.12mol), keeping the temperature for reaction for 30-45min after dropwise adding, and destroying excessive nitrous acid by using sulfamic acid (99.5% of Shandong Ming Daichemical science and technology Co., Ltd.) to obtain the product of the aqueous suspension of compound 6.
The seventh step: synthesis of Compound I-1
The compound I-1 is formed by coupling a compound 6 and a compound 4.
And dropwise adding the aqueous suspension of the compound 6 obtained in the sixth step into the aqueous solution of the compound 4 obtained in the fourth step at room temperature, adjusting the pH value to 4-6 by using NaOH with the concentration of 5%, and stirring for reacting for 2-3h to obtain the product, namely the aqueous solution of the red reactive dye compound I-1, wherein the structure of the red reactive dye compound I-1 is shown as the compound I-1, and the maximum absorption wavelength lambda in water is 510 nm. Obtaining solid powder by adopting a freeze drying mode (the freeze drying temperature is-20-0 ℃, the freeze drying time is 48 hours), and obtaining the element analysis result after purification treatment: theoretical value (%) C, 36.11; h, 2.25; n, 10.80; experimental value (%) C, 36.32; h, 2.27; n, 10.69; ESI (M/z)1297.8(M + H). The cotton is dyed in a non-aqueous medium, so that the cotton fiber is in bright red and the dye-uptake is 93.7 percent.
Example 2
First step, condensation of cyanuric chloride with H acid
Cyanuric chloride (9.2g, 0.05mol, 98% from Zhejiang Longsheng dye chemical Co., Ltd.) was mixed with 100mL of water (containing 1% of emulsifier TX-100, 98% from Nantong Yongle chemical Co., Ltd.), cooled to 0-5 deg.C, and adjusted to pH 5-6 with 5% NaOH. H acid (16.0g, 0.05mol, Zhejiang dragon dye chemical Co., Ltd., wet cake, solid content 85.48%) was mixed with water (200mL), and 10% NaOH was added to dissolve it (pH < 7). Slowly dripping the H acid solution into the aqueous suspension of the cyanuric chloride at the temperature of 0-5 ℃, continuously dripping NaOH with the concentration of 5 percent to adjust the pH value to be 5-6, and reacting for 2-3H under the condition of heat preservation to generate the aqueous solution of the compound 7.
Second step, coupling of Compound 1 with Compound 7
The synthesis of compound 1 is shown in example 1.
The aqueous suspension of compound 1, para-anisidine-3-sulfonic acid diazonium salt, prepared in example 1, was slowly added dropwise to the aqueous solution of compound 7 at 0 to 5 c, while NaOH at 5% concentration was continuously added dropwise to adjust pH 5 to 6, and the reaction was allowed to proceed for 2 to 3 hours while maintaining the temperature, to yield an aqueous solution of compound 8.
In the third step, the gamma acid is condensed with a compound 8
Gamma acid (12.0g, 0.05mol, wet cake, solid content 95.36% from Zhejiang dragon dye chemical Co., Ltd.) was mixed with 100ml of water, 10% NaOH was added dropwise to dissolve it (pH <7), the solution was heated to 30-35 ℃ and gamma acid solution was slowly added dropwise to the above compound 8 aqueous solution, while 5% NaOH was continuously added dropwise to adjust pH 4-6, and the reaction was maintained for 2-3 hours, producing compound 9 aqueous solution.
The fourth step, Synthesis of Compound I-2
Compound I-2 is formed by coupling compound 9 and compound 6, and the details of the synthesis of compound 6 are shown in example 1.
The aqueous suspension of compound 6 prepared in example 1 was added dropwise to the aqueous solution of compound 9 above at a temperature of 30 to 35 c, while NaOH at a concentration of 5% was continuously added dropwise to adjust the pH to 4 to 6, and the reaction was maintained for 2 to 3 hours to give an aqueous solution of compound I-2. The maximum absorption wavelength λ of the solution was 515 nm. Obtaining solid powder by adopting a freeze drying mode (the freeze drying temperature is-20-0 ℃, and the freeze drying time is 48 hours), and obtaining the purified elemental analysis result: theoretical value (%): C, 36.11; h, 2.25; n, 10.80; the experimental value (%) is C, 36.01; h, 2.21; n, 10.59; ESI (M/z):1297.8(M + H). The cotton is dyed in a non-aqueous medium, so that the cotton fiber is in bright red and the dye-uptake is 94.8 percent.
Example 3
First step, diazotization of meta-ester-4-sulfonic acid
Meta-ester-4-sulfonic acid (18.0g, 0.05mol, 56.5% solid content wet cake from Zhejiang Longsheng dye chemical Co., Ltd.) was mixed with 150mL of water, 30% hydrochloric acid was added dropwise to adjust pH to 3, the mixture was cooled to 0-5 ℃, sodium nitrite (4.2g, 0.06mol) was added dropwise, and the mixture was reacted for 2 hours while maintaining the temperature. Excess nitrous acid was destroyed with sulfamic acid and the product formed was an aqueous suspension of compound 10.
Second step, Synthesis of Compound I-3
Compound I-3 is formed by coupling compound 10 and compound 9, and the details of the synthesis of compound 9 are shown in example 2.
An aqueous suspension of the above compound 10 was added dropwise to an aqueous solution of the compound 9 prepared in example 2 at room temperature, while continuously adding 5% NaOH dropwise to adjust pH 4 to 6, and the reaction was maintained for 2 to 3 hours, to give an aqueous solution of the compound I-3 having a maximum absorption wavelength λ 508 nm. Adopting a freeze drying mode (the freeze drying temperature is-20-0 ℃, the freeze drying time is 48 hours) to obtain solid powder, and obtaining a purified elemental analysis result, namely a theoretical value (%) C, 33.01; h, 2.15; n, 9.62; experimental value (%) C, 33.21; h, 2.10; n, 9.47; ESI (M/z)1455.7(M + H). The cotton is dyed in a non-aqueous medium, so that the cotton fiber is in bright red and the dye-uptake is 92.8 percent.
Example 4
First step, Synthesis of Compound 11
Compound 11 is formed by the condensation of J acid and compound 8, and the details of the synthesis of compound 8 are given in example 2.
J acid (23.9g, 0.1mol, wet cake, solid content 90.76% from zhejiang dragon flourishing dye chemical co., ltd.) was mixed with 250mL of water, and hydrochloric acid of 30% concentration was added dropwise to adjust pH 5 to 6 and completely dissolve the J acid. The aqueous solution of compound 8 prepared in example 2 was heated to 30-35 c, and the J acid solution was slowly added dropwise thereto while NaOH at a concentration of 5% was continuously added dropwise to adjust the pH to 5-6, and the reaction was maintained for 2-3h to give an aqueous solution of compound 11.
Second step, Synthesis of Compound I-4
Compound I-4 is formed by coupling compound 11 and compound 10, and the details of the synthesis of compound 10 are shown in example 3.
An aqueous suspension of compound 10 prepared in example 3 was slowly added dropwise to an aqueous solution of compound 11 as described above at room temperature, while NaOH at a concentration of 5% was continuously added dropwise to adjust pH 5 to 6, and the reaction was maintained for 2 to 3 hours, to give an aqueous solution of compound I-4 having a maximum absorption wavelength λ of 500 nm. Adopting a freeze drying mode (the freeze drying temperature is-20-0 ℃, the freeze drying time is 48 hours) to obtain solid powder, and obtaining a purified elemental analysis result, namely a theoretical value (%) C, 33.01; h, 2.15; n, 9.62; (ii) a Experimental value (%) C, 33.51; h, 2.20; n, 9.38; ESI (M/z)1455.7(M + H). The cotton is dyed in a non-aqueous medium, so that the cotton fiber is in bright red and the dye-uptake is 98 percent.
Comparative example 1
The cotton is dyed by commercial dye (reactive red M-3BE, C.I. reactive red 195, Zhejiang dragon dye chemical Co., Ltd.) in non-aqueous medium by the same method, and the dye uptake is 70.23%. The structure of active red M-3BE is as follows:
dyeing method
Pretreatment of cotton fabric:
cotton fabric (commercially available bleached plain cloth) 10g was soaked in Na at a concentration of 20g/L2CO3The solution is soaked for 30min, and then the swelled cotton fabric is put into a centrifuge tube provided with a steel mesh for supporting a sample, and is centrifuged for 3.5min at the rotating speed of 1400 rpm. And (4) accurately weighing the centrifuged fabric, and then putting the fabric into an oven to be dried until the moisture content of the cotton fabric is 2%.
Dyeing:
1g (to. + -. 0.0002g) of the above pretreated cotton fabric (commercially available bleached plain cloth) was weighed and 30mg (to. + -. 0.0002g) was weighed at a colour intensity of 3%. Measuring 5mL of DMSO/PCE mixed solution according to a bath ratio (cotton fabric/DMSO/PCE (tetrachloroethylene) ═ 1: 5-25), adding the mixed solution into a small glass bottle filled with 30mg of dye, and fully dissolving the dye to form a solution 1.
Adding the solution 1 and the pretreated cotton fabric into one dyeing tank to serve as an experimental group, only adding the solution 1 into the other dyeing tank to serve as a control experiment without discharging the cotton fabric, heating to 25 ℃, heating to 55 ℃ at the speed of 1 ℃/min, preserving heat for 10min, adding 5-20 ml of PCE into both dyeing tanks, then heating to 95 ℃ at the speed of 1 ℃/min, preserving heat for 2h, then cooling to room temperature, taking out the cotton fabric and squeezing to dry.
Determination of the dye uptake:
respectively adding 10ml of methanol into the two dyeing tanks to uniformly mix the solvents in the dyeing tanks (DMSO and PCE are not mutually soluble, and the undyed dye is on a DMSO layer), respectively pouring the dye solutions in the two dyeing tanks into a 50ml volumetric flask, fixing the volume to 50ml, then measuring the mixed solution in a 2ml blank control group dyeing tank, diluting by n times, and measuring the absorbance A0Then measuring the absorbance A of the dye liquor in the dyeing tank containing cotton cloth1(there is a need to dilute the dye liquor as the case may be). The formula for the dye uptake is as follows:
dye uptake rate ═ a0(n+1)-A1)/(A0(n+1))×100％
A0Diluting the mixed solution in the blank control group staining tank by n times and then testing the absorbance value;
A1diluting the mixed solution in the experimental dye tank by n times and then testing the absorbance value;
and n is the dilution multiple.
Although the present invention has been described with reference to a preferred embodiment, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (1)
1. Use of a red reactive dye as a reactive dye for dyeing cotton-containing fabrics in a non-aqueous medium;
wherein the red reactive dye is a compound shown as a formula I-1, I-2, I-3 or I-4:
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2748966A1 (en) * | 1977-11-02 | 1979-05-03 | Hoechst Ag | HYDRO-SOLUBLE COLORS, PROCESS FOR THEIR PRODUCTION, THEIR USE AS FIBER-REACTIVE COLORS FOR COLORING AND PRINTING FIBER MATERIALS AND FIBER MATERIALS DYED WITH THEM |
| US5200511A (en) * | 1991-04-27 | 1993-04-06 | Basf Aktiengesellschaft | Cholorotriazine dyes with two azo chromophores exhibiting further reactive groups |
| CN1167785A (en) * | 1996-04-24 | 1997-12-17 | 希巴特殊化学控股公司 | Fibre-reactive dyes, their preparation and their use |
| CN107419553A (en) * | 2016-05-23 | 2017-12-01 | 海宁绿宇纺织科技有限公司 | A kind of colouring method of silicon substrate non-aqueous media suitable for reactive dye |
-
2019
- 2019-03-06 CN CN201910166237.XA patent/CN109825108B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2748966A1 (en) * | 1977-11-02 | 1979-05-03 | Hoechst Ag | HYDRO-SOLUBLE COLORS, PROCESS FOR THEIR PRODUCTION, THEIR USE AS FIBER-REACTIVE COLORS FOR COLORING AND PRINTING FIBER MATERIALS AND FIBER MATERIALS DYED WITH THEM |
| US5200511A (en) * | 1991-04-27 | 1993-04-06 | Basf Aktiengesellschaft | Cholorotriazine dyes with two azo chromophores exhibiting further reactive groups |
| CN1167785A (en) * | 1996-04-24 | 1997-12-17 | 希巴特殊化学控股公司 | Fibre-reactive dyes, their preparation and their use |
| CN107419553A (en) * | 2016-05-23 | 2017-12-01 | 海宁绿宇纺织科技有限公司 | A kind of colouring method of silicon substrate non-aqueous media suitable for reactive dye |
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