CN108912725B - Sulfonamide blue disperse dye and preparation method thereof - Google Patents

Sulfonamide blue disperse dye and preparation method thereof Download PDF

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CN108912725B
CN108912725B CN201810572931.7A CN201810572931A CN108912725B CN 108912725 B CN108912725 B CN 108912725B CN 201810572931 A CN201810572931 A CN 201810572931A CN 108912725 B CN108912725 B CN 108912725B
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dye
sulfonamide
blue
disperse dye
blue disperse
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CN108912725A (en
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崔志华
王星
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Shaoxing Jincao Chemical Co ltd
Zhejiang Sci Tech University ZSTU
Shangyu Industrial Technology Research Institute of ZSTU
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Shaoxing Jincao Chemical Co ltd
Zhejiang Sci Tech University ZSTU
Shangyu Industrial Technology Research Institute of ZSTU
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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
    • C09B57/00—Other synthetic dyes of known constitution
    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008—Preparations of disperse dyes or solvent dyes

Abstract

The invention discloses a sulfonamide blue disperse dye, which has a structural general formula as follows:
Figure DDA0001686382060000011
in the formula: r is H, CnH2n+1、OCnH2n+1Cl, Br or NO2Wherein n is any integer from 1 to 12. The invention also discloses a preparation method thereof: reacting indigo dye and benzene sulfonyl chloride (or derivatives thereof) in a solvent under the action of potassium carbonate serving as an acid-binding agent; and (3) decompressing the reaction product, distilling off the solvent, and sequentially carrying out acid washing, water washing and drying on the obtained residue to obtain the blue sulfonamide disperse dye. The dye obtained by the invention has certain solubility in water, so that the efficient dyeing of the terylene can be realized in a water system, the oxidation resistance and the heat resistance of the dye are improved, and the color fastness of the dye on the terylene fiber is further improved.

Description

Sulfonamide blue disperse dye and preparation method thereof
Technical Field
The invention relates to a sulfonamide blue disperse dye and a preparation method thereof.
Background
In 2015, a group of researchers led by doctor Jixun Zhan at utah state university in usa produced an indigo dye called indigo dye with escherichia coli and mass production was achieved. Indigo dye of indigo has pure blue hue, and can be used as coloring agent in food, beverage or cosmetic after further purification treatment. The blue natural dye has attracted more and more attention in the textile industry due to the characteristics of no toxicity, no harm, no pollution and the like. However, the dye structure has two primary amine groups, has poor oxidation resistance and heat resistance, and can quickly fade blue under boiling conditions to become a brown substance. Furthermore, indigo is poorly soluble in solvents and only poorly soluble in DMF and DMSO, making it difficult to achieve staining with aqueous media. Therefore, it is possible to improve the solubility, oxidation resistance and heat resistance of the dye by structurally modifying it.
Figure BDA0001686382050000011
The terylene is an important variety in synthetic fibers, and is a fiber prepared by using Purified Terephthalic Acid (PTA) or dimethyl terephthalate (DMT) and Ethylene Glycol (EG) as raw materials to prepare a fiber-forming high polymer, namely polyethylene terephthalate (PET), through esterification or ester exchange and polycondensation reactions, and spinning and post-treatment. The output of polyester fiber in the textile industry at present exceeds the dominant position of cotton fiber.
The polyester fiber is dyed by mainly adopting disperse dye, and the dyeing temperature is usually close to or over 100 ℃. After the polyester fiber is dyed by the disperse dye, the dye and the fiber are combined through weak van der Waals force and hydrogen bonding force. The Van der Waals force and the hydrogen bond force are large, the dye has high affinity on the fiber and good color fastness, and the dye shows high dye uptake; on the contrary, the color fastness is poor and the dye uptake is low. A large number of benzene ring structures and relatively more ester groups exist on a polyester macromolecular chain, so that the polyester fiber molecular chain has certain polarity and rigidity.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a sulfonamide blue disperse dye and a preparation method thereof, wherein the dye has certain solubility in water, so that the dye can realize efficient dyeing of terylene in a water system, and the oxidation resistance and heat resistance of the dye are improved, thereby improving the color fastness of the dye on terylene fibers.
In order to solve the technical problems, the invention provides a sulfonamide blue disperse dye, the molecular structure of which contains a sulfonamide group, and the structural general formula of which is as follows:
Figure BDA0001686382050000021
in the formula: r is H, CnH2n+1、OCnH2n+1Cl, Br or NO2Wherein n is any integer from 1 to 12.
The invention also provides a preparation method of the novel blue disperse dye, which is prepared by reacting indigo dye with benzene sulfonyl chloride or derivatives thereof, and specifically comprises the following steps:
1) dissolving indigo dye in N, N-Dimethylformamide (DMF) to obtain a dye solution;
dissolving benzenesulfonyl chloride or its derivatives in N, N-Dimethylformamide (DMF), adding into the dye solution, adding potassium carbonate as acid-binding agent, and reacting at room temperature for 0.5-6 hr;
the indigo dye: benzenesulfonyl chloride or derivatives thereof: potassium carbonate in a molar ratio of 1:2: 4;
the structural formula of the indigo dye is as follows:
Figure BDA0001686382050000022
2) and decompressing the reaction product obtained in the step 1) to evaporate DMF (dimethyl formamide) serving as a solvent under the pressure of (-0.09MPa, at 90 ℃, and sequentially carrying out acid washing, water washing and drying on the obtained residue to obtain the sulfonamide blue disperse dye.
As an improvement of the preparation method of the blue disperse dye of the invention:
the benzenesulfonyl chloride derivatives are p-methylbenzenesulfonyl chloride, m-methylbenzenesulfonyl chloride, p-chlorobenzenesulfonyl chloride, p-methoxybenzenesulfonyl chloride and p-nitrobenzenesulfonyl chloride; there are other configurations depending on the value of n.
As a further improvement of the preparation method of the blue disperse dye of the invention:
10-30 ml of N, N-Dimethylformamide (DMF) is added to every 0.01mol of indigo dye;
10-30 ml of N, N-Dimethylformamide (DMF) is added to every 0.02mol of arylsulfonyl chloride.
The sulfonamide blue disperse dye is used for dyeing polyester fibers, and the dyeing process comprises the following steps:
adding 5-10 g of the sulfonamide blue disperse dye, 5-10 g of a dispersant NNO, 200g of zirconium beads (with the particle size of 1-2 mm) and 50-100 g of water into a sand mill, sanding for 2-10 hours, filtering by using a Buchner funnel, and obtaining a 120-mesh steel wire mesh as a filter screen to obtain dye color paste; transferring dye color paste according to the chromaticity requirement of 0.5-2%, and mixing according to the bath ratio of 1: 15-30, adding water, transferring the mixture into a dyeing tube, adding the polyester fabric to be dyed into a high-temperature high-pressure dyeing instrument, heating to 130 ℃ at a heating rate of 2 ℃/min, keeping the temperature for 1 hour, cooling to room temperature, taking out a dyed cloth sample, washing, combining dyeing residual liquid and washing liquid, measuring the absorbance of the dyeing residual liquid and the washing liquid at constant volume, and calculating the dye uptake of the dye by using a working curve.
Aiming at the characteristics of the indigo dye, the invention considers that if aromatic rings are introduced into molecules of the indigo dye, the pi-pi acting force between dye molecules and polyester fiber macromolecules can be improved, and the dye uptake and the color fastness of the dye can be improved. In addition, electron-withdrawing groups (such as sulfone groups, carbonyl groups and the like) are introduced to the amino structure, so that the electron cloud density on the N atom of the amino can be reduced, and the oxidation resistance and the heat-resistant stability of the dye are improved.
According to the invention, different aromatic sulfonamide groups are introduced into the dye structure, so that the affinity of the dye to polyester fibers can be improved, the dye-uptake rate is improved, and the molecular polarity of the dye is increased, thereby being beneficial to improving the sublimation fastness of the dye. In addition, the introduction of the sulfone group can effectively reduce the electron cloud density on the amino group and improve the light fastness of the dye.
The invention develops a sulfonamide blue disperse dye, and the dye can adjust the affinity between the dye and the polyester fiber by changing the type of a sulfonamide group connecting end group; meanwhile, the introduction of the benzene ring in the dye structure increases the pi-pi acting force between the dye and the polyester fiber, and is beneficial to the improvement of the dye uptake and the color fastness. In addition, the strong electric absorption property of the sulfone group in the sulfonamide structure can obviously reduce the electron cloud density on an amino N atom in the indigo dye parent structure, and improve the oxidation resistance and the heat-resistant stability of the dye. The dye is simple in synthesis process and can be prepared by condensing indigo dye and arylsulfonyl chloride. The developed blue sulfonamide disperse dye has affinity adjustability and excellent color fastness, and has wide application prospect.
Detailed Description
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
example 1, a method for preparing a blue sulfonamide disperse dye, sequentially comprising the steps of:
1) adding 0.01mol of indigo dye and 10mLDMF into a three-necked bottle provided with a stirrer and a thermometer, and heating to 60 ℃ for dissolving for later use;
2) then adding a mixed solution of 0.02mol of benzenesulfonyl chloride and 30ml of DMF into the dye solution, then adding 0.04mol of potassium carbonate serving as an acid-binding agent, and reacting for 6 hours at room temperature;
3) after the reaction is finished, distilling out the DMF solvent at 90 ℃ under reduced pressure (-0.09 MPa) to obtain a residue; the residue was subjected to acid washing (50 ml of aqueous hydrochloric acid solution at a concentration of 5% each time, 3 times in total), water washing (50 ml each time, 3 times in total), and drying (50 ℃ C. to constant weight) in this order to obtain a blue sulfonamide disperse dye.
The structural formula of the sulfonamide blue disperse dye is as follows:
Figure BDA0001686382050000041
that is, with respect to the above general structural formula, in the formula: r is H.
1H NMR(400MHz,DMSO-d6)：δ10.08(s,2H),7.93(d,4H),7.54(t,4H),7.30(t,2H),5.69(s,2H),2.01(s,2H)；ESI MS(m/z,％):527.04([M-H]-,100)。
Example 2, a method for preparing a blue sulfonamide disperse dye, sequentially comprising the following steps:
1) adding 0.01mol of indigo dye and 10mLDMF into a three-necked bottle provided with a stirrer and a thermometer, and heating to 60 ℃ for dissolving for later use;
2) then adding a mixed solution of 0.02mol of p-toluenesulfonyl chloride and 30ml of DMF into the dye solution, subsequently adding 0.04mol of potassium carbonate as an acid-binding agent, and reacting for 0.5hr at room temperature;
3) after the reaction is finished, distilling off the DMF solvent at 90 ℃ under reduced pressure to obtain a residue; and (4) sequentially carrying out acid washing, water washing and drying on the residue to obtain the sulfonamide blue disperse dye.
The structural formula of the sulfonamide blue disperse dye is as follows:
Figure BDA0001686382050000051
that is, with respect to the above general structural formula, in the formula: r is CH3In the para position with respect to the sulfone group.
1H NMR(400MHz,DMSO-d6)：δ10.05(s,2H),7.81(d,4H),7.34(d,4H),5.69(s,2H),2.35(t,2H),2.03(s,2H)；ESI MS(m/z,％):555.07([M-H]-,100)。
Example 3, a method for preparing a blue sulfonamide disperse dye, sequentially comprising the steps of:
1) adding 0.01mol of indigo dye and 10mLDMF into a three-necked bottle provided with a stirrer and a thermometer, and heating to 60 ℃ for dissolving for later use;
2) then adding a mixed solution of 0.02mol of m-methylbenzenesulfonyl chloride and 30ml of DMF into the dye solution, subsequently adding 0.04mol of potassium carbonate serving as an acid-binding agent, and reacting for 0.5hr at room temperature;
3) after the reaction is finished, distilling off the DMF solvent at 90 ℃ under reduced pressure to obtain a residue; and (4) sequentially carrying out acid washing, water washing and drying on the residue to obtain the sulfonamide blue disperse dye.
The structural formula of the sulfonamide blue disperse dye is as follows:
Figure BDA0001686382050000052
that is, with respect to the above general structural formula, in the formula: r is CH3In the meta position relative to the sulfone group.
1H NMR(400MHz,DMSO-d6)：δ10.06(s,2H),7.74(m,4H),7.42(t,2H),7.10(d,2H),5.69(s,2H),2.35(t,2H),2.06(s,2H)；ESI MS(m/z,％):555.03([M-H]-,100)。
Example 4, a method for preparing a blue sulfonamide disperse dye, sequentially comprising the steps of:
1) adding 0.01mol of indigo dye and 10mLDMF into a three-necked bottle provided with a stirrer and a thermometer, and heating to 60 ℃ for dissolving for later use;
2) then adding a mixed solution of 0.02mol of p-methoxybenzenesulfonyl chloride and 30ml of DMF into the dye solution, subsequently adding 0.04mol of potassium carbonate serving as an acid-binding agent, and reacting for 0.5hr at room temperature;
3) after the reaction is finished, distilling off the DMF solvent at 90 ℃ under reduced pressure to obtain a residue; and (4) sequentially carrying out acid washing, water washing and drying on the residue to obtain the sulfonamide blue disperse dye.
The structural formula of the sulfonamide blue disperse dye is as follows:
Figure BDA0001686382050000061
that is, with respect to the above general structural formula, in the formula: r is OCH3In the para position with respect to the sulfone group.
1H NMR(400MHz,DMSO-d6)：δ10.01(s,2H),7.82(d,4H),7.05(d,4H),5.69(s,2H),2.01(s,2H)；ESI MS(m/z,％):587.06([M-H]-,100)。
Example 5, a method for preparing a blue sulfonamide disperse dye, sequentially comprising the steps of:
1) adding 0.01mol of indigo dye and 10mLDMF into a three-necked bottle provided with a stirrer and a thermometer, and heating to 60 ℃ for dissolving for later use;
2) then adding a mixed solution of 0.02mol of p-chlorobenzenesulfonyl chloride and 30ml of DMF into the dye solution, subsequently adding 0.04mol of potassium carbonate as an acid-binding agent, and reacting for 0.5hr at room temperature;
3) after the reaction is finished, distilling off the DMF solvent at 90 ℃ under reduced pressure to obtain a residue; and (4) sequentially carrying out acid washing, water washing and drying on the residue to obtain the sulfonamide blue disperse dye.
The structural formula of the sulfonamide blue disperse dye is as follows:
Figure BDA0001686382050000071
that is, with respect to the above general structural formula, in the formula: r is Cl and is positioned at the para position of the sulfuryl.
1H NMR(400MHz,DMSO-d6)：δ10.01(s,2H),7.87(d,4H),7.55(d,4H),5.69(s,2H),2.05(s,2H)；ESI MS(m/z,％):594.96([M-H]-,100)。
Example 6, a method for preparing a blue sulfonamide disperse dye, sequentially comprising the steps of:
1) adding 0.01mol of indigo dye and 10ml of DMDMF into a three-necked bottle provided with a stirrer and a thermometer, and heating to 60 ℃ for dissolving for later use;
2) then adding a mixed solution of 0.02mol of p-nitrobenzenesulfonyl chloride and 30ml of DMF into the dye solution, then adding 0.04mol of potassium carbonate serving as an acid-binding agent, and reacting for 0.5hr at room temperature;
3) after the reaction is finished, distilling off the DMF solvent at 90 ℃ under reduced pressure to obtain a residue; and (4) sequentially carrying out acid washing, water washing and drying on the residue to obtain the sulfonamide blue disperse dye.
The structural formula of the sulfonamide blue disperse dye is as follows:
Figure BDA0001686382050000072
that is, with respect to the above general structural formula, in the formula: r is NO2In the para position with respect to the sulfone group.
1H NMR(400MHz,DMSO-d6)：δ10.07(s,2H),8.47(d,4H),8.19(d,4H),5.73(s,2H),2.09(s,2H)；ESI MS(m/z,％):587.06([M-H]-,100)。
The application of the sulfonamide blue disperse dye in dyeing polyester fiber is illustrated by experiments.
Experiment 1,
5-10 g of the sulfonamide blue disperse dye synthesized in the embodiment, 5-10 g of a dispersant NNO, 200g of zirconium beads (with the particle size of 1-2 mm) and 50-100 g of water are added into a sand mill to be sanded for 2-10 hours, a Buchner funnel is used for filtering, and a filter screen is a 120-mesh steel wire mesh to obtain dye color paste; transferring the disperse dye color paste according to the chromaticity requirement of 0.5-2%, and mixing the disperse dye color paste according to the bath ratio of 1: 15-30, adding water, transferring the mixture into a dyeing tube, adding the polyester fabric to be dyed, putting the polyester fabric into a high-temperature high-pressure dyeing instrument, heating to 130 ℃ at a heating rate of 2 ℃/min, keeping the temperature for 1 hour, cooling to room temperature, taking out a dyed cloth sample, washing, combining dyeing residual liquid and washing liquid, determining the absorbance of a constant volume detector, and solving the dye uptake of the dye by utilizing the Lambert-beer law; the dyed cloth sample is subjected to reduction cleaning by adopting a post-treatment method of the color light and intensity of disperse dye dyeing of the national standard (GB/T2394-. The results are shown in Table 1.
TABLE 1
Figure BDA0001686382050000081
Comparative experiment 1,
The sulfonamide blue disperse dye in experiment 1 was changed to indigo dye, the rest of experiment 1. The results are as follows: the dye uptake was 3.5%, and the dye residue changed from blue to brown (the dye was poor in heat resistance or oxidized) after dyeing. After reduction washing, the terylene cloth has no color. The stability of the dye is obviously improved after the dye is modified by benzene sulfonyl chloride, the dye can be used as a dye for dyeing polyester fabrics, and various color fastness is excellent.
Finally, it is also noted that the above-mentioned lists merely illustrate a few specific embodiments of the invention. It is obvious that the invention is not limited to the above embodiments, but that many variations are possible. All modifications which can be derived or suggested by a person skilled in the art from the disclosure of the present invention are to be considered within the scope of the invention.

Claims (4)

1. The sulfonamide blue disperse dye is characterized by having a structural general formula as follows:
Figure FDA0002224255240000011
in the formula: r is H, CnH2n+1、OCnH2n+1Cl, Br or NO2Wherein n is 1.
2. The method for preparing blue disperse sulfonamide dyes according to claim 1, wherein the step of reacting indigo dye with benzenesulfonyl chloride or its derivatives comprises the steps of:
1) dissolving indigo dye in N, N-dimethylformamide to obtain a dye solution;
dissolving benzenesulfonyl chloride or its derivative in N, N-dimethylformamide, adding into the dye solution, adding potassium carbonate as acid-binding agent, and reacting at room temperature for 0.5-6 hr;
the indigo dye: benzenesulfonyl chloride or derivatives thereof: potassium carbonate in a molar ratio of 1:2: 4;
the structural formula of the indigo dye is as follows:
Figure FDA0002224255240000012
2) and decompressing the reaction product obtained in the step 1) to evaporate DMF (dimethyl formamide) serving as a solvent, and sequentially carrying out acid washing, water washing and drying on the obtained residue to obtain the sulfonamide blue disperse dye.
3. The method for preparing the sulfonamide blue disperse dye according to claim 2, wherein:
the benzene sulfonyl chloride derivative is p-methyl benzene sulfonyl chloride, m-methyl benzene sulfonyl chloride, p-chlorobenzene sulfonyl chloride, p-methoxy benzene sulfonyl chloride, or p-nitrobenzene sulfonyl chloride.
4. The method for preparing the sulfonamide blue disperse dye according to claim 3, wherein:
10-30 mL of N, N-dimethylformamide is matched with each 0.01mol of indigo dye;
10-30 mL of N, N-dimethylformamide is added to every 0.02mol of benzenesulfonyl chloride or its derivative.
CN201810572931.7A 2018-06-06 2018-06-06 Sulfonamide blue disperse dye and preparation method thereof Active CN108912725B (en)

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