CN111635643A - Disperse dye compound and preparation and application methods thereof - Google Patents

Disperse dye compound and preparation and application methods thereof Download PDF

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CN111635643A
CN111635643A CN202010610684.2A CN202010610684A CN111635643A CN 111635643 A CN111635643 A CN 111635643A CN 202010610684 A CN202010610684 A CN 202010610684A CN 111635643 A CN111635643 A CN 111635643A
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reaction
disperse dye
dye compound
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冯高峰
郭小燕
钱红飞
方帅军
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University of Shaoxing
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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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • 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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • C09B29/0801—Amino benzenes containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H, OPO3H2; SO2NHSO2R or salts thereof, R being hydrocarbonyls
    • C09B29/0802—Amino benzenes containing acid groups, e.g. COOH, SO3H, PO3H2, OSO3H, OPO3H2; SO2NHSO2R or salts thereof, R being hydrocarbonyls containing COOH
    • 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
    • D06P1/16—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 dispersed, e.g. acetate, dyestuffs
    • D06P1/18—Azo dyes
    • 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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/26—Polyamides; Polyurethanes using dispersed dyestuffs

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  • Organic Chemistry (AREA)
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Abstract

The application provides a disperse dye compound and preparation and application methods thereof, belonging to the technical field of monoazo dyes prepared by a coupling method. The disperse dye compound has the following structural formula:
Figure DDA0002561698890000011
wherein R is1Is H or Cl, R2Is H or Cl. The disperse dye compound introduces ester groups and amide groups, improves the interaction between the dye and fibers, and greatly improves the dyeing performance and color fastness on chinlon.

Description

Disperse dye compound and preparation and application methods thereof
Technical Field
The application relates to a disperse dye compound and preparation and application methods thereof, belonging to the technical field of monoazo dyes prepared by a coupling method.
Background
Disperse dyes are the most widespread dye class of the current hydrophobic fiber dyeing dyes. The disperse dyes may be azo type, anthraquinone type, heterocyclic type depending on the type of color body. The azo type disperse dye is the most main type of disperse dye, accounts for about 60 percent, has complete chromatogram, and can obtain different spectral properties and dyeing properties by changing the electronic effect of substituent groups on the diazo component and the coupling component.
Disperse dyes have been developed with the development of synthetic fibers. At present, with the appearance of superfine polyester fibers, environment-friendly polylactic acid fibers, differential terylene easy-to-dye fibers and novel fibers, most of the existing disperse dyes have poor affinity with the fibers, and are easy to generate heat migration after being heated, so that the fibers have poor washing fastness and poor application performance. Therefore, new synthetic methods and strategies are needed to be developed to rapidly obtain novel high-performance disperse dyes with various structures so as to meet the dyeing requirements of the dyes on various fibers.
The magnitude of the acting force between the disperse dye and the fiber fundamentally determines the dyeing performance and the color fastness of the disperse dye. From the analysis of the disperse dye coloring mechanism, the fiber structure and the like, the following methods can be adopted to improve the disperse dye dyeing performance and the color fastness:
1. according to the principle of 'similar compatibility', special functional groups such as ester groups, amide groups and the like are introduced into the disperse dye, and the functional groups such as the ester groups, the amide groups and the like can form hydrogen bonds with fibers, so that stronger interaction is obtained to improve the dyeing performance of the disperse dye;
2. effectively increase the molecular weight of the dye. Along with the increase of molecular weight, the acting force between dye molecules and fibers is increased, and the dyeing properties such as heat migration resistance fastness, sublimation resistance fastness and the like are improved.
The development of a proper synthetic method and a proper synthetic strategy, the effective regulation and control of the molecular weight of the disperse dye and the introduction of a special functional group capable of interacting with fibers are the key points of the development of the high-performance disperse dye. The method has the advantages of simple and easily obtained multi-component reaction raw materials, rapid and efficient reaction, various product skeleton structures and substituent groups, easy regulation and control of molecular weight, and introduction of special groups capable of interacting with fibers, and is an ideal method and strategy for obtaining high-performance disperse dyes.
Disclosure of Invention
The first aspect of the invention aims to provide a novel high-performance disperse dye compound which has a remarkable effect on the dyeing performance and color fastness of chinlon as a disperse dye or a disperse dye component.
Specifically, the technical scheme adopted by the scheme is as follows:
a disperse dye compound having the structural formula:
Figure BDA0002561698870000021
wherein: r1Is H or Cl, R2Is H or Cl.
The disperse dye compound has the structural characteristics that: has moderate molecular weight and volume, and contains one ester group and two amide groups (RCOO-, -CONR)2-CONHR), which structural features have a significant influence on the improvement of the dyeing properties and of the colorfastness of the novel dyes, as summarized in detail below:
(1) the effective increase of the molecular volume and the molecular weight of the dye improves the contact surface between the dye and the fiber, and enhances the Van der Waals force between the dye and the fiber, thereby improving the affinity between the dye and the fiber, and improving the dyeing performance and the color fastness of the dye and the fiber.
(2) By introducing characteristic groups such as ester group and amide group, hydrogen bonds can be formed with hydrogen receiving groups and hydrogen supplying groups in the fibers, and the characteristic groups are suitable for the structure of the polyester fibers, so that the acting force between the characteristic groups and the polyester fibers is enhanced, and the dyeing performance can be improved.
(3) In the synthesis of the azo disperse dye, the number of groups on the diazo component and the electronic effect have important influence on the maximum absorption wavelength and the color of the dye. Under the condition that the coupling components are the same, the azo disperse dyes with different colors can be obtained by selecting different substituted diazo components, thereby providing great convenience for the diversity synthesis of the azo disperse dyes.
Specifically, the disperse dye compound may be selected from any one of the following compounds:
Figure BDA0002561698870000031
in the preparation process of the disperse dye compound, a coupling component is generally prepared firstly, and the preparation process comprises the following two steps:
step one, acid synthesis: 13.0mmol succinic anhydride, 1.0mmol DMAP and 15mL CH are added in turn2Cl210.0mmol triethylamine and 10.0mmol N-ethyl-N-hydroxyethylaniline form a reaction mixed solution, stirring for 4 hours at room temperature, carrying out thin layer sample application to track the reaction process, carrying out reduced pressure concentration and vacuum drying on the reaction solution by using a rotary evaporator after the reaction is finished, and directly using the residue in the bottle for the Ugi four-component reaction;
step two, a Ugi four-component reaction: adding 70mL of anhydrous methanol, 12.0mmol of p-methylaniline and 12.0mmol of benzaldehyde, transferring the anhydrous methanol into the acid synthesized in the step (1), finally adding 10mmol of cyclohexylacetonitrile, heating and stirring in an oil bath at 80 ℃ for 48h, concentrating under reduced pressure after the reaction is finished, dissolving in 20mL of ethyl acetate, adding 10mL of petroleum ether, cooling until a large amount of white solid is separated out, carrying out suction filtration, washing by using an ethyl acetate/petroleum ether organic mixed solvent with the volume ratio of 1:5, and drying to obtain a coupling component.
The synthesis of the disperse dye compound of formula 1da also requires the following two steps:
(1) synthesis of diazonium salt:
dissolving 5.27mmol of sodium nitrite with 5mL of water, placing the solution in an ice water bath for 2min to form a sodium nitrite aqueous solution, mixing 5mL of water with 5mL of 36.5% hydrochloric acid, dropwise adding the mixture into 5.27mmol of 4-nitroaniline, dissolving the mixture for 1h at 40-60 ℃, cooling the solution to room temperature, placing the solution in the ice water bath, dropwise and slowly adding the sodium nitrite aqueous solution, and reacting the solution for 1h in the ice water bath after dropwise adding is finished to obtain 4-nitrophenyl diazonium salt;
(2) coupling reaction:
3.51mmol of the coupling component is added with 30mL of methanol, heated and stirred in an oil bath at the temperature of 80 ℃ until the coupling component is completely dissolved, cooled to room temperature, 4-nitrophenyldiazonium salt obtained in the step (1) is slowly dripped in under the condition of ice-water bath, stirred for 24 hours at the temperature of 0-5 ℃, filtered after the reaction is finished, washed and dried by ethyl acetate/petroleum ether organic mixed solvent with the volume ratio of 1:5, purified by adopting a column chromatography method to obtain pure dye, and eluted and dried by using ethyl acetate and petroleum ether mixed solvent with the volume ratio of 1:2 as eluent.
The synthesis of the disperse dye compound of formula 1db further requires the following two steps:
(1) synthesis of diazonium salt:
dissolving 5.27mmol of sodium nitrite with 5mL of water, placing the mixture in an ice water bath for 2min to form a sodium nitrite aqueous solution, mixing the 5mL of water with 5mL of 36.5% hydrochloric acid, dropwise adding the mixture into 5.27mmol of 2-chloro-4-nitroaniline, dissolving the mixture at 40-60 ℃, cooling the mixture to room temperature, placing the mixture in the ice water bath, dropwise and slowly adding the sodium nitrite aqueous solution, and reacting the mixture in the ice water bath for 1h after dropwise adding is finished to obtain 2-chloro-4-nitrophenyldiazonium salt;
(2) coupling reaction:
3.51mmol of the coupling component is added with 30mL of methanol, heated and stirred in an oil bath at the temperature of 80 ℃ until the coupling component is completely dissolved, cooled to room temperature, slowly and dropwise added with the 2-chloro-4-nitrophenyl diazonium salt in the step (1) under the condition of ice-water bath, stirred for 24 hours at the temperature of 0-5 ℃, filtered by suction after the reaction is finished, washed by an ethyl acetate/petroleum ether organic mixed solvent with the volume ratio of 1:5, and dried.
The synthesis of the disperse dye compound of formula 1dc requires the following two steps:
(1) synthesis of diazonium salt:
5.27mmol of sodium nitrite in 5mL of H2Dissolving O, placing in an ice water bath for 2min to obtain a sodium nitrite aqueous solution, mixing 5mL of water with 5mL of 36.5% hydrochloric acid, dropwise adding the mixture into 5.27mmol of 2, 6-dichloro-4-nitroaniline, dissolving at 40-60 ℃, placing in the ice water bath after cooling to room temperature, dropwise and slowly adding the sodium nitrite aqueous solution, and reacting in the ice water bath for 1h after dropwise adding is finished to obtain the 2, 6-dichloro-nitrophenyl diazonium salt.
(2) Coupling reaction:
3.51mmol of the coupling component is added with 30mL of methanol, heated and stirred in an oil bath at the temperature of 80 ℃ until the coupling component is completely dissolved, cooled to room temperature, the 2, 6-dichloro-nitrophenyl diazonium salt synthesized in the step (1) is slowly and dropwise added under the condition of ice-water bath, stirred for 24 hours at the temperature of 0-5 ℃, and after the reaction is finished, filtered, washed by an ethyl acetate/petroleum ether organic mixed solvent with the volume ratio of 1:5, and dried.
The second aspect of the present invention is to provide a method for preparing the above disperse dye compound, comprising the steps of:
(1) acid synthesis: in an organic solvent, adding a certain amount of N-ethyl-N-hydroxyethylaniline, succinic anhydride, DMAP and triethylamine into a reaction flask for reaction at room temperature. After the reaction is finished, directly carrying out reduced pressure concentration on the reaction liquid to obtain corresponding carboxylic acid for the next step of Ugi reaction;
(2) ugi reaction: in an organic solvent, the acid synthesized in the last step, benzaldehyde, p-methylaniline and cyclohexyl isonitrile are subjected to an Ugi four-component reaction at a certain temperature. After the reaction is finished, the reaction liquid is decompressed and concentrated, and a white Ugi product, namely the coupling component of the disperse dye compound, is obtained by adopting an ethyl acetate recrystallization method.
(3) Coupling reaction: in an organic solvent, the obtained coupling component and the 4-nitrophenyldiazonium compound are coupled at a certain temperature. After the reaction is finished, filtering, washing, drying and the like are carried out on the solid to obtain the novel azo disperse dye compound.
The above preparation process can be represented by the following reaction equation:
Figure BDA0002561698870000061
preferably, the further settings are as follows:
in the step (1):
the organic solvent is any one of dichloromethane, dichloroethane and acetonitrile.
The molar ratio of the N-ethyl-N-hydroxyethyl aniline to the succinic anhydride to the DMAP to the triethylamine is 1: 1.2-1.5: 0.1-0.2: 1-1.5.
The reaction temperature is between room temperature and 50 ℃, and the reaction time is 1-5 h.
In the step (2):
the organic solvent is any one of toluene, methanol, ethanol or acetonitrile.
The molar ratio of the acid to the benzaldehyde to the cyclohexyl isonitrile to the aniline is 1:1.2:1: 1.2.
The reaction temperature is 40-100 ℃, the reaction conditions are mild, and the reaction time is as follows: 36-48 h.
In the step (3):
the molar ratio of the coupling component to the 4-nitrophenyldiazonium salt is: 1: 1.5-1.2.
The reaction temperature is 0-5 ℃, and the reaction time is 24-36 h.
The third aspect of the invention aims to provide an application of the disperse dye compound in dyeing of nylon fabrics, and in the application process, the disperse dye compound can be directly added as disperse red, and can also be used as one component of the disperse dye to be mixed with other components for adding. The dyeing process comprises the following steps: weighing a disperse dye compound, fully mixing the disperse dye compound with a dispersant NNO according to the mass ratio of 1:1, and adding water to prepare 1g/L dye mother liquor; preparing dye liquor by adding water into 1g/L dye mother liquor, 5g/L ammonium sulfate mother liquor and 5g/L dispersant NNO solution, wherein the dye concentration is 0.5% (o.w.f), the ammonium sulfate concentration is 1g/L, the NNO concentration is 1g/L, and the bath ratio is 50: 1; putting chinlon into a dye solution at room temperature, starting dyeing at 40 ℃, increasing the temperature to 120 ℃ at a heating rate of 1 ℃/min, then keeping the temperature for 70min, and then cooling to 90 ℃ at full speed; after dyeing is finished, soaping the dyed sample by using a 2g/L standard soap powder aqueous solution, washing for 15min at 95 ℃ in a bath ratio of 50:1, taking out, washing with tap water, and airing in a natural state.
The preparation process has the following remarkable technical effects:
first, coupling components with different molecular weights and different molecular volumes can be obtained by changing any component (substituent or structure) of initial Ugi four-component reaction, so that the molecular volume and molecular weight of the novel disperse dye can be effectively controlled, and the dyeing property and color fastness of the disperse dye can be regulated and controlled.
Secondly, by the synthetic method of the invention, an ester group and two amide groups are introduced into the novel disperse dye, and the ester group and the two amide groups can form interaction with fibers to improve the dyeing performance.
And thirdly, performing the following steps. The invention can obtain series of novel disperse dyes with different spectral properties by adopting different diazonium salts, and provides a novel strategy and a novel method for the diversity synthesis of novel high-performance azo disperse dyes.
The invention is further described in detail below with reference to the following figures and detailed description.
Drawings
FIG. 1 is a NMR chart of a coupling component 1d prepared in example 1;
FIG. 2 is a NMR chart of a disperse dye compound 1da prepared in example 2;
FIG. 3 is a NMR chart of a disperse dye compound 1db prepared in example 3;
FIG. 4 is a hydrogen nuclear magnetic resonance graph of a disperse dye compound 1dc prepared in example 4.
Detailed Description
Example 1: preparation of 1d
(1) Acid synthesis:
to a 100mL round bottom flask were added succinic anhydride (1.3g, 13.0mmol, 1.3eq), DMAP (122.2mg, 1.0mmol, 0.1eq), CH in that order2Cl2(15mL), triethylamine (1.27mL, 10.0mmol, 1.0eq) and N-ethyl-N-hydroxyethylaniline (1.66mL, 10.0mmol, 1.0 eq). And stirring the reaction mixed solution at room temperature for 4 hours, carrying out thin-layer sample application to track the reaction process, carrying out reduced pressure concentration and vacuum drying on the reaction solution by using a rotary evaporator after the reaction is finished, and directly using the residue in the bottle for the Ugi four-component reaction.
(2) Ugi four-component reaction:
to a 250mL round bottom flask, anhydrous methanol (70mL), p-methylaniline (1.3g, 12.0mmol, 1.2eq) and benzaldehyde (1.28mL, 12.0mmol, 1.2eq) were added in that order, the acid synthesized in (1) was transferred to the flask with anhydrous methanol, and finally cyclohexylacetonitrile (1.25mL, 10mmol, 1.0eq) was added. Heating and stirring the reaction mixed solution in an oil bath at the temperature of 80 ℃ for 48h, carrying out thin-layer sample application to track the reaction process, carrying out reduced pressure concentration on the reaction solution by using a rotary evaporator after the reaction is finished, dissolving the residue in a bottle into 20mL of ethyl acetate, adding 10mL of petroleum ether, and placing the bottle in a refrigerator until a large amount of white solid is separated out. And (3) carrying out suction filtration, washing the mixture for multiple times by using an organic mixed solvent (the volume ratio of ethyl acetate to petroleum ether is 1:5), and drying the mixture to obtain 5.01g of white solid. The reaction equation is as follows:
Figure BDA0002561698870000081
of coupling component 1d1H-NMR、13C-NMR data are as follows:
1H NMR(400MHz,CDCl3)ppm 7.25-7.18(m,5H,Ar-H),7.15-7.13(m,2H,Ar-H),7.03(br s, 2H,Ar-H),6.73(d,J＝8.4Hz,2H,Ar-H),6.70(dd,J＝7.2,7.2Hz,1H,Ar-H),6.08(s,1H, COCHN),5.89(d,J＝8.0Hz,1H,NH),4.24(t,J＝6.4Hz,2H,CH2O),3.91-3.81(m,1H,NCH), 3.56(t,J＝6.8Hz,2H,CH2CH2N),3.41(q,J＝7.2Hz,2H,CH3CH2N),2.64(t,J＝6.8Hz,2H, OCOCH2),2.37-2.32(m,2H,CH2CON),2.30(s,3H,Ar-CH3),1.99(d,J＝14.0Hz,1H,Cy-H), 1.90(d,J＝11.6Hz,1H,Cy-H),1.18(t,J＝7.2Hz,3H,CH3),1.73-1.59(m,3H,Cy-H),1.39-1.29 (m,2H),1.20-1.04(m,3H,Cy-H).
13C NMR(100MHz,CDCl3)ppm 173.1,172.2,168.7,147.5,138.1,137.3,134.8,130.4(×2), 130.0(×2),129.7,129.4(×2),128.2(×2),128.2,116.1,111.9(×2),65.3,61.8,48.7,45.2,32.9,32.8, 29.8,29.4,25.5,24.9,24.8,21.1,12.2.
example 2: synthesis of disperse dye 1da
(1) Synthesis of diazonium salt:
4-nitroaniline (0.73g,5.27mmol,1.5eq) was added to a 50mL round-bottomed flask, 5mL of water and 5mL of concentrated hydrochloric acid (36.5%) were mixed and added dropwise to the flask, and the mixture was dissolved at 40-60 ℃ (about 1 h). After cooling the solution to room temperature, it was placed in an ice-water bath. Sodium nitrite (0.37g,5.27mmol,1.5eq) was dissolved in 5mL of water in a small beaker and placed in an ice-water bath for about 2 min. And (3) slowly adding the sodium nitrite aqueous solution dropwise, and reacting in an ice water bath for 1h after the dropwise addition is finished.
(2) Coupling reaction:
in a 150mL round bottom flask, 30mL of methanol and coupling component 1d (2.00g, 3.51mmol, 1.0eq) were added, heated and stirred in an oil bath at 80 ℃ until the coupling component was completely dissolved, and then the mixture was cooled to room temperature. Under the condition of ice-water bath, the 4-nitrophenyl diazonium salt is slowly dripped dropwise, the mixture is stirred for 24 hours at the temperature of 0-5 ℃, and the reaction process is tracked by thin-layer spotting. After the reaction is finished, the mixture is filtered, washed by an organic mixed solvent (the volume ratio of ethyl acetate to petroleum ether is 1:5), and dried to obtain a red solid. Purifying by column chromatography to obtain pure dye 1da, eluting with mixed solvent of ethyl acetate and petroleum ether at volume ratio of 1:2, drying, and weighing to obtain dye 1da 2.17 g. The reaction equation is as follows:
Figure BDA0002561698870000091
of disperse dye 1da1H-NMR、13C-NMR data are as follows:
1H NMR(400MHz,CDCl3)ppm 8.36(d,J＝8.8Hz,2H,Ar-H),7.95(d,J＝9.2Hz,2H,Ar-H), 7.92(d,J＝9.2Hz,2H,Ar-H),7.23-7.18(m,4H,Ar-H),7.14-7.11(m,3H,Ar-H),7.02(br s,2H, Ar-H),6.81(d,J＝9.2Hz,2H,Ar-H),6.05(s,1H,CONCH),5.73(d,J＝8.4Hz,1H,NH),4.31(t, J＝6.4Hz,2H,CH2O),3.89-3.80(m,1H,NCH),3.71(t,J＝6.4Hz,2H,CH2CH2N),3.55(q,J＝ 7.2Hz,2H,CH3CH2N),2.64(t,J＝7.2Hz,2H,OCOCH2),2.38-2.34(m,2H,CH2CON),2.30(s, 3H,Ar-CH3),1.96(d,J＝12.8Hz,1H,Cy-H),1.88(d,J＝10.0Hz,1H,Cy-H),1.71-1.58(m,3H, Cy-H),1.38-1.25(m,3H,Cy-H),1.27(t,J＝7.2Hz,3H,CH3),1.18-1.03(m,2H,Cy-H).
13C NMR(100MHz,CDCl3)ppm 173.0,172.1,168.6,156.8,151.2,147.4,143.9,138.1,137.2, 134.7,130.4(×2),130.0(×2),129.7(×2),128.3(×3),126.3(×2),124.7(×2),122.6(×2),111.4(×2), 65.4,61.3,48.8,48.7,45.7,32.8,32.8,29.8,29.4,25.5,24.9,24.8,21.0,12.3.
example 3: synthesis of disperse dye 1db
(1) And (3) diazonium salt synthesis:
2-chloro-4-nitroaniline (0.91g,5.27mmol,1.5eq) was added to a 50mL round-bottomed flask, 5mL of water and 5mL of concentrated hydrochloric acid (36.5%) were mixed and added dropwise to the flask, and the mixture was dissolved at 40 to 60 ℃. After cooling the solution to room temperature, it was placed in an ice-water bath. Sodium nitrite (0.37g,5.27mmol,1.5eq) was dissolved in 5mL of water in a small beaker and placed in an ice-water bath for about 2 min. And (3) slowly adding the sodium nitrite aqueous solution dropwise, and reacting in an ice water bath for 1h after the dropwise addition is finished.
(2) Coupling reaction:
in a 150mL round bottom flask, 30mL of methanol and coupling component 1d (2.00g, 3.51mmol, 1.0eq) were added, heated and stirred in an oil bath at 80 ℃ until the coupling component was completely dissolved, and then the mixture was cooled to room temperature. Under the condition of ice-water bath, the 2-chloro-4-nitrophenyldiazonium salt is slowly dripped dropwise, the mixture is stirred for 24 hours at the temperature of 0-5 ℃, and the reaction process is tracked by thin-layer spotting. After the reaction, the mixture is filtered, washed by an organic mixed solvent (the volume ratio of ethyl acetate to petroleum ether is 1:5), dried to obtain a dark red solid, and dried and weighed to obtain 2.41 g. The reaction equation is as follows:
Figure BDA0002561698870000101
of disperse dye 1db1H-NMR、13C-NMR data are as follows:
1H NMR(400MHz,CDCl3)ppm 8.39(d,J＝2.4Hz,1H,Ar-H),8.16(dd,J＝9.2,2.4Hz,1H, Ar-H),7.95(d,J＝8.8Hz,2H,Ar-H),7.79(d,J＝9.2Hz,1H,Ar-H),7.22-7.17(m,4H,Ar-H), 7.13-7.12(m,2H,Ar-H),7.02(br s,2H,Ar-H),6.81(d,J＝9.6Hz,2H,Ar-H),6.05(s,1H, COCHN),5.76(d,J＝8.0Hz,1H,NH),4.31(t,J＝6.4Hz,2H,CH2O),3.88-3.80(m,1H,NCH), 3.71(t,J＝6.4Hz,2H,CH2CH2N),3.55(q,J＝6.8Hz,2H,CH3CH2N),2.64(t,J＝6.8Hz,2H, OCOCH2),2.38(m,2H,CH2CON),2.29(s,3H,Ar-CH3),1.96(d,J＝10.4Hz,1H,Cy-H),1.86(d, J＝12.4Hz,1H,Cy-H),1.71-1.57(m,3H,Cy-H),1.38-1.25(m,3H,Cy-H),1.27(t,J＝7.2Hz,3H, CH3),1.18-1.03(m,2H,Cy-H).
13C NMR(100MHz,CDCl3)ppm 173.0,172.1,168.6,153.1,151.7,147.1,144.4,138.1,137.2, 134.7,134.0,130.4(×2),130.0(×2),129.7(×2),128.3(×3),127.0(×2),126.0,122.6,118.0,111.5 (×2),65.4,61.3,48.8,48.8,45.9,32.8,32.8,29.9,29.4,25.5,24.9,24.8,21.1,12.3.
example 4: synthesis of disperse dye 1dc
(1) And (3) diazonium salt synthesis:
2, 6-dichloro-4-nitroaniline (1.10g, 5.27mmol,1.5eq) was added to a 50mL round-bottomed flask, 5mL of water and 5mL of concentrated hydrochloric acid (36.5%) were mixed and added dropwise to the flask, and the mixture was dissolved at 40 to 60 ℃. After cooling the solution to room temperature, it was placed in an ice-water bath. Sodium nitrite (0.37g,5.27mmol,1.5eq) was charged with 5mL of H2Dissolving O in a small beaker, and placing in an ice water bath for about 2 min. And (3) slowly adding the sodium nitrite aqueous solution dropwise, and reacting in an ice water bath for 1h after the dropwise addition is finished.
(2) Coupling reaction:
in a 150mL round bottom flask, 30mL of methanol and coupling component 1d (2.00g, 3.51mmol, 1.0eq) were added, heated and stirred in an oil bath at 80 ℃ until the coupling component was completely dissolved, and then the mixture was cooled to room temperature. Under the condition of ice-water bath, the 2, 6-dichloro-nitrophenyl diazonium salt is slowly dripped dropwise, the mixture is stirred for 24 hours at the temperature of 0-5 ℃, and the reaction process is tracked by thin-layer spotting. After the reaction is finished, the mixture is filtered, washed by an organic mixed solvent (the volume ratio of ethyl acetate to petroleum ether is 1:5), dried to obtain a dark yellow solid, and dried and weighed to obtain 1dc 2.02g of the dye. The reaction equation is as follows:
Figure BDA0002561698870000111
of disperse dyes 1dc1H-NMR、13C-NMR data are as follows:
1H NMR(400MHz,CDCl3)ppm 8.29(s,2H,Ar-H),7.93(d,J＝9.2Hz,2H,Ar-H),7.22-7.17(m, 4H,Ar-H),7.14-7.12(m,2H,Ar-H),7.02(br s,2H,Ar-H),6.83(d,J＝9.2Hz,2H,Ar-H),6.05(s, 1H,CONCH),5.75(d,J＝8.0Hz,1H,NH),4.31(t,J＝6.4Hz,2H,CH2O),3.88-3.81(m,1H, NCH),3.72(t,J＝6.4Hz,2H,CH2CH2N),3.56(q,J＝7.6Hz,2H,CH3CH2N),2.65(t,J＝6.4Hz, 2H,OCOCH2),2.36(q,J＝6.0Hz,2H,CH2CON),2.30(s,3H,Ar-CH3),1.96(d,J＝10.4Hz,1H, Cy-H),1.88(d,J＝11.2Hz,1H,Cy-H),1.77-1.58(m,4H,Cy-H),1.38-1.24(m,2H,Cy-H),1.28(t, J＝7.2Hz,3H,CH3),1.18-1.06(m,2H,Cy-H).
13C NMR(100MHz,CDCl3)ppm 173.0,172.1,168.6,154.0,151.9,145.2,143.5,138.1,137.2, 134.8,130.4(×2),130.0(×2),129.7(×2),128.3(×3),128.1(×2),126.5(×2),124.2(×2),111.3(×2), 65.4,61.2,48.9,48.7,45.9,32.9,32.8,29.9,29.4,25.5,24.9,24.8,21.0,12.2.
example 5: detection of 1da, 1db, 1dc color fastness performance of novel dye
The novel disperse dyes 1da, 1db and 1dc prepared by the invention and the conventional dyes C.I. disperse red 1 and C.I. disperse red 13 with the same parent structure are applied to dyeing of chinlon, and the color fastness performance of the chinlon is tested. The test method is as follows, and the fastness test results are shown in table 1.
The test method comprises the following steps: respectively and accurately weighing 0.5000g (accurate to +/-0.1 mg) of dye 1da, 1db, 1dc, C.I. disperse red 1 and C.I. disperse red 13, fully mixing the dye 1da, the 1db, the 1dc, the C.I. disperse red 1 and the C.I. disperse red 13 with a dispersant NNO according to the mass ratio of 1:1, adding a small amount of water, continuously grinding for 30min in a mortar, transferring the ground dye into a 500mL volumetric flask, adding water to fix the volume, preparing 1g/L of dye mother liquor, and uniformly shaking for later use. 5 pieces of chinlon with the weight of 5.0g are sheared, 25mL of 1g/L dye mother liquor, 50mL of 5g/L ammonium sulfate mother liquor, 50mL of 5g/L dispersant NNO solution and 125mL of water are absorbed to prepare 250mL of dye liquor. The dye concentration is 0.5% (o.w.f), the ammonium sulfate concentration is 1g/L, the NNO concentration is 1g/L, and the bath ratio is 50: 1. One portion of each of the above 5 dye stock solutions of 1g/L was prepared. Respectively putting 5 parts of chinlon into 5 parts of dye solution at room temperature, putting a dyeing cup into an oil bath sample dyeing machine, dyeing from 40 ℃, heating to 120 ℃ at a heating rate of 1 ℃/min, then preserving heat for 70min, and then cooling to 90 ℃ at full speed. And after dyeing is finished, soaping the dyed sample by using a 2g/L standard soap powder aqueous solution, washing for 15min at 95 ℃ in a bath ratio of 50:1, taking out, washing by using tap water, and airing in a natural state to be tested. The color fastness to washing is determined by adopting ISO 105-C06:1994(E) standard, the color fastness to dry heat is determined by adopting ISO105-P01:1993(E) standard, the rubbing fastness is determined by adopting GB/T3920-2008 standard, and the light fastness is determined by adopting ISO 105-B02 standard.
TABLE 1 comparison of color fastness properties of dyes on polyamide dyeing
Figure BDA0002561698870000121
Figure BDA0002561698870000131
From the experimental data of table 1: the novel azo disperse dyes 1da, 1db and 1dc prepared in the embodiment are detected, the maximum absorption wavelengths λ max are 487, 509 and 438 respectively, and the color is red; the dye is applied to dyeing of chinlon under the same condition, the sublimation staining resistance fastness and the washing resistance fastness of the dye are greatly improved compared with those of disperse red 1 and disperse red 13, and the sublimation staining resistance fastness and the washing resistance of the three new dyes reach the expected effect, which shows that ester groups and amide groups are introduced into the novel dyes 1da, 1db and 1dc, the molecular weight and the molecular size are increased moderately, the acting force and the affinity of the dyes on fibers are enhanced, and the dyes are not easy to migrate out from the inside.
The structural formulae of disperse red 1 and disperse red 13 in table 1 are shown below:
Figure BDA0002561698870000132

Claims (10)

1. a disperse dye compound, wherein the disperse dye compound has the formula:
Figure FDA0002561698860000011
wherein R is1Is H or Cl, R2Is H or Cl.
2. The disperse dye compound according to claim 1, wherein the disperse dye compound has a structural formula
Figure FDA0002561698860000012
The preparation process comprises the following steps:
(1) acid synthesis: 13.0mmol succinic anhydride, 1.0mmol DMAP and 15mL CH are added in turn2Cl210.0mmol of triethylamine and 10.0mmol of N-ethyl-N-hydroxyethylaniline form a reaction mixed solution, stirring for 4 hours at room temperature, and after the reaction is finished, concentrating under reduced pressure and drying in vacuum;
(2) ugi four-component reaction: adding 70mL of anhydrous methanol, 12.0mmol of p-methylaniline and 12.0mmol of benzaldehyde, transferring the anhydrous methanol into the acid synthesized in the step (1), finally adding 10mmol of cyclohexylacetonitrile, heating and stirring in an oil bath at 80 ℃ for 48 hours, concentrating under reduced pressure after the reaction is finished, dissolving in 20mL of ethyl acetate, adding 10mL of petroleum ether, cooling until a large amount of white solid is separated out, carrying out suction filtration, washing by using an ethyl acetate/petroleum ether organic mixed solvent with the volume ratio of 1:5, and drying to obtain a coupling component;
(3) synthesis of diazonium salt: dissolving 5.27mmol of sodium nitrite with 5mL of water, placing the solution in an ice water bath for 2min to form a sodium nitrite aqueous solution, mixing 5mL of water with 5mL of 36.5% hydrochloric acid, dropwise adding the mixture into 5.27mmol of 4-nitroaniline, dissolving the mixture for 1h at 40-60 ℃, cooling the solution to room temperature, placing the cooled solution in the ice water bath, dropwise and slowly adding the sodium nitrite aqueous solution, and reacting the solution for 1h in the ice water bath after dropwise adding is finished to obtain 4-nitrophenyl diazonium salt;
(4) coupling reaction: adding 30mL of methanol into 3.51mmol of coupling component, heating and stirring in an oil bath at 80 ℃ until the coupling component is completely dissolved, cooling to room temperature, slowly dropwise adding the 4-nitrophenyl diazonium salt obtained in the step (3) under the condition of ice-water bath, stirring at 0-5 ℃ for 24 hours, performing suction filtration after the reaction is finished, washing and drying by using an ethyl acetate/petroleum ether organic mixed solvent with the volume ratio of 1:5, purifying by adopting a column chromatography method, and eluting and drying by using a mixed solvent of ethyl acetate and petroleum ether with the volume ratio of 1:2 as an eluent.
3. The disperse dye compound according to claim 1, wherein the disperse dye compound has a structural formula
Figure FDA0002561698860000021
The preparation process comprises the following steps:
(1) acid synthesis: 13.0mmol succinic anhydride, 1.0mmol DMAP and 15mL CH are added in turn2Cl210.0mmol of triethylamine and 10.0mmol of N-ethyl-N-hydroxyethylaniline form a reaction mixed solution, stirring the reaction mixed solution at room temperature for 4 hours, concentrating the reaction solution under reduced pressure after the reaction is finished, drying the reaction solution in vacuum, and directly using the residue in the bottle for the reaction of the four components of Ugi;
(2) ugi four-component reaction: adding 70mL of anhydrous methanol, 12.0mmol of p-methylaniline and 12.0mmol of benzaldehyde, transferring the anhydrous methanol into the acid synthesized in the step (1), finally adding 10mmol of cyclohexylacetonitrile, heating and stirring in an oil bath at 80 ℃ for 48 hours, concentrating under reduced pressure after the reaction is finished, dissolving in 20mL of ethyl acetate, adding 10mL of petroleum ether, cooling until a large amount of white solid is separated out, carrying out suction filtration, washing by using an ethyl acetate/petroleum ether organic mixed solvent with the volume ratio of 1:5, and drying to obtain a coupling component;
(3) synthesis of diazonium salt: dissolving 5.27mmol of sodium nitrite with 5mL of water, placing the mixture in an ice water bath for 2min to form a sodium nitrite aqueous solution, mixing the 5mL of water with 5mL of 36.5% hydrochloric acid, dropwise adding the mixture into 5.27mmol of 2-chloro-4-nitroaniline, dissolving the mixture at 40-60 ℃, cooling the mixture to room temperature, placing the mixture in the ice water bath, dropwise and slowly adding the sodium nitrite aqueous solution, and reacting the mixture in the ice water bath for 1h after dropwise adding is finished to obtain 2-chloro-4-nitrophenyldiazonium salt;
(4) coupling reaction: adding 30mL of methanol into 3.51mmol of coupling component, heating and stirring in an oil bath at 80 ℃ until the coupling component is completely dissolved, cooling to room temperature, slowly and dropwise adding the 2-chloro-4-nitrophenyldiazonium salt obtained in the step (3) under the condition of ice-water bath, stirring for 24 hours at 0-5 ℃, filtering after the reaction is finished, washing by using an ethyl acetate/petroleum ether organic mixed solvent with the volume ratio of 1:5, and drying.
4. The disperse dye compound according to claim 1, wherein the disperse dye compound has a structural formula
Figure FDA0002561698860000022
The preparation process comprises the following steps:
(1) acid synthesis: 13.0mmol succinic anhydride, 1.0mmol DMAP and 15mL CH are added in turn2Cl210.0mmol of triethylamine and 10.0mmol of N-ethyl-N-hydroxyethylaniline form a reaction mixed solution, stirring the reaction mixed solution at room temperature for 4 hours, concentrating the reaction solution under reduced pressure after the reaction is finished, drying the reaction solution in vacuum, and directly using the residue in the bottle for the reaction of the four components of Ugi;
(2) ugi four-component reaction: adding 70mL of anhydrous methanol, 12.0mmol of p-methylaniline and 12.0mmol of benzaldehyde, transferring the anhydrous methanol into the acid synthesized in the step (1), finally adding 10mmol of cyclohexylacetonitrile, heating and stirring in an oil bath at 80 ℃ for 48 hours, concentrating under reduced pressure after the reaction is finished, dissolving in 20mL of ethyl acetate, adding 10mL of petroleum ether, cooling until a large amount of white solid is separated out, carrying out suction filtration, washing by using an ethyl acetate/petroleum ether organic mixed solvent with the volume ratio of 1:5, and drying to obtain a coupling component;
(3) synthesis of diazonium salt: 5.27mmol of sodium nitrite in 5mL of H2Dissolving O, placing in an ice water bath for 2min to obtain a sodium nitrite aqueous solution, mixing 5mL of water with 5mL of 36.5% hydrochloric acid, dropwise adding the mixture into 5.27mmol of 2, 6-dichloro-4-nitroaniline, dissolving the mixture at 40-60 ℃, cooling to room temperature, placing in the ice water bath, dropwise and slowly adding the sodium nitrite aqueous solution, and reacting in the ice water bath for 1h after dropwise adding is finished to obtain 2, 6-dichloro-nitrophenyl diazonium salt;
(4) coupling reaction: adding 30mL of methanol into 3.51mmol of coupling component, heating and stirring in an oil bath at 80 ℃ until the coupling component is completely dissolved, cooling to room temperature, slowly and dropwise adding the 2, 6-dichloro-nitrophenyldiazonium salt synthesized in the step (3) under the condition of ice-water bath, stirring for 24 hours at 0-5 ℃, filtering after the reaction is finished, washing by using an ethyl acetate/petroleum ether organic mixed solvent with the volume ratio of 1:5, and drying.
5. A method for preparing a disperse dye compound, comprising the steps of:
(1) acid synthesis: in an organic solvent, reacting N-ethyl-N-hydroxyethyl aniline, succinic anhydride, DMAP and triethylamine at room temperature to generate corresponding acid, and directly spin-drying reaction liquid under a reduced pressure condition to obtain acid;
(2) ugi reaction: in an organic solvent, carrying out Ugi reaction on the synthesized acid, benzaldehyde, p-methylaniline and cyclohexyl isonitrile, and carrying out reduced pressure concentration and ethyl acetate recrystallization on the reaction liquid to obtain a white Ugi product, namely a coupling component for synthesizing the azo disperse dye;
(3) coupling reaction: and (3) coupling the obtained coupling component with a 4-nitrophenyldiazonium compound in an organic solvent, and filtering, washing and drying the solid to obtain the disperse dye compound.
6. The process for preparing a disperse dye compound according to claim 5, wherein: in the step (1), the organic solvent is any one of dichloromethane, dichloroethane and acetonitrile; the molar ratio of N-ethyl-N-hydroxyethyl aniline, succinic anhydride, DMAP and triethylamine is 1: 1.2-1.5: 0.1-0.2: 1-1.5, the reaction temperature is from room temperature to 50 ℃, and the reaction time is 1-5 h.
7. The process for preparing a disperse dye compound according to claim 5, wherein: in the step (2), the organic solvent is any one of toluene, methanol, ethanol or acetonitrile; in the step (2), the molar ratio of the acid to the benzaldehyde to the cyclohexyl isonitrile to the p-methylaniline is 1:1.2:1:1.2, the reaction temperature is 40-100 ℃, and the reaction time is 36-48 h.
8. The process for preparing a disperse dye compound according to claim 5, wherein: in the step (3), the molar ratio of the coupling component to the 4-nitrophenyldiazonium salt is 1: 1.5-1.2, the reaction temperature is 0-5 ℃, and the reaction time is 24-36 hours.
9. A method of using a disperse dye compound, comprising: the disperse dye compound according to claim 1, which is used as a disperse dye or as one of the components of a disperse dye for dyeing nylon.
10. The method of claim 9, wherein the dyeing process comprises: weighing a disperse dye compound, fully mixing the disperse dye compound with a dispersant NNO according to the mass ratio of 1:1, and adding water to prepare 1g/L dye mother liquor; 1g/L of dye mother liquor, 5g/L of ammonium sulfate mother liquor and 5g/L of dispersant NNO solution are taken, water is added to prepare dye liquor, the dye concentration is 0.5 percent (o.w.f), the ammonium sulfate concentration is 1g/L, the NNO concentration is 1g/L, and the bath ratio is 50: 1; putting chinlon into a dye solution at room temperature, starting dyeing at 40 ℃, increasing the temperature to 120 ℃ at a heating rate of 1 ℃/min, then keeping the temperature for 70min, and then cooling to 90 ℃ at full speed; after dyeing is finished, soaping the dyed sample by using a 2g/L standard soap powder aqueous solution, washing for 15min at 95 ℃ in a bath ratio of 50:1, taking out, washing by using tap water, and airing in a natural state.
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CN115386242A (en) * 2022-07-29 2022-11-25 浙江嘉欣兴昌印染有限公司 Preparation and application of flexible chain connected bisazo orange high-water-washing disperse dye compound

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115386242A (en) * 2022-07-29 2022-11-25 浙江嘉欣兴昌印染有限公司 Preparation and application of flexible chain connected bisazo orange high-water-washing disperse dye compound
CN115386242B (en) * 2022-07-29 2024-03-19 浙江嘉欣兴昌印染有限公司 Preparation and application of flexible chain-connected disazo orange high-water-washing disperse dye compound

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