Low-melting fast yellow disperse dyes, methods of making and use thereof

Abstract

The application provides a low-melting-point light yellow disperse dye, a preparation method and application, and particularly relates to the technical field of dye chemical industry. The low-melting-point light yellow disperse dye has a structure shown in formula I: wherein R1 is C1-C8 alkyl; R2 is C1-C8 alkyl; and R3 is C1-C8 alkyl. The low-melting-point light yellow disperse dye has a melting point of 113-117 DEG C, which is lower than a dyeing temperature. At the dyeing temperature, the low-melting-point light yellow disperse dye is melted in a dyeing solution and uniformly attached to a fabric without the dispersion effect of a dispersant, and after being applied to the fabric, the low-melting-point light yellow disperse dye does not cause dyeing unevenness, color spots and the like. After being applied to polyester fibers and blended fabrics, the low-melting-point light yellow disperse dye presents a bright light yellow color, and can be used alone or in combination with other disperse dyes with the same characteristics. The low-melting-point light yellow disperse dye has excellent dyeing performance, including a water washing fastness of more than 4 levels, a perspiration fastness of more than 4 levels, a sublimation color fastness of more than 3 levels, and a sunlight fastness of more than 5 levels.

Description

TECHNICAL FIELD

[0001] The present application relates to the dye chemical technology field, especially to a low melting point yellowish dispersion dye, a preparation method and application thereof. BACKGROUND

[0002] The dispersion dye is a kind of dye with small molecule, simple structure and no water-soluble group on the structure, which is in a non-ionic state with extremely low solubility in water. It must be uniformly dispersed in the dyeing solution with the help of dispersant for dyeing. It can be applied to dye polyester fiber, acetate fiber and polyamide fiber. Generally, high temperature and high pressure method is used for dyeing. The dyeing temperature is 130 DEG C, and the dyeing time is 30-60 min.

[0003] The water-solubility of the dispersion dye is very small, and it almost completely depends on the dispersant to form hydrophilic dye colloidal particles, so as to be dispersed in water. In addition, the melting point of most dispersion dyes is relatively high, which is 140-200 DEG C. At the dyeing temperature of 130 DEG C, the dye cannot be completely melted. Therefore, during the heating, holding and cooling processes of the dispersion dye, the 'binding energy' between the dye and the dispersant will gradually decrease, and even part of the dye colloidal particles will be broken. The free dye particles will be aggregated due to the high melting point and the repulsion of water, so that the small dye particles will gradually become large dye aggregates. As a result, the color, brightness and dyeing fastness of the fabric will be reduced, and the serious problem of tar spots will be caused.

[0004] In addition, the addition of a large amount of dispersant in the dispersion dye will cause a series of environmental problems. Because quinoline, polycyclic aromatic hydrocarbons and formaldehyde are the key environmental problems, the problem must be paid attention to with the increasing environmental requirements.

[0005] At present, there is no research on how to solve the problem in the industry. The related products are far away from the market. Therefore, the market urgently needs a yellowish dispersion dye with low melting point, low dependence on dispersant and excellent performance.

[0006] In view of this, the present application is proposed. SUMMARY

[0007] One of the purposes of the present application is to provide a low melting point yellowish dispersion dye, so as to solve the technical problems of high melting point of the dispersion dye in the prior art, and the poor dyeing performance at high temperature.

[0008] The second purpose of the present application is to provide a preparation method of the low melting point yellowish dispersion dye.

[0009] The third object of the present application is to provide an application of a low-melting point light yellow disperse dye in dyeing or printing of polyester fiber and its blended fiber products.

[0010] In order to achieve the above object of the present application, the following technical solutions are adopted:

[0011] The first aspect of the present application provides a low-melting point light yellow disperse dye having a structure shown in Formula I:

[0012]

[0013] wherein R1 is C1-C8 alkyl; R2 is C1-C8 alkyl; and R3 is C1-C8 alkyl.

[0014] Further, R1 is C1-C4 alkyl; R2 is C1-C4 alkyl; and R3 is C1-C4 alkyl.

[0015] Further, R1 is selected from methyl, ethyl, propyl or isopropyl; R2 is selected from ethyl or propyl; and R3 is selected from ethyl, propyl, isopropyl or butyl.

[0016] The second aspect of the present application provides a preparation method of the low-melting point light yellow disperse dye, comprising the following steps:

[0017] A. adding an aromatic amine compound shown in Formula II into an aqueous solution of hydrochloric acid, and then adding a diazotization reagent to perform a diazotization reaction to obtain a diazo liquid;

[0018]

[0019] B. adding the diazo liquid into a pyridone derivative solution shown in Formula III to perform a coupling reaction, and then filtering, washing with water and drying to obtain the low-melting point light yellow disperse dye;

[0020]

[0021] wherein R1 is C1-C8 alkyl; R2 is C1-C8 alkyl; and R3 is C1-C8 alkyl.

[0022] Further, the mass concentration of the aqueous solution of hydrochloric acid is 10wt.%-36wt.%.

[0023] In the diazotization reaction, the molar ratio of hydrochloric acid to the aromatic amine compound is 1-5:1, and the molar ratio of the diazotization reagent to the aromatic amine compound is 1-1.2:1.

[0024] The diazotization reagent comprises sodium nitrite.

[0025] The diazotization reaction is carried out at a temperature of -5℃ to 35℃ for 1h to 6h.

[0026] Further, the molar ratio of the pyridone derivative to the aromatic amine compound is 1 to 1.2:1.

[0027] The coupling reaction is carried out at a pH of 7 to 10, a temperature of 0℃ to 25℃ for 1h to 5h.

[0028] Further, the aromatic amine compound is prepared by mixing m-amidophenol and an alkylbenzenesulfonyl chloride compound at a molar ratio of 1:1 to 1.3, and then performing esterification reaction in an alkaline environment, wherein the esterification reaction is carried out at a temperature of 0℃ to 100℃ for 2h to 5h to obtain a benzenesulfonate compound; and performing acidolysis reaction on the benzenesulfonate compound to obtain the aromatic amine compound.

[0029] Further, the alkylbenzenesulfonyl chloride compound has the structure shown in formula IV:

[0030]

[0031] The benzenesulfonate compound has the structure shown in formula V:

[0032]

[0033] R1 is C1-C8 alkyl;

[0034] The acidolysis reaction is carried out at a temperature of 50℃ to 150℃ for 1h to 4h.

[0035] Further, the pyridone derivative is prepared by condensation reaction of methyl cyanoacetate and an alkoxyalkyl amine compound at a molar ratio of 1:1 to 1.2 in a solvent-free environment, wherein the condensation reaction is carried out at a temperature of 0℃ to 100℃ for 1h to 5h to obtain a cyanoacetyl alkyl amine compound; and condensation cyclization reaction of the cyanoacetyl alkyl amine compound and methyl acetoacetate to obtain the pyridone derivative.

[0036] Further, the alkylbenzenesulfonyl chloride compound has the structure shown in formula IV:

[0037] R3OR2NH2

[0038] Formula VI;

[0039] R2 is C1-C8 alkyl; and R3 is C1-C8 alkyl.

[0040] The cyanoacetyl alkyl amine compound has the structure shown in formula VII:

[0041] CNCH2CONHR2OR3

[0042] Formula VII;

[0043] R2 is C1-C8 alkyl; R3 is C1-C8 alkyl;

[0044] In the condensation cyclization reaction, the molar ratio of cyanoacetyl alkylamine compound to methyl acetoacetate is 1:1-1.3;

[0045] The condensation cyclization reaction is carried out at a temperature of 0-100℃ for 1-30h.

[0046] The third aspect of the application provides the application of the low-melting-point light yellow disperse dye in dyeing or printing of polyester fiber and its blended fiber products.

[0047] Compared with the prior art, the application has at least the following beneficial effects:

[0048] The low-melting-point light yellow disperse dye provided by the application has a melting point of 113-117℃, which is lower than the dyeing temperature. At the dyeing temperature, the low-melting-point light yellow disperse dye is melted in the dyeing solution and uniformly attached to the fabric, without the need of the dispersion effect of a dispersant. After being applied to polyester fiber and its blended fabric, the light yellow disperse dye presents a bright light yellow color, and can be used alone or in combination with other disperse dyes of the same characteristics. The light yellow disperse dye not only has a novel structure, but also has excellent dyeing performance: the water washing fastness is greater than 4, the perspiration fastness is greater than 4, the sublimation color fastness is greater than 3, and the sunlight fastness is greater than 5, and the performance is excellent.

[0049] The preparation method provided by the application has continuous process steps, strong controllability, large processing capacity, and is suitable for large-scale industrial production.

[0050] The application provided by the application provides a light yellow disperse dye with better performance for polyester fiber and its blended fiber products, improves the dyeing quality, reduces the waste rate, and reduces the fabric production cost. DETAILED DESCRIPTION

[0051] The embodiments of the application will be described in detail below with reference to the embodiments and examples, but those skilled in the art will understand that the following embodiments and examples are only used to illustrate the application, and should not be regarded as limiting the scope of the application. Based on the examples in the application, all other examples obtained by those skilled in the art without creative labor are within the scope of protection of the application.

[0052] The first aspect of the application provides a low-melting-point light yellow disperse dye having a structure shown in Formula I:

[0053]

[0054] wherein R1 is a C1-C8 alkyl group; R2 is a C1-C8 alkyl group; and R3 is a C1-C8 alkyl group.

[0055] The low-melting-point light yellow disperse dye provided by the present application has a melting point of 113-117°C, which is lower than the dyeing temperature. At the dyeing temperature, the low-melting-point light yellow disperse dye melts in the dyeing solution and uniformly adheres to the fabric, without the need of the dispersion effect of a dispersant. After the dyeing of the polyester fiber and its blended fabric, a bright light yellow color is presented, which can be used as a single color or in combination with other disperse dyes of the same characteristics. The low-melting-point light yellow disperse dye has novel structure and excellent dyeing performance, including a water washing fastness of >4, a perspiration fastness of >4, a sublimation color fastness of >3, and a sunlight fastness of >5.

[0056] Typically but not exclusively, R1 can be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, neopentyl, hexyl, heptyl or octyl; R2 can be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, neopentyl, hexyl, heptyl or octyl; and R3 can be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, neopentyl, hexyl, heptyl or octyl. It should be noted that R1, R2 and R3 can be the same or different.

[0057] Further, R1 is a C1-C4 alkyl group; R2 is a C1-C4 alkyl group; and R3 is a C1-C4 alkyl group.

[0058] Further, R1 is selected from methyl, ethyl, propyl or isopropyl; R2 is selected from ethyl or propyl; and R3 is selected from ethyl, propyl, isopropyl or butyl.

[0059] The second aspect of the present application provides a preparation method of the low-melting-point light yellow disperse dye, which comprises the following steps:

[0060] A. adding an aromatic amine compound shown in Formula II into an aqueous hydrochloric acid solution, and then adding a diazotization reagent to perform a diazotization reaction to obtain a diazo liquid;

[0061]

[0062] B. adding the diazo liquid into a pyridone derivative solution shown in Formula III to perform a coupling reaction, and then filtering, washing with water and drying to obtain the low-melting-point light yellow disperse dye;

[0063]

[0064] wherein R1 is a C1-C8 alkyl group; R2 is a C1-C8 alkyl group; and R3 is a C1-C8 alkyl group.

[0065] The preparation method provided by the present application has continuous process steps, strong controllability, large processing capacity, and is suitable for large-scale industrial production.

[0066] Further, the mass concentration of the aqueous hydrochloric acid solution is 10wt.% to 36wt.%, preferably 10wt.% to 20wt.%. Typically but not limitedly, the mass concentration of the aqueous hydrochloric acid solution is, for example, 10wt.%, 14wt.%, 18wt.%, 20wt.%, 22wt.%, 26wt.%, 30wt.% or 36wt.%.

[0067] In the diazotization reaction, the molar ratio of hydrochloric acid to the aromatic amine compound is 1 to 5:1, preferably 1 to 3:1; the molar ratio of diazotization reagent to the aromatic amine compound is 1 to 1.2:1, preferably 1 to 1.1:1.

[0068] Typically but not limitedly, the molar ratio of hydrochloric acid to the aromatic amine compound can be, for example, 1:1, 2:1, 3:1, 4:1 or 5:1; the molar ratio of diazotization reagent to the aromatic amine compound can be, for example, 1:1, 1.1:1 or 1.2:1.

[0069] The diazotization reagent includes sodium nitrite.

[0070] The temperature of the diazotization reaction is -5°C to 35°C, preferably 0°C to 25°C; the time is 1h to 6h, preferably 2h to 5h. The progress of the diazotization reaction can be monitored by a conventional test method in the art (such as TLC), with the disappearance of the aromatic amine compound as the reaction endpoint.

[0071] Further, the molar ratio of the pyridone derivative to the aromatic amine compound is 1 to 1.2:1; preferably 1 to 1.1:1.

[0072] The pH value of the coupling reaction is 7 to 10, preferably 6 to 8; the temperature is 0°C to 25°C, preferably 0°C to 10°C; the time is 1h to 5h, preferably 1h to 3h.

[0073] The pH value is adjusted to the above range using a base, which can be, for example, sodium bicarbonate, sodium carbonate or sodium hydroxide.

[0074] The progress of the coupling reaction can be monitored by a conventional test method in the art (such as the ring diffusion coloration method), with the coloration of a slight excess of the pyridone derivative as the reaction endpoint.

[0075] Further, the preparation method of the aromatic amine compound is as follows: mixing m-aminoacetophenone and alkyl benzene sulfonyl chloride compound with a molar ratio of 1:1-1.3, and performing esterification reaction in alkaline environment, the temperature of the esterification reaction is 0-100℃, and the time is 2-5h, to obtain benzene sulfonate compound; performing acidolysis reaction on the benzene sulfonate compound to obtain the aromatic amine compound.

[0076] Preferably, the molar ratio of m-aminoacetophenone and alkyl benzene sulfonyl chloride compound is 1:1-1.2.

[0077] Preferably, the temperature of the esterification reaction is 25-70℃, and the time is 2-3h. The progress of the esterification reaction can be monitored by conventional test method in the art (such as HPLC), with ≤1% of the m-aminoacetophenone as the reaction end point.

[0078] The esterification reaction is performed in alkaline environment, and the base is preferably aqueous solution of sodium bicarbonate, sodium carbonate or sodium hydroxide.

[0079] Further, the alkyl benzene sulfonyl chloride compound has the structure shown in formula IV:

[0080]

[0081] The benzene sulfonate compound has the structure shown in formula V:

[0082]

[0083] R1 is C1-C8 alkyl;

[0084] The esterification reaction is shown in the following reaction formula I:

[0085]

[0086] The acidolysis reaction is shown in the following reaction formula II:

[0087]

[0088] The acid used in the acidolysis reaction can be hydrochloric acid or sulfuric acid. In the acidolysis reaction, the molar ratio of the benzene sulfonate compound and the acid is 1:1-6, preferably 1:1-4.

[0089] The temperature of the acidolysis reaction is 50-150℃, preferably 70-120℃; and the time is 1-4h, preferably 1-3h.

[0090] The progress of the acidolysis reaction can be monitored by conventional test method in the art (such as HPLC), with ≤1% of the benzene sulfonate compound as the reaction end point.

[0091] Further, the preparation method of the pyridinone derivative is as follows: condensation reaction of methyl cyanoacetate and alkoxyalkyl amine compound in a molar ratio of 1:1-1.2 in a solvent-free environment, the condensation reaction temperature is 0-100℃, the time is 1-5h, to obtain cyanoacetyl alkyl amine compound; condensation cyclization reaction of the cyanoacetyl alkyl amine compound and methyl acetoacetate, to obtain the pyridinone derivative.

[0092] Preferably, the molar ratio of methyl cyanoacetate and alkoxyalkyl amine compound is 1:1-1.2, preferably 1:1-1.1.

[0093] Preferably, the condensation reaction temperature is 20-60℃, the time is 1-3h. The progress of the condensation reaction can be monitored by conventional test methods in the art (such as GC), and the reaction end point is that the reaction of the methyl cyanoacetate is complete.

[0094] The alkoxyalkyl amine compound has the structure shown in formula VI:

[0095] R3OR2NH2

[0096] Formula VI;

[0097] R2 is C1-C8 alkyl; R3 is C1-C8 alkyl.

[0098] The cyanoacetyl alkyl amine compound has the structure shown in formula VII:

[0099] CNCH2CONHR2OR3

[0100] Formula VII;

[0101] R2 is C1-C8 alkyl; R3 is C1-C8 alkyl.

[0102] The condensation reaction is shown in the following reaction formula III:

[0103] CNCH2COOCH3+R3OR2NH2→CNCH2CONHR2OR3+CH3OH

[0104] Reaction formula III

[0105] The condensation cyclization reaction is shown in the following reaction formula IV:

[0106]

[0107] In the condensation cyclization reaction, the molar ratio of cyanoacetyl alkyl amine compound and methyl acetoacetate is 1:1-1.3, preferably 1:1-1.2.

[0108] The condensation cyclization reaction is carried out at a temperature of 0°C to 100°C, preferably 50°C to 100°C, for a time period of 1h to 30h, preferably 10h to 20h. The progress of the condensation cyclization reaction can be monitored by conventional test methods in the art, such as HPLC, to a reaction end point of < 2% of the alkoxylalkylamine compound.

[0109] The third aspect of the present application provides the use of the low-melting point Light Yellow disperse dye in dyeing or printing of polyester fiber and its blended fiber products.

[0110] The polyester fiber, i.e. polyethylene terephthalate fiber (polyester) and its blended fiber products, such as polyester / cotton, polyester / viscose, polyester / spandex, are conventional polyester fiber and its blended fiber products in the art.

[0111] The blended fiber products can be in the form of fibers, yarns, woven fabrics, knitted fabrics or nonwovens, which are conventional in the art.

[0112] The use provided by the present application provides a Light Yellow disperse dye with better performance for polyester fiber and its blended fiber products, improves the dyeing quality, reduces the waste rate and lowers the fabric production cost.

[0113] The present application is further illustrated by the following specific examples and comparative examples, but it should be understood that these examples are only used for more detailed illustration and should not be understood as limiting the present application in any form. The raw materials used in the examples and comparative examples of the present application are prepared under conventional conditions or the conditions recommended by the manufacturer, unless otherwise specified. The reagents or instruments used are conventional products that can be purchased on the market, unless otherwise specified.

[0114] Example 1

[0115] This example provides an aromatic amine compound, and the preparation method is as follows:

[0116] 1. Add 100ml water into a 250ml three-necked flask, then add 0.2mol m-acetamidophenol and 0.24mol p-toluenesulfonyl chloride under stirring, stir uniformly, then warm up to 30°C, and add 0.24mol liquid caustic from a constant pressure dropping funnel. Control the temperature at 30-32°C for 2h, after completion of the addition, keep the temperature at 30-35°C for 1h. Then warm up to 35-40°C for 1h, take a sample for HPLC detection and analysis, and the m-amidophenylacetamide is ≤1%, which means the esterification reaction is completed.

[0117] 2, after cooling, add 0.8 mol of hydrochloric acid, stir uniformly, and then heat to 110°C, and keep the temperature for 2 h. Take a sample for HPLC detection to analyze the hydrolysis of benzene sulfonate compounds. After cooling to room temperature, adjust the pH to neutral with a small amount of liquid alkali, filter, wash with water, and dry to obtain the aromatic amine compound-1 (R1 is methyl), the structure of which is shown in the following formula II-1.

[0118]

[0119] Example 2-4

[0120] This example provides an aromatic amine compound, which corresponds to replacing the p-toluenesulfonyl chloride in Example 1 with p-ethylbenzenesulfonyl chloride, p-n-propylbenzenesulfonyl chloride, and p-isopropylbenzenesulfonyl chloride. The remaining raw materials and methods are the same as those in Example 1, and are not described here again.

[0121] The experimental data and structural identification data of the product alkylbenzenesulfonyl chloride compound of Example 1-4 are shown in Table 1 below. The LC-MS data described in the present application are obtained by testing with a Waters UPLC-SQD liquid chromatograph-mass spectrometer (mobile phase: acetonitrile / water system, 60% to 90% acetonitrile V / V, column temperature 40°C).

[0122] Table 1

[0123]

[0124] Example 5

[0125] This example provides a pyridone derivative, the preparation method of which is as follows:

[0126] 1. In a 250 ml three-necked flask, add 0.5 mol of methyl cyanoacetate, and then slowly drop 0.525 mol of 3-ethoxypropylamine from a constant-pressure dropping funnel under water bath conditions at 25-30°C. Control the temperature at 25-30°C for about 2 h of dropping. After completion of dropping, keep the temperature at 25-30°C for 30 min. Then heat to 50-55°C and keep the temperature for 1 h to complete the condensation reaction.

[0127] 2. After cooling to room temperature, add 0.55 mol of methyl acetoacetate and 0.6 mol of ammonia water to the reaction solution, stir uniformly, heat to 70-75°C, keep the temperature for 5 h, then heat to 80-85°C for 8 h, and finally keep the temperature at 83-85°C for 4 h. Take a sample for HPLC detection to analyze the condensation and cyclization reaction of cyanoacetyl alkylamine compounds ≤5%. After cooling, the pyridone derivative-1 (R2 is propyl, and R3 is ethyl) is obtained, the structure of which is shown in the following formula III-1.

[0128]

[0129] Example 6-12

[0130] The experimental data and structural identification data of the product pyridone derivative obtained by replacing 3-ethoxypropylamine with the corresponding material in Examples 6-12 are shown in Table 2 below.

[0131] Table 2

[0132]

[0133] Example 13

[0134] This example provides a low-melting tender yellow disperse dye, which is prepared according to the following method:

[0135] In a 100 mL three-necked flask, 45 mL of water was measured, and 0.05 mol of the aromatic amine compound provided in Example 1 and 0.2 mol of hydrochloric acid were added under stirring. After stirring uniformly, the temperature was lowered to 0-5°C in an ice water bath, and then 0.0525 mol of sodium nitrite aqueous solution was slowly added under temperature control at below 5°C. After about 1 h of addition, the transparent diazonium solution was obtained and preserved at 0-5°C for 3 h. Then, the pyridone derivative provided in Example 6 was added dropwise within 1 h to complete the coupling. The reaction temperature was controlled at 0-5°C by adding ice, and the coupling was completed at 0-5°C for 2 h. After natural stirring to room temperature, filtration, water washing, drying, and sand milling treatment with water, and then spray drying, a low-melting tender yellow disperse dye (R1 is methyl, R2 is propyl, and R3 is ethyl) was obtained.

[0136] The structural formula is shown in the following Formula I-1.

[0137]

[0138] Examples 14-20

[0139] According to the preparation method of Example 13, any one of the aromatic amine compounds in Examples 1-4 and any one of the pyridone derivatives in Examples 5-12 were selected to obtain a low-melting tender yellow disperse dye with the corresponding structure. The specific experimental data and structural identification data are shown in Table 3.

[0140] Table 3

[0141]

[0142] Comparative Example 1

[0143] This comparative example provides C.I. Disperse Yellow 114:

[0144]

[0145] Test Example 1

[0146] The low melting point yellowish dispersion dyes obtained from Examples 13-20 and the C.I. Disperse Yellow 114 stock dye of Comparative Example 1 were subjected to melting point test, and the test results are listed in Table 4.

[0147] The low melting point yellowish dispersion dyes obtained from Examples 13-20 and the C.I. Disperse Yellow 114 stock dye of Comparative Example 1 were subjected to melting point test, and the test results are listed in Table 4.

[0148] The C.I. Disperse Yellow 114 stock dye of Comparative Example 1 was dissolved in 500 ml of water to form a dye solution.

[0149] The C.I. Disperse Yellow 114 stock dye of Comparative Example 1 was dissolved in 500 ml of water to form a dye solution.

[0150] Table 4

[0151]

[0152] As can be seen from Table 4, the yellowish dispersion dyes of the present application have a low melting point of 113-117°C, and can be melted in the dye liquor at a temperature lower than the dyeing temperature of 130°C and uniformly attached to the fabric. No dispersion agent is needed, and no dyeing unevenness or color spots occur after dyeing the fabric. The C.I. Disperse Yellow 114 stock dye of Comparative Example 1 has a high melting point, and dyeing unevenness and color spots occur on the dyed fabric without using a dispersion agent. The results are far worse than those of the dispersion dyes of the present application.

[0153] Test Example 2

[0154] The dyed fabric samples obtained from Test Example 1 were subjected to test for water washing fastness, perspiration fastness, light fastness and sublimation color fastness according to ISO 105C10 C(3), ISO 105E04, ISO 105B02 and GB / T5718-1997 standards, respectively. The test results are shown in Table 5.

[0155] Table 5

[0156]

[0157] (The values in the water washing fastness, perspiration fastness, light fastness and sublimation color fastness in Table 5 refer to the number of grades).

[0158] As can be seen from Table 5, the yellowish dispersion dyes of the present application also have excellent dyeing properties and dyeing fastness.

[0159] It should be noted that the above embodiments are only used to illustrate the technical solutions of the present application, and are not intended to limit the present application; although the present application has been described in detail with reference to the above embodiments, those skilled in the art should understand that the technical solutions recorded in the above embodiments can be modified, or some or all of the technical features can be replaced by equivalents; and these modifications or replacements do not make the essence of the corresponding technical solutions deviate from the scope of the technical solutions of the embodiments of the present application.

Claims

1. A low melting point light yellow disperse dye, characterized by, has a structure shown in formula I: Formula I R1 is C1-C8 alkyl; R2 is C1-C8 alkylene; R3 is C1-C8 alkyl.

2. The low melting fast yellow disperse dye according to claim 1, characterized in that, R1 is C1-C4 alkyl; R2 is C1-C4 alkylene; R3 is C1-C4 alkyl.

3. The low melting fast yellow disperse dye according to claim 1, characterized in that, R1 is C1-C4 alkyl; R2 is C1-C4 alkylene; R3 is C1-C4 alkyl.

4. A process for the preparation of a low melting fast yellow disperse dye according to any one of claims 1 to 3, characterized in that R1 is C1-C4 alkyl; R2 is C1-C4 alkylene; R3 is C1-C4 alkyl. The method comprises the following steps: A. adding an aromatic amine compound shown in formula II into an aqueous hydrochloric acid solution, and then adding a diazotization reagent to perform a diazotization reaction to obtain a diazonium liquid; Formula II B. adding the diazonium liquid into a pyridone derivative solution shown in formula III to perform a coupling reaction, and then performing filtration, water washing and drying to obtain a low-melting fast yellow disperse dye; Formula III 5. The preparation method according to claim 4, characterized in that, R1 is C1-C8 alkyl; R2 is C1-C8 alkylene; R3 is C1-C8 alkyl. The mass concentration of the aqueous hydrochloric acid solution is 10wt.%-36wt.%; In the diazotization reaction, the molar ratio of hydrochloric acid to the aromatic amine compound is 1-5:1, and the molar ratio of the diazotization reagent to the aromatic amine compound is 1-1.2:1; The diazotization reagent comprises sodium nitrite; 6. The preparation method according to claim 4, characterized in that, The temperature of the diazotization reaction is-5℃-35℃, and the time is 1h-6h. The molar ratio of the pyridone derivative to the aromatic amine compound is 1-1.2:1; 7. The preparation method according to claim 4, characterized in that, The pH value of the coupling reaction is 7-10, the temperature is 0℃-25℃, and the time is 1h-5h.

8. The production method according to claim 7, characterized by, The preparation method of the aromatic amine compound is as follows: mixing molar ratio 1:1-1.3 of m-acetamidophenol and an alkyl benzene sulfonyl chloride compound, performing esterification reaction in an alkaline environment, the temperature of the esterification reaction is 0℃-100℃, the time is 2h-5h, to obtain a benzene sulfonate compound; performing acidolysis reaction on the benzene sulfonate compound to obtain the aromatic amine compound. The alkyl benzene sulfonyl chloride compound has a structure shown in formula IV: Formula IV The benzene sulfonate compound has a structure shown in formula V: Formula V R1 is C1-C8 alkyl; 9. The preparation method according to claim 4, characterized in that, The temperature of the acidolysis reaction is 50℃-150℃, and the time is 1h-4h. The preparation method of the pyridone derivative is as follows: performing condensation reaction on molar ratio 1:1-1.2 of methyl cyanoacetate and an alkoxy alkyl amine compound in a solvent-free environment, the temperature of the condensation reaction is 0℃-100℃, the time is 1h-5h, to obtain a cyanoacetyl alkyl amine compound; performing condensation cyclization reaction on the cyanoacetyl alkyl amine compound and methyl acetoacetate to obtain the pyridone derivative; The alkoxy alkyl amine compound has a structure shown in formula VI: Formula VI R2 is C1-C8 alkylene; R3 is C1-C8 alkyl; The cyanoacetyl alkyl amine compound has a structure shown in formula VII: Formula VII R2 is C1-C8 alkylene; R3 is C1-C8 alkyl; In the condensation cyclization reaction, the molar ratio of the cyanoacetyl alkyl amine compound to methyl acetoacetate is 1:1-1.3; The temperature of the condensation cyclization reaction is 0℃-100℃, and the time is 1h-30h.

10. Use of a low melting point safranin disperse dye according to any one of claims 1 to 3 or a low melting point safranin disperse dye prepared according to the process of any one of claims 4 to 9 for dyeing or printing polyester fibres and articles of manufacture comprising polyester fibres.

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