A reactive yellow to orange dye composition and dye article

Abstract

The application discloses a reactive yellow to orange dye composition and a dye product. The reactive yellow to orange dye composition comprises component A and component B, wherein the component A is selected from at least one of dye compounds shown in formula (I), and the component B is selected from at least one of dye compounds shown in formula (II); the mass percentage of the component A in the reactive yellow to orange dye composition is 20-70%, and the mass percentage of the component B is 30-80%. The reactive yellow to orange dye composition has the characteristics of good build-up, good compatibility, high fixation rate, excellent color fastness, especially outstanding water washing fastness and the like when being used for printing and dyeing of nitrogen-containing and / or hydroxyl-containing fiber materials.

Description

TECHNICAL FIELD

[0001] The present application relates to a kind of active yellow to orange dye compositions, in particular to a kind of active yellow to orange dye compositions suitable for printing and dyeing of nitrogen-containing and / or hydroxyl-containing fiber materials and dye products. BACKGROUND

[0002] Azo dyes are produced by diazotization of aromatic amines and coupling with suitable coupling components, which can be obtained in various colors and play an important role as colorants in the textile industry. In recent years, the market has higher requirements for the fastness of dyed textiles, for example, many buyers of textile products require good evaluation of color fastness after multiple washes according to ISO 105-C09, and good wash-resistant dyes can extend the service life of textiles, but the existing dyes on the market still cannot meet the requirements well, especially the active yellow to orange dyes are relatively lacking, therefore, it is necessary to explore more high-quality active yellow to orange dyes to meet the needs of the middle-end and high-end markets. SUMMARY

[0003] The present application provides an active yellow to orange dye composition, which has good wash fastness, high fixation rate and good build-up, and is suitable for printing and dyeing of nitrogen-containing and / or hydroxyl-containing fiber materials and their blended fabrics.

[0004] To achieve the above-mentioned application purposes, the technical solutions adopted by the present application are as follows:

[0005] The present application provides an active yellow to orange dye composition, which comprises component A and component B, wherein component A is selected from at least one of the dye compounds shown in formula (I), and component B is selected from at least one of the dye compounds shown in formula (II); the mass percentage content of component A in the active yellow to orange dye composition is 20-70%, and the mass percentage content of component B is 30-80%:

[0006]

[0007] In formula (I):

[0008] R 1 is C1-C4 alkyl, R 2 , R 3 are each independently H, C1-C4 alkyl, C1-C4 alkoxy or sulfonic acid group, M 1 , M 2 is H or alkali metal, X 1 is halogen or a group of the following formula (a),

[0009]

[0010] wherein, R4 , R 5 each independently H, C1-C4 alkyl, C1-C4 alkoxy or sulfonic acid group, Y 1 , Y 2 each independently -CH=CH2, -CH2CH2OSO3M 3 , the M 3 is H or alkali metal;

[0011] in the formula (II) :

[0012] D 1 , D 2 each independently a group represented by the following formula (b) or (c) or (d) :

[0013]

[0014] in the above formula (b), (c), (d) : R 6 , R 7 , R 9 , R 10 , R 12 , R 13 each independently H, C1-C4 alkyl, C1-C4 alkoxy or sulfonic acid group; x and y each independently a natural number between 1 and 3, and each R 8 each independently selected from H, sulfonic acid group, ureido group or C1-C4 alkylamido group; each R 11 each independently selected from H, hydroxyl group or sulfonic acid group;

[0015] X 2 , X 3 , X 4 each independently -SO2Y 3 , Y 3 is -CH=CH2 or -C2H4OSO3M 4 , M 4 is H or alkali metal.

[0016] In the present invention, the C1-C4 alkyl group can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, etc.; the C1-C4 alkoxy group can be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, t-butoxy, etc.

[0017] Further, R 1 is methyl or ethyl, R 2 , R 3 , R 4 , R 5 each independently hydrogen, methyl, methoxy or sulfonic acid group.

[0018] Further, D 1 , D2 all are groups of formula (b), which substituents can be the same or different; or D 1 is selected from the group of formula (b), D 2 is selected from the group of formula (c) or formula (d).

[0019] further, R 6 , R 7 , R 9 , R 10 , R 12 , R 13 are each independently H, methyl, methoxy or sulfo.

[0020] further, R 8 is hydrogen, sulfo, ureido or acetylamino.

[0021] Further, the active yellow to orange dye composition according to the present application preferably comprises the following dye components:

[0022] Component A: at least one dye compound selected from the group of formula (I);

[0023] Component B: at least one dye compound selected from the group of formula (II);

[0024] Further, the active yellow to orange dye composition according to the present application consists of Component A and Component B.

[0025] Still further, the active yellow to orange dye composition according to the present application preferably consists of the following dye components:

[0026] Component A: at least one dye compound of formula (I);

[0027] Component B: at least one dye compound of formula (II);

[0028] In particular, Component A is preferably selected from at least one of the following dye compounds of formula (I-1) to (I-8) and their alkali metal salts:

[0029]

[0030]

[0031] In particular, Component B is preferably selected from at least one of the following dye compounds of formula (II-1) to (II-25) and their alkali metal salts:

[0032]

[0033]

[0034]

[0035]

[0036]

[0037] Furthermore, component B is preferably at least one of the compounds shown in formulas (II-2)-(II-8), (II-12)-(II-16) and their alkali metal salts.

[0038] The reactive yellow to orange dye compositions of the present invention use dye compounds (I) to (II) which can be synthesized by conventional methods, for example by using suitable components known to those skilled in the art and using the necessary proportions by means of conventional diazotization and coupling reactions.

[0039] Furthermore, in the reactive yellow to orange dye composition of the present invention, the dye component can be an alkali metal salt, preferably a sodium or potassium salt. It is well known to those skilled in the art that dye compounds in free acid form and dye compounds in alkali metal salt (such as sodium or potassium salts) form have essentially the same dyeing properties. Typically, the structural formula of each monochrome dye compound is defined using the free acid form, but in actual synthesis, it is usually prepared and separated in the form of its alkali metal salt (such as sodium or potassium salt), and is also used for dyeing in its salt form, which is also well known to those skilled in the art.

[0040] The reactive yellow to orange dye composition of the present invention is prepared by mixing the dye components according to the aforementioned proportions. The mixing can be carried out by conventional mechanical methods, such as in a grinder, kneader, or homogenizer. During the mixing process, individual dye compounds can exist in the form of powder, granules, aqueous solution, or synthetic solution. When individual dye compounds are mixed in the form of synthetic solution, the composite reactive yellow to orange dye of the present invention can be separated from the synthetic solution by commonly known methods, such as salting out the dye from the reaction medium with an electrolyte (such as sodium chloride or potassium chloride), or evaporating or spray drying the mixed solution. Therefore, each dye component and its dye composition usually contain conventional electrolyte salts (such as sodium chloride, sodium sulfate, etc.) commonly found in reactive dyes.

[0041] The active yellow to orange dye composition of the present application, when sold as a product, can be free of auxiliary agents or can contain conventional auxiliary agents used in commercial dyes, such as solubilizers, dispersants, alkali-resistant auxiliary agents, dust-proofing agents, surfactants, buffering agents, and dyeing accelerators. Therefore, the present application also provides an active yellow to orange dye product containing the active yellow to orange dye composition. Preferably, the active yellow to orange dye product contains the active yellow to orange dye composition and auxiliary agents. The weight of the auxiliary agents is not more than 40% of the weight of the active yellow to orange dye composition, preferably not more than 30%. The auxiliary agents are preferably one or a combination of the following: naphthalene sulfonic acid formaldehyde condensate (NNO), methyl naphthalene sulfonic acid formaldehyde condensate (dispersant MF), dispersant CNF (benzyl naphthalene sulfonate formaldehyde condensate), sodium sulfate (industrial sodium sulfate), lignin sulfonate, sodium acetate, sodium bicarbonate, sodium citrate, sodium dihydrogen phosphate, disodium hydrogen phosphate, thickening agents, and the like. The auxiliary agents are all commercially available conventional types.

[0042] The active yellow to orange dye product of the present application is suitable for dyeing and printing of nitrogen-containing and / or hydroxyl-containing fiber materials, which can be cellulose fibers, preferably cotton fibers or regenerated fibers, and of course other plant fibers such as hemp fibers or fabrics; polyamide fibers, preferably animal fiber materials including skin, hair, or silk, and synthetic fiber materials such as nylon 6 and nylon 66. When dyeing and printing the above-mentioned fiber materials using the active yellow to orange dye product of the present application, known methods for dyeing with reactive dyes can be used, such as the conventional dyeing method by immersion and the padding method. The immersion dyeing method is a method in which the fabric is immersed in a dyeing solution, and the dye is gradually absorbed by the fabric, and generally involves the steps of dyeing - fixing - washing - soaping - washing - dehydration - drying. The padding method is a method in which the fabric is first immersed in a dyeing solution, then passed through a nip roller to uniformly apply the dyeing solution to the interior of the fabric, and then subjected to steaming or heat melting, and generally involves the steps of immersion in the dyeing solution - drying - (immersion in a fixing solution) - steaming or baking - washing - soaping - washing - drying.

[0043] The padding method is a method in which the fabric is first immersed in a dyeing solution, then passed through a nip roller to uniformly apply the dyeing solution to the interior of the fabric, and then subjected to steaming or heat melting, and generally involves the steps of immersion in the dyeing solution - drying - (immersion in a fixing solution) - steaming or baking - washing - soaping - washing - drying.

[0044] Generally, due to different requirements of dyeing shades on fabrics, the amount of dye used will also be different, when using dip dyeing method, the depth of dyeing (owf) is generally 0.1% to 10% (dye percentage of fabric weight), bath ratio 1:2 to 1:60 (weight ratio of fabric to dye, preferably 1:10 to 1:30), initial dyeing temperature control 30 to 60, ℃ dyeing time 10 to 30 minutes, soaping temperature 85 to 95, ℃ soaping time 10 to 15 minutes, fixation temperature 60 to 100, ℃ fixation time 10 to 50 minutes, fixation pH value 9 to 11. When using padding method, the padding rate of cellulose fiber is generally 60 to 80%, steaming temperature 100 to 103, ℃ steaming time 1 to 3 minutes. In the padding method, the cold pad-batch dyeing method is currently more commonly used, the dye and alkaline substance are introduced into the padding machine, and the fixation is carried out by rolling and stacking at room temperature for 2 to 30 hours, and then thorough rinsing is carried out.

[0045] The active yellow to orange dye composition and the product described in the application have the characteristics of good build-up, good compatibility, high fixation rate, excellent color fastness, especially outstanding water washing fastness, etc. when printing and dyeing nitrogen-containing and / or hydroxyl-containing fiber materials. DETAILED DESCRIPTION

[0046] The application will be further described below in combination with specific examples, but the protection scope of the application is not limited to this:

[0047] The dye compounds used in the examples of the application are prepared and separated in the form of their sodium salts in the actual synthesis process, and are also used for dyeing in the form of sodium salts, but for the convenience of writing, all chemical formulas of the dye compounds in the examples are embodied in the form of free acid, and the substantive dyeing performance is equivalent to the form of sodium salt.

[0048] Example 1:

[0049] 50 parts of the dye compound represented by formula (I-1), 50 parts of the dye compound represented by formula (II-2), and 15 parts of sodium sulfate are mechanically mixed to obtain a composite dye, which is used to dye cotton yellow by conventional dip dyeing method, the water washing staining fastness, especially the nylon and wool staining fastness, reaches level 4 or above (referring to ISO 105C10-2006), the build-up is excellent (referring to GB / T21875-2016), and the fixation rate reaches 80% (referring to GB / T2391-2014).

[0050]

[0051] Example 2:

[0052] 60 parts of the dye compound shown in formula (I-2), 20 parts of the dye compound shown in formula (II-2), 20 parts of the dye compound shown in formula (II-12) and 10 parts of meta alumina are mechanically mixed to obtain a composite dye, which is used to dye cotton into yellow by conventional dip dyeing method, and the fastness to water washing and especially the fastness to nylon and wool is up to grade 4 or above (referring to ISO 105C10-2006), the build-up is excellent (referring to GB / T21875-2016), and the fixation rate is up to 81% (referring to GB / T2391-2014).

[0053]

[0054]

[0055] Examples 3-30

[0056] According to the method described in one of Examples 1-2, the dyes in Table 1 are mechanically mixed in the proportions listed, and cotton is dyed into yellow to orange according to the conventional reactive dyeing method, and the fastness to water washing and especially the fastness to nylon and wool is up to grade 4 or above (referring to ISO 105C10-2006), the build-up is excellent (referring to GB / T21875-2016), and the fixation rate is up to 81% or above (referring to GB / T2391-2014).

[0057] Table 1

[0058]

[0059]

[0060] The reactive yellow to orange dye provided in the present application has obvious improvement in the fastness to water washing and fixation rate compared with the existing yellow to orange dyes on the market, and can meet the printing and dyeing requirements of medium or high-grade textiles.

Claims

1. An active yellow to orange dye composition comprising component A and component B, wherein component A is selected from at least one of the dye compounds represented by formula (I) and component B is selected from at least one of the dye compounds represented by formula (II); the mass percentage of component A in the active yellow to orange dye composition is 20-70% and the mass percentage of component B is 30-80%. In formula (I): R 1 is C1-C4 alkyl, R 2 , R 3 each independently is H, C1-C4 alkyl, C1-C4 alkoxy or sulfo, M 1 , M 2 is H or an alkali metal, X 1 is halogen or a group of the formula (a) wherein R 4 , R 5 each independently H, C1-C4 alkyl, C1-C4 alkoxy or a sulfonic acid group, Y 1 , Y 2 each independently -CH=CH2, -CH2CH2OSO3M 3 , said M 3 is H or an alkali metal; In formula (II): D 1 , D 2 each independently is a group of the formula (b) or (c) or (d): in the above formulae (b), (c), (d): R 6 , R 7 , R 9 , R 10 , R 12 , R 13 each independently H, C1-C4 alkyl, C1-C4 alkoxy or sulfonic acid group; x and y are each independently a natural number between 1 and 3, and each R 8 is each independently selected from H, sulfonic acid group, ureido group or C1-C4 alkylamido group; each R 11 is each independently selected from H, hydroxyl group or sulfonic acid group; X 2 , X 3 , X 4 each independently -SO2Y 3 , Y 3 -CH=CH2or -C2H4OSO3M 4 , M 4 is H or an alkali metal.

2. The active yellow to orange dye composition according to claim 1, consisting of component A and component B, wherein the mass percentage of component A is 20-70% and the mass percentage of component B is 30-80%.

3. The active yellow to orange dye composition according to claim 1, wherein: The component A is selected from at least one of the dye compounds represented by formula (I-1) to (I-8) and alkali metal salts thereof:

4. The active yellow to orange dye composition according to claim 1, wherein: The component B is selected from at least one of the dye compounds represented by formula (II-1) to (II-25) and alkali metal salts thereof:

5. The active yellow to orange dye composition according to claim 4, wherein: ###0002### The component B is selected from at least one of the dye compounds represented by formula (II-2) to (II-8), (II-12) to (II-16) and alkali metal salts thereof.

6. An activated yellow to orange dye composition according to any one of claims 3 to 4, characterised in that: The alkali metal salt is sodium salt or potassium salt.

7. An active yellow to orange dye product, characterized by: The active yellow to orange dye composition according to any one of claims 1 to 4 and an auxiliary agent, wherein the auxiliary agent is naphthalene sulfonic acid formaldehyde condensate, methyl naphthalene sulfonic acid formaldehyde condensate, dispersant CNF, anhydrous sodium sulfate, lignin sulfonate, sodium acetate, sodium bicarbonate, sodium citrate, sodium dihydrogen phosphate, disodium hydrogen phosphate, thickening agent.

8. The active yellow to orange dye product according to claim 7, wherein the weight of the auxiliary agent is not more than 40% of the weight of the active yellow to orange dye composition.

9. The active yellow to orange dye product according to claim 7 or 8, for dyeing application on nitrogen-containing and / or hydroxyl-containing materials.

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