Reactive yellow-to-orange dye composition and dye product

Abstract

The invention discloses a reactive yellow-to-orange dye composition and a dye product. The reactive yellow-to-orange dye composition comprises a component A and a component B, the component A is selected from at least one of dye compounds shown in a formula (I), and the component B is selected from at least one of dye compounds shown in a formula (II); in the reactive yellow-to-orange dye composition, the mass percentage content of the component A is 20-70%, and the mass percentage content of the component B is 30-80%. When the reactive yellow-to-orange dye composition is used for printing and dyeing a nitrogen-containing and / or hydroxyl-containing fiber material, the reactive yellow-to-orange dye composition has the characteristics of good lifting property, good compatibility, high fixation rate, excellent color fastness, particularly outstanding washing fastness and the like. # imgabs0 #

Description

Technical Field

[0001] The invention relates to a reactive yellow to orange dye composition, in particular to a reactive yellow to orange dye composition suitable for dyeing and printing nitrogen-containing and / or hydroxyl-containing fiber materials and a dye product. Background Art

[0002] Azo dyes are produced by diazotization of aromatic amines and coupling with suitable coupling components. They can produce various colors and play an important role as colorants in the textile industry. In recent years, the market has increased its requirements for the fastness of dyed textiles. For example, many buyers of textile products require a good evaluation of color fastness after multiple washes according to ISO 105-C09. Good wash fastness dyes can extend the service life of textiles, but the existing dyes on the market still cannot meet the requirements well, especially the lack of yellow to orange reactive dyes. Therefore, it is necessary to explore more high-quality reactive yellow to orange dyes to meet the needs of the mid-end and high-end markets. Summary of the invention

[0003] The present inventors have provided a reactive yellow to orange dye composition through optimized design, which has the characteristics of good water washing fastness, high color fixation rate, good lifting power, etc., and is suitable for printing and dyeing nitrogen-containing and / or hydroxyl-containing fiber materials and their blended fabrics.

[0004] In order to achieve the above-mentioned invention object, the present invention adopts the following technical solutions:

[0005] The present invention provides a reactive yellow to orange dye composition, comprising 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); in the reactive yellow to orange dye composition, the mass percentage of component A is 20-70%, and the mass percentage of component B is 30-80%:

[0006]

[0007] In formula (I):

[0008] R 1 C 1 ~C 4 Alkyl, R 2 , R 3 Each is independent of H and C 1 ~C 4 Alkyl, C 1 ~C 4 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] Among them, R 4 , R 5 Each is independent of H and C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy or sulfonic acid group, Y 1 , Y 2 Each is independently -CH=CH 2 、-CH 2 CH 2 OSO 3 M 3 , the M 3 is H or an alkali metal;

[0011] In formula (II):

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

[0013]

[0014] In the above formulas (b), (c), and (d): R 6 , R 7 , R 9 , R 10 , R 12 , R 13 Each is independent of H and C 1 ~C 4 Alkyl, C 1 ~C 4 Alkoxy or sulfonic acid; x and y are each independently a natural number between 1 and 3, each R 8 Each independently selected from H, sulfonic acid, urea or C 1 ~C 4 alkanoylamino; each R 11 Each is independently selected from H, hydroxyl or sulfonic acid;

[0015] X 2 , X 3 , X 4 Each is independent of -SO 2 Y 3 , Y 3 -CH=CH 2 or -C 2 H 4 OSO 3 M 4 , M 4It is H or an alkali metal.

[0016] In the present invention, the C 1 ~C 4 The alkyl group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.; 1 ~C 4 The alkoxy group may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, or the like.

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

[0018] Further, D 1 , D 2 are all derived from the group of general formula (b), and the substituents may be the same or different; or D 1 is selected from the group represented by formula (b), D 2 A group selected from the group represented by formula (c) or formula (d).

[0019] Further, R 6 , R 7 , R 9 , R 10 , R 12 , R 13 Each is independently H, methyl, methoxy or sulfonic acid.

[0020] Further, R 8 It is hydrogen, sulfonic acid, urea or acetylamino.

[0021] Furthermore, the reactive yellow to orange dye composition of the present invention preferably comprises the following dye components:

[0022] Component A: at least one selected from the dye compounds represented by formula (I);

[0023] Component B: at least one selected from the dye compounds represented by formula (II);

[0024] Furthermore, the reactive yellow to orange dye composition consists of component A and component B.

[0025] Furthermore, the reactive yellow to orange dye composition of the present invention is preferably composed of the following dye components:

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

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

[0028] Specifically, the component A is preferably at least one of the dye compounds represented by the following formulas (I-1) to (I-8) and their alkali metal salts:

[0029]

[0030]

[0031] Specifically, the component B is preferably at least one of the dye compounds represented by the following formulas (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 represented by formulae (II-2) to (II-8), (II-12) to (II-16) and their alkali metal salts.

[0038] The reactive yellow to orange dye composition of the present invention, the dye compounds (I) to (II) used can be synthesized by conventional methods, for example, by using appropriate components well known to those skilled in the art and using necessary proportions with the aid of conventional diazotization reactions and coupling reactions.

[0039] In addition, in the reactive yellow to orange dye composition of the present invention, the dye component may be an alkali metal salt, and preferably, the alkali metal salt is a sodium salt or a potassium salt. It is clear to those skilled in the art that the dye compound in the form of a free acid and the dye compound in the form of an alkali metal salt (such as a sodium salt, a potassium salt, etc.) have the same substantial dyeing performance, and generally the structural formula of each monochromatic dye compound is defined in the form of a free acid, and in the actual synthesis process, it is generally prepared and separated in the form of an alkali metal salt (such as a sodium salt or a potassium salt), and is also used for dyeing in the form of a salt, which is also well known to those skilled in the art.

[0040] The active yellow to orange dye composition of the present invention comprises a preparation method comprising mixing the dye components according to the aforementioned ratio. The mixing can be carried out in a conventional mechanical manner, such as in a grinder, a kneader or a homogenizer. During the mixing process, the individual dye compounds can be in the form of powder, granules, aqueous solution or synthetic solution. When the individual dye compounds are mixed in the form of a synthetic solution, the composite active yellow to orange dye of the present invention can be separated from the synthetic solution by a generally known method, such as using an electrolyte (such as sodium chloride or potassium chloride) to filter out the dye salt from the reaction medium, or evaporating and spray drying the mixed solution. Therefore, the dye components and the dye composition thereof usually contain conventional electrolyte salts (such as sodium chloride, sodium sulfate, etc.) in active dyes.

[0041] The active yellow to orange dye composition of the present invention may not be added with auxiliary agents when sold as a commodity, or conventional auxiliary agents in commercial dyes may be added, such as cosolvents, dispersants, alkali-resistant auxiliary agents, dust-proof agents, surfactants, buffers and dyeing accelerators. Therefore, the present invention also provides an active yellow to orange dye product, which contains 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 agent does not exceed 40% of the weight of the active yellow to orange dye composition, preferably not more than 30%. The auxiliary agent is preferably one of the following or a combination of any of the following: naphthalenesulfonic acid formaldehyde condensate (NNO), methylnaphthalenesulfonic acid formaldehyde condensate (dispersant MF), diffusant CNF (benzylnaphthalenesulfonate formaldehyde condensate), glauber powder (industrial sodium sulfate), lignin sulfonate, sodium acetate, sodium bicarbonate, sodium citrate, sodium dihydrogen phosphate, disodium hydrogen phosphate, thickener, etc. The auxiliary agents are all commercially available conventional varieties.

[0042] The reactive yellow to orange dye product of the present invention is suitable for printing and dyeing nitrogen-containing and / or hydroxyl-containing fiber materials, which can be cellulose fibers, polyamide fibers and fabrics thereof, wherein the cellulose fibers are preferably cotton fibers or regenerated fibers, and of course can also include other plant fibers, such as hemp fibers or fabrics; polyamide fibers are preferably animal fiber materials including leather, wool or silk, and synthetic fiber materials such as nylon 6 and nylon 66. When the reactive yellow to orange dye product of the present invention is used to print and dye the above-mentioned fiber materials, it can be carried out in accordance with known reactive dyeing methods, such as the commonly used reactive dyeing exhaust dyeing method and pad dyeing method. The exhaust dyeing method is a method in which the fabric is immersed in a dyeing solution to gradually dye the fabric with the dye, which usually requires dyeing-fixing-washing-soap boiling-washing-dehydration-drying and other processes.

[0043] The pad dyeing is a dyeing method in which the fabric is first immersed in the dye solution, then the fabric is passed through rollers to evenly roll the dye solution into the fabric, and then subjected to steaming or hot melting treatment. It usually requires the following steps: padding dye solution - drying - (pad fixing solution) - steaming or baking - washing - soaping - washing - drying.

[0044] Usually, due to the different requirements for the coloring of fabrics, the amount of dye used will also be different. When using the exhaust dyeing method, the dyeing depth (owf) is generally 0.1% to 10% (the percentage of dye in the weight of the fabric), the bath ratio is 1:2 to 1:60 (the weight ratio of fabric to dye liquor, preferably 1:10 to 1:30), the initial dyeing temperature is controlled at 30 to 60°C, the dyeing time is 10 to 30 minutes, the soap boiling temperature is 85 to 95°C, the soap boiling time is 10 to 15 minutes, the color fixing temperature is 60 to 100°C, the color fixing time is 10 to 50 minutes, and the color fixing pH value is 9 to 11. When using the pad dyeing method for dyeing, the rolling rate of cellulose fiber is generally 60 to 80%, the steaming temperature is 100 to 103°C, and the steaming time is 1 to 3 minutes. Among the pad dyeing methods, the cold padding pile dyeing method is currently more commonly used, in which the dye and alkaline substance are introduced into the pad dyeing machine, and rolled and piled at room temperature for 2 to 30 hours for color fixing, and then thoroughly rinsed.

[0045] The reactive yellow to orange dye composition and product of the present invention, when used for dyeing and printing nitrogen-containing and / or hydroxyl-containing fiber materials, has the characteristics of good lifting performance, good compatibility, high color fixation rate, excellent color fastness, especially outstanding water washing fastness, etc. DETAILED DESCRIPTION

[0046] The present invention is further described below in conjunction with specific embodiments, but the protection scope of the present invention is not limited thereto:

[0047] The dye compounds used in the embodiments of the present invention are prepared and separated in the form of their sodium salts during the actual synthesis process, and are also used for dyeing in the form of sodium salts. However, for the convenience of writing, all chemical formulas of the dye compounds in the embodiments are expressed in the form of free acids, and their actual dyeing performance is equivalent to that of the sodium salts.

[0048] Embodiment 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 exhaust dyeing method. The composite dye has water-washing staining resistance, especially the staining fastness of nylon and wool is above grade 4 (refer to ISO 105C10-2006), excellent lifting power (refer to GB / T21875-2016), and the color fixation rate is 80% (refer to GB / T2391-2014).

[0050]

[0051] Embodiment 2:

[0052] 60 parts of the dye compound represented by formula (Ⅰ-2), 20 parts of the dye compound represented by formula (Ⅱ-2), 20 parts of the dye compound represented by formula (Ⅱ-12) and 10 parts of sodium sulfate are mechanically mixed to obtain a composite dye, which is used to dye cotton yellow by conventional exhaust dyeing method, and has water-washing staining resistance, especially nylon and wool staining fastness of more than grade 4 (refer to ISO 105C10-2006), excellent lifting power (refer to GB / T21875-2016), and a fixation rate of 81% (refer to GB / T2391-2014).

[0053]

[0054]

[0055] Embodiments 3 to 30

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

[0057] Table 1

[0058]

[0059]

[0060] The reactive yellow to orange dye provided by the present invention has significantly improved color fastness to washing and color fixation rate compared with the existing yellow to orange dyes on the market, and can meet the printing and dyeing needs of mid-range or high-end textiles.

Claims

1. A reactive yellow to orange dye composition, comprising 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); in the reactive yellow to orange dye composition, the mass percentage of component A 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 is independently H, C1-C4 alkyl, C1-C4 alkoxy or sulfonic acid, M 1 、M 2 is H or alkali metal, X 1 is halogen or a group of the following formula (a), in, R 4 , R 5 Each is independently H, C1-C4 alkyl, C1-C4 alkoxy or sulfonic acid, Y 1 , Y 2 Each is independently -CH=CH2, -CH2CH2OSO3M 3 , the M 3 is H or an alkali metal; In formula (II): D 1 , D 2 Each is independently a group represented by the following formula (b), (c) or (d): In the above formulas (b), (c), and (d): R 6 , R 7 , R 9 , R 10 , R 12 , R 13 Each independently represents H, C1-C4 alkyl, C1-C4 alkoxy or sulfonic acid; x and y are each independently a natural number between 1 and 3, and each R 8 Each R is independently selected from H, sulfonic acid, urea or C1-C4 alkanoylamino; 11 Each is independently selected from H, hydroxyl or sulfonic acid; X 2 , X 3 , X 4 Each is independent of -SO2Y 3 , Y 3 -CH=CH2 or -C2H4OSO3M 4 , M 4 It is H or an alkali metal.

2. The reactive yellow to orange dye composition as claimed in claim 1, comprising component A and component B, wherein the mass percentage of component A is 20 to 70%, and the mass percentage of component B is 30 to 80%.

3. The reactive yellow to orange dye composition as claimed in claim 1, characterized in that: The component A is selected from at least one of the dye compounds represented by the following formulas (I-1) to (I-8) and their alkali metal salts:

4. The reactive yellow to orange dye composition as claimed in claim 1, characterized in that: The component B is selected from at least one of the dye compounds represented by the following formulas (II-1) to (II-25) and their alkali metal salts:

5. The reactive yellow to orange dye composition as claimed in claim 4, characterized in that: 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 their alkali metal salts.

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

7. A reactive yellow to orange dye product, characterized in that: The invention comprises 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 naphthalenesulfonic acid formaldehyde condensate, methylnaphthalenesulfonic acid formaldehyde condensate, a diffusant CNF, sodium sulfate, lignin sulfonate, sodium acetate, sodium bicarbonate, sodium citrate, sodium dihydrogen phosphate, disodium hydrogen phosphate, and a thickener.

8. A reactive yellow to orange dye product as claimed in claim 7, wherein the weight of the auxiliary agent does not exceed 40% of the weight of the reactive yellow to orange dye composition.

9. A reactive yellow to orange dye product as claimed in claim 7 or 8, for dyeing on nitrogen-containing and / or hydroxyl-containing materials.

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