An active red dye composition and a dye product

Abstract

The application discloses a kind of active red dye compositions, including component A, component B and component C, wherein component A is selected from at least one of the dye compounds as shown in formula (I), component B is selected from at least one of the dye compounds as shown in formula (II), component C is selected from at least one of the dye compounds as shown in formula (III);The mass percentage content of component A in the active red dye composition is 1-25%, the mass percentage content of component B is 50-95%, and the mass percentage content of component C is 1-25%.The active red dye composition of the application has excellent characteristics such as wash fastness, rubbing fastness, light fastness, etc. when used for printing and dyeing of nitrogen-containing and / or hydroxyl-containing fiber materials.

Description

Technical Field

[0001] This invention relates to a reactive red dye composition, and more particularly to a reactive red dye composition and dye product suitable for printing and dyeing nitrogen-containing and / or hydroxyl-containing fiber materials. Background Technology

[0002] In recent years, the market has raised its requirements for the fastness of dyed textiles. There is now a need for reactive dyes that possess sufficient affinity and allow for easy washing away of unfixed portions. Furthermore, they should have good fixation rates and high reactivity, particularly high wet and light fastness. However, currently available dyes on the market still do not adequately meet these requirements.

[0003] Therefore, the purpose of this invention is to discover new and improved reactive dyes, particularly red reactive dyes, which can be used for dyeing and printing fiber materials to meet the dyeing and printing needs of the mid-to-high-end market. Summary of the Invention

[0004] Through optimized design, the inventors have provided a reactive red dye composition with excellent washability, abrasion resistance, and light fastness, which is suitable for printing and dyeing nitrogen-containing and / or hydroxyl-containing fiber materials and their blended fabrics.

[0005] To achieve the above-mentioned objectives, the present invention adopts the following technical solution:

[0006] This invention provides a reactive red dye composition comprising component A, component B, and component C, wherein component A is selected from at least one dye compound of formula (I), component B is selected from at least one dye compound of formula (II), and component C is selected from at least one dye compound of formula (III); wherein the reactive red dye composition comprises component A at a mass percentage of 1-25%, component B at a mass percentage of 50-95%, and component C at a mass percentage of 1-25%.

[0007]

[0008]

[0009] In formula (Ⅰ):

[0010] R 1 It is a C1 to C4 alkyl group, R 2 R 3 Each group is independently H, C1-C4 alkyl, C1-C4 alkoxy, or sulfonic acid group, M 1 M 2 H or alkali metal, X 1 It is a halogen or a group of formula (a).

[0011]

[0012] Among them, R 13 R 14 Each group is independently H, C1-C4 alkyl, C1-C4 alkoxy, or sulfonic acid group, Y 1 Y 4 Each can be independently represented as -CH=CH2 or -CH2CH2OSO3M 5 The M 5 It is H or an alkali metal;

[0013] In formula (II):

[0014] R 4 R is a hydrogen or sulfonic acid group. 5 It is H or C1-C4 alkyl, X 2 For halogens, R 6 R 7 Each group is independently H, C1-C4 alkyl, C1-C4 alkoxy, or sulfonic acid group, Y 2 -CH=CH2, -CH2CH2OSO3M 6 The M 3 M 4 M 6 It is H or an alkali metal;

[0015] In formula (Ⅲ):

[0016] R 8 R 9 R 11 R 12 Each group is independently H, C1-C4 alkyl, C1-C4 alkoxy, or sulfonic acid group, R 10 It is a C1-C4 alkyl or hydroxyethyl group, n is a natural number from 2 to 6, X 3 For halogen, Y 3 -CH=CH2, -CH2CH2OSO3M 7 The M 7 It is H or an alkali metal.

[0017] In this invention, the C1-C4 alkyl group can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.; the C1-C4 alkoxy group can be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, etc.

[0018] Furthermore, R 1 It is methyl or ethyl, R 2 R 3 Each can be independently a hydrogen, methyl, methoxy, or sulfonic acid group.

[0019] Furthermore, R 6R 7 Each can be independently represented by H, methyl, methoxy, or sulfonic acid groups.

[0020] Furthermore, R 8 R 9 R 11 R 12 Each can be independently represented by H, methyl, methoxy, or sulfonic acid groups.

[0021] Furthermore, the reactive red dye composition comprises component A, component B, and component C.

[0022] Specifically, component A is preferably at least one of the dye compounds and their alkali metal salts represented by the following formulas (I-1) to (I-8):

[0023]

[0024]

[0025] Specifically, component B is preferably at least one of the dye compounds and their alkali metal salts represented by the following formulas (II-1) to (II-11):

[0026]

[0027]

[0028]

[0029] Specifically, component C is preferably at least one of the dye compounds and their alkali metal salts represented by formulas (Ⅲ-1) to (Ⅲ-10):

[0030]

[0031]

[0032]

[0033] The reactive red dye composition of the present invention uses dye compounds (I) to (III), which are all publicly reported dyes and can be synthesized by methods described in the literature, for example by using suitable components known to those skilled in the art and using the necessary proportions by means of conventional diazotization, coupling and condensation reactions.

[0034] Furthermore, in the reactive red 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 formulas of various monochrome dye compounds are defined using the free acid form, but in actual synthesis, they are usually prepared and separated in the form of their alkali metal salt (such as sodium or potassium salt), and are also used for dyeing in their salt form, which is also well known to those skilled in the art.

[0035] The reactive red dye composition of the present invention is prepared by mixing the dye components according to the aforementioned ratio. The mixing can be carried out by conventional mechanical means, 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 red 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.

[0036] The reactive red dye composition of the present invention, when sold commercially, may be sold without auxiliaries, or may contain conventional auxiliaries found in commercial dyes, such as solubilizers, dispersants, alkali-resistant auxiliaries, dust suppressants, surfactants, buffers, and dyeing accelerators. Therefore, the present invention also provides a reactive red dye product containing the aforementioned reactive red dye composition. Preferably, the reactive red dye product contains the aforementioned reactive red dye composition and auxiliaries. The weight of the auxiliaries does not exceed 40% of the weight of the reactive red dye composition, preferably not exceeding 30%. The auxiliaries preferably include one or any combination of the following: naphthalenesulfonic acid formaldehyde condensate (NNO), methylnaphthalenesulfonic acid formaldehyde condensate (dispersant MF), CNF (benzylnaphthalenesulfonate formaldehyde condensate), sodium sulfate (industrial sodium sulfate), lignin sulfonate, sodium acetate, sodium bicarbonate, sodium citrate, sodium dihydrogen phosphate, disodium hydrogen phosphate, thickeners, etc. All auxiliaries are commercially available conventional varieties.

[0037] The reactive red dye product of this invention is suitable for dyeing and printing on nitrogen-containing and / or hydroxyl-containing fiber materials. These materials can be cellulose fibers, polyamide fibers, and their fabrics. Cellulose fibers are preferably cotton fibers or regenerated fibers, but may also include other plant fibers, such as hemp fibers or fabrics. Polyamide fibers are preferably animal fibers, including leather, wool, or silk, as well as synthetic fibers such as nylon 6 and nylon 66. When dyeing the aforementioned fiber materials using the reactive red dye product of this invention, known reactive dyeing methods can be followed, such as the commonly used reactive dye immersion dyeing method and pad dyeing method. Immersion dyeing involves immersing the fabric in a dye bath, allowing the dye to gradually coat the fabric. This typically requires processes such as dyeing, fixing, washing, soaping, washing, dehydration, and drying.

[0038] Padding dyeing involves first immersing the fabric in a dye solution, then passing the fabric through rollers to evenly roll the dye solution into the fabric, followed by steaming or hot melting treatment. It typically involves processes such as padding with dye solution, drying, (padding with fixing solution), steaming or baking, washing, soaping, washing, and drying.

[0039] Generally, the amount of dye used varies depending on the desired color on the fabric. When using immersion dyeing, the owf (color depth) is typically 0.1%–10% (dye weight percentage of fabric), the liquor ratio is 1:2–1:60 (fabric to dye liquor weight ratio, preferably 1:10–1:30), the initial dyeing temperature is controlled at 30–60°C, the dyeing time is 10–30 minutes, the soaping temperature is 85–95°C, the soaping time is 10–15 minutes, the fixing temperature is 60–100°C, the fixing time is 10–50 minutes, and the fixing pH is 9–11. When using pad dyeing, the pad residue of cellulose fibers is typically 60–80%, the steaming temperature is 100–103°C, and the steaming time is 1–3 minutes. Currently, cold pad-batch dyeing is commonly used in pad dyeing. In this method, dye and alkaline substances are introduced into the pad dyeing machine and the dye is rolled up and piled at room temperature for 2–30 hours for fixing, followed by thorough rinsing.

[0040] The reactive red dye composition and products of the present invention, when used for printing and dyeing nitrogen-containing and / or hydroxyl-containing fiber materials, have the characteristics of good enhancement, good compatibility and excellent color fastness, especially outstanding wash fastness. Detailed Implementation

[0041] The present invention will be further described below with reference to specific embodiments, but the scope of protection of the present invention is not limited thereto:

[0042] The dye compounds used in the embodiments of the present invention are prepared and separated in the form of sodium salts during the actual synthesis process, and are also used for dyeing in the form of sodium salts. However, for the sake of convenience, all chemical formulas of the dye compounds in the embodiments are represented in the form of free acids, and their dyeing performance is equivalent to that of sodium salts.

[0043] Example 1:

[0044] Ten parts of the dye compound shown in formula (Ⅰ-1), 80 parts of the dye compound shown in formula (Ⅱ-1), 10 parts of the dye compound shown in formula (Ⅲ-1), and 15 parts of sodium sulfate were mechanically mixed to obtain a composite dye that dyed cotton red using conventional immersion dyeing methods. The dye exhibited a water washing staining fastness, especially for nylon and wool, of grade 4 or higher (refer to ISO 105C10-2006), a light fastness of grade 5-6 (refer to ISO 105-B02), and a rubbing fastness of grade 4 or higher (refer to ISO 105-X12).

[0045]

[0046] Example 2:

[0047] Five parts of the dye compound shown in formula (Ⅰ-2), 75 parts of the dye compound shown in formula (Ⅱ-2), 20 parts of the dye compound shown in formula (Ⅲ-2), and 10 parts of sodium sulfate were mechanically mixed to obtain a composite dye that dyed cotton red using conventional immersion dyeing methods. The dye exhibited a water washing staining fastness, especially for nylon and wool, of grade 4 or higher (refer to ISO 105C10-2006), a light fastness of grade 5-6 (refer to ISO 105-B02), and a rubbing fastness of grade 4 or higher (refer to ISO 105-X12).

[0048]

[0049] Examples 3-30

[0050] According to the method described in any one of Examples 1 to 2, the dyes listed in Table 1 are mechanically mixed and dyed red cotton using conventional reactive dyeing methods. The color fastness to washing staining, especially to nylon and wool, reaches grade 4 or above (refer to ISO 105 C10-2006), the light fastness reaches grade 5 to 6 (refer to ISO 105-B02), and the rubbing fastness reaches grade 4 or above (refer to ISO 105-X12).

[0051] Table 1

[0052]

[0053]

[0054] The reactive red dye provided by this invention has superior washing fastness, light fastness and rubbing fastness compared to existing red dyes on the market, which can meet the printing and dyeing needs of mid-range or high-end textiles.

Claims

1. An active red dye composition comprising component A, component B and component C, wherein component A is selected from at least one of the dye compounds represented by formula (I), component B is selected from at least one of the dye compounds represented by formula (II), and component C is selected from at least one of the dye compounds represented by formula (III); the active red dye composition has a mass percentage of component A of 1-25%, a mass percentage of component B of 50-95%, and a mass percentage of component C of 1-25%; formula (I) is: ###0001### formula (II) is: ###0002### formula (III) is: ###0003### the mass percentage of component A is 1-25%, the mass percentage of component B is 50-95%, and the mass percentage of component C is 1-25%. 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: ###0004### The component B is selected from at least one of the dye compounds represented by formula (II-1) to (II-11) and alkali metal salts thereof: ###0005### The component C is selected from at least one of the dye compounds represented by formula (III-1) to (III-10) and alkali metal salts thereof: ###0006### The alkali metal salt is a sodium salt or a potassium salt. 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 13 , R 14 each independently H, C1-C4 alkyl, C1-C4 alkoxy or a sulfonic acid group, Y 1 , Y 4 each independently -CH=CH2, -CH2CH2OSO3M 5 , said M 5 is H or an alkali metal; The active red dye composition of any one of claims 1 to 5 and an auxiliary agent, the auxiliary agent being 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. R 4 is hydrogen or a sulfonic acid group, R 5 is H or C1-C4 alkyl, X 2 is halogen, R 6 , R 7 each independently is H, C1-C4 alkyl, C1-C4 alkoxy or a sulfonic acid group, Y 2 is -CH=CH2, -CH2CH2OSO3M 6 , said M 3 , M 4 , M 6 is H or an alkali metal; 8. The active red dye product of claim 7, the auxiliary agent having a weight of not more than 40% of the weight of the active red dye composition. R 8 , R 9 , R 11 , R 12 each independently H, C1-C4 alkyl, C1-C4 alkoxy or sulfonic acid group, R 10 is C1-C4 alkyl or hydroxyethyl, n is a natural number from 2 to 6, X 3 is halogen, Y 3 is -CH=CH2, -CH2CH2OSO3M 7 , said M 7 is H or an alkali metal.

2. The active red dye composition according to claim 1, consisting of Component A, Component B, and Component C, wherein, 9. The active red dye product of claim 7 or 8, for dyeing use on nitrogen-containing and / or hydroxyl-containing materials.

3. The active red dye composition according to claim 1, wherein: ​ 4. The activated red dye composition of claim 1, wherein: ​ 5. The active red dye composition according to claim 1, wherein: ​ 6. An activated red dye composition according to any one of claims 3 to 5, wherein: ​ 7. An active red dye product, characterized by: ​ ​ ​

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