A yellow to orange dispersion dye composition and dye article

Abstract

The present application provides a yellow to orange dye composition, comprising component A and component B, wherein component A is at least one of the dye compounds shown in formula (I), and component B is at least one of the dye compounds shown in formula (II) and / or formula (III); when the dye composition is applied to hydrophobic fiber material for dyeing, it has excellent dyeing fastness, especially outstanding fastness to sunlight, and can meet the printing and dyeing needs of automobile interior fabric.

Description

(I) Technical Field

[0001] This invention relates to a disperse yellow to orange dye composition and dye article, and more particularly to a disperse yellow to orange dye composition and dye article with high lightfastness suitable for printing and dyeing hydrophobic fiber materials. (II) Background Technology

[0002] In recent years, with the increasing sophistication of automobiles in my country, automotive interior materials are shifting from the widely used polyvinyl chloride (PVC) to polyester fibers. The dye requirements for these polyester fibers are higher than the lightfastness standards for ordinary clothing dyes. While the lightfastness test for general clothing textiles is conducted at around 60℃, the test for automotive interior fabrics is performed at 80-90℃ with longer exposure times. Currently, the dyes used for automotive interior fabrics are mostly a mixture of three basic colors: anthraquinone yellow, anthraquinone red, and anthraquinone blue. However, the dyeing effect is not satisfactory, and the production process of most anthraquinone dyes is not environmentally friendly. Therefore, researching a product with good dyeing performance that can replace or reduce the use of anthraquinone dyes has become a market need. (III) Summary of the Invention

[0003] The purpose of this invention is to provide a disperse yellow to orange dye composition that exhibits excellent dyeing performance, especially superior light fastness, when applied to the dyeing of hydrophobic fiber materials, thus meeting the high-standard requirements of special fabrics such as automotive fabrics.

[0004] The technical solution adopted in this invention is:

[0005] A disperse yellow to orange dye composition comprising component A and component B, wherein component A is at least one of the dye compounds shown in formula (I), and component B is at least one of the dye compounds shown in formula (II) and / or formula (III), wherein, based on components A and B, the mass percentage content of component A is 5-50%, and the mass percentage content of component B is 50-95%.

[0006]

[0007]

[0008] In formula (I):

[0009] R 1 It is a C1-C4 alkyl, phenyl, benzyl, C1-C4 alkyl or nitro-substituted benzyl, methoxyethyl, ethoxyethyl, methoxycarbonylethyl; R 2 R 3 Each is independently a C1 to C4 alkyl group, R 4 It is a C1-C4 alkyl or cyanoethyl;

[0010] In formula (II):

[0011] R 5 C1-C4 alkyl or C1-C4 alkoxy substituted C1-C4 alkyl, R 6 R is hydrogen or nitro. 7 It is a nitro group, halogen, C1-C4 alkoxy group, -COOC2H4O-Ph, -OCOOCH2-Ph, -OSO2-Ph or -SO2N(CH3)2, wherein Ph is a phenyl group;

[0012] In formula (Ⅲ):

[0013] R 8 For H or Br, R 9 It is -CONHC2H5 or -CON(CH3)2.

[0014] In this invention, the C1-C4 alkyl group can be methyl, ethyl, straight-chain or branched propyl, or straight-chain or branched butyl.

[0015] Preferably, component A is one of the following formulas or a mixture of two or more of them in any proportion:

[0016]

[0017]

[0018]

[0019] Preferably, component B is one of the following formulas or a mixture of two or more of them in any proportion:

[0020]

[0021]

[0022]

[0023] Furthermore, based on the aforementioned components A and B, the mass percentage content of component A is 5-40%, and the mass percentage content of component B is 60-95%.

[0024] As a further preferred embodiment, the disperse yellow to orange dye composition comprises component A and component B, wherein:

[0025] Component A is selected from at least one of formulas (I-1) to (I-4);

[0026] Component B is selected from at least one of formulas (II-5) to (II-8) and (III-1) to (III-2).

[0027] The mass percentage of component A is 5-50%, and the mass percentage of component B is 50-95%.

[0028] As a particularly preferred embodiment, the disperse yellow to orange dye composition comprises component A and component B, wherein the mass percentage of component A is 5-50% and the mass percentage of component B is 50-95%.

[0029] It should be noted that, due to the special nature of the dye industry, it is difficult and unnecessary to produce pure products from components A and B. Small amounts of byproducts are usually generated during their synthesis. These byproducts do not need to be separated and can be used together in the blending of dyes. The amount of byproducts should preferably be controlled within 15% (based on the weight of the dye components, excluding auxiliaries).

[0030] The disperse yellow to orange dye composition of the present invention may also allow the addition of dyes of formulas (Ⅳ-1) to (Ⅳ-3) thereof in a mass percentage not exceeding 10%:

[0031]

[0032] The disperse yellow to orange dye composition described in this invention refers to dye filter cake (original dye), which does not include any finishing agents, but is allowed to contain a small amount of impurities introduced during synthesis. These impurities do not affect the performance of the dye. The dye mass percentage is calculated based on the dry weight of the dye filter cake.

[0033] When the disperse yellow to orange dye composition of the present invention is sold commercially or used for coloring textile materials, it usually requires the addition of auxiliaries for post-treatment. Therefore, the present invention also provides a disperse yellow to orange dye product, which is composed of the disperse yellow to orange dye composition and auxiliaries, wherein the weight ratio of auxiliaries to disperse yellow to orange dye composition is 0.2 to 5:1. The auxiliaries are dispersants, diffusion agents and other surfactants commonly used in the compounding of disperse dyes, preferably from one or a mixture of two or more of the following: naphthalene sulfonate formaldehyde condensate, lignin sulfonate, alkyl naphthalene sulfonate formaldehyde condensate (such as methyl naphthalene sulfonate formaldehyde condensate (dispersant MF)), naphthalene sulfonate formaldehyde condensate (diffusion agent NNO), benzyl naphthalene sulfonate formaldehyde condensate (diffusion agent CNF), sodium lignin sulfonate (lignin 85A, lignin 83A), sodium sulfate, etc.

[0034] The preparation method of the disperse yellow to orange dye of the present invention is as follows: The aforementioned dye monomer compounds (original dyes) are mixed according to the specified ratio, and then micronized using a pulverizer such as a sand mill or grinding mill in the presence of auxiliaries and water; alternatively, the dye monomer compounds can be micronized separately using a pulverizer such as a sand mill or grinding mill in the presence of auxiliaries and water, and then mixed in a specified ratio. The disperse yellow to orange dye of the present invention, after being ground using a sand mill or grinding mill, is in liquid form, and after spray drying, it can be in powder or granular form. This is a preparation method known to those skilled in the art.

[0035] The dye compounds of formulas (I) to (IV) used in this invention can be conveniently synthesized in a manner well known to those skilled in the art, or commercially available products can be used. Formulations made using the dye compositions of this invention can be used to dye hydrophobic fiber materials (such as polyester and its blended fabrics) in the manner commonly used in the industry, such as using ordinary immersion dyeing or high temperature and high pressure dyeing. The hydrophobic fiber materials are pretreated, immersed in a dye vat, and after dyeing, washed with cold water until neutral, wrung dry, and then subjected to reduction washing and drying, etc.

[0036] The disperse yellow to orange dye products provided by this invention exhibit excellent light fastness, wash fastness, and sublimation fastness when applied to the dyeing of polyester and its blended fabrics, and can meet the dyeing requirements of automotive interior fabrics. (IV) Detailed Implementation

[0037] 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:

[0038] Example 1:

[0039] Mix 25 grams of the dye shown in formula (I-1), 75 grams of the dye shown in formula (II-5), 245 grams of dispersant MF, and 1950 grams of water, then grind, disperse, and dry to obtain the finished product. This finished product can provide an orange hue for polyester and its blended fabrics.

[0040]

[0041] Example 2:

[0042] Mix 30 grams of the dye shown in formula (I-1), 40 grams of the dye shown in formula (II-6), 30 grams of the dye shown in formula (III-1), 235 grams of dispersing agent CNF, and 2100 grams of water. Grind, disperse, and dry to obtain the finished product. This finished product provides an orange hue to polyester and its blended fabrics.

[0043]

[0044] Examples 3-30

[0045] The method described in Examples 1-2 is different in that the dyes and their weights shown in Components A and B in Table 1 are used, 205 grams of auxiliaries are added (100 grams of dispersant MF and 105 grams of sodium lignosulfonate), 2000 grams of water are added and mixed to form a slurry, which is then ground, dispersed and dried to obtain the finished product. This dye can provide polyester and its blended fabrics with excellent yellow to orange hues.

[0046] Table 1

[0047]

[0048]

[0049] Example 31:

[0050] Mix 30 grams of the dye shown in formula (I-1), 45 grams of the dye shown in formula (II-5), 20 grams of the dye shown in formula (III-1), 5 grams of the dye shown in formula (IV-3), and 256 grams of dispersant MF with 2550 grams of water. Grind, disperse, and dry to obtain the finished product. This finished product provides a red hue for polyester and its blended fabrics.

[0051]

[0052] Staining Example:

[0053] Two grams of each of the disperse yellow to orange dye products prepared in Examples 1-31 were weighed and treated with polyester fabrics using a conventional high-temperature and high-pressure dyeing method. During the treatment, the dyeing depth (owf) was controlled at 2.0%, the liquor ratio at 1:25, the pH of the dye bath at 4-5, and the dyeing was carried out at room temperature. The temperature was increased to 130°C at a rate of 1°C / min and held at that temperature for 60 minutes. The fabrics were then subjected to reduction washing, water washing, and drying according to standard procedures, and then cooled to 70°C before removal. The color fastness of the samples was observed, and the sublimation resistance and water washing fastness were tested using standards ISO 105-P01 and AATCC 61-2A, respectively. The results are listed in Table 2 below.

[0054] Lightfastness test:

[0055] Referring to the method for determining light fastness in GB / T-16422.2-2022, a high-energy xenon lamp was used with an irradiation density of 162 W / m². 2 The blackboard temperature was 89℃±3℃, and the irradiation was carried out for 38 cycles. Each cycle included 3.8 hours of irradiation time and 1 hour of non-irradiation time. The discoloration and fading of the irradiated part were determined with reference to the gray scale of discoloration and fading in JISL-0804. The results are listed in Table 2 below.

[0056] Table 2

[0057]

[0058]

[0059] As shown in the table above, the disperse yellow to orange dye composition prepared by this invention has excellent sublimation resistance and wash fastness when used for printing and dyeing polyester fabrics. Moreover, according to the stringent light fastness test, its fastness can reach the highest level of 5, which can fully meet the printing and dyeing requirements of automotive interior fabrics.

Claims

1. A disperse yellow to orange dye composition comprising component A and component B, wherein component A is at least one of the dye compounds shown in formula (I), and component B is at least one of the dye compounds shown in formula (II) and / or formula (III), wherein, based on said components A and B, the mass percentage content of component A is 5-50%, and the mass percentage content of component B is 50-95%. In formula (I): R 1 It is a C1-C4 alkyl, phenyl, benzyl, C1-C4 alkyl or nitro-substituted benzyl, methoxyethyl, ethoxyethyl, methoxycarbonylethyl; R 2 R 3 Each is independently a C1 to C4 alkyl group, R 4 It is a C1-C4 alkyl or cyanoethyl; In formula (II): R 5 C1-C4 alkyl or C1-C4 alkoxy substituted C1-C4 alkyl, R 6 R is hydrogen or nitro. 7 It is a nitro group, halogen, C1-C4 alkoxy group, -COOC2H4O-Ph, -OCOOCH2-Ph, -OSO2-Ph or -SO2N(CH3)2, wherein Ph is a phenyl group; In formula (Ⅲ): R 8 For H or Br, R 9 It is -CONHC2H5 or -CON(CH3)2.

2. The disperse yellow to orange dye composition according to claim 1, characterized in that, The R mentioned 4 It is cyanoethyl, R 5 It can be methyl or ethyl.

3. The disperse yellow to orange dye composition according to claim 1, characterized in that, Component A is selected from one of the following formulas or a mixture of two or more of them in any proportion:

4. The disperse yellow to orange dye composition according to claim 1, characterized in that, Component B is selected from one of the following formulas or a mixture of two or more of them in any proportion:

5. The disperse yellow to orange dye composition according to claim 1, characterized in that, It consists of component A and component B.

6. The disperse yellow to orange dye composition according to claim 3, characterized in that, Component A is selected from at least one of formulas (I-1) to (I-4).

7. The disperse yellow to orange dye composition according to claim 4, characterized in that, Component B is selected from at least one of formulas (Ⅱ-5) to (Ⅱ-8) and (III-1) to (III-2).

8. A disperse yellow to orange dye product, comprising an auxiliary agent and the disperse yellow to orange dye composition of claim 1, wherein the weight ratio of the two is 0.2 to 5:1, and the auxiliary agent is a dispersant, diffusion agent or other surfactant commonly used in the compounding of disperse dyes.

9. The application of a disperse yellow to orange dye product as described in claim 8 in dyeing polyester and its blended fabrics.

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