Blue-to-black disperse dye composition and dye product

Abstract

The invention discloses a blue-to-black disperse dye composition and a dye product. The blue-to-black disperse dye composition comprises a component A, a component B, a component C and a component D. The component A is selected from at least one of compounds shown in a formula (I), the component B is selected from at least one of compounds shown in a formula (II), the component C is selected from at least one of compounds shown in a formula (III), and the component D is selected from at least one of compounds shown in a formula (III). The component D is selected from at least one of compounds shown in a formula (IV). The invention provides a blue-to-black disperse dye product which comprises the blue-to-black disperse dye composition and an auxiliary agent, and the weight ratio of the auxiliary agent to the blue-to-black disperse dye composition is (0.2-5): 1. When the blue-to-black disperse dye product provided by the invention is applied to hydrophobic fiber material dyeing, various color fastnesses such as water soaking resistance, sublimation resistance, friction resistance, soaping resistance and the like are excellent. # imgabs0 #

Description

(I) Technical field

[0001] The invention relates to a blue to black disperse dye composition and a dye product. (II) Background technology

[0002] In recent years, polyester-ammonia blended fabrics have been welcomed by the market due to their good elasticity, wrinkle resistance, skin-friendliness and sweat absorption. At the same time, the cleaning conditions of the blended fabrics are not high, and they can be hand washed, machine washed, or dry cleaned, usually without causing any damage to the fabrics, meeting the needs of sports fabrics and other mid-to-high-end clothing fabrics. At present, the disadvantage of the blended fabrics is that the stability is relatively poor compared to pure polyester fabrics and it is easy to fade. Therefore, higher requirements are put forward for its coloring dyes, among which the blue-black series of disperse dyes are used the most. The color fastness of the blue-black dyes currently used for polyester-ammonia blended fabrics on the market needs to be further improved. (III) Summary of the invention

[0003] The present invention aims to provide a blue to black disperse dye composition and a dye product, which, when used for dyeing hydrophobic fiber materials, has excellent color fastnesses such as resistance to blistering, resistance to sublimation, resistance to friction, resistance to soaping, etc.

[0004] In order to achieve the above-mentioned invention object, the technical solution adopted by the present invention is:

[0005] The invention provides a blue to black disperse dye composition, comprising component A, component B, component C and component D, wherein the selected component A is selected from at least one of the compounds represented by formula (I), the component B is selected from at least one of the compounds represented by formula (II), the component C is selected from at least one of the compounds represented by formula (III), and the component D is selected from at least one of the compounds represented by formula (IV). In the composition, the mass percentage of component A is 5-90%, the mass percentage of component B is 5-90%, the mass percentage of component C is 1-60%, and the mass percentage of component D is 1-60%.

[0006]

[0007]

[0008] In formula (I):

[0009] R 1 is hydrogen or C1-C4 alkoxy, preferably methoxy;

[0010] R 2 is a C1-C4 alkyl group, preferably a methyl group;

[0011] R 3 is a C1-C4 alkyl group, preferably a methyl group or an ethyl group;

[0012] m is 1 or 2;

[0013] In formula (II):

[0014] R 4 is hydrogen, cyano, chlorine or bromine;

[0015] R 5 is nitro or cyano;

[0016] R 6 , R 7 Each is independently C1-C4 alkyl, preferably methyl R 8 is a C1-C4 alkyl group, preferably a methyl group or an ethyl group;

[0017] n is 1 or 2;

[0018] In formula (III):

[0019] D 1 A group selected from the following formulae (1) to (6);

[0020]

[0021] X 1 For chlorine and bromine;

[0022] X 2 For chlorine and bromine;

[0023] X 3 is chlorine, bromine or cyano;

[0024] X 4 is hydrogen, chlorine, bromine, nitro or cyano;

[0025] X 5 , X 6 are each independently chlorine or bromine, and X 5 , X 6 In the 5th, 6th or 6th, 7th position;

[0026] R 9 is a C1-C4 alkyl group, preferably a methyl group;

[0027] R 10 is a C1-C4 alkyl group, preferably a methyl group or an ethyl group;

[0028] p is 1 or 2;

[0029] In formula (IV):

[0030] R 11 C1~C8 alkyl or -(CH2) q -Ph, wherein q is 1 or 2, Ph is phenyl, preferably methyl, ethyl, benzyl;

[0031] R12 , R 13 Each is independently hydrogen, halogen, nitro, C1-C4 alkoxy, -COOC2H4OC2H4OCH3, -OSO2-Ph, -OCH2-Ph or -SO2NHK 1 , where Ph is phenyl, K 1 C1~C 18 Alkyl, preferably R 12 , R 13 Each is independently hydrogen, nitro, methoxy or -OSO2-Ph.

[0032] The blue to black disperse dye composition of the present invention may further comprise component E, wherein the component E is selected from at least one of the compounds represented by formula (V), formula (VI) and formula (VII), wherein the mass percentage of component A is 5 to 90%, the mass percentage of component B is 5 to 90%, the mass percentage of component C is 1 to 60%, the mass percentage of component D is 1 to 60%, and the mass percentage of component E is 1 to 40%;

[0033]

[0034] In formula (V) to formula (VII):

[0035] R 14 is hydrogen or C1-C4 alkoxy, preferably methoxy;

[0036] R 15 , R 20 , R 21 , R 24 Each is independently a C1-C4 alkyl group, preferably a methyl group;

[0037] R 16 With R 17 At the same time -CH2CH2CN or -(CH2) a COOK 2 , where a is 1 or 2, K 2 is C1-C4 alkyl, preferably R 16 With R 17 Simultaneously -CH2CH2CN, -CH2COOCH3, -CH2COOCH2CH3 or -CH2CH2COOCH3;

[0038] R 18 is hydrogen, cyano, chlorine or bromine;

[0039] R 19 is nitro or cyano;

[0040] R 22 With R 23At the same time -CH2CH2CN or -(CH2) b COOK 3 , where b is 1 or 2, K 3 is C1-C4 alkyl, preferably R 22 With R 23 Simultaneously -CH2CH2CN, -CH2COOCH3, -CH2COOCH2CH3 or -CH2CH2COOCH3;

[0041] D 2 With the above D 1 The definition is the same as;

[0042] R 25 With R 26 At the same time -CH2CH2CN or -(CH2) c COOK 4 , where c is 1 or 2, K 4 is C1-C4 alkyl, preferably R 25 With R 26 At the same time, it is -CH2CH2CN, -CH2COOCH3, -CH2COOCH2CH3 or -CH2CH2COOCH3.

[0043] Furthermore, the component A is preferably selected from one of the following formulae or a mixture of two or more thereof:

[0044]

[0045]

[0046] Furthermore, component A is preferably at least one of formula (I-1) to formula (I-3). Further, component B is preferably one of the following formulae or a mixture of two or more thereof:

[0047]

[0048]

[0049]

[0050]

[0051] Furthermore, component B is preferably at least one of formula (II-1) to formula (II-15). Furthermore, component C is preferably one of the following formulae or a mixture of two or more thereof:

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] Furthermore, component C is preferably at least one of formula (III-1) to formula (III-15). Furthermore, component D is preferably one of the following formulae or a mixture of two or more thereof:

[0058]

[0059]

[0060]

[0061] Furthermore, component D is preferably at least one of formula (IV-1) to formula (IV-6). Further, component E is preferably one of the following formulae or a mixture of two or more thereof:

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075] Furthermore, component E is preferably at least one of formula (V-1) to formula (V-4), formula (VI-1) to formula (VI-8), and formula (VII-1) to formula (VII-20).

[0076] Preferably, the blue to black disperse dye composition of the present invention comprises component A, component B, component C and component D, wherein the mass percentage of component A is 10-75%, the mass percentage of component B is 10-75%, the mass percentage of component C is 5-50%, and the mass percentage of component D is 5-50%.

[0077] Preferably, the blue to black disperse dye composition of the present invention comprises component A, component B, component C, component D and component E, wherein the mass percentage of component A is 10-75%, the mass percentage of component B is 10-75%, the mass percentage of component C is 5-50%, the mass percentage of component D is 5-50%, and the mass percentage of component E is 1-30%.

[0078] As further preferred, the blue to black disperse dye composition of the present invention consists of component A, component B, component C and component D, wherein the mass percentage of component A is 10-75%, the mass percentage of component B is 10-75%, the mass percentage of component C is 5-50%, and the mass percentage of component D is 5-50%.

[0079] As further preferred, the blue to black disperse dye composition of the present invention consists of component A, component B, component C, component D and component E, wherein the mass percentage of component A is 10-75%, the mass percentage of component B is 10-75%, the mass percentage of component C is 5-50%, the mass percentage of component D is 5-50%, and the mass percentage of component E is 1-30%.

[0080] A particularly preferred scheme 1 of the present invention is: the blue to black disperse dye composition comprises component A, component B, component C and component D, wherein:

[0081] Component A is selected from at least one of formula (I-1) to formula (I-3),

[0082] Component B is selected from at least one of formula (II-1) to formula (II-15),

[0083] Component C is selected from at least one of formula (III-1) to formula (III-15),

[0084] Component D is selected from at least one of formula (IV-1) to formula (IV-6),

[0085] In the composition, the mass percentage of component A is 10-75%, the mass percentage of component B is 10-75%, the mass percentage of component C is 5-50%, and the mass percentage of component D is 5-50%.

[0086] A particularly preferred scheme 2 of the present invention is: the blue to black disperse dye composition comprises component A, component B, component C, component D and component E, wherein:

[0087] Component A is selected from at least one of formula (I-1) to formula (I-3),

[0088] Component B is selected from at least one of formula (II-1) to formula (II-15),

[0089] Component C is selected from at least one of formula (III-1) to formula (III-15),

[0090] Component D is selected from at least one of formula (IV-1) to formula (IV-6),

[0091] Component E is selected from at least one of formula (V-1) to formula (V-4), formula (VI-1) to formula (VI-8), and formula (VII-1) to formula (VII-20),

[0092] In the composition, the mass percentage of component A is 10-75%, the mass percentage of component B is 10-75%, the mass percentage of component C is 5-50%, the mass percentage of component D is 5-50%, and the mass percentage of component E is 1-30%.

[0093] A particularly preferred scheme 3 of the present invention is: the blue to black disperse dye composition is composed of component A, component B, component C and component D, wherein:

[0094] Component A is selected from at least one of formula (I-1) to formula (I-3),

[0095] Component B is selected from at least one of formula (II-1) to formula (II-15),

[0096] Component C is selected from at least one of formula (III-1) to formula (III-15),

[0097] Component D is selected from at least one of formula (IV-1) to formula (IV-6),

[0098] In the composition, the mass percentage of component A is 10-75%, the mass percentage of component B is 10-75%, the mass percentage of component C is 5-50%, and the mass percentage of component D is 5-50%.

[0099] A particularly preferred scheme 4 of the present invention is: the blue to black disperse dye composition is composed of component A, component B, component C, component D and component E, wherein:

[0100] Component A is selected from at least one of formula (I-1) to formula (I-3),

[0101] Component B is selected from at least one of formula (II-1) to formula (II-15),

[0102] Component C is selected from at least one of formula (III-1) to formula (III-15),

[0103] Component D is selected from at least one of formula (IV-1) to formula (IV-6),

[0104] Component E is selected from at least one of formula (V-1) to formula (V-4), formula (VI-1) to formula (VI-8), and formula (VII-1) to formula (VII-20),

[0105] The mass percentage of component A is 10-75%, the mass percentage of component B is 10-75%, the mass percentage of component C is 5-50%, the mass percentage of component D is 5-50%, and the mass percentage of component E is 1-30%.

[0106] When the blue to black disperse dye composition of the present invention is sold as a commodity or used for coloring textile materials, it is usually necessary to add an auxiliary agent for post-treatment.

[0107] Therefore, the present invention also provides a blue to black disperse dye product, which includes the blue to black disperse dye composition and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the blue to black disperse dye composition is 0.2 to 5:1. Preferably, the dye product is composed of the auxiliary agent and the blue to black disperse dye composition. The auxiliary agent is a dispersant, a diffusant and other surfactants commonly used in disperse dye compounding, preferably one of the following or a mixture of two or more thereof: lignin sulfonate (such as sodium lignin sulfonate (lignin 85A, lignin 83A)), alkylnaphthalenesulfonic acid formaldehyde condensate (such as methylnaphthalenesulfonic acid formaldehyde condensate (dispersant MF)), naphthalenesulfonic acid formaldehyde condensate (diffuser NNO), benzylnaphthalenesulfonic acid formaldehyde condensate (diffuser CNF), sodium sulfate, etc.

[0108] The preparation method of the blue to black disperse dye product of the present invention is as follows:

[0109] The dye monomer compounds (original dyes, dye filter cakes) corresponding to the above components are mixed according to a ratio, and then micronized with a pulverizer such as a sand mill or a grinder in the presence of an auxiliary agent and water; in addition, the above dye monomer compounds can also be micronized with a pulverizer such as a sand mill or a grinder in the presence of an auxiliary agent and water, and then mixed according to a ratio. The blue to black disperse dye product of the present invention is liquid after grinding with a sand mill or a grinder, and can be powdery or granular after spray drying, which is a preparation method well known to those skilled in the art.

[0110] In the present invention, the dye compounds represented by formula (I) to (VII) can be conveniently synthesized by diazotization and coupling methods well known to those skilled in the art, or commercially available products can be used.

[0111] The dye product made by the dye composition of the present invention can be used to dye hydrophobic fiber materials (such as polyester and its blended interwoven fabrics) in the usual way in the industry, such as dyeing by ordinary exhaust dyeing method or high temperature and high pressure dyeing method, and can also be used for direct printing. Among them, the ordinary exhaust dyeing method is such as pre-treating the hydrophobic fiber material, putting it into the dyeing tank for exhaust dyeing, washing it with cold water to neutrality after dyeing, wringing it, and then performing reduction washing and drying; direct printing is such as pre-treating the fabric, drying, shaping it, printing disperse dye paste on the printing machine, and then steaming it, using steaming to fix the dye on the fabric, and finally washing it with water and stretching it for shaping.

[0112] Compared with the prior art, the beneficial effects of the present invention are that the blue to black disperse dye composition and dye product provided by the present invention, when used for dyeing hydrophobic fiber materials, have excellent color fastness such as resistance to blistering, resistance to sublimation, resistance to friction, resistance to soaping, etc. (IV) Specific implementation methods

[0113] The present invention is further described below in conjunction with specific embodiments, but the protection scope of the present invention is not limited thereto:

[0114] Embodiment 1:

[0115] 15 g of component A of the compound of formula (Ⅰ-1), 46 g of component B of the compound of formula (Ⅱ-1), 12 g of component C of the compound of formula (Ⅲ-1), 27 g of component D of the compound of formula (Ⅳ-1) and 150 g of dispersant MF are mixed with 650 g of water, ground, dispersed and dried to obtain the finished product. The dye can provide black color with excellent fastness properties to polyester and its blended fabrics.

[0116]

[0117] Embodiment 2:

[0118] 15 g of component A of the compound of formula (Ⅰ-2), 72 g of component B of the compound of formula (Ⅱ-2), 8 g of component C of the compound of formula (Ⅲ-1), 5 g of component D of the compound of formula (Ⅳ-2) and 150 g of dispersant MF are mixed with 650 g of water, ground, dispersed and dried to obtain the finished product. The dye can provide a navy blue color with excellent fastness properties to polyester and its blended fabrics.

[0119]

[0120]

[0121] Embodiment 3:

[0122] 33 grams of component A of the compound of formula (Ⅰ-1), 31 grams of component B of the compound of formula (Ⅱ-1), 15 grams of component C of the compound of formula (Ⅲ-1), 16 grams of component D of the compound of formula (Ⅳ-5), 5 grams of component E of the compound of formula (Ⅵ-2) and 140 grams of dispersant MF are mixed with 650 grams of water, ground, dispersed and dried to obtain the finished product. The dye can provide polyester and its blended fabrics with excellent black color fastness properties.

[0123]

[0124]

[0125] Embodiments 4 to 60:

[0126] According to the method described in Examples 1 to 3, except that the structures and masses of components A to E in Table 1 are used, 200 grams of auxiliary agents (150 grams of dispersant MF and 50 grams of sodium lignin sulfonate) are added, 650 grams of water are added and mixed to form a slurry, which is ground, dispersed, and dried to obtain a finished product. The dye can provide polyester and its blended fabrics with excellent fastness properties in blue to black.

[0127] Table 1

[0128]

[0129]

[0130]

[0131] Dyeing Example:

[0132] 2 g of disperse blue to black dyes prepared in Examples 1 to 60 were weighed respectively, and polyester-spandex knitted fabrics were treated by conventional high temperature and high pressure dyeing and heat setting. During the treatment process, the dyeing depth (owf) was controlled to be 4.0%, the bath ratio was 1:40, the pH value of the dye bath was adjusted to 4-5, dyeing was carried out at room temperature, the temperature was raised to 130°C at 1°C / min, and the dyeing was carried out by keeping the temperature for 30min. The conventional method was used for washing, reduction cleaning (2 g / L caustic soda, 3 g / L hydrosulfite, 85°C x 20min), acid washing and neutralization (2 g / L acetic acid, 40°C x 15min), washing and drying, and heat setting at 180°C for 30 seconds to obtain blue to black dyed fabrics. The fastness to rubbing (refer to ISO105-X12), fastness to blistering [2g of blue to black dyed fabric was soaked in 95℃ (5g / L washing powder) for 15min, with a bath ratio of 1:50, and its fastness to blistering was evaluated], fastness to sublimation (refer to ISO105-P01), and fastness to washing (refer to ISO105-C10). The results are shown in Table 2 below.

[0133] Table 2

[0134]

[0135]

[0136]

[0137] It can be seen from the above table that the disperse blue to black dye composition and the dye product thereof in the present invention have excellent fastness properties and can meet the printing and dyeing of fabrics with high fastness requirements.

Claims

1. A blue to black disperse dye composition, characterized in that: The blue to black disperse dye composition comprises component A, component B, component C and component D, wherein the selected component A is selected from at least one of the compounds represented by formula (I), the component B is selected from at least one of the compounds represented by formula (II), the component C is selected from at least one of the compounds represented by formula (III), and the component D is selected from at least one of the compounds represented by formula (IV). In the composition, the mass percentage of component A is 5-90%, the mass percentage of component B is 5-90%, the mass percentage of component C is 1-60%, and the mass percentage of component D is 1-60%; In formula (I): R 1 is hydrogen or C1-C4 alkoxy, preferably methoxy; R 2 is a C1-C4 alkyl group, preferably a methyl group; R 3 is a C1-C4 alkyl group, preferably a methyl group or an ethyl group; m is 1 or 2; In formula (II): R 4 is hydrogen, cyano, chlorine or bromine; R 5 is nitro or cyano; R 6 , R 7 Each is independently C1-C4 alkyl, preferably methyl R 8 is a C1-C4 alkyl group, preferably a methyl group or an ethyl group; n is 1 or 2; In formula (III): D 1 A group selected from the following formulae (1) to (6); X 1 For chlorine and bromine; X 2 For chlorine and bromine; X 3 is chlorine, bromine or cyano; X 4 is hydrogen, chlorine, bromine, nitro or cyano; X 5 , X 6 are each independently chlorine or bromine, and X 5 , X 6 In the 5th, 6th or 6th, 7th position; R 9 is a C1-C4 alkyl group, preferably a methyl group; R 10 is a C1-C4 alkyl group, preferably a methyl group or an ethyl group; p is 1 or 2; In formula (IV): R 11 C1~C8 alkyl or -(CH2) q -Ph, wherein q is 1 or 2, Ph is phenyl, preferably methyl, ethyl, benzyl; R 12 , R 13 Each is independently hydrogen, halogen, nitro, C1-C4 alkoxy, -COOC2H4OC2H4OCH3, -OSO2-Ph, -OCH2-Ph or -SO2NHK 1 , where Ph is phenyl, K 1 C1~C 18 Alkyl, preferably R 12 , R 13 Each is independently hydrogen, nitro, methoxy or -OSO2-Ph.

2. The blue to black disperse dye composition as claimed in claim 1, characterized in that: The blue to black disperse dye composition consists of component A, component B, component C and component D.

3. The blue to black disperse dye composition as claimed in claim 1, characterized in that: The blue to black disperse dye composition further comprises component E, wherein component E is selected from at least one of the compounds represented by formula (V), formula (VI) and formula (VII), and in the composition, the mass percentage of component A is 5-90%, the mass percentage of component B is 5-90%, the mass percentage of component C is 1-60%, the mass percentage of component D is 1-60%, and the mass percentage of component E is 1-40%; In formula (V) to formula (VII): R 14 is hydrogen or C1-C4 alkoxy, preferably methoxy; R 15 , R 20 , R 21 , R 24 Each is independently a C1-C4 alkyl group, preferably a methyl group; R 16 With R 17 At the same time -CH2CH2CN or -(CH2) a COOK 2 , where a is 1 or 2, K 2 is C1-C4 alkyl, preferably R 16 With R 17 Simultaneously -CH2CH2CN, -CH2COOCH3, -CH2COOCH2CH3 or -CH2CH2COOCH3; R 18 is hydrogen, cyano, chlorine or bromine; R 19 is nitro or cyano; R 22 With R 23 At the same time -CH2CH2CN or -(CH2) b COOK 3 , where b is 1 or 2, K 3 is C1-C4 alkyl, preferably R 22 With R 23 Simultaneously -CH2CH2CN, -CH2COOCH3, -CH2COOCH2CH3 or -CH2CH2COOCH3; D 2 With the above D 1 The definition is the same as; R 25 With R 26 At the same time -CH2CH2CN or -(CH2) c COOK 4 , where c is 1 or 2, K 4 is C1-C4 alkyl, preferably R 25 With R 26 At the same time, it is -CH2CH2CN, -CH2COOCH3, -CH2COOCH2CH3 or -CH2CH2COOCH3.

4. The blue to black disperse dye composition as claimed in claim 3, characterized in that: The blue to black disperse dye composition consists of component A, component B, component C, component D and component E.

5. A blue to black disperse dye composition as claimed in any one of claims 1 to 4, characterized in that: The component A is selected from one of the following formulae or a mixture of two or more thereof:

6. A blue to black disperse dye composition as claimed in any one of claims 1 to 4, characterized in that: The component B is selected from one of the following formulae or a mixture of two or more thereof:

7. A blue to black disperse dye composition as claimed in any one of claims 1 to 4, characterized in that: The component C is selected from one of the following formulae or a mixture of two or more thereof:

8. A blue to black disperse dye composition as claimed in any one of claims 1 to 4, characterized in that: The component D is selected from one of the following formulae or a mixture of two or more thereof:

9. The blue to black disperse dye composition as claimed in claim 3 or 4, characterized in that: The component E is selected from one of the following formulae or a mixture of two or more thereof:

10. The blue to black disperse dye composition according to claim 1 or 2, characterized in that: In the blue to black disperse dye composition: Component A is selected from at least one of formula (I-1) to formula (I-3), Component B is selected from at least one of formula (II-1) to formula (II-15), Component C is selected from at least one of formula (III-1) to formula (III-15), Component D is selected from at least one of formula (IV-1) to formula (IV-6), In the composition, the mass percentage of component A is 10-75%, the mass percentage of component B is 10-75%, the mass percentage of component C is 5-50%, and the mass percentage of component D is 5-50%; 11. The blue to black disperse dye composition according to claim 3 or 4, characterized in that: In the blue to black disperse dye composition: Component A is selected from at least one of formula (I-1) to formula (I-3), Component B is selected from at least one of formula (II-1) to formula (II-15), Component C is selected from at least one of formula (III-1) to formula (III-15), Component D is selected from at least one of formula (IV-1) to formula (IV-6), Component E is selected from at least one of formula (V-1) to formula (V-4), formula (VI-1) to formula (VI-8), and formula (VII-1) to formula (VII-20), In the composition, the mass percentage of component A is 10-75%, the mass percentage of component B is 10-75%, the mass percentage of component C is 5-50%, the mass percentage of component D is 5-50%, and the mass percentage of component E is 1-30%; 12. A blue to black disperse dye product, characterized in that: The blue to black disperse dye product comprises the blue to black disperse dye composition according to any one of claims 1 to 11 and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the blue to black disperse dye composition is 0.2 to 5:1.

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