High temperature blue to black disperse dye compositions and articles thereof

Abstract

The present invention discloses a high-temperature type blue to black disperse dye composition, comprising component A of formula (I), component B of formula (II), component C of formula (III), component D of formula (IV) and / or (V), the high-temperature type disperse blue to black dye product prepared by the present invention has good washing fastness and water bubble fastness when dyeing hydrophobic fiber materials.

Description

Technical Field

[0001] This invention relates to a disperse dye composition and its products, particularly a high-temperature blue to black disperse dye composition and dye products suitable for printing and dyeing hydrophobic fiber materials. Background Technology

[0002] Disperse blue to black dyes are an important type of dye, widely used in textiles, inkjet printing, and other fields. With increasing environmental awareness and growing consumer demand for high-quality, high-performance dyes, high performance and multi-functionality are key development trends for disperse dyes. Disperse dyes need to possess properties such as higher color fastness, a wider dyeing range, better uniformity, and higher vibrancy. In recent years, the industry has raised certain requirements for the water fastness of disperse dyes. Water fastness refers to the ability of disperse dyes to resist washing after being fixed on fabric. Water fastness is one of the important indicators for evaluating the quality of disperse dyes, as it determines the degree of color fading of dyed fabrics during washing. Summary of the Invention

[0003] This invention provides a high-temperature blue to black disperse dye composition comprising component A, component B, component C, and component D. Component A is selected from at least one of formula (I), component B is selected from at least one of formula (II), component C is selected from at least one of formula (III), and component D is selected from at least one of formulas (IV) and / or (V). The mass percentage of component A is 20–80%, the mass percentage of component B is 1–45%, the mass percentage of component C is 1–45%, and the mass percentage of component D is 1–30%.

[0004]

[0005]

[0006] In equation (I), R 1 It is a halogen or cyano group, R 2 R 3 Each is independently a C1 to C4 alkyl group, R 4 R 5 Each group is independently a C1-C4 alkyl group, or may be prefixed with an alkenyl group, cyano group, hydroxyl group, C1-C4 alkoxy group, -OCOC6H5 group, -OC6H5 group, -C6H5 group, or -COOK group. 1 -OCOK 2 Substituted C1-C4 alkyl groups, wherein K 1 K 2 Each is an independent C1 to C4 alkyl group;

[0007] In equation (II), R6 For halogens, R 7 It is a C1-C4 alkyl or amino group, R 8 R 9 Each is independently a C1-C6 alkyl group or a C1-C4 alkyl group substituted with a C1-C4 alkoxy group;

[0008] In equation (III), R 10 R 11 Each can be independently hydrogen, halogen, or nitro, R 12 It is a C1-C4 alkyl or cyanoethyl group, R 13 It is benzyl or phenylethyl, R 14 It is hydrogen or C1-C4 alkyl;

[0009] In equation (IV), R 15 R 16 Each can be independently hydrogen, halogen, cyano, or nitro, R 17 It is hydrogen or C1-C4 alkoxy.

[0010] R 18 Hydrogen or -NHCOK 3 K 3 It is a C1 to C4 alkyl group, and when R 15 R 16 When both are halogens, R 18 Not hydrogen;

[0011] In equation (V), R 19 R is hydrogen or C1-C4 alkoxy. 20 Hydrogen or NHCOK 4 K 4 It is a C1 to C4 alkyl group, and D can be one of the groups in formulas (1) to (3):

[0012]

[0013] Among them, X 1 X 2 Each is an independent halogen.

[0014] The C1-C4 or C1-C6 alkyl group can be a straight-chain or branched alkyl group, preferably methyl, ethyl, propyl, or butyl. The C1-C4 alkoxy group can be methoxy, ethoxy, straight-chain or branched propoxy, or straight-chain or branched butoxy. The halogen can be fluorine, chlorine, bromine, or iodine, preferably chlorine or bromine.

[0015] In the preferred composition of the present invention, R is a compound of formula (I). 1 For halogens, R is more preferably preferred. 1 It is chlorine or bromine.

[0016] In the preferred composition of the present invention, R is a compound of formula (I). 2 R 3 Each is independently a C1 to C4 alkyl group, and more preferably, R 2 R 3 Each can be methyl or ethyl.

[0017] In the preferred composition of the present invention, R is a compound of formula (I). 4 R 5 Each can be independently a C1-C4 alkyl or allyl group, or be modified by a cyano, C1-C4 alkoxy, or -COOK group. 1 -OCOK 2 Substituted C1-C4 alkyl groups, K 1 K 2 As defined above, R is more preferably preferred. 4 R 5 Each is independently ethyl and allyl, and R 5 Chlorine or bromine and R 2 R 3 Each can be methyl or ethyl.

[0018] In the preferred composition of the present invention, R is a compound of formula (II). 6 For halogens, R is more preferably preferred. 6 It is chlorine or bromine.

[0019] In the preferred composition of the present invention, R is a compound of formula (II). 7 It is a C1-C4 alkyl or amino group, and more preferably, R 7 It is methyl or amino.

[0020] In the preferred composition of the present invention, R is a compound of formula (II). 8 R 9 Each alkyl group is independently a C1-C6 alkyl group or a C1-C4 alkyl group substituted with a C1-C4 alkoxy group. More preferably, R 8 R 9 Each is independently ethyl or propyl, and R 6 Chlorine or bromine and R 7 It is methyl or amino.

[0021] In the preferred composition of the present invention, R is a compound of formula (III). 10 R 11 Each can be independently hydrogen, halogen, or nitro, with R being more preferably... 10 R 11 Each is hydrogen on its own.

[0022] In the preferred composition of the present invention, R is a compound of formula (III). 12It is either ethyl or cyanoethyl.

[0023] In the preferred composition of the present invention, R is a compound of formula (III). 14 It is hydrogen or C1-C4 alkyl, more preferably, R 14 It is hydrogen or methyl, and R 10 R 11 Each is independently hydrogen and R 12 R 13 Each is independently cyanoethyl and benzyl.

[0024] In the preferred composition of the present invention, R is a compound of formula (IV). 15 R 16 Each can be independently hydrogen, halogen, cyano, or nitro, with R being more preferred. 15 R 16 Each can be independently composed of hydrogen, chlorine, bromine, cyano, or nitro groups.

[0025] In the preferred composition of the present invention, R is a compound of formula (IV). 17 It is hydrogen or C1-C4 alkoxy, and more preferably, R 17 It is hydrogen or methoxy.

[0026] In the preferred composition of the present invention, R is a compound of formula (IV). 18 Hydrogen or -NHCOK 3 K 3 As defined above, R is more preferably preferred. 18 It is hydrogen or -NHCOCH3, and R 15 R 16 Each can be independently composed of hydrogen, chlorine, bromine, cyano or nitro groups, and R. 17 It is hydrogen or methoxy.

[0027] In the preferred composition of the present invention, R is a compound of formula (V). 19 It is hydrogen or C1-C4 alkoxy, more preferably, R 19 It is hydrogen or methoxy.

[0028] In the preferred composition of the present invention, R is a compound of formula (V). 20 Hydrogen or NHCOK 4 K 4 As defined above, R is more preferably preferred. 20 It is hydrogen or NHCOCH3, and R 19 It is hydrogen or methoxy.

[0029] Particularly preferred, component A of the present invention contains at least one dye of formula (I) selected from the following compounds:

[0030]

[0031]

[0032] Particularly preferred, component B of the present invention contains at least one dye of formula (II) selected from the following compounds:

[0033]

[0034]

[0035]

[0036] Particularly preferred, component C of the present invention contains at least one dye of formula (III) selected from the following compounds:

[0037]

[0038]

[0039] Particularly preferred, component D of the present invention contains at least one dye of formula (IV) and / or (V) selected from the following compounds:

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046] Based on the total amount of dye, the high-temperature blue to black disperse dye composition of the present invention preferably contains 20-75% by mass of dye of formula (I), 1-40% by mass of dye of formula (II), 1-40% by mass of dye of formula (III), and 1-25% by mass of dye of formula (IV) and / or formula (V).

[0047] The disperse dye compositions of the present invention, wherein the dye compounds (I) to (V) used can be synthesized by conventional methods, such as by using suitable components known to those skilled in the art and using the necessary proportions by means of conventional diazotization and coupling reactions, or by referring to the method or similar method in patent US3573273A.

[0048] This invention also provides a high-temperature disperse blue to black dye product, which mainly contains the aforementioned high-temperature disperse blue to black dye composition and auxiliaries, with the weight ratio of auxiliaries to disperse dye composition being 0.2 to 5:1. Preferably, the disperse dye product is composed of the aforementioned disperse dye composition and auxiliaries. The auxiliaries are dispersants, diffusion agents, and other surfactants commonly used in disperse dye compounding, preferably from one or a mixture of two or more of the following in any proportion: 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. Therefore, the disperse blue to black dye composition of this invention can be sold directly as a commercial product, or it can be sold as a commercial product or used for coloring textile materials after adding conventional auxiliaries.

[0049] The preparation method of the disperse dye product of the present invention is as follows: The dye monomer compounds (original dyes) constituting the high-temperature disperse blue to black dye composition are mixed according to a specified ratio, and then micronized using a pulverizer such as a sand mill or grinding mill in the presence of auxiliaries, water, or other wetting agents; alternatively, each dye monomer compound 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 blue to black dye product of the present invention, after being ground with 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.

[0050] The disperse dyes prepared according to the present invention can be used for dyeing by ordinary immersion dyeing and pad dyeing. Ordinary immersion dyeing involves pretreating the polyester fabric, immersing it in a dye vat, washing it with cold water until neutral, wringing it out, performing reduction washing, and drying it. Direct printing involves pretreating the fabric, drying it, setting it, printing the disperse dye paste on a printing machine, steaming it to fix the dye on the fabric, washing it with water, and then stretching and setting it.

[0051] The high-temperature disperse blue to black dye products prepared using this invention exhibit excellent lifting power and dyeing rate when dyeing hydrophobic fiber materials, while also demonstrating excellent fastness properties, especially wash fastness. Detailed Implementation

[0052] 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.

[0053] Example 1

[0054] 33g of compound (I-4), 27g of compound (II-5), 30g of compound (III-3), 10g of compound (IV-1) and 250g of dispersant MF are mixed with 1000g of water, ground, dispersed and dried to obtain the finished product. This dye can provide polyester and its blended fabrics with excellent fastness properties.

[0055]

[0056] Example 2:

[0057] 50 grams of compound (I-3), 25 grams of compound (II-6), 20 grams of compound (III-3), 5 grams of compound (V-5), and 200 grams of sodium lignosulfonate are mixed with 1200 grams of water, ground, dispersed, and dried to obtain the finished product. This dye can provide polyester and its blended fabrics with excellent fastness properties of blue.

[0058]

[0059]

[0060] Examples 3-30:

[0061] The method described in Example 1 or 2 is different in that the structures and weights of dyes I to V in the table are used. 250 grams of auxiliaries (200 grams of dispersant MF and 50 grams of sodium lignosulfonate) are added, and 1600 grams of water are added to form a slurry. This slurry is then ground, dispersed, and dried to obtain the finished product. This dye can provide polyester and its blended fabrics with excellent fastness properties ranging from blue to black, as shown in Table 1 below.

[0062] Table 1

[0063]

[0064]

[0065] Comparative Example 1:

[0066] Example 35 of ZL99104177.1 was used as Comparative Example 1:

[0067]

[0068] Staining Example:

[0069] Two grams of the disperse dyes prepared in Examples 1-30 and Comparative Example 1 were weighed out respectively. Polyester fabric was treated with conventional high-temperature and high-pressure dyeing and heat setting methods. During the treatment, the dyeing depth (owf) was controlled at 6.0%, the liquor ratio at 1:20, the pH was adjusted to 4.5 with acetic acid, the temperature was raised to 60°C, and then gradually increased to 130°C at a rate of approximately 1°C / min. The fabric was then dyed at this temperature for 60 minutes. After cooling to 80°C, the fabric was washed in 240 ml of 80°C reducing cleaning solution for 20 minutes. Finally, it was acid-washed with 240 ml of 2 g / L acetic acid solution at 40°C for 15 minutes, dried, and heat-set at 180°C for 30 seconds. The color fastness to sublimation and perspiration was determined using the methods described in ISO 105-P01 and ISO 105-E04, respectively. The color fastness to immersion was also tested. The results are shown in Table 2 below.

[0070] Table 2

[0071]

[0072]

[0073] As can be seen from the table above, the disperse dyes of the present invention have better color fastness.

Claims

1. A high temperature blue to black disperse dye composition comprising component A selected from at least one of the following formula (I), component B selected from at least one of the following formula (II), component C selected from at least one of the following formula (III), and component D selected from at least one of the following formula (IV) and / or (V), the mass percentage of component A is 20-80%, the mass percentage of component B is 1-45%, the mass percentage of component C is 1-45%, and the mass percentage of component D is 1-30%: ###0001### ###0002### ###0003### ###0004### In formula (I), R 1 is halogen or cyano, R 2 , R 3 are each independently C1-C4 alkyl, R 4 , R 5 are each independently C1-C4 alkyl, or C1-C4 alkyl substituted by alkenyl, cyano, hydroxy, C1-C4 alkoxy, -OCOC6H5, -OC6H5, -C6H5, -COOK 1 , -OCOK 2 , wherein K 1 , K 2 are each independently C1-C4 alkyl; In formula (II), R 6 is halogen, R 7 is C1-C4 alkyl or amino, R 8 , R 9 each independently is C1-C6 alkyl or C1-C4 alkyl substituted by C1-C4 alkoxy; in the formula (III), R 10 , R 11 each independently is hydrogen, halogen or nitro, R 12 is C1-C4 alkyl, cyanoethyl, R 13 is benzyl or phenethyl, R 14 is hydrogen or C1-C4 alkyl; in formula (IV) R 15 , R 16 are each independently hydrogen, halogen, cyano or nitro, R 17 is hydrogen or C1-C4 alkoxy, R 18 is hydrogen or -NHCOK 3 , wherein K 3 is C1-C4 alkyl, and when R 15 , R 16 are both halogen, R 18 is not hydrogen; In formula (V), R 19 is hydrogen or C1-C4alkoxy, R 20 is hydrogen or NHCOK 4 , K 4 is C1-C4alkyl, and D is one of the following groups (1) to (3): wherein, X 1 , X 2 each independently is halogen.

2. The high temperature blue to black disperse dye composition according to claim 1, wherein component A comprises at least one dye of formula (I) selected from the following compounds: ###0005### 3. The high temperature blue to black disperse dye composition according to claim 1, wherein component B comprises at least one dye of formula (II) selected from the following compounds: ###0006### 4. The high temperature blue to black disperse dye composition according to claim 1, wherein component C comprises at least one dye of formula (III) selected from the following compounds: ###0007### 5. The high temperature blue to black disperse dye composition according to claim 1, wherein component D comprises at least one dye of formula (IV) and / or (V) selected from the following compounds: ###0008### ###0009### 6. The high temperature blue to black disperse dye composition according to claim 1, wherein the mass percentage of the dye of formula (I) is 20-75%, the mass percentage of the dye of formula (II) is 1-40%, the mass percentage of the dye of formula (III) is 1-40%, and the mass percentage of the dye of formula (IV) and / or (V) is 1-25%, based on the total amount of the dye.

7. A dye preparation comprising the high temperature blue to black disperse dye composition according to claim 1, which mainly comprises the high temperature blue to black dye composition and an auxiliary, the weight ratio of the auxiliary to the high temperature blue to black dye composition is 0.2-5:1, and the auxiliary is selected from one or a mixture of two or more thereof in any ratio: naphthalene sulfonate formaldehyde condensate, lignin sulfonate, alkyl naphthalene sulfonate formaldehyde condensate, and anhydrous sodium sulfate.

8. The use of the dye preparation according to claim 7 for dyeing polyester and its blended fabrics.

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