A blue to black disperse dye composition and articles thereof

Abstract

The present application discloses a 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 component E of formula (V). The disperse blue to black dye product prepared by the present application has excellent build-up and dye-uptake when dyeing hydrophobic fiber materials, and has excellent fastnesses such as washing fastness, sublimation fastness and rubbing fastness.

Description

TECHNICAL FIELD

[0001] The present application relates to a disperse dye composition and its product, in particular, an environment-friendly blue to black disperse dye composition and dye product suitable for dyeing hydrophobic fiber materials. BACKGROUND

[0002] Polyester is the fastest growing and most widely used synthetic fiber, which is widely used in the field of textile and garment. Disperse dye is the most commonly used dye in the dyeing process of polyester fabric, and its performance has been widely concerned in the industry. Disperse dyes with different structures, or similar parent structures and different substituent groups, have great differences in their performance, especially complex dyes. If not properly selected, the color fastness of dyed fabrics will fluctuate greatly due to factors such as mechanical equipment, dyeing bath ratio, dyeing auxiliaries, process control, etc. It is very difficult for ordinary dyes to achieve high color fastness. In addition, slight fluctuations in process conditions will also cause a series of quality problems such as color difference and color mottle. SUMMARY

[0003] The present application provides a blue to black disperse dye composition, which comprises component A, component B, component C, component D and component E, wherein the component A is selected from at least one of the following formula (I), the component B is selected from at least one of the following formula (II), the component C is selected from at least one of the following formula (III), the component D is selected from at least one of the following formula (IV), and the component E is selected from at least one of the following formula (V), wherein the mass percentage of component A is 1-50%, the mass percentage of component B is 20-85%, the mass percentage of component C is 5-50%, the mass percentage of component D is 2-50%, and the mass percentage of component E is 1-30%:

[0004]

[0005]

[0006] In formula (I), R 1 is halogen, R 2 is hydrogen or halogen, R 3 is hydrogen or -NHCOR 4 , R 4 is C1-C4 alkyl, and R 1 is halogen, R 2 is hydrogen, R 3 is not -NHCOR 4 ;

[0007] In formula (II), R 5 is halogen or cyano, R 6 , R 7each independently C1-C4alkyl, R 8 , R 9 each independently C1-C4alkyl, or C1-C4alkyl substituted by alkenyl, cyano, hydroxy, C1-C4alkoxy, -OCOC6H5, -OC6H5, -C6H5, -COOK 1 , -OCOK 2 , -OCOK 1 , -OCOK 2 each independently C1-C4alkyl;

[0008] in formula (III), R 10 is halogen, R 11 is C1-C4alkyl or amino, R 12 , R 13 each independently C1-C6alkyl or C1-C4alkyl substituted by C1-C4alkoxy;

[0009] in formula (IV), R 14 is C1-C4alkyl or cyanoethyl, R 15 is benzyl or phenethyl;

[0010] in formula (V), R 16 is hydrogen or C1-C4alkoxy, R 17 is hydrogen or NHCOK 3 , K 3 is C1-C4alkyl, D can be one of the following groups of formulae (1) to (3):

[0011]

[0012] wherein X 1 , X 2 each independently halogen.

[0013] The C1-C4alkyl or C1-C6alkyl can be straight-chain or branched alkyl, preferably methyl, ethyl, propyl or butyl. The C1-C4alkoxy can be methoxy, ethoxy, straight-chain or branched propoxy, straight-chain or branched butoxy. Halogen can be fluorine, chlorine, bromine or iodine, preferably chlorine or bromine.

[0014] Preferred compositions according to the application contain a compound of formula (I) in which R 1 , R 2 each independently halogen, more preferably R 1 , R 2 each independently chlorine or bromine.

[0015] Preferred compositions according to the application contain a compound of formula (I) in which R 3 is hydrogen or -NHCOCH3.

[0016] Preferred compounds of formula (II) in the composition according to the application are those wherein R 5 is halogen, more preferred R 5 is chlorine or bromine.

[0017] Preferred compounds of formula (II) in the composition according to the application are those wherein R 6 , R 7 are each independently C1-C4 alkyl, more preferred R 6 , R 7 are each independently methyl or ethyl.

[0018] Preferred compounds of formula (II) in the composition according to the application are those wherein R 8 , R 9 are each independently C1-C4 alkyl, or C1-C4 alkyl substituted by alkenyl, cyano, C1-C4 alkoxy, -COOK 1 , -OCOK 2 , K 1 , K 2 are as defined above, more preferred R 8 , R 9 are each independently ethyl, allyl, and R 5 is chlorine or bromine and R 6 , R 7 are each independently methyl or ethyl.

[0019] Preferred compounds of formula (III) in the composition according to the application are those wherein R 10 is halogen, more preferred R 10 is chlorine or bromine.

[0020] Preferred compounds of formula (III) in the composition according to the application are those wherein R 11 is C1-C4 alkyl or amino, more preferred R 11 is methyl or amino.

[0021] Preferred compounds of formula (III) in the composition according to the application are those wherein R 12 , R 13 are each independently C1-C6 alkyl or C1-C4 alkyl substituted by C1-C4 alkoxy, more preferred R 12 , R 13 are each independently ethyl or propyl, and R 10 is chlorine or bromine and R 11 is methyl or amino.

[0022] Preferred compounds of formula (IV) in the composition according to the application are those wherein R 14 , R 15Each of the following is independently C1-C4 alkyl, cyanoethyl, benzyl, or phenethyl; more preferably, R 14 R 15 Each can be cyano or benzyl.

[0023] In the preferred composition of the present invention, R is a compound of formula (V). 16 It is hydrogen or C1-C4 alkoxy, more preferably, R 16 It is hydrogen or methoxy.

[0024] In the preferred composition of the present invention, R is a compound of formula (V). 17 Hydrogen or NHCOK 3 K 3 As defined above, R is more preferably preferred. 17 It is hydrogen or NHCOCH3, and R 16 It is hydrogen or methoxy.

[0025] The blue to black disperse dye composition provided by this invention may further include dye F as shown in formula (VI):

[0026]

[0027] Among them, R 18 R 19 Each can be independently hydrogen, halogen, cyano, or nitro, R 20 It is hydrogen or C1-C4 alkoxy; R 21 Hydrogen or -NHCOK 4 K 4 It is a C1 to C4 alkyl group, and when R 18 R 19 When both are halogens, R 21 It is not hydrogen.

[0028] In the preferred composition of the present invention, R is a compound of formula (VI). 18 R 19 Each can be independently hydrogen, halogen, cyano, or nitro, with R being more preferred. 18 R 19 Each can be independently composed of hydrogen, chlorine, bromine, cyano, or nitro groups.

[0029] In the preferred composition of the present invention, R is a compound of formula (VI). 20 It is hydrogen or C1-C4 alkoxy, and more preferably, R 20 It is hydrogen or methoxy.

[0030] In the preferred composition of the present invention, R is a compound of formula (VI). 21 For hydrogen or -NHCO K 4 K 4More preferably, R is hydrogen or -NHCOCH3. 21 More preferably, R is hydrogen or -NHCOCH3.

[0031] Particularly preferred, component A of the present application contains at least one dye of formula (I) selected from the following compounds:

[0032]

[0033] Particularly preferred, component B of the present application contains at least one dye of formula (II) selected from the following compounds:

[0034]

[0035]

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

[0037]

[0038]

[0039]

[0040] Particularly preferred, component D of the present application contains at least one dye of formula (IV) selected from the following compounds:

[0041]

[0042]

[0043] Particularly preferred, component E of the present application contains at least one dye of formula (V) selected from the following compounds:

[0044]

[0045]

[0046]

[0047] Particularly preferred, the composition of the present application comprises dyes of formula (I), formula (II), formula (III), formula (IV), formula (V) and formula (VI), wherein the dye component F of formula (VI) is selected from at least one of formulae (VI-1) to (VI-17):

[0048]

[0049]

[0050]

[0051]

[0052] The blue to black disperse dye composition of the present application preferably contains 1 to 45% by mass of the dye of formula (I), 20 to 80% by mass of the dye of formula (II), 5 to 45% by mass of the dye of formula (III), 1 to 45% by mass of the dye of formula (IV), and 1 to 20% by mass of the dye of formula (V), based on the total amount of the dyes.

[0053] The dye of formula (VI) is preferably contained in an amount of 0 to 30% by mass, preferably 0 to 20% by mass, based on the total amount of the dyes.

[0054] The dye compounds (I) to (VI) used in the disperse dye composition of the present application can be synthesized by conventional methods, for example, by using suitable components well known to those skilled in the art and by means of usual diazotization and coupling reactions using the necessary proportions, or by referring to the methods or similar methods described in GB 2123845A and JP 1985015460A.

[0055] The present application also provides a disperse blue to black dye product which mainly contains the disperse blue to black dye composition and an auxiliary agent, the weight ratio of the auxiliary agent to the disperse dye composition being 0.2 to 5: 1. Preferably, the disperse dye product consists of the disperse dye composition and the auxiliary agent. The auxiliary agent is a dispersing agent, a diffusing agent and other surfactants commonly used in the compounding of disperse dyes, and is preferably selected from one or a mixture of two or more thereof in any proportion from the following: naphthalene sulfonic acid formaldehyde condensate, lignin sulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate [e.g., methyl naphthalene sulfonic acid formaldehyde condensate (dispersing agent MF)], naphthalene sulfonic acid formaldehyde condensate (diffusing agent NNO), benzyl naphthalene sulfonic acid formaldehyde condensate (diffusing agent CNF), sodium lignin sulfonate (lignin 85A, lignin 83A), sodium sulfate (sodium sulfate), and the like. Thus, the disperse blue to black dye composition of the present application can be sold as a product as it is, or can be sold or used for coloring textile materials after being added with a conventional auxiliary agent.

[0056] The preparation method of the dispersion dye product is as follows: the dye monomer compounds (primary dyes) constituting the dispersion blue to black dye composition are mixed according to the proportion, and then are micronized by a pulverizer such as a sand mill or a grinding mill in the presence of an auxiliary agent, water or other wetting agent; alternatively, the dye monomer compounds are respectively micronized by a pulverizer such as a sand mill or a grinding mill in the presence of an auxiliary agent, water, and then are mixed according to the proportion. The dispersion blue to black dye product is in a liquid state after being ground by a sand mill or a grinding mill, and can be in a powder or granular shape after being spray dried, which is a preparation method known to those skilled in the art.

[0057] The dispersion dye prepared according to the present application can be used for dyeing by a common dip dyeing method or a padding method. In the common dip dyeing method, for example, a polyester fabric is pretreated, is put into a dyeing vat for dip dyeing, is washed with cold water to neutralization after dyeing, is wrung out, is subjected to reduction cleaning, and is dried; in direct printing, for example, a fabric is subjected to pretreatment before dyeing, is dried, is shaped, is printed with a dispersion dye paste on a printing machine, is subjected to steaming, is fixed by steam, and is finally washed and tenter framed.

[0058] The dispersion blue to black dye product prepared according to the present application has excellent build-up and dye uptake when being used for dyeing a hydrophobic fiber material, and has excellent fastnesses such as washing fastness, sublimation fastness and rubbing fastness, and good color fading performance in water. DETAILED DESCRIPTION

[0059] The present application is further described below in combination with specific examples, but the protection scope of the present application is not limited to this.

[0060] Example 1

[0061] 15 grams of the compound of formula (I-1), 35 grams of the compound of formula (II-3), 20 grams of the compound of formula (III-1), 28 grams of the compound of formula (IV-1), 2 grams of the compound of formula (V-1) and 250 grams of dispersing agent MF are mixed with 650 grams of water, are ground, dispersed and dried to obtain a product, which can provide a black color with excellent fastness properties for polyester and blended fabrics.

[0062]

[0063] Example 2

[0064] 10 grams of the compound of formula (I-1), 35 grams of the compound of formula (II-4), 25 grams of the compound of formula (III-5), 25 grams of the compound of formula (IV-3), 2 grams of the compound of formula (V-9) and 3 grams of the compound of formula (VI-2) and 250 grams of dispersing agent MF are mixed with 650 grams of water, are ground, dispersed and dried to obtain a product, which can provide a black color with excellent fastness properties for polyester and blended fabrics.

[0065]

[0066] Examples 3-29:

[0067] According to the method described in Example 1 or 2, except that the structure and weight of the dyes I-VI in the table are used, 250 grams of auxiliary (200 grams of dispersant MF and 50 grams of sodium lignosulfonate) are added, 800 grams of water are mixed, and then a slurry is prepared, ground and dispersed, dried, and the finished product is prepared. The dyes can provide excellent blue to black color shades for polyester and its blended fabrics in various fastness properties, as shown in Table 1 below:

[0068] Table 1

[0069]

[0070] Comparative Example 1:

[0071] Example 35 of ZL99104177.1 is used as Comparative Example 1:

[0072]

[0073] Dyeing Examples:

[0074] 2 grams of the dispersed dyes prepared in Examples 1-29 and Comparative Example 1 are weighed, respectively, and conventional high-temperature and high-pressure dyeing method and heat setting treatment are used for polyester fabric. During the treatment process, the dyeing depth (o.w.f) is controlled at 6.0%, the bath ratio is 1:20, the pH is adjusted to 4.5 with acetic acid, the temperature is raised to 60°C, and then the temperature is continuously raised to 130°C at a gradient of about 1°C / min, and the dyeing is maintained for 60 minutes. After the temperature is lowered to 80°C, the fabric is placed in 240 milliliters of 80°C reduction cleaning solution for 20 minutes. Finally, the fabric is acid washed in 240 milliliters of 2g / L acetic acid solution at 40°C for 15 minutes, dried, and heat set at 180°C for 30 seconds. The sublimation resistance, wash fastness, and water blistering fastness are measured according to the methods described in ISO 105-P01 and ISO 105-C10, respectively, and the results are shown in Table 2 below:

[0075] Table 2

[0076]

[0077] Dye uptake test:

[0078] According to the method described in the dyeing examples, the dyes prepared in Example 1 and Comparative Example 1 of the present application are used to dye polyester fabric at a temperature range of 70-130°C and a dyeing depth of 2.0%. The dye uptake is tested according to the method described in GB / T 9337, and the results are shown in Table 3:

[0079] Table 3

[0080]

[0081] From the above table, it can be seen that the dye color fastness and dye uptake of the present application are both improved.

Claims

1. A blue to black disperse dye composition comprising component A, component B, component C, component D and component E, said component A is selected from at least one of the following formula (I), said component B is selected from at least one of the following formula (II), said component C is selected from at least one of the following formula (III), said component D is selected from at least one of the following formula (IV), said component E is selected from at least one of the following formula (V), wherein the mass percentage of component A is 1-50%, the mass percentage of component B is 20-85%, the mass percentage of component C is 5-50%, the mass percentage of component D is 2-50%, the mass percentage of component E is 1-30%: ###0001### ###0002### ###0003### ###0004### ###0005### In formula (I), R 1 halogen, R 2 is hydrogen or halogen, R 3 is hydrogen or -NHCOR 4 , R 4 is C1-C4 alkyl, and R 1 is halogen, R 2 is hydrogen, R 3 is not -NHCOR 4 ; In formula (II), R 5 is halogen or cyano, R 6 , R 7 are each independently C1-C4 alkyl, R 8 , R 9 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 (III), R 10 is halogen, R 11 is C1-C4 alkyl or amino, R 12 , R 13 each independently is C1-C6 alkyl or C1-C4 alkyl substituted by C1-C4 alkoxy; In formula (IV), R 14 is C1-C4 alkyl or cyanoethyl, R 15 is benzyl or phenethyl; In formula (V), R 16 is hydrogen or C1-C4alkoxy, R 17 is hydrogen or NHCOK 3 , K 3 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 blue to black disperse dye composition according to claim 1, further comprising a dye F of formula (VI): ###0006### wherein R 18 , R 19 each independently is hydrogen, halogen, cyano or nitro, R 20 is hydrogen or C1-C4 alkoxy; R 21 is hydrogen or -NHCOK 4 wherein K 4 is C1-C4 alkyl, and when R 18 , R 19 are both halogen, R 21 is not hydrogen.

3. The blue to black disperse dye composition according to claim 1, wherein component A contains at least one dye of formula (I) selected from the following compounds: ###0007### 4. The blue to black disperse dye composition according to claim 1, wherein component B contains at least one dye of formula (II) selected from the following compounds: ###0008### 5. The blue to black disperse dye composition according to claim 1, wherein component C contains at least one dye of formula (III) selected from the following compounds: ###0009### 6. The blue to black disperse dye composition according to claim 1, wherein component D contains at least one dye of formula (IV) selected from the following compounds: ###0010### 7. The blue to black disperse dye composition according to claim 2, wherein component E contains at least one dye of formula (V) selected from the following compounds: ###0011### 8. The blue to black disperse dye composition according to claim 1, wherein component F is selected from at least one of the following formula (VI-1) to (VI-17): ###0012### ###0013### ###0014### ###0015### ###0016### ###0017### ###0018### ###0019### ###0020### ###0021### ###0022### 9. A dye product comprising the blue to black disperse dye composition according to claim 1 or claim 2, which mainly contains said blue to black disperse dye composition and an auxiliary, the weight ratio of the auxiliary to the disperse dye composition being 0.2-5:1, said auxiliary being 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, anhydrous sodium sulfate.

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