A dark colour disperse dye composition and dyeing articles thereof

Abstract

The present invention provides a dark color disperse dye comprising component A of formula (I), component B of formula (II) and component C of formula (III). The dark color disperse dye product prepared by the present invention has excellent fastness to perspiration and blistering when dyeing hydrophobic fiber materials.

Description

TECHNICAL FIELD

[0001] The present application relates to a disperse dye composition and its products, in particular, an environmentally friendly dark disperse dye composition and dye products suitable for printing and dyeing hydrophobic fiber materials. BACKGROUND

[0002] Dark disperse dyes play an important role in the dye industry, especially in recent years, with the increasing demand for high-quality and high-performance dyes and the increasing demand for environmental protection, environmental protection and sustainable development are important development directions of dark disperse dyes. In order to meet the increasingly stringent environmental protection requirements, researchers are constantly optimizing the dyeing process and formula, such as improving color fastness, expanding dyeing range, improving uniformity and brightness, etc. With the rapid development of domestic textile, leather, papermaking, plastic and other industries, the demand for dark disperse dyes will continue to grow, especially the increasing proportion of polyester fibers in the textile market will further promote the expansion of the dark disperse dye market. SUMMARY

[0003] The present application provides a dark disperse dye composition, comprising component A, component B and component C, 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), and the component C is selected from at least one of the following formula (III), wherein the mass percentage of component A is 1-50%, the mass percentage of component B is 20-85%, and the mass percentage of component C is 1-50%:

[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 7 each independently is C1-C4 alkyl, R 8 , R 9each independently C1-C4 alkyl, or C1-C4 alkyl substituted by alkenyl, cyano, hydroxy, C1-C4 alkoxy, -OCOC6H5, -OC6H5, -C6H5, -COOK 1 , -OCOK 2 , -OCOK 1 , -OCOK 2 each independently C1-C4 alkyl;

[0008] In formula (III), R 10 is halogen, R 11 is C1-C4 alkyl or amino, R 12 , R 13 each independently C1-C6 alkyl or C1-C4 alkyl substituted by C1-C4 alkoxy.

[0009] The C1-C4 alkyl or C1-C6 alkyl can be straight-chain or branched alkyl, preferably methyl, ethyl, propyl or butyl. The C1-C4 alkoxy can be methoxy, ethoxy, straight-chain or branched propoxy, straight-chain or branched butoxy. The halogen can be fluorine, chlorine, bromine or iodine, preferably chlorine or bromine.

[0010] 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.

[0011] Preferred compositions according to the application contain a compound of formula (I) in which R 3 is hydrogen or -NHCOCH3.

[0012] Preferred compositions according to the application contain a compound of formula (II) in which R 5 is halogen, more preferably R 5 is chlorine or bromine.

[0013] Preferred compositions according to the application contain a compound of formula (II) in which R 6 , R 7 each independently C1-C4 alkyl, more preferably R 6 , R 7 each independently methyl or ethyl.

[0014] Preferred compositions according to the application contain a compound of formula (II) in which R 8 , R 9 each independently C1-C4 alkyl, or C1-C4 alkyl substituted by alkenyl, cyano, C1-C4 alkoxy, -COOK 1 , -OCOK 2 , -OCOKsubstituted C1-C4alkyl, K 1 , K 2 More preferably, 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.

[0015] More preferably, R 10 is halogen, and R 10 is chlorine or bromine.

[0016] More preferably, R 11 is C1-C4alkyl or amino, and R 11 is methyl or amino.

[0017] More preferably, R 12 , R 13 are each independently C1-C6alkyl or C1-C4alkyl substituted by C1-C4alkoxy, and R 12 , R 13 are each independently ethyl or propyl, and R 10 is chlorine or bromine and R 11 is methyl or amino.

[0018] In particular, component A of the present application comprises at least one dye of the formula (I) selected from the following compounds:

[0019]

[0020] In particular, component B of the present application comprises at least one dye of the formula (II) selected from the following compounds:

[0021]

[0022]

[0023]

[0024]

[0025] In particular, component C of the present application comprises at least one dye of the formula (III) selected from the following compounds:

[0026]

[0027]

[0028]

[0029] The dark color disperse dye composition according to the present application can further comprise a dye D represented by Formula (IV) and / or Formula (V):

[0030]

[0031] In Formula (IV), R 14 , R 15 are each independently hydrogen, halogen or nitro, R 16 , R 17 are each independently C1-C4 alkyl, cyanoethyl, benzyl or phenethyl, R 18 is hydrogen or C1-C4 alkyl;

[0032] In Formula (V), R 19 , R 20 are each independently hydrogen, halogen, cyano or nitro, R 21 is hydrogen or C1-C4 alkoxy,

[0033] R 22 is hydrogen or -NHCOR 23 wherein R 23 is C1-C4 alkyl, and when R 19 , R 20 are both halogen, R 22 is not hydrogen.

[0034] The preferred composition according to the present application contains a compound of Formula (IV) wherein R 16 , R 17 are each independently C1-C4 alkyl, cyanoethyl, benzyl or phenethyl, more preferably R 16 , R 17 are each independently cyano or benzyl.

[0035] The preferred composition according to the present application contains a compound of Formula (IV) wherein R 18 is hydrogen or C1-C4 alkyl, more preferably R 18 is hydrogen or methyl, and R 14 , R 15 are each independently hydrogen, and R 16 , R 17 are each independently cyano or benzyl.

[0036] The preferred composition according to the present application contains a compound of Formula (V) wherein R 19 , R 20 are each independently hydrogen, halogen, cyano or nitro, more preferably R 19each independently is hydrogen, chlorine, bromine, cyano or nitro. 20 each independently is hydrogen, chlorine, bromine, cyano or nitro.

[0037] Preferred compositions of the present application contain a compound of formula (V) wherein R 21 is hydrogen or C1-C4 alkoxy, more preferably R 21 is hydrogen or methoxy.

[0038] Preferred compositions of the present application contain a compound of formula (V) wherein R 22 is hydrogen or -NHCOR 23 , R 23 is as defined above, more preferably R 22 is hydrogen or -NHCOCH3, and R 19 , R 20 each independently is hydrogen, chlorine, bromine, cyano or nitro and R 21 is hydrogen or methoxy.

[0039] Particularly preferred, the dye composition of the present application comprises component A, component B, component C, component D, wherein component D is selected from at least one of formulae (IV-1) to (IV-8), or at least one of formulae (V-1) to (V-17):

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046] The dark shade 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), and 1 to 45% by mass of the dye of formula (III), based on the total amount of the dyes.

[0047] Further, the dark shade disperse dye composition of the present application consists of 1 to 45% by mass of the dye of formula (I), 20 to 80% by mass of the dye of formula (II), and 1 to 45% by mass of the dye of formula (III), based on the total amount of the dyes.

[0048] The dye of formula (IV) is preferably contained in an amount of 0 to 30% by mass, more preferably 1 to 25% by mass, based on the total amount of the dyes. The dye of formula (IV) is preferably contained in an amount of 0 to 30% by mass, more preferably 1 to 25% by mass, based on the total amount of the dyes.

[0049] The mass percentage of the dye of formula (V) is preferably 0 to 30% and more preferably 1 to 25% based on the total amount of the dye.

[0050] The dye compounds (I) to (V) used in the dark color 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 necessary proportions.

[0051] The present application also provides a dark color disperse dye product which mainly contains the dark color disperse dye composition and an auxiliary agent, and the weight ratio of the auxiliary agent to the disperse dye composition is 0.2 to 5:1. Preferably, the dark color disperse dye product consists of the dark color 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 (sulfate), etc. Thus, the dark color disperse blue to black dye composition of the present application can be directly sold as a product, or can be sold or applied to textile material coloring after being added with a conventional auxiliary agent.

[0052] The method for preparing the dark color disperse dye product of the present application is as follows: the dye monomer compounds (primary dyes) constituting the dark color disperse dye composition are mixed in a proportion, and then are micronized by a sand mill or a grinder or other pulverizer in the presence of an auxiliary agent, water or other wetting agent; alternatively, each of the dye monomer compounds is micronized by a sand mill or a grinder or other pulverizer in the presence of an auxiliary agent, water or other wetting agent, and then is mixed in a proportion. The dark color disperse blue to black dye product of the present application is in a liquid state after being ground by a sand mill or a grinder, and is in a powder or granular state after being spray dried, which is a preparation method well known to those skilled in the art.

[0053] The dark color disperse dye product prepared according to the present application can be dyed by using a common dip dyeing method or a padding method. Among them, the common dip dyeing method is as follows: the 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; the direct printing is as follows: the fabric is subjected to a dyeing pretreatment, is dried, is shaped, is printed with a disperse dye paste on a printing machine, is subjected to steaming, is fixed by using a steaming method, and is finally washed and stentered.

[0054] The dark color dispersion 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, rubbing fastness, and good water-bubble color-fading performance. DETAILED DESCRIPTION

[0055] The present application is further described below in connection with specific examples, but the scope of protection of the present application is not limited to the following.

[0056] Example 1

[0057] Mixing 40 grams of the compound of formula (I-1), 33 grams of the compound of formula (II-3), 27 grams of the compound of formula (III-5), 260 grams of dispersing agent MF, and 1650 grams of water, grinding and dispersing, and drying, to obtain the finished product. The dye can provide black color with excellent fastness properties for polyester and its blended fabrics.

[0058]

[0059] Example 2

[0060] Mixing 25 grams of the compound of formula (I-1), 35 grams of the compound of formula (II-4), 30 grams of the compound of formula (III-5), 10 grams of the compound of formula (IV-3), 230 grams of sodium lignosulfonate, and 1150 grams of water, grinding and dispersing, and drying, to obtain the finished product. The dye can provide black color with excellent fastness properties for polyester and its blended fabrics.

[0061]

[0062] Examples 3-39

[0063] According to the method described in Example 1 or 2, except that the structures and weights of dyes I-V in Table 1 are used, 250 grams of auxiliary (200 grams of dispersing agent MF and 50 grams of sodium lignosulfonate) are added, 1800 grams of water is mixed to form a slurry, grinding and dispersing, and drying, to obtain the finished product. The dye can provide blue to black color shades with excellent fastness properties for polyester and its blended fabrics.

[0064] Table 1

[0065]

[0066]

[0067]

[0068] Dyeing Examples

[0069] 2 grams of each of the dispersion dyes prepared in Examples 1 to 39 were taken and used to dye terylene fabric by conventional high temperature and high pressure dyeing method and heat setting treatment. During the treatment, the dyeing depth (o.w.f) was controlled to be 6.0%, the bath ratio was 1:20, the pH was adjusted to 4.5 with acetic acid, the temperature was raised to 60°C, then the temperature was continuously raised to 130°C at a gradient of about 1°C / min, and the dyeing was carried out for 60 minutes. After the temperature was lowered to 80°C, the fabric was washed in 240 ml of 80°C reduction cleaning solution for 20 min. Finally, the fabric was pickled in 240 ml of 2 g / L acetic acid solution at 40°C for 15 min, dried, and heat set at 180°C for 30 seconds. The fastness to sublimation, the fastness to perspiration, and the color fastness to water bubbling were determined by the methods described in ISO 105-P01 and ISO 105-E04, and the results are shown in Table 2 below:

[0070] Table 2

[0071]

[0072]

[0073] Comparative Example 1

[0074] Example 35 of ZL99104177.1 was used as Comparative Example 1:

[0075]

[0076]

[0077] Migration test:

[0078] The dyes prepared in Example 2 of the present application and Comparative Example 1 were used to dye terylene fabric by the method described in the dyeing examples at a temperature of 70-130°C and a dyeing depth of 4.0%, and the migration was tested according to the method described in GB / T 10663. The results showed that the migration rate of the dye in Example 2 of the present application was 66.39%, and the migration rate of the dye in Comparative Example 1 was 59.64%.

[0079] As can be seen, the dark dispersion dyes of the present application have good dyeing effect, and the dyeing performance is better than that of the existing dyes.

Claims

1. A dark shade disperse dye composition comprising component A, component B and component C, 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), and said component C is selected from at least one of the following formula (III), wherein the mass percentage of component A is 1-50%, the mass percentage of component B is 20-85%, and the mass percentage of component C is 1-50%: ###0001### ###0002### ###0003### 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.

2. The dark shade disperse dye composition according to claim 1, further comprising a dye D of formula (IV) and / or formula (V): ###0004### ###0005### In formula (IV), R 14 , R 15 each independently is hydrogen, halogen or nitro, R 16 , R 17 each independently is C1-C4 alkyl, cyanoethyl, benzyl or phenethyl, R 18 is hydrogen or C1-C4 alkyl; in formula (V), R 19 , R 20 each independently is hydrogen, halogen, cyano or nitro, R 21 is hydrogen or C1-C4 alkoxy, R 22 is hydrogen or -NHCOR 23 wherein R 23 is C1-C4 alkyl, and when R 19 , R 20 are both halogen, R 22 is not hydrogen.

3. The dark shade disperse dye composition according to claim 1, wherein component A comprises at least one dye of formula (I) selected from the following compounds: ###0006### 4. The dark shade disperse dye composition according to claim 1, wherein component B comprises at least one dye of formula (II) selected from the following compounds: ###0007### 5. The dark shade disperse dye composition according to claim 1, wherein component C comprises at least one dye of formula (III) selected from the following compounds: ###0008### 6. The dark shade disperse dye composition according to claim 2, wherein component D comprises at least one dye of formula (IV) and / or formula (V) selected from the following compounds: ###0009### ###0010### 7. A dye preparation comprising the dark shade disperse dye composition according to claim 1 or claim 2, which mainly comprises said dark shade disperse dye composition and an auxiliary, the weight ratio of the auxiliary to the disperse dye composition being 0.2-5:1, and said auxiliary is selected from one or a mixture of two or more thereof in any ratio: naphthalene sulfonic acid formaldehyde condensate, lignin sulfonate, alkyl naphthalene sulfonic acid formaldehyde condensate, and sodium sulfate.

8. Use of the dye preparation according to claim 7 on polyester and its blended fabrics.

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