Disperse navy to black dye compositions and articles

Abstract

The present application discloses a kind of dispersed navy to black dye composition and product.The dispersed navy to black dye composition includes component A, component B, component C and component D, the component A is selected from at least one of the dye compounds shown in the following formula (I), the component B is selected from at least one of the dye compounds shown in the following formula (II), and the component C is selected from at least one of the dye compounds shown in the following formula (III).The present application provides a kind of dispersed navy to black dye product, containing the dispersed navy to black dye composition and auxiliary agent.Using the dispersed navy to black dye of the present application, hydrophobic fiber material has good migration, and each color fastness is excellent, especially resistant to sublimation, wash fastness and water bubble color fastness.

Description

TECHNICAL FIELD

[0001] The present application relates to a kind of dispersed dyes, especially a kind of dispersed navy to black dye composition suitable for printing and dyeing hydrophobic fiber material and product. BACKGROUND

[0002] Dispersed navy to black dye is always the most popular color system in dye market, conventional dispersed navy, such as dispersed black ECT, dispersed black S-4BL, is all medium temperature type dye, although relatively low price, but the general promotion, also can not meet the requirements in color fastness.Especially for high temperature type dispersed navy to black dye, there are generally poor levelness, migration and covering defects.Therefore, there is an urgent need for a kind of dispersed navy to black dye with outstanding performance in migration, water blister fastness, washing fastness and so on and good lifting force on the market. SUMMARY

[0003] The purpose of the present application is to provide a kind of dispersed navy to black dye composition and its dye product, when hydrophobic fiber material is dyed with the dispersed navy to black dye, it has good migration, excellent color fastness, especially resistance to sublimation, washing fastness and water blister color fastness.

[0004] To achieve the above-mentioned purpose of the application, the technical scheme adopted by the present application is as follows:

[0005] The present application provides a kind of dispersed navy to black dye composition, comprising component A, component B, component C and component D, the component A is selected from at least one of the dye compounds shown in the following formula (I), the component B is selected from at least one of the dye compounds shown in the following formula (II), the component C is selected from at least one of the dye compounds shown in the following formula (III), and the component D is selected from at least one of the dye compounds shown in the following formula (IV), wherein the mass percentage content of component A is 1-50%, the mass percentage content of component B is 15-85%, the mass percentage content of component C is 5-50%, and the mass percentage content of component D is 1-30%:

[0006]

[0007]

[0008] Wherein

[0009] R 1 , R 2 Each independently is hydrogen or halogen, and R 1 , R 2 Is not hydrogen at the same time;

[0010] R 3 Is hydrogen or -NHCOR4 R 4 It is a C1 to C4 alkyl group, and R 1 R 2 When one is halogen and the other is hydrogen, R 3 Not for -NHCOR 4 ;

[0011] R 5 It is either halogenated or cyano-based;

[0012] R 6 R 7 Each is an independent C1 to C4 alkyl group;

[0013] R 8 R 9 Each can be independently hydrogen, C1-C4 alkyl, or prefixed with alkenyl, cyano, hydroxyl, C1-C4 alkoxy, -OCOC6H5, -OC6H5, -C6H5, or -COOK. 1 -OCOK 2 Substituted C1-C4 alkyl groups, wherein K 1 K 2 Each is an independent C1 to C4 alkyl group;

[0014] R 10 It is a halogen;

[0015] R 11 It is a C1-C4 alkyl or amino group;

[0016] R 12 R 13 Each is independently a C1-C6 alkyl group or a C1-C4 alkyl group substituted with a C1-C4 alkoxy group;

[0017] R 14 It is hydrogen or C1-C4 alkoxy;

[0018] R 15 Hydrogen or NHCOK 3 K 3 It is a C1 to C4 alkyl group;

[0019] D is a group represented by formula (1), (2), or (3) below:

[0020]

[0021] Among them, X 1 X 2 Each is an independent halogen.

[0022] The C1-C4 alkyl group can be methyl, ethyl, straight or branched propyl, straight or branched butyl. The C1-C4 alkoxy group can be methoxy, ethoxy, straight or branched propoxy, straight or branched butoxy. The halogen can be fluorine, chlorine, bromine or iodine, preferably chlorine or bromine.

[0023] Preferred compositions of the present application contain a compound of formula (I) wherein R 1 , R 2 are each independently chlorine or bromine.

[0024] Preferred compositions of the present application contain a compound of formula (I) wherein R 3 is hydrogen or -NHCOCH3.

[0025] Preferred compositions of the present application contain a compound of formula (II) wherein R 5 is halogen, more preferably R 5 is chlorine or bromine.

[0026] Preferred compositions of the present application contain a compound of formula (II) wherein R 6 , R 7 are each independently methyl or ethyl.

[0027] Preferred compositions of the present application contain a compound of formula (II) wherein R 8 , R 9 are each independently C1-C4 alkyl, allyl, or C1-C4 alkyl substituted by cyano, C1-C4 alkoxy, -COOK 1 , -OCOK 2 , K 1 , K 2 as defined above. 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.

[0028] Preferred compositions of the present application contain a compound of formula (III) wherein R 10 is chlorine or bromine.

[0029] Preferred compositions of the present application contain a compound of formula (III) wherein R 11 is methyl or amino.

[0030] Preferred compositions of the present application contain a compound of formula (III) wherein R 12 , R 13 are each independently ethyl or propyl. More preferably R 12 , R 13each independently is ethyl or propyl, and R 10 is chloro or bromo and R 11 is methyl or amino.

[0031] Preferred compositions according to the application contain a compound of the formula (IV) in which R 14 is hydrogen or methoxy.

[0032] Preferred compositions according to the application contain a compound of the formula (IV) in which R 15 is hydrogen or NHCOCH3, and R 14 is hydrogen or methoxy.

[0033] Particularly preferred, component A is selected from at least one of the following dye compounds:

[0034]

[0035]

[0036] Particularly preferred, component B is selected from at least one of the following dye compounds:

[0037]

[0038]

[0039]

[0040]

[0041] Particularly preferred, component C is selected from at least one of the following dye compounds:

[0042]

[0043]

[0044]

[0045] Particularly preferred, component D is selected from at least one of the following dye compounds:

[0046]

[0047]

[0048]

[0049] The disperse navy to black dye composition of the present application preferably contains 1 to 45% by mass of component A, 20 to 85% by mass of component B, 5 to 45% by mass of component C and 1 to 25% by mass of component D, based on the total amount of the dye.

[0050] Further, the disperse navy to black dye composition of the present application consists of 1 to 40% by mass of component A, 20 to 80% by mass of component B, 5 to 40% by mass of component C and 1 to 20% by mass of component D, based on the total amount of the dye.

[0051] The disperse dye composition of the present application can also add toning components, such as C.I. Disperse Orange 25, C.I. Disperse Blue 365, as needed, and the content of the toning components is generally within 10% by mass of the total mass of the dye composition.

[0052] The disperse dye composition of the present application uses dye compounds (II) to (V) which are known dyes and can be synthesized by conventional methods, such as by using suitable components well known to those skilled in the art and using necessary proportions by means of usual diazotization and coupling reactions.

[0053] For example, the dye compound of formula (I) can be prepared according to the conventional diazotization and coupling method of disperse dyes:

[0054] (1) Preparation of the coupling component of formula (I-b):

[0055] The aniline is reacted with benzyl chloride in an organic solvent at 90°C to obtain the compound of formula (I-b);

[0056] (2) Diazotization:

[0057] The compound of formula (I-a) is diazotized with nitrosyl sulfuric acid in an acidic medium, and the temperature is controlled between 0 to 20°C;

[0058] (3) Coupling reaction:

[0059] The diazonium salt obtained in step (2) is coupled with the compound of formula (I-b) obtained in step (1) by double dropwise addition, and the temperature is controlled between 0 to 20°C. After the reaction is completed, the material is warmed to 45 to 65°C for 1 to 2 hours, and then filtered and washed to neutral to obtain the dye compound of formula (I);

[0060]

[0061] R 1 , R 2 , R 3The definition of the formula (I) is the same as the formula (I).

[0062] The present application also provides a disperse navy to black dye product, which mainly contains the disperse navy to black dye composition and an auxiliary, and the weight ratio of the auxiliary to the disperse dye composition is 0.2-5:1. Preferably, the disperse dye product is composed of the disperse dye composition and the auxiliary. The auxiliary 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 ratio from the following: lignin sulfonate (such as sodium lignin sulfonate (lignin 85A, lignin 83A)), alkyl naphthalene sulfonate formaldehyde condensate [such as methyl naphthalene sulfonate formaldehyde condensate (dispersing agent MF)], naphthalene sulfonate formaldehyde condensate (diffusing agent NNO), benzyl naphthalene sulfonate formaldehyde condensate (diffusing agent CNF), sodium sulfate, etc. Therefore, the disperse navy to black dye composition of the present application can be directly sold as a product, or can also be sold or applied to textile material coloring after being added with a conventional auxiliary.

[0063] The preparation method of the disperse dye product of the present application is as follows: the dye compounds (primary dyes) constituting the disperse navy to black dye composition are mixed according to the ratio, and then are micronized by a sand mill or a grinding mill and the like in the presence of an auxiliary, water or other wetting agent; alternatively, each dye compound is separately micronized by a sand mill or a grinding mill and the like in the presence of an auxiliary, water, and then is mixed according to the ratio. The disperse navy to black dye product of the present application is in a liquid state after being ground by a sand mill or a grinding mill, and can be in a powder or granular form after being spray-dried, which is a preparation method known to those skilled in the art.

[0064] The disperse dye prepared according to the present application can be used for dyeing by a common dip dyeing method, a padding method, or can be used for direct printing. Among them, the common dip dyeing method is as follows: the polyester fabric is pretreated, is put into a dyeing vat for dip dyeing, after dyeing, is washed with cold water to neutral, is wrung out, then is subjected to reduction cleaning, and is dried; the direct printing is as follows: the fabric is subjected to dyeing pretreatment, is dried, is shaped, is printed with a disperse dye paste on a printing machine, then is steamed, the dye on the fabric is fixed by steaming, and finally is washed and is stentered.

[0065] Compared with the prior art, the present application has the beneficial effects that: when the disperse navy to black dye prepared by the present application is used for dyeing a hydrophobic fiber material, it has good migration, and the color fastnesses are excellent, especially the fastnesses to sublimation, washing and water-bubble fading. BRIEF DESCRIPTION OF DRAWINGS

[0066] Figure 1 is a mass spectrum of the compound of formula (I-1) prepared in Example 1. DETAILED DESCRIPTION

[0067] The application will be further described in connection with the following examples, but the scope of the application is not limited to them.

[0068] Example 1:

[0069] Preparation of coupling component: In a 150 mL four-necked flask, 9.4 g of aniline, 50 mL of water, 20 mL of ethanol, and 13 g of soda ash were added. After stirring and heating to 75°C, 27.5 g of benzyl chloride was added dropwise, and the temperature of the system was controlled between 75-85°C during the addition, which took 2-3 h. After the addition was completed, the temperature was raised to 90°C and maintained for 12 h, and then lowered to 70°C. 80 mL of water was added to wash and separate the oil phase, which was the coupling component shown as (I-b1) (liquid phase purity of more than 98%, yield of 99%). The oil phase was diluted with 200 mL of acetic acid for standby use.

[0070]

[0071] Diazonium synthesis: In a 150 mL container, 30.5 g of 98% sulfuric acid, 0.105 mol of 40% nitrosyl sulfuric acid solution, and 0.1 mol of 2,4-dichloro-4-nitroaniline (I-a1) were added. After stirring and cooling to 10°C, the temperature of the system was controlled between 10-20°C during the addition, which took 1 h. After the addition was completed, the temperature was maintained at 15-20°C for 7-8 h to obtain a diazonium solution.

[0072]

[0073]

[0074] Coupling reaction: In a 500 mL container, 300 g of water, 1 g of emulsifier-15, and 0.5 g of sulfamic acid were added. After slurry at room temperature for 30 min, the temperature was lowered to 10°C. The diazonium solution of (I-a1) and the component (I-b1) were reacted by double-dropwise addition, with the temperature controlled between 10-15°C, the dropwise addition time controlled at about 1 h, and the reaction temperature maintained at 10-15°C for 2 h after the double-dropwise addition was completed. After the reaction was completed (determined by the penetration test), the temperature was raised to 55°C, and maintained for 1 h. After filtration and washing to neutral, the dye compound shown as formula (I-1) was obtained, with λmax of 425 nm in DMF. After adding the auxiliary MF, lignin, and water, and grinding uniformly, the dispersion dye was obtained after drying and dehydration. The weight ratio of MF, lignin, and the dye compound was 0.5:0.5:1, and the amount of water was 1.5 times the total weight of MF, lignin, and the dye compound.

[0075]

[0076] Example 2:

[0077] The 25 grams of compound of formula (I-1), 45 grams of compound of formula (II-4), 25 grams of compound of formula (III-5), 5 grams of compound of formula (IV-1) and 250 grams of dispersing agent MF are mixed with 1650 grams of water, ground, dispersed and dried to obtain the product. The dye can provide excellent fastness properties of blue color to polyester and its blended fabrics.

[0078]

[0079]

[0080] Examples 3-30:

[0081] The method described in Example 2 is used, except that the structure and weight of dyes I-IV 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 added to mix to form a slurry, which is ground, dispersed and dried to obtain the product. The dye can provide excellent fastness properties of blue to black color to polyester and its blended fabrics:

[0082] Table 1

[0083]

[0084]

[0085] Comparative Example 1:

[0086] Example 35 of ZL99104177.1 is used as Comparative Example 1:

[0087]

[0088]

[0089] Dyeing Examples:

[0090] 2 grams of the dispersed dye prepared in Examples 2-31 and Comparative Example 1 are weighed, respectively, and a 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 to be 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, washing fastness and water blistering fastness are measured using the methods described in ISO 105-P01 and ISO 105-C10, respectively. The results are shown in Table 2 below:

[0091] Table 2

[0092]

[0093]

[0094] Migrating test:

[0095] According to the method described in the dyeing example, the dye prepared in Example 2 and Comparative Example 1 of the present application is used to dye polyester fabric under the conditions of temperature range of 70-130℃ and dyeing depth of 4.0%, and the migrating property is tested according to the method described in GB / T 10663, and the results show that the migrating rate of the dye in Example 2 of the present application is 65.87%, and the migrating rate of the dye in Comparative Example 1 is 59.64%.

Claims

1. A disperse navy to black dye composition characterised in that: The dispersed navy blue to black dye composition comprises component A, component B, component C, and component D, wherein component A is selected from at least one dye compound of formula (I), component B is selected from at least one dye compound of formula (II), component C is selected from at least one dye compound of formula (III), and component D is selected from at least one dye compound of formula (IV), wherein the mass percentage of component A is 1-50%, the mass percentage of component B is 15-85%, the mass percentage of component C is 5-50%, and the mass percentage of component D is 1-30%. in R 1 , R 2 each independently is hydrogen or halogen, and R 1 , R 2 are not simultaneously hydrogen; R 3 is hydrogen or -NHCOR 4 , R 4 is C1-C4 alkyl, and R 1 , R 2 R 3 is not -NHCOR 4 ; R 5 R is halo or cyano; R 6 , R 7 each independently is C1-C4alkyl; R 8 , R 9 each independently is hydrogen, C1-C4alkyl, or C1-C4alkyl substituted by alkenyl, cyano, hydroxy, C1-C4alkoxy, -OCOC6H5, -OC6H5, -C6H5, -COOK 1 , -OCOK 2 , -COK 1 , K 2 each independently is C1-C4alkyl; R 10 is halogen; R 11 is C1-C4alkyl or amino; R 12 , R 13 each independently is C1-C6alkyl or C1-C4alkyl substituted with C1-C4alkoxy; R 14 is hydrogen or CrC4alkoxy; R 15 is hydrogen or NHCOK 3 , K 3 is C1-C4alkyl; D is a group represented by formula (1), (2), or (3) below: wherein X 1 , X 2 each independently is halogen.

2. A disperse navy to black dye composition according to claim 1 wherein: R 1 , R 2 each independently is chlorine or bromine; R 3 is hydrogen or -NHCOCH3; R 5 is chloro or bromo; R 6 , R 7 each independently is methyl or ethyl; R 8 , R 9 each independently is C1-C4alkyl, allyl, or C1-C4alkyl substituted by cyano, C1-C4alkoxy, -COOK 1 , -OCOK 2 or -COOH; R 10 is chloro or bromo; R 11 is methyl or amino; R 12 , R 13 each independently is ethyl or propyl; R 14 is hydrogen or methoxy; R 15 is hydrogen or NHCOCH3.

3. The disperse navy to black dye composition of claim 1, wherein: Component A is selected from at least one of the following dye compounds:

4. The disperse navy to black dye composition of claim 1, wherein: Component B is selected from at least one of the following dye compounds:

5. The disperse navy to black dye composition of claim 1, wherein: Component C is selected from at least one of the following dye compounds:

6. The disperse navy to black dye composition of claim 1, wherein: Component D is selected from at least one of the following dye compounds:

7. Disperse blue to black dye composition according to one of claims 1 to 6, characterized in that: The dispersed navy blue to black dye composition contains component A at a mass percentage of 1-45%, component B at a mass percentage of 20-85%, component C at a mass percentage of 5-45%, and component D at a mass percentage of 1-25%.

8. A disperse navy to black dye composition according to claim 7, wherein: The dispersed navy blue to black dye composition comprises component A, component B, component C, component D, component D, component D, component D, component C, component C, component D, component D, component D, component D, component D, component B, component B, component B, component C, component C, component D ...

9. A dispersion of a dark blue to black dye product, characterized by: The composition comprises a disperse navy blue to black dye composition according to any one of claims 1-8 and an auxiliary agent, wherein the weight ratio of the auxiliary agent to the disperse navy blue to black dye composition is 0.2 to 5:

1.

10. A dispersed navy to black dye preparation according to claim 9, characterised in that: The disperse navy blue to black dye product is composed of the disperse navy blue to black dye composition and auxiliaries.

11. A disperse navy to black dye preparation according to claim 9 or 10 characterised in that: The adjuvant is selected from one or more of the following in any proportion: lignin sulfonate, alkyl naphthalene sulfonate formaldehyde condensate, naphthalene sulfonate formaldehyde condensate, benzyl naphthalene sulfonate formaldehyde condensate, and sodium sulfate.

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