CN108148449B - Reactive black dye composition and application thereof - Google Patents

Reactive black dye composition and application thereof Download PDF

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CN108148449B
CN108148449B CN201711494390.2A CN201711494390A CN108148449B CN 108148449 B CN108148449 B CN 108148449B CN 201711494390 A CN201711494390 A CN 201711494390A CN 108148449 B CN108148449 B CN 108148449B
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component
formula
reactive black
black dye
dye composition
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CN108148449A (en
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何旭斌
张桂香
王小红
邱雯
陈东
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ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD
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ZHEJIANG LONGSHENG CHEMICAL RESEARCH CO LTD
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0046—Mixtures of two or more azo dyes
    • C09B67/0055—Mixtures of two or more disazo dyes
    • C09B67/0057—Mixtures of two or more reactive disazo dyes
    • C09B67/0059—Mixtures of two or more reactive disazo dyes all the reactive groups are not directly attached to a heterocyclic system
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes
    • D06P1/384—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive dyes reactive group not directly attached to heterocyclic group
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/58—Material containing hydroxyl groups
    • D06P3/60—Natural or regenerated cellulose
    • D06P3/66—Natural or regenerated cellulose using reactive dyes
    • D06P3/666—Natural or regenerated cellulose using reactive dyes reactive group not directly attached to heterocyclic group

Abstract

The invention provides a reactive black dye compositionThe compound comprises a component A, a component B, a component C, a component D and a component E, wherein the component A is at least one of compounds shown in a formula (1), the component B is at least one of compounds shown in a formula (2), the component C is at least one of compounds shown in a formula (3), the component D is at least one of compounds shown in a formula (4), and the component E is at least one of compounds shown in a formula (5). When the reactive black dye is used for printing and dyeing fabrics, the reactive black dye has good deep dyeing property and excellent color fastness, particularly has outstanding washing fastness and rubbing fastness, and is an environment-friendly economical reactive black dye composition.

Description

Reactive black dye composition and application thereof
(I) technical field
The invention relates to a reactive black dye composition, in particular to a reactive black dye composition suitable for printing and dyeing cellulose fibers or materials containing the cellulose fibers.
(II) background of the invention
In the reactive dyes, the consumption of dark dyes is large, especially the consumption of black reactive dyes, and the consumption of reactive black KN-B is large due to low price, good fastness, high fixation rate and easy washability, and no environmental problems including AOX. But also has the defects of poor lifting force, insufficient blackness and the like, thereby limiting the wide application of the composite material.
In the prior art, reactive black dyes obtained by color matching mainly with reactive black KN-B appear, and the dyeing performance of the reactive black dyes is improved, such as patents CN105542510A, CN105778562A and CN102558907A, but the products still have room for further improvement in the aspects of washing fastness and rubbing fastness.
Disclosure of the invention
The invention aims to provide a reactive black dye composition which has good deep dyeing property and excellent various color fastness, particularly has outstanding washing fastness and rubbing fastness.
The technical scheme adopted by the invention is as follows:
a reactive black dye composition comprises a component A, a component B, a component C, a component D and a component E, wherein the component A is at least one of compounds shown in a formula (1), the component B is at least one of compounds shown in a formula (2), the component C is at least one of compounds shown in a formula (3), the component D is at least one of compounds shown in a formula (4), the component E is at least one of compounds shown in a formula (5), and based on the total weight of the components A to E, the weight parts of the component A are 30-85 parts, the weight parts of the component B are 1-40 parts, the weight parts of the component C are 5-50 parts, the weight parts of the component D are 5-50 parts, and the weight parts of the component E are 1-40 parts:
Figure BDA0001536182110000011
Figure BDA0001536182110000021
in the formulae (1) to (5),
Y1～Y6each independently is-C2H4OSO3M13or-CH ═ CH2Wherein Y is1Is preferably-C2H4OSO3M13、Y2preferably-CH ═ CH2；
M1～M13Each independently of the other is hydrogen or an alkali metal, preferably Na or K, particularly preferably M1～M13Each independently is preferably H or Na.
The component A is preferably a dye compound represented by the formula (1-1) and/or (1-2):
Figure BDA0001536182110000022
the component B is preferably a dye compound represented by the formula (2-1) and/or (2-2):
Figure BDA0001536182110000023
Figure BDA0001536182110000031
the component C is preferably a dye compound represented by the formula (3-1) and/or (3-2):
Figure BDA0001536182110000032
the component D is preferably at least one of dye compounds represented by the formulae (4-1) to (4-4):
Figure BDA0001536182110000033
Figure BDA0001536182110000041
the component E is preferably a dye compound represented by the formula (5-1) and/or (5-2):
Figure BDA0001536182110000042
preferably, based on the mass sum of the components A to E, the mass percentage of the component A is 30-85%, the mass percentage of the component B is 1-40%, the mass percentage of the component C is 5-50%, the mass percentage of the component D is 5-50%, and the mass percentage of the component E is 1-30%.
More preferably, the reactive black dye composition comprises a component A of a formula (1-1), a component B of a formula (2-1), a component C of a formula (3-1), a component D of a formula (4-1) and a component E of a formula (5-1), wherein based on the mass sum of the components A to E, the mass percentage of the component A is 30-85%, the mass percentage of the component B is 1-40%, the mass percentage of the component C is 5-40%, the mass percentage of the component D is 5-40%, and the mass percentage of the component E is 1-30%.
Particularly preferably, the reactive black dye composition comprises a component A of a formula (1-1), a component B of a formula (2-1), a component C of a formula (3-1), a component D of a formula (4-1) and a component E of a formula (5-1), wherein based on the mass sum of the components A to E, the mass percentage of the component A is 30-85%, the mass percentage of the component B is 1-40%, the mass percentage of the component C is 5-40%, the mass percentage of the component D is 5-40%, and the mass percentage of the component E is 1-30%.
The compounds of the formulae (1) to (5) according to the present invention may be free of the acid (M)1～M13Is hydrogen) or a salt (M)1～M13As an alkali metal), preferably as a salt, which may be an alkali metal salt (M)1～M13As alkali metal), the reactive dye compositions according to the invention, in free acid form (M)1～M13Is hydrogen) and in the salt form (M)1～M13Alkali metal) are interconvertible without impairing the dyeing effect, the dyes are usually present in the form of salts during the preparation and can also be acidified with acid to give the free acid form, particularly preferably as sodium or potassium salt (M)1～M13Na or K).
The reactive black dye compositions according to the invention, the dye compounds of the formulae (1) to (5) used, can be obtained by customary methods, for example by synthesis using suitable components known to the person skilled in the art and using the necessary proportions by means of customary diazotization and coupling reactions, or by reference to the methods or analogous methods in the publications CN101250334A, CN104968732A and CN 1524904A.
The preparation method of the active black dye composition comprises the steps of mixing the dye components A to E according to the proportion, wherein the mixing can be carried out by adopting a conventional mechanical mode, for example in a mill, kneader or homogenizer, in which the individual dye compounds of the formulae (1) to (5) can be present in the form of powders, granules, aqueous solutions or synthetic solutions, when the individual dye compounds are mixed in the form of a synthesis solution, the isolation of the complex reactive black dyes according to the invention from the synthesis solution can be carried out by generally known methods, for example by salting out the dyes from the reaction medium with electrolytes, such as sodium chloride or potassium chloride, or the mixed solution is evaporated and spray-dried, so that the dye components A to E and the dye composition thereof usually contain electrolyte salts (such as sodium chloride, sodium sulfate, etc.) which are conventional in reactive dyes.
When the active black dye composition is sold as a commodity or applied to textile material coloring, no auxiliary agent is added, and conventional auxiliary agents in the commodity dye, such as a cosolvent, a dispersing agent, an alkali-resistant auxiliary agent, a dust-proof agent, a surfactant, a buffering agent, an accelerating agent and the like, can also be added. The auxiliary agent is preferably one or the combination of any several of the following components: naphthalenesulfonic acid formaldehyde condensate (NNO), methylnaphthalenesulfonic acid formaldehyde condensate (dispersant MF), benzylnaphthalenesulfonate formaldehyde condensate (dispersant CNF), and sodium sulfate (industrial sodium sulfate). The auxiliary agents are all conventional types sold in the market, and the weight ratio of the reactive black dye to the auxiliary agents is 100: 0 to 45, preferably 100: 0 to 40.
The reactive black dye composition is suitable for printing and dyeing of cellulose fibers, polyamide fibers and fabrics thereof, wherein the cellulose fibers are preferably cotton fibers or regenerated fibers, and can also comprise other plant fibers such as hemp fibers or fabrics; the polyamide fiber is preferably an animal fiber material including a sheath, a wool or a silk, and a synthetic fiber material such as nylon 6 and nylon 66. When the fiber material is printed and dyed by using the active navy blue to black dye composition, the dyeing can be carried out according to a known active dye dyeing method, such as a common active dye dip dyeing method and a pad dyeing method, wherein the dip dyeing method is a method of dipping the fabric into a dye solution to gradually dye the fabric, and the procedures of dyeing, fixing color, washing, soaping, washing, dewatering, drying and the like are generally required.
The pad dyeing is a dyeing method that a fabric is soaked in a dye solution, then the fabric passes through a roller, the dye solution is uniformly rolled into the fabric, and then the fabric is steamed or hot-melted and the like, and generally the procedures of pad dyeing, drying- (pad fixing solution), steaming or baking, washing, soaping, washing, drying and the like are needed.
The invention has the following beneficial effects: the reactive black dye composition is used for printing and dyeing fabrics, has good deep dyeing property and excellent color fastness, particularly has outstanding washing fastness and rubbing fastness, and is an environment-friendly economical reactive black dye composition.
(IV) detailed description of the preferred embodiments
The following embodiments are combinedThe invention is further described, but the scope of protection of the invention is not limited thereto (the compounds described as formula in the examples are shown in the form of their sodium salts, i.e. M1～M13Na, since it is usually prepared and isolated in the form of a salt, preferably a sodium or potassium salt):
example 1:
by mechanically mixing 55 parts of component A of the formula (1-1), 15 parts of component B of the formula (2-1), 10 parts of component C of the formula (3-1), 15 parts of component D of the formula (4-1), 5 parts of component E of the formula (5-1) and 15 parts of anhydrous sodium sulphate, a dye composition is obtained which gives fabrics which are dyed black.
Figure BDA0001536182110000061
Example 2:
by mechanically mixing 60 parts of component A of the formula (1-2), 10 parts of component B of the formula (2-2), 10 parts of component C of the formula (3-1), 10 parts of component D of the formula (4-1), 10 parts of component E of the formula (5-1) and 15 parts of anhydrous sodium sulphate, a dye composition is obtained which can dye fabrics black.
Figure BDA0001536182110000071
Examples 3 to 30:
according to the method described in the embodiment 1 or 2, the components A to E and the types and the weights of the auxiliary agents in the table 1 are adopted, and the mechanical mixing is also carried out, so that the reactive dye can dye the fabric into black:
TABLE 1
Figure BDA0001536182110000072
Figure BDA0001536182110000081
Figure BDA0001536182110000091
Comparative examples 1 to 3:
examples 67 in CN105542510A, 1 in CN105778562A and 1 in CN102558907A were used as comparative examples 1 to 3, respectively.
Dyeing example:
the dye compounds obtained in examples 1 to 30 and the dye compounds obtained in comparative examples 1 to 3 were each added to a dye bath containing 60g/L of anhydrous sodium sulphate at 30 ℃ (dye concentration 2.0%, bath ratio 1:25), the temperature was raised to 60 ℃ at 2 ℃/min, and the fabric was dyed for 30 minutes by this method, 15g/L of soda was added and dyed for 60 minutes at this temperature, and then the dyed material was rinsed, soaped with a nonionic detergent for 15 minutes, rinsed and dried. The fastness to washing and to rubbing was tested according to the methods defined in ISO105-C10 and ISO 105X 12, respectively, with the results given in Table 2 below:
TABLE 2 color fastness
Figure BDA0001536182110000092
As can be seen from Table 2, the reactive dyes of examples 1 to 30 obtained by the method of the present invention have washing fastness and rubbing fastness which are 0.5 to 1 grade higher than those of the reactive dyes of comparative examples 1 to 3, and the performances are significantly improved.

Claims (9)

1. A reactive black dye composition comprises a component A, a component B, a component C, a component D and a component E, wherein the component A is at least one of compounds shown in a formula (1), the component B is at least one of compounds shown in a formula (2), the component C is at least one of compounds shown in a formula (3), the component D is at least one of compounds shown in a formula (4), the component E is at least one of compounds shown in a formula (5), and based on the total weight of the components A to E, the weight parts of the component A are 30-85 parts, the weight parts of the component B are 1-40 parts, the weight parts of the component C are 5-50 parts, the weight parts of the component D are 5-50 parts, and the weight parts of the component E are 1-40 parts:
Figure FDA0002227581610000011
in the formulae (1) to (5),
Y1～Y6each independently is-C2H4OSO3M13or-CH ═ CH2，M1～M13Each independently hydrogen or an alkali metal.
2. A reactive black dye composition according to claim 1, Y1is-C2H4OSO3M13、Y2is-CH ═ CH2；M1～M13Each independently hydrogen, Na or K.
3. A reactive black dye composition according to claim 1, wherein component A is selected from dye compounds represented by the formulae (1-1) and/or (1-2):
Figure FDA0002227581610000021
4. a reactive black dye composition according to claim 3, wherein component B is selected from dye compounds represented by the formulae (2-1) and/or (2-2):
Figure FDA0002227581610000022
5. a reactive black dye composition according to claim 4, wherein component C is selected from dye compounds represented by the formulae (3-1) and/or (3-2):
Figure FDA0002227581610000023
6. a reactive black dye composition according to claim 5, wherein component D is at least one dye compound selected from the group consisting of dye compounds represented by the formulae (4-1) to (4-4):
Figure FDA0002227581610000031
7. a reactive black dye composition according to claim 6, wherein component E is selected from dye compounds represented by the formulae (5-1) and/or (5-2):
Figure FDA0002227581610000032
Figure FDA0002227581610000041
8. a reactive black dye composition according to claim 7, wherein: the composite material is composed of a component A of a formula (1-1), a component B of a formula (2-1), a component C of a formula (3-1), a component D of a formula (4-1) and a component E of a formula (5-1), wherein based on the mass sum of the components A to E, the mass percentage of the component A is 30-85%, the mass percentage of the component B is 1-40%, the mass percentage of the component C is 5-40%, the mass percentage of the component D is 5-40%, and the mass percentage of the component E is 1-30%.
9. The reactive black dye composition according to any one of claims 1 to 7, wherein the reactive black dye composition is added as a conventional auxiliary agent in a commercial dye when being sold as a commodity or applied to textile material coloring, and the weight ratio of the reactive black dye composition to the auxiliary agent is 100: 0 to 45.
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Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100338146C (en) * 2005-04-01 2007-09-19 上海科华染料工业有限公司 Composite active black dye
CN101117449B (en) * 2007-09-04 2012-05-16 大连理工大学 High-concentration composite reactive dye
CN100478403C (en) * 2007-10-31 2009-04-15 浙江瑞华化工有限公司 Reactive dye composition and preparing process and application thereof
CN102558907B (en) * 2011-12-30 2014-07-09 浙江科永化工有限公司 Compound active black dye composition
CN105542510B (en) * 2015-09-09 2020-02-21 上海科华染料工业有限公司 Reactive black dye composition and dye product
CN105778562A (en) * 2016-03-17 2016-07-20 浙江瑞华化工有限公司 Black active dye composition and preparation method and use thereof
CN107501997A (en) * 2017-07-28 2017-12-22 浙江科永化工有限公司 A kind of reactive navy blue is to black dye composition and dye preparations

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