CN103194094B - A kind of blue to black disperse dye composition - Google Patents

A kind of blue to black disperse dye composition Download PDF

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CN103194094B
CN103194094B CN201310109439.3A CN201310109439A CN103194094B CN 103194094 B CN103194094 B CN 103194094B CN 201310109439 A CN201310109439 A CN 201310109439A CN 103194094 B CN103194094 B CN 103194094B
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component
formula
alkyl
composition
dye
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CN103194094A (en
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欧其
吕建娟
高怀庆
陈伟章
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Zhejiang Longsheng Group Co Ltd
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Zhejiang Longsheng Group Co Ltd
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Abstract

The invention provides a kind of blue to black disperse dye composition, its dye component mainly comprises the component A of at least one structure as shown in formula I of 1 ~ 55 mass parts, the B component of at least one structure as shown in formula II of 25 ~ 85 mass parts and the component C of at least one structure as shown in formula III of 5 ~ 45 mass parts; Disperse dye composition of the present invention, after commercial treatment, can liquid state, emulsifiable paste state after corpusculed or carry out dried powdery, graininess supply dyeing by spray-drying process etc.When disperse dye composition of the present invention contaminates hydrophobic fiber material, every dyeing behavior and colour fastness excellence, and meet the requirement of Oeko-Tex Standard 100; By the ratio between adjustment different components, can obtain blue to black dyeing and weaving thing.

Description

A kind of blue to black disperse dye composition
(1) technical field
The present invention relates to a kind of blue to black disperse dye composition, especially a kind of blueness of applicable printing hydrophobic filamentary material is to black disperse dye composition.
(2) background technology
In dispersed dye, blue-black series dyes usage quantity is comparatively large, but this series dyes is difficult to have excellent dyeing behavior and fastness ability simultaneously at present, and as the dyeing colour fastness in publication CN1085924A is excellent, but lifting force is poor; Dyestuff lifting force in CN101768376A is good, but light fastness is unsatisfactory; Dyestuff lifting force in CN102344694A and light fastness are all very good, but product Benzene Chloride and chlorinated toluenes (Chlorinated benzenes and toluenes) content do not meet the requirement of Oeko-Tex Standard 100.Benzene Chloride and chlorinated toluenes not easily decompose, not only to human central nervous system have suppression and anesthetic action, to skin and mucous membrane irritant, belong to Equations of The Second Kind carcinogenic substance; And have serious harm to environment, can pollute water body, soil and air, be that one has persistence and highly toxic compound, and their regulations are on the textile limited the quantity only 1.0ppm.
(3) summary of the invention
For solving the problem, the invention provides the disperse dye composition of a kind of blueness to black, when being applied to hydrophobic fiber material dyeing, every dyeing behavior and colour fastness excellence, and meet the requirement of Oeko-Tex Standard 100.
The technical solution used in the present invention is:
A kind of blue to black disperse dye composition, add except conventional auxiliary agent except during preparation, its dye component mainly comprises the component A of at least one structure as shown in formula I of 1 ~ 55 mass parts, the B component of at least one structure as shown in formula II of 25 ~ 85 mass parts and the component C of at least one structure as shown in formula III of 5 ~ 45 mass parts;
In formula II:
X 1for Cl, Br or cyano group;
R 1, R 2respective is independently C 1~ C 4alkyl, be preferably methyl;
R 3, R 4respective is independently C 1~ C 4alkyl ,-CH 2cH=CH 2, cyanoethyl, by C 1~ C 4alkoxyl group or-COOR 13the C replaced 1~ C 4alkyl, wherein R 13for C 1~ C 4alkyl;
And, work as X 1=Br, R 1, R 2for methyl, R 3, R 4for-CH 2cH=CH 2time, formula II is two or more composition.
In formula III:
X 2for Cl, Br or cyano group;
R 5, R 6respective is independently C 1~ C 4alkyl, or by cyano group, C 1~ C 4alkoxyl group or-COOR 14the C replaced 1~ C 4alkyl, wherein R 14for C 1~ C 4alkyl;
R 7for C 1~ C 4alkyl, be preferably methyl.
Preferably, based on described component A, B component and component C, the mass percentage of component A is 1 ~ 55%, the mass percentage of B component be 25 ~ 85%, component C mass percentage be 5 ~ 45%.
More preferred, described composition dye composition is made up of component A, B component and component C, and based on described component A, B component and component C, the mass percentage of component A is 1 ~ 50%, the mass percentage of B component be 25 ~ 80%, component C mass percentage be 10 ~ 45%.
Further, described composition dye composition also can comprise the component D shown at least one formula IV ~ formula VI;
In formula IV:
X 3for halogen, be preferably chlorine or bromine;
R 8for C 1~ C 4alkyl, be preferably methyl;
R 9for hydrogen or C 1~ C 4alkoxyl group;
R 10for C 1~ C 4alkyl or allyl group.
In formula (V):
R 11for hydrogen, cyano group or C 1~ C 4alkyl.
In formula VI:
X 4, X 5respective is independently hydrogen, halogen, nitro, cyano group, C 1~ C 4alkyl, C 1~ C 4alkoxyl group ,-COOC 2h 4oC 2h 4oCH 3or-OSO 2-Ph, wherein Ph represents phenyl;
R 12for hydrogen or C 1~ C 4alkyl.
Preferably, described composition dye composition is made up of component A, B component, component C and component D, based on described component A, B component, component C and component D, the mass percentage of component A is 1 ~ 55%, the mass percentage of B component is 25 ~ 80%, the mass percentage of component C be 5 ~ 45%, component D mass percentage be 1 ~ 25%.
Described B component is preferably one of following or wherein two or more mixtures:
And during B component selecting type (II-2) compound, must be two or more mixtures (namely B component can not be separately formula (II-2) compound).
Described component C is preferably one of following or wherein two or more mixtures:
Described component D is preferably one of following or wherein two or more mixtures:
Preferably, described composition is made up of dye component (A+B+C or A+B+C+D) and auxiliary agent, and the mass ratio of auxiliary agent and dye component is 0.3 ~ 5:1.
Due to the singularity of dye industry, be difficult to also there is no need to make sterling, usually can with the impurity in some preparation process, also allow the physical impurity of moisture containing a small amount of and trace when dye composite of the present invention makes finished product.
Disperse dye composition of the present invention, except conven-tional adjuvants, described dye component is preferably composed as follows:
Component A: formula I
B component: formula (II-1), or the combination of formula (II-1) and formula (II-2)
Component C: formula (III-1) or formula (III-2) or its combination;
Or disperse dye composition of the present invention, except conven-tional adjuvants, described dye component is preferably composed as follows:
Component A: formula I
B component: formula (II-1), or the combination of formula (II-1) and formula (II-2)
Component C: formula (III-1) or formula (III-2) or its combination
Component D: at least one in formula (IV-1) ~ formula (IV-4);
Or disperse dye composition of the present invention, except conven-tional adjuvants, described dye component is preferably composed as follows:
Component A: formula I
B component: formula (II-1), or the combination of formula (II-1) and formula (II-2)
Component C: formula (III-1) or formula (III-2) or its combination
Component D: at least one in formula (V-1), formula (VI-1) ~ formula (VI-6);
Disperse dye composition of the present invention, the component A used ~ component D, can synthesize by mode well known to those skilled in the art easily, as diazotization conveniently, couling process preparation, or the method to describe in A and GB1326124A according to publication US4980459A, EP0038527A, GB2123845A, JP58-109561A, CN 1491992 or the preparation of similar method, also can adopt commercially available prod.
Disperse dye composition of the present invention, as commodity selling or when using, generally include dye component and auxiliary agent two portions, its compound method can be carried out in a known manner, such as, after being mixed by above-mentioned proportioning by each dye monomer, under the existence of auxiliary agent, water or other wetting agent, carry out corpusculed with the pulverizer such as sand mill or shredder; Also mix with above-mentioned ratio after each dye monomer can being carried out corpusculed process with the pulverizer such as sand mill or shredder respectively under the existence of auxiliary agent, water or other wetting agent in addition.
Dispersion agent, diffusant and tensio-active agent etc. conventional when described auxiliary agent is dispersed dye commercialization, preferably one of following or its mixture several arbitrarily: the anionic dispersing agents such as naphthalene sulfonic acidformaldehyde condensation product, alkyl naphthalene sulfonic acid formaldehyde condensation products, benzyl naphthalene sulfonic formaldehyde condensation compound, sulfonated lignin.Particularly, naphthalene sulfonic acidformaldehyde condensation product is as dispersing agent NNO, alkyl naphthalene sulfonic acid formaldehyde condensation products is as Dispersant MF (condensation compound of methyl naphthalene sulfonic acid and formaldehyde), benzyl naphthalene sulfonic formaldehyde condensation compound is as dispersing agent CNF etc., and sulfonated lignin are as sodium lignosulfonate (as commercial dispersants Reax83A, Reax85A) etc.
According to the disperse dye composition made of the present invention, common dip method can be adopted, pad-dyeing method dyes, also can be used for direct printing.Wherein, common dip method, as polyester textile is carried out pre-treatment, is put into dye vat and is contaminated, and dye finishes, and cold water cleaning is to neutral, and strand is dry, then carries out reduction clearing, dries; Direct printing, as fabric is carried out dye pre-treatment, is dried, and setting, printing machine prints dispersed dye mill base, then evaporates, and utilizes the dye fixing that decatize mode makes on fabric, finally washes, stentering forming.
Disperse dye composition of the present invention, after commercial treatment, can liquid state, emulsifiable paste state after corpusculed or carry out dried powdery, graininess supply dyeing by spray-drying process etc.When disperse dye composition of the present invention contaminates hydrophobic fiber material, every dyeing behavior and colour fastness excellence, and meet the requirement of Oeko-Tex Standard 100; By the ratio between adjustment different components, can obtain blue to black dyeing and weaving thing.
(4) embodiment
Below in conjunction with specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in this:
Embodiment 1:
By the component A of 40 grams of formula I, 25 grams of formulas (II-1) and the B component of 12 grams (II-2), the component C of 23 grams of formulas (III-1), the Dispersant MF of 150 grams, the sodium lignosulfonate (Reax85A) of 30 grams, add water 750 grams and stir, grinding distribution is also dry, get product, this dyestuff can be supplied to the excellent black of the every fastness ability of fabric.
Embodiment 2:
By the component A of 40 grams of formula I, 20 grams of formulas (II-1) and the B component of 15 grams (II-2), 10 grams of formulas (III-1) and the component C of 10 grams of formulas (III-2), the component D of 5 grams of formulas (V-1), the Dispersant MF of 150 grams, the sodium lignosulfonate (Reax85A) of 30 grams, add water 750 grams and stir, grinding distribution is also dry, get product, this dyestuff can be supplied to the excellent black of the every fastness ability of fabric.
Embodiment 3:
By the component A of 10 grams of formula I, 25 grams of formulas (II-1) and the B component of 25 grams (II-2), the component C of 35 grams of formulas (III-1), the component D of 5 grams of formulas (VI-1), the Dispersant MF of 150 grams, the sodium lignosulfonate (Reax85A) of 50 grams, add water 750 grams and stir, grinding distribution is also dry, get product, this dyestuff can be supplied to the excellent blueness of the every fastness ability of fabric.
Embodiment 4 ~ 43:
According to the method described in embodiment 2, unlike adopting the weight of component A in table 1 and B component, component C, the structure of component D and weight, add auxiliary agent 200 grams (Dispersant MF is 150 grams, and sodium lignosulfonate Reax85A is 50 grams), after the 750 grams of blendings that add water, stir, make slurries, grinding distribution, dry, obtained finished product, this dyestuff can be supplied to the excellent blueness of the every fastness ability of fabric to black.
Table 1
Comparative example 1:
Embodiment 6 in patent CN102344694A: by the compound of the compound of 40 grams of formulas (I-1), the compound of 22.4 grams of formulas (II-1), 9.6 grams (II-2), the compound of 28 grams of formulas (III-1), the Dispersant MF of 200 grams, add water and mix, grinding, spraying dry, obtains composite disperse dye.
Take the embodiment of the present invention 1 respectively, the dispersed dye that comparative example 1 obtains, Benzene Chloride and chlorinated toluenes (Chlorinated benzenesand toluenes) content is measured by the method described in US EPA8081 B:2007, the content recorded in the embodiment of the present invention 1 dispersed dye and after 5% this dyeing in polyester fabric is and does not detect, and the content in comparative example 1 dispersed dye reaches 52ppm, content after 5% this dyeing in polyester fabric reaches 1.8ppm, more than the 1.0ppm index that Oeko-Tex Standard 100 pairs of Benzene Chloride and chlorinated toluenes (Chlorinated benzenes andtoluenes) limit.
Comparative example 2:
Embodiment 8 in patent CN1085924A: by the compound of the compound of 55 grams of formulas (I-2), 25 grams of formulas (II-2), the compound of 20 grams of formulas (III-2), the lignosulfonic acid dipersant of 250 grams, add water and mix, grinding, spraying dry, obtains composite disperse dye.
Take the embodiment of the present invention 1 ~ 43 respectively, dispersed dye that comparative example 2 obtains, by the method test lifting force described in GB GB/T2397, result is as following table 2:
Table 2
Embodiment Lifting force
Embodiment 1 ~ 43 A
Comparative example 2 A-B
As seen from the above table, the dispersed dye lifting force that obtains of the present invention is excellent.

Claims (6)

1. blueness is to a black disperse dye composition, and its dye component mainly comprises B component as shown in formula II of the component A of at least one structure as shown in formula I, at least one structure and the component C of at least one structure as shown in formula III; Based on described component A, B component and component C, the mass percentage of component A is 1 ~ 50%, the mass percentage of B component be 25 ~ 80%, component C mass percentage be 10 ~ 45%;
In formula II:
X 1for Cl, Br or cyano group;
R 1, R 2respective is independently C 1~ C 4alkyl;
R 3, R 4respective is independently C 1~ C 4alkyl ,-CH 2cH=CH 2, cyanoethyl, by C 1~ C 4alkoxyl group or-COOR 13the C replaced 1~ C 4alkyl, wherein R 13for C 1~ C 4alkyl;
And, work as X 1=Br, R 1, R 2for methyl, R 3, R 4for-CH 2cH=CH 2time, formula II is two or more mixture;
In formula III:
X 2for Cl, Br or cyano group;
R 5, R 6respective is independently C 1~ C 4alkyl, or by cyano group, C 1~ C 4alkoxyl group or-COOR 14the C replaced 1~ C 4alkyl, wherein R 14for C 1~ C 4alkyl; R 7for C 1~ C 4alkyl.
2. composition as claimed in claim 1, is characterized in that: described composition dye composition also comprises the component D shown at least one formula IV ~ formula VI;
In formula IV:
X 3for halogen;
R 8for C 1~ C 4alkyl;
R 9for hydrogen or C 1~ C 4alkoxyl group;
R 10for C 1~ C 4alkyl or allyl group;
In formula (V):
R 11for hydrogen, cyano group or C 1~ C 4alkyl;
In formula VI:
X 4, X 5respective is independently hydrogen, halogen, nitro, cyano group, C 1~ C 4alkyl, C 1~ C 4alkoxyl group ,-COOC 2h 4oC 2h 4oCH 3or-OSO 2-Ph, wherein Ph represents phenyl;
R 12for hydrogen or C 1~ C 4alkyl, described composition dye composition is made up of component A, B component, component C and component D, based on described component A, B component, component C and component D, the mass percentage of component A is 1 ~ 55%, the mass percentage of B component is 25 ~ 80%, the mass percentage of component C be 5 ~ 45%, component D mass percentage be 1 ~ 25%.
3. composition as claimed in claim 1 or 2, is characterized in that described B component is one of following or wherein two or more mixture:
And during B component selecting type (II-2) compound, must be two or more mixtures.
4. composition as claimed in claim 1 or 2, is characterized in that described component C is one of following or wherein two or more mixture:
5. composition as claimed in claim 2, is characterized in that described component D is one of following or wherein two or more mixture:
6. composition as claimed in claim 1 or 2, it is characterized in that described composition is made up of dye component and auxiliary agent, the mass ratio of auxiliary agent and dye component is 0.3 ~ 5:1.
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CN103709789B (en) * 2013-12-30 2015-12-30 浙江闰土股份有限公司 Disperse black dye composition, dispersed dye and preparation method and purposes
CN106147291A (en) * 2015-04-08 2016-11-23 上海汇友精密化学品有限公司 A kind of disperse dye composition
CN109504127A (en) * 2018-12-10 2019-03-22 杭州申航新材料有限公司 A kind of high fastness disperse black dye composition and preparation method
CN112574595B (en) * 2020-12-31 2023-05-23 浙江龙盛染料化工有限公司 Blue-to-black disperse dye composition and dye product
CN114316628B (en) * 2022-01-13 2024-02-02 上海青石化学有限公司 Monoazo disperse dye with high lifting force, preparation and application methods

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ES2124334T3 (en) * 1993-04-19 1999-02-01 Dystar Textilfarben Gmbh & Co MIXTURE OF DISPERSING DYES AND COLORING PROCEDURE USING IT.
EP0945493A1 (en) * 1998-03-23 1999-09-29 DyStar Textilfarben GmbH & Co. Deutschland KG Mixtures of monoazo disperse dyes
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CN101798472A (en) * 2010-03-26 2010-08-11 浙江闰土股份有限公司 Black and blue disperse dye composition
CN102061106A (en) * 2010-12-08 2011-05-18 浙江吉华集团有限公司 Azo disperse dye mixture and dye product thereof
CN102344695A (en) * 2011-11-14 2012-02-08 浙江闰土股份有限公司 Composite dye composition, composite disperse dye and preparation method thereof
CN102924975A (en) * 2012-11-12 2013-02-13 浙江闰土股份有限公司 Disperse dye composition and disperse dyes, and preparation method and purpose thereof

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2124334T3 (en) * 1993-04-19 1999-02-01 Dystar Textilfarben Gmbh & Co MIXTURE OF DISPERSING DYES AND COLORING PROCEDURE USING IT.
EP0714956A1 (en) * 1994-12-02 1996-06-05 DyStar Japan Ltd. Blue disperse dye mixture
EP0945493A1 (en) * 1998-03-23 1999-09-29 DyStar Textilfarben GmbH & Co. Deutschland KG Mixtures of monoazo disperse dyes
CN1844260A (en) * 2006-04-29 2006-10-11 浙江闰土股份有限公司 Combined disperse dye consisting of blended black and blue series
CN101798472A (en) * 2010-03-26 2010-08-11 浙江闰土股份有限公司 Black and blue disperse dye composition
CN102061106A (en) * 2010-12-08 2011-05-18 浙江吉华集团有限公司 Azo disperse dye mixture and dye product thereof
CN102344695A (en) * 2011-11-14 2012-02-08 浙江闰土股份有限公司 Composite dye composition, composite disperse dye and preparation method thereof
CN102924975A (en) * 2012-11-12 2013-02-13 浙江闰土股份有限公司 Disperse dye composition and disperse dyes, and preparation method and purpose thereof

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