CN109320996A - A kind of composite active black dye mixture and its application - Google Patents
A kind of composite active black dye mixture and its application Download PDFInfo
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- CN109320996A CN109320996A CN201811324341.9A CN201811324341A CN109320996A CN 109320996 A CN109320996 A CN 109320996A CN 201811324341 A CN201811324341 A CN 201811324341A CN 109320996 A CN109320996 A CN 109320996A
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- formula
- black dye
- composite active
- dye mixture
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Classifications
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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
- C09B67/0047—Mixtures of two or more reactive azo dyes
- C09B67/005—Mixtures of two or more reactive azo dyes all the reactive groups being 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
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
The present invention provides a kind of composite active black dye mixture and its application, and dye mixture includes at least two kinds of dye compositions shown in the following general formula (1), general formula (2), M1、M2For H, Na, K, R1、R2、R3、R4、R5、R6、R9、R10For group independent of each other.Composite active black dye prepared by the present invention, reactivity with higher, good degree of fixation, splendid depth and higher pitch black degree are suitable for cotton fibre and dye, be a kind of good environment-friendly type reactive black dye of comprehensive performance.
Description
Technical field
The invention belongs to dye fields, and in particular to a kind of composite active dye, in particular to a kind of composite reactive black dye
Expect mixture and its application in terms of stock-dye.
Background technique
In recent years, the reactive dye of compounding are increasingly by the attention of people, the dyestuff of different activities group mix (including
Different dyes parent), play the role of complementing each other, reactive dye similar in structure mix, and play synergistic function.In cotton
In stock-dye, black-dyeing almost accounts for 40%-50%, with more direct dyes and sulfur dye due to environmental issue
And disabled and limited use.Reactive dye red M-3BE (C.I. reactive black 5) is due to cheap, and fastness is good, higher fixation
Rate and easy to wash property, may be not present the environmental issue including AOX, therefore dosage is larger.But Reactive dye red M-3BE there is
The defects of lifting force is poor, pitch black degree is inadequate limits being widely used for it.Dyestuff researcher is in active black dye in recent years
Research and development aspect has done a large amount of work.Existing reactive black dye colorant match product still has depth in actual application
It is not strong, color fastness is not good enough, dyed fabric not easy cleaning the problems such as, such as patent CN101283054A, CN106566281A etc..
Summary of the invention
The purpose of the present invention is overcome the deficiencies of the prior art and provide a kind of composite active black dye mixture and its answer
With, composite active black dye mixture prepared by the present invention reactivity with higher and solubility, good degree of fixation, pole
Good depth (enhancing rate of fabric deep colour dyeing) and higher pitch black degree are suitable for cotton fibre and dye, and are a kind of comprehensive
Environment-friendly type reactive black dye of good performance is closed, the defect of Reactive dye red M-3BE is compensated for.
The purpose of the present invention is what is realized by the following technical solution:
A kind of composite active black dye mixture, comprising the following general formula (1), two class dye compositions shown in general formula (2),
Wherein, dye composition shown in general formula (1) is dye composition shown at least one general formula (1), is contaminated shown in general formula (2)
Expect that compound is dye composition shown at least one general formula (2),
In general formula (1), (2), M1、M2It is independently of one another H, Na, K, preferably Na；R1、R2、R3、R4、R5、R6、R9、R10For
Group independent of each other, and at least one is fibrous active radical.
Fibrous active radical be understood to those can with the hydroxyl of cellulose, in wool and silk amino, carboxyl,
Hydroxyl and mercapto, or react with the amino of synthesizing polyamides and possible carboxyl and to form covalent chemical bond.Fiber-reactive base
Group is usually directly connected to dye groups or is connect by a bridging unit with dye groups.Suitable fibrous active radical example
Those of substituent group can be removed at least one on aliphatic, aromatic series or heterocyclic group in this way or those are wherein mentioned
And group contain the group being suitable for the fiber-reactive, such as vinyl groups.
Preferably, group R1、R2、R3、R4、R5、R6、R9、R10Independently of one another for selected from H, C1-C4Alkyl or following formula
One of (2a), (2b), (2c), (2d), (2e), (2f):
-SO3M, M H, Na, K (2a)
-SO2CH2CH2OSO3M, M H, Na, K (2b)
-C1-C4Alkoxy (2c)
-SO2NHCH2CH2SO2CH2CH2OSO3Na (2d)
-SO2C2H4OH (2e)
-SO2CH=CH2 (2f)。
Preferably, which is also added with auxiliary agent, and auxiliary agent is selected from least one of dust-proofing agent, filler, prevents
Dust agent selects polyoxyethylene oleic acid ester mixture etc., and filler selects anhydrous sodium sulphate (Na2SO4) etc..
Preferably, formula (1) is following formula (1a) compound represented:
In the structure of formula (1a), A, B, C portion are identical or different group independently of one another, and it includes phenyl ring or naphthalene nucleus
Structure, wherein R1、R2、R3、R4、R5、R6Respectively stand alone as H, C1-C4Alkyl, C1-C4Alkoxy, carboxyl, hydroxyl ,-NHCONH2、-
SO3M、-SO2CH2CH2OSO3M, M H, Na, K.
It is further preferred that formula (1) compound represented is selected from one of following formula (1-1)~(1-15) compound represented:
It is further preferred that at least two groups are same or similar among A, B, C in formula (1) dye structure general formula.
Preferably, formula (2) compound represented is selected from one of following formula (2-1)~(2-8) compound represented:
It is further preferred that formula (2) structure dye composition is C.I active blue 19 4, it is shown below:
。
Preferably, the dye mixture according to parts by weight, the compound comprising 15-30 parts of general formulas (1) and 70-85 parts
General formula (2) compound, it is further preferred that compound and 76-82 parts of general formula (2) comprising 18-24 parts of general formula (1)
Compound.
Composite active black dye mixture of fibers dyeing of the present invention, is particularly suitable for cotton fibre dyeing.
Composite active black dye mixture provided by the invention is by a kind of trisazo- orange and C.I. active blue 19 4
Made of compounding, according to the basic principle of three primary colors subtractive colour mixture, enhance the compatibility between their dyeing, so that yarn dyed fabric has
High level-dyeing property, high degree of fixation, in dyeing fiber materials, dosage is few, while loose dyestuff is easier to clean.Furthermore draw
Into more active groups, the reactivity of dyeing is improved.
Composite active black dye mixture of the present invention can be mixed with well-known method, such as by formula (1), formula
(2) preferred dye composition and auxiliary agent are obtained through abundant mechanical mixture in parts by weight.
Formula (1) compound is made using the following raw material:
Wherein formula (I), the R in formula (II)7、R8Respectively stand alone as H, C1-C4Alkyl, C1-C4Alkoxy, carboxyl, hydroxyl ,-
NHCONH2、-SO3M、-SO2CH2CH2OSO3M, M H, Na, K；Formula (II) is naphthalene nucleus or benzene ring compound.Specific preparation step is such as
Under:
A. formula (II) diazo reaction: is subjected to diazo reaction under the action of sodium nitrite and hydrochloric acid；
B. above-mentioned formula (II) diazonium salt and formula (I) coupling reaction: are subjected to a coupling reaction；
C. double formula (II) two diazo reactions: is subjected to diazo reaction under the action of sodium nitrite and hydrochloric acid；
D. two coupling reactions: by above-mentioned formula (II) double diazonium salt and a coupling product carry out it is secondary, be three times coupled
Reaction obtains the reactive dye of the structure as shown in formula (1) after reaction.
Preferred embodiment as above-mentioned preparation method:
Diazo reaction in above-mentioned steps a, c is required to carry out under sodium nitrite and hydrochloric acid effect, and temperature is controlled in 0-
10 DEG C, pH value control is carried out at 1.0-2.0；
A coupling reaction in step b, at 5-20 DEG C, pH value control is carried out at 3.0-5.0 for temperature control；
Secondary, coupling reaction three times in step d need to react under sodium bicarbonate or soda ash effect, and temperature control exists
0-10 DEG C, pH value control is carried out at 5.0-8.0.
Invention effect
Compared with the prior art, the advantages of the present invention are as follows: composite active black dye mixture of the invention is by two kinds of groups
The dyestuff divided compounds, and mixed synergistic effect makes dyestuff reactivity with higher, and good degree of fixation is splendid
Depth and higher pitch black degree have good color fixation fastness and high pitch-black richness when dyeing to cotton fabric.
Specific embodiment
The production of each composite dye can use well-known method, make furtherly below with reference to embodiment to the present invention
Bright, but the scope of the present invention is not limited thereto.
Embodiment 1:
The compound of 20g formula (1-1) and 80g formula (2-1) compound are obtained into of the invention answer through sufficiently mechanical mix
Close reactive black dye 1.
Embodiment 2:
The compound of 22g formula (1-2) and 78g formula (2-3) compound are obtained into of the invention answer through sufficiently mechanical mix
Close reactive black dye 2.
Embodiment 3:
The compound of 15g formula (1-7) compound, 5g anhydrous sodium sulphate and 80g formula (2-4) is obtained this through sufficiently mechanical mix
The composite active black dye 3 of invention.
Embodiment 4:
It is obtained by the compound of 20g formula (1-8) compound, 5g anhydrous sodium sulphate and 75g formula (2-6) and through sufficiently mechanical mix
Composite active black dye 4 of the invention.
Embodiment 5:
It will be obtained with 15g formula (1-9) compound and the compound of 85g formula (2-8) through sufficiently mechanical mixing of the invention
Composite active black dye 5.
Comparative example 1:
100g C.I reactive black 5 is individually subjected to dye test below.
Comparative example 2:
100g C.I active blue 19 4 is individually subjected to dye test below.
Comparative example 3:
The compound of 85g formula (2-1) and 15g following formula: compound are obtained into the compound of comparative example 3 through sufficiently mechanical mix
Reactive black dye carries out dye test below.
Dyeing explanation:
It takes 1g by dyestuff made from Examples 1 to 5, comparative example 1,2,3, is first sufficiently dissolved with suitable water, then constant volume
In 250m1 volumetric flask, draws 50ml dye solution and mixed with 50m1 water, 5g cotton, 6g sodium sulphate is then added, then with 10
DEG C/heating rate of min is warming up to 60 DEG C, 2g sodium carbonate is added after being kept for 30 minutes, then keep 60 DEG C of dyeing 30min, then
It takes out by dye cotton non-ionic cleaning agent boiling soap boiling 15min, is washed with water and is dried at 70 DEG C or so.Coloration result is such as
Shown in table 1.
Embodiment and comparative example service check method execute national dyestuff and unify test stone.
1 embodiment of table and comparative example dyeability compare
From the point of view of the record of table 1, composite active black dye of the present invention has high colour-fast rate, high dye uptake, high lifting force, Gao Rong
Xie Du has good color fixation fastness and high pitch-black richness when dyeing to cotton fabric, while non-fixing part is easier to clearly
It washes, cellulosic fibre material can be dyed to the good black of good level-dyeing property, washing fastness.Compared to comparative example 1 (C.I. reactive black 5),
Comparative example 2 (C.I. active blue 19 4) and comparative example 3 are in terms of crock fastness, washing fastness, enhancing, degree of fixation, pitch black degree
There is better performance；Dyestuff dye-uptake is close with comparative example.
Exhaustive presentation carried out to the present invention above, specific case used herein is to the principle of the present invention and embodiment party
Formula is expounded, and the explanation of the above implementation is merely used to help understand method and its core concept of the invention；Meanwhile for
Those of ordinary skill in the art have change according to the thought of the present invention in specific embodiments and applications
Place will be possible, the conception and scope without exceeding accessory claim defined to change and improvement of the invention, comprehensive
Upper described, the contents of this specification are not to be construed as limiting the invention.
Claims (9)
1. a kind of composite active black dye mixture, it is characterised in that: include the dye of two classes shown in the following general formula (1), general formula (2)
Expect compound,
In general formula (1), (2), M1、M2It is independently of one another H, Na, K；R1、R2、R3、R4、R5、R6、R9、R10For base independent of each other
Group, and at least one is fibrous active radical.
2. composite active black dye mixture according to claim 1, it is characterised in that: group R1、R2、R3、R4、R5、R6、
R9、R10Independently of one another for selected from H, C1-C4Alkyl or following formula (2a), (2b), (2c), (2d), (2e), one in (2f)
Kind:
-SO3M, M H, Na, K (2a)
-SO2CH2CH2OSO3M, M H, Na, K (2b)
-C1-C4Alkoxy (2c)
-SO2NHCH2CH2SO2CH2CH2OSO3Na (2d)
-SO2C2H4OH (2e)
-SO2CH=CH2 (2f)。
3. composite active black dye mixture according to claim 1, it is characterised in that: it is also added with auxiliary agent, it is described to help
Agent is selected from least one of dust-proofing agent, filler.
4. composite active black dye mixture according to claim 1, it is characterised in that: formula (1) is shown in following formula (1a)
Compound:
In the structure of formula (1a), A, B, C portion are identical or different group independently of one another, and it includes phenyl ring or naphthalene nucleus knots
Structure, wherein R1、R2、R3、R4、R5、R6Respectively stand alone as H, C1-C4Alkoxy ,-SO3M、-SO2CH2CH2OSO3M, M H, Na, K.
5. composite active black dye mixture according to claim 4, it is characterised in that: the choosing of formula (1) compound represented
From one of following formula (1-1)~(1-15) compound represented:
6. composite active black dye mixture according to claim 4, it is characterised in that: at least two base among A, B, C
Group is identical.
7. composite active black dye mixture according to claim 1, it is characterised in that: the choosing of formula (2) compound represented
From one of following formula (2-1)~(2-8) compound represented:
8. composite active black dye mixture according to claim 1, it is characterised in that: include 15- according to parts by weight
The compound of 30 parts of general formula (1) and the compound of 70-85 parts of general formula (2).
9. the application of composite active black dye mixture according to claim 1-8, it is characterised in that: be suitable for
Cotton fibre dyeing.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110079123A (en) * | 2019-04-08 | 2019-08-02 | 泰兴锦云染料有限公司 | A kind of compound active black dye composition |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103703083A (en) * | 2011-08-04 | 2014-04-02 | 亨斯迈先进材料（瑞士）有限公司 | Mixtures of reactive dyes and their use |
| WO2014063822A1 (en) * | 2012-10-25 | 2014-05-01 | Dystar Colours Distribution Gmbh | Mixtures of fiber-reactive azo dyes, their preparation and their use |
| CN108102424A (en) * | 2017-12-25 | 2018-06-01 | 泰兴锦云染料有限公司 | A kind of composite active black dye mixture, its preparation method and application |
| CN108530943A (en) * | 2017-03-01 | 2018-09-14 | 湖北丽源科技股份有限公司 | A kind of black reactive dye mixture and its application |
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2018
- 2018-11-08 CN CN201811324341.9A patent/CN109320996B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103703083A (en) * | 2011-08-04 | 2014-04-02 | 亨斯迈先进材料（瑞士）有限公司 | Mixtures of reactive dyes and their use |
| WO2014063822A1 (en) * | 2012-10-25 | 2014-05-01 | Dystar Colours Distribution Gmbh | Mixtures of fiber-reactive azo dyes, their preparation and their use |
| CN108530943A (en) * | 2017-03-01 | 2018-09-14 | 湖北丽源科技股份有限公司 | A kind of black reactive dye mixture and its application |
| CN108102424A (en) * | 2017-12-25 | 2018-06-01 | 泰兴锦云染料有限公司 | A kind of composite active black dye mixture, its preparation method and application |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110079123A (en) * | 2019-04-08 | 2019-08-02 | 泰兴锦云染料有限公司 | A kind of compound active black dye composition |
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