CN106977976B - Yellow disperse dye compound and its synthetic method and tint applications - Google Patents
Yellow disperse dye compound and its synthetic method and tint applications Download PDFInfo
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- CN106977976B CN106977976B CN201710271093.5A CN201710271093A CN106977976B CN 106977976 B CN106977976 B CN 106977976B CN 201710271093 A CN201710271093 A CN 201710271093A CN 106977976 B CN106977976 B CN 106977976B
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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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
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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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/0014—Monoazo dyes prepared by diazotising and coupling from diazotized aminonaphthalene
-
- 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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
- C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
- C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
- C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
- C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
- C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
- C09B29/363—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O) from diazotized amino carbocyclic rings
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/328—Inkjet printing inks characterised by colouring agents characterised by dyes
-
- 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
- D06P1/16—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 dispersed, e.g. acetate, dyestuffs
- D06P1/18—Azo dyes
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- 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
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/30—Ink jet printing
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Dispersion Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Coloring (AREA)
Abstract
The present invention provides a kind of Yellow disperse dye compound and its synthetic method and tint applications.The disperse dye compound is indicated with general formula (1) shown below or general formula (2) indicates:R in general formula1To R5, n is defined as in the description.The Yellow disperse dye compound can form according to a certain percentage disperse dyes with auxiliary agent, and bright in color light, depth is good, and pH tolerance is wide, have excellent every dyefastness.The Yellow disperse dye is nontoxic, and without carcinogenic sensitization, safety and environmental protection, three waste discharge is few, and synthesis technology is simple, cheap, and market development and industrialized production is suitble to need.
Description
Technical field
Tint applications the present invention relates to a kind of new disperse dye compound and preparation method thereof and on fibrous material
And preparation method.Specifically, the present invention relates to a kind of Yellow disperse dye compound and preparation method thereof and in fibrous material
On tint applications.
Background technique
With the fast development of recent textile fiber material, there is spring Asia spinning, peach face, suede nap, superfine denier polyester
Fiber etc., these new materials are soft, comfortable and easy to wear, have become domestic and international textile enterprise for developing grade textiles
Popular textile raw material.Although conventional disperse dyes upper reluctantly to these new materials can contaminate at present, the knot of dyestuff and fiber
Resultant force is insufficient, and not only dye-uptake is greatly reduced, and the various aspects fastness of fabric also has different degrees of decline after dye, this is just to dispersion
Dyestuff is put forward new requirements.
The kind being widely used in Current Yellow disperse dyes kind mainly has: C.I. disperse yellow 114, C.I. disperse yellow
211, structural formula is respectively as follows:
C.I. disperse yellow 114:
C.I. DISPERSE Yellow 211:
The dyeing of above-mentioned dyestuff is beautiful in colour, has preferable dyefastness and certain tint applications performances.But when it is answered
Use when washing on ammonia fabric and superfine denier polyester fiber that ammonia homochromatism is poor, depth deficiency, dyefastness difference etc. there have been washing
Problem, it is difficult to meet the requirement currently printed and dyed.
The present inventor is by a large amount of development test, the yellow point that surprisingly the discovery present invention logical (1) and general formula (2) indicate
Dye species series is dissipated, beautiful in colour, enhancing is good, and pH tolerance is wide, washs ammonia homochromatism, depth and excellent with excellent
Every dyefastness, be particularly suitable for spring Asia spinning, peach face, suede nap, dacron ultrafine fiber, polyester-cotton fabric and wash ammonia fabric
Dyeing.
Tint applications practice have shown that, Yellow disperse dye compound represented by general formula (1) and general formula (2) have very
Wide application prospect.
Summary of the invention
The present inventor surprisingly has found Yellow disperse dye represented by general formula (1) and general formula (2) by a large number of experiments
Object is closed, it is beautiful in colour, ammonia homochromatism, depth and excellent every dyefastness are washed with excellent, is particularly suitable for spring Asia
Spinning, peach face, suede nap, dacron ultrafine fiber, polyester-cotton fabric and wash ammonia textile dyeing.
A large amount of tint applications test practice have shown that, before Yellow disperse dye compound of the present invention has wide application
Scape.
The Yellow disperse dye compound that the general formula (1) and general formula (2) that one aspect of the present invention provides indicate, structure
It is as follows:
In formula:
R1、R2It is separately-H ,-NO2、-Cl、-Br、-CN、-CF3、-SO2CH3、-SO2F、-O(CH2)pCH3、-OH
Or-COOR6Group；
R3For C1-C4 alkyl, by the intermittent C2-C6 alkyl of oxygen, substituted or unsubstituted phenyl or benzene nucleus be substituted or not
ReplaceGroup；
R4And R5It is separately-H ,-NO2,-Cl ,-Br ,-CN or-COOR7Group；
N is the integer in 1-4；
R6、R7It is separately C1-C4Alkyl, by the intermittent C of oxygen2-C6What alkyl or benzene nucleus were substituted or unsubstitutedGroup；
P is the integer in 0-3.
Another aspect of the present invention provides the method for Yellow disperse dye compound of the present invention.This method includes following step
It is rapid:
(1) by aromatic amine compound diazotising shown in general formula (3) or general formula (4), diazonium salt is obtained；
R in general formula (3) and general formula (4)1、R2、R4、R5As described above；
(2) step (1) resulting diazonium salt and general formula (5) compound represented are coupled to get the yellow
Disperse dye compound.
R in general formula (5)3, n it is as described above.
For those skilled in the art, compound represented by general formula (3), general formula (4) and general formula (5) is known
Or it can be prepared by known method by known compound.The compound as represented by general formula (5) can be by " Tetrahedron
Letters " V47 (2006), p8583-8586 and " e-EROS Encyclopedia of Reagents for Organic
Synthesis " (2005), it is prepared by method described in p1-8.Another aspect of the present invention provides a kind of Yellow disperse dye
Composition, it includes Yellow disperse dye compound and dyeing assistant of the invention.
Another aspect of the present invention provides Yellow disperse dye compound and to hydrophobic material and is containing hydrophobic material
Mixing material carry out dyeing and stamp in application.
Another aspect of the present invention provides a mean for the ink that ink-jetting process carries out stamp, and the ink includes above-mentioned
The Yellow disperse dye compound that general formula (1) or (2) indicate.
Yellow disperse dye compound of the invention and its disperse dye composition formed according to a certain percentage with auxiliary agent,
Bright in color light, depth is good, and pH tolerance is wide, has excellent every dyefastness.The Yellow disperse dye is nontoxic without carcinogenic
Sensitization, safety and environmental protection, three waste discharge is few, and synthesis technology is simple, cheap, and market development and industrialized production is suitble to need.
Detailed description of the invention
Figure 1A is the schematic diagram of dyeing in dyeability test.
Figure 1B is the schematic diagram of alkali washing process in dyeability test.
Fig. 2 is the schematic diagram of polyester-cotton blend one bath dyeing technology.
Specific embodiment
In one preferred embodiment, R in general formula (1)1For-NO2,-CN or-Br group；R2For-O (CH2)pCH3
Or-COOR6Group, p are 0 or 1, R6For C1-C4Alkyl or by the intermittent C of oxygen2-C6Alkyl；R3For substituted or unsubstituted benzene
What base or benzene nucleus were substituted or unsubstitutedGroup, wherein substituent group can be-NO2、-Cl、-Br、-CN、-CH3
Or-OCH3；N is 1 or 2.
In another preferred embodiment, R in general formula (2)4And R5It is separately-H ,-NO2,-Br ,-CN base
Group, and at least one is-NO2；R3Substituted or unsubstituted phenyl or benzene nucleus are substituted or unsubstituted
Group, wherein substituent group can be-NO2、-Cl、-Br、-CN、-CH3Or-OCH3；N is 1 or 2.
In the present invention, the Yellow disperse dye compound that general formula (1) indicates, for example including following example:
In the present invention, the Yellow disperse dye compound that general formula (2) indicates, for example including following example:
The preparation method of the Yellow disperse dye compound, includes the following steps:
(1) aromatic amine compound shown in general formula (3) or general formula (4) diazo-reaction is carried out to obtain in diazo reagent
Diazonium salt, the diazo reagent refer to that the mixing of the mixed solution or sulfuric acid and nitrosyl sulfuric acid of hydrochloric acid and sodium nitrite is molten
Liquid；
R in general formula (3) and general formula (4)1、R2、R4、R5As mentioned before；
(2) step (1) resulting diazonium salt and general formula (5) compound represented are coupled to get the yellow
Disperse dye compound；
R in general formula (5)3, n it is as mentioned before.
When the Yellow disperse dye compound is applied to dyeing, to reach application requirement, often by the yellow dispersion
Dye composition and auxiliary agent, water or other wetting agents sand mill or grinder carry out corpusculed processing, and the auxiliary agent is
The mixture of following one or two or more: alkyl naphthalene sulfonic acid formaldehyde condensation products such as Dispersant MF (methyl naphthalene sulfonic acid and formaldehyde
Condensation product), naphthalene sulfonic acid-formaldehyde condensation product such as dispersing agent NNO, benzyl naphthalene sulfonic acid-formaldehyde condensation product such as dispersing agent CNF, lignin
Dispersing agent such as lignin 83A, 85A；Wherein the weight ratio of auxiliary agent and Yellow disperse dye compound is 0.2-5:1.
Can the Yellow disperse dye is dyed through the invention hydrophobic fibre be not particularly limited, include but not
Be limited to terylene, acetate fiber, polypropylene fiber and containing the blended of above-mentioned fiber or be blended material, be particularly suitable for spring Asia spin, peach
Pi Rong, suede nap, dacron ultrafine fiber, polyester-cotton fabric and wash ammonia fabric.
The present invention also provides the ink that can be used for ink-jet printed technique, which includes the Yellow disperse dye chemical combination
Object.
Yellow disperse dye compound coloured light of the invention is gorgeous, and pH tolerance is wide, to fiber affinity height, has excellent
Wash ammonia homochromatism, depth and excellent every dyefastness.What the Yellow disperse dye compound and auxiliary agent were mixed to prepare
Yellow disperse dye product have excellent low temperature diffusion and High Temperature Dispersion Stability, to spring Asia spinning, peach face, suede nap,
Dacron ultrafine fiber, polyester-cotton fabric wash ammonia fabric with excellent tint applications performance.
The present invention is described further combined with specific embodiments below, but protection scope of the present invention is not limited in
This.
Embodiment
The present embodiment includes the preparation of the synthesis example, Yellow disperse dye product of Yellow disperse dye compound of the present invention
Example and its tint applications example.
1, the synthesis of Yellow disperse dye compound of the present invention and dye preparations preparation
1) synthesis and preparation examples 1 (synthesis of dyestuff I -2 and dye preparations preparation)
Diazotising:
23.9 grams of such as formula 3-1 compounds represented of addition in 250 milliliters of four-hole boiling flasks with stirring, 150 milliliters of water,
30.42 gram of 30% hydrochloric acid stirring and dissolving is added, is cooled to 5 DEG C hereinafter, 0-5 DEG C of temperature of maintenance, is slowly added dropwise 23 gram of 30% nitrous
Acid sodium aqueous solution carries out diazo-reaction, and reaction about needs 2 hours, and it is spare that a small amount of sulfamic acid eliminates excessive sodium nitrite.
Coupling reaction:
Above-mentioned diazo liquid is slowly added into 29.4 grams of coupling components as shown in formula 4-1,150 milliliters of water and appropriate 30%
In the weak alkaline aqueous solution of the PH=7-8 of sodium hydroxide solution composition, during which 5-10 DEG C of maintaining reaction temperature, is added dropwise 15% frequently
It is 6.0-6.5 that aqueous sodium carbonate, which adjusts reaction solution PH, and reaction about needs 2-3 hours.
It after coupling reaction, filters, washing, it is dry obtained I -2 compound of dyestuff (λ max [DMF]=435nm).
Dyestuff I-2 obtained will be synthesized, by purification, liquid phase separation purifies laggard row element analysis, elemental analysis result
It is listed in Table 1 below.
Table 1
Auxiliary agent MF and water are added into dye composition shown in formula (I-2), carries out grinding distribution with grinder, then through height
Temperature, which is spray-dried, is made dye powder, and wherein the weight ratio of Dispersant MF and dye composition is 3:1, and water is dye composition
The sum of with the weight of auxiliary agent MF.Resulting product is for following various dyeability tests.
2) synthesis and preparation examples 2 (synthesis of dyestuff I -7 and dye preparations preparation)
Diazotising:
16.81 grams of 4- methoxyl group -2- nitroanilines of addition in 250 milliliters of four-hole boiling flasks with stirring, 100 milliliters
30.42 gram of 30% hydrochloric acid stirring and dissolving is added in water, is cooled to 5 DEG C hereinafter, 0-5 DEG C of temperature of maintenance, is slowly added dropwise 23 gram of 30% Asia
Sodium nitrate aqueous solution carries out diazo-reaction, and reaction about needs 2 hours, and it is spare that a small amount of sulfamic acid eliminates excessive sodium nitrite.
Coupling reaction:
Above-mentioned diazo liquid is slowly added into 37 grams of coupling components as shown in formula 4-2,350 milliliters of water and appropriate 30% hydrogen
In the weak alkaline aqueous solution of the PH=7-8 of sodium hydroxide solution composition, during which 5-10 DEG C of maintaining reaction temperature, is added dropwise 15% carbon frequently
It is 6.0-6.5 that acid sodium aqueous solution, which adjusts reaction solution PH, and reaction about needs 2-3 hours.
It after coupling reaction, filters, washing, it is dry obtained I -7 compound of dyestuff (λ max [DMF]=475nm).
Dyestuff I-7 obtained will be synthesized, by purification, liquid phase separation purifies laggard row element analysis, elemental analysis result
It is listed in Table 2 below.
Table 2
Auxiliary agent lignin 83A and water are added into dye composition shown in formula (I-7), carries out grinding point with grinder
It dissipates, then dye powder is made through high temperature spray-drying, wherein the weight ratio of auxiliary agent lignin and dye composition is 1:1, water
For the sum of dye composition and the weight of auxiliary agent lignin.
3) synthesis and preparation examples 3 (synthesis of dyestuff II -1 and dye preparations preparation)
Diazotising:
23.3 grams of 2,4- dinitro-naphthalidines, 20 milliliter of 98% sulphur are added in 250 milliliters of four-hole boiling flasks with stirring
Acid, stirring and dissolving maintain 30-40 DEG C of temperature, and the 42% nitrosyl sulfuric acid solution that equivalent is slowly added dropwise carries out diazo-reaction,
Reaction about need 2 hours, be cooled to 10 DEG C or less it is spare.
Coupling reaction:
Above-mentioned diazo liquid is slowly added into 38.4 grams of coupling components as shown in formula 4-3,260 milliliters of water and appropriate 30%
In the weak alkaline aqueous solution of the PH=7-8 of sodium hydroxide solution composition, during which 5-10 DEG C of maintaining reaction temperature, is added dropwise 30% frequently
It is 6.0-6.5 that sodium hydroxide solution, which adjusts reaction solution PH, and reaction about needs 4-5 hours.
It after coupling reaction, filters, washing, it is dry obtained II -1 compound of dyestuff (λ max [DMF]=456nm).
Dyestuff II -1 obtained will be synthesized, by purification, liquid phase separation purifies laggard row element analysis, elemental analysis result
It is listed in Table 3 below.
Table 3
Auxiliary agent MF, lignin 85A and water are added into dye composition shown in formula (II -1), is ground with grinder
Dispersion, then dye powder is made through high temperature spray-drying, wherein the weight ratio of dispersing agent and dye composition is 2:1, MF and wood
The weight ratio 1:1 of quality 85A, water are the sum of dye composition and the weight of auxiliary agent.Resulting product is used for following various dyes
Color performance test.
2, the Application Example of Yellow disperse dye of the present invention
Every test method of Application Example
The properties of the present embodiment are tested by following every test methods
1), dyeability test: selection five kinds of terylene substrates, have: resistance polyester fiber knitting fabric, spring Asia spinning, peach face, suede nap,
Dacron ultrafine fiber, according to dyeing (the A expression in Figure 1A: disperse dyes: X%o.w.f., HAC+NaAC adjusting pH of Figure 1A
=4, Argalevel BAP (being purchased from Shanghai Argus Textile Chemical Co., Ltd.) 0.5g/L) it is dyed, dye level is
2% (dyestuff is to fabric weight) carries out alkali according to the alkali washing process of Figure 1B (B is sodium hydrosulfite: 3g/L and caustic soda: 2g/L) after dyeing
It washes, finally under the conditions of constant temperature and humidity in light box, observes the uniformity that five kinds of terylene substrate cloth covers obtain color.
2), pH tolerance is tested: on resistance polyester fiber knitting fabric, according to the dyeing of Figure 1A, dye level 2%o.w.f.
(dyestuff is to fabric weight) carries out under the conditions of pH value is 3.0,3.5,4.0,4.5,5.0,5.5,6.0,6.5,7.0,8.0,9.0
Dyeing carries out alkali cleaning according still further to the alkali washing process of Figure 1B, finally tests it with Datacolor colour photometer under the conditions of constant temperature and humidity
Color difference CIEDE and power part wgt is simultaneously recorded.
3), fastness to soaping is tested: after resistance polyester fiber knitting fabric dyed fabric alkali cleaning, then 180 DEG C of sizing 45S, by the world
Standard ISO105C10-2006C measurement.
4), sublimation reliability is tested: after resistance polyester fiber knitting fabric dyed fabric alkali cleaning, then 180 DEG C of sizing 45S, by international standard
ISO105-P01 measurement.
5) it, washs ammonia homochromatism: resistance polyester fiber knitting fabric, spandex thread proportionally 92/8 is dyed according to the dyeing of Figure 1A,
Dye level is 2%o.w.f. (dyestuff is to fabric weight), compares and washs in light box under the conditions of constant temperature and humidity after dyeing
Color degree of closeness on synthetic fibre looped fabric and spandex thread.
6), polyester-cotton blend one-bath process: on terylen cotton knitting cloth, according to Fig. 2 dyeing (in Fig. 2 A include: disperse dyes,
Reactive dye, Argabuffer 07 (being purchased from Shanghai Argus Textile Chemical Co., Ltd.) and anhydrous sodium sulphate) it is dyed, it contaminates
Color depth is 2%o.w.f. (dyestuff is to fabric weight), after dyeing under the conditions of constant temperature and humidity in light box, observes polyester-cotton blend
Fabric obtains the uniformity of color.
Auxiliary agent MF, lignin are separately added into dye composition shown in formula (I-3), (I-6), (II -1), (II -5)
85A and water carry out grinding distribution with grinder, then dye powder product are made through high temperature spray-drying, wherein auxiliary agent and dyestuff
The weight ratio of compound is the weight ratio 1:1 of 2:1, MF and lignin 85A, water for dye composition and auxiliary agent weight it
With.Application examples implementation is carried out using Yellow disperse dye product shown in the following table 4.
Table 4
Performance test embodiment 1
Dyeability test
Yellow disperse dye of the invention can be in five kinds of substrates of terylene: resistance polyester fiber knitting fabric, spring Asia spinning, peach face, chamois leather
Cloth cover obtains that color is uniform on suede, dacron ultrafine fiber, suitable for contaminating different dacrons, practical application value with higher.
Performance test embodiment 2
The pH tolerance of each dye preparations is measured by above-described embodiment measuring method, colour examining result is reported in Table 5 below.
Table 5
Yellow disperse dye product of the invention can be dyed in pH value 3.0 to 8.0, and pH tolerance is very wide, in practical dyeing
Technique is easy to control in the process, convenient for operation, it is not easy to dyeing defect, practical application value with higher.
Performance test embodiment 3
Fastness to soaping
The fastness to soaping of following dye preparations is measured by above-described embodiment measuring method, test result is recorded in table 6
In.
Table 6
Yellow disperse dye product of the invention has excellent fastness to soaping.
Performance test embodiment 4
Sublimation reliability
The sublimation reliability of following dye preparations is measured by above-described embodiment measuring method, test result is reported in Table 7 below.
Table 7
Yellow disperse dye product of the invention has excellent sublimation reliability.
Performance test embodiment 5
Wash ammonia homochromatism
Disperse dyes product of the present invention form and aspect on resistance polyester fiber knitting fabric and spandex thread are close, and homochromatism is good, washing ammonia fabric
On can reach splendid even dyeing effect.
Performance test embodiment 6
Polyester-cotton blend one-bath process
For disperse dyes product of the present invention in polyester-cotton blend one-bath process, it is more uniform that cloth cover obtains color ratio, can a bath solve polyester-cotton blend dyeing
Problem reduces dyeing time, improves production efficiency.
Claims (10)
1. a kind of Yellow disperse dye compound, which is indicated with general formula (1) shown below or general formula (2)
It indicates:
In formula:
R1、R2It is separately-H ,-NO2、-Cl、-Br、-CN、-CF3、-SO2CH3、-SO2F、-O(CH2)pCH3,-OH or-
COOR6Group；
R3For C1-C4Alkyl, by the intermittent C of oxygen2-C6Alkyl, substituted or unsubstituted phenyl, benzene nucleus are substituted or unsubstitutedGroup；
R4And R5It is separately-H ,-NO2,-Cl ,-Br ,-CN or-COOR7Group；
N is the integer in 1-4；
R6、R7It is separately C1-C4Alkyl, by the intermittent C of oxygen2-C6Alkyl, benzene nucleus are substituted or unsubstitutedGroup；
P is the integer in 0-3.
2. Yellow disperse dye compound described in claim 1, which is characterized in that R in general formula (1)1For-NO2,-CN or-Br
Group；R2For-O (CH2)pCH3Or-COOR6Group, p are 0 or 1, R6For C1-C4Alkyl, by the intermittent C of oxygen2-C6Alkyl；R3To take
Generation or unsubstituted phenyl, benzene nucleus are substituted or unsubstitutedGroup；N is 1 or 2.
3. Yellow disperse dye compound described in claim 1, which is characterized in that R in general formula (2)4And R5Separately
For-H ,-NO2,-Br ,-CN group, and at least one be-NO2；R3For substituted or unsubstituted phenyl, benzene nucleus be substituted or not
ReplaceGroup；N is 1 or 2.
4. Yellow disperse dye compound described in claim 1, characteristic are, the dye composition of general formula (1) is selected from such as
Lower compound:
5. Yellow disperse dye compound described in claim 1, characteristic are, the dye composition of general formula (2) is selected from such as
Lower compound:
6. the method for preparing Yellow disperse dye compound described in claim 1, which comprises the steps of:
(1) by aromatic amine compound diazotising shown in general formula (3) or general formula (4), diazonium salt is obtained；
R in general formula (3) and general formula (4)1、R2、R4、R5As described in claim 1；
(2) step (1) resulting diazonium salt and general formula (5) compound represented are coupled to get the yellow dispersion
Dye composition；
R in general formula (5)3, n it is as described in claim 1.
7. a kind of yellow disperse dye composition, it includes that Yellow disperse dye compound described in claim 1 and dyeing help
Agent.
8. yellow disperse dye composition as claimed in claim 7, which is characterized in that the dyeing assistant is following one
Kind or two kinds or more of mixture: alkyl naphthalene sulfonic acid formaldehyde condensation products, naphthalene sulfonic acid-formaldehyde condensation product, the contracting of benzyl naphthalenesulfonateformaldehyde formaldehyde
Close object and lignin type；Wherein the weight ratio of dyeing assistant and Yellow disperse dye compound is 0.2-5:1.
9. Yellow disperse dye compound described in claim 1-5 to hydrophobic material and is containing the mixing of hydrophobic material
Material carries out the application in dyeing and stamp.
10. a kind of for carrying out the ink of stamp by ink-jetting process, the ink includes yellow as described in claim 1
Disperse dye compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710271093.5A CN106977976B (en) | 2017-04-24 | 2017-04-24 | Yellow disperse dye compound and its synthetic method and tint applications |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710271093.5A CN106977976B (en) | 2017-04-24 | 2017-04-24 | Yellow disperse dye compound and its synthetic method and tint applications |
Publications (2)
| Publication Number | Publication Date |
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