CN106810905A - A kind of active red dye and its preparation and application - Google Patents
A kind of active red dye and its preparation and application Download PDFInfo
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- CN106810905A CN106810905A CN201611103380.7A CN201611103380A CN106810905A CN 106810905 A CN106810905 A CN 106810905A CN 201611103380 A CN201611103380 A CN 201611103380A CN 106810905 A CN106810905 A CN 106810905A
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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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
- C09B62/507—Azo dyes
- C09B62/51—Monoazo 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
- 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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- Textile Engineering (AREA)
- Chemical & Material Sciences (AREA)
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Abstract
The invention discloses a kind of active red dye and its preparation and application, wherein active red dye has structure shown in formula (I), wherein, X is F or Cl, A are with SO2CHCH2Or CONHC2H4SO2CHCH2The monosubstituted or polysubstituted phenyl or naphthyl of group, D is with SO2CHCH2Or CONHC2H4SO2CHCH2The monosubstituted or polysubstituted phenyl of group, R is C1~5The C of alkyl, phenyl or phenyl substitution1~3Alkyl；M is hydrogen or alkali metal.Active red dye structure of the invention is novel, excellent performance, with good degree of fixation, color fastness, the consumption of resource can effectively be reduced, there is good stability after dyeing, bright in color light, the dyeing such as the dip-dye of the cotton Products such as polyester-cotton blend, fiber crops, synthetic cotton, pad dyeing, ink-jet printed, and low production cost can be widely used in, can be with large-scale promotion application.
Description
Technical field
The invention belongs to field of fine chemical, and in particular to a kind of reactive dye, more particularly to a kind of active red dye and
Its preparation method and the application in cotton fiber printing and dyeing.
Background technology
Reactive dye (reaction dye) be also chemically-reactive dyes.Contain chemically active group in molecule, can be
The dyestuff of common key is formed in the aqueous solution with the fiber-reactive such as cotton, hair.Although double-active group can improve the properties of dyestuff,
But there are some shortcomings, such as active red B-6BF poor solubilities, coloured light is not bright-coloured, and degree of fixation is low, and washing fastness is poor.B-6BF is red
Structure is as follows：
The reactive dye of multi-active base have a more preferable degree of fixation than single active group reactive dye, but blindness piles up active group
Group is not of practical significance in itself for dyestuff, can only increase the cost of DYE PRODUCTION, and the hydrolysis of dyestuff will also result in work
The waste of property group.Therefore, the synthesis of the reactive dyes with multi-reactive groups of stabilization is still the hot topic of research with exploitation.
The content of the invention
The purpose of the present invention is on the basis of existing technology, there is provided a kind of structure is novel, the active red of excellent performance dye
Material.The dyestuff has good solubility, degree of fixation, color fastness, there is good stability after dyeing, and bright in color light can be extensively
The dyeing such as the dip-dye of the fibres such as cotton, fiber crops, synthetic cotton, pad dyeing, ink-jet printed, and low production cost are applied to, can
With large-scale promotion application.
It is a further object of the present invention to provide a kind of preparation method of above-mentioned active red dye.
The third object of the present invention is to provide a kind of application of above-mentioned active red dye in terms of scrim printing and dyeing.
The purpose of the present invention can be reached by following measures：
The active red dye of structure shown in a kind of formula (I),
Wherein,
X is F or Cl；
A is with-SO2CHCH2Or-CONHC2H4SO2CHCH2The monosubstituted or polysubstituted phenyl or naphthyl of group, its
Substitution base includes C1~3Alkyl or-SO3M；
D is with-SO2CHCH2Or-CONHC2H4SO2CHCH2The monosubstituted or polysubstituted phenyl of group, its substitution base
Including C1~3Alkyl or-SO3M；
R is C1~5The C of alkyl, phenyl or phenyl substitution1~3Alkyl；
M is hydrogen or alkali metal.
A groups in the present invention are at least provided with-SO2CHCH2Or-CONHC2H4SO2CHCH2The phenyl or naphthyl of group, A
In group can also contain except first two group in addition to other substitution bases, including but not limited to C1~3Alkyl or-SO3M。
In a kind of preferred scheme, A groups are selected from the one kind in following group：
D groups in the present invention are at least provided with-SO2CHCH2Or-CONHC2H4SO2CHCH2The phenyl of group, in D groups
Can also contain except first two group in addition to other substitution bases, including but not limited to C1~3Alkyl or-SO3M。
In a kind of preferred scheme, D is selected from following group：
In a kind of preferred scheme, R is selected from methyl, ethyl, n-propyl, isopropyl, phenyl, benzyl or phenethyl.
In a kind of preferred scheme, the M in the present invention is H, Na or K.
Active red dye in the present invention, wherein it is preferred that following compounds：
The invention discloses a kind of preparation method of above-mentioned active red dye, it comprises the following steps：
(1), formula (II) diazol and formula (III) compound are through being coupled (IV) compound
Wherein, A1It is with-SO2CH2CH2OSO3H or-CONHC2H4SO2CH2CH2OSO3The A groups of H；
(2), formula (IV) compound and formula (V) compound obtain formula (VI) compound through condensation reaction；
(3), formula (VII) compound and formula (VIII) compound obtain formula (Ⅸ) compound through reductive amination process；
Wherein, D1It is with-SO2CH2CH2OSO3H or-CONHC2H4SO2CH2CH2OSO3The D groups of H；
(4), formula (VI) compound and formula (Ⅸ) compound obtain formula (I ') compound through condensation reaction.
(5), formula (I ') compound obtains formula (I) compound after basic hydrolysis
In a kind of preferred scheme, in step (1), formula (II) diazol is added in formula (III) chemical combination material, adjusted
Section pH=5-8,0-10 DEG C of temperature is coupled, and obtains (IV) compound.
In a kind of preferred scheme, in step (2), formula (V) compound ice is ground and is beaten, add formula (IV) compound
Condensation reaction is carried out, pH=3-5 is adjusted, fully formula (VI) compound is obtained after reaction.
In a kind of preferred scheme, in step (3), formula (VII) compound and formula (VIII) compound are in 40-80 DEG C of temperature
Lower catalytic hydrogenating reduction, obtains obtaining formula (Ⅸ) compound.
In a kind of preferred scheme, in step (4), formula (Ⅸ) compound is with formula (VI) compound in pH=3-5,40-
Condensation reaction is carried out at 60 DEG C, formula (I ') compound is obtained；In step (5), formula (I ') compound heats up under pH=9-10
40-70 DEG C, obtain formula (I) compound.
Unless otherwise indicated, the 1-20 saturation of carbon atom of " alkyl " expression for using in the specification and in the claims
Aliphatic group, including straight chain and branched group (digital scope mentioned in this specification, such as " 1-20 " they refer to the group, now
It is alkyl, 1 carbon atom, 2 carbon atoms, 3 carbon atoms etc. can be contained, until including 20 carbon atoms).It is former containing 1-5 carbon
The alkyl of son is referred to as low alkyl group.When low alkyl group does not replace base, unsubstituted low alkyl group is called.More preferably
It is that alkyl is that have the 1-10 medium sized alkyl of carbon atom, such as methyl, ethyl, propyl group, 2- propyl group, normal-butyl, isobutyl
Base, the tert-butyl group, amyl group etc..Preferably, alkyl is have the 1-5 low alkyl group of carbon atom, such as methyl, ethyl, propyl group, 2- third
Base, normal-butyl, isobutyl group or tert-butyl group etc..Alkyl can be substituted or unsubstituted.
The invention discloses a kind of dye composite, it is aided with dyestuff neck with above-mentioned active red dye as active component
Auxiliary agent in domain.
The dyestuff finished product being made using active red dye of the invention can be existed with solid particle, powder or solution, be contained
Common cosolvent, stabilization in some electrolyte salts, such as sodium chloride, potassium chloride, sodium sulphate, potassium sulfate and commercial dyes
Agent.
Active red dye of the invention can be applicable in scrim printing and dyeing, particularly in cotton, fiber crops or artificial cotton fiber
Dip-dye, pad dyeing or ink-jet printed aspect.
The invention provides application of the active red dye in scrim printing and dyeing.The scrim can be
The materials such as cotton, fiber crops, synthetic cotton.Compared with prior art, active red dye monomeric compound structure of the invention is novel, and performance is excellent
Different, with bright in color light, solubility is high, and degree of fixation is high, dye stabilizer, and washable, rub resistance, sun-resistant degree well, are combined with fiber
Good stability, finished product has excellent vividness, is suitable to large-scale promotion application.
Specific embodiment
With reference to specific embodiment, the present invention is described further, and the scope of the present invention is included but is not limited only to
This embodiment.
Embodiment 1：The preparation of formula (I -1) compound
(1) diazo coupling
In 250ml beakers, 20 parts of (mass parts) ice, 24.3 part of 30% hydrochloric acid, 28.1 parts of meta esters, ice mill mashing are added
30min, 6.97 parts of natrium nitrosums are slowly added to generate diazol, and 1h is stirred for after natrium nitrosum is added completely into, and use amino sulphur
Acid eliminates micro- excessive natrium nitrosum；Diazol is slowly dropped in 31.9 parts of H acid, pH=is adjusted with sodium bicarbonate when being added dropwise
5.5-8.0, continues to react 2h after adding, and diazol is wholly absent, while it is 0-10 DEG C to keep system temperature.
(2) coupling component and cyanuric fluoride primary condensation
In the flask of 1000ml, 50 parts (mass parts) ice is added to coupling feed liquid, 13.5 parts of (foldings hundred) three are then added dropwise
Poly- fluorine cyanogen adjusts pH=3.5-5.0 in wherein with sodium bicarbonate, and 0-10 DEG C of keeping temperature reacts 4-6h, and feed clarification is transparent, uses
Amino agents detect reaction end, and keeping temperature stabilization treats secondary condensation.
(3) reduction amination of aldehyde and amine
In 1000ml flasks, addition 7.2 parts of hutanals and 28.1 parts of para-esters, 50 parts of ethanol, 1 part of Raney nickel,
10MPaH2, 60-80 DEG C reduces 12h, and Filtration of catalyst, solvent evaporated obtains product secondary amine.
(4), secondary amine secondary condensation
Secondary amine is added in a contracting component, and reaction solution is warming up into 40-60 DEG C, while adjusting pH=3.5- with sodium bicarbonate
5.0,40-60 DEG C of keeping temperature reacts 4-6h, and feed clarification is transparent, and reaction end is detected with amino agents.
(5), sulfate ester hydrolysis
To soda ash is added in above-mentioned solution, pH=9-10 is adjusted, be warming up to 40-70 DEG C, react 8-10h.It is normalized to add
Dyestuff finished product is dried to obtain in work, spraying.(after purification, its MS：[M+H] +=845.07)
Embodiment 2：The preparation of formula (I -2) compound
(1) diazo coupling
In 250ml beakers, 20 parts of ice, 24.3 part of 30% hydrochloric acid, 28.1 parts of para-esters, ice mill are added to be beaten 30min, 6.97
Part natrium nitrosum is slowly added to generate diazol, and 1h is stirred for after natrium nitrosum is added completely into, and micro- mistake is eliminated with sulfamic acid
The natrium nitrosum of amount；Diazol is slowly dropped in 31.9 parts of H acid, pH=5.5-8.0 is adjusted with sodium bicarbonate when being added dropwise, plus
Continue to react 2h after complete, diazol is wholly absent, while it is 0-10 DEG C to keep system temperature.
(2) coupling component and cyanuric fluoride primary condensation
In the flask of 1000ml, 50 parts (mass parts) ice is added to coupling feed liquid, 13.5 parts of (foldings hundred) three are then added dropwise
Poly- fluorine cyanogen adjusts pH=3.5-5.0 in wherein with sodium bicarbonate, and 0-10 DEG C of keeping temperature reacts 4-6h, and feed clarification is transparent, uses
Amino agents detect reaction end, and keeping temperature stabilization treats secondary condensation.
(3) reduction amination of aldehyde and amine
In 1000ml flasks, addition 10.6 parts of benzaldehydes and 28.1 parts of para-esters, 50 parts of ethanol, 1 part of Raney nickel,
10MPaH2, 60-80 DEG C reduces 12h, and Filtration of catalyst, solvent evaporated obtains product secondary amine.
(4), secondary amine secondary condensation
Secondary amine is added in a contracting component, and reaction solution is warming up into 40-60 DEG C, while adjusting pH=3.5- with sodium bicarbonate
5.0,40-60 DEG C of keeping temperature reacts 4-6h, and feed clarification is transparent, and reaction end is detected with amino agents.
(5), sulfate ester hydrolysis
To soda ash is added in above-mentioned solution, pH=9-10 is adjusted, be warming up to 40-70 DEG C, react 8-10h.It is normalized to add
Dyestuff finished product is dried to obtain in work, spraying.(after purification, its MS：[M+H] +=925.04)
Embodiment 3：The preparation of formula (I -3) compound
(1) diazo coupling
In 250ml beakers, 20 parts of ice, 24.3 part of 30% hydrochloric acid, 35.2 parts of 2- [2- (3-AB base) second are added
Base sulfuryl] ethanol sulfuric acid ester, ice mill mashing 30min, 6.97 parts of natrium nitrosums are slowly added to generate diazol, treat that natrium nitrosum is complete
1h is stirred for after full addition, micro- excessive natrium nitrosum is eliminated with sulfamic acid；Diazol is slowly dropped to 31.9 parts of H acid
In, pH=5.5-8.0 is adjusted with sodium bicarbonate when being added dropwise, continue to react 2h after adding, diazol is wholly absent, while keeping body
It is that temperature is 0-10 DEG C.
(2) coupling component and Cyanuric Chloride primary condensation
In the flask of 1000ml, 50 parts (mass parts) ice is added to coupling feed liquid, be then added to 18.5 for being beaten
In part (folding hundred) Cyanuric Chloride, pH=3.5-5.0 is adjusted with sodium bicarbonate, 0-10 DEG C of keeping temperature reacts 4-6h, and feed clarification is saturating
It is bright, reaction end is detected with amino agents, keeping temperature stabilization treats secondary condensation.
(3) the reduction amine of aldehyde and amine
In 1000ml flasks, addition 12 parts of phenylacetaldehydes and 28.1 parts of para-esters, 50 parts of ethanol, 1 part of Raney nickel,
10MPaH2, 60-80 DEG C reduces 12h, and Filtration of catalyst, solvent evaporated obtains product secondary amine.
(4), secondary amine secondary condensation
Secondary amine is added in a contracting component, and reaction solution is warming up into 40-60 DEG C, while adjusting pH=3.5- with sodium bicarbonate
5.0,40-60 DEG C of keeping temperature reacts 4-6h, and feed clarification is transparent, and reaction end is detected with amino agents.
(5), sulfate ester hydrolysis
To soda ash is added in above-mentioned solution, pH=9-10 is adjusted, be warming up to 40-70 DEG C, react 8-10h.It is normalized to add
Dyestuff finished product is dried to obtain in work, spraying.(after purification, its MS：[M+H] +=1026.06)
Embodiment 4：The preparation of formula (I -4) compound
(1) diazo coupling
In 250ml beakers, 20 parts of ice are added, 24.3 part of 30% hydrochloric acid, 41 parts of 6- hydroxyethyl sulfuryl sulfuric ester -2- naphthylamines -
1- sulfonic acid, ice mill mashing 30min, 6.97 parts of natrium nitrosums are slowly added to generate diazol, after natrium nitrosum is added completely into again
Stirring 1h, micro- excessive natrium nitrosum is eliminated with sulfamic acid；Diazol is slowly dropped in 31.9 parts of H acid, when being added dropwise
PH=5.5-8.0 is adjusted with sodium bicarbonate, continues to react 2h after adding, diazol is wholly absent, while it is 0- to keep system temperature
10℃。
(2) coupling component and Cyanuric Chloride primary condensation
In the flask of 1000ml, 50 parts (mass parts) frozen water is added, 18.5 parts of (folding hundred) Cyanuric Chlorides are beaten 1h, above-mentioned
Coupling solution is added in Cyanuric Chloride slurries, and pH=3.5-5.0 is adjusted with sodium bicarbonate, and 0-10 DEG C of keeping temperature reacts 4-6h, feed liquid
Clear, reaction end is detected with amino agents, and keeping temperature stabilization treats secondary condensation.
(3) reduction amination of aldehyde and amine
In 1000ml flasks, 7.2 parts of hutanals and 36.1 parts of sulfonation para-esters, 50 parts of ethanol, 1 part of nickel catalysis are added
Agent, 10MPaH2, 60-80 DEG C reduces 12h, and Filtration of catalyst, solvent evaporated obtains product secondary amine.
(4), secondary amine secondary condensation
Secondary amine is added in a contracting component, and reaction solution is warming up into 40-60 DEG C, while adjusting pH=3.5- with sodium bicarbonate
5.0,40-60 DEG C of keeping temperature reacts 4-6h, and feed clarification is transparent, and reaction end is detected with amino agents.
(5), sulfate ester hydrolysis
To soda ash is added in above-mentioned solution, pH=9-10 is adjusted, be warming up to 40-70 DEG C, react 8-10h.It is normalized to add
Dyestuff finished product is dried to obtain in work, spraying.(after purification, its MS：[M+H] +=1160.91)
Embodiment 5：
According to the methods described of embodiment 4, the difference is that step 3 is changed to acetaldehyde and is urged in ethanol as solvent, nickel with meta ester
Agent, 10MPaH2, 60-80 DEG C reduces 12h, and Filtration of catalyst, solvent evaporated obtains product secondary amine, and other operations are substantially not
Become, normalized processing, dyestuff finished product I -5 is dried to obtain in spraying.(after purification, its MS：[M+H] +=1030.94).
Embodiment 6：
According to the methods described of embodiment 4, unlike sulfonation para-ester in step 3 be changed to meta ester other operations, match somebody with somebody
Than being basically unchanged, dyestuff finished product I -6 is dried to obtain in normalized processing, spraying.(after purification, its MS：[M+H] +=1058.98).
Dyeing Example 1：
Take 2g active red dye and glauber salt are obtained according to embodiment 1-7 and be made into 530ml dye liquors.At a constant temperature by cotton cloth impregnated
After dye a period of time, a certain amount of soda ash is added to heat up 60 DEG C of fixation for a period of time, then washed, soaped, dried.Press respectively
Method in GB/T 3920-2008, GB/T 3922-1995 and GB/T 3921-2008 tests its colour fastness to rubbing, resistance to day
Fastness, washing fastness are shone, it is red with the B-6BF of same type to compare, as a result such as table 2.
The Performance comparision of 2 Dyeing Example of table 1
Note：Dye level 3%
From coloration result as can be seen that the bath raio that the active red dye of embodiment 1,3,5,6 that the present invention is provided is dyeed is 1：8
Redder than B-6BF, the red CL-5B of Drimarene dye bath ratio 1：20 is small by 60%, saves dyeing water consumption up to 60%；Embodiment 2 is lived
Property red dyeing bath raio be 1：10 is redder than B-6BF, the dye bath ratio 1 of the red CL-5B of Drimarene：20 is small by 50%, saves dye
Color water consumption is up to 50%；The bath raio of the active red dye of embodiment 4 dyeing is 1：5 is redder than B-6BF, the dye of the red CL-5B of Drimarene
Color bath raio 1：20 is small by 75%, greatlys save dyeing water consumption up to 75%；
The active red dye staining power that embodiment 1-6 is provided reaches 115-140%, contaminates the dyestuff use that same depth is used
Measuring, Drimarene red CL-5B redder than B-6BF can save dyestuff up to 15-40%；Same dyeing time shortens 20-30 minutes, section
About energy consumption 20-30%；
Dyeing is washed after terminating, the water consumption soaped is for 800ml is redder than B-6BF, the red CL-5B of Drimarene 1000ml
Few 20%, while washing fastness improves 1-2 grades；
The every fastness ability of dyeing is excellent, and particularly crock fastness (dry) is redder than B-6BF, the red CL-5B raisings of Drimarene
1-2 grades, crock fastness (wet) is redder than B-6BF, the red CL-5B of Drimarene improve 1-2 grades, sunlight fastness is redder than B-6BF,
The red CL-5B of Drimarene improve 1-2 grades.
Although an embodiment of the present invention has been shown and described, for the ordinary skill in the art, can be with
Understanding can carry out various changes, modification, replacement to these embodiments without departing from the principles and spirit of the present invention
And modification, the scope of the present invention be defined by the appended.
Claims (10)
1. the active red dye of structure shown in a kind of formula (I),
Wherein,
X is F or Cl；
A is with-SO2CHCH2Or-CONHC2H4SO2CHCH2The monosubstituted or polysubstituted phenyl or naphthyl of group, its substitution
Base includes C1~3Alkyl or-SO3M；
D is with-SO2CHCH2Or-CONHC2H4SO2CHCH2The monosubstituted or polysubstituted phenyl of group, its substitution base includes
C1~3Alkyl or-SO3M；
R is C1~5The C of alkyl, phenyl or phenyl substitution1~3Alkyl；
M is hydrogen or alkali metal.
2. active red dye according to claim 1, wherein A is selected from following group：
3. active red dye according to claim 1, wherein D is selected from following group：
4. active red dye according to claim 1, wherein R is selected from methyl, ethyl, n-propyl, isopropyl, phenyl, benzene
Methyl or phenethyl.
5. active red dye according to claim 1, wherein M is H, Na or K.
6. the active red dye according to any one in Claims 1 to 5, wherein selected from following compounds：
7. the preparation method of the active red dye described in a kind of claim 1, it comprises the following steps：
(1), formula (II) diazol and formula (III) compound are through being coupled (IV) compound
Wherein, A1It is with-SO2CH2CH2OSO3H or-CONHC2H4SO2CH2CH2OSO3The A groups of H；
(2), formula (IV) compound and formula (V) compound obtain formula (VI) compound through condensation reaction；
(3), formula (VII) compound and formula (VIII) compound obtain formula (Ⅸ) compound through reductive amination process；
Wherein, D1It is with-SO2CH2CH2OSO3H or-CONHC2H4SO2CH2CH2OSO3The D groups of H；
(4), formula (VI) compound and formula (Ⅸ) compound obtain formula (I ') compound through condensation reaction.
(5), formula (I ') compound obtains formula (I) compound after basic hydrolysis
8. preparation method according to claim 7, wherein in step (1), formula (II) diazol is added into formula (III)
In chemical combination material, pH=5-8 is adjusted, 0-10 DEG C of temperature is coupled, and obtains (IV) compound；In step (2), formula (V) is changed
Compound ice mill is beaten, and adds formula (IV) compound to carry out condensation reaction, adjusts pH=3-5, fully obtains formula (VI) chemical combination after reaction
Thing；In step (3), formula (VII) compound and formula (VIII) the compound catalytic hydrogenating reduction at 40-80 DEG C of temperature obtain obtaining formula
(Ⅸ) compound；In step (4), formula (Ⅸ) compound is condensed with formula (VI) compound at pH=3-5,40-60 DEG C
Reaction, obtains formula (I ') compound；In step (5), 40-70 DEG C of the intensification under pH=9-10 of formula (I ') compound obtains formula (I)
Compound.
9. a kind of dye composite, its active red dye described in any one in Claims 1 to 5 is auxiliary as active component
With the auxiliary agent in dye field.
10. application of the active red dye in Claims 1 to 5 described in any one in scrim printing and dyeing, particularly exists
The dip-dye of cotton, fiber crops or artificial cotton fiber, pad dyeing or it is ink-jet printed in application.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110452140A (en) * | 2019-08-31 | 2019-11-15 | 台州学院 | A kind of environment-friendly preparation method thereof of high-purity benzene amine N- monoalkyl compounds |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1503828A (en) * | 2001-04-20 | 2004-06-09 | 克莱里安特财务(Bvi)有限公司 | Fiber-reactive mono-Azo dyes |
| CN1568354A (en) * | 2001-10-17 | 2005-01-19 | 克莱里安特财务(Bvi)有限公司 | Trichromatic dyeing process and dye mixtures used therein |
| CN101255283A (en) * | 2008-04-08 | 2008-09-03 | 赵卫国 | Reactive red M-2B dye and preparation method thereof |
| WO2016180641A1 (en) * | 2015-05-12 | 2016-11-17 | Huntsman Advanced Materials (Switzerland) Gmbh | Mixtures of reactive dyes and their use for the dyeing or printing of textile fibre materials |
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2016
- 2016-12-05 CN CN201611103380.7A patent/CN106810905B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1503828A (en) * | 2001-04-20 | 2004-06-09 | 克莱里安特财务(Bvi)有限公司 | Fiber-reactive mono-Azo dyes |
| CN1568354A (en) * | 2001-10-17 | 2005-01-19 | 克莱里安特财务(Bvi)有限公司 | Trichromatic dyeing process and dye mixtures used therein |
| CN101255283A (en) * | 2008-04-08 | 2008-09-03 | 赵卫国 | Reactive red M-2B dye and preparation method thereof |
| WO2016180641A1 (en) * | 2015-05-12 | 2016-11-17 | Huntsman Advanced Materials (Switzerland) Gmbh | Mixtures of reactive dyes and their use for the dyeing or printing of textile fibre materials |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110452140A (en) * | 2019-08-31 | 2019-11-15 | 台州学院 | A kind of environment-friendly preparation method thereof of high-purity benzene amine N- monoalkyl compounds |
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