CN107722663A - A kind of azo dyes compounds and its preparation method and application - Google Patents

A kind of azo dyes compounds and its preparation method and application Download PDF

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Publication number
CN107722663A
CN107722663A CN201710936350.2A CN201710936350A CN107722663A CN 107722663 A CN107722663 A CN 107722663A CN 201710936350 A CN201710936350 A CN 201710936350A CN 107722663 A CN107722663 A CN 107722663A
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China
Prior art keywords
alkyl
phenyl
ethyl
hydrogen
azo dyes
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CN201710936350.2A
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Chinese (zh)
Inventor
俞杏英
姚晨华
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Zhejiang Wanfeng Chemical Co Ltd
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Zhejiang Wanfeng Chemical Co Ltd
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Priority to CN201710936350.2A priority Critical patent/CN107722663A/en
Publication of CN107722663A publication Critical patent/CN107722663A/en
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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
    • C09B29/0025—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds
    • C09B29/0029—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom
    • C09B29/0033—Monoazo dyes prepared by diazotising and coupling from diazotized amino heterocyclic compounds the heterocyclic ring containing only nitrogen as heteroatom containing a five-membered heterocyclic ring with one nitrogen atom
    • 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
    • C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08—Amino benzenes
    • 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
    • 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
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/24—Polyamides; Polyurethanes
    • D06P3/26—Polyamides; Polyurethanes using dispersed dyestuffs
    • 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
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
    • 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
    • D06P3/70—Material containing nitrile groups
    • D06P3/72—Material containing nitrile groups using dispersed dyestuffs
    • 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
    • D06P3/79—Polyolefins
    • D06P3/794—Polyolefins using dispersed 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
    • 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
    • D06P3/82—Textiles which contain different kinds of fibres

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Dispersion Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

The present invention relates to a kind of azo dyes compounds and its preparation method and application, the structural formula of the compound is：The present invention is very suitable for dyeing and printing hydrophobic material aspect, particularly textile material；Gained product dyed thereby and jet recorded matter on fabric significant effect, especially it is worth mentioning that excellent sweat proof, colour fastness to rubbing, excellent migration property energy and good lifting force.

Description

A kind of azo dyes compounds and its preparation method and application
Technical field
The invention belongs to disperse dyes field, more particularly to a kind of azo dyes compounds and its preparation method and application.
Background technology
CN101522816 discloses a series of azo dyes compounds of base esters of oxolanyl alkane containing 2-, series compound tool There is washable and fastness to sublimation advantage.But the dyed fabric that known dyestuff obtains can not meet to work as in all cases Modern demand, particularly fastness to perspiration, fastness to rubbing and lifting force requirement.Therefore a kind of more preferable reactive monoazo dyestuffs of performance are needed.
The content of the invention
The technical problems to be solved by the invention are to provide a kind of azo dyes compounds and its preparation method and application, should Compound is very suitable for dyeing and printing hydrophobic material aspect, particularly textile material；Gained product dyed thereby and jet recorded matter on fabric effect Fruit is notable, especially it is worth mentioning that excellent sweat proof, colour fastness to rubbing, excellent migration property energy and good lifting force.
The invention provides a kind of azo dyes compounds, the structural formula of the compound is as follows：
Wherein
R1It is C1-C12Alkyl；
R2It is hydrogen, C1-C6Alkyl ,-NHCO (C1-C6Alkyl) or-NHCO aryl, the aryl be substituted or unsubstituted benzene Base；
R 3It is hydrogen, C1-C6Alkyl, the C of substitution1-C6Alkyl, C1-C6Alkoxy, phenyl or the phenyl arbitrarily substituted；
R4It is C1-C6Alkyl, the C of substitution1-C6Alkyl, phenyl or the phenyl arbitrarily substituted；
X1And X2Independently for halogen, hydrogen, cyano group or nitro；
Alkyl described above is unsubstituted branched-chain or straight-chain alkyl.
Further, the R1It is C1-C4Alkyl；
R2It is hydrogen, C1-C4Alkyl ,-NHCO (C1-C4Alkyl) or-NHCO phenyl；
R3It is hydrogen, C1-C4Alkyl, the C of substitution1-C4Alkyl, phenyl or the phenyl arbitrarily substituted；
R4It is C1-C4Alkyl, the C of substitution1-C4Alkyl, phenyl or the phenyl arbitrarily substituted；
X1And X2Independently for halogen, hydrogen, cyano group or nitro；
Alkyl described above is unsubstituted branched-chain or straight-chain alkyl.
Preferably, the R1It is methyl, ethyl, n-propyl, isopropyl or normal-butyl；
R2It is hydrogen, methyl, ethyl, propyl group, acetylamino, propionamido or benzamido；
R3It is hydrogen, methyl, ethyl, propyl group, butyl, benzyl, phenylethyl, Phenoxyethyl, methoxy ethyl or cyano group Ethyl；R4It is methyl, ethyl or phenyl；
X1And X2Independently for hydrogen, Cl, Br, cyano group or nitro.
Most preferably, the R1It is methyl or ethyl；
R2It is methyl, ethyl or propyl group；
R 3It is methyl or ethyl；
R4It is methyl or ethyl；
X1And X2Independently for hydrogen, Cl, Br, cyano group or nitro.
Present invention also offers a kind of preparation method of azo dyes compounds, including：
By Formula II compound
Diazotising is simultaneously coupled to formula III compound Produce.
Generally, the diazotising of Formula II compound is carried out in known manner, such as makes it in acid with such as hydrochloric acid or sulfuric acid The aqueous medium of property uses to be used in natrium nitrosum, or the sulfuric acid in dilution, phosphoric acid or the mixture of acetic acid and propionic acid Nitrosyl sulphuric acid.Preferable temperature range is between 0 DEG C and 15 DEG C.
Equally, the compound that diazotizing compound is coupled to formula III is generally also carried out in known manner, such as In acid, water-based, water-based-organic or organic media, it proved especially advantageous that, carried out at a temperature of less than 10 DEG C.Acid used is special It is not sulfuric acid, acetic acid or propionic acid.
Logical formula (II) and the compound of (III) are known, and can be prepared by known method.
Present invention also offers a kind of application of azo dyes compounds, applied to hydrophobic material or contain hydrophobicity material The blended material dyeing of material or stamp.
Present invention also offers a kind of dye composite containing azo dyes compounds, the change of at least one Formulas I is included Compound and other at least one dye compositions.
Present invention also offers a kind of application of dye composite, applied to hydrophobic material or contains hydrophobic material Blended material dyes or stamp.
Present invention also offers a kind of dyestuff containing azo dyes compounds and dispersant.
Described hydrophobic material includes terylene, polyamide fibre, spandex, polypropylene fibre, polyvinyl chloride fibre or acrylic fibers.
Described blended material is that hydrophobic material waits until that natural fiber mixes spinning and is made into other cotton wools, silk, fiber crops Textile material, including such as polyester-cotton blend, hofa, sheep rabbit hair blending.
Formula (I) compound of the present invention or the dye composite containing formula (I) compound are in the dye for hydrophobic material , it is necessary to add auxiliary agent during the use of color and stamp, the auxiliary agent is dispersant conventional when disperse dyes compound, diffusant And other surfactants etc..Preferable auxiliary agent includes one of following or its mixture：Naphthalene sulfonic acid-formaldehyde condensation product, sulfomethylated lignin Hydrochlorate, alkyl naphthalene sulfonic acid formaldehyde condensation products.Such as condensation compound of methyl naphthalene sulfonic acid and formaldehyde (Dispersant MF), naphthalene sulfonic acid-formaldehyde condensation product (dispersing agent NNO), benzyl naphthalene sulfonic acid-formaldehyde condensation product (dispersing agent CNF), sodium lignin sulfonate (lignin 83A, 85A) etc..It is logical Often, it is 0.6~4.8 to add the weight of auxiliary agent and the weight ratio of formula (I) compound or the composition containing formula (I) compound: 1。
Beneficial effect
The present invention is very suitable for dyeing and printing hydrophobic material aspect, particularly textile material；Gained product dyed thereby and Jet recorded matter on fabric significant effect, especially it is worth mentioning that excellent sweat proof, colour fastness to rubbing, excellent migration property energy and good Lifting force.I.e. convenient dyeing concentration improves, and the color fastness for the textile that compound of the invention dyeing obtains is also very outstanding.This Invention dyestuff has good combination property, and either fastness or homogenized diet is all very excellent, and with dye well Deep performance.
Brief description of the drawings
Fig. 1 is the lifting force curve of the dyestuff of the compound of embodiment 1.
Embodiment
With reference to specific embodiment, the present invention is expanded on further.It should be understood that these embodiments are merely to illustrate the present invention Rather than limitation the scope of the present invention.In addition, it is to be understood that after the content of the invention lectured has been read, people in the art Member can make various changes or modifications to the present invention, and these equivalent form of values equally fall within the application appended claims and limited Scope.
Embodiment 1
Step 1
N-ethyl-m-toluidine 13.5g is added in 100ml three-necked flasks, adds hydroquinones 0.15g and zinc chloride 1.5g, Stirring, acrylic acid 9.0g is slowly added dropwise at 50~60 DEG C, it is complete to HPLC display reactions in 60 DEG C or so insulation reactions after adding. 50 DEG C are cooled to, toluene 40g is added, is slowly added to soda ash 9.5g, sodium bromide 1.0g, is warming up to 80 DEG C, at 80~90 DEG C slowly Chlroacetone 12.5g is added dropwise, reacts complete to HPLC display reactions, is evaporated under reduced pressure out toluene, is cooled to 60 DEG C plus water 50g processing, Take upper strata grease stand-by.
Step 2
In 150ml three-necked flasks add sulfuric acid 112g, stirring, less than 60 DEG C be slowly added into 32g N- methyl -4- amino - 3,5- dibromo phthalimides, are stirred to clarify, and are then cooled to 5~10 DEG C and are slowly added into nitrosyl sulfuric acid (40%) 31.5g, add 5~10 DEG C and be incubated diazonium 3 hours, wait to be coupled.
Step 3
500g mixture of ice and water is added in 1000ml beakers, stirring, sulfamic acid 2.5g is added, is slowly added at 5 DEG C The diazo liquid of above-mentioned steps 2, the coupling component of above-mentioned steps 1 is then slowly added into, added in 10 DEG C or so insulation reactions 5~6 Hour, 65 DEG C are directly warming up to, stirring, is incubated 1 hour, filtering, neutrality is washed to, column chromatography for separation, obtains formula (I-1) compound 50g, HPLC purity>99%.1H-NMR(DMSO,300MHZ)：1.15 (3H, t), 2.23-2.35 (6H, d), 2.64 (2H, t), 3.05 (3H, s), 3.45 (2H, m), 3.81 (2H, t), 5.2 (2H, S), 6.79-6.87 (2H, m), 7.69 (1H, d), 8.48 (1H,s)。
Embodiment 2
According to the similar approach of embodiment 1, formula (I-2) compound, HPLC purity>99%.1H-NMR(DMSO, 300MHZ)：1.15 (3H, t), 2.23-2.35 (6H, d), 2.64 (2H, t), 3.05 (3H, s), 3.45 (2H, m), 3.81 (2H, T), 5.2 (2H, S), 6.79-6.87 (2H, m), 7.69 (1H, d), 8.25 (1H, s).
Embodiment 3
According to the similar approach of embodiment 1, formula (I-3) compound, HPLC purity>99%.1H-NMR(DMSO, 300MHZ)：1.16 (3H, t), 2.23-2.35 (6H, d), 2.64 (2H, t), 3.05 (3H, s), 3.41 (2H, m), 3.76 (2H, T), 5.23 (2H, S), 6.79-6.87 (2H, m), 7.69 (1H, d), 9.15 (1H, s).
Embodiment 4
According to the method for embodiment 1, formula (I) compound of following table is prepared.
Embodiment 5
Above-described embodiment I-1~I-24 compound is mixed with MF, dried, disperse dye composition is made, uses moisture The disperse dyes suspension that mass percent concentration is 1% and 3% is not configured to, draws 20ml disperse dyes suspension and 80ml Water mixing, adjust dye bath pH to 5 with acetic acid, be then warming up to 60 DEG C, while be respectively put into 2g polyester fibers to carry out high temperature high Color is padded, 130 DEG C were warming up in 35 minutes, 30 minutes is incubated, is cooled to 80 DEG C of samplings.
Embodiment 6
The above-claimed cpd prepared using GBT3920-2008 method test according to embodiment 5 dyes the rub resistance of cloth specimen Fastness, fastness are represented with rank.As shown in table 1, the dyestuff crock fastness of the compounds of this invention is very outstanding, and dense when dyeing Degree lifting, crock fastness are also very outstanding.
Table 1
Embodiment 7
The above-claimed cpd prepared using GB/T 14576-2009 method test according to embodiment 5 dyes the resistance to of cloth specimen Perspiration fastness, fastness are represented with rank.As shown in table 2, the dyestuff color fastness to perspiration of the compounds of this invention is very outstanding, and when dye Colour saturation is lifted, and color fastness to perspiration is also very outstanding.
Table 2
Embodiment 8
Using GBT 10663-2014 method, test the above-claimed cpd prepared according to embodiment 5 and dye cloth specimen, take The cloth specimen of 1% concentration printing and dyeing, tests migration property energy.As shown in table 3, the dyestuff homogenized diet of the compounds of this invention is very outstanding.
Table 3
Embodiment 9
The above-claimed cpd prepared using GBT3921-2008 method test according to embodiment 5 dyes the water-fastness of cloth specimen Fastness
Embodiment 10
The above-claimed cpd of embodiment 1 and MF mixed numbers are obtained into dyestuff, according to 0.5%, 1%, 3%, 5%, 8%, 10% Concentration, according to embodiment 5 method dye, obtained cloth specimen use GBT 2397-2012 method, test its lifting force. As shown in figure 1, the compound has good lifting force.

Claims (9)

  1. A kind of 1. azo dyes compounds, it is characterised in that：The structural formula of the compound is as follows：
    Wherein
    R1It is C1-C12Alkyl；
    R2It is hydrogen, C1-C6Alkyl ,-NHCO (C1-C6Alkyl) or-NHCO aryl, the aryl be substituted or unsubstituted phenyl；
    R3It is hydrogen, C1-C6Alkyl, the C of substitution1-C6Alkyl, C1-C6Alkoxy, phenyl or the phenyl arbitrarily substituted；
    R4It is C1-C6Alkyl, the C of substitution1-C6Alkyl, phenyl or the phenyl arbitrarily substituted；
    X1And X2Independently for halogen, hydrogen, cyano group or nitro；
    Alkyl described above is unsubstituted branched-chain or straight-chain alkyl.
  2. A kind of 2. azo dyes compounds according to claim 1, it is characterised in that：The R1It is C1-C4Alkyl；
    R2It is hydrogen, C1-C4Alkyl ,-NHCO (C1-C4Alkyl) or-NHCO phenyl；
    R3It is hydrogen, C1-C4Alkyl, the C of substitution1-C4Alkyl, phenyl or the phenyl arbitrarily substituted；
    R4It is C1-C4Alkyl, the C of substitution1-C4Alkyl, phenyl or the phenyl arbitrarily substituted；
    X1And X2Independently for halogen, hydrogen, cyano group or nitro；
    Alkyl described above is unsubstituted branched-chain or straight-chain alkyl.
  3. A kind of 3. azo dyes compounds according to claim 2, it is characterised in that：The R1It is methyl, ethyl, positive third Base, isopropyl or normal-butyl；
    R2It is hydrogen, methyl, ethyl, propyl group, acetylamino, propionamido or benzamido；
    R3It is hydrogen, methyl, ethyl, propyl group, butyl, benzyl, phenylethyl, Phenoxyethyl, methoxy ethyl or cyano ethyl；
    R4It is methyl, ethyl or phenyl；
    X1And X2Independently for hydrogen, Cl, Br, cyano group or nitro.
  4. A kind of 4. azo dyes compounds according to claim 3, it is characterised in that：The R1It is methyl or ethyl；
    R2It is methyl, ethyl or propyl group；
    R3It is methyl or ethyl；
    R4It is methyl or ethyl；
    X1And X2Independently for hydrogen, Cl, Br, cyano group or nitro.
  5. 5. a kind of preparation method of azo dyes compounds as claimed in claim 1, including：
    By Formula II compound
    Diazotising is simultaneously coupled to formula III compoundProduce.
  6. A kind of 6. application of azo dyes compounds as claimed in claim 1, it is characterised in that：Applied to hydrophobic material or Blended material dyeing or stamp containing hydrophobic material.
  7. 7. a kind of dye composite containing azo dyes compounds as claimed in claim 1, includes the change of at least one Formulas I Compound and other at least one dye compositions.
  8. A kind of 8. application of dye composite as claimed in claim 7, it is characterised in that：Applied to hydrophobic material or contain The blended material dyeing of hydrophobic material or stamp.
  9. A kind of 9. dyestuff containing azo dyes compounds as claimed in claim 1 and dispersant.
CN201710936350.2A 2017-10-10 2017-10-10 A kind of azo dyes compounds and its preparation method and application Pending CN107722663A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108947765A (en) * 2018-08-15 2018-12-07 江苏常源新材料科技有限公司 A kind of method of bis-diazotized reaction one-step synthesis o-dibromobenzene

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1711319A (en) * 2002-11-11 2005-12-21 西巴特殊化学品控股有限公司 Phthalimidyl-azo dyes, process for their preparation and their use
CN101454402A (en) * 2006-06-14 2009-06-10 德意志戴斯达纺织品及染料两合公司 Disperse dyes, production and their use
CN104403348A (en) * 2014-11-18 2015-03-11 李百春 Purple disperse dye with high washing fastness and sublimation fastness and preparation method of purple disperse dye
CN104448894A (en) * 2014-11-18 2015-03-25 昌邑福莱蒽特精细化工有限公司 Greenish-blue disperse dye with high washing fastness and sublimation fastness and preparation method thereof
CN104448892A (en) * 2014-11-18 2015-03-25 李百春 Sapphire-blue disperse dye with high washing fastness and sublimation fastness and preparation method thereof
CN104448893A (en) * 2014-11-18 2015-03-25 杭州福莱蒽特精细化工有限公司 Red disperse dye with high washing fastness and sublimation fastness and preparation method thereof
CN105566940A (en) * 2016-01-27 2016-05-11 杭州福莱蒽特精细化工有限公司 Phthalimidyl azo dye and preparation method and application thereof

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1711319A (en) * 2002-11-11 2005-12-21 西巴特殊化学品控股有限公司 Phthalimidyl-azo dyes, process for their preparation and their use
CN101454402A (en) * 2006-06-14 2009-06-10 德意志戴斯达纺织品及染料两合公司 Disperse dyes, production and their use
CN104403348A (en) * 2014-11-18 2015-03-11 李百春 Purple disperse dye with high washing fastness and sublimation fastness and preparation method of purple disperse dye
CN104448894A (en) * 2014-11-18 2015-03-25 昌邑福莱蒽特精细化工有限公司 Greenish-blue disperse dye with high washing fastness and sublimation fastness and preparation method thereof
CN104448892A (en) * 2014-11-18 2015-03-25 李百春 Sapphire-blue disperse dye with high washing fastness and sublimation fastness and preparation method thereof
CN104448893A (en) * 2014-11-18 2015-03-25 杭州福莱蒽特精细化工有限公司 Red disperse dye with high washing fastness and sublimation fastness and preparation method thereof
CN105566940A (en) * 2016-01-27 2016-05-11 杭州福莱蒽特精细化工有限公司 Phthalimidyl azo dye and preparation method and application thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108947765A (en) * 2018-08-15 2018-12-07 江苏常源新材料科技有限公司 A kind of method of bis-diazotized reaction one-step synthesis o-dibromobenzene

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