CN106433184B - Cumarin base heterocycle azo disperse dyes and preparation method thereof - Google Patents

Cumarin base heterocycle azo disperse dyes and preparation method thereof Download PDF

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CN106433184B
CN106433184B CN201610805225.3A CN201610805225A CN106433184B CN 106433184 B CN106433184 B CN 106433184B CN 201610805225 A CN201610805225 A CN 201610805225A CN 106433184 B CN106433184 B CN 106433184B
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formula
component
diazo
preparation
disperse dyes
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CN106433184A (en
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唐炳涛
邱金晶
具本植
张淑芬
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Dalian University of Technology
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Dalian University of Technology
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    • 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
    • C09B29/3678—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only oxygen as heteroatom
    • 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
    • C09B29/3682—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only sulfur as heteroatom
    • 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
    • C09B29/3691—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing nitrogen and sulfur as heteroatom
    • 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
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008—Preparations of disperse dyes or solvent 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
    • D—TEXTILES; PAPER
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    • 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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    • 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
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    • 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
    • D06P3/40—Cellulose acetate
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    • 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
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    • D06P3/79—Polyolefins
    • D06P3/794—Polyolefins using dispersed dyes

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Abstract

The present invention relates to a kind of cumarin base heterocycle azo disperse dyes and preparation method thereof, the cumarin base heterocycle azo disperse dyes are made of diazo component and coupling component two parts, the wherein described coupling component is the heterocycle active methylene compound being coupled under alkaline condition or heterocycle phenolic compound, the diazo component alkalescent heterocycle arylamine or alkalescent anil.The preparation method is in the presence of a stabilizer, to carry out diazotising to alkalescent heterocycle arylamine or alkalescent anil in organic solvent, stable diazosalt solid is precipitated, and after solid is obtained by filtration, it is applied to alkaline coupling, obtains target dyestuff.The dyestuff can be applied to polyester fiber, Fypro, acid fiber by polylactic, polypropylene fibre, acetate fiber dyeing, have excellent dyeing brightness.

Description

Cumarin base heterocycle azo disperse dyes and preparation method thereof
Technical field
The present invention relates to a kind of heterocycle azo disperse dyes and preparation method thereof.
Background technology
Synthetic fibers close structure, crystallinity is high, and dyeing is more difficult, is generally dyed using disperse dyes, to improve The binding force of dyestuff and hydrophobic fibre.
Without containing water soluble groups such as sulfonic group or carboxyls in disperse dyes structure, it is insoluble in water.It need to be with when being commercialized Dispersant is ground together, and when application is dispersed in water by dispersant with insoluble minuteness particle, is used for the high temperature of synthetic fibers High pressure or high temperature pad-dry-cure dyeing.Synthetic fibers include mainly the classes such as azo, anthraquinone, nitrodiphenylamine by structure point with disperse dyes Type, and azo type disperse dyes cover red, yellow, blue whole chromatogram system due to simple in structure, occupy in disperse dyes extremely heavy The status wanted.Disperse dyes containing heterocyclic group have bright in color light, coloring intensity high, have preferable hyperchromic effect and compared with The characteristics such as high molar extinction coefficient are dye species important in disperse dyes.
Azo type heterocyclic disperse dyes are made of diazo component and coupling component two parts.When diazo component can be in hydrochloric acid When middle progress diazotising (diazo component is aniline, chlorine substituted aniline, 1- nitros substituted aniline at this time), coupling component can be Heterocycle arylamine, phenol or heterocycle active methylene compound, (at this time when diazo component is merely able to carry out diazotising in concentrated sulfuric acid Diazo component is alkalescent arylamine, such as：Aminothiophene, aminothiazole, aminobenzothiazole, 2,4- dinitroanilines, 4- nitros- 2- cyano-anilines, 4- nitros -2,6-DCA etc.), coupling component can only be the aniline derivatives being coupled in acid condition Object or heterocycle arylamine.And heterocycle active methylene compound, heterocycle phenolic compound need to be coupled under alkaline condition, alkalescent Arylamine carries out diazotising in concentrated sulfuric acid, when system is transferred to alkalinity, will generate a large amount of inorganic salts, it is difficult to obtain corresponding dyestuff.
Therefore, the purpose of the present invention is to develop a new class of heterocycle azo disperse dyes and its technology of preparing, such dyestuff Coupling component be the heterocycle active methylene compound being coupled under alkaline condition, heterocycle phenolic compound；Diazo component is Alkalescent arylamine；Preparation method is to carry out diazotising to alkalescent arylamine in organic solvent, and it is solid that stable diazol is precipitated It after solid is obtained by filtration, is applied to alkaline coupling, obtains target dyestuff by body.
Invention content
The first aspect of the present invention provides a kind of new heterocycle azo disperse dyes, and the dyestuff is by diazo component and coupling Group is divided into two parts composition, wherein the coupling component is the heterocycle active methylene compound or miscellaneous being coupled under alkaline condition Ring phenolic compound, the diazo component are that can carry out diazotizing heterocycle arylamine or alkalescent aniline derivatives in concentrated sulfuric acid Object.
A kind of heterocycle azo type disperse dyes, the structure with general formula (I)：
A-N=N-B
(Ⅰ)
The diazol and the residue after coupling component coupling that A is the diazo component that diazo component is obtained through diazotising in formula I, The diazo component be selected from general formula (II -1), (II -2), (II -3), (II -4), (II -5), (II -6), (II -7), (II -8), The structure of (II -9) and (II -10)：
In formula (II -1)：
Ra 1For-H ,-CN ,-NO2、-COR、-COAr、-CONH2、-CONHR、-SO2,-COOR or-COAr；
Ra 2For-H ,-R ,-OR ,-NO2,-Cl or-Br；
Ra 3For-H ,-CN ,-NO2、-Ar、-COR、-COAr、-COOR、-COOAr、-CONH2、-CONHR、-SCN、- OCOR ,-CONHAr or-CHO；
In formula (II -2)：
Rb 1For-H ,-R ,-Ar ,-CF3、-CN、-COOR、-CONH2Or-CH2OH；
Rb 2For-H ,-NO2、-R、-ROH、-Ar、-COOR、-CONH2、-SO2R、-SO2Ar or-CN；
In formula (II -3)：
RC 1And RC 2It is each independently selected from-H ,-Cl ,-Br ,-NO2、-R、-OR、-CN、-SO2R、-SO2NR and-CF3；
RC 2For in 1,2 or 3 substituent group；
In formula (II -4)：
Rd 1For-NO2,-Cl ,-Br or-H；
Rd 2For-H ,-Cl or-Br；
In formula (II -5)：
ReFor-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl or-CCl3；
In formula (II -6)：
RfFor-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl or-CCl3；
In formula (II -7)：
RgFor-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-NO2, CN ,-Cl or-CCl3；
In formula (II -8)：
Rh 1For-CN ,-H ,-COOH or-COOCH3；
Rh 2For-SCH ,-H ,-CONH2Or-CH2CN；
Rh 3For-H, phenyl or cyclohexyl；
In formula (II -9)：
Ri 1For-CN ,-NO2,-Cl ,-Br or-I；
Ri 2For-H ,-CN ,-NO2,-Cl ,-Br or-I, and work as Ri 1For-Cl ,-Br or-I when, Ri 2Cannot be-H；
In formula (II -10)：
RjFor-H ,-CN ,-NO2,-Cl ,-Br or-I；
B is the residue after the diazol coupling of coupling component and diazo component in formula (I), and the coupling component is selected from logical Structure shown in formula (III -1), (III -2), (III -3), (III -4), (III -5), (III -6), (III -7) and (III -8)：
In formula (III -1)：
Rj 1For-H ,-CH3、-Ar、-CF3,-CN ,-COOR or-CONHR；Rj 2For-H ,-Ar ,-ArCl or-ArSO2NHR；
In formula (III -2)：
Rk 1For-R ,-OR ,-NHR, COOR ,-Ar or-CN；
Rk 2For-H, R ,-Ar ,-CN ,-COOR ,-SO2NHR or-CONHR；
Rk 3For-R ,-Ar or cyclohexyl；
In formula (III -3)：
RLFor-R ,-OR ,-NO2,-CN ,-Cl ,-Br ,-COOR or-Ar；
In formula (III -4)：
Rm 1For-R ,-OR, COOR ,-Ar or-CN；
Rm 2For-H, R ,-Ar ,-CN ,-COOR ,-SO2NHR or-CONHR；
In formula (III -5)：
Rn 1For-R ,-OR, COOR ,-Ar or-CN；
Rn 2For-H, R ,-Ar ,-CN ,-COOR ,-SO2NHR or-CONHR；
In formula (III -6)：
Ro 1For-R ,-CH2CH2CH2OH、-CH2CH2OH、-CH2CH2CN or-Ar；
Ro 2For-H, R ,-Ar ,-CN ,-COOR ,-SO2NHR or-CONHR；
In formula (III -7)：
Rp 1For-R, cyclohexyl ,-CH2CH2CH2OH、-CH2CH2OH、-CH2CH2CN or-Ar；
Rp 2For-H ,-NO2、-CN、-Cl、-Br、-COOR、-SO2NHR or-CONHR；
In formula (III -8)：
Rq 1For-R, cyclohexyl ,-CH2CH2CH2OH、-CH2CH2OH、-CH2CH2CN or-Ar；
Rq 2For-R, cyclohexyl ,-CH2CH2CH2OH、-CH2CH2OH、-CH2CH2CN or-Ar；
In formula (II -1) to formula (II -7) and formula (III -1) to formula (III -8)：
R is hydrogen, C1-4Alkyl or C1-4Alkoxy；
Ar is phenyl.
The second aspect of the present invention provides the system of the heterocycle azo type disperse dyes of the present invention shown in general formula (I) Preparation Method, this method comprises the following steps：
(1) diazo component described in claim 1, the concentrated sulfuric acid, organic solvent and stabilizer are added in reaction vessel A, After being cooled to 0010 DEG C, diazo reagent is added portionwise, reacts 0.1010h, the diazosalt solid of diazo component is obtained by filtration；
(2) coupling component described in claim 1 and water are added in reaction vessel B, with 10% sodium hydroxide tune pH value To 8012, coupling component is made to dissolve, be cooled to 0010 DEG C, the diazol for being added with stirring the diazo component that step (1) obtains is solid Body, while being reacted 1010h in 8010 ranges with the pH value of 10% sodium carbonate liquor control reaction at 0010 DEG C, obtaining formula (I) Compound；
The wherein described diazo reagent be nitrosyl sulfuric acid, butyl nitrite, nitrite tert-butyl, isoamyl nitrite, Amyl nitrite, isobutyl nitrite, Isopropyl Nitrite, the sodium nitrite solution that mass concentration is 30%, sub- sour sodium solid One or both of.
Further, the molar ratio of the diazo reagent described in step (1) and diazo component is 101.05:1.
Further, the molar ratio of the diazo component described in step (1), the concentrated sulfuric acid and stabilizer is 1:103: 103
Further, the total amount that the diazo component described in step (1), the concentrated sulfuric acid are added with stabilizer accounts for reaction system The 5030% of total weight.
Further, the molar ratio of the diazosalt solid of the coupling component described in step (2) and diazo component It is 0.801:0.801.05.
Further, in step (1), the addition time of diazo reagent is 0.101h.
Further, in step (2), the time for being added with stirring the diazosalt solid of diazo component is 5060min.
Further, the organic solvent is ethyl acetate, ether, glycol monoethyl ether, glycol dimethyl ether, second two One kind in diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, ethyl alcohol, isopropanol, dioxane, Two or three.
Further, the stabilizer be fluoboric acid, sodium fluoborate, zinc acetate, zinc chloride, benzene sulfonic acid, 1-naphthalene sulfonic aicd, One kind in 2- naphthalene sulfonic acids, bis- naphthalene sulfonic acids of 1,5-, bis- naphthalene sulfonic acids of 2,6-, methylene dinaphthalene sulfonic acid, di-2-ethylhexylphosphine oxide methyl naphthalene sulfonic acid Or two kinds.
The third aspect of the present invention provide heterocycle azo type dye of the present invention polyester fiber, Fypro, Application in acid fiber by polylactic, polypropylene fibre, acetate fiber dyeing.
Compared with the existing technology, beneficial effects of the present invention：
1. its coupling component is heterocycle active methylene compound, heterocycle phenols chemical combination in the structure of the compound of the present invention Object, diazo component are alkalescent arylamine, and the dyeing brightness of acquisition is high.
2. being to carry out diazotising to alkalescent arylamine in organic solvent in the preparation method of the compound of the present invention, it is precipitated Stable diazosalt solid, after solid is obtained by filtration, by it applied to alkaline coupling, acquisition target dyestuff, this method and in sulphur It carries out diazotizing conventional method in acid to compare, sulfuric acid dosage is down to 2 moles times of amounts hereinafter, reducing 8 moles of sulfuric acid times amount or more； And the diazol that this method obtains is stable solid, can be used for alkaline coupling, obtains Novel disperse dyestuff.
3. the compounds of this invention can be used for polyester fiber, Fypro, acid fiber by polylactic, polypropylene fibre, acetic acid The dyeing of fiber, part of compounds can be additionally used in pH sensitivity detection fields.
Description of the drawings
Fig. 1 is the mass spectrogram of dye composition 1#；
The FT-IR that Fig. 2 is dye composition 1# schemes；
Fig. 3 is the nuclear magnetic spectrogram of dye composition 1#；
Fig. 4 is the mass spectrogram of dye composition 2#；
The FT-IR that Fig. 5 is dye composition 2# schemes；
Fig. 6 is the nuclear magnetic spectrogram of dye composition 2#；
Fig. 7 is the mass spectrogram of dye composition 3#；
The FT-IR that Fig. 8 is dye composition 3# schemes；
Fig. 9 is the nuclear magnetic spectrogram of dye composition 3#；
Figure 10 is uv-visible absorption spectras of the dye composition 3# at different pH；
Figure 11 is the mass spectrogram of dye composition 4#；
The FT-IR that Figure 12 is dye composition 4# schemes；
Figure 13 is the nuclear magnetic spectrogram of dye composition 4#.
Specific implementation mode
In order to keep the purpose of the present invention, scheme, flow and advantage more clear apparent, in conjunction with the accompanying drawings and embodiments to this hair It is bright to be described in further detail, it is notable that specific embodiment is not used to only as the present invention is illustrated herein Limit the present invention.In following embodiments, unless otherwise specified, used experimental method is conventional method, material therefor, examination Agent etc. can chemically company be bought.
Unless otherwise stated, the technical term used in the present invention has following meaning.
The term " alkyl " used in the present invention includes straight chained alkyl and branched alkyl.Such as refer to single alkyl such as " third Base ", then only refer in particular to straight chained alkyl, such as refers to that single branched alkyl such as " isopropyl ", then only refers in particular to branched alkyl.For another example " C1-4Alkane Base " includes C1-3Alkyl, methyl, ethyl, n-propyl, isopropyl and tertiary butyl.Similar rule is also suitable to be made in this manual Other groups.
In formula (II -1)：Ra 1Preferably-H ,-CN ,-NO2、-COR、-COAr、-CONH2；More preferably-H ,-CN ,-NO2； Most preferably-H ,-NO2；Ra 2Preferably-H ,-R ,-OR ,-NO2、-Cl；More preferably-H ,-R ,-OR ,-NO2；Most preferably-H ,- NO2；Ra 3Preferably-H ,-CN ,-NO2,-Ar ,-COR ,-COAr, more preferably-H ,-CN ,-NO2、-Ar、-COAr；Most preferably- H、-NO2、-Ar。
In formula (II -2)：Rb 1Preferably-H ,-R ,-Ar ,-CF3、-CN、-COOR；More preferably-H ,-R ,-Ar ,-CF3、- CN；Most preferably-H ,-Ar ,-CF3、-CN；Rb 2Preferably-H ,-NO2、-R、-ROH、-Ar、-COOR、-SO2Ar or-CN；It is more excellent It is selected as-H ,-NO2、-Ar、-COOR、-SO2Ar or-CN；Most preferably-H ,-NO2、-Ar、-SO2Ar。
In formula (II -3)：It is preferred that RC 1And RC 2It is each independently selected from-H ,-Cl ,-Br ,-NO2、-R、-OR；More preferably- H、-Cl、-NO2、-OR；Most preferably-H ,-Cl ,-NO2；RC 2It is preferably located on 1,2 positions；More preferably it is located in 1.
In formula (II -4)：Rd 1Preferably-NO2,-Cl or-H；More preferably-NO2Or-H；Most preferably-NO2；Rd 2It is preferred that For-H ,-Cl；More preferably-H.
In formula (II -5)：RePreferably-H ,-Ar ,-OR ,-CN ,-Cl or-CCl3；More preferably-H ,-Ar ,-CN or- CCl3；Most preferably-H ,-CN or-CCl3。
In formula (II -6)：RfPreferably-H ,-R ,-Ar ,-OR ,-CN,；More preferably-H ,-Ar ,-OR ,-CN；Most preferably For-H ,-Ar ,-CN.
In formula (II -7)：RgPreferably-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl；More preferably-H ,-R ,-Ar ,-CN ,- Cl；Most preferably-H ,-Ar ,-CN.
In formula (II -8)：Rh 1Preferably-CN ,-H ,-COOCH3；More preferably-CN ,-H；Rh 2Preferably-CONH2、-H、 Or-CH2CN；More preferably-H or-CH2CN；Rh 3Preferably-H, phenyl；More preferably phenyl.
In formula (II -9)：Ri 1Preferably-CN ,-NO2,-Br or-Cl；More preferably-CN ,-NO2Or-Cl；Most preferably- NO2Or-Cl；Ri 2Preferably-H ,-CN ,-NO2,-Br or-Cl, more preferably-H ,-NO2、-Cl；Most preferably-H ,-Cl；And work as Ri 1For Cl, Br or I when, Ri 2Cannot be H.
In formula (II -10)：RjPreferably-H ,-CN ,-NO2、-Br；More preferably-H ,-NO2；Most preferably-H.
In formula (III -1)：Rj 1Preferably-H ,-CH3,-Ar ,-COOR or-CONHR；More preferably-H ,-CH3,-Ar or- CONHR；Most preferably-H ,-Ar；Rj 2Preferably-H ,-Ar or-ArSO2NHR；More preferably-H ,-Ar；Most preferably-Ar.
In formula (III -2)：Rk 1Preferably-R ,-OR ,-NHR, COOR or-CN；More preferably-R ,-NHR, COOR or-CN；Most Preferably-R, COOR or-CN；Rk 2Preferably R ,-Ar ,-CN or-CONHR；More preferably R ,-Ar ,-CN；Most preferably R ,-Ar； Rk 3Preferably-R ,-Ar；More preferably-R.
In formula (III -3)：RLPreferably-R ,-OR ,-NO2,-COOR or-Ar；More preferably-R ,-NO2,-COOR or-Ar； Most preferably-R ,-NO2、-COOR。
In formula (III -4)：Rm 1Preferably-R ,-OR, COOR；More preferably-R, COOR；Most preferably-R；Rm 2For-H, R ,- Ar、-CN、-COOR；More preferably-H ,-Ar ,-CN ,-COOR；Most preferably-H ,-Ar.
In formula (III -5)：Rn 1Preferably-R ,-OR, COOR ,-Ar；More preferably-R ,-OR, COOR；Most preferably-R ,- OR；Rn 2Preferably-H, R ,-Ar ,-SO2NHR or-CONHR；More preferably-H, R ,-Ar or-CONHR；Most preferably-H, R.
In formula III -6：Ro 1Preferably-R ,-CH2CH2CH2OH、-CH2CH2OH；More preferably-R ,-CH2CH2OH；Ro 2It is preferred that For-H, R ,-Ar ,-SO2NHR or-CONHR；More preferably-H, R ,-Ar ,-CONHR；Most preferably-H ,-Ar.
In formula (III -7)：Rp 1Preferably-R, cyclohexyl ,-CH2CH2CH2OH、CH2CH2CN；More preferably-R ,- CH2CH2CH2OH、CH2CH2CN；Most preferably-R, CH2CH2CN；Rp 2Preferably-H ,-NO2、-CN、-Cl、-Br；More preferably- H、-NO2、-CN、-Cl；Most preferably-H ,-NO2。
In formula (III -8)：Rq 1Preferably-R ,-CH2CH2CH2OH、-CH2CH2OH；More preferably-R ,-CH2CH2OH；Rq 2It is excellent It is selected as-R ,-CH2CH2CH2OH、-CH2CH2OH；More preferably-R ,-CH2CH2OH。
In formula (II -1) to formula (II -7) and formula (III -1) to formula (III -8)：R is preferably-H, C1-4Alkyl or C1-4Alcoxyl Base；More preferably hydrogen, C1-2Alkyl or C1-2Alkoxy；Further preferably-H, ethyl, methoxyl group.
Ar is phenyl.
On the other hand, the present invention also provides the preparation method of compound described above, which is in dense sulphur In the presence of acid, diazotising is carried out to diazo component in organic solvent, stable diazosalt solid is precipitated, the solid is obtained by filtration Afterwards, coupling reaction is carried out with coupling component under alkaline condition, obtains target dyestuff.Specifically comprise the following steps：
(1) diazo component of the present invention, the concentrated sulfuric acid, organic solvent and stabilizer are added in reaction vessel A, cooling To after 0010 DEG C, diazo reagent is added portionwise, reacts 0.1010h, the diazosalt solid of diazo component is obtained by filtration；
(2) coupling component described in claim 1 and water are added in reaction vessel B, with 10% sodium hydroxide tune pH value To 8012, coupling component is made to dissolve, be cooled to 0010 DEG C, the diazol for being added with stirring the diazo component that step (1) obtains is solid Body is dissolved in control pH value in reaction to 8010 ranges with 10% sodium carbonate, reacts 1010h at 0010 DEG C, obtain the chemical combination of formula (I) Object；
The wherein described diazo reagent be nitrosyl sulfuric acid, butyl nitrite, nitrite tert-butyl, isoamyl nitrite, Amyl nitrite, isobutyl nitrite, Isopropyl Nitrite, the sodium nitrite solution that mass concentration is 30%, sub- sour sodium solid One or both of.
In preferred technical solution, the diazo reagent is nitrosyl sulfuric acid, butyl nitrite, the tertiary fourth of nitrous acid One or both of ester, isoamyl nitrite, amyl nitrite, isobutyl nitrite；More preferably nitrosyl sulfuric acid, nitrous Tert-butyl acrylate, isoamyl nitrite, isobutyl nitrite；Most preferably nitrosyl sulfuric acid, nitrite tert-butyl.
In preferred technical solution, the molar ratio of diazo reagent and diazo component described in step (1) It is 1.0501:1, more preferably 1.0201:1, most preferably 1:1；The molar ratio of diazo component and the concentrated sulfuric acid is 1:103, More preferably 1:102.5 most preferably 1:102.
In preferred technical solution, diazo component, the concentrated sulfuric acid and stabilizer described in step (1) feed intake mole Than being 1:103:103, more preferably 1:102.5:102.5 most preferably 1:102:102.
In preferred technical solution, total amount that diazo component, the concentrated sulfuric acid described in step (1) are added with stabilizer Account for the 5030% of reaction system total weight, more preferably 5020%, most preferably 5015%.
In preferred technical solution, the diazosalt solid of coupling component and diazo component described in step (2) Molar ratio is 1:101.05；More preferably 1:101.03 most preferably 1:1.
In preferred technical solution, in step (1), the time that diazo reagent is added dropwise is 0.101h, more preferably 0.100.5h。
In preferred technical solution, in step (2), the time for being added with stirring the diazosalt solid of diazo component is 5060min, more preferably 10040min.
In preferred technical solution, the organic solvent is ethyl acetate, ether, glycol monoethyl ether, ethylene glycol Dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, ethyl alcohol, isopropanol, dioxy six One kind, two or three, more preferably ethyl acetate, glycol monoethyl ether, glycol dimethyl ether, ethylene glycol diethyl in ring One kind in ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran, dioxane, two or three, most preferably For ethyl acetate, glycol monoethyl ether, glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, ethylene glycol diethyl One kind in ether, two or three.
In preferred technical solution, the stabilizer is fluoboric acid, sodium fluoborate, zinc acetate, zinc chloride, benzene sulphur One or both of acid, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, 1,5-, bis- naphthalene sulfonic acids, 2,6-, bis- naphthalene sulfonic acids, NNO, MF, more preferably Fluoboric acid, zinc chloride, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, bis- naphthalene sulfonic acids of 1,5-, bis- naphthalene sulfonic acids of 2,6-, methylene dinaphthalene sulfonic acid, methylene The double methyl naphthalene sulfonic acids of base are one or two kinds of, most preferably fluoboric acid, 1,5-, bis- naphthalene sulfonic acids, 2,6-, bis- naphthalene sulfonic acids, methylene dinaphthalene Sulfonic acid, di-2-ethylhexylphosphine oxide methyl naphthalene sulfonic acid are one or two kinds of.
The preparation of 1 compound 1# of embodiment
(1) by 1.5g 5-Amino-2-benzimidazolinones, the 1g concentrated sulfuric acids, 80ml ethylene glycol diethyl ethers, 5g 1,5- naphthalenedisulfonic acids It is added in there-necked flask, 5 DEG C is cooled in ice-water bath, 3g nitrite tert-butyls are added dropwise, time for adding 0.5h is anti-after being added dropwise It answers 2 hours；Diazosalt solid is obtained after filtering；(2) 1.34g 3- methyl-1s--5 pyrazolone of phenyl, 100ml water are added anti- It answers in device, with 10% sodium hydroxide solution tune pH value to 10, is cooled to 5 DEG C, be added with stirring the 5- aminobenzenes that step (1) obtains And imidazolone diazol, it is used in combination 10% sodium carbonate liquor control ph to be added in 9, half an hour, and react 2hr at 5 DEG C；Reaction It finishes, filters, it is neutrality to be washed till filtrate using ice water, obtains heterocycle azo disperse dyes (compound 1#) after dry, is coupled Rate is 95%.
Occurs [M-H]-quasi-molecular ions of compound 1# in mass spectrum (Fig. 1) at m/z 333.1, in infrared spectrum (Fig. 2) In 1700cm-1For carbonyl characteristic peak, 8.5-10ppm is Hydrogen Proton peak on aromatic ring in H-NMR nuclear magnetic spectrograms (Fig. 3).
The preparation of 2 compound 2# of embodiment
(1) by 1.83g 2,4- dinitroanilines, the 2g concentrated sulfuric acids, 40ml glycol dimethyl ethers, 4g 1,5- naphthalenedisulfonic acids add Enter in there-necked flask, 3 DEG C are cooled in ice-water bath, 3g nitrosyl sulfuric acids are added dropwise, time for adding 0.5h reacts 2 after being added dropwise Hour；Diazosalt solid is obtained after filtering；(2) 0.81g 3- Methyl-5-pyrazolones, 80ml water are added in reactor, are used 10% sodium hydroxide solution tune pH value is cooled to 4 DEG C to 11, is added with stirring 2, the 4- dinitroaniline weights that step (1) obtains Nitrogen salt is used in combination 10% sodium carbonate liquor control ph to be added in 9, half an hour, and 2hr is reacted at 5 DEG C；Reaction finishes, filtering, It is neutrality to be washed till filtrate using ice water, and heterocycle azo disperse dyes (compound 2#) are obtained after dry, and coupling yield is 99%.
Occur [M-H] of compound 2# at m/z 291 in mass spectrum (Fig. 4)-Quasi-molecular ions, in infrared spectrum (Fig. 5) 1690cm-1For carbonyl characteristic peak, 8.2-9.5ppm is Hydrogen Proton peak on aromatic ring in H-NMR nuclear magnetic spectrograms (Fig. 6).
The preparation of 3 compound 3# of embodiment
(1) by 1.45g 2- amino -5- nitrothiazoles, 60ml ethyl acetate, the 5g concentrated sulfuric acids, (30% is water-soluble for 5g zinc acetates Liquid) be added in there-necked flask, be cooled to 005 degree Celsius in ice-water bath, 2g nitrosyl sulfuric acids be added, after react 2 hours；Filtering After obtain diazosalt solid；(2) 0.97g 8-hydroxyquinolines, 80ml water are added in reactor, with 10% sodium hydroxide solution It adjusts pH value to 10, is cooled to 5 DEG C, is added with stirring the 2- amino -5- nitrothiazole diazols obtained in step (1), is used in combination 10% sodium carbonate liquor control ph adds in 9, half an hour, and 2hr is reacted at 5 DEG C；Reaction finishes, and filtering utilizes ice water It is neutrality to be washed till filtrate, and heterocycle azo disperse dyes (compound 3#) are obtained after dry, and coupling yield is 80%.
Occur [M-H] of compound 3# at m/z 300 in mass spectrum (Fig. 7)-Quasi-molecular ions, in infrared spectrum (Fig. 8) 1550cm-1With 1350cm-1For nitro characteristic peak, 8.2-9.5ppm is Hydrogen Proton peak on aromatic ring in H-NMR nuclear magnetic spectrograms (Fig. 9). It is purple in its uv-visible absorption spectra (Figure 10) as can be seen that when solution ph is 6, when solution ph is 8, The a length of 626nm of maximum absorption wave, for blue, color change is notable, has pH sensitive color change characteristics, can be used for the bore hole inspection of pH It surveys.
The preparation of 4 compound 4# of embodiment
(1) by 2.07g 4- nitros -2,6-DCA, the 3g concentrated sulfuric acids, 50ml glycol dimethyl ethers, 3g 1,5- naphthalenes two Sulfonic acid is added in there-necked flask, is cooled to 4 degrees Celsius in ice-water bath, be added dropwise sodium nitrite solution (30%, institute's dripping quantity and diazonium group The molar ratio divided is 1.05：1), time for adding 0.5h reacts 1 hour after being added dropwise；Diazosalt solid is obtained after filtering； (2) 1.24g 3- methyl-1s--5 pyrazolone of phenyl, 50ml water are added in reactor, with 10% sodium hydroxide solution tune pH Value is cooled to 6 DEG C, is added with stirring 4- nitros -2,6-DCA diazol to 11, and 10% sodium carbonate liquor is used in combination to control pH Value adds in 10, half an hour, and 2h is reacted at 8 DEG C；Reaction finishes, filtering, and it is neutrality to be washed till filtrate using ice water, after dry Heterocycle azo disperse dyes (compound 4#) are obtained, coupling yield is 92%.
Occur [M-H] of compound 3# at m/z 390 in mass spectrum (Figure 11)-Quasi-molecular ions, in infrared spectrum (Figure 12) It is carbonyl characteristic peak 1660,7-8.6ppm is Hydrogen Proton peak on aromatic ring in nuclear magnetic spectrogram (Figure 13).
Embodiment 5
(1) by 1.96g 2- amino -3,5- dinitro thiophenes, the 1g concentrated sulfuric acids, 60ml glycol dimethyl ethers, 5g 2,6- naphthalenes Disulfonic acid is added in there-necked flask, and 3 DEG C are cooled in ice-water bath, and 4g isoamyl nitrites are added dropwise, and time for adding 0.5h is dripped It is reacted 2 hours after finishing；Diazosalt solid is obtained after filtering；(2) by 1.74g N- ethyl -3- cyano -4- methyl -6- hydroxyls -2- Pyridone, 100ml water are added in reactor, with 10% sodium hydroxide solution tune pH value to 11, are cooled to 5 DEG C, are added with stirring In 2- amino -3,5- dinitro thiophene diazols that step (1) obtains, it is used in combination 10% sodium carbonate liquor control ph small 9, half When it is interior add, and at 5 DEG C react 2hr；Reaction finishes, filtering, and it is neutrality to be washed till filtrate using ice water, and heterocycle idol is obtained after dry Nitrogen disperse dyes.
Embodiment 6
(1) by 1.0g thiazolamines, 60ml ethyl acetate, the 5g concentrated sulfuric acids, 5g fluoboric acid (40% aqueous solution) addition three In mouthful bottle, 5 DEG C are cooled in ice-water bath, 0.7g sodium nitrites are added, after react 2 hours；It is solid that diazol is obtained after filtering Body；(2) 1.62g 4 hydroxy coumarins, 80ml water are added in reactor, it is cold with 10% sodium hydroxide solution tune pH value to 11 But to 8 DEG C, it is added with stirring the thiazolamine diazol that step (1) obtains, 10% sodium carbonate liquor control ph is used in combination to exist 9, it adds in half an hour, and 2hr is reacted at 5 DEG C；Reaction finishes, filtering, and it is neutrality to be washed till filtrate using ice water, is obtained after dry Heterocycle azo disperse dyes.
Embodiment 7-22
Utilize 3- cyano -6- hydroxy-4-methyl -2- pyridones, N- ethyl -3- cyano -4- methyl -6- hydroxyl -2- pyridines Ketone, hexahydroxy pyridone, 3- formamido group -4- methyl -6- hydroxy-ns-ethylpyridine ketone, 4 hydroxy coumarin, 7- nitros -4- Hydroxycoumarin, 7- methyl -4 hydroxy coumarin, 4- oxyquinolines, 2,4- dihydroxy quinoline, 7- chloro-4-hydroxyls quinoline, N- first Base -4- hydroxyl -2- quinolinones, 4- hydroxyl -1,8- naphthalimides, N- methyl -4- hydroxyl -1,8- naphthalimides, 1- (4- chlorphenyls) -3- methyl -5- pyrazolones, 1- phenyl -3- methyl -4- benzoyl -5- pyrazolones, 3- methyl -5- pyrroles Oxazolone replace embodiment 1 in 3- methyl-1s--5 pyrazolone of phenyl, under alkaline condition respectively with 5-Amino-2-benzimidazolinone Diazosalt solid coupling, obtain corresponding heterocycle azo disperse dyes.
Embodiment 23-30
Utilize 2,4- dinitroanilines, 4- nitros -2,6- dibromo aniline, 4- nitro -2- cyano-anilines, 2- amino benzo thiophenes Azoles, 6- nitrothiazoles, 5- amino benzo -1,2,3- thiadiazoles, 2- aminothiophenes, 1- phenyl -3- methyl -4- cyano -5- amino Pyrazoles replaces the 5-Amino-2-benzimidazolinone in embodiment 1, carries out diazotising, corresponding diazosalt solid is obtained, in alkaline condition It is lower respectively with 3- methyl-1s--5 pyrazolone of phenyl, obtain corresponding heterocycle azo disperse dyes.
Embodiment 31-38
Utilize ethyl acetate, ether, glycol monoethyl ether, glycol dimethyl ether, tetrahydrofuran, ethyl alcohol, isopropanol, dioxy Six rings replace the ethylene glycol diethyl ether in embodiment 1 as the diazotizing solvent of 5-Amino-2-benzimidazolinone, obtain corresponding diazonium Salt solid is coupled with 3- methyl-1s--5 pyrazolone of phenyl respectively under alkaline condition, obtains corresponding heterocycle azo dispersion dye Material.
Embodiment 39-46
Using fluoboric acid, sodium fluoborate, zinc acetate, benzene sulfonic acid, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, bis- naphthalene sulfonic acids of 2,6-, NNO, MF replaces stabilizer of 1, the 5- naphthalenedisulfonic acids as 5-Amino-2-benzimidazolinone in embodiment 1, obtains corresponding diazosalt solid, It is coupled respectively with 3- methyl-1s--5 pyrazolone of phenyl under alkaline condition, obtains corresponding heterocycle azo disperse dyes.
Embodiment 47-54
Utilize nitrosyl sulfuric acid, butyl nitrite, isoamyl nitrite, amyl nitrite, isobutyl nitrite, nitrous acid Isopropyl ester replaces diazo reagent of the nitrite tert-butyl as 5-Amino-2-benzimidazolinone in embodiment 1, obtains corresponding weight Nitrogen salt solid obtains corresponding heterocycle azo disperse dyes with 3- methyl-1s--5 pyrazolone of phenyl respectively under alkaline condition.
Embodiment 55-70
Utilize 3- cyano -6- hydroxy-4-methyl -2- pyridones, hexahydroxy pyridone, 3- formamido group -4- methyl -6- hydroxyls Base-N- ethylpyridines ketone, 4 hydroxy coumarin, 7- nitros -4 hydroxy coumarin, 7- methyl -4 hydroxy coumarin, 4- hydroxyl quinolines Quinoline, 2,4- dihydroxy quinoline, 7- chloro-4-hydroxyls quinoline, N- methyl -4- hydroxyl -2- quinolinones, two formyl of 4- hydroxyls -1,8- naphthalene Imines, N- methyl -4- hydroxyl -1,8- naphthalimides, 1- (4- chlorphenyls) -3- methyl -5- pyrazolones, 1- phenyl -3- Methyl -4- benzoyl -5- pyrazolones, 3- Methyl-5-pyrazolones replace the 3- Methyl-5-pyrazolones in embodiment 2, in alkali Property under the conditions of respectively with the diazosalt solid of 2,4- dinitroanilines be coupled, obtain corresponding heterocycle azo disperse dyes.
Embodiment 71-78
Utilize 2- amino -3,5- dinitro thiophenes, 4- nitro -2,6- dibromo anilines, 4- nitro -2- cyano-anilines, 2- ammonia Base benzothiazole, 6- nitrothiazoles, 5- amino benzo -1,2,3- thiadiazoles, 2- aminothiophenes, 1- phenyl -3- methyl -4- cyanogen Base -5- amino-pyrazols replace 2, the 4- dinitroanilines in embodiment 2, carry out diazotising, corresponding diazosalt solid are obtained, in alkali Property under the conditions of respectively with 3- Methyl-5-pyrazolones be coupled, obtain corresponding heterocycle azo disperse dyes.
Embodiment 79-86
Utilize ethyl acetate, ether, glycol monoethyl ether, ethylene glycol diethyl ether, tetrahydrofuran, ethyl alcohol, isopropanol, dioxy Six rings replace the glycol dimethyl ether in embodiment 2 as the diazotizing solvent of 2,4- dinitroanilines, obtain corresponding diazol Solid is coupled respectively with 3- Methyl-5-pyrazolones, obtains corresponding heterocycle azo disperse dyes under alkaline condition.
Embodiment 87-94
Utilize fluoboric acid, sodium fluoborate, zinc acetate, benzene sulfonic acid, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, bis- naphthalene sulfonic acids of 2,6-, methylene Two naphthalene sulfonic acids of base, di-2-ethylhexylphosphine oxide methyl naphthalene sulfonic acid replace 1, the 5- naphthalenedisulfonic acids in embodiment 2 as 2,4- dinitroaniline weights The stabilizer of nitrogen salt obtains corresponding diazosalt solid, is coupled respectively with 3- Methyl-5-pyrazolones under alkaline condition, obtains phase Answer heterocycle azo disperse dyes.
Embodiment 95-102
Utilize isoamyl nitrite, butyl nitrite, nitrite tert-butyl, amyl nitrite, isobutyl nitrite, nitrous Isopropyl propionate replaces diazo reagent of the nitrosyl sulfuric acid as 2,4- dinitroanilines in embodiment 2, obtains corresponding diazonium Salt solid is coupled respectively with 3- Methyl-5-pyrazolones, obtains corresponding heterocycle azo disperse dyes under alkaline condition.
Embodiment 103-118
Utilize 3- cyano -6- hydroxy-4-methyl -2- pyridones, hexahydroxy pyridone, 3- formamido group -4- methyl -6- hydroxyls Base-N- ethylpyridines ketone, 7- nitros -4 hydroxy coumarin, 7- methyl -4 hydroxy coumarin, 4- oxyquinolines, 2,4- dihydroxy Quinoline, 7- chloro-4-hydroxyls quinoline, N- methyl -4- hydroxyl -2- quinolinones, 4- hydroxyl -1,8- naphthalimides, N- methyl -4- Hydroxyl -1,8- naphthalimides, 1- (4- chlorphenyls) -3- methyl -5- pyrazolones, 1- phenyl -3- methyl -4- benzoyls Base -5- pyrazolones, 3- Methyl-5-pyrazolones replace embodiment 3 in 8-hydroxyquinoline, under alkaline condition respectively with 2- ammonia The diazosalt solid of base -5- nitrothiazoles is coupled, and obtains corresponding heterocycle azo disperse dyes.
Embodiment 119-126
Utilize 2,4- dinitroanilines, 4- nitros -2,6- dibromo aniline, 4- nitro -2- cyano-anilines, 2- amino benzo thiophenes Azoles, 6- nitrothiazoles, 5- amino benzo -1,2,3- thiadiazoles, 2- aminothiophenes, 1- phenyl -3- methyl -4- cyano -5- amino Pyrazoles replaces the 2- amino -5- nitrothiazoles in embodiment 3, carries out diazotising, corresponding diazosalt solid is obtained, in alkaline condition It is lower to be coupled respectively with 8-hydroxyquinoline, obtain corresponding heterocycle azo disperse dyes.
Embodiment 127-134
Using glycol dimethyl ether, ether, glycol monoethyl ether, ethylene glycol diethyl ether, tetrahydrofuran, ethyl alcohol, isopropanol, Dioxane replaces the conduct diazotizing solvent of 2- amino -5- nitrothiazoles of ethyl acetate in embodiment 3, obtains corresponding diazonium Salt solid is coupled respectively with 8-hydroxyquinoline, obtains corresponding heterocycle azo disperse dyes under alkaline condition.
Embodiment 135-142
Utilize 1,5- naphthalenedisulfonic acids, sodium fluoborate, fluoboric acid, benzene sulfonic acid, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, 2,6- dinaphthyl sulphurs Acid, methylene dinaphthalene sulfonic acid, di-2-ethylhexylphosphine oxide methyl naphthalene sulfonic acid replace the zinc acetate in embodiment 3 as 2- amino -5- nitro thiophenes The stabilizer of azoles diazol obtains corresponding diazosalt solid, is coupled respectively with 8-hydroxyquinoline under alkaline condition, obtains corresponding Heterocycle azo disperse dyes.
Embodiment 143-150
It is different using isoamyl nitrite, sodium nitrite, butyl nitrite, nitrite tert-butyl, amyl nitrite, nitrous acid Butyl ester, Isopropyl Nitrite replace diazo reagent of the nitrosyl sulfuric acid as 2- amino -5- nitrothiazoles in embodiment 3, Corresponding diazosalt solid is obtained, is coupled respectively with 8-hydroxyquinoline under alkaline condition, obtains corresponding heterocycle azo disperse dyes.
Embodiment 151-166
Utilize 3- cyano -6- hydroxy-4-methyl -2- pyridones, hexahydroxy pyridone, 3- formamido group -4- methyl -6- hydroxyls Base-N- ethylpyridines ketone, 7- nitros -4 hydroxy coumarin, 7- methyl -4 hydroxy coumarin, 4- oxyquinolines, 2,4- dihydroxy Quinoline, 7- chloro-4-hydroxyls quinoline, N- methyl -4- hydroxyl -2- quinolinones, 4- hydroxyl -1,8- naphthalimides, N- methyl -4- Hydroxyl -1,8- naphthalimides, 1- (4- chlorphenyls) -3- methyl -5- pyrazolones, 1- phenyl -3- methyl -4- benzoyls Base -5- pyrazolones, 3- Methyl-5-pyrazolones replace 3- methyl-1s--5 pyrazolone of phenyl in embodiment 4, in alkaline item It is coupled respectively with the diazosalt solid of 4- nitros -2,6-DCA under part, obtains corresponding heterocycle azo disperse dyes.
Embodiment 167-174
Using 2,4- dinitroanilines, thiazolamine, 4- nitros -2,6- dibromo aniline, 4- nitro -2- cyano-anilines, 2- aminobenzothiazoles, 6- nitrothiazoles, 5- amino benzo -1,2,3- thiadiazoles, 2- aminothiophenes, 1- phenyl -3- methyl -4- Cyano -5- amino-pyrazols replace 4- nitros -2,6-DCA in embodiment 4, carry out diazotising, and it is solid to obtain corresponding diazol Body is coupled respectively with 3- methyl-1s--5 pyrazolone of phenyl, obtains corresponding heterocycle azo disperse dyes under alkaline condition.
Application examples 1
Experiment is sanded in the dyestuff that embodiment 1 obtains：The dispersant NNO of dyestuff, 1.00g that the embodiment 1 of 0.50g is obtained It is placed in the water of 2.80g equipped with pearl is sanded and is sanded in the sand milling pipe of stick, 1h is sanded in stirring, the dyestuff diffusion that embodiment 1 obtains Performance reaches as defined in HGT3399-2001 5 grades.
Application examples 2
Experiment is sanded in the dyestuff that embodiment 2 obtains：The dispersant NNO of dyestuff, 1.00g that the embodiment 2 of 0.50g is obtained It is placed in the water of 2.80g equipped with pearl is sanded and is sanded in the sand milling pipe of stick, 1h is sanded in stirring, the dyestuff diffusion that embodiment 2 obtains Performance reaches as defined in HGT3399-2001 5 grades.
Application examples 3
Experiment is sanded in the dyestuff that embodiment 4 obtains：The dispersant NNO of dyestuff, 1.00g that the embodiment 4 of 0.50g is obtained It is placed in the water of 2.80g equipped with pearl is sanded and is sanded in the sand milling pipe of stick, 1h is sanded in stirring, the dyestuff diffusion that embodiment 4 obtains Performance reaches as defined in HGT3399-2001 5 grades.
Application examples 4
The dyestuff that embodiment 1 obtains is tested for dyeing terylene：Terylene is dyed by GBT9337-2009, bath raio 1： 20, coloration 1.5%, pH=5~6,270.02 ╳ 103Pa, high-temperature pressure dyeing, degree of exhaustion >=98%, dyeing are carried out at 130 DEG C Fiber brightness of cloth specimen after electronics color measurement and color match instrument measures dyeing is 71.65.
The dyestuff that embodiment 2 obtains is tested for dyeing terylene：Terylene is dyed by GBT9337-2009, bath raio 1： 20, coloration 1.5%, pH=5~6,270.02 ╳ 103Pa, high-temperature pressure dyeing, degree of exhaustion >=98%, dyeing are carried out at 130 DEG C Fiber brightness of cloth specimen after electronics color measurement and color match instrument measures dyeing is 80.51.
The dyestuff that embodiment 4 obtains is tested for dyeing terylene：Terylene is dyed by GBT9337-2009, bath raio 1： 20, coloration 1.5%, pH=5~6,270.02 ╳ 103Pa, high-temperature pressure dyeing, degree of exhaustion 98.2%, dyeing are carried out at 130 DEG C Fiber brightness of cloth specimen after electronics color measurement and color match instrument measures dyeing is 80.88.The brightness of this coloured fibre is apparently higher than with N, N- diethylanilines are the brightness after dyestuff (the Comparison study embodiment 1) dyeing of coupling component；The brightness of this coloured fibre is bright The aobvious brightness higher than after being dyed as the dyestuff (Comparison study embodiment 2) of coupling component using N- ethyl-N-cyanoethyl anilines shows Using alkalescent arylamine serving as diazotization ingredient, using heterocycle active methylene compound or heterocycle phenols as coupling component, it is even to obtain heterocycle Nitrogen disperse dyes have excellent dyeing brightness.
Comparison study embodiment 1
Sand milling experiment is carried out using the dyestuff of such as lower structure A：By 0.50g dyestuffs, the dispersant NNO and 2.80g of 1.00g Water is placed in equipped with pearl is sanded and is sanded in the sand milling pipe of stick, and 1h is sanded in stirring, and dyestuff diffusion reaches HGT3399-2001 rule Fixed 5 grades.Above-mentioned dyestuff is tested for dyeing terylene：Terylene is dyed by GBT9337-2009, bath raio 1：20, coloration 1.5%, pH=5~6,270.02 ╳ 103Pa, high-temperature pressure dyeing, degree of exhaustion 97.9%, coloured fibre warp are carried out at 130 DEG C The brightness of cloth specimen is 38.24 after the measurement dyeing of electronics color measurement and color match instrument.
Comparison study embodiment 2
Sand milling experiment is carried out using the dyestuff of such as lower structure B：By 0.50g dyestuffs, the dispersant NNO and 2.80g of 1.00g Water is placed in equipped with pearl is sanded and is sanded in the sand milling pipe of stick, and 1h is sanded in stirring, and dyestuff diffusion reaches HGT3399-2001 rule Fixed 5 grades.Above-mentioned dyestuff is tested for dyeing terylene：Terylene is dyed by GBT9337-2009, bath raio 1：20, coloration 1.5%, pH=5~6,270.02 ╳ 103Pa, high-temperature pressure dyeing at 130 DEG C, degree of exhaustion 98.5%, coloured fibre is through electronics The brightness of cloth specimen is 40.91 after the measurement dyeing of color measurement and color match instrument.

Claims (8)

1. a kind of preparation method of cumarin base heterocycle azo disperse dyes, which is characterized in that this method comprises the following steps：
(1) diazo component, the concentrated sulfuric acid, organic solvent and stabilizer are added in reaction vessel A, after being cooled to 0~10 DEG C, in batches Diazo reagent is added, reacts 0.1~10h, the diazosalt solid of diazo component is obtained by filtration；
(2) coupling component and water are added in reaction vessel B, with 10% sodium hydroxide tune pH value to 8~12, keep coupling component molten Solution, is cooled to 0~10 DEG C, is added with stirring the diazosalt solid for the diazo component that step (1) obtains, while with 10% sodium carbonate The pH value of solution control reaction reacts 1~10h at 0~10 DEG C, obtains the compound of formula (I) in 8~10 ranges；
The wherein described diazo reagent is nitrosyl sulfuric acid, butyl nitrite, nitrite tert-butyl, isoamyl nitrite, nitrous In sour pentyl ester, isobutyl nitrite, Isopropyl Nitrite, the sodium nitrite solution that mass concentration is 30%, sub- sour sodium solid It is one or two kinds of；
The molar ratio of diazo component, the concentrated sulfuric acid and stabilizer described in step (1) is 1:1~3:1~3；
The cumarin base heterocycle azo disperse dyes, the structure with general formula I：
A-N=N-B (I)
A is diazol and the residue after coupling component coupling, the institute for the diazo component that diazo component is obtained through diazotising in formula (I) State structure of the diazo component selected from general formula (II -2), (II -9) and (II -10)：
In formula (II -2)：
Rb 1For-R ,-Ar ,-CF3、-CN、-COOR、-CONH2Or-CH2OH；
Rb 2For-NO2、-R、-Ar、-COOR、-CONH2、-SO2R、-SO2Ar or-CN；
In formula (II -9)：
Ri 1For-CN ,-NO2,-Cl ,-Br or-I；
Ri 2For-H ,-CN ,-NO2,-Cl ,-Br or-I, and work as Ri 1For-Cl ,-Br or-I when, Ri 2Cannot be-H；
In formula (II -10)：
RjFor-H ,-CN ,-NO2,-Cl ,-Br or-I；
B is the residue after the diazol coupling of coupling component and diazo component in formula (I), and the coupling component is selected from general formula Structure shown in (III -3)：
In formula (III -3)：
RLFor-R ,-OR ,-NO2,-CN ,-Cl ,-Br ,-COOR or-Ar；
In formula (II -2) and formula (III -3)：
R is C1-4Alkyl；
Ar is phenyl.
2. preparation method according to claim 1, which is characterized in that diazo reagent described in step (1) with again The molar ratio of nitrogen component is 1~1.05:1.
3. preparation method according to claim 1, which is characterized in that diazo component, the concentrated sulfuric acid described in step (1) The total amount being added with stabilizer accounts for the 5~30% of reaction system total weight.
4. preparation method according to claim 1, which is characterized in that the coupling component described in step (2) and diazonium The molar ratio of the diazosalt solid of component is 0.8~1:0.8~1.05.
5. preparation method according to claim 1, which is characterized in that in step (1), the addition time of diazo reagent For 0.1~1h.
6. preparation method according to claim 1, which is characterized in that in step (2), be added with stirring diazo component The time of diazosalt solid is 5~60min.
7. according to any one of them preparation method of claim 1~6, which is characterized in that the organic solvent is acetic acid Ethyl ester, ether, glycol monoethyl ether, glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl One kind in ether, tetrahydrofuran, ethyl alcohol, isopropanol, dioxane, two or three；The stabilizer is fluoboric acid, fluorine boron Sour sodium, zinc acetate, zinc chloride, benzene sulfonic acid, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, bis- naphthalene sulfonic acids of 1,5-, bis- naphthalene sulfonic acids of 2,6-, methylene One or both of two naphthalene sulfonic acids, di-2-ethylhexylphosphine oxide methyl naphthalene sulfonic acid.
8. the cumarin base heterocycle azo disperse dyes that the method as described in claim 1 is prepared are in polyester fiber, polyamides Application in amine fiber, acid fiber by polylactic, polypropylene fibre or acetate fiber dyeing.
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