CN106433184A - Coumarin-based heterocyclic azo disperse dye and preparation method therefor - Google Patents

Coumarin-based heterocyclic azo disperse dye and preparation method therefor Download PDF

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CN106433184A
CN106433184A CN201610805225.3A CN201610805225A CN106433184A CN 106433184 A CN106433184 A CN 106433184A CN 201610805225 A CN201610805225 A CN 201610805225A CN 106433184 A CN106433184 A CN 106433184A
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formula
diazo
component
preparation
coupling
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CN106433184B (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
    • 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
    • D06P3/40—Cellulose acetate
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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
    • D06P3/34—Material containing ester groups
    • D06P3/52—Polyesters
    • D06P3/54—Polyesters using dispersed dyestuffs
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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
    • D06P3/79—Polyolefins
    • D06P3/794—Polyolefins using dispersed dyes

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Abstract

The invention relates to a coumarin-based heterocyclic azo disperse dye and a preparation method therefor. The coumarin-based heterocyclic azo disperse dye is prepared from two parts, i.e., a diazo component and a coupling component, wherein the coupling component is a heterocyclic active methylene compound or heterocyclic phenolic compound which is coupled under alkaline conditions, and the diazo component is alkalescent heterocyclic arylamine or an alkalescent aniline derivative. The preparation method comprises the steps of carrying out diazotization on the alkalescent heterocyclic arylamine or alkalescent aniline derivative in an organic solvent in the presence of a stabilizer so as to separate out stable diazo salt solids, carrying out filtering to obtain solids, and then, applying the solids to alkaline coupling, thereby obtaining the target dye. The dye can be applied to the dyeing of polyester fibers, polyamide fibers, polylactic-acid fibers, polypropylene fibers and acetate fibers and has 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, degree of crystallinity is high, and dyeing is more difficult, is typically dyeed using disperse dyes, to improve Dyestuff and the adhesion of hydrophobic fibre.
Do not contain the water soluble groups such as sulfonic group or carboxyl in disperse dyes structure, be insoluble in water.Need to be with during its commercialization Dispersant grinds together, is dispersed in water with insoluble minuteness particle by dispersant during application, for the high temperature of synthetic fibers High pressure or high temperature pad-dry-cure dyeing.Synthetic fibers disperse dyes divide the classes such as main inclusion azo, anthraquinone, nitrodiphenylamine by structure Type, and azo type disperse dyes are simple due to structure, cover red, yellow, blue whole chromatogram system, occupy extremely heavy in disperse dyes The status wanted.Disperse dyes containing heterocyclic group, it is high to have bright in color light, a coloring intensity, has preferable hyperchromic effect and relatively The characteristics such as high molar extinction coefficient, are important dye species in disperse dyes.
Azo type heterocyclic disperse dyes are made up of with coupling component two parts diazo component.When diazo component can be in hydrochloric acid In when carrying out diazotising (now diazo component is aniline, chlorine substituted aniline, 1- nitro substituted aniline), its coupling component can be Heterocycle arylamine, phenol or heterocycle active methylene compound, when diazo component is merely able to carry out diazotising in concentrated sulfuric acid (now Diazo component is alkalescent arylamine, such as：Aminothiophene, aminothiazole, aminobenzothiazole, 2,4- dinitroaniline, 4- nitro- 2- cyano-aniline, 4- nitro -2,6-DCA etc.), its coupling component can only be the aniline derivatives of coupling in acid condition Thing or heterocycle arylamine.And heterocycle active methylene compound, heterocycle phenolic compound need coupling in the basic conditions, alkalescent Arylamine carries out diazotising in concentrated sulfuric acid, when system is transferred to alkalescence, will produce a large amount of inorganic salts it is difficult to obtain corresponding dyestuff.
Therefore, the purpose of the present invention is the new heterocycle azo disperse dyes of exploitation one class and its technology of preparing, this kind of dyestuff Coupling component be the heterocycle active methylene compound of coupling in the basic conditions, heterocycle phenolic compound；Diazo component is Alkalescent arylamine；Its preparation method is that in organic solvent alkalescent arylamine is carried out with diazotising, separates out stable diazol solid Body, after being filtrated to get solid, it is applied to alkaline coupling, obtains target dyestuff.
Content of the invention
A first aspect of the present invention, provides a kind of new heterocycle azo disperse dyes, this dyestuff is by diazo component and coupling Component two parts form, and wherein said coupling component is the heterocycle active methylene compound or miscellaneous of coupling in the basic conditions Ring phenolic compound, described diazo component is to carry out diazotizing heterocycle arylamine or alkalescent aniline derivatives in concentrated sulfuric acid Thing.
A kind of heterocycle azo type disperse dyes, have the structure of formula (I)：
A-N=N-B
(Ⅰ)
Residue after the diazol of diazo component that in formula I, A obtains through diazotising for diazo component and coupling component coupling, Described diazo component be selected from formula (II -1), (II -2), (II -3), (II -4), (II -5), (II -6), (II -7), (II -8), (II -9) and the structure of (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 2It is the substituent at 1,2 or 3；
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 1During for-Cl ,-Br or-I, Ri 2Can not be-H；
In formula (II -10)：
RjFor-H ,-CN ,-NO2,-Cl ,-Br or-I；
In formula (I), B is the residue after coupling component and the diazol coupling of diazo component, and described 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) are to formula (III -8)：
R is hydrogen, C1-4Alkyl or C1-4Alkoxyl；
Ar is phenyl.
A second aspect of the present invention provides the system of the heterocycle azo type disperse dyes shown in (I) by formula of the present invention Preparation Method, the method comprises the 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, it is dividedly in some parts diazo reagent, react 0.1010h, be filtrated to get the diazosalt solid of diazo component；
(2) coupling component described in claim 1 and water are added in reaction vessel B, adjust pH value with 10% NaOH To 8012, so that coupling component is dissolved, be cooled to 0010 DEG C, the diazol of the lower diazo component adding step (1) to obtain of stirring is solid Body, controls the pH value of reaction in the range of 8010 with 10% sodium carbonate liquor simultaneously, reacts 1010h, obtain formula (I) at 0010 DEG C Compound；
Wherein said diazo reagent be nitrosyl sulfuric acid, butyl nitrite, nitrite tert-butyl, isoamyl nitrite, Amyl nitrite, isobutyl nitrite, Isopropyl Nitrite, mass concentration are 30% sodium nitrite solution, sub- acid sodium solid One of or two kinds.
Further, the diazo reagent described in step (1) and the molar ratio of diazo component are 101.05:1.
Further, the molar ratio of the diazo component, the concentrated sulfuric acid and stabilizer described in step (1) 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 gross weight.
Further, the molar ratio of the diazosalt solid of the coupling component described in step (2) and diazo component For 0.801:0.801.05.
Further, in step (1), the joining day of diazo reagent is 0.101h.
Further, in step (2), the time of the lower diazosalt solid adding diazo component of stirring is 5060min.
Further, described organic solvent is ethyl acetate, ether, glycol monoethyl ether, glycol dimethyl ether, second two One of diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, oxolane, ethanol, isopropanol, dioxane, Two or three.
Further, described stabilizer be fluoboric acid, sodium fluoborate, zinc acetate, zinc chloride, benzene sulfonic acid, 1-naphthalene sulfonic aicd, One of 2- naphthalene sulfonic acids, 1,5- bis- naphthalene sulfonic acids, 2,6- bis- naphthalene sulfonic acids, methylene dinaphthalene sulfonic acid, di-2-ethylhexylphosphine oxide methyl naphthalene sulfonic acid Or two kinds.
A third aspect of the present invention provide heterocycle azo type dye of the present invention polyester fiber, Fypro, Acid fiber by polylactic, polypropylene fibre, acetate fiber dyeing in application.
With respect to prior art, beneficial effects of the present invention：
1. in the structure of the compound of the present invention, its coupling component is heterocycle active methylene compound, heterocycle phenols chemical combination Thing, diazo component is alkalescent arylamine, and the dyeing brightness of acquisition is high.
2. it is in organic solvent diazotising to be carried out to alkalescent arylamine in the preparation method of the compound of the present invention, separate out Stable diazosalt solid, after being filtrated to get solid, it is applied to alkaline coupling, obtains target dyestuff, the method with sulphur Carry out diazotizing conventional method in acid to compare, sulfuric acid dosage is down to below 2 moles of times amount, reduce more than 8 moles of times amount of sulfuric acid； And the diazol that the method obtains is stable solid, can be used for alkaline coupling, obtain 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 field.
Brief description
Fig. 1 is the mass spectrogram of dye composition 1#；
Fig. 2 is the FT-IR figure of dye composition 1#；
Fig. 3 is the nuclear magnetic spectrogram of dye composition 1#；
Fig. 4 is the mass spectrogram of dye composition 2#；
Fig. 5 is the FT-IR figure of dye composition 2#；
Fig. 6 is the nuclear magnetic spectrogram of dye composition 2#；
Fig. 7 is the mass spectrogram of dye composition 3#；
Fig. 8 is the FT-IR figure of dye composition 3#；
Fig. 9 is the nuclear magnetic spectrogram of dye composition 3#；
Figure 10 is uv-visible absorption spectra under different pH for the dye composition 3#；
Figure 11 is the mass spectrogram of dye composition 4#；
Figure 12 is the FT-IR figure of dye composition 4#；
Figure 13 is the nuclear magnetic spectrogram of dye composition 4#.
Specific embodiment
In order that the purpose of the present invention, scheme, flow process and advantage are more clear distinct, in conjunction with the accompanying drawings and embodiments to this Bright be described in further detail it is notable that herein specific embodiment be only used as illustrate the present invention, be not used to Limit the present invention.In following embodiments, if no special instructions, the experimental technique being used is conventional method, material therefor, examination Agent etc. all can chemically company be bought.
Unless otherwise indicated, used in the present invention, technical term has following implication.
Used in the present invention, term " alkyl " includes straight chained alkyl and branched alkyl.As mentioned by single alkyl such as " third Base ", then only refer in particular to straight chained alkyl, as mentioned by single branched alkyl such as " isopropyl ", then only refers in particular to branched alkyl.And for example " C1-4Alkane Base " includes C1-3Alkyl, methyl, ethyl, n-propyl, isopropyl and the tert-butyl group.Similar rule is also applied for making in this specification Other groups.
In formula (II -1)：Ra 1It is preferably-H ,-CN ,-NO2、-COR、-COAr、-CONH2；More preferably-H ,-CN ,-NO2； Most preferably-H ,-NO2；Ra 2It is preferably-H ,-R ,-OR ,-NO2、-Cl；More preferably-H ,-R ,-OR ,-NO2；Most preferably-H ,- NO2；Ra 3It is preferably-H ,-CN ,-NO2,-Ar ,-COR ,-COAr, more preferably-H ,-CN ,-NO2、-Ar、-COAr；Most preferably- H、-NO2、-Ar.
In formula (II -2)：Rb 1It is preferably-H ,-R ,-Ar ,-CF3、-CN、-COOR；More preferably-H ,-R ,-Ar ,-CF3、- CN；Most preferably-H ,-Ar ,-CF3、-CN；Rb 2It is preferably-H ,-NO2、-R、-ROH、-Ar、-COOR、-SO2Ar or-CN；More excellent Elect-H ,-NO as2、-Ar、-COOR、-SO2Ar or-CN；Most preferably-H ,-NO2、-Ar、-SO2Ar.
In formula (II -3)：Preferably 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 positioned at 1.
In formula (II -4)：Rd 1It is preferably-NO2,-Cl or-H；More preferably-NO2Or-H；Most preferably-NO2；Rd 2Preferably For-H ,-Cl；More preferably-H.
In formula (II -5)：ReIt is preferably-H ,-Ar ,-OR ,-CN ,-Cl or-CCl3；More preferably-H ,-Ar ,-CN or- CCl3；Most preferably-H ,-CN or-CCl3.
In formula (II -6)：RfBe preferably-H ,-R ,-Ar ,-OR ,-CN,；More preferably-H ,-Ar ,-OR ,-CN；Most preferably For-H ,-Ar ,-CN.
In formula (II -7)：RgIt is preferably-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl；More preferably-H ,-R ,-Ar ,-CN ,- Cl；Most preferably-H ,-Ar ,-CN.
In formula (II -8)：Rh 1It is preferably-CN ,-H ,-COOCH3；More preferably-CN ,-H；Rh 2It is preferably-CONH2、-H、 Or-CH2CN；More preferably-H or-CH2CN；Rh 3It is preferably-H, phenyl；More preferably phenyl.
In formula (II -9)：Ri 1It is preferably-CN ,-NO2,-Br or-Cl；More preferably-CN ,-NO2Or-Cl；Most preferably- NO2Or-Cl；Ri 2It is preferably-H ,-CN ,-NO2,-Br or-Cl, more preferably-H ,-NO2、-Cl；Most preferably-H ,-Cl；And work as Ri 1During for Cl, Br or I, Ri 2Can not be H.
In formula (II -10)：RjIt is preferably-H ,-CN ,-NO2、-Br；More preferably-H ,-NO2；Most preferably-H.
In formula (III -1)：Rj 1It is preferably-H ,-CH3,-Ar ,-COOR or-CONHR；More preferably-H ,-CH3,-Ar or- CONHR；Most preferably-H ,-Ar；Rj 2It is preferably-H ,-Ar or-ArSO2NHR；More preferably-H ,-Ar；Most preferably-Ar.
In formula (III -2)：Rk 1It is preferably-R ,-OR ,-NHR, COOR or-CN；More preferably-R ,-NHR, COOR or-CN；? It is preferably-R, COOR or-CN；Rk 2It is preferably R ,-Ar ,-CN or-CONHR；More preferably R ,-Ar ,-CN；Most preferably R ,-Ar； Rk 3It is preferably-R ,-Ar；More preferably-R.
In formula (III -3)：RLIt is preferably-R ,-OR ,-NO2,-COOR or-Ar；More preferably-R ,-NO2,-COOR or-Ar； Most preferably-R ,-NO2、-COOR.
In formula (III -4)：Rm 1It is preferably-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 1It is preferably-R ,-OR, COOR ,-Ar；More preferably-R ,-OR, COOR；Most preferably-R ,- OR；Rn 2It is preferably-H, R ,-Ar ,-SO2NHR or-CONHR；More preferably-H, R ,-Ar or-CONHR；Most preferably-H, R.
In formula III -6：Ro 1It is preferably-R ,-CH2CH2CH2OH、-CH2CH2OH；More preferably-R ,-CH2CH2OH；Ro 2Preferably For-H, R ,-Ar ,-SO2NHR or-CONHR；More preferably-H, R ,-Ar ,-CONHR；Most preferably-H ,-Ar.
In formula (III -7)：Rp 1It is preferably-R, cyclohexyl ,-CH2CH2CH2OH、CH2CH2CN；More preferably-R ,- CH2CH2CH2OH、CH2CH2CN；Most preferably-R, CH2CH2CN；Rp 2It is preferably-H ,-NO2、-CN、-Cl、-Br；More preferably- H、-NO2、-CN、-Cl；Most preferably-H ,-NO2.
In formula (III -8)：Rq 1It is preferably-R ,-CH2CH2CH2OH、-CH2CH2OH；More preferably-R ,-CH2CH2OH；Rq 2Excellent Elect-R ,-CH as2CH2CH2OH、-CH2CH2OH；More preferably-R ,-CH2CH2OH.
In formula (II -1) to formula (II -7) and formula (III -1) are to formula (III -8)：R is preferably-H, C1-4Alkyl or C1-4Alcoxyl Base；More preferably hydrogen, C1-2Alkyl or C1-2Alkoxyl；More preferably-H, ethyl, methoxyl group.
Ar is phenyl.
On the other hand, present invention also offers the preparation method of compound described above, this preparation method is in dense sulphur In the presence of acid, in organic solvent diazo component is carried out with diazotising, separate out stable diazosalt solid, be filtrated to get this solid Afterwards, carry out coupling reaction in the basic conditions with coupling component, obtain target dyestuff.Specifically include 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, it is dividedly in some parts diazo reagent, react 0.1010h, be filtrated to get the diazosalt solid of diazo component；
(2) coupling component described in claim 1 and water are added in reaction vessel B, adjust pH value with 10% NaOH To 8012, so that coupling component is dissolved, be cooled to 0010 DEG C, the diazol of the lower diazo component adding step (1) to obtain of stirring is solid Body, controls pH value in reaction in the range of 8010 with 10% sodium carbonate dissolving, reacts 1010h, obtain the chemical combination of formula (I) at 0010 DEG C Thing；
Wherein said diazo reagent be nitrosyl sulfuric acid, butyl nitrite, nitrite tert-butyl, isoamyl nitrite, Amyl nitrite, isobutyl nitrite, Isopropyl Nitrite, mass concentration are 30% sodium nitrite solution, sub- acid sodium solid One of or two kinds.
In preferred technical scheme, described diazo reagent is nitrosyl sulfuric acid, butyl nitrite, the tertiary fourth of nitrous acid One of ester, isoamyl nitrite, amyl nitrite, isobutyl nitrite or two kinds；More preferably nitrosyl sulfuric acid, nitrous Tert-butyl acrylate, isoamyl nitrite, isobutyl nitrite；Most preferably nitrosyl sulfuric acid, nitrite tert-butyl.
In preferred technical scheme, the molar ratio of diazo reagent described in step (1) and diazo component For 1.0501:1, more preferably 1.0201:1, most preferably 1:1；Diazo component is 1 with the molar ratio of the concentrated sulfuric acid:103, More preferably 1:102.5, most preferably 1:102.
In preferred technical scheme, the feeding intake mole of diazo component described in step (1), the concentrated sulfuric acid and stabilizer Than for 1:103:103, more preferably 1:102.5:102.5, most preferably 1:102:102.
In preferred technical scheme, the total amount that the diazo component described in step (1), the concentrated sulfuric acid are added with stabilizer Account for the 5030% of reaction system gross weight, more preferably 5020%, most preferably 5015%.
In preferred technical scheme, coupling component described in step (2) and the diazosalt solid of diazo component Molar ratio is 1:101.05；More preferably 1:101.03, most preferably 1:1.
In preferred technical scheme, in step (1), the time of dropping diazo reagent is 0.101h, more preferably 0.100.5h.
In preferred technical scheme, in step (2), the time of the lower diazosalt solid adding diazo component of stirring is 5060min, more preferably 10040min.
In preferred technical scheme, described 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, oxolane, ethanol, isopropanol, dioxy six One of ring, two or three, more preferably ethyl acetate, glycol monoethyl ether, glycol dimethyl ether, ethylene glycol diethyl One of ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, oxolane, 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 of ether, two or three.
In preferred technical scheme, described stabilizer is fluoboric acid, sodium fluoborate, zinc acetate, zinc chloride, benzene sulphur Acid, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, 1,5- bis- naphthalene sulfonic acids, 2,6- bis- naphthalene sulfonic acids, one of NNO, MF or two kinds, more preferably Fluoboric acid, zinc chloride, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, 1,5- bis- naphthalene sulfonic acids, 2,6- bis- naphthalene sulfonic acids, methylene dinaphthalene sulfonic acid, methylene The double methyl naphthalene sulfonic acid of base one or two, 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 one or two.
The preparation of embodiment 1 compound 1#
(1) by 1.5g 5-Amino-2-benzimidazolinone, the 1g concentrated sulfuric acid, 80ml ethylene glycol diethyl ether, 5g 1,5- naphthalenedisulfonic acid Add in there-necked flask, in ice-water bath, be cooled to 5 DEG C, drip 3g nitrite tert-butyl, time for adding is 0.5h, anti-after completion of dropping Answer 2 hours；Diazosalt solid is obtained after filtration；(2) 1.34g 3- methyl isophthalic acid-phenyl -5 pyrazolone, 100ml water are added instead Answer in device, adjust pH value to 10 with 10% sodium hydroxide solution, be cooled to 5 DEG C, the lower 5- aminobenzene adding step (1) to obtain of stirring And imidazolone diazol, and with 10% sodium carbonate liquor control ph 9, add in half an hour, and react 2hr at 5 DEG C；Reaction Finish, filter, being washed till filtrate using frozen water is neutrality, obtains heterocycle azo disperse dyes (compound 1#), coupling obtains after being dried Rate is 95%.
[the M-H]-quasi-molecular ions of compound 1# is occurred in that at m/z 333.1, in infrared spectrum (Fig. 2) in mass spectrum (Fig. 1) In 1700cm-1For carbonyl characteristic peak, in H-NMR nuclear magnetic spectrogram (Fig. 3), 8.5-10ppm is Hydrogen Proton peak on aromatic ring.
The preparation of embodiment 2 compound 2#
(1) by 1.83g 2,4- dinitroaniline, the 2g concentrated sulfuric acid, 40ml glycol dimethyl ether, 4g 1,5- naphthalenedisulfonic acid adds Enter in there-necked flask, in ice-water bath, be cooled to 3 DEG C, drip 3g nitrosyl sulfuric acid, time for adding is 0.5h, after completion of dropping, react 2 Hour；Diazosalt solid is obtained after filtration；(2) 0.81g 3- Methyl-5-pyrazolone, 80ml water are added in reactor, use 10% sodium hydroxide solution adjusts pH value to 11, is cooled to 4 DEG C, lower 2, the 4- dinitroaniline weight adding step (1) to obtain of stirring Nitrogen salt, and with 10% sodium carbonate liquor control ph 9, add in half an hour, and react 2hr at 5 DEG C；Reaction finishes, and filters, Being washed till filtrate using frozen water is neutrality, obtains heterocycle azo disperse dyes (compound 2#), coupling yield is 99% after being dried.
Occur in that [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, in H-NMR nuclear magnetic spectrogram (Fig. 6), 8.2-9.5ppm is Hydrogen Proton peak on aromatic ring.
The preparation of embodiment 3 compound 3#
(1) by 1.45g 2- amino -5- nitrothiazole, 60ml ethyl acetate, the 5g concentrated sulfuric acid, (30% is water-soluble for 5g zinc acetate Liquid) add in there-necked flask, it is cooled to 005 degree Celsius in ice-water bath, adds 2g nitrosyl sulfuric acid, react 2 hours after finishing；Filter After obtain diazosalt solid；(2) 0.97g 8-hydroxyquinoline, 80ml water are added in reactor, use 10% sodium hydroxide solution Adjust pH value to 10, be cooled to 5 DEG C, be added in the 2- amino -5- nitrothiazole diazol that step (1) obtains under stirring, be used in combination 10% sodium carbonate liquor control ph 9, adds in half an hour, and reacts 2hr at 5 DEG C；Reaction finishes, and filters, using frozen water Being washed till filtrate is neutrality, obtains heterocycle azo disperse dyes (compound 3#) after being dried, and coupling yield is 80%.
Occur in that [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, in H-NMR nuclear magnetic spectrogram (Fig. 9), 8.2-9.5ppm is Hydrogen Proton peak on aromatic ring. As can be seen that when solution ph is 6, being purple in its uv-visible absorption spectra (Figure 10), when solution ph is 8, The a length of 626nm of maximum absorption wave, for blueness, color change is notable, has pH sensitive color change characteristic, can be used for the bore hole inspection of pH Survey.
The preparation of embodiment 4 compound 4#
(1) by 2.07g 4- nitro -2,6-DCA, the 3g concentrated sulfuric acid, 50ml glycol dimethyl ether, 3g 1,5- naphthalene two Sulfonic acid adds in there-necked flask, is cooled to 4 degrees Celsius in ice-water bath, and dropping sodium nitrite solution (30%, institute's dripping quantity and diazonium group The mol ratio divided is 1.05：1), time for adding is 0.5h, reacts 1 hour after completion of dropping；Diazosalt solid is obtained after filtration； (2) 1.24g 3- methyl isophthalic acid-phenyl -5 pyrazolone, 50ml water are added in reactor, adjust pH with 10% sodium hydroxide solution It is worth to 11, is cooled to 6 DEG C, stirring is lower to add 4- nitro -2,6-DCA diazol, and controls pH with 10% sodium carbonate liquor Value 10, adds in half an hour, and reacts 2h at 8 DEG C；Reaction finishes, and filters, and being washed till filtrate using frozen water is neutrality, after being dried Obtain heterocycle azo disperse dyes (compound 4#), coupling yield is 92%.
Occur in that [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, in nuclear magnetic spectrogram (Figure 13), 7-8.6ppm is Hydrogen Proton peak on aromatic ring.
Embodiment 5
(1) by 1.96g 2- amino -3,5- dinitro thiophene, the 1g concentrated sulfuric acid, 60ml glycol dimethyl ether, 5g 2,6- naphthalene Disulfonic acid adds in there-necked flask, is cooled to 3 DEG C in ice-water bath, drips 4g isoamyl nitrite, and time for adding is 0.5h, drips React 2 hours after finishing；Diazosalt solid is obtained after filtration；(2) by 1.74g N- ethyl -3- cyano group -4- methyl -6- hydroxyl -2- Pyridone, 100ml water add in reactor, adjust pH value to 11 with 10% sodium hydroxide solution, are cooled to 5 DEG C, and stirring is lower to be added 2- amino -3 obtaining in step (1), 5- dinitro thiophene diazol, and little 9, half with 10% sodium carbonate liquor control ph When interior add, and 5 DEG C react 2hr；Reaction finishes, and filters, and being washed till filtrate using frozen water is neutrality, obtains heterocycle even after being dried Nitrogen disperse dyes.
Embodiment 6
(1) by 1.0g thiazolamine, 60ml ethyl acetate, the 5g concentrated sulfuric acid, 5g fluoboric acid (40% aqueous solution) adds three In mouth bottle, in ice-water bath, it is cooled to 5 DEG C, adds 0.7g natrium nitrosum, react 2 hours after finishing；Diazol is obtained solid after filtration Body；(2) 1.62g 4 hydroxy coumarin, 80ml water are added in reactor, adjust pH value to 11 with 10% sodium hydroxide solution, cold But to 8 DEG C, the lower thiazolamine diazol adding step (1) to obtain of stirring, and existed with 10% sodium carbonate liquor control ph 9, add in half an hour, and react 2hr at 5 DEG C；Reaction finishes, and filters, and being washed till filtrate using frozen water is neutrality, obtains after being dried Heterocycle azo disperse dyes.
Embodiment 7-22
Using 3- cyano group -6- hydroxy-4-methyl -2- pyridone, N- ethyl -3- cyano group -4- methyl -6- hydroxyl -2- pyridine Ketone, hexahydroxy pyridone, 3- formamido group -4- methyl -6- hydroxy-n-ethylpyridine ketone, 4 hydroxy coumarin, 7- nitro -4- Hydroxycoumarin, 7- methyl -4 hydroxy coumarin, 4- oxyquinoline, 2,4- dihydroxy quinoline, 7- chloro-4-hydroxyl quinoline, N- first Base -4- hydroxyl -2- quinolinone, 4- hydroxyl -1,8- naphthalimide, N- methyl -4- hydroxyl -1,8- naphthalimide, 1- (4- chlorphenyl) -3- methyl -5- pyrazolone, 1- phenyl -3- methyl -4- benzoyl -5- pyrazolone, 3- methyl -5- pyrrole Oxazolone replace embodiment 1 in 3- methyl isophthalic acid-phenyl -5 pyrazolone, in the basic conditions respectively with 5-Amino-2-benzimidazolinone Diazosalt solid coupling, obtain corresponding heterocycle azo disperse dyes.
Embodiment 23-30
Using 2,4- dinitroaniline, 4- nitro -2,6- dibromo aniline, 4- nitro -2- cyano-aniline, 2- amino benzo thiophene Azoles, 6- nitrothiazole, 5- amino benzo -1,2,3- thiadiazoles, 2- aminothiophene, 1- phenyl -3- methyl -4- cyano group -5- amino Pyrazoles replaces the 5-Amino-2-benzimidazolinone in embodiment 1, carries out diazotising, obtains corresponding diazosalt solid, in alkalescence condition Lower respectively with 3- methyl isophthalic acid-phenyl -5 pyrazolone, obtain corresponding heterocycle azo disperse dyes.
Embodiment 31-38
Using ethyl acetate, ether, glycol monoethyl ether, glycol dimethyl ether, oxolane, ethanol, 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, in the basic conditions respectively with 3- methyl isophthalic acid-phenyl -5 pyrazolone coupling, obtain 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, 2,6- bis- naphthalene sulfonic acids, NNO, MF replaces 1, the 5- naphthalenedisulfonic acid in embodiment 1 as the stabilizer of 5-Amino-2-benzimidazolinone, obtains corresponding diazosalt solid, In the basic conditions respectively with 3- methyl isophthalic acid-phenyl -5 pyrazolone coupling, obtain corresponding heterocycle azo disperse dyes.
Embodiment 47-54
Using nitrosyl sulfuric acid, butyl nitrite, isoamyl nitrite, amyl nitrite, isobutyl nitrite, nitrous acid Isopropyl ester replaces the nitrite tert-butyl in embodiment 1 as the diazo reagent of 5-Amino-2-benzimidazolinone, obtains and accordingly weighs Nitrogen salt solid, in the basic conditions respectively with 3- methyl isophthalic acid-phenyl -5 pyrazolone, obtain corresponding heterocycle azo disperse dyes.
Embodiment 55-70
Using 3- cyano group -6- hydroxy-4-methyl -2- pyridone, hexahydroxy pyridone, 3- formamido group -4- methyl -6- hydroxyl Base-N- ethylpyridine ketone, 4 hydroxy coumarin, 7- nitro -4 hydroxy coumarin, 7- methyl -4 hydroxy coumarin, 4- hydroxyl quinoline Quinoline, 2,4- dihydroxy quinoline, 7- chloro-4-hydroxyl quinoline, N- methyl -4- hydroxyl -2- quinolinone, 4- hydroxyl -1,8- naphthalene two formyl Imines, N- methyl -4- hydroxyl -1,8- naphthalimide, 1- (4- chlorphenyl) -3- methyl -5- pyrazolone, 1- phenyl -3- Methyl -4- benzoyl -5- pyrazolone, 3- Methyl-5-pyrazolone replace the 3- Methyl-5-pyrazolone in embodiment 2, in alkali Diazosalt solid coupling with 2,4- dinitroaniline respectively under the conditions of property, obtains corresponding heterocycle azo disperse dyes.
Embodiment 71-78
Using 2- amino -3,5- dinitro thiophene, 4- nitro -2,6- dibromo aniline, 4- nitro -2- cyano-aniline, 2- ammonia Base benzothiazole, 6- nitrothiazole, 5- amino benzo -1,2,3- thiadiazoles, 2- aminothiophene, 1- phenyl -3- methyl -4- cyanogen Base -5- amino-pyrazol replaces 2, the 4- dinitroaniline in embodiment 2, carries out diazotising, obtains corresponding diazosalt solid, in alkali Under the conditions of property respectively with 3- Methyl-5-pyrazolone coupling, obtain corresponding heterocycle azo disperse dyes.
Embodiment 79-86
Using ethyl acetate, ether, glycol monoethyl ether, ethylene glycol diethyl ether, oxolane, ethanol, isopropanol, dioxy Six rings replace the glycol dimethyl ether in embodiment 2 as the diazotizing solvent of 2,4- dinitroaniline, obtain corresponding diazol Solid, in the basic conditions respectively with 3- Methyl-5-pyrazolone coupling, obtain corresponding heterocycle azo disperse dyes.
Embodiment 87-94
Using fluoboric acid, sodium fluoborate, zinc acetate, benzene sulfonic acid, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, 2,6- bis- naphthalene sulfonic acids, methylene Base two naphthalene sulfonic acids, di-2-ethylhexylphosphine oxide methyl naphthalene sulfonic acid replace 1, the 5- naphthalenedisulfonic acid in embodiment 2 as 2,4- dinitroaniline weight The stabilizer of nitrogen salt, obtain corresponding diazosalt solid, in the basic conditions respectively with 3- Methyl-5-pyrazolone coupling, obtain phase Answer heterocycle azo disperse dyes.
Embodiment 95-102
Using isoamyl nitrite, butyl nitrite, nitrite tert-butyl, amyl nitrite, isobutyl nitrite, nitrous Isopropyl propionate replaces the nitrosyl sulfuric acid in embodiment 2 as the diazo reagent of 2,4- dinitroaniline, obtains corresponding diazonium Salt solid, in the basic conditions respectively with 3- Methyl-5-pyrazolone coupling, obtain corresponding heterocycle azo disperse dyes.
Embodiment 103-118
Using 3- cyano group -6- hydroxy-4-methyl -2- pyridone, hexahydroxy pyridone, 3- formamido group -4- methyl -6- hydroxyl Base-N- ethylpyridine ketone, 7- nitro -4 hydroxy coumarin, 7- methyl -4 hydroxy coumarin, 4- oxyquinoline, 2,4- dihydroxy Quinoline, 7- chloro-4-hydroxyl quinoline, N- methyl -4- hydroxyl -2- quinolinone, 4- hydroxyl -1,8- naphthalimide, N- methyl -4- Hydroxyl -1,8- naphthalimide, 1- (4- chlorphenyl) -3- methyl -5- pyrazolone, 1- phenyl -3- methyl -4- benzoyl Base -5- pyrazolone, 3- Methyl-5-pyrazolone replace embodiment 3 in 8-hydroxyquinoline, in the basic conditions respectively with 2- ammonia The diazosalt solid coupling of base -5- nitrothiazole, obtains corresponding heterocycle azo disperse dyes.
Embodiment 119-126
Using 2,4- dinitroaniline, 4- nitro -2,6- dibromo aniline, 4- nitro -2- cyano-aniline, 2- amino benzo thiophene Azoles, 6- nitrothiazole, 5- amino benzo -1,2,3- thiadiazoles, 2- aminothiophene, 1- phenyl -3- methyl -4- cyano group -5- amino Pyrazoles replaces the 2- amino -5- nitrothiazole in embodiment 3, carries out diazotising, obtains corresponding diazosalt solid, in alkalescence condition Lower respectively with 8-hydroxyquinoline coupling, obtain corresponding heterocycle azo disperse dyes.
Embodiment 127-134
Using glycol dimethyl ether, ether, glycol monoethyl ether, ethylene glycol diethyl ether, oxolane, ethanol, isopropanol, Dioxane replace ethyl acetate in embodiment 3 as the diazotizing solvent of 2- amino -5- nitrothiazole, obtain corresponding diazonium Salt solid, in the basic conditions respectively with 8-hydroxyquinoline coupling, obtain corresponding heterocycle azo disperse dyes.
Embodiment 135-142
Using 1,5- naphthalenedisulfonic acid, sodium fluoborate, fluoboric acid, benzene sulfonic acid, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, 2,6- dinaphthyl sulphur 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 thiophene The stabilizer of azoles diazol, obtains corresponding diazosalt solid, in the basic conditions respectively with 8-hydroxyquinoline coupling, obtain corresponding Heterocycle azo disperse dyes.
Embodiment 143-150
Different using isoamyl nitrite, natrium nitrosum, butyl nitrite, nitrite tert-butyl, amyl nitrite, nitrous acid Butyl ester, Isopropyl Nitrite replace the nitrosyl sulfuric acid in embodiment 3 as the diazo reagent of 2- amino -5- nitrothiazole, Obtain corresponding diazosalt solid, in the basic conditions respectively with 8-hydroxyquinoline coupling, obtain corresponding heterocycle azo disperse dyes.
Embodiment 151-166
Using 3- cyano group -6- hydroxy-4-methyl -2- pyridone, hexahydroxy pyridone, 3- formamido group -4- methyl -6- hydroxyl Base-N- ethylpyridine ketone, 7- nitro -4 hydroxy coumarin, 7- methyl -4 hydroxy coumarin, 4- oxyquinoline, 2,4- dihydroxy Quinoline, 7- chloro-4-hydroxyl quinoline, N- methyl -4- hydroxyl -2- quinolinone, 4- hydroxyl -1,8- naphthalimide, N- methyl -4- Hydroxyl -1,8- naphthalimide, 1- (4- chlorphenyl) -3- methyl -5- pyrazolone, 1- phenyl -3- methyl -4- benzoyl Base -5- pyrazolone, 3- Methyl-5-pyrazolone replace 3- methyl isophthalic acid-phenyl -5 pyrazolone in embodiment 4, in alkaline bar Under part, the diazosalt solid coupling with 4- nitro -2,6-DCA respectively, obtains corresponding heterocycle azo disperse dyes.
Embodiment 167-174
Using 2,4- dinitroaniline, thiazolamine, 4- nitro -2,6- dibromo aniline, 4- nitro -2- cyano-aniline, 2- aminobenzothiazole, 6- nitrothiazole, 5- amino benzo -1,2,3- thiadiazoles, 2- aminothiophene, 1- phenyl -3- methyl -4- Cyano group -5- amino-pyrazol replaces the 4- nitro -2,6-DCA in embodiment 4, carries out diazotising, obtains corresponding diazol solid Body, in the basic conditions respectively with 3- methyl isophthalic acid-phenyl -5 pyrazolone coupling, obtain corresponding heterocycle azo disperse dyes.
Application examples 1
The dyestuff sand milling test that embodiment 1 obtains：Dyestuff that the embodiment 1 of 0.50g is obtained, the dispersant NNO of 1.00g It is placed in the sand milling pipe equipped with sand milling pearl and sand milling rod with the water of 2.80g, stir sand milling 1h, the dyestuff diffusion that embodiment 1 obtains Performance reaches 5 grades of HGT3399-2001 regulation.
Application examples 2
The dyestuff sand milling test that embodiment 2 obtains：Dyestuff that the embodiment 2 of 0.50g is obtained, the dispersant NNO of 1.00g It is placed in the sand milling pipe equipped with sand milling pearl and sand milling rod with the water of 2.80g, stir sand milling 1h, the dyestuff diffusion that embodiment 2 obtains Performance reaches 5 grades of HGT3399-2001 regulation.
Application examples 3
The dyestuff sand milling test that embodiment 4 obtains：Dyestuff that the embodiment 4 of 0.50g is obtained, the dispersant NNO of 1.00g It is placed in the sand milling pipe equipped with sand milling pearl and sand milling rod with the water of 2.80g, stir sand milling 1h, the dyestuff diffusion that embodiment 4 obtains Performance reaches 5 grades of HGT3399-2001 regulation.
Application examples 4
The dyestuff that embodiment 1 obtains is used for dyeing terylene to be tested：By GBT9337-2009, terylene is dyeed, bath raio 1： 20, colourity 1.5%, pH=5～6,270.02 103Pa, carry out high-temperature pressure dyeing at 130 DEG C, degree of exhaustion >=98%, dyeing The brightness that fiber measures cloth specimen after dyeing through electronics color measurement and color match instrument is 71.65.
The dyestuff that embodiment 2 obtains is used for dyeing terylene to be tested：By GBT9337-2009, terylene is dyeed, bath raio 1： 20, colourity 1.5%, pH=5～6,270.02 103Pa, carry out high-temperature pressure dyeing at 130 DEG C, degree of exhaustion >=98%, dyeing The brightness that fiber measures cloth specimen after dyeing through electronics color measurement and color match instrument is 80.51.
The dyestuff that embodiment 4 obtains is used for dyeing terylene to be tested：By GBT9337-2009, terylene is dyeed, bath raio 1： 20, colourity 1.5%, pH=5～6,270.02 103Pa, carry out high-temperature pressure dyeing at 130 DEG C, degree of exhaustion 98.2%, dyeing The brightness that fiber measures cloth specimen after dyeing through electronics color measurement and color match instrument is 80.88.The brightness of this coloured fibre apparently higher than with N, N- diethylaniline is the brightness after dyestuff (the Comparison study embodiment 1) dyeing of coupling component；The brightness of this coloured fibre is bright Brightness after showing higher than dyestuff (the Comparison study embodiment 2) dyeing with N- ethyl-N-cyanoethyl aniline as coupling component, shows With alkalescent arylamine serving as diazotization ingredient, with heterocycle active methylene compound or heterocycle phenols as coupling component, obtain heterocycle even Nitrogen disperse dyes have excellent dyeing brightness.
Comparison study embodiment 1
Dyestuff using following structure A carries out sand milling test：By 0.50g dyestuff, dispersant NNO and 2.80g of 1.00g Water is placed in the sand milling pipe equipped with sand milling pearl and sand milling rod, stirs sand milling 1h, and dyestuff diffusion reaches HGT3399-2001 rule Fixed 5 grades.Above-mentioned dyestuff is used for dyeing terylene to be tested：By GBT9337-2009, terylene is dyeed, bath raio 1：20, colourity 1.5%, pH=5～6,270.02 103Pa, carry out high-temperature pressure dyeing, degree of exhaustion 97.9%, coloured fibre warp at 130 DEG C The brightness that electronics color measurement and color match instrument measures cloth specimen after dyeing is 38.24.
Comparison study embodiment 2
Dyestuff using following structure B carries out sand milling test：By 0.50g dyestuff, dispersant NNO and 2.80g of 1.00g Water is placed in the sand milling pipe equipped with sand milling pearl and sand milling rod, stirs sand milling 1h, and dyestuff diffusion reaches HGT3399-2001 rule Fixed 5 grades.Above-mentioned dyestuff is used for dyeing terylene to be tested：By GBT9337-2009, terylene is dyeed, bath raio 1：20, colourity 1.5%, pH=5～6,270.02 103Pa, high-temperature pressure dyeing, degree of exhaustion 98.5% at 130 DEG C, coloured fibre is through electronics The brightness that color measurement and color match instrument measures cloth specimen after dyeing is 40.91.

Claims (10)

1. a kind of cumarin base heterocycle azo disperse dyes, have the structure of formula I：
A-N=N-B (I)
Residue after the diazol of diazo component that in formula (I), A obtains through diazotising for diazo component and coupling component coupling, institute State diazo component be selected from formula (II -1), (II -2), (II -3), (II -4), (II -5), (II -6), (II -7), (II -8), (II -9) and the structure of (II -10)：
In formula (II -1)：
Ra 1For-H ,-CN ,-NO2、-COR、-CONHR、-SO2,-COOR or-COAr；
Ra 2For-R ,-OR ,-NO2,-Cl or-Br；
Ra 3For-CN ,-NO2,-Ar ,-COR ,-COAr ,-COOR ,-COOAr ,-CONHR ,-SCN ,-OCOR ,-CONHAr or-CHO；
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 -3)：
RC 1And RC 2It is each independently selected from-Cl ,-Br ,-NO2、-R、-OR、-CN、-SO2R、-SO2N or-CF3；
RC 2It is the substituent at 1,2 or 3；
In formula (II -4)：
Rd 1For-NO2,-Cl ,-Br or-H；
Rd 2For-H ,-Cl or-Br；
In formula (II -5)：
ReFor-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl or-CCl3；
In formula (II -6)：
RfFor-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl or-CCl3；
In formula (II -7)：
RgFor-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 1During for-Cl ,-Br or-I, Ri 2Can not be-H；
In formula (II -10)：
RjFor-H ,-CN ,-NO2,-Cl ,-Br or-I；
In formula (I), B is the residue after coupling component and the diazol coupling of diazo component, and described coupling component is selected from formula Structure shown in (III -3)：
In formula (III -3)：
RLFor-R ,-OR ,-NO2,-CN ,-Cl ,-Br ,-COOR or-Ar；
In formula (II -1) to formula (II -7) and formula (III -3)：
R is hydrogen, C1-4Alkyl or C1-4Alkoxyl；
Ar is phenyl.
2. the preparation method of cumarin base heterocycle azo disperse dyes as claimed in claim 1 is it is characterised in that the method bag Include following steps：
(1) diazo component described in claim 1, the concentrated sulfuric acid, organic solvent and stabilizer are added in reaction vessel A, cooling To after 0010 DEG C, it is dividedly in some parts diazo reagent, react 0.1010h, be filtrated to get the diazosalt solid of diazo component；
(2) coupling component described in claim 1 and water are added in reaction vessel B, adjust pH value extremely with 10% NaOH 8012, so that coupling component is dissolved, be cooled to 0010 DEG C, the diazosalt solid of the lower diazo component adding step (1) to obtain of stirring, Control the pH value of reaction in the range of 8010 with 10% sodium carbonate liquor simultaneously, react 1010h at 0010 DEG C, obtain formula (I) Compound；
Wherein said diazo reagent is nitrosyl sulfuric acid, butyl nitrite, nitrite tert-butyl, isoamyl nitrite, nitrous Sour pentyl ester, isobutyl nitrite, Isopropyl Nitrite, mass concentration be 30% sodium nitrite solution, in sub- acid sodium solid One or two.
3. preparation method according to claim 2 is it is characterised in that diazo reagent described in step (1) and weight The molar ratio of nitrogen component is 101.05:1.
4. preparation method according to claim 2 is it is characterised in that diazo component described in step (1), the concentrated sulfuric acid Molar ratio with stabilizer is 1:103:103.
5. preparation method according to claim 2 is it is characterised in that diazo component described in step (1), the concentrated sulfuric acid The total amount being added with stabilizer accounts for the 5030% of reaction system gross weight.
6. preparation method according to claim 2 is it is characterised in that the coupling component described in step (2) and diazonium The molar ratio of the diazosalt solid of component is 0.801:0.801.05.
7. preparation method according to claim 2 is it is characterised in that in step (1), the joining day of diazo reagent For 0.101h.
8. preparation method according to claim 2 is it is characterised in that in step (2), stirring is lower to add diazo component The time of diazosalt solid is 5060min.
9. the preparation method according to any one of claim 2～8 is it is characterised in that described 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 of ether, oxolane, ethanol, isopropanol, dioxane, two or three；Described stabilizer is fluoboric acid, fluorine boron Sour sodium, zinc acetate, zinc chloride, benzene sulfonic acid, 1-naphthalene sulfonic aicd, 2- naphthalene sulfonic acids, 1,5- bis- naphthalene sulfonic acids, 2,6- bis- naphthalene sulfonic acids, methylene One of two naphthalene sulfonic acids, di-2-ethylhexylphosphine oxide methyl naphthalene sulfonic acid or two kinds.
10. cumarin base heterocycle azo disperse dyes as claimed in claim 1 are in polyester fiber, Fypro, PLA Application in fiber, polypropylene fibre or acetate fiber dyeing.
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