CN105038316A - Heterocyclic-ring disperse azo dye and preparation method thereof - Google Patents

Heterocyclic-ring disperse azo dye and preparation method thereof Download PDF

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Publication number
CN105038316A
CN105038316A CN201510443025.3A CN201510443025A CN105038316A CN 105038316 A CN105038316 A CN 105038316A CN 201510443025 A CN201510443025 A CN 201510443025A CN 105038316 A CN105038316 A CN 105038316A
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formula
iii
coor
preparation
diazo
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CN201510443025.3A
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Chinese (zh)
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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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Priority to CN201610805297.8A priority Critical patent/CN106433182B/en
Priority to CN201610805225.3A priority patent/CN106433184B/en
Priority to CN201610806688.1A priority patent/CN106398309A/en
Priority to CN201610806537.6A priority patent/CN106433183B/en
Priority to CN201510443025.3A priority patent/CN105038316A/en
Priority to CN201610805313.3A priority patent/CN106380891B/en
Priority to CN201610805222.XA priority patent/CN106433181B/en
Publication of CN105038316A publication Critical patent/CN105038316A/en
Pending legal-status Critical Current

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    • C09B29/0848—Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 substituted by NO2
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    • 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
    • C09B29/3678—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
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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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    • 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
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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

Abstract

The invention relates to a heterocyclic-ring disperse azo dye and a preparation method thereof. The heterocyclic-ring disperse azo dye consists of a heavy nitrogen component and a coupling component, wherein the coupling component is a heterocyclic-ring active methylene compound or a heterocyclic-ring phenolic compound coupled under the alkaline condition, and the heavy nitrogen component is a slightly-alkaline heterocyclic-ring arylamine or a slightly-alkaline aniline derivative. According to the preparation method, the slightly-alkaline heterocyclic-ring arylamine or the slightly-alkaline aniline derivative is diazotized in an organic solvent in the presence of a stabilizer to precipitate out stable diazonium salt solid, the solid obtained through filtration is applied to alkaline coupling so as to obtain the target dye. The dye can be applied to dyeing of polyester fiber, polyamide fiber, polylactic acid fiber, polypropylene fiber and cellulose acetate fiber and has excellent dyeing brightness.

Description

Heterocycle azo dispersed dye and preparation method thereof
Technical field
The present invention relates to a kind of heterocycle azo dispersed dye and preparation method thereof.
Background technology
Synthon close structure, degree of crystallinity is high, dyes more difficult, and the general dispersed dye that adopt dye, to improve the bonding force of dyestuff and hydrophobic fibre.
Not containing the water soluble group such as sulfonic group or carboxyl in disperse dyes structure, be insoluble in water.Need grind together with dispersion agent during its commercialization, be scattered in water by dispersion agent with insoluble minuteness particle during application, for the synthesis of High Temperature High Pressure or the high temperature pad-dry-cure dyeing of fiber.Synthon dispersed dye divide by structure types such as mainly comprising azo, anthraquinone, nitrodiphenylamine, and azo type disperse dyes is simple due to structure, covers red, yellow, blue whole chromatogram system, occupies extremely important status in dispersed dye.Containing the dispersed dye of heterocyclic group, have bright in color light, coloring intensity is high, having the characteristics such as good hyperchromic effect and higher molar extinction coefficient, is dye species important in dispersed dye.
Azo type heterocyclic dispersed dye are made up of diazo component and coupling component two portions.When diazo component can carry out diazotization in hydrochloric acid, (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 diazotization in concentrated sulfuric acid, (now diazo component is weakly alkaline arylamine, as: aminothiophene, aminothiazole, aminobenzothiazole, 2, 4-dinitraniline, 4-nitro-2-cyano-aniline, 4-nitro-2, 6-dichlorphenamide bulk powder etc.), its coupling component can only be anils or the heterocycle arylamine of coupling in acid condition.And heterocycle active methylene compound, heterocycle phenolic compound need coupling in the basic conditions, weakly alkaline arylamine carries out diazotization in concentrated sulfuric acid, when system is transferred to alkalescence, will produce a large amount of inorganic salt, is difficult to obtain corresponding dyestuff.
Therefore, the object of the invention is the new heterocycle azo dispersed dye of exploitation one class and technology of preparing thereof, the coupling component of this kind of dyestuff is the heterocycle active methylene compound of coupling in the basic conditions, heterocycle phenolic compound; Diazo component is weakly alkaline arylamine; Its preparation method carries out diazotization to weakly alkaline arylamine in organic solvent, separates out stable diazosalt solid, filters after obtaining solid, it is applied to alkaline coupling, obtains target dyestuff.
Summary of the invention
A first aspect of the present invention, a kind of new heterocycle azo dispersed dye are provided, this dyestuff is made up of diazo component and coupling component two portions, wherein said coupling component is heterocycle active methylene compound or the heterocycle phenolic compound of coupling in the basic conditions, and described diazo component is for can carry out diazotizing heterocycle arylamine or weakly alkaline anils in concentrated sulfuric acid.
A kind of heterocycle azo type dispersed dye, have the structure of logical formula I:
A-N＝N-B
(Ⅰ)
In formula I, A is the residue after the diazonium salt of the diazo component that diazo component obtains through diazotization and coupling component coupling, and described diazo component is selected from the structure of general formula (II-1), (II-2), (II-3), (II-4), (II-5), (II-6), (II-7), (II-8), (II-9) and (II-10):
In formula (II-1):
R a 1for-H ,-CN ,-NO 2,-COR ,-COAr ,-CONH 2,-CONHR ,-SO 2,-COOR or-COAr;
R a 2for-H ,-R ,-OR ,-NO 2,-Cl or-Br;
R a 3for-H ,-CN ,-NO 2,-Ar ,-COR ,-COAr ,-COOR ,-COOAr ,-CONH 2,-CONHR ,-SCN ,-OCOR ,-CONHAr or-CHO;
In formula (II-2):
R b 1for-H ,-R ,-Ar ,-CF 3,-CN ,-COOR ,-CONH 2or-CH 2oH;
R b 2for-H ,-NO 2,-R ,-ROH ,-Ar ,-COOR ,-CONH 2,-SO 2r ,-SO 2ar or-CN;
In formula (II-3):
R c 1and R c 2be selected from-H ,-Cl ,-Br ,-NO independently of one another 2,-R ,-OR ,-CN ,-SO 2r ,-SO 2nR and-CF 3;
R c 2for at the substituting group of 1,2 or 3;
In formula (II-4):
R d 1for-NO 2,-Cl ,-Br or-H;
R d 2for-H ,-Cl or-Br;
In formula (II-5):
R efor-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl or-CCl 3;
In formula (II-6):
R ffor-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl or-CCl 3;
In formula (II-7):
R gfor-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-NO 2, CN ,-Cl or-CCl 3;
In formula (II-8):
R h 1for-CN ,-H ,-COOH or-COOCH 3;
R h 2for-SCH ,-H ,-CONH 2or-CH 2cN;
R h 3for-H, phenyl or cyclohexyl;
In formula (II-9):
R i 1for-CN ,-NO 2,-Cl ,-Br or-I;
R i 2for-H ,-CN ,-NO 2,-Cl ,-Br or-I, and work as R i 1during for-Cl ,-Br or-I, R i 2can not be-H;
In formula (II-10):
R jfor-H ,-CN ,-NO 2,-Cl ,-Br or-I;
In formula I, B is the residue after the diazonium salt coupling of coupling component and diazo component, and described coupling component is selected from general formula (III-1), (III-2), (III-3), (III-4), (III-5), (III-6), the structure shown in (III-7) and (III-8):
In formula (III-1):
R j 1for-H ,-CH 3,-Ar ,-CF 3,-CN ,-COOR or-CONHR;
R j 2for-H ,-Ar ,-ArCl or-ArSO 2nHR;
In formula (III-2):
R k 1for-R ,-OR ,-NHR, COOR ,-Ar or-CN;
R k 2for-H, R ,-Ar ,-CN ,-COOR ,-SO 2nHR or-CONHR;
R k 3for-R ,-Ar or cyclohexyl;
In formula (III-3):
R lfor-R ,-OR ,-NO 2,-CN ,-Cl ,-Br ,-COOR or-Ar;
In formula (III-4):
R m 1for-R ,-OR, COOR ,-Ar or-CN;
R m 2for-H, R ,-Ar ,-CN ,-COOR ,-SO 2nHR or-CONHR;
In formula (III-5):
R n 1for-R ,-OR, COOR ,-Ar or-CN;
R n 2for-H, R ,-Ar ,-CN ,-COOR ,-SO 2nHR or-CONHR;
In formula (III-6):
R o 1for-R ,-CH 2cH 2cH 2oH ,-CH 2cH 2oH ,-CH 2cH 2cN or-Ar;
R o 2for-H, R ,-Ar ,-CN ,-COOR ,-SO 2nHR or-CONHR;
In formula (III-7):
R p 1for-R, cyclohexyl ,-CH 2cH 2cH 2oH ,-CH 2cH 2oH ,-CH 2cH 2cN or-Ar;
R p 2for-H ,-NO 2,-CN ,-Cl ,-Br ,-COOR ,-SO 2nHR or-CONHR;
In formula (III-8):
R q 1for-R, cyclohexyl ,-CH 2cH 2cH 2oH ,-CH 2cH 2oH ,-CH 2cH 2cN or-Ar;
R q 2for-R, cyclohexyl ,-CH 2cH 2cH 2oH ,-CH 2cH 2oH ,-CH 2cH 2cN or-Ar;
In formula (II-1) to formula (II-7) and formula (III-1) in formula (III-8):
R is hydrogen, C 1- 4alkyl or C 1- 4alkoxyl group;
Ar is phenyl.
A second aspect of the present invention provides the preparation method by the heterocycle azo type dispersed dye shown in logical formula I of the present invention, and the method comprises the steps:
(1) diazo component according to claim 1, the vitriol oil, organic solvent and stablizer are added in reaction vessel A, after being cooled to 0 ~ 10 DEG C, add diazo reagent in batches, reaction 0.1 ~ 10h, filters the diazosalt solid obtaining diazo component;
(2) coupling component according to claim 1 and water are added in reaction vessel B, with 10% sodium hydroxide adjust pH to 8 ~ 12, coupling component is dissolved, be cooled to 0 ~ 10 DEG C, the diazosalt solid of the diazo component that step (1) obtains is added under stirring, control the pH value of reaction in 8 ~ 10 scopes with 10% sodium carbonate solution simultaneously, at 0 ~ 10 DEG C, react 1 ~ 10h, obtain the compound of formula I;
One or both in the sodium nitrite solution that wherein said diazo reagent is nitrosyl sulfuric acid, butyl nitrite, nitrite tert-butyl, Isopentyl nitrite, amyl nitrite, isobutyl nitrite, nitrous acid isopropyl ester, mass concentration are 30%, sub-sour sodium solid.
Further, the diazo reagent described in step (1) and the molar ratio of diazo component are 1 ~ 1.05:1.
Further, the molar ratio of diazo component, the vitriol oil and stablizer described in step (1) is 1:1 ~ 3:1 ~ 3
Further, the total amount that diazo component, the vitriol oil and stablizer described in step (1) are added accounts for 5 ~ 30% of reaction system gross weight.
Further, the molar ratio of the coupling component described in step (2) and the diazosalt solid of diazo component is 0.8 ~ 1:0.8 ~ 1.05.
Further, in step (1), the joining day of diazo reagent is 0.1 ~ 1h.
Further, in step (2), the time adding the diazosalt solid of diazo component under stirring is 5 ~ 60min.
Further, described organic solvent is the one, two or three in ethyl acetate, ether, ethylene glycol monomethyl ether, glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran (THF), ethanol, Virahol, dioxane.
Further, described stablizer is fluoroboric acid, Sodium tetrafluoroborate, zinc acetate, zinc chloride, Phenylsulfonic acid, 1-naphthalene sulfonic aicd, 2-naphthene sulfonic acid, 1, one or both in 5-bis-naphthene sulfonic acid, 2,6-bis-naphthene sulfonic acid, methylene dinaphthalene sulfonic acid, methylene-bis methyl naphthalene sulfonic acid.
A third aspect of the present invention provides the application of heterocycle azo type dye of the present invention in trevira, tynex, acid fiber by polylactic, polypropylene fibre, cellulose acetate dyeing.
Relative to prior art, beneficial effect of the present invention:
1. in the structure of compound of the present invention, its coupling component is heterocycle active methylene compound, heterocycle phenolic compound, and diazo component is weakly alkaline arylamine, and the dyeing brightness of acquisition is high.
2. the preparation method of compound of the present invention carries out diazotization to weakly alkaline arylamine in organic solvent, separate out stable diazosalt solid, after filtration obtains solid, it is applied to alkaline coupling, obtain target dyestuff, the method with carry out compared with diazotizing traditional method in sulfuric acid, sulfuric acid dosage is down to below 2 moles of times amount, reduces more than sulfuric acid 8 moles of times amount; And the diazonium salt that the method obtains is stable solid, can be used for alkaline coupling, obtain Novel disperse dyestuff.
3. the compounds of this invention may be used for the dyeing of trevira, tynex, acid fiber by polylactic, polypropylene fibre, cellulose acetate, and part of compounds also can be used for the responsive detection field of pH.
Accompanying drawing explanation
Fig. 1 is the mass spectrum 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 spectrum 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 spectrum 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 the uv-visible absorption spectra of dye composition 3# under different pH;
Figure 11 is the mass spectrum 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#.
Embodiment
In order to make object of the present invention, scheme, flow process and advantage clearly distinct, the present invention is described in further detail in conjunction with the accompanying drawings and embodiments, it should be noted that specific embodiment only illustratively illustrates the present invention, is not intended to limit the present invention herein.In following embodiment, if no special instructions, the experimental technique used is ordinary method, and material therefor, reagent etc. all can chemically company be bought.
Unless otherwise indicated, the technical term used in the present invention has following implication.
The term " alkyl " used in the present invention comprises straight chained alkyl and branched-chain alkyl.As mentioned, single alkyl is as " propyl group ", then only refer in particular to straight chained alkyl, and as mentioned, single branched-chain alkyl is as " sec.-propyl ", then only refer in particular to branched-chain alkyl.And for example " C 1-4alkyl " comprise C 1-3alkyl, methyl, ethyl, n-propyl, sec.-propyl and the tertiary butyl.Similar rule is also applicable to other group used in this specification sheets.
In formula (II-1): R a 1be preferably-H ,-CN ,-NO 2,-COR ,-COAr ,-CONH 2; Be more preferably-H ,-CN ,-NO 2; Most preferably be-H ,-NO 2; R a 2be preferably-H ,-R ,-OR ,-NO 2,-Cl; Be more preferably-H ,-R ,-OR ,-NO 2; Most preferably be-H ,-NO 2; R a 3be preferably-H ,-CN ,-NO 2,-Ar ,-COR ,-COAr, be more preferably-H ,-CN ,-NO 2,-Ar ,-COAr; Most preferably be-H ,-NO 2,-Ar.
In formula (II-2): R b 1be preferably-H ,-R ,-Ar ,-CF 3,-CN ,-COOR; Be more preferably-H ,-R ,-Ar ,-CF 3,-CN; Most preferably be-H ,-Ar ,-CF 3,-CN; R b 2be preferably-H ,-NO 2,-R ,-ROH ,-Ar ,-COOR ,-SO 2ar or-CN; Be more preferably-H ,-NO 2,-Ar ,-COOR ,-SO 2ar or-CN; Most preferably be-H ,-NO 2,-Ar ,-SO 2ar.
In formula (II-3): preferably R c 1and R c 2be selected from-H ,-Cl ,-Br ,-NO independently of one another 2,-R ,-OR; Be more preferably-H ,-Cl ,-NO 2,-OR; Most preferably be-H ,-Cl ,-NO 2; R c 2be preferably located on 1,2 positions; More preferably 1 is positioned at.
In formula (II-4): R d 1be preferably-NO 2,-Cl or-H; Be more preferably-NO 2or-H; Most preferably be-NO 2; R d 2be preferably-H ,-Cl; Be more preferably-H.
In formula (II-5): R ebe preferably-H ,-Ar ,-OR ,-CN ,-Cl or-CCl 3; Be more preferably-H ,-Ar ,-CN or-CCl 3; Most preferably be-H ,-CN or-CCl 3.
In formula (II-6): R fbe preferably-H ,-R ,-Ar ,-OR ,-CN; Be more preferably-H ,-Ar ,-OR ,-CN; Most preferably be-H ,-Ar ,-CN.
In formula (II-7): R gbe preferably-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl; Be more preferably-H ,-R ,-Ar ,-CN ,-Cl; Most preferably be-H ,-Ar ,-CN.
In formula (II-8): R h 1be preferably-CN ,-H ,-COOCH 3; Be more preferably-CN ,-H; R h 2be preferably-CONH 2,-H or-CH 2cN; Be more preferably-H or-CH 2cN; R h 3be preferably-H, phenyl; Be more preferably phenyl.
In formula (II-9): R i 1be preferably-CN ,-NO 2,-Br or-Cl; Be more preferably-CN ,-NO 2or-Cl; Most preferably be-NO 2or-Cl; R i 2be preferably-H ,-CN ,-NO 2,-Br or-Cl, be more preferably-H ,-NO 2,-Cl; Most preferably be-H ,-Cl; And work as R i 1during for Cl, Br or I, R i 2can not be H.
In formula (II-10): R jbe preferably-H ,-CN ,-NO 2,-Br; Be more preferably-H ,-NO 2; Most preferably be-H.
In formula (III-1): R j 1be preferably-H ,-CH 3,-Ar ,-COOR or-CONHR; Be more preferably-H ,-CH 3,-Ar or-CONHR; Most preferably be-H ,-Ar; R j 2be preferably-H ,-Ar or-ArSO 2nHR; Be more preferably-H ,-Ar; Most preferably be-Ar.
In formula (III-2): R k 1be preferably-R ,-OR ,-NHR, COOR or-CN; Be more preferably-R ,-NHR, COOR or-CN; Most preferably be-R, COOR or-CN; R k 2be preferably R ,-Ar ,-CN or-CONHR; Be more preferably R ,-Ar ,-CN; Most preferably be R ,-Ar; R k 3be preferably-R ,-Ar; Be more preferably-R.
In formula (III-3): R lbe preferably-R ,-OR ,-NO 2,-COOR or-Ar; Be more preferably-R ,-NO 2,-COOR or-Ar; Most preferably be-R ,-NO 2,-COOR.
In formula (III-4): R m 1be preferably-R ,-OR, COOR; Be more preferably-R, COOR; Most preferably be-R; R m 2for-H, R ,-Ar ,-CN ,-COOR; Be more preferably-H ,-Ar ,-CN ,-COOR; Most preferably be-H ,-Ar.
In formula (III-5): R n 1be preferably-R ,-OR, COOR ,-Ar; Be more preferably-R ,-OR, COOR; Most preferably be-R ,-OR; R n 2be preferably-H, R ,-Ar ,-SO 2nHR or-CONHR; Be more preferably-H, R ,-Ar or-CONHR; Most preferably be-H, R.
In formula III-6: R o 1be preferably-R ,-CH 2cH 2cH 2oH ,-CH 2cH 2oH; Be more preferably-R ,-CH 2cH 2oH; R o 2be preferably-H, R ,-Ar ,-SO 2nHR or-CONHR; Be more preferably-H, R ,-Ar ,-CONHR; Most preferably be-H ,-Ar.
In formula (III-7): R p 1be preferably-R, cyclohexyl ,-CH 2cH 2cH 2oH, CH 2cH 2cN; Be more preferably-R ,-CH 2cH 2cH 2oH, CH 2cH 2cN; Most preferably be-R, CH 2cH 2cN; R p 2be preferably-H ,-NO 2,-CN ,-Cl ,-Br; Be more preferably-H ,-NO 2,-CN ,-Cl; Most preferably be-H ,-NO 2.
In formula (III-8): R q 1be preferably-R ,-CH 2cH 2cH 2oH ,-CH 2cH 2oH; Be more preferably-R ,-CH 2cH 2oH; R q 2be preferably-R ,-CH 2cH 2cH 2oH ,-CH 2cH 2oH; Be more preferably-R ,-CH 2cH 2oH.
In formula (II-1) to formula (II-7) and formula (III-1) in formula (III-8): R is preferably-H, C 1-4alkyl or C 1-4alkoxyl group; Be more preferably hydrogen, C 1-2alkyl or C 1-2alkoxyl group; 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 under the vitriol oil exists, in organic solvent diazotization is carried out to diazo component, separate out stable diazosalt solid, after filtration obtains this solid, carry out coupled reaction with coupling component in the basic conditions, obtain target dyestuff.Specifically comprise the steps:
(1) diazo component of the present invention, the vitriol oil, organic solvent and stablizer are added in reaction vessel A, after being cooled to 0 ~ 10 DEG C, add diazo reagent in batches, reaction 0.1 ~ 10h, filters the diazosalt solid obtaining diazo component;
(2) coupling component according to claim 1 and water are added in reaction vessel B, with 10% sodium hydroxide adjust pH to 8 ~ 12, coupling component is dissolved, be cooled to 0 ~ 10 DEG C, the diazosalt solid of the diazo component that step (1) obtains is added under stirring, dissolve with 10% sodium carbonate and control, in the scope of pH value in reaction to 8 ~ 10, at 0 ~ 10 DEG C, to react 1 ~ 10h, obtain the compound of formula I;
One or both in the sodium nitrite solution that wherein said diazo reagent is nitrosyl sulfuric acid, butyl nitrite, nitrite tert-butyl, Isopentyl nitrite, amyl nitrite, isobutyl nitrite, nitrous acid isopropyl ester, mass concentration are 30%, sub-sour sodium solid.
In preferred technical scheme, described diazo reagent is one or both in nitrosyl sulfuric acid, butyl nitrite, nitrite tert-butyl, Isopentyl nitrite, amyl nitrite, isobutyl nitrite; Be more preferably nitrosyl sulfuric acid, nitrite tert-butyl, Isopentyl nitrite, isobutyl nitrite; Most preferably be nitrosyl sulfuric acid, nitrite tert-butyl.
In preferred technical scheme, the diazo reagent described in step (1) and the molar ratio of diazo component are 1.05 ~ 1:1, are more preferably 1.02 ~ 1:1, most preferably are 1:1; The molar ratio of diazo component and the vitriol oil is 1:1 ~ 3, is more preferably 1:1 ~ 2.5, most preferably is 1:1 ~ 2.
In preferred technical scheme, the molar ratio of diazo component, the vitriol oil and stablizer described in step (1) is 1:1 ~ 3:1 ~ 3, is more preferably 1:1 ~ 2.5:1 ~ 2.5, most preferably is 1:1 ~ 2:1 ~ 2.
In preferred technical scheme, the total amount that diazo component, the vitriol oil and stablizer described in step (1) are added accounts for 5 ~ 30% of reaction system gross weight, is more preferably 5 ~ 20%, most preferably is 5 ~ 15%.
In preferred technical scheme, the molar ratio of the coupling component described in step (2) and the diazosalt solid of diazo component is 1:1 ~ 1.05; Be more preferably 1:1 ~ 1.03, most preferably be 1:1.
In preferred technical scheme, in step (1), the time dripping diazo reagent is 0.1 ~ 1h, is more preferably 0.1 ~ 0.5h.
In preferred technical scheme, in step (2), the time adding the diazosalt solid of diazo component under stirring is 5 ~ 60min, is more preferably 10 ~ 40min.
In preferred technical scheme, described organic solvent is ethyl acetate, ether, ethylene glycol monomethyl ether, glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran (THF), ethanol, Virahol, one in dioxane, two or three, be more preferably ethyl acetate, ethylene glycol monomethyl ether, glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran (THF), one in dioxane, two or three, most preferably be ethyl acetate, ethylene glycol monomethyl ether, glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, one in ethylene glycol diethyl ether, two or three.
In preferred technical scheme, described stablizer is fluoroboric acid, Sodium tetrafluoroborate, zinc acetate, zinc chloride, Phenylsulfonic acid, 1-naphthalene sulfonic aicd, 2-naphthene sulfonic acid, 1, 5-bis-naphthene sulfonic acid, 2, 6-bis-naphthene sulfonic acid, NNO, one or both in MF, be more preferably fluoroboric acid, zinc chloride, 1-naphthalene sulfonic aicd, 2-naphthene sulfonic acid, 1, 5-bis-naphthene sulfonic acid, 2, 6-bis-naphthene sulfonic acid, methylene dinaphthalene sulfonic acid, methylene-bis methyl naphthalene sulfonic acid one or both, most preferably be fluoroboric acid, 1, 5-bis-naphthene sulfonic acid, 2, 6-bis-naphthene sulfonic acid, methylene dinaphthalene sulfonic acid, methylene-bis methyl naphthalene sulfonic acid one or both.
The preparation of embodiment 1 compound 1#
(1) by 1.5g5-aminobenzimidazole ketone, the 1g vitriol oil, 80ml ethylene glycol diethyl ether, 5g1,5-naphthalene disulfonic acid adds in there-necked flask, is cooled to 5 DEG C in ice-water bath, and drip 3g nitrite tert-butyl, time for adding is 0.5h, dropwises rear reaction 2 hours; Diazosalt solid is obtained after filtration; (2) 1.34g3-methyl isophthalic acid-phenyl-5 pyrazolone, 100ml water are added in reactor, with 10% sodium hydroxide solution adjust pH to 10, be cooled to 5 DEG C, the 5-Amino-2-benzimidazolinone diazonium salt that step (1) obtains is added under stirring, and by 10% sodium carbonate solution control ph 9, add in half an hour, and at 5 DEG C of reaction 2hr; React complete, filter, utilize frozen water to be washed till filtrate for neutrality, obtain heterocycle azo dispersed dye (compound 1#) after drying, coupling yield is 95%.
[the M-H]-quasi-molecular ions of compound 1# has been there is at m/z333.1 place, at 1700cm in infrared spectra (Fig. 2) in mass spectrum (Fig. 1) -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 1.83g2,4-dinitraniline, the 2g vitriol oil, 40ml glycol dimethyl ether, 4g1,5-naphthalene disulfonic acid adds in there-necked flask, is cooled to 3 DEG C in ice-water bath, and drip 3g nitrosyl sulfuric acid, time for adding is 0.5h, dropwises rear reaction 2 hours; Diazosalt solid is obtained after filtration; (2) 0.81g3-Methyl-5-pyrazolone, 80ml water are added in reactor, with 10% sodium hydroxide solution adjust pH to 11, be cooled to 4 DEG C, add under stirring that step (1) obtains 2,4-dinitroaniline diazonium salt, and by 10% sodium carbonate solution control ph 9, add in half an hour, and at 5 DEG C of reaction 2hr; React complete, filter, utilize frozen water to be washed till filtrate for neutrality, obtain heterocycle azo dispersed dye (compound 2#) after drying, coupling yield is 99%.
Occur at m/z291 place in mass spectrum (Fig. 4) [M-H] of compound 2# -quasi-molecular ions, at 1690cm in infrared spectra (Fig. 5) -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 1.45g2-amino-5-nitrothiazole, 60ml ethyl acetate, the 5g vitriol oil, 5g zinc acetate (30% aqueous solution) adds in there-necked flask, is cooled to 0 ~ 5 degree Celsius, adds 2g nitrosyl sulfuric acid in ice-water bath, after reaction 2 hours; Diazosalt solid is obtained after filtration; (2) 0.97g8-hydroxyquinoline, 80ml water are added in reactor, with 10% sodium hydroxide solution adjust pH to 10, be cooled to 5 DEG C, 2-amino-5-nitrothiazole the diazonium salt that step (1) obtains is added under stirring, and by 10% sodium carbonate solution control ph 9, add in half an hour, and at 5 DEG C of reaction 2hr; React complete, filter, utilize frozen water to be washed till filtrate for neutrality, obtain heterocycle azo dispersed dye (compound 3#) after drying, coupling yield is 80%.
Occur at m/z300 place in mass spectrum (Fig. 7) [M-H] of compound 3# -quasi-molecular ions, at 1550cm in infrared spectra (Fig. 8) -1with 1350cm -1for nitro characteristic peak, in nuclear magnetic spectrogram (Fig. 9), 8.2-9.5ppm is Hydrogen Proton peak on aromatic ring.Can find out in its uv-visible absorption spectra (Figure 10), when solution ph is 6, be purple, when solution ph is 8, maximum absorption wavelength is 626nm, is blueness, colour-change is remarkable, has pH sensitive color change characteristic, can be used for the open hole detection of pH.
The preparation of embodiment 4 compound 4#
(1) by 2.07g4-nitro-2,6-dichlorphenamide bulk powder, the 3g vitriol oil, 50ml glycol dimethyl ether, 3g1,5-naphthalene disulfonic acid adds in there-necked flask, be cooled to 4 degrees Celsius in ice-water bath, drip sodium nitrite solution (30%, the mol ratio of institute's dripping quantity and diazo component is 1.05:1), time for adding is 0.5h, dropwises rear reaction 1 hour; Diazosalt solid is obtained after filtration; (2) 1.24g3-methyl isophthalic acid-phenyl-5 pyrazolone, 50ml water are added in reactor, with 10% sodium hydroxide solution adjust pH to 11, be cooled to 6 DEG C, 4-nitro-2 is added under stirring, 6-dichlorphenamide bulk powder diazonium salt, and by 10% sodium carbonate solution control ph 10, add in half an hour, and at 8 DEG C of reaction 2h; React complete, filter, utilize frozen water to be washed till filtrate for neutrality, obtain heterocycle azo dispersed dye (compound 4#) after drying, coupling yield is 92%.
Occur at m/z390 place in mass spectrum (Figure 11) [M-H] of compound 3# -quasi-molecular ions is carbonyl characteristic peak 1660 in infrared spectra (Figure 12), and in H-NMR nuclear magnetic spectrogram (Figure 13), 7-8.6ppm is Hydrogen Proton peak on aromatic ring.
Embodiment 5
(1) by amino for 1.96g2--3,5-dinitro thiophenes, the 1g vitriol oil, 60ml glycol dimethyl ether, 5g2,6-naphthalene disulfonic acid adds in there-necked flask, is cooled to 3 DEG C in ice-water bath, drip 4g Isopentyl nitrite, time for adding is 0.5h, dropwises rear reaction 2 hours; Diazosalt solid is obtained after filtration; (2) 1.74gN-ethyl-3-cyano group-4-methyl-6-hydroxyl-2-pyridone, 100ml water are added in reactor, with 10% sodium hydroxide solution adjust pH to 11, be cooled to 5 DEG C, the 2-amino-3 that step (1) obtains is added under stirring, 5-dinitro thiophene diazonium salt, and by 10% sodium carbonate solution control ph 9, add in half an hour, and at 5 DEG C of reaction 2hr; React complete, filter, utilize frozen water to be washed till filtrate for neutrality, after drying, obtain heterocycle azo dispersed dye.
Embodiment 6
(1) by 1.0g2-aminothiazole, 60ml ethyl acetate, the 5g vitriol oil, 5g fluoroboric acid (40% aqueous solution) adds in there-necked flask, is cooled to 5 DEG C, adds 0.7g Sodium Nitrite in ice-water bath, after reaction 2 hours; Diazosalt solid is obtained after filtration; (2) 1.62g4-Hydroxycoumarin, 80ml water are added in reactor, with 10% sodium hydroxide solution adjust pH to 11, be cooled to 8 DEG C, the thiazolamine diazonium salt that step (1) obtains is added under stirring, and by 10% sodium carbonate solution control ph 9, add in half an hour, and at 5 DEG C of reaction 2hr; React complete, filter, utilize frozen water to be washed till filtrate for neutrality, after drying, obtain heterocycle azo dispersed dye.
Embodiment 7-22
Utilize 3-cyano group-6-hydroxy-4-methyl-2-pyridone, N-ethyl-3-cyano group-4-methyl-6-hydroxyl-2-pyridone, hexahydroxy-pyridone, 3-formamido group-4-methyl-6-hydroxy-n-ethylpyridine ketone, 4 hydroxy coumarin, 7-nitro-4 hydroxy coumarin, 7-methyl-4 hydroxy coumarin, 4-hydroxyquinoline, 2, 4-dihydroxyl 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-chloro-phenyl-)-3-methyl-5-pyrazolone, 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone, 3-Methyl-5-pyrazolone replaces 3-methyl isophthalic acid-phenyl-5 pyrazolone in embodiment 1, in the basic conditions respectively with the diazosalt solid coupling of 5-Amino-2-benzimidazolinone, obtain corresponding heterocycle azo dispersed dye.
Embodiment 23-30
Utilize 2,4-dinitraniline, 4-nitro-2, the amino phendioxin of 6-dibromo aniline, 4-nitro-2-cyano-aniline, 2-aminobenzothiazole, 6-nitrothiazole, 5-, 2,3-thiadiazoles, 2-aminothiophene, 1-phenyl-3-methyl-4-cyano group-5-amino-pyrazol replace the 5-Amino-2-benzimidazolinone in embodiment 1, carry out diazotization, obtain corresponding diazosalt solid, in the basic conditions respectively with 3-methyl isophthalic acid-phenyl-5 pyrazolone, obtain corresponding heterocycle azo dispersed dye.
Embodiment 31-38
Ethyl acetate, ether, ethylene glycol monomethyl ether, glycol dimethyl ether, tetrahydrofuran (THF), ethanol, Virahol, dioxane is utilized to replace ethylene glycol diethyl ether in embodiment 1 as the diazotizing solvent of 5-Amino-2-benzimidazolinone, obtain corresponding diazosalt solid, in the basic conditions respectively with the coupling of 3-methyl isophthalic acid-phenyl-5 pyrazolone, obtain corresponding heterocycle azo dispersed dye.
Embodiment 39-46
Utilize fluoroboric acid, Sodium tetrafluoroborate, zinc acetate, Phenylsulfonic acid, 1-naphthalene sulfonic aicd, 2-naphthene sulfonic acid, 2,6-bis-naphthene sulfonic acid, NNO, MF replace 1 in embodiment 1,5-naphthalene disulfonic acid is as the stablizer of 5-Amino-2-benzimidazolinone, obtain corresponding diazosalt solid, in the basic conditions respectively with the coupling of 3-methyl isophthalic acid-phenyl-5 pyrazolone, obtain corresponding heterocycle azo dispersed dye.
Embodiment 47-54
Nitrosyl sulfuric acid, butyl nitrite, Isopentyl nitrite, amyl nitrite, isobutyl nitrite, nitrous acid isopropyl ester is utilized to replace the nitrite tert-butyl in embodiment 1 as the diazo reagent of 5-Amino-2-benzimidazolinone, obtain corresponding diazosalt solid, in the basic conditions respectively with 3-methyl isophthalic acid-phenyl-5 pyrazolone, obtain corresponding heterocycle azo dispersed dye.
Embodiment 55-70
Utilize 3-cyano group-6-hydroxy-4-methyl-2-pyridone, hexahydroxy-pyridone, 3-formamido group-4-methyl-6-hydroxy-n-ethylpyridine ketone, 4 hydroxy coumarin, 7-nitro-4 hydroxy coumarin, 7-methyl-4 hydroxy coumarin, 4-hydroxyquinoline, 2, 4-dihydroxyl 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-chloro-phenyl-)-3-methyl-5-pyrazolone, 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone, 3-Methyl-5-pyrazolone replaces the 3-Methyl-5-pyrazolone in embodiment 2, in the basic conditions respectively with 2, the diazosalt solid coupling of 4-dinitraniline, obtain corresponding heterocycle azo dispersed dye.
Embodiment 71-78
Utilize 2-amino-3,5-dinitro thiophene, 4-nitro-2, the amino phendioxin of 6-dibromo aniline, 4-nitro-2-cyano-aniline, 2-aminobenzothiazole, 6-nitrothiazole, 5-, 2,3-thiadiazoles, 2-aminothiophene, 1-phenyl-3-methyl-4-cyano group-5-amino-pyrazol replace 2,4-dinitranilines in embodiment 2, carry out diazotization, obtain corresponding diazosalt solid, in the basic conditions respectively with the coupling of 3-Methyl-5-pyrazolone, obtain corresponding heterocycle azo dispersed dye.
Embodiment 79-86
Ethyl acetate, ether, ethylene glycol monomethyl ether, ethylene glycol diethyl ether, tetrahydrofuran (THF), ethanol, Virahol, dioxane is utilized to replace glycol dimethyl ether in embodiment 2 as 2, the diazotizing solvent of 4-dinitraniline, obtain corresponding diazosalt solid, in the basic conditions respectively with the coupling of 3-Methyl-5-pyrazolone, obtain corresponding heterocycle azo dispersed dye.
Embodiment 87-94
Utilize fluoroboric acid, Sodium tetrafluoroborate, zinc acetate, Phenylsulfonic acid, 1-naphthalene sulfonic aicd, 2-naphthene sulfonic acid, 2,6-bis-naphthene sulfonic acid, methylene dinaphthalene sulfonic acid, methylene-bis methyl naphthalene sulfonic acid replace in embodiment 21,5-naphthalene disulfonic acid is as 2, the stablizer of 4-dinitroaniline diazonium salt, obtain corresponding diazosalt solid, in the basic conditions respectively with the coupling of 3-Methyl-5-pyrazolone, obtain corresponding heterocycle azo dispersed dye.
Embodiment 95-102
Isopentyl nitrite, butyl nitrite, nitrite tert-butyl, amyl nitrite, isobutyl nitrite, nitrous acid isopropyl ester is utilized to replace nitrosyl sulfuric acid in embodiment 2 as 2, the diazo reagent of 4-dinitraniline, obtain corresponding diazosalt solid, in the basic conditions respectively with the coupling of 3-Methyl-5-pyrazolone, obtain corresponding heterocycle azo dispersed dye.
Embodiment 103-118
Utilize 3-cyano group-6-hydroxy-4-methyl-2-pyridone, hexahydroxy-pyridone, 3-formamido group-4-methyl-6-hydroxy-n-ethylpyridine ketone, 7-nitro-4 hydroxy coumarin, 7-methyl-4 hydroxy coumarin, 4-hydroxyquinoline, 2, 4-dihydroxyl 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-chloro-phenyl-)-3-methyl-5-pyrazolone, 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone, 3-Methyl-5-pyrazolone replaces the oxine in embodiment 3, in the basic conditions respectively with the diazosalt solid coupling of 2-amino-5-nitrothiazole, obtain corresponding heterocycle azo dispersed dye.
Embodiment 119-126
Utilize 2,4-dinitraniline, 4-nitro-2, the amino phendioxin of 6-dibromo aniline, 4-nitro-2-cyano-aniline, 2-aminobenzothiazole, 6-nitrothiazole, 5-, 2,3-thiadiazoles, 2-aminothiophene, 1-phenyl-3-methyl-4-cyano group-5-amino-pyrazol replace the 2-amino-5-nitrothiazole in embodiment 3, carry out diazotization, obtain corresponding diazosalt solid, in the basic conditions respectively with oxine coupling, obtain corresponding heterocycle azo dispersed dye.
Embodiment 127-134
Utilize glycol dimethyl ether, ether, ethylene glycol monomethyl ether, ethylene glycol diethyl ether, tetrahydrofuran (THF), ethanol, Virahol, dioxane replace ethyl acetate in embodiment 3 as the diazotizing solvent of 2-amino-5-nitrothiazole, obtain corresponding diazosalt solid, in the basic conditions respectively with oxine coupling, obtain corresponding heterocycle azo dispersed dye.
Embodiment 135-142
Utilize 1,5-naphthalene disulfonic acid, Sodium tetrafluoroborate, fluoroboric acid, Phenylsulfonic acid, 1-naphthalene sulfonic aicd, 2-naphthene sulfonic acid, 2,6-bis-naphthene sulfonic acid, methylene dinaphthalene sulfonic acid, methylene-bis methyl naphthalene sulfonic acid replace the zinc acetate in embodiment 3 as the stablizer of 2-amino-5-nitrothiazole diazonium salt, obtain corresponding diazosalt solid, in the basic conditions respectively with oxine coupling, obtain corresponding heterocycle azo dispersed dye.
Embodiment 143-150
Isopentyl nitrite, Sodium Nitrite, butyl nitrite, nitrite tert-butyl, amyl nitrite, isobutyl nitrite, nitrous acid isopropyl ester is utilized to 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 oxine coupling, obtain corresponding heterocycle azo dispersed dye.
Embodiment 151-166
Utilize 3-cyano group-6-hydroxy-4-methyl-2-pyridone, hexahydroxy-pyridone, 3-formamido group-4-methyl-6-hydroxy-n-ethylpyridine ketone, 7-nitro-4 hydroxy coumarin, 7-methyl-4 hydroxy coumarin, 4-hydroxyquinoline, 2, 4-dihydroxyl 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-chloro-phenyl-)-3-methyl-5-pyrazolone, 1-phenyl-3-methyl-4-benzoyl-5-pyrazolone, 3-Methyl-5-pyrazolone replaces 3-methyl isophthalic acid-phenyl-5 pyrazolone in embodiment 4, in the basic conditions respectively with 4-nitro-2, the diazosalt solid coupling of 6-dichlorphenamide bulk powder, obtain corresponding heterocycle azo dispersed dye.
Embodiment 167-174
Utilize 2,4-dinitraniline, thiazolamine, 4-nitro-2, the amino phendioxin of 6-dibromo aniline, 4-nitro-2-cyano-aniline, 2-aminobenzothiazole, 6-nitrothiazole, 5-, 2,3-thiadiazoles, 2-aminothiophene, 1-phenyl-3-methyl-4-cyano group-5-amino-pyrazol replace the 4-nitro-2 in embodiment 4,6-dichlorphenamide bulk powder, carry out diazotization, obtain corresponding diazosalt solid, in the basic conditions respectively with the coupling of 3-methyl isophthalic acid-phenyl-5 pyrazolone, obtain corresponding heterocycle azo dispersed dye.
Application examples 1
The dyestuff sand milling test that embodiment 1 obtains: the water of the dyestuff embodiment 1 of 0.50g obtained, dispersion agent NNO and the 2.80g of 1.00g is placed in the sand milling pipe that sand milling pearl and sand milling rod are housed, stir sand milling 1h, the dye diffusion performance that embodiment 1 obtains reaches 5 grades of HGT3399-2001 regulation.
Application examples 2
The dyestuff sand milling test that embodiment 2 obtains: the water of the dyestuff embodiment 2 of 0.50g obtained, dispersion agent NNO and the 2.80g of 1.00g is placed in the sand milling pipe that sand milling pearl and sand milling rod are housed, stir sand milling 1h, the dye diffusion performance that embodiment 2 obtains reaches 5 grades of HGT3399-2001 regulation.
Application examples 3
The dyestuff sand milling test that embodiment 4 obtains: the water of the dyestuff embodiment 4 of 0.50g obtained, dispersion agent NNO and the 2.80g of 1.00g is placed in the sand milling pipe that sand milling pearl and sand milling rod are housed, stir sand milling 1h, the dye diffusion performance that embodiment 4 obtains reaches 5 grades of HGT3399-2001 regulation.
Application examples 4
The dyestuff that embodiment 1 obtains is tested for dyeing terylene: dye to terylene by GBT9337-2009, bath raio 1:20, colourity 1.5%, pH=5 ~ 6,270.02 × 10 3pa, carry out high-temperature pressure dyeing, degree of exhaustion>=98% at 130 DEG C, the brightness that coloured fibre measures cloth specimen after dyeing through electronics color measurement and color match instrument is 71.65.
The dyestuff that embodiment 2 obtains is tested for dyeing terylene: dye to terylene by GBT9337-2009, bath raio 1:20, colourity 1.5%, pH=5 ~ 6,270.02 × 10 3pa, carry out high-temperature pressure dyeing, degree of exhaustion>=98% at 130 DEG C, the brightness that coloured fibre measures cloth specimen after dyeing through electronics color measurement and color match instrument is 80.51.
The dyestuff that embodiment 4 obtains is tested for dyeing terylene: dye to terylene by GBT9337-2009, bath raio 1:20, colourity 1.5%, pH=5 ~ 6,270.02 × 10 3pa, carry out high-temperature pressure dyeing, degree of exhaustion 98.2% at 130 DEG C, the brightness that coloured fibre 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-Diethyl Aniline be coupling component dyestuff (Comparison study embodiment 1) dyeing after brightness; The brightness of this coloured fibre is apparently higher than the brightness after the dyestuff being coupling component with N-ethyl-N-cyanoethyl aniline (Comparison study embodiment 2) dyeing, show with weakly alkaline arylamine be diazo component, with heterocycle active methylene compound or heterocycle phenols for coupling component, obtain heterocycle azo dispersed dye and there is excellent dyeing brightness.
Comparison study embodiment 1
Adopt the dyestuff of following structure A to carry out sand milling test: the water of dispersion agent NNO and the 2.80g of 0.50g dyestuff, 1.00g to be placed in the sand milling pipe that sand milling pearl and sand milling rod are housed, stir sand milling 1h, dye diffusion performance reaches 5 grades of HGT3399-2001 regulation.Above-mentioned dyestuff is used for dyeing terylene test: dye to terylene by GBT9337-2009, bath raio 1:20, colourity 1.5%, pH=5 ~ 6,270.02 × 10 3pa, carry out high-temperature pressure dyeing, degree of exhaustion 97.9% at 130 DEG C, the brightness that coloured fibre measures cloth specimen after dyeing through electronics color measurement and color match instrument is 38.24.
Comparison study embodiment 2
Adopt the dyestuff of following structure B to carry out sand milling test: the water of dispersion agent NNO and the 2.80g of 0.50g dyestuff, 1.00g to be placed in the sand milling pipe that sand milling pearl and sand milling rod are housed, stir sand milling 1h, dye diffusion performance reaches 5 grades of HGT3399-2001 regulation.Above-mentioned dyestuff is used for dyeing terylene test: dye to terylene by GBT9337-2009, bath raio 1:20, colourity 1.5%, pH=5 ~ 6,270.02 × 10 3pa, high-temperature pressure dyeing at 130 DEG C, degree of exhaustion 98.5%, the brightness that coloured fibre measures cloth specimen after dyeing through electronics color measurement and color match instrument is 40.91.

Claims (10)

1. heterocycle azo type dispersed dye, have the structure of formula I:
A-N＝N-B
In formula I, A is the residue after the diazonium salt of the diazo component that diazo component obtains through diazotization and coupling component coupling, and described diazo component is selected from the structure of general formula (II-1), (II-2), (II-3), (II-4), (II-5), (II-6), (II-7), (II-8), (II-9) and (II-10):
In formula (II-1):
R a 1for-H ,-CN ,-NO 2,-COR ,-COAr ,-CONH 2,-CONHR ,-SO 2,-COOR or-COAr;
R a 2for-H ,-R ,-OR ,-NO 2,-Cl or-Br;
R a 3for-H ,-CN ,-NO 2,-Ar ,-COR ,-COAr ,-COOR ,-COOAr ,-CONH 2,-CONHR ,-SCN ,-OCOR ,-CONHAr or-CHO;
In formula (II-2):
R b 1for-H ,-R ,-Ar ,-CF 3,-CN ,-COOR ,-CONH 2or-CH 2oH;
R b 2for-H ,-NO 2,-R ,-ROH ,-Ar ,-COOR ,-CONH 2,-SO 2r ,-SO 2ar or-CN;
In formula (II-3):
R c 1and R c 2be selected from-H ,-Cl ,-Br ,-NO independently of one another 2,-R ,-OR ,-CN ,-SO 2r ,-SO 2n or-CF 3;
R c 2for at the substituting group of 1,2 or 3;
In formula (II-4):
R d 1for-NO 2,-Cl ,-Br or-H;
R d 2for-H ,-Cl or-Br;
In formula (II-5):
R efor-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl or-CCl 3;
In formula (II-6):
R ffor-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-Cl or-CCl 3;
In formula (II-7):
R gfor-H ,-R ,-Ar ,-OR ,-CN ,-SCN ,-NO 2, CN ,-Cl or-CCl 3;
In formula (II-8):
R h 1for-CN ,-H ,-COOH or-COOCH 3;
R h 2for-SCH ,-H ,-CONH 2or-CH 2cN;
R h 3for-H, phenyl or cyclohexyl;
In formula (II-9):
R i 1for-CN ,-NO 2,-Cl ,-Br or-I;
R i 2for-H ,-CN ,-NO 2,-Cl ,-Br or-I, and work as R i 1during for-Cl ,-Br or-I, R i 2can not be-H;
In formula (II-10):
R jfor-H ,-CN ,-NO 2,-Cl ,-Br or-I;
In formula I, B is the residue after the diazonium salt coupling of coupling component and diazo component, and described coupling component is selected from general formula (III-1), (III-2), (III-3), (III-4), (III-5), (III-6), the structure shown in (III-7) and (III-8):
In formula (III-1):
R j 1for-H ,-CH 3,-Ar ,-CF 3,-CN ,-COOR or-CONHR;
R j 2for-H ,-Ar ,-ArCl or-ArSO 2nHR;
In formula (III-2):
R k 1for-R ,-OR ,-NHR, COOR ,-Ar or-CN;
R k 2for-H, R ,-Ar ,-CN ,-COOR ,-SO 2nHR or-CONHR;
R k 3for-R ,-Ar or cyclohexyl;
In formula (III-3):
R lfor-R ,-OR ,-NO 2,-CN ,-Cl ,-Br ,-COOR or-Ar;
In formula (III-4):
R m 1for-R ,-OR, COOR ,-Ar or-CN;
R m 2for-H, R ,-Ar ,-CN ,-COOR ,-SO 2nHR or-CONHR;
In formula (III-5):
R n 1for-R ,-OR, COOR ,-Ar or CN;
R n 2for-H, R ,-Ar ,-CN ,-COOR ,-SO 2nHR or-CONHR;
In formula (III-6):
R o 1for-R ,-CH 2cH 2cH 2oH ,-CH 2cH 2oH ,-CH 2cH 2cN or-Ar;
R o 2for-H, R ,-Ar ,-CN ,-COOR ,-SO 2nHR or-CONHR;
In formula (III-7):
R p 1for-R, cyclohexyl ,-CH 2cH 2cH 2oH ,-CH 2cH 2oH ,-CH 2cH 2cN or-Ar;
R p 2for-H ,-NO 2,-CN ,-Cl ,-Br ,-COOR ,-SO 2nHR or-CONHR;
In formula (III-8):
R q 1for-R, cyclohexyl ,-CH 2cH 2cH 2oH ,-CH 2cH 2oH ,-CH 2cH 2cN or-Ar;
R q 2for-R, cyclohexyl ,-CH 2cH 2cH 2oH ,-CH 2cH 2oH ,-CH 2cH 2cN or-Ar;
In formula (II-1) to formula (II-7) and formula (III-1) in formula (III-8):
R is hydrogen, C 1- 4alkyl or C 1- 4alkoxyl group;
Ar is phenyl.
2. the preparation method of heterocycle azo type dispersed dye as claimed in claim 1, it is characterized in that, the method comprises the steps:
(1) diazo component according to claim 1, the vitriol oil, organic solvent and stablizer are added in reaction vessel A, after being cooled to 0 ~ 10 DEG C, add diazo reagent in batches, reaction 0.1 ~ 10h, filters the diazosalt solid obtaining diazo component;
(2) coupling component according to claim 1 and water are added in reaction vessel B, with 10% sodium hydroxide adjust pH to 8 ~ 12, coupling component is dissolved, be cooled to 0 ~ 10 DEG C, the diazosalt solid of the diazo component that step (1) obtains is added under stirring, control the pH value of reaction in 8 ~ 10 scopes with 10% sodium carbonate solution simultaneously, at 0 ~ 10 DEG C, react 1 ~ 10h, obtain the compound of formula I;
One or both in the sodium nitrite solution that wherein said diazo reagent is nitrosyl sulfuric acid, butyl nitrite, nitrite tert-butyl, Isopentyl nitrite, amyl nitrite, isobutyl nitrite, nitrous acid isopropyl ester, mass concentration are 30%, sub-sour sodium solid.
3. preparation method according to claim 2, is characterized in that, the diazo reagent described in step (1) and the molar ratio of diazo component are 1 ~ 1.05:1.
4. preparation method according to claim 2, is characterized in that, the molar ratio of diazo component, the vitriol oil and stablizer described in step (1) is 1:1 ~ 3:1 ~ 3.
5. preparation method according to claim 2, is characterized in that, the total amount that diazo component, the vitriol oil and stablizer described in step (1) are added accounts for 5 ~ 30% of reaction system gross weight.
6. preparation method according to claim 2, is characterized in that, the molar ratio of the coupling component described in step (2) and the diazosalt solid of diazo component is 0.8 ~ 1:0.8 ~ 1.05.
7. preparation method according to claim 2, is characterized in that, in step (1), the joining day of diazo reagent is 0.1 ~ 1h.
8. preparation method according to claim 2, is characterized in that, in step (2), the time adding the diazosalt solid of diazo component under stirring is 5 ~ 60min.
9. preparation method according to claims 2 to 8, it is characterized in that, described organic solvent is the one, two or three in ethyl acetate, ether, ethylene glycol monomethyl ether, glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, tetrahydrofuran (THF), ethanol, Virahol, dioxane; Described stablizer is one or both in fluoroboric acid, Sodium tetrafluoroborate, zinc acetate, zinc chloride, Phenylsulfonic acid, 1-naphthalene sulfonic aicd, 2-naphthene sulfonic acid, 1,5-bis-naphthene sulfonic acid, 2,6-bis-naphthene sulfonic acid, methylene dinaphthalene sulfonic acid, methylene-bis methyl naphthalene sulfonic acid.
10. the application of heterocycle azo type dye as claimed in claim 1 in the dyeing of trevira, tynex, acid fiber by polylactic, polypropylene fibre or cellulose acetate.
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