CN106967303A - A kind of blue azo dyes of gorgeous color and its preparation method and application - Google Patents

A kind of blue azo dyes of gorgeous color and its preparation method and application Download PDF

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Publication number
CN106967303A
CN106967303A CN201710301117.7A CN201710301117A CN106967303A CN 106967303 A CN106967303 A CN 106967303A CN 201710301117 A CN201710301117 A CN 201710301117A CN 106967303 A CN106967303 A CN 106967303A
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CN
China
Prior art keywords
azo dyes
represent
gorgeous color
blue azo
color
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Pending
Application number
CN201710301117.7A
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Chinese (zh)
Inventor
李百春
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
HANGZHOU FULAI'ENTE FINECHEMICAL Co Ltd
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HANGZHOU FULAI'ENTE FINECHEMICAL Co Ltd
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Priority to CN201710301117.7A priority Critical patent/CN106967303A/en
Publication of CN106967303A publication Critical patent/CN106967303A/en
Priority to TW107104577A priority patent/TW201843244A/en
Priority to KR1020180016342A priority patent/KR102137478B1/en
Pending legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/06Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08Amino benzenes
    • C09B29/0833Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B51/00Nitro or nitroso dyes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/06Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08Amino benzenes
    • C09B29/0833Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
    • C09B29/0834Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -O-
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/06Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08Amino benzenes
    • C09B29/0833Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5
    • C09B29/0836Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -N=
    • C09B29/0838Amino benzenes characterised by the substituent on the benzene ring excepted the substituents: CH3, C2H5, O-alkyl, NHCO-alkyl, NHCOO-alkyl, NHCO- C6H5, NHCOO-C6H5 linked through -N= specific alkyl-CO-N-, aralkyl CON-, cycloalkyl CON-, alkyl OCON-
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/16General 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
    • D06P1/18Azo dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/16General 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
    • D06P1/19Nitro dyes
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • D06P3/54Polyesters using dispersed dyestuffs
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34Material containing ester groups
    • D06P3/52Polyesters
    • D06P3/56Preparing azo dyes on the material

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

Abstract

The invention discloses blue azo dyes of a kind of gorgeous color and its preparation method and application, shown in structural formula such as formula (I), application of the blue azo dyes of gorgeous color in dyeing polyester fibers or stamp in the present invention.The blue azo dyes of gorgeous color is mixed with selected from least one of general structure (I) compound and obtains disperse dye composition, the disperse dye composition can be applicable in dyeing polyester fibers or stamp.When the present invention is dyed, its fastness to washing, fastness to rubbing, fastness to perspiration, sunlight fastness and dye uptake are all good, the disperse dye composition staining power of the present invention is high, bright in colour, dyeability is good, especially possesses excellent washing fastness, color stability, not fugitive color, cost is relatively low.

Description

A kind of blue azo dyes of gorgeous color and its preparation method and application
Technical field
The invention belongs to technical field of dye, and in particular to a kind of blue azo dyes of gorgeous color and its preparation method and application.
Background technology
Into after 21 century, the competition in world textile market is more and more fierce, and the economy in Southeast Asia has turned into low cost, height The synonym of growth, and the textile industry business in Europe, U.S. etc. also accelerates to shift to Asia.Swash to adapt to piece market The situation of strong competition, makes the production cost of textile constantly reduce, product quality is improved constantly, carrying capacity of environment constantly mitigates, As the common target of textile enterprise.
Disperse dyes solubility in water is very low, and particle is very thin, is in dispersion in dye liquor, belongs to nonionic dye, It is mainly used in the dyeing of terylene, its dyefastness is higher.
Azo dyes (azo group two ends connect a class organic compound of aryl) is fabric clothing in dyeing and printing process Most widely used class synthetic dyestuffs, for dyeing and the stamp of a variety of natural and synthetic fibers, be also used for paint, plastics, The coloring of rubber etc..Azo dyes has multiple color, such as red, yellow, green, blue, but existing blue azo contaminates There is washing fastness in material, easily migrated out under the high temperature conditions from fabric fibre inside, have a strong impact on dyestuff To the dyefastness of fabric.
The content of the invention
The technical problem to be solved in the present invention is to provide a kind of blue azo dyes of gorgeous color, with preferable dyefastness.
In order to solve the above-mentioned technical problem, the technical scheme is that:
A kind of blue azo dyes of gorgeous color, shown in structural formula such as formula (I):
Wherein R1Represent H, CH3O or C2H5O;
R2Represent C1~C4Alkyl;
R3Represent C1~C4Alkyl.
Preferably, R1Represent CH3O。
Preferably, R2Represent ethyl.
Preferably, R3Represent methyl.
Preferably, comprising the following steps:
1) bromo- 2, the 4- dinitroanilines of 6- carry out diazotising with nitrosyl sulfuric acid, then carry out being coupled instead with coupling component Should, structural formula shown in formula (1) is dried to obtain in filtering washing:
Wherein R1Represent H, CH3O or C2H5O;R2Represent C1~C4Alkyl;R3Represent C1~C4Alkyl;
The coupling component is the structural formula shown in (2) formula:
Wherein R1Represent H, CH3O or C2H5O, R2Represent C1~C4Alkyl, R3Represent C1~C4Alkyl;
2) formula (1) is subjected to cyanogenation with zinc salt and mantoquita in dimethyl acetamide, filters out crude product;
3) crude product is carried out in water with acidic ferric chloride removing poison, the blue azo dyes of gorgeous color is washed to obtain in filtering.
Present invention also offers a kind of disperse dyes, contain the blue azo dyes of above-mentioned gorgeous color, the blue azo dyes of gorgeous color Selected from least one of general structure (I) compound.
It should be noted that due to the particularity of dye industry, each component is difficult also It is not necessary to which sterling is made, it will usually Containing a small amount of moisture content and micro physical impurity, the presence of this part moisture content and physical impurity is in tolerance range of the invention Within.
The dye composite of the present invention can be obtained by preparation method conventional in the industry, for example, press group each component After default proportioning mixing, sand mill or grinding are used in the presence of auxiliary agent (including dispersant, water or other wetting agents, etc.) The reducing mechanisms such as machine carry out corpusculed, that is, obtain the disperse dye composition;Can also first by each component respectively auxiliary agent, Corpusculed is carried out with reducing mechanisms such as sand mill or grinders in the presence of water or other wetting agents, is then matched somebody with somebody according to default Than being mixed, that is, obtain the dispersed black dye mixture.
Present invention also offers application of the blue azo dyes of above-mentioned gorgeous color in dyeing polyester fibers or stamp.
Present invention also offers application of the above-mentioned disperse dye composition in dyeing polyester fibers or stamp.
Present invention also offers it is a kind of dyed using the blue azo dyes of above-mentioned gorgeous color or stamp Polyester Fibers.
Present invention also offers it is a kind of dyed using above-mentioned disperse dyes or stamp Polyester Fibers.
Compared with prior art, beneficial effects of the present invention are embodied in:
When the present invention is dyed, its fastness to washing, fastness to rubbing, fastness to perspiration, sunlight fastness and colouring Rate is all good, and disperse dye composition staining power of the invention is high, bright in colour, dyeability is good, especially possesses excellent Washing fastness, color stability, not fugitive color, cost is relatively low.
Embodiment
Embodiment 1
A kind of blue azo dyes of gorgeous color of the present embodiment, structural formula is as follows:
Wherein R1Represent H;
R2Represent methyl;
R3Represent ethyl.
The preparation method of the blue azo dyes of the gorgeous color is as follows:
1) add between a certain amount of sulfuric acid and nitrosyl sulfuric acid, 20~25 degree of temperature of control, slowly add in diazonium kettle Enter bromo- 2, the 4- dinitroanilines of 6-, add 20~25 degree of insulation reactions 4 hours, terminal is detected with frozen water, it is qualified rear standby.
2) added water in coupling bucket, sulfuric acid and sulfamic acid, be then slowly added into coupling component (3-N, N- dipropyl acyl-oxygen Methyl-antifebrin) dissolving, dissolving is completely on the rocks to be cooled to 0 degree or so, is slowly added into the above-mentioned diazol got ready and is coupled Reaction, it is terminal that diazol, which adds and continues stirring until diazol and disappear, is passed through steam and is warming up to 55~60 degree insulations to turn brilliant 1 small When, 50 degree of hot wash filter cakes of filtering to neutrality, discharging drying obtains following structural formula:
Wherein R1Represent H;R2Represent methyl;R3Represent ethyl.
3) dimethyl acetamide is added in cyaniding kettle, input structure above is warming up to 90~95 degree of dissolvings, is cooled to 80 degree or so, add zinc salt and mantoquita, 85~90 degree of keeping temperature is reacted 1 hour, sampling detects terminal, it is qualified after be cooled to 20 ~40 degree, water is slowly added into, crude product is filtered to obtain.
4) added water in except malicious kettle, put into crude product, mashing adds acid chlorization ferrous solution, be warming up to 60~65 to uniform The blue azo dyes of above-mentioned gorgeous color is washed to obtain in degree reaction 2 hours, filtering.
Embodiment 2
A kind of blue azo dyes of gorgeous color of the present embodiment, structural formula is as follows:
Wherein R1Represent CH3O;
R2Represent ethyl;
R3Represent methyl.
The preparation method of the blue azo dyes of the gorgeous color is with reference to embodiment 1, and difference is that coupling component is differed.
Embodiment 3
A kind of blue azo dyes of gorgeous color of the present embodiment, structural formula is as follows:
Wherein R1Represent C2H5O;
R2Represent butyl;
R3Represent ethyl.
The preparation method of the blue azo dyes of the gorgeous color is with reference to embodiment 1, and difference is that coupling component is differed.
Embodiment 4
A kind of blue azo dyes of gorgeous color of the present embodiment, structural formula is as follows:
Wherein R1Represent CH3O;
R2Represent ethyl;
R3Represent propyl group.
The preparation method of the blue azo dyes of the gorgeous color is with reference to embodiment 1, and difference is that coupling component is differed.
Embodiment 5
A kind of blue azo dyes of gorgeous color of the present embodiment, structural formula is as follows:
Wherein R1Represent C2H5O;
R2Represent methyl;
R3Represent butyl.
The preparation method of the blue azo dyes of the gorgeous color is with reference to embodiment 1, and difference is that coupling component is differed.
Detect example 1
Dispersed black dye mixture made from 1.0g embodiments 1~5 is respectively taken, is scattered in 500mL water, dispersion liquid is obtained, 20mL dispersion liquids are drawn again to mix with 60mL water, dye liquor is obtained, and it is 5 to adjust dye bath pH with acetic acid, and 4g is put into when being warming up to 70 DEG C Polyester fiber is dyed, and with dye bath temperature is warming up into 130 DEG C from 70 DEG C in 30min, is incubated at 130 DEG C after 30min It is cooled to 90 DEG C, sampling.Sample cloth coloured light is observed, and national standard GB/T3921-1997, GB/T3920-1997, GB/ is respectively adopted The washing fastness of T3922-1997, GB/T8427-1998 test specimens cloth, fastness to rubbing, fastness to perspiration and sun-resistant Fastness, dyestuff dye uptake is determined using GB/T9337-2009 methods, and test result is shown in Table 1.
Table 1
Every fastness ability of the dye composite prepared from table 1, embodiment 1~5 is more excellent;
Wherein, R is worked as1Represent CH3O、R2Represent ethyl, R3When representing methyl, the dyeing of the blue azo dyes of prepared gorgeous color Fastness, washing fastness and dye uptake are optimal.
Embodiment 6
A kind of disperse dyes of the present embodiment, the gorgeous color shown in the blue azo dyes of gorgeous color shown in embodiment 1, embodiment 2 is blue The blue azo dyes of color shown in azo dyes and embodiment 3, according to mass ratio 1:2:2 ratio is mixed.
Embodiment 7
A kind of disperse dyes of the present embodiment, the gorgeous color shown in the blue azo dyes of gorgeous color shown in embodiment 2 and embodiment 3 is blue Azo dyes, according to mass ratio 2:3 ratio is mixed.
Embodiment 8
A kind of disperse dyes of the present embodiment, the gorgeous color shown in the blue azo dyes of gorgeous color shown in embodiment 3 and embodiment 4 is blue Azo dyes, according to mass ratio 3:1 ratio is mixed.
Embodiment 9
A kind of disperse dyes of the present embodiment, the gorgeous color shown in the blue azo dyes of gorgeous color shown in embodiment 1 and embodiment 5 is blue Azo dyes, according to mass ratio 1:3 ratio is mixed.
Embodiment 10
A kind of disperse dyes of the present embodiment, the gorgeous color shown in the blue azo dyes of gorgeous color shown in embodiment 1, embodiment 2 is blue Azo dyes, by shown in the blue azo dyes of gorgeous color and embodiment 5 shown in the blue azo dyes of gorgeous color shown in embodiment 3, embodiment 4 The blue azo dyes of gorgeous color, according to mass ratio 1:2:4:3:1 ratio is mixed.
Detect example 2
Disperse dyes made from 1.0g embodiments 6~10 are taken, using with detecting the identical method of example 1, are disperseed using above-mentioned Dye composite is dyed to polyester fiber cloth, and the fastness to washing of test specimens cloth, fastness to rubbing, fastness to perspiration, Sunlight fastness and dye uptake, test result are shown in Table 2.
Table 2
Every fastness ability of the disperse dyes prepared from table 2, embodiment 6~10 is more excellent;Wherein, implement The dyefastness of dye composite prepared by example 6, washing fastness and dye uptake are optimal.

Claims (10)

1. a kind of blue azo dyes of gorgeous color, it is characterised in that shown in structural formula such as formula (I):
Wherein R1Represent H, CH3O or C2H5O;
R2Represent C1~C4Alkyl;
R3Represent C1~C4Alkyl.
2. the blue azo dyes of gorgeous color as claimed in claim 1, it is characterised in that R1Represent CH3O。
3. the blue azo dyes of gorgeous color as claimed in claim 1, it is characterised in that R2Represent ethyl.
4. the blue azo dyes of gorgeous color as claimed in claim 1, it is characterised in that R3Represent methyl.
5. the preparation method of the blue azo dyes of gorgeous color as claimed in claim 1, it is characterised in that comprise the following steps:
1) bromo- 2, the 4- dinitroanilines of 6- carry out diazotising with nitrosyl sulfuric acid, then carry out coupling reaction, mistake with coupling component Drainage, which is washed, dries to obtain structural formula shown in formula (1):
Wherein R1Represent H, CH3O or C2H5O;R2Represent C1~C4Alkyl;R3Represent C1~C4Alkyl;
The coupling component is the structural formula shown in (2) formula:
Wherein R1Represent H, CH3O or C2H5O, R2Represent C1~C4Alkyl, R3Represent C1~C4Alkyl;
2) formula (1) is subjected to cyanogenation with zinc salt and mantoquita in dimethyl acetamide, filters out crude product;
3) crude product is carried out in water with acidic ferric chloride removing poison, the blue azo dyes of gorgeous color is washed to obtain in filtering.
6. a kind of disperse dyes, it is characterised in that described gorgeous containing the blue azo dyes of the gorgeous color as described in Claims 1 to 4 is any Color orchid azo dyes is selected from least one of general structure (I) compound.
7. application of the blue azo dyes of the gorgeous color as described in Claims 1 to 4 is any in dyeing polyester fibers or stamp.
8. application of the disperse dye composition as claimed in claim 6 in dyeing polyester fibers or stamp.
9. it is a kind of dyed using the blue azo dyes of the gorgeous color as described in Claims 1 to 4 is any or stamp polyester fiber material Material.
10. it is a kind of dyed using disperse dyes as claimed in claim 6 or stamp Polyester Fibers.
CN201710301117.7A 2017-05-02 2017-05-02 A kind of blue azo dyes of gorgeous color and its preparation method and application Pending CN106967303A (en)

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CN201710301117.7A CN106967303A (en) 2017-05-02 2017-05-02 A kind of blue azo dyes of gorgeous color and its preparation method and application
TW107104577A TW201843244A (en) 2017-05-02 2018-02-08 Chromic blue azo dye as well as preparation method and application thereof
KR1020180016342A KR102137478B1 (en) 2017-05-02 2018-02-09 Brilliant blue azo dye and method of preparation thereof, and its use

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CN107892824B (en) * 2017-10-26 2019-05-17 浙江闰土研究院有限公司 A kind of preparation method of environment-friendly type azo dispersion dyes

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Application publication date: 20170721