CN101284800B - Monoazo compounds with alkoxy, preparation method and uses thereof - Google Patents

Monoazo compounds with alkoxy, preparation method and uses thereof Download PDF

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CN101284800B
CN101284800B CN2008100155986A CN200810015598A CN101284800B CN 101284800 B CN101284800 B CN 101284800B CN 2008100155986 A CN2008100155986 A CN 2008100155986A CN 200810015598 A CN200810015598 A CN 200810015598A CN 101284800 B CN101284800 B CN 101284800B
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compound
formula
alkoxyl group
dispersed dye
monoazo compound
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CN101284800A (en
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王喆
王淑香
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Zhejiang Yutai Dyeing Technology Co.,Ltd.
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ZHEJIANG HUIDELONG CHEMICAL CO Ltd
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Abstract

The invention discloses a mono-azo compound provided with an alkoxyl, wherein, the structural formula is shown in (1). In the formula, OR1 is in para-position or ortho-position of an azo-group; R1 is C2-6 alkyl; R2 = H, CH3, C1, Br; n = 0 - 2; the compound is obtained by reacting with acid-binding agent and alkylating agent in strong polar solvent. The compound is used as disperse dye, has excellent alkali resistance, high washing fastness, high dyeing rate, and is environmental-friendly.

Description

A kind of Monoazo compound, Its Preparation Method And Use with alkoxyl group
Technical field:
The present invention relates to a kind of Monoazo compound, Its Preparation Method And Use, belong to the fine chemical technology field with alkoxyl group.
Background technology:
Be used for the azo-type compound of dispersed dye at present, mainly contain:
1.C.I. DISPERSE YELLOW 70, its structural formula is:
Figure S2008100155986D00011
2. Chinese patent application numbers 87100778.9, and its structural formula is:
Figure S2008100155986D00012
3. Chinese patent application number 03124687.7, and its structural formula is:
In the formula, X is Cl, Br or CN, n=1 ~ 2
R 1Be OH, R 2Be H or X
R 2Be OH, R 1Be H or X
Though above-claimed cpd obtains using in the certain limit of dispersed dye, but because the progress of weaving and printing technology, the dyeing and printing process of some environmental protection and energy saving is had higher requirement to the alkali resistance of dyestuff, above-mentioned dyestuff can not satisfy new requirement, alkali resistance is not good, not can be applicable to the environment-protective process of basic dyeing.
Summary of the invention:
The objective of the invention is to overcome the deficiency of above-mentioned prior art and provide a kind of have alkoxyl group Monoazo compound, Its Preparation Method And Use, this dispersed dye alkali resistance is splendid, the washing fastness height, the dye uptake height, environmental protection is widely used in trevira, hyperfine polyester fiber, washs the dyeing of ammonia BLENDED FABRIC.
Purpose of the present invention can reach by following measure: a kind of Monoazo compound with alkoxyl group is characterized in that its general structure is shown in (1):
Figure S2008100155986D00021
In the formula, OR 1At azo-group contraposition or ortho position,
R 1For
Figure S2008100155986D00022
Figure S2008100155986D00023
C 2 ~ 6Alkyl, this alkyl is from C 2Upwards, wherein can insert or not insert Sauerstoffatom;
R 2＝H、CH 3、Cl、Br；n＝0~2；
Described Monoazo compound preferred construction general formula with alkoxyl group is shown in (1a):
Figure S2008100155986D00024
R wherein 1Definition with above-mentioned formula (1).
Described Monoazo compound preferred construction general formula with alkoxyl group is shown in (1b):
Figure S2008100155986D00025
R wherein 1Definition with above-mentioned formula (1).
Described Monoazo compound preferred construction general formula with alkoxyl group is shown in (1c):
R wherein 1Definition with above-mentioned formula (1).
A kind of preparation method with Monoazo compound of alkoxyl group, it comprises the steps: the compound shown in the formula (2) is reacted with acid binding agent and alkylating agent in intensive polar solvent, and phenolic hydroxyl group hydrogen is replaced, and obtains described formula (1) monoazo nitrogen compound;
Figure S2008100155986D00032
In the formula, OH is at azo-group contraposition or ortho position,
R 2＝H、CH 3、Cl、Br；n＝0~2；
The preferred sulfone class of described intensive polar solvent, amides, ethylene glycol or its ethers, polyoxyethylene glycol or its ether organic solvent, or at least a in its aqueous solution; At least a in described acid binding agent preferred alkali metal hydroxide, alkaline earth metal hydroxides or its carbonate; At least a in described alkylating agent preferably sulfuric acid ester class, benzene sulfonate class, the halogenated hydrocarbon compound.
Monoazo compound with alkoxyl group of the present invention is used as dispersed dye.
Described dispersed dye comprise the mixture of the compound of general structure shown in (1) of at least two kinds of different structures.
Described dispersed dye comprise at least a general structure compound as the formula (1) and the composite mixture of other dispersed dye, and the weight of the compound shown in the formula (1) surpasses 10% of the former dyestuff gross weight of other dispersed dye.
Described dispersed dye are used as trevira, hyperfine polyester fiber, wash the dyeing on the ammonia BLENDED FABRIC.
The present invention can produce following positively effect compared with the prior art: Monoazo compound of the present invention, its alkali resistance is greatly improved, light fastness is good, applicable to fabric Dyeing in Alkali Bath technologies such as the many trevira of advantage, also be applicable to trevira, hyperfine polyester fiber, wash the dyeing of ammonia BLENDED FABRIC etc., can obtain dark heavy colour, washing fastness is good, has high washing fastness, exhaustion during dip-dye, fixation, dyebath stability, temperature dependency is all good, and high dye uptake is arranged, and dyeing waste-water is almost colourless, be beneficial to environmental protection, and dispersed dye of the present invention are also suitable to the composite mixing of other dispersed dye.
Embodiment:
With specific embodiment the present invention is described below, but protection scope of the present invention is not limited to this.
Embodiment 1:
In the there-necked flask of 250ml, add the 50ml dimethyl sulfoxide (DMSO), under agitation slowly add 20gN`-(2 then, 4-dinitrophenyl) benzene-1,4-diamine is 4-(2,4-oil of mirbane imino-)-4 '-hydroxyazobenzene, rise to 40 ℃ in water-bath, add 3.2g sodium hydroxide and be stirred to molten entirely.Then slowly drip the 8.5ml ethyl sulfate down, and insulation reaction to terminal at 40-50 ℃.Product is diluted in the 500ml water, filters washing, obtain following formula: compound:
Figure S2008100155986D00041
Compound maximum absorption wavelength in ethylene glycol monoethyl ether is λ max=385nm.
Embodiment 2:
In the 250ml there-necked flask, add 50ml ethylene glycol monomethyl ether and 30ml water, under agitation slowly add 20.5g 4-(2 then, 4-dinitrobenzene imines)-2 '-hydroxyl-5 '-methyl-benzene, be warming up to 40 ℃ in water-bath, adding 4.5g yellow soda ash is stirred to molten entirely, then adds the 6ml Benzyl Chloride and rises to 90 ℃, reaction to terminal, be diluted in the there-necked flask that fills 500ml water under stirring, filter washing, get following formula: compound:
Figure S2008100155986D00042
The maximum absorption wavelength λ max=380nm of compound in ethylene glycol monoethyl ether.
Embodiment 3:
In the there-necked flask of 250ml, add the 80ml ethylene glycol monoethyl ether, under agitation slowly add 20.5g 4-(2 then, 4-dinitrobenzene imines)-2 '-methyl-4 '-hydroxyazobenzene, in oil bath, be warming up to 40 ℃, adding 3.0g potassium hydroxide is stirred to molten entirely, then add the 10ml n-butyl bromide, rise to the boiling reflux reaction again, along with the consumption of n-butyl bromide reaction, the corresponding rising of reflux temperature is warming up to 110 ℃ then and is reacted to terminal point, be cooled to 80 ℃, be diluted in the 500ml water, filter washing, obtain following formula: compound:
The maximum absorption wavelength λ max=391nm of compound in ethylene glycol monoethyl ether.
Embodiment 4:
In the there-necked flask of 250ml, add the 80ml N-BUTYL ACETATE, under agitation add 10g 4-(2 then, 4-dinitrobenzene imines)-2 '-hydroxyl-5 '-methyl-benzene and 10g 4-(2,4-dinitrobenzene imines)-2 '-methyl-4 '-hydroxyazobenzene, in water-bath, be heated to 50 ℃, add 4.5g yellow soda ash and rise to 80 ℃ of stirring and dissolving 2 hours, then drip the reaction of 8.5ml ethyl sulfate to terminal down at 80-85 ℃, add 50ml hot water, steam except that N-BUTYL ACETATE filtration washing with water vapour, get the following formula mixture:
With
Figure S2008100155986D00052
The maximum absorption wavelength λ max=386nm of mixture in ethylene glycol monoethyl ether.
Embodiment 5-17:
Compound structure as the formula (1), synthetic method is seen the table 1 with reference to embodiment.
Figure S2008100155986D00053
Embodiment table 1
Embodiment With reference to embodiment OR 1 R 2 n λmax
5 3 4`-OC 4H 9 H / 386
6 2 4`-OCH 2C 6H 5 H / 382
7 1，4 4`-OC 2H 5 2`-CH 3 1 390
8 2 4`-OCH 2C 6H 5 2`-CH 3 1 387
9 1，4 4`-OC 2H 5 3`-CH 3 1 389
10 3 4`-OC 4H 9 3`-CH 3 1 391
11 2 4`-OCH 2C 6H 5 3`-CH 3 1 388
12 1，4 2`-OC 2H 5 5`-CH 3 1 383
13 3 2`-OC 4H 9 5`-CH 3 1 384
14 1，4 4`-OC 2H 5 Br 1 384
15 1，4 4`-OC 2H 5 Cl 1 383
16 2 4`-OCH 2C 6H 5 Br 1 381
17 2 4`-OCH 2C 6H 5 Cl 1 380
Embodiment 18:
Monoazo compound with the embodiment 1 of 1 weight part
Figure S2008100155986D00061
With the water of 7 weight parts and the dispersing agent MF sand milling of 2 weight parts, spraying drying obtains DISPERSE YELLOW A then in sand mill.Use this dyestuff, utilize High Temperature High Pressure to dye model machine, under pH value 4-4.5 condition,, hyperfine polyester fiber is dyeed, and carry out reduction clearing, obtain golden yellow and dye sample in 130 ℃ of dyeing 60 minutes.Dyeing sample oven dry back is surveyed washing (six fine the contaminations) fastness at 180 ℃ of typing 30sec with AATCC IIA method, and its result is shown in table (1):
Table (1)
Figure S2008100155986D00062
Substantially dye when this dyestuff is warming up to 120 ℃ to the greatest extent, can be used for rapid dyeing, dye uptake is up to more than 98%, and raffinate is almost colourless, is beneficial to the environmental protection treatment of dyeing waste liquid.
Embodiment 19:
Embodiment 18 made DISPERSE YELLOW A utilize High Temperature High Pressure to dye model machine, under pH value 12 conditions, in 130 ℃ of dyeing 60 minutes, hyperfine polyester fiber is dyeed, and carry out reduction clearing.The tone and the tinctorial strength that obtain dying sample are consistent with the painted result of embodiment 18 methods.
Embodiment 20:
The DISPERSE YELLOW A that embodiment 18 is made has high fastness to sublimation, can with the collocation of S-type dispersed dye, be more suitable for the dyeing of pad-dry-cure dyeing technology.
Blend together dye mixture disperse grass green M. and get 4g disperse grass green M as piecing together with the ratio (weight ratio) of DISPERSE YELLOW A: DISPERSE NAVY BLUE EXSF 300﹠ BLUE 56 100 S-2GL (C.I.B79:1): dispersed ruby S-2GFL (C.I.R167:1)=56: 42: 2,6g sodium alginate and 400ml water, be made into the dispersed dye padding liquor, pure polyester plain is immersed in the dye liquor, on little pad fix machine, roll dried then, pad altogether twice, the mylar of pad dyeing is dried down at 100-105 ℃, again at 210 ℃ of following hot melts after 60 seconds, reduction clearing, clean the back oven dry, dye green black colour.
To sum up, the dispersed dye of The compounds of this invention preparation are suitable for different dyeings, applied widely, especially dyeing speed is fast, and dye uptake is high, and stronger alkali resistance is arranged, be suitable for trevira, hyperfine polyester fiber, wash of the dyeing of the weak acid of ammonia BLENDED FABRIC to highly basic dye bath and differing temps, and excellent washing (six fine the contaminations) fastness is arranged, remedied the deficiency of known dyestuff, can be adapted to weaving and printing technology progressive needs.

Claims (9)

1. Monoazo compound with alkoxyl group is characterized in that its general structure is shown in (1):
Figure FSB00000256155000011
In the formula, OR 1At azo-group contraposition or ortho position,
R 1For
Figure FSB00000256155000012
Figure FSB00000256155000013
C 2～6Alkyl;
R 2＝H、CH 3、Cl、Br；n＝0～2。
2. a kind of Monoazo compound with alkoxyl group according to claim 1 is characterized in that its general structure is shown in (1a):
Figure FSB00000256155000014
R wherein 1Definition with above-mentioned formula (1).
3. a kind of Monoazo compound with alkoxyl group according to claim 1 is characterized in that its general structure is shown in (1b):
Figure FSB00000256155000015
R wherein 1Definition with above-mentioned formula (1).
4. a kind of Monoazo compound with alkoxyl group according to claim 1 is characterized in that its general structure is shown in (1c):
Figure FSB00000256155000021
R wherein 1Definition with above-mentioned formula (1).
5. the described a kind of preparation method of claim 1 with Monoazo compound of alkoxyl group, it is characterized in that it comprises the steps: the compound shown in the formula (2) is reacted with acid binding agent and alkylating agent in intensive polar solvent, phenolic hydroxyl group hydrogen is replaced, obtain described formula (1) Monoazo compound; Wherein said intensive polar solvent is sulfone class, amides, ethylene glycol or its ethers, polyoxyethylene glycol or its ether organic solvent; Described acid binding agent is at least a in alkali metal hydroxide, alkaline earth metal hydroxides or its carbonate; Described alkylating agent is at least a in sulfuric acid ester, benzene sulfonate class, the halogenated hydrocarbon compound;
Figure FSB00000256155000022
In the formula, OH is at azo-group contraposition or ortho position,
R 2＝H、CH 3、Cl、Br；n＝0～2。
6. the described a kind of application of claim 1-4 with Monoazo compound of alkoxyl group as dispersed dye.
7. a kind of application with Monoazo compound of alkoxyl group as dispersed dye according to claim 6 is characterized in that described dispersed dye are the mixture of the compound of general structure shown in (1) of single structure or at least two kinds of different structures.
8. a kind of application according to claim 6 with Monoazo compound of alkoxyl group as dispersed dye, it is characterized in that described dispersed dye comprise at least a general structure compound as the formula (1) and the composite mixture of other dispersed dye, the weight of the compound shown in the formula (1) surpasses 10% of the former dyestuff gross weight of other dispersed dye.
9. according to claim 6 or 7 or 8 described a kind of application, it is characterized in that described dispersed dye, as trevira, hyperfine polyester fiber, wash the dyeing of ammonia BLENDED FABRIC with Monoazo compound of alkoxyl group as dispersed dye.
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Cited By (1)

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Publication number Priority date Publication date Assignee Title
CN104194384A (en) * 2014-09-04 2014-12-10 恒升化工有限公司 Method for preparing cyanuric chloride type acid dye

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CN102250485B (en) * 2011-05-23 2013-05-15 蓬莱嘉信染料化工有限公司 Yellow disperse dye capable of dyeing in acid and alkaline baths
CN104711867B (en) * 2013-12-16 2017-02-22 上海安诺其集团股份有限公司 Application of disperse dye capable of alkaline dyeing
CN104710812B (en) * 2013-12-16 2017-02-22 上海安诺其集团股份有限公司 Preparation method of disperse dye capable of alkaline dyeing
CN104926684B (en) * 2015-06-03 2017-06-16 湖北大学 A kind of novel photochromic azobenzene compound and its synthetic method
CN117326972A (en) * 2018-03-29 2024-01-02 蓬莱嘉信染料化工股份有限公司 Compound, preparation method thereof and application thereof in dye
JP7121986B2 (en) * 2018-08-16 2022-08-19 株式会社常磐植物化学研究所 Method for producing alkoxyflavone derivative

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CN104194384A (en) * 2014-09-04 2014-12-10 恒升化工有限公司 Method for preparing cyanuric chloride type acid dye

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