CN106146348B - A kind of preparation method of disperse dye compound - Google Patents
A kind of preparation method of disperse dye compound Download PDFInfo
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- CN106146348B CN106146348B CN201510162053.8A CN201510162053A CN106146348B CN 106146348 B CN106146348 B CN 106146348B CN 201510162053 A CN201510162053 A CN 201510162053A CN 106146348 B CN106146348 B CN 106146348B
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- disperse dye
- dye compound
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- cyano
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Abstract
The present invention provides a kind of preparation methods of disperse dye compound, include the following steps：Cyano-aniline is subjected to diazotising with sodium nitrite or nitrosyl sulfuric acid in acid medium, then carries out coupling with N- propylene-N- ethyl ketones aniline and is made, wherein, shown in the structural formula such as formula (1) of the disperse dye compound,
Description
Technical field
The present invention relates to a kind of preparation methods of disperse dye compound.
Background technology
At present, in the disperse dyes that market uses, maximum absorption wavelength λ max are equal to or less than the yellow cultivars of 450nm,
Mostly pyridinone azo-compound, such as C.I. disperse yellows 114, C.I. disperse yellows 119, C.I. DISPERSE Yellow 211s etc..It is this kind of
The yellow color soundness of dyestuff is simultaneously not bery high.Therefore, in order to meet the needs of market is to high fixing degree disperse dyes, the present invention carries
A kind of Yellow disperse dye kind of high color soundness is supplied.
The content of the invention
The present invention provides a kind of yellow of high color soundness point to meet the needs of market is to high fixing degree disperse dyes
The preparation method of dye composition is dissipated, is included the following steps：Cyano-aniline is used into sodium nitrite or nitrosyl in acid medium
Sulfuric acid carries out diazotising, then carries out coupling with N- propylene-N- ethyl ketones aniline and be made, wherein, the knot of the disperse dye compound
Shown in structure formula such as formula (1),
In formula (1)：X is cyano.
The disperse dye compound being prepared using the method for the present invention can possess excellent color soundness.
Specific embodiment
To describe the technical solutions in the embodiments of the present invention more clearly, described below is only some realities of the invention
Example is applied, for those of ordinary skill in the art, without having to pay creative labor, is equal or changed
Other embodiment.
Embodiment 1：
(1) diazo liquid is prepared：
11.10 grams of 1- cyano are weighed into 150 milliliters of beakers, 2- nitro-analines add in 20 milliliters of water, are weighed into 24.3 grams
30% hydrochloric acid stirs 30 minutes；
20 grams of ice are added in, then start that the solution that 5.8 grams of sodium nitrites and 20 milliliters of water prepare is added dropwise in less than 10 DEG C；
After adding, when less than 10 DEG C insulated and stirreds 1 are small.
(2) it is coupled：
A small amount of water and appropriate ice are added in 2000 milliliters of beakers, adds above-mentioned diazo liquid；In less than 5 DEG C by 14.50
Gram N- propylene-N- ethyl ketones aniline is instilled in diazo liquid.Continued at after adding 10 DEG C it is stirred below 1.5 it is small when；
Filtering, is washed to that filtrate is colourless, neutral, obtains the former dyestuff filter-cakes of structure such as (1),
In formula (1)：X is cyano；
Embodiment 2
Disperse dyes are prepared, former dyestuff filter-cakes prepared by 10 grams of embodiments 1 are weighed, with 100 grams of glass in sand mill is tested
Glass pearl be abrasive media, be sanded together with 37 grams of water and 10 grams of dispersing agent MFs 4 it is small when.Detect 4-5 grades of slurry diffusance.
Bead is filtered out, slurry is spray-dried.Control 115-120 DEG C of hot wind inlet temperature, outlet temperature 62-65
℃.Obtain the powdery disperse dyes of formula (1).
Effect example 1：
By former dyestuff filter-cakes made from embodiment 1, powdery disperse dyes, dye dosage 5%, bath raio is made through embodiment 2
1：12, room temperature carries out pollutant dyeing 5min after adding in dyestuff, then is warming up to 60 DEG C with the heating rate of 2 DEG C/min, operation
Sodium carbonate is added in after 20min (to add with first slow rear fast curve feed way 30min；Additive amount is 20g/L, with the body of dye liquor
Product meter), 60min is kept the temperature, discharges dye liquor, the post-processing steps such as is washed, neutralized, soaped to pollutant.Simultaneously using strictly according to the facts
The method for applying example 1 and embodiment 2 changes the group of X, respectively by the substitution matrix manufacturing comparative example 1,2 and 3 in table 1, and tests dye
The color soundness of sample, testing result see the table below 1；
And color soundness is calculated according to the following formula：
Color soundness=(the dyestuff summation of dye dosage-not upper dye)/dye dosage
Wherein, the dyestuff summation of dye " not upper " refers to after dyeing residual liquid and dyeing the dyestuff in respectively step washing, dyeing residual liquid and
After dyeing respectively step washing in dyestuff by test it can be learnt that.
The color soundness table of comparisons of 1. different dyes of table
| X group | Color soundness | |
| Embodiment 1 | Cyano | ○ |
| Comparative example 1 | Chlorine | △ |
| Comparative example 2 | Nitro | △ |
| Comparative example 3 | Methoxyl group | × |
It is excellent (color soundness is more than 85%) that ◎ represents color soundness；
Zero to represent color soundness good (color soundness as 60-85%)；
It is medium (color soundness as 40-59%) that △ represents color soundness；
× to represent color soundness bad (color soundness be less than 40%).
* the other components in dye composite are organic solvent.
From table 1：When the X substituent groups in formula (1) compound are cyano, the color soundness of dyestuff is apparent excellent in other
Substituent group.
Obviously, various changes and modifications can be made to the invention without departing from essence of the invention by those skilled in the art
God and scope.In this way, if these modifications and changes of the present invention belongs to the scope of the claims in the present invention and its equivalent technologies
Within, then the present invention is also intended to comprising including these modification and variations.
Claims (1)
1. a kind of preparation method of disperse dye compound, which is characterized in that include the following steps：Cyano-aniline is situated between in acidity
Diazotising is carried out with sodium nitrite or nitrosyl sulfuric acid in matter, then carries out coupling with N- propylene-N- ethyl ketones aniline and is made, wherein,
Shown in the structural formula of the disperse dye compound such as formula (1),
In formula (1)：X is cyano
Wherein, when the diazotizing condition is that less than 10 DEG C insulated and stirreds 1 are small.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201510162053.8A CN106146348B (en) | 2015-04-08 | 2015-04-08 | A kind of preparation method of disperse dye compound |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510162053.8A CN106146348B (en) | 2015-04-08 | 2015-04-08 | A kind of preparation method of disperse dye compound |
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| CN106146348A CN106146348A (en) | 2016-11-23 |
| CN106146348B true CN106146348B (en) | 2018-05-29 |
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| CN201510162053.8A Active CN106146348B (en) | 2015-04-08 | 2015-04-08 | A kind of preparation method of disperse dye compound |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4420308A (en) * | 1981-09-08 | 1983-12-13 | Cassella Aktiengesellschaft | Process for the production of reserve effects on polyester textiles and polyester/cellulose mixed fibre textiles: discharge printing with disperse azo dye with alkyl or alkoxy carbonyl, cyand and hydroxy phenyl group |
| US5521050A (en) * | 1994-12-16 | 1996-05-28 | Eastman Kodak Company | UV dyes for laser ablative recording process |
| CN101204357A (en) * | 2006-12-14 | 2008-06-25 | 欧莱雅 | Cosmetic product for dry-dyeing hair, applications and method of using same |
-
2015
- 2015-04-08 CN CN201510162053.8A patent/CN106146348B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4420308A (en) * | 1981-09-08 | 1983-12-13 | Cassella Aktiengesellschaft | Process for the production of reserve effects on polyester textiles and polyester/cellulose mixed fibre textiles: discharge printing with disperse azo dye with alkyl or alkoxy carbonyl, cyand and hydroxy phenyl group |
| US5521050A (en) * | 1994-12-16 | 1996-05-28 | Eastman Kodak Company | UV dyes for laser ablative recording process |
| CN101204357A (en) * | 2006-12-14 | 2008-06-25 | 欧莱雅 | Cosmetic product for dry-dyeing hair, applications and method of using same |
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| CN106146348A (en) | 2016-11-23 |
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