CN104987747B - A kind of benzimidazolone AZOpigments and its preparation and application - Google Patents
A kind of benzimidazolone AZOpigments and its preparation and application Download PDFInfo
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- CN104987747B CN104987747B CN201510460922.5A CN201510460922A CN104987747B CN 104987747 B CN104987747 B CN 104987747B CN 201510460922 A CN201510460922 A CN 201510460922A CN 104987747 B CN104987747 B CN 104987747B
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Abstract
The invention belongs to technical field of dye, more particularly to a kind of benzimidazolone AZOpigments and its preparation and application.Pigment (BI) is as led to the compound shown in formula (I)；Preparation is, by the arylamine shown in logical formula (II), the diazo liquid obtained through diazo-reaction, gained diazo liquid carry out coupling reaction with coupling component shown in (III), obtain the benzimidazolone AZOpigments (BI) shown in logical formula (I)；The benzimidazolone AZOpigments of the present invention, with the gorgeous purple of bright-coloured blue light, tinctorial strength is higher, transparency is good, heat endurance and the features such as outstanding resistance to migration, can be applicable in plastics, ink and coating as colouring agent.In formula：R is selected from H, OCH3, or CH3.
Description
Technical field
The invention belongs to technical field of dye, more particularly to a kind of benzimidazolone AZOpigments and its preparation and answers
With.
Background technology
In generation nineteen fifty, CIBA and Hoechst companies successively research and develop successfully and commodity to benzimidazolone AZOpigments
The high-grade organic pigment of change, is widely used in the coloring such as plastic cement, ink, coating.
Benzimidazolone AZOpigments colour system is more complete, only has a C.I. pigment violet 32, be dark reddish purple color in its violet, its
Structure is as follows：
C.I. 2 specific surface area of pigment violet 3 is 56m2/ g, average grain diameter are 120nm, are mainly used in printing-ink, paint, modeling
Material；Heat resistance is only 200-220 DEG C, on the coloring resin slightly lower to heat resistant requirements in can use, cannot but meet resistance to
The hot application having high demands.
Accordingly, it would be desirable to research and develop the purple benzo miaow of a kind of high tinctorial strength, good heat endurance and resistance to migration
Oxazolone AZOpigments, to meet used in the higher plastics of heat resistant requirements.Meanwhile, the pigment is met in ink and coating
The requirement of application.
Content of the invention
It is an object of the invention to provide a kind of benzimidazolone AZOpigments and its preparation and application.
For achieving the above object, the present invention adopt technical scheme for：
A kind of benzimidazolone AZOpigments, pigment (BI) is as led to the compound shown in formula (I)：
In formula：R is selected from H, OCH3Or CH3.
Pigment BI-1, R=CH3；BI-2, R=OCH3；BI-3, R=H.
Present invention additionally comprises a kind of preparation method of benzimidazolone AZOpigments, the arylamine shown in logical formula (II) is passed through
The diazo liquid that diazo-reaction is obtained, gained diazo liquid carry out coupling reaction with coupling component shown in (III), obtain logical formula (I)
Shown benzimidazolone AZOpigments (BI)；
Arylamine structure shown in logical formula (II) is as follows：
In formula：R is selected from H, OCH3Or CH3；
The structure of coupling component 2- picolines simultaneously [5,1b] quinazolinone is as shown in (III)：
In 0-30 DEG C in the presence of ethanol, coupling system pH is for coupling component shown in the gained diazo liquid and (III)
Coupling reaction is carried out under 6-7, is then warming up to 60-80 DEG C of process 1-8 hour.
Further, the diazol for the arylamine shown in formula (II) being obtained through diazo-reaction, gained diazo liquid and knot
Coupling component shown in structure formula (III) is carried out according to 1:1 proportioning, reaction obtain benzimidazolone AZOpigments shown in logical formula (I).
Arylamine structure shown in logical formula (II) is as follows：
In formula：R is selected from H, OCH3Or CH3.
The structure of simultaneously [5,1b] quinazolinone of coupling component 2- picolines needed for synthesis is as shown in (III)：
Diazol is prepared by formula (II) compound diazotising using conventional method, temperature be preferably controlled in 0-10 DEG C it
Between.Reaction equation is：
In formula：R is selected from H, OCH3Or CH3.
Coupling reaction formula is：
In formula：R is selected from H, OCH3Or CH3.
Coupled processes are as described below：
Coupling component is suspended in ethanol, adds NaOH, stirring to be allowed to all dissolvings, coupling solution is obtained.Add
Acetic acid solution adjusts pH value to 6-7.Diazo liquid is dropped in coupling solution, is simultaneously introduced sodium bicarbonate solution pH value is kept as 6-
7, terminate without diazol, reaction in being to react to reactant liquor at 0-30 DEG C in temperature.The suitable temperature of coupling reaction is 15-25
℃.Alkaline aqueous solution detection method using H acid (1- amino-8-naphthol -3,6- disulfonic acid) is judging reaction end.Reaction terminates
Afterwards, 60-80 DEG C is warming up to, 1-8 hours are incubated, the azo-compound slurry shown in logical formula (I) is obtained.
Wherein：R=CH3, pigment is BI-1；R=OCH3, pigment is BI-2；R=H, pigment are BI-3.
A kind of benzimidazolone AZOpigments as shown in logical formula (I) is in plastics, ink and coating as colouring agent
Application.
The present invention has the advantage that：
Benzimidazolone AZOpigments shown in the logical formula (I) of the present invention is a kind of blue light violet pigment, fresh with coloured light
Gorgeous, tinctorial strength is higher, transparency is good, heat resistance reaches more than 280 DEG C, and dispersiveness is excellent, and heat endurance and resistance to migration are excellent
Show, the features such as can preferably meeting the high heat colouring of resin and use, can meet the general requirement of pigment application, and be particularly well-suited to
Application in high temperature plastics coloring.Blue light purple benzimidazolone AZOpigments shown in logical formula (I) can also be used for ink with
And as colouring agent in coating.
Specific embodiment
Below by way of specific operational instances, the present invention is further elaborated and explanation, but the present invention is not limited to this
A little operational instances.In example, raw materials used and P.V.32 (control sample) can be by commercially available acquisition.
Example 1：The synthesis of BI-1 pigment
Prepare diazo liquid：16.7 grams of 5- methyl -6- aminobenzimidazole ketone are added in 140 milliliters of water, are subsequently adding
26 gram of 35% hydrochloric acid, is kept for 0.5 hour.On the rocks be cooled to 0-5 DEG C, 36.3 grams of 20% sodium nitrite solution is added dropwise, keeps 1 little
When.Add 1 gram of active carbon adsorption impurity.Filter, collection filtrate is diazo liquid.
Prepare coupling solution：By 20.1 grams of 2- picolines, simultaneously [5,1b] quinazolinone and 14 grams of NaOH are added to 240
In milliliter ethanol, stir to all dissolvings, add 30 grams and be cooled to 15-20 DEG C.
Prepare azo dyes：PH 6--7 are adjusted with 20 (v) % acetic acid, the diazo liquid and 10% sodium carbonate of preparation is simultaneously added dropwise
Solution, maintains pH6-7.Finishing, extracting reaction solution 1 drop, drip on filter paper, the alkalescent for the 1 drop H acid of circle side drop being oozed at which is water-soluble
Liquid, as do not developed the color, shows that, without diazol excess, reaction terminates；If aobvious redness, must add coupling solution in right amount.After the completion of reaction
Obtain dark reddish purple mill base material.
Pigmentation process：Reaction gained slurry, is slowly warmed up to 75 DEG C, and isothermal holding 4 hours at this temperature, cooling
To room temperature, filter, washing, obtain the pigment BI-1 of structure shown in logical formula (I).
Example 2：The synthesis of BI-2 pigment
During pigment is prepared, replace 5- methyl -6- aminobenzenes with 17.9 grams of 5- methoxyl group -6- aminobenzimidazole ketone
And imidazolone, other chargings and operation equivalent example 1, obtain the pigment BI-2 of structure shown in logical formula (I).
Example 3：The synthesis of BI-3 pigment
During pigment is prepared, replace 5- methyl -6- aminobenzimidazole ketone with 14.9 grams of 5-Amino-2-benzimidazolinones,
Other chargings and operation equivalent example 1, obtain the pigment BI-3 of structure shown in logical formula (I).
Example 4：Application effect is tested
Method of testing：Using injection machine (injection temperature is 200-220 DEG C), the color chips of HDPE is made, pigment addition is
0.1 (wt) %, then with D65/10 ° of colour photometer (thinking scholar), the color distortion of each pigment color chips of comparison.
Intensity comparative approach：Using injection machine (injection temperature is 200-220 DEG C), the color chips of HDPE is made, pigment adds
Measure as 0.1 (wt) %, TiO2(Du Pont R-902) addition is 0.5 (wt) %, then uses D65/10 ° of colour photometer (thinking scholar), than
The strength difference of more each pigment.
Method for Measuring Heat-resistibility：Make HDPE's using injection machine (injection temperature is 280 DEG C, and the holdup time is 5 minutes)
Color chips, pigment addition are 0.1 (wt) %, TiO2(Du Pont R-902) addition is 0.5 (wt) %, is then compared with colour photometer
The aberration of 5 minutes color chips of 220 DEG C of color chips of each pigment and 280 DEG C of delays, heat endurance are stated with the size of △ E values.
Testing result is listed in the following table：
1. colour examining data of table
2. dispersed test data data of table
By 1 data analysis of table, the coloring intensity of pigment is preferably (Integ values reach more than 9)；△ E numerical value≤
1.3, its temperature tolerance test data shows that, in the case of 280 DEG C, its changes of shade is less, and heat resistance is significantly better than P.V.32.
The cold and hot roller of 2 data of table disperses test data, and both show Data Comparison, and such pigment has more excellent dispersion
Property.
Claims (3)
1. a kind of benzimidazolone AZOpigments, it is characterised in that：Pigment is as led to the compound shown in formula (I)：
In formula：R is selected from H, OCH3Or CH3.
2. the preparation method of the benzimidazolone AZOpigments described in a kind of claim 1, it is characterised in that by logical formula (II) institute
The arylamine for showing, the diazo liquid obtained through diazo-reaction, gained diazo liquid carry out coupling reaction with coupling component shown in (III),
Obtain the benzimidazolone AZOpigments shown in logical formula (I)；
Arylamine structure shown in logical formula (II) is as follows：
In formula：R is selected from H, OCH3Or CH3；
The structure of coupling component 2- picolines simultaneously [5,1b] quinazolinone is as shown in (III)：
In 0-30 DEG C in the presence of ethanol, coupling system pH is under 6-7 for coupling component shown in the gained diazo liquid and (III)
Coupling reaction is carried out, 60-80 DEG C of process 1-8 hour is then warming up to.
3. a kind of according to described in claim 1 as lead to the benzimidazolone AZOpigments shown in formula (I) plastics, ink and
In coating as colouring agent application.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11192893B2 (en) | 2017-05-18 | 2021-12-07 | The Rockefeller University | Pyrazoloquinazolinone antitumor agents |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108047750A (en) * | 2017-12-29 | 2018-05-18 | 东营安诺其纺织材料有限公司 | A kind of production technology of disperse yellow |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3468872A (en) * | 1965-08-21 | 1969-09-23 | Basf Ag | Phthalimide dyes of the monoazo series |
| CN1662610A (en) * | 2002-06-20 | 2005-08-31 | 科莱恩有限公司 | Method for producing disazo pigments |
| CN103562325A (en) * | 2011-05-20 | 2014-02-05 | 三菱化学株式会社 | Azo compound and ink containing same |
-
2015
- 2015-07-30 CN CN201510460922.5A patent/CN104987747B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3468872A (en) * | 1965-08-21 | 1969-09-23 | Basf Ag | Phthalimide dyes of the monoazo series |
| CN1662610A (en) * | 2002-06-20 | 2005-08-31 | 科莱恩有限公司 | Method for producing disazo pigments |
| CN103562325A (en) * | 2011-05-20 | 2014-02-05 | 三菱化学株式会社 | Azo compound and ink containing same |
Non-Patent Citations (1)
| Title |
|---|
| 苯并咪唑酮颜料及其应用;沈永嘉;《化工科技市场》;20010415(第04期);全文 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11192893B2 (en) | 2017-05-18 | 2021-12-07 | The Rockefeller University | Pyrazoloquinazolinone antitumor agents |
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