CN104987747A - Benzimidazolone azo pigment and preparation and application thereof - Google Patents
Benzimidazolone azo pigment and preparation and application thereof Download PDFInfo
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- CN104987747A CN104987747A CN201510460922.5A CN201510460922A CN104987747A CN 104987747 A CN104987747 A CN 104987747A CN 201510460922 A CN201510460922 A CN 201510460922A CN 104987747 A CN104987747 A CN 104987747A
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- azo pigment
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Abstract
The invention belongs to the technical field of dye, and specifically relates to a benzimidazolone azo pigment and preparation and application therefor. Pigment (BI) is a compound shown by a general formula (I). The preparation method comprises steps of: obtaining a diazo solution by performing a diazotization reaction on aromatic amines shown in a general formula (II); performing a coupling reaction on the obtained diazo solution and a coupling component shown by a general formula (III), so as to obtain the benzimidazolone azo pigment (BI) shown in the general formula (I). The benzimidazolone azo pigment provided by the invention has the advantages of: having a bright blue brilliant purple color, being relatively high in coloration intensity, good in transparency, excellent in thermal stability and migration resistance, and can be used as a colorant in plastics, inks and coatings. In the formula as shown in the specification, R is chosen from H, OCH3, or CH3.
Description
Technical field
The invention belongs to technical field of dye, relate to a kind of benzimidazolone azo pigment and preparation and application thereof particularly.
Background technology
Benzimidazolone azo pigment is in generation nineteen fifty, CIBA and Hoechst company successively researches and develops successfully and commercial high-grade pigment dyestuff, is widely used in plastic cement, ink, coating etc. painted.
Benzimidazolone azo pigment colour system is comparatively complete, and only have a C.I. pigment violet 32 in its violet, be dark reddish purple look, its structure is as follows:
C.I. pigment violet 32 specific surface area is 56m
2/ g, median size is 120nm, is mainly used in printing-ink, paint, plastics; Thermotolerance is only 200-220 DEG C, can use the coloring resin slightly low to heat resistant requirements is upper, but cannot meet the high application of heat resistant requirements.
Therefore, need the purple benzimidazolone azo pigment researching and developing a kind of high tinctorial strength, good thermostability and resistance to migration, use in the plastics that heat resistant requirements is higher to meet.Meanwhile, this pigment meets the requirement of applying in ink and coating.
Summary of the invention
The object of the present invention is to provide a kind of benzimidazolone azo pigment and preparation and application thereof.
For achieving the above object, the present invention adopts technical scheme to be:
A kind of benzimidazolone azo pigment, the compound of pigment (BI) as shown in general formula (I):
In formula: R is selected from H, OCH
3or CH
3.
Pigment BI-1, R=CH
3; BI-2, R=OCH
3; BI-3, R=H.
The present invention also comprises a kind of preparation method of benzimidazolone azo pigment, by the arylamine shown in general formula (II), through the diazo liquid that diazotization reaction obtains, gained diazo liquid carries out coupled reaction with coupling component shown in (III), obtains the benzimidazolone azo pigment (BI) shown in general formula (I);
Arylamine structure shown in general formula (II) is as follows:
In formula: R is selected from H, OCH
3or CH
3;
The structure of coupling component 2-picoline also [5,1b] quinazolinone is as shown in (III):
Described gained diazo liquid and coupling component shown in (III) are in 0-30 DEG C under ethanol exists, and coupling system pH is carry out coupled reaction under 6-7, are then warming up to 60-80 DEG C of process 1-8 hour.
Further, by the diazonium salt that the arylamine shown in formula (II) obtains through diazotization reaction, shown in gained diazo liquid and structural formula (III), coupling component carries out according to 1:1 proportioning, is obtained by reacting benzimidazolone azo pigment shown in general formula (I).
Arylamine structure shown in general formula (II) is as follows:
In formula: R is selected from H, OCH
3or CH
3.
The structure of the required coupling component 2-picoline of synthesis also [5,1b] quinazolinone is as shown in (III):
Adopt conventional method to prepare diazonium salt by formula (II) compound diazotization, temperature preferably controls between 0-10 DEG C.Reaction formula is:
In formula: R is selected from H, OCH
3or CH
3.
Coupled reaction formula is:
In formula: R is selected from H, OCH
3or CH
3.
Coupled processes is as described below:
Coupling component is suspended in ethanol, adds sodium hydroxide, stir and make it whole dissolving, obtained coupling solution.Add acetic acid solution adjust pH to 6-7.Dropped to by diazo liquid in coupling solution, add sodium hydrogen carbonate solution to keep pH value for 6-7 simultaneously, react without diazonium salt to reaction solution at temperature is 0-30 DEG C, reaction terminates.The temperature that coupled reaction is suitable is 15-25 DEG C.The alkaline aqueous solution detection method of H acid (1-amino-8-naphthol-3,6-disulfonic acid) is adopted to judge reaction end.After reaction terminates, be warming up to 60-80 DEG C, insulation 1-8 hour, obtains the azo-compound slurry shown in general formula (I).
Wherein: R=CH
3, pigment is BI-1; R=OCH
3, pigment is BI-2; R=H, pigment is BI-3.
A kind of benzimidazolone azo pigment as shown in general formula (I) in plastics, ink and coating as the application of tinting material.
The advantage that the present invention has:
Benzimidazolone azo pigment shown in general formula of the present invention (I) is a kind of blue light violet pigment, there is bright in color light, tinctorial strength is higher, transparency good, thermotolerance reaches more than 280 DEG C, excellent dispersion, thermostability and resistance to migration outstanding, the features such as resin height heat colouring use can be met preferably, the general requirement of pigment applications can be met, and be specially adapted to the application in high temperature plastics is painted.Blue light purple benzimidazolone azo pigment shown in general formula (I) also can be used in ink and coating as tinting material.
Embodiment
Below by way of concrete operational instances, the present invention is further elaborated and illustrate, but the present invention is not limited to these operational instances.In example, raw materials used and P.V.32 (control sample) all can by commercially available acquisition.
The synthesis of example 1:BI-1 pigment
Prepare diazo liquid: join in 140 ml waters by 16.7 grams of 5-methyl-6-aminobenzimidazole ketone, then add 26 gram of 35% hydrochloric acid, keep 0.5 hour.On the rocksly be cooled to 0-5 DEG C, drip 20% sodium nitrite solution 36.3 grams, keep 1 hour.Add 1 gram of activated carbon adsorption impurity.Filter, collection filtrate is diazo liquid.
Prepare coupling solution: by 20.1 grams of 2-picolines also [5,1b] quinazolinone and 14 grams of sodium hydroxide join in 240 milliliters of ethanol, be stirred to whole dissolving, add 30 grams and be cooled to 15-20 DEG C.
Prepare azoic dyestuff: adjust pH 6--7 with 20 (v) % acetic acid, drip diazo liquid and 10% sodium carbonate solution of preparation simultaneously, maintain pH6-7.Finish, extract reaction solution 1, drip on filter paper, ooze at it weak alkaline aqueous solution that 1 H acid is dripped in circle side, if do not developed the color, it is excessive to show without diazonium salt, and reaction terminates; If aobvious red, then must add coupling solution in right amount.Dark reddish purple mill base material is obtained after having reacted.
Pigmenting process: reaction gained slurry, is slowly warmed up to 75 DEG C, and isothermal holding 4 hours at this temperature, be cooled to room temperature, filter, washing, obtain the pigment BI-1 of structure shown in general formula (I).
The synthesis of example 2:BI-2 pigment
Preparing in pigment process, replacing 5-methyl-6-aminobenzimidazole ketone with 17.9 grams of 5-methoxyl group-6-aminobenzimidazole ketone, other reinforced and equivalent examples 1 of operation, obtain the pigment BI-2 of structure shown in general formula (I).
The synthesis of example 3:BI-3 pigment
Preparing in pigment process, replacing 5-methyl-6-aminobenzimidazole ketone by 14.9 grams of 5-Amino-2-benzimidazolinones, other reinforced and equivalent examples 1 of operation, obtain the pigment BI-3 of structure shown in general formula (I).
Example 4: effect is tested
Testing method: use injection moulding machine (injection temperature is 200-220 DEG C), make the color chips of HDPE, pigment addition is 0.1 (wt) %, then uses color measurement instrument (thinking scholar) D65/10 °, the color distortion of more each pigment color chips.
Intensity comparative approach: use injection moulding machine (injection temperature is 200-220 DEG C), make the color chips of HDPE, pigment addition is 0.1 (wt) %, TiO
2(Du Pont R-902) addition is 0.5 (wt) %, then uses color measurement instrument (thinking scholar) D65/10 °, the strength difference of more each pigment.
Method for Measuring Heat-resistibility: use injection moulding machine (injection temperature is 280 DEG C, and the residence time is 5 minutes) to make the color chips of HDPE, pigment addition is 0.1 (wt) %, TiO
2(Du Pont R-902) addition is 0.5 (wt) %, and be then detained the aberration of 5 minutes color chips with the more each pigment of color measurement instrument 220 DEG C of color chips and 280 DEG C, thermostability is stated with the size of △ E value.
Detected result is listed in the following table:
Table 1. colour examining data
The dispersed test data data of table 2.
Known by table 1 data analysis, the coloring intensity of pigment better (Integ value reaches more than 9); △ E numerical value≤1.3, its temperature tolerance test data shows that, in 280 DEG C of situations, its changes of shade is less, and thermotolerance is significantly better than P.V.32.
Table 2 data cold and hot roller dispersion test data, both show by Data Comparison, and such pigment has comparatively excellent dispersiveness.
Claims (4)
1. a benzimidazolone azo pigment, is characterized in that: the compound of pigment as shown in general formula (I):
In formula: R is selected from H, OCH
3or CH
3.
2. the preparation method of a benzimidazolone azo pigment according to claim 1, it is characterized in that, by the arylamine shown in general formula (II), through the diazo liquid that diazotization reaction obtains, gained diazo liquid carries out coupled reaction with coupling component shown in (III), obtains the benzimidazolone azo pigment shown in general formula (I);
Arylamine structure shown in general formula (II) is as follows:
In formula: R is selected from H, OCH
3or CH
3;
The structure of coupling component 2-picoline also [5,1b] quinazolinone is as shown in (III):
3. according to preparation method according to claim 2, it is characterized in that: coupling component shown in described gained diazo liquid and (III) under ethanol exists in 0-30 DEG C, coupling system pH is carry out coupled reaction under 6-7, is then warming up to 60-80 DEG C of process 1-8 hour.
4. one kind according to the benzimidazolone azo pigment as shown in general formula (I) according to claim 1 in plastics, ink and coating as the application of tinting material.
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|---|---|---|---|
| CN201510460922.5A CN104987747B (en) | 2015-07-30 | 2015-07-30 | A kind of benzimidazolone AZOpigments and its preparation and application |
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|---|---|---|---|
| CN201510460922.5A CN104987747B (en) | 2015-07-30 | 2015-07-30 | A kind of benzimidazolone AZOpigments and its preparation and application |
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| CN104987747B CN104987747B (en) | 2017-03-15 |
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Cited By (2)
| 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 |
| EP3624805A4 (en) * | 2017-05-18 | 2020-11-18 | Tarun M. Kapoor | Pyrazoloquinazolinone antitumor agents |
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 | The preparation method of disazo pigment |
| 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 (4)
| 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 | The preparation method of disazo pigment |
| US20060167236A1 (en) * | 2002-06-20 | 2006-07-27 | Clariant Gmbh | 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 |
|---|
| 沈永嘉: "苯并咪唑酮颜料及其应用", 《化工科技市场》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3624805A4 (en) * | 2017-05-18 | 2020-11-18 | Tarun M. Kapoor | Pyrazoloquinazolinone antitumor agents |
| 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 |
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| Publication number | Publication date |
|---|---|
| CN104987747B (en) | 2017-03-15 |
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