CN103013159A - Method for anhydrously preparing isoindoline pigment - Google Patents
Method for anhydrously preparing isoindoline pigment Download PDFInfo
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- CN103013159A CN103013159A CN2012105415810A CN201210541581A CN103013159A CN 103013159 A CN103013159 A CN 103013159A CN 2012105415810 A CN2012105415810 A CN 2012105415810A CN 201210541581 A CN201210541581 A CN 201210541581A CN 103013159 A CN103013159 A CN 103013159A
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- organic solvent
- diiminoisoindole
- reaction
- pigment
- barbituric acid
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Abstract
The invention provides a method for anhydrously preparing an isoindoline pigment, comprising the following steps of: dissolving or suspending barbituric acid into an organic solvent A; adding an organic solvent B containing 1,3-diimino isoindoline to react; in a reaction process, fractionating generated ammonia gas; and then, collecting the isoindoline pigment from a reaction product. The method disclosed by the invention has the beneficial effects are very obvious; a pure organic solvent reaction system is adopted and a product yield is high; only the organic solvents need to be recycled; the production cost is low and the environmental pollution is small; and the method is convenient for industrial production.
Description
Technical field
The present invention relates to a kind of production technique of isoindoline yellow pigment.
Background technology
Isoindoline class pigment is owing to existing intermolecular, intramolecular hydrogen bond, and consists of solid netted piling up, and makes it to have good solvent resistance, resistance to migration, acid and alkali-resistance, resistance to oxidation reductibility and thermotolerance.In plastics, coating and printing ink, be used widely.Because such pigment is except indivedual documents, isoindoline class pigment is by 1,3-diiminoisoindole and barbituric acid and derivative thereof are synthetic, main intermediate 1, and the 3-diiminoisoindole can be that raw material is synthetic by containing substituting group phthalic nitrile or Tetra hydro Phthalic anhydride on the phenyl ring.
DE2041999 has reported the employing low-temp reaction, and heat treated mode prepares pigment in DMF/HOAc again, although this patent has used DMF to be solvent, has used organic acid in reaction process.US4166179 reported and made spent glycol, and water, formic acid (or diprotic acid of C4-C6) are as reaction system, and the pigment product that obtains is easily disperseed, and the transparency is good, and this patent has used formic acid as alkali-binding agent.US5091532 has reported that use phthalic nitrile and sodium methylate direct reaction (not passing into ammonia) obtain intermediate in the patent of Bayer, in methanol-water-formic acid (acetic acid) system, react preparation PY139 with barbituric acid again, but the pigment yield that adopts this method to obtain is low.The Ciba patent report a kind of synthetic method that improves the pigment opacifying power, under the organic solvent-free system, add glacial acetic acid as alkali-binding agent, stage by stage the synthetic PY139 of conditioned reaction temperature.Chinese patent CN200810139252.7 has reported that a kind of use organic acid is as alkali-binding agent and the synthetic PY139 of solvent, in building-up process, there is not the introducing of water, the crude product that is synthesized obtains tinting strength behind pigmenting high, and the oxidation-resistance in plastic applications and photostabilization all are improved, but this patent has been used a large amount of organic acids, will be a greatly test to the erosion resistance of equipment.
The above patent documentation of introducing all uses a large amount of organic acids, and it is large that this class organic acid has a consumption, and corrodibility is strong, price is high, and cost recovery is high and be difficult to whole recyclings, and product yield is at 70-80%, product yield is low, and by product is many, brings very large difficulty to wastewater treatment.
Summary of the invention
The purpose of this invention is to provide a kind of anhydrous method for preparing isoindoline pigment, the defects that exists to overcome prior art.
Method of the present invention comprises the steps:
With barbituric acid dissolving or be suspended in the organic solvent A, add the organic solvent B that contains 1,3-diiminoisoindole, at 50-140 ℃ of reaction 10-30h, fractionate out the ammonia of generation in the reaction process, then collect described isoindoline pigment from reaction product, its structural formula is as follows:
Wherein:
R
1, R
2, R
3, R
4Represent respectively H, the straight-chain paraffin of C1-C10 or branched paraffin;
R
5Represent NO
2-, Cl-, Br-, C
1-C
5Alkane etc.;
In the organic solvent A, the concentration of barbituric acid is 4～6g/100ml;
Contain among the organic solution B of 1,3-diiminoisoindole, the concentration of 1,3-diiminoisoindole is 9～15g/100ml;
Barbituric acid: 1,3-diiminoisoindole=1: 2.0～3.0, mol ratio;
Preferably, adopt the mode that drips, add the organic solution that contains 1,3-diiminoisoindole, time for adding is 10～60 minutes;
Organic solvent A and organic solvent B all are selected from amides, alcohols, dimethyl sulfoxide (DMSO) or N-Methyl pyrrolidone etc.;
Described amides is selected from DMF, N,N-dimethylacetamide or N, N-dimethyl propylene acid amides;
Described alcohols is selected from carbonatoms less than 10 alcoholic solvent, particular methanol, ethanol or ethylene glycol etc.;
The invention has the beneficial effects as follows fairly obviously, adopt pure organic solvent reaction system, product yield is high, only needs to reclaim organic solvent, and production cost is low, and environmental pollution is little, is convenient to suitability for industrialized production.
Embodiment
Embodiment 1
In reactor, add 800ml N, dinethylformamide, 37.5g(0.293 mole) barbituric acid, be warming up to 55 ℃ of dissolvings, in 30 minutes, be added dropwise to the 19.2g(0.132 mole) 1, the 3-diiminoisoindole is dissolved in the solution of 200ml DMF, reacted the ammonia that vacuum fractionation goes out to produce in the reaction process 30 hours.Be cooled to 20-30 ℃, filter, methanol wash, vacuum-drying obtains pigment 46g, yield 95%.
Embodiment 2
In reactor, add 800ml N, the N-N,N-DIMETHYLACETAMIDE, 37.5g(0.293 mole) barbituric acid, be warming up to 140 ℃ of dissolvings, in 30 minutes, be added dropwise to the 19.2g(0.132 mole) 1, the 3-diiminoisoindole is dissolved in the solution of 200ml N,N-dimethylacetamide, reaction 15h, the ammonia that vacuum fractionation goes out to produce in the reaction process.Be cooled to 20-30 ℃, filter, methanol wash, vacuum-drying obtains pigment 45g, yield 94%.
Embodiment 3
In reactor, add 800ml ethylene glycol, 37.5g(0.293 mole) barbituric acid, be warming up to 110 ℃ of dissolvings, in 30 minutes, be added dropwise to the 19.2g(0.132 mole) 1, the 3-diiminoisoindole is dissolved in 200ml ethylene glycol, reacted the ammonia that vacuum fractionation goes out to produce in the reaction process, the ammonia that vacuum fractionation goes out to produce in the reaction process 25 hours.Be cooled to 20-30 ℃, filter, methanol wash, vacuum-drying obtains pigment 45g, yield 94%.
Embodiment 4
In reactor, add 800ml methyl alcohol, 37.5g(0.293 mole) barbituric acid, be warming up to 55 ℃, dissolving was added dropwise to the 19.2g(0.132 mole in 30 minutes) 1, the 3-diiminoisoindole is dissolved in 200ml ethylene glycol, reacted 5 hours, vacuum fractionation is except ammonia in the reaction process.Be warming up to backflow, stirring reaction 30h, fractionation is except ammonia in the reaction process.Be cooled to 20-30 ℃, filter, methanol wash, vacuum-drying obtains pigment 43g, yield 90%.
Embodiment 5
In reactor, add 800ml DMF, 46.8g(0.293 mole) 1, the 3-dimethyl barbituric acid, be warming up to 110 ℃, dissolving was added dropwise to the 19.2g(0.132 mole in 30 minutes) 1, the 3-diiminoisoindole is dissolved in 200ml N, the solution of dinethylformamide reacted the ammonia that vacuum fractionation goes out in the reaction process 19 hours, the ammonia that vacuum fractionation goes out in the reaction process.Be cooled to 20-30 ℃, filter, methanol wash, vacuum-drying obtains pigment 43g, yield 90%.
Embodiment 6
In reactor, add 800ml N, dinethylformamide, 37.5g(0.293 mole) barbituric acid, be warming up to 55 ℃, dissolving was added dropwise to the 25.08g(0.132 mole in 30 minutes) 5-nitro-1, the 3-diiminoisoindole is dissolved in 200ml N, the solution of dinethylformamide reacted 30 hours, the ammonia that vacuum fractionation goes out to produce in the reaction process.Be cooled to 20-30 ℃, filter, methanol wash, vacuum-drying obtains pigment 46g, yield 95%.
Embodiment 7
In reactor, add 800ml methyl alcohol, 50.7g(0.396 mole) barbituric acid, be warming up to 55 ℃, dissolving was added dropwise to the 19.2g(0.132 mole in 30 minutes) 1, the 3-diiminoisoindole is dissolved in 200ml ethylene glycol, reacted 5 hours, vacuum fractionation is except ammonia in the reaction process.Be warming up to backflow, stirring reaction 30h, fractionation is except ammonia in the reaction process.Be cooled to 20-30 ℃, filter, methanol wash, vacuum-drying obtains pigment 43g, yield 95%.
Claims (7)
1. the anhydrous method for preparing isoindoline pigment, it is characterized in that, comprise the steps, with barbituric acid dissolving or be suspended in the organic solvent A, add the organic solvent B reaction that contains 1,3-diiminoisoindole, fractionate out the ammonia of generation in the reaction process, then collect described isoindoline pigment from reaction product, its structural formula is as follows:
Wherein:
R
1, R
2, R
3, R
4Represent respectively H, the straight-chain paraffin of C1-C10 or branched paraffin;
R
5Represent NO
2-, Cl-, Br-, C
1-C
5Alkane.
2. method according to claim 1 is characterized in that, at 50-140 ℃ of reaction 10-30h.
3. method according to claim 1 is characterized in that, in the organic solvent A, the concentration of barbituric acid is 4～6g/100ml; Contain among the organic solution B of 1,3-diiminoisoindole, the concentration of 1,3-diiminoisoindole is 9～15g/100ml.
4. method according to claim 1 is characterized in that, barbituric acid: 1,3-diiminoisoindole=1: 2.0～3.0, mol ratio.
5. method according to claim 1 is characterized in that, adopts the mode that drips, and adds the organic solution that contains 1,3-diiminoisoindole.
6. each described method is characterized in that according to claim 1～5, and organic solvent A and organic solvent B all are selected from amides, alcohols, dimethyl sulfoxide (DMSO) or N-Methyl pyrrolidone.
7. method according to claim 6 is characterized in that, described amides is selected from DMF, N,N-dimethylacetamide or N, N-dimethyl propylene acid amides;
Described alcohols is selected from carbonatoms less than 10 alcohols.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012105415810A CN103013159A (en) | 2012-12-13 | 2012-12-13 | Method for anhydrously preparing isoindoline pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012105415810A CN103013159A (en) | 2012-12-13 | 2012-12-13 | Method for anhydrously preparing isoindoline pigment |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103013159A true CN103013159A (en) | 2013-04-03 |
Family
ID=47962289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2012105415810A Pending CN103013159A (en) | 2012-12-13 | 2012-12-13 | Method for anhydrously preparing isoindoline pigment |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103013159A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114573998A (en) * | 2022-01-28 | 2022-06-03 | 山东世纪连泓新材料有限公司 | Pigment yellow 139 synthesis process |
| WO2023243354A1 (en) * | 2022-06-13 | 2023-12-21 | Dic株式会社 | Isoindoline compound |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166179A (en) * | 1976-06-24 | 1979-08-28 | Basf Aktiengesellschaft | Manufacture of organic pigments |
| US4480097A (en) * | 1980-02-27 | 1984-10-30 | Basf Aktiengesellschaft | Isoindoline colorants |
| US4492796A (en) * | 1980-06-19 | 1985-01-08 | Bayer Aktiengesellschaft | Isoindolenine derivatives, processes for their preparation and their use as intermediate products for the preparation of dyestuffs |
| US5091532A (en) * | 1989-10-27 | 1992-02-25 | Bayer Aktiengesellschaft | Process for the preparation of pigments based on isoindole |
| CN102585542A (en) * | 2011-12-27 | 2012-07-18 | 百合花集团有限公司 | Method for preparing C.I. pigment yellow 139 |
-
2012
- 2012-12-13 CN CN2012105415810A patent/CN103013159A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166179A (en) * | 1976-06-24 | 1979-08-28 | Basf Aktiengesellschaft | Manufacture of organic pigments |
| US4480097A (en) * | 1980-02-27 | 1984-10-30 | Basf Aktiengesellschaft | Isoindoline colorants |
| US4492796A (en) * | 1980-06-19 | 1985-01-08 | Bayer Aktiengesellschaft | Isoindolenine derivatives, processes for their preparation and their use as intermediate products for the preparation of dyestuffs |
| US5091532A (en) * | 1989-10-27 | 1992-02-25 | Bayer Aktiengesellschaft | Process for the preparation of pigments based on isoindole |
| CN102585542A (en) * | 2011-12-27 | 2012-07-18 | 百合花集团有限公司 | Method for preparing C.I. pigment yellow 139 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114573998A (en) * | 2022-01-28 | 2022-06-03 | 山东世纪连泓新材料有限公司 | Pigment yellow 139 synthesis process |
| CN114573998B (en) * | 2022-01-28 | 2024-03-05 | 山东世纪连泓新材料有限公司 | Pigment yellow 139 synthesis process |
| WO2023243354A1 (en) * | 2022-06-13 | 2023-12-21 | Dic株式会社 | Isoindoline compound |
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Application publication date: 20130403 |