CN103289434A - Method for producing isoindoline yellow pigment - Google Patents
Method for producing isoindoline yellow pigment Download PDFInfo
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- CN103289434A CN103289434A CN2012100434092A CN201210043409A CN103289434A CN 103289434 A CN103289434 A CN 103289434A CN 2012100434092 A CN2012100434092 A CN 2012100434092A CN 201210043409 A CN201210043409 A CN 201210043409A CN 103289434 A CN103289434 A CN 103289434A
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- acid
- isoindoline
- barbituric
- pigment
- reaction
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Abstract
The invention discloses a method for producing an isoindoline yellow pigment. The method comprises the following steps of: adding barbituric acid and 1,3-diimino-isoindoline into an inorganic acid aqueous solution to react for 1-30 hours at 10-100 DEG C; and then collecting a pigment yellow PY139 as shown by a formula (1) from reaction products. The method has very obvious beneficial effects as follows: low-cost inorganic acid replaces organic acid, wastewater is easy to treat and does not need to be recycled, the production cost is low, the environmental pollution is little, the energy consumption is low, and industrial production is facilitated. A chemical reaction equation is as shown in the specification.
Description
Technical field
The present invention relates to the new production technique of a kind of isoindoline yellow pigment.
Background technology
Pigment Yellow 73 P.Y.139 belongs to isoindoline class pigment, is the ruddiness Huang, is used for plastics, coating and printing ink.Because there is intermolecular, intramolecular hydrogen bond in such pigment, and constitutes solid netted piling up, make it to have good solvent resistance, resistance to migration, acid and alkali-resistance, resistance to oxidation reductibility and thermotolerance.Except indivedual documents, Pigment Yellow 73 P.Y.139 is synthetic by 1,3-diimino isoindoline and barbituric acid, main intermediate 1, and 3-diimino isoindoline can be that raw material is synthetic by phthalic nitrile or Tetra hydro Phthalic anhydride.
DE2041999 has reported the employing low-temp reaction, and heat treated mode prepares pigment in DMF/HOAc again, and the pigment that obtains is coarse, opacifying power is low, particle is tiny but reunite spottiness.US4166179 reported and made spent glycol, and water, formic acid (or diprotic acid of C4-C6) add sodium alkyl naphthalene sulfonate as tensio-active agent simultaneously as reaction system in reaction process, and the pigment product that obtains is easily disperseed, and the transparency is good.The document is reacted in water-based system, and temperature is widened to 150 ℃, should comprise the preparation of covering plate pigment.US5091532 has reported that use phthalic nitrile and sodium methylate direct reaction (not feeding ammonia) obtain intermediate in the patent of Bayer, again with barbituric acid prepared in reaction PY139 in methanol-water-formic acid (acetic acid) system, 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 the tinting strength height behind pigmenting, and the oxidation-resistance in plastic applications and photostabilization all are improved.
The used acid of the above patent documentation of introducing all has organic acid (monoprotic acid or diprotic acid), and as formic acid, it is big that acetic acid, Succinic Acid etc., this class organic acid have a consumption, the price height, and cost recovery is high and be difficult to shortcoming such as all recyclings.
Summary of the invention
The production method that the purpose of this invention is to provide a kind of isoindoline yellow pigment is to overcome the above-mentioned defective that prior art exists.
Method of the present invention comprises the steps:
Barbituric acid and 1,3-diimino isoindoline are added inorganic acid aqueous solution, then 10-100 ℃ of reaction 1-30h, the Pigment Yellow 73 PY139 shown in the collection type (1) from reaction product then;
Temperature of reaction is preferably 60～70 ℃, and the reaction times is preferably 10～15 hours;
Described mineral acid comprises phosphoric acid, hydrochloric acid, sulfuric acid, nitric acid or sulfurous acid etc., preferred hydrochloric acid;
The weight concentration of inorganic acid aqueous solution is 1.0～10%, preferably 1.40～5.0%;
The mol ratio of barbituric acid and 1,3-diimino isoindoline is:
Barbituric acid: 1,3-diimino isoindoline=2: 1;
The weight of mineral acid is 0.1～1 times of barbituric acid, preferred 0.23～0.97 times;
Chemical equation is expressed as follows:
The invention has the beneficial effects as follows fairly obviously, adopt cheap mineral acid to substitute organic acid, wastewater treatment is easy, need not reclaim, and production cost is low, and environmental pollution is little, and energy consumption is low, is convenient to suitability for industrialized production.
Embodiment
Embodiment 1
In reactor, add 3717 gram water, the 1237g weight concentration is 20% hydrochloric acid, add 256g (2 moles) barbituric acid and 145g (1 mole) 1 again, 3-diimino isoindoline is warming up to 70 ℃, stirring reaction 15h, filter, at 85 ℃ of hot washes with 55 ℃ of 3000 grams, 110 ℃ of dry 10h, obtain Pigment Yellow 73 PY139 348.6g, yield 95%.
Wherein: the weight concentration of aqueous hydrochloric acid is 4.99%; The weight of hydrochloric acid is 0.97 times of barbituric acid.
Embodiment 2
In reactor, add 3717 gram water, the 294g weight concentration is 20% hydrochloric acid, add 256g (2 moles) barbituric acid and 145g (1 mole) 1 again, 3-diimino isoindoline is warming up to 60 ℃, stirring reaction 10h, filter, with the hot wash of 8550 ℃ of 3000 grams, 110 ℃ of dry 10h, obtain Pigment Yellow 73 PY139 348.6g, yield 90%.
Wherein the weight concentration of aqueous hydrochloric acid is 1.47%; The weight of hydrochloric acid is 0.23 times of barbituric acid.
Embodiment 3
Substitute the hydrochloric acid of 1237g 20% with the hydrochloric acid of 539g weight concentration 20%, repeat embodiment 1, yield 92%.
Wherein the weight concentration of aqueous hydrochloric acid is 2.69%; The weight of hydrochloric acid is 0.23 times of barbituric acid.
Embodiment 4
Substitute the hydrochloric acid of 1237g 20% with the phosphoric acid of 418g weight concentration 20%, repeat embodiment 1, yield 92%.
Wherein the weight concentration of phosphate aqueous solution is 2.02%; The weight of phosphoric acid is 0.33 times of barbituric acid.
Embodiment 5
Substitute the hydrochloric acid of 1237g 20% with the nitric acid of 693g weight concentration 20%, repeat embodiment 1, yield 94%.
Wherein the weight concentration of aqueous nitric acid is 3.35%; The weight of nitric acid is 0.54 times of barbituric acid.
Embodiment 6
Substitute the hydrochloric acid of 1237g 20% with the sulfuric acid of 650g weight concentration 20%, repeat embodiment 1, yield 93%.
Wherein the weight concentration of aqueous sulfuric acid is 3.14%; The weight of sulfuric acid is 0.51 times of barbituric acid.
Claims (8)
1. the production method of isoindoline yellow pigment is characterized in that, comprises the steps: barbituric acid and 1,3-diimino isoindoline are added inorganic acid aqueous solution, and 10-100 ℃ of reaction 1-30 h collects Pigment Yellow 73 PY139 then from reaction product then.
2. method according to claim 1 is characterized in that, temperature of reaction is 60～70 ℃, and the reaction times is 10～15 hours.
3. method according to claim 1 is characterized in that, described mineral acid comprises phosphoric acid, hydrochloric acid, sulfuric acid, nitric acid or sulfurous acid.
4. method according to claim 2 is characterized in that, described mineral acid comprises phosphoric acid, hydrochloric acid, sulfuric acid, nitric acid or sulfurous acid.
5. according to each described method of claim 1～4, it is characterized in that the weight concentration of inorganic acid aqueous solution is 1～10%.
6. method according to claim 5 is characterized in that, the mol ratio of barbituric acid and 1,3-diimino isoindoline is: barbituric acid: 1,3-diimino isoindoline=2: 1.
7. method according to claim 5 is characterized in that, the weight of mineral acid is 0.1～1 times of barbituric acid.
8. method according to claim 7 is characterized in that, the weight of mineral acid is 0.23～0.97 times of barbituric acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012100434092A CN103289434A (en) | 2012-02-24 | 2012-02-24 | Method for producing isoindoline yellow pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012100434092A CN103289434A (en) | 2012-02-24 | 2012-02-24 | Method for producing isoindoline yellow pigment |
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| Publication Number | Publication Date |
|---|---|
| CN103289434A true CN103289434A (en) | 2013-09-11 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN2012100434092A Pending CN103289434A (en) | 2012-02-24 | 2012-02-24 | Method for producing isoindoline yellow pigment |
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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 (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166179A (en) * | 1976-06-24 | 1979-08-28 | Basf Aktiengesellschaft | Manufacture of organic pigments |
| 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 |
| CN101654565A (en) * | 2008-08-21 | 2010-02-24 | 山东宇虹颜料有限公司 | Method for preparing isoindoline pigment |
-
2012
- 2012-02-24 CN CN2012100434092A patent/CN103289434A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166179A (en) * | 1976-06-24 | 1979-08-28 | Basf Aktiengesellschaft | Manufacture of organic pigments |
| 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 |
| CN101654565A (en) * | 2008-08-21 | 2010-02-24 | 山东宇虹颜料有限公司 | Method for preparing isoindoline pigment |
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: 20130911 |