CN102585542A - Method for preparing C.I. pigment yellow 139 - Google Patents
Method for preparing C.I. pigment yellow 139 Download PDFInfo
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- CN102585542A CN102585542A CN2011104476526A CN201110447652A CN102585542A CN 102585542 A CN102585542 A CN 102585542A CN 2011104476526 A CN2011104476526 A CN 2011104476526A CN 201110447652 A CN201110447652 A CN 201110447652A CN 102585542 A CN102585542 A CN 102585542A
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Abstract
The invention relates to a method for preparing C.I. pigment yellow 139. The method comprises the following steps of: (1) preparing 1,3-diiminoisoindoline from phthalonitrile; (2) reacting the 1,3-diiminoisoindoline with barbituric acid to prepare a crude C.I. pigment yellow 139 product; and (3) performing pigmentation on the crude C.I. pigment yellow 139 product. The method is characterized in that ammonia water is added or ammonia gas is introduced in the reaction in the step (1). The yield of the C.I. pigment yellow 139 is improved, and the obtained pigment has high performance (such as high coloring power, bright color, high dispersibility, extremely high light fastness and weathering fastness and the like).
Description
Technical field
The present invention relates to a kind of preparation method of isoindoline class pigment, specifically, relate to the preparation method of C.I. pigment yellow 13 9.
Background technology
C.I. pigment yellow 13 9 contains carbonyl, imino-, cyanic acid and carboxamido-group etc. as one of isoindoline class pigment owing in its molecule, thereby forms intramolecularly and intermolecular ydrogen bonding, causes molecular structure to have more planarity.Therefore, C.I. pigment yellow 13 9 is a kind of pigment dyestuffs with excellent heat-resisting, solvent resistance, and its structure is suc as formula shown in the I:
EP424,759 (or US.Pat.No.5,091; 532) a kind of method for preparing isoindoline class pigment is provided, its key step is: under the alkali existence condition, reacted in alcohol by phthalic nitrile earlier; The gained midbody reacts with the barbituric acid compounds more then, obtains target compound.
Though aforesaid method successfully obtains isoindoline class pigment (comprising C.I. pigment yellow 13 9), no matter be at the pigment yield, or room for improvement arranged all aspect the pigment performance.
Summary of the invention
The present invention provides the method for a kind of C.I. of preparation pigment yellow 13 9 (compound shown in the formula I), and purpose is, improves the yield and the performance thereof of C.I. pigment yellow 13 9.
A kind of method for preparing C.I. pigment yellow 13 9 (compound shown in the formula I) provided by the present invention comprises the steps:
(1) by phthalic nitrile (its structure is suc as formula shown in the II) preparation 1, the step of 3-diimino isoindoline (its structure is shown in formula III);
(2) by 1, the step of 3-diimino isoindoline and barbituric acid prepared in reaction bullion C.I. pigment yellow 13 9;
(3) step of the pigmenting of bullion C.I. pigment yellow 13 9; It is characterized in that, in the described reaction of step (1), add ammoniacal liquor or feed ammonia.
Contriver of the present invention finds after deliberation: in by the reaction system of compound shown in the compound formula III shown in the formula II, add ammoniacal liquor or feed ammonia; And under the effect of catalyzer; Not only can improve the yield (yield can reach 97%) of compound shown in the formula III, and the purity of compound shown in the formula III that is obtained is more than 99%.
Embodiment
In optimized technical scheme of the present invention, compound shown in the formula II is 1 with the mol ratio of the ammonia that feeds: (1～2), (additional proportion of ammoniacal liquor is converted to ammonia), preferred mol ratio is 1.0: (1.2～1.6).
The method for preparing C.I. pigment yellow 13 9 provided by the present invention specifically comprises the steps:
(1) phthalic nitrile (its structure is suc as formula shown in the II), catalyzer and organic solvent place reactor drum; Stir; Add ammoniacal liquor again or feed ammonia, and be warming up to 30 ℃～60 ℃ (preferred 40 ℃～55 ℃), and under this state, keep 2 hours～7 hours (preferred 3 hours～4 hours); Get 1,3-diimino isoindoline (its structure is shown in formula III);
(2) earlier with 1; 3-diimino isoindoline (its structure is shown in formula III) and mixed solution (the pH value is 2.5～5.0) reaction of being made up of barbituric acid, acid and water 1 hour～2 hours are warming up to reflux state then, and kept 2 hours～5 hours at reflux state; Cooling; Filter, get filter cake (bullion pigment), reclaim mother liquor and can be recycled;
(3) will in water, pull an oar by the filter cake of step (2) gained; And then adding tensio-active agent; Move in the pressure reaction still again; Under 1Kg～4Kg pressure condition and 100 ℃～130 ℃ states, keep 2 hours～5 hours (temperature ranges is different, and the form and aspect that obtain pigment are different), obtain title product through cooling, filtration, washing and drying;
Wherein, described catalyzer is: the carbonate of basic metal or earth alkali metal, alkoxide or oxyhydroxide, nitrogenous Lewis base (like organic amine or nitrogen heterocyclic ring), or lithium alkylide;
Described organic solvent is: C
1～C
6Aliphatic monobasic alcohol;
Described acid is: water-soluble organic carboxyl acid is or/and mineral acid;
Described tensio-active agent is: alkyl benzene sulphonate(ABS) sodium salt, alkyl naphthalene sulfonic acid sodium salt, aromatic carboxylic acid and R (CH
2CH
2O) nCOCH
2CH (SO
3Na) CO
2Na, wherein R be that nilox resin acid, gum resin are sour, hydroabietic acid, disproportionated rosin amine, gum resin amine, nilox resin acid amides, gum resin acid amides or gum resin-vinylformic acid adducts.
In another optimal technical scheme of the present invention, used organic solvent is: C
1～C
4Aliphatic monobasic alcohol, the organic solvent that the present invention recommends to use is: methyl alcohol, ethanol or Virahol.
In another optimal technical scheme of the present invention, used catalyzer is: triethylamine, pyridine, salt of wormwood or sodium alkoxide etc.
In another optimal technical scheme of the present invention, used acid is: water-soluble C
1～C
6Aliphatic carboxylic acid is or/and mineral acid, and the present invention recommends the acid used, is selected from: mixture a kind of or that (contain two kinds) more than two kinds in formic acid, acetate, Hydrocerol A, sulfuric acid or the hydrochloric acid.
Compared with prior art, the present invention has following advantage:
(1) the pigment yield is high, reach 95% (and EP424, the pigment yield less than 80% of 759 schemes);
(2) midbody (1,3-diimino isoindoline) need not to separate, and can directly drop into next step use; The solvent for use boiling point is low, and through with recyclable applying mechanically after pigment separates, the entire synthesis process technological operation is simple;
Excellent properties such as (3) adopt that method provided by the present invention is applied to that pigment has the tinting strength height, coloured light is bright-coloured, dispersing property good, light fastness and fastness to weathering are splendid, and the hazardous and noxious substances of noresidue in the pigment meet Environmental Safety property.
Below through embodiment the present invention is done further elaboration, its purpose only is better to understand content of the present invention, and unrestricted protection scope of the present invention.
Embodiment 1
(1) phthalonitrile 19.2g, triethylamine 0.8g, methyl alcohol 150ml are dropped in the four-hole boiling flask successively, open and stir, slowly feed ammonia (with the minusing metering, total feeding amount is 3g), system temperature simultaneously raises.40～50 ℃ of reactions 4 hours.
(2) in another flask, add the 39.5g barbituric acid, 400ml water begins to stir; Fully disperse; Add 5.6g formic acid and vitriolic mixture again, at room temperature will in 1～1.5 hour, dropwise then, temperature rising reflux reaction 2 hours by the resultant of step (1) gained.The cold filtration of lowering the temperature then, mother liquor is recycled, and filter cake is subsequent use.
(3) will add 0.4g butene dioic acid di-sec-octyl sodium sulfonate by step (2) gained filter cake water making beating,, filter then 130 ℃ of reaction under high pressures 3 hours, washing, oven dry, at last pigment 52.54g (brief note is pigment-1), yield is 95.5%.
Embodiment 2
(1) phthalonitrile 19.2g, salt of wormwood 1.2g, Virahol 150ml are dropped in the four-hole boiling flask successively, under whipped state, slowly dropping ammonia (25%) 12.6g after dropwising, begins the system temperature that raises.40～50 ℃ of reactions 3～4 hours.
(2) in another flask, add the 39.5g barbituric acid, 400ml water begins to stir; Fully disperse; The mixture that adds 6.7g Hydrocerol A and hydrochloric acid more at room temperature will be dropwised in 1～1.5 hour by the resultant of step (1) then, temperature rising reflux reaction 2 hours.The cold filtration of lowering the temperature then, mother liquor is recycled, and filter cake is subsequent use.
(3) by step (2) gained filter cake water making beating, add the 0.54g phenylformic acid, 105 ℃ of reaction under high pressures 2 hours, filter then, washing, oven dry, at last pigment 52.40g (brief note is pigment-2), yield is 95.3%.
Embodiment 3
Step (1) and (2) are with embodiment 1; With gained filter cake water making beating, add the 0.5g Rosinyl polyoxyethylene ether sulfosuccinic monoester disodium salt then,, filter then 130 ℃ of reaction under high pressures 5 hours, washing, oven dry, at last pigment 52.36g (brief note is pigment-3), yield is 95.2%.
Embodiment 4
(1) phthalonitrile 25.6g, triethylamine 2.0g, ethanol 200ml are dropped in the four-hole boiling flask successively, under whipped state, feed ammonia (with the minusing metering, total feeding amount is 4g), system temperature simultaneously raises.40～50 ℃ of reactions 3～4 hours.
(2) in another flask, add the 52.6g barbituric acid, 450ml water begins to stir, and fully disperses, and adds the mixture of 10.2g formic acid and dilute sulphuric acid again, at room temperature will in 1 hour, be dropwised temperature rising reflux reaction 2 hours then by the resultant of step (1).The cold filtration of lowering the temperature then, mother liquor is recycled, and filter cake is subsequent use.
(3) by step (2) gained filter cake water making beating, add 1.0g isopropyl naphthalene sulfonate sodium, 120 ℃ of reaction under high pressures 3 hours, filter then, washing, oven dry, at last pigment 69.4g (brief note is pigment-4), yield is 95.3%.
Embodiment 5
The trade names Paliotol Yellow L2140HD (note by abridging and be L2140HD) of BASF AG as standard specimen, is made paint with pigment-3 and detects contrast; , make paint with pigment-4 and detect contrast as standard specimen with Paliotol Yellow L1970 (brief note is L1970); , do plastics with pigment-2 and detect contrast as standard specimen with Paliotol YellowK1841 (brief note is K1841); Simultaneously the different samples of gained being carried out weathering resistance detects.
A. paint detects:
In glass cylinder, claim Synolac 30g, aminoresin 10g, YLENE 6g, pigment powder 4g; Granulated glass sphere 75g, the 2h that in shaker, vibrates, the gained slurry is scraped appearance respectively; Claim white alkyd paint 18g again, above-mentioned slurry 2g mixes back vibration 10min and obtains watering down slurry; Scrape appearance then, toast 30min down at 150 ℃, the pigment performance contrast is as shown in table 1 below.
B. plastics detect:
Claim 75gPVC, each 3 parts of 3g white titanium pigments, 0.15g pigment powder, behind the mixing in 160 ℃; The roller degree is that 25rpm and frictional force are roll extrusion 10min on 1: 1.2 the twin-roll machine, is cooled to 130 ℃ then, continues roll extrusion 10min again; Compressing tablet, colour examining, the pigment performance contrast is as shown in table 1 below.
C. weathering resistance detects:
A gained base China ink is scraped lining bar with 8# on iron foil, scrape appearance, with scale oven dry, will drying scale then, to put into model be Q-Sun Xenon Test Chamber ageing device, was exposed to the sun 1000 hours at 63 ℃ in 150 ℃ of baking ovens.Scale before and after being exposed to the sun is compared, and the result is as shown in table 2.
Table 1
Table 2
* reduced pigment is the prepared pigment of method that discloses by EP 424,759.
Claims (8)
1. method for preparing C.I. pigment yellow 13 9, it comprises the steps:
(1) by phthalic nitrile preparation 1, the step of 3-diimino isoindoline;
(2) by 1, the step of 3-diimino isoindoline and barbituric acid prepared in reaction bullion C.I. pigment yellow 13 9;
(3) step of the pigmenting of bullion C.I. pigment yellow 13 9; It is characterized in that, in the described reaction of step (1), add ammoniacal liquor or feed ammonia.
2. method according to claim 1 is characterized in that wherein the mol ratio of phthalic nitrile and ammonia is 1: (1～2).
3. method according to claim 1 or claim 2 is characterized in that said method comprises the steps:
(1) phthalic nitrile, catalyzer and organic solvent place reactor drum, stir, and add ammoniacal liquor again or feed ammonia, and be warming up to 30 ℃～60 ℃, and under this state, kept 2 hours～7 hours, get 1,3-diimino isoindoline;
(2) earlier with 1,3-diimino isoindoline and the mixed solution reaction of being made up of barbituric acid, acid and water 1 hour～2 hours are warming up to reflux state then; And reflux state maintenance 2 hours～5 hours, cooling was filtered; Get filter cake, reclaim mother liquor and can be recycled;
(3) will in water, pull an oar by the filter cake of step (2) gained; And then adding tensio-active agent; Move into again in the pressure reaction still, under 1Kg～4Kg pressure and 100 ℃～130 ℃ states, kept 2 hours～5 hours, obtain title product through cooling, filtration, washing and drying;
Wherein, described catalyzer is: the carbonate of basic metal or earth alkali metal, alkoxide or oxyhydroxide, nitrogenous Lewis base, or lithium alkylide; Described organic solvent is: C
1～C
6Aliphatic monobasic alcohol; Described acid is: water-soluble organic carboxyl acid is or/and mineral acid; Described tensio-active agent is: alkyl benzene sulphonate(ABS) sodium salt, alkyl naphthalene sulfonic acid sodium salt, aromatic carboxylic acid and R (CH
2CH
2O) nCOCH
2CH (SO
3Na) CO
2Na, wherein R be that nilox resin acid, gum resin are sour, hydroabietic acid, disproportionated rosin amine, gum resin amine, nilox resin acid amides, gum resin acid amides or gum resin-vinylformic acid adducts.
4. like the said method of claim 3, it is characterized in that wherein used organic solvent is: C
1～C
4Aliphatic monobasic alcohol.
5. like the said method of claim 4, it is characterized in that wherein used organic solvent is: methyl alcohol, ethanol or Virahol.
6. like the said method of claim 3, it is characterized in that wherein used catalyzer is: triethylamine, pyridine, salt of wormwood or sodium alkoxide.
7. like the said method of claim 3, it is characterized in that wherein used acid is: water-soluble C
1～C
6Aliphatic carboxylic acid is or/and mineral acid,
8. like the said method of claim 7, it is characterized in that wherein used acid is selected from: a kind of or mixture more than two kinds in formic acid, acetate, Hydrocerol A, sulfuric acid or the hydrochloric acid.
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| CN2011104476526A CN102585542A (en) | 2011-12-27 | 2011-12-27 | Method for preparing C.I. pigment yellow 139 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103013158A (en) * | 2012-12-13 | 2013-04-03 | 先尼科化工（上海）有限公司 | Synthetic method of isoindoline yellow pigment |
| CN103013159A (en) * | 2012-12-13 | 2013-04-03 | 先尼科化工（上海）有限公司 | Method for anhydrously preparing isoindoline pigment |
| CN110746653A (en) * | 2019-10-30 | 2020-02-04 | 东莞理工学院 | Thermoplastic resin coated pigment yellow 139 or derivatives thereof, process for preparing same and downstream products thereof |
| 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 |
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|---|---|---|---|---|
| US4166179A (en) * | 1976-06-24 | 1979-08-28 | Basf Aktiengesellschaft | Manufacture of organic pigments |
| US5091532A (en) * | 1989-10-27 | 1992-02-25 | Bayer Aktiengesellschaft | Process for the preparation of pigments based on isoindole |
| US20070119345A1 (en) * | 2004-02-20 | 2007-05-31 | Mca Technologies, Gmbh | Process for the preparation of organic materials |
| CN101490178A (en) * | 2006-07-18 | 2009-07-22 | 巴斯夫欧洲公司 | Isoindoline pigments |
| CN101654565A (en) * | 2008-08-21 | 2010-02-24 | 山东宇虹颜料有限公司 | Method for preparing isoindoline pigment |
| CN101896556A (en) * | 2007-12-10 | 2010-11-24 | 巴斯夫欧洲公司 | Equiaxial isoindoline yellow pigment |
-
2011
- 2011-12-27 CN CN2011104476526A patent/CN102585542A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166179A (en) * | 1976-06-24 | 1979-08-28 | Basf Aktiengesellschaft | Manufacture of organic pigments |
| US5091532A (en) * | 1989-10-27 | 1992-02-25 | Bayer Aktiengesellschaft | Process for the preparation of pigments based on isoindole |
| US20070119345A1 (en) * | 2004-02-20 | 2007-05-31 | Mca Technologies, Gmbh | Process for the preparation of organic materials |
| CN101490178A (en) * | 2006-07-18 | 2009-07-22 | 巴斯夫欧洲公司 | Isoindoline pigments |
| CN101896556A (en) * | 2007-12-10 | 2010-11-24 | 巴斯夫欧洲公司 | Equiaxial isoindoline yellow pigment |
| 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 (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103013158A (en) * | 2012-12-13 | 2013-04-03 | 先尼科化工（上海）有限公司 | Synthetic method of isoindoline yellow pigment |
| CN103013159A (en) * | 2012-12-13 | 2013-04-03 | 先尼科化工（上海）有限公司 | Method for anhydrously preparing isoindoline pigment |
| CN110746653A (en) * | 2019-10-30 | 2020-02-04 | 东莞理工学院 | Thermoplastic resin coated pigment yellow 139 or derivatives thereof, process for preparing same and downstream products thereof |
| 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 |
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Address after: 311222, Xiaoshan Town, Hangzhou, Zhejiang Applicant after: Lily Group Co., Ltd. Applicant after: East China University of Science and Technology Address before: 311222, Xiaoshan Town, Hangzhou, Zhejiang Applicant before: Lily Group Co., Ltd. Applicant before: East China University of Science and Technology |
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