CN101654565A - Method for preparing isoindoline pigment - Google Patents
Method for preparing isoindoline pigment Download PDFInfo
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- CN101654565A CN101654565A CN200810139252A CN200810139252A CN101654565A CN 101654565 A CN101654565 A CN 101654565A CN 200810139252 A CN200810139252 A CN 200810139252A CN 200810139252 A CN200810139252 A CN 200810139252A CN 101654565 A CN101654565 A CN 101654565A
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Abstract
The invention discloses a method for preparing an isoindoline pigment, and relates to a preparation method for a pigment. The method is characterized in that a raw material formula comprises the following components by mass: 102.4 to 153.6 grams of organic acid, 10.24 grams (0.08 mol) of barbituric acid (or derivatives thereof), 4.61 to 6.45 grams of 1,3-diiminoisoindoline, 0.10 to 0.41 gram of antioxidant, proper amount of (3 to 10 percent) alkali, 278 to 1,042.5 grams of water, and 0.15 to 1.5 grams of surfactant. The preparation method comprises the following steps: 1, pigment synthesis; 2,surfactant solution preparation; and 3, pigmentation. Compared with the traditional product, the pigment obtained by the formula and the preparation method has the advantages of good brilliance, highpigment yield and strong tinting strength; and the oxidation resistance and light resistance of the pigment in plastic application are further improved.
Description
Technical field:
The present invention relates to a kind of preparation method of pigment, especially the preparation method of isoindoline class pigment.
Background technology
Isoindoline class pigment is one of important kind of pigment dyestuff with practical value, contains imino-and carbonyl in such pigment molecule, can form intermolecular hydrogen bonding, has tangible planarity, has excellent heat-resisting, fast light, solvent resistance.German patent DE 1012406 has been introduced and has been adopted 1,3-diimino isoindoline and barbituric acid prepared in reaction yellow ultramarine: under agitation with 1, the hydrothermal solution of 3-diimino isoindoline adds in the veronal aqueous acid, under the ammonia effect, generate yellow mercury oxide, filtration, methyl alcohol are washed, the dry yellow ultramarine that gets; In the U.S. Pat 4166179 room temperature with barbituric acid and derivative thereof mix with water, acid suspension, 1,3-diimino isoindoline adds in the suspension gradually, adopts stirring at room 1h, boil 4h, reaction obtains isoindoline pigment under the condition of pH value 1-6.Because the existence of water medium is arranged, weakened the acidity of condensation reaction medium in the above patent, the vividness of pigment is bad and the pigment yield is not high.Temperature of reaction and time and pH value have a direct impact the performance of pigment, and the pigmenting power that adopts above-mentioned condition to obtain is unsatisfactory, and the oxidation-resistance in plastic applications, photostabilization problem remain further to be improved.
Summary of the invention
The isoindoline class method for preparing pigment that the purpose of this invention is to provide a kind of optimization, prior art pigment yield is low to solve, problem such as vividness, coloured light and tinting strength is bad, heat-resisting, fast light, oxidation-resistance and easily disperse difference in the pigment coloring.
The technical solution adopted for the present invention to solve the technical problems composition of raw materials weight ratio is: organic acid 102.4～153.6g, barbituric acid (or derivatives thereof) 10.24g (0.08mol), 1,3-diimino isoindoline 4.61～6.45g, oxidation inhibitor 0.10～0.41g, alkali (3%～10%) an amount of, water 278～1042.5g, tensio-active agent 0.15～1.5g;
Isoindoline class pigment of the present invention has the compound of following structural formula:
In the formula: R
1, R
2, R
3, R
4Can be selected from-H ,-CH
3,-C
2H
5,-C
3H
7,-C
4H
9,-C
5H
11,-C
6H
13, C
6H
12, preferred-H ,-CH
3Its preparation method is as follows:
1, pigment is synthetic: barbituric acid (or derivatives thereof) is mixed obtaining suspension in room temperature with acid, with 1,3-diimino isoindoline adds in 0.5-2h in the suspension gradually, adopts the segmentation insulation reaction, at room temperature reaction 1-2h, be warming up to 60-80 ℃ again, stirring reaction 1-5h adds oxidation inhibitor, continue to be warming up to reflux temperature, suction filtration behind the insulation reaction 2-8h, filtrate is recycled, and filter cake is standby.
Acid suitable in synthetic is aliphatics and aromatic carboxylic acid, as formic acid, acetate, propionic acid, oxalic acid, Succinic Acid, pentanedioic acid, citric acid, phenylformic acid, phthalic acid or its mixture.The ammonia that discharges in the condensation course neutralizes with acid, and acid is used as organic solvent again both as alkali-binding agent.The present invention selects strongly-acid ambient condition pH=0.5-2.5 for use.Acid is 10～15: 1 with the weight ratio of barbituric acid (or derivatives thereof); 1, the weight ratio of 3-diimino isoindoline and barbituric acid is 0.45～0.63: 1, preferred 0.566: 1.
Used oxidation inhibitor is hindered phenol antioxygen, polyphenol antioxidant, as 2, the 6-ditertbutylparacresol, four [β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid] pentaerythritol ester, β-(3, the 5-di-tert-butyl-hydroxy phenyl) propionic acid octadecanol ester, the weight ratio of addition and barbituric acid is 0.01～0.04: 1, the oxidation-resistance when adopting adding oxidation inhibitor raising pigment to use in plastics.
2. the configuration of surfactant soln: a kind of or its mixture of anion surfactant, nonionogenic tenside, cats product, amphoterics, polymkeric substance polymeric surface active agent is dissolved in the hot water (solvent), is mixed with 10% solution for standby.Anion surfactant is a higher fatty acid salt, higher alcohol sulfate salt, alkylsulfonate and phosphate ester salt; Nonionogenic tenside is the Fatty Alcohol(C12-C14 and C12-C18) ethylene oxide adduct, alkylphenol ethylene oxide adduct, lipid acid ethylene oxide adduct, the aliphatic amide ethylene oxide adduct, fatty acid amide ethylene oxide adduct, pentaerythritol fatty ester, the Sorbitol Powder fatty acid ester, the fatty acid alcohol acid amides; Cats product is quaternary ammonium salt, aliphatic amide alcoxyl hydrochlorate, aliphatic amine polyoxyethylene ether, binary aliphatic amide, polyamine; Amphoterics is the lauryl sodium acrylate, lauryl dimethyl trimethyl-glycine, alkyl imidazoline; The polymkeric substance polymeric surface active agent is multi-functional pigment dispersing agent, contain the specific pigment particles surface is had the multiple spot anchor formula group of avidity and is easy in its molecule and can be selected for use the SOLSPERSE series product of ICI company by dispersion medium compatible polymers solvent chain.Preferred C
12-
18The compound of fatty alcohol-polyoxyethylene ether (20) ether and SOLSPERSE27000, C
12-
18The weight ratio of fatty alcohol-polyoxyethylene ether (20) ether and SOLSPERSE27000 is 1: 1, and just it is dissolved in the hot water and dissolves, and is made into 10% solution, C
12-18The weight ratio of fatty alcohol-polyoxyethylene ether (20) ether and SOLSPERSE27000 addition and barbituric acid is 0.015～0.146: 1.
3. pigmenting: filter cake adds and contains in the water of surfactant soln, after the stirring and dissolving, add sig water, adjust pH=4.0-8.0, be warming up to 100 ℃ at normal pressure, insulation reaction 0.5-3h is for the pigment that obtains high covering power also can be warming up to 110 ℃-160 ℃, insulation reaction 0.5-5h in autoclave, filter, hot wash, the oven dry, pulverize finished product.Described filter cake solid content is 20～40%, and the weight ratio of filter cake and water is 1: 8-15; Used alkali is sodium hydroxide, potassium hydroxide, and yellow soda ash, salt of wormwood, its concentration of lye is 3%～10%, is used to adjust the pH value, to improve pigmenting power, improves the coloured light of pigment.
Embodiment
Embodiment 1:
1. pigment is synthetic: in the 500ml four-hole bottle of reflux exchanger, thermometer is housed, add formic acid 110g, barbituric acid 10.24g (0.08mol), stir into suspension, 1,3-diimino isoindoline 5.8g (0.04mol) added room temperature reaction 1h in 30 minutes, adjust PH values 1.0, be warming up to 70 ℃ of reaction 3h, add 2,6-ditertbutylparacresol 0.2g, continue to be warming up to backflow, back flow reaction 5h, suction filtration, the filtrate recycling, filter cake is standby.
2. the configuration of surfactant soln: accurately take by weighing C
12-18Fatty alcohol-polyoxyethylene ether (20) ether 0.28g, SOLSPERSE 27000 0.28g, heating for dissolving is good standby in the adding 5g water.
3. pigmenting: in beaker, add entry 450g, pigment filter cake (solid content 25%) and surfactant soln, the sodium hydroxide solution of adding 5% after the stirring and dissolving, adjust pH=5, be warming up to 100 ℃, insulation 2h filters, hot wash, the oven dry, pulverize finished product 13.9g, gained pigment tool high luminance relay power and bright-coloured ruddiness yellow.
Embodiment 2:
1. pigment is synthetic: in the 500ml four-hole bottle of reflux exchanger, thermometer is housed, add formic acid 120g, N, N-dimethyl barbituric acid 12.5g (0.08mol), stir into suspension, 1,3-diimino isoindoline 5.8g (0.04mol) added in 30 minutes, room temperature reaction 1h adjusts PH values 1.0, is warming up to 80 ℃ of reaction 3h, add 2,6 ditertiary butyl p cresol 0.2g, continue to be warming up to backflow, back flow reaction 5h, suction filtration, the filtrate recycling, filter cake is standby.
2, the configuration of surfactant soln: accurately take by weighing C
12-18Fatty alcohol-polyoxyethylene ether (20) ether 0.28g, SOLSPERSE 27000 0.28g, heating for dissolving is good standby in the adding 5g water.
3, pigmenting: in beaker, add entry 450g, pigment filter cake (solid content 25%) and surfactant soln, add 5% sodium hydroxide solution after the stirring and dissolving, adjust pH=4.5, be warming up to 100 ℃, insulation 2h filters, hot wash, the oven dry, pulverize the pigment finished product.
Embodiment 3:
With embodiment 1, only when pigmenting, replace 5% caustic lye of soda to obtain than the green partially yellow ultramarine of embodiment 1 coloured light with 5% yellow soda ash liquid.
Embodiment 4:
With embodiment 1, only when pigmenting, adjust pH=6.5, obtain the ruddiness crescendo, the yellow ultramarine that look power is higher.
Embodiment 5:
The configuration of the synthetic and surfactant soln of pigment is with embodiment 1;
Pigmenting: in autoclave, add entry 500g, pigment filter cake (solid content 25%) and surfactant soln, add 5% sodium hydroxide solution after the stirring and dissolving, adjust pH=5, be warming up to 130 ℃, insulation 2h filters, hot wash, the oven dry, pulverize the pigment finished product.Products obtained therefrom is higher than embodiment 1 opacifying power, and ruddiness is stronger.
Embodiment 6:
With embodiment 1, only when the configuration of surfactant soln, take by weighing C
12-18Fatty alcohol-polyoxyethylene ether (20) ether 0.42g, SOLSPERSE 27000 0.42g, heating for dissolving is good standby in the adding 7.5g water.
Claims (1)
1, a kind of method for preparing isoindoline pigment, it is characterized in that the composition of raw materials weight ratio is: organic acid 102.4～153.6g, barbituric acid (or derivatives thereof) 10.24g (0.08mol), 1,3-diimino isoindoline 4.61～6.45g, oxidation inhibitor 0.10～0.41g, alkali (3%～10%) an amount of, water 278～1042.5g, tensio-active agent 0.15～1.5g;
Its preparation method may further comprise the steps:
(1) pigment is synthetic: barbituric acid (or derivatives thereof) is mixed obtaining suspension in room temperature with acid, in 0.5-2h, add in the suspension gradually 1.3-diimino isoindoline, adopt the segmentation insulation reaction,, be warming up to 60-80 ℃ again at room temperature reaction 1-2h, stirring reaction 1-5h, add oxidation inhibitor, continue to be warming up to reflux temperature, suction filtration behind the insulation reaction 2-8h, filtrate is recycled, and filter cake is standby.
(2) surfactant soln configuration: a kind of or its mixture of anion surfactant, nonionogenic tenside, cats product, amphoterics, polymkeric substance polymeric surface active agent is dissolved in the hot water (solvent), is mixed with 10% solution for standby; Preferred C
12-18The compounded surfactant solution of fatty alcohol-polyoxyethylene ether (20) ether and SOLSPERSE27000.
(3) pigmenting: filter cake adds and contains in the water of surfactant soln, after the stirring and dissolving, add sig water, adjust pH=4.0-8.0, be warming up to 100 ℃ at normal pressure, insulation reaction 0.5-3h is for the pigment that obtains high covering power also can be warming up to 110 ℃-160 ℃, insulation reaction 0.5-5h in autoclave, filter, hot wash, the oven dry, pulverize finished product.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200810139252A CN101654565B (en) | 2008-08-21 | 2008-08-21 | Method for preparing isoindoline pigment |
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|---|---|---|---|
| CN200810139252A CN101654565B (en) | 2008-08-21 | 2008-08-21 | Method for preparing isoindoline pigment |
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| CN101654565A true CN101654565A (en) | 2010-02-24 |
| CN101654565B CN101654565B (en) | 2012-10-24 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN103289434A (en) * | 2012-02-24 | 2013-09-11 | 先尼科化工（上海）有限公司 | Method for producing isoindoline yellow pigment |
| CN103937333A (en) * | 2014-04-18 | 2014-07-23 | 广州艾科化学有限公司 | Mill base for foaming waterborne polyurethane |
| JP2019112537A (en) * | 2017-12-25 | 2019-07-11 | 東洋インキＳｃホールディングス株式会社 | Coloring agent for color filter, coloring composition and color filter |
| 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 |
| JP7017006B1 (en) | 2020-07-15 | 2022-02-08 | 東洋インキＳｃホールディングス株式会社 | Pigment compositions, coloring compositions, paints, inks, ink sets, printed matter, and packaging materials |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2628409C3 (en) * | 1976-06-24 | 1986-10-02 | Basf Ag, 6700 Ludwigshafen | Process for the production of pigment dyes |
| DE3022839A1 (en) * | 1980-06-19 | 1982-01-07 | Bayer Ag, 5090 Leverkusen | ISOINDOLENE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INTERMEDIATE PRODUCTS FOR THE PRODUCTION OF DYES |
| US6143067A (en) * | 1998-01-28 | 2000-11-07 | Ciba Specialty Chemicals Corporation | Isoindoline pigment having improved low shear dispersibility |
| EP1725619A1 (en) * | 2004-02-20 | 2006-11-29 | MCA Technologies GMBH | Process for the preparation of organic pigments |
-
2008
- 2008-08-21 CN CN200810139252A patent/CN101654565B/en active Active
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN103289434A (en) * | 2012-02-24 | 2013-09-11 | 先尼科化工（上海）有限公司 | Method for producing isoindoline yellow pigment |
| CN103937333A (en) * | 2014-04-18 | 2014-07-23 | 广州艾科化学有限公司 | Mill base for foaming waterborne polyurethane |
| CN103937333B (en) * | 2014-04-18 | 2016-01-20 | 广州艾科新材料股份有限公司 | A kind of waterborne polyurethane foaming mill base |
| JP2019112537A (en) * | 2017-12-25 | 2019-07-11 | 東洋インキＳｃホールディングス株式会社 | Coloring agent for color filter, coloring composition and color filter |
| JP7124313B2 (en) | 2017-12-25 | 2022-08-24 | 東洋インキＳｃホールディングス株式会社 | Colorant for color filter, coloring composition and color filter |
| 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 |
| JP7017006B1 (en) | 2020-07-15 | 2022-02-08 | 東洋インキＳｃホールディングス株式会社 | Pigment compositions, coloring compositions, paints, inks, ink sets, printed matter, and packaging materials |
| JP2022031604A (en) * | 2020-07-15 | 2022-02-21 | 東洋インキＳｃホールディングス株式会社 | Pigment composition, coloring composition, paint, ink, ink set, printed article, and packaging material |
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| CN101654565B (en) | 2012-10-24 |
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Address after: 253000 Shandong province Dezhou City Tianqu Industrial Park Orchard Road No. 6 Applicant after: Shandong Yuhong New Pigment Co., Ltd. Address before: 253000 Shandong province Dezhou City Tianqu Industrial Park Orchard Road No. 6 Applicant before: Shandong Yuhong Pigment Co., Ltd. |
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Free format text: CORRECT: APPLICANT; FROM: SHANDONG YUHONG PAINT CO., LTD. TO: SHANDONG YUHONG NEW PIGMENT CO., LTD. |
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Address after: 253000 Shandong province Dezhou City Tianqu Industrial Park Orchard Road No. 6 Patentee after: Yuhong Pigment Co., Ltd. Address before: 253000 Shandong province Dezhou City Tianqu Industrial Park Orchard Road No. 6 Patentee before: Shandong Yuhong New Pigment Co., Ltd. |