CN103374238B - A kind of method preparing transparent type Pigment Yellow 73 180 - Google Patents
A kind of method preparing transparent type Pigment Yellow 73 180 Download PDFInfo
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- CN103374238B CN103374238B CN201210129934.6A CN201210129934A CN103374238B CN 103374238 B CN103374238 B CN 103374238B CN 201210129934 A CN201210129934 A CN 201210129934A CN 103374238 B CN103374238 B CN 103374238B
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Abstract
The invention discloses a kind of method preparing transparent type Pigment Yellow 73 180, comprise: prepare diazo solution, prepare Coupling Solution, use ammonium chloride and ammoniacal liquor configuration buffered soln, control pH=7 ~ 7.5, and add two-octadecyl-alkyl dimethyl ammonium chloride, then the Coupling Solution of 1/20-1/8 is first instilled, then drip diazo solution and Coupling Solution, control dropwise reaction time 15min ~ 8h, temperature of reaction controls at 10 ~ 50 DEG C simultaneously; Dropping terminates rear continuation stirring and treats that coupled reaction is thorough, and then filtration washing removing inorganic salt and part aqueous impurity, obtain crude product, adds auxiliary agent, water, hyperthermic treatment, and last filtering drying is pulverized and obtained finished product.The method, what produce in process of production is of reduced contamination, and cost is low, and the pigment particle size of output is evenly distributed, particle is soft, crystalline structure is consistent with the product of organic solvent process with crystallographic dimension, the tinctorial strength of product is high, bright in color light, and fast light, solvent resistance is good.Because the amide group in the group of Pigment Yellow 73 180 molecule makes its intermolecular binding strength improve greatly, thus improve its solvent resistance, every fastness such as thermotolerance.
Description
Technical field
The present invention relates to the preparation method of pigment, be specifically related to a kind of method preparing transparent type Pigment Yellow 73 180.
Background technology
C.I.P.Y180(Pigment Yellow 73 180) belong to benzoglyoxaline ketone pigment, its molecular formula of CAS.NO:77804-81-0 is:
Early stage azo pigment structure is simple, and molecular weight is little, colour fastness not high.Fastness to solvent, light fastness, weather-proof fastness cannot compared with high performance pigments.Its raw materials is BAPE(ethylene glycol (2 mainly, 2'-diamino) phenyl ether), Coupling Solution is AABI(5-acetoacetylaminobenzimidazolone), its preparation method and the approximate such as moral patent (DE2347532) of general benzimidazolone pigment.First diazotization reaction, dissolve Coupling Solution, then adopt the crude product pigmenting process after cis coupling synthesis as at organic solvent isopropylcarbinol, in DMF, thermal treatment is see European patent (ep10212) and US Patent No. 4370269, , the weak point of these techniques is that the pigment coloured light prepared is bright-coloured not, tinting strength is relatively general, technical process is long in addition, energy consumption is high, the problems such as solvent recuperation difficulty is large, it is crucial that the pigment that these methods are prepared is all the type of high covering power, this is restricted in the application of ink, therefore research and develop a kind of method preparing transparent type Pigment Yellow 73 180 newly tool is of great significance.
Summary of the invention
Goal of the invention: for the deficiencies in the prior art, the object of this invention is to provide a kind of method preparing transparent type Pigment Yellow 73 180, of reduced contamination with what realize producing in production process, and cost is low, the pigment particle size of output is evenly distributed, particle is soft, crystalline structure is consistent with the product of organic solvent process with crystallographic dimension, the tinctorial strength of product is high, bright in color light, and fast light, solvent resistance is good.
Technical scheme: in order to realize foregoing invention object, the technical solution used in the present invention is as follows:
Prepare a method for transparent type Pigment Yellow 73 180, comprise the following steps:
(1) with general diazotization methods, diazotization reaction is carried out to BAPE, prepare diazo solution for subsequent use;
(2) dissolve AABI with potassium hydroxide, prepare Coupling Solution for subsequent use;
(3) ammonium chloride and ammoniacal liquor configuration buffered soln is used, control pH=7 ~ 7.5, and add two-octadecyl-alkyl dimethyl ammonium chloride, then the Coupling Solution of 1/20-1/8 is first instilled, then drip diazo solution and Coupling Solution simultaneously, control dropwise reaction time 15min ~ 8h, temperature of reaction controls at 10 ~ 50 DEG C; Dropping terminates rear continuation stirring and treats that coupled reaction is thorough, and then filtration washing removing inorganic salt and part aqueous impurity, obtain crude product;
(4) in crude product, add auxiliary agent, water, hyperthermic treatment, last filtering drying is pulverized and is obtained finished product.
In step (3), the dropwise reaction time is 2 ~ 5h.
In step (3), temperature of reaction controls at 15 ~ 40 DEG C.
Prepare a method for transparent type Pigment Yellow 73 180, concrete steps are:
(1) get ethylene glycol (2,2'-diamino) phenyl ether 24.5g, add 36%HCI50g, add water 500mL and dissolve, be cooled to 0 ~ 5 DEG C, add NANO
2excessive to it, remove with urea reaction the nitrous acid filtered after stirring 3h, then decolorization filtering obtains diazonium salt solution, for subsequent use to 1000mL with frozen water adjustment volume;
(2) get 5-acetoacetyl amido benzimidazolone 57.2g, add in 500mL water, add potassium hydroxide 37.3g dissolution filter it, collect filtrate and add pure water adjustment volume to 1050mL, for subsequent use;
(3) ammonium chloride 107g is got, add in 2000mL water, add two-octadecyl-alkyl dimethyl ammonium chloride 5g, 28% ammoniacal liquor 30g, after being configured to buffered soln, control temperature starts first to drip 50mL Coupling Solution after 25-30 DEG C, then drip diazo solution and Coupling Solution, 4h drips end simultaneously, continues to stir 3h, then be warming up to 100 DEG C and keep 2h, filtration washing obtains crude product.
(4) crude product is added in the four-hole bottle of 2000mL, add 10g auxiliary pva 400, add after then pure water 1400mL is heated to 105 DEG C of maintenance 10h and filter, dry, pulverize and obtain finished product.
The present invention adopts in the buffered soln between ammoniacal liquor/ammonium chloride control pH=7-7.5 and carries out coupling, and more rapidly thoroughly, the granules of pigments of production is more tiny in reaction; And the pH of the easy hierarchy of control of coupling of stream stablizes, the diazo solution of the systems such as equivalent and Coupling Solution drip simultaneously can guarantee system stable; Adopt more high performance dispersant aid in coupled processes, such as two alkyl dimethyl ammonium halide, the pigment that coupling goes out such as alkyl diethanolamine scatter rapidly after separating out, and reduces its size of particles, impels it more transparent; Pigmenting post-processing stages adopts water treatment, and add polyvinyl alcohol series and make the crystal formation conversion of pigment more fast thoroughly as dispersing auxiliary, pigment product dispersiveness also can increase substantially.
Beneficial effect: prepare in Pigment Yellow 73 180 process with existing, use that a large amount of poisonous and hazardous organic solvents, coupled reaction condition are harsh, the opacifying power of pigment is too high, transparency not, compare, the preparation method of Pigment Yellow 73 180 of the present invention, what produce in process of production is of reduced contamination, and cost is low, the pigment particle size of output is evenly distributed, particle is soft, crystalline structure is consistent with the product of organic solvent process with crystallographic dimension, the tinctorial strength of product is high, bright in color light, and fast light, solvent resistance is good.Because the amide group in the group of Pigment Yellow 73 180 molecule makes its intermolecular binding strength improve greatly, thus improve its solvent resistance, every fastness such as thermotolerance.
Embodiment
Below in conjunction with specific embodiment, the present invention is described further.
Embodiment 1
Get ethylene glycol (2,2'-diamino) phenyl ether 24.5g, add HCI(36%) 50g, add water 500mL and dissolve, be cooled to 0 ~ 5 DEG C, add NANO
2excessive to it, remove with urea reaction the nitrous acid filtered after stirring 3h, then decolorization filtering obtains diazonium salt solution, for subsequent use to 1000mL. with frozen water adjustment volume.
Get 5-acetoacetyl amido benzimidazolone 57.2g, add in 500mL water, add potassium hydroxide 37.3g dissolution filter it, collect filtrate and add pure water adjustment volume to 1050mL, for subsequent use.
Get ammonium chloride 107g, add in 2000mL water, add auxiliary agent two-octadecyl-alkyl dimethyl ammonium chloride 5g, 28% ammoniacal liquor 30g, after being configured to buffered soln, control temperature starts first to drip 50mL Coupling Solution after 25-30 DEG C, then drip diazo solution and Coupling Solution, 4h drips end simultaneously, continues to stir 3h, then be warming up to 100 DEG C and keep 2h, filtration washing obtains crude product.
Crude product is added in the four-hole bottle of 2000mL, add 10g auxiliary pva 400, add after then pure water 1400mL is heated to 105 DEG C of maintenance 10h and filter, dry, pulverize and obtain finished product 72.8g.
Embodiment 2
Get ethylene glycol (2,2'-diamino) phenyl ether 24.5g, add HCI(36%) 60g, add water 500mL and dissolve, be cooled to 0 ~ 5 DEG C, add NANO
2excessive to it, remove with urea reaction the nitrous acid filtered after stirring 3h, then decolorization filtering obtains diazonium salt solution, for subsequent use to 1000mL with frozen water adjustment volume.
Get 5-acetoacetyl amido benzimidazolone 57.2g, add in 500mL water, add potassium hydroxide 44.7g dissolution filter it, collect filtrate and add pure water adjustment volume to 1100mL, for subsequent use.
Get ammonium chloride 153g, add in 2000mL water, add auxiliary agent two-octadecyl-alkyl dimethyl ammonium chloride 5g, 28% ammoniacal liquor 45g, after being configured to buffered soln, control temperature starts first to drip 100mL Coupling Solution after 30-35 DEG C, then drip diazo solution and Coupling Solution, 6h drips end simultaneously, continues to stir 2h, then be warming up to 90 DEG C and keep 2h, filtration washing obtains crude product.
Crude product is added in the four-hole bottle of 2000mL, add 12 grams of auxiliary pvas 600, add after then pure water 1400mL is heated to 100 DEG C of maintenance 8h and filter, dry, pulverize and obtain finished product 73.0g.
Embodiment 3
Get ethylene glycol (2,2'-diamino) phenyl ether 24.5g, add HCI(36%) 75g, add water 500mL and dissolve, be cooled to 0 ~ 5 DEG C, add NANO
2excessive to it, remove with urea reaction the nitrous acid filtered after stirring 3h, then decolorization filtering obtains diazonium salt solution, for subsequent use to 1000mL with frozen water adjustment volume.
Get 5-acetoacetyl amido benzimidazolone 57.2g, add in 500mL water, add potassium hydroxide 56.0g dissolution filter it, collect filtrate and add pure water adjustment volume to 1075mL, for subsequent use.
Get ammonium chloride 214g, add in 2000mL water, add auxiliary agent two-octadecyl-alkyl dimethyl ammonium chloride 5g, 28% ammoniacal liquor 60g, after being configured to buffered soln, control temperature starts first to drip 75mL Coupling Solution after 15-18 DEG C, then drip diazo solution and Coupling Solution, 6h drips end simultaneously, continues to stir 3h, then be warming up to 90 DEG C and keep 2h, filtration washing obtains crude product.
Crude product is added in the four-hole bottle of 2000mL, add 14g auxiliary pva 800, add after then pure water 1400mL is heated to 105 DEG C of maintenance 15h and filter, dry, pulverize and obtain finished product 73.1g.
Claims (2)
1. prepare a method for transparent type Pigment Yellow 73 180, it is characterized in that, comprise the following steps:
(1) with general diazotization methods, diazotization reaction is carried out to BAPE, prepare diazo solution for subsequent use;
(2) dissolve AABI with potassium hydroxide, prepare Coupling Solution for subsequent use;
(3) ammonium chloride and ammoniacal liquor preparation buffered soln is used, control pH=7.5, and add two-octadecyl-alkyl dimethyl ammonium chloride, then the Coupling Solution of 1/20 ~ 1/8 is first instilled, then drip diazo solution and Coupling Solution simultaneously, control dropwise reaction time 4-6h, temperature of reaction controls at 25-30 DEG C or 30-35 DEG C or 15-18 DEG C; Dropping terminates rear continuation stirring and treats that coupled reaction is thorough, and then filtration washing removing inorganic salt and part aqueous impurity, obtain crude product;
(4) in crude product, add auxiliary agent, water, hyperthermic treatment, last filtering drying is pulverized and is obtained finished product.
2. prepare a method for transparent type Pigment Yellow 73 180, it is characterized in that, concrete steps are:
(1) get ethylene glycol (2,2 '-diamino) phenyl ether 24.5g, add 36%HCl50g, add water 500mL and dissolve, be cooled to 0 ~ 5 DEG C, add NaNO
2excessive to it, remove excessive nitrous acid with urea reaction after stirring 3h, then decolorization filtering obtains diazonium salt solution, for subsequent use to 1000mL with frozen water adjustment volume;
(2) get 5-acetoacetylaminobenzimidazolone 57.2g, add in 500mL water, add potassium hydroxide 37.3g dissolution filter it, collect filtrate and add pure water adjustment volume to 1050mL, for subsequent use;
(3) ammonium chloride 107g is got, add in 2000mL water, add two-octadecyl-alkyl dimethyl ammonium chloride 5g, 28% ammoniacal liquor 30g, after being mixed with buffered soln, control temperature starts to drip 50mL Coupling Solution after 25-30 DEG C, then drip diazo solution and Coupling Solution, 4h drips end simultaneously, continues to stir 3h, then be warming up to 100 DEG C and keep 2h, filtration washing obtains crude product;
(4) crude product is added in the four-hole bottle of 2000mL, add 10g auxiliary pva 400, add after then pure water 1400mL is heated to 105 DEG C of maintenance 10h and filter, dry, pulverize and obtain finished product.
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| CN103788680B (en) * | 2013-12-25 | 2015-07-22 | 连云港锐华化工有限公司 | Preparation method of covering green-light benzimidazolone yellow HGRW for solvent treatment |
| CN113024889B (en) * | 2021-04-30 | 2021-10-15 | 鞍山辉虹颜料科技有限公司 | Organic colorant for coloring resin and preparation method thereof |
| CN114085543B (en) * | 2021-11-17 | 2023-11-07 | 龙口联合化学股份有限公司 | Application of quaternary ammonium salt derivative in preparation of red pigment, red pigment and preparation method |
| GB2617469A (en) * | 2021-11-17 | 2023-10-11 | Longkou Union Chemical Co Ltd | Use of quaternary ammonium salt derivative in preparation of red pigment, red pigment, and preparation method |
| CN115353751B (en) * | 2022-08-26 | 2023-11-14 | 浙江闰土染料有限公司 | Method for preparing monoazo disperse dye |
| CN116004028B (en) * | 2022-12-28 | 2024-07-02 | 江苏丽王科技有限公司 | Preparation method of pigment yellow 180 mixed crystal |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1408777A (en) * | 2001-09-21 | 2003-04-09 | 大日本油墨化学工业株式会社 | Pigment, process for producing pigment, pigment disperser and powder toner for static charge developing |
| CN1569968A (en) * | 2004-04-29 | 2005-01-26 | 华东理工大学 | Yellow, orange benzimidazolone like azo dye making method |
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| JP2002341594A (en) * | 2001-05-16 | 2002-11-27 | Dainippon Ink & Chem Inc | Electrostatic charge image developing toner |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1408777A (en) * | 2001-09-21 | 2003-04-09 | 大日本油墨化学工业株式会社 | Pigment, process for producing pigment, pigment disperser and powder toner for static charge developing |
| CN1569968A (en) * | 2004-04-29 | 2005-01-26 | 华东理工大学 | Yellow, orange benzimidazolone like azo dye making method |
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