CN104031401A - Preparation method of C.I. pigment yellow 128 - Google Patents
Preparation method of C.I. pigment yellow 128 Download PDFInfo
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Abstract
The invention relates to a preparation method of a C.I. pigment yellow 128. The preparation method comprises the steps: adding a diazo component 3-amino-4-chloro-benzoic acid dissolved by a sodium hydroxide solution into hydrochloric acid, adding an NaNO2 solution, carrying out diazotization, and thus obtaining a diazo salt solution; adding the diazo salt solution into a coupling component N,N'-(2-chloro-5-methyl-1,4-phenylene)bis(3-oxobutyramide) dispersed by an organic solvent, coupling, and thus obtaining a bisazo dicarboxylic acid intermediate; and finally carrying out a condensation reaction and pigmentation to obtain the C.I. pigment yellow 128 product. The organic solvent-water mixed solvent is adopted in the coupling reaction, and the problem that a generated monoazo by-product is precipitated due to small solubility in the medium when one mole of diazo salt and one mole of the coupling component are coupled in the bisazo pigment preparation process is effectively solved. In addition, the polar solvent high-temperature treatment method is adopted in the pigmentation, so that the product process is simplified, and the cost is reduced; and the prepared pigment is bright in colored light and easy to disperse, and has excellent heat resistance and solvent resistance.
Description
Technical field
The present invention relates to a kind of synthetic and pigmenting of azo condensation pigment, be specifically related to a kind of preparation method of C.I. pigment Yellow 12 8.
Background technology
The spectral range of azo condensation pigment is wider, from the yellow with strong green glow to blue light redness (or purple) until brown.In the molecular structure of azo condensation pigment, contain multiple amide groups, the introducing of amide group has improved solvent resistance and the resistance to migration of pigment greatly, because its production cost is higher, although so they can be used to each industrial sector, but they are mainly used to high-grade occasion, the fields such as especially high-grade plastics, synthon original liquid coloring, high-grade printing-ink and sedan car top coat.
At present, market there is no domestic azo condensation pigment commodity at home, and domestic production producer, because some sport technique segments cannot be broken through, causes this field to be monopolized by external major company always, and required commodity depend on import.The current a kind of technique simple to operate, with low cost of exploitation of needing badly.In the preparation process of C.I. pigment Yellow 12 8 (as shown in formula I), relate to a kind of tetrazo dicarboxylic acid intermediate (as shown in formula II), this intermediate preparation is generally to form with diazonium salt and the coupling of one mole of bifunctional coupling component of two moles, but the product that actual production obtains not is desired, because in the time of one mole of diazonium salt and one mole of coupling component coupling, the by product monoazo carboxylic acid cpd generating is separated out because the solubleness in WATER AS FLOW MEDIUM is minimum, and so reaction below just cannot be carried out.There is people by the monoazo carboxylic acid byproduct generating is carried out to sand milling for this reason, attempt to subtract short grained size method and complete subsequent reactions, but produce little effect.Also someone attempts to carry out diazotization and coupled reaction in machine solvent, but these attempt all can not get highly purified intermediate.
A kind of method of utilizing microreactor technology to prepare C.I. Pigment Yellow 73 93 was once disclosed in patent of invention US6437104.
By microreactor or ordinary method, carry out coupled reaction with 3-amino-4-chloro-benzoic acid diazonium salt of two equivalents and the sodium hydroxide solution of monovalent 2-methyl-5-chloro di-acetyl acetyl-p-phenylenediamine, after filtration, washing, the dry tetrazo dicarboxylic acid intermediate of preparing, gained intermediate is added and in orthodichlorobenzene, forms suspension, suspension is added in microreactor with pump, in microreactor, mix and carry out acyl chloride reaction with the o-dichlorobenzene solution of the thionyl chloride adding simultaneously, carry out condensation reaction again with the 3-chloro-2-methyl aniline that orthodichlorobenzene dissolves, last 180 DEG C of pyroprocessing.The suspension flowing out from microreactor after filtration, hot orthodichlorobenzene washes, methyl alcohol is washed, washing etc., obtains pigment product 80 DEG C of vacuum-dryings.
A kind of yellow azo condensation pigment preparation method of (comprising C.I. Pigment Yellow 73 93,94,95,128 and 166) was once disclosed in patent of invention US3413279, the method by the diazonium salt of diazo component 3-amino-4-chloro-benzoic acid and the chloro-5-methyl of coupling component 2-di-acetyl acetyl-p-phenylenediamine at 105-110 DEG C in orthodichlorobenzene coupling make tetrazo dicarboxylic acid intermediate, because this method is inhomogeneous reaction, cause reaction to be difficult to carry out completely, productive rate is lower.In addition, preparing the required substituted aromatic amines intermediate of this class pigment and do not accomplish scale production, is also the commercial reason of this type of pigment of restriction.
The pigmentation method of C.I. Pigment Yellow 73 93 is disclosed in patent of invention US5194088.In the method, C.I. Pigment Yellow 73 93 crude products, anhydrous sodium sulphate and steel ball are placed in to ball grinder, ball milling 48h under room temperature.Treat that ball milling is complete, under room temperature, ball milling gained crude product is processed to 2h in dimethyl sulfoxide (DMSO), through hot water making beating washing, dryly can obtain the application fastness identical with the commodity Chromophtal Yellow3G of C.I. Pigment Yellow 73 93 but more high-strength product.
Summary of the invention
Main purpose of the present invention is the situation being monopolized by external major company for current C .I. pigment Yellow 12 8 commodity markets, proposes a kind of technique preparation method simple, with low cost, to realize the production domesticization of C.I. pigment Yellow 12 8.
For achieving the above object, the present invention has adopted the mode of first coupling after condensation to prepare C.I. pigment Yellow 12 8, and concrete route is as follows:
The preparation method of C.I. pigment Yellow 12 8 of the present invention, comprises the following steps:
(1) the chloro-phenylformic acid of diazo component 3-amino-4-is dissolved with sodium hydroxide solution, fully stirring and dissolving, being added concentration is that in 37% hydrochloric acid, on the rocks being cooled to-10～20 DEG C, add NaNO
2solution carries out diazotization, and reaction 0.1～1h, abolishes excessive NaNO with urea
2, regulate pH4～5 with anhydrous sodium acetate, make diazo liquid for subsequent use;
(2) chloro-coupling component 2-5-methyl di-acetyl acetyl-p-phenylenediamine, acid binding agent are added in organic solvent, add dispersion agent, fully stir and form uniform coupling solution; After step (1) gained diazo liquid is filtered, add and in coupling solution, carry out coupled reaction, coupling time 0.2～2h, 10～40 DEG C of coupling temperature, the complete pH of coupling is 4～10, after filtration, wash, be dried, grind and to obtain tetrazo dicarboxylic acid intermediate (as shown in formula II);
(3) step (2) gained tetrazo dicarboxylic acid intermediate is added in organic solvent, add acylating agent, back flow reaction 0.5～8h, through underpressure distillation, makes the muriatic suspension of tetrazo dicarboxylic dihydrazides; In suspension, add 2-(4-chlorophenoxy)-5-5-trifluoromethylaniline and catalyzer, under 80～180 DEG C of conditions, react 2～12h, after filtration, washing, dry, grind and obtain C.I. pigment Yellow 12 8 crude products;
(4) step (3) gained crude pigment product is added in organic solvent, under 60～180 DEG C of conditions, process 1～10h, after filtration, wash, be dried, grind and to obtain C.I. pigment Yellow 12 8 products.
The described diazo component 3-amino-4-chloro-benzoic acid of step (1) and diazo reagent NaNO
2mol ratio be 1:1.05～1.1.
In the described reaction of step (2), diazo component 3-amino-4-chloro-benzoic acid and the chloro-5-methyl of coupling component 2-di-acetyl acetyl-p-phenylenediamine mol ratio are 1: 0.48～0.52.
The described acid binding agent of step (2) is pyridine or triethylamine; Organic solvent is any one in DMF, Isosorbide-5-Nitrae-dioxane, tetrahydrofuran (THF) or methyl alcohol equal solvent; In reaction, to account for mixed solvent volume ratio be 30%～70% to organic solvent.
In the described reaction of step (2), dispersion agent used is any one in the tensio-active agents such as Sodium dodecylbenzene sulfonate, sodium metnylene bis-naphthalene sulfonate or alkylphenol polyoxyethylene.
Step (2) 0.2～2h of described coupling time, 10～40 DEG C of coupling temperature.
The described organic solvent of step (3) is orthodichlorobenzene, chlorobenzene or oil of mirbane; Described acylating agent be in thionyl chloride, phosphorus trichloride and phosphorus oxychloride any one.
The described catalyzer of step (3) is pyridine or triethylamine; N (two diimide dicarboxylic dihydrazides muriate): n (2-(4-chlorophenoxy)-5-5-trifluoromethylaniline): n (pyridine or triethylamine)=1:2～2.2:0.5～2 (mol ratio)
The described organic solvent of step (4) be in orthodichlorobenzene, oil of mirbane, DMF, N-Methyl pyrrolidone, 95% ethanol or dimethyl sulfoxide (DMSO) equal solvent any one.
Preparation method involved in the present invention, compared with patent US3413279, US2936306 and US6437104, has that technique is simple, actually operating safety, lower-cost feature, has made up the deficiencies in the prior art.
In the present invention, coupled reaction adopts water-organic solvent to mix while efficiently solving in traditional double azo pigment preparation process one mole of diazonium salt and one mole of coupling component coupling as solvent, and the monoazo by product of generation is due to the little problem of separating out of the solubleness in WATER AS FLOW MEDIUM.In addition, in pigmenting process, adopt the method for pyroprocessing in polar solvent can simplify production technique, reduce production costs, and obtained pigment colour is bright and new gorgeous, be easy to disperse, there is good heat-resisting, solvent resistance.
Brief description of the drawings
Fig. 1 is the thermogravimetric curve of the C.I. pigment Yellow 12 8 of preparation.
Embodiment
Further illustrate the present invention below in conjunction with specific embodiment, in embodiment, agents useful for same and instrument are all commercial product.
Embodiment 1
C.I. the preparation method of pigment Yellow 12 8, step is as follows:
(1) diazotization reaction: 13.8g3-amino-4-chloro-benzoic acid is dissolved in to the sodium hydroxide solution of 32g10%, fully stirring and dissolving, is then added in 35g concentrated hydrochloric acid, is on the rocksly cooled to 0～5 DEG C, adds the NaNO of 14.5g40%
2solution carries out diazotization, and reaction 0.5h, abolishes excessive NaNO with a small amount of urea
2, with anhydrous sodium acetate adjusting reaction solution pH to 4～5, make diazo liquid for subsequent use.
(2) coupled reaction: chloro-12.5g2-5-methyl di-acetyl Acetanilide, 9.1g pyridine are scattered in 34.5ml methyl alcohol, add 0.78g sodium metnylene bis-naphthalene sulfonate, fully stir to form uniform coupling solution.Diazo liquid that step (1) is made adds in coupling solution and carries out coupled reaction after filtering, 20 DEG C of coupling temperature, and coupling time 1h, the complete pH of coupling is 8.5, after filtration, ethanol washes, washes, and is dried, grinds and to obtain yellow powder 25.2g.
(3) C.I. pigment Yellow 12 8 is synthetic: by 17.2g tetrazo dicarboxylic acid intermediate, 29.7g SOCl
2, 4 droplets DMFs add in 120ml orthodichlorobenzene, back flow reaction 2h, underpressure distillation, obtains the orthodichlorobenzene suspension of tetrazo dicarboxyl acyl chlorides.In suspension, add 14.3g2-(4-chlorophenoxy)-5-5-trifluoromethylaniline, 3.68g pyridine and 80ml orthodichlorobenzene, under 140 DEG C of conditions, react 2h, wash, wash through ethanol, be dried, grind and to obtain yellow solid powder 28.3g, productive rate 92.1%.
(4) pigmenting: step (3) gained crude pigment product 12.3g is added in 150ml dimethyl sulfoxide (DMSO), back flow reaction 2h, cooling, filter, wash, be dried, grind and to obtain green phase yellow powder 11.7g through ethanol.
Products obtained therefrom and standard specimen Clariant8GNP are carried out to coloured light contrast test, and result shows, gained sample and standard specimen are similar to micro-compared with standard specimen, and colour examining result as shown in Table 1.
The tristimulus coordinates of table one C.I. pigment Yellow 12 8 samples and standard specimen Clariant8GNP
Embodiment 2
C.I. the preparation method of pigment Yellow 12 8, is characterized in that comprising following steps:
(1) diazotization reaction: 13.8g3-amino-4-chloro-benzoic acid is dissolved in to the sodium hydroxide solution of 32g10%, fully stirring and dissolving, is then added in 35g concentrated hydrochloric acid, and on the rocks being cooled to below 5 DEG C, adds the NaNO of 18.7g40%
2solution carries out diazotization, and reaction 1h, abolishes excessive NaNO with a small amount of urea
2, with anhydrous sodium acetate adjusting reaction solution pH to 4～5, make diazo liquid for subsequent use.
(2) coupled reaction: chloro-12.5g2-5-methyl di-acetyl Acetanilide, 9.1g pyridine are scattered in 34.5ml tetrahydrofuran (THF), add 0.78g OP-10, fully stir to form homodisperse coupling solution.Diazo liquid that step (1) is made adds in coupling solution and carries out coupled reaction after filtering, 30 DEG C of coupling temperature, and coupling time 2h, the complete pH of coupling is 6, after filtration, ethanol washes, washes, and is dried, grinds and to obtain yellow powder 25.6g.
(3) C.I. pigment Yellow 12 8 is synthetic: by 17.2g tetrazo dicarboxylic acid intermediate, 34.3g PCl
3, 4 droplets DMFs add in 120ml chlorobenzene, back flow reaction 2h, underpressure distillation, obtains the chlorobenzene suspension of tetrazo dicarboxyl acyl chlorides.In suspension, add 14.3g2-(4-chlorophenoxy)-5-5-trifluoromethylaniline, 4.7g triethylamine and 80ml chlorobenzene, under 160 DEG C of conditions, react 2h, wash, wash through ethanol, be dried, grind and to obtain yellow solid powder 28.8g.
(4) pigmenting: step (3) gained crude pigment product 12.3g is added in 150ml DMF, back flow reaction 2h, cooling, filter, wash, be dried, grind and to obtain green phase yellow powder 11.4g through ethanol.
Products obtained therefrom and standard specimen Clariant8GNP are carried out to tinting strength test, result show that gained sample tinting strength is standard specimen 105%, as shown in Table 2.Through thermotolerance test, show products obtained therefrom excellent heat resistance, as shown in table three and Fig. 1.
The tinting strength test of table two C.I. pigment Yellow 12 8 samples and standard specimen Clariant8GNP
The 8 sample heat-resistant stability tests of table three C.I. pigment Yellow 12
Embodiment 3
C.I. the preparation method of pigment Yellow 12 8, is characterized in that comprising following steps:
(1) diazotization reaction: 13.8g3-amino-4-chloro-benzoic acid is dissolved in to the sodium hydroxide solution of 32g10%, fully stirring and dissolving, is then added in 35g concentrated hydrochloric acid, and on the rocks being cooled to below 5 DEG C, adds the NaNO of 15.2g40%
2solution carries out diazotization, and reaction 0.25h, abolishes excessive NaNO with a small amount of urea
2, with anhydrous sodium acetate adjusting reaction solution pH to 4～5, make diazo liquid for subsequent use.
(2) coupled reaction: chloro-12.5g2-5-methyl di-acetyl Acetanilide, 9.1g pyridine are scattered in 34.5ml ethanol, add 0.78g OP-10, fully stir to form homodisperse coupling solution.Diazo liquid that step (1) is made adds in coupling solution and carries out coupled reaction after filtering, 40 DEG C of coupling temperature, and coupling time 0.5h, the complete pH of coupling is 9, after filtration, ethanol washes, washes, and is dried, grinds and to obtain yellow powder 25.3g.
(3) C.I. pigment Yellow 12 8 is synthetic: by 17.2g tetrazo dicarboxylic acid intermediate, 38.3g POCl
3, 4 droplets DMFs add in 120ml oil of mirbane, back flow reaction 2h, underpressure distillation, obtains the oil of mirbane suspension of tetrazo dicarboxyl acyl chlorides.In suspension, add 14.3g2-(4-chlorophenoxy)-5-5-trifluoromethylaniline, 9.4g triethylamine and 80ml chlorobenzene, under 120 DEG C of conditions, react 2h, wash, wash through ethanol, be dried, grind and to obtain yellow solid powder 28.6g.
(4) pigmenting: process C.I. pigment Yellow 12 8 with method similar to Example 2, difference is: process solvent 95% ethanol and substitute dimethyl sulfoxide (DMSO), treatment time 3h, obtains green phase yellow powder 11.9g.
Embodiment 4
C.I. the preparation method of pigment Yellow 12 8, is characterized in that comprising following steps:
(1) diazotization reaction: reaction times 0.75h, the other the same as in Example 1.
(2) coupled reaction: with the synthetic tetrazo dicarboxylic acid intermediate of method similar to Example 1, difference is: coupled reaction solvent is with 1,4-dioxane instead of methanol, in reaction 1,4-dioxane accounts for mixed solvent volume 30%, 10 DEG C of coupled reaction temperature, the complete pH of coupling is 6.5, obtains tetrazo dicarboxylic acid intermediate 25.3g.
(3) C.I. pigment Yellow 12 8 is synthetic: with the synthetic C.I. pigment Yellow 12 8 of method similar to Example 2, difference is: tetrazo dicarboxylic dihydrazides muriate, 2-(4-chlorophenoxy)-5-5-trifluoromethylaniline and triethylamine molar ratio 1:2.1:1 are 2-(4-chlorophenoxy)-5-5-trifluoromethylaniline 15.0g, triethylamine 2.35g that feeds intake that feeds intake, and obtain crude pigment product 28.4g.
(4) pigmenting: process C.I. pigment Yellow 12 8 with method similar to Example 2, difference is: process solvent orthodichlorobenzene and substitute dimethyl sulfoxide (DMSO), treatment time 12h, obtains green phase yellow powder 11.9g.
Embodiment 5
C.I. the preparation method of pigment Yellow 12 8, is characterized in that comprising following steps:
(1) diazotization reaction: with embodiment 4.
(2) coupled reaction: with the synthetic tetrazo dicarboxylic acid intermediate of method similar to Example 4, difference is: coupled reaction solvent Isosorbide-5-Nitrae-dioxane accounts for mixed solvent volume 50%, obtains tetrazo dicarboxylic acid intermediate 25.5g.
(3) C.I. pigment Yellow 12 8 is synthetic: with the synthetic C.I. pigment Yellow 12 8 of method similar to Example 1; difference is: acylating agent substitutes thionyl chloride by phosphorus oxychloride; tetrazo dicarboxylic dihydrazides muriate and 2-(4-chlorophenoxy)-5-5-trifluoromethylaniline molar ratio is that 1:2.2 is 2-(4-chlorophenoxy)-5-5-trifluoromethylaniline 15.8g that feeds intake, and obtains crude pigment product 28.6g.
(4) pigmenting: process C.I. pigment Yellow 12 8 with method similar to Example 1, difference is: process solvent N-Methyl pyrrolidone and substitute DMF, obtain green phase yellow powder 11.2g.
Embodiment 6
C.I. the preparation method of pigment Yellow 12 8, is characterized in that comprising following steps:
(1) diazotization reaction: with embodiment 1.
(2) coupled reaction: with the synthetic tetrazo dicarboxylic acid intermediate of method similar to Example 4, difference is: in coupled reaction, solvent Isosorbide-5-Nitrae-dioxane accounts for mixed solvent volume 70%, obtains tetrazo dicarboxylic acid intermediate 25.8g.
(3) C.I. pigment Yellow 12 8 is synthetic: with the synthetic C.I. pigment Yellow 12 8 of method similar to Example 3, difference is: the molar ratio of tetrazo dicarboxylic acid intermediate and phosphorus oxychloride is that 1:6 is the phosphorus oxychloride 22.9g that feeds intake, and obtains crude pigment product 28.4g.
(4) pigmenting: process C.I. pigment Yellow 12 8 with method similar to Example 1, difference is: process solvent oil of mirbane and substitute DMF, treatment time 6h, obtains green phase yellow powder 11.6g.
Embodiment 7
C.I. the preparation method of pigment Yellow 12 8, is characterized in that comprising following steps:
(1) diazotization reaction: with embodiment 1.
(2) coupled reaction: with the synthetic tetrazo dicarboxylic acid intermediate of method similar to Example 1, difference is: the chloro-5-methyl of 3 amino in coupled reaction-4-chloro-benzoic acid and 2-di-acetyl acetyl-p-phenylenediamine molar ratio 1:0.52 is the chloro-5-methyl of the 2-di-acetyl acetyl-p-phenylenediamine 13.6g that feeds intake, and obtains tetrazo dicarboxylic acid intermediate 26.2g.
(3) C.I. pigment Yellow 12 8 is synthetic: with the synthetic C.I. pigment Yellow 12 8 of method similar to Example 3, difference is: the molar ratio of tetrazo dicarboxylic acid intermediate and phosphorus oxychloride is that 1:2 is the phosphorus oxychloride 7.64g that feeds intake, and obtains crude pigment product 27.4g.
(4) pigmenting: process C.I. pigment Yellow 12 8 with method similar to Example 2, difference is: the treatment time is reduced to 1h by 2h, obtains green phase yellow powder 11.6g.
Embodiment 8
C.I. the preparation method of pigment Yellow 12 8, is characterized in that comprising following steps:
(1) diazotization reaction: with embodiment 1.
(2) coupled reaction: with the synthetic tetrazo dicarboxylic acid intermediate of method similar to Example 1, difference is: the chloro-5-methyl of 3 amino in coupled reaction-4-chloro-benzoic acid and 2-di-acetyl acetyl-p-phenylenediamine molar ratio is 1:0.5, be the chloro-5-methyl of the 2-di-acetyl acetyl-p-phenylenediamine 13.1g that feeds intake, obtain tetrazo dicarboxylic acid intermediate 25.8g.
(3) C.I. pigment Yellow 12 8 is synthetic: with the synthetic C.I. pigment Yellow 12 8 of method similar to Example 3, difference is: the molar ratio of tetrazo dicarboxylic acid intermediate and phosphorus oxychloride is 1:8, be the phosphorus oxychloride 30.6g that feeds intake, condensation reaction time is increased to 12h by 2h, obtains crude pigment product 28.2g.
(4) pigmenting: process C.I. pigment Yellow 12 8 with method similar to Example 3, difference is: the treatment time is increased to 6h by 3h, obtains green phase yellow powder 11.7g.
Claims (8)
1. a preparation method for C.I. pigment Yellow 12 8, is characterized in that comprising the following steps:
(1) the chloro-phenylformic acid of diazo component 3-amino-4-is joined in 5-30% sodium hydroxide solution, stir dissolution, after dissolving, being added concentration is that in 37% hydrochloric acid, on the rocks being cooled to-10～20 DEG C, add NaNO
2solution carries out diazotization reaction, and reaction 0.1～1h, abolishes excessive NaNO with urea
2, regulate pH4～5 with anhydrous sodium acetate, make diazo liquid for subsequent use;
(2) chloro-coupling component 2-5-methyl di-acetyl acetyl-p-phenylenediamine, acid binding agent are added in organic solvent, add dispersion agent, fully stir and form uniform coupling solution; After will step (1) gained diazo liquid filtering, add in coupling solution and carry out coupled reaction, coupling time 0.2～2h, 10～40 DEG C of coupling temperature, the complete pH of coupling is 4～10, after filtration, wash, be dried, grind and to obtain tetrazo dicarboxylic acid intermediate;
(3) step (2) gained tetrazo dicarboxylic acid intermediate is added in organic solvent, add acylating agent, back flow reaction 0.5～8h, through underpressure distillation, makes the muriatic suspension of tetrazo dicarboxylic dihydrazides; In suspension, add 2-(4-chlorophenoxy)-5-5-trifluoromethylaniline and catalyzer, under 80～180 DEG C of conditions, react 2～12h, after filtration, washing, dry, grind and obtain C.I. pigment Yellow 12 8 crude products;
(4) step (3) gained crude pigment product is added in organic solvent, under 60～180 DEG C of conditions, process 1～10h, after filtration, wash, be dried, grind and to obtain C.I. pigment Yellow 12 8 products.
2. the method for claim 1, is characterized in that the mol ratio of the described diazo component 3-amino-4-chloro-benzoic acid of step (1) and diazo reagent is 1:1.05～1.1.
3. the method for claim 1, is characterized in that in the described reaction of step (2) that diazo component and coupling component mol ratio are 1: 0.48～0.52.
4. the method for claim 1, is characterized in that the described acid binding agent of step (2) is pyridine or triethylamine; Organic solvent is DMF, Isosorbide-5-Nitrae-dioxane, tetrahydrofuran (THF) or methyl alcohol; In reaction, to account for mixed solvent volume ratio be 30%～70% to organic solvent.
5. the method for claim 1, is characterized in that in the described reaction of step (2), dispersion agent used is Sodium dodecylbenzene sulfonate, sodium metnylene bis-naphthalene sulfonate or alkylphenol polyoxyethylene.
6. the method for claim 1, is characterized in that the described organic solvent of step (3) is orthodichlorobenzene, chlorobenzene or oil of mirbane; Described acylating agent is thionyl chloride, phosphorus trichloride and phosphorus oxychloride.
7. the method for claim 1, it is characterized in that the described catalyzer of step (3) is pyridine or triethylamine, n (two diimide dicarboxylic dihydrazides muriate): n (2-(4-chlorophenoxy)-5-5-trifluoromethylaniline): n (pyridine or triethylamine)=1:2～2.2:0.5～2 (mol ratio).
8. the method for claim 1, is characterized in that the described organic solvent of step (4) is orthodichlorobenzene, oil of mirbane, DMF, N-Methyl pyrrolidone, 95% ethanol or dimethyl sulfoxide (DMSO).
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| CN1330115A (en) * | 2000-07-01 | 2002-01-09 | 克拉里安特国际有限公司 | Method for preparting tetrazo condensation pigment in micro-reactor |
| CN103160135A (en) * | 2011-12-08 | 2013-06-19 | 中国中化股份有限公司 | Strong green light yellow disazo organic pigment |
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| CN103224715A (en) * | 2013-04-03 | 2013-07-31 | 中国中化股份有限公司 | Preparation method of double-acetyl-p-phenylenediamine bisazo compound |
| CN103275518A (en) * | 2013-05-30 | 2013-09-04 | 鞍山七彩化学股份有限公司 | Method for preparing high-transparency high-strength pigment yellow 155 for water-based ink and water-based paint |
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Address after: 253000 Shandong province Dezhou City Tianqu Industrial Park Orchard Road No. 6 Co-patentee after: Tianjin University Patentee after: Yuhong Pigment Co., Ltd. Address before: 253000 Shandong province Dezhou City Tianqu Industrial Park Orchard Road No. 6 Co-patentee before: Tianjin University Patentee before: Shandong Yuhong New Pigment Co., Ltd. |