CN1078602C - Preparation technology of dihalo substituted quinacridone organic-pigment - Google Patents
Preparation technology of dihalo substituted quinacridone organic-pigment Download PDFInfo
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- CN1078602C CN1078602C CN98112582A CN98112582A CN1078602C CN 1078602 C CN1078602 C CN 1078602C CN 98112582 A CN98112582 A CN 98112582A CN 98112582 A CN98112582 A CN 98112582A CN 1078602 C CN1078602 C CN 1078602C
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- quinacridone
- dihalo
- pigment
- present
- terephthalic acid
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B48/00—Quinacridones
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- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a preparation technique for quinacridone as an organic pigment, and the quinacridone comprises dihalo-substituted groups. The present invention belongs to the technical field of preparing serial organic quinacridone pigments. The technique of using dihalo-substituted anilino-terephthalic acid to prepare dihalo-substituted quinacridone pigments in polyphosphoric acid [PPA] in a closed loop way. The present invention has the advantages of reasonable and feasible preparation technique, high product yield and stable product quality.
Description
The invention belongs to quinacridone and show the organic dye preparing technical field.
Quinacridone organic-pigment is a kind of tone by orange to purple high-grade pigment dyestuff, and its thermotolerance, anti-dissolubility and resistance to migration are splendid, can be widely used in coating, plastics, printing ink, dissolve the painted of spinning etc.The synthetic method of quinacridone is more, and its main difference by playing raw material can be divided into: the succinate method; The Resorcinol method; Dibromo is to two phthalic acid methods; The ketene dimer method; 2,5-two amido terephthalic acid.1. succinate method: du pont company adopted the succinate method to produce quinacridone in 1958, its production process be succinate under the effect of sodium ethylate, by contracting certainly, acidifying gets the succinyl diethyl succinate then in relevant solvent; Succinyl diethyl succinate and aniline condensation get 2,5-hexichol amido-3,6-dihydro diethyl terephthalate under the effect of aniline salt; 2,5-hexichol amido-3,6-dihydro diethyl terephthalate is closed loop under the effect of the living A in road, gets 6, the 13-quinacridone; 6, the 13-quinacridone is in basic solution, and under the effect of oxygenant, oxydehydrogenation gets quinacridone.The Resorcinol method.This method is as follows by the process of Badiscche Anilin and Sodafalrik development: 1. use the salicylate similar methods, obtain Resorcinol-2, the 5-dioctyl phthalate.2. with Resorcinol-2, the condensation under the effect of ammonium vanadate of 5-dioctyl phthalate and aniline gets 3,5-hexichol amido-2,5-dicarboxyl-1,4-benzoquinones.3. with 3,5-hexichol amido-2,5-dicarboxyl-1,4-benzoquinones closed loop in the vitriol oil, quinacridone quinone.4. quinacridone quinone available metal powder, zinc powder for example, in the low molten mixture of alchlor and urea, reaction in the time of 80 ℃, quinacridone promptly is reduced into quinacridone.3. dibromoterephthalic acid method.This method is by Sandoz company development, and process is as follows: 1. 2, the 5-dibromoterephthalic acid under the effect of neutralized verdigris and potassiumiodide, in ethylene glycol solvent with aniline condensation, 2,5-hexichol amido terephthalic acid.2. 2,5-hexichol amido terephthalic acid closed loop in polyphosphoric acid gets quinacridone.4.2,5-hexichol amido terephthalic acid method.This method is by du pont company development, and process is as follows: 1. 2,5-hexichol amido terephthalic acid under the vitriolic effect with excessive cyclohexanone condensation, make the octahydro quinacridone earlier.2. the octahydro quinacridone gets quinacridone through the pyrolysis dehydrogenation.5. ketene dimer method.This method is the development of Lonza company, and production process is as follows: diketene is earlier oxidized, again by alcoholysis γ-chloroacetyl acetacetic ester.2. γ-chloroacetyl acetacetic ester from contract the succinyl diethyl succinate.3. succinyl diethyl succinate and aniline condensation, and then oxidation, saponification and acidifying get 2,5-hexichol amido terephthalic acid.4. 2,5-hexichol amido terephthalic acid closed loop in polyphosphoric acid gets quinacridone.In the method for above-mentioned five kinds of synthetic quinacridones, in fact have only two kinds of methods in industrial-scale production, to use at present, that is: succinate method and diketene method.Other three kinds of methods are expensive because of raw material, cost is high, complicated, need specific installation etc. former thereby do not adopt.At present, produce the quinacridone pigment overwhelming majority in the world and all adopt the succinate method, but the preparation method is not quite similar.
The present invention adopts phenyl-dihalide amido terephthalic acid to make raw material, and closed loop system contains the method for dihalo substituted quinacridone in polyphosphoric acid, and this preparation method controls easily, the yield height, and environmental pollution is few.
Feature of the present invention is that raw material directly adopts phenyl-dihalide amido terephthalic acid, in polyphosphoric acid PPA after the closed loop, add auxiliary agent, product enters precipitating in the solvent, and then in solvent, carry out pigmenting and handle, row making beating again, adding alkali when making beating, to make PH be 5-10, products therefrom press filtration, washing, drying, packing finally become the dihalo quinacridone to show machine pigment.
Fig. 1 is a schema of the present invention.
Following illustrative example, " part " in the example are by weight.Example: the polyphosphoric acid PPA100 part for preparing is added in the reactor, be warming up to 70 ℃, start stirring, slowly add 15 part 2,5-two p-Chlorobenzoic acid amide base terephthalic acids (DCTA) are warming up to 120-140 ℃, constant temperature 2-4 hour, add auxiliary agent then, product is poured in 150 parts of methyl alcohol that stirring and is heated up, and backflow 2-6 hour, cooling, filter washing, filter cake is put back in 120 parts of water and is pulled an oar, and adds alkali and transfers PH to 5-10, filter, wash, dry, pulverize 12.5 parts of products 2,9-dichloro quinacridone C.I.PR202 (DCTA meter, yield 91.2%).
Claims (1)
1. one kind contains dihalo substituted quinacridone organic-pigment preparation method, it is characterized in that: raw material directly adopts phenyl-dihalide amido terephthalic acid, in polyphosphoric acid PPA after the closed loop, add auxiliary agent, product enters precipitating in the solvent, and then carries out pigmenting and handle in solvent, row making beating again, the time adding alkali in making beating, to make PH be 5-10, and products therefrom press filtration, washing, drying, packing finally become the dihalo quinacridone to show machine pigment.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98112582A CN1078602C (en) | 1998-08-07 | 1998-08-07 | Preparation technology of dihalo substituted quinacridone organic-pigment |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN98112582A CN1078602C (en) | 1998-08-07 | 1998-08-07 | Preparation technology of dihalo substituted quinacridone organic-pigment |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1244553A CN1244553A (en) | 2000-02-16 |
| CN1078602C true CN1078602C (en) | 2002-01-30 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN98112582A Expired - Fee Related CN1078602C (en) | 1998-08-07 | 1998-08-07 | Preparation technology of dihalo substituted quinacridone organic-pigment |
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| CN (1) | CN1078602C (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1080283A (en) * | 1992-05-12 | 1994-01-05 | 赫彻斯特股份公司 | 2, the preparation method of 5-diphenyl amino-terephthalic acid and dialkyl ester thereof |
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1998
- 1998-08-07 CN CN98112582A patent/CN1078602C/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1080283A (en) * | 1992-05-12 | 1994-01-05 | 赫彻斯特股份公司 | 2, the preparation method of 5-diphenyl amino-terephthalic acid and dialkyl ester thereof |
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| Publication number | Publication date |
|---|---|
| CN1244553A (en) | 2000-02-16 |
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