CN105670339A - Preparation method of C.I. pigment yellow 12 - Google Patents
Preparation method of C.I. pigment yellow 12 Download PDFInfo
- Publication number
- CN105670339A CN105670339A CN201610021759.7A CN201610021759A CN105670339A CN 105670339 A CN105670339 A CN 105670339A CN 201610021759 A CN201610021759 A CN 201610021759A CN 105670339 A CN105670339 A CN 105670339A
- Authority
- CN
- China
- Prior art keywords
- pigment yellow
- add
- preparation
- microreactor
- pot
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
- C09B67/0065—Preparation of organic pigments of organic pigments with only non-macromolecular compounds
-
- 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
- C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
- C09B35/02—Disazo dyes
- C09B35/021—Disazo dyes characterised by two coupling components of the same type
- C09B35/035—Disazo dyes characterised by two coupling components of the same type in which the coupling component containing an activated methylene group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention provides a preparation method of C.I. pigment yellow 12. The preparation method comprises the following steps: carrying out diazotization by the use of nitrosyl sulfuric acid, reacting in a microreactor and reacting in a coupling vessel for coupling so as to finally prepare the C.I. pigment yellow 12. The product has advantages of uniform particle size, soft particle, excellent brightness, strong tinting strength, good light resistance and good transparency and covering power.
Description
Technical field
The present invention relates to pigment preparing technical field, the preparation method being specifically related to C.I. pigment Yellow 12.
Background technology
Along with the development of fine chemistry industry, the development of organic pigment is extremely swift and violent, and the annual production of organic pigment brings up to 46.84 ten thousand t of 2010 from 210,000 t of 2000, is doubled and redoubled. Organic pigment is widely used in multiple industries such as leaflet, automobile industry, coatings industry, processing of high molecular material industry and textile fabric. Yellow organic pigment is one of wherein most popular kind. From the 1950's so far, synthesis technique and the application performance of organic pigment Huang are constantly improved by scientific research personnel so that it is application expands gradually.
Benzidine yellow series organic pigment put goods on the market at late 1930s, the beginning of the forties, and development is exceedingly fast, but owing to benzidine yellow serial pigment can decompose when 200 ~ 240 DEG C, it is applied in and is restricted to a certain extent. By improving, produce the second filial generation kind of benzidine yellow, including C.I. pigment Yellow 12, pigment yellow 114, pigment yellow 106 etc., there is more excellent tinting strength, tinting power, resistance to fastness and solvent resistance, be widely used in ink industry.
Pigment Yellow 12 is mainly used in ink, rubber, polyethylene, takes the painted of ethylene, polystyrene, polrvinyl chloride and the plastics such as phenolic aldehyde, urea aldehyde, is also used for the pigment printing of textile, it may also be used for coating and paper painted. These product have excellent vividness, strong coloring force, and sun-proof is good, and has good transparency and covering power, of many uses. The structure of pigment yellow is as follows:
Existing document is reported for work the method for synthetic dyestuff Huang 12:
In patent of invention 96110811.8, the coupling component dissolving by sodium hydroxide, and precipitate out with acetic acid, prepare the coupling component that granule is thinner, and add the cationic surfactant of 0.5～20% weight or amine oxide surfactant carries out coupling, and it is modified with the hydrogenated resin of 10～40% weight. Although preparing product dispersibility, glossiness better, opacity increases. But coupled processes needs add alkali dissolution and precipitate out with acetic acid, increase product cost and increase the COD of waste water. And be modified by substantial amounts of hydrogenated resin, obtaining the modified of pigment, unit Dry Sack rate is just relatively low.
There is disclosed patent 201210583237.8, adopt in the preparation process of pigment Yellow 12, add silica gel (m-SiO2) and Colophonium, make full use of the Dispersion on surface effect of Colophonium, the high absorption property of m-SiO2 and even particle size distribution characteristic thereof, make the pigment particles prepared can be firmly bonded to m-SiO2 surface and form Organic-inorganic composite pigment, and make the composite pigment particles size distribution obtained concentrate, thus improving the performance of pigment Yellow 12.Diazotising adopts hydrochloric acid and aminotriacetic acid rising temperature for dissolving precipitation of lowering the temperature, and uses sodium nitrite diazotising, and coupling component adopts liquid caustic soda to dissolve, and precipitates out with acetic acid and add sodium acetate buffer. Although, can prepare be firmly combined with and particle size distribution concentrate inorganic-organic pigment compound particle, thus improving the characteristic of pigment Yellow 12. But adopting heating, cooling process and coupling component employing first to dissolve in diazo coupling process and use acetic acid acid out, sodium acetate buffer again, cost can be higher on the one hand, increases the COD of waste water on the other hand.
Summary of the invention
The preparation method that the invention provides a kind of C.I. pigment Yellow 12, the method diazonium adopts nitrosyl sulfuric acid to carry out diazotising, and coupling is first reacted in microreactor, then reacts in coupling pot again; The C.I. pigment Yellow 12 uniform particle sizes, the granule that finally prepare are soft, have excellent vividness, strong coloring force, and sun-proof is good, and has good transparency and covering power.
The preparation method of a kind of C.I. pigment Yellow 12, comprises the steps:
(1) in diazonium pot, add 45～275kg sulphuric acid, open stirring, add 286～515kg nitrosyl sulfuric acid, be cooled to 20 DEG C, it is initially added into the 3 of 253kg, 3 '-dichloro-benzidine, feed time 2～3 hours, charge temperature 15～20 DEG C, finish, be incubated 2 hours, temperature 15～20 DEG C; 3,3 '-dichloro-benzidine: sulphuric acid: the mol ratio of nitrosyl sulfuric acid is 1:0.5～3.0:0.99～1.05;
(2) in dilution pot, 1200～1500kg water and 3000～3500kg ice are added, open stirring, start diazonium dilution, temperature is maintained at 5～10 DEG C, dilution time 1～2 hour, and dilution completes, it is incubated 15 minutes, add and remove nitrosyl material and adsorbent, stir 15 minutes, start filter pressing standby; Going nitrosyl material addition is 3, the 2～5% of 3 '-dichloro-benzidine quality, and adsorbent addition is 3, the 1～3% of 3 '-dichloro-benzidine quality;
(3) in dissolving pan, add 1200～1500kg water, open stirring, add 111.5～334.5kg phosphate under room temperature, to being completely dissolved; Being subsequently adding 339.8～371.7kgN-alpha.-acetylacetanilide, stirring is to being completely dissolved; 3,3 '-dichloro-benzidine: the mol ratio of acetoacetanilide is 1:0.95～1.05; Phosphatic addition is the 30～90% of acetoacetanilide quality;
(4) in microreactor, 10～12kg water is then first added, open stirring and the chilled brine of minisize reaction, it is cooled to 5 DEG C, first start the acetoacetanilide solution that dropping is dissolved, then start to drip the diazo liquid filtered, speed of controlling well makes acetoacetanilide solution and diazo liquid to drip off simultaneously, 1～2 hour time, and temperature controls at 5～10 DEG C;
(5) in coupling pot, 400～500kg water is added, open stirring, mixed liquor in microreactor is in overflow to coupling pot, after diazo liquid and acetoacetanilide solution dropwise, the residue liquid storage of microreactor is also put to coupling pot, and rinses microreactor with 10kg water; After being added dropwise to complete, stir 10 minutes at coupling pot, survey terminal, acetoacetanilide should be kept micro-excessive; After reaction terminates, heating up, be incubated 1 hour after adding surfactant, filter, be washed to pH for neutrality, inorganic salt is washed off; The addition of surfactant is 3, the 1～5% of 3 '-dichloro-benzidine quality;
(6) filter cake is placed in 80 DEG C of baking ovens and carries out drying and processing, add surfactant and can obtain pigment Yellow 12 finished product through grinding;The addition of surfactant is the 1～3% of filter cake quality.
In described step (1), the quality solubility of described nitrosyl sulfuric acid is 25～45%.
In described step (2), the described nitrosyl material that goes is carbamide or sulfamic acid.
In described step (2), described adsorbent is activated carbon or hargil or kieselguhr.
In described step (3), described phosphate is one or more in disodium hydrogen phosphate, tertiary sodium phosphate.
In described step (4), microreactor first drips acetoacetanilide solution, then is simultaneously added dropwise diazo liquid and acetoacetanilide, and drip off simultaneously.
In described step (5), mixed liquor is from overflow to coupling pot.
Described surfactant is one or more in peregal, sodium lignin sulfonate, OP-10.
Described surfactant is one or more in pelopon A, dodecyl sodium sulfate salt, Colophonium.
Wherein diazo component is 3,3 '-dichloro-benzidine, its structural formula:
Wherein as the acetoacetanilide of coupling component, its structural formula:
Its reaction equation is:
(1) diazo-reaction
(2) coupling reaction
Compared with prior art, beneficial effects of the present invention is embodied in:
(1), adopting nitrosyl sulfuric acid to prepare diazotization process, diazotising is comparatively complete, improves diazotising yield, reduces energy resource consumption, reduces brine waste.
(2), tertiary sodium phosphate is adopted to dissolve coupling component, the method for microreactor diazo liquid, coupling component double; two dropping premixing reaction, improves reaction rate, improves the application performance of pigment Yellow 12. Also can reduce ammonia nitrogen value and the COD of waste water.
(3), post processing is ground and is added dodecylbenzene sodium sulfonate so that pigment Yellow 12 uniform particle sizes, and color and luster is better, has excellent vividness, strong coloring force, and sun-proof is good, and has good transparency and covering power.
Detailed description of the invention
Embodiment 1
Diazonium pot adds 100kg sulphuric acid, opens stirring, add the nitrosyl sulfuric acid of 460kg28%, be cooled to 20 DEG C, it is initially added into the 3 of 253kg, 3 '-dichloro-benzidine, feed time 2～3 hours, charge temperature 15～20 DEG C, finish, be incubated 2 hours, temperature 15～20 DEG C.
Adding 1500kg water and 3000kg ice in dilution pot, open stirring, start diazonium dilution, temperature is maintained at 5～10 DEG C, dilution time 1～2 hour, and dilution completes, and is incubated 15 minutes, adds 6kg carbamide and 5kg activated carbon, stirs 15 minutes, starts filter pressing standby.
Dissolving pan adds 1500kg water, opens stirring, add 150kg tertiary sodium phosphate under room temperature, to being completely dissolved. Being subsequently adding 370kgN-alpha.-acetylacetanilide, stirring is to being completely dissolved.
Then in microreactor, first add 10kg water, open stirring and the chilled brine of minisize reaction, it is cooled to 5 DEG C, first start the coupling component that dropping is dissolved, then start to drip the diazo liquid filtered, control that speed, coupling component and diazo liquid should almost the time drips off well, 1～2 hour time, temperature controls at 5～10 DEG C.
Adding 500kg water in coupling pot, open stirring, the mixed liquor in microreactor is in overflow to coupling pot, and after diazo liquid and coupling component dropwise, a small amount of liquid storage at microreactor is also put to coupling pot, and rinses microreactor with 10kg water. After being added dropwise to complete, stir 10 minutes at coupling pot, survey terminal, coupling component should be kept micro-excessive. After reaction terminates, heating up, be incubated 1 hour after adding 5kg peregal, filter, be washed to pH for neutrality, inorganic salt is washed off substantially.
Filter cake is placed in 80 DEG C of baking ovens and carries out drying and processing, add 10kg dodecylbenzene sodium sulfonate and can obtain 580kg pigment Yellow 12 finished product through grinding.
Embodiment 2
Diazonium pot adds 240kg sulphuric acid, opens stirring, add the nitrosyl sulfuric acid of 322kg40%, be cooled to 20 DEG C, it is initially added into the 3 of 253kg, 3 '-dichloro-benzidine, feed time 2～3 hours, charge temperature 15～20 DEG C, finish, be incubated 2 hours, temperature 15～20 DEG C.
Adding 1200kg water and 3500kg ice in dilution pot, open stirring, start diazonium dilution, temperature is maintained at 5～10 DEG C, dilution time 1～2 hour, and dilution completes, and is incubated 15 minutes, adds 7kg carbamide and 6kg activated carbon, stirs 15 minutes, starts filter pressing standby.
Dissolving pan adds 1200kg water, opens stirring, add 334.5kg disodium hydrogen phosphate under room temperature, to being completely dissolved. Being subsequently adding 371.7kgN-alpha.-acetylacetanilide, stirring is to being completely dissolved.
Then in microreactor, first add 12kg water, open stirring and the chilled brine of minisize reaction, it is cooled to 5 DEG C, first start the coupling component that dropping is dissolved, then start to drip the diazo liquid filtered, control that speed, coupling component and diazo liquid should almost the time drips off well, 1～2 hour time, temperature controls at 5～10 DEG C.
Adding 400kg water in coupling pot, open stirring, the mixed liquor in microreactor is in overflow to coupling pot, and after diazo liquid and coupling component dropwise, a small amount of liquid storage at microreactor is also put to coupling pot, and rinses microreactor with 10kg water. After being added dropwise to complete, stir 10 minutes at coupling pot, survey terminal, coupling component should be kept micro-excessive. After reaction terminates, heating up, be incubated 1 hour after adding 6kg peregal, filter, be washed to pH for neutrality, inorganic salt is washed off substantially.
Filter cake is placed in 80 DEG C of baking ovens and carries out drying and processing, add 10kg dodecyl sodium sulfate and can obtain 575kg pigment Yellow 12 finished product through grinding.
Embodiment 3
Diazonium pot adds 45kg sulphuric acid, opens stirring, add the nitrosyl sulfuric acid of 515kg25%, be cooled to 20 DEG C, it is initially added into the 3 of 253kg, 3 '-dichloro-benzidine, feed time 2～3 hours, charge temperature 15～20 DEG C, finish, be incubated 2 hours, temperature 15～20 DEG C.
Adding 1500kg water and 3000kg ice in dilution pot, open stirring, start diazonium dilution, temperature is maintained at 5～10 DEG C, dilution time 1～2 hour, dilution completes, and is incubated 15 minutes, add 5.6kg carbamide and 2.5kg activated carbon, stir 15 minutes, start filter pressing standby.
Dissolving pan adds 1500kg water, opens stirring, add 120kg tertiary sodium phosphate under room temperature, to being completely dissolved. Being subsequently adding 370kgN-alpha.-acetylacetanilide, stirring is to being completely dissolved.
Then in microreactor, first add 10kg water, open stirring and the chilled brine of minisize reaction, it is cooled to 5 DEG C, first start the coupling component that dropping is dissolved, then start to drip the diazo liquid filtered, control that speed, coupling component and diazo liquid should almost the time drips off well, 1～2 hour time, temperature controls at 5～10 DEG C.
Adding 500kg water in coupling pot, open stirring, the mixed liquor in microreactor is in overflow to coupling pot, and after diazo liquid and coupling component dropwise, a small amount of liquid storage at microreactor is also put to coupling pot, and rinses microreactor with 10kg water.After being added dropwise to complete, stir 10 minutes at coupling pot, survey terminal, coupling component should be kept micro-excessive. After reaction terminates, heating up, be incubated 1 hour after adding 5kg peregal, filter, be washed to pH for neutrality, inorganic salt is washed off substantially.
Filter cake is placed in 80 DEG C of baking ovens and carries out drying and processing, add 10kg Colophonium and can obtain 575kg pigment Yellow 12 finished product through grinding.
Embodiment 4
Diazonium pot adds 200kg sulphuric acid, opens stirring, add the nitrosyl sulfuric acid of 368kg35%, be cooled to 20 DEG C, it is initially added into the 3 of 253kg, 3 '-dichloro-benzidine, feed time 2～3 hours, charge temperature 15～20 DEG C, finish, be incubated 2 hours, temperature 15～20 DEG C.
Adding 1500kg water and 3000kg ice in dilution pot, open stirring, start diazonium dilution, temperature is maintained at 5～10 DEG C, dilution time 1～2 hour, dilution completes, and is incubated 15 minutes, add 12.6kg carbamide and 7.5kg hargil, stir 15 minutes, start filter pressing standby.
Dissolving pan adds 1500kg water, opens stirring, add 250kg disodium hydrogen phosphate under room temperature, to being completely dissolved. Being subsequently adding 365kgN-alpha.-acetylacetanilide, stirring is to being completely dissolved.
Then in microreactor, first add 10kg water, open stirring and the chilled brine of minisize reaction, it is cooled to 5 DEG C, first start the coupling component that dropping is dissolved, then start to drip the diazo liquid filtered, control that speed, coupling component and diazo liquid should almost the time drips off well, 1～2 hour time, temperature controls at 5～10 DEG C.
Adding 500kg water in coupling pot, open stirring, the mixed liquor in microreactor is in overflow to coupling pot, and after diazo liquid and coupling component dropwise, a small amount of liquid storage at microreactor is also put to coupling pot, and rinses microreactor with 10kg water. After being added dropwise to complete, stir 10 minutes at coupling pot, survey terminal, coupling component should be kept micro-excessive. After reaction terminates, heating up, be incubated 1 hour after adding 10kg sodium lignin sulfonate, filter, be washed to pH for neutrality, inorganic salt is washed off substantially.
Filter cake is placed in 80 DEG C of baking ovens and carries out drying and processing, add 10kg dodecylbenzene sodium sulfonate and can obtain 570kg pigment Yellow 12 finished product through grinding.
Embodiment 5
Diazonium pot adds 275kg sulphuric acid, opens stirring, add the nitrosyl sulfuric acid of 286kg45%, be cooled to 20 DEG C, it is initially added into the 3 of 253kg, 3 '-dichloro-benzidine, feed time 2～3 hours, charge temperature 15～20 DEG C, finish, be incubated 2 hours, temperature 15～20 DEG C.
Adding 1500kg water and 3000kg ice in dilution pot, open stirring, start diazonium dilution, temperature is maintained at 5～10 DEG C, dilution time 1～2 hour, dilution completes, and is incubated 15 minutes, add 6kg sulfamic acid and 5kg activated carbon, stir 15 minutes, start filter pressing standby.
Dissolving pan adds 1500kg water, opens stirring, add 100kg tertiary sodium phosphate under room temperature, to being completely dissolved. Being subsequently adding 370kgN-alpha.-acetylacetanilide, stirring is to being completely dissolved.
Then in microreactor, first add 10kg water, open stirring and the chilled brine of minisize reaction, it is cooled to 5 DEG C, first start the coupling component that dropping is dissolved, then start to drip the diazo liquid filtered, control that speed, coupling component and diazo liquid should almost the time drips off well, 1～2 hour time, temperature controls at 5～10 DEG C.
Adding 500kg water in coupling pot, open stirring, the mixed liquor in microreactor is in overflow to coupling pot, and after diazo liquid and coupling component dropwise, a small amount of liquid storage at microreactor is also put to coupling pot, and rinses microreactor with 10kg water.After being added dropwise to complete, stir 10 minutes at coupling pot, survey terminal, coupling component should be kept micro-excessive. After reaction terminates, heating up, be incubated 1 hour after adding 5kgOP-10, filter, be washed to pH for neutrality, inorganic salt is washed off substantially.
Filter cake is placed in 80 DEG C of baking ovens and carries out drying and processing, add 10kg dodecylbenzene sodium sulfonate and can obtain 575kg pigment Yellow 12 finished product through grinding.
Comparative example 1
253kg3,3'-dichloro-benzidine, 608kg30% hydrochloric acid and 1188kg water are added in reactor and stir, ice bath is cooled to 0～5 DEG C, the sodium nitrite of 139.38kg is made into 30% solution add wherein, carry out diazo-reaction, and ensureing that solution is highly acid, temperature is lower than 5 DEG C, and sodium nitrite is micro-excessive. Finish continuation reaction 0.5h, add activated carbon decolorizing 10min, filter light brown obtains nitrogen liquid, standby coupling is used.
460.2kg alpha.-acetylacetanilide add in coupling still, and add 320kg30% sodium hydroxide and 1188kg water stirs to clarify, be gradually added into 156kg glacial acetic acid temperature 10～15 DEG C, stir to obtain suspension, adjusting pH value is 6.5～7, and standby coupling is used. 3 are added temperature 10～15 DEG C, 3 '-dichloro-benzidine diazonium salt solution is added drop-wise in the suspension of alpha.-acetylacetanilide, feed time is about 0.5h, then continue and stir 1h, ooze circle and control reaction end, finally heated to 90～95 DEG C, and it is incubated 1h, cooling, filters and is washed to neutrality, in less than 60 DEG C drying. Add 30kg turkey red oil and can obtain 580kg pigment Yellow 12 finished product through grinding.
Comparative example 2
253kg3,3'-dichloro-benzidine, 608kg30% hydrochloric acid and 1188kg water are added in reactor and stir, ice bath is cooled to 0～5 DEG C, the sodium nitrite of 139.38kg is made into 30% solution add wherein, carry out diazo-reaction, and ensureing that solution is highly acid, temperature is lower than 5 DEG C, and sodium nitrite is micro-excessive. Finish continuation reaction 0.5h, add activated carbon decolorizing 10min, filter light brown obtains nitrogen liquid, standby coupling is used.
460.2kg alpha.-acetylacetanilide add in coupling still, and add 136kg soda and 1188kg water stirs to clarify, be gradually added into 156kg glacial acetic acid temperature 10～15 DEG C, stir to obtain suspension, adjusting pH value is 6.5～7, and standby coupling is used. 3 are added temperature 10～15 DEG C, 3 '-dichloro-benzidine diazonium salt solution is added drop-wise in the suspension of alpha.-acetylacetanilide, feed time is about 0.5h, then continue and stir 1h, ooze circle and control reaction end, finally heated to 90～95 DEG C, and it is incubated 1h, cooling, filters and is washed to neutrality, in less than 60 DEG C drying. Add 10kg turkey red oil and can obtain 555kg pigment Yellow 12 finished product through grinding.
Embodiment 1 ~ 5 is as shown in table 1 with the performance comparison of comparative example 1 ~ 2:
Table 1
| Numbering | Outward appearance | Coloured light | Tinting strength, tinting power % | Dispersion force | (kg) must be measured |
| Embodiment 1 | Granule is uniform, soft | Bright-coloured | 107 | Good | 580 |
| Embodiment 2 | Granule is uniform, soft | Bright-coloured | 105 | Good | 575 |
| Embodiment 3 | Granule is uniform, soft | Bright-coloured | 109 | Good | 575 |
| Embodiment 4 | Granule is uniform, soft | Bright-coloured | 106 | Good | 570 |
| Embodiment 5 | Granule is uniform, soft | Bright-coloured | 105 | Good | 575 |
| Comparative example 1 | Granule is soft | Bright-coloured | 92 | Bad | 580 |
| Comparative example 2 | Granule is hard | Dark | 98 | Good | 555 |
From upper contrast it can be seen that the C.I. pigment Yellow 12 uniform particle sizes that obtains of the present invention, granule are soft, having excellent vividness, strong coloring force, dispersion force is good, and has good transparency and covering power. Yield.
Claims (9)
1. the preparation method of a C.I. pigment Yellow 12, it is characterised in that comprise the steps:
(1) in diazonium pot, add 45～275kg sulphuric acid, open stirring, add 286～515kg nitrosyl sulfuric acid, be cooled to 20 DEG C, it is initially added into the 3 of 253kg, 3 '-dichloro-benzidine, feed time 2～3 hours, charge temperature 15～20 DEG C, finish, be incubated 2 hours, temperature 15～20 DEG C;3,3 '-dichloro-benzidine: sulphuric acid: the mol ratio of nitrosyl sulfuric acid is 1:0.5～3.0:0.99～1.05;
(2) in dilution pot, 1200～1500kg water and 3000～3500kg ice are added, open stirring, start diazonium dilution, temperature is maintained at 5～10 DEG C, dilution time 1～2 hour, and dilution completes, it is incubated 15 minutes, add and remove nitrosyl material and adsorbent, stir 15 minutes, start filter pressing standby; Going nitrosyl material addition is 3, the 2～5% of 3 '-dichloro-benzidine quality, and adsorbent addition is 3, the 1～3% of 3 '-dichloro-benzidine quality;
(3) in dissolving pan, add 1200～1500kg water, open stirring, add 111.5～334.5kg phosphate under room temperature, to being completely dissolved; Being subsequently adding 339.8～371.7kgN-alpha.-acetylacetanilide, stirring is to being completely dissolved; 3,3 '-dichloro-benzidine: the mol ratio of acetoacetanilide is 1:0.95～1.05; Phosphatic addition is the 30～90% of acetoacetanilide quality;
(4) in microreactor, 10～12kg water is then first added, open stirring and the chilled brine of minisize reaction, it is cooled to 5 DEG C, first start the acetoacetanilide solution that dropping is dissolved, then start to drip the diazo liquid filtered, speed of controlling well makes acetoacetanilide solution and diazo liquid to drip off simultaneously, 1～2 hour time, and temperature controls at 5～10 DEG C;
(5) in coupling pot, 400～500kg water is added, open stirring, mixed liquor in microreactor is in overflow to coupling pot, after diazo liquid and acetoacetanilide solution dropwise, the residue liquid storage of microreactor is also put to coupling pot, and rinses microreactor with 10kg water; After being added dropwise to complete, stir 10 minutes at coupling pot, survey terminal, acetoacetanilide should be kept micro-excessive; After reaction terminates, heating up, be incubated 1 hour after adding surfactant, filter, be washed to pH for neutrality, inorganic salt is washed off; The addition of surfactant is 3, the 1～5% of 3 '-dichloro-benzidine quality;
(6) filter cake is placed in 80 DEG C of baking ovens and carries out drying and processing, add surfactant and can obtain pigment Yellow 12 finished product through grinding; The addition of surfactant is the 1～3% of filter cake quality.
2. the preparation method of C.I. pigment Yellow 12 according to claim 1, it is characterised in that in step (1), the quality solubility of described nitrosyl sulfuric acid is 25～45%.
3. the preparation method of C.I. pigment Yellow 12 according to claim 1, it is characterised in that in step (2), the described nitrosyl material that goes is carbamide or sulfamic acid.
4. the preparation method of C.I. pigment Yellow 12 according to claim 1, it is characterised in that in step (2), described adsorbent is activated carbon or hargil or kieselguhr.
5. the preparation method of C.I. pigment Yellow 12 according to claim 1, it is characterised in that in step (3), described phosphate is one or more in disodium hydrogen phosphate, tertiary sodium phosphate.
6. the preparation method of C.I. pigment Yellow 12 according to claim 1, it is characterised in that in step (4), first drips acetoacetanilide solution in microreactor, then is simultaneously added dropwise diazo liquid and acetoacetanilide, and drip off simultaneously.
7. the preparation method of C.I. pigment Yellow 12 according to claim 1, it is characterised in that in step (5), mixed liquor is from overflow to coupling pot.
8. the preparation method of C.I. pigment Yellow 12 according to claim 1, it is characterised in that in step (5), described surfactant is one or more in peregal, sodium lignin sulfonate, OP-10.
9. the preparation method of C.I. pigment Yellow 12 according to claim 1, it is characterised in that in step (5), described surfactant is one or more in pelopon A, dodecyl sodium sulfate salt, Colophonium.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610021759.7A CN105670339A (en) | 2016-01-14 | 2016-01-14 | Preparation method of C.I. pigment yellow 12 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610021759.7A CN105670339A (en) | 2016-01-14 | 2016-01-14 | Preparation method of C.I. pigment yellow 12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105670339A true CN105670339A (en) | 2016-06-15 |
Family
ID=56300349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610021759.7A Pending CN105670339A (en) | 2016-01-14 | 2016-01-14 | Preparation method of C.I. pigment yellow 12 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105670339A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107488361A (en) * | 2017-07-05 | 2017-12-19 | 清华大学 | A kind of method that serialization prepares azo dyes in microreactor |
| CN108727857A (en) * | 2018-05-25 | 2018-11-02 | 安徽华辉塑业科技股份有限公司 | One kind is to be modified composite pigment Huang as orange powdery paints made of raw material |
| CN112321969A (en) * | 2020-11-23 | 2021-02-05 | 安徽嘉美包装有限公司 | Anti-aging plastic packaging film and preparation method thereof |
| CN114752228A (en) * | 2022-05-16 | 2022-07-15 | 广东艾德仕新材料有限公司 | Preparation method and application of modified composite pigment yellow |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN1175053C (en) * | 2000-02-09 | 2004-11-10 | 克拉里安特国际有限公司 | Method for prodn. of azo dyes in microreactors |
| WO2005105927A1 (en) * | 2004-04-22 | 2005-11-10 | Clariant Produkte (Deutschland) Gmbh | Process for producing high-purity azo dyes |
| US20100229760A1 (en) * | 2009-03-11 | 2010-09-16 | Clariant International Ltd. | Pigment Red 112 With Enhanced Dispersibility |
| CN103013172A (en) * | 2012-12-27 | 2013-04-03 | 天津城市建设学院 | Preparation method of modified pigment yellow 12 |
-
2016
- 2016-01-14 CN CN201610021759.7A patent/CN105670339A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1175053C (en) * | 2000-02-09 | 2004-11-10 | 克拉里安特国际有限公司 | Method for prodn. of azo dyes in microreactors |
| 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 |
| WO2005105927A1 (en) * | 2004-04-22 | 2005-11-10 | Clariant Produkte (Deutschland) Gmbh | Process for producing high-purity azo dyes |
| US20100229760A1 (en) * | 2009-03-11 | 2010-09-16 | Clariant International Ltd. | Pigment Red 112 With Enhanced Dispersibility |
| CN103013172A (en) * | 2012-12-27 | 2013-04-03 | 天津城市建设学院 | Preparation method of modified pigment yellow 12 |
Non-Patent Citations (2)
| Title |
|---|
| HELMUT PENNEMANN: "《Improvement of Dye Properties of the Azo Pigment Yellow 12 Using a Micromixer-Based Process》", 《ORGANIC PROCESS RESEARCH & DEVELOPMENT》 * |
| 赵玉潮等: "《微化工技术在化学反应中的应用进展》", 《中国科技论文在线》 * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107488361A (en) * | 2017-07-05 | 2017-12-19 | 清华大学 | A kind of method that serialization prepares azo dyes in microreactor |
| CN107488361B (en) * | 2017-07-05 | 2019-08-16 | 清华大学 | A kind of method that serialization prepares azo dyes in microreactor |
| CN108727857A (en) * | 2018-05-25 | 2018-11-02 | 安徽华辉塑业科技股份有限公司 | One kind is to be modified composite pigment Huang as orange powdery paints made of raw material |
| CN112321969A (en) * | 2020-11-23 | 2021-02-05 | 安徽嘉美包装有限公司 | Anti-aging plastic packaging film and preparation method thereof |
| CN112321969B (en) * | 2020-11-23 | 2022-08-02 | 安徽嘉美包装有限公司 | Anti-aging plastic packaging film and preparation method thereof |
| CN114752228A (en) * | 2022-05-16 | 2022-07-15 | 广东艾德仕新材料有限公司 | Preparation method and application of modified composite pigment yellow |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105670339A (en) | Preparation method of C.I. pigment yellow 12 | |
| CN102816456B (en) | Method for preparing core pigment red 170 by inorganic nano material modification | |
| CN105670333A (en) | Preparation method of C.I. pigment yellow 13 | |
| CN103102712B (en) | Industrial production method for pigment yellow 81 | |
| CN103387754B (en) | Method for producing pigment red 48:2 with excellent heat resistance and migration resistance | |
| CN105647222A (en) | Preparation method of C.I. pigment yellow 83 | |
| CN109651836A (en) | A kind of industrialized preparing process of the low PCBs environment-friendly type yellow pigment PY83 of plastic cement | |
| CN105541674B (en) | A kind of compound and preparation method thereof and the application in terms of dyestuff | |
| CN104403349B (en) | A kind of industrialized preparing process of pigment yellow 97 | |
| CN103773077B (en) | Preparation method of solvent treatment covering type P.Y.83HR-70-RW | |
| CN105647221B (en) | Method for preparing C.I. pigment red 185 | |
| CN104130590A (en) | Industrial production method for migration-resistant bright red pigment 150 used for PU | |
| CN106590012A (en) | Method of using CLT acid isomer mixture to prepare acid dye powder and production | |
| CN103044949B (en) | Preparation method of yellow pigment | |
| CN104478887A (en) | Reactive turquoise blue dye semifinished product, and preparation method and application thereof | |
| CN106590013B (en) | The isomer mixture of CLT acid prepares acid dyes original powder and product | |
| CN103254661B (en) | Industrialized production method of transference-resistant blue light red pigment for PU (Poly Urethane) | |
| CN106590015A (en) | Direct orange S dye preparation process | |
| CN104877368A (en) | Chrysophenine G production process | |
| CN106634042B (en) | A kind of one-step method for synthesizing of active black dye | |
| CN112322069A (en) | Monoazo yellow acid dye and preparation method thereof | |
| CN114539804B (en) | Preparation method of red direct blending dye | |
| CN112322068B (en) | Monoazo yellow organic pigment and preparation method thereof | |
| CN106928751A (en) | A kind of bi-component disperse dyes and processing technology | |
| CN109054430A (en) | A kind of preparation method of acid dye finished product |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20160615 |
|
| RJ01 | Rejection of invention patent application after publication |