CN112592603A - Green method for preparing solvent orange 60 with low pollution - Google Patents
Green method for preparing solvent orange 60 with low pollution Download PDFInfo
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- CN112592603A CN112592603A CN202011528038.8A CN202011528038A CN112592603A CN 112592603 A CN112592603 A CN 112592603A CN 202011528038 A CN202011528038 A CN 202011528038A CN 112592603 A CN112592603 A CN 112592603A
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- solvent orange
- filter cake
- diaminonaphthalene
- washing
- solvent
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- ZPSZXWVBMOMXED-UHFFFAOYSA-N 2-(2-bromo-5-chlorophenyl)acetic acid Chemical compound OC(=O)CC1=CC(Cl)=CC=C1Br ZPSZXWVBMOMXED-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 238000000034 method Methods 0.000 title claims abstract description 23
- 239000012065 filter cake Substances 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000005406 washing Methods 0.000 claims abstract description 16
- YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000010438 heat treatment Methods 0.000 claims abstract description 15
- 238000003756 stirring Methods 0.000 claims abstract description 14
- 238000001035 drying Methods 0.000 claims abstract description 12
- 239000000706 filtrate Substances 0.000 claims abstract description 11
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims abstract description 10
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000002791 soaking Methods 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 238000001816 cooling Methods 0.000 claims abstract description 8
- 238000000967 suction filtration Methods 0.000 claims abstract description 6
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 230000007935 neutral effect Effects 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims 2
- 239000000047 product Substances 0.000 abstract description 13
- 241000282326 Felis catus Species 0.000 abstract description 2
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 abstract description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 238000004806 packaging method and process Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 5
- 238000011109 contamination Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 230000008570 general process Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 239000011973 solid acid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VODSHQYSLMKQCD-UHFFFAOYSA-N 38478-71-6 Chemical compound C12=CC=CC=C2N2C(=O)C3=CC=CC=C3C3=NC=CC1=C32 VODSHQYSLMKQCD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- GBROPGWFBFCKAG-UHFFFAOYSA-N benzochrysene Natural products C1=CC2=C3C=CC=CC3=CC=C2C2=C1C1=CC=CC=C1C=C2 GBROPGWFBFCKAG-UHFFFAOYSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- -1 picene ketone Chemical class 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
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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
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/002—Aminoketone dyes, e.g. arylaminoketone dyes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention provides a green method for preparing solvent orange 60 with low pollution. The preparation method comprises the following steps: heating to 40-60 ℃, sequentially adding 1, 8-diaminonaphthalene, phthalic anhydride and SA cat into NMP, uniformly stirring, heating to 110-125 ℃ and reacting for 9-11 hours; cooling to 20-35 ℃, stirring for 1.5-2.5 hours, and performing suction filtration to obtain a filter cake and filtrate; washing and soaking the filter cake with hot water, collecting washing and soaking liquid and filtrate, and distilling and recovering; and washing the filter cake to be neutral by using hot water, and drying to obtain the solvent orange 60 dye. The solvent orange 60 dye obtained by the preparation method has the delta E of less than 1.0, the delta C of slightly brilliant 0.5 and the pressure value of less than 0.3, and the product quality can meet the application requirements of high-end customers.
Description
Technical Field
The invention relates to a preparation method of a dye, in particular to a preparation method of a low-pollution picene ketone type amino ketone dye solvent orange 60 dye, and belongs to the technical field of dye preparation.
Background
Solvent Orange 60, also known as fluorescence Orange 3G and transparent Orange 3G, has a chemical name of 12H-phthalin-12-one and a chemical name of Solvent Orange 60 and a molecular formula of C18H10N2O, molecular weight 270.29, CAS number 6925-69-5. The appearance is orange powder, insoluble in water and slightly soluble in organic solvents such as alcohol, chloroform, benzene, toluene, xylene and the like. The solvent orange 60 is mainly used for coloring various resins such as rigid polyvinyl chloride, polystyrene, ABS resin, organic glass, and the like. Also used for coloring the primary pulp of the polyester fiber. Has excellent heat resistance, sun resistance and migration resistance, good tinting strength, high transparency and wide application range.
At present, the general process for producing solvent orange 60 is as follows: adding 577 kg of water into a 10000L condensation kettle through a metering tank in the condensation kettle, starting stirring, adding 240 kg of packaged and metered 1, 8-diaminonaphthalene, 245 kg of phthalic anhydride and 1.12 kg of emulsifier OP, covering a kettle cover, adding 44.6 kg of 30% hydrochloric acid through the metering tank, then opening a jacket steam inlet valve, starting heating, heating to 100 and 105 ℃ for maintaining reflux, refluxing the condensate into the condensation kettle through first-stage freezing condensation, and sampling for 24-26h for reaction to measure the condensation end point. After the reaction is finished, cooling jacket water to 40-45 ℃, filtering, vacuum-pumping mother liquor, and washing filter cakes to neutrality by using hot water at 80-90 ℃; and drying the filter cake in an oven, crushing, mixing and packaging to obtain a finished product of the solvent orange 60. The solvent orange 60 product produced by the process has poor quality and poor color consistency, the hue delta C is less than or equal to 0.5 and accounts for about 80 percent of the total yield, and part of single-batch products can reach qualified quality only by solvent refining, thereby causing resource waste and pollution to the environment; the reaction yield is low, about 95 percent, side reactions generated in the reaction process are not easy to control, and the reaction selectivity and the product yield are influenced.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provides a preparation method of a solvent orange 60 dye, which has excellent hue and high product yield.
In order to achieve the technical purpose, the invention provides a green method for preparing solvent orange 60 with low pollution, which comprises the following steps:
heating to 40-60 ℃, sequentially adding 1, 8-diaminonaphthalene, phthalic anhydride and SA catalyst into NMP (N-methylpyrrolidone), uniformly stirring, heating to 110-;
cooling to 20-35 ℃, stirring for 1.5-2.5 hours, and performing suction filtration to obtain a filter cake and filtrate;
washing and soaking the filter cake with hot water, collecting washing and soaking liquid and filtrate, and distilling and recovering; and washing the filter cake to be neutral by using hot water, and drying to obtain the solvent orange 60 dye.
In one embodiment of the invention, the weight ratio of phthalic anhydride to 1, 8-diaminonaphthalene is from 0.8 to 1.0:1 (preferably from 0.9 to 1.0: 1). The weight ratio of the SA catalyst to the 1, 8-diaminonaphthalene is 0.002-0.01: 1 (preferably 0.005-0.01: 1). The mass ratio of the 1, 8-diaminonaphthalene to the NMP is 1: 2-3.5.
In one embodiment of the invention, the hot water is at a temperature of 80 ℃ to 100 ℃.
In one embodiment of the invention, the recovered solvent is distilled for the next batch of preparation. When the distilled and recovered solvent is used for the next batch of preparation, the distilled and recovered solvent is heated to 100-110 ℃ for dehydration, and then 1, 8-diaminonaphthalene and other raw materials are added for reaction.
The green method for preparing the solvent orange 60 with low pollution can specifically comprise the following steps:
(a) sequentially adding NMP into a reaction vessel, heating to 50 ℃, adding 1, 8-diaminonaphthalene, phthalic anhydride and an SA catalyst, uniformly stirring, continuously heating to 110-;
(b) then cooling to 20 ℃, stirring for 2 hours, and carrying out suction filtration to obtain a filter cake and filtrate;
(c) washing and soaking the filter cake with a proper amount of hot water, collecting soaking liquid and filtrate, and distilling and recovering; and washing the filter cake to be neutral by using hot water, and drying to obtain the solvent orange 60 dye.
The green method for preparing the solvent orange 60 with low pollution adopts a solvent phase reaction, the naphthylamine raw material can be well dissolved, and the reaction homogeneous phase is rapidly carried out; by adding the SA catalyst, the ideal effect can be achieved only by adding a very small amount of the SA catalyst, the dosage of the SA catalyst is about 1/10 of the dosage of the traditional acid catalyst, the production cost is reduced, the side reaction in the production process of the water phase method is inhibited, and the product quality is improved.
The green method for preparing the solvent orange 60 with low pollution adopts the reaction in the NMP solvent, the naphthylamine raw material can be well dissolved in the NMP, so that the reaction homogeneous phase is rapidly carried out, the reaction time is greatly shortened compared with the traditional process, and the reaction time is reduced to 5 hours from the original 22 hours.
According to the green method for preparing the solvent orange 60 with low pollution, the solid acid catalyst is added to replace the traditional inorganic acid in the nucleophilic substitution reaction, so that satisfactory high selectivity is obtained.
The green method for preparing the solvent orange 60 with low pollution adopts the solvent phase reaction, can avoid impurities generated by low selectivity caused by competitive side reaction in the prior art, obviously improves the product purity, improves the HPLC purity of the final product from less than 95 percent to more than 99 percent, ensures that the yield can be improved by about 5 percent compared with the prior art, can reach more than 98 percent, greatly reduces the production cost, has obvious economic benefit and reduces the pollutant discharge amount; more importantly, the obtained solvent orange 60 dye has delta E of less than 1.0, delta C of more than 0.5 and pressure value of less than 0.3, and the product quality can meet the application requirements of high-end customers.
According to the low-pollution green method for preparing the solvent orange 60, NMP is used as a reaction solvent, so that the method is green and environment-friendly, the decomposition is less in the solvent recovery process, a very small amount of solid acid is not required to be recovered, the ideal effect can be achieved only by a very small amount of addition, the dosage of the traditional inorganic acid catalyst is about 1/10, the production cost is reduced, and the safety of the production process is greatly improved.
Drawings
FIG. 1 shows the reaction equation of the green process for preparing solvent orange 60 with low contamination according to the present invention.
Fig. 2 is a process flow diagram of the green method for preparing solvent orange 60 with low pollution according to the present invention.
Detailed Description
Example 1
This example provides a green method for preparing solvent orange 60 with low pollution, the mechanism of which is shown in fig. 1, and the process flow of the reaction is shown in fig. 2, and the method includes the following steps:
(a) sequentially adding 600 kg of NMP into a reaction vessel, heating to 50 ℃, adding 240 kg of 1, 8-diaminonaphthalene, 230 kg of phthalic anhydride and 1.5 kg of SA cat, uniformly stirring, continuously heating to 115-125 ℃ for reaction for 5 hours, and determining a reaction end point by HPLC (high performance liquid chromatography) detection;
(b) then cooling to 20 ℃, stirring for 2 hours, and carrying out suction filtration to obtain a filter cake and filtrate;
(c) washing and soaking the filter cake with 500 kilograms of hot water, collecting washing and soaking liquid and filtrate, and distilling to recover the solvent; washing the filter cake to be neutral by hot water at the temperature of 90-100 ℃, drying, crushing and packaging to obtain 407 kg of finished solvent orange 60; the yield thereof was found to be 99.2%. Delta E0.833, Delta C0.705 are brilliant and the pressure value is 0.15.
Example 2
This example provides a green process for preparing solvent orange 60 with low contamination, which is substantially identical to that of example 1, except that: the amount of phthalic anhydride added in step (a) is 240 kg; finally, drying, crushing and packaging to obtain 401 kg of solvent orange 60 finished products; the yield thereof was found to be 98%. Δ E0.893, Δ C0.779, and pressure value 0.21.
Example 3
This example provides a green process for preparing solvent orange 60 with low contamination, which is substantially identical to that of example 1, except that: 720 kg of NMP is added in the step (a); finally, drying, crushing and packaging to obtain 403 kg of finished solvent orange 60; the yield thereof was found to be 98.3%. Δ E0.924, Δ C0.741 slightly brilliant, pressure value 0.09.
Example 4
This example provides a green process for preparing solvent orange 60 with low contamination, which is substantially identical to that of example 1, except that: the addition amount of the SA catalyst in the step (a) is 2.4 kg; finally, 405 kg of solvent orange 60 finished product is obtained after drying, crushing and packaging; the yield thereof was found to be 98.7%. Δ E0.722, Δ C0.518 are more brilliant, pressure value 0.16.
Example 5
This example provides a green process for preparing solvent orange 60 with low contamination, which is substantially identical to that of example 1, except that: in the step (b), the filtering temperature is raised to 35 ℃, and 402 kg of finished solvent orange 60 is obtained through drying, crushing and packaging; the yield thereof was found to be 98%. Delta E0.639, Delta C0.526 of brilliant color, pressure value 0.13
Comparative example 1
The comparative example provides a comparative production method of solvent orange 60 dye, which is carried out by adopting a general process, and specifically comprises the following steps: adding 577 kg of water into a 10000L condensation kettle, starting stirring, adding 240 kg of packaged and measured 1, 8-diaminonaphthalene, 265 kg of phthalic anhydride and 1.12 kg of emulsifier OP, covering a kettle cover, adding 44.6 kg of 30% hydrochloric acid through a metering tank, then opening a jacket steam inlet valve, starting heating to 100 plus 105 ℃ to maintain reflux, refluxing the condensate into the condensation kettle through first-stage freezing condensation, and sampling for 24-26h for reaction to detect the condensation end point. After the reaction is finished, cooling jacket water to 40-45 ℃, filtering, vacuum-pumping mother liquor, and washing filter cakes to neutrality by using hot water at 80-90 ℃; and drying the filter cake in a drying oven, crushing, mixing and packaging to obtain 390 kg of finished product of solvent orange 60, wherein the yield is 95.1%.
Comparative example 2
This comparative example provides a process for the production of a solvent orange 60 dye, essentially the same as example 1, except that: stirring uniformly, and then continuously heating to 135 ℃ for reaction for 2 hours. Then cooling to 15 ℃, stirring for 1 hour, and carrying out suction filtration to obtain a filter cake and filtrate. Packing to obtain 392 kilograms of finished product of solvent orange 60, with the yield of 95.5 percent. Δ E1.209, Δ C-0.821 off-dark, pressure value 0.32.
The above embodiments are merely illustrative of the technical ideas and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the contents of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (7)
1. A green method for preparing solvent orange 60 with low pollution, wherein the preparation method comprises the following steps:
heating to 40-60 ℃, sequentially adding 1, 8-diaminonaphthalene, phthalic anhydride and SA catalyst into NMP, uniformly stirring, heating to 110-125 ℃ and reacting for 5 hours;
cooling to 20-35 ℃, stirring for 1.5-2.5 hours, and performing suction filtration to obtain a filter cake and filtrate;
washing and soaking the filter cake with hot water, collecting washing and soaking liquid and filtrate, and distilling and recovering; and washing the filter cake to be neutral by using hot water, and drying to obtain the solvent orange 60 dye.
2. The production method according to claim 1, wherein the weight ratio of the phthalic anhydride and the 1, 8-diaminonaphthalene is 0.8 to 1.0: 1.
3. The method of claim 1, wherein the weight ratio of the SA catalyst to the 1, 8-diaminonaphthalene is 0.002-0.01: 1.
4. the production method according to claim 1, wherein the mass ratio of the 1, 8-diaminonaphthalene to NMP is 1: 2-3.5.
5. The method of claim 1, wherein the hot water has a temperature of 80 ℃ to 100 ℃.
6. The production method according to claim 1, wherein the recovered solvent is distilled for production of the next batch.
7. The production method according to claim 6, wherein the solvent recovered by distillation is used for the production of the next batch by first heating the solvent recovered by distillation to 100 ℃ to 110 ℃ for dehydration and then adding the 1, 8-diaminonaphthalene and other raw materials for reaction.
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| CN202011528038.8A CN112592603A (en) | 2020-12-22 | 2020-12-22 | Green method for preparing solvent orange 60 with low pollution |
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| CN202011528038.8A CN112592603A (en) | 2020-12-22 | 2020-12-22 | Green method for preparing solvent orange 60 with low pollution |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1379064A (en) * | 2001-03-29 | 2002-11-13 | 拜尔公司 | New crystal shape of dyestuff peri-ketone |
| CN101294005A (en) * | 2008-05-30 | 2008-10-29 | 海宁市现代化工有限公司 | Red naphtocyclinon solvent dye and preparation method thereof |
| CN101565556A (en) * | 2009-03-23 | 2009-10-28 | 南通龙翔化工有限公司 | Preparation method for solvent orange 60 |
| CN103275515A (en) * | 2013-06-18 | 2013-09-04 | 海宁市现代化工有限公司 | Orange naphtocyclinon dye and preparation method thereof |
| CN109762362A (en) * | 2019-01-22 | 2019-05-17 | 南通龙翔新材料科技股份有限公司 | The preparation method of pyrene ketones solvent dyestuff |
-
2020
- 2020-12-22 CN CN202011528038.8A patent/CN112592603A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1379064A (en) * | 2001-03-29 | 2002-11-13 | 拜尔公司 | New crystal shape of dyestuff peri-ketone |
| CN101294005A (en) * | 2008-05-30 | 2008-10-29 | 海宁市现代化工有限公司 | Red naphtocyclinon solvent dye and preparation method thereof |
| CN101565556A (en) * | 2009-03-23 | 2009-10-28 | 南通龙翔化工有限公司 | Preparation method for solvent orange 60 |
| CN103275515A (en) * | 2013-06-18 | 2013-09-04 | 海宁市现代化工有限公司 | Orange naphtocyclinon dye and preparation method thereof |
| CN109762362A (en) * | 2019-01-22 | 2019-05-17 | 南通龙翔新材料科技股份有限公司 | The preparation method of pyrene ketones solvent dyestuff |
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