CN107474053A - The preparation method of Yi Zhong piceneketone type solvent dyes - Google Patents
The preparation method of Yi Zhong piceneketone type solvent dyes Download PDFInfo
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- CN107474053A CN107474053A CN201710748242.2A CN201710748242A CN107474053A CN 107474053 A CN107474053 A CN 107474053A CN 201710748242 A CN201710748242 A CN 201710748242A CN 107474053 A CN107474053 A CN 107474053A
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
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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
- C09B57/12—Perinones, i.e. naphthoylene-aryl-imidazoles
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention discloses the preparation method of Yi Zhong piceneketone type solvent dyes, comprise the following steps：(I) under blanket of nitrogen and reducing agent duplicate protection, 1,8- diaminonaphthalene in the presence of phase transfer catalyst polyethylene glycol, reacts with phthalic anhydride (or 1,8- naphthalic anhydride) in the DMF aqueous solution under reflux temperature；(II) to after being condensed terminal, reaction solution is cooled to room temperature, filtering, filter cake is washed with the low concentration DMF aqueous solution.Involved dyestuff is specially solvent orange 60 (C.I.564100) and solvent red 179 (C.I.564150).Under reducing agent and the duplicate protection of blanket of nitrogen; by means of phase transfer catalyst; target product is generated in high conversion rate in DMF water mixed solvents; the dyestuff of high-quality is obtained through simple separation; and more than 90% (in terms of DMF) solvent recovery can be used, be a kind of environment-friendly preparation method thereof.
Description
Technical field
The present invention relates to dyestuff preparation technology field, more particularly to the green preparation side of Yi Zhong piceneketone type solvent dyes
Method.
Background technology
The Representative Cultivars of piceneketone type solvent dye are mainly solvent orange 60, solvent of red 135, solvent red 179, its synthesis technique
It is roughly divided into Aqueous phase and the major class of solvent method two.The product quality of solvent method is relatively preferable, but cost is higher；The product of Aqueous phase
Cost is relatively low, but quality relative mistake, material nodeless mesh, is not received by the market." Aqueous phase " herein is not in absolute sense
Aqueous phase, generally referred to as solvent is not recycled below 20%, and to solvent, while Aqueous phase technique is led to
Catalyst often is made using 5~10% acid, it is more serious to equipment corrosion.
CN100413928C discloses a kind of production technology that solvent red 179 is produced using glacial acetic acid as solvent.1,8- naphthalene anhydrides
With 1,8- naphthylenediamines in 10-15 times of glacial acetic acid of its weight summation, in the presence of appropriate flower king auxiliary agent A -60, in 110-116
DEG C backflow 10-15 hours, the mol ratio of 1,8- naphthalene anhydride and 1,8- naphthylenediamine is 1:1.01, after reaction terminates, cooling filtering, from
The heart, filter cake washing drying, female filtrate are distilled to recover 105-115 DEG C of cut and recycled.The process recovery ratio 95.5%, gained
Product quality is preferable.But the technique has the disadvantage that：First, glacial acetic acid makees solvent, it is serious to equipment corrosion；Second, in filter cake
The acetic acid of residual is difficult to recycle, and waste water COD is very high.In general, the technique is not belonging to friendly process.
US5830931 discloses a kind of synthesis technique of fused ring compound.The technique belongs to Aqueous phase, in aqueous medium,
Acid catalysis and dielectric constant are in the presence of 20~60 hydrophilic compounds, atmospheric pressure reflux or anti-with carrying out being condensed under modest pressure
Should.Technical scheme is：50-150 DEG C of reaction temperature, suitable temperature are 90-140 DEG C, are typically carried out at ambient pressure, but can also
Carried out in negative pressure or with pressure.Negative pressure is 1-20 bars, the suitable reaction with pressure of 105-160 DEG C of reaction temperature.Added in reaction medium
Inorganic or organic acid is as optimization experiment scheme.Wherein, possible inorganic acid, such as hydrochloric acid, sulfuric acid, phosphoric acid or carbonic acid；May
Organic acid, such as methanesulfonic acid, acetic acid, formic acid, propionic acid, lactic acid or hydroxyacetic acid.Hydrochloric acid or sulfuric acid use preferably.The amount of acid
For the 0.1-20% of reaction medium weight.Water of the reaction medium suitably containing medium-weight 50-85%, 0.5-20% hydrophiles
Matter.Suitable hydrophilic substance is lactams, lactones or its mixture, such as N- methyl-butyrolactam, ε-valerolactam
And gamma-butyrolacton.Embodiment 1, embodiment 3 illustrate solvent orange 60, solvent red 179 respectively.The technique has the disadvantage that：One
It is the sulfuric acid concentration 5~8% of reaction system, and reaction temperature is more than 90 DEG C, to the seriously corroded of consersion unit；Second, add
About 5~8% hydroaropic substance, is neither reclaimed, and is not had mother liquid recycle again, be will be present in waste water, causes COD very high.It is overall
For, the technique is also not belonging to friendly process.
US5530130 discloses the preparation method of Yi Zhong piceneketone dyestuffs.The technique belongs to solvent method, and technical scheme is：Adopt
Solvent have chlorobenzene, o-dichlorohenzene, trichloro-benzenes, dimethylbenzene, DMF, 1-METHYLPYRROLIDONE, acetic acid, propionic acid, phenol, cresols,
Phenoxyethanol, ethylene glycol and its single or double alkyl ether, methanol, ethanol, isopropanol, dilute sulfuric acid etc.；The catalyst used then has chlorine
Change the inorganic or organic acids such as zinc, p-aminobenzene sulfonic acid, hydrochloric acid, sulfuric acid, glacial acetic acid, benzoic acid；Reaction temperature is at 80-150 DEG C.Its
Middle embodiment 67, embodiment 69 list solvent orange 60, solvent red 179 respectively, make solvent and catalyst, reaction temperature using phenol
Degree is at 130-150 DEG C.The shortcomings that technique is that solvent load is big, the methanol that should be distilled to recover in phenol, high temperature rectifying again
Phenol is reclaimed, production cost is higher；Process recovery ratio is relatively lower slightly.
CN101565556B discloses a kind of preparation method of solvent orange 60.The technique belongs to Aqueous phase, by the amount of material
Than for 1:1 phthalic anhydride and 1,8- naphthylenediamines and hydrochloric acid solution of the mass concentration for 1~5%, water-miscible polarity
Organic solvent and the mixing of ion inactive catalyst, flow back 8~15 hours.Hydrochloric acid dosage is 10~20 times of 1,8- naphthylenediamines；
Polar organic solvent dosage is the 1-50% of reaction medium total amount；The catalyst amount for reaction medium total amount 0.01~
2%.Polar organic solvent includes ethanol, acetic acid, DMF, 1-METHYLPYRROLIDONE, and the ion inactive catalyst used is nonyl
Phenol polyethenoxy ether.The technique has the disadvantage that：First, the hydrochloric acid solution of low concentration is chronically at high temperature reflux state, pair set
Standby seriously corroded；Second, NPE (NPEO) has larger harm to environment；Third, the waste water containing organic solvent
COD is very high, and wastewater flow rate is big, does not also recycle, and the technique is also not belonging to friendly process.
The content of the invention
The technical problem to be solved in the present invention is to provide the environment-friendly preparation method thereof of Yi Zhong piceneketone type solvent dyes.
Piceneketones type solvent dye is involved by this invention：Solvent orange 60 number (C.I.564100), solvent red No. 179 numbers
(C.I.564150).Corresponding chemical structural formula such as following formula：
Solvent orange 60 solvent red 179
The environment-friendly preparation method thereof of Yi Zhong piceneketones type solvent dye disclosed by the invention, its step include：
(I) under blanket of nitrogen and reducing agent duplicate protection, 1,8- diaminonaphthalene and phthalic anhydride (or 1,8- naphthalic anhydride),
In the presence of phase transfer catalyst polyethylene glycol, reacted 6~12 hours under reflux temperature in DMF aqueous medium；
(II) after condensation terminal arrives, reaction solution is cooled to room temperature, filtering, filter cake is washed with the low concentration DMF aqueous solution；
(III) female filtrate merges with washing filtrate, is distilled to recover.Less than 115 DEG C of cut is washed as next batch and used；
The reaction medium that more than 115 DEG C of cut is used as next batch is used.
Wherein, the reducing agent described in step (I) is：In sodium hydrogensulfite, sodium sulfite, sodium dithionite it is a kind of or
A variety of mixing, its dosage are the 3~6% of 1,8- diaminonaphthalene molal quantitys.
Phase transfer catalyst polyethylene glycol described in step (I) is specially：PEG-400 or PEG 600.
The dosage of phase transfer catalyst described in step (I) is the 2~8% of 1,8- diaminonaphthalene weight.
DMF concentration of aqueous solution described in step (I) is 40~90%.
Low concentration DMF concentration of aqueous solution described in step (II) is 10~30%.
The DMF mass concentrations of 100~115 DEG C of cuts described in step (III) are about 10~35%.
The DMF mass concentrations of more than 115 DEG C cuts described in step (III) are 75~85%.
The present invention has been provided in particular in synthesizing the green system of high-quality solvent orange 60 and solvent red 179 under a kind of non-acid catalysis
Preparation Method.The innovation of the preparation technology of the present invention is：It is corrosion-free to equipment without using acidic catalyst；Support the use
Phase transfer catalyst polyethylene glycol, ensure the high conversion of reaction；Reducing agent and blanket of nitrogen whole process protection 1,8- diaminonaphthalenes are complete
Prevent the oxidized possibility of its high temperature entirely, reaction conversion ratio is high, superior product quality.
Ortho position aromatic diamines and aromatic anhydride dehydration condensation Sheng Cheng piceneketone compounds, are generally both needed to acid
Matter makees catalyst, has used acidic catalyst (US5530130 bar none in the pertinent literature of background technology description section
Middle phenol is also similarly), so those skilled in the art are due to conventional inertial thinking, it is difficult to expect that acidic catalyst can be abandoned.
In fact, the present inventor is inadvertently found that under polyethylene glycol and phase transfer catalyst synergy, can
To complete the synthesis of solvent orange 60 and solvent red 179 well.And the synthesis that same technique is used for solvent of red 135 is then undesirable
(see comparative example 5), illustrate that the Gong Yi Dui piceneketone type solvent dyes of the present invention do not have universality.DMF is alkalescence material, therefore,
Without using acidic catalyst, the preparation for solvent orange 60 and solvent red 179 is that a Chao Chu piceneketones type solvent dye routinely closes
It is notable to the corrosive effect of reduction consersion unit and its subsidiary pipeline into the new technology of method, also substantially improve working environment.
The experiment of the present invention confirmed (see comparative example 1,2,3,4) no phase transfer catalyst polyethylene glycol or without acidic materials or
In the presence of not having reducing agent, either solvent orange 60 or the reaction yield of solvent red 179 is all relatively low, and coloured light is partially dark.
The technique of the present invention is both different from Aqueous phase, also different from solvent method, can be referred to as " half solvent method ", it reacted
Journey can be described as closer to solvent method：1,8- diaminonaphthalenes and phthalic anhydride (or 1,8- naphthalic anhydrides) are at a reflux temperature
In the 40-90%DMF aqueous solution, there is certain solubility, and solubility very little, phase transfer catalyst gather product under this condition
Ethylene glycol plays a part of promoting raw material continued dissolution, is effectively isolated raw material and product so that raw material is not wrapped up by product, keeps
Reaction speed, smoothly reaches reaction end, then may separate out the product of high-quality by cooling down, filtering.Reaction equation is as follows.
The chemical equation of solvent orange 60
The chemical equation of solvent red 179
Compared with conventional production process, its outstanding advantage is the present invention：
(1) this technique is to equipment no corrosion；
(2) product has crystallization, and quality is good, cost-effective, meets the requirement of high-end market.
(3) solvent recovery applies mechanically the (rate of recovery>90%), it is friendly process.
It is described further with reference to the preparation method of specific embodiment Dui this invention piceneketone type solvent dyes.
Embodiment
The experimental method of unreceipted actual conditions in the following example, generally according to normal condition, or according to manufacturer
Proposed condition.Ratio and percentage are based on weight, unless stated otherwise.
Embodiment 1
In 250ml four-hole bottles, nitrogen is passed through, adds 80%DMF aqueous solution 230g, stirs lower addition sodium sulfite
0.8g, hundred 1,8- diaminonaphthalenes 15.8g (0.1mol) is rolled over, roll over hundred phthalic anhydride 15.1g (0.102mol), 0.6g PEG-400.
It is warming up to micro- backflow (about 108~115 DEG C) and is incubated 10 hours, sampling detection terminal, after terminal reaches, is cooled to room temperature, mistake
Filter, filter cake is embathed, drained at twice with 50g 30%DMF, then is embathed and drained with 60 DEG C or so hot water of 25g, and filtrate, which merges, treats back
Receive.Again with 60 DEG C or so hot washes to color is not descended, 105 DEG C dry filter cake.Obtain bright orange solvent orange 60 crystallization 25.9g (yields
95.9%), coloured light, intensity Δ C 0.14, Δ E 0.42, intensity 99.8% compared with standard items.
Reclaim DMF：In 500ml equipped with the four-hole boiling flask of thermometer, filled column, condenser and receiving bottle, add and treat back
DMF filtrates are received, distillation, collect 100-115 DEG C of cut 70g (DMF concentration of aqueous solution is 31.3%), more than 115 DEG C cut 195g
(DMF concentration of aqueous solution is 83.5%), DMF recovery rate 92.8%.
Embodiment 2
With " PEG-600 " replacement " PEG-400 ", remaining is the same as embodiment 1.Obtain bright orange solvent orange 60 crystallization 25.7g (yields
95.2%), Δ C 0.24, Δ E 0.46, intensity 100.9% compared with standard items.
DMF removal process is the same as embodiment 1, DMF recovery rate 92.1%.
Embodiment 3
In 500ml four-hole bottles, nitrogen is passed through, adds 70%DMF aqueous solution 270g, stirs lower addition sodium dithionite
0.65g, hundred 1,8- diaminonaphthalenes 15.8g (0.1mol) is rolled over, roll over hundred phthalic anhydride 15.1g (0.102mol), 0.8g PEG-
400.It is warming up to micro- backflow (about 105~112 DEG C) and is incubated 12 hours, sampling detection terminal, after terminal reaches, is cooled to room
Temperature, filtering, filter cake is embathed at twice with 50g 20%DMF, then with 60 DEG C or so hot washes of 25g once, is drained, and filtrate is closed
It is and to be recycled.With 60 DEG C or so hot washes to color is not descended, 103 DEG C dry filter cake.Obtain bright orange solvent orange 60 crystallization 25.4g
(yield 94.1%), Δ C 0.12, Δ E 0.35, intensity 99.6% compared with standard items.
Reclaim DMF：In 500ml flasks, DMF filtrates to be recycled are added, are distilled, collect 100~115 DEG C of cut 100g
(DMF concentration of aqueous solution is 26.2%), more than 115 DEG C cut 188g (DMF concentration of aqueous solution is 82.6%), DMF recovery rate is about
91.2%.
Embodiment 4
In 500ml four-hole bottles, nitrogen is passed through, adds 50%DMF aqueous solution 330g, stirs lower addition sodium hydrogensulfite
0.7g, hundred 1,8- diaminonaphthalenes 15.8g (0.1mol) is rolled over, rolls over hundred 1,8- naphthalic anhydrides 20.0g (0.101mol),
0.8g PEG-400.It is warming up to micro- backflow (about 104~110 DEG C) and is incubated 8 hours, sampling detection terminal, after terminal reaches, drop
Warming to room temperature, filter, filter cake is embathed, drained at twice with 50g 20%DMF, then is embathed and drained with 60 DEG C or so hot water of 25g,
Filtrate merges to be recycled.With 60 DEG C or so hot washes to color is not descended, 105 DEG C dry filter cake.Rufous solvent red 179 is obtained to crystallize
31.3g (yield 97.7%), Δ C 0.10, Δ E 0.36, intensity 100.3% compared with standard items.
Reclaim DMF：In 500ml equipped with the four-hole boiling flask of thermometer, filled column, condenser and receiving bottle, add and treat back
The distillation of DMF filtrates is received, collects 98-115 DEG C of cut 226g (DMF concentration of aqueous solution is 23.3%), more than 115 DEG C cut 130g
(DMF concentration of aqueous solution is 81.4%), DMF recovery rate 90.6%.
Embodiment 5
So that " " sodium hydrogensulfite 0.7g ", remaining is the same as embodiment 4 for sodium sulfite 0.8g " replacements.Obtain rufous solvent red 179
Crystallize 31.2g (yield 97.4%), Δ C 0.26, Δ E 0.48, intensity 100.3% compared with standard items.
DMF removal process is the same as example 4, DMF recovery rate 90.5%.
Embodiment 6
With " PEG-600 " replacement " PEG-400 ", remaining is the same as embodiment 4.Obtain rufous solvent red 179 and crystallize 31.2g (receipts
Rate 97.4%), Δ C 0.18, Δ E 0.37, intensity 99.7% compared with standard items.
DMF removal process is the same as example 4, DMF recovery rate 90.8%.
Embodiment 7
So that " " 50%DMF aqueous solution 330g ", in 12 hours reaction time, remaining is the same as real for 40%DMF aqueous solution 370g " replacements
Apply example 4.Rufous solvent red 179 crystallize 30.8g (yield 96.2%), with standard items compared with Δ C-0.15, Δ E 0.45, by force
Degree 100.6%.
DMF removal process is the same as example 4, DMF recovery rate 90.1%.
For prominent beneficial effects of the present invention and the scope of application of the present invention, following comparative example experiment has also been carried out：
Comparative example 1
In addition to PEG-400 is not added with, remaining presses embodiment 1.Obtain orange solvent orange 60 and crystallize 23.8g (yield 88.1%), with
Standard items are compared to Δ C-0.18, Δ E 0.85, intensity 101.1%.
Comparative example 2
In addition to sodium sulfite is not added with, remaining presses embodiment 1.Obtain orange solvent orange 60 and crystallize 23.0g (yield 85.3%), with
Standard items are compared to Δ C-0.52, Δ E 2.16, intensity 102.4%.
Comparative example 3
In addition to PEG-400 is not added with, remaining presses embodiment 4.Obtain rufous solvent red 179 and crystallize 29.7g (yield 92.7%),
Δ C-0.18, Δ E 0.65, intensity 100.5% compared with standard items.
Comparative example 4
In addition to sodium sulfite is not added with, remaining presses embodiment 4.Obtain rufous solvent red 179 and crystallize 30.0g (yields
93.6%), Δ C-0.35, Δ E 0.78, intensity 101.0% compared with standard items.
Comparative example 5
In 500ml four-hole bottles, nitrogen is passed through, adds 85%DMF aqueous solution 360g, stirs lower addition sodium hydrogensulfite
0.7g, hundred 1,8- diaminonaphthalenes 15.8g (0.1mol) is rolled over, roll over hundred tetrachlorophthalic anhydride 29.2g (0.102mol), 0.8g PEG-
400.It is warming up to micro- backflow (about 104~110 DEG C) and is incubated 12 hours, sampling detection terminal, after terminal reaches, is cooled to room
Temperature, filtering, filter cake is embathed, drained at twice with 50g 20%DMF, then is embathed and drained with 60 DEG C or so hot water of 25g.Filter cake is used
To color is not descended, 105 DEG C dry for 60 DEG C or so hot washes.Red solvent of red 135 crystallization 32.7g (yield 80.1%) is obtained, with mark
Quasi- condition is than Δ C-0.67, Δ E 1.86, intensity 98.8%.
Embodiment described above is only that the preferred embodiment of the present invention is described, not to the model of the present invention
Enclose and be defined, on the premise of design spirit of the present invention is not departed from, technical side of the those of ordinary skill in the art to the present invention
The various modifications and improvement that case is made, it all should fall into the protection domain of claims of the present invention determination.
Claims (10)
1. the preparation method of Yi Zhong piceneketone type solvent dyes, comprises the following steps：
(I) under blanket of nitrogen and reducing agent duplicate protection, the work of 1,8- diaminonaphthalene and phthalic anhydride in phase transfer catalyst polyethylene glycol
Under, reacted in the DMF aqueous solution under reflux temperature；
(II) to after being condensed terminal, reaction solution is cooled to room temperature, filtering, filter cake is washed with the low concentration DMF aqueous solution.
2. according to the preparation method of claim 1 Suo Shu piceneketone type solvent dyes, it is characterised in that：Also include step (III),
Female filtrate merges with washing filtrate, is distilled to recover；Less than 115 DEG C of cut is washed as next batch and used；More than 115 DEG C evaporate
The reaction medium as next batch is divided to use.
3. according to the preparation method of claim 2 Suo Shu piceneketone type solvent dyes, it is characterised in that：In step (I), 1,8-
The molar ratio of diaminonaphthalene and phthalic anhydride is 1:1~1.05.
4. according to the preparation method of any one of claim 1-3 Suo Shu piceneketone type solvent dyes, it is characterised in that：Phthalic anhydride is replaced
It is changed to 1,8- naphthalic anhydrides.
5. according to the preparation method of any one of claim 1-4 Suo Shu piceneketone type solvent dyes, it is characterised in that：Step (I)
In, described reducing agent is one or more mixing in sodium hydrogensulfite, sodium sulfite, sodium dithionite；Reducing agent
Dosage is the 3~6% of 1,8- diaminonaphthalene molal quantitys.
6. according to the preparation method of any one of claim 1-4 Suo Shu piceneketone type solvent dyes, it is characterised in that：Step (I)
In, described phase transfer catalyst polyethylene glycol, specially PEG-400 or PEG-600.
7. according to the preparation method of any one of claim 1-4 Suo Shu piceneketone type solvent dyes, it is characterised in that：Step (I)
In, the dosage of described phase transfer catalyst is the 2~8% of 1,8- diaminonaphthalene weight.
8. according to the preparation method of any one of claim 1-3 Suo Shu piceneketone type solvent dyes, it is characterised in that：Step (I)
In, described DMF aqueous solution mass concentration is 60~90%.
9. according to the preparation method of claim 4 Suo Shu piceneketone type solvent dyes, it is characterised in that：It is described in step (I)
DMF aqueous solution mass concentration is 40~70%.
10. according to the preparation method of any one of claim 1-4 Suo Shu piceneketone type solvent dyes, it is characterised in that：Step
(II) in, described low concentration DMF aqueous solution mass concentration is 10~30%.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108047753A (en) * | 2017-12-26 | 2018-05-18 | 江苏道博化工有限公司 | The synthetic method of red naphthalene nucleus ketone dyes |
| 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 |
| CN114958028A (en) * | 2022-07-16 | 2022-08-30 | 安徽清科瑞洁新材料有限公司 | Synthetic method of solvent red 179 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108047753A (en) * | 2017-12-26 | 2018-05-18 | 江苏道博化工有限公司 | The synthetic method of red naphthalene nucleus ketone dyes |
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| CN114958028A (en) * | 2022-07-16 | 2022-08-30 | 安徽清科瑞洁新材料有限公司 | Synthetic method of solvent red 179 |
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