CN107474053B - The preparation method of Yi Zhong piceneketone type solvent dye - Google Patents
The preparation method of Yi Zhong piceneketone type solvent dye Download PDFInfo
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- CN107474053B CN107474053B CN201710748242.2A CN201710748242A CN107474053B CN 107474053 B CN107474053 B CN 107474053B CN 201710748242 A CN201710748242 A CN 201710748242A CN 107474053 B CN107474053 B CN 107474053B
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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)
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Abstract
The invention discloses the preparation methods of Yi Zhong piceneketone type solvent dye; the following steps are included: under (I) nitrogen atmosphere and reducing agent duplicate protection; 1; 8- diaminonaphthalene and phthalic anhydride (or 1; 8- naphthalic anhydride) under the action of phase transfer catalyst polyethylene glycol, it is reacted under reflux temperature in DMF aqueous solution；(II) to after being condensed terminal, reaction solution is cooled to room temperature, and filtering washs filter cake with low concentration DMF aqueous solution.Related dyestuff is specially solvent orange 60 (C.I.564100) and solvent red 179 (C.I.564150).Under reducing agent and the duplicate protection of nitrogen atmosphere; by means of phase transfer catalyst; target product is generated in high conversion rate in DMF- water mixed solvent; the dyestuff of high-quality is obtained through simple separation; and the solvent recovery of 90% or more (in terms of DMF) can be used, be a kind of environment-friendly preparation method thereof.
Description
Technical field
The present invention relates to dyestuff preparation process fields, more particularly to the green preparation side of Yi Zhong piceneketone type solvent dye
Method.
Background technique
The Representative Cultivars of piceneketone type solvent dye are mainly solvent orange 60, solvent of red 135, solvent red 179, synthesis technology
It is roughly divided into Aqueous phase and solvent method two major classes.The product quality of solvent method is relatively preferable, but higher cost；The product of Aqueous phase
Cost is relatively low, but quality relative mistake, and material nodeless mesh is not received by the market." Aqueous phase " herein is not in absolute sense
Aqueous phase, generally referred to as solvent content 20% hereinafter, and solvent is not recycled, while Aqueous phase technique is logical
The acid for being often used 5~10% makees catalyst, corrodes to equipment more serious.
CN100413928C discloses a kind of production technology that solvent red 179 is produced using glacial acetic acid as solvent.1,8- naphthalene anhydride
With 1,8- naphthylenediamine in 10-15 times of glacial acetic acid of its weight summation, in the presence of appropriate flower king's auxiliary agent A -60, in 110-116
DEG C reflux 10-15 hour, 1,8- naphthalene anhydride and 1, the molar ratio of 8- naphthylenediamine was 1:1.01, and after reaction, cooling is filtered, from
The heart, filter cake washing drying, female filtrate are distilled to recover 105-115 DEG C of fraction and are recycled.The process recovery ratio 95.5%, gained
Product quality is preferable.But the technique has the following disadvantages: first is that glacial acetic acid makees solvent, severe corrosion to equipment；Second is that in filter cake
Remaining acetic acid is difficult to recycle, and waste water COD is very high.In general, which is not belonging to friendly process.
US5830931 discloses a kind of synthesis technology of fused ring compound.The technique belongs to Aqueous phase, in an 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
It answers.Technical solution are as follows: 50-150 DEG C of reaction temperature, suitable temperature is 90-140 DEG C, is generally carried out under normal pressure, but can also be with
It is carried out in negative pressure or with pressure.Negative pressure is 1-20 bars, and 105-160 DEG C of reaction temperature is suitable for reaction with pressure.It is 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；It 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.Reaction medium is suitable for the water containing medium-weight 50-85%, 0.5-20% hydrophile
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 following disadvantages: 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 is that be added
About 5~8% hydroaropic substance, is neither recycled, and does not have mother liquid recycle, be will be present in waste water, is caused COD very high.It is overall
For, which is also not belonging to friendly process.
US5530130 discloses the preparation method of Yi Zhong piceneketone dyestuff.The technique belongs to solvent method, technical solution are as follows: adopts
Solvent have chlorobenzene, o-dichlorohenzene, trichloro-benzenes, dimethylbenzene, DMF, N-Methyl pyrrolidone, acetic acid, propionic acid, phenol, cresols,
Phenoxyethanol, ethylene glycol and its single or double alkyl ether, methanol, ethyl alcohol, 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 usage is big, the methanol that should be distilled to recover in phenol, high temperature rectifying again
Phenol is recycled, production cost is higher；Process recovery ratio is relatively slightly lower.
CN101565556B discloses a kind of preparation method of solvent orange 60.The technique belongs to Aqueous phase, by the amount of substance
Than be 1~5% for 1:1 phthalic anhydride and 1,8- naphthylenediamine and mass concentration hydrochloric acid solution, 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- naphthylenediamine；
Polar organic solvent dosage is the 1-50% of reaction medium total amount；The catalyst amount be reaction medium total amount 0.01~
2%.Polar organic solvent includes ethyl alcohol, acetic acid, DMF, N-Methyl pyrrolidone, and the ion inactive catalyst used is nonyl
Phenol polyethenoxy ether.The technique has the following disadvantages: first is that the hydrochloric acid solution of low concentration is chronically at high temperature reflux state, to setting
Standby seriously corroded；Second is that nonylphenol polyoxyethylene ether (NPEO) has biggish harm to environment；Third is that the waste water containing organic solvent
COD is very high, and wastewater flow rate is big, does not also recycle, which is also not belonging to friendly process.
Summary of the invention
The technical problem to be solved in the present invention is to provide the environment-friendly preparation method thereofs of Yi Zhong piceneketone type solvent dye.
This invention Suo is related to piceneketone type solvent dye: 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 piceneketone type solvent dye disclosed by the invention, step includes:
(I) under nitrogen atmosphere and reducing agent duplicate protection, 1,8- diaminonaphthalene and phthalic anhydride (or 1,8- naphthalic anhydride),
Under the action 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, and filtering washs filter cake with low concentration DMF aqueous solution；
(III) female filtrate merges with washing filtrate, is distilled to recover.115 DEG C of fractions below are washed as next batch and are used；
The reaction medium that 115 DEG C or more of fraction is used as next batch is used.
Wherein, reducing agent described in step (I) are as follows: sodium hydrogensulfite, sodium sulfite, it is a kind of in sodium dithionite or
A variety of mixing, dosage are the 3~6% of 1,8- diaminonaphthalene molal quantity.
Phase transfer catalyst polyethylene glycol described in step (I) specifically: 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 concentration of 100~115 DEG C of fractions is about 10~35% described in step (III).
The DMF mass concentration of 115 DEG C or more fractions described in step (III) is 75~85%.
The present invention has been provided in particular in the green system that high-quality solvent orange 60 and solvent red 179 are synthesized under a kind of non-acid catalysis
Preparation Method.The innovation of preparation process of the invention is: acidic catalyst is not used, it is corrosion-free to equipment；It matches
Phase transfer catalyst polyethylene glycol guarantees the high conversion of reaction；Reducing agent and nitrogen atmosphere whole process protection 1,8- diaminonaphthalene are complete
Prevent the possibility that its high temperature is oxidized entirely, reaction conversion ratio is high, superior product quality.
Ortho position aromatic diamines and aromatic anhydride dehydration condensation Sheng Cheng piceneketone compound, are both needed to acid under normal circumstances
Matter makees catalyst, has used acidic catalyst (US5530130 bar none in the pertinent literature of background technique description section
Middle phenol is also similarly), so those skilled in the art due to conventional inertial thinking, are difficult to expect that acidic catalyst can be abandoned.
In fact, the present inventor is inadvertently had found under polyethylene glycol and phase transfer catalyst synergistic effect, it can
To complete the synthesis of solvent orange 60 and solvent red 179 well.And synthesis of the same technique for solvent of red 135 is then undesirable
(see comparative example 5) illustrates that Gong Yi Dui piceneketone type solvent dye of the invention does not have universality.DMF is alkalescence substance, therefore,
Without using acidic catalyst, the preparation for solvent orange 60 and solvent red 179 is that a Chao Chu piceneketone type solvent dye routinely closes
It is significant to the corrosive effect for reducing consersion unit and its subsidiary pipeline at the new process of method, also substantially improve working environment.
Experiment (see comparative example 1,2,3,4) of the invention confirm in 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.
Technique of the invention is both different from Aqueous phase, also different from solvent method, can be referred to as " half solvent method ", react
Journey can be described as closer to solvent method: 1,8- diaminonaphthalene and phthalic anhydride (or 1,8- naphthalic anhydride) are at a reflux temperature
In 40-90%DMF aqueous solution, there is certain solubility, and solubility very little, phase transfer catalyst are poly- under this condition for product
Ethylene glycol plays the role 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, 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, outstanding advantage is the present invention:
(1) this technique is to equipment no corrosion；
(2) product has crystallization, high-quality, and cost performance is high, meets the requirement of high-end market.
(3) solvent recovery applies (rate of recovery > 90%), is friendly process.
It is described further below with reference to the preparation method of specific embodiment Dui this Fa Ming piceneketone type solvent dye.
Specific embodiment
In the following examples, the experimental methods for specific conditions are not specified, usually 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 bottle, it is passed through nitrogen, 80%DMF aqueous solution 230g is added, is added with stirring sodium sulfite
0.8g rolls over hundred 1,8- diaminonaphthalene 15.8g (0.1mol), rolls over hundred phthalic anhydride 15.1g (0.102mol), 0.6g PEG-400.
It is warming up to micro- reflux (about 108~115 DEG C) and keeps the temperature 10 hours, sample detection terminal is cooled to room temperature, mistake after terminal reaches
Filter, filter cake is embathed in two times with 50g 30%DMF, is drained, then is embathed and drained with 60 DEG C of 25g or so hot water, and filtrate merges wait return
It receives.Filter cake is washed with 60 DEG C or so hot water to color is not descended again, and 105 DEG C dry.It obtains bright orange solvent orange 60 and crystallizes 25.9g (yield
95.9%), coloured light, intensity Δ C 0.14, Δ E 0.42, intensity 99.8% compared with standard items.
It recycles DMF: in four-hole boiling flask of the 500ml equipped with thermometer, filled column, condenser and receiving bottle, being added wait return
DMF filtrate is received, 100-115 DEG C of fraction 70g (DMF concentration of aqueous solution is 31.3%), 115 DEG C or more fraction 195g are collected in distillation
(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.It obtains bright orange solvent orange 60 and crystallizes 25.7g (yield
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 bottle, it is passed through nitrogen, 70%DMF aqueous solution 270g is added, is added with stirring sodium dithionite
0.65g rolls over hundred 1,8- diaminonaphthalene 15.8g (0.1mol), rolls over hundred phthalic anhydride 15.1g (0.102mol), 0.8g PEG-
400.It is warming up to micro- reflux (about 105~112 DEG C) and keeps the temperature 12 hours, sample detection terminal after terminal reaches, is cooled to room
Temperature, filtering, filter cake is embathed in two times with 50g 20%DMF, then washed once with 60 DEG C of 25g or so hot water, is drained, and filtrate is closed
And it is to be recycled.Filter cake is washed with 60 DEG C or so hot water to color is not descended, and 103 DEG C dry.It obtains bright orange solvent orange 60 and crystallizes 25.4g
(yield 94.1%), Δ C 0.12, Δ E 0.35, intensity 99.6% compared with standard items.
Recycling DMF: in 500ml flask, being added DMF filtrate to be recycled, distills, and collects 100~115 DEG C of fraction 100g
(DMF concentration of aqueous solution is 26.2%), 115 DEG C or more fraction 188g (DMF concentration of aqueous solution is 82.6%), DMF recovery rate is about
91.2%.
Embodiment 4
In 500ml four-hole bottle, it is passed through nitrogen, 50%DMF aqueous solution 330g is added, is added with stirring sodium hydrogensulfite
0.7g rolls over hundred 1,8- diaminonaphthalene 15.8g (0.1mol), rolls over hundred 1,8- naphthalic anhydride 20.0g (0.101mol),
0.8g PEG-400.It is warming up to micro- reflux (about 104~110 DEG C) and keeps the temperature 8 hours, sample detection terminal, after terminal reaches, drop
It warming to room temperature, filters, filter cake is embathed in two times with 50g 20%DMF, is drained, then is embathed and drained with 60 DEG C of 25g or so hot water,
Filtrate merges to be recycled.Filter cake is washed with 60 DEG C or so hot water to color is not descended, and 105 DEG C dry.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.
It recycles DMF: in four-hole boiling flask of the 500ml equipped with thermometer, filled column, condenser and receiving bottle, being added wait return
The distillation of DMF filtrate is received, 98-115 DEG C of fraction 226g (DMF concentration of aqueous solution is 23.3%), 115 DEG C or more fraction 130g are collected
(DMF concentration of aqueous solution is 81.4%), DMF recovery rate 90.6%.
Embodiment 5
With " sodium sulfite 0.8g " replacement " sodium hydrogensulfite 0.7g ", remaining is the same as embodiment 4.Obtain rufous solvent red 179
It crystallizes 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.It obtains rufous solvent red 179 and crystallizes 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
With " 40%DMF aqueous solution 370g " replacement " 50%DMF aqueous solution 330g ", the reaction time 12 hours, remaining was the same as real
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 invention, following comparative example test has also been carried out:
Comparative example 1
In addition to PEG-400 is not added, remaining presses embodiment 1.60 crystallization 23.8g (yield 88.1%) of orange solvent orange is obtained, with
Standard items compare Δ C-0.18, Δ E 0.85, intensity 101.1%.
Comparative example 2
In addition to sodium sulfite is not added, remaining presses embodiment 1.60 crystallization 23.0g (yield 85.3%) of orange solvent orange is obtained, with
Standard items compare Δ C-0.52, Δ E 2.16, intensity 102.4%.
Comparative example 3
In addition to PEG-400 is not added, remaining presses embodiment 4.It obtains rufous solvent red 179 and crystallizes 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, remaining presses embodiment 4.It obtains rufous solvent red 179 and crystallizes 30.0g (yield
93.6%), Δ C-0.35, Δ E 0.78, intensity 101.0% compared with standard items.
Comparative example 5
In 500ml four-hole bottle, it is passed through nitrogen, 85%DMF aqueous solution 360g is added, is added with stirring sodium hydrogensulfite
0.7g rolls over hundred 1,8- diaminonaphthalene 15.8g (0.1mol), rolls over hundred tetrachlorophthalic anhydride 29.2g (0.102mol), 0.8g PEG-
400.It is warming up to micro- reflux (about 104~110 DEG C) and keeps the temperature 12 hours, sample detection terminal is cooled to room after terminal reaches
Temperature, filtering, filter cake is embathed in two times with 50g 20%DMF, is drained, then is embathed and drained with 60 DEG C of 25g or so hot water.Filter cake is used
60 DEG C or so hot water are washed to color is not descended, and 105 DEG C dry.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 only describe the preferred embodiments of the invention, not to model of the invention
It encloses and is defined, without departing from the spirit of the design of the present invention, those of ordinary skill in the art are to technical side of the invention
The various changes and improvements that case is made should all be fallen into the protection scope that claims of the present invention determines.
Claims (9)
1. the preparation method of Yi Zhong piceneketone type solvent dye, comprising the following steps:
(I) under nitrogen atmosphere and reducing agent duplicate protection, the work of 1,8- diaminonaphthalene and phthalic anhydride in phase transfer catalyst polyethylene glycol
Under, reacted under reflux temperature in DMF aqueous solution；
(II) to after being condensed terminal, reaction solution is cooled to room temperature, and filtering washs filter cake with low concentration DMF aqueous solution；Described is low
Concentration DMF aqueous solution mass concentration is 10~30%.
2. according to the preparation method of claim 1 Suo Shu piceneketone type solvent dye, it is characterised in that: it further include step (III),
Female filtrate merges with washing filtrate, is distilled to recover；115 DEG C of fractions below are washed as next batch and are used；115 DEG C or more 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 dye, it is characterised in that: in step (I), 1,8-
The molar ratio of diaminonaphthalene and phthalic anhydride is 1:1~1.05.
4. the preparation method of the piceneketone type solvent dye of -3 any Xiang Suoshu according to claim 1, it is characterised in that: replace phthalic anhydride
It is changed to 1,8- naphthalic anhydride.
5. the preparation method of the piceneketone type solvent dye of -4 any Xiang Suoshu according to claim 1, it is characterised in that: step (I)
In, the reducing agent is one of sodium hydrogensulfite, sodium sulfite, sodium dithionite or a variety of mixing；Reducing agent
Dosage is the 3~6% of 1,8- diaminonaphthalene molal quantity.
6. the preparation method of the piceneketone type solvent dye of -4 any Xiang Suoshu according to claim 1, it is characterised in that: step (I)
In, the phase transfer catalyst polyethylene glycol, specially PEG-400 or PEG-600.
7. the preparation method of the piceneketone type solvent dye of -4 any Xiang Suoshu according to claim 1, it is characterised in that: step (I)
In, the dosage of the phase transfer catalyst is the 2~8% of 1,8- diaminonaphthalene weight.
8. the preparation method of the piceneketone type solvent dye of -3 any Xiang Suoshu according to claim 1, it is characterised in that: step (I)
In, the DMF aqueous solution mass concentration is 60~90%.
9. according to the preparation method of claim 4 Suo Shu piceneketone type solvent dye, it is characterised in that: described in step (I)
DMF aqueous solution mass concentration is 40~70%.
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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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|---|---|---|---|---|
| JPS5285218A (en) * | 1976-01-08 | 1977-07-15 | Yamamoto Kagaku Gosei Kk | Process for manufacture of perinone series dyestuffs |
| US5530130A (en) * | 1993-08-19 | 1996-06-25 | Bayer Aktiengesellschaft | Phthaloperinone dyestuffs |
| US5830931A (en) * | 1995-12-22 | 1998-11-03 | Bayer Aktiengesellschaft | Process for the preparation of polycyclic compounds |
| CN1919931A (en) * | 2006-08-25 | 2007-02-28 | 南通龙翔化工有限公司 | Preparation technique of solvent red 179 |
| CN101565556A (en) * | 2009-03-23 | 2009-10-28 | 南通龙翔化工有限公司 | Preparation method for solvent orange 60 |
-
2017
- 2017-08-28 CN CN201710748242.2A patent/CN107474053B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5285218A (en) * | 1976-01-08 | 1977-07-15 | Yamamoto Kagaku Gosei Kk | Process for manufacture of perinone series dyestuffs |
| US5530130A (en) * | 1993-08-19 | 1996-06-25 | Bayer Aktiengesellschaft | Phthaloperinone dyestuffs |
| US5830931A (en) * | 1995-12-22 | 1998-11-03 | Bayer Aktiengesellschaft | Process for the preparation of polycyclic compounds |
| CN1919931A (en) * | 2006-08-25 | 2007-02-28 | 南通龙翔化工有限公司 | Preparation technique of solvent red 179 |
| CN101565556A (en) * | 2009-03-23 | 2009-10-28 | 南通龙翔化工有限公司 | Preparation method for solvent orange 60 |
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