CN106748810A - A kind of processing method of disperse dyes intermediate - Google Patents
A kind of processing method of disperse dyes intermediate Download PDFInfo
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- CN106748810A CN106748810A CN201611254254.1A CN201611254254A CN106748810A CN 106748810 A CN106748810 A CN 106748810A CN 201611254254 A CN201611254254 A CN 201611254254A CN 106748810 A CN106748810 A CN 106748810A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
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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
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
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Abstract
A kind of processing method of disperse dyes intermediate, it is characterised in that the described method comprises the following steps：The disperse dyes intermediate is mixed with water and sour agent, is distilled.After the disperse dyes intermediate is processed through the inventive method, chlorobenzene and chloromethane benzene content meet the limitation to dyestuff on fabric in Oeko Tex Standard100 in synthesized dyestuff chemistry product, the characteristics of with environmental protection.
Description
Technical field
The present invention relates to a kind of processing method of disperse dyes intermediate.
Background technology
Now, Green Textiles and environmental protection type dye have turned into the emphasis of textile industry and dye industry development, environment-friendly type
Dyestuff is one of essential condition of guarantee Green Textiles.
Environmental protection type dye is also needed full in addition to possessing necessary use technique applicability, application performance and fastness ability
The requirement that toe ring is guaranteed the quality.Environment-friendly quality has its tangible index and content, and on the one hand the structure with dyestuff in itself is relevant, belongs to
Internal cause.Specifically include：It is not that explicitly provided can the decomposition under given conditions of German Government and the European Community discharges carcinogenic fragrance
The azo dyes of amine；It is not irritative dye；It is not carcinogenicity dyestuff；It is not acute toxicity dyestuff；The content of contained heavy metal
Below limits value.The content of another aspect is external, belongs to external cause, and the factor of generation is a lot, as produced by side reaction, not
The raw material of reaction, additional additive and auxiliary agent etc., specifically include：Without environmental hormone；Change without meeting generation environment pollution
Learn material, such as VOC, containing chlorine carrier；Without variability chemical combination material and persistence organic pollutant；No
Containing confined agricultural chemicals.The environment-friendly quality index of dyestuff from the beginning of the seventies, it has been proposed that and constantly improve, but dye product is past so far
Toward not reaching the requirement in market, still current western countries, to the technology barriers of dyestuff producer, and are not also to influence me for this
One of factor of state's quality of textile products.
Current most of dyestuffs or dyestuff intermediate containing chlorobenzene and severe overweight containing chlorotoluene, after dyeing on fabric
Chlorobenzene and chloromethane benzene content do not meet the limitation requirement of Oeko-Tex Standard100.
The content of the invention
It is chlorobenzene and chlorotoluene content overproof in solving the problems, such as dyestuff or dyestuff intermediate, the present invention provides a kind of dispersion
The processing method of dyestuff intermediate, after the disperse dyes intermediate is processed through the inventive method, synthesized disperse dyes are produced
Product are used not only for after dyeing the limitation that the chlorobenzene of dyestuff and the content of chlorotoluene on fabric meet Oeko-Tex Standard100
It is required that, the content of disperse dyes product middle chlorobenzene and chlorotoluene in itself also reaches Oeko-Tex Standard100 to being contaminated on fabric
The limitation requirement of chlorobenzene and chlorotoluene in material.
The present invention is achieved through the following technical solutions：
The present invention provides a kind of processing method of disperse dyes intermediate, it is characterised in that methods described includes following step
Suddenly：The disperse dyes intermediate is mixed with water and sour agent, is then distilled.
Preferably, the disperse dyes intermediate includes being selected from paranitroanilinum, the chloro- 4- nitroanilines of 2-, 2- cyano group -4-
Nitroaniline, 2- nitro -4- chloroanilines, 3,4- dichloroanilines, 2,4- dinitroanilines, 2,6- Dichloro-4-nitroanilines, 2,6-
One or more in two bromo- 4- nitroanilines, 2 cyano 4 nitro 6 bromo aniline, 2- cyano group -4- nitro -6- chloroanilines.
Preferably, the sour agent is included selected from one or more in hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid；Preferably,
The sour agent be sulfuric acid, hydrochloric acid in one or more；Preferably, the sour agent is 98% sulfuric acid or 30% hydrochloric acid.
Preferably, the disperse dyes intermediate and the mol ratio of sour agent are 1:1~6, preferably 1:1.5~3；It is preferred that
The weight ratio of ground, the disperse dyes intermediate and water is 1:1~15, preferably 1:2~10.
Preferably, the distillation is air-distillation or vacuum distillation；Preferably, described distillation is that the moisture amount of steaming is to add water
The 10%~50% of amount.
Preferably, following process step is also included after distilation steps：Cooling and/or addition alkaline agent.
Preferably, to adding auxiliary agent in disperse dyes intermediate, water, the mixed system of sour agent；
Preferably, the auxiliary agent is selected from one or more in dispersant, dyeing auxiliaries, surfactant, bactericide；It is preferred that
Ground, the dispersant is selected from naphthalene sulfonic formaldehyde condensation compound, lignosulfonates (lignin 83A, lignin 85A) or glauber salt
One or more in (sodium sulphate)；Preferably, the surfactant is selected from AEO, polyalcohol, sulfuric acid
Change one or more in castor oil；Preferably, the auxiliary agent is selected from naphthalene sulfonic acid-formaldehyde condensation product (dispersing agent NNO), methyl naphthalene
Sulfonic formaldehyde condensation compound (Dispersant MF), benzyl naphthalene sulfonic acid-formaldehyde condensation product (dispersing agent CNF), lignin 83A, lignin 85A,
One or more in peregal, glauber salt；Preferably, the auxiliary agent includes MF, lignin.
The present invention also provides a kind of disperse dyes intermediate, it is characterised in that the disperse dyes intermediate is using above-mentioned
Processing method processed；Preferably, the disperse dyes intermediate includes being selected from paranitroanilinum, the chloro- 4- nitros of 2-
Aniline, 2 cyano 4 nitro aniline, 2- nitro -4- chloroanilines, 3,4- dichloroanilines, 2,4- dinitroanilines, 2,6- bis- are chloro-
The bromo- 4- nitroanilines of 4- nitroanilines, 2,6- bis-, 2 cyano 4 nitro 6 bromo aniline, 2- cyano group -4- nitro -6- chloroanilines
In one or more.
The present invention also provides a kind of preparation method of disperse dyes, it is characterised in that including disperse dyes intermediate is pressed
The step of being processed according to above-mentioned processing method；Preferably, the disperse dyes are selected from disperse red 74, disperse yellow 121, dispersion
The related dye that orange 80, disperse orange 288, disperse orange 44, Red 167, Red-1 200 53 etc. are synthesized by above-mentioned dyestuff intermediate,
The dyestuff intermediate is selected from paranitroanilinum, the chloro- 4- nitroanilines of 2-, 2 cyano 4 nitro aniline, 2- nitro -4- chlorobenzenes
The bromo- 4- nitroanilines of amine, 3,4- dichloroanilines, 2,4- dinitroanilines, 2,6- Dichloro-4-nitroanilines, 2,6- bis-, 2- cyanogen
One or more in base -4- nitro -6- bromanilines, 2- cyano group -4- nitro -6- chloroanilines.
The present invention a kind of disperse dyes are also provided, selected from disperse red 74, disperse yellow 121, disperse orange 80, disperse orange 288, point
Dissipate orange 44, Red 167, Red-1 200 53, it is characterised in that the preparation method of the disperse dyes is included in disperse dyes
The step of mesosome is processed according to above-mentioned processing method, the disperse dyes intermediate is selected from paranitroanilinum, the chloro- 4- of 2-
Nitroaniline, 2 cyano 4 nitro aniline, 2- nitro -4- chloroanilines, 3,4- dichloroanilines, 2,4- dinitroanilines, 2,6- bis-
The bromo- 4- nitroanilines of chloro- 4- nitroanilines, 2,6- bis-, 2 cyano 4 nitro 6 bromo aniline, 2- cyano group -4- nitro -6- chlorobenzenes
One or more in amine.
The beneficial effects of the invention are as follows：After the disperse dyes intermediate is processed through the inventive method, thus disperse dyes
The disperse dyes product of intermediate synthesis is used not only for after dyeing the chlorobenzene of dyestuff and the content of chlorotoluene on fabric and meets Oeko-
The limitation requirement of Tex Standard100, the content of disperse dyes product middle chlorobenzene and chlorotoluene in itself also reaches Oeko-Tex
Standard100 is to the limitation requirement of chlorobenzene and chlorotoluene in dyestuff on fabric, the advantage with environmental protection.
Wherein, the content of the chlorobenzene and chlorotoluene be 2- chlorotoluenes, 3- chlorotoluenes, 4- chlorotoluenes, 1,3- dichloro-benzenes, 1,
4- dichloro-benzenes, 1,2- dichloro-benzenes, 2,4 di chloro toluene, 2,5- dichlorotoleune, 2,6- dichlorotoleune, 1,3,5- trichloro-benzenes, 3,4-
Dichlorotoleune, 2,3 dichloro toluene, 1,2,4- trichloro-benzenes, 1,2,3- trichloro-benzenes, 1,2,3,5- tetrachlorobenzenes, 1,2,4,5- tetrachloros
Benzene, 1,2,3,4- tetrachlorobenzenes, toluene tetrachloride, pentachlorobenzene, 2,3,4,5,6- toluene pentachlorides, hexachloro-benzene, 2,3,6- benzotrichlorides, 2,
The total content of 4,5- benzotrichlorides and monochloro-benzene.
Specific embodiment
With reference to specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in
This.
Paranitroanilinum, 3,4- dichloroanilines employed in following embodiments and comparative example, chloro- 4 nitroanilines of 2- are equal
It is commercially available product.
Embodiment 1：Intermediate processes the C.I. disperse reds 74 of synthesis through the inventive method
Water 240g is added in the four-hole boiling flask of 500ml, paranitroanilinum 30g (percentage amount) and 98% sulfuric acid is added
26g, intensification air-distillation steams cut 45g.
Distillation terminates, on the rocks that the reaction system is cooled into less than 5 DEG C, then controls less than 5 DEG C dropwise addition natrium nitrosums molten
Liquid carries out diazo-reaction, and completion of dropwise addition insulation reaction obtains final product diazo liquid in 2 hours, average to being added in the diazo liquid that reaction is obtained
Plus 0.5g, urea 0.5g and appropriate ice, then to N is slowly added dropwise in the system, N- diacetyl oxy ethyl aniline is coupled,
Completion of dropping, is incubated 3 hours, then heats to 60 DEG C and is incubated 2 hours, and suction filtration, washing obtain final product disperse red 74.
The diazo liquid prepared by the above method can also be used to synthesize disperse yellow 121, disperse orange 80 etc..
Comparative example 1：The C.I. disperse reds 74 of the unprocessed synthesis of intermediate
It is disperse dyes intermediate with the paranitroanilinum processed without the inventive method, according to the side that embodiment 1 is recorded
Method, synthesis C.I. disperse reds 74.
Embodiment 2：Intermediate processes the C.I. disperse oranges 288 of synthesis through the inventive method
Water 240g is added in the four-hole boiling flask of 500ml, paranitroanilinum 30g (percentage amount) and 98% sulfuric acid is added
60g, intensification air-distillation steams cut 25g.
Distillation terminates, on the rocks that the reaction system is cooled into less than 5 DEG C, and then controlling less than 5 DEG C is added dropwise nitrosyl sulfuric acid
Diazo-reaction is carried out, completion of dropwise addition insulation reaction obtains final product diazo liquid in 2 hours；Above-mentioned diazo liquid is diluted in frozen water, is controlled
15%, then add peregal 1g, urea 0.5g and a certain amount of N- cyanoethyls-Phenhenzamine carries out idol to acid number
Close, 20 DEG C are incubated 3 hours, 30 DEG C are incubated 3 hours, 40 DEG C are incubated 3 hours, be finally warming up to 75 DEG C and be incubated 2 hours, suction filtration, wash
Wash and obtain final product disperse orange 288.
Comparative example 2：The C.I. disperse oranges 288 of the unprocessed synthesis of intermediate
It is disperse dyes intermediate with the paranitroanilinum processed without the inventive method, according to the side that embodiment 2 is recorded
Method, synthesizes disperse orange 288.
Embodiment 3：Intermediate processes the C.I. disperse oranges 44 of synthesis through the inventive method
Water 100g is added in the four-hole boiling flask of 500ml, paranitroanilinum 30g (percentage amount) and 30% hydrochloric acid is added
55g, intensification air-distillation steams cut 35g.
Distillation terminates, and the reaction system is cooled into 15 DEG C, and the liquor natrii hypochloritis 130g that content is 10%, insulation is added dropwise
Reaction 0.5h, sampling detection terminal, treats that terminal is arrived, if terminal less than, continue that liquor natrii hypochloritis is added dropwise, until terminal is arrived,
Filtering and washing obtains the chloro- 4- nitroanilines of 2-.
The chloro- 4- nitroanilines of 2- obtained above are first beaten in frozen water system, are subsequently adding a certain amount of hydrochloric acid,
Sodium nitrite solution is added dropwise then at 0 DEG C or so carries out diazo-reaction, and reaction terminates a certain amount of average to being added in the system
It is subject to and urea, N is finally added dropwise inside, N- dicyanoethyl-aniline solution is coupled, completion of dropwise addition, insulation reaction 2 hours,
Then heat to 60 DEG C and be incubated 2 hours, suction filtration, washing obtain final product disperse orange 44.
The diazo liquid prepared by the above method can also be used to synthesize Red 167 etc..
Comparative example 3：The C.I. disperse oranges 44 of the unprocessed synthesis of intermediate
It is disperse dyes intermediate with the paranitroanilinum processed without the inventive method, according to the side that embodiment 3 is recorded
Method, synthesis C.I. disperse oranges 44.
Embodiment 4：Intermediate processes the C.I. Red-1 200s 53 of synthesis through the inventive method
Water 150g is added in the four-hole boiling flask of 250ml, the hydrochloric acid 30g of 3,4-DCA 40g and 30% is added, risen
Normal temperature and pressure distills, and steams cut 30g.
Distillation terminates, and cools the temperature to 80 DEG C, is then slowly dropped into ammonium thiocyanate solution, and completion of dropping is to slowly warm up to
95 DEG C of insulation reactions, reaction terminates, and is cooled to 80 DEG C, and suction filtration, washing obtain final product 3,4- dichlorophenyl thiocarbamides.
3,4- dichlorophenyl thiocarbamides in sulfuric acid system with bromine as catalyst closed loop synthesize 2- amino -5,6 (6,7) -
Dichlorobenzothiazole, then 0 DEG C or so be added dropwise nitrosyl sulfuric acid carry out diazotising, finally in frozen water system with N- ethyls-
N- cyanoethyl anilines be coupled and obtain the filter cake of Red-1 200 53.
The 3,4- dichlorophenyl thiocarbamides prepared by the above method can also be used to synthesize Red-1 200 53:1 etc..
Comparative example 4：The C.I. Red-1 200s 53 of the unprocessed synthesis of intermediate
It is disperse dyes intermediate with the 3,4-DCA processed without the inventive method, is recorded according to embodiment 4
Method, synthesis C.I. Red-1 200s 53.
Comparative example 5：
3,4- dichloroanilines are carried out with the processing method according to the embodiment 12 in specification table 1 in CN104725897A
Treatment, according to the method that embodiment 4 is recorded, synthesis C.I. Red-1 200s 53.
Embodiment 5：
Water 250g is added in the four-hole boiling flask of 500ml, 2- chloro- 4 nitroaniline 50g (percentage amount) and 30% is added
Hydrochloric acid 80g, intensification air-distillation steams cut 42g；Distillation terminates slow cooling analysis of material, treats that temperature is down to less than 35 DEG C, suction filtration
Chloro- 4 nitroanilines of environment-friendly type 2- are washed to obtain, mother liquor is collected and is applied to next group.
With reference to the method for GB/T24167-2009 (solvent extraction, gas chromatograph-mass spectrometer (GC-MS) GC-MS), to synthesized
Disperse dyes product in the content of chlorobenzene and chlorotoluene be measured.Result is listed in the table below.
Note：ND=is not detected, detection limit=0.1ppm, hundred a ten thousandths of ppm==mg/kg=mg/kgs
After can be seen that disperse dyes intermediate through disposal methods of the invention by upper table data, synthesized divides
The content for dissipating chlorobenzene and chlorotoluene in dye product has been reached in Oeko-Tex Standard100 in dye for fabrics after dyeing
The limitation requirement of chlorobenzene and chloride toluene level, the advantage with environmental protection.
The preferred embodiment of the present invention described in detail above, but, the present invention is not limited in above-mentioned implementation method
Detail, in range of the technology design of the invention, various simple variants can be carried out to technical scheme, this
Plant simple variant and belong to protection scope of the present invention.
Claims (10)
1. a kind of processing method of disperse dyes intermediate, it is characterised in that the described method comprises the following steps：By the dispersion
Dyestuff intermediate mixes with water and sour agent, is then distilled.
2. processing method according to claim 1, it is characterised in that the disperse dyes intermediate includes being selected to nitro
The chloro- 4- nitroanilines of aniline, 2-, 2 cyano 4 nitro aniline, 2- nitro -4- chloroanilines, 3,4- dichloroanilines, 2,4- dinitros
The bromo- 4- nitroanilines of base aniline, 2,6- Dichloro-4-nitroanilines, 2,6- bis-, 2 cyano 4 nitro 6 bromo aniline, 2- cyano group-
One or more in 4- nitro -6- chloroanilines.
3. processing method according to claim 1 and 2, it is characterised in that the sour agent includes being selected from hydrochloric acid, sulfuric acid, phosphorus
Acid, one or more in acetic acid；Preferably, the sour agent be sulfuric acid, hydrochloric acid in one or more；Preferably, institute
Sour agent is stated for 98% sulfuric acid or 30% hydrochloric acid.
4. the processing method according to any one of claim 1-3, it is characterised in that the disperse dyes intermediate and acid
The mol ratio of agent is 1:1~6, preferably 1:1.5~3；Preferably, the weight ratio of the disperse dyes intermediate and water is 1:1
~15, preferably 1:2~10.
5. the processing method according to any one of claim 1-4, it is characterised in that the distillation is air-distillation or subtracts
Pressure distillation；Preferably, it is described to distill for the moisture amount of steaming is the 10%~50% of amount of water.
6. the processing method according to any one of claim 1-5, it is characterised in that also include after distilation steps with
Lower process step：Cooling and/or addition alkaline agent.
7. the processing method according to any one of claim 1-6, it is characterised in that to disperse dyes intermediate, water, acid
Auxiliary agent is added in the mixed system of agent；
Preferably, the auxiliary agent is selected from one or more in dispersant, dyeing auxiliaries, surfactant, bactericide；Preferably,
The dispersant is selected from one or more in naphthalene sulfonic formaldehyde condensation compound, lignosulfonates or glauber salt；Preferably, institute
State one or more during surfactant is selected from AEO, polyalcohol, sulfated castor oil.
8. a kind of disperse dyes intermediate, it is characterised in that the disperse dyes intermediate uses any one of claim 1-7 institute
The processing method stated is processed；Preferably, the disperse dyes intermediate includes being selected from paranitroanilinum, the chloro- 4- nitre of 2-
Base aniline, 2 cyano 4 nitro aniline, 2- nitro -4- chloroanilines, 3,4- dichloroanilines, 2,4- dinitroanilines, 2,6- bis-
The bromo- 4- nitroanilines of chloro- 4- nitroanilines, 2,6- bis-, 2 cyano 4 nitro 6 bromo aniline, 2- cyano group -4- nitro -6- chlorobenzenes
One or more in amine.
9. a kind of preparation method of disperse dyes, it is characterised in that including by disperse dyes intermediate according in claim 1-7
The step of processing method described in any one is processed；Preferably, the disperse dyes be selected from disperse red 74, disperse yellow 121,
The related dye that disperse orange 80, disperse orange 288, disperse orange 44, Red 167, Red-1 200 53 etc. are synthesized by above-mentioned dyestuff intermediate
Material, the dyestuff intermediate is selected from paranitroanilinum, the chloro- 4- nitroanilines of 2-, 2 cyano 4 nitro aniline, 2- nitro -4- chlorine
The bromo- 4- nitroanilines of aniline, 3,4- dichloroanilines, 2,4- dinitroanilines, 2,6- Dichloro-4-nitroanilines, 2,6- bis-, 2- cyanogen
One or more in base -4- nitro -6- bromanilines, 2- cyano group -4- nitro -6- chloroanilines.
10. a kind of disperse dyes, selected from disperse red 74, disperse yellow 121, disperse orange 80, disperse orange 288, disperse orange 44, disperse red
167th, Red-1 200 53, it is characterised in that the preparation method of the disperse dyes includes will according to right by disperse dyes intermediate
The step of asking the processing method any one of 1-7 to be processed, the disperse dyes intermediate is selected from paranitroanilinum, 2-
Chloro- 4- nitroanilines, 2 cyano 4 nitro aniline, 2- nitro -4- chloroanilines, 3,4- dichloroanilines, 2,4- dinitroanilines,
The bromo- 4- nitroanilines of 2,6- Dichloro-4-nitroanilines, 2,6- bis-, 2 cyano 4 nitro 6 bromo aniline, 2- cyano group -4- nitros -
One or more in 6- chloroanilines.
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| CN201611254254.1A CN106748810B (en) | 2016-12-30 | 2016-12-30 | Treatment method of disperse dye intermediate |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113527909A (en) * | 2021-07-23 | 2021-10-22 | 杭州吉华江东化工有限公司 | Synthesis process of environment-friendly dye |
| CN114316629A (en) * | 2021-12-23 | 2022-04-12 | 江苏格罗瑞化学有限公司 | Green and environment-friendly disperse dye intermediate treatment method |
| CN115651422A (en) * | 2022-10-25 | 2023-01-31 | 杭州吉华江东化工有限公司 | Synthetic method of environment-friendly heterocyclic disperse red dye |
| CN117417649A (en) * | 2023-10-12 | 2024-01-19 | 济宁阳光化学有限公司 | Environment-friendly high-performance pigment red P.R.2 and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101570648A (en) * | 2009-06-01 | 2009-11-04 | 陶国来 | Disperse red dye |
| CN104725897A (en) * | 2013-12-23 | 2015-06-24 | 浙江龙盛集团股份有限公司 | Ecological environment-friendly treatment method of dye or dye intermediate |
-
2016
- 2016-12-30 CN CN201611254254.1A patent/CN106748810B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101570648A (en) * | 2009-06-01 | 2009-11-04 | 陶国来 | Disperse red dye |
| CN104725897A (en) * | 2013-12-23 | 2015-06-24 | 浙江龙盛集团股份有限公司 | Ecological environment-friendly treatment method of dye or dye intermediate |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113527909A (en) * | 2021-07-23 | 2021-10-22 | 杭州吉华江东化工有限公司 | Synthesis process of environment-friendly dye |
| CN114316629A (en) * | 2021-12-23 | 2022-04-12 | 江苏格罗瑞化学有限公司 | Green and environment-friendly disperse dye intermediate treatment method |
| CN115651422A (en) * | 2022-10-25 | 2023-01-31 | 杭州吉华江东化工有限公司 | Synthetic method of environment-friendly heterocyclic disperse red dye |
| CN115651422B (en) * | 2022-10-25 | 2024-02-09 | 杭州吉华江东化工有限公司 | Synthesis method of environment-friendly heterocyclic disperse red dye |
| CN117417649A (en) * | 2023-10-12 | 2024-01-19 | 济宁阳光化学有限公司 | Environment-friendly high-performance pigment red P.R.2 and preparation method and application thereof |
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| Publication number | Publication date |
|---|---|
| CN106748810B (en) | 2021-04-27 |
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