CN106008376A - Preparation method of ultraviolet absorbent UV-329 - Google Patents
Preparation method of ultraviolet absorbent UV-329 Download PDFInfo
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- CN106008376A CN106008376A CN201610346337.7A CN201610346337A CN106008376A CN 106008376 A CN106008376 A CN 106008376A CN 201610346337 A CN201610346337 A CN 201610346337A CN 106008376 A CN106008376 A CN 106008376A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
- C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
Abstract
The invention discloses a preparation method of an ultraviolet absorbent UV-329. The preparation method comprises the following steps that an azo intermediate shown as the formula (I) is reduced into an oxynitride shown as the formula (II) by a reducing agent; then, the oxynitride is reduced into a product shown as the formula (III) by a reducing agent; the reducing agent is formed by sintering metal powder and an adsorbent, wherein the formula (I), the formula (II) and the formula (III) are shown as the accompanying drawing. The preparation method has the beneficial effects that the method provided by the invention has the advantages that the consumption of the metal powder is low; the environment pollution is little; the operation is convenient and simple; the product yield is high.
Description
Technical field
The present invention relates to the preparation method of a kind of UV absorbent, more specifically, it relates to a kind of UV absorbent
The preparation method of UV-329.
Background technology
The synthetic method of existing Benzotriazole Ultraviolet Stabilizer, mainly from azobenzene compound be raw material, according to difference
Reducing process reduce.Different according to the reducing agent used, the reduction of benzotriazole compound, can be divided into one-step method and
Two-step method.Azo dye is i.e. reduced to product with a kind of reducing agent by so-called one-step method, and so-called two-step method is the most first with a kind of reducing agent
It is that nitrogen oxides according to circumstances can be separated or not branch away by nitrogen oxides by reducing dyes, then with another kind of reducing agent
It is end product by nitrogen oxides intermediate reduction.
Substantial amounts of experiment shows: the condition of synthetic nitrogen oxide compares mitigation, and the condition that it is reduced to product further is more violent
Stronger.If only using a kind of reducing agent, being difficult to control reaction, not reaching good effect.It addition, compared with azo intermediate,
Nitrogen oxides is more more stable, and the most fragile ring generates aminated compounds.Therefore, just product can be studied on the basis of one-step method further
Raw two-step method.
In two-step method, documents 1 (" synthesising process research of benzotriazole ultraviolet absorber ", Zhu Yinghua, " Nanjing
Polytechnics's master thesis ", 20101029) disclose a kind of use glucose and zinc powder by two steps reduction from diphenyl diimide
Compound obtains the method for benzotriazole light stabilizer.Documents 2 (201310321244.5) discloses a kind of BTA
The preparation method of class UV absorbent.This preparation method utilize aluminium powder and sodium sulfite as reducing agent, in the middle of diphenyl diimide
Body obtains Benzotriazole Ultraviolet Stabilizer, it is to avoid use zinc powder to bring the pollution to environment.
Documents 1 uses zinc powder as reducing agent, and the contaminated wastewater of generation is the most serious.Documents 2 use aluminium powder and
Sodium sulfite, as reducing agent, when adding aluminium powder, causes by-product to increase in order to avoid local response is too fast, documents
Use the form being dividedly in some parts.But batch mode manually controls, have inaccurate, and workload can be increased.
Summary of the invention
The deficiency existed for prior art, it is an object of the invention to provide the preparation of a kind of UV absorbent UV-329
Method.It is few that the method that the present invention provides has metal powder usage amount, low in the pollution of the environment, easy to operate simple advantage.
For achieving the above object, the technical scheme is that
The preparation method of a kind of UV absorbent UV-329, comprises the steps:
Step 1: join in reaction vessel by the azo intermediate as shown in formula (I), alkali and the first solvent, adds reducing agent,
Back flow reaction 1-3h；
Step 2: mixed solution step 1 obtained carries out purifying the nitrogen oxides obtained as shown in formula (II) for the first time；
Step 3: join in reaction vessel by the nitrogen oxides as shown in formula (II), acid, the second solvent, adds reducing agent, returns
Stream reaction 1-3h；
Step 4: mixed solution step 3 obtained carries out second time and purifies the product obtained as shown in formula (III)；
Described reducing agent is that metal powder forms with adsorbent sintering；
Wherein Formulas I, II, III are respectively as follows:
As preferably, described metal powder is selected from the one in zinc powder, aluminium powder and iron powder, metal in the reducing agent in described step 1
The mol ratio of powder and azo intermediate is 0.7-1.2: 1；Metal powder and the mol ratio of nitrogen oxides in reducing agent in described step 3
For 0.7-1.2: 1.
As preferably, described alkali selects sodium hydroxide, according to mol ratio, described alkali: azo intermediate=1.9-3.0: 1, described
One of which in hydrochloric acid, sulphuric acid, according to mol ratio, hydrion in described acid: nitrogen oxides=3.0-7.8: 1 are selected in acid.
As preferably, described first solvent is according to volume ratio, methanol: the mixed solvent of water=3.6-5: 1 mixing, described idol
The quality of nitrogen intermediate: the first solvent volume=0.12-0.18: 1g/mL, described second solvent is according to volume ratio, toluene: water
The mixed solvent of=1: 0.5-0.6 mixing, the quality of described nitrogen oxides: the second solvent volume=0.17-0.2: 1g/mL.
As preferably, the reducing agent in described step 1 and step 3 is all slowly added to when controlling reaction temperature at 60-70 DEG C.
As preferably, the pH that step is the solution that regulating step 1 obtains that described first time purifies, to producing precipitation, filters,
Wash with water, be dried, obtain the nitrogen oxides as shown in formula (II)；The step that described second time purifies is for obtain step 3
Solution filter, filtrate is poured into water, crystallisation by cooling, filter, wash with water, be dried, obtain as shown in formula (III)
Product.
As preferably, described step 2 use hydrochloric acid pH is adjusted to 6.
As preferably, described adsorbent selects one of which in coke and clay.
Another goal of the invention of the present invention is to provide the preparation method of a kind of reducing agent, comprises the steps:
1. by metal powder and adsorbent at twin-spiral mixer mix homogeneously；
The most compressing；
The most under nitrogen protection, control temperature to be 500-1200 DEG C and be sintered；
4. cool down molding, obtain reducing agent.
As preferably, the weight ratio of described metal powder and adsorbent is 0.5-2: 1, described in be cooled to water-cooled.
By using technique scheme, the present invention has the beneficial effect that:
(1) metal powder is sintered using as reducing agent by the present invention with coke or clay, it is possible to play the Controlled release to metal powder
Effect, reduces chain carrier, it is to avoid response speed is too fast, thus reduces metal powder usage amount, increases the safety of reaction
Can, and avoid localized metallic powder too much to cause side reaction to increase, improve yield, reduce and pollute；
(2) it is suppressed due to the reactivity of metal powder, controls to make step in conjunction with conditions such as solvent, reaction temperature, pH in step 1
Azo intermediate can only be reduced to nitrogen oxides by the metal powder in 1, and can not be reduced directly to final products, and in step 3
The reaction conditions such as middle change solvent, pH, strengthen the reproducibility of metal powder, enable nitrogen oxides to be directly reduced to final products.
Thus in the case of realizing using identical reducing agent at the same time, it is possible to control first step reduction reaction and be only reacted to nitrogen oxides, and
Will not react further, it is achieved the requirement of two step reduction such that it is able to reduce the demand to reducing agent kind, reduce and produce
Difficulty.And this point is in the prior art from being not directed to；
(3) coke or clay have bigger specific surface area, it is possible to play decolorization in course of reaction；
(4) in the preparation method of reducing agent, use water-cooled, the hot water obtained can be recycled, improve capacity usage ratio after water-cooled；
(5) reducing agent can disposably put into, and reduces the operation requirement adding reducing agent；
(6) using butanol as solvent in documents 2, and the present invention uses methanol as solvent.Owing to the boiling point of butanol is higher than methanol,
So in purification process, the dissolvent residual of butanol is more, makes yield decline, pollute simultaneously.The cost of butanol is also simultaneously
Higher than methanol.Therefore, methanol is substantially due to butanol.
Detailed description of the invention
Embodiment 1-4 is the preparation method of reducing agent
Embodiment 1
1. according to weight ratio, aluminium powder: adsorbent=0.5: 1, add metal powder and coke mix homogeneously toward twin-spiral mixer；
The most compressing；
The most under nitrogen protection, control temperature to be 1200 DEG C and be sintered；
4. it is water-cooled molding, obtains the reducing agent of soybean grain size, a diameter of 2mm.
Embodiment 2
1. according to weight ratio, iron powder: adsorbent=2: 1, add metal powder and clay mix homogeneously toward twin-spiral mixer；
The most compressing；
The most under nitrogen protection, control temperature to be 700 DEG C and be sintered；
4. it is water-cooled molding, obtains the reducing agent of soybean grain size, a diameter of 6mm.
Embodiment 3
1. according to weight ratio, zinc powder: adsorbent=1.5: 1, add metal powder and coke mix homogeneously toward twin-spiral mixer；
The most compressing；
The most under nitrogen protection, control temperature to be 900 DEG C and be sintered；
4. it is water-cooled molding, obtains the reducing agent of soybean grain size, a diameter of 10mm.
Embodiment 4
1. according to weight ratio, aluminium powder: adsorbent=1: 1, add metal powder and clay mix homogeneously toward twin-spiral mixer；
The most compressing；
The most under nitrogen protection, control temperature to be 500 DEG C and be sintered；
4. it is water-cooled molding, obtains the reducing agent of soybean grain size, a diameter of 2mm.
Embodiment 5-10 is the preparation method of UV absorbent UV-329
Embodiment 5
Step 1: by homemade 2-nitro-2 '-hydroxyl-5 '-t-octyl diphenyl diimide (97.8%), 36.3g (0.1021mol), hydroxide
Sodium 10g, methanol 180ml and water 50ml, join in 500ml four-hole boiling flask, control reaction temperature 60 DEG C be slowly added to by
According to the reducing agent 4.04g of embodiment 4 preparation, back flow reaction 2 hours, solution becomes light yellow and is reaction end；
Step 2: be slowly added dropwise the hydrochloric acid of 30%, neutralizing reactant liquor PH is 6, produces a large amount of yellow mercury oxide, filters, uses 50ml respectively
Wash 2 times, be dried, obtain intermediate 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole nitrogen oxides 32.3g, yield
It is 95.3%；
Step 3: take step gained 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole nitrogen oxides 32.3g (0.0999mol),
The hydrochloric acid 30ml of 30%, toluene 100ml and water 60ml, join in 500ml four-hole boiling flask, controls reaction temperature at 60 DEG C
Being slowly added to the reducing agent 4.04g according to embodiment 4 preparation, back flow reaction 2 hours, solution becomes oyster and is reaction eventually
Point；
Step 4: solution is first filtered to remove insoluble matter, filtrate is poured in 100ml water, crystallisation by cooling, filters, uses 50ml water respectively
Washing 2 times, be dried, obtain product 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole 28.8g, yield is 89.2%, molten
Point is for 103-105 DEG C.
Embodiment 6
Step 1: by homemade 2-nitro-2 '-hydroxyl-5 '-t-octyl diphenyl diimide (97.8%), 36.3g (0.1021mol), hydroxide
Sodium 8g, methanol 200ml and water 50ml, join in 500ml four-hole boiling flask, control reaction temperature 70 DEG C be slowly added to by
According to the reducing agent 6.34g of embodiment 1 preparation, back flow reaction 2 hours, solution becomes light yellow and is reaction end；
Step 2: be slowly added dropwise the hydrochloric acid of 30%, neutralizing reactant liquor PH is 6, produces a large amount of yellow mercury oxide, filters, uses 50ml respectively
Wash 2 times, be dried, obtain intermediate 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole nitrogen oxides 32.6g, yield
It is 96.2%；
Step 3: take step gained 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole nitrogen oxides 32.6g (0.1008mol),
The hydrochloric acid 60ml of 30%, toluene 120ml and water 60ml, join in 500ml four-hole boiling flask, controls reaction temperature at 70 DEG C
Being slowly added to the reducing agent 5.79g according to embodiment 1 preparation, back flow reaction 2 hours, solution becomes oyster and is reaction eventually
Point；
Step 4: solution is first filtered to remove insoluble matter, filtrate is poured in 100ml water, crystallisation by cooling, filters, uses 50ml water respectively
Washing 2 times, be dried, obtain product 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole 28.9g, yield is 89.5%, molten
Point is for 103-105 DEG C.
Embodiment 7
Step 1: by homemade 2-nitro-2 '-hydroxyl-5 '-t-octyl diphenyl diimide (97.8%), 36.3g (0.1021mol), hydroxide
Sodium 12g, methanol 150ml and water 50ml, join in 500ml four-hole boiling flask, control reaction temperature 62 DEG C be slowly added to by
According to the reducing agent 5.79g of embodiment 1 preparation, back flow reaction 2 hours, solution becomes light yellow and is reaction end；
Step 2: be slowly added dropwise the hydrochloric acid of 30%, neutralizing reactant liquor PH is 6, produces a large amount of yellow mercury oxide, filters, uses 50ml respectively
Wash 2 times, be dried, obtain intermediate 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole nitrogen oxides 31.8g, yield
It is 93.8%；
Step 3: take step gained 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole nitrogen oxides 31.8g (0.0983mol),
The sulphuric acid 10ml of 98%, toluene 100ml and water 60ml, join in 500ml four-hole boiling flask, controls reaction temperature at 62 DEG C
Being slowly added to the reducing agent 6.34g according to embodiment 1 preparation, back flow reaction 2 hours, solution becomes oyster and is reaction eventually
Point；
Step 4: solution is first filtered to remove insoluble matter, filtrate is poured in 100ml water, crystallisation by cooling, filters, uses 50ml water respectively
Washing 2 times, be dried, obtain product 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole 28.1g, yield is 87.0%, molten
Point is for 103-105 DEG C.
Embodiment 8
Step 1: by homemade 2-nitro-2 '-hydroxyl-5 '-t-octyl diphenyl diimide (97.8%), 36.3g (0.1021mol), hydroxide
Sodium 10g, methanol 250ml and water 50ml, join in 500ml four-hole boiling flask, control reaction temperature 64 DEG C be slowly added to by
According to the reducing agent 6.34g of embodiment 1 preparation, back flow reaction 2 hours, solution becomes light yellow and is reaction end；
Step 2: be slowly added dropwise the hydrochloric acid of 30%, neutralizing reactant liquor PH is 6, produces a large amount of yellow mercury oxide, filters, uses 50ml respectively
Wash 2 times, be dried, obtain intermediate 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole nitrogen oxides 31.6g, yield
It is 93.2%；
Step 3: take step gained 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole nitrogen oxides 31.6g (0.0977mol),
The sulphuric acid 20ml of 98%, toluene 120ml and water 60ml, join in 500ml four-hole boiling flask, controls reaction temperature at 64 DEG C
Being slowly added to the reducing agent 5.79g according to embodiment 1 preparation, back flow reaction 2 hours, solution becomes oyster and is reaction eventually
Point；
Step 4: solution is first filtered to remove insoluble matter, filtrate is poured in 100ml water, crystallisation by cooling, filters, uses 50ml water respectively
Washing 2 times, be dried, obtain product 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole 27.8g, yield is 86.1%, molten
Point is for 103-105 DEG C.
Embodiment 9
Step 1: by homemade 2-nitro-2 '-hydroxyl-5 '-t-octyl diphenyl diimide (97.8%), 36.3g (0.1021mol), hydroxide
Sodium 10g, methanol 180ml and water 50ml, join in 500ml four-hole boiling flask, control reaction temperature 66 DEG C be slowly added to by
According to the reducing agent 4.04g of embodiment 4 preparation, back flow reaction 2 hours, solution becomes light yellow and is reaction end；
Step 2: be slowly added dropwise the hydrochloric acid of 30%, neutralizing reactant liquor PH is 6, produces a large amount of yellow mercury oxide, filters, uses 50ml respectively
Wash 2 times, be dried, obtain intermediate 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole nitrogen oxides 32.1g, yield
It is 94.7%；
Step 3: take step gained 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole nitrogen oxides 32.1g (0.0947mol),
The hydrochloric acid 30ml of 30%, toluene 100ml and water 60ml, join in 500ml four-hole boiling flask, controls reaction temperature at 66 DEG C
Being slowly added to the reducing agent 10.29g according to embodiment 2 preparation, back flow reaction 2 hours, solution becomes oyster and is reaction
Terminal；
Step 4: solution is first filtered to remove insoluble matter, filtrate is poured in 100ml water, crystallisation by cooling, filters, uses 50ml water respectively
Washing 2 times, be dried, obtain product 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole 28.7g, yield is 88.9%, molten
Point is for 103-105 DEG C.
Embodiment 10
Step 1: by homemade 2-nitro-2 '-hydroxyl-5 '-t-octyl diphenyl diimide (97.8%), 36.3g (0.1021mol), hydroxide
Sodium 10g, methanol 180ml and water 50ml, join in 500ml four-hole boiling flask, control reaction temperature 68 DEG C be slowly added to by
According to the reducing agent 12.72g of embodiment 3 preparation, back flow reaction 2 hours, solution becomes light yellow and is reaction end；
Step 2: be slowly added dropwise the hydrochloric acid of 30%, neutralizing reactant liquor PH is 6, produces a large amount of yellow mercury oxide, filters, uses 50ml respectively
Wash 2 times, be dried, obtain intermediate 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole nitrogen oxides 31.9g, yield
It is 94.1%；
Step 3: take step gained 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole nitrogen oxides 31.9g (0.0941mol),
The hydrochloric acid 30ml of 30%, toluene 100ml and water 60ml, join in 500ml four-hole boiling flask, controls reaction temperature at 68 DEG C
Being slowly added to the reducing agent 12.72g according to embodiment 3 preparation, back flow reaction 2 hours, solution becomes oyster and is reaction
Terminal；
Step 4: solution is first filtered to remove insoluble matter, filtrate is poured in 100ml water, crystallisation by cooling, filters, uses 50ml water respectively
Washing 2 times, be dried, obtain product 2-(2 '-hydroxyl-5 '-t-octyl phenyl) benzotriazole 28.5g, yield is 88.2%, molten
Point is for 103-105 DEG C.
The above is only the preferred embodiment of the present invention, and protection scope of the present invention is not limited merely to above-described embodiment,
All technical schemes belonged under thinking of the present invention belong to protection scope of the present invention.It should be pointed out that, for the art is general
For logical technical staff, some improvements and modifications without departing from the principles of the present invention, these improvements and modifications also should be regarded as
Protection scope of the present invention.
Claims (10)
1. a preparation method for UV absorbent UV-329, is characterized in that: comprise the steps:
Step 1: the azo intermediate as shown in formula (I), alkali and the first solvent are joined in reaction vessel, adds
Enter reducing agent, back flow reaction 1-3h；
Step 2: mixed solution step 1 obtained carries out purifying the nitrogen oxidation obtained as shown in formula (II) for the first time
Thing；
Step 3: join in reaction vessel by the nitrogen oxides as shown in formula (II), acid, the second solvent, adds
Reducing agent, back flow reaction 1-3h；
Step 4: mixed solution step 3 obtained carries out second time and purifies the product obtained as shown in formula (III)；
Described reducing agent is that metal powder forms with adsorbent sintering；
Wherein Formulas I, II, III are respectively as follows:
The preparation method of a kind of UV absorbent UV-329 the most according to claim 1, is characterized in that: institute
State metal powder one in zinc powder, aluminium powder and iron powder, metal powder and idol in the reducing agent in described step 1
The mol ratio of nitrogen intermediate is 0.7-1.2: 1；Metal powder and nitrogen oxides in reducing agent in described step 3
Mol ratio is 0.7-1.2: 1.
The preparation method of a kind of UV absorbent UV-329 the most according to claim 1, is characterized in that: institute
Stating alkali selects sodium hydroxide, according to mol ratio, described alkali: azo intermediate=1.9-3.0: 1, described acid to select
One of which in hydrochloric acid, sulphuric acid, according to mol ratio, hydrion in described acid: nitrogen oxides=3.0-7.8: 1.
The preparation method of a kind of UV absorbent UV-329 the most according to claim 1, is characterized in that: institute
State the first solvent for according to volume ratio, methanol: the mixed solvent of water=3.6-5: 1 mixing, described azo intermediate
Quality: the first solvent volume=0.12-0.18: 1g/mL, described second solvent is according to volume ratio, toluene:
The mixed solvent of water=1: 0.5-0.6 mixing, the quality of described nitrogen oxides: the second solvent volume=0.17-0.2: 1
g/mL。
The preparation method of a kind of UV absorbent UV-329 the most according to claim 1, is characterized in that: institute
State the reducing agent in step 1 and step 3 to be all slowly added to when controlling reaction temperature at 60-70 DEG C.
The preparation method of a kind of UV absorbent UV-329 the most according to claim 1, is characterized in that: institute
State the pH that step is the solution that regulating step 1 obtains purified for the first time to producing precipitation, filter, wash with water
Wash, be dried, obtain the nitrogen oxides as shown in formula (II)；The step that described second time purifies is by step 3
The solution obtained filters, and filtrate is poured into water, crystallisation by cooling, filters, washes with water, is dried, obtains
Product as shown in formula (III).
The preparation method of a kind of UV absorbent UV-329 the most according to claim 1, is characterized in that: institute
State and step 2 uses hydrochloric acid pH is adjusted to 6.
The preparation method of a kind of benzotriazole UV absorbers the most according to claim 1, its feature
It is: described adsorbent selects one of which in coke and clay.
9. a preparation method for reducing agent as claimed in claim 1, is characterized in that: comprise the steps:
1. by metal powder and adsorbent at twin-spiral mixer mix homogeneously；
The most compressing；
The most under nitrogen protection, control temperature to be 500-1200 DEG C and be sintered；
4. cool down molding, obtain reducing agent.
The preparation method of a kind of reducing agent the most according to claim 9, is characterized in that: described metal powder and suction
The weight ratio of attached dose is 0.5-2: 1, described in be cooled to water-cooled.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110066252A (en) * | 2019-05-29 | 2019-07-30 | 襄阳金达成精细化工有限公司 | A kind of preparation method of ultraviolet absorbing agent UV-329 |
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| CN103011434A (en) * | 2012-12-31 | 2013-04-03 | 福建金源泉科技发展有限公司 | Filter cartridge material |
| CN104327002A (en) * | 2014-09-16 | 2015-02-04 | 德州宏坤医药中间体有限公司 | Producing technology of benzotriazole-typed ultraviolet absorber |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103011434A (en) * | 2012-12-31 | 2013-04-03 | 福建金源泉科技发展有限公司 | Filter cartridge material |
| CN104327002A (en) * | 2014-09-16 | 2015-02-04 | 德州宏坤医药中间体有限公司 | Producing technology of benzotriazole-typed ultraviolet absorber |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110066252A (en) * | 2019-05-29 | 2019-07-30 | 襄阳金达成精细化工有限公司 | A kind of preparation method of ultraviolet absorbing agent UV-329 |
| CN110066252B (en) * | 2019-05-29 | 2020-11-03 | 襄阳金达成精细化工有限公司 | Preparation method of ultraviolet absorbent UV-329 |
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