CN105523949A - Method for preparing triethanolamine acrylate compound - Google Patents
Method for preparing triethanolamine acrylate compound Download PDFInfo
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- CN105523949A CN105523949A CN201610029306.9A CN201610029306A CN105523949A CN 105523949 A CN105523949 A CN 105523949A CN 201610029306 A CN201610029306 A CN 201610029306A CN 105523949 A CN105523949 A CN 105523949A
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- Prior art keywords
- methyl acrylate
- vinylformic acid
- acrylate compound
- ester compound
- preparation
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- -1 triethanolamine acrylate compound Chemical class 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 13
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims abstract description 27
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229940102001 zinc bromide Drugs 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 229960004418 trolamine Drugs 0.000 claims description 31
- 238000002360 preparation method Methods 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 238000011068 loading method Methods 0.000 claims description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002808 molecular sieve Substances 0.000 claims description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000007983 Tris buffer Substances 0.000 claims description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 3
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 claims description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 abstract description 10
- SHDIPWPAGQDYTH-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanol;prop-2-enoic acid Chemical compound OC(=O)C=C.OCCN(CCO)CCO SHDIPWPAGQDYTH-UHFFFAOYSA-N 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000010792 warming Methods 0.000 description 6
- 238000009835 boiling Methods 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- NPSSWQJHYLDCNV-UHFFFAOYSA-N prop-2-enoic acid;hydrochloride Chemical compound Cl.OC(=O)C=C NPSSWQJHYLDCNV-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention relates to a method for preparing a triethanolamine acrylate compound. The method comprises the following steps of adding an organic solvent, a catalyst, a polymerization inhibitor and a methyl acrylate compound into a reactor, dropwise adding triethanolamine into a reaction system, and carrying out a reaction for 0.5-15 hours at the temperature of 0-90 DEG C, so as to produce the triethanolamine acrylate compound, wherein the mole ratio of the catalyst to the methyl acrylate is 0.01-20%; the mole ratio of the raw materials, i.e., the triethanolamine to the methyl acrylate is (1: 3.0) to (1: 15.0); and the catalyst is supported zinc bromide, and the methyl acrylate compound is methyl acrylate and methyl methacrylate. According to the method disclosed by the invention, the triethanolamine acrylate product can be prepared in a high-efficiency and environment-friendly manner under relatively mild experimental conditions.
Description
Technical field
The present invention relates to ester class building-up reactions field, specifically relate to and carry out from methyl acrylate compound and trolamine the method that transesterification reaction prepares vinylformic acid trolamine ester compound.
Background technology
Vinylformic acid trolamine ester compound is the important fine-chemical intermediate of a class, this compounds has the higher amido of reactive behavior and vinyl Liang Zhong functional group simultaneously, can be widely used in the numerous areas such as polymeric flocculant, zwitter-ion linking agent, quaternary ammonium salt antiseptic-germicide, polycarboxylate water-reducer, cement grinding aid.Be subject to the extensive concern of the numerous researcher in various countries in recent years.
The synthetic method report of vinylformic acid trolamine ester compound is more, patent CN200910232784.X and research paper (FoodChemistry, 2015,172,56-62; Imaging science and photochemistry, 2008,26,403) reporting respectively with triethylamine is acid binding agent, acrylate chloride and methacrylic chloride react the reaction preparing vinylformic acid methyl triethanol amine ester, methacrylic acid methyl triethanolamine ester respectively with trolamine, generate triethylamine hydrochloride by product in this reaction process.In patent CN201080055967.X, methacrylic acid and trolamine carry out esterification, use methylbenzene azeotropic band water preparing product.This reaction uses a large amount of corrodibility methylsulfonic acids.Therefore, research and develop a kind of easy, environmental protection, efficiently prepare the technique of vinylformic acid trolamine ester compound and become one of the study hotspot in this field current.
Summary of the invention
Technical problem to be solved by this invention overcomes the deficiencies in the prior art, propose a kind of can efficiently, environmental protection, low cost the method preparing vinylformic acid trimethylammonium amido ethyl ester compound.
In the reaction of acrylic acid synthesizing trolamine ester compound, usually adopt the method for esterification.The method preparing vinylformic acid trolamine ester compound of bibliographical information, conventional triethylamine, mesylate compound etc., these compound amount are large, price is high, not easily reclaim, and its application is by restriction to a certain extent.Zinc bromide is the important inorganic salt product of a class, can as catalyzer, stablizer, additive etc., and range of application is extremely wide.It is the catalyzer of excellent performance in the reaction, has the features such as catalytic efficiency is high, Heat stability is good, is day by day subject to the attention of numerous scientific research personnel in organic synthesis.But zinc bromide solvability in this reaction system is poor, by its load on the carriers such as gac, aluminum oxide, silicon oxide, molecular sieve, can reduce consumption, improve its catalytic activity, be conducive to catalyst recovery.
The present invention is a kind of preparation method of vinylformic acid trolamine ester compound, and it is characterized in that, the method comprises the following steps:
In reactor, add organic solvent, catalyzer, stopper and methyl acrylate compound, in reaction system, drip trolamine, at 0 ~ 90 DEG C, react 0.5 ~ 15h, generate vinylformic acid trolamine ester compound; Wherein, the mol ratio of described catalyzer and methyl acrylate compound is 0.01 ~ 20%; The mol ratio of raw material trolamine and methyl acrylate compound is 1:3.0 ~ 1:15.0; Described catalyzer is loading type zinc bromide, and described methyl acrylate compound is methyl acrylate and methyl methacrylate.
In above-mentioned preparation method, the carrier of described loading type zinc bromide is the one in gac, aluminum oxide, silicon oxide, molecular sieve.
The mol ratio of described catalyzer and methyl acrylate compound is 0.1 ~ 5%; The temperature of described transesterification reaction is 50 ~ 90 DEG C.
Described organic solvent is preferably one or more solvents in acetone, butanone, toluene, chloroform, tetracol phenixin, hexane, hexanaphthene, heptane, octane, acetonitrile, tetrahydrofuran (THF), glycol dimethyl ether.
Described stopper is preferably at least one in the compounds such as nitroxyl free radical piperidine alcohols, piperidines free radical tris phosphite, hydroquinone monomethyl ether, thiodiphenylamine, tert.-butyl phenol, Resorcinol.
The preparation method of vinylformic acid trolamine ester compound of the present invention is compared with existing preparation method, beneficial effect is: 1) the present invention adopts loading type zinc bromide to be catalyzer, make preparation feedback condition relatively gentle, and vinylformic acid trolamine ester compound can be obtained within a short period of time; 2) adopt the inventive method preparation, the cost of product propylene triethylenetetraminehexaacetic acid alkanolamine ester compounds is lower, and present method is more efficient, environmental protection, is suitable for large-scale production.
Embodiment
Below in conjunction with concrete example, the present invention is described in detail, but be not limited to these examples, and raw material used in the present invention is commercially available.
Embodiment 1
Be furnished with in the reactor of reaction and rectification device to 5000ml, add 2064g methyl acrylate, 450g hexanaphthene, nitroxyl free radical piperidine alcohols stopper 18.8g, the Zinc Bromide catalyst (charge capacity 19%) that 45.8g is activated carbon supported, open stirring, be warming up to 70 DEG C, drip 596g trolamine, be warming up to backflow, control of reflux ratio 8:1.After reaction terminates, filtering recovering catalyst, rectification under vacuum, steams low-boiling compound, obtains trolamine triacrylate 646g.
Embodiment 2
Be furnished with in the reactor of reaction and rectification device to 5000ml, add 2500g methyl methacrylate, 400g toluene, hydroquinone monomethyl ether's stopper 19.3g, the Zinc Bromide catalyst (charge capacity 15%) of 56.4g gama-alumina load, stir, be warming up to 70 DEG C, drip 596g trolamine, be warming up to backflow, control of reflux ratio 9:1.After reaction terminates, filtering recovering catalyst, rectification under vacuum, steams low-boiling compound, obtains trolamine trimethacrylate 650g.
Embodiment 3
Be furnished with in the reactor of reaction and rectification device to 5000ml, add 2580g methyl acrylate, 400g hexanaphthene, piperidines free radical tris phosphite stopper 27.6g, the Zinc Bromide catalyst (charge capacity 17%) that 54.2gZSM-5 is molecular sieve carried, stir, be warming up to 70 DEG C, drip 596g trolamine, be warming up to backflow, control of reflux ratio 9:1.After reaction terminates, filtering recovering catalyst, rectification under vacuum, steams low-boiling compound, obtains trolamine triacrylate 684g.
Claims (5)
1. a preparation method for vinylformic acid trolamine ester compound, is characterized in that, said method comprising the steps of:
In reactor, add organic solvent, catalyzer, stopper and methyl acrylate compound, in reaction system, drip trolamine, at 0 ~ 90 DEG C, react 0.5 ~ 15h, generate vinylformic acid trolamine ester compound; Wherein, the mol ratio of described catalyzer and methyl acrylate compound is 0.01 ~ 20%; The mol ratio of raw material trolamine and methyl acrylate compound is 1:3.0 ~ 1:15.0; Described catalyzer is loading type zinc bromide, and described methyl acrylate compound is methyl acrylate and methyl methacrylate.
2. the preparation method of vinylformic acid trolamine ester compound according to claim 1, is characterized in that, the carrier of described loading type zinc bromide is the one in gac, aluminum oxide, silicon oxide, molecular sieve.
3. the preparation method of vinylformic acid trolamine ester compound according to claim 1, is characterized in that, the mol ratio of described catalyzer and methyl acrylate compound is 0.1 ~ 5%; The temperature of described transesterification reaction is 50 ~ 90 DEG C.
4. the preparation method of vinylformic acid trolamine ester compound according to claim 1, it is characterized in that, described organic solvent is one or more solvents in acetone, butanone, toluene, chloroform, tetracol phenixin, hexane, hexanaphthene, heptane, octane, acetonitrile, tetrahydrofuran (THF), glycol dimethyl ether.
5. the preparation method of vinylformic acid trolamine ester compound according to claim 1, it is characterized in that, described stopper is at least one in the compounds such as nitroxyl free radical piperidine alcohols, piperidines free radical tris phosphite, hydroquinone monomethyl ether, thiodiphenylamine, tert.-butyl phenol, Resorcinol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610029306.9A CN105523949A (en) | 2016-01-15 | 2016-01-15 | Method for preparing triethanolamine acrylate compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610029306.9A CN105523949A (en) | 2016-01-15 | 2016-01-15 | Method for preparing triethanolamine acrylate compound |
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| Publication Number | Publication Date |
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| CN105523949A true CN105523949A (en) | 2016-04-27 |
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| CN201610029306.9A Pending CN105523949A (en) | 2016-01-15 | 2016-01-15 | Method for preparing triethanolamine acrylate compound |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107868008A (en) * | 2017-11-22 | 2018-04-03 | 许昌学院 | A kind of formaldehyde scavenger and its synthetic method |
| KR101872164B1 (en) * | 2017-09-20 | 2018-06-27 | 동우 화인켐 주식회사 | Acrylate Compound and Photocurable Composition Comprising the Same |
| CN112175592A (en) * | 2019-07-02 | 2021-01-05 | 中石化南京化工研究院有限公司 | Dendritic cationic polyacrylamide coating agent for water-based drilling fluid and preparation method thereof |
| CN112250831A (en) * | 2020-10-12 | 2021-01-22 | 深圳飞扬兴业科技有限公司 | UV resin and preparation method thereof |
| CN113731120A (en) * | 2021-09-22 | 2021-12-03 | 河南佳诺威木业有限公司 | MDF tail gas standard emission process |
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| US3872161A (en) * | 1972-03-06 | 1975-03-18 | Nippon Catalytic Chem Ind | Process for the manufacture of alkylaminoalkyl acrylates |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101872164B1 (en) * | 2017-09-20 | 2018-06-27 | 동우 화인켐 주식회사 | Acrylate Compound and Photocurable Composition Comprising the Same |
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| CN112175592A (en) * | 2019-07-02 | 2021-01-05 | 中石化南京化工研究院有限公司 | Dendritic cationic polyacrylamide coating agent for water-based drilling fluid and preparation method thereof |
| CN112175592B (en) * | 2019-07-02 | 2022-11-29 | 中石化南京化工研究院有限公司 | Dendritic cationic polyacrylamide coating agent for water-based drilling fluid and preparation method thereof |
| CN112250831A (en) * | 2020-10-12 | 2021-01-22 | 深圳飞扬兴业科技有限公司 | UV resin and preparation method thereof |
| CN113731120A (en) * | 2021-09-22 | 2021-12-03 | 河南佳诺威木业有限公司 | MDF tail gas standard emission process |
| CN113731120B (en) * | 2021-09-22 | 2024-03-26 | 河南佳诺威木业有限公司 | MDF tail gas standard emission process |
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