CN105348208A - Preparation method of tris(2-hydroxycyclohexyl) isocyanuric acid triacrylate - Google Patents
Preparation method of tris(2-hydroxycyclohexyl) isocyanuric acid triacrylate Download PDFInfo
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- CN105348208A CN105348208A CN201510931213.0A CN201510931213A CN105348208A CN 105348208 A CN105348208 A CN 105348208A CN 201510931213 A CN201510931213 A CN 201510931213A CN 105348208 A CN105348208 A CN 105348208A
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- VTXRDCQMLXABHJ-QRHSGQBVSA-N CCC1(C)[C@@H](C)[C@@H](C)CCC1 Chemical compound CCC1(C)[C@@H](C)[C@@H](C)CCC1 VTXRDCQMLXABHJ-QRHSGQBVSA-N 0.000 description 1
- XNMAYZPLKLWLBL-OUAUKWLOSA-N CCC[C@H]1[C@@H](C)CC[C@@H](C)C1 Chemical compound CCC[C@H]1[C@@H](C)CC[C@@H](C)C1 XNMAYZPLKLWLBL-OUAUKWLOSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
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Abstract
The invention discloses a preparation method of tris(2-hydroxycyclohexyl) isocyanuric acid triacrylate. The preparation method comprises the steps of adding tris(2-hydroxycyclohexyl) isocyanuric acid, acrylic acid, a solvent, a catalyst, a first polymerization inhibitor and an antioxygen in a reactor, and uniformly mixing to obtain a reaction system; keeping the temperature of the reaction system at 90 to 150 DEG C, and pumping air into the reaction system to enable the reaction system to back flow to a reaction endpoint at constant temperature under normal pressure, so as to obtain a reaction product; sequentially washing the reaction product by water, alkali and salt, then standing for layering, and taking an upper layer to obtain an organic phase; adding the organic phase into a second polymerization inhibitor, performing reduced pressure distillation to remove the solvent in the organic phase, and performing pressure filtration on the organic phase to obtain the tris(2-hydroxycyclohexyl) isocyanuric acid triacrylate. The curing speed is fast, the mechanical performance is good, the shrinking percentage is low, the thermal stability and outdoor weather ability are excellent, the preparation steps are simple, and the cost is relatively low; an esterification reaction only needs 4 to 8h.
Description
Technical field
The present invention relates to a kind of preparation method of fine chemicals, in particular a kind of preparation method of three (2-hydroxy-cyclohexyl) tricarbimide triacrylate.
Background technology
Ultraviolet photocureable material is not because it is containing volatile organic solvent, and being applied to multiple fields such as coating, paint, ink, tackiness agent and matrix material as a kind of green environmental friendly coatings, is a kind of importance of coatings industry cleaner production.UV coating forms primarily of four major parts, i.e. oligopolymer, reactive thinner, light trigger and auxiliary agent.The properties and application of UV coating depends on performance and the composition of above-mentioned substance completely.Conventional oligopolymer in UV coating, as high temperature resistant in oligopolymer such as epoxy acrylate, urethane acrylate, polyester acrylate, polyether acrylates and mechanical property is not ideal enough.
And containing the stable hexa-atomic synthesize of rigidity (triazine ring) structure in three (2-hydroxy-cyclohexyl) chlorinated isocyanurates, there is excellent chemical stability and thermostability.The reactive behavior having 3 active hydroxyl groups in its molecule if utilize and cyclohexyl structure carry out acroleic acid esterification and obtain three (2-hydroxy-cyclohexyl) tricarbimide triacrylate, the intensity of UV coating, thermotolerance, weathering resistance and flame retardant resistance can be improved, and because of its huge structure, molecular chain is piled up lax, can be used for the star-like or dendritic compound synthesizing Gao Zhiduization, and then prepare the UV coating of low viscosity, high solids content.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, provide a kind of preparation method of three (2-hydroxy-cyclohexyl) tricarbimide triacrylate, can production cost be reduced.
The present invention is achieved by the following technical solutions: the present invention includes following steps:
(1) add three (2-hydroxy-cyclohexyl) chlorinated isocyanurates, vinylformic acid, solvent, catalyzer, the first stopper and oxidation inhibitor in the reactor successively, after mixing, obtain reaction system;
(2) temperature of reaction system remains on 90 ~ 150 DEG C, in reaction system, pass into air, makes described reaction system be back to reaction end under constant temperature normal pressure, obtains reaction product;
(3) described reaction product is washed successively, alkali cleaning, salt washes rear stratification, get its upper strata and obtain organic phase;
(4) described organic phase is added the second stopper and the solvent in organic phase is sloughed in underpressure distillation, pressure filtration is carried out to organic phase, obtains three (2-hydroxy-cyclohexyl) tricarbimide triacrylate.
As one of optimal way of the present invention, in described step (2), temperature of reaction is 115 ~ 125 DEG C, and the reaction times is 4 ~ 8h.
As one of optimal way of the present invention, described three (2-hydroxy-cyclohexyl) chlorinated isocyanurates and acrylic acid mol ratio are 1:2 ~ 8, the consumption of described catalyzer is 2.5 ~ 8.5% of three (2-hydroxy-cyclohexyl) chlorinated isocyanurates and vinylformic acid total mass, the consumption of described oxidation inhibitor is 0.1 ~ 1% of vinylformic acid quality, the consumption of described first stopper is 0.1 ~ 0.8% of vinylformic acid quality, and the consumption of described second stopper is 0.05 ~ 0.2% of vinylformic acid quality.
As one of optimal way of the present invention, described three (2-hydroxy-cyclohexyl) chlorinated isocyanurates and acrylic acid mol ratio are 1:2.5 ~ 4.5.
As one of optimal way of the present invention, in described step (2), after the acid number≤0.1mgKOH/g of reaction product, stopped reaction.
As one of optimal way of the present invention, in described step (4), until the content <500ppm of solvent, obtain product.
As one of optimal way of the present invention, in described step (1), described solvent be selected from toluene, ethyl acetate, tetracol phenixin and hexanaphthene one or more.
As one of optimal way of the present invention, described solvent be selected from toluene and ethyl acetate one or both, the consumption of described solvent is 60 ~ 100% of three (2-hydroxy-cyclohexyl) chlorinated isocyanurates and vinylformic acid total mass.
As one of optimal way of the present invention, described catalyzer is sulfonic compound.
As one of optimal way of the present invention, described catalyzer is tosic acid or methylsulphonic acid, and the consumption of described catalyzer is 4.5 ~ 6.5% of three (2-hydroxy-cyclohexyl) chlorinated isocyanurates and vinylformic acid total mass.
As one of optimal way of the present invention, described oxidation inhibitor is the salt compounds of ortho phosphorous acid or ortho phosphorous acid.
As one of optimal way of the present invention, described oxidation inhibitor is ortho phosphorous acid, and the consumption of described oxidation inhibitor is 0.4 ~ 0.7% of vinylformic acid quality.
As one of optimal way of the present invention, described first stopper be selected from cupric chloride, Salzburg vitriol, MEHQ and 2,6 ditertiary butyl p cresol one or more.
As one of optimal way of the present invention, described first stopper be selected from Salzburg vitriol or MEHQ one or both, the consumption of described first stopper is 0.3 ~ 0.6% of vinylformic acid quality.
As one of optimal way of the present invention, described second stopper is selected from MEHQ, to one or more in phenyl methylcarbamate, p-tert.-butyl cresol, p-ten.-butylcatechol.
As one of optimal way of the present invention, described second stopper be selected from MEHQ or p-ten.-butylcatechol one or both.
As one of optimal way of the present invention, vacuum tightness when described upper organic phase carries out underpressure distillation is-0.09 ~-0.1MPa, and temperature is 40 ~ 80 DEG C, and the time is 2 ~ 6 hours.
As one of optimal way of the present invention, vacuum tightness when described upper organic phase carries out underpressure distillation is-0.095 ~-0.098MPa, and temperature is 55 ~ 65 DEG C, and the time is 6 ~ 8 hours.
As described in three (2-hydroxy-cyclohexyl) tricarbimide triacrylate of obtaining of preparation method.
The present invention has the following advantages compared to existing technology: curing speed of the present invention is fast, good mechanical property, shrinking percentage is low, thermostability and outdoor weatherability excellence, and preparation process is simple, esterification 4 ~ 8 hours, cost is lower, can three (2-hydroxy-cyclohexyl) tricarbimide triacrylate of mass production.
Embodiment
Elaborate to embodiments of the invention below, the present embodiment is implemented under premised on technical solution of the present invention, give detailed embodiment and concrete operating process, but protection scope of the present invention is not limited to following embodiment.
Embodiment 1
The reaction principle of three (2-hydroxy-cyclohexyl) tricarbimide triacrylate of the present embodiment is as follows:
Concrete preparation process is as follows:
(1) successively 38.7g tri-(2-hydroxy-cyclohexyl) tricarbimide triacrylate, 14.2g vinylformic acid, 48g toluene, 3.3g methylsulphonic acid, 0.096g Salzburg vitriol, 0.117g ortho phosphorous acid are put in the 500ml four-hole boiling flask that thermometer, water trap, prolong, stirring rake are housed;
(2) oil bath heating and whipping appts is opened, temperature of reaction system is made to rise to 90 DEG C, air is passed in reaction system, and make the backflow 4 hours under constant temperature normal pressure in the reactor of described reaction system, carry out esterification dehydration reaction, after the acid number≤0.1mgKOH/g of reaction product to be obtained, stopped reaction;
(3) temperature of reaction system cooling is down to 40 DEG C, the deionized water adding 32g in reaction system wash after stratification, obtain the product after washing; Add in the product after described washing 80g mass concentration be 10% NaOH solution carry out alkali cleaning after stratification obtain the product after alkali cleaning; The mass concentration of 32g is added for (NH in the product after described alkali cleaning
4)
2sO
4solution carry out salt and wash rear stratification and get its upper organic phase.
(4) in described upper organic phase, 0.025 MEHQ is added, mix at 40 DEG C, vacuum tightness is that-0.09MPa carries out underpressure distillation and within 2 hours, sloughs solvent in organic phase, until the content <500ppm of solvent, obtains product.
The acid number of the finished product, purity and colourity are measured:
The acid number detection method of product in the present embodiment is measured by the method for GB/T12008.5-2010.
Chromatography of gases detection method gas chromatograph condition: carrier gas (high-purity helium), packed column PorapakQS, column temperature: 100 degree, injection port 220 degree, detector 220 degree, sampling volume 2ul, FID detect, SE-54 type capillary chromatographic column (30m × 0.32mm × 0.25um), ethylbenzene is internal standard substance.
Form and aspect APHA detection method measures by the method for GB/T605-1988.
The transformation efficiency of the preparation method of the present embodiment is 82%, and the purity of products obtained therefrom is 97%, and product colourity is APHA≤20.
Embodiment 2
The preparation method of the present embodiment comprises the following steps:
(1) successively 38.7g tri-(2-hydroxy-cyclohexyl) tricarbimide triacrylate, 56.8g vinylformic acid, 48g toluene, 3.3g methylsulphonic acid, 0.096g Salzburg vitriol, 0.117g ortho phosphorous acid are put in the 500ml four-hole boiling flask that thermometer, water trap, prolong, stirring rake are housed;
(2) oil bath heating and whipping appts is opened, temperature of reaction system is made to rise to 150 DEG C, air is passed in reaction system, and make the backflow 4 hours under constant temperature normal pressure in the reactor of described reaction system, carry out esterification dehydration reaction, after the acid number≤0.1mgKOH/g of reaction product to be obtained, stopped reaction;
(3) temperature of reaction system cooling is down to 40 DEG C, the deionized water adding 32g in reaction system wash after stratification, obtain the product after washing; Add in the product after described washing 80g mass concentration be 10% NaOH solution carry out alkali cleaning after stratification obtain the product after alkali cleaning; The mass concentration of 32g is added for (NH in the product after described alkali cleaning
4)
2sO
4solution carry out salt and wash rear stratification and get its upper organic phase;
(4) in described upper organic phase, 0.025 MEHQ is added, mix at 40 DEG C, vacuum tightness is that-0.09MPa carries out underpressure distillation and within 2 hours, sloughs solvent in organic phase, until the content <500ppm of solvent, obtains product.
The transformation efficiency of the preparation method of the present embodiment is 86%, and the purity of products obtained therefrom is 96%, and product colourity is APHA≤30.
Other embodiments are identical with embodiment 1.
Embodiment 3
The preparation method of the present embodiment comprises the following steps:
(1) successively 38.7g tri-(2-hydroxy-cyclohexyl) tricarbimide triacrylate, 21.3g vinylformic acid, 48g toluene, 3.3g methylsulphonic acid, 0.096g Salzburg vitriol, 0.117g ortho phosphorous acid are put in the 500ml four-hole boiling flask that thermometer, water trap, prolong, stirring rake are housed;
(2) oil bath heating and whipping appts is opened, temperature of reaction system is made to rise to 120 DEG C, air is passed in reaction system, and make the backflow 6 hours under constant temperature normal pressure in the reactor of described reaction system, carry out esterification dehydration reaction, after the acid number≤0.1mgKOH/g of reaction product to be obtained, stopped reaction;
(3) temperature of reaction system cooling is down to 40 DEG C, the deionized water adding 32g in reaction system wash after stratification, obtain the product after washing; Add in the product after described washing 80g mass concentration be 10% NaOH solution carry out alkali cleaning after stratification obtain the product after alkali cleaning; The mass concentration of 32g is added for (NH in the product after described alkali cleaning
4)
2sO
4solution carry out salt and wash rear stratification and get its upper organic phase;
(4) in described upper organic phase, 0.025 MEHQ is added, mix at 60 DEG C, vacuum tightness is that-0.095MPa carries out underpressure distillation and within 4 hours, sloughs solvent in organic phase, until the content <500ppm of solvent, obtains product.
The transformation efficiency of the preparation method of the present embodiment is 90%, and the purity of products obtained therefrom is 98%, and product colourity is APHA≤10.
Other embodiments are identical with embodiment 1.
Embodiment 4
The preparation method of the present embodiment, comprises the following steps:
(1) successively 38.7g tri-(2-hydroxy-cyclohexyl) tricarbimide triacrylate, 21.3g vinylformic acid, 24g ethyl acetate, 1.5g tosic acid, 0.096g cupric chloride, 0.117g inferior sodium phosphate are put in the 500ml four-hole boiling flask that thermometer, water trap, prolong, stirring rake are housed;
(2) oil bath heating and whipping appts is opened, temperature of reaction system is made to rise to 120 DEG C, air is passed in reaction system, and make the backflow 6 hours under constant temperature normal pressure in the reactor of described reaction system, carry out esterification dehydration reaction, after the acid number≤0.1mgKOH/g of reaction product to be obtained, stopped reaction;
(3) temperature of reaction system cooling is down to 40 DEG C, the deionized water adding 32g in reaction system wash after stratification, obtain the product after washing; Add in the product after described washing 80g mass concentration be 10% NaOH solution carry out alkali cleaning after stratification obtain the product after alkali cleaning; The mass concentration of 32g is added for (NH in the product after described alkali cleaning
4)
2sO
4solution carry out salt and wash rear stratification and get its upper organic phase.
(4) in described upper organic phase, add 0.025 pair of phenyl methylcarbamate, mix at 60 DEG C, vacuum tightness is that-0.095MPa carries out underpressure distillation and within 4 hours, sloughs solvent in organic phase, until the content <500ppm of solvent, obtains product.
The transformation efficiency of the preparation method of the present embodiment is 86%, and the purity of products obtained therefrom is 96%, and product colourity is APHA≤30.
Other embodiments are identical with embodiment 1.
Embodiment 5
The preparation method of the present embodiment comprises the following steps:
(1) successively 38.7g tri-(2-hydroxy-cyclohexyl) tricarbimide triacrylate, 21.3g vinylformic acid, 72g tetracol phenixin, 5.1g methylsulphonic acid, 0.096g MEHQ, 0.117g inferior sodium phosphate are put in the 500ml four-hole boiling flask that thermometer, water trap, prolong, stirring rake are housed;
(2) oil bath heating and whipping appts is opened, temperature of reaction system is made to rise to 120 DEG C, air is passed in reaction system, and make the backflow 8 hours under constant temperature normal pressure in the reactor of described reaction system, carry out esterification dehydration reaction, after the acid number≤0.1mgKOH/g of reaction product to be obtained, stopped reaction;
(3) temperature of reaction system cooling is down to 40 DEG C, the deionized water adding 32g in reaction system wash after stratification, obtain the product after washing; Add in the product after described washing 80g mass concentration be 10% NaOH solution carry out alkali cleaning after stratification obtain the product after alkali cleaning; The mass concentration of 32g is added for (NH in the product after described alkali cleaning
4)
2sO
4solution carry out salt and wash rear stratification and get its upper organic phase.
(4) in described upper organic phase, 0.025 p-tert.-butyl cresol is added, mix at 80 DEG C, vacuum tightness is that-0.1MPa carries out underpressure distillation and within 6 hours, sloughs solvent in organic phase, until the content <500ppm of solvent, obtains product.
The transformation efficiency of the preparation method of the present embodiment is 87%, and the purity of products obtained therefrom is 97%, and product colourity is APHA≤40.
Other embodiments are identical with embodiment 1.
Embodiment 6
The preparation method of the present embodiment comprises the following steps:
(1) successively 38.7g tri-(2-hydroxy-cyclohexyl) tricarbimide triacrylate, 21.3g vinylformic acid, 48g hexanaphthene, 3.3g methylsulphonic acid, 0.0213g2,6-ditertbutylparacresol, 0.0213g inferior sodium phosphate are put in the 500ml four-hole boiling flask that thermometer, water trap, prolong, stirring rake are housed;
(2) oil bath heating and whipping appts is opened, temperature of reaction system is made to rise to 120 DEG C, air is passed in reaction system, and make the backflow 8 hours under constant temperature normal pressure in the reactor of described reaction system, carry out esterification dehydration reaction, after the acid number≤0.1mgKOH/g of reaction product to be obtained, stopped reaction;
(3) temperature of reaction system cooling is down to 40 DEG C, the deionized water adding 32g in reaction system wash after stratification, obtain the product after washing; Add in the product after described washing 80g mass concentration be 10% NaOH solution carry out alkali cleaning after stratification obtain the product after alkali cleaning; The mass concentration of 32g is added for (NH in the product after described alkali cleaning
4)
2sO
4solution carry out salt and wash rear stratification and get its upper organic phase.
(4) in described upper organic phase, add 0.01 MEHQ, mix at 80 DEG C, vacuum tightness is that-0.1MPa carries out underpressure distillation and within 6 hours, sloughs solvent in organic phase, until the content <500ppm of solvent, obtains product.
The transformation efficiency of the preparation method of the present embodiment is 86%, and the purity of products obtained therefrom is 98%, and product colourity is APHA≤40.
Other embodiments are identical with embodiment 1.
Embodiment 7
The preparation method of the present embodiment comprises the following steps:
(1) successively 38.7g tri-(2-hydroxy-cyclohexyl) tricarbimide triacrylate, 21.3g vinylformic acid, 24g toluene, 24g ethyl acetate, 3.3g methylsulphonic acid, 0.17g Salzburg vitriol, 0.213g inferior sodium phosphate are put in the 500ml four-hole boiling flask that thermometer, water trap, prolong, stirring rake are housed;
(2) oil bath heating and whipping appts is opened, temperature of reaction system is made to rise to 120 DEG C, air is passed in reaction system, and make the backflow 8 hours under constant temperature normal pressure in the reactor of described reaction system, carry out esterification dehydration reaction, after the acid number≤0.1mgKOH/g of reaction product to be obtained, stopped reaction;
(3) temperature of reaction system cooling is down to 40 DEG C, the deionized water adding 32g in reaction system wash after stratification, obtain the product after washing; Add in the product after described washing 80g mass concentration be 10% NaOH solution carry out alkali cleaning after stratification obtain the product after alkali cleaning; The mass concentration of 32g is added for (NH in the product after described alkali cleaning
4)
2sO
4solution carry out salt and wash rear stratification and get its upper organic phase.
(4) in described upper organic phase, 0.04g p-ten.-butylcatechol is added, mix at 80 DEG C, vacuum tightness is that-0.1MPa carries out underpressure distillation and within 8 hours, sloughs solvent in organic phase, until the content <500ppm of solvent, obtains product.
The transformation efficiency of the preparation method of the present embodiment is 88%, and the purity of products obtained therefrom is 96%, and product colourity is APHA≤20.
Other embodiments are identical with embodiment 1.
The foregoing is only preferred embodiment of the present invention, not in order to limit the present invention, all any amendments done within the spirit and principles in the present invention, equivalent replacement and improvement etc., all should be included within protection scope of the present invention.
Claims (10)
1. the preparation method of three (2-hydroxy-cyclohexyl) tricarbimide triacrylate, is characterized in that, comprise the following steps:
(1) add three (2-hydroxy-cyclohexyl) chlorinated isocyanurates, vinylformic acid, solvent, catalyzer, the first stopper and oxidation inhibitor in the reactor successively, after mixing, obtain reaction system;
(2) temperature of reaction system remains on 90 ~ 150 DEG C, in reaction system, pass into air, makes described reaction system be back to reaction end under constant temperature normal pressure, obtains reaction product;
(3) described reaction product is washed successively, alkali cleaning, salt washes rear stratification, get its upper strata and obtain organic phase;
(4) described organic phase is added the second stopper and the solvent in organic phase is sloughed in underpressure distillation, pressure filtration is carried out to organic phase, obtains three (2-hydroxy-cyclohexyl) tricarbimide triacrylate.
2. the preparation method of a kind of three (2-hydroxy-cyclohexyl) tricarbimide triacrylate according to claim 1, it is characterized in that, described three (2-hydroxy-cyclohexyl) chlorinated isocyanurates and acrylic acid mol ratio are 1:2 ~ 8, the consumption of described catalyzer is 2.5 ~ 8.5% of three (2-hydroxy-cyclohexyl) chlorinated isocyanurates and vinylformic acid total mass, the consumption of described oxidation inhibitor is 0.1 ~ 1% of vinylformic acid quality, the consumption of described first stopper is 0.1 ~ 0.8% of vinylformic acid quality, the consumption of described second stopper is 0.05 ~ 0.2% of vinylformic acid quality.
3. the preparation method of a kind of three (2-hydroxy-cyclohexyl) tricarbimide triacrylate according to claim 1, is characterized in that, in described step (2), after the acid number≤0.1mgKOH/g of reaction product, and stopped reaction.
4. the preparation method of a kind of three (2-hydroxy-cyclohexyl) tricarbimide triacrylate according to claim 1, is characterized in that, in described step (4), until the content <500ppm of solvent, obtain product.
5. the preparation method of a kind of three (2-hydroxy-cyclohexyl) tricarbimide triacrylate according to claim 1, it is characterized in that, in described step (1), described solvent be selected from toluene, ethyl acetate, tetracol phenixin and hexanaphthene one or more, the consumption of described solvent is 40 ~ 120% of three (2-hydroxy-cyclohexyl) chlorinated isocyanurates and vinylformic acid total mass.
6. the preparation method of a kind of three (2-hydroxy-cyclohexyl) tricarbimide triacrylate according to claim 1, it is characterized in that, described oxidation inhibitor is the salt compounds of ortho phosphorous acid or ortho phosphorous acid.
7. the preparation method of a kind of three (2-hydroxy-cyclohexyl) tricarbimide triacrylate according to claim 1, it is characterized in that, described first stopper be selected from cupric chloride, Salzburg vitriol, MEHQ and 2,6 ditertiary butyl p cresol one or more.
8. the preparation method of a kind of three (2-hydroxy-cyclohexyl) tricarbimide triacrylate according to claim 1, it is characterized in that, described second stopper is selected from MEHQ, to one or more in phenyl methylcarbamate, p-tert.-butyl cresol, p-ten.-butylcatechol.
9. the preparation method of a kind of three (2-hydroxy-cyclohexyl) tricarbimide triacrylate according to claim 1, it is characterized in that, vacuum tightness when described upper organic phase carries out underpressure distillation is-0.09 ~-0.1MPa, and temperature is 40 ~ 80 DEG C, and the time is 2 ~ 6 hours.
10. three (2-hydroxy-cyclohexyl) tricarbimide triacrylate that the preparation method as described in any one of claim 1 ~ 9 obtains.
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| CN201510931213.0A CN105348208A (en) | 2015-12-11 | 2015-12-11 | Preparation method of tris(2-hydroxycyclohexyl) isocyanuric acid triacrylate |
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| CN109796421A (en) * | 2017-11-17 | 2019-05-24 | 上海飞凯光电材料股份有限公司 | A kind of acrylate and its synthetic method, coating |
| CN115728427A (en) * | 2022-12-09 | 2023-03-03 | 常州斯威克光伏新材料有限公司 | Acid value determination method for photovoltaic adhesive film and auxiliary materials |
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| CN102260221A (en) * | 2011-06-07 | 2011-11-30 | 华南理工大学 | Preparation method of isocyanurate acrylate or isocyanurate methacrylate monomer |
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| CN109796421A (en) * | 2017-11-17 | 2019-05-24 | 上海飞凯光电材料股份有限公司 | A kind of acrylate and its synthetic method, coating |
| CN115728427A (en) * | 2022-12-09 | 2023-03-03 | 常州斯威克光伏新材料有限公司 | Acid value determination method for photovoltaic adhesive film and auxiliary materials |
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