CN115028531A - Epoxy cyclohexane hydroxyethyl methacrylate, epoxy cyclohexane hydroxyethyl acrylate and synthesis method thereof - Google Patents
Epoxy cyclohexane hydroxyethyl methacrylate, epoxy cyclohexane hydroxyethyl acrylate and synthesis method thereof Download PDFInfo
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- CN115028531A CN115028531A CN202210815743.9A CN202210815743A CN115028531A CN 115028531 A CN115028531 A CN 115028531A CN 202210815743 A CN202210815743 A CN 202210815743A CN 115028531 A CN115028531 A CN 115028531A
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- Prior art keywords
- hydroxyethyl methacrylate
- hydroxyethyl
- synthesis method
- epoxy cyclohexane
- epoxy
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- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 title claims abstract description 28
- 238000001308 synthesis method Methods 0.000 title claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000004593 Epoxy Substances 0.000 claims abstract description 13
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 239000003112 inhibitor Substances 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims abstract description 6
- 238000007599 discharging Methods 0.000 claims abstract description 6
- 238000005070 sampling Methods 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical group COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 6
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 5
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 239000002879 Lewis base Substances 0.000 claims description 2
- 238000006266 etherification reaction Methods 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 150000007527 lewis bases Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 239000000178 monomer Substances 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 4
- 238000003848 UV Light-Curing Methods 0.000 abstract description 3
- 238000001723 curing Methods 0.000 abstract description 3
- 238000000576 coating method Methods 0.000 description 4
- -1 i.e. Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 230000010062 adhesion mechanism Effects 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229950006298 cicrotoic acid Drugs 0.000 description 1
- 239000011141 cosmetic packaging material Substances 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/28—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group
- C07C67/29—Preparation of carboxylic acid esters by modifying the hydroxylic moiety of the ester, such modification not being an introduction of an ester group by introduction of oxygen-containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides epoxy cyclohexane hydroxyethyl methacrylate, epoxy cyclohexane hydroxyethyl acrylate and a synthesis method thereof, belonging to the technical field of organic synthesis. Adding hydroxyethyl methacrylate, a catalyst and a polymerization inhibitor into a reactor, starting stirring, cooling in a water bath, dropwise adding cyclohexene oxide, controlling the reaction temperature below 60 ℃, keeping the temperature at 60 +/-2 ℃ for 0.5-1.5h after the dropwise adding of the cyclohexene oxide is finished, sampling to determine the epoxy value, and discharging to obtain the epoxy cyclohexane hydroxyethyl methacrylate when the epoxy value is not more than 0.05 after the reaction is finished. The invention relates to a monoacrylate with a six-membered ring, which is a novel UV curing monomer, has good dilutability and high curing rate, has small thermal shrinkage and good thermal stability due to the existence of the six-membered ring, is a third acrylate monomer, and has wide application prospect.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to epoxy cyclohexane hydroxyethyl methacrylate, epoxy cyclohexane hydroxyethyl acrylate and a synthesis method thereof.
Background
Among the coating components, the film-forming substances, i.e., resins (oligomers) and monomers, have the greatest effect on adhesion. The influencing factors of adhesion are very complex and up to now there is no perfect theory explaining all adhesion mechanisms. The application of UV coating on plastic base material is very extensive, and relates to the fields of electronic products, automobile interior and exterior decorations, cosmetic packaging materials and the like. Common plastic substrates include ABS, PC, ABS + PC alloy, PET, PMMA, and the like. Among them, adhesion is a focus of great attention. In published professional books of UV coatings, the relationship between the adhesion and the chemical structure of a film forming agent is explained more comprehensively, and the concept and data of measurement are lacked. At the same time, the effect of "volume shrinkage" is mostly emphasized: it is believed that acrylic double bonds are converted from intermolecular distances to intramolecular distances during polymerization, and thus volume shrinkage occurs, causing internal stress, and finally affecting the adhesion of the coating film on the substrate. However, in practice, this interpretation is often quite different from the practical result, causing great confusion to the practitioner.
Disclosure of Invention
The invention aims to provide epoxy cyclohexane hydroxyethyl methacrylate, epoxy cyclohexane hydroxyethyl acrylate and a synthesis method thereof, relates to monoacrylate with a six-membered ring, is a novel UV curing monomer, has good dilutability and high curing rate, has small thermal shrinkage and good thermal stability due to the existence of the six-membered ring, is a third type acrylate monomer, and has wide application prospect.
The technical scheme of the invention is realized as follows:
the invention provides a method for synthesizing epoxy cyclohexane hydroxyethyl methacrylate, which comprises the step of carrying out etherification reaction on epoxy cyclohexane acyl and hydroxyethyl methacrylate in the presence of Lewis acid or Lewis base to generate epoxy cyclohexane hydroxyethyl methacrylate.
As a further improvement of the invention, the specific preparation method is as follows: adding hydroxyethyl methacrylate, a catalyst and a polymerization inhibitor into a reactor, starting stirring, cooling in a water bath, dropwise adding cyclohexene oxide, controlling the reaction temperature below 60 ℃, keeping the temperature at 60 +/-2 ℃ for 0.5-1.5h after the dropwise adding of the cyclohexene oxide is finished, sampling to determine the epoxy value, and discharging to obtain the epoxy cyclohexane hydroxyethyl methacrylate when the epoxy value is not more than 0.05 after the reaction is finished.
As a further improvement of the invention, the molar ratio of the cyclohexene oxide to the hydroxyethyl methacrylate is 1-1.05: 1.
as a further improvement of the invention, the catalyst is selected from at least one of boron trifluoride diethyl etherate, metallic sodium, sodium methoxide, potassium hydroxide or sodium hydroxide.
As a further improvement of the invention, the mass ratio of the catalyst to the hydroxyethyl methacrylate is 0.001-0.01: 1.
as a further improvement of the invention, the polymerization inhibitor is p-hydroxyanisole.
As a further improvement of the invention, the mass ratio of the polymerization inhibitor to the hydroxyethyl methacrylate is 0.001-0.01: 1.
the invention further protects the epoxy cyclohexane hydroxyethyl methacrylate prepared by the synthesis method.
The invention further provides a synthesis method of the epoxy cyclohexane hydroxyethyl acrylate, wherein the hydroxyethyl methacrylate is replaced by hydroxyethyl acrylate, and the prepared product is the epoxy cyclohexane hydroxyethyl acrylate.
The invention further protects the epoxy cyclohexane acrylic acid hydroxyethyl ether prepared by the synthesis method.
The invention has the following beneficial effects: the invention relates to a monoacrylate with a six-membered ring, which is a novel UV curing monomer, has good dilutability and high curing speed, has small thermal shrinkage and good thermal stability due to the existence of the six-membered ring, is a third type acrylate monomer, and has wide application prospect.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to these drawings without creative efforts.
FIG. 1 is a schematic diagram showing the synthesis of hydroxyethyl epoxycyclohexane acrylate;
FIG. 2 is a schematic diagram of the synthesis of hydroxyethyl epoxycyclohexane methacrylate.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Referring to FIG. 1, 348g of hydroxyethyl acrylate, 1.7g of p-hydroxyanisole and 1g of boron trifluoride diethyl etherate complex are put into a 1000mL flask, stirring is started, water bath cooling is carried out, 294g of epoxy cyclohexanoyl is added into a constant pressure dropping funnel, the reaction temperature is controlled to be less than 60 ℃, 1.5h of dropping is finished, the reaction is carried out at 60 +/-2 ℃ for 1h, sampling is carried out, the epoxy value is detected to be 0.003, discharging is carried out, 644.0g of product is obtained, the yield is 99.9%, the product is colorless and transparent in appearance, and the viscosity is 39cps (25 ℃).
Example 2
As shown in figure 1, 390g of hydroxyethyl acrylate and 1.7g of p-hydroxyanisole are put into a 1000mL flask, stirring is started, 1.2g of sodium metal is slowly added, the sodium metal is completely dissolved after 20min, cooling is carried out by using a water bath, 294g of epoxy cyclohexanoyl is added into a constant-pressure dropping funnel, the reaction temperature is controlled to be less than 60 ℃, 1.5h of epoxy cyclohexanoyl is added, reaction is carried out at 60 +/-2 ℃ for 1h, the epoxy value is 0.002 by sampling detection, discharging is carried out, 696.0g of a product is obtained, the yield is 99.9%, the product is colorless and transparent in appearance, and the viscosity is 45cps (25 ℃).
Example 3
As shown in FIG. 2, 393g of hydroxyethyl methacrylate was put into a 1000mL flask, stirred, cooled in a water bath, and then 1.7g of p-hydroxyanisole and 1.5g of sodium methoxide were added thereto and mixed well. 294g of epoxy-cyclohexanoyl is added into a constant-pressure dropping funnel, the reaction temperature is controlled to be less than 60 ℃, the dropwise addition is finished within 1.5h, the temperature is kept at 60 +/-2 ℃ for 1h, the temperature is kept for reaction, the epoxy value is sampled and detected to be 0.004, the material is discharged, 689g of the product is obtained, the yield is 99.9%, the appearance of the product is colorless and transparent, and the viscosity is 40cps (25 ℃).
Example 4
As shown in FIG. 1, 348kg of hydroxyethyl acrylate was charged into 1m 3 2.5kg of p-hydroxyanisole and 2kg of boron trifluoride etherate are added to a stainless steel reaction kettle of (2), stirring is started, 294kg of cyclohexene oxide is weighed, and then 0.5m of cyclohexene oxide is charged 3 The high-order dripping groove. Opening a cooling valve of an inner disc of the reaction kettle, opening an outlet valve of the high-position dripping groove to control the feeding speed, maintaining the temperature of the material liquid in the kettle to be less than 60 ℃, after 2.5 hours, finishing the feeding of the epoxy cyclohexane, carrying out heat preservation reaction at 60 +/-2 ℃ for 1.5 hours, sampling and detecting the epoxy value to be 0.001, stopping the reaction, filtering and discharging by using 300-mesh filter cloth to obtain 642kg of a product, wherein the yield is 99 percent, the appearance of the product is colorless and transparent, and the viscosity is 38cps (25 ℃).
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A synthesis method of epoxy cyclohexane hydroxyethyl methacrylate is characterized in that epoxy cyclohexane and hydroxyethyl methacrylate are subjected to etherification reaction in the presence of Lewis acid or Lewis base to generate epoxy cyclohexane hydroxyethyl methacrylate.
2. The synthesis method according to claim 1, characterized in that the specific preparation method is as follows: adding hydroxyethyl methacrylate, a catalyst and a polymerization inhibitor into a reactor, starting stirring, cooling in a water bath, dropwise adding cyclohexene oxide, controlling the reaction temperature below 60 ℃, keeping the temperature at 60 +/-2 ℃ for 0.5-1.5h after the dropwise adding of the cyclohexene oxide is finished, sampling to determine the epoxy value, and discharging to obtain the epoxy cyclohexane hydroxyethyl methacrylate when the epoxy value is not more than 0.05 after the reaction is finished.
3. The synthesis method according to claim 2, wherein the molar ratio of cyclohexene oxide to hydroxyethyl methacrylate is 1-1.05: 1.
4. the method of claim 2, wherein the catalyst is at least one selected from boron trifluoride etherate, sodium metal, sodium methoxide, potassium hydroxide, and sodium hydroxide.
5. The synthesis method according to claim 4, wherein the mass ratio of the catalyst to the hydroxyethyl methacrylate is 0.001-0.01: 1.
6. the synthesis method according to claim 2, wherein the polymerization inhibitor is p-hydroxyanisole.
7. The synthesis method according to claim 6, wherein the mass ratio of the polymerization inhibitor to the hydroxyethyl methacrylate is 0.001-0.01: 1.
8. epoxycyclohexane hydroxyethyl methacrylate prepared by the synthesis method as described in any one of claims 1 to 7.
9. A method for synthesizing hydroxyethyl epoxycyclohexane acrylate, characterized in that hydroxyethyl methacrylate is replaced by hydroxyethyl acrylate according to any one of claims 1 to 7, and the obtained product is hydroxyethyl epoxycyclohexane acrylate.
10. A hydroxyethyl epoxycyclohexane acrylate prepared according to the method of claim 9.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210815743.9A CN115028531A (en) | 2022-07-12 | 2022-07-12 | Epoxy cyclohexane hydroxyethyl methacrylate, epoxy cyclohexane hydroxyethyl acrylate and synthesis method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210815743.9A CN115028531A (en) | 2022-07-12 | 2022-07-12 | Epoxy cyclohexane hydroxyethyl methacrylate, epoxy cyclohexane hydroxyethyl acrylate and synthesis method thereof |
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| CN115028531A true CN115028531A (en) | 2022-09-09 |
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| CN202210815743.9A Pending CN115028531A (en) | 2022-07-12 | 2022-07-12 | Epoxy cyclohexane hydroxyethyl methacrylate, epoxy cyclohexane hydroxyethyl acrylate and synthesis method thereof |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03120263A (en) * | 1989-10-02 | 1991-05-22 | Daicel Chem Ind Ltd | Preparation of (meth)acrylate compound |
| JPH04283575A (en) * | 1991-03-12 | 1992-10-08 | Daicel Chem Ind Ltd | Production of epoxidized (meth)acrylate compound |
| CN101591312A (en) * | 2008-08-27 | 2009-12-02 | 岳阳昌德化工实业有限公司 | A kind of glycidyl ether that contains cyclohexyl binary ether alcohol and preparation method thereof |
| CN103030559A (en) * | 2012-12-17 | 2013-04-10 | 南昌大学 | Method for synthesizing ultraviolet curable photosensitive diluent-2-ethyl hexyl glycidyl ether acrylate |
| CN114315671A (en) * | 2020-09-28 | 2022-04-12 | 山东康乔生物科技有限公司 | Organic sulfur compound and preparation method and application thereof |
| WO2022133680A1 (en) * | 2020-12-21 | 2022-06-30 | 张佩嫦 | Uv-curable low-viscosity polyester and method for preparation thereof |
-
2022
- 2022-07-12 CN CN202210815743.9A patent/CN115028531A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03120263A (en) * | 1989-10-02 | 1991-05-22 | Daicel Chem Ind Ltd | Preparation of (meth)acrylate compound |
| JPH04283575A (en) * | 1991-03-12 | 1992-10-08 | Daicel Chem Ind Ltd | Production of epoxidized (meth)acrylate compound |
| CN101591312A (en) * | 2008-08-27 | 2009-12-02 | 岳阳昌德化工实业有限公司 | A kind of glycidyl ether that contains cyclohexyl binary ether alcohol and preparation method thereof |
| CN103030559A (en) * | 2012-12-17 | 2013-04-10 | 南昌大学 | Method for synthesizing ultraviolet curable photosensitive diluent-2-ethyl hexyl glycidyl ether acrylate |
| CN114315671A (en) * | 2020-09-28 | 2022-04-12 | 山东康乔生物科技有限公司 | Organic sulfur compound and preparation method and application thereof |
| WO2022133680A1 (en) * | 2020-12-21 | 2022-06-30 | 张佩嫦 | Uv-curable low-viscosity polyester and method for preparation thereof |
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