CN108383988A - A kind of epoxy acrylic resin and its preparation method and application of five degrees of functionality - Google Patents
A kind of epoxy acrylic resin and its preparation method and application of five degrees of functionality Download PDFInfo
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- CN108383988A CN108383988A CN201810271002.2A CN201810271002A CN108383988A CN 108383988 A CN108383988 A CN 108383988A CN 201810271002 A CN201810271002 A CN 201810271002A CN 108383988 A CN108383988 A CN 108383988A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/102—Printing inks based on artificial resins containing macromolecular compounds obtained by reactions other than those only involving unsaturated carbon-to-carbon bonds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
- C09D171/02—Polyalkylene oxides
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J171/00—Adhesives based on polyethers obtained by reactions forming an ether link in the main chain; Adhesives based on derivatives of such polymers
- C09J171/02—Polyalkylene oxides
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Paints Or Removers (AREA)
Abstract
The invention discloses a kind of epoxy acrylic resins and its preparation method and application of five degrees of functionality, have the following structure formula：
Description
Technical field
The invention belongs to photo-curing material technical fields, and in particular to a kind of epoxy acrylic resin of five degree of functionality and its
Preparation method and application.
Background technology
A kind of efficient, energy saving, economic, environmentally friendly, wide adaptability new material of photo-curing material, especially because country is to molten
The use of agent is limited, and photo-curing material is increasingly taken seriously as a kind of environment-friendly materials.Wherein, epoxy acrylic
Ester resin is that current application surface is the most extensive, the maximum Photocurable oligomers of market demand, in coating, ink, adhesive
Equal sector applications are more and more extensive, many fields substituted material it is traditional contain solvent material.
Currently, epoxy acrylic resin on the market is substantially following several types：Bisphenol A epoxy acrylate class, phenol
Aldehyde Epoxy Acrylates, the Epoxy Acrylates of various modifications and epoxidized oil esters of acrylic acid.Wherein bisphenol-A epoxy third
Olefin(e) acid esters dosage is maximum, but its light aging resisting and anti-yellowing property are poor.The Epoxy Acrylates of various modifications are substantially
Bisphenol A-type, equally exist the problem of light aging resisting and anti-yellowing property difference.Epoxy Phenolic Acrylates class is polyfunctionality
Resin, but its viscosity is larger, and the curing rate of epoxidized oil esters of acrylic acid is too slow, resin that can only be high with other activity is taken
With use.
Invention content
To solve the defect of above-mentioned prior art problem, the primary purpose of the present invention is that providing a kind of ring of five degrees of functionality
Oxypropylene acid resin, the resin have many advantages, such as that viscosity is low, curing rate is fast, light aging resisting and anti-yellowing property are good.
Another object of the present invention is to provide the preparation methods of the epoxy acrylic resin of above-mentioned five degree of functionality.
The present invention is achieved through the following technical solutions：
A kind of epoxy acrylic resin of five degrees of functionality, has the following structure formula：
R3Represent H or CH3；
N=0~5000.
The epoxy acrylic resin of five degree of functionality of the present invention, is made of the component including following parts by weight：
（A）Five 18~55 parts of function polyalcohols
（B）32~63 parts of acid anhydrides
（C）28~120 parts of alicyclic epoxy acrylate
（D）1 0.02~0.5 part of catalyst
（E）2 0.02~0.5 part of catalyst
（F）0.02~0.5 part of polymerization inhibitor.
The five functions polyalcohol is in xylitol, ethoxyquin xylitol, the third oxidation xylitol or caprolactone xylitol
One or more of mixing.
The acid anhydrides is succinic anhydride, glutaric anhydride, maleic anhydride, phthalic anhydride, pentahydro- phthalic anhydride, hexahydrophthalic anhydride, methyl
The mixing of one or more of hexahydrophthalic anhydride or cyclopentene dicarboxylic anhydride.
The alicyclic epoxy acrylate is 3,4- epoxycyclohexyl-methyls methacrylate or 3,4- epoxy hexamethylenes
The mixing of one or both of methyl acrylate.
The catalyst 1 is the mixing of one or more of organic tin catalyst or organo-bismuth class catalyst.
The catalyst 2 is one or more of five Phenylphosphines, five butylammonium bromides or five ethylbenzylammonium chlorides
Mixing.
The polymerization inhibitor is p-hydroxyanisole, hydroquinone, 2- tert-butyl hydroquinone or 2, and 5- di-t-butyls are to benzene
The mixing of one or more of diphenol.
The epoxy acrylic resin of five degree of functionality is 60000-120000cps in 25 DEG C of viscosity, preferably
65000-85000 cps, viscosity is according to GB/T10247-2008 standard testings.
The present invention also provides the preparation methods of the epoxy acrylic resin of above-mentioned five degree of functionality, include the following steps：
It counts in parts by weight, 18~55 part of five function polyalcohol, 32~63 parts of acid anhydrides, 0.02~0.5 part of catalyst 1 is added
Into reaction vessel, it is heated to 70-130 DEG C, is stirred to react 3~6 hours, when surveying acid value to heat preceding total acid number 1/2 ± 3%,
Cool to room temperature, 28~50 parts of alicyclic epoxy acrylate of input, 0.02~0.5 part of polymerization inhibitor, 0.02~0.5 part of catalysis
In agent 2 to reaction vessel, be heated to 80~140 DEG C, until survey acid value be less than 5mgKOH/g when, the clear, colorless of cooling discharge or
Weak yellow liquid resin is the epoxy acrylic resin of five degrees of functionality.
The present invention also provides epoxy acrylic resin the answering in coating, ink or adhesive of five above-mentioned degrees of functionality
With.
Compared with prior art, the present invention having the advantages that：
（1）The present invention substitutes traditional bisphenol A epoxy acrylate and phenolic aldehyde ring by introducing alicyclic epoxy acrylate
Oxypropylene acid esters so that the Epocryl viscosity for five degrees of functionality prepared substantially reduces, and production technology obtains very
Big simplification, meanwhile, it solves the problems, such as that the light aging resisting of traditional Epocryl and anti-yellowing property are poor, prepares
The Epocryl of five obtained degrees of functionality is low with viscosity, curing rate is fast, light aging resisting and anti-yellowing property are good
The advantages that, it can be widely used in coating, ink or adhesive area；
（2）The present invention is different from conventional epoxy acrylate by introducing five function polyalcohols, the design of novel structure
The mostly structure of two functions, makes its curing rate and hardness greatly improve, and further widens its application.
Specific implementation mode
It is further illustrated the present invention below by specific implementation mode, following embodiment is the specific embodiment party of the present invention
Formula, but embodiments of the present invention are not limited by following embodiments, other any Spirit Essences without departing from the present invention
With under principle made by changes, modifications, substitutions, combinations, simplifications, should be equivalent substitute mode, be included in the present invention
Within protection domain.
Embodiment 1：
It counts in parts by weight, 15 parts of xylitols, 49 parts of maleic anhydrides, 0.1 part of organic tin catalyst is added to reaction
In container, 100 DEG C are heated to, is stirred to react 5 hours, when surveying acid value to heat preceding total acid number 1/2 ± 3%, cools to room temperature,
100 parts of 3,4- epoxycyclohexyl-methyls methacrylates, 0.1 part of hydroquinone, 0.1 part of five butylammonium bromide are put into instead
It answers in container, is heated to 110 DEG C, when being less than 5mgKOH/g until surveying acid value, the clear, colorless or weak yellow liquid of cooling discharge
Resin is the epoxy acrylic resin A of five degrees of functionality.
The viscosity of the epoxy acrylic resin of five degrees of functionality being prepared, curing rate, weather resistance are shown in Table 1.
Embodiment 2：
It counts in parts by weight, 20 parts of ethoxyquin xylitols, 38 parts of glutaric anhydrides, 0.1 part of organic tin catalyst is added to instead
It answers in container, is heated to 110 DEG C, be stirred to react 4 hours, when surveying acid value to heat preceding total acid number 1/2 ± 3%, cool to room
Temperature, 44 parts of 3,4- epoxycyclohexyl-methyls acrylate of input, 0.1 part of hydroquinone, 0.1 part of five butylammonium bromide to reaction
In container, 100 DEG C are heated to, when being less than 5mgKOH/g until surveying acid value, the clear, colorless of cooling discharge or weak yellow liquid tree
Fat is the epoxy acrylic resin B of five degrees of functionality.
The viscosity of the epoxy acrylic resin of five degrees of functionality being prepared, curing rate, weather resistance are shown in Table 1.
Embodiment 3：
It counts in parts by weight, aoxidizing xylitol, 45 parts of cyclopentene dicarboxylic anhydrides, 0.1 part of organic tin catalyst by 30 part third adds
Enter into reaction vessel, be heated to 120 DEG C, is stirred to react 3 hours, when surveying acid value to heat preceding total acid number 1/2 ± 3%, cooling
To room temperature, 45 parts of 3,4- epoxycyclohexyl-methyls acrylate of input, 0.1 part of hydroquinone, 0.1 part of five butylammonium bromide arrive
In reaction vessel, 95 DEG C are heated to, when being less than 5mgKOH/g until surveying acid value, the clear, colorless or weak yellow liquid of cooling discharge
Resin is the epoxy acrylic resin C of five degrees of functionality.
The viscosity of the epoxy acrylic resin of five degrees of functionality being prepared, curing rate, weather resistance are shown in Table 1.
Embodiment 4：
It counts in parts by weight, 45 parts of caprolactone xylitols, 55 parts of succinic anhydrides, 0.1 part of organic tin catalyst is added to
In reaction vessel, 95 DEG C are heated to, is stirred to react 5 hours, when surveying acid value to heat preceding total acid number 1/2 ± 3%, cools to room
Temperature, 50 parts of 3,4- epoxycyclohexyl-methyls methacrylates of input, 0.1 part of hydroquinone, 0.1 part of five butylammonium bromide arrive
In reaction vessel, 115 DEG C are heated to, when being less than 5mgKOH/g until surveying acid value, the clear, colorless or light yellow liquid of cooling discharge
Body resin is the epoxy acrylic resin D of five degrees of functionality.
The viscosity of the epoxy acrylic resin of five degrees of functionality being prepared, curing rate, weather resistance are shown in Table 1.
Comparative example 1：
It counts in parts by weight, 15 parts of xylitols, 49 parts of maleic anhydrides, 0.1 part of organic tin catalyst is added to reaction
In container, 100 DEG C are heated to, is stirred to react 5 hours, when surveying acid value to heat preceding total acid number 1/2 ± 3%, cools to room temperature,
195 parts of bisphenol A type epoxy resins, 0.1 part of hydroquinone, 0.1 part of tetrabutylammonium bromide, 36 parts of acrylic acid are put into reaction to hold
In device, 110 DEG C are heated to, when being less than 5mgKOH/g until surveying acid value, the clear, colorless or weak yellow liquid resin of cooling discharge
For the epoxy acrylic resin E of five degrees of functionality.
The viscosity of the epoxy acrylic resin of five degrees of functionality being prepared, curing rate, weather resistance are shown in Table 1.
Comparative example 2：
Count in parts by weight, by 40 parts of novolac epoxy resins, 0.1 part of hydroquinone, 0.1 part of tetrabutylammonium bromide, 15 part third
Olefin(e) acid is added in reaction vessel, is heated to 110 DEG C, when being less than 5mgKOH/g until surveying acid value, the clear, colorless of cooling discharge
Or the epoxy acrylic resin F that weak yellow liquid resin is.
The viscosity of the epoxy acrylic resin being prepared, curing rate, weather resistance are shown in Table 1.
The performance test results of 1 embodiment and comparative example of table
| Cps/25 DEG C of viscosity | Solidification energy mJ/cm2 | Weatherability | ||
| Embodiment 1 | Resin A | 72314 | 55 | Ok |
| Embodiment 2 | Resin B | 72453 | 52 | Ok |
| Embodiment 3 | Resin C | 74352 | 56 | Ok |
| Embodiment 4 | Resin D | 73546 | 52 | Ok |
| Comparative example 1 | Resin E | 362341 | 68 | Turn yellow |
| Comparative example 2 | Resin F | 201232 | 81 | Slightly turn yellow |
Each performance test methods or standard：
Viscosity：GB/T10247-2008
Weatherability：GB1767-7989.
Claims (9)
1. a kind of epoxy acrylic resin of five degrees of functionality, has the following structure formula：
R3Represent H or CH3；
N=0~5000.
2. the epoxy acrylic resin of five degree of functionality according to claim 1, which is characterized in that by including following parts by weight
Several components are made：
（A）Five 18~55 parts of function polyalcohols
（B）32~63 parts of acid anhydrides
（C）28~50 parts of alicyclic epoxy acrylate
（D）1 0.02~0.5 part of catalyst
（E）2 0.02~0.5 part of catalyst
（1）0.02~0.5 part of polymerization inhibitor.
3. the epoxy acrylic resin of five degree of functionality according to claim 2, which is characterized in that the five functions polyalcohol
For the mixing of one or more of xylitol, ethoxyquin xylitol, the third oxidation xylitol or caprolactone xylitol.
4. the epoxy acrylic resin of five degree of functionality according to claim 2, which is characterized in that the acid anhydrides is succinic acid
Acid anhydride, glutaric anhydride, maleic anhydride, phthalic anhydride, pentahydro- phthalic anhydride, hexahydrophthalic anhydride, methyl hexahydrophthalic anhydride or cyclopentene dicarboxylic anhydride
One or more of mixing.
5. the epoxy acrylic resin of five degree of functionality according to claim 2, which is characterized in that the alicyclic epoxy third
Olefin(e) acid ester be 3,4- epoxycyclohexyl-methyls methacrylate or one kind in 3,4- epoxycyclohexyl-methyl acrylate or
Two kinds of mixing.
6. the epoxy acrylic resin of five degree of functionality according to claim 2, which is characterized in that the catalyst 1 is to have
The mixing of one or more of machine tin catalyst or organo-bismuth class catalyst；The catalyst 2 is five Phenylphosphines, five butyl
The mixing of one or more of ammonium bromide or five ethylbenzylammonium chlorides；The polymerization inhibitor is p-hydroxyanisole, to benzene two
Phenol, 2- tert-butyl hydroquinone or 2, the mixing of one or more of 5- di-tert-butyl hydroquinones.
7. according to the preparation method of the epoxy acrylic resin of five degree of functionality of claim 1-6 any one of them, feature exists
In the epoxy acrylic resin of, five degree of functionality in 25 DEG C of viscosity be 60000-120000cps, preferably 65000-
85000 cps, viscosity is according to GB/T10247-2008 standard testings.
8. the preparation method of the epoxy acrylic resin of five degree of functionality of claim 1-7 any one of them, which is characterized in that packet
Include following steps：
It counts in parts by weight, 18~55 part of five function polyalcohol, 32~63 parts of acid anhydrides, 0.02~0.5 part of catalyst 1 is added
Into reaction vessel, it is heated to 70-130 DEG C, is stirred to react 3~6 hours, when surveying acid value to heat preceding total acid number 1/2 ± 3%,
Cool to room temperature, 28~50 parts of alicyclic epoxy acrylate of input, 0.02~0.5 part of polymerization inhibitor, 0.02~0.5 part of catalysis
In agent 2 to reaction vessel, be heated to 80~140 DEG C, until survey acid value be less than 5mgKOH/g when, the clear, colorless of cooling discharge or
Weak yellow liquid resin is the epoxy acrylic resin of five degrees of functionality.
9. the epoxy acrylic resin of five degree of functionality of claim 1-7 any one of them is in coating, ink or adhesive
Using.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810271002.2A CN108383988B (en) | 2018-03-29 | 2018-03-29 | Epoxy acrylic resin with five-functionality degree, and preparation method and application thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810271002.2A CN108383988B (en) | 2018-03-29 | 2018-03-29 | Epoxy acrylic resin with five-functionality degree, and preparation method and application thereof |
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| CN108383988A true CN108383988A (en) | 2018-08-10 |
| CN108383988B CN108383988B (en) | 2020-05-19 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111423574A (en) * | 2020-04-28 | 2020-07-17 | 淮安巴德聚氨酯科技有限公司 | Dispersing agent for polymer polyol with cyclohexane structure and preparation method thereof |
| CN112279999A (en) * | 2020-11-09 | 2021-01-29 | 广东石油化工学院 | Biodegradable radiation-curable urethane (meth) acrylate and preparation method thereof |
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| JPH02142748A (en) * | 1988-11-24 | 1990-05-31 | Daicel Chem Ind Ltd | Polyether compound |
| CN102358717A (en) * | 2011-07-07 | 2012-02-22 | 华东理工大学 | Alicyclic epoxy acrylate prepolymer and preparation method thereof |
| CN105733421A (en) * | 2014-12-09 | 2016-07-06 | 比亚迪股份有限公司 | Ultraviolet-curing protective coating and preparation method thereof |
| CN107828050A (en) * | 2017-11-16 | 2018-03-23 | 广州日高新材料科技有限公司 | Modified epoxy acrylate resin and preparation method thereof |
-
2018
- 2018-03-29 CN CN201810271002.2A patent/CN108383988B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02142748A (en) * | 1988-11-24 | 1990-05-31 | Daicel Chem Ind Ltd | Polyether compound |
| CN102358717A (en) * | 2011-07-07 | 2012-02-22 | 华东理工大学 | Alicyclic epoxy acrylate prepolymer and preparation method thereof |
| CN105733421A (en) * | 2014-12-09 | 2016-07-06 | 比亚迪股份有限公司 | Ultraviolet-curing protective coating and preparation method thereof |
| CN107828050A (en) * | 2017-11-16 | 2018-03-23 | 广州日高新材料科技有限公司 | Modified epoxy acrylate resin and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 胡剑飞等: "一种脂肪族多官能度环氧丙烯酸酯低聚物的合成与性能", 《现代涂料与涂装》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111423574A (en) * | 2020-04-28 | 2020-07-17 | 淮安巴德聚氨酯科技有限公司 | Dispersing agent for polymer polyol with cyclohexane structure and preparation method thereof |
| CN112279999A (en) * | 2020-11-09 | 2021-01-29 | 广东石油化工学院 | Biodegradable radiation-curable urethane (meth) acrylate and preparation method thereof |
| CN112279999B (en) * | 2020-11-09 | 2022-03-11 | 广东石油化工学院 | Biodegradable radiation-curable urethane (meth) acrylate and preparation method thereof |
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| CN108383988B (en) | 2020-05-19 |
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