CN112724796A - Photochromic composition based on epoxy modification, product and preparation method - Google Patents
Photochromic composition based on epoxy modification, product and preparation method Download PDFInfo
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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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
- C09D163/10—Epoxy resins modified by unsaturated compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2369/00—Characterised by the use of polycarbonates; Derivatives of polycarbonates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
- C08J2463/10—Epoxy resins modified by unsaturated compounds
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Abstract
The invention provides an epoxy-modified photochromic composition, an article and a preparation method thereof, wherein the composition comprises polyol, olefin anhydride, a catalyst, alicyclic epoxy, oxetane, photochromic powder, a photoinitiator, an antioxidant, an ultraviolet light absorber, a leveling agent and a defoaming agent. According to the invention, carbon-carbon unsaturated double bonds and flexible chain segments of polyhydric alcohols are introduced into an epoxy system and compounded with oxetane to form a dual-curing system, the introduction of epoxy groups can reduce the shrinkage rate and improve the adhesive force, and then the photochromic composition is well adhered to the surface of a transparent substrate through EB radiation curing. The damage of ultraviolet light to the photochromic powder is avoided, the photochromic composition is cured into a film within a few seconds, the production efficiency and the qualification rate of finished products are improved, and the energy consumption and the production cost are reduced.
Description
Technical Field
The invention belongs to the field of optical films, and particularly relates to an epoxy modification-based photochromic composition, a product and a preparation method thereof, which are mainly applied to production and processing of photochromic glasses and photochromic films.
Background
At present, the photochromic glasses on the market are divided into two types, one is base material photochromic, and photochromic powder is dissolved in resin or monomer, then poured in a mould and cured and formed at high temperature. The process has several drawbacks: 1. the depth of discolouring appears when discolouring and differs from each other, and the visual sense of bear cat eye appears easily, brings extremely not good visual experience for the customer. 2. When preparing a semi-finished product, a lot of color-changing powder is wasted when the semi-finished product is polished and ground, resulting in a great cost burden. 3. Due to the limitation of raw materials, the process can only prepare 1.56 and 1.61 lenses, and cannot prepare 1.67 or 1.71 high value-added lenses.
The other is a coating color-changing technology, which is a process that the lens is cured, a layer of color-changeable coating is coated on the surface of the lens, and the lens is cured to form a film under certain conditions. The process perfectly solves the three defects of the substrate color changing technology. However, the technology is always monopolized abroad due to the high development difficulty, long research and development period and strict technological requirements. Domestic eyeglass manufacturers imitate for many years, the imitation degree of the technology reaches 80%, the coating color-changing technology is a thermosetting technology, and the coating color-changing liquid is coated on a lens base material and is heated for 2 hours at the temperature of about 120 ℃ to be cured into a film. The technology has long time consumption, high energy consumption and low production efficiency, and the product percent of pass is only about 50 percent. The main reason why many domestic eyeglass manufacturers try to develop coating color-changing curing techniques is that the photochromic powder has a certain service life and becomes yellow or even loses the color-fading capability under the ultraviolet light with higher radiation light intensity. In the prior art, a process of radiating an LED with the wavelength of 405nm for 1min and then thermally setting the LED for 1 hour is mentioned, and although the process shortens the time by a half, the process still has high energy consumption and low production efficiency and cannot realize intelligent mechanical production.
Disclosure of Invention
The invention aims to provide a photochromic composition based on epoxy modification, which can effectively solve the problem of damage of ultraviolet light to photochromic powder, greatly shorten the production time of coated photochromic glasses, improve the yield of products and further reduce the production cost.
The specific technical scheme is as follows: an epoxy-modified photochromic composition comprises the following components in parts by weight:
the catalyst is any one or more of 2, 4, 6-tri (dimethylaminomethyl) phenol, boron trifluoride diethyl etherate, dimethyl imidazole or triphenylphosphine; the polymerization inhibitor is any one or more of hydroquinone, 2-tert-butylhydroquinone, methyl hydroquinone and 4-methoxyphenol.
As a second aspect of the present invention, there is provided a method for preparing the above epoxy-based modified photochromic composition, wherein the amounts of the components are as described above, and the method comprises the following steps:
firstly, vacuumizing polyol at 100-130 ℃, preferably 120 ℃ for 1-2 hours, cooling to 60-80 ℃, adding alkene anhydride, keeping the temperature at 80-100 ℃, preferably 90 ℃, and uniformly stirring; adding a catalyst, a polymerization inhibitor and alicyclic epoxy resin, heating to 100-130 ℃, preferably 120 ℃, and stirring for 1-2 hours under heat preservation; adding oxetane and photochromic powder, and stirring for 1-2 hours at the temperature of 60-90 ℃, preferably 80 ℃ under heat preservation; and adding a photoinitiator, an antioxidant, an ultraviolet absorber, a leveling agent and a defoaming agent, and uniformly stirring to obtain the photochromic composition.
As a third aspect of the present invention, there is provided a method for preparing an article comprising the above epoxy-modified photochromic composition, wherein the amounts of the components are as described above in parts by weight, comprising the steps of:
firstly, vacuumizing polyol at 120 ℃ for 1-2 hours, cooling to 60-80 ℃, adding olefin anhydride, and keeping the temperature at 90 ℃ and stirring uniformly; adding catalyst, polymerization inhibitor and alicyclic epoxy resin, heating to 120 ℃, and stirring for 2 hours under heat preservation; adding oxetane and photochromic powder, and stirring for 1-2 hours at the temperature of 80 ℃; adding a photoinitiator, an antioxidant, an ultraviolet light absorber, a leveling agent and a defoaming agent, and uniformly stirring to obtain a photochromic composition; and coating the photochromic composition on a substrate material, and curing by EB radiation under the protection of nitrogen to form a film to obtain the product.
Further, the substrate material is any one of a polycarbonate material, a polyurethane material or a polyacrylic acid material.
Further, the EB radiation curing is carried out under the conditions of 110-120 kv voltage and 30-50 KGy radiation dose, and preferably 120kv voltage and 50KGy radiation dose.
As a fourth aspect of the present invention, there is provided an article comprising the above epoxy-based modified photochromic composition, which is prepared by the above preparation method.
Wherein the polyol is any one or the combination of more than two of polyether polyol, polycarbonate polyol, polycaprolactone polyol, polyester polyol, dihydric alcohol or dihydric mercaptan;
the alkene anhydride is any one or the combination of more than two of 4-methyl-4-cyclohexene-1, 2-dicarboxylic anhydride, 2-dodecenyl-succinic anhydride and maleic anhydride;
the alicyclic epoxy resin is any one of TTA21, TTA26 and TTA 2081;
the oxetane is any one of TCM101, TCM102, TCM201 and TCM 204;
the photoinitiator is any one of 6976M, 6992M, YQ-II-65 and LSR-IV-020;
the antioxidant is one of 2, 6-di-tert-butyl-p-cresol, bis (3, 5-tertiary butyl-4-hydroxyphenyl) thioether, tetra [ beta- (3, 5-tertiary butyl-4-hydroxyphenyl) propionic acid ] pentaerythritol ester and thiodipropionic acid diester;
the ultraviolet light absorber is any one of LOWILITE22, LOWILITE26, LOWILITE28 or LOWILITE 234;
the photochromic powder is any one or a combination of more than two of midnight grey, volcanic grey and misty grey of eel company;
the leveling agent is any one or the combination of more than two of Levaslip8629, Levaslip839, Levaslip837 or Levaslip 810;
the defoaming agent is any one or the combination of more than two of Defom2700, Defom5500, Defom8700 or Defom 6500;
the voltage used for EB curing can be 100kv, 110kv or 120kv, and the dosage can be 40KGy, 50KGy or 60 Kgy; preferably 120kv voltage, 50KGy radiation dose.
The principle of the invention is as follows: the unsaturated carbon-carbon double bond of the alkene anhydride and the flexible chain segment of the polyalcohol are introduced into an epoxy system, and the alkene anhydride is introduced, so that a free radical curing method can be provided, and the hardness and the solvent resistance after curing can be provided; the introduction of the polyol flexible chain segment can improve the toughness after curing and can also improve the color changing speed and the color fading speed of the color changing coating; meanwhile, the epoxy group can provide a cation curing method to form a dual curing system, and an interpenetrating network structure is formed after curing, so that the solvent resistance is further improved, the shrinkage rate can be reduced, the adhesive force of the coating on the lens is improved, and the purpose of 0 grade of the hundred is achieved. By adopting an EB radiation curing mode, the carbon-carbon double bonds in polymer molecules are bombarded by high-energy electron beams to be broken to generate free radicals, a free radical initiator is not required to be added, the conversion rate of the double bonds can be increased to more than 95%, the crosslinking density and the solvent resistance are increased to the maximum extent, and the photochromic composition is well attached to the surface of the transparent base material. The damage of ultraviolet light to the photochromic powder is avoided, the photochromic composition is cured into a film within a few seconds, the production efficiency and the qualification rate of finished products are improved, and the energy consumption and the production cost are reduced.
The preparation method and the implementation method of the photochromic composition provided by the invention enable the photochromic coating composition to have good light transmittance, firmness, aging resistance and corrosion resistance on a substrate, and have good discoloration depth and discoloration speed.
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.
The present invention is further illustrated by the following specific examples. It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.
The following examples use the names of the compounds (all of which are commercially available starting materials):
PEG 1000: polyethylene glycol (molecular weight 1000)
The PCD 1000: polycarbonate diol (molecular weight 1000)
PCL 1000: polycaprolactone diol (molecular weight 1000)
PDA 1000: polyester diol (molecular weight 1000)
PTMEG 1000: polytetrahydrofuran diol (molecular weight 1000)
Catalyst TPP: triphenylphosphine
Polymerization inhibitor MEHQ 4-methoxyphenol
Jiangsutaer alicyclic epoxy resin: TTA21
Jiangsu strong oxetane: TCM102
Zhejiang poplar photoinitiator: 6976M
De modest defoaming agent Defom8700
Dre leveling agent Levaslip810
Lotilite 22 as an ultraviolett ultraviolet absorber
Photo-variable toner midnight gray by Wiegar corporation
Photo-variable toner misty grey by eel corporation
Antioxidant BHT 2, 6-di-tert-butyl-p-cresol
Example 1
Example 1.1
Adding 30.8g PEG1000 into a container, vacuumizing at 120 ℃ for 2h, cooling to 70 ℃, adding 10.4g 4-methyl-4-cyclohexene-1, 2-dicarboxylic anhydride, stirring at 90 ℃ for 2h, adding 38.85g TTA21, 0.24g TPP and 0.02g HEMQ, stirring at 120 ℃ for 2h, adding 15g TCM102, 2.5g midnight gray and 2.5g misty gray, stirring at 80 ℃ for 1 h, adding 0.02g BHT, 0.02g LOWILITE22, 0.1g Defom8700, 0.1g Levaslip810 and 1g 6976M, and mixing uniformly to obtain the photochromic coating composition. The photochromic coating composition is sprayed on the surface of a Polycarbonate (PC) lens, rotated at the rotating speed of 800rpm for 20 seconds, and cured by EB under the protection of nitrogen gas by adopting the voltage of 110kv and the dosage of 30KGy, and finally the PC photochromic lens is obtained.
Example 1.2
Adding 30.8g PEG1000 into a container, vacuumizing at 120 ℃ for 2h, cooling to 70 ℃, adding 10.4g 4-methyl-4-cyclohexene-1, 2-dicarboxylic anhydride, stirring at 90 ℃ for 2h, adding 38.85g TTA21, 0.24g TPP and 0.02g HEMQ, stirring at 120 ℃ for 2h, adding 15g TCM102, 2.5g midnight gray and 2.5g misty gray, stirring at 80 ℃ for 1 h, adding 0.02g BHT, 0.02g LOWILITE22, 0.1g Defom8700, 0.1g Levaslip810 and 1g 6976M, and mixing uniformly to obtain the photochromic coating composition. The photochromic coating composition is sprayed on the surface of a PC lens, rotated at the rotating speed of 800rpm for 20 seconds, cured by EB under the protection of nitrogen, and finally the PC photochromic lens is obtained by adopting the voltage of 120kv and the dosage of 50 KGy.
Example 2:
adding 30.8g of PCD1000 into a container, vacuumizing at 120 ℃ for 1.5h, cooling to 70 ℃, adding 10.4g of 4-methyl-4-cyclohexene-1, 2-dicarboxylic anhydride, heating to 90 ℃, keeping the temperature and stirring for 2 hours, adding 38.85g of TTA21, 0.24g of TPP and 0.02g of HEMQ, keeping the temperature and stirring at 120 ℃ for 2 hours, then adding 15g of TCM102, 2.5g of midnight grey and 2.5g of misty grey, keeping the temperature and stirring at 80 ℃ for 1 hour, adding 0.02g of BHT, 0.02g of LOWILITE22, 0.1g of Defom8700, 0.1g of Levassli 810 and 1g of 6976M, and uniformly mixing to obtain the photochromic coating composition. The photochromic coating composition is sprayed on the surface of a PC lens, rotated at the rotating speed of 800rpm for 20 seconds, cured by EB under the protection of nitrogen, and finally the PC photochromic lens is obtained by adopting the voltage of 120kv and the dosage of 50 KGy.
Example 3:
example 3.1
Adding 30.8g of PCL1000 into a container, vacuumizing for 2h at 120 ℃, cooling to 80 ℃, adding 10.4g of 4-methyl-4-cyclohexene-1, 2-dicarboxylic anhydride, stirring at 80 ℃ for 2h, adding 38.85g of TTA21, 0.24g of TPP and 0.02g of HEMQ, stirring at 120 ℃ for 2h, adding 15g of TCM102, 2.5g of midnight gray and 2.5g of misty gray, stirring at 70 ℃ for 1 h, adding 0.02g of BHT, 0.02g of WILOLITE 22, 0.1g of Defom8700, 0.1g of Levaslip810 and 1g of 6976M, and uniformly mixing to obtain the photochromic coating composition. The photochromic coating composition is sprayed on the surface of a PC lens, rotated at the rotating speed of 800rpm for 20 seconds, cured by EB under the protection of nitrogen, and subjected to 110kv voltage and 30KGy radiation dose to finally obtain the PC photochromic lens.
Example 3.2
Adding 30.8g of PCL1000 into a container, vacuumizing for 2h at 120 ℃, cooling to 80 ℃, adding 10.4g of 4-methyl-4-cyclohexene-1, 2-dicarboxylic anhydride, stirring at 80 ℃ for 2h, adding 38.85g of TTA21, 0.24g of TPP and 0.02g of HEMQ, stirring at 120 ℃ for 2h, adding 15g of TCM102, 2.5g of midnight gray and 2.5g of misty gray, stirring at 70 ℃ for 1 h, adding 0.02g of BHT, 0.02g of WILOLITE 22, 0.1g of Defom8700, 0.1g of Levaslip810 and 1g of 6976M, and uniformly mixing to obtain the photochromic coating composition. The photochromic coating composition is sprayed on the surface of a PC lens, rotated at the rotating speed of 800rpm for 20 seconds, cured by EB under the protection of nitrogen, and subjected to voltage of 120kv and radiation dose of 50KGy to finally obtain the PC photochromic lens.
Example 4:
30.8g of PDA1000 is added into a container, the container is vacuumized at 120 ℃ for 2h, the temperature is reduced to 60 ℃, 10.4g of 4-methyl-4-cyclohexene-1, 2-dicarboxylic anhydride is added, the mixture is kept at 100 ℃ for 2 hours and stirred, then 38.85g of TTA21, 0.24g of TPP and 0.02g of HEMQ are added, the mixture is kept at 120 ℃ for 2 hours and stirred, then 15g of TCM102, 2.5g of midnight gray and 2.5g of misty gray are added, after 1 hour of keeping at 60 ℃ and stirring, 0.02g of BHT, 0.02g of LOWILITE22, 0.1g of DEfom8700, 0.1g of Levaslip810 and 1g of 6976M are added, and the photochromic coating composition is obtained after uniform mixing. The photochromic coating composition is sprayed on the surface of a PC lens, rotated at the rotating speed of 800rpm for 20 seconds, cured by EB under the protection of nitrogen, and finally the PC photochromic lens is obtained by adopting the voltage of 120kv and the dosage of 50 KGy.
Example 5:
adding 30.8g of PTMEG1000 into a container, vacuumizing at 120 ℃ for 2h, cooling to 70 ℃, adding 10.4g of 4-methyl-4-cyclohexene-1, 2-dicarboxylic anhydride, stirring at 90 ℃ for 2h, adding 38.85g of TTA21, 0.24g of TPP and 0.02g of HEMQ, stirring at 130 ℃ for 2h, adding 15g of TCM102, 2.5g of midnight gray and 2.5g of misty gray, stirring at 90 ℃ for 1 h, adding 0.02g of BHT, 0.02g of LOWILITE22, 0.1g of Defom8700, 0.1g of Levaslip810 and 1g of 6976M, and uniformly mixing to obtain the photochromic coating composition. The photochromic coating composition is sprayed on the surface of a PC lens, rotated at the rotating speed of 800rpm for 20 seconds, cured by EB under the protection of nitrogen, and finally the PC photochromic lens is obtained by adopting the voltage of 120kv and the dosage of 50 KGy.
TABLE 1 test results for optical articles prepared in examples 1-5
According to the experimental results, the PEG dihydric alcohol, the PCL dihydric alcohol and the PTMEG dihydric alcohol can obtain faster fading rate under the condition of the same adding proportion of the dihydric alcohol, wherein the PEG dihydric alcohol has the best performance; PDA, PCL and PCD with rigid groups can obtain higher hardness and better chemical resistance; the weather resistance is not different, and the standard requirement of the optical lens is basically met; in summary, PCL diol is the best choice, and photochromic lenses satisfying the photochromic property, chemical resistance and hardness at the same time can be obtained without applying a second protective layer. When the voltage of 120kv is selected as the EB curing condition and the dosage of 50KGy is used, the optical product obtained by comparing example 1.1 with example 1.2 and comparing example 3.1 with example 3.2 has higher pencil hardness and better chemical resistance.
Claims (10)
1. The epoxy-modified photochromic composition is characterized by comprising the following components in parts by weight:
the catalyst is any one or more of 2, 4, 6-tri (dimethylaminomethyl) phenol, boron trifluoride diethyl etherate, dimethyl imidazole or triphenylphosphine; the polymerization inhibitor is any one or more of hydroquinone, 2-tert-butylhydroquinone, methyl hydroquinone and 4-methoxyphenol.
2. A method for preparing the epoxy-modified photochromic-based composition according to claim 1, wherein the components are used in the amount of parts by weight according to claim 1, and the method comprises the following steps:
firstly, vacuumizing the polyhydric alcohol at 100-130 ℃ for 1-2 hours, cooling to 60-80 ℃, adding the alkene anhydride, and keeping the temperature at 80-100 ℃ and stirring uniformly; adding a catalyst, a polymerization inhibitor and alicyclic epoxy resin, heating to 100-130 ℃, and stirring for 1-2 hours while keeping the temperature; adding oxetane and photochromic powder, and stirring for 1-2 hours at the temperature of 60-90 ℃; and adding a photoinitiator, an antioxidant, an ultraviolet absorber, a leveling agent and a defoaming agent, and uniformly stirring to obtain the photochromic composition.
3. A method for preparing an article comprising the epoxy-modified photochromic composition of claim 1, wherein the components are used in the amounts indicated in claim 1, and wherein the method comprises the following steps:
firstly, vacuumizing polyol at 120 ℃ for 1-2 hours, cooling to 60-80 ℃, adding olefin anhydride, and keeping the temperature at 90 ℃ and stirring uniformly; adding catalyst, polymerization inhibitor and alicyclic epoxy resin, heating to 120 ℃, and stirring for 2 hours under heat preservation; adding oxetane and photochromic powder, and stirring for 1-2 hours at the temperature of 80 ℃; adding a photoinitiator, an antioxidant, an ultraviolet light absorber, a leveling agent and a defoaming agent, and uniformly stirring to obtain a photochromic composition; and coating the photochromic composition on a substrate material, and curing by EB radiation under the protection of nitrogen to form a film to obtain the product.
4. The method for preparing the product according to claim 3, wherein the substrate material is any one of polycarbonate material, polyurethane material or polyacrylic acid material.
5. The method of claim 3, wherein the EB radiation curing is performed under a voltage of 110 to 120kv and a radiation dose of 30 to 50 KGy.
6. The method of claim 3 or 5, wherein the EB radiation curing is performed at a voltage of 120kv and a radiation dose of 50 KGy.
7. An article comprising a coating made from the epoxy-modified photochromic-based composition of claim 1.
8. An article produced by the production method according to claim 3, 4 or 5.
9. The epoxy-modified-based photochromic composition of claim 1, wherein: the polyol is any one or the combination of more than two of polyether polyol, polycarbonate polyol, polycaprolactone polyol, polyester polyol, dihydric alcohol or dihydric mercaptan.
10. The epoxy-modified-based photochromic composition of claim 1, wherein: the alkene anhydride is any one or the combination of more than two of 4-methyl-4-cyclohexene-1, 2-dicarboxylic anhydride, 2-dodecenyl-succinic anhydride and maleic anhydride.
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| CN202110012456.XA CN112724796B (en) | 2021-01-06 | 2021-01-06 | Photochromic composition based on epoxy modification, product and preparation method |
| PCT/CN2021/074182 WO2022147865A1 (en) | 2021-01-06 | 2021-01-28 | Epoxy modification-based photochromic composition, product and preparation method |
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| KR101286988B1 (en) * | 2011-03-03 | 2013-07-23 | 성락두 | Paint composition, method for coating and case for portable electronic device comprising the coating layer |
| CN102432463A (en) * | 2011-09-06 | 2012-05-02 | 南京工业大学 | Modified epoxy acrylate prepolymer, preparation method and application |
| CN103265871A (en) * | 2013-05-28 | 2013-08-28 | 华南理工大学 | Waterborne epoxy acrylic acid UV (Ultraviolet) curable coating and preparation method thereof |
| CN104293164A (en) * | 2014-10-13 | 2015-01-21 | 东南大学 | Oleic acid modified aliphatic epoxy polyurethane acrylic ester ultraviolet curing coating and preparation method thereof |
| JP2017114982A (en) * | 2015-12-22 | 2017-06-29 | Jnc株式会社 | Curable resin composition, laminate, and glasses |
| CN105860954A (en) * | 2016-04-09 | 2016-08-17 | 佛山市三水森诺建材有限公司 | Novel photochromic transparent plate |
| CN107513345A (en) * | 2017-09-19 | 2017-12-26 | 上海纵港广告器材股份有限公司 | A kind of preparation method of unsaturated type polyurethane coating |
| CN107513345B (en) * | 2017-09-19 | 2019-05-17 | 上海纵港广告器材股份有限公司 | A kind of preparation method of unsaturation type polyurethane coating |
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| WO2022147865A1 (en) | 2022-07-14 |
| CN112724796B (en) | 2022-02-11 |
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