CN112920680A - Preparation method of photosensitive resin composition and preparation method of photocuring coating - Google Patents
Preparation method of photosensitive resin composition and preparation method of photocuring coating 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
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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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
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Abstract
The invention relates to the field of photocuring coatings, and discloses a preparation method of a photosensitive resin composition and a preparation method of a photocuring coating. Mixing epoxy resin and a toughening agent, sequentially adding a cationic photoinitiator and a free radical photoinitiator, mixing, and adding a leveling agent to obtain a photosensitive resin composition; the photosensitive resin composition is coated on a substrate, and after photocuring, the photocured coating is obtained. In the formula of the invention, alicyclic epoxy resin, preferably tetrahydroindene diepoxide is used as main resin, and toughening agent polycaprolactone polyol and the like are combined, so that the prepared photosensitive resin composition has the advantages of high curing speed, no oxygen inhibition in the curing process, yellowing resistance and abrasion resistance of the cured coating, and excellent adhesive force to a plurality of substrates.
Description
Technical Field
The invention belongs to the field of photocureable coatings, and relates to a photosensitive resin composition suitable for photocureable coatings on the surfaces of different base materials, in particular to a preparation method of the photosensitive resin composition and a preparation method of the photocureable coating.
Background
The photocuring coating has protection and decoration effects on the base material, whether the performance is excellent or not mainly depends on whether the photocuring coating has good adhesive force to the base material and whether the photocuring coating is wear-resistant, and if the photocuring coating has poor adhesive force to the base material or has poor wear resistance, the prepared product is easy to cause coating desorption and easy to wear in the use process, so that the product has poor use efficiency and short service life. Most of raw materials used for photocuring coatings in the market at present are free radical photosensitive resin and photoinitiator, so that the coatings prepared by ultraviolet irradiation usually have excellent adhesive force only for a certain specific base material, but are not suitable for other base materials accompanied with oxygen inhibition, the application range of products is narrow, and the coatings are difficult to cure and have sticky surfaces and cannot be used due to the existence of the oxygen inhibition. Therefore, the development of the photosensitive resin composition for the photocureable coating which has no oxygen inhibition, can be quickly crosslinked and cured, has excellent performances of yellowing resistance, abrasion resistance and the like of the cured coating and has excellent adhesive force to most of base materials is worthy, and has very important significance for the market of the photocureable coating field.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention provides the photosensitive resin composition for the photocuring coating, which can be quickly crosslinked and cured, has yellowing resistance, abrasion resistance and no oxygen inhibition, and has excellent adhesive force to most of base materials, and the photocuring coating prepared by the photosensitive resin composition.
In order to realize the purpose of the invention, the invention adopts the following technical scheme:
the preparation method of the photosensitive resin composition comprises the following steps: mixing the epoxy resin and the toughening agent, sequentially adding the cationic photoinitiator and the free radical photoinitiator, mixing, and adding the leveling agent to obtain the photosensitive resin composition.
A method for preparing a photocuring coating comprises the following steps: mixing epoxy resin and a toughening agent, sequentially adding a cationic photoinitiator and a free radical photoinitiator, mixing, and adding a leveling agent to obtain a photosensitive resin composition; the photosensitive resin composition is coated on a substrate and photocured to obtain a photocured coating.
The photosensitive resin composition is used for preparing a photocuring coating, and consists of epoxy resin, a toughening agent, a cationic photoinitiator, a free radical photoinitiator and a leveling agent; the photosensitive resin composition comprises, by weight, 40-100 parts of epoxy resin, 0-20 parts of a toughening agent, 0-10 parts of a cationic photoinitiator, 0-5 parts of a free radical photoinitiator and 0-1 part of a leveling agent, wherein the components of an acrylate oligomer, the toughening agent, the cationic photoinitiator, the free radical photoinitiator and the leveling agent are not 0; further preferably, the photosensitive resin composition comprises, by weight, 100 parts of an epoxy resin, 5-15 parts of a toughening agent, 2-8 parts of a cationic photoinitiator, 0.2-2 parts of a radical photoinitiator, and 0.1-0.5 part of a leveling agent.
In the present invention, the epoxy resin is one or more of alicyclic epoxy resin, bisphenol A type epoxy resin, and aliphatic epoxy resin, preferably alicyclic epoxy resin, such as 3,4-epoxycyclohexylmethyl 3, 4-epoxycyclohexanecarboxylate (TTA21), bis ((3, 4-epoxycyclohexyl) methyl) adipate (TTA26), poly [ (2-oxiranyl) -1, 2-cyclohexanediol ] 2-ethyl-2- (hydroxymethyl) -1, 3-propanediol ether (3:1) (TTA3150), 1, 2-epoxy-4-vinylcyclohexane (TTA11), 3, 4-epoxycyclohexylmethylmethacrylate (TTA15), 1-methyl-4- (2-methyloxiranyl) -7-oxabicyclo [4.1.0] heptane (TTA20), 4-vinyl-1-cyclohexene diepoxide (TTA22), dicyclopentadiene diepoxide (TTA27), tetrahydroindene diepoxide (TTA28), 3,4,3 ', 4' -diepoxybicyclohexane (TTA800), and more preferably tetrahydroindene diepoxide (TTA 28).
In the present invention, the toughening agent is polyester polyol or polyether polyol, such as one or more of polycaprolactone polyol, polyester polyol and polyether polyol, and is more preferably selected from polycaprolactone polyol.
In the present invention, the cationic photoinitiator is an onium salt, such as one or more of triarylsulfonium hexafluorophosphate, triarylsulfonium hexafluoroantimonate, and diaryliodonium salts, and is more preferably selected from triarylsulfonium hexafluorophosphate (TTA UV-692).
In the invention, the free radical photoinitiator is 2-hydroxy-2-methyl-1-phenyl-1-acetone.
In the invention, the flatting agent is an organic silicon flatting agent.
The photosensitive resin composition prepared by the invention is used for preparing photocuring coatings on the surfaces of different base materials, wherein the base materials are plastic, glass, metal and other materials, and preferably, the base materials are PP, PET, PVC, PMMA, glass, copper materials, tinplate and other materials. The photocuring is ultraviolet curing, and the light intensity is 30-80 mW/cm during photocuring2According to the thickness of a conventional coating, the exposure time is 5-20 s; on the surfaces of a plurality of base materials, the composition can be quickly crosslinked and cured, has yellowing resistance and abrasion resistance, does not have oxygen inhibition and has excellent adhesive force to most base materials.
The invention has the following characteristics
In the formula of the invention, alicyclic epoxy resin, preferably tetrahydroindene diepoxide (TTA28), is used as main resin, and toughening agents such as polycaprolactone polyol are combined, so that the prepared photosensitive resin composition has the advantages of high curing speed, no oxygen inhibition in the curing process, yellowing resistance and abrasion resistance of the cured coating, and excellent adhesive force to most of substrates. The toughening agent is added in the formula, so that a coating cured by the photosensitive resin composition has good toughness and higher impact resistance. According to the invention, the epoxy resin and the toughening agent are mixed and then sequentially added with the cationic photoinitiator and the free radical photoinitiator, and the leveling agent is added after mixing to obtain the photosensitive resin composition.
Drawings
FIG. 1 is a photograph of the coating before and after testing of example four;
FIG. 2 is a photograph of a prior art coating before and after testing.
Detailed Description
The raw materials for the photosensitive resin composition of the present invention can be produced by an existing or conventional method or can be commercially available. The photosensitive resin composition of the present invention can be prepared by mixing and stirring given amounts of the alicyclic epoxy resin, the toughening agent, the cationic photoinitiator, the radical photoinitiator, and the leveling agent, and the stirring/mixing can be carried out using a conventional apparatus (high-speed shear disperser, planetary mixer, etc.), specifically, a conventional technique. For example, the specific preparation method of the photosensitive resin composition is as follows:
(1) mixing the epoxy resin and the toughening agent, and uniformly stirring;
(2) adding a cationic photoinitiator into the mixture obtained in the step (1), and after the cationic photoinitiator is uniformly dispersed, adding a free radical photoinitiator and uniformly stirring and dispersing;
(3) adding a leveling agent into the mixture obtained in the step (2), and mixing and stirring uniformly at room temperature;
the obtained photosensitive resin composition has excellent curability, can form a glue layer by ultraviolet irradiation, and can be suitably used as a photocuring coating on the surfaces of different substrates. The coating obtained by curing the photosensitive resin composition has the advantages of high curing speed, no oxygen inhibition in the curing process, yellowing resistance, abrasion resistance and excellent adhesive force to most base materials.
Characteristic evaluation (test method)
Oxygen inhibition effect: to compare whether the photosensitive resin composition is affected by oxygen inhibition during curing, photosensitive resin compositions of different formulations were respectively roll-coated on a glass substrate with a coating of the same thickness (20 μm) and under the same light source (UV mercury lamp) and light intensity (40 mW/cm)2) At the same irradiation height (150mm), the surface was completely dry and evaluated as √ when exposed to light for the same time (5 s); the surface finger touched a fingerprint but did not stick was rated as O; surface finger tack was rated x.
And (3) testing the adhesive force: in order to compare the adhesion of the photosensitive resin composition to the substrates, the adhesion rating of the subbing layer (thickness: 20 μm) on different substrates was measured according to the ISO2409-2013 paint and varnish cross-hatch test, and the adhesion rating of 1 or less was rated as √; the adhesion rating of more than 1 grade but 3 or less was rated as O; an adhesion rating of greater than 3 was rated as x.
And (3) wear resistance test: in order to compare the abrasion resistance of the photosensitive resin composition, a paint film abrader (model: JM-V, Shanghai modern environmental engineering service Co., Ltd.) was used. The abrasion resistance of the coating is tested according to ISO7784-2:1997 (rotating rubber grinding wheel method for determining abrasion resistance of paints and varnishes), the number of times of abrasion is more than or equal to 1000 times and the coating is evaluated as √; the number of rubbing was less than 1000 times but not less than 500 times and was evaluated as O without breakage; the number of abrasion was less than 500 times, and the breakage was evaluated as X.
The present invention will be described more specifically with reference to the following examples, but the present invention is not limited to these examples.
The details of the components used in the examples of the present invention and comparative examples are as follows.
A. Alicyclic epoxy resin: tetrahydroindene diepoxide (bicyclonoadiene diopoxide, TTA28, jiangsu titel new materials science and technology ltd); can be prepared by taking tetrahydroindene, dichloromethane, sodium carbonate and DPN (pyridine nucleotide diphosphate) as materials;
B. acrylate oligomer: polyester Acrylate (Polyester Acrylate, DR-E524, Happy materials industries, Inc.);
C. a toughening agent: polycaprolactone polyol (Polycaprolactone polyol, PCL-3057, new materials science and technology ltd for polymer kernels in Hunan);
D. cationic photoinitiator: 4- (phenylthio) phenyldiphenylsulfonium hexafluorophosphate & Bis (4- (diphenylsulfonium) phenyl) sulfide-Bis hexafluorophosphate (Diphenyl [4- (phenylthio) phenyl ] sulfonium hexafluorophosphate & Bis (4- (diphenylthio) phenyl) sulfate Bis (hexafluoro phosphate), TTA UV-692, butte thol new materials science co);
E. free radical photoinitiator: 2-hydroxy-2-methyl-1-phenyl-1-propanone (2-hydroxy-2-methyl-1-phenyl-1-acetone, 1173, new material for Tianjin Jiu Co., Ltd.);
F. leveling agent: polyether Modified Polydimethylsiloxane Copolymers (BYK-333, Dalian Cheng trade Co., Ltd.).
The photosensitive resin compositions of examples and comparative examples were prepared by the following methods:
component A, component B, component C in the amounts (unit: parts by weight) listed in Table 1 were mixed by ordinary stirring without solvent for 15 minutes; then, component D was added to the mixture, followed by stirring and mixing for 5 minutes, then component E was added, followed by stirring and mixing for 15 minutes, and finally component F was added, followed by stirring and mixing at room temperature, thereby preparing a photosensitive resin composition.
Table 1 example and comparative example formulations and performance testing
| A | B | C | D | E | F | Degree of surface dryness | Wear-resisting eraser | |
| Example one | 100 | 0 | 5 | 5 | 1 | 0.2 | ○ | ○ |
| Example two | 100 | 0 | 15 | 5 | 1 | 0.2 | √ | ○ |
| EXAMPLE III | 80 | 20 | 10 | 4 | 1 | 0.2 | ○ | √ |
| Example four | 100 | 0 | 10 | 5 | 1 | 0.2 | √ | √ |
| Comparative example 1 | 20 | 80 | 10 | 1 | 4 | 0.2 | × | ○ |
| Comparative example II | 0 | 100 | 10 | 0 | 5 | 0.2 | × | × |
| Comparative example III | 100* | 0 | 10 | 5 | 1 | 0.2 | √ | ○ |
| Comparative example four | 100 | 0 | 0 | 5 | 0 | 0.2 | √ | × |
| Comparative example five | 100 | 0 | 10 | 5 | 0 | 0 | √ | × |
| Comparative example VI | 100 | 0 | 10 | 5 | 1 | 0.2 | √ | √ |
Note that, in comparative example three, the alicyclic epoxy resin TTA28 was replaced with 3,4-Epoxycyclohexylmethyl 3, 4-epoxycyclohexanecarboxylate (3,4-Epoxycyclohexylmethyl 3, 4-epoxycyclohexylamine Carboxylate, TTA21, jiangsu taier new material science and technology ltd). In comparative example six, component a, component C, component D, component E, and component F were added together in a vessel without a solvent, and mixed with stirring at room temperature, thereby preparing a photosensitive resin composition.
Table 2 examples and comparative formulations adhesion test
Note that seven different substrates were selected for this test, and a wire bar was used to roll-coat a coating of the same thickness (20 μm) on the surface of the different substrates, using the same light source (UV mercury lamp), the same as the UV mercury lampLight intensity (40 mW/cm)2) And standing for 24h after exposure for the same time (10s) at the same irradiation height (150mm), and then carrying out an adhesion test.
Example four rub resistance test 2000 times unbroken, the photographs of the coating before and after the test are shown in figure 1; the abrasion resistance of the existing widely-used commercially-available epoxy photocureable coating is tested to be 860 times of damage, and photos of the coating before and after the test are shown in figure 2; the epoxy resin of example four was replaced with 3, 4-epoxycyclohexylmethylmethacrylate (TTA15), and the abrasion resistance was tested for 270 breaks with the remainder unchanged. Example three rub resistance test 1770 breaks; the toughener of example four was replaced with a linear polyester diol
T1136 (Yingchuang specialty Chemicals (Shanghai) Co., Ltd.), the rest is unchanged, and the abrasion resistance is 1250 times of damage; comparative example six rub resistance tests 1865 breaks.
As shown in table 1, the photosensitive resin composition of the present invention, a coating obtained by ultraviolet irradiation curing, exhibits excellent properties, has a fast curing rate, does not have oxygen inhibition during curing, and the cured coating is resistant to yellowing and abrasion. As shown in Table 2, the photosensitive resin composition of the present invention produced a coating having excellent adhesion to most substrates. On the other hand, the comparison of the comparative examples shows that the photosensitive resin composition obtained by mixing the epoxy resin and the toughening agent, sequentially adding the cationic photoinitiator and the free radical photoinitiator, mixing and adding the leveling agent has the best wear resistance. The photosensitive resin composition has very important significance in the market of the field of photocureable coatings due to the excellent performance of the photosensitive resin composition after curing to form a film.
Claims (10)
1. The preparation method of the photosensitive resin composition is characterized in that the epoxy resin and the toughening agent are mixed and then sequentially added with the cationic photoinitiator and the free radical photoinitiator, and the leveling agent is added after mixing to obtain the photosensitive resin composition.
2. The method for preparing the photosensitive resin composition according to claim 1, wherein the photosensitive resin composition comprises, by weight, 40 to 100 parts of an epoxy resin, 0 to 20 parts of a toughening agent, 0 to 10 parts of a cationic photoinitiator, 0 to 5 parts of a radical photoinitiator, and 0 to 1 part of a leveling agent, wherein the components of the acrylate oligomer, the toughening agent, the cationic photoinitiator, the radical photoinitiator, and the leveling agent are not 0.
3. The method for preparing the photosensitive resin composition according to claim 2, wherein the photosensitive resin composition comprises, by weight, 100 parts of an epoxy resin, 5 to 15 parts of a toughening agent, 2 to 8 parts of a cationic photoinitiator, 0.2 to 2 parts of a radical photoinitiator, and 0.1 to 0.5 part of a leveling agent.
4. The method of claim 1, wherein the epoxy resin is one or more of a cycloaliphatic epoxy resin, a bisphenol a type epoxy resin, and an aliphatic epoxy resin.
5. The method of preparing the photosensitive resin composition according to claim 4, wherein the epoxy resin is a cycloaliphatic epoxy resin.
6. The method for preparing the photosensitive resin composition according to claim 1, wherein the toughening agent is a polyester polyol or a polyether polyol.
7. The method for preparing the photosensitive resin composition according to claim 1, wherein the cationic photoinitiator is an onium salt; the free radical photoinitiator is 2-hydroxy-2-methyl-1-phenyl-1-acetone; the leveling agent is an organic silicon leveling agent.
8. A preparation method of a photocuring coating is characterized in that epoxy resin and a toughening agent are mixed and then sequentially added with a cationic photoinitiator and a free radical photoinitiator, and a leveling agent is added after mixing to obtain a photosensitive resin composition; the photosensitive resin composition is coated on a substrate and photocured to obtain a photocured coating.
9. The method of claim 8, wherein the substrate is plastic, glass or metal.
10. The method for producing a photocurable coating according to claim 8, wherein the intensity of light is 30 to 80mW/cm when photocured2。
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Cited By (3)
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| CN115746703A (en) * | 2022-11-21 | 2023-03-07 | 东莞市雄驰电子有限公司 | Method for preparing photocureable coating composition and coating based on epoxy fluorobenzene silicone resin and application of photocureable coating composition and coating |
| CN115806764A (en) * | 2023-01-05 | 2023-03-17 | 湖南松井新材料股份有限公司 | Insulating paint for new energy automobile battery and preparation method thereof |
| CN116804667A (en) * | 2023-08-28 | 2023-09-26 | 深圳田十科技有限公司 | Method and device for evaluating oxygen polymerization inhibition performance of photo-cured product |
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