Photocuring material as well as preparation method and application thereof

Abstract

The invention discloses a photo-curing material as well as a preparation method and application thereof, belongs to the technical field of resin materials, and solves the problem that the waterproof performance of a photo-curing material in the prior art is not ideal enough. The preparation method of the photocuring material comprises the following steps: mixing an organic fluorine monomer and a castor oil-based oligomer according to a mass ratio of 1: (4-9), and adding a reactive diluent and a photoinitiator to obtain a mixed solution; mixing and stirring the mixed solution under a heating condition to obtain the photocuring material. According to the preparation method provided by the invention, castor oil-based resin is taken as a research object, hexafluorobutyl methacrylate is introduced into the molecular structure of castor oil according to different mass proportions, and fluorine is introduced to modify the existing castor oil resin so as to endow the material with hydrophobicity; due to the active reaction characteristic of the introduced-NCO group, the chemical crosslinking degree of the material can be increased.

Description

Technical Field

[0001] The present invention relates to the technical field of resin materials, and more specifically to a photocurable material and a preparation method and application thereof. Background Art

[0002] In the field of chemical polymers, UV curing is a process in which the photoinitiator in the liquid UV curing material is photo-initiated to become a free radical or cation under the UV radiation of medium and short wavelength UV light (300-800nm), thereby initiating the polymerization of the liquid resin containing active functional groups into an insoluble and infusible solid film. It is an environmentally friendly technology with low volatile organic compound (VOC) emissions. In the prior art, petroleum-based compounds are often used as raw materials to prepare UV curing materials.

[0003] However, existing UV-curable materials cannot meet the requirements of their application in waterproof scenarios, and a UV-curable material with excellent waterproof performance is urgently needed to be discovered. Summary of the invention

[0004] The invention provides a photocurable material and a preparation method and application thereof, which are used to solve the problem that the waterproof performance of the photocurable material in the prior art is not ideal.

[0005] In a first aspect, the present invention provides a method for preparing a photocurable material, comprising the following steps: mixing an organic fluorine monomer and a castor oil-based oligomer in a mass ratio of 1:4 to 9, adding an active diluent and a photoinitiator to obtain a mixed solution; mixing and stirring the mixed solution under heating conditions to obtain the photocurable material.

[0006] As a possible implementation, the active diluent is any one of isobornyl acrylate and trimethylolpropane triacrylate; and / or, the amount of the active diluent added is such that the mass ratio of the active diluent to the mixed solution is 5% to 15%; and / or, the photoinitiator is any one of 2-hydroxy-2-methyl-1-phenyl-1-propanone, 2-hydroxy-2-methyl-1-phenylpropanone, 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-propanone, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, and ethyl 2,4,6-trimethylbenzoylphenylphosphonate; and / or, the amount of the photoinitiator added is such that the mass ratio of the photoinitiator to the mixed solution is 3% to 7%.

[0007] As a possible implementation, the mass ratio of the organic fluorine monomer to the castor oil-based oligomer is 1:9; and / or the reactive diluent is trimethylolpropane triacrylate, and the mass ratio of the trimethylolpropane triacrylate to the mixed liquid is 15%; and / or the photoinitiator is 2-hydroxy-2-methyl-1-phenyl-1-propanone, and the mass ratio of the trimethylolpropane triacrylate to the mixed liquid is 5%.

[0008] As a possible implementation method, the preparation of the organic fluorine monomer includes the following steps: mixing hexafluorobutyl methacrylate, 2-mercaptoethanol and azobisisobutyronitrile in an organic solvent at a molar ratio of 1:0.5 to 1.5:0.001 to 0.01, mixing and reacting at a constant temperature of 70 to 100° C. and stirring for 6 to 10 hours, and cooling to room temperature; adding isophorone diisocyanate to the reaction system, heating to 40 to 90° C., adding a catalyst, and reacting for 1 to 3 hours to obtain the organic fluorine monomer.

[0009] As a possible implementation method, the organic solvent is any one of toluene, acetone, butanone, dichloromethane, N,N-dimethylformamide (DMF), and dimethylacetamide (DMAc); and / or the catalyst is any one of dibutyltin dilaurate, dibutyltin dilaurate, pentamethyldiethylenetriamine, N,N-dimethylcyclohexylamine, and organic bismuth.

[0010] As a possible implementation method, the preparation of the castor oil-based oligomer includes the following steps: mixing castor oil, isophorone diisocyanate and isobornyl acrylate, reacting at 40-50° C. and stirring for 0.5-1.5 hours; adding a catalyst, reacting for 1.5-2.5 hours until the isocyanate content drops to half of the initial value, thereby obtaining a castor oil-isocyanate intermediate; adding hydroxyethyl acrylate and an inhibitor to the castor oil-isocyanate intermediate, reacting at a temperature of 70-90° C. and a stirring rate of 200-250 r / min until the isocyanate group completely disappears, thereby obtaining the castor oil-based oligomer.

[0011] As a possible implementation method, the reaction degree of isophorone diisocyanate is detected by a di-n-butylamine method; the catalyst is any one of dibutyltin dilaurate, pentamethyldiethylenetriamine, N,N-dimethylcyclohexylamine, and organic bismuth; and / or the inhibitor is any one of 2,6-di-tert-butyl-p-cresol, hydroquinone, 4,4-dihydroxybiphenyl, and 3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate.

[0012] In a second aspect, the present invention provides a photocurable material prepared by the preparation method described in any possible implementation of the first aspect.

[0013] In a third aspect, the present invention provides a photocurable film obtained by spreading the photocurable material described in the second aspect into a film and then irradiating the film under ultraviolet light.

[0014] As a possible implementation manner, the duration of the ultraviolet light irradiation is 1 to 2 minutes.

[0015] Castor oil (CO) is extracted from castor seeds. It is not only low-cost, environmentally friendly, renewable and biodegradable, but also an important chemical raw material. It is recognized as the "king of oils" and "green oil". Its chemical derivatives have reached more than 3,000 kinds. The main components of castor oil hydrolysis are: 80% to 85% ricinoleic acid, 7% oleic acid, 3% linoleic acid, 2% palmitic acid, and 1% stearic acid. Among natural vegetable oils, castor oil contains cis-12-hydroxyoctadecene-9-acid, which has active hydroxyl groups with an average functionality of 2.7, which can directly react with isocyanate groups.

[0016] In the preparation method of the photocurable material provided by the present invention, castor oil-based resin is used as the research object, hexafluorobutyl methacrylate (HFBMA) is introduced into the molecular structure of castor oil according to different mass proportions, and the existing castor oil resin is modified by introducing fluorine element. The fluorine element has a small surface energy and is easy to migrate to the surface of the material during ultraviolet curing, thereby giving the material excellent hydrophobicity; the introduced -NCO group is easy to chemically react with the active hydrogen group due to its active characteristics, and the NCO group of the organic fluorine monomer can react with the hydroxyl group in the castor oil oligomer, thereby increasing the crosslinking degree of the material.

[0017] The preparation method of the photocurable material provided by the present invention monitors the content of the isocyanate group of the intermediate product by the di-n-butylamine method, uses a Fourier infrared spectrometer to detect whether the expected product is successfully synthesized, and uses an ultraviolet light curing method to cure the castor oil-based ultraviolet light curing prepolymer to form a film. During the curing process, only different proportions of active diluents need to be added to adjust the performance of the material, and the energy consumption is low, and it is green and clean. The preparation method provided by the present invention has a simple reaction process, few by-products, and low energy consumption. In addition to having excellent hydrophobic properties, the product may continue to be developed in the future as one of the bio-based polymer materials that completely replaces traditional petroleum-based polymer materials.

[0018] The photocurable material provided by the present invention is a new technology and material that is green, energy-saving and environmentally friendly. It utilizes vegetable oil, a natural and harmless organic compound, so that both the material itself and the products made from the material as raw materials achieve the effect of energy saving and environmental protection. In addition, the photocurable film provided by the present invention has excellent hydrophobic properties and has excellent performance in applications. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings required for use in the embodiments or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying creative work.

[0020] Figure 1 The synthetic route of the organic fluorine monomer (HFMA) provided in the embodiment of the present invention.

[0021] Figure 2 The synthetic route of castor oil-based oligomers (COPUA) provided in the embodiments of the present invention.

[0022] Figure 3 This is an infrared spectrum of the isocyanate intermediate (CO-IPDI) provided in an embodiment of the present invention.

[0023] Figure 4 This is an infrared spectrum of castor oil based oligomer (COPUA) provided in an embodiment of the present invention.

[0024] Figure 5 This is an infrared spectrum curve of hexafluorobutyl methacrylate (HFBMA) provided in an embodiment of the present invention, wherein blue indicates before the reaction and red indicates near the end of the reaction.

[0025] Figure 6 The infrared spectra of samples with different isobornyl acrylate (IBOA) contents when HFMA:COPUA=1:9 are provided in the embodiments of the present invention.

[0026] Figure 7 The infrared spectra of samples with different trimethylolpropane triacrylate (TMPTA) contents when HFMA:COPUA=1:9 are provided in the embodiments of the present invention.

[0027] Figure 8 The infrared spectra of samples with different IBOA contents when HFMA:COPUA=2:8 provided in the embodiment of the present invention, wherein the control group does not add any active diluent.

[0028] Fig. 9 The infrared spectra of samples with different TMPTA contents when HFMA:COPUA=2:8 provided in the embodiment of the present invention, wherein the control group does not add any active diluent. DETAILED DESCRIPTION

[0029] The following will be combined with the drawings in the embodiments of the present invention to clearly and completely describe the technical solutions in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without creative work are within the scope of protection of the present invention.

[0030] In order to solve the problem that the photocurable material preparation process in the prior art is not environmentally friendly, an embodiment of the present invention provides a photocurable material and a preparation method and application thereof.

[0031] Figure 1 The synthetic route of the organic fluorine monomer (HFMA) provided in the embodiment of the present invention is shown. Figure 2 The synthetic route of castor oil based oligomer (COPUA) provided by the embodiment of the present invention is shown. Figure 1 and Figure 2 As shown, the preparation experiment of the organic fluorine monomer and castor oil-based oligomer provided in the embodiment of the present invention verified the successful synthesis of HFMA and COPUA, and the reaction process is simple, with few by-products and low energy consumption. In addition, the preparation cost of raw materials is low, environmentally friendly and sustainable.

[0032] Furthermore, an embodiment of the present invention provides an experiment for preparing a photocurable film, from which it can be seen that the reactive diluent has little effect on the spatial structure of the photocurable material.

[0033] Furthermore, the embodiment of the present invention provides a test experiment of the hydrophobicity of the photocurable film. It can be seen that the photocurable film obtained by using the organic fluorine-modified castor oil resin as the preparation raw material has better hydrophobicity.

[0034] The technical solution of the present invention will be further described below in conjunction with specific embodiments.

[0035] Example 1

[0036] This example provides an experiment for preparing an organic fluorine monomer and a castor oil-based oligomer.

[0037] 2.33g of hexafluorobutyl methacrylate (HFBMA), 0.36g of 2-mercaptoethanol, and 0.02g of azobisisobutyronitrile (AIBN) were mixed in 2.33g of toluene, and reacted for 8h at a constant temperature of 80°C and under stirring conditions; cooled to room temperature, 1.024g of isophorone diisocyanate (IPDI) was added to the reaction system, heated to 85°C, and then the catalyst dibutyltin dilaurate (DBTDL) was added, and the reaction was continued for 2h to obtain the organic fluorine monomer (HFMA). Its synthesis route is as follows Figure 1 shown.

[0038] Mix 28.9g of isophorone diisocyanate (IPDI), 43.5g of castor oil (CO) and 9.70g of isobornyl acrylate (IBOA), and react at 45°C with stirring for 1h; add 0.15g of catalyst dibutyltin dilaurate (DBTDL) and react for 2h to obtain isocyanate intermediate (CO-IPDI). Add 16.97g of hydroxyethyl acrylate (HEA) and 0.12g of inhibitor 2,6-di-tert-butyl-p-cresol (264) to CO-IPDI, and react at 80°C and stirring rate of 225r / min until the isocyanate group reacts completely to obtain castor oil-based oligomer (COPUA). Its synthesis route is as follows: Figure 2 shown.

[0039] The hydroxyl structure in castor oil can react with isocyanate to generate a polyurethane structure. Therefore, in castor oil modification, it is particularly important to control the progress of the first step reaction. This embodiment uses the di-n-butylamine method to titrate the amount of the remaining isocyanate in the reactant. The basic principle is that isocyanate and di-n-butylamine react to generate urea, and the excess di-n-butylamine is titrated with a standard hydrochloric acid solution. The specific operation steps are: after a certain reaction time, accurately weigh about 1g of the reaction sample, put the sample in a 250mL conical flask, and use a pipette to accurately pipette 40mL of a 0.1mol / L di-n-butylamine-toluene solution and add it to the sample, shake and mix evenly, and place it for 20min; then add 50mL of isopropanol to terminate the reaction, drip 2 to 3 drops of bromocresol green ethanol solution indicator, and the system is blue at this time; titrate with a 0.1mol / L hydrochloric acid standard solution until the blue disappears, gradually from green to cyan and then to yellow, and keep it for 30s without discoloration, which is the titration end point. And do a blank experiment without adding a sample. Calculate the -NCO value according to formula Ⅰ;

[0040]

[0041] In formula I, V0 represents the volume of hydrochloric acid consumed by the blank sample (mL); V1 represents the volume of hydrochloric acid consumed by the test sample (mL); C0 represents the concentration of the hydrochloric acid standard solution; W(-NCO) represents the -NCO value, that is, the real-time NCO content of the sample.

[0042] Fourier transform infrared spectrometer (Nicolet I S10, Thermo Fisher Scientific Inc.) was used for the liquid sample. A 25 mm × 4 mm potassium bromide window was used. The scanning measurement range of the infrared spectrometer was 4000 cm -1 Up to 400cm -1 ; Infrared spectroscopy analysis was performed on CO-IPDI, COPUA and HFBMA in the preparation process to obtain Figure 3 , Figure 4 and Figure 5 Results shown.

[0043] Depend on Figure 3 It can be seen that 3400cm -1 , 2800cm -1 The absorption peak at 2250cm is the stretching vibration of the hydroxyl (-OH) and -CH2, -CH3 groups in the castor oil molecular structure. -1 There is a strong absorption peak nearby, which is the characteristic absorption peak of isocyanate group (-NCO).

[0044] Depend on Figure 4 and Figure 3 By comparison, 2250cm -1 The characteristic absorption peak of isocyanate disappears, indicating that the isocyanate group (-NCO) has reacted completely. During the reaction, the isocyanate group in isophorone diisocyanate reacts with the hydroxyl group of the intermediate to form a carbamate group (-NHCOO-). -1 There is no absorption peak nearby. At 3300cm -1 and 1750cm -1 Nearby is the characteristic absorption peak of carbamate (-NHCOO-). 1500cm -1 The absorption peaks near the amide structure are characteristic absorption peaks. In summary, COPUA was successfully synthesized.

[0045] Figure 5 The blue curve in the middle is the infrared spectrum before the reaction, where 3400cm -1 The absorption peak is the stretching vibration of -OH; 2900cm -1 The absorption peak is the -CH2 group of saturated carbon; compared with the red curve near the end of the reaction, the red curve at the beginning of the reaction is at 2200cm -1 There is a strong absorption peak at Figure 2 From the reaction steps, it can be seen that this is the characteristic absorption peak of the isocyanate (R-NCO) group in the reactant isophorone diisocyanate (IPDI). Figure 5 The red curve in the middle is the infrared spectrum curve near the end of the reaction, where 3400cm -1 The absorption peak is the stretching vibration of -OH, 2900 cm -1 The absorption peak is the -CH2 group of saturated carbon; 1700cm -1 ~1800cm -1 The strong absorption peaks are the characteristic absorption peaks of carbonyl and non-cyclic ester groups; 1500cm -1 There is a small absorption peak, which is the amide vibration in the carbamate (-NHCOO-) group; 1000cm -1 Comparison of strong absorption peaks on the left and right Figure 2 It can be seen that it is the bending vibration absorption peak of the amino group -NH2. In summary, the desired product was successfully synthesized.

[0046] Example 2

[0047] This example provides an experiment for preparing a photocurable film.

[0048] The HFMA and COPUA prepared in Example 1 were mixed and reacted in a mass ratio of 1:9 to prepare an organic fluorine-modified castor oil resin (HFMA-COPUA). HFMA-COPUA was placed in a container, and a diluent and 5% by mass of 2-hydroxy-2-methyl-1-phenyl-1-propanone (photoinitiator 1173) were added; the mixture was stirred for 10 minutes under heating conditions to obtain a castor oil resin sample; the castor oil resin sample was spread on a glass plate at a uniform speed using a four-sided preparation device, with uniform force and uniform coating thickness during the spreading process, and then the glass plate was placed under ultraviolet light for 1 to 2 minutes until the castor oil resin sample became a solid film, thereby obtaining a photocurable film A.

[0049] The HFMA and COPUA prepared in Example 1 were mixed and reacted in a mass ratio of 2:8 to prepare an organic fluorine-modified castor oil resin (HFMA-COPUA). HFMA-COPUA was placed in a container, and a diluent and 5% by mass of 2-hydroxy-2-methyl-1-phenyl-1-propanone (photoinitiator 1173) were added; the mixture was mixed and stirred for 10 minutes under heating conditions to obtain a castor oil resin sample; the castor oil resin sample was spread on a glass plate at a uniform speed using a four-sided preparation device, with uniform force and uniform coating thickness during the spreading process, and then the glass plate was placed under ultraviolet light for 1 to 2 minutes until the castor oil resin sample became a solid film, thereby obtaining a photocurable film B.

[0050] The HFMA prepared in Example 1 and a common petroleum-based oligomer (petroleum-based material B-39 from Guangdong Boxing New Materials Technology Co., Ltd.) were mixed and reacted at a mass ratio of 1:9 to prepare a petroleum-based resin. The petroleum-based resin was placed in a container, and a diluent and a 5% mass ratio of a photoinitiator 1173 were added; mixed and stirred for 10 minutes under heating conditions to obtain a petroleum-based sample; the petroleum-based sample was spread on a glass plate at a uniform speed using a four-sided preparation device, and the force and coating thickness were uniform during the spreading process, and then the glass plate was placed under ultraviolet light for 1 to 2 minutes until the petroleum-based sample became a solid film, and a photocured film C was obtained.

[0051] The HFMA prepared in Example 1 and a common petroleum-based oligomer (petroleum-based material B-39 from Guangdong Boxing New Materials Technology Co., Ltd.) were mixed and reacted at a mass ratio of 2:8 to prepare a petroleum-based resin. The petroleum-based resin was placed in a container, and a diluent and a 5% mass ratio of a photoinitiator 1173 were added; mixed and stirred for 10 minutes under heating conditions to obtain a petroleum-based sample; the petroleum-based sample was spread on a glass plate at a uniform speed using a four-sided preparation device, and the force and coating thickness were uniform during the spreading process, and then the glass plate was placed under ultraviolet light for 1 to 2 minutes until the petroleum-based sample became a solid film, and a photocured film D was obtained.

[0052] The diluents used in this embodiment are: 5%, 10%, 15% by weight of isobornyl acrylate (IBOA) or 5%, 10%, 15% by weight of trimethylolpropane triacrylate (TMPTA). Taking the photocurable film A as an example, infrared spectroscopy analysis was performed on castor oil resin samples with different types and different addition ratios of diluents, and the following results were obtained: Figure 6 and Figure 7 The results shown. Figure 6 and Figure 7 It can be seen that no matter how the content or type of the active diluent changes, the spectral waveform is roughly the same, which shows that the addition of active diluent has no significant effect on the spatial structure of the castor oil resin sample; the more obvious part is the characteristic absorption peak of the terminal carbon-carbon double bond, which shows that the increase in the active diluent content has an improving effect on the fluidity, curing activity and cross-linking density of the sample.

[0053] Taking the photocurable film B as an example, the infrared spectrum analysis of castor oil resin samples with different types and different added proportions of diluents was carried out, and the following results were obtained: Figure 8 and Fig. 9 The results shown in the figure show that adding active diluent does not change the infrared spectrum waveform of the sample. Figure 6 and Figure 7 It can be seen that the active diluent has no significant effect on the structure of the sample. This experiment also conducted a mechanical properties analysis, and the results showed that when the diluent was 15% TMPTA by mass, the mechanical and other comprehensive properties were optimal. Therefore, the diluent of the photocurable film used in subsequent experiments was 15% TMPTA by mass.

[0054] Example 3

[0055] This embodiment provides an experiment to test the hydrophobicity of the photocured film.

[0056] The wettability of a solid surface is usually measured by the static contact angle (CA) of a water drop on a solid horizontal surface. When CA < 90°, CA < 5°, they are called hydrophilic and super hydrophilic materials respectively; when CA > 90°, CA > 150°, they are called hydrophobic and super hydrophobic materials respectively.

[0057] In this example, a static hydrophobic angle measurement experiment was performed on the photocured films A to D prepared in Example 2 using a contact angle meter (SL200KS, Kono, USA) in a laboratory environment, and the results shown in Table 1 were obtained.

[0058] Table 1 Static hydrophobic angle measurement results

[0059] CA / ° Photocurable film A 151.8 Light Curing Film B 153.1 Light Curing Film C 121.3 Light Curing Film D 109.5

[0060] As shown in Table 1, the photocurable films A and B meet the standard of super-hydrophobic materials, while the hydrophobicity of the photocurable films C and D is hydrophobic materials. This shows that the photocurable films obtained by using organic fluorine-modified castor oil resin as the preparation raw material have better hydrophobicity.

[0061] Although the preferred embodiments of the present invention have been described, those skilled in the art may make other changes and modifications to these embodiments once they have learned the basic creative concept. Therefore, the appended claims are intended to be interpreted as including the preferred embodiments and all changes and modifications that fall within the scope of the present invention.

[0062] Obviously, those skilled in the art can make various changes and modifications to the present invention without departing from the spirit and scope of the present invention. Thus, if these modifications and variations of the present invention fall within the scope of the claims of the present invention and their equivalents, the present invention is also intended to include these modifications and variations.

Claims

1. A method for preparing a photocurable material, characterized in that: The following steps are involved: The organic fluorine monomer and the castor oil-based oligomer are mixed in a mass ratio of 1:4 to 9, and a reactive diluent and a photoinitiator are added to obtain a mixed solution; The mixed liquid is mixed and stirred under heating conditions to obtain the photocurable material.

2. The preparation method according to claim 1, characterized in that: The active diluent is any one of isobornyl acrylate and trimethylolpropane triacrylate; And / or, the amount of the active diluent added is such that the mass ratio of the active diluent to the mixed solution is 5% to 15%; And / or, the photoinitiator is any one of 2-hydroxy-2-methyl-1-phenyl-1-propanone, 2-hydroxy-2-methyl-1-phenylpropanone, 2-methyl-2-(4-morpholinyl)-1-[4-(methylthio)phenyl]-1-propanone, 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, and ethyl 2,4,6-trimethylbenzoylphenylphosphonate; And / or, the amount of the photoinitiator added is such that the mass ratio of the photoinitiator to the mixed solution is 3% to 7%.

3. The preparation method according to claim 1, characterized in that: The mass ratio of the organic fluorine monomer to the castor oil-based oligomer is 1:9; And / or, the active diluent is trimethylolpropane triacrylate, and the mass ratio of the active diluent to the mixed solution is 15%; And / or, the photoinitiator is 2-hydroxy-2-methyl-1-phenyl-1-propanone, and the mass ratio of the photoinitiator to the mixed solution is 5%.

4. The preparation method according to claim 1, characterized in that: The preparation of the organic fluorine monomer comprises the following steps: Hexafluorobutyl methacrylate, 2-mercaptoethanol and azobisisobutyronitrile are mixed in an organic solvent at a molar ratio of 1:0.5-1.5:0.001-0.01, mixed and reacted for 6-10 hours at a constant temperature of 70-100° C. with stirring, and cooled to room temperature; Add isophorone diisocyanate to the reaction system, heat to 40-90° C., then add a catalyst, and react for 1-3 hours to obtain the organic fluorine monomer.

5. The preparation method according to claim 4, characterized in that: The organic solvent is any one of toluene, acetone, butanone, dichloromethane, N,N-dimethylformamide, and dimethylacetamide; And / or, the catalyst is any one of dibutyltin dilaurate, pentamethyldiethylenetriamine, N,N-dimethylcyclohexylamine, and organic bismuth.

6. The preparation method according to claim 1, characterized in that: The preparation of the castor oil-based oligomer comprises the following steps: Castor oil, isophorone diisocyanate and isobornyl acrylate are mixed and reacted at 40-50° C. for 0.5-1.5 hours under stirring conditions; a catalyst is added and reacted until the isocyanate content is reduced to half of the initial value to obtain a castor oil-isocyanate intermediate; Hydroxyethyl acrylate and a polymerization inhibitor are added to the castor oil-isocyanate intermediate, and the mixture is reacted at a temperature of 70 to 90° C. and a stirring rate of 200 to 250 r / min until the isocyanate group completely disappears, thereby obtaining the castor oil-based oligomer.

7. The preparation method according to claim 6, characterized in that: The reaction degree of the isophorone diisocyanate is detected by the di-n-butylamine method; And / or, the catalyst is any one of dibutyltin dilaurate, pentamethyldiethylenetriamine, N,N-dimethylcyclohexylamine, and organic bismuth; And / or, the polymerization inhibitor is any one of 2,6-di-tert-butyl-p-cresol, hydroquinone, 4,4-dihydroxybiphenyl, and 3-(3,5-di-tert-butyl-4-hydroxyphenyl) propionate.

8. A photocurable material, characterized in that: The compound is prepared by the preparation method according to any one of claims 1 to 7.

9. A photocurable film, characterized in that: The method is obtained by spreading the photocurable material according to claim 8 into a film and then irradiating the film under ultraviolet light.

10. The photocurable film according to claim 9, characterized in that: The duration of the ultraviolet light irradiation is 1 to 2 minutes.

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