Dental repair resin added with cysteine and preparation method thereof

Abstract

The invention discloses a cysteine-added dental restoration resin and a preparation method thereof. The dental restoration resin is prepared from the following components in parts by weight: 60 to 70 parts of bisphenol A glycerol dimethacrylate, 30 to 40 parts of triethylene glycol dimethacrylate, 0.6 to 0.8 part of camphorquinone, 0.8 to 1.0 part of dimethylaminoethyl methacrylate, 0 to 3 parts (not 0) of 2-(methacryloyloxy) ethyl (2, 3-dihydroxybenzoyl) lysine salt, and 0 to 0.87 part (not 0) of cysteine. And then pouring into a mold, curing under visible blue light, and drying, so as to obtain the product. A light-cured resin system is formed by adding cysteine in a specific proportion into a resin system, and the mechanical properties such as the antibacterial property, the adhesive property and the hardness of the resin can be remarkably improved.

Description

Technical Field

[0001] The present invention belongs to the technical field of dental materials, and relates to a dental restoration resin added with cysteine and a preparation method thereof. Background Art

[0002] Tooth diseases have always been a problem of great concern to the general population and are also the most important part for maintaining human health. In recent years, more and more people have paid attention to tooth diseases such as dental plaque, dental caries, gingivitis, periodontitis, etc., and there have been more and more related studies. However, after dental filling treatment, the filling falls off and secondary caries appear, and the failure rate of tooth restoration increases. Therefore, it is necessary to develop a filling resin or adhesive with good biocompatibility, excellent adhesion performance and good antibacterial performance.

[0003] In the complex seawater environment, marine mussels can rely on the adhesive proteins they secrete to firmly adhere to reefs and other materials. Inspired by marine mussels, scholars have conducted fruitful mussel bionic bonding research in the oral field. Reference 1 [Kang Li, Chenmin Yao, Yuhong Sun, et al. Enhancing resin-dentin bond durability using a novel mussel-inspired monomer. Materials Today Bio, 2021, 12: 2590-0064.] studied N-(3,4-dihydroxyphenylethyl) methacrylamide (DMA) as a functional monomer in the dentin bonding system and found that the carbon-carbon double bond of DMA can polymerize with the bonding monomer without affecting the degree of conversion and elastic modulus, and can also cross-link with dentin collagen through non-covalent bonds. The catechol group can cross-link with dentin collagen and inhibit the matrix metalloproteinases (MMPs) that start and activate the hydrolytic degradation of the underlying collagen. The amide bond has hydrolytic stability, which can enhance the integrity of the resin-dentin interface and the durability of the bonding. However, the catechol group is easily oxidized, which affects the bonding and mechanical properties of the curing system. Reference 2 [Zunhan Hu, Wenzhen Wu, Meizhe Yu, et al. Mussel-inspired polymer with catechol and cationic Lys functionalities for dentin wet bonding. Materials Today Bio, 2023, 18, 100506: 2590-0064.] synthesized a monomer CLM and found that it has a certain inhibitory effect on the resin system, and the catechol group is easily oxidized. The catechol structure is the key component that can cure into a hard and stable structure while having excellent bonding ability, that is, the oxidation of the catechol structure will lead to a decrease in adhesion, and the mechanical properties are also poor due to the low degree of polymerization. Summary of the invention

[0004] The present invention aims to provide a dental restoration resin added with cysteine and a preparation method thereof.

[0005] The technical solution for achieving the purpose of the present invention is as follows:

[0006] Dental restorative resin with added cysteine, comprising the following components in parts by mass:

[0007] 60 - 70 parts of bisphenol A glycerol dimethacrylate, 30 - 40 parts of triethylene glycol dimethacrylate, 0.6 - 0.8 parts of camphorquinone, 0.8 - 1.0 parts of dimethylaminoethyl methacrylate, 0 - 3 parts but not 0 of 2-(methacryloyloxy)ethyl(2,3-dihydroxybenzoyl)lysine salt (CLM), 0 - 0.87 parts but not 0 of cysteine.

[0008] Furthermore, 70 parts of bisphenol A glycerol dimethacrylate, 30 parts of triethylene glycol dimethacrylate, 0.6 parts of camphorquinone, 0.8 parts of dimethylaminoethyl methacrylate, 1 - 3 parts of 2-(methacryloyloxy)ethyl(2,3-dihydroxybenzoyl)lysine salt, and 0.87 parts of cysteine.

[0009] Furthermore, the molar ratio of cysteine to camphorquinone is 1 - 2:1.

[0010] The preparation method of the above-mentioned dental restoration resin added with cysteine includes the following steps:

[0011] According to the formula, mix bisphenol A glycerol dimethacrylate, triethylene glycol dimethacrylate, camphorquinone, dimethylaminoethyl methacrylate, 2-(methacryloyloxy)ethyl(2,3-dihydroxybenzoyl)lysine salt and cysteine, perform ultrasonic cleaning under light - shielding conditions, remove bubbles, and then pour it into a mold and cure under visible blue light, and dry to obtain the dental restoration resin.

[0012] Furthermore, the ultrasonic time is 60 - 120 s.

[0013] Furthermore, the curing time is 60 - 120 s.

[0014] Furthermore, the drying temperature is 37 °C and the drying time is 24 - 48 h.

[0015] Compared with the prior art, the present invention has the following advantages:

[0016] In the present invention, by adding cysteine containing a mercapto group to the original dental restoration resin system, due to the excellent antioxidant effect, free radical scavenging effect, etc. of the mercapto group, the inhibition effect of CLM is greatly weakened, the degree of photo - initiated free radical polymerization of the resin system increases to 71.54%, catechol is effectively protected during curing, its oxidation is reduced, the resin color becomes significantly lighter, the bonding performance of the system is increased by 1.7 times, and the mechanical properties such as hardness are increased by 1.4 times, having excellent mechanical properties. Description of the Drawings

[0017] Figure 1 is the double - bond conversion rate of the photocuring resin of each system;

[0018] Figure 2are the results of lap shear tensile tests on mica sheets;

[0019] Figure 3 are the volume shrinkage rates Vs of different resin systems;

[0020] Figure 4 are the water absorption rates W of different resin systems;

[0021] Figure 5 are the results of Vickers hardness HV tests on different resins.

[0022] Figure 6 is a bar chart of the results of direct contact antibacterial test data of the resin against Staphylococcus aureus;

[0023] Figure 7 are the results of direct contact antibacterial tests of the resin against Staphylococcus aureus in an environment with pH = 5.5;

[0024] Figure 8 are the results of direct contact antibacterial tests of the resin against Staphylococcus aureus in an environment with pH = 7.4. Detailed implementation manners

[0025] In order to make the objectives, technical solutions, and advantages of the present invention clearer and more understandable, the present invention will be further described in detail below with reference to specific embodiments and the accompanying drawings. It should be understood that the specific embodiments described herein are only used to explain the present invention and are not used to limit the present invention.

[0026] In the following embodiments, bisphenol A glycerol dimethacrylate was purchased from Nanjing Jiaozi Teng Scientific Equipment Co., Ltd., triethylene glycol dimethacrylate, camphorquinone, and dimethylaminoethyl methacrylate were all purchased from Aladdin Reagent Co., Ltd., and cysteine was purchased from Shanghai Yian Chemical Technology Co., Ltd.

[0027] The structural formula of 2-(methacryloyloxy)ethyl (2,3-dihydroxybenzoyl)lysine salt (CLM) is: Reference [Zunhan Hu, Wenzhen Wu, Meizhe Yu, et al. Mussel-inspired polymer with catechol and cationic Lys functionalities for dentin wet bonding. Materials Today Bio, 2023, 18, 100506: 2590 - 0064.]

[0028] Comparative Example 1

[0029] Put 70 parts of bisphenol A glycerol dimethacrylate, 30 parts of triethylene glycol dimethacrylate, 0.6 part of camphorquinone, and 0.8 part of dimethylaminoethyl methacrylate into a 2-ml centrifuge tube. After manually mixing evenly, wrap it completely with tin foil. Place the centrifuge tube in an ultrasonic cleaner and ultrasonicate for 60 s to remove the tiny bubbles in the system. Pour the mixed solution into a polytetrafluoroethylene 6-well mold with a diameter of 10 mm and a height of 3 mm. After clamping both ends with cover glasses, use a curing lamp to cure both sides at a distance of no more than 2 mm for 60 s respectively. After completion, carefully take out the resin sheet from the mold and put it into a constant temperature oven at 37 °C for 48 h to obtain the photocured resin material.

[0030] Comparative Example 2

[0031] Put 70 parts of bisphenol A glycerol dimethacrylate, 30 parts of triethylene glycol dimethacrylate, 0.6 part of camphorquinone, 0.8 part of dimethylaminoethyl methacrylate, and 1 part of CLM into a 2-ml centrifuge tube. After manually mixing evenly, wrap it completely with tin foil. Place the centrifuge tube in an ultrasonic cleaner and ultrasonicate for 60 s to remove the tiny bubbles in the system. Pour the mixed solution into a polytetrafluoroethylene 6-well mold with a diameter of 10 mm and a height of 3 mm. After clamping both ends with cover glasses, use a curing lamp to cure both sides at a distance of no more than 2 mm for 60 s respectively. After completion, carefully take out the resin sheet from the mold and put it into a constant temperature oven at 37 °C for 48 h to obtain the photocured resin material.

[0032] Comparative Example 3

[0033] Put 70 parts of bisphenol A glycerol dimethacrylate, 30 parts of triethylene glycol dimethacrylate, 0.6 part of camphorquinone, 0.8 part of dimethylaminoethyl methacrylate, and 2 parts of CLM into a 2-ml centrifuge tube. After manually mixing evenly, wrap it completely with tin foil. Place the centrifuge tube in an ultrasonic cleaner and ultrasonicate for 60 s to remove the tiny bubbles in the system. Pour the mixed solution into a polytetrafluoroethylene 6-well mold with a diameter of 10 mm and a height of 3 mm. After clamping both ends with cover glasses, use a curing lamp to cure both sides at a distance of no more than 2 mm for 60 s respectively. After completion, carefully take out the resin sheet from the mold and put it into a constant temperature oven at 37 °C for 48 h to obtain the photocured resin material.

[0034] Comparative Example 4

[0035] Put 70 parts of bisphenol A glycerol dimethacrylate, 30 parts of triethylene glycol dimethacrylate, 0.6 parts of camphorquinone, 0.8 parts of dimethylaminoethyl methacrylate, and 3 parts of CLM into a 2-ml centrifuge tube. After manually mixing evenly, wrap it completely with tinfoil. Place the centrifuge tube in an ultrasonic cleaner and ultrasonicate for 60 s to remove the tiny air bubbles in the system. Pour the mixed solution into a polytetrafluoroethylene 6-well mold with a diameter of 10 mm and a height of 3 mm. After clamping both ends with glass slides, use a curing lamp to cure both sides at a distance of no more than 2 mm for 60 s respectively. After completion, carefully take out the resin sheet from the mold and put it into a constant-temperature oven at 37 °C for 48 h to obtain a photocurable resin material.

[0036] Example 1

[0037] Put 70 parts of bisphenol A glycerol dimethacrylate, 30 parts of triethylene glycol dimethacrylate, 0.6 parts of camphorquinone, 0.8 parts of dimethylaminoethyl methacrylate, 1 part of CLM, and 0.87 parts of cysteine into a 2-ml centrifuge tube. After manually mixing evenly, wrap it completely with tinfoil. Place the centrifuge tube in an ultrasonic cleaner and ultrasonicate for 60 s to remove the tiny air bubbles in the system. Pour the mixed solution into a polytetrafluoroethylene 6-well mold with a diameter of 10 mm and a height of 3 mm. After clamping both ends with glass slides, use a curing lamp to cure both sides at a distance of no more than 2 mm for 60 s respectively. After completion, carefully take out the resin sheet from the mold and put it into a constant-temperature oven at 37 °C for 48 h to obtain a dental restoration resin.

[0038] Example 2

[0039] Put 70 parts of bisphenol A glycerol dimethacrylate, 30 parts of triethylene glycol dimethacrylate, 0.6 parts of camphorquinone, 0.8 parts of dimethylaminoethyl methacrylate, 2 parts of CLM, and 0.87 parts of cysteine into a 2-ml centrifuge tube. After manually mixing evenly, wrap it completely with tinfoil. Place the centrifuge tube in an ultrasonic cleaner and ultrasonicate for 60 s to remove the tiny air bubbles in the system. Pour the mixed solution into a polytetrafluoroethylene 6-well mold with a diameter of 10 mm and a height of 3 mm. After clamping both ends with glass slides, use a curing lamp to cure both sides at a distance of no more than 2 mm for 60 s respectively. After completion, carefully take out the resin sheet from the mold and put it into a constant-temperature oven at 37 °C for 48 h to obtain a dental restoration resin.

[0040] Example 3

[0041] 70 parts of bisphenol A glycerol dimethacrylate, 30 parts of triethylene glycol dimethacrylate, 0.6 parts of camphorquinone, 0.8 parts of dimethylaminoethyl methacrylate, 3 parts of CLM, and 0.87 parts of cysteine were placed in a 2-ml centrifuge tube. After manual mixing, it was completely wrapped with tin foil. The centrifuge tube was placed in an ultrasonic cleaner and sonicated for 60 s to remove the tiny air bubbles in the system. The mixed solution was poured into a polytetrafluoroethylene 6-well mold with a diameter of 10 mm and a height of 3 mm. After clamping both ends with cover glasses, it was cured on both sides with a curing lamp at a distance of no more than 2 mm for 60 s. After that, the resin sheet was carefully taken out of the mold and placed in a constant temperature oven at 37 °C for 48 h to obtain a dental restoration resin.

[0042] Performance test example

[0043] The photocurable resin materials prepared in each comparative example and example were subjected to resin polymerization degree test, direct contact antibacterial test, bonding property test, volume shrinkage rate, water absorption rate, water contact angle test, and Vickers hardness test, as follows.

[0044] 1. Resin polymerization degree test

[0045] The resin systems prepared in Comparative Examples 1-4 and Examples 1-3 were respectively tested for infrared spectra before and after photocuring by a Fourier-transform infrared spectrometer (FT-IR), and then quantitatively analyzed through the peak areas in the spectra. Using the benzene ring (1608 cm -1 ) that is not affected by the polymerization process as the reference absorption peak, the content change of the C═C double bond (1637 cm -1 ) before and after the polymerization reaction was quantitatively analyzed. The double bond conversion rate (DC) obtained by formula (1) is the polymerization degree of the resin system. Double bond conversion rate calculation formula:

[0046]

[0047] Among them,

[0048] A C＝C is the C═C peak area before curing,

[0049] A 苯环 is the benzene ring peak area before curing,

[0050] A′ C＝C is the C═C peak area after curing,

[0051] A′ 苯环 is the benzene ring peak area after curing.

[0052] After the cured resin sheet was appropriately ground with an agate mortar, FT-IR spectroscopic tests were carried out to obtain the infrared spectra of each test group. By calculating the double bond conversion rate through the above formula (1), the degree of polymerization under different formulations can be obtained, thereby determining the optimal addition amounts of CLM and L-cys.

[0053] The results show that Figure 1 compared with Comparative Example 1, in Examples 2 and 3 with added cysteine, the double bond conversion rates of the resins are higher than those of the resin without addition. Moreover, based on the polymerization degree of only 12.80% in Comparative Example 4, the polymerization degree of Example 3 with added cysteine reaches 68.54%. It can be seen that the addition of cysteine greatly increases the polymerization degree of the resin and weakens the inhibition phenomenon of CLM. The highest polymerization degree of the resin in Example 2 reaches 71.54%.

[0054] 2. Adhesion performance test

[0055] The material mixtures in Comparative Examples 1-4 and Examples 1-3 were respectively mixed evenly, wrapped completely with tin foil and stored in the dark for standby. A clean transparent mica sheet with a specification of 50 mm in length, 17 mm in width and 0.14 mm in thickness was taken out. An appropriate amount of the resin mixture was poured on one mica sheet and covered with another mica sheet. Then, curing was carried out on both sides with a curing lamp at a distance of about 1 mm, moving while irradiating to ensure that each part was illuminated. After curing, it was placed in an oven at 37 °C for a 48-hour dark reaction. At least 3 specimens were prepared for each group. After completion, the lap shear tensile specimens were prepared.

[0056] The prepared specimens were subjected to lap shear tensile tests through a universal testing machine. The parameters of each specimen were set respectively. The operating system was tension, and the loading head moving speed was set to 1 mm / min for tensile testing. After completion, the shear strength σ of different experimental groups was calculated through formula (2) c . The calculation formula for lap shear strength is as follows:

[0057]

[0058] where

[0059] F max is the failure load, N,

[0060] A is the lap area, mm 2 .

[0061] From Figure 2It can be seen from the lap shear tensile test results that the bonding strengths of Examples 1, 2, and 3 with cysteine added are 2.5, 3.2, and 3.4 times that of Comparative Example 1 respectively. The bonding strength of Comparative Example 3 is slightly greater than that of Comparative Example 1. The bonding strength of Comparative Example 4 is lower than that of Comparative Example 1 due to low curing degree. It can be seen that the addition of cysteine greatly improves the bonding strength of the resin system.

[0062] 3. Volume shrinkage rate test

[0063] After mixing the material mixtures in Comparative Examples 1-4 and Examples 1-3 evenly and removing small bubbles by ultrasonic oscillation, carefully suck about 15 mm of the resin mixture with a spotting capillary of 0.3×100 mm specification. There should be no small bubbles in the liquid column. Accurately measure the height L0 of the liquid column with a vernier caliper, cure it with a handheld curing lamp for 120 s, place it in an oven at 37 °C for dark reaction for 48 h, and then measure the height of the cured liquid column, denoted as L1. The calculation formula for the resin volume shrinkage rate Vs is as follows:

[0064]

[0065] The results are as Figure 3 shown. It can be seen that the resin volume shrinkage rates of Examples 1, 2, and 3 with cysteine added all decrease. The decrease in the volume shrinkage rates of Comparative Examples 3 and 4 is due to low polymerization degree as known from the previous experiments. In dental restorative resins, the smaller the volume shrinkage change, the more meaningful the clinical application.

[0066] 4. Water absorption rate test

[0067] After taking out the resin sheets of Examples 1-3 and Comparative Examples 1-4 from the oven at 37 °C, accurately weigh their masses, denoted as M0. Subsequently, place the resins in centrifuge tubes containing 4 mL of deionized water and keep them in the oven at a constant temperature of 37 °C. After 24 h, take out the resin sheets from the centrifuge tubes, dry the water on the surface of the resin sheets with filter paper, and then weigh their masses, denoted as M1. According to formula (4), the water absorption rate W of the resin sheets can be obtained:

[0068]

[0069] The results are as Figure 4 shown. The water absorption rate of dental restorative resins is generally low, usually between 0.5% and 3%. The water absorption rate represents the ability of the material to absorb water. A lower water absorption rate is beneficial to reducing the volume expansion and property degradation of the material in a humid environment. The water absorption rates of Examples 1 and 2 meet the standard and are lower than 3%.

[0070] 5. Water contact angle test

[0071] The resin sheets of Comparative Examples 1-4 and Examples 1-3 were taken out from an oven at 37 °C, and the surface was polished with 300-mesh water sandpaper until flat. Then, one side of the resin was firmly adhered to an appropriate position on a glass slide with double-sided tape to obtain a contact angle test specimen. Subsequently, it was tested with a JGW-600 contact angle tester. After obtaining the test pictures, the contact angle CA was accurately measured with Image-Pro Plus analysis software.

[0072] The data of the water contact angle of each resin are shown in Table 1. The water contact angle of dental restorative resins is usually between 20° and 90°. A lower water contact angle indicates a higher affinity of the resin for water, that is, water is more likely to wet the resin surface, and bacteria are less likely to adhere to the resin surface. From the data of the water contact angle of the resins in Examples 1 and 2, the addition of cysteine has no obvious effect on it. Compared with Comparative Example 1, the hydrophilicity is greatly enhanced.

[0073] Table 1 Water contact angles of each resin

[0074] Experimental group Comparative example 1 Comparative example 2 Comparative example 3 Comparative example 4 Example 1 Example 2 Example 3 Contact angle 93.5 91.7 75.9 0.0 82.8 76.8° 72.0°

[0075] 6. Vickers hardness test

[0076] The resin sheets of Comparative Examples 1, 3, 4 and Examples 2, 3 were taken out from an oven at 37 °C, and the surface was polished with 300-mesh water sandpaper until flat. The surface of the specimen was tested at 5 scattered points with an HVS-10(Z) (automatic turret) digital display Vickers hardness tester, with a load of 25 g and a load time of 15 s. The formula for calculating Vickers hardness is:

[0077]

[0078] Among them,

[0079] d is the average value of the two diagonals of the indentation.

[0080] The results are as Figure 5 shown. It can be seen that the Vickers hardness values of the resins in Examples 2 and 3 with the addition of cysteine are higher than those of Comparative Examples 1, 3, 4. It can be known that the addition of cysteine enhances the hardness of the resin. The HV value of Comparative Example 3 is higher than that of the control group, and the HV value of Comparative Example 4 is lower than that of the control group. It can be known that the hardness of the resin decreases with the increase of the CLM content, but the hardness of the resin in Example 3 after adding cysteine is still 1.44 times that of Comparative Example 1. It can be seen that cysteine has a significant effect on enhancing the hardness of the resin system.

[0081] 7. Direct contact antibacterial test

[0082] After the resin sheets of Comparative Examples 1-3 and Example 2 were sterilized under an ultraviolet lamp for 30 min, they were transferred to a 24-well plate with sterile forceps, and 10 μL of a concentration of 105 A freshly diluted Staphylococcus aureus (S. aureus) suspension at CFU / mL was dropped onto the resin sheet in the well, and then covered with a film to ensure uniform contact between the bacterial solution and the surface of the resin sheet. The microplate was placed in an incubator at a constant temperature of 37°C and a constant humidity for 18 hours. After incubation, the microplate was taken out and placed on a laminar flow bench. The resin sheet was taken out with sterile forceps and put into a sterile test tube containing 2 mL of PBS, sealed with a rubber stopper, and shaken thoroughly with a vortex mixer for 2 minutes to elute the bacteria on the resin sheet completely. Subsequently, it was diluted by a factor of two with PBS solution. 100 μL was taken out with a pipette for plating, marked, and then placed in an incubator at a constant temperature of 37°C and a constant humidity for 48 hours. After taking it out, the number of remaining bacteria was counted by the plate counting method, and the bacterial survival rate of Comparative Example 2-3 and Example 2 compared with Comparative Example 1 was statistically analyzed. The formula for bacterial survival rate is expressed as:

[0083]

[0084] Among them,

[0085] Ne is the number of surviving bacteria in the experimental group,

[0086] Nc is the number of surviving bacteria in the control group.

[0087] The results are as Figures 6-8 shown. It can be seen that the antibacterial performance of CLM is excellent. In Comparative Example 3, all Staphylococcus aureus were killed in an environment with pH = 5.5 (the antibacterial result is as Figure 7 ) and pH = 7.4 (the antibacterial result is as Figure 8 ). And there was no obvious change in the antibacterial result of Example 2 after adding cysteine compared with Comparative Example 3, and both had excellent antibacterial performance.

[0088] In summary, it can be known that compared with Comparative Example 1, Examples 2 and 3 have better polymerization degree, lap shear tensile strength, Vickers hardness and direct contact antibacterial property, and lower volume shrinkage rate and water contact angle; due to low curing degree, the mechanical properties of Comparative Example 4 are poor; compared with Comparative Example 3 and 4, in the systems of Examples 2-3, due to the addition of cysteine, their polymerization degree, lap shear tensile strength and Vickers hardness are stronger, and cysteine has no obvious effect on the antibacterial performance of CLM, the volume shrinkage rate is lower, and the water contact angle and water absorption rate are within the standard range.

[0089] The above are only the preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent replacements, and improvements made within the spirit and principle of the present invention should be included in the protection scope of the present invention.

Claims

1. A dental restorative resin added with cysteine, characterized in that, By mass parts, it includes the following components: 60 - 70 parts of bisphenol A glycerol dimethacrylate, 30 - 40 parts of triethylene glycol dimethacrylate, 0.6 - 0.8 part of camphorquinone, 0.8 - 1.0 part of dimethylaminoethyl methacrylate, 0 - 3 parts but not 0 of 2-(methacryloyloxy)ethyl(2,3-dihydroxybenzoyl)lysine salt, 0 - 0.87 part but not 0 of cysteine.

2. The dental restoration resin according to claim 1, wherein By mass parts, it includes the following components: 70 parts of bisphenol A glycerol dimethacrylate, 30 parts of triethylene glycol dimethacrylate, 0.6 part of camphorquinone, 0.8 part of dimethylaminoethyl methacrylate, 1 - 3 parts of 2-(methacryloyloxy)ethyl(2,3-dihydroxybenzoyl)lysine salt, 0.87 part of cysteine.

3. The dental restoration resin according to claim 1, characterized in that, The molar ratio of cysteine to camphorquinone is 1 - 2:

1.

4. The preparation method of the dental restoration resin according to claims 1 to 3, characterized in that, It includes the following steps: According to the formula, mix bisphenol A glycerol dimethacrylate, triethylene glycol dimethacrylate, camphorquinone, dimethylaminoethyl methacrylate, 2-(methacryloyloxy)ethyl(2,3-dihydroxybenzoyl)lysine salt and cysteine, perform ultrasonic cleaning under light - shielding conditions, remove bubbles, then pour into a mold and cure under visible blue light, and dry to obtain dental restorative resin.

5. The preparation method according to claim 4, characterized in that, The ultrasonic time is 60 - 120 s.

6. The preparation method according to claim 4, characterized in that, The curing time is 60 - 120 s.

7. The preparation method according to claim 4, characterized in that, The drying temperature is 37 °C and the drying time is 24 - 48 h.

Images