CN113797100B - High-biocompatibility bio-based antibacterial dental restoration material and preparation method thereof - Google Patents
High-biocompatibility bio-based antibacterial dental restoration material and preparation method thereof Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/69—Medicaments
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/831—Preparations for artificial teeth, for filling teeth or for capping teeth comprising non-metallic elements or compounds thereof, e.g. carbon
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- Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Dental Preparations (AREA)
Abstract
The invention provides a high-biocompatibility bio-based antibacterial dental restoration material and a preparation method thereof, wherein the material is prepared by taking 5', 5-diallyl-2, 2' -biphenol and pentaerythritol tetramercaptoacetate as reactants, tetraene silane as a filler and 2-isopropyl thioxanthone as a catalyst through addition polymerization. The method utilizes the tetraethylene silane to replace the traditional silica filler, and the tetraene silane and the pentaerythritol tetramercaptoacetate are subjected to addition polymerization, so that the organic thermosetting resin and the filler are combined in a chemical bond form, the hardness and the wear resistance of the material can be improved, and the material has good mechanical property and stable quality. The dental restoration material prepared by using 5', 5-diallyl-2, 2' -biphenol as a raw material has a long-acting antibacterial effect, and the service life of the dental restoration material is prolonged; and has high biocompatibility, and solves the risk that other chemical synthesis photo-curing dental resin materials stay in the human body for a long time to generate toxicity.
Description
Technical Field
The invention relates to the technical field of materials, in particular to a high-biocompatibility bio-based antibacterial dental restoration material and a preparation method thereof.
Background
The light-cured resin dental restoration material has the characteristics of low price, simple forming, good individual matching property and the like, and is a dental restoration material commonly used in the oral medical industry at present. However, the light-cured resin dental restorative material has the problem that bacteria are easy to adhere to the dental restorative material, so that dental caries lesion is caused. Therefore, the development of antibacterial composite resin dental restorative materials is an important way for improving the light-cured resin dental restorative materials.
At present, the industry mainly adds metal silver/copper nano particles in the composite resin dental restorative material to endow the resin with an antibacterial function. Patent document No. CN104887535B discloses a preparation method of a low-volume-shrinkage antibacterial dental resin composite material, which comprises the steps of preparing a dental resin solution by using bifunctional acrylate resin and phosphoryl-containing acrylate resin, and then adding a silver source compound, a photoinitiator and an inorganic filler, wherein the silver source compound can release nano silver to play an antibacterial role; and finally injecting the mixture into a mold, and irradiating the mixture by adopting blue light or ultraviolet light to prepare the dental filling material with low volume shrinkage and antibacterial effect. However, the antibacterial performance of the antibacterial resin in the above patent is in positive correlation with the release performance of the antibacterial substance, so that the release amount of the antibacterial substance is reduced and the antibacterial ability of the resin is reduced or disappeared with the lapse of time; in addition, the release of the antibacterial nano particles can also influence the mechanical properties of the resin, so that the dental restorative material adopting the composite resin added with the metal silver/copper nano particles has the problems of short antibacterial period and short service life.
In view of the above, there is a need to design an improved bio-based antibacterial material with high biocompatibility for the field of dental restorative materials to solve the above problems.
Disclosure of Invention
The invention aims to provide a high-biocompatibility bio-based antibacterial dental prosthetic material which has the characteristics of long-acting antibacterial effect, high biocompatibility, low preparation process cost, stable quality, good mechanical property and the like.
In order to realize the aim, the invention provides a high-biocompatibility bio-based antibacterial dental prosthetic material and a preparation method thereof. The dental prosthetic material comprises components of a first monomer, a second monomer, a filler and a catalyst; the catalyst is prepared from a first monomer, a second monomer and a filler, wherein the first monomer is 5', 5-diallyl-2, 2' -biphenol, the second monomer is pentaerythritol tetramercapto acetate, the filler is tetraene silane, and the catalyst is 2-isopropyl thioxanthone.
In a further improvement of the present invention, the mass part ratio of the first monomer, the second monomer, the filler and the catalyst is 38 to 45.
A method for preparing the high-biocompatibility bio-based antibacterial dental restorative material, which comprises the following steps:
s1, stirring and mixing the 5', 5-diallyl-2, 2' -biphenol and the pentaerythritol tetramercapto acetate at 110 ℃ to completely dissolve the compounds;
s2, adding the 2-isopropyl thioxanthone into the mixed solution obtained in the step S1, and stirring until the 2-isopropyl thioxanthone is completely dissolved;
s3, adding the tetraene silane into the S2 mixed solution, and uniformly stirring to obtain a mixed solution;
and S4, performing vacuum defoaming treatment on the mixed solution obtained in the step S3 at 110 ℃ to obtain a white or yellow viscous high-biocompatibility bio-based antibacterial dental restoration material.
As a further improvement of the invention, the white or yellow viscous high-biocompatibility bio-based antibacterial dental restoration material needs to be subjected to photocuring treatment during application.
As a further improvement of the invention, the light curing treatment is to irradiate for 5 to 10min by adopting a light source with the wavelength of 200 to 500 nm.
As a further improvement of the invention, the stirring speed is 200-400 r/min.
The beneficial effects of the invention are:
1. the invention provides a high-biocompatibility bio-based antibacterial dental restoration material and a preparation method thereof, the material is prepared by taking 5', 5-diallyl-2, 2' -biphenyl diphenol and pentaerythritol tetramercaptoacetate as reactants, tetraene silane as a filler and 2-isopropyl thioxanthone as a catalyst through addition polymerization, and the material is applied through photocuring treatment under a light source. Wherein the 5', 5-diallyl-2, 2' -biphenol is plant extract, has pharmacological effects of resisting inflammation, bacteria, pathogenic microorganism, ulcer and oxidation, and can be used for treating acute enteritis, bacillary dysentery, amebic dysentery, chronic gastritis, etc. In the aspect of antibacterial action, the 5', 5-diallyl-2, 2' -biphenol has obvious antibacterial activity on gram-positive bacteria, acid-resistant bacteria and filamentous fungi, has more obvious antibacterial action on streptococcus mutans, and has the strongest inhibition effect on staphylococcus. In addition, the compound is thiol-ene click reaction, phenolic hydroxyl does not participate in the reaction in the curing process, so that the dental material after curing still has antibacterial capability, and therefore, the bio-based antibacterial material prepared from 5', 5-diallyl-2, 2' -biphenol has long-acting antibacterial effect when being used as a dental restoration material, prolongs the service life, and has beneficial effects on stomach diseases and oral diseases.
2. In the preparation process of the material, tetraene silane is added to replace the conventional silicon dioxide SiO 2 Inorganic filler, vinyl on tetraene silane can carry out addition polymerization with the hydrosulfide group on pentaerythritol tetramercaptoacetate, and a chemical connection effect is achieved, so that the binding capacity of resin and filler is greatly increased. In addition, the addition of the tetraethylene silane can increase the hardness and the wear resistance of the teeth, so that the mechanical property is good, the quality is stable, the implanted teeth are easy to clean and brush, and the appearance of the teeth is bright and white.
3. The dental restorative material prepared from the natural biomass compound 5', 5-diallyl-2, 2' -biphenol used in the invention has excellent biocompatibility, is applied to the dental restorative material, has low manufacturing process cost, and solves the risk that other chemical synthesis light-cured dental resin materials are retained in a human body for a long time to generate toxicity.
Drawings
FIG. 1 is a molecular structural diagram of the bio-based antibacterial dental restorative material prepared by the present invention after curing.
FIG. 2 is an infrared spectrum of the bio-based antibacterial dental restorative material prepared in example 1 of the present invention.
FIG. 3 is an infrared spectrum of the bio-based antibacterial dental restorative material prepared in example 2 of the present invention.
FIG. 4 is a graph showing the results of testing the effects of examples 1 and 2 of the present invention and comparative example 1 on the activity of L929 cells by the CCK-8 method.
FIG. 5 is a graph showing the results of measuring the absorbance of the co-cultured bacterial liquid by the UV-Vis spectrophotometry in examples 1-2 and comparative examples 1-2.
Detailed Description
The following detailed description of the preferred embodiments of the present invention, taken in conjunction with the accompanying drawings, will make the objects, advantages and features of the present invention more comprehensible and clear for those skilled in the art, and thus define the scope of the present invention.
It should be noted that, in order to avoid obscuring the present invention with unnecessary details, only the structures and/or processing steps closely related to the solution of the present invention are shown in the drawings, and other details not closely related to the present invention are omitted.
In addition, it is also to be noted that the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus.
A high-biocompatibility bio-based antibacterial dental restorative material comprises a first monomer, a second monomer, a filler and a catalyst; wherein the first monomer is 5', 5-diallyl-2, 2' -biphenol, the second monomer is pentaerythritol tetramercaptoacetate, the filler is tetraethenylsilane, and the catalyst is 2-isopropyl thioxanthone. The mass parts of the first monomer, the second monomer, the filler and the catalyst are 38-45.
Specifically, a network polymer obtained by photocuring a high-biocompatibility bio-based antibacterial dental restorative material under a lighting condition, wherein the molecular structural formula of the dental restorative material after curing is as follows:
the reaction equation of photocuring of a high-biocompatibility bio-based antibacterial dental restorative material is as follows:
a preparation method of a high-biocompatibility bio-based antibacterial dental restoration material comprises the following steps:
s1, stirring and mixing 5', 5-diallyl-2, 2' -biphenol and pentaerythritol tetramercapto acetate at 110 ℃, wherein the stirring speed is 200-400 r/min, so that the 5', 5-diallyl-2, 2' -biphenol and pentaerythritol tetramercapto acetate are completely dissolved, and the mass part ratio of the 5', 5-diallyl-2, 2' -biphenol to the pentaerythritol tetramercapto acetate is 38-45;
s2, adding 2-Isopropyl Thioxanthone (ITX) into the mixed solution obtained in the step S1, and stirring until the mixture is completely dissolved, wherein the mass part ratio of the 2-Isopropyl Thioxanthone (ITX) to the S1 mixed solution is 1-3;
s3, adding tetraene silane into the S2 mixed solution, wherein the mass part ratio of the tetraene silane to the S2 mixture is 20-40;
s4, carrying out vacuum defoaming treatment on the mixed solution obtained in the step S3 at 110 ℃ to obtain a white or yellow viscous high-biocompatibility bio-based antibacterial dental restoration material;
wherein, the white or yellow viscous high-biocompatibility bio-based antibacterial dental restoration material needs to be subjected to photocuring treatment when being applied; the light curing treatment is to irradiate for 5-10 min by adopting a light source with the wavelength of 200-500 nm.
In particular, the high-biocompatibility bio-based antibacterial material is used for preparing dental prosthetic materials, and 5', 5-diallyl-2, 2' -biphenol has pharmacological effects of anti-inflammation, antibiosis, pathogenic microorganism resistance, ulcer resistance, oxidation resistance and the like as a medicament, and is commonly used for treating acute enteritis, bacillary or amoebic dysentery, chronic gastritis and the like. In the aspect of antibacterial action, the 5', 5-diallyl-2, 2' -biphenol has obvious antibacterial activity on gram-positive bacteria, acid-resistant bacteria and filamentous fungi, has more obvious antibacterial action on streptococcus mutans, and has the strongest inhibition effect on staphylococcus. In addition, the compound is thiol-ene click reaction, and phenolic hydroxyl does not participate in the reaction in the curing process, so that the dental material after curing still has antibacterial capability, and therefore, the bio-based antibacterial material prepared by using 5', 5-diallyl-2, 2' -biphenol or derivatives thereof has long-acting antibacterial and antibacterial effects when being used as a dental restoration material, prolongs the service life, and has beneficial effects on stomach diseases and oral diseases.
Adding tetraene silane to replace conventional silicon dioxide SiO 2 Inorganic filler, vinyl on tetraene silane can carry out addition polymerization with the hydrosulfide group on pentaerythritol tetramercaptoacetate, and a chemical connection effect is achieved, so that the binding capacity of resin and filler is greatly increased. In addition, the addition of the tetraethylene silane can increase the hardness and the wear resistance of the teeth, so that the mechanical property is good, the quality is stable, the implanted teeth are easy to clean and brush, and the appearance of the teeth is bright and white.
The 5', 5-diallyl-2, 2' -biphenol used in the invention is a natural biomass compound, and the material prepared by using the 5', 5-diallyl-2, 2' -biphenol has excellent biocompatibility, and when the material is applied to a dental prosthetic material, the manufacturing process cost is low, and the risk that other chemical synthesis light-cured dental resin materials are retained in a human body for a long time to generate toxicity is solved.
Example 1
The preparation method of the bio-based antibacterial material applied to the dental prosthetic material in the embodiment 1 of the invention comprises the following steps:
s1, stirring and mixing 3.8g of 5', 5-diallyl-2, 2' -biphenyl diphenol and 6.2g of pentaerythritol tetramercaptoacetate at 110 ℃, wherein the stirring speed is 200r/min, so that the 5', 5-diallyl-2, 2' -biphenyl diphenol and the pentaerythritol tetramercaptoacetate are completely dissolved;
s2, adding 100mg of 2-Isopropyl Thioxanthone (ITX) into the mixed solution obtained in the step S1, and stirring until the ITX is completely dissolved;
s3, adding 2g of tetraene silane into the mixed solution obtained in the step S2 and uniformly stirring;
and S4, performing vacuum defoaming treatment on the mixed solution obtained in the step S3 at 110 ℃ to obtain a white or yellow viscous high-biocompatibility bio-based antibacterial dental restoration material.
The dental restorative material obtained in example 1 was coated on a teflon plate and exposed to ultraviolet light having a wavelength of 365nm for 10min to cure the dental material, and then the cured dental restorative material was characterized as follows.
Referring to FIGS. 1-2, FIG. 2 is an infrared spectrum of the bio-based antibacterial dental restorative material prepared in example 1, from which it can be seen that 1635cm after polymerization of the reactants -1 Of
Characteristic peak sum 2571cm -1 Of (2)
The characteristic peak disappeared at 1134.71cm -1 Appear by
Characteristic peaks prove the successful synthesis of the bio-based antibacterial material. The structural formula of the material after curing is shown as figure 1:
FIG. 4 is a graph showing the results of CCK-8 assay on the activity of L929 cells in examples 1 and 2 and a blank control group according to the present invention. The relative cell survival rate of 24h in example 1 is 98.65%, which proves that the bio-based antibacterial material of the invention has very excellent cell compatibility and can be applied to dental prosthetic materials.
Example 2
The preparation method of the bio-based antibacterial material applied to the dental prosthetic material in the embodiment 2 of the invention comprises the following steps:
s1, stirring and mixing 4.5g of 5', 5-diallyl-2, 2' -biphenyl diphenol and 5.5g of pentaerythritol tetramercaptoacetate at 110 ℃, wherein the stirring speed is 200r/min, so that the components are completely dissolved;
s2, adding 300mg of 2-Isopropyl Thioxanthone (ITX) into the mixed solution obtained in the step S1, and stirring until the ITX is completely dissolved;
s3, adding 4g of tetraene silane into the S2 mixed solution and uniformly stirring;
and S4, performing vacuum defoaming treatment on the mixed solution obtained in the step S3 at 110 ℃ to obtain a white or yellow viscous high-biocompatibility bio-based antibacterial dental restoration material.
The dental restorative material obtained in example 2 was coated on a teflon plate and cured by irradiation with ultraviolet light having a wavelength of 365nm for 10min, and then the cured dental restorative material was characterized as follows.
Referring to FIG. 3, FIG. 3 is an infrared spectrum of the bio-based antibacterial material prepared in example 2, from which it can be seen that 1635cm was obtained after polymerization of the reactants -1 Of (2)
Characteristic peak sum 2571cm -1 Of
The characteristic peak disappeared at 1134.99cm -1 Appear by
Characteristic peaks prove the successful synthesis of the bio-based antibacterial material.
FIG. 4 is a graph showing the results of CCK-8 assay on the activity of L929 cells in examples 1 and 2 and a blank control group according to the present invention. The relative cell survival rate of 24h in example 2 is 99.16%, which proves that the bio-based antibacterial material has excellent cell compatibility and can be well applied to dental restoration materials.
Comparative example 1
Comparative example 1 is a blank control group, which is a pure bacterial solution cultured at 37 ℃ for 24 hours, and the absorbance thereof was measured by the ultraviolet-visible spectrophotometry.
Comparative example 2
Comparative example 2 is a glass ionomer cement group, which was cultured with commercially available dental materials and pure bacterial solutions at 37 ℃ for 24h, and the absorbance was measured by uv-vis spectrophotometry.
Referring to FIG. 5, FIG. 5 is a graph showing the results of measuring the absorbance of the co-cultured bacterial liquid by UV-Vis spectrophotometry in examples 1-2 and comparative examples 1-2. The bacteria used in the test are staphylococcus aureus, and the mass ratio of the bacteria liquid to the dental restorative material is 200. The experimental method comprises the following steps: the bio-based antibacterial material prepared in the above example 1-2 was co-cultured with staphylococcus aureus liquid for 24 hours at 37 ℃, and the absorbance of the solution at 600nm wavelength, i.e., the cell density OD600 of the cells, was measured by uv-vis spectrophotometry, and the bacteriostatic rate was calculated. In the figure, comparative example 1 is a blank control group, which is a pure bacterial solution cultured at 37 ℃ for 24 hours, and the OD600 value is measured by an ultraviolet-visible spectrophotometry method; comparative example 2 OD600 value after 24h of coculture of the dental restorative material of glass ion cement and pure bacteria solution in the group of glass ion cement; in the figure, data of examples 1-2 are OD600 values measured by UV-visible spectrophotometry after co-culturing the dental restorative materials prepared in examples 1 and 2 above with a pure bacterial solution at 37 ℃ for 24 hours. The results were: the OD value of comparative example 1 was 0.693; comparative example 2 had an OD of 0.657; the OD value of the sample 1 is 0.053, and compared with a blank control group, the bacteriostasis rate is 92.35%; the OD value of the sample 2 is 0.043, and compared with the blank control group, the bacteriostasis rate is 93.80%. The antibacterial and bacteriostatic effects of the bio-based antibacterial material are very good, and when the bio-based antibacterial material is applied to a dental restoration material, the long-acting antibacterial property can be endowed.
Example 3
The preparation method of the bio-based antibacterial material applied to the dental prosthetic material in the embodiment 3 of the invention comprises the following steps:
s1, stirring and mixing 3.8g of 5', 5-diallyl-2, 2' -biphenol and 6.2g of pentaerythritol tetramercaptoacetate at 110 ℃, wherein the stirring speed is 200r/min, so that the 5', 5-diallyl-2, 2' -biphenol and the pentaerythritol tetramercaptoacetate are completely dissolved;
s2, adding 200mg of 2-Isopropyl Thioxanthone (ITX) into the mixed solution obtained in the step S1, and stirring until the ITX is completely dissolved;
s3, adding 3g of tetraene silane into the S2 mixed solution and uniformly stirring;
and S4, carrying out vacuum defoaming treatment on the mixed solution obtained in the step S3 at 110 ℃ to obtain a white or yellow viscous high-biocompatibility bio-based antibacterial dental restoration material.
Example 4
The preparation method of the bio-based antibacterial material applied to the dental prosthetic material in the embodiment 4 of the invention comprises the following steps:
s1, stirring and mixing 3.8g of 5', 5-diallyl-2, 2' -biphenol and 6.2g of pentaerythritol tetramercaptoacetate at 110 ℃, wherein the stirring speed is 200r/min, so that the 5', 5-diallyl-2, 2' -biphenol and the pentaerythritol tetramercaptoacetate are completely dissolved;
s2, adding 300mg of 2-Isopropyl Thioxanthone (ITX) into the mixed solution obtained in the step S1, and stirring until the ITX is completely dissolved;
s3, adding 4g of tetraene silane into the S2 mixed solution and uniformly stirring;
and S4, performing vacuum defoaming treatment on the mixed solution obtained in the step S3 at 110 ℃ to obtain a white or yellow viscous high-biocompatibility bio-based antibacterial dental restoration material.
Example 5
The preparation method of the bio-based antibacterial material applied to the dental prosthetic material in the embodiment 5 of the invention comprises the following steps:
s1, stirring and mixing 4.0g of 5', 5-diallyl-2, 2' -biphenol and 6.0g of pentaerythritol tetramercapto acetate at 110 ℃, wherein the stirring speed is 200r/min, so that the components are completely dissolved;
s2, adding 100mg of 2-Isopropyl Thioxanthone (ITX) into the mixed solution obtained in the step S1, and stirring until the ITX is completely dissolved;
s3, adding 2g of tetraene silane into the S2 mixed solution and uniformly stirring;
and S4, performing vacuum defoaming treatment on the mixed solution obtained in the step S3 at 110 ℃ to obtain a white or yellow viscous high-biocompatibility bio-based antibacterial dental restoration material.
Example 6
The preparation method of the bio-based antibacterial material applied to the dental prosthetic material in the embodiment 6 of the invention comprises the following steps:
s1, stirring and mixing 4.0g of 5', 5-diallyl-2, 2' -biphenol and 6.0g of pentaerythritol tetramercapto acetate at 110 ℃, wherein the stirring speed is 200r/min, so that the components are completely dissolved;
s2, adding 200mg of 2-Isopropyl Thioxanthone (ITX) into the mixed solution obtained in the step S1, and stirring until the ITX is completely dissolved;
s3, adding 3g of tetraene silane into the S2 mixed solution and uniformly stirring;
and S4, performing vacuum defoaming treatment on the mixed solution obtained in the step S3 at 110 ℃ to obtain a white or yellow viscous high-biocompatibility bio-based antibacterial dental restoration material.
Example 7
The preparation method of the bio-based antibacterial material applied to the dental prosthetic material in the embodiment 7 of the invention comprises the following steps:
s1, stirring and mixing 4.0g of 5', 5-diallyl-2, 2' -biphenol and 6.0g of pentaerythritol tetramercapto acetate at 110 ℃, wherein the stirring speed is 200r/min, so that the components are completely dissolved;
s2, adding 300mg of 2-Isopropyl Thioxanthone (ITX) into the mixed solution obtained in the step S1, and stirring until the ITX is completely dissolved;
s3, adding 4g of tetraene silane into the S2 mixed solution and uniformly stirring;
and S4, performing vacuum defoaming treatment on the mixed solution obtained in the step S3 at 110 ℃ to obtain a white or yellow viscous high-biocompatibility bio-based antibacterial dental restoration material.
Example 8
The preparation method of the bio-based antibacterial material applied to the dental prosthetic material in the embodiment 8 of the invention comprises the following steps:
s1, stirring and mixing 4.5g of 5', 5-diallyl-2, 2' -biphenyl diphenol and 5.5g of pentaerythritol tetramercaptoacetate at 110 ℃, wherein the stirring speed is 200r/min, so that the pentaerythritol tetramercaptoacetate is completely dissolved;
s2, adding 100mg of 2-Isopropyl Thioxanthone (ITX) into the mixed solution obtained in the step S1, and stirring until the ITX is completely dissolved;
s3, adding 2g of tetraene silane into the S2 mixed solution and uniformly stirring;
and S4, performing vacuum defoaming treatment on the mixed solution obtained in the step S3 at 110 ℃ to obtain a white or yellow viscous high-biocompatibility bio-based antibacterial dental restoration material.
Example 9
The preparation method of the bio-based antibacterial material applied to the dental prosthetic material in the embodiment 9 of the invention comprises the following steps:
s1, stirring and mixing 4.5g of 5', 5-diallyl-2, 2' -biphenyl diphenol and 5.5g of pentaerythritol tetramercaptoacetate at 110 ℃, wherein the stirring speed is 200r/min, so that the components are completely dissolved;
s2, adding 200mg of 2-Isopropyl Thioxanthone (ITX) into the mixed solution obtained in the step S1, and stirring until the ITX is completely dissolved;
s3, adding 3g of tetraene silane into the S2 mixed solution and uniformly stirring;
and S4, performing vacuum defoaming treatment on the mixed solution obtained in the step S3 at 110 ℃ to obtain a white or yellow viscous high-biocompatibility bio-based antibacterial dental restoration material.
In conclusion, the high-biocompatibility bio-based antibacterial dental restoration material and the preparation method thereof are prepared by performing addition polymerization by using 5', 5-diallyl-2, 2' -biphenol and pentaerythritol tetrathioglycolate as reactants, tetraene silane as a filler and 2-isopropyl thioxanthone as a catalyst; the material can be cured and applied under the irradiation of a light source. The filler is combined with the organic thermosetting resin in a chemical bond mode, so that the hardness and the wear resistance of the material can be improved, and the material has good mechanical property and stable quality. In addition, the bio-based antibacterial material prepared by using the 5', 5-diallyl-2, 2' -biphenol or the derivatives thereof can play a long-acting antibacterial and bacteriostatic role when being applied to a dental restoration material, and the service life is prolonged; and the material has excellent biocompatibility, not only has low manufacturing process cost, but also solves the toxicity risk that other chemical synthesis photo-curing dental resin materials are retained in human bodies for a long time.
Although the present invention has been described in detail with reference to the preferred embodiments, it will be understood by those skilled in the art that various changes may be made and equivalents may be substituted for elements thereof without departing from the spirit and scope of the present invention.
Claims (5)
1. A high-biocompatibility bio-based antibacterial dental restorative material, which is characterized in that the dental restorative material comprises a first monomer, a second monomer, a filler and a catalyst; the catalyst is 2-isopropyl thioxanthone, wherein the first monomer is 5', 5-diallyl-2, 2' -biphenyl diphenol, the second monomer is pentaerythritol tetramercaptoacetate, the filler is tetraene silane, and the catalyst is 2-isopropyl thioxanthone; the mass part ratio of the first monomer to the second monomer to the filler to the catalyst is 38 to 45, and the mass part ratio of the filler to the catalyst is as follows.
2. A method for preparing a highly biocompatible bio-based antibacterial dental restorative material as defined in claim 1, comprising the steps of:
s1, stirring and mixing the 5', 5-diallyl-2, 2' -biphenol and the pentaerythritol tetramercapto acetate at 110 ℃ to completely dissolve the compounds;
s2, adding the 2-isopropyl thioxanthone into the mixed solution obtained in the step S1, and stirring until the 2-isopropyl thioxanthone is completely dissolved;
s3, adding the tetraene silane into the S2 mixed solution, and uniformly stirring to obtain a mixed solution;
and S4, carrying out vacuum defoaming treatment on the mixed solution obtained in the step S3 at 110 ℃ to obtain a white or yellow viscous high-biocompatibility bio-based antibacterial dental restoration material.
3. The method for preparing a highly biocompatible bio-based antibacterial dental restorative material as defined in claim 2, wherein the highly biocompatible bio-based antibacterial dental restorative material in a white or yellow viscous state is applied by photo-curing.
4. The method for preparing a highly biocompatible, bio-based antibacterial dental restorative material as defined in claim 3, wherein the light curing treatment is performed by irradiating with a light source having a wavelength of 200 to 500nm for 5 to 10min.
5. The preparation method of the high-biocompatibility bio-based antibacterial dental restorative material as claimed in claim 2, wherein the stirring speed is 200 to 400r/min.
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