CN115386256A - Caries-preventing invisible orthodontic appliance with antibacterial coating and preparation method and application thereof - Google Patents
Caries-preventing invisible orthodontic appliance with antibacterial coating and preparation method and application thereof Download PDFInfo
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- CN115386256A CN115386256A CN202211209386.8A CN202211209386A CN115386256A CN 115386256 A CN115386256 A CN 115386256A CN 202211209386 A CN202211209386 A CN 202211209386A CN 115386256 A CN115386256 A CN 115386256A
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- orthodontic appliance
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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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
- A61C7/00—Orthodontics, i.e. obtaining or maintaining the desired position of teeth, e.g. by straightening, evening, regulating, separating, or by correcting malocclusions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
- A61C7/00—Orthodontics, i.e. obtaining or maintaining the desired position of teeth, e.g. by straightening, evening, regulating, separating, or by correcting malocclusions
- A61C7/08—Mouthpiece-type retainers or positioners, e.g. for both the lower and upper arch
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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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- General Health & Medical Sciences (AREA)
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- Oral & Maxillofacial Surgery (AREA)
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Abstract
The invention provides an anti-caries invisible orthodontic appliance with an antibacterial coating, a preparation method and application thereof, wherein the anti-caries invisible orthodontic appliance comprises an invisible orthodontic appliance and an antibacterial coating arranged on the contact surface of the invisible orthodontic appliance and teeth; the raw materials for preparing the antibacterial coating comprise a photocuring polymerization monomer, a diluent, a photoinitiator, a polymerization inhibitor, an antibacterial agent and an antioxidant; through coating antibacterial coating on the contact surface with the stealthy orthodontic appliance of caries prevention of tooth direct contact, fundamentally has restrained the field planting of plaque on the tooth face, and then has realized the prevention to chalk spot through the biological activity and the bacterial colony quantity that reduce the plaque, just the stealthy orthodontic appliance of caries prevention has antibiotic duration long, antibiotic effectual and dress a great deal of advantages such as being difficult for droing.
Description
Technical Field
The invention belongs to the technical field of dental materials, and particularly relates to an anti-caries invisible orthodontic appliance with an antibacterial coating, and a preparation method and application thereof.
Background
With the continuous improvement of the economic income of people, people have more and more demands on tooth health and whitening, so that the invisible orthodontic appliance is developed very rapidly in China. The invisible orthodontic technology is characterized in that a transparent plastic movable appliance is manufactured on an ideal model and worn on teeth of a patient to facilitate normal growth and development of the dentognathic face and realize correction of the teeth of the patient, generally, the wearing period is 1-2 weeks, the invisible orthodontic appliance is worn for more than 20 hours every day, and the period of orthodontic treatment is longer and is 1-3 years. Because the wearing time of stealthy just abnormal ware is long, make the tooth be in the state of isolated saliva for a long time, the tooth face is difficult clean, and plaque is easy field planting, pile up on the tooth face, forms the biomembrane, and the plaque produces acid simultaneously makes enamel surface pH value reduce, leads to the tooth to demineralize, causes the incidence of disease of enamel chalk spot to rise, and the treatment process is longer, and at the in-process of treatment, need clean stealthy ware of correcting every day to guarantee the cleanliness factor of stealthy ware of correcting.
At present, fluoride is a recognized substance effective in preventing caries. Fluoride inhibits the growth of cariogenic bacteria in the oral cavity, inhibits bacterial acidogenesis, and simultaneously reduces the solubility of enamel surface in the teeth and promotes remineralization of demineralized enamel. Proper amount of fluoride is taken in during the development of teeth, so that the cusps are blunt and the fissure becomes shallow; this change in tooth morphology allows the tooth to be easily self-cleaning and provides enhanced resistance to caries formation. CN113197693A discloses an anticarious film, an anticarious solution, a dental appliance with the anticarious film and a method for forming the anticarious film on the dental appliance, wherein the main anticarious mechanism is that a coating containing fluoride is coated on a shell-shaped dental appliance body to achieve the function of fluoride anticarious. CN105232165A discloses a hidden orthodontic tooth socket with caries preventing ability and a caries preventing method, wherein the tooth socket comprises a tooth socket body, and a protective film is coated on the tooth socket body to play a role in preventing caries; the protective film is a fluorine protective agent in the fluorine-containing coating, the fluorine-containing gel or the fluorine-containing foam, and the protective film is coated on one side of the interior of the tooth socket body, which is close to the teeth. However, fluoride is added to generate fluoride ions, and the fluoride ions are continuously exuded to generate remineralization reaction with teeth, so that the long-term fluorine release capacity and fluorine release amount are difficult to maintain, the effect of preventing the orthodontic chalky stains for a long time cannot be achieved, and the problem of the orthodontic chalky stains cannot be fundamentally solved.
Therefore, the development of the caries-prevention invisible orthodontic appliance which can effectively prevent the colonization and propagation of dental plaque in the tooth socket and further can prevent chalk spots and has good antibacterial effect and long antibacterial time is an urgent technical problem to be solved in the field.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide an anti-caries invisible orthodontic appliance with an antibacterial coating, and a preparation method and application thereof.
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the invention provides an anti-caries invisible orthodontic appliance with an antibacterial coating, which comprises an invisible orthodontic appliance and an antibacterial coating arranged on the contact surface of the invisible orthodontic appliance and teeth;
the raw materials for preparing the antibacterial coating comprise a photocuring polymerization monomer, a diluent, a photoinitiator, a polymerization inhibitor, an antibacterial agent and an antioxidant.
The caries-preventing invisible orthodontic appliance with the antibacterial coating comprises an invisible orthodontic appliance and an antibacterial coating arranged on the contact surface of the invisible orthodontic appliance and teeth, and from the pathological change mechanism of generating chalk spots, a layer of antibacterial masking liquid is coated on the contact surface of the invisible orthodontic appliance and the teeth, and the antibacterial coating formed by photocuring the antibacterial masking liquid can be tightly bonded with the invisible orthodontic appliance and cannot fall off, so that the durability of an antibacterial effect is ensured; the raw materials for preparing the antibacterial coating comprise a photocuring polymerization monomer, a diluent, a photoinitiator, a polymerization inhibitor, an antibacterial agent and an antioxidant, and the antibacterial agent is added into the antibacterial coating, so that the antibacterial coating has an excellent antibacterial effect, and then the dental caries prevention invisible orthodontic appliance can effectively prevent the colonization and reproduction of dental plaque in the tooth socket after being worn, thereby effectively blocking the formation of a dental plaque biomembrane, inhibiting tooth demineralization and realizing the effect of preventing dental caries.
Preferably, the invisible orthodontic appliance is prepared by using orthodontic diaphragms.
In the invention, the orthodontic diaphragm can be directly purchased from a commercial product, and then the customized invisible orthodontic appliance is prepared according to personal customized data and a hot-press forming process.
Preferably, the thickness of the antimicrobial coating is 10 to 60 μm, such as 15 μm, 20 μm, 25 μm, 30 μm, 35 μm, 40 μm, 45 μm, 50 μm, or 55 μm, and the like.
Preferably, the raw materials for preparing the antibacterial coating comprise the following components in parts by weight:
wherein the photo-curable monomer may be 61 parts by weight, 62 parts by weight, 63 parts by weight, 64 parts by weight, 65 parts by weight, 66 parts by weight, 67 parts by weight, 68 parts by weight, 69 parts by weight, or the like.
The diluent may be 31 parts by weight, 32 parts by weight, 33 parts by weight, 34 parts by weight, 35 parts by weight, 36 parts by weight, 37 parts by weight, 38 parts by weight, 39 parts by weight, or the like.
The photoinitiator may be 0.55, 0.6, 0.65, 0.7, 0.75, 0.8, 0.85, 0.9, or 0.95 parts by weight, or the like.
The polymerization inhibitor may be 0.55 parts by weight, 0.6 parts by weight, 0.65 parts by weight, 0.7 parts by weight, 0.75 parts by weight, 0.8 parts by weight, 0.85 parts by weight, 0.9 parts by weight, 0.95 parts by weight, or the like.
The antioxidant can be 0.27, 0.29, 0.31, 0.33, 0.35, 0.37, 0.39, 0.41, 0.043, 0.45, 0.47, or 0.49 parts by weight or the like.
The antimicrobial agent may be 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, or 1.9 parts by weight, or the like.
Preferably, the photo-curable polymeric monomer comprises a photo-curable acrylate monomer, and more preferably BIS-GMA.
Preferably, the diluent comprises TEGDMA.
Preferably, the photoinitiator comprises camphorquinone.
Preferably, the polymerization inhibitor comprises 2-ethylhexyl 4- (dimethylamino) benzoate.
Preferably, the antioxidant comprises 2, 6-di-tert-butyl-p-cresol.
Preferably, the antibacterial agent is an inorganic nano antibacterial agent.
Preferably, the inorganic nano antibacterial agent comprises any one of zinc oxide, magnesium oxide or titanium dioxide or a combination of at least two of the zinc oxide, the magnesium oxide and the titanium dioxide.
In a second aspect, the present invention provides a method for preparing the caries preventing invisible orthodontic appliance according to the first aspect, wherein the method comprises the following steps:
(1) Mixing a photo-curing polymerization monomer, a diluent, a photoinitiator, a polymerization inhibitor, an antibacterial agent and an antioxidant to obtain an antibacterial coating liquid;
(2) And (3) coating the antibacterial liquid masking liquid obtained in the step (1) on the contact surface of the invisible orthodontic appliance and teeth, and performing photocuring to obtain the caries-prevention invisible orthodontic appliance.
Preferably, the mixing in step (1) comprises: mixing a photo-curing polymerization monomer and a diluent, adding a photoinitiator, a polymerization inhibitor and an antioxidant, mixing, and adding an antibacterial agent, mixing to obtain the antibacterial coating liquid.
Preferably, the step (2) further comprises the steps of cleaning and drying after the photocuring.
Preferably, the cleaning is ultrasonic cleaning.
In a third aspect, the present invention provides a use of an anticaries invisible orthodontic appliance according to the first aspect in a dental appliance.
Compared with the prior art, the invention has the following beneficial effects:
the invention provides an anti-caries invisible orthodontic appliance with an antibacterial coating, which comprises an invisible orthodontic appliance and an antibacterial coating arranged on the contact surface of the invisible orthodontic appliance and teeth, wherein the raw materials for preparing the antibacterial coating comprise a photocuring polymerization monomer, a diluent, a photoinitiator, a polymerization inhibitor, an antibacterial agent and an antioxidant; according to the invention, the tooth contact surface of the invisible orthodontic appliance is coated with the antibacterial coating liquid, the antibacterial coating formed after photocuring can be tightly bonded with the invisible orthodontic appliance, the invisible orthodontic appliance can not fall off, the light transmittance is higher than 60%, the antibacterial effect is durable and excellent, the antibacterial rate to streptococcus mutans is 64.57-76.67%, and further the dental plaque can be effectively prevented from being fixedly planted and propagated in the tooth socket after the caries-preventing orthodontic appliance is worn, so that the formation of a dental plaque biomembrane is effectively blocked, the tooth demineralization is inhibited, and the caries-preventing effect is realized.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Example 1
An anti-caries invisible orthodontic appliance with an antibacterial coating, which comprises an invisible orthodontic appliance and an antibacterial coating arranged on a tooth contact surface of the invisible orthodontic appliance, wherein the thickness of the antibacterial coating is 50 microns;
the antibacterial coating comprises the following raw materials in parts by weight:
the preparation method of the caries prevention invisible orthodontic appliance provided by the embodiment comprises the following steps:
(1) Adding Bis-GMA into a double-planet stirring pot, adding TEGDMA, stirring at 50 ℃ and 35rpm for 1h, adding 2-ethylhexyl 4- (dimethylamino) benzoate, camphorquinone and 2, 6-di-tert-butyl-p-cresol, continuing stirring for 1h, adding zinc oxide, continuing stirring for 1h, vacuumizing to-0.08 MPa, maintaining the pressure for 30min, and removing bubbles to obtain an antibacterial coating liquid;
(2) And (2) coating the antibacterial masking liquid obtained in the step (1) on the tooth contact surface of a customized invisible orthodontic appliance, uniformly irradiating for 5min by using a photocuring lamp (with the wavelength of 385-515 nm), then placing the appliance into an ultrasonic cleaning machine, carrying out ultrasonic cleaning for 5min under the condition of 400W, removing uncured antibacterial masking liquid, placing the appliance into a ventilation drying cabinet, and drying by air to remove moisture, thus obtaining the anti-caries invisible orthodontic appliance.
Example 2
The cariostatic invisible orthodontic appliance with the antibacterial coating is only different from the embodiment 1 in that the preparation raw materials of the antibacterial coating comprise the following components in parts by weight:
the other structures and preparation methods are the same as those of example 1.
Example 3
An anti-caries invisible orthodontic appliance with an antibacterial coating is different from the embodiment 1 only in that the antibacterial coating is prepared from the following raw materials in parts by weight:
the other structures and preparation methods are the same as those of example 1.
Example 4
An anti-caries invisible orthodontic appliance with an antibacterial coating is different from the appliance in example 1 only in that zinc oxide in raw materials for preparing the antibacterial coating is replaced by magnesium oxide, and other components, the using amount and the preparation method are the same as those in example 1.
Example 5
An anti-caries invisible orthodontic appliance with an antibacterial coating is different from the appliance in example 1 only in that zinc oxide in raw materials for preparing the antibacterial coating is replaced by titanium dioxide, and other components, the using amount and the preparation method are the same as those in example 1.
Example 6
An anti-caries invisible orthodontic appliance with an antibacterial coating is different from the embodiment 1 only in that the antibacterial coating is prepared from the following raw materials in parts by weight:
the other structures and preparation methods are the same as those of example 1.
Example 7
An anti-caries invisible orthodontic appliance with an antibacterial coating is different from the embodiment 1 only in that the antibacterial coating is prepared from the following raw materials in parts by weight:
the other structures and preparation methods are the same as those of example 1.
Comparative example 1
An anti-caries invisible orthodontic appliance with an antibacterial coating is different from the appliance in example 1 only in that zinc oxide is not added in raw materials for preparing the antibacterial coating, and other components, the using amount and the preparation method are the same as those in example 1.
Comparative example 2
An invisible orthodontic appliance differed from example 1 only in that it contained only an invisible orthodontic appliance without an antimicrobial coating applied. And (3) performance testing:
(1) Fluidity: preparing a flat untreated orthodontic diaphragm, drawing a straight line at one end close to the edge, and marking three original points; dipping the antibacterial masking liquid (obtained in the step (1) of the preparation method) by using a metal probe, and naturally dropping one drop to the original point of the orthodontic diaphragm; vertically downwards arranging the orthodontic diaphragm, enabling the sample to naturally flow downwards, and recording the flowing distance for 1 min; the fluidity of the sample is judged by the distance of flow per unit time in the above method,
wherein v represents the velocity of flow in millimeters per minute (mm/min);
l distance of flow of the material in millimeters (mm);
t represents the time of the test in minutes (min);
(2) Light transmittance: measuring the light transmittance of the sample at 550nm by using a spectrophotometer;
(3) The antibacterial rate is as follows: taking a bacterial suspension of the cultured streptococcus mutans (BNCC 336931, purchased from Beijing BeiNai Chuanglian Biotechnology research institute), dropwise adding 100 mu L of the bacterial suspension on a sample to be tested, uniformly coating for 20min, putting the sample into a 10mL test tube of PBS (phosphate buffer solution) by using sterile forceps, fully and uniformly mixing, and properly diluting; selecting 2-3 dilution gradients, sucking 1mL of diluent, inoculating the diluent to a plate by an agar pouring method, culturing the diluent at 35 +/-2 ℃ for 48 hours, and counting bacterial colonies, wherein two of each group are parallel; the samples were repeated 3 times and the inhibition was calculated as follows: x = (a-B)/a × 100%; in the formula: x represents the bacteriostatic rate (%); a represents the average colony number of the tested sample before oscillation; b represents the average colony number of the tested sample after shaking.
The caries preventing invisible orthodontic appliances provided in examples 1 to 7 and comparative examples 1 to 2 were tested according to the above test methods, and the test results are shown in table 1:
TABLE 1
| Fluidity (mm/min) | Light transmittance (%) | Antibacterial ratio (%) | |
| Example 1 | 1.3 | 69.26 | 72.54 |
| Example 2 | 1.2 | 65.18 | 76.67 |
| Example 3 | 1.4 | 68.35 | 70.26 |
| Example 4 | 1.3 | 60.27 | 65.28 |
| Example 5 | 1.3 | 64.31 | 64.57 |
| Example 6 | 0.7 | 59.86 | 55.34 |
| Example 7 | 1.4 | 47.12 | 67.53 |
| Comparative example 1 | 1.3 | 71.53 | 0 |
| Comparative example 2 | / | 72.63 | 0 |
As can be seen from the data in table 1: the caries-preventing invisible orthodontic appliance provided by the invention has an excellent antibacterial effect.
Specifically, the fluidity of the antibacterial masking liquid adopted in the caries-preventing invisible orthodontic appliance obtained in the embodiments 1 to 5 is not lower than 1.2mm/min, so that more operation time can be provided for doctors in clinical operation, and the antibacterial coating can be more easily and uniformly coated; the light transmittance of the obtained anti-caries invisible orthodontic appliance is higher than 60%, and the difference of the light transmittance of the anti-caries invisible orthodontic appliance and the light transmittance of the anti-caries invisible orthodontic appliance (comparative example 2) which is not coated with the antibacterial coating is small, so that the wearing comfort and the attractiveness are not influenced by the arrangement of the antibacterial coating; the antibacterial tests show that the antibacterial rate of the anti-caries invisible orthodontic appliances obtained in the examples 1 to 5 is 64.57 to 76.67 percent, which shows that the anti-caries invisible orthodontic appliances can effectively inhibit the permanent planting of dental plaque and have excellent antibacterial performance.
As can be seen from comparison of example 1 and comparative examples 1 to 2, the orthodontic appliances obtained without adding an antibacterial agent to the coating or without directly providing an antibacterial coating have no antibacterial effect and are not very effective in preventing caries.
Comparing example 1 with examples 6 to 7, it can be found that the lower amount of the antibacterial agent in the antibacterial coating (example 6) causes the antibacterial property of the obtained orthodontic appliance to be reduced; while higher amounts of the antimicrobial agent in the antimicrobial coating (example 7) resulted in poor light transmission of the resulting orthodontic appliance.
Further comparison of examples 1 and 4 to 5 reveals that zinc oxide is most effective as an antibacterial agent.
The applicant states that the present invention is described by the above examples to provide an anti-caries invisible orthodontic appliance with an antibacterial coating, and a method for making and using the same, but the present invention is not limited to the above process steps, i.e., it is not meant that the present invention must rely on the above process steps to be implemented. It will be apparent to those skilled in the art that any modification of the present invention, equivalent substitutions of selected materials and additions of auxiliary components, selection of specific modes and the like, which are within the scope and disclosure of the present invention, are contemplated by the present invention.
Claims (10)
1. An anti-caries invisible orthodontic appliance with an antibacterial coating is characterized by comprising an invisible orthodontic appliance and the antibacterial coating arranged on the contact surface of the invisible orthodontic appliance and teeth;
the raw materials for preparing the antibacterial coating comprise a photocuring polymerization monomer, a diluent, a photoinitiator, a polymerization inhibitor, an antibacterial agent and an antioxidant.
2. The caries prevention invisible orthodontic appliance of claim 1 wherein the invisible orthodontic appliance is made from orthodontic film.
3. The caries prevention invisible orthodontic appliance of claim 1 or 2 wherein the thickness of the antibacterial coating is 10 to 60 μm.
4. The caries prevention invisible orthodontic appliance according to any one of claims 1 to 3, wherein the raw materials for preparing the antibacterial coating comprise the following components in parts by weight:
5. the caries preventing invisible orthodontic appliance according to any one of claims 1 to 4 wherein the photo-curable polymeric monomer comprises a photo-curable acrylate monomer, preferably BIS-GMA;
preferably, the diluent comprises TEGDMA;
preferably, the photoinitiator comprises camphorquinone.
6. The caries prevention invisible orthodontic appliance of any one of claims 1 to 5 wherein the polymerization inhibitor comprises 2-ethylhexyl 4- (dimethylamino) benzoate;
preferably, the antioxidant comprises 2, 6-di-tert-butyl-p-cresol;
preferably, the antibacterial agent is an inorganic nano antibacterial agent;
preferably, the inorganic nano antibacterial agent comprises any one or a combination of at least two of zinc oxide, magnesium oxide or titanium dioxide.
7. The method for preparing the caries prevention invisible orthodontic appliance according to any one of the claims 1 to 6, characterized by comprising the following steps:
(1) Mixing a photo-curing polymerization monomer, a diluent, a photoinitiator, a polymerization inhibitor, an antibacterial agent and an antioxidant to obtain an antibacterial masking liquid;
(2) And (3) coating the antibacterial liquid masking liquid obtained in the step (1) on the contact surface of the invisible orthodontic appliance and teeth, and performing photocuring to obtain the caries-prevention invisible orthodontic appliance.
8. The preparation method according to claim 7, wherein the mixing in step (1) comprises: mixing a photo-curing polymerization monomer and a diluent, adding a photoinitiator, a polymerization inhibitor and an antioxidant, mixing, adding an antibacterial agent, and mixing to obtain the antibacterial masking liquid.
9. The method according to claim 7 or 8, wherein the step (2) further comprises the steps of washing and drying after the photocuring;
preferably, the cleaning is ultrasonic cleaning.
10. Use of the caries preventing invisible orthodontic appliance according to any one of claims 1 to 6 in dental instruments.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202211209386.8A CN115386256A (en) | 2022-09-30 | 2022-09-30 | Caries-preventing invisible orthodontic appliance with antibacterial coating and preparation method and application thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202211209386.8A CN115386256A (en) | 2022-09-30 | 2022-09-30 | Caries-preventing invisible orthodontic appliance with antibacterial coating and preparation method and application thereof |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6162533A (en) * | 1997-08-27 | 2000-12-19 | Lintec Corporation | Hard coat sheet containing an antibacterial agent |
| CN103113521A (en) * | 2013-02-04 | 2013-05-22 | 武汉理工大学 | Preparation method of surface double-bond modified titanium-dioxide nanoparticle composited light-cured resins |
| CN112618064A (en) * | 2020-12-11 | 2021-04-09 | 南方医科大学口腔医院 | Invisible appliance and preparation method thereof |
-
2022
- 2022-09-30 CN CN202211209386.8A patent/CN115386256A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6162533A (en) * | 1997-08-27 | 2000-12-19 | Lintec Corporation | Hard coat sheet containing an antibacterial agent |
| CN103113521A (en) * | 2013-02-04 | 2013-05-22 | 武汉理工大学 | Preparation method of surface double-bond modified titanium-dioxide nanoparticle composited light-cured resins |
| CN112618064A (en) * | 2020-12-11 | 2021-04-09 | 南方医科大学口腔医院 | Invisible appliance and preparation method thereof |
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