Composition for forming intraoral mounting device, method of preparing intraoral mounting device and intraoral mounting device prepared thereby

Abstract

A composition for forming an intraoral appliance, a method for manufacturing an intraoral appliance, and an intraoral appliance manufactured by the method are disclosed. The composition for forming an intraoral appliance includes a photocurable compound and an incomplete curing indicator, and the incomplete curing indicator has both a photopolymerization initiation function and an incomplete curing indicator function.

Description

[Technical Field]

[0001] A composition for forming an intraoral appliance, a method for manufacturing an intraoral appliance, and an intraoral appliance manufactured by the method are disclosed. More specifically, a composition for forming an intraoral appliance, a method for manufacturing an intraoral appliance, and an intraoral appliance manufactured by the method are disclosed, which allow for easy determination of whether or not a 3D printed output is incompletely cured. [Background technology]

[0002] As an example, a transparent orthodontic device, which is a type of intraoral appliance, is a thermoplastic device that achieves the desired tooth movement by hot-pressing a plate-shaped transparent polymer composite resin (hereinafter referred to as resin). Unlike conventional orthodontic appliances, transparent orthodontic appliances do not have protruding structures or metal wires that stick out from the teeth, and are almost transparent in color, making them aesthetically superior to conventional orthodontic appliances. Therefore, many people who want to undergo orthodontic treatment refrain from doing so out of concern that having orthodontic appliances attached to their teeth will have a negative impact on their work life, interpersonal relationships, and self-confidence. Transparent orthodontic appliances eliminate these burdens, allowing people to undergo orthodontic treatment more comfortably. In addition, the device is thin and easy to wear, and can be removed from the mouth for meals and tooth brushing, causing minimal inconvenience in daily life. As a result, malocclusion is extremely common among the population, and public interest and demand for orthodontic treatment using transparent orthodontic devices is growing, leading to a continuous expansion of the market size related to transparent orthodontic devices. Transparent orthodontic appliances, or thermo-pressed resin appliances, commonly called aligners, achieve planned tooth movement in a continuous manner by gradually imitating tooth movement within the elastic limits of the resin and then wearing the appliance in the patient's mouth. To achieve this effect, the tooth movement pattern must be reproduced in stages in the dental model (mold) used to thermo-press the aligner. There are two methods used to reproduce the gradual movement of teeth in a mold: The first method is manual. A plaster model of the patient's dentition is prepared, and each tooth is separated from the prepared plaster model using a jigsaw. Taking into consideration the direction of tooth movement and the elastic limit of the resin, each individual tooth is moved to an appropriate position and then reattached to the prepared plaster model using adhesive or wax. The resulting plaster model is used as a mold for hot press molding. When the resulting aligner is placed in the patient's mouth, the next step of tooth movement information embodied in the aligner is transmitted to the teeth by the elastic restoring force of the resin, resulting in tooth movement. The aligner must be worn long enough (generally 16-21 hours a day for 7-14 days or more) until the tooth movement embodied in the aligner is visible on the actual teeth. After that, to obtain the aligner for the next stage of tooth movement, another impression of the patient's mouth is taken, and dental plaster is poured over it to obtain a plaster model of the patient's dentition, which is then hardened. The above process is then repeated continuously to obtain the desired tooth alignment. This method is based on 3D scanning and 3D printing technology. A 3D image of the patient's dentition is obtained using a scanner, and this image is used to simulate step-by-step tooth movement using a computer program, taking into account the desired direction of tooth movement and the elasticity of the resin. Individual tooth movements are realized step by step from the initial position to the final position. After that, a 3D printer is used to output molds for thermo-compression molding of the resin one by one for each step. Thermo-compression molding is then performed on these molds to obtain aligners for each step of tooth movement. The advantage of this method over manual methods is that it does not require repeated impressions from the patient, and a step-by-step simulation of tooth movement based on a 3D image of the dentition is displayed on a computer screen, allowing you to confirm and adjust whether the tooth movement is set reasonably in advance. This allows communication between the patient and doctor, or between the doctor and the service provider, regarding the final treatment results and treatment process, preventing any errors that may occur. A representative service of this method is Invisalign (Align Technology). As mentioned above, transparent orthodontic appliances offer superior aesthetics and ease of use, making them very attractive to people seeking orthodontic treatment compared to conventional wire orthodontic appliances. However, existing transparent orthodontic appliances are manufactured in an incompletely cured state, and when attached to the patient's teeth, resin leachate seeps out, causing discomfort to the patient, and they have problems such as low strength, which do not meet the desired physical properties. Summary of the Invention [Problem to be solved by the invention]

[0003] One embodiment of the present invention provides a composition for forming an intraoral appliance that allows for easy determination of whether or not a 3D printing output has been incompletely cured. Another embodiment of the present invention provides a method for producing an intraoral appliance, comprising the step of preparing the composition for forming the intraoral appliance. Yet another embodiment of the present invention provides an intraoral appliance manufactured by the method for manufacturing an intraoral appliance. [Means for solving the problem]

[0004] One aspect of the present invention is a photocurable compound and an incompletely cured indicator; The incomplete cure indicating agent provides a composition for forming an intraoral appliance having both a photopolymerization initiation function and an incomplete cure indicating function. The incomplete cure indicator can include phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, phenylglyoxylic acid methyl ester, and diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide. The composition for forming an intraoral appliance may contain 0.5 to 14 parts by weight of the phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, 0.5 to 8 parts by weight of the phenylglyoxylic acid methyl ester, and 0.5 to 8 parts by weight of the diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide relative to 100 parts by weight of the photocurable compound. The composition for forming an intraoral appliance may not contain a separate photoinitiator. The composition for forming an intraoral appliance may further contain 0.1 to 2 parts by weight of an antioxidant relative to 100 parts by weight of the photocurable compound. The composition for forming an intraoral garment may be free of pigments. The composition for forming an intraoral appliance may be free of solvent. The composition for forming an intraoral appliance may have a viscosity of 300 to 800 cps. The composition for forming an intraoral appliance may be liquid, photocurable, and suitable for 3D printing. Another aspect of the present invention is a step (S10) of preparing a composition for forming an oral appliance; Step (S20) of 3D printing the composition for forming an intraoral appliance to prepare a partially cured intraoral appliance; and The method for manufacturing an intraoral appliance includes a step (S30) of completely curing the partially cured intraoral appliance to manufacture a final intraoral appliance. Yet another aspect of the present invention is The present invention also provides an intraoral article manufactured by the method for manufacturing an intraoral article. The intraoral appliance may be an artificial tooth, a transparent orthodontic appliance, a surgical guide, or a splint. [Effects of the Invention]

[0005] The composition for forming an intraoral appliance according to one embodiment of the present invention allows easy determination of whether or not it has been incompletely cured, and can provide an intraoral appliance that has been completely cured and has excellent physical properties such as strength. [Brief explanation of the drawings]

[0006] [Figure 1] FIG. 1 is a flow chart showing a method for manufacturing an intraoral appliance according to an embodiment of the present invention. DETAILED DESCRIPTION OF THE INVENTION

[0007] a photocurable compound and an incompletely cured indicator; The incomplete cure indicating agent provides a composition for forming an intraoral appliance having both a photopolymerization initiation function and an incomplete cure indicating function, The incomplete cure indicator can include phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, phenylglyoxylic acid methyl ester, and diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide. Hereinafter, a composition for forming an intraoral appliance according to one embodiment of the present invention will be described in detail. A composition for forming an intraoral appliance according to one embodiment of the present invention includes a photocurable compound and an incompletely cured indicator. The incomplete curing indicator has both a photopolymerization initiation function and an incomplete curing indicator function. Specifically, the incomplete curing indicator takes on a fluorescent color if the composition for forming an oral appliance (i.e., the photocurable compound) is in an incomplete cured state when cured, and the fluorescent color disappears if the composition is in a completely cured state, allowing the presence or absence of incomplete curing to be determined by visual observation. For example, the incomplete cure indicator can include phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, phenylglyoxylic acid methyl ester, and diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide. The photocurable compound is not particularly limited, and any monomer or oligomer that can be used in the manufacture of oral appliances and does not contradict the purpose of the present invention, which is to easily determine whether or not incomplete curing has occurred, can be used. For example, the photocurable compound can include N,N-dimethylacrylamide, difunctional aliphatic urethane methacrylate (e.g., Bomar BR-952), bisphenol A glycerolate dimethacrylate, 3,5-di-tert-butyl-4-hydroxytoluene, or a combination thereof. Furthermore, the composition for forming an intraoral appliance may contain 0.5 to 14 parts by weight of the phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, 0.5 to 8 parts by weight of the phenylglyoxylic acid methyl ester, and 0.5 to 8 parts by weight of the diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide, relative to 100 parts by weight of the photocurable compound. When the contents of the phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, the phenylglyoxylic acid methyl ester, and the diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide are each within the above ranges, the composition for forming an intraoral appliance will take on a fluorescent color if it is in an incompletely cured state upon curing, and will no longer have a fluorescent color if it is in a completely cured state, allowing the presence or absence of incomplete curing to be determined by visual observation. The composition for forming an intraoral appliance may not include a separate photoinitiator. That is, the phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, the phenylglyoxylic acid methyl ester, and the diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide can serve as an indicator for determining whether or not the composition is incompletely cured during curing, and can also serve as a photoinitiator, so a separate photoinitiator is not required.

[0008] The composition for forming an intraoral appliance may further contain 0.1 to 2 parts by weight of an antioxidant per 100 parts by weight of the photocurable compound. If the content of the antioxidant is within the above range, a sufficient antioxidant effect can be obtained without adversely affecting other physical properties of the intraoral appliance. The antioxidant may include hindered phenolic compounds such as 2,6-di-tert-butyl-para-cresol and 4,4'-methylenebis(6-tert-butyl-ortho-cresol); aromatic amine compounds such as dioctyldiphenylamine and α-phenylnaphthalene; sulfur compounds; phosphorus compounds; dialkyldithiophosphates, which are sulfur and phosphorus complexes (e.g., sulfurized fatty acids, dicetyl sulfide, dibenzyl disulfide, alkyldithiophosphates); disalicyldiaminopropane; didodecylthiobenzimidazole; or combinations thereof. The composition for forming an intraoral appliance may not contain a pigment. The composition for forming an intraoral appliance may have a viscosity of 300 to 800 cps (centipoise). In this specification, "viscosity" refers to the viscosity measured at room temperature (25°C) using a Brookfield DV-Heometer RPM (shear rate: 25 / s). The composition for forming an oral appliance may not contain a solvent, but the present invention is not limited thereto, and the composition for forming an oral appliance may further contain a solvent. The solvent can include ethanol, methanol, isopropanol, butanol, water, methylene glycol, ethylene glycol, propylene glycol, butylene glycol, neopentyl glycol, hexylene glycol, acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, cyclohexanone, cyclohexane, methylene chloride, chloroform, carbon tetrachloride, trichloroethylene, perchloroethylene, methyl glycol acetate, toluene, benzene, diethyl ether, benzyl alcohol, glycerin, or combinations thereof. The composition for forming an intraoral appliance may further contain additives such as a stabilizer and a plasticizer. The stabilizer may include a benzophenone, an oxanilide, a benzotriazole, a halogenated benzotriazole, a triazine, or a combination thereof. The plasticizer can include glycerin, propylene glycol, polyethylene glycol, ethylene glycol, sorbitol, mannitol, or combinations thereof. The composition for forming an intraoral appliance may be liquid (or suspension), photocurable, and suitable for 3D printing.

[0009] A method for manufacturing an intraoral appliance according to an embodiment of the present invention will now be described in detail. FIG. 1 is a flow chart showing a method for manufacturing an intraoral appliance according to an embodiment of the present invention. Referring to FIG. 1, a method for manufacturing an intraoral appliance according to one embodiment of the present invention includes a step of preparing a composition for forming an intraoral appliance (S10), a step of 3D printing the composition for forming an intraoral appliance to prepare a partially cured intraoral appliance (S20), and a step of completely curing the partially cured intraoral appliance to prepare a final intraoral appliance (S30). In step (S10), the mixing ratio of the photocurable compound, the phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, the phenylglyoxylic acid methyl ester, and the diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide can be appropriately adjusted so that a fully cured intraoral appliance having the desired physical properties is obtained, while the appliance has a fluorescent color in an incompletely cured state and the fluorescent color disappears in a fully cured state. The step (S20) can be performed using a 3D printer, and the composition for forming an intraoral appliance is partially cured by continuously or intermittently irradiating the printed composition for forming an intraoral appliance during the 3D printing process with ultraviolet light to form the shape of the intraoral appliance. In this specification, the term "partial curing" is used as a concept that includes "incomplete curing" and means that the curing rate is 40% to 90%. In step S30, the partially cured intraoral appliance is completely cured using a separate curing device to produce a final intraoral appliance. Whether the intraoral appliance is completely cured can be determined by whether it is fluorescent, and this can be verified using a separate curing level measuring device for cross-checking. For example, if the intraoral appliance is fluorescent, it is determined to be incompletely cured, and if the fluorescent color disappears, it is determined to be completely cured. In this specification, "complete curing" means that the curing rate is 99% to 100%. Hereinafter, the intraoral appliance manufactured by the method for manufacturing the intraoral appliance will be described in detail. The intraoral appliance is completely cured by continuing to cure until the fluorescent color disappears, so it is highly safe to use (no leaching of eluates) and can perfectly realize the intended physical properties and shade. The intraoral appliance may be an artificial tooth, a transparent orthodontic appliance, a surgical guide, or a splint. The present invention will be described below with reference to examples, but the present invention is not limited to these examples.

[0010] Examples 1-1 to 1-12 and Comparative Examples 1-1 to 1-6: Production of compositions for forming transparent orthodontic appliances Transparent orthodontic appliance compositions were prepared containing N,N-dimethylacrylamide (PP1), difunctional aliphatic urethane methacrylate (Bomar BR-952) (PP2), bisphenol A glycerolate dimethacrylate (PP3), and 3,5-di-tert-butyl-4-hydroxytoluene (PP4) as photocurable compounds, phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (ID1), phenylglyoxylic acid methyl ester (ID2), and diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide (ID3) as incomplete cure indicators, and 2,6-di-tert-butyl-para-cresol as an antioxidant. The materials and their contents used in each example and comparative example are listed in Table 1 below. In Table 1, the units are parts by weight. The contents of the incomplete cure indicator and antioxidant are based on 100 parts by weight of the total weight of the four photopolymerizable compounds. [Table 1] Examples 2-1 to 2-12 and Comparative Examples 2-1 to 2-6: Manufacturing of transparent orthodontic devices The transparent orthodontic appliances manufactured in each of the Examples and Comparative Examples were printed using a 3D printer and partially cured to produce partially cured transparent orthodontic appliances. The partially cured transparent orthodontic appliances were then fully cured using a curing device to produce the final transparent orthodontic appliances. The 3D printer and curing device were manufactured as a set and are products of Ray Dent Studio. Here, whether or not the appliances had fully cured was measured using a separate hardening degree measuring device. Three transparent orthodontic appliances were manufactured using each transparent orthodontic appliance-forming composition.

[0011] Evaluation example: Evaluation of incomplete hardening of transparent orthodontic appliances In each of the examples and comparative examples, the color of the transparent teeth (DV1) printed and partially cured using a 3D printer and the final transparent orthodontic appliance (DV2) fully cured using a curing device was observed, and the results are shown in Table 2 below. In the table below, "◯" means that the tooth has a fluorescent color, and "×" means that the tooth does not have a fluorescent color. [Table 2] Referring to Table 2, in Examples 2-1 to 2-12, the transparent orthodontic appliances were fluorescent when in an incompletely cured state and not fluorescent when in a fully cured state. This allowed the worker to easily determine whether the appliance was fully cured by visual inspection when post-curing the 3D printer output in a curing device. This prevented the worker from completing the production of a transparent orthodontic appliance in an incompletely cured state during post-curing. Furthermore, it was found that the incompletely cured indicator's ability to determine whether the appliance was fully cured remained unchanged even when the composition of the photocurable compound was changed. On the other hand, in Comparative Examples 2-1 to 2-6, since there is no difference in appearance between the transparent orthodontic device in an incompletely cured state and in a cured state, workers cannot accurately determine whether the device is fully cured or not, and end up completing production in an incompletely cured state, resulting in problems caused by incomplete curing. Alternatively, workers must complete production by checking the point of complete curing using a separate curing degree measuring device each time, which complicates the manufacturing process due to repeated measurements of the curing degree, increases manufacturing time, and significantly reduces productivity.

[0012] While the preferred embodiment of the present invention has been described above with reference to the drawings and examples, it is understood that this is merely an example and that various modifications and equivalent embodiments are possible. Therefore, the scope of protection of the present invention should be determined based on the appended claims. [Industrial Applicability]

[0013] The composition for forming an intraoral appliance according to the present invention allows easy determination of whether or not it has hardened incompletely, and is expected to be widely used in the orthodontic industry, which utilizes transparent orthodontic appliances, by preventing leaching of the transparent orthodontic appliance while allowing the strength of the transparent orthodontic appliance to be fully expressed.

Claims

1. a photocurable compound and an incompletely cured indicator; The incomplete cure indicator has both a photopolymerization initiation function and an incomplete cure indicator function, The incomplete cure indicator comprises phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, phenylglyoxylic acid methyl ester, and diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide; the photocurable compound contains 0.5 to 14 parts by weight of the phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide, 0.5 to 8 parts by weight of the phenylglyoxylic acid methyl ester, and 0.5 to 8 parts by weight of the diphenyl(2,4,6-trimethylbenzoyl)phosphine oxide, relative to 100 parts by weight of the photocurable compound; A composition for forming an intraoral article.

2. A step (S10) of preparing a composition for forming an oral appliance according to claim 1; Step (S20) of 3D printing the composition for forming an intraoral appliance to prepare a partially cured intraoral appliance; and The method for manufacturing an intraoral appliance includes a step (S30) of completely curing the partially cured intraoral appliance to manufacture a final intraoral appliance.

3. An intraoral appliance manufactured by the method for manufacturing an intraoral appliance according to claim 2.

4. The intraoral appliance according to claim 3, wherein the intraoral appliance is an artificial tooth, a transparent orthodontic appliance, a surgical guide, or a splint.

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