JPH02191207A - Adhesive for correcting tooth - Google Patents

Abstract

PURPOSE:To obtain the title adhesive consisting of the first mixed liquid of polymerizable monomer containing a reducing agent and photosensitizer and the second mixed liquid of polymerizable monomer containing an organic peroxide and/or photosensitizer and having extremely excellent workability as well as excellent bond strength. CONSTITUTION:The title adhesive consisting of the first mixed liquid of polymerizable monomer containing a reducing agent (e.g. tert. amine, sulfinic acid, aralkylbarbituric acid) and photosensitizer (e.g. camphorquinone or benzil) and the second mixed liquid of polymerizable monomer containing an organic peroxide (e.g. benzoyl peroxide) and/or photosensitizer. The typical polymerizable monomer includes (meth)acrylic acid ester (e.g. methyl methacrylate). When the above-mentioned adhesive is inserted between a base face and tooth face of bracket for correcting tooth having light transmission properties, prescribed bond strength is obtained by short-term light irradiation and time causing pain by opening of mouth to a patient can be shortened.

Description

Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a new type of dental adhesive that uses both photopolymerization and chemical polymerization, particularly an orthodontic adhesive. be.

(Problems to be solved by conventional technology and invention) Currently,
In the field of orthodontics, direct bonding systems, in which orthodontic brackets are directly bonded to tooth surfaces using a resin adhesive, are widely used.

Furthermore, the brackets used are also changing from metal to plastic, ceramic, composite, etc., which have excellent aesthetics.

By the way, chemical polymerization type adhesives and photopolymerization type adhesives are used as adhesives for these brackets.

However, chemical polymerization type adhesives have the drawback that the adhesion operation is complicated and the curing time is fixed, making it difficult to adjust the adhesion operation time and the bracket try-in time.

On the other hand, photopolymerizable adhesives have the advantage of being easy to bond and allowing flexible operation time adjustment. It has the disadvantage of being time consuming.

Therefore, conventionally, there has been no adhesive that is satisfactory for adhering brackets to tooth surfaces in orthodontics.

(Means for Solving the Problems) As a result of intensive research to solve these problems, the present inventors found that by combining a photopolymerization type initiator system and a chemical polymerization type initiator system, extremely operability can be achieved. The present inventors have discovered that an orthodontic adhesive can be obtained that has good adhesive properties and excellent adhesive strength, and has completed the present invention.

That is, the present invention provides (1) a first liquid mixture consisting of a polymerizable monomer mixture containing a reducing agent and a photosensitizer, and a polymerizable monomer mixture containing an organic peroxide and/or a photosensitizer. (2) a first mixed liquid comprising a polymerizable monomer mixed liquid containing a reducing agent and a photosensitizer; Orthodontic use for adhering a translucent orthodontic bracket to a tooth surface, characterized by comprising a second liquid mixture consisting of a polymerizable monomer mixture containing a peroxide and/or a photosensitizer. It is an adhesive.

It is also preferable that the orthodontic adhesive contains a known inorganic or organic filler to increase the strength of the adhesive.

Further, in actual bonding work using the adhesive of the present invention, for example, after mixing the adhesive with two liquids, the first mixed liquid and the second mixed liquid, immediately before applying the mixed liquid of the two liquids to the tooth. and/or the base surface of a translucent plastic bracket to press the two surfaces together, or separately apply the first mixed solution to the tooth surface and the second mixed solution to the base surface of the plastic bracket, This can be done by pressing both surfaces together.

The reducing agent in the first mixed solution includes tertiary amine,
Sulfinic acid (salt), aralkylbarbic acid, acid anhydride, etc. can be used, and as the photosensitizer, camphorquinone, benzyl, biryllium salt, etc. can be used.

Examples of the organic peroxide in the second mixed solution include benzoyl peroxide, lauroyl peroxide, t-butyl peroxide, t-butyl peroxybenzoate, and 2.5-dimethyl-2°5-di(benzoylperoxy)hexane. etc. can be used.

The polymerizable monomer can be used in common for the first and second mixed liquids.

Typical polymerizable monomers include methacrylic esters and acrylic esters.

As monomethacrylate, methyl methacrylate,
Examples include ethyl methacrylate, butyl methacrylate, cyclomethacrylate, and benzyl methacrylate.

As dimethacrylate, ethylene glycol dimethacrylate, diethylene glycol dimethacrylate,
Bisphenol A dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, 2°2-bis(P-2′-hydroxy-3°-methacryloxypropoxyphenyl)propane, di(methacryloxyethyl)trimethylhexamethyl Examples include diurethane, 2,2-bis(4-methacryloxypolyethoxyphenyl)propane, and 4,8-di(methacryloxymethylene)tricyclo[5,2,1°02.6]decane.

Examples of monoacrylates include methyl acrylate, ethyl acrylate, butyl acrylate, cyclohexyl acrylate, benzyl acrylate, and the like.

Examples of the diacrylate include ethylene glycol diacrylate, diethylene glycol diacrylate, triethylene glycol diacrylate, and tetraethylene glycol diacrylate.

It goes without saying that other known polymerizable monomers can also be used in the present invention.

Known inorganic and organic fillers are used as fillers, such as silica powder, glass powder, quartz powder, ceramic powder such as alumina, and plastic powder, and fillers that have been surface-treated with a silane coupling agent are also used. It can be used suitably.

As the orthodontic bracket, any known bracket can be used, but translucent ceramic brackets, composite plastic brackets, etc. can be preferably used. When the adhesive of the present invention is interposed between the base surface and the tooth surface of a translucent bracket and light irradiation is first performed, the irradiated light passes through the translucent bracket body and the adhesive under the base surface. Reach and make it light and heavy.

Therefore, when bonding brackets in orthodontic operations, the operator can obtain the desired bonding strength by irradiating light for a short period of time. The treatment is completed in a very short time.

Therefore, not only can the patient's pain in opening the mouth be significantly reduced, but also the work can be made more efficient.

After Kojukin, the types of chemical polymerization catalysts,
By selecting the amount, chemical polymerization can proceed continuously and sufficient adhesive strength can be provided.

(Example) The present invention will be specifically explained with reference to Examples.

Example 1: [Preparation of first mixed liquid] 80 parts by weight of 2.2-bis(P-2'-hydroxy-3methacryloxypropoxyphenyl)propane, 10 parts by weight of methyl methacrylate, 10 parts by weight of triethylene glycol dimethacrylate. A viscous first liquid mixture is prepared by thoroughly mixing 0.25 parts by weight of camphorquinone and 0.5 parts by weight or more of N,N-dimethyl-P-)luidine.

[Preparation of second mixed solution 2. 80 parts by weight of 2-bis(P-2'-hydroxy-3゜methacryloxypropoxyphenyl)propane, 10 parts by weight of methyl methacrylate, 10 parts by weight of triethylene glycol dimethacrylate, 0.0 parts by weight of camphorquinone. 25 parts by weight of benzoyl peroxide 0.25 parts by weight or more are thoroughly mixed to prepare a viscous second liquid mixture.

[Adhesive operation] Prepare an adhesive mixture by mixing 0.5 parts by weight of the first mixed liquid and 0.5 parts by weight of the second mixture, and apply the adhesive mixture to a composite plastic bracket (""Efthera"
Apply the intervening material between the base surface of the translucent composite braget (made by Morita Tokyo Seisakusho) and the enamel surface of the natural tooth, and after contact, apply the visible light irradiator ("Quick Light"). (manufactured by Morita Seisakusho) for 5 seconds.

After 5 minutes, the compressive shear adhesive strength was measured using the measuring device shown in FIG. 1, and the adhesive strength was 240 kg/cm2.

FIG. 1 shows a schematic cross-sectional view of a measuring device for measuring the adhesive strength of an orthodontic adhesive and a bracket held in a holder in an embodiment of the present invention, in which 1 is a plastic bracket, 2 is a bracket held in a holder; 3 is an indenter for compression, 3 is an adhesive of the present invention, 4 is a natural tooth, 5 is an embedding material, and 6 is a block holder.

In the figure, an embedding material 5 made of plastic is filled and fixed in a block holder 6 having a deep recess. The embedding material 5 includes a translucent plastic bracket 1 whose base surface is adhered to the surface of the natural tooth 4 with an adhesive 3.
The body part excluding the bonding surface part of the natural tooth 4 on which is protruded,
It is buried and fixed.

The adhesive strength was measured using a plastic bracket 1 bonded to the surface of the natural tooth fixed with the block holder and the embedding material.
The compressive shearing indenter 2 is pressed against the base part of the adhesive, and the force at which the adhesive part breaks is measured and determined as the compressive shearing strength.

Next, when this adhesive test piece was immersed in water at 37°C for 6 months, the adhesive strength was measured, and it was found to be 210 kg/
c.Tsuru” and maintained sufficient strength for clinical use.

Furthermore, when brackets were bonded to 20 teeth in the upper and lower jaws using this adhesive, the entire treatment took about 4 minutes to complete.

Example 2: [Preparation of 1st mixture] 2.2-bis(P-2°-hydroxy-3'methacryloxypropoxyphenyl)propane 40 parts by weight di(methacryloxyethyl)trimethylhexamethylene diurethane 20 parts by weight Triethylene glycol dimethacrylate 20 parts by weight Methyl methacrylate 20 parts by weight Aerosil R972 (trade name: Fine silica powder manufactured by Nippon Aerosil Co., Ltd.) 7 parts by weight Camphorquinone
0.4 parts by weight tri-n-butylamine 0.
8 parts by weight or more are thoroughly mixed to obtain a viscous 1st degree mixed liquid.

[Preparation of 2nd' mixture] 40 parts by weight of 2.2-bis(P-2°-hydroxy-3°-methacryloxypropoxyphenyl)propane, 20 parts by weight of di(methacryloxyethyl)trimethylhexamethylene diurethane 20 parts by weight of triethylene glycol dimethacrylate, 0.4 parts by weight of camphorquinone, and 0.4 parts by weight of benzoyl peroxide are thoroughly mixed to obtain a viscous second mixed solution.

[Adhesive operation] First, 0.5 parts by weight of the above 1st mixed solution was applied onto the enamel of the dentition, and then 5 parts by weight of the above 2' mixed solution O0 was applied to the base surface of a composite plastic bracket ("Efcera"). Apply.

Next, after the two surfaces were brought into contact and pasted together, visible light was irradiated for 10 seconds using "R Quick Light", and after 5 minutes, the compressive shear adhesive strength was measured (using the same measuring device shown in Figure 1 as in Example 1). The adhesive strength was 225 kg/am''.

Furthermore, the adhesive strength after immersing this adhesive specimen in water at 37°C for 6 months was 205 kg/am'', which was sufficient for clinical use.

Furthermore, when brackets were bonded to 20 teeth in the upper and lower jaws using this adhesive, the entire treatment took about 3 minutes to complete.

Example 3: Preparation 1 of 1st Mixed Liquid 50 parts by weight of 2.2-bis(P-2°-hydroxy-3°-methacryloxypropoxyphenyl)propane 2.2-bis(4-methacryloxypolyethoxy) (phenyl)propane 10 parts by weight Triethylene glycol dimethacrylate 20 parts by weight Ethyl methacrylate 20 parts by weight Aerosil R972 (product name: Fine silica powder manufactured by Nippon Aerosil Co., Ltd.) 15 parts by weight Camphorquinone
0.4 parts by weight of N-N-dimethyl-P-toluidine and 0.4 parts by weight or more are thoroughly mixed to obtain a viscous 1'' mixed liquid.

[Preparation of second mixed solution] 50 parts by weight of 2.2-bis(P-2°-hydroxy-3°-methacryloxy-10boxyphenyl)propane 20 parts by weight of 2.2-bis(4-methacryloxypolyethoxyphenyl)propane parts triethylene glycol dimethacrylate 20 parts ethyl methacrylate 20 parts camphorquinone 0.4 parts benzoyl peroxide
0.4 parts by weight of BPOO and 2 parts by weight or more are thoroughly mixed to obtain a viscous 2'' mixed liquid.

[Adhesive operation] First, 0.5 parts by weight of the above-mentioned 1st" mixed solution and 0.5 parts by weight of the 2nd" mixed solution
．． 5 parts by weight to prepare an adhesive mixture, and after bonding a Composite 1 Rust Bracket ("Efcera") and a natural tooth with the adhesive mixture, "Quick Light"
Visible light was irradiated for 5 seconds.

After 5 minutes, the compressive shear adhesive strength was measured (measured using the same measuring device shown in Figure 1 as in Example 1) and found to be 24.
It showed an adhesive strength of 0 kg/am''.

Furthermore, the adhesive strength after immersing this adhesive test piece in water at 37°C for 6 months was 210 kg/as'', which was sufficient for clinical use.

Furthermore, when brackets were bonded to 20 teeth in the upper and lower jaws using this adhesive, the entire treatment took about 3 minutes to complete.

Comparative Example 1: The tooth surface was etched for 15 seconds with a 35% phosphoric acid solution. After washing with water and drying, "Efcera" was applied to the enamel of natural teeth using Heliosit (a light-curing orthodontic adhesive manufactured by Vivadent). It was pasted together and irradiated with light for 20 seconds.

After 5 minutes, the compressive shear adhesive strength was measured using the same measuring method as in Example 1 and found to be 135 kHz/am2.

Further, after this adhesive test piece was immersed in water at 37° C. for 6 months, the adhesive strength had decreased to 90 kg/am”.

Furthermore, when brackets were bonded to 20 teeth in the upper and lower jaws using this adhesive, it took about 12 minutes to complete the entire treatment.

Comparative Example 2: The tooth surface was etched for 15 seconds with a 35% phosphoric acid solution.Then, after washing with water and drying, "Transbond Brimer" was applied to the base surface of "Efcera". After applying the agent), press it against the tooth surface and
Light was irradiated for 5 seconds.

After 5 minutes, the compressive shear adhesive strength was measured using the same measuring method as in Example 1 and found to be 150 kg/am2.

Furthermore, after immersing this adhesive specimen in water at 37° C. for 6 months, the adhesive strength decreased to 125 kg/c+a2.

Furthermore, when brackets were bonded to 20 teeth in the upper and lower jaws using this adhesive, it took about 8 minutes to complete the entire procedure.

(Effects of the Invention) As explained above, by using the orthodontic adhesive of the present invention, it is possible to easily bond an orthodontic bracket to a tooth, and the adhesive strength after bonding is also sufficiently satisfactory. It becomes something you get.

In particular, when the adhesive of the present invention is interposed between the base surface of the translucent bracket and the tooth surface, the operator can achieve the desired bond by applying light for a short period of time during bracket bonding work in orthodontic operations. Because of this strength, the entire procedure can be completed in a very short time, especially when bonding brackets to a large number of teeth in a patient's mouth. Therefore, not only can the patient's pain in opening the mouth be significantly reduced, but
Work efficiency will also be improved.

[Brief explanation of the drawing]

FIG. 1 shows a schematic cross-sectional view of a measuring device for measuring the adhesive strength of an orthodontic adhesive and a bracket held by a holder in an embodiment of the present invention. 1 nib bracket, 2: compression indenter, 3: adhesive,
4: Natural tooth, 5: Embedding material, 6: Block holder,

Claims (3)

[Claims] (1) A first mixture consisting of a polymerizable monomer mixture containing a reducing agent and a photosensitizer, and a second mixture consisting of a polymerizable monomer mixture containing an organic peroxide and/or a photosensitizer. An orthodontic adhesive characterized by comprising a mixed liquid. (2) A first mixture consisting of a polymerizable monomer mixture containing a reducing agent and a photosensitizer, and a second mixture consisting of a polymerizable monomer mixture containing an organic peroxide and/or a photosensitizer. An orthodontic adhesive for bonding a translucent orthodontic bracket to a tooth surface, characterized by comprising a mixed liquid. (3) An orthodontic adhesive according to claim 1 or 2, characterized in that the orthodontic adhesive contains a filler.