JP3157922B2 - Dental temporary sealing material composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a dental curable composition. Specifically, a temporary dental filler (hereinafter, referred to as a dental filler) that develops a sealing property by expanding in a cavity after filling.
(Referred to as a temporary sealing material).

[0002]

2. Description of the Related Art A temporary sealing material is a temporary filling material that is filled in a cavity for several days from returning a patient during the course of dental treatment until resuming treatment. It is frequently used in tooth preservation treatment and endodontic treatment, and the filling period is usually about one week.

The purpose of filling the temporary sealing material is mainly to protect endodontic tissue during the course of treatment. Specifically, they are prevention of bacterial infection, blocking of external stimuli, prevention of drug leakage, and the like, which are important factors for continuing successful treatment.

[0004] The required properties of the temporary sealing material are that it has a tight sealing effect, that it withstands occlusal pressure and that it does not break, drop or deform, that it has no harm to the hard tissues and pulp of the teeth, that it is filled and removed. Although the operation is easy, there has been no material that satisfies all of them. The reason is that the conditions of "having a sealing property" and "not easily falling off" and the condition of "easy removal operation" are contradictory. Only met.

[0005] Conventional temporary sealing materials are roughly classified into the following three types. Thermoplastic resin (temporary stopping), hydraulic temporary sealing material, dental cement (eugenol cement, non-eugenol cement, zinc phosphate cement).

[0006] Thermoplastic resins are used after being heated and softened, and then filled into cavities. Since the filling and removing operations are simple, they are widely used. However, since it shrinks during cooling and hardening, the effect of tightly closing the cavity cannot be expected.

The hydraulic temporary sealing material is a material which reacts with saliva in the oral cavity and hardens. Although it is a simple one that can be simply taken out of the container and filled into the cavity as it is, it has drawbacks such as requiring several hours for curing and abrasion and falling off easily.

[0008] Dental cement is a material that becomes a hardened body of moderate hardness in a few minutes, and some have an analgesic, sedative and antibacterial action. However, most of them require complicated and skillful powder-liquid mixing operations. Moreover, the removal operation is difficult because the cured product is hard.

[0009] Temporary sealing materials are materials frequently used in dental treatment, and play a large role in protecting endodontic tissue during the course of treatment, even for a short period of time. However, if the sealability is poor or it falls off, it will not be used for endodontic tissue protection,
At present, there is often a problem that the filling and removing operations are difficult and it takes time. In general, those that can be easily filled and removed have poor sealing properties, and those that have good sealing properties require complicated filling and removing operations. That is, there is no conventional temporary sealing material that can be sufficiently satisfied by clinicians. Therefore, the development of a temporary sealing material excellent in both physical properties and operability has been strongly desired.

[0010]

DISCLOSURE OF THE INVENTION The present inventors have intensively studied to develop a temporary sealing material which is easy to fill and remove, has excellent sealing properties, and is less likely to fall off.

[0011]

As a result, it has been found that a composition obtained by blending a superabsorbent resin with a curable composition whose cured body is an elastic body has preferable properties as a temporary sealing material. The present invention has been developed.

That is, the present invention provides (A) 20 to 90 parts by weight of a polymerizable monomer having a polymer elongation of 10% or more, (B) 10 to 80 parts by weight of a filler, and (C) a polymerization initiator 0 .01-5
Parts by weight, and (D) 0.1 to 10 parts by weight of the superabsorbent resin [However, the total amount of (A) and (B) is 100 parts by weight,
(C) is the amount per 100 parts by weight of (A), and (D) is the amount per 100 parts by weight of (A) + (B).] It is a temporary sealing material composition.

The polymerizable monomer used in the present invention is a cured product obtained by polymerizing and curing only the polymerizable monomer among known radical polymerizable monomers having an acryl group and / or a methacryl group. Is required to be 10% or more. When a polymerizable monomer having an elongation of the cured product of less than 10% is used, the cured product of the composition has poor elasticity, and the water-absorbing swelling effect of the superabsorbent resin is not sufficiently exhibited. In the present invention, the elongation of the cured product is defined by JIS
It means the elongation defined in K6301 (Vulcanized Rubber Physical Test Method).

Typical examples of the polymerizable monomer having the specific elongation used in the present invention include nonylphenoxyethyl acrylate and 2-hydroxy-
Monofunctional monomers such as 3-phenoxypropyl acrylate, acrylate-blocked polydimethylsiloxane at one end or methacrylate thereof; polyethylene glycol dimethacrylate, 1,6-hexanediol dimethacrylate, polydimethylsiloxane blocked at both ends methacrylate or these Difunctional monomers such as acrylates; 2-hydroxyethyl methacrylate, 2-
Hydroxypropyl methacrylate, glycidol dimethacrylate or a monomer having a hydroxyl group such as acrylate and trimethylhexamethylene diisocyanate, diisocyanatomethylcyclohexane, isophorone diisocyanate, hexamethylene diisocyanate, diisocyanate methylbenzene, methylene bis (4-cyclohexyl isocyanate) Examples thereof include urethane-based monomers obtained by addition with such a diisocyanate compound. These polymerizable monomers are used alone or in combination of two or more.

The compounding amount of the polymerizable monomer of the present invention is 20
~ 90 parts by weight is suitable. If the amount is less than 20 parts by weight, the cured product of the composition will have poor elasticity, so that the water-absorbing swelling effect of the superabsorbent resin will not be sufficiently exhibited. If the amount exceeds 90 parts by weight, the strength of the cured product of the composition is insufficient, and a good temporary sealing material cannot be obtained. The total amount of the polymerizable monomer and the filler described later is 1
It is a value when it is set to be 00 parts by weight.

The filler used in the present invention may be any of inorganic powders, organic powders, organic-inorganic composite powders, etc., as long as they do not inhibit the radical reaction, and may be a mixture of these powders. good. Typical examples are as follows: ground quartz, wet silica, dry silica, carbon black, diatomaceous earth, glass fiber, alumina, magnesia, calcium carbonate, magnesium carbonate, ground polymer, powder polymer, composite filler (inorganic oxide And a composite of a polymer and a crushed polymer).

The compounding amount of the filler is suitably from 10 to 80 parts by weight. If the amount is less than 10 parts by weight, the strength of the cured product of the composition becomes insufficient, and a good temporary sealing material cannot be obtained. If the amount exceeds 80 parts by weight, the cured product of the composition will have poor elasticity, so that the water-absorbing swelling effect of the highly water-absorbent resin will not be sufficiently exhibited.

The polymerization initiator used in the present invention is not particularly limited as long as it is generally used for a polymerizable monomer polymerized by a radical mechanism. Examples of the polymerization initiator include a photopolymerization initiator, a redox-based polymerization initiator composed of an organic peroxide and a tertiary amine, and a heat polymerization initiator. Among them, a photopolymerization initiator that does not require kneading or heating is particularly preferable. It is preferably used. An ordinary photopolymerization initiator is used in combination with a photosensitizer and a photopolymerization accelerator. Typical examples of the photosensitizer include α-diketones such as benzyl, camphorquinone, α-naphthyl, P, P′-dimethoxybenzyl, and the like. Typical examples of the photopolymerization accelerator include ethyl N, N-dimethylbenzoate, N, N-dimethyl-P-toluidine, N, N-dihydroxyethyl-P-toluidine, N, N-dimethyl. And tertiary amines such as aniline. A cured product can be obtained by irradiating a visible light of 390 to 700 nm to the temporary sealing material composition containing these photopolymerization initiators.

The amount of the polymerization initiator is preferably 0.01 to 5 parts by weight per 100 parts by weight of the polymerizable monomer.
If the amount is less than 0.01 parts by weight, the composition cannot be rapidly cured by light irradiation. If the amount is more than 5 parts by weight, a problem occurs in storage stability, which is not preferable.

The superabsorbent resin used in the present invention is:
It is a polymer compound in which the chains of electrolyte polymers, which are originally water-soluble, are loosely bridged, and can hold water in the mesh of several tens to 1000 times or more their own weight.

Specific examples of the superabsorbent resin used in the present invention include sodium polyacrylate, acrylic acid / vinyl alcohol copolymer, vinyl acetate / acrylate copolymer saponified product, Polyvinyl alcohol / maleic anhydride reactant, isobutylene / maleic acid copolymer crosslinked product, polyacrylonitrile-based saponified product, starch /
Examples thereof include a saponified acrylonitrile graft copolymer and a crosslinked carboxymethyl cellulose. These superabsorbent resins are pulverized by a known method such as a jet mill to form a powder having a particle size of several hundred μm to 0.1 μm. In particular, in order to expand the temporary sealing material composition as uniformly as possible, those having a smaller particle size of 20 μm or less are preferable.

The dental temporary sealing material composition containing the superabsorbent resin is filled in the cavity, and after being cured, it absorbs saliva and swells appropriately to polymerize the polymerizable monomer. It compensates for the polymerization shrinkage that occurs at the time, adheres to the wall of the cavity, and exhibits excellent sealing properties and holding power.

The amount of the superabsorbent resin is preferably 0.1 to 10 parts by weight per 100 parts by weight of the total of the polymerizable monomer and the filler. If the amount is less than 0.1 part by weight, the water-absorbing swelling amount is so small that good sealing properties cannot be exhibited. If the amount is more than 10 parts by weight, the water absorption swelling amount is too large and the composition may protrude from the cavity, which is not preferable. In the dental temporary sealing material composition of the present invention, other additives may be further added as long as the physical properties are not significantly reduced. Examples of such additives include a polymerization inhibitor, an ultraviolet absorber, a plasticizer, a pigment, an antioxidant, an antibacterial agent, and a surfactant.

The method for preparing the dental temporary sealing material composition of the present invention is not different from the known method for preparing a dental filler composition. That is, by weighing appropriate amounts of various polymerizable monomers, fillers, polymerization initiators, superabsorbent resins, additives, and the like, and kneading them until uniform using a general kneading machine such as a raikai machine, to form a paste. Can be obtained. However, when a photopolymerization initiator is used as the polymerization initiator, care must be taken, such as kneading in a light-shielded state.

The method of using the dental temporary sealing material composition of the present invention is basically the same as a normal temporary sealing material. That is, after the cavity is formed in the tooth, the temporary sealing material composition is filled, and the pit and fissure are appropriately formed. At this time, when a photopolymerization initiator is used as the polymerization initiator, visible light of
Irradiate for 0 to 60 seconds to cure the temporary sealing material composition. Also,
When a redox polymerization initiator is used, a temporary sealing material composition containing an organic peroxide and a temporary sealing material composition containing a tertiary amine before filling are kneaded using a mixing rod or the like. It is necessary to. When the temporary sealing material composition is removed from the cavity, the composition may be excavated with an instrument such as an explorer or an excavator.

[0026]

The temporary sealing material composition for dental use obtained according to the present invention undergoes moderate water absorption and expansion in the cavity after hardening and adheres tightly to the cavity wall surface, thus exhibiting excellent sealing properties and holding power. Therefore, the problem of infection and shedding is unlikely to occur. Also,
In the removal operation, since it is not adhered to the wall of the fossa, it can be easily removed as a lump simply by circling it with an instrument such as an explorer or an excavator.
Further, when using a photopolymerization initiator as a polymerization initiator,
The filling operation becomes extremely easy. That is, it is only necessary to take out an appropriate amount of the present composition from the container, fill the cavity, and cure using a light irradiator commonly used for composite resin, and the time and skill required for the filling operation can be reduced. .

[0027]

EXAMPLES The present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples.

Table 1 shows the polymerizable monomers used in the following Examples and Comparative Examples, Table 2 shows the polymerization initiator, and Table 3 shows the superabsorbent resin powder and the average particle size. However, the elongation of the polymer of the polymerizable monomer shown in Table 1 is a numerical value measured in accordance with JIS K 6301 (Vulcanized rubber physical test method). That is, a cured body sample molded into a dumbbell-shaped No. 1 shape is
It is determined by measuring the length between the marked lines when pulled at a speed of 500 mm / min and cut.

[0029]

[Table 1]

[0030]

[Table 2]

[0031]

[Table 3]

In the examples and comparative examples, the evaluation of the dental temporary sealing material composition was performed by the following method, and the same sample was measured or evaluated three times and the average value was recorded.

(1) Shore A hardness A cured product is prepared by a method according to the sample such as light irradiation,
After being immersed in water at 7 ° C. for 24 hours, it is measured by a Shore A hardness tester. The measurement was in accordance with JIS K6301 (vulcanized rubber test method).

(2) Sealability A cavity having a diameter of 3 mm and a depth of 2 mm is carved in the crown of the extracted fresh bovine tooth, and the sample is filled. It is cured by a method such as light irradiation according to the sample, and is immersed in water at 37 ° C. for 24 hours.
Then, in a fuchsin aqueous solution having a concentration of 0.1%,
A heat cycle of 60 ° C. and 60 ° C. is performed 60 times. After the heat cycle, the filled sample is removed, and the state of penetration of the dye is visually observed. The evaluation has the following three stages.

A: No intrusion of dye is observed.

B: Invasion of a dye is partially observed.

C: Dye has penetrated the whole cavity.

(3) Filling operability A cavity having a diameter of 3 mm and a depth of 2 mm is carved in the crown of the extracted fresh bovine tooth, and the sample is filled. The ease of filling at that time,
The following three levels are used for evaluation.

A: Easy filling.

B: Filling requires skill.

C: The operation is complicated and filling is difficult.

(4) Removal operability A cavity having a diameter of 3 mm and a depth of 2 mm is carved in the crown portion of the extracted fresh bovine tooth, and the sample is filled. It is cured by a method such as light irradiation according to the sample, and is immersed in water at 37 ° C. for 24 hours.
Thereafter, a removing operation is performed by an explorer, and the operability is evaluated in the following three stages.

A: Easily removed as a lump.

B: Partially remains in the cavity due to shattering.

C: It is too hard to remove.

Examples 1 to 9, Comparative Examples 1 and 2 Materials having the respective compositions shown in Table 4 were kneaded with a raikai machine to prepare a paste-like temporary sealing material composition. A test was performed using each composition according to the above evaluation method. Table 4 shows the results
Are shown together.

The composite filler used in the following examples was 30 parts by weight of triethylene glycol, 2,2-
70 parts by weight of bis (4-hydroxy-3-methacryloxypropoxyphenyl) propane, Leolosil QS-1
02 (manufactured by Tokuyama Soda Co., Ltd.) and 1 part by weight of methyl ethyl ketone peroxide are kneaded, and then kneaded.
After polymerization at 120 ° C. for 4 hours under a nitrogen pressure of Kg / cm ² , the cured product was pulverized by a ball mill for 6 hours and used after passing through a 200-mesh sieve.

Dry silica is Leolosil QS-102.
(Manufactured by Tokuyama Soda Co., Ltd.). As the wet silica, Fine Seal X-70 (manufactured by Tokuyama Soda Co., Ltd.) was used. Quartz powder having an average particle diameter of 3 μm was used.

[0049]

[Table 4]

Example 10 Polymerizable monomer no. 50 parts by weight, fumed silica; 30
20 parts by weight of a composite filler; 20 parts by weight of benzoyl peroxide; 0.25 part by weight of a superabsorbent resin powder a; Polymerizable monomer No. 50 parts by weight, fumed silica;
30 parts by weight, composite filler; 20 parts by weight, DEPT;
A composition obtained by kneading 0.25 parts by weight of the superabsorbent resin powder a; 2 parts by weight with a raikai machine is referred to as a B paste.
By kneading the A paste and the B paste in equal amounts, a cured product can be obtained. Using this composition, a test was conducted according to the evaluation method described above. As a result, the Shore A hardness was 79, the sealing property was A, the filling operability was A, and the removing operability was A.

Comparative Examples 3 to 8 Temporary Stopping (manufactured by GC Corporation), Temporary Stopping (manufactured by Matsukaze), Cavitre (manufactured by GC Corporation), seal ( Chofu (Matsukaze), Kafoods (Showa Yakuhin), and Neodyne (Neo Yakuhin)
A test similar to the example was performed. Table 5 shows the results.

[0052]

[Table 5]

Comparative Example 9 A test was conducted in the same manner as in Example 3 except that nonaethylene glycol dimethacrylate (polymer elongation: 5%) was used in place of the polymerizable monomer MAc15S. As a result, the Shore A hardness was 85, the sealing property was B, the filling operability was A, and the removing operability was B.

Claims (1)

(57) [Claims] (A) 20 to 90 parts by weight of a polymerizable monomer having a polymer elongation of 10% or more, (B) 10 to 80 parts by weight of a filler, and (C) 0.01 to 5 parts of a polymerization initiator. Parts by weight and (D) 0.1 to 10 parts by weight of the superabsorbent resin [however, (A)
And the total amount of (B) is 100 parts by weight, and (C) is (A)
(D) is (A) + (B)
In total per 100 parts by weight of a dental temporary sealing material composition.