JP2003040723A - Dental curing composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a dental curing composition comprising an organopolysiloxane curing composition, especially a composition preventing sagging of a paste while suppressing the viscosity to a low level and readily carrying out uniform piling on a coated surface of a denture, etc., even to the border in a flexible lining material or a dental mucosal regulating material. SOLUTION: This dental curing composition comprises the organopolysiloxane curing composition. The dental curing composition is characterized as comprising (I) a silicone resin filler and/or a silica filler and (II) a liquid polyether such as polyethylene glycol or polypropylene glycol.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a dental curable composition comprising an organopolysiloxane curable composition.

[0002]

BACKGROUND OF THE INVENTION Organopolysiloxane-based curable compositions have stable elasticity and are extremely harmless to living organisms.
Since a cured product with excellent stability over time of the material can be obtained,
In recent years, it has been widely used as a dental material such as a denture base lining material, an impression material, and a compatibility test material.

In order to cure these dental curable compositions (hereinafter also referred to simply as "curable compositions") in the intended shape, it is important to prevent sagging during the application of paste and the deposition. is there. In particular, when it is used as a lining material for denture base such as a dental mucosa conditioning material or a soft lining material, it is extremely important to improve its properties as described below.

That is, when a denture is used for a long period of time, the compatibility with the denture gradually deteriorates due to absorption of the alveolar ridge, etc., and maintenance and stability become poor. If the incompatible denture is continuously used as it is, uneven pressure is applied to the submucosa of the denture, which may cause ulcer or inflammation on the mucous membrane or cause pain due to occlusal pressure. When the above-mentioned incompatibility occurs, it is necessary to repair the denture or create a new denture, or to line up the denture in use with a soft material to restore the compatibility of the denture to the mucous membrane. Dental mucosa conditioning materials and soft lining materials made of available acrylate-based or organopolysiloxane-based curable compositions are used.

Here, the dental mucosa conditioner is used for treating the oral mucosa before the repair of the denture.
For that purpose, high flexibility is required. Since the period of use is a relatively short period of one week to several weeks until the oral mucosa is restored to a healthy state, a material that can be easily removed is desired. At present, many types consist of an acrylate-based polymer, a plasticizer and an alcohol with an emphasis on adhesiveness to a denture, but there is a drawback that it is difficult to remove from the denture base after treatment. On the other hand, the type composed of an organopolysiloxane-based curable composition has excellent removability from the denture base, but is widely used as a mucosa conditioner because it is difficult to achieve both flexibility and paste properties that are difficult to sag as described below. It has not become popular.

The soft lining material is a material for repairing a denture, and is required to have hardness and strength that will not deform for a long period after repair. Since this material is relatively harder than the mucosa conditioner, an organopolysiloxane curable composition is mainly used, and the above performance can be satisfied by adjusting the degree of crosslinking of the cured product and the content of the filler. Is designed to.

Generally, as a method for preparing an organopolysiloxane-based curable composition, two materials, that is, a member containing a paste or liquid curing catalyst (upper material) and a member not containing a curing catalyst (second material) are stored separately. It is carried out by kneading both before use. The curable composition preferably has a low viscosity from the viewpoint of kneading operability, particularly kneading, and the content of the filler component to be blended is reduced from the viewpoint of improving mechanical strength, It is necessary to achieve the purpose. Further, as described above, in the dental mucosa regulating material for which the hardened body is required to have particularly high flexibility, it is necessary to keep the amount of the filler component used as low as possible in order to satisfy the properties.

However, the organopolysiloxane-based curable composition used for these denture base lining materials, particularly the composition having a reduced viscosity for the above-mentioned reasons, tends to sag the mixture of both materials kneaded, resulting in denture. There was a problem that it was difficult to arrange. In addition, when the mixture easily sags, when the curable composition is cured in the patient's oral cavity, the mixture disposed on the denture base edge is washed away, and the shape of the lining material formed is in the oral cavity of the denture. Will no longer have the rounded shape necessary for strong adsorption to.

From the above viewpoint, a dental curable composition comprising an organopolysiloxane curable composition, especially a soft lining material or a dental mucosa conditioning material, prevents sagging of the paste while keeping the viscosity low. However, it has been a major problem to provide a composition that can easily be evenly applied to the coated surface of a denture or the like up to the peripheral portion.

[0010]

Means for Solving the Problems As a result of intensive studies to solve the above-mentioned problems of the prior art, the present inventors have found that in a dental curable composition comprising an organopolysiloxane curable composition, (I) It has been found that the above problems can be overcome by using a dental curable composition comprising a silicone resin-based filler and / or a silica-based filler, and (II) a liquid polyether. Has been completed.

That is, the present invention provides a dental curable composition comprising an organopolysiloxane curable composition,
A dental curable composition comprising (I) a silicone resin-based filler and / or a silica-based filler, and (II) a liquid polyether.

[0012]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention can be applied without limitation to a known dental curable composition comprising an organopolysiloxane curable composition. It is preferable that the curable composition has a viscosity of 10 to 3000 poise at 25 ° C. at the time of kneading, because the paste easily sags and the effect of the present invention is remarkably exhibited. The soft lining material usually has a viscosity of 300 to 1500 poises, and the present invention can be preferably applied to it. Furthermore, since the viscosity of the dental mucosa conditioner is particularly low at 100 to 1000 poises, the present invention can be applied particularly suitably.

The organopolysiloxane-based curable composition in the present invention is a type of curable composition in which a compound having a siloxane bond as a main chain is polymerized and cured. The cured product is usually called silicone rubber and has stable elasticity.

Examples of the polymerization mode for curing include thermal vulcanization type, condensation type, addition type, and ultraviolet curing type. When the curable composition is the denture base lining material, The room-temperature addition polymerization type is preferable because it can be directly cured in the oral cavity of a patient and no by-products are generated.

As the room temperature addition-polymerization type organopolysiloxane type curable composition, known compositions which are cured by a hydrosilylation reaction can be used without any limitation. Usually, as a curing component, carbon is added to the (A) terminal. An organopolysiloxane having at least two organic groups having a carbon unsaturated bond in the molecule, (B1) an organohydrogenpolysiloxane having at least three hydrogen atoms directly bonded to a silicon atom in the molecule, and (C) Those containing a hydrosilylation catalyst are used.

Here, the organopolysiloxane having at least two organic groups having a carbon-carbon unsaturated bond at the end of the component (A) is a hydrogen directly bonded to the silicon atom of the component (B1). The hydrosilylation catalyst of component (C) acts as a catalyst for the cross-linking hydrosilylation reaction, which acts as a cross-linking agent for cross-linking the organohydrogenpolysiloxane having at least three atoms in the molecule.

For convenience of explanation, "carbon at the terminal-
"Organopolysiloxane having at least two organic groups having a carbon unsaturated bond in the molecule" and "Organohydrogenpolysiloxane having a hydrogen atom (corresponding to SiH group) directly bonded to a silicon atom in the molecule"
Are simply “unsaturated bond-containing siloxane” and “S
Also referred to as "iH siloxane".

Component (A) is not limited in its structure as long as it is an organopolysiloxane having at least two organic groups having a carbon-carbon unsaturated bond at the end in its molecule, and may have a straight chain structure. It may be branched or a mixture thereof.

The viscosity is not particularly limited, but from the viewpoint of the properties of the paste before curing, the properties of the cured product obtained after curing, etc., it is 10 to 3000 poises at 25 ° C., particularly,
It is preferably from 10 to 1500 poise. When several kinds of unsaturated bond-containing siloxanes are mixed and used as the component (A), the above viscosity means the viscosity of the mixture.

The organic group having a carbon-carbon unsaturated bond at the terminal existing in the molecule of the unsaturated bond-containing siloxane of the component (A) is preferably a vinyl group, an allyl group or 1-
Examples thereof include butenyl group and ethynyl group. Of these, a vinyl group is most preferable because it is easily synthesized and available. The organic group having a carbon-carbon unsaturated bond at these ends may be present at either the end of the molecular chain of the organosiloxane, the middle thereof, or both of them. In order for the reactivity during curing and the cured product after curing to have excellent physical properties, at least one is preferably present at the terminal.

The organic group other than the above-mentioned "organic group having a carbon-carbon unsaturated bond at the terminal" present in the molecule of the unsaturated bond-containing siloxane of the component (A) is a methyl group, an ethyl group or a propyl group. , Butyl group, alkyl group such as octyl group, aryl group such as phenyl group, chloromethyl group,
Substituted alkyl groups such as 3,3,3-trifluoropropyl group are exemplified. Of these, a methyl group is most preferable because it is easy to synthesize and obtain, and gives good physical properties after curing.

Typical components (A) that can be used in the present invention are represented by the general formulas:

[0023]

[Chemical 1]

(However, a is an integer of 400 to 1500, b is an integer of 0 to 5, R1 to R7 are the same or different alkyl groups or aryl groups, and R8 is carbon-carbon unsaturated. Organopolysiloxane represented by the formula (1), which is an organic group having a bond. In particular,

[0025]

[Chemical 2]

(However, Ph represents a phenyl group.) And the like.

The repeating order of the repeating constitutional units in the unsaturated bond-containing siloxanes used in the above compounds and the examples and comparative examples described below is completely arbitrary, and the number of the repeating constitutional units shown in the structural formula is It only indicates the total amount of each structural unit.

Component (B1) that can be used in the present invention
Is an organohydrogenpolysiloxane in which at least three hydrogen atoms directly bonded to silicon atoms are present in the molecule. In order to react with the unsaturated bond-containing siloxane to form a crosslinked structure, at least three hydrogen atoms (that is, SiH groups) directly bonded to silicon atoms are necessary in the molecule. It is preferable to have 3 to 50 pieces. If the number of SiH groups present in the molecule is less than 3, a crosslinked structure is not formed and a rubber elastic body cannot be obtained.

The organic group present in the SiH siloxane molecule in the component (B1) is not particularly limited, and for example, the "terminal carbon-carbon present in the molecule of the unsaturated bond-containing siloxane of the component (A) described above. Examples of the organic group other than the “organic group having an unsaturated bond” are illustrated, but the methyl group is most preferable because it is easy to synthesize and obtain, and provides good physical properties after curing. The SiH siloxane may be linear, branched or cyclic, and may be a mixture thereof.

A typical example of the component (B1) that can be used in the present invention is represented by the general formula:

[0031]

[Chemical 3]

(However, c is an integer of 1 to 100,
d is an integer of 3 to 50, R9 to R15 are the same or different alkyl groups or aryl groups, R16 is an alkyl group, an aryl group or a hydrogen atom, and R17
Is a hydrogen atom. ). The SiH siloxane shown by these is mentioned. In particular,

[0033]

[Chemical 4]

(However, Ph represents a phenyl group.) And the like.

The order of bonding of the repeating structural units in the SiH siloxane and the SiH siloxane used in Examples and Comparative Examples described later is completely arbitrary, and the number of repeating structural units shown in the structural formula is the same for each constituent. It only indicates the total amount of units.

Further, in the above room temperature addition-type organopolysiloxane curable composition, further, (B2) an organohydrogen having one or two hydrogen atoms directly bonded to silicon atoms is present in the molecule. The reaction may be carried out in the presence of polysiloxane. When this component (B2) is blended, the elastic modulus tends to be small, and it becomes easy to adjust the viscoelasticity of the cured product.

The organic group present in the SiH siloxane molecule in component (B2) is not particularly limited, and for example, the "terminal carbon-carbon present in the unsaturated bond-containing siloxane molecule in component (A) described above is present. Examples of the organic group other than the “organic group having an unsaturated bond” are illustrated, but the methyl group is most preferable because it is easy to synthesize and obtain, and provides good physical properties after curing. The hydrogen atom directly bonded to the silicon atom may be present either at the terminal of the molecular chain of the organosiloxane or in the middle thereof, or in the case of having two hydrogen atoms, both of them. In order for the reactivity during curing and the cured product after curing to have excellent physical properties, at least one is preferably present at the terminal. The SiH siloxane may be linear, branched or cyclic, and may be a mixture thereof.

Typical compounds represented by the formula (B2) which can be used in the present invention are represented by the general formulas:

[0039]

[Chemical 5]

(However, e is an integer of 1 to 100,
R18 to R23 are the same or different alkyl groups or aryl groups, R24 is an alkyl group, an aryl group or a hydrogen atom, and R25 is a hydrogen atom. ). The SiH siloxane shown by these is mentioned. In particular,

[0041]

[Chemical 6]

(However, Ph represents a phenyl group.) And the like.

The bonding order of the repeating constitutional units in the SiH siloxane and the SiH siloxanes used in Examples and Comparative Examples described later is completely arbitrary, and the number of repeating constitutional units shown in the structural formula is the same for each constitution. It only indicates the total amount of units.

In the dental curable composition of the present invention, the amount ratio of the component (A) and the component (B1) to be reacted is such that the component (B1) with respect to the total number of terminal carbon-carbon unsaturated bonds of the component (A). It is preferable that the amount ratio is 0.2 to 3.0, particularly 0.3 to 2.0 in terms of the ratio of the total number of hydrogen atoms bonded to the silicon atom. In particular, when the curable composition is a dental mucosa conditioner, this ratio is 0.3-1.
It is preferable that the amount ratio be 0. On the other hand, if the curable composition is a soft backing, this ratio will be 0.7-2.
It is preferable that the amount ratio be 0.

Further, in the composition in which the component (B2) is coexisted, the ratio of the amounts of the component (A), the component (B1) and the component (B2) to be reacted is such that the terminal carbon-carbon content of the component (A) does not change. The component (B1) and the component (B
It is preferable that the amount ratio is 0.5 to 5.0, particularly 0.7 to 5.0 in terms of the ratio of the total number of hydrogen atoms bonded to silicon atoms in 2). In particular, when the curable composition is a dental mucosa modifier, this ratio is preferably 0.7 to 2.0. On the other hand, when the curable composition is a soft backing material, it is preferable that this ratio is a quantitative ratio of 1.5 to 4.0.

The hydrosilylation catalyst of component (C) that can be used in the present invention is the above component (A) and component (B1).
And a component (B2) which is further added if necessary, which acts as a catalyst for forming a matrix composed of a crosslinked organopolysiloxane by reacting (specifically, hydrosilylation reaction). Component (C) is
As long as they have such a catalytic action, those usually used as a hydrosilylation reaction catalyst can be used without limitation.

Specific examples of the component (C) that can be preferably used include chloroplatinic acid, alcohol-modified products thereof, platinum-based catalysts such as platinum vinylsiloxane complex, and similar rhodium-based catalysts. it can. Among these, platinum-based catalysts are preferable from the viewpoint of easy availability. In addition,
In order to improve the storage stability, it is preferable to use a substance having a low chlorine content such as a platinum vinylsiloxane complex.

The blending amount of the component (C) is not particularly limited as long as the hydrosilylation reaction is sufficiently advanced. In general, the rate of the hydrosilylation reaction increases to a certain extent with an increase in the amount of the component (C), but the use of an excessive amount is not economically advantageous because the effect corresponding to the amount is not obtained. On the contrary, it tends to be difficult to control the crosslinking reaction and causes problems such as coloring. Therefore, in determining the blending amount of the component (C), it may be determined appropriately for each system in consideration of such points. By the way, when the component (C) is a platinum-based catalyst, the preferable blending amount of the component (C) is as a platinum amount, the component (A), the component (B1) and the component (B2) which is blended as necessary. In the range of 0.1 to 1000 ppm.

The above organopolysiloxane-based curable composition used as a dental material is usually mixed with a filler in order to impart mechanical strength to the cured product. In the present invention, (I) a silicone resin-based filler and / or a silica-based filler is used as the filler.
These filler components not only supplement the mechanical strength of the cured product obtained by curing the dental curable composition, but also coexist with the component (II) liquid polyether described below to form a paste. It has the role of reducing sagging.

As the component (I) used in the present invention,
Any known one can be used without any limitation as long as it does not inhibit the curing reaction of the organopolysiloxane.

Specific examples of silicone resin fillers that are preferably used include polymethylsilsesquioxane and poly (0.1 to 99.9 mol% methyl + 0.1 to 0.1%).
99.9 mol% phenyl) silsesquioxane, poly (99-99.9 mol% methyl + 0.1-1 mol%
Hydrogen) silsesquioxane and the like.

Among these, those obtained by hydrolyzing and condensing organotrialkoxysilane or a mixture of one or more hydrolyzed and condensed products thereof in an aqueous solution of ammonia or amines are chlorine atoms, It is preferable that it has almost no impurities such as alkaline earth metals and alkali metals and that it is spherical.

The average particle diameter of the silicone resin-based filler used in the present invention is 0.1 to 100 μm, preferably 0.1.
Those having a thickness of 1 to 20 μm are used. If it is less than 0.1 μm, it is difficult to manufacture, and it is difficult to fill the necessary amount of the curable composition. If it exceeds 100 μm,
It tends to be difficult to obtain the required reinforcing effect for the cured product.

Specific examples of the silica-based filler that is preferably used include crushed quartz, fused silica powder, wet silica, and dry silica powder.

Further, in order to improve the dispersibility in the organic solvent, these silica-based fillers are treated with a surface treatment agent such as trimethylchlorosilane, dimethyldichlorosilane, methyltrichlorosilane, hexamethyldisilazane, and silicone oil to make the particles hydrophobic. It is preferable to use a compound that has been subjected to a chemical treatment.

The average particle size of the silica-based filler used in the present invention is 10 μm or less, preferably 0.001 to 1 μm.
Used. If it exceeds 10 μm, it tends to be difficult to obtain the reinforcing effect required for the silicone rubber cured product.

The addition amount of the component (I) used in the present invention is optional depending on the physical properties (hardness, tensile strength, tear strength, etc.) required for the cured product obtained by curing the curable composition. Although it may be prepared, it is preferably in the range of 1 to 30% by weight based on the total amount of the curable composition. In particular, when the curable composition is a dental mucosa conditioner, the content of the component (I) is kept as low as 1 to 20% by weight in order to make the cured body more flexible. However, when the content of the filler is reduced in this way, the paste becomes extremely liable to sag as described above, and the effect of the present invention is particularly remarkable. On the other hand, when the curable composition is a soft lining material, the content of the filler component (I) is preferably 10 to 30% by weight.

The most important feature of the present invention is that in the organopolysiloxane curable composition containing the above (I) silicone resin filler and / or silica filler, the component (II) liquid polyether is contained. Is to let. As a result, the viscosity of the paste and the flexibility of the cured body are hardly changed, and drooling of the paste is significantly suppressed,
A denture base lining material can greatly improve the operability and the certainty of mounting in the oral cavity.

The component (II) liquid polyether is a compound which is liquid at 25 ° C., and any known compound may be used as long as it does not hinder the curing reaction of the organopolysiloxane, and any one or more of them may be used. Can be used in combination. The liquid state may be a viscous state as long as it maintains fluidity at the temperature.

A liquid polyether that can be preferably used is a polyether having a polyalkylene oxide unit as a repeating unit. The alkylene oxide group is preferably one having a linear or branched alkylene group having 2 to 4 carbon atoms.

Specific examples thereof include liquid polyalkylene glycols such as polyethylene glycol, polypropylene glycol and polybutylene glycol, and polyethers in which the polyalkylene glycol is ether-bonded to the hydroxyl groups of glycerin.

Of these, polyalkylene glycols are preferable from the viewpoints of the high effect and biotoxicity, and particularly polyethylene glycol having a molecular weight of 200 to 600,
Most preferred is polypropylene glycol having a molecular weight of 400-3500.

The amount of the component (II) used in the present invention is 0.01 to 5% by weight based on the total amount of the curable composition.
Is preferable, and 0.03 to 3% by weight is particularly preferable.
Even if the addition amount is more than 5% by weight, the effect corresponding to the addition amount cannot be obtained and it is economically disadvantageous, and if it is less than 0.01% by weight, the effect cannot be obtained.

The component (II) may be added together with the other components, or may be added to the surface of the filler by being mixed with the component (I) in advance. .

In the dental curable composition of the present invention, the above component (I) is used as long as the physical properties of the cured product are not impaired.
You may add various fillers and various additives other than.

As the above-mentioned other fillers, fillers generally added to silicone rubber and the like can be used without any limitation. Examples of such fillers include fluorocarbon resin-based fillers such as polytetrafluoroethylene powder and polyvinylidene fluoride powder; other polymer powders; carbon black; glass fiber; composite filler (composite of inorganic oxide and polymer Crushed) and the like.

Further, the above-mentioned various additives specifically include a hydrogen gas absorbent such as black platinum or fine palladium;
Reaction inhibitors such as 1,3-divinyltetramethyldisiloxane; pigments such as titanium dioxide; antioxidants such as BHT;
Antibacterial agents such as chitosan; plasticizers such as silicone oil;

The above-mentioned various fillers and various additives are appropriately added according to the purpose, and when various fillers and various additives are blended, these respective components are added before the crosslinking curing reaction. It may be blended.

The method for preparing the dental curable composition of the present invention is not particularly limited, but an ordinary temperature addition type organopolysiloxane curable composition will be described below as an example.

First, the necessary components are appropriately weighed out of the component (I), the component (II), the component (A), the component (C) and, if necessary, various fillers and various additives, and kneader, planetary are used. A paste-like or liquid curable composition (upper material) can be obtained by kneading and stirring with a general kneader such as the above, or a general stirrer until uniform.

Subsequently, the component (I), the component (II), the component (A), the component (B1) and, if necessary, the component (B2),
A paste-like or liquid curable composition (Otsuka) can be obtained by appropriately measuring necessary components from various fillers and various additives and performing the same operation as the above-mentioned upper material.

These upper material and second material are stored separately and kneaded immediately before use to be used as a paste-like mixture.

[0073]

EXAMPLES Examples will be shown to more specifically describe the present invention, but the present invention is not limited to these examples.

In the following Examples and Comparative Examples, the components used in the tests are shown below. 1) Component (A) -Polysiloxane 1: α, ω-divinylpolydimethylsiloxane represented by the following formula (viscosity 100 poise; GE Toshiba Silicone XC86-A9609)

[0075]

[Chemical 7]

Polysiloxane 2: α, ω-dihydroxypolydimethylsiloxane represented by the following formula (viscosity 1
Poise; Toray Dow Corning PRX413)

[0077]

[Chemical 8]

2) Component (B1) -SiH siloxane 1: a compound represented by the following formula

[0079]

[Chemical 9]

3) Component (B2) SiH siloxane 2: compound represented by the following formula

[0081]

[Chemical 10]

4) Component (C) -Platinum catalyst: Platinum vinyl siloxane complex-Tin catalyst: Bis (2-ethylhexanoate) tin in 50% polydimethylsiloxane solution 5) Component (I) -Filler 1 ( Silicone resin-based filler): Polymethylsilsesquioxane powder obtained by hydrolyzing methyltrimethoxysilane (average particle size 3 μm) -Filler 2 (silica-based filler): fumed silica (average particle size 0) 0.01 μm; Reokuro MT10 manufactured by Tokuyama) 6) Component (II) Polyether 1: Polyethylene glycol having a molecular weight of 400 (viscosity 1 poise; PEG400 manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.) Polyether 2: Polypropylene glycol having a molecular weight of 3000 (viscosity 6) Poise; Asahi Denka Co., Ltd. P3000) 7) Other components ・ Tetraethoxysilane (GE Toshiba Silicone Co., Ltd.) S
L8124) Polyether 3: polyethylene glycol having a molecular weight of 6000 (flakes; PEG600 manufactured by Dai-ichi Kogyo Seiyaku Co., Ltd.)
0) Moreover, in the following Examples and Comparative Examples, the dental curable compositions were evaluated by the following methods. 1) Evaluation of sagging property of admixture 1 g of each of upper material and second material was collected on kneading paper and kneaded with a spatula for 30 seconds. After that, the above mixture was placed on a PP sheet and attached to a graduated glass plate with a double-sided tape. 55 seconds after the start of kneading, the scale on the tip was read (A value), and 5 seconds after that, the glass plate was stood vertically. The state was maintained for 1 minute, and the scale at the tip of the kneaded product was read 2 minutes after the start of kneading (B value). The value of sag D was calculated by the following formula. D (mm) = B−A 2) At a viscosity of 25 ° C., the above-mentioned upper material and the second material are kneaded for 30 seconds, and immediately after the kneading, the viscosity of this mixture is measured with a CS rheometer (manufactured by Calime) with a torque of 30,000 dyne. -Measured under the condition of cm. 3) Shore A hardness of the cured product A cured product having a diameter of 9 mm and a height of 12 mm was prepared and stored in water at 37 ° C for 2 hours. Then, it was left standing in a room at 23 ° C. for 5 minutes, and a spring type hardness tester (A type) was used for 9.8
A load of N was applied and the value after 30 seconds was taken as the Shore A hardness. The Shore A hardness of 15 or less can be preferably used as the mucous membrane conditioner, and 20 to 40 can be preferably used as the soft lining material.

Example 1 A dental mucosa conditioning material comprising the following upper and lower materials was manufactured.

10 parts by weight of filler 1, 5 parts by weight of filler 2, 1 part by weight of polyether 1, 1 part of polysiloxane 1
00 parts by weight was weighed, and stirred and mixed for 30 minutes with a 2 L planetary mixer (manufactured by Inoue Seisakusho). Thereafter, 0.5 part by weight of a platinum catalyst was added, the mixture was further stirred for 20 minutes, and then decompressed by depressurizing with a vacuum pump for 10 minutes to prepare an upper material.

Further, 10 parts by weight of the filler 1, 5 parts by weight of the filler 2, 1 part by weight of polyether 1 and 100 parts by weight of polysiloxane 1 were weighed and mixed by a planetary mixer for 30 minutes. After that, add 0.8% polysiloxane 1.
By weight, polysiloxane 2 (3.3 parts by weight) was added, the mixture was further stirred for 20 minutes, and then defoamed by depressurizing with a vacuum pump for 10 minutes to prepare Otsuka material.

The sag property of the mixture prepared by kneading the above-mentioned upper material and the second material was measured to be 4 mm. The viscosity was 550 poise. Further, the Shore A hardness of the cured product was 10.9.

Examples 2 to 4 The same procedures as in Example 1 were carried out except that the composition of the upper material and the second material of Example 1 was changed. Table 1 shows the evaluation results
Shown in.

Comparative Example 1 The same procedure as in Example 1 was carried out except that the silicone resin-based filler and the silica-based filler which were the components (I) were not included. The sagging property (D) is 25 mm,
If the component (I) was not added, the effect of lowering the sagging property could not be obtained.

Comparative Example 2 The procedure of Example 1 was repeated, except that the liquid polyether of component (II) was not included. The dripping property (D) was 14 mm, and the effect of lowering the dripping property was small unless the component (II) was added.

Comparative Example 3 The procedure of Example 1 was repeated, except that the liquid polyether of component (II) was replaced by the flaky polyether 3. The sagging property (D) was 23 mm, and the effect of decreasing the sagging property was not obtained with the flaky polyether.

[0091]

[Table 1]

[0092]

EFFECTS OF THE INVENTION According to the present invention, the drooping property of the dental curable composition can be greatly improved without increasing the viscosity. Therefore, when applied to the denture base lining material, after kneading, the operation of placing on the denture is easy, and when the denture is mounted by curing the curable composition placed in the oral cavity of the patient. Since the lining material can be sufficiently present up to the denture base edge, stable attachment of the denture is possible. In particular, when it is a dental mucosa conditioner, the above-mentioned effects are particularly remarkably exhibited, excellent operability and flexibility, and a denture which can firmly adsorb a denture in the oral cavity can be provided.

Claims (6)

[Claims] 1. A dental curable composition comprising an organopolysiloxane curable composition, comprising: (I) a silicone resin filler and / or a silica filler; and (I)
I) A dental hardenable composition comprising a liquid polyether. 2. The organopolysiloxane-based curable composition has a structure in which (A) an organopolysiloxane having at least two organic groups having a carbon-carbon unsaturated bond at a terminal, and (B1) a direct bond to a silicon atom. The dental curable composition according to claim 1, which comprises an organohydrogenpolysiloxane having at least three hydrogen atoms present in the molecule, and (C) a hydrosilylation catalyst. 3. The organopolysiloxane-based curable composition further comprises (B2) an organohydrogenpolysiloxane having one or two hydrogen atoms directly bonded to silicon atoms in the molecule. Item 3. The dental curable composition according to Item 2. 4. The dental curable composition according to claim 1, wherein the liquid polyether (II) is polyethylene glycol or polypropylene glycol. 5. The dental curable composition according to claim 1, which is a lining material for a denture base. 6. The dental curable composition according to claim 5, wherein the denture backing material is a dental mucosa conditioner.