Photocuring silicone impression material with improved storage stability

Abstract

The present invention provides a silicone composition for dental impression materials that can extend the storage stability of dental impression materials. [Solution] This disclosure generally relates to a curable one-component silicone composition. The curable one-component silicone composition comprises an organic polysiloxane compound having at least two unsaturated groups, an organic hydrogen polysiloxane compound having at least two Si-H groups, a catalyst that enables the addition of silicon-bonded hydrogen atoms to the unsaturated groups, and at least one surface-treated particulate filler. The curable one-component silicone composition is useful as a dental impression material. More specifically, the curable one-component silicone composition comprising the surface-treated filler extends the storage stability of the dental impression material. This disclosure also provides a method for preparing such a curable one-component silicone composition.

Description

Technical Field

[0001] The present disclosure generally relates to curable one - part silicone compositions. The curable one - part silicone composition includes an organopolysiloxane compound having at least two unsaturated groups, an organohydrogenpolysiloxane compound having at least two Si - H groups, a catalyst that enables a hydrogen atom bonded to silicon of the organohydrogenpolysiloxane compound to add to the unsaturated group of the organopolysiloxane compound, and at least one surface - treated particulate filler. This curable one - part silicone composition is useful for the preparation of dental impression materials, soft relining materials for dentures, and template materials for provisional crowns and bridge restorations. More specifically, the curable one - part silicone composition containing the surface - treated filler extends the storage stability of dental impression materials. The present disclosure also provides a method for preparing such curable one - part silicone compositions.

Background Art

[0002] In dentistry, addition - type silicones are the most widely used impression materials. Addition - curable silicones are widely used as impression materials in dentistry due to their high accuracy and dimensional stability. These are usually two - part types, cured by a hydrosilylation reaction, passed through a mixing tip, and hardened within a few minutes in the mouth to give an accurate impression. They also contain silica fillers to provide reinforcement and increase hardness. A catalyst often used for this reaction is the Karstedt catalyst, which is a complex of platinum(0) and divinyltetramethyldisiloxane (DVTMDS). However, since the total time for taking an impression is shortened, it would be advantageous to cure a single - component material upon demand.

[0003] Photocurable silicones used in industrial applications are typically cured by platinum-based catalysts that do not catalyze hydrosilylation reactions in the presence of hydrogen-functionalized polydimethylsiloxane (HPDMS), except for exposure. Common catalysts used in this application are platinum diacetacetate (Pt(acac)2) and trimethyl(methylcyclopentadienyl)platinum ((Me-Cp)Pt(Me)3). However, these catalysts are unstable in the presence of crosslinking agents or HPDMS and silica fillers. Their pot life is on the order of hours to days. Therefore, they are pre-mixed within hours of use. While this instability is unacceptable for dental impression materials, the expected shelf life at room temperature is over one year.

[0004] Oxman and Boardman's U.S. Patent No. 5,145,886 describes dental impression LC silicone preparations based primarily on the use of platinum(II) acetylacetonate {Pt(acac)2} as a catalyst. While inhibitors such as acetylene alcohol and phosphates are mentioned, stability exceeding 150 days is claimed without the use of inhibitors. In our experience, one of the exemplary preparations mentioned exhibited stability for several hours, more similar to photocurable silicones currently marketed for industrial applications, such as Uvisil by Wacker and similar materials by Momentive.

[0005] Irmer et al.'s U.S. Patent Application Publication US2008 / 0033071 describes a two-component LC silicone preparation optionally containing alkinol and vinylsiloxane as inhibitors. These extend the pot life of the mixture by several hours for the intended application.

[0006] Marrot et al.'s U.S. Patent Application Publication S2014 / 0004359 describes a two-component LC silicone system used as a release liner film for packaging applications. It further discloses the use of acetylenediol with an acid to extend the pot life after mixing to approximately 24 hours.

[0007] All one-component photocurable silicones that can be cured by hydrosilylation reactions use silica as a filler to obtain the desired strength and viscosity characteristics. However, based on controlled studies, it has been suggested that silica may catalyze the formation of platinum zero species Pt(0), which can lead to degradation (JC Kenvin et al, Langmuir Vol.7, 1198 (1991) and M. Womes et al, Catalysis Letters Vol.85, pg.25 (2003)). [Overview of the project] [Problems that the invention aims to solve]

[0008] As mentioned above, there is still a need for curable impression materials containing silica filler and possessing greater stability and good curability. Furthermore, curing a single-component material would be advantageous as it reduces the total impression-taking time. [Means for solving the problem]

[0009] The object of this disclosure is to provide a curable one-component silicone composition for dental impression materials that can extend the storage stability of dental impression materials. This is achieved by including surface-treated particulate fillers in the composition. The surface-treated particulate fillers reduce the reactivity of surface silanol groups.

[0010] A first aspect of this disclosure discloses a curable one-component silicone composition for dental impression materials. The silicone composition comprises (a) an organic polysiloxane compound having at least two unsaturated groups, (b) an organic hydrogen polysiloxane compound having at least two Si-H groups, (c) a catalyst that enables the addition of hydrogen atoms bonded to the silicon of the organic hydrogen polysiloxane compound to the unsaturated groups of the organic polysiloxane compound, and (d) at least one surface-treated particulate filler.

[0011] According to one embodiment of a curable one-component silicone composition, a surface-treated filler extends the storage stability of dental impression material.

[0012] According to another embodiment of the curable one-component silicone composition, the organic polysiloxane compound having at least two unsaturated groups includes a vinyl-terminated polydimethylsiloxane.

[0013] According to one embodiment of a curable one-component silicone composition, the organic hydrogen polysiloxane compound having at least two Si-H groups is HPDMS.

[0014] According to another embodiment of the curable one-component silicone composition, the catalyst is selected from the group consisting of Pt(acac)2, platinum(II)bis(benzoylmethanate), platinum(II)bis(benzoylacetonate), and (Me-Cp)Pt(Me)3.

[0015] According to one embodiment of a curable one-component silicone composition, at least one surface-treated particulate filler is selected from the group consisting of inorganic particulate fillers, submicron silica or oxides, and inorganic fillers.

[0016] In one particular embodiment, at least one surface-treated particulate filler is a calcium aluminosilicate filler coated with a cross-linked acrylic resin.

[0017] According to one embodiment of a curable one-component silicone composition, surface-treated particulate fillers are prepared by a process for preparing composite filler particles. This process is (a) A coating composition comprising a film-forming agent that forms a coating layer on the surface of a particulate filler, comprising the step of coating a particulate filler having a median particle size (D50) of 100 to 1200 nm, wherein the coating layer exhibits reactive groups on the surface of the coating layer, and the reactive groups are selected from addition polymerizable groups and stepwise polymerizable groups that thereby form the coated particulate filler, and thereafter or simultaneously, (b) To provide a granule of coated particulate filler, a step of granulating coated particulate filler in the presence of a further crosslinking agent and further particulate filler that does not exhibit reactive groups, wherein the granule contains coated particulate filler particles and further particulate filler particles bound together via at least one coating layer, and the at least one coating layer may be crosslinked by crosslinking groups obtained by the reaction of reactive groups and further crosslinking agents, thereby the granulation is carried out by spray granulation or growth granulation, (c) A step of milling, classifying, and sieving granules of coated particulate filler, (d) A step of further crosslinking the coated particulate filler granules, Includes, The prepared filler particles have a median particle size (D50) of 1 to 70 μm. The reactive group is converted into a crosslinking group obtained by the reaction of the reactive group with a further crosslinking agent. Particulate fillers are the main component by volume of composite filler particles.

[0018] Other aspects are described below, some of which will become apparent from the description or will be learned from the practice of this disclosure. [Modes for carrying out the invention]

[0019] Disclosed herein are a curable one - part silicone composition, a method of using the curable one - part silicone composition for preparing a dental impression material, a soft relining material for dentures, and a template material for provisional crowns and bridge restorations, and a method of preparing such a curable one - part silicone composition.

[0020] In a first aspect of the present disclosure, a curable one - part silicone composition for a dental impression material is provided. The curable one - part silicone composition generally comprises (a) an organopolysiloxane compound having at least two unsaturated groups, (b) an organohydrogenpolysiloxane compound having at least two Si - H groups, (c) a catalyst that enables a hydrogen atom bonded to silicon of the organohydrogenpolysiloxane compound to add to the unsaturated group of the organopolysiloxane compound, and (d) at least one surface - treated particulate filler.

[0021] (a) an organopolysiloxane compound having at least two unsaturated groups The unsaturated group is selected from a vinyl group or an acetylene group. In certain embodiments of the curable one - part silicone composition disclosed herein, the organopolysiloxane compound having at least two unsaturated groups is selected from the group consisting of vinyl - terminated polydimethylsiloxane, trifunctional siloxane, tetrafunctional siloxane, and organopolysiloxane having a phenyl group.

[0022] Examples of trifunctional siloxane include trifunctional polydimethylsiloxane having a vinyl group. The trifunctional polydimethylsiloxane having a vinyl group is vinyl T - structure polymer VTT - 106 (Gelest).

[0023] Examples of tetrafunctional siloxane include tetrafunctional siloxane having a vinyl group. The tetrafunctional siloxane having a vinyl group can be vinyl Q resin dispersion VQM - 135 (Gelest) and Momentive H6 polymer (a mixture of QM resin and vinyl polysiloxane resin).

[0024] The QM resin dispersion has a viscosity of about 5,000 to 60,000 cps. These dispersions may contain a plurality of dispersion components having a desired viscosity and amount of QM resin. The QM resin constitutes about 20 to 25% by weight of each dispersion.

[0025] Examples of the organopolysiloxane having a phenyl group include vinyl-terminated diphenylsiloxane-dimethylsiloxane copolymers. The vinyl-terminated diphenylsiloxane-dimethylsiloxane copolymers can be PDV-0325 and PDV-1631 (Gelest).

[0026] In one particular embodiment of the curable one-part silicone composition disclosed herein, the organopolysiloxane compound having at least two unsaturated groups is of the vinyl-terminated polydimethylsiloxane type (divinyl PDMS).

[0027] In certain embodiments of the curable one-part silicone composition disclosed herein, the organopolysiloxane compound having at least two unsaturated groups is present at a concentration of 10% to 90% by weight based on the total weight of the silicone composition. In one embodiment, the concentration range is 20% to 80% by weight.

[0028] <000010�>(b) An organohydrogenpolysiloxane compound having at least two Si-H groups In certain embodiments of the curable one-part silicone composition disclosed herein, the organohydrogenpolysiloxane compound having at least two Si-H groups is HPDMS.

[0029] In certain embodiments of the curable one-part silicone composition disclosed herein, the amount of hydride in HPDMS is about 3.5 mmol / g to about 4.9 mmol / g, and in some embodiments, the amount of hydride in HPDMS is 4.3 mmol / g.

[0030] In one embodiment of the curable one-component silicone composition disclosed herein, an organohydrogen polysiloxane compound having at least two Si-H groups is present at a concentration of 1% to 20% by weight, such as in a concentration range of 3% to 10% by weight, based on the total weight of the silicone composition.

[0031] (c) Catalyst A useful catalyst for catalyzing the reaction between the hydrogen atom bonded to the silicon in an organic hydrogen polysiloxane compound and the unsaturated group of the organic polysiloxane compound by exposure may be a platinum(II) compound or a platinum(IV) compound.

[0032] Examples of platinum(II) compounds may include, but are not limited to, Pt(acac)2, platinum(II) bis(dibenzoylmethanate), and platinum(II) bis(benzoylacetonate).

[0033] Examples of platinum(IV) compounds include (Me-Cp)Pt(Me)3.

[0034] In some embodiments of the curable one-component silicone compositions disclosed herein, the catalyst is selected from the group consisting of Pt(acac)2, platinum(II)bis(benzoylmethanate), platinum(II)bis(benzoylacetonate), and (Me-Cp)Pt(Me)3.

[0035] In certain embodiments of the curable one-component silicone compositions disclosed herein, the catalyst is Pt(acac)2.

[0036] In one embodiment of the curable one-component silicone composition disclosed herein, the catalyst is added in an amount of about 20 to 500 ppm, such as in a concentration range of 50 to 200 ppm, based on the total weight of the silicone composition.

[0037] (d) Surface-treated particulate filler The particulate fillers have a median particle size (D50) of 1 to 1200 nm, particularly 20 to 800 nm, when measured, for example, using electron microscopy or conventional laser diffraction particle sizing methods such as those embodied by the MALVERN Mastersizer S or MALVERN Mastersizer 2000 instruments.

[0038] According to a specific embodiment, the particulate filler has a median particle size (D50) of 100 to 800 nm.

[0039] The microparticle fillers are not particularly limited, as long as the material of the microparticle filler is acceptable for dental use.

[0040] A curable one-component silicone composition may contain more than one surface-treated microparticle filler.

[0041] In one embodiment of a curable one-component silicone composition disclosed herein, at least one surface-treated particulate filler is selected from the group consisting of inorganic particulate fillers, submicron silica or oxides, and inorganic fillers.

[0042] Inorganic microparticles include, but are not limited to, dental glass, fused silica, quartz, crystalline silica, amorphous silica, soda glass beads, glass rods, ceramic oxides, microparticle silicate glass, and radiopaque glass.

[0043] While finely powdered materials and powdered hydroxyapatite can also be used, materials that react with the silane coupling agent are preferred.

[0044] In some embodiments of the curable one-component silicone compositions disclosed herein, the submicron silica or oxide is selected from the group consisting of fumed silica, precipitated silica, and aluminosilicates.

[0045] Examples of aluminosilicates include, but are not limited to, calcium aluminosilicate, strontium aluminosilicate, and barium aluminosilicate.

[0046] The inorganic filler may be YF3, La2O3, ZrO2, BiPO4, CaWO4, BaWO4, SrF2, or Bi2O3.

[0047] Surface-treated filler particles are generally obtained by processes for preparing composite filler particles, as disclosed in U.S. Patent No. 9,193,849, which is incorporated herein by reference in whole.

[0048] In one embodiment of a curable one-component silicone composition disclosed herein, surface-treated particulate fillers are prepared by a process for preparing composite filler particles. This process is (a) A coating composition comprising a film-forming agent that forms a coating layer on the surface of a particulate filler, comprising the step of coating a particulate filler having a median particle size (D50) of 100 to 1200 nm, wherein the coating layer exhibits reactive groups on the surface of the coating layer, and the reactive groups are selected from addition polymerizable groups and stepwise polymerizable groups that thereby form the coated particulate filler, and thereafter or simultaneously, (b) To provide a granule of coated particulate filler, a step of granulating coated particulate filler in the presence of a further crosslinking agent and further particulate filler that does not exhibit reactive groups, wherein the granule contains coated particulate filler particles and further particulate filler particles bound together via at least one coating layer, and the at least one coating layer may be crosslinked by crosslinking groups obtained by the reaction of reactive groups and further crosslinking agents, thereby the granulation is carried out by spray granulation or growth granulation, (c) A step of milling, classifying, and sieving granules of coated particulate filler, (d) A step of further crosslinking the coated particulate filler granules, Includes, The prepared filler particles have a median particle size (D50) of 1 to 70 μm. The reactive group is converted into a crosslinking group obtained by the reaction of the reactive group with a further crosslinking agent. Particulate fillers are the main component by volume of composite filler particles.

[0049] In one particular embodiment, the surface-treated particulate filler is a particulate calcium aluminosilicate filler coated with a cross-linked acrylic resin.

[0050] In one embodiment of the curable one-component silicone composition disclosed herein, the surface-treated silica filler is present at a concentration of 10% to 80% by weight, such as in a concentration range of 15% to 60% by weight, based on the total weight of the composition.

[0051] In some embodiments of the curable one-component silicone compositions disclosed herein, the surface-treated particulate fillers have a median particle size of 1 to 50 μm. The particle size of the surface-treated particulate fillers may be less than 74 μm. In some embodiments, the particle size of the surface-treated particulate fillers is less than 40 μm.

[0052] According to one embodiment of a curable one-component silicone composition, a surface-treated filler extends the storage stability of dental impression material.

[0053] Surface-treated particulate fillers reduce the reactivity of surface silanol groups.

[0054] Preparation of a curable one-component silicone composition A second aspect of this disclosure discloses a method for preparing a curable one-component silicone composition. The curable one-component silicone composition can be prepared by combining an organic polysiloxane compound having at least two unsaturated groups, an organic hydrogen polysiloxane compound having at least two Si-H groups, and a catalyst, in essentially any order, while stirring, to form an activated silicone resin composition. At least one surface-treated particulate filler is then added to the activated silicone resin composition.

[0055] A curable one-component silicone composition can be prepared by first combining an organic polysiloxane compound having at least two unsaturated groups with an organic hydrogen polysiloxane compound having at least two Si-H groups, then adding a catalyst to form an activated silicone resin composition, and then adding at least one surface-treated microparticle filler to the activated silicone resin composition.

[0056] Use and curing of a curable one-component silicone composition A curable one-component silicone composition can be used to form a curing agent. Curing can generally be achieved at temperatures in the range of 20 to 23°C. The curable one-component silicone composition of this disclosure can be cured by an LED dental curing light equipped with a special head that emits light in the range of 350 nm to 700 nm. In particular, the LED dental curing light emits light in the range of 405 nm.

[0057] The hardening agent is used in dental impression materials, soft relining materials for dentures, and template materials for provisional crowns and bridge restorations.

[0058] In one particular embodiment, the curing material is an impression material, and more specifically, a photocurable silicone paste.

[0059] The disclosures described herein are further illustrated by the compositions described in the following examples, but these examples should not be construed as limiting the scope of the disclosure.

[0060] experiment Test method Curing was achieved using an LED dental curing light (Fusion Lite) equipped with a special head that emits light at 405nm. Stability was tested by placing the paste in a forced-air oven at 50°C or in a temperature-controlled room with fluctuations of 22-27°C. Polymerization was evaluated by poking with a plastic stick. Polymerization was determined when the material did not easily penetrate. Consistency was measured according to ISO 4823 guidelines. The diameter was measured after using a 500g weight for 30 seconds. Compressive strain was applied according to ISO 4823. Both sides of an 8mm x 10mm test specimen were exposed for 20 seconds. Shore A hardness was tested according to DIN 53505. The mold size was 8 mm in diameter and 10 mm in depth. Exposure was 20 seconds on one side only. Curing depth: Tested according to ISO 4049 guidelines. Opacity: Tested according to ISO 4049 guidelines.

[0061] Exemplary preparations Examples of preparations are shown in Table 1. Activated silicone resin compositions are shown in Table 1. To prepare the activated silicone resins, platinum catalyst Pt(acac)2 was added to obtain a final concentration of 0.01% or 100 ppm. Paste preparations containing the following types of surface-treated microparticle fillers are shown in Table 2: Sipernat D13 (Evonik) is a hydrophobic precipitated silica, Aerosil R972 (Evonik) is a hydrophobic fumed silica, and 1.5 μm sized surface-treated microparticle calcium aluminosilicate fillers coated with cross-linked acrylic resin were prepared according to the procedure of Example 10 described in US9193849 and EP2790639 (SphereTec process), the entire disclosure of which is incorporated herein by reference. Table 3 summarizes the stability studies. [Table 1] [Table 2] [Table 3]

[0062] These results indicate that the use of the coated filler described herein, i.e., particulate calcium aluminosilicate filler coated with a cross-linked acrylic resin prepared by the process described in US9193849, in a one-component addition-type silicone impression preparation results in extended stability.

[0063] Those skilled in the art will see that various modifications can be made to the exemplary embodiments and descriptions herein without departing from the spirit and scope of this disclosure. Other embodiments of the invention are described throughout this application. Any embodiment described in relation to one aspect is similarly applicable to other embodiments, and vice versa. Each embodiment and its obvious variations described herein will be understood to be applicable to all embodiments of the invention. Given the descriptions herein, in combination with the knowledge of those skilled in the art to which the invention belongs, any embodiment described herein can be readily achieved and / or further practiced with respect to any use, method, compound, composition, obvious variation thereof, or any combination thereof. All such modifications within the spirit and scope of this disclosure are intended to be encompassed by the accompanying claims.

[0064] The present invention includes the following embodiments. (1) A curable one-component silicone composition for dental impression materials, (a) an organopolysiloxane compound having at least two unsaturated groups, (b) an organohydrogen polysiloxane compound having at least two Si-H groups, (c) A catalyst that enables the addition of hydrogen atoms bonded to silicon in the organic hydrogen polysiloxane compound to the unsaturated group of the organic hydrogen polysiloxane compound, (d) at least one surface-treated particulate filler, The surface-treated filler extends the storage stability of the dental impression material. A curable, one-component silicone composition. (2) The curable one-component silicone composition according to (1), wherein the organic polysiloxane compound having at least two unsaturated groups is selected from the group consisting of vinyl-terminated polydimethylsiloxane, trifunctional siloxane, tetrafunctional siloxane, and organic polysiloxane having a phenyl group. (3) The curable one-component silicone composition according to (2), wherein the organic polysiloxane compound having at least two unsaturated groups comprises a vinyl-terminated polydimethylsiloxane. (4) The curable one-component silicone composition according to (1), wherein the organic hydrogen polysiloxane compound having at least two Si-H groups is a hydrogen-functionalized polydimethylsiloxane (HPDMS). (5) The curable one-component silicone composition according to (4), wherein the amount of hydride in the HPDMS is about 3.5 mmol / g to about 4.9 mmol / g. (6) The curable one-component silicone composition according to (1), wherein the catalyst is selected from the group consisting of Pt(acac)2, platinum(II)bis(benzoylmethanate), platinum(II)bis(dibenzoylacetonate), and (Me-Cp)Pt(Me)3. (7) The curable one-component silicone composition according to (6), wherein the catalyst is Pt(acac)2. (8) The curable one-component silicone composition according to (1), wherein the at least one surface-treated microparticle filler is selected from the group consisting of inorganic microparticle fillers, submicron silica or oxides, and inorganic fillers. (9) The curable one-component silicone composition according to (8), wherein the inorganic fine particles are selected from the group consisting of dental glass, fused silica, quartz, crystalline silica, amorphous silica, soda glass beads, glass rods, ceramic oxides, fine particle silicate glass, and radiopaque glass. (10) The curable one-component silicone composition according to (8), wherein the submicron silica or oxide is selected from the group consisting of fumed silica, precipitated silica, and aluminosilicate. (11) The curable one-component silicone composition according to (10), wherein the aluminosilicate is selected from the group consisting of calcium aluminosilicate, strontium aluminosilicate, and barium aluminosilicate. (12) The curable one-component silicone composition according to (8), wherein the inorganic filler is selected from the group consisting of YF3, La2O3, ZrO2, BiPO4, CaWO4, BaWO4, SrF2, and Bi2O3. (13) The curable one-component silicone composition according to (1), wherein the organic polysiloxane compound having at least two unsaturated groups is present in a concentration of 10% to 90% by weight based on the total weight of the silicone composition. (14) The curable one-component silicone composition according to (1), wherein the organic hydrogen polysiloxane compound having at least two Si-H groups is present in a concentration of 1% to 20% by weight based on the total weight of the silicone composition. (15) The curable one-component silicone composition according to (1), wherein the catalyst is added in an amount of about 20 to 500 ppm based on the total weight of the silicone composition. (16) The curable one-component silicone composition according to (1), wherein the surface-treated silica filler is present at a concentration of 10% to 80% by weight based on the total weight of the composition. (17) The surface-treated particulate filler is prepared by a process for preparing composite filler particles, and the process is (a) A coating composition comprising a film-forming agent that forms a coating layer on the surface of a particulate filler, comprising the step of coating a particulate filler having a median particle size (D50) of 100 to 1200 nm, wherein the coating layer exhibits reactive groups on the surface of the coating layer, and the reactive groups are selected from addition polymerizable groups and stepwise polymerizable groups that thereby form the coated particulate filler, and thereafter or simultaneously, (b) A step of granulating coated particulate fillers in the presence of a further crosslinking agent and further particulate fillers that do not exhibit reactive groups, in order to provide granules of coated particulate fillers, wherein the granules contain coated particulate filler particles and further particulate filler particles bound together via at least one coating layer, the at least one coating layer may be crosslinked by crosslinking groups obtained by the reaction of reactive groups and further crosslinking agents, thereby the granulation is carried out by spray granulation or growth granulation, (c) A step of milling, classifying, and sieving granules of coated particulate filler, (d) A step of further crosslinking the coated particulate filler granules, Includes, The prepared filler particles have a median particle size (D50) of 1 to 70 μm. The reactive group is converted into a crosslinking group obtained by the reaction of the reactive group with a further crosslinking agent. The aforementioned fine particle filler is the main component in volume of the composite filler particles, as described in (1) for the curable one-component silicone composition. (18) The one-component silicone composition according to (17), wherein the surface-treated fine particle filler has a median particle size of 1 to 50 μm. (19) The one-component silicone composition according to (17), wherein the surface-treated fine particle filler is a calcium aluminosilicate filler coated with a cross-linked acrylic resin. (20) A method for preparing a curable one-component silicone composition, (a) A step of mixing an organic polysiloxane compound having at least two unsaturated groups with an organic hydrogen polysiloxane compound having at least two Si-H groups and a catalyst in order to form an activated silicone resin composition, (b) Adding at least one surface-treated particulate filler to the activated silicone resin composition, Methods that include... (twenty one) (a) an organopolysiloxane compound having at least two unsaturated groups, (b) an organohydrogen polysiloxane compound having at least two Si-H groups, (c) A catalyst that enables the addition of hydrogen atoms bonded to silicon in the organic hydrogen polysiloxane compound to the unsaturated group of the organic hydrogen polysiloxane compound, (d) at least one surface-treated particulate filler, A hardened dental material obtained by hardening a composition containing [the specified substance]. (twenty two) The hardened dental material according to (21), wherein the dental material is a dental impression material, a soft relining material for dentures, a template material for provisional crowns and bridge restorations. (twenty three) The cured dental material according to (21), which has storage stability for 210 days at a temperature of 22°C to 27°C.

Claims

1. A curable one-component silicone composition for dental impression materials, (a) an organic polysiloxane compound having at least two unsaturated groups, (b) an organohydrogen polysiloxane compound having at least two Si-H groups, (c) A catalyst that enables the addition of hydrogen atoms bonded to silicon in the organic hydrogen polysiloxane compound to the unsaturated group of the organic hydrogen polysiloxane compound, (d) Coated calcium aluminosilicate filler, The curable one-component silicone composition contains, and has storage stability for at least 125 days at a temperature of 22°C to 27°C. A curable, one-component silicone composition.

2. The curable one-component silicone composition according to claim 1, wherein the organic polysiloxane compound having at least two unsaturated groups is selected from the group consisting of vinyl-terminated polydimethylsiloxane, trifunctional siloxane, quadrifunctional siloxane, and organic polysiloxane having a phenyl group.

3. The curable one-component silicone composition according to claim 2, wherein the organic polysiloxane compound having at least two unsaturated groups comprises a vinyl-terminated polydimethylsiloxane.

4. The curable one-component silicone composition according to claim 1, wherein the organic hydrogen polysiloxane compound having at least two Si-H groups is hydrogen-functionalized polydimethylsiloxane (HPDMS).

5. The curable one-component silicone composition according to claim 4, wherein the amount of hydride in the HPDMS is 3.5 mmol / g to 4.9 mmol / g.

6. The catalyst is Pt(acac) ２ Platinum(II) bis(benzoylmethanate), platinum(II) bis(dibenzoylacetonate), and (Me-Cp)Pt(Me) ３ A curable one-component silicone composition according to claim 1, selected from the group consisting of the following.

7. The catalyst is Pt(acac) ２ The curable one-component silicone composition according to claim 6.

8. The curable one-component silicone composition according to claim 1, wherein the organic polysiloxane compound having at least two unsaturated groups is present in a concentration of 10% to 90% by weight based on the total weight of the silicone composition.

9. The curable one-component silicone composition according to claim 1, wherein the organic hydrogen polysiloxane compound having at least two Si-H groups is present in a concentration of 1% to 20% by weight based on the total weight of the silicone composition.

10. The curable one-component silicone composition according to claim 1, wherein the catalyst is added in an amount of 20 to 500 ppm based on the total weight of the silicone composition.

11. The curable one-component silicone composition according to claim 1, wherein the surface-treated silica filler is present in a concentration of 10% to 80% by weight based on the total weight of the composition.

12. The one-component silicone composition according to claim 1, wherein the coated calcium aluminosilicate filler has a median particle size of 1 to 50 μm.

13. The one-component silicone composition according to claim 1, wherein the coated calcium aluminosilicate filler is a calcium aluminosilicate filler coated with a cross-linked acrylic resin.

14. A method for preparing a curable one-component silicone composition, (a) A step of mixing an organic polysiloxane compound having at least two unsaturated groups with an organic hydrogen polysiloxane compound having at least two Si-H groups and a catalyst in order to form an activated silicone resin composition, (b) Adding a calcium aluminosilicate filler coated to the activated silicone resin composition, The curable one-component silicone composition contains, and has storage stability for at least 125 days at a temperature of 22°C to 27°C. method.

15. (a) an organic polysiloxane compound having at least two unsaturated groups, (b) an organohydrogen polysiloxane compound having at least two Si-H groups, (c) A catalyst that enables the addition of hydrogen atoms bonded to silicon in the organic hydrogen polysiloxane compound to the unsaturated group of the organic hydrogen polysiloxane compound, (d) Coated calcium aluminosilicate filler, A cured dental material obtained by curing a composition containing, The composition is a dental material having storage stability for at least 125 days at a temperature of 22°C to 27°C.

16. The hardened dental material according to claim 15, wherein the dental material is a dental impression material, a soft relining material for dentures, a template material for provisional crowns and bridge restorations.

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