One-component dental adhesive composition

Abstract

To provide one-component dental adhesive compositions that can exhibit high adhesion to a wide range of visible-light-curing dental materials without pre-curing.SOLUTION: There is provided a one-component dental adhesive composition containing 0.5 to 5 pts.mass of an α-aminoacetophenone-type photoinitiator such as 2-benzyl-2-(dimethylamino)-4'-morpholinobtyrophenone to 100 pts.mass of a polymerizable monomer component containing acidic group-containing polymerizable monomer, and becoming curable by further containing 0.1 to 4 pts.mass of camphorquinone or by visible light irradiation by supplying camphorquinone from the outside (for example, a visible light-curable dental material containing camphorquinone, which is to be an adherend).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a one-component dental adhesive composition. [Background technology]

[0002] Composite resins, commonly used in dental treatment, are dental materials composed of a hardenable composition containing a polymerizable monomer, a polymerization initiator, and an optional filler. They are used to restore teeth by filling the cavity of a tooth after caries removal and then hardening. Composite resin cements, on the other hand, are hardenable compositions with the same composition as the composite resins. They are dental materials used to restore teeth by applying and pressing onto dental prosthetic restorative materials such as metals, ceramics, and polymeric materials. These dental materials (hereinafter sometimes abbreviated as "CRs, etc.") are classified according to the polymerization initiator used: chemical polymerization types using chemical polymerization initiators, photopolymerization types using photopolymerization initiators, and dual-cure types using both polymerization initiators. Light-curing and dual-cure types that can be cured by light irradiation (hereinafter also referred to as "light-curing CRs, etc.") are widely used. Since these CRs and the like have almost no adhesive properties to tooth structure by themselves, when performing treatment (tooth restoration), dental adhesives (also called bonding materials) must be applied to the tooth surface before filling or pressing the CR and the like into the tooth structure in order to firmly bond the hardened CR and the like to the tooth structure.

[0003] Such dental adhesives are generally known to be composed of a polymerizable monomer component containing a polymerizable monomer having a functional group, such as an acidic group, for improving adhesiveness, and a curable composition containing a polymerization initiator. Similar to CR and the like, they are classified according to the type of polymerization initiator, and are used appropriately based on the characteristics of each type (see Patent Documents 1 and 2). When a chemical polymerization initiator is used, light irradiation using a light irradiator is not required, but the two liquids must be stored separately and mixed before use. In contrast, when only a photopolymerization initiator is used, although light irradiation is required, the adhesive has the advantage of being able to be stored as a single liquid, eliminating the need for a mixing operation.

[0004] When using these conventional dental adhesives, it is common to apply them to the surface of the tooth to be treated (restored), then polymerize and harden them to form a pre-adhesive layer before filling with CR or other materials. However, hardening before filling with CR or other materials (hereinafter also referred to as "pre-hardening") not only requires the necessary polymerization procedures and time, but also places a certain burden on the patient due to the heat generated by polymerization. Furthermore, there is a risk that the surface of the adhesive layer may become contaminated with saliva or blood during the procedure, making it impossible to achieve the desired adhesive strength. For this reason, dental adhesives that do not require pre-hardening have also been developed.

[0005] For example, Patent Document 3 describes a one-component dental adhesive that not only has the above-mentioned feature of not requiring pre-curing but also does not require a mixing operation at the time of application, and describes a one-component dental adhesive composition for adhering a photocurable filling material containing an aromatic amine to a tooth structure, the dental adhesive composition comprising 100 parts by mass of (A) a polymerizable monomer including 1 part by mass to 40 parts by mass of (a1) an acidic group-containing polymerizable monomer, 0.05 parts by mass to 2 parts by mass of (B) a divalent copper compound, and 0.05 parts by mass to 2 parts by mass of (C) a divalent copper compound. The document discloses a "dental adhesive composition that contains (C) a peroxide containing at least one of (c1) an organic peroxide in an amount of 0.1 part by mass to 10 parts by mass and (c2) an inorganic peroxide in an amount of 0.01 part by mass to 5 parts by mass, (D) a photopolymerization initiator containing 0.1 part by mass to 10 parts by mass of (d1) a bisacylphosphine oxide, 1 part by mass to 50 parts by mass of (E) water, and 10 parts by mass to 300 parts by mass of (F) an organic solvent, and that does not contain a reducing agent." [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Laid-Open No. 2009-137960 [Patent Document 2] Japanese Patent Application Publication No. 2018-027913 [Patent Document 3] Japanese Patent Publication No. 2020-138911 [Patent Document 4] Japanese Patent Application Laid-Open No. 2005-89729 [Patent Document 5] Patent No. 6250245 [Patent Document 6] International Publication No. 2020 / 050123 Brochure [Non-patent literature]

[0007] [Non-Patent Document 1] Bunichiro Yamada, "Chemistry of Dental Organic Materials: Basic Knowledge and Applications," 1st Edition, Yamamoto Precious Metals Co., Ltd., July 5, 2016, p. 72 Summary of the Invention [Problem to be solved by the invention]

[0008] The dental adhesive composition disclosed in Patent Document 3 has a one-component structure, but exhibits the excellent effect of forming an adhesive layer with high adhesive strength by applying CR or the like and curing the composition simultaneously with the curing of the CR or the like without post-application curing. However, to achieve this effect, it is necessary to use a photocurable dental filling material (photocurable CR or the like) containing an aromatic amine as the dental filling material (CR or the like). That is, the dental adhesive composition is cured by irradiating the photopolymerization initiator (D) contained therein with light irradiated when curing the CR or the like. However, since the intensity of the light reaching the adhesive is reduced by transmission through the layer of CR or the like, photocuring alone is insufficient. Therefore, to form an adhesive layer with sufficient curing strength, it is necessary to form a highly active chemical polymerization initiator using the divalent copper compound (B) and peroxide (C) contained in the dental adhesive composition and the aromatic amine supplied from the dental filling material, and to make this initiator function.

[0009] Because ultraviolet light is harmful to the human body, typical photocurable CRs are visible light-curable, capable of being cured by irradiation with light (470 nm) from a typical dental light irradiator, and many of these contain an amine compound as a reducing agent. However, aliphatic amines are sometimes used as the amine compound (see Patent Document 4). When the dental adhesive composition is applied to photocurable CRs that use only aliphatic amines, the highly active chemical polymerization initiator is not formed, and the desired effect cannot be achieved. Furthermore, even when the dental adhesive composition is applied to photocurable CRs that contain aromatic amines as reducing agents, the type and amount of aromatic amines contained vary, raising concerns that sufficient effects may not be achieved.

[0010] Therefore, an object of the present invention is to provide a one-component dental adhesive composition that, when used with a visible light-curable CR or the like, can be filled with a visible light-curable CR or the like and cured simultaneously with the visible light-curable CR or the like without pre-curing, regardless of whether the visible light-curable CR or the like contains an amine compound, or even if it contains an amine compound, regardless of the type or amount of the amine compound, and can form an adhesive layer with high strength through the curing at that time. [Means for solving the problem]

[0011] The present invention solves the above-mentioned problems, and a first aspect of the present invention is A dental adhesive comprising a hardenable composition that is applied to a tooth surface before applying a photocurable dental material, in order to bond a tooth to a cured product of the photocurable dental material, the photocurable composition comprising a polymerizable monomer and a photopolymerization initiator and that is hardened by visible light irradiation. The dental adhesive is a one-component dental adhesive composition that is used as a dental adhesive that is hardened by visible light irradiation that is performed to harden the photocurable dental material after application, without being hardened before application of the photocurable dental material, and that achieves the bonding. The one-component dental adhesive composition is: a polymerizable monomer component containing an acidic group-containing polymerizable monomer: 100 parts by mass; an α-aminoacetophenone-type photopolymerization initiator: 0.5 to 5 parts by mass; and further comprising camphorquinone: 0.1 to 4 parts by mass; or When the photocurable dental material contains a photopolymerization initiator containing camphorquinone, the photocurable dental material Camphorquinone is supplied from The aforementioned The one-component dental adhesive composition is characterized by being curable by irradiation with visible light.

[0012] The one-component dental adhesive composition of the above form (hereinafter also referred to as "the one-component dental adhesive composition of the present invention" or "the adhesive composition of the present invention") preferably contains 0.1 to 4 parts by mass of camphorquinone. Furthermore, the one-component dental adhesive composition of the present invention may contain only an α-aminoacetophenone-type photopolymerization initiator as the photopolymerization initiator, or may contain a photopolymerization initiator consisting of only an α-aminoacetophenone-type photopolymerization initiator and camphorquinone.

[0013] Book The one-component dental adhesive composition of the present invention contains a polymerizable monomer and a photopolymerization initiator containing camphorquinone, The aforementioned A one-component dental adhesive composition for a photocurable dental material, which is made of a photocurable composition that is cured by irradiation with visible light, and which contains camphorquinone. Contains and camphorquinone is supplied from the light-curing dental material, The aforementioned Also included is a one-component dental adhesive composition that can be cured by irradiation with visible light.

[0014] In the one-component dental adhesive composition of the present invention, the α-aminoacetophenone-type photopolymerization initiator is a compound represented by the following general formula (1):

[0015] [ka]

[0016] (In the formula, Ph represents a phenyl group, and R 1 , R 2 , R 3 and R 4 each independently represents a monovalent organic group or a hydrogen atom. and the α-aminoacetophenone type photopolymerization initiator is preferably a compound that undergoes a triplet energy transfer photosensitization reaction and has a triplet excitation energy of 62 kcal / mol or less.

[0017] Furthermore, it is preferable that the composition further contains 1 to 5 parts by mass of a tertiary amine (excluding α-aminoacetophenone type photopolymerization initiators), and it is also preferable that the composition further contains 20 to 450 parts by mass of a solvent component consisting of water and / or an organic solvent.

[0018] A second aspect of the present invention is a photocurable dental material comprising a photocurable composition that contains a polymerizable monomer and a photopolymerization initiator and is cured by irradiation with visible light; The one-component type of the present invention and a dental adhesive composition, wherein the photocurable dental material is a dental restoration kit comprising a combination of a photocurable dental material and a dental adhesive composition, and the photocurable dental material is a dental restoration kit comprising a dental adhesive composition and a dental adhesive composition, the photocurable dental material being a dental restoration kit comprising a dental restoration kit and a dental adhesive composition, the photocurable dental material being a dental restoration kit comprising a dental restoration kit and a dental adhesive composition, the photocurable dental material being a dental restoration kit and a dental adhesive composition, ) A light-curing dental material having a contrast ratio defined as the ratio of Yb / Yw of 0.45 or less, The one-component dental adhesive composition is a dental adhesive comprising a curable composition that is applied to the tooth surface before applying a light-curable dental material in order to bond a tooth to a cured product of the light-curable dental material, the photocurable composition comprising a polymerizable monomer and a photopolymerization initiator and cured by visible light irradiation, and the dental restoration kit is used for dental restoration by curing and bonding the one-component dental adhesive composition by visible light irradiation that is performed to harden the light-curable dental material after application, without hardening the one-component dental adhesive composition before application of the light-curable dental material. The dental repair kit (hereinafter also referred to as "the kit of the present invention") is characterized by the following:

[0019] In addition, the one-component dental adhesive composition of the present invention Contains α-aminoacetophenone type photopolymerization initiator and camphorquinone Possible Visible light radical polymerization initiator of Hereinafter, this will also be referred to as the "visible light radical polymerization initiator of the present invention." 。 [Effects of the Invention]

[0020] The visible light-type radical polymerization initiator of the present invention can sufficiently cure a radically polymerizable monomer even by irradiation with low-intensity visible light (e.g., light in the wavelength range of 400 to 500 nm). Furthermore, the one-component dental adhesive composition of the present invention contains the visible light-type radical polymerization initiator of the present invention, or can form the visible light-type radical polymerization initiator of the present invention by utilizing camphorquinone supplied from the adhesive target, such as a visible light-curable CR, which cures upon irradiation with visible light during use. Therefore, the visible light-curable CR or the like (or its cured product) can be bonded to tooth structure with high adhesive strength even without pre-curing. This reduces the burden on the patient and prevents a decrease in adhesive strength due to the adhesion of saliva, blood, etc. to the adhesive layer.

[0021] Furthermore, since the above-mentioned effects are not affected by components such as amine compounds contained in visible light-curable CRs, the one-component dental adhesive composition of the present invention can be applied to a very wide range of visible light-curable CRs. DETAILED DESCRIPTION OF THE INVENTION

[0022] 1. Overview of the visible light radical polymerization initiator of the present invention and the one-component dental adhesive composition of the present invention The visible light-curable CRs and the like to which the one-component dental adhesive composition described in Patent Document 3 is applicable must contain an aromatic amine, thereby narrowing the range of applicable visible light-curable CRs and the like. The aromatic amine is essential because it, together with the components contained in the dental adhesive composition, constitutes a specific chemical polymerization initiator. Therefore, the present inventors believed that the visible light-curable CRs and the like to which the composition is applicable would not be limited if they could be sufficiently cured by the action of a photopolymerization initiator alone, without relying on the action of a chemical polymerization initiator. They therefore investigated photopolymerization initiators that provide sufficient cure strength even with (low-intensity) transmitted light. As a result, they found that although α-aminoacetophenone-type photopolymerization initiators are not activated by visible light alone, when coexisting with camphorquinone, they can exhibit high polymerization activity even with low-intensity visible light irradiation.

[0023] The present inventors then came to the conclusion that (1) if an α-aminoacetophenone-type photopolymerization initiator having the above-mentioned properties and a visible light-type radical polymerization initiator containing camphorquinone (the visible light-type radical polymerization initiator of the present invention) are used as a photopolymerization initiator for a one-component dental adhesive composition, the composition can be cured simultaneously with the curing of any visible light-curable CR, etc., without the need for pre-curing, thereby forming a high-strength adhesive layer, and (2) that if camphorquinone is contained in the photocurable dental material to be adhered, this camphorquinone can also be used, and have completed the present invention.

[0024] α-Aminoacetophenone-type photopolymerization initiators have an absorption wavelength range of 300 to 430 nm in the ultraviolet region and are therefore used in UV offset inks and liquid resists. However, they do not undergo photoreaction with the light (470 nm) of a typical dental light irradiator (requiring ultraviolet light irradiation, which is harmful to the human body), and therefore are not generally used in photocurable materials that are applied directly to the human body in dental treatment. Camphorquinone is also widely used as a component of photopolymerization initiators for photocurable CRs and the like (see Non-Patent Document 1), and even when camphorquinone contained in the photocurable dental material (2) is used, the range of applicable visible light-curable CRs and the like is quite wide.

[0025] While the present invention is not bound by any theory, it is presumed that the reason for the above-mentioned effects is as follows. Specifically, the reason why the visible light-type radical polymerization initiator of the present invention, in which an α-aminoacetophenone-type photopolymerization initiator coexists with camphorquinone, can exhibit high polymerization activity even when irradiated with low-intensity visible light is presumed to be due to the interaction of one camphorquinone molecule with multiple molecules of the α-aminoacetophenone-type photopolymerization initiator, generating initiating radicals. For example, in the case of (2) above, if an adhesive composition of the present invention not containing camphorquinone is applied to the inner surface of a cavity formed in a tooth, and then a photocurable CR or the like is filled in (without curing), and curing is performed by irradiating visible light, the camphorquinone contained in the photocurable CR or the like, including a portion that has migrated into the adhesive composition of the present invention, absorbs visible light and becomes excited. The α-aminoacetophenone-type photopolymerization initiator contained in the adhesive composition then decomposes due to interaction with excited camphorquinone present in the vicinity of or inside the adhesive composition, generating initiating radicals, which then progresses curing. On the other hand, camphorquinone returns to the ground state and repeats the above cycle, which is presumably why high polymerization activity was obtained even with low-intensity visible light irradiation.

[0026] Thus, even if the adhesive composition of the present invention does not specifically contain camphorquinone, it is believed that the α-aminoacetophenone-type photopolymerization initiator is activated by a small amount of camphorquinone or excited camphorquinone supplied from a photocurable CR or the like, and functions effectively as a radical polymerization initiator (enabling the generation of radicals necessary for polymerization curing), thereby obtaining high adhesive strength. In principle, the combination of camphorquinone and a tertiary amine generates one initiating radical molecule from one camphorquinone molecule, so sufficient curing cannot be obtained even if this combination is used in an adhesive composition without using an α-aminoacetophenone-type photopolymerization initiator.

[0027] The visible light radical polymerization initiator of the present invention preferably contains 0.04 to 1.6 parts by mass, particularly 0.08 to 0.8 parts by mass, of camphorquinone per 1 part by mass of the α-aminoacetophenone photopolymerization initiator. Furthermore, it preferably contains 0.4 to 2 parts by mass, particularly 0.8 to 1.6 parts by mass, of a tertiary amine (other than the α-aminoacetophenone photopolymerization initiator) described below, based on the above criteria.

[0028] The following provides a detailed description of the photocurable CRs and the like (hereinafter also referred to as "target photocurable CRs and the like") for which the one-component dental adhesive composition of the present invention is used, and the one-component dental adhesive composition of the present invention. In this specification, unless otherwise specified, the expression "x to y" using numerical values ​​x and y means "x or more and y or less." In such an expression, when a unit is assigned only to the numerical value y, the unit also applies to the numerical value x. Furthermore, in this specification, the term "(meth)acrylic" means both "acrylic" and "methacrylic." Similarly, the term "(meth)acrylate" means both "acrylate" and "methacrylate," and the term "(meth)acryloyl" means both "acryloyl" and "methacryloyl."

[0029] 2. Targeted light-curing CR etc. and kit of the present invention As described above, the photocurable CR, etc. for which the one-component dental adhesive composition of the present invention is used (target photocurable CR, etc.) varies slightly depending on whether the one-component dental adhesive composition of the present invention contains camphorquinone. If the one-component dental adhesive composition contains camphorquinone, there are no particular restrictions. However, if the one-component dental adhesive composition does not (substantially) contain camphorquinone, the photocurable CR, etc. contains camphorquinone.

[0030] The photocurable CRs and the like are not particularly limited to those made of photocurable compositions containing a polymerizable monomer and a photopolymerization initiator; those used in conventional photocurable CRs and the like can be used without limitation. As the polymerizable monomer, for example, those suitable for use as "(a2) acidic group-free polymerizable monomer" in the adhesive composition of the present invention described below can be suitably used. Furthermore, photopolymerization initiators suitable for use in photocurable CRs and the like, particularly visible light-curable CRs, can be used without limitation, but a combination of camphorquinone and a tertiary amine is preferred. As the tertiary amine, those suitable for use as "(C) tertiary amine" in the adhesive composition of the present invention described below can be suitably used. The contents of camphorquinone (CQ) and tertiary amine are typically 0.2 to 2 parts by mass of CQ and 0.01 to 10 parts by mass of tertiary amine per 100 parts by mass of polymerizable monomer, and preferably 0.2 to 0.5 parts by mass of CQ and 0.02 to 10 parts by mass of tertiary amine.

[0031] In order to enhance polishability and mechanical strength, the target light-curing dental filling material preferably contains 50 to 1500 parts by mass, particularly 70 to 1000 parts by mass, of an inorganic filler such as silica, zirconia, or silica-zirconia (which may be treated with a surface treatment agent such as a silane coupling agent) per 100 parts by mass of the polymerizable monomer.

[0032] Furthermore, additives such as a chemical polymerization initiator, a polymerization inhibitor, an ultraviolet absorber, and a pigment may be appropriately contained.

[0033] Ordinary light-curing CRs and the like have a certain degree of translucency so that they can be cured to the inside by irradiation with light (visible light, which serves as activating light). Therefore, the light during the irradiation reaches the one-component dental adhesive composition of the present invention that has been applied in advance, and cures it to form a film, thereby eliminating the need for pre-curing. From the viewpoint of reliably obtaining a desired adhesive strength without the need for pre-curing even for light-curing CRs and the like in relatively deep cavities during treatment, the one-component dental adhesive composition of the present invention is preferably used as a dental restoration kit (the kit of the present invention) in combination with a light-curing dental material (such as a target light-curing CR) having a contrast ratio Yb / Yw of 0.45 or less, which is defined as the ratio of the Y stimulus value on a black background: Yb (black background) to the Y stimulus value on a white background: Yw (white background), as measured by a color-difference meter using a 1 mm-thick cured sample against black and white backgrounds. When used in such a kit, sufficient adhesive strength can be obtained without the need for pre-curing even if the light-curing dental material (such as a target light-curing CR) has a thickness of, for example, 2.0 mm. From the viewpoint of such effects, it is preferable to use the one-component dental adhesive composition in a dental restoration kit in combination with a light-curing dental material (such as a target light-curing CR) having a Yb / Yw ratio of 0.40 or less. The lower limit of Yb / Yw is not particularly limited, but is usually 0.25 or more, preferably 0.3 or more.

[0034] The contrast ratio Yb / Yw is an index of the transparency of the cured product, and the lower the contrast ratio, the higher the transparency. The contrast ratio (transparency) of CR before curing does not necessarily match the contrast ratio of the cured product, and may be slightly lower or higher depending on the composition. However, since light is also irradiated onto the cured product (after curing) during curing of photocurable CR, if the contrast ratio of the cured product is within the above range, sufficient adhesive strength can be obtained without the need for pre-curing.

[0035] The light-curing dental material (target light-curing CR, etc.) used in the kit of the present invention is not particularly limited as long as it satisfies the above-mentioned conditions. However, it is preferable to use a light-curing CR, etc. (hereinafter also referred to as a "structural color CR"), which uses a structural color that develops color through the interference of light, etc., as described in Patent Documents 5 or 6, for the reasons that it contains a small amount of coloring agents such as pigments that reduce transparency (increase the contrast ratio: Yb / Yw), and has high color harmony with teeth, thereby omitting color matching with coloring agents and allowing for restoration with high color harmony (or high aesthetics) for natural teeth that have a variety of colors.

[0036] Here, the structural color CR refers to a CR or the like made of a curable composition that contains (1) a polymerizable monomer, (2) inorganic particles comprising one or more “spherical particle groups of the same size” (G-PID) consisting of a group of spherical particles having a predetermined average primary particle diameter in the range of 100 to 1000 nm, where the individual particles constituting the spherical particle group are substantially made of the same material and 90% (in number) or more of the individual particles are present within a range of 5% around the average primary particle diameter, and (3) a photopolymerization initiator, where the refractive index of the spherical particles constituting the G-PID to the sodium D line at 25°C is higher than the refractive index of the cured product of the polymerizable monomer, and the cured product of the curable composition exhibits a structural color of a constant tone regardless of changes in the angle of incidence of light.

[0037] 3. Components of the one-component dental adhesive composition of the present invention 3-1. (A) Polymerizable monomer component The polymerizable monomer (A) component is a compound having at least one radically polymerizable unsaturated group in one molecule. The adhesive composition of the present invention is cured by radical polymerization of the monomer (A). The monomer (A) contains at least an acidic group-containing polymerizable monomer (acid monomer) (a1).

[0038] 3-1-1. (a1) Acidic group-containing polymerizable monomer (acid monomer) (a1) Acidic Group-Containing Polymerizable Monomer (Acid Monomer) refers to a polymerizable monomer containing at least one acidic group in addition to at least one radically polymerizable unsaturated group per molecule. (a1) Acid Monomer primarily improves adhesion to tooth tissue (dentin, enamel), base metals (iron, nickel, chromium, cobalt, tin, aluminum, copper, titanium, etc., or alloys containing these as primary components), and metal oxides containing oxygen as primary components of metals such as zirconium (zirconia ceramics, alumina, titania, etc.). (a1) Acid Monomer also has the effect of demineralizing tooth tissue and improving permeability into tooth tissue, thereby improving adhesion of filling and restorative materials to tooth tissue.

[0039] The acid monomer (a1) used in the present invention is not particularly different from the acid monomer used in conventional dental adhesives, and has a radical polymerizable unsaturated group such as an acryloyl group, a methacryloyl group, an acrylamide group, a methacrylamide group, or a styryl group, and an acidic group such as a phosphono group {-P(=O)(OH)}, a carboxyl group {-C(=O)OH}, a dihydrogen phosphate monoester group {-OP(=O)(OH)}, a hydrogen phosphate diester group {(-O-)P(=O)OH}, a sulfo group (-SOH), and an acid anhydride skeleton {-C(=O)-OC(=O)-}, and is not particularly limited. Among these, from the viewpoint of adhesion to CR, etc., the polymerizable unsaturated group is preferably an acryloyl group and / or a methacryloyl group. Furthermore, polymerizable monomers having at least one group selected from a carboxyl group, a dihydrogen phosphate monoester group, and a hydrogen phosphate diester group are preferred, as they have high stability against water and can slowly dissolve the smear layer on the tooth surface and demineralize the teeth, and polymerizable monomers having at least one group selected from a dihydrogen phosphate monoester group or a hydrogen phosphate diester group are most preferred.

[0040] Examples of suitable (a1) acid monomers include the following: those having a carboxyl group include acrylic acid, methacrylic acid, 4-(meth)acryloxyethyltrimellitic acid, 11-(meth)acryloyloxy-1,1-undecanedicarboxylic acid, 1,4-di(meth)acryloyloxypyromellitic acid, 2-(meth)acryloyloxyethylmaleic acid, 2-(meth)acryloyloxyethylphthalic acid, and 2-(meth)acryloyloxyethylhexahydrophthalic acid; and those having a sulfo group include 2-methacrylamido-2-methylpropanesulfonic acid, 2-acrylamido-2-methylpropanesulfonic acid, p-vinylbenzenesulfonic acid, and vinylsulfonic acid. Furthermore, examples of compounds having a dihydrogen phosphate monoester group or a hydrogen phosphate diester group include 2-(meth)acryloyloxyethyl dihydrogen phosphate, bis[2-(meth)acryloyloxyethyl]hydrogen phosphate, 2-(meth)acryloyloxyethylphenyl hydrogen phosphate, 6-(meth)acryloyloxyhexyl dihydrogen phosphate, 6-(meth)acryloyloxyhexylphenyl hydrogen phosphate, 10-(meth)acryloyloxydecyl dihydrogen phosphate, 1,3-di(meth)acryloylpropane-2-dihydrogen phosphate, 1,3-di(meth)acryloylpropane-2-phenyl hydrogen phosphate, and bis[5-{2-(meth)acryloyloxyethoxycarbonyl}heptyl]hydrogen phosphate.

[0041] These acidic group-containing polymerizable monomers may be used alone or in combination of two or more.

[0042] The amount of the (a1) acid monomer in the target adhesive composition is preferably 3 to 30 parts by mass, and more preferably 5 to 20 parts by mass, when the total mass of the (A) monomer component, i.e., the total mass of the (a1) acid monomer and the (a2) non-acid monomer described below, is taken as 100 parts by mass.

[0043] 3-1-2.(a2) Polymerizable monomers not containing acidic groups (non-acid monomers) (a2) The acidic group-free polymerizable monomer (non-acid monomer) can be any known compound without any particular limitation, as long as it does not contain an acidic group and contains one or more radically polymerizable unsaturated groups in one molecule. The radically polymerizable unsaturated groups are preferably acryloyl and / or methacryloyl groups, as in the acid monomer.

[0044] Examples of (a2) non-acid monomers that can be suitably used include the following: Monofunctional polymerizable monomers include methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, glycidyl (meth)acrylate, 2-cyanomethyl (meth)acrylate, benzyl methacrylate, polyethylene glycol mono(meth)acrylate, allyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, and glyceryl mono(meth)acrylate. Furthermore, examples of polyfunctional polymerizable monomers include 2,2'-bis{4-[2-hydroxy-3-(meth)acryloyloxypropoxy]phenyl}propane, triethylene glycol methacrylate, 2,2-bis[(4-(meth)acryloyloxypolyethoxyphenyl)propane], 1,6-bis(methacrylethyloxycarbonylamino)-2,2,4-trimethylhexane, 1,6-bis(methacrylethyloxycarbonylamino)-2,4,4-trimethylhexane, and trimethylolpropane trimethacrylate.

[0045] The non-acid monomer (a2) may be used alone or in combination of two or more.

[0046] The blending ratio of the (a2) non-acid monomer is the remainder obtained by subtracting the content of the (a1) acid monomer from the mass of the (A) monomer component. In other words, the content of the (a2) non-acid monomer per 100 parts by mass of the (A) monomer component is preferably 70 parts by mass to 97 parts by mass, and more preferably 80 parts by mass to 95 parts by mass.

[0047] 3-2.(B) α-aminoacetophenone type photopolymerization initiator In order to eliminate the need for light irradiation before filling with CR or the like, the adhesive composition of the present invention contains (B) an α-aminoacetophenone-type photopolymerization initiator as a component that interacts with camphorquinone in CR or the like.

[0048] (B) The α-aminoacetophenone type photopolymerization initiator means a compound represented by the following general formula (1), which generates radicals through a cleavage reaction upon irradiation with light.

[0049] [ka]

[0050] In the above general formula (1), Ph represents a phenyl group, and R 1 , R 2 , R 3 and R 4 each independently represents a monovalent organic group or a hydrogen atom. The monovalent organic group is preferably a methyl group, an ethyl group, or a benzyl group.

[0051] The α-aminoacetophenone photopolymerization initiator is preferably a compound that satisfies the above conditions and undergoes a triplet energy transfer photosensitization reaction, and more preferably a compound with a triplet excitation energy of 62 kcal / mol or less due to its high polymerization activity. Suitable compounds include 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone (manufactured by BASF Japan, trade name IRGACURE 369: triplet excitation energy 60 kcal / mol), 2-(4-methylbenzyl)-2-(dimethylamino)-4'-morpholinobutyrophenone (manufactured by BASF Japan, trade name IRGACURE 379: triplet excitation energy 60 kcal / mol), and 2-methyl-4'-(methylthio)-2-morpholinopropiophenone (manufactured by BASF Japan, trade name IRGACURE 907: triplet excitation energy 61 kcal / mol).

[0052] The amount of the (B) α-aminoacetophenone type photopolymerization initiator in the target adhesive composition is 0.5 to 5 parts by mass, preferably 1 to 4 parts by mass, when the total mass of the (A) monomers, i.e., the total mass of the (a1) acid monomers and the (a2) non-acid monomers, is taken as 100 parts by mass.

[0053] 3-3. (C) Other photopolymerization initiator components The one-component dental adhesive composition of the present invention may contain, as a photopolymerization initiator component, (C) other photopolymerization initiator components other than (B) the α-aminoacetophenone-type photopolymerization initiator. Here, the photopolymerization initiator component refers to a compound that becomes excited upon light irradiation and generates radicals through a hydrogen abstraction reaction or a cleavage reaction, or a compound that promotes the generation of such radicals. As the photopolymerization initiator, any known photopolymerization initiator can be used without limitation, and examples that can be used include α-diketones such as camphorquinone, acylphosphine oxides, and thioxanthones.

[0054] Among these, it is preferable to contain (c1) camphorquinone so that the one-component dental adhesive composition of the present invention contains the visible light radical polymerization initiator of the present invention, from the viewpoint of broadening the range of applicable light-curable CRs, etc. The content of camphorquinone is usually 0.1 to 4 parts by mass, preferably 0.2 to 2 parts by mass, per 100 parts by mass of the total mass of the (A) monomer.

[0055] Furthermore, for the purpose of improving adhesiveness, it is preferable to include (c2) a tertiary amine as another photopolymerization initiator component. (c2) A tertiary amine not only increases polymerization activity as a hydrogen donor but also improves adhesiveness by reducing polymerization inhibition caused by oxygen.

[0056] Such a tertiary amine (c2) is not particularly limited as long as it is a tertiary amine other than an α-aminoacetophenone-type photopolymerization initiator, and any known compound such as an aromatic tertiary amine having an aromatic ring in the molecule or an aliphatic tertiary amine having no aromatic ring in the molecule can be used without limitation.

[0057] Examples of aromatic tertiary amines that can be suitably used include the following: methyl p-dimethylaminobenzoate, ethyl p-dimethylaminobenzoate, propyl p-dimethylaminobenzoate, amyl p-dimethylaminobenzoate, isoamyl p-dimethylaminobenzoate, ethyl p-diethylaminobenzoate, and propyl p-diethylaminobenzoate.

[0058] Examples of aliphatic tertiary amines that can be suitably used include the following: triethanolamine, N-methyldiethanolamine, triethylamine, tributylamine, N,N-dimethylaminoethyl methacrylate, and N,N-diethylaminoethyl methacrylate.

[0059] The above-mentioned (c1) aromatic tertiary amine and (c2) aliphatic tertiary amine can each be used alone or in combination of two or more kinds.

[0060] In particular, in the present invention, aliphatic tertiary amines are preferred from the viewpoint of adhesiveness, and N,N-dimethylaminoethyl methacrylate containing a radically polymerizable unsaturated group is most preferred.

[0061] The amount of the tertiary amine (c2) in the target adhesive composition is preferably 1 to 5 parts by mass, more preferably 2 to 4 parts by mass, per 100 parts by mass of the total mass of the monomers (A).

[0062] 3-4.(D) Solvent Components From the viewpoint of ease of handling and storage stability, the adhesive composition of the present invention preferably contains a solvent component (D) consisting of water and / or an organic solvent.

[0063] (D) The water, which is a solvent component, is preferably substantially free of harmful impurities from the viewpoints of storage stability, biocompatibility, and adhesiveness, and examples thereof include deionized water and distilled water.

[0064] Examples of organic solvents that can be used include alcohols such as methanol, ethanol, isopropyl alcohol, butanol, and isobutyl alcohol; ketones such as acetone and methyl ethyl ketone; ethers such as ethyl ether, 1,4-dioxane, and tetrahydrofuran; esters such as ethyl acetate and ethyl formate; aromatic solvents such as toluene, xylene, and benzene; hydrocarbon solvents such as pentane, hexane, heptane, and octane; chlorine-based solvents such as methylene chloride, chloroform, and 1,2-dichloroethane; and fluorine-based solvents such as trifluoroethanol. Among these, ketones and alcohols are preferred from the viewpoints of solubility and storage stability, and acetone, methyl ethyl ketone, ethanol, isopropyl alcohol, and tertiary butyl alcohol are particularly preferred.

[0065] Furthermore, the blending amount of the (D) solvent component in the target adhesive composition is preferably 20 to 450 parts by mass, and more preferably 40 to 200 parts by mass, per 100 parts by mass of the total mass of the (A) monomers.

[0066] 3-5.Other ingredients The one-component dental adhesive composition of the present invention may contain various additives other than the above-mentioned components, as needed, such as fillers and polymerization inhibitors.

[0067] The filler is blended to improve the mechanical strength and operability of the adhesive layer obtained by curing the dental adhesive composition. There are no particular limitations on the filler, and known inorganic fillers, organic fillers, and inorganic-organic composite fillers can be used.

[0068] Examples of the polymerization inhibitor include hydroquinone, hydroquinone monomethyl ether, and dibutylhydroxytoluene.

[0069] Furthermore, some of the components of a chemical polymerization initiator consisting of a combination of multiple compounds may be included to the extent that they do not function as a chemical polymerization initiator (to the extent that they can be stored as a single liquid). For example, the dental adhesive composition described in Patent Document 3 may contain the divalent copper compound (B) and peroxide (C), which are included in the dental adhesive composition described in Patent Document 3. In this case, when a target photocurable CR or the like containing an aromatic amine is used, a highly active chemical polymerization initiator is formed, similar to the dental adhesive composition described in Patent Document 3, and curability can be further improved. [Example]

[0070] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples.

[0071] 1. Raw materials First, the substances used as raw materials in the Examples, Comparative Examples, and Reference Examples and their abbreviations are shown below.

[0072] 1-1.(A) Polymerizable monomers (a1) Acidic group-containing polymerizable monomer (acid monomer) MDP: 10-methacryloxydecyl dihydrogen phosphate · SPM: A mixture of mono(2-methacryloxyethyl) acid phosphate and bis(2-methacryloxyethyl) acid phosphate.

[0073] (a2) Polymerizable monomers not containing acidic groups (non-acid monomers) BisGMA: 2,2'-bis[4-(2-hydroxy-3-methacryloxypropoxy)phenyl]propane 3G: Triethylene glycol dimethacrylate HEMA: 2-hydroxyethyl methacrylate UDMA: 2,2,4-trimethylhexamethylenebis(2-carbamoyloxyethyl)dimethacrylate D-2,6E: 2,2-bis(4-methacryloyloxypolyethoxyphenyl).

[0074] 1-2.(B) α-aminoacetophenone type photopolymerization initiator IC369: 2-benzyl-2-(dimethylamino)-4'-morpholinobutyrophenone (BASF Japan, IRGACURE369) IC379: 2-(4-methylbenzyl)-2-(dimethylamino)-4'-morpholinobutyrophenone (BASF Japan, IRGACURE379) IC907: 2-methyl-4'-(methylthio)-2-morpholinopropiophenone (BASF Japan, IRGACURE907).

[0075] 1-3. (c1) Photopolymerization initiators other than α-aminoacetophenone type CQ: Camphorquinone ·BTPO: Bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide.

[0076] 1-4.(c2) Tertiary amines DMEM: 2-(dimethylamino)ethyl methacrylate TEA: Triethanolamine ·DMBE: Ethyl 4-(dimethylamino)benzoate.

[0077] 1-5.(D) Solvent ·acetone ·ethanol IPA: Isopropanol ·water.

[0078] 2. Examples and Comparative Examples Example 1 (1) Preparation of one-component adhesive composition An adhesive composition was obtained by mixing 20 parts by mass of the acid monomer MDP, 33 parts by mass of non-acid monomers Bis-GMA and 22 parts by mass of 3G, 25 parts by mass of HEMA, 2.5 parts by mass of (B) IRGACURE369, an α-aminoacetophenone type photopolymerization initiator, 40 parts by mass of ethanol as a solvent, and 20 parts by mass of water.

[0079] (2) Target light-curing CR, etc. The adhesive strength to tooth structure was evaluated using the dental composite resin (CR), such as the light-cured CR, Estelite Universal Flow Shade CE (manufactured by Tokuyama Dental Co., Ltd., contrast ratio: Yb / Yw=0.39, hereinafter sometimes abbreviated as EUF(CE)). The contrast ratio was measured by placing the CR in a mold with a through-hole of 7 mm diameter x 1 mm, pressing polyester films on both sides, and then irradiating the CR with a visible light irradiator (for example, Eliper, manufactured by 3M, irradiation intensity 1200 mW / cm). 2 The Yb / Yw value was determined based on the Yb and Yw measured on a 1 mm thick cured sample obtained by irradiating both sides of the sample with light for 10 seconds each in a vacuum oven. The Yb / Yw value was determined based on the Yb and Yw measured on a black and white background using a color difference meter (Tokyo Denshoku Corporation, "TC-1800MKII")

[0080] (3) Evaluation of adhesive strength to tooth structure A bovine front tooth extracted within 24 hours after slaughter was polished with waterproof abrasive paper P600 under running water, and the dentin plane was scraped off so that it was parallel to the labial surface. Double-sided tape with a 3 mm diameter hole was then attached to the polished surface. Next, the adhesive composition was applied to the adhesive surface exposed through the hole in the double-sided tape, and the adhesive composition was dried with an air blow for 5 seconds.

[0081] A 0.5 mm thick paraffin wax with an 8 mm diameter hole was attached to the adhesive surface coated with the dental adhesive composition so that the hole in the paraffin wax and the hole in the double-sided tape were concentric, creating a simulated cavity with a depth of 0.5 mm. The simulated cavity was filled with the EUF(CE) and lightly pressed with a polyester film. After that, a visible light irradiator (Elipar, manufactured by 3M, irradiation intensity 1200 mW / cm) was used. 2 The adhesive was then photocured for 10 seconds using a SUS304 round bar (diameter 8 mm, height 18 mm) that had been polished in advance using resin cement (Bistite II, manufactured by Tokuyama Dental Co., Ltd.). Finally, the bar was immersed in water at 37°C for 24 hours to obtain a sample for measuring adhesive strength. The composite resin used (Estelite Universal Flow) is a photopolymerizable composition containing CQ.

[0082] The tensile adhesive strength (adhesion strength) of the prepared samples was measured using an autograph (crosshead speed 2 mm / min) manufactured by Shimadzu Corporation. The measured values ​​of four samples were averaged to obtain the measurement result, which was 12.0 MPa. A tensile strength of 10 MPa or more is considered to be good.

[0083] Examples 2 to 29 One-component dental adhesive compositions of the present invention were obtained and evaluated in the same manner as in Example 1, except that the compositions were changed as shown in Tables 1 and 2. The evaluation results are shown in Tables 1 and 2. In these tables, "↑" means "same as above."

[0084] [Table 1]

[0085] [Table 2]

[0086] Comparative Examples 1 to 4 A one-component dental adhesive composition of the present invention was obtained and evaluated in the same manner as in Example 1, except that the composition was changed as shown in Table 3. The evaluation results are shown in Table 3. In Table 3, "↑" means "same as above."

[0087] [Table 3]

[0088] As shown in Tables 1 and 2, in all cases of Examples 1 to 26, the results of the adhesion test were good.

[0089] On the other hand, as shown in Table 3, Comparative Example 1 did not contain (B) an α-aminoacetophenone-type photopolymerization initiator, and therefore had low adhesive strength. Comparative Example 2 did not contain an acid monomer that exhibits adhesiveness to tooth structure, and therefore had low adhesive strength. Furthermore, Comparative Examples 3 and 4, which used (B) a photopolymerization initiator other than an α-aminoacetophenone-type, did not provide good adhesion test results.

[0090] Example 30 (1) Preparation of samples for curability evaluation A sample for evaluating curability was obtained by mixing 20 parts by mass of MDP, an acid monomer, 33 parts by mass of Bis-GMA and 22 parts by mass of 3G, which are non-acid monomers, 25 parts by mass of HEMA, (B) 0.4 parts by mass of IRGACURE369, an α-aminoacetophenone type photopolymerization initiator, (C) 0.5 parts by mass of DMBE, which is a tertiary amine other than an α-aminoacetophenone type photopolymerization initiator, and 0.3 parts by mass of CQ.

[0091] (2) Evaluation of hardening properties of hardened body A polytetrafluoroethylene mold with a 6 mm diameter x 1.0 mm hole was filled with a sample for curing evaluation and pressed against a polypropylene film. A visible light irradiator (Eliper, 3M) was used to irradiate the polypropylene film with the irradiator in close contact with the film for the specified time to prepare a cured product. The Vickers hardness of the resulting cured product was measured using a Vickers indenter on a Matsuzawa Seiki MHT-1 microhardness tester, measuring the diagonal length of the indentation made in the test specimen under a load of 50 gf and a load hold time of 30 seconds. The results are shown in Table 4. The Vickers hardness obtained was 5.6 for a 5-second light exposure time and 6.7 for a 20-second light exposure time. To compare cured products with different monomer compositions, the immediate cure rate was defined as the ratio (%) of the Vickers hardness at 5 seconds to the Vickers hardness at 20 seconds of exposure. A higher immediate cure rate indicates a superior photopolymerization initiator, capable of curing even with short (weak) light exposure.

[0092] Comparative Examples 5 to 8 A sample for curability evaluation was obtained and evaluated in the same manner as in Example 30, except that the composition was changed as shown in Table 4. The evaluation results are shown in Table 4.

[0093] [Table 4]

[0094] As shown in Table 4, Example 30 contained (a1) an acid monomer, (B) an α-aminoacetophenone-type photopolymerization initiator, and CQ, which was added in anticipation of supply from dental materials, and therefore had a high degree of immediate curing and was judged to be an excellent photopolymerization initiator. On the other hand, as shown in Table 4, in Comparative Example 5, the composition did not contain (B) an α-aminoacetophenone type photopolymerization initiator, and therefore the instantaneous curing degree was low. In Comparative Example 6, since CQ was not contained, hardening did not proceed, and as a result, the Vickers hardness could not be measured. In Comparative Example 7, the acid monomer (a1) was not contained, and therefore the instantaneous curing degree was low. In Comparative Example 8, since (a1) the acid monomer and (B) the α-aminoacetophenone type photopolymerization initiator were not contained, the instantaneous curing degree was low. The Vickers hardness of Comparative Example 7 was lower than that of Comparative Example 8, suggesting that when (A) monomer not containing (a1) acid monomer is used, (B) α-aminoacetophenone type photopolymerization initiator inhibits polymerization.

[0095] Examples 31-32 The adhesive strength to tooth structure was evaluated in the same manner as in Example 1, except that the dental composite resin filled in the simulated cavity in Example 1 was changed to Esthelite Universal Flow Medium Shade A1 (manufactured by Tokuyama Dental Co., Ltd., contrast ratio 0.51) in Example 31 and to Esthelite Universal Flow Medium Shade A4 (manufactured by Tokuyama Dental Co., Ltd., contrast ratio 0.53) in Example 32. The adhesive strength in Example 31 was 11.5 MPa, and the adhesive strength in Example 32 was 11.3 MPa.

[0096] Examples 33 to 35 The thickness of the paraffin wax, which was originally 0.5 mm thick and had an 8 mm diameter hole, was changed to 2.0 mm, making the depth of the simulated cavity 2.0 mm, and the dental composite resin filled into the simulated cavity was changed to that shown in Table 5. Except for this, the adhesive strength to tooth structure was evaluated in the same manner as in Example 1. The results are shown in Table 5.

[0097] The abbreviations in the Dental Composite Resin: CR column in Table 5 each represent the following CRs.

[0098] EUF (CE): The same as in Example 1, Esthelite Universal Flow Medium Shade CE (manufactured by Tokuyama Dental Co., Ltd., contrast ratio 0.39) OCF: Omnichroma Flow (Tokuyama Dental structural color CR, contrast ratio 0.31) OC: Omnichroma (Structural color system CR manufactured by Tokuyama Dental, contrast ratio 0.39).

[0099] Table 5

Claims

1. A dental adhesive comprising a hardenable composition that is applied to a tooth surface before applying a photocurable dental material, in order to bond a tooth to a cured product of the photocurable dental material, the photocurable composition comprising a polymerizable monomer and a photopolymerization initiator and that is hardened by visible light irradiation, the photocurable dental material comprising a hardenable composition that is hardened by visible light irradiation, the hardenable composition containing the polymerizable monomer and the photopolymerization initiator, the dental adhesive being a one-component dental adhesive composition that is used as a dental adhesive that is hardened by visible light irradiation after application to harden the photocurable dental material, without being hardened before application of the photocurable dental material, The one-component dental adhesive composition contains 100 parts by mass of a polymerizable monomer component containing an acidic group-containing polymerizable monomer and 0.5 to 5 parts by mass of an α-aminoacetophenone-type photopolymerization initiator, and further contains 0.1 to 4 parts by mass of camphorquinone, or when a photopolymerization initiator containing camphorquinone is used as the photocurable dental material, camphorquinone is supplied from the photocurable dental material, thereby making the composition curable by irradiation with visible light. A one-component dental adhesive composition comprising:

2. 2. The one-component dental adhesive composition according to claim 1, comprising 0.1 to 4 parts by mass of camphorquinone.

3. 2. The one-component dental adhesive composition according to claim 1, comprising, as a photopolymerization initiator, either an α-aminoacetophenone-type photopolymerization initiator alone, or a photopolymerization initiator consisting of an α-aminoacetophenone-type photopolymerization initiator and camphorquinone alone.

4. A one-component dental adhesive composition for a photocurable dental material, comprising a photocurable composition that contains a polymerizable monomer and a photopolymerization initiator containing camphorquinone and that is cured by irradiation with visible light, 2. The one-component dental adhesive composition according to claim 1, which does not contain camphorquinone and is curable by irradiation with visible light as a result of camphorquinone being supplied from the photocurable dental material.

5. The α-aminoacetophenone type photopolymerization initiator is represented by the following general formula (1): 【Chemistry 1】 (wherein Ph represents a phenyl group, R １ , R ２ , R ３ and R ４ each independently represents a monovalent organic group or a hydrogen atom.

5. The one-component dental adhesive composition according to claim 1, comprising a compound represented by the formula:

6. The one-component dental adhesive composition according to any one of claims 1 to 5, wherein the α-aminoacetophenone type photopolymerization initiator is a compound that undergoes a triplet energy transfer type photosensitized reaction and has a triplet excitation energy of 62 kcal / mol or less.

7. The one-component dental adhesive composition according to any one of claims 1 to 6, further comprising 1 to 5 parts by mass of a tertiary amine (excluding α-aminoacetophenone type photopolymerization initiators).

8. 8. The one-component dental adhesive composition according to claim 1, further comprising 20 to 450 parts by mass of a solvent component consisting of water and / or an organic solvent.

9. A dental restoration kit comprising a combination of the one-component dental adhesive composition according to any one of claims 1 to 8 and a photocurable dental material comprising a photocurable composition that contains a polymerizable monomer and a photopolymerization initiator and is cured by irradiation with visible light, The light-curable dental material is a light-curable dental material in which a contrast ratio Yb / Yw, defined as the ratio of the Y stimulus value on a black background: Yb (black background) to the Y stimulus value on a white background: Yw (white background), obtained by measuring tristimulus values ​​using a color difference meter with black and white backgrounds on a 1 mm-thick sample made of a cured product of the light-curable dental material, is 0.45 or less; The one-component dental adhesive composition is a dental adhesive comprising a curable composition that is applied to a tooth surface before applying a light-curable dental material, in order to bond a tooth to a cured product of the light-curable dental material, the photocurable composition comprising a polymerizable monomer and a photopolymerization initiator and cured by visible light irradiation, The dental restoration kit is characterized in that it is used for performing dental restoration by curing and bonding the one-component dental adhesive composition with visible light irradiation, which is used to harden the light-curable dental material after application, without hardening the one-component dental adhesive composition before application of the light-curable dental material.

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