JP2013193982A - Dental pretreatment agent - Google Patents
Dental pretreatment agent Download PDFInfo
- Publication number
- JP2013193982A JP2013193982A JP2012062020A JP2012062020A JP2013193982A JP 2013193982 A JP2013193982 A JP 2013193982A JP 2012062020 A JP2012062020 A JP 2012062020A JP 2012062020 A JP2012062020 A JP 2012062020A JP 2013193982 A JP2013193982 A JP 2013193982A
- Authority
- JP
- Japan
- Prior art keywords
- group
- acid
- dental
- pretreatment agent
- dentin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
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- 239000002253 acid Substances 0.000 claims abstract description 61
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Landscapes
- Dental Preparations (AREA)
Abstract
Description
本発明は、予め生体歯牙組織表面に前処理を施すのに主として使用される歯科用前処理剤に関する。より詳しくは、酸水溶液による歯牙のエッチング処理によりスメア層を除去し、また歯牙表面に微細な凹凸を作ることにより歯牙と歯科用硬化性組成物（歯科用象牙質接着材、歯科接着用レジンセメント、合着用セメント、シーラント、歯科用充填剤等）と歯牙との間の接着力を高める歯科用前処理剤に関する。 The present invention relates to a dental pretreatment agent mainly used for pretreatment of the surface of a living tooth tissue in advance. More specifically, the tooth and dental curable composition (dental dentin adhesive, dental adhesive resin cement by removing the smear layer by etching the tooth with an acid aqueous solution and making fine irregularities on the tooth surface. , Cement, sealant, dental filler, etc.) and dental pretreatment agents that increase the adhesion between teeth.
従来より、生体歯牙組織と該組織を修復する歯科用硬化性組成物（歯科用象牙質接着材、歯科接着用レジンセメント、合着用セメント、シーラント、歯科用充填剤等）とを強力に接着する目的で、あるいは被着面の清掃処理を目的として、予め、歯牙表面を歯科用前処理剤で処理する方法が広く行われている。 Conventionally, a living dental tissue and a dental curable composition for repairing the tissue (dental dentin adhesive, dental adhesive resin cement, cement for bonding, sealant, dental filler, etc.) are strongly bonded. For the purpose or for the purpose of cleaning the adherend surface, a method of treating the tooth surface with a dental pretreatment agent in advance has been widely performed.
歯牙組織のエナメル質と象牙質を研削すると、スメアー層と呼ばれる粉砕されたハイドロキシアパタイトとタンパク質とから成る混合物が歯牙研削面に生成する。スメアー層は機械的強さが弱く、脱灰除去しなければエナメル質や象牙質に歯科用硬化性組成物を強固に接着することはできない。前記の前処理剤として一般に使用されているのは、リン酸、クエン酸、エチレンジアミン四酢酸等の酸水溶液等からなる歯科用前処理剤である。この酸水溶液の歯科用前処理剤を歯牙研削面に作用させることで、歯牙を切削した際に生じるスメアー層を酸により溶解・除去することができる。さらに、歯牙表面に微細な凹凸をつくってアンカー効果を発揮させることにより、修復材料を強固に接着させることが行われている。 When the enamel and dentin of the tooth tissue are ground, a mixture of ground hydroxyapatite and protein called a smear layer is formed on the tooth grinding surface. The smear layer is weak in mechanical strength, and unless it is decalcified, the dental curable composition cannot be firmly bonded to enamel or dentin. Generally used as the pretreatment agent is a dental pretreatment agent comprising an acid aqueous solution such as phosphoric acid, citric acid, and ethylenediaminetetraacetic acid. By applying the dental pretreatment agent of the acid aqueous solution to the tooth grinding surface, the smear layer generated when the tooth is cut can be dissolved and removed by the acid. Furthermore, the restoration material is firmly adhered by creating fine irregularities on the tooth surface to exert an anchor effect.
しかしながら、前処理剤として酸水溶液を使用する場合には、エナメル質に対する歯科用硬化性組成物の接着力を高めることができるが、象牙質に作用させた場合に接着力が低くなるという問題がある。この問題は、酸水溶液による前処理ではエッチング、水洗により研削した象牙質表面に生じたスメヤー層と共に象牙質の無機成分までもが失われ機械的強度が低くなること、さらには、エアー乾燥の操作によりエッチング材が作用した象牙質部分に残った有機成分のコラーゲン線維が収縮し、その後に適用する歯科用硬化性組成物の象牙質への浸透を阻害するためと考えられている。 However, when an acid aqueous solution is used as the pretreatment agent, the adhesive force of the dental curable composition to the enamel can be increased, but there is a problem that the adhesive force is lowered when it is applied to the dentin. is there. This problem is caused by the pretreatment with acid aqueous solution, the smear layer formed on the surface of the dentin ground by etching and washing with water, and the inorganic components of the dentin are lost and the mechanical strength is lowered. It is considered that the collagen fiber of the organic component remaining in the dentin portion where the etching material has acted is contracted by this, and the penetration of the dental curable composition applied thereafter to the dentin is inhibited.
このような問題を解消するために、歯科用前処理剤による処理後、プライマーを用いることによって予め重合性単量体成分を浸透させておく等、歯科用前処理剤処理後の象牙質表面を接着に適する状態に改質する必要があった。つまり研削象牙質に接着を行う際、歯科用前処理剤による処理の後で、プライマーによる処理を再度行う手間のかかる処置を必要とした。 In order to eliminate such problems, the surface of the dentin after treatment with the dental pretreatment agent, such as preliminarily infiltrating the polymerizable monomer component by using a primer after treatment with the dental pretreatment agent, is used. It was necessary to modify to a state suitable for adhesion. In other words, when bonding to the ground dentin, the treatment with the primer is required after the treatment with the dental pretreatment agent.
一方で、このような問題を解決するために、界面活性剤を含有することを特徴とする歯科用前処理剤が提案されている（例えば、特許文献１の特許請求の範囲を参照）。このような界面活性剤を含有する前処理剤を用いることで象牙質の接着性を向上することができる。 On the other hand, in order to solve such a problem, a dental pretreatment agent characterized by containing a surfactant has been proposed (see, for example, the claims of Patent Document 1). The adhesiveness of dentin can be improved by using a pretreatment agent containing such a surfactant.
前述の特許文献１で記載された歯科用前処理剤は、その実施例に具体的な例示があるように、クエン酸などの弱酸からなる水溶液を使用する場合には、処理後に適用する歯科用硬化性材料の象牙質への接着性において、比較的良好な（実施例１〜３において９．０ＭＰａ〜１２．６ＭＰａの）強度の向上効果が認められる。しかしながら、リン酸水溶液を使用した場合（実施例４）は接着性の向上効果は認められるものの６．０ＭＰａと依然不十分であり、その比較例１の象牙質に対する接着性（５．１ＭＰａ）と大差ない値しか得られていなかった。本発明者等の検討においても、リン酸のような強酸からなる水溶液で象牙質を処理した場合は、象牙質への接着性の低下の問題が依然としてあり、実用上十分な（およそ１０ＭＰａ以上の）象牙質接着性を容易に達成可能な方法が望まれていた。一方で、クエン酸のような弱酸を使用した場合は、象牙質への接着性は比較的良好なものの、エナメル質、特に非切削エナメル質の脱灰力が不十分であった。 The dental pretreatment agent described in Patent Document 1 is a dental pretreatment agent that is applied after treatment when an aqueous solution composed of a weak acid such as citric acid is used, as shown in the specific examples. In the adhesiveness of the curable material to the dentin, a relatively good strength improvement effect (from 9.0 MPa to 12.6 MPa in Examples 1 to 3) is recognized. However, when the phosphoric acid aqueous solution was used (Example 4), although the effect of improving the adhesiveness was recognized, it was still insufficient with 6.0 MPa, and the adhesiveness to the dentin of Comparative Example 1 (5.1 MPa) Only values that were not very different were obtained. Even in the study by the present inventors, when the dentin was treated with an aqueous solution composed of a strong acid such as phosphoric acid, there was still a problem of decreased adhesion to the dentin, which was practically sufficient (approximately 10 MPa or more). ) A method that can easily achieve dentin adhesiveness has been desired. On the other hand, when a weak acid such as citric acid was used, although the adhesion to dentin was relatively good, the decalcification power of enamel, particularly non-cut enamel, was insufficient.
即ち、エナメル質、特に非切削エナメル質の十分な脱灰性を付与するために、歯科用前処理剤としてリン酸のような強酸の水溶液を用いた場合においても、これを象牙質に前処理しても、その後に適用する歯科用硬化性材料が該象牙質に対して高強度に接着できるものを開発することが大きな課題となっていた。 That is, in order to give sufficient decalcification of enamel, especially non-cutting enamel, even when an aqueous solution of strong acid such as phosphoric acid is used as a dental pretreatment agent, this is pretreated into dentin. Even so, it has been a major challenge to develop a dental curable material to be applied thereafter that can adhere to the dentin with high strength.
本発明者らは、上記課題を達成するために、リン酸等の強酸を含む水溶液からなる歯科用前処理剤を使用した場合の象牙質への接着性低下の抑制効果について鋭意検討した結果、強酸を含む酸水溶液にアルキルスルホン酸アミド系界面活性剤を含ませることで前記の課題を解決しうることを見いだし、本発明を完成するに到った。 In order to achieve the above-mentioned problems, the present inventors have intensively studied the inhibitory effect on adhesiveness degradation to dentin when using a dental pretreatment agent comprising an aqueous solution containing a strong acid such as phosphoric acid, It has been found that the above-mentioned problems can be solved by including an alkylsulfonic acid amide surfactant in an acid aqueous solution containing a strong acid, and the present invention has been completed.
即ち、本発明は、（Ａ）２３℃における水中でのｐＫａが２．５以下の酸を含む酸水溶液、および（Ｂ）アルキルスルホン酸アミド系界面活性剤を含有することを特徴とする歯科用前処理剤である。 That is, the present invention comprises (A) an acid aqueous solution containing an acid having a pKa in water at 25 ° C. of 2.5 or less, and (B) an alkylsulfonic acid amide surfactant. It is a pretreatment agent.
本発明の歯科用前処理剤によれば、（Ａ）２３℃における水中でのｐＫａが２．５以下の酸を含む酸水溶液を使用することで、エナメル質、特に非切削エナメル質への高い脱灰性が達成される。更に、本発明の歯科用前処理剤は（Ｂ）アルキルスルホン酸アミド系界面活性剤を含むことで、強酸水溶液（ｐＫａが２．５以下の酸を含む酸水溶液）からなる歯科用前処理剤で切削象牙質をエッチング処理した場合も、その後に適用する歯科用硬化性材料の象牙質への接着性の低下を抑制することができる。 According to the dental pretreatment agent of the present invention, (A) by using an acid aqueous solution containing an acid having a pKa in water at 23 ° C. of 2.5 or less, the enamel, particularly the non-cutting enamel is high. Demineralization is achieved. Furthermore, the dental pretreatment agent of the present invention comprises (B) an alkylsulfonic acid amide surfactant, so that the dental pretreatment agent comprises a strong acid aqueous solution (an acid aqueous solution containing an acid having a pKa of 2.5 or less). Even when the cut dentin is subjected to etching treatment, it is possible to suppress a decrease in adhesion of the dental curable material applied thereafter to the dentin.
本発明におけるアルキルスルホン酸アミド系界面活性剤の作用機序は定かではないものの、（Ｂ）アルキルスルホン酸アミド系界面活性剤と象牙質のコラーゲン線維との相互作用により、象牙質の濡れ性が向上し、その後に適用する歯科用硬化性組成物の重合性単量体成分等の象牙質への浸透性が向上するためと本発明者等は考察している。また、エッチング処理後の象牙質のコラーゲン線維に（Ｂ）アルキルスルホン酸アミド系界面活性剤が残ることで、その後のエアー乾燥操作によるコラーゲン線維の収縮が抑制されるためではないかと本発明者等は考察している。 Although the mechanism of action of the alkylsulfonic acid amide surfactant in the present invention is not clear, (B) the wettability of the dentin is caused by the interaction between the alkylsulfonic acid amide surfactant and the dentin collagen fibers. The present inventors consider that the penetration of the polymerizable monomer component of the dental curable composition applied thereafter and dentin is improved. Moreover, the present inventors, etc., may be because the (B) alkylsulfonic acid amide-based surfactant remains in the dentin collagen fibers after the etching treatment, thereby suppressing the contraction of the collagen fibers by the subsequent air drying operation. Is considering.
本発明の歯科前処理剤は、（Ａ）２３℃における水中でのｐＫａが２．５以下の酸を含む酸水溶液、および（Ｂ）アルキルスルホン酸アミド系界面活性剤を含有する歯科用前処理剤、である。 The dental pretreatment agent of the present invention is a dental pretreatment containing (A) an acid aqueous solution containing an acid having a pKa in water of 2.5 or less at 23 ° C., and (B) an alkylsulfonic acid amide surfactant. Agent.
本発明においては、エナメル質、特に非切削エナメル質への高い脱灰性を達成するために、２３℃におけるｐＫａが２．５以下の強酸を使用する。あまり酸の強度が強すぎても象牙質への接着性は低下傾向になるため、２３℃におけるｐＫａは１．０以上であるのが望ましい。 In the present invention, a strong acid having a pKa at 23 ° C. of 2.5 or less is used in order to achieve high decalcification to enamel, particularly non-cutting enamel. Even if the acid strength is too strong, the adhesiveness to the dentin tends to be lowered. Therefore, the pKa at 23 ° C. is preferably 1.0 or more.
本発明の歯科用前処理剤に使用する（Ａ）２３℃における水中でのｐＫａが２．５以下の酸を含む酸水溶液は、２３℃における水中でのｐＫａが２．５以下の従来公知の酸を含む水溶液が何ら制限なく使用できる。このような２３℃におけるｐＫａが２．５以下の酸を例示すれば、硫酸、硝酸、塩酸、過塩素酸、臭化水素酸、トリクロロ酢酸、ジクロロ酢酸、リン酸、2,6-ジオキシ安息香酸、ニトロ酢酸、シアノ酢酸、o-ニトロ安息香酸、マレイン酸、ピルビン酸、グルタミン酸、アスパラギン酸、タウリン、シュウ酸、エチレンジアミン四酢酸、トリフロロ酢酸、等が挙げられる。これらの中で、生体への為害性を考慮するとリン酸、マレイン酸、ピルビン酸、グルタミン酸、アスパラギン酸、タウリン、シュウ酸、エチレンジアミン四酢酸の使用が好ましく、高いエナメル質、特に非切削エナメル質への脱灰性が得られる観点から特にはリン酸を使用することが好ましい。こちらの酸は単独で又は２種以上を配合して使用することができる。 The acid aqueous solution containing an acid having a pKa in water at 23 ° C. of 2.5 or less used in the dental pretreatment agent of the present invention is a conventionally known acid having a pKa in water at 23 ° C. of 2.5 or less. An aqueous solution containing an acid can be used without any limitation. Examples of such acids having a pKa at 23 ° C. of 2.5 or less are sulfuric acid, nitric acid, hydrochloric acid, perchloric acid, hydrobromic acid, trichloroacetic acid, dichloroacetic acid, phosphoric acid, 2,6-dioxybenzoic acid. Nitroacetic acid, cyanoacetic acid, o-nitrobenzoic acid, maleic acid, pyruvic acid, glutamic acid, aspartic acid, taurine, oxalic acid, ethylenediaminetetraacetic acid, trifluoroacetic acid, and the like. Among these, in consideration of harm to the living body, it is preferable to use phosphoric acid, maleic acid, pyruvic acid, glutamic acid, aspartic acid, taurine, oxalic acid, ethylenediaminetetraacetic acid, and to high enamel, especially non-cutting enamel In particular, it is preferable to use phosphoric acid from the viewpoint of obtaining the deashing property. These acids can be used alone or in combination of two or more.
本発明の歯科用前処理剤に使用する（Ａ）２３℃における水中でのｐＫａが２．５以下の酸を含む酸水溶液の酸濃度は特に限定されない。高い清掃効果またはエッチング効果が得られることから、酸濃度の好ましい範囲は１質量％以上８０質量％以下の範囲である。当該歯牙組織の修復面のエッチング剤として使用する場合であれば、酸濃度は１０重量％以上７０重量％以下の範囲であるのが特に好ましく、３０質量％以上６０質量％以下の範囲であるのが最も好ましい。他方、被着面に付着した唾液や歯垢等の汚れを除去する清掃剤として使用するのであれば、酸濃度は５質量％以上６０質量％以下の範囲であるのが特に好ましい。 (A) The acid concentration of the acid aqueous solution containing the acid whose pKa in water at 23 degreeC is 2.5 or less used for the dental pretreatment agent of this invention is not specifically limited. Since a high cleaning effect or etching effect is obtained, the preferable range of the acid concentration is in the range of 1% by mass to 80% by mass. When used as an etchant for the restoration surface of the tooth tissue, the acid concentration is particularly preferably in the range of 10% by weight to 70% by weight, and in the range of 30% by weight to 60% by weight. Is most preferred. On the other hand, when used as a cleaning agent for removing dirt such as saliva and plaque adhering to the adherend surface, the acid concentration is particularly preferably in the range of 5 mass% to 60 mass%.
本発明の酸水溶液に使用する水としては蒸留、濾過、イオン交換等によって、有害な不純物を含まないものを用いることが好ましい。 As the water used in the acid aqueous solution of the present invention, it is preferable to use water that does not contain harmful impurities by distillation, filtration, ion exchange or the like.
本発明の歯科用前処理剤は、（Ｂ）アルキルスルホン酸アミド系界面活性剤を更に含有している。かかる（Ｂ）アルキルスルホン酸アミド系界面活性剤は、親水基としてアルキルスルホン酸アミド基および従来公知の疎水基を有する化合物からなる界面活性剤であり、これを満足する公知の化合物が制限なく使用できる。 The dental pretreatment agent of the present invention further contains (B) an alkylsulfonic acid amide surfactant. Such (B) alkylsulfonic acid amide surfactant is a surfactant comprising a compound having an alkylsulfonic acid amide group as a hydrophilic group and a conventionally known hydrophobic group, and a known compound that satisfies this is used without limitation. it can.
本発明において、（Ｂ）アルキルスルホン酸アミド系界面活性剤として下記式（１）の構造を有するものは入手が容易でありまた高い接着性が得られることから好ましい。
ＭＳＯ３−Ｒ１−Ｎ（Ｒ２）（Ｃ＝Ｏ）−Ｒ３・・・式（１）
（式中Ｍは、水素原子または１価の対カチオンであり、
Ｒ１は、炭素数５以下のアルキレン基であり、
Ｒ２は、水素原子、又は炭素数６以下のアルキル基若しくは炭素数３〜６のシクロアルキル基であり、
Ｒ３は、炭素数４〜３０のアルキル基、炭素数４〜３０のアルケニル基、炭素数４〜１０のシクロアルキル基、又は炭素数６〜３０の芳香族炭化水素基である）
前記一般式（１）中、Ｒ１の炭素数５以下のアルキレン基としては、メチレン基、エチレン基、ｎ−プロピレン基、ｎ−ブチレン基、ｎ−ペンチレン基、２−メチル−ｎ−プロピレン基、２−エチル−ｎ−プロピレン基、２−メチル−ｎ−ブチレン基等の直鎖または分岐状のものが例示できる。また、これらのアルキレン基は、ハロゲン基、アミド基、カルボキシル基、シアノ基、アミノ基、イミノ基、ニトロ基、ヒドロキシ基、リン酸基、スルホン酸基等の置換基を有していてもよい。
In the present invention, (B) an alkylsulfonic acid amide surfactant having the structure of the following formula (1) is preferred because it is easily available and high adhesiveness is obtained.
MSO 3 -R 1 -N (R 2 ) (C = O) -R 3 ··· Equation (1)
(In the formula, M is a hydrogen atom or a monovalent counter cation,
R 1 is an alkylene group having 5 or less carbon atoms,
R 2 is a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms,
R 3 is an alkyl group having 4 to 30 carbon atoms, an alkenyl group having 4 to 30 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 30 carbon atoms)
In the general formula (1), the alkylene group having 5 or less carbon atoms of R 1 includes a methylene group, an ethylene group, an n-propylene group, an n-butylene group, an n-pentylene group, and a 2-methyl-n-propylene group. , 2-ethyl-n-propylene group, 2-methyl-n-butylene group and the like can be exemplified. Further, these alkylene groups may have a substituent such as a halogen group, an amide group, a carboxyl group, a cyano group, an amino group, an imino group, a nitro group, a hydroxy group, a phosphoric acid group, or a sulfonic acid group. .
前記一般式（１）中、炭素数６以下のＲ２のアルキル基としては、メチル基、エチル基、ｎ−プロピル基、ｎ−ブチル基、ｎ−ペンチル基、ｎ−ヘキシル基、２−メチル−ｎ−プロピル基、２−エチル−ｎ−プロピル基、２−メチル−ｎ−ブチル基、３−メチル−ｎ−ペンチル基等の直鎖または分岐状のものが例示できる。これらのアルキル基も、上記Ｒ１の炭素数５以下のアルキレン基と同様の置換基を有していてもよい。また、Ｒ２の炭素数３〜６のシクロアルキル基としては、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基等が例示できる。これらのシクロアルキル基も、上記Ｒ１のアルキレン基と同様の置換基を有していてもよい。 In the general formula (1), the R 2 alkyl group having 6 or less carbon atoms includes a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, and 2-methyl. Examples include linear or branched groups such as -n-propyl group, 2-ethyl-n-propyl group, 2-methyl-n-butyl group, and 3-methyl-n-pentyl group. These alkyl groups may also have the same substituent as the alkylene group having 5 or less carbon atoms of R 1 . Further, the cycloalkyl group having 3 to 6 carbon atoms R 2, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group and the like. These cycloalkyl groups may also have the same substituent as the alkylene group for R 1 described above.
前記一般式（１）中、Ｒ３の炭素数４〜３０のアルキル基としては、ｎ−ブチル基、ｎ−ペンチル基、ｎ−ヘキシル基、ｎ−ヘプチル基、ｎ−オクチル基、ｎ−ノニル基、ｎ−デシル基、ｎ−ウンデシル基、ｎ−ドデシル基、ｎ−トリデシル基、ｎ−テトラデシル基、ｎ−ペンタデシル基、ｎ−ヘキサデシル基、ｎ−ヘプタデシル基、ｎ−オクタデシル基、ｎ−ノナデシル基、ｎ−エイコデシル基、ｎ−ヘキコシル基、ｎ−ドコシル基、ｎ−トリコシル基、ｎ−テトラコシル基、ｎ−ペンタコシル基、ｎ−ヘキサコシル基、ｎ−ヘプタコシル基、ｎ−オクタコシル基、ｎ−ノナコシル基、ｎ−トリアコシル基、２−ブチル−ｎ−ウンデシル基、３−ブチル−ｎ−ウンデシル基、４−ブチル−ｎ−ウンデシル基、５−ペンチル−ｎ−ウンデシル基、２−プロピル−ｎ−ドデシル基、３−プロピル−ｎ−ドデシル基、４−プロピル−ｎ−ドデシル基、５−プロピル−ｎ−ドデシル基、２−ペンチル−ｎ−ドデシル基、３−メチル−ｎ−ドデシル基、４−エチル−ｎ−ドデシル基、２−プロピル−ｎ−ドデシル基、３−ブチル−ｎ−ドデシル基、２−オクチル−ｎ−ドデシル基、２−デシル−ｎ−ドデシル基等の直鎖または分岐状のものが挙げられる。これらのアルキレン基も、上記Ｒ１の炭素数５以下のアルキレン基と同様の置換基を有していてもよい。 In the general formula (1), the alkyl group having 4 to 30 carbon atoms of R 3 includes n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, and n-nonyl. Group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group Group, n-eicodecyl group, n-hexosyl group, n-docosyl group, n-tricosyl group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group Group, n-triacosyl group, 2-butyl-n-undecyl group, 3-butyl-n-undecyl group, 4-butyl-n-undecyl group, 5-pentyl-n-undecyl Group, 2-propyl-n-dodecyl group, 3-propyl-n-dodecyl group, 4-propyl-n-dodecyl group, 5-propyl-n-dodecyl group, 2-pentyl-n-dodecyl group, 3-methyl -N-dodecyl group, 4-ethyl-n-dodecyl group, 2-propyl-n-dodecyl group, 3-butyl-n-dodecyl group, 2-octyl-n-dodecyl group, 2-decyl-n-dodecyl group Linear or branched ones such as These alkylene groups may also have the same substituent as the alkylene group having 5 or less carbon atoms of R 1 .
また、Ｒ３の炭素数４〜３０のアルケニル基としては、ブテニル基、ペンテニル基、ヘキセニル基、ヘプテニル基、オクテニル基、ノネニル基、デセニル基、ウンデセニル基、ドデセニル基、テトラデセニル基、ペンタデセニル基、ヘキサデセニル基、ヘプタデセニル基、オクタデニセニル基、ノナデセニル基、エイコセニル基、ヘキコセニル基、ドコセニル基、トリコセニル基、テトラコセニル基、ペンタコセニル基、ヘキサコセニル基、ヘプタコセニル基、オクタコセニル基、ノナコセニル基、トリアコセニル基、２−ブチル−ウンデセニル基、３−ブチル−ウンデセニル基、４−ブチル−ウンデセニル基、５−ペンチル−ウンデセニル基、２−プロピル−ドデセニル基、３−プロピル−ドデセニル基、４−プロピル−ドデセニル基、５−プロピル−ドデセニル基、２−ペンチル−ドデセニル基、３−メチル−ドデセニル基、４−エチル−ドデセニル基、２−プロピル−ドデセニル基、３−ブチル−ドデセニル基、２−オクチル−ドデセニル基、２−デシル−ドデセニル基、２−ペンテニル−ヘプタデセニル基、２−ブテニルーオクタデセニル基等の直鎖または分岐状のものが挙げられる。これらのアルケニル基も、上記Ｒ１の炭素数５以下のアルキレン基と同様の置換基を有していてもよい。 Examples of the alkenyl group having 4 to 30 carbon atoms of R 3 include butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, tetradecenyl group, pentadecenyl group, hexadecenyl group Group, heptadecenyl group, octadecenyl group, nonadecenyl group, eicocenyl group, hecocenyl group, dococenyl group, tricocenyl group, tetracocenyl group, pentacocenyl group, hexacocenyl group, heptacocenyl group, octacocenyl group, nonacosenyl group, triacocenyl group, 2-butyl-undecenyl group 3-butyl-undecenyl group, 4-butyl-undecenyl group, 5-pentyl-undecenyl group, 2-propyl-dodecenyl group, 3-propyl-dodecenyl group, 4-propyl-dodecenyl group, 5 -Propyl-dodecenyl group, 2-pentyl-dodecenyl group, 3-methyl-dodecenyl group, 4-ethyl-dodecenyl group, 2-propyl-dodecenyl group, 3-butyl-dodecenyl group, 2-octyl-dodecenyl group, 2- Examples thereof include linear or branched decyl-dodecenyl groups, 2-pentenyl-heptadecenyl groups, 2-butenyl-octadecenyl groups, and the like. These alkenyl groups may also have the same substituent as the alkylene group having 5 or less carbon atoms of R 1 .
また、Ｒ３の炭素数４〜１０のシクロアルキル基としては、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基または、シクロオクチル基等が挙げられる。これらのシクロアルキル基も、上記Ｒ１の炭素数５以下のアルキレン基と同様の置換基を有していてもよい。 In addition, examples of the cycloalkyl group having 4 to 10 carbon atoms of R 3 include a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. These cycloalkyl groups may also have the same substituent as the alkylene group having 5 or less carbon atoms of R 1 .
さらに、Ｒ３の炭素数６〜３０の芳香族炭化水素基としては、フェニル基、メチルフェニル基、ジメチルフェニル基、エチルフェノル基、プロピルフェニル基、ブチルフェニル基、ペンチルフェニル基、ヘキシルフェニル基、ヘプチルフェニル基、オクチルフェニル基、ノニルフェニル基、デシルフェニル基、ウンデシルフェニル基、ドデシルフェニル基、トリデシルフェニル基、テトラデシルフェニル基、ペンタデシルフェニル基、ヘキサデシルフェニル基、ヘプタデシルフェニル基、オクタデシルフェニル基、ノナデシルフェニル基、エイコデシルフェニル基、ヘキコシルフェニル基、ドコシルフェニル基、トリコシルフェニル基、テトラコシルフェニル基、モノスチレン化フェニル基、ジスチレン化フェニル基、トリスチレン化フェニル基、ナフチル基、メチルナフチル基、エチルナフチル基、プロピルナフチル基、ブチルナフチル基、ペンチルナフチル基、ヘキシルナフチル基、ヘプチルナフチル基、オクチルナフチル基、ノニルナフチル基、デシルナフチル基、ウンデシルナフチル基、ドデシルナフチル基、トリデシルナフチル基、テトラデシルナフチル基、ペンタデシルナフチル基、ヘキサデシルナフチル基、ヘプタデシルナフチル基、オクタデシルナフチル基、ノナデシルナフチル基、エイコデシルナフチル基、アントラセニル基、フェナントラセニル基、テトラセニル基、クリセニル基、ペンタセニル基、ヘキサセニル基、および、へプタセニル基等が挙げられる。これらの芳香族炭化水素基も、上記Ｒ１の炭素数５以下のアルキレン基と同様の置換基を有していてもよい。 Furthermore, as the aromatic hydrocarbon group having 6 to 30 carbon atoms of R 3 , phenyl group, methylphenyl group, dimethylphenyl group, ethylphenol group, propylphenyl group, butylphenyl group, pentylphenyl group, hexylphenyl group, heptyl Phenyl group, octylphenyl group, nonylphenyl group, decylphenyl group, undecylphenyl group, dodecylphenyl group, tridecylphenyl group, tetradecylphenyl group, pentadecylphenyl group, hexadecylphenyl group, heptadecylphenyl group, octadecyl Phenyl group, nonadecylphenyl group, eicodecylphenyl group, hexosylphenyl group, docosylphenyl group, tricosylphenyl group, tetracosylphenyl group, monostyrenated phenyl group, distyrenated phenyl group, tristyrenated phenyl Group, naphthyl group, methylnaphthyl group, ethylnaphthyl group, propylnaphthyl group, butylnaphthyl group, pentylnaphthyl group, hexylnaphthyl group, heptylnaphthyl group, octylnaphthyl group, nonylnaphthyl group, decylnaphthyl group, undecylnaphthyl group , Dodecylnaphthyl, tridecylnaphthyl, tetradecylnaphthyl, pentadecylnaphthyl, hexadecylnaphthyl, heptadecylnaphthyl, octadecylnaphthyl, nonadecylnaphthyl, eicodecylnaphthyl, anthracenyl, phenanthracene Nyl group, tetracenyl group, chrycenyl group, pentacenyl group, hexacenyl group, heptacenyl group and the like can be mentioned. These aromatic hydrocarbon groups may also have the same substituent as the alkylene group having 5 or less carbon atoms of R 1 .
また、Ｍの１価の対カチオンは、ナトリウムイオン、カリウムイオン等のアルカリ金属イオンなどが挙げられる。 Examples of the monovalent counter cation of M include alkali metal ions such as sodium ion and potassium ion.
本発明で使用される（Ｂ）アルキルスルホン酸アミド系界面活性剤として、特に入手が容易でかつ象牙質への接着性の低下抑制効果が高いために好適な化合物を具体的に例示すると以下の化合物が挙げられる。
２−［ラウロイル(メチル)アミノ］エタンスルホン酸ナトリウム
As the (B) alkyl sulfonic acid amide surfactant used in the present invention, specific examples of compounds that are particularly easily available and highly effective in suppressing the decrease in adhesion to dentin are given below. Compounds.
2- [Lauroyl (methyl) amino] ethanesulfonic acid sodium salt
２−（Ｎ−メチル−Ｎ−ステアロイルアミノ）エタンスルホン酸ナトリウム 2- (N-methyl-N-stearoylamino) ethanesulfonic acid sodium salt
２−（Ｎ−メチル−Ｎ−パルミトイルアミノ）エタンスルホン酸ナトリウム 2- (N-methyl-N-palmitoylamino) ethanesulfonic acid sodium salt
Ｎ−ミリストイル−Ｎ−メチルタウリンナトリウム N-myristoyl-N-methyltaurine sodium
２−［シクロヘキシル（１−オキソテトラデシル）アミノ］エタンスルホン酸ナトリウム 2- [Cyclohexyl (1-oxotetradecyl) amino] ethanesulfonic acid sodium salt
２−［メチル（１−オキソ−９−オクタデセニル）アミノ］エタンスルホン酸ナトリウム 2- [Methyl (1-oxo-9-octadecenyl) amino] ethanesulfonic acid sodium salt
２−［シクロヘキシル（１−オキソオクタデシル）アミノ］エタンスルホン酸ナトリウム 2- [Cyclohexyl (1-oxooctadecyl) amino] ethanesulfonic acid sodium salt
２−［シクロヘキシル（１−オキソヘキサデシル）アミノ］エタンスルホン酸ナトリウム 2- [Cyclohexyl (1-oxohexadecyl) amino] ethanesulfonic acid sodium salt
２−［（１−オキソドデシル）アミノ］エタンスルホン酸ナトリウム 2-[(1-oxododecyl) amino] ethanesulfonic acid sodium salt
２−［［（Ｚ）−１−オキソ−９−オクタデセニル］アミノ］エタンスルホン酸ナトリウム 2-[[(Z) -1-oxo-9-octadecenyl] amino] ethanesulfonic acid sodium salt
２−［メチル［（９Ｚ，１２Ｚ）−１−オキソ−９，１２−オクタデカジエニル］アミノ］エタンスルホン酸ナトリウム
2- [Methyl [(9Z, 12Z) -1-oxo-9,12-octadecadienyl] amino] ethanesulfonic acid sodium salt
Ｎ−オクタデカノイルタウリンナトリウム N-octadecanoyl taurine sodium
２−（Ｎ−メチル−Ｎ−ラウロイルアミノ）エタンスルホン酸ナトリウム 2- (N-methyl-N-lauroylamino) ethanesulfonic acid sodium salt
２−［メチル（トリデカノイル）アミノ］エタンスルホン酸ナトリウム 2- [Methyl (tridecanoyl) amino] ethanesulfonic acid sodium salt
２−（Ｎ−メチル−Ｎ−ミリストイルアミノ）エタンスルホン酸ナトリウム 2- (N-methyl-N-myristoylamino) ethanesulfonic acid sodium salt
２−［メチル（ペンタデカノイル）アミノ］エタンスルホン酸ナトリウム
2- [Methyl (pentadecanoyl) amino] ethanesulfonic acid sodium salt
２−［メチル（１−オキソイコシル）アミノ］エタンスルホン酸ナトリウム 2- [Methyl (1-oxoicosyl) amino] ethanesulfonic acid sodium salt
２−［Ｎ−［２−メルカプトメチル−３−フェニルプロパノイル］−Ｎ−メチルアミノ］エタンスルホン酸ナトリウム 2- [N- [2-Mercaptomethyl-3-phenylpropanoyl] -N-methylamino] ethanesulfonic acid sodium salt
２−［Ｎ−［２−アセチルチオメチル−３−フェニルプロパノイル］−Ｎ−メチルアミノ］エタンスルホン酸ナトリウム Sodium 2- [N- [2-acetylthiomethyl-3-phenylpropanoyl] -N-methylamino] ethanesulfonate
これらのアルキルスルホン酸アミド系界面活性剤の具体例の中で、特にＲ３が炭素数１５〜２０のアルキル基またはアルケニル基であるものは、特に親水性と疎水性のバランスに優れ、象牙質への接着性の低下抑制効果が高く特に好ましい。このような化合物は、２−（Ｎ−メチル−Ｎ−ステアロイルアミノ）エタンスルホン酸ナトリウム、２−（Ｎ−メチル−Ｎ−パルミトイルアミノ）エタンスルホン酸ナトリウム、２−［メチル（１−オキソ−９−オクタデセニル）アミノ］エタンスルホン酸ナトリウム、２−［シクロヘキシル（１−オキソオクタデシル）アミノ］エタンスルホン酸ナトリウム、２−［シクロヘキシル（１−オキソヘキサデシル）アミノ］エタンスルホン酸ナトリウム、２−［［（Ｚ）−１−オキソ−９−オクタデセニル］アミノ］エタンスルホン酸ナトリウム、２−［メチル［（９Ｚ，１２Ｚ）−１−オキソ−９，１２−オクタデカジエニル］アミノ］エタンスルホン酸ナトリウム、２−［メチル（１−オキソイコシル）アミノ］エタンスルホン酸ナトリウムが挙げられる。 Among the specific examples of these alkylsulfonic acid amide surfactants, those in which R 3 is an alkyl group or alkenyl group having 15 to 20 carbon atoms are particularly excellent in the balance between hydrophilicity and hydrophobicity, and the dentine This is particularly preferable because of its high effect of suppressing the decrease in adhesiveness to the surface. Such compounds include sodium 2- (N-methyl-N-stearoylamino) ethanesulfonate, sodium 2- (N-methyl-N-palmitoylamino) ethanesulfonate, 2- [methyl (1-oxo-9 -Octadecenyl) amino] sodium ethanesulfonate, sodium 2- [cyclohexyl (1-oxooctadecyl) amino] ethanesulfonate, sodium 2- [cyclohexyl (1-oxohexadecyl) amino] ethanesulfonate, 2-[[( Z) sodium 1-oxo-9-octadecenyl] amino] ethanesulfonate, sodium 2- [methyl [(9Z, 12Z) -1-oxo-9,12-octadecadienyl] amino] ethanesulfonate, 2 -[Methyl (1-oxoicosyl) amino] ethanesulfonic acid sodium And the like.
本発明の歯科用前処理剤において、（Ｂ）アルキルスルホン酸アミド系界面活性剤は１種類だけを使用しても良いし、複数種類のものを混合して使用しても良い。また、本発明の歯科用前処理剤における（Ｂ）アルキルスルホン酸アミド系界面活性剤の配合量は特に限定されないが、（Ａ）２３℃における水中でのｐＫａが２．５以下の酸を含む酸水溶液１００質量部に対して、象牙質への接着性の低下抑制効果が高いことから好ましくは０.０００１〜２０質量部、より好ましくは０.０１〜５質量部の割合である。 In the dental pretreatment agent of the present invention, only one type of (B) alkylsulfonic acid amide surfactant may be used, or a plurality of types may be used in combination. Further, the blending amount of the (B) alkyl sulfonic acid amide surfactant in the dental pretreatment agent of the present invention is not particularly limited, but (A) an acid having a pKa in water at 23 ° C. of 2.5 or less. Preferably, the ratio is 0.0001 to 20 parts by mass, more preferably 0.01 to 5 parts by mass, because the effect of suppressing the decrease in adhesion to dentin is high relative to 100 parts by mass of the acid aqueous solution.
本発明の歯科用前処理剤には、歯科用前処理剤を歯牙に塗布する際に垂れにくい性状とする等の操作性を改良するために、更に増粘剤を入れることができる。かかる増粘剤としては、従来公知の増粘材を使用することができる。例えば、本発明の歯科用前処理剤に可溶な高分子化合物を溶解して増粘することもできるし、無機増粘剤を分散して増粘することができる。 The dental pretreatment agent of the present invention may further contain a thickener in order to improve operability such as making it difficult to sag when the dental pretreatment agent is applied to the teeth. As such a thickener, a conventionally known thickener can be used. For example, the polymer compound soluble in the dental pretreatment agent of the present invention can be dissolved and thickened, or the inorganic thickener can be dispersed and thickened.
上述した高分子化合物としては、本発明の歯科用前処理剤に溶解可能な従来公知の高分子化合物をその増粘効果や保存安定性を考慮して適宜選択して使用することができる。このような高分子化合物としては、本発明の歯科用前処理剤に更に有機溶媒を添加し、ポリメタクリル酸メチル、ポリメタクリル酸エチル、ポリメタクリル酸プロピル、ポリメタクリル酸ブチル等のポリアルキルメタクリレート類やポリ酢酸ビニル等の非水溶性高分子を溶解させる、または非水溶性高分子を有機フィラーとして分散状態で含ませて増粘することもできるが、水溶性高分子を溶解し、増粘する方法が高い増粘効果が得られ、より好ましい。 As the above-described polymer compound, a conventionally known polymer compound that can be dissolved in the dental pretreatment agent of the present invention can be appropriately selected and used in consideration of its thickening effect and storage stability. As such a polymer compound, an organic solvent is further added to the dental pretreatment agent of the present invention, and polyalkyl methacrylates such as polymethyl methacrylate, polyethyl methacrylate, polypropyl methacrylate, and polybutyl methacrylate. It is possible to dissolve water-insoluble polymers such as polyvinyl acetate or water-insoluble polymers in the dispersed state as organic fillers, but to dissolve and thicken water-soluble polymers. The method is more preferable because a high thickening effect can be obtained.
このような水溶性高分子としては、水溶性のものであれば従来公知の高分子が制限なく使用できる。カチオン性水溶性高分子としては、ポリエチレンイミンやポリアリルアミン、ポリビニルアミン、ジメチルアミノエチルデキストラン、イミダゾール基などを含有した水溶性の高分子などが挙げられる。アニオン性水溶性高分子としては、キサンタンガム、カラギーナン、アルギン酸ナトリウム、アラビアガム、ペクチン、カルボキシビニルポリマー等のほか、ヒアルロン酸、コンドロイチン硫酸、デルマタン硫酸、ケラタン硫酸、ヘパラン硫酸等の多糖類およびこれらの塩等を挙げることができる。非イオン性水溶性高分子を例示すると、メチルセルロース、ヒドロキシメチルセルロース、ヒドロキシプロピルセルロース等のセルロース低級アルキルエーテル化合物、ポリビニルピロリドン、ポリビニルアルコール等のビニル化合物、プルラン、でんぷん等の多糖類およびその誘導体、ポリグルコシルオキシエチルメタクリレート等のポリアクリルアミド、ポリエチレンオキサイド、またはポリオキシエチレングリコール、ポリオキシプロピレングリコール、ポリオキシエチレングリコールとポリオキシプロピレングリコールのブロックコポリマー等のポリオキシアルキレングリコール等が挙げられる。 As such a water-soluble polymer, any conventionally known polymer can be used without limitation as long as it is water-soluble. Examples of the cationic water-soluble polymer include water-soluble polymers containing polyethyleneimine, polyallylamine, polyvinylamine, dimethylaminoethyldextran, imidazole group, and the like. Examples of anionic water-soluble polymers include xanthan gum, carrageenan, sodium alginate, gum arabic, pectin, carboxyvinyl polymer, etc., as well as polysaccharides such as hyaluronic acid, chondroitin sulfate, dermatan sulfate, keratan sulfate, heparan sulfate, and salts thereof. Etc. Examples of nonionic water-soluble polymers include cellulose lower alkyl ether compounds such as methyl cellulose, hydroxymethyl cellulose, and hydroxypropyl cellulose, vinyl compounds such as polyvinyl pyrrolidone and polyvinyl alcohol, polysaccharides such as pullulan and starch, and derivatives thereof, polyglucosyl Examples include polyacrylamide such as oxyethyl methacrylate, polyethylene oxide, or polyoxyalkylene glycol such as polyoxyethylene glycol, polyoxypropylene glycol, and a block copolymer of polyoxyethylene glycol and polyoxypropylene glycol.
上述した高分子化合物の重量平均分子量や分子量分布は特に限定されない。重量平均分子量が大きいほど増粘効果は高くなるので、重量平均分子量は５００以上が好ましく、特に好ましくは１５００以上である。重量平均分子量が大きすぎると歯科用前処理剤への溶解に時問がかかり、また粘度を高めようと添加量を増やした場合に糸引き状態になる場合があるので、重量平均分子量は１５０万以下が好ましく、特には８０万以下が好ましい。なお、水溶性高分子は、一種類を使用するだけでなく、二種類以上を混合して使用しても良い。 The weight average molecular weight and molecular weight distribution of the polymer compound described above are not particularly limited. Since the thickening effect increases as the weight average molecular weight increases, the weight average molecular weight is preferably 500 or more, particularly preferably 1500 or more. If the weight average molecular weight is too large, it will take time to dissolve in the dental pretreatment agent, and if the added amount is increased to increase the viscosity, it may be in a stringing state, so the weight average molecular weight is 1.5 million. The following is preferable, and 800,000 or less is particularly preferable. In addition, not only one type of water-soluble polymer but also two or more types may be mixed and used.
特に、保存安定性および易取扱性の観点から、非イオン性水溶性高分子であるポリビニルピロリドン、ポリビニルアルコールまたはポリオキシアルキレングリコールを用いることが好ましい。 In particular, from the viewpoint of storage stability and ease of handling, it is preferable to use polyvinyl pyrrolidone, polyvinyl alcohol, or polyoxyalkylene glycol, which are nonionic water-soluble polymers.
本発明の歯科用前処理剤における高分子化合物の含有量は、歯科用前処理剤組成物１００質量部中に、０．００１〜１０質量部が適当な粘度が得られやすいことから好ましい。０．００１質量部以上とすると、歯科用前処理剤組成物の増粘効果を高めることができる。また、１０質量部以上ではその分子量にもよるが粘度が高くなりすぎて糸引き状態となり操作性が不良となる場合がある。特に好ましい高分子化合物の含有量は、０．００３質量部以上７質量部以下の範囲であり、特に好ましくは０．００５〜５質量部の範囲である。 The content of the polymer compound in the dental pretreatment agent of the present invention is preferably 0.001 to 10 parts by mass in 100 parts by mass of the dental pretreatment composition because an appropriate viscosity is easily obtained. When it is 0.001 part by mass or more, the thickening effect of the dental pretreatment composition can be enhanced. On the other hand, when the amount is 10 parts by mass or more, although depending on the molecular weight, the viscosity becomes too high and the threading state may occur, resulting in poor operability. The content of the polymer compound is particularly preferably in the range of 0.003 parts by mass to 7 parts by mass, and particularly preferably in the range of 0.005 to 5 parts by mass.
また、無機増粘剤を本発明の歯科用前処理剤に分散することによって、増粘剤として使用することができる。このような無機増粘剤としては、従来公知の無機粒子を使用することができる。このような無機増粘剤を例示すると、シリカ（乾式法や湿式法で調製されたもの等）、シリカアルミナ、アルミナ、アルミナ石英、ガラス（バリウムガラスを含む）、チタニア、ジルコニア（酸化ジルコニウム）、炭酸カルシウム、カオリン、クレー、雲母、硫酸アルミニウム、硫酸バリウム、硫酸カルシウム、酸化チタン、リン酸カルシウムなどを挙げることができる。これらの無機増粘剤はあらかじめシランカップリング剤やチタネートカップリング剤で表面処理されていてもよい。これらの中でも乾式法で製造されたシリカであるフュームドシリカを使用し、増粘する方法が高い増粘効果が得られ、より好ましい。 Moreover, an inorganic thickener can be used as a thickener by dispersing it in the dental pretreatment agent of the present invention. As such an inorganic thickener, conventionally known inorganic particles can be used. Examples of such inorganic thickeners include silica (prepared by a dry method or a wet method), silica alumina, alumina, alumina quartz, glass (including barium glass), titania, zirconia (zirconium oxide), Examples thereof include calcium carbonate, kaolin, clay, mica, aluminum sulfate, barium sulfate, calcium sulfate, titanium oxide, and calcium phosphate. These inorganic thickeners may be surface-treated with a silane coupling agent or a titanate coupling agent in advance. Among these, a fumed silica, which is silica produced by a dry method, is used, and a method of thickening is preferable because a high thickening effect is obtained.
本発明における無機増粘剤の含有量は、好適な粘度が得られることから本発明の歯科用前処理剤１００質量部中に好ましくは０.１〜５０質量部、より好ましくは１〜３０質量部の範囲で含有される。好適なヒュームドシリカの含有量は４〜１０質量部であり、特に好適には５〜８質量部である。 The content of the inorganic thickener in the present invention is preferably 0.1 to 50 parts by mass, more preferably 1 to 30 parts by mass in 100 parts by mass of the dental pretreatment agent of the present invention because a suitable viscosity is obtained. In a range of parts. The preferable fumed silica content is 4 to 10 parts by mass, and particularly preferably 5 to 8 parts by mass.
本発明の歯科用前処理剤に使用する増粘剤としては、上述した高分子化合物または無機増粘剤のいずれかを単独で使用しても良いし、高分子化合物および無機増粘剤のそれぞれ１種類以上を組み合わせて使用しても良い。 As the thickener used in the dental pretreatment agent of the present invention, either the above-described polymer compound or inorganic thickener may be used alone, or each of the polymer compound and inorganic thickener. One or more types may be used in combination.
本発明の歯科用前処理剤組成物には、本発明の効果に悪影響を及ぼさない限り、他の添加剤を配合しても良い。例えば、各種天然色素類やタール色素類等の着色剤、蛍光剤または香味剤を添加しても良い。また、抗菌性を付与する目的で、塩化ベンザルコニウム、セチルピリジニウムクロライド等の抗菌性物質を添加しても良い。また、マトリクスメタプロテアーゼ等のタンパク質分解酵素の活性を阻害するクロルヘキシジン等の薬効成分を配合しても良い。更には、各種有機溶媒、各種重合性単量体や各種化学・光重合開始剤を添加してもよい。 Other additives may be added to the dental pretreatment composition of the present invention as long as the effects of the present invention are not adversely affected. For example, coloring agents such as various natural pigments and tar pigments, fluorescent agents, and flavoring agents may be added. Further, for the purpose of imparting antibacterial properties, antibacterial substances such as benzalkonium chloride and cetylpyridinium chloride may be added. Moreover, you may mix | blend medicinal ingredients, such as chlorhexidine which inhibits the activity of proteolytic enzymes, such as matrix metaprotease. Furthermore, various organic solvents, various polymerizable monomers, and various chemical / photopolymerization initiators may be added.
このような有機溶媒としては、エタノール、プロパノール、ブタノール等のアルコール類やアセトン等が使用できる。これら有機溶媒の使用量は特に限定されないが、通常（Ａ）酸水溶液１００質量部に対して１〜１０００質量部、好ましくは１０〜５００質量部である。 As such an organic solvent, alcohols such as ethanol, propanol and butanol, acetone and the like can be used. Although the usage-amount of these organic solvents is not specifically limited, Usually, it is 1-1000 mass parts with respect to 100 mass parts of (A) acid aqueous solution, Preferably it is 10-500 mass parts.
また、重合性単量体を含ませた場合は、本発明の歯科用前処理剤による処理と同時に重合性単量体を象牙質に浸透できる。 Moreover, when a polymerizable monomer is included, the polymerizable monomer can penetrate into the dentin simultaneously with the treatment with the dental pretreatment agent of the present invention.
このような重合性単量体としては、（メタ）アクリル酸メチルなどの（メタ）アクリル酸の脂肪族エステル類；トリエチレングリコールジ（メタ）アクリレートなどのポリエチレングリコールジ（メタ）アクリレート類；プロピレングリコールジ（メタ）アクリレートなどのポリプロピレングリコールジ（メタ）アクリレート類；２−（メタ）アクリロイルオキシエチルイソシアネート、２,２,４−トリメチルヘキサメチレンジイソシアネート、又は１,３,５−トリメチルヘキサメチレンジイソシアネートと２−ヒドロキシエチル（メタ）アクリレートとの付加物などのウレタン結合を有する（メタ）アクリレート類；ビスフェノールＡにオキシエチレンを付加させた生成物にさらに（メタ）アクリル酸を縮合させた２,２−ビス（４−（メタ）アクリロイルオキシポリエトキシフェニル）プロパン類；２−ヒドロキシエチル（メタ）アクリレートなどの水酸基含有の（メタ）アクリレート類；メチロール（メタ）アクリルアミド、Ｎ−（メタ）アクリロイル−２,３−ジヒドロキシプロピルアミンなどの水酸基含有の（メタ）アクリルアミド類；１モルのビスフェノールＡと２モルのグリシジル（メタ）アクリレート（メタクリレートの場合ＧＭＡ）の付加反応生成物（メタクリレートの場合Ｂｉｓ−ＧＭＡ）などのＧＭＡと脂肪族もしくは芳香族ポリオール（フェノールを含む）との付加生成物；スチレン、４−メチルスチレン、４−クロルメチルスチレン、ジビニルベンゼンなどのスチレン誘導体類；酢酸ビニルなどを挙げることができる。 Examples of the polymerizable monomer include aliphatic esters of (meth) acrylic acid such as methyl (meth) acrylate; polyethylene glycol di (meth) acrylates such as triethylene glycol di (meth) acrylate; propylene Polypropylene glycol di (meth) acrylates such as glycol di (meth) acrylate; 2- (meth) acryloyloxyethyl isocyanate, 2,2,4-trimethylhexamethylene diisocyanate, or 1,3,5-trimethylhexamethylene diisocyanate (Meth) acrylates having a urethane bond such as an adduct with 2-hydroxyethyl (meth) acrylate; a product obtained by adding oxyethylene to bisphenol A and further condensing (meth) acrylic acid; Bis (4- (Meta (Acryloyloxypolyethoxyphenyl) propanes; hydroxyl-containing (meth) acrylates such as 2-hydroxyethyl (meth) acrylate; methylol (meth) acrylamide, N- (meth) acryloyl-2,3-dihydroxypropylamine, etc. Hydroxyl-containing (meth) acrylamides; GMA such as 1 mol of bisphenol A and 2 mol of glycidyl (meth) acrylate (GMA in the case of methacrylate) addition product (Bis-GMA in the case of methacrylate) and aliphatic or aromatic Addition products with a group polyol (including phenol); styrene derivatives such as styrene, 4-methylstyrene, 4-chloromethylstyrene, divinylbenzene; vinyl acetate, and the like.
同様に、重合性単量体として、分子内に少なくとも１つの、酸性基と重合性基とを有する重合性単量体が挙げられる。重合性基として、例えば（メタ）アクリロイル基、スチリル基、ビニル基、アリル基などを有するラジカル重合可能な不飽和基を挙げることができる。また、酸性基としては、カルボキシル酸基、リン酸基、チオリン酸基、スルホン酸基およびスルフィン酸基などを挙げることができる。このような酸性基と重合性基を有する重合性単量体としては、（メタ）アクリル酸、１１−（メタ）アクリロイルオキシ−１,１−ウンデカンジカルボン酸（メタクリレートの場合：ＭＡＣ−１０）等のカルボキシル基を有するもの；２−（メタ）アクリロイルオキシエチルアシドホスフェート、６−（メタ）アクリロイルオキシヘキシルアシドホスフェート、１０−（メタ）アクリロイルオキシデシルアシドホスフェート等のリン酸基を有するもの；２または１−スルホ−１または２−プロピル（メタ）アクリレート、１,１−ジメチル−２−スルホエチル（メタ）アクリルアミドなどのスルホン酸基を有するもの；等を挙げることができる。 Similarly, examples of the polymerizable monomer include polymerizable monomers having at least one acidic group and polymerizable group in the molecule. Examples of the polymerizable group include radically polymerizable unsaturated groups having, for example, a (meth) acryloyl group, a styryl group, a vinyl group, and an allyl group. Examples of the acidic group include a carboxylic acid group, a phosphoric acid group, a thiophosphoric acid group, a sulfonic acid group, and a sulfinic acid group. Examples of the polymerizable monomer having an acidic group and a polymerizable group include (meth) acrylic acid, 11- (meth) acryloyloxy-1,1-undecanedicarboxylic acid (in the case of methacrylate: MAC-10), and the like. Having a carboxyl group of 2; having a phosphate group such as 2- (meth) acryloyloxyethyl acid phosphate, 6- (meth) acryloyloxyhexyl acid phosphate, 10- (meth) acryloyloxydecyl acid phosphate; 2 or Examples thereof include those having a sulfonic acid group such as 1-sulfo-1 or 2-propyl (meth) acrylate and 1,1-dimethyl-2-sulfoethyl (meth) acrylamide.
これらの重合性単量体は、単独で使用してもよく、また複数種類を組み合わせて使用することもできる。本発明の歯科用前処理剤に含ませる重合性単量体の量は特に限定されない。通常、歯科用前処理剤１００質量部に対し重合性単量体を１質量部以上４００質量部以下である。 These polymerizable monomers may be used alone or in combination of a plurality of types. The amount of the polymerizable monomer contained in the dental pretreatment agent of the present invention is not particularly limited. Usually, the polymerizable monomer is 1 part by mass or more and 400 parts by mass or less with respect to 100 parts by mass of the dental pretreatment agent.
本発明の歯科用前処理剤には、従来公知の各種化学・光重合開始剤を配合することができる。化学重合開始剤としては、有機過酸化物／アミン化合物、有機過酸化物／アミン化合物／スルフィン酸塩からなるレドックス型の重合開始剤；アリールボレート塩等の酸と反応して重合を開始する有機金属型の重合開始剤；および（チオ）バルビツール酸誘導体／第二銅イオン／ハロゲン化合物からなる重合開始剤；等が例示できる。また、光重合開始剤としては、光増感剤のみからなるもの；光増感材／光重合促進剤からなるもの；色素／光酸発生剤／アリールボレート塩からなるもの等が挙げられる。これらは単独で、または複数を組み合わせて添加することができる。本発明の歯科用前処理剤に含ませる重合開始剤の量は特に限定されない。通常、歯科用前処理剤１００質量部に対し重合開始剤を０．０１質量部以上５０質量部以下である。 Various conventionally known chemical / photopolymerization initiators can be blended in the dental pretreatment agent of the present invention. Chemical polymerization initiators include redox type polymerization initiators composed of organic peroxide / amine compounds, organic peroxides / amine compounds / sulfinates; organics that react with acids such as aryl borate salts to initiate polymerization. Examples thereof include metal type polymerization initiators; and (thio) barbituric acid derivatives / cupric ion / halogen compound polymerization initiators; Moreover, as a photoinitiator, what consists only of photosensitizers; what consists of a photosensitizer / photopolymerization accelerator; what consists of pigment | dye / photoacid generator / aryl borate salt etc. are mentioned. These can be added alone or in combination. The amount of the polymerization initiator contained in the dental pretreatment agent of the present invention is not particularly limited. Usually, the polymerization initiator is 0.01 parts by mass or more and 50 parts by mass or less with respect to 100 parts by mass of the dental pretreatment agent.
本発明の歯科用前処理剤の包装形態は、種々の方法で行われる。例えば、歯科用前処理剤をシリンジ、点眼瓶、チューブ、または袋等の容器に包装できる。また、歯科用前処理剤を使用時に混合できるように、固体および液体の配合物を別々に包装しても良い。上記した包装形態の中でも、直接歯牙表面に吐出して適用・塗布することができ操作が簡便であることから、シリンジによる包装が好ましい。このようなシリンジは、従来公知のシリンジが制限なく使用できるが、長期間保管後の気密性が高いものが保存安定性の観点から好ましく、またルアーロックタイプのものがチップの予期せぬ脱離による内容物の飛散を防止できて好適である。 The packaging form of the dental pretreatment agent of the present invention is performed by various methods. For example, the dental pretreatment agent can be packaged in a container such as a syringe, an eye drop bottle, a tube, or a bag. Also, the solid and liquid formulations may be packaged separately so that the dental pretreatment agent can be mixed at the time of use. Among the packaging forms described above, packaging with a syringe is preferable because it can be directly applied to the tooth surface for application and application, and the operation is simple. As such a syringe, a conventionally known syringe can be used without limitation, but a highly airtight after long-term storage is preferable from the viewpoint of storage stability, and a luer lock type is unexpectedly detached from the chip. It is preferable to prevent the contents from scattering.
次に、本発明の歯科用前処理剤の使用方法について説明する。まず、患者の歯牙の欠損部分や非切削歯牙の表面等の被着面に、歯科用前処理剤をブラシやスポンジで塗布またはシリンジから直接供給する。数秒ないし数分間作用させた後、処理面を洗浄し乾燥する。次に、その部分に接着剤またはコンポジットレジン等の歯科用硬化性組成物を塗布あるいは充填する。 Next, a method for using the dental pretreatment agent of the present invention will be described. First, a dental pretreatment agent is applied with a brush or a sponge or directly supplied from a syringe onto an adherend surface such as a defective portion of a patient's tooth or the surface of a non-cut tooth. After acting for several seconds to several minutes, the treated surface is cleaned and dried. Next, a dental curable composition such as an adhesive or a composite resin is applied or filled into the portion.
本発明の歯科用前処理剤は、歯牙のエナメル質のみならず、エナメル質の下層に存在する象牙質、セメント質等に適用しても良い。さらに・金属製・セラミックス製、コンポジットレジン製等の歯牙修復材料に対しても清掃等の目的で使用することができる。本発明の歯科用前処理剤を用いることによって、象牙質に適用した場合もその後に適用する歯科用硬化性組成物の接着性の低下が低減できるため、効果的に歯牙の修復を行うことができる。 The dental pretreatment agent of the present invention may be applied not only to tooth enamel, but also to dentin, cement and the like existing in the lower layer of the enamel. Furthermore, it can be used for the purpose of cleaning or the like for tooth restoration materials made of metal, ceramics, composite resin or the like. By using the dental pretreatment agent of the present invention, even when applied to dentin, the decrease in adhesiveness of the dental curable composition applied thereafter can be reduced, so that the tooth can be effectively restored. it can.
以下実施例により本発明の歯科用前処理剤を具体的に説明するが、本発明はこれらの実施例によって何ら限定されるものではない。 EXAMPLES The dental pretreatment agent of the present invention will be specifically described below with reference to examples, but the present invention is not limited to these examples.
尚、実施例および比較例で使用した化合物とその略称を（１）に、エナメル質および象牙質への接着試験力の測定方法を（２）に示した。 The compounds used in Examples and Comparative Examples and their abbreviations are shown in (1), and the method for measuring the adhesion test force to enamel and dentin is shown in (2).
（１）実施例および比較例に使用した化合物とその略称
〔酸水溶液〕
酸水溶液１：３６質量％のリン酸水溶液（８５％リン酸を４２．４質量部と水を５７．６質量部の混合物）
酸水溶液２：１０質量％の塩酸水溶液
酸水溶液３：５５質量％のリン酸水溶液（８５％リン酸を６４．７質量部と水を３５．３質量部の混合物）
酸水溶液４：３６質量％のクエン酸水溶液
〔界面活性剤〕
・アルキルスルホン酸アミド系界面活性剤
Ｓ１；２−［メチル（１−オキソ−９−オクタデセニル）アミノ］エタンスルホン酸ナトリウム
Ｓ２；２−［［（Ｚ）−１−オキソ−９−オクタデセニル］アミノ］エタンスルホン酸ナトリウム
Ｓ３；２−（Ｎ−メチル−Ｎ−ステアロイルアミノ）エタンスルホン酸ナトリウム
Ｓ４；２−［シクロヘキシル（１−オキソテトラデシル）アミノ］エタンスルホン酸ナトリウム
Ｓ５；２−［ラウロイル（メチル）アミノ］エタンスルホン酸ナトリウム
・その他の界面活性剤
Ｓ６；ドデシルベンゼンスルホン酸ナトリウム
(1) Compounds used in Examples and Comparative Examples and their abbreviations [acid aqueous solution]
Acid aqueous solution 1: 36% by mass phosphoric acid aqueous solution (a mixture of 42.4 parts by mass of 85% phosphoric acid and 57.6 parts by mass of water)
Acid aqueous solution 2: 10 mass% hydrochloric acid aqueous solution 3: 55 mass% phosphoric acid aqueous solution (mixture of 64.7 parts by mass of 85% phosphoric acid and 35.3 parts by mass of water)
Acid aqueous solution 4:36 mass% citric acid aqueous solution [surfactant]
Alkylsulfonic acid amide-based surfactant S1; 2- [methyl (1-oxo-9-octadecenyl) amino] ethanesulfonic acid sodium S2; 2-[[(Z) -1-oxo-9-octadecenyl] amino] Sodium ethanesulfonate S3; Sodium 2- (N-methyl-N-stearoylamino) ethanesulfonate S4; Sodium 2- [cyclohexyl (1-oxotetradecyl) amino] ethanesulfonate S5; 2- [Lauroyl (methyl) Amino] sodium ethanesulfonate / other surfactant S6; sodium dodecylbenzenesulfonate
（２）エナメル質および象牙質への接着試験力の測定方法
屠殺後２４時間以内の牛前歯のエナメル質平面又は象牙質平面を注水下、＃６００のエメリーペーパーで唇面に平行になるように削り出した。次にその面に圧縮空気を約１０秒間吹きつけて乾燥した後、そのエナメル質平面又は象牙質平面に、直径３ｍｍの孔のあいた両面テープを貼った。次に、厚さ０．５ｍｍ直径８ｍｍの孔の開いたパラフィンワックスを上記円孔上に同一中心となるように固定して模擬窩洞を形成した。この模擬窩洞内の上記直径３ｍｍの孔内のエナメル質平面又は象牙質平面に、表１に示す実施例および比較例の歯科用前処理剤を歯科用マイクロブラシを使用し塗布し、１０秒間処理し、１０秒間歯科用水銃で水洗後、圧縮空気により１０秒間乾燥した。次いで、上記直径３ｍｍの孔内のエナメル質または象牙質の歯科用前処理剤処理面に歯質用象牙質接着材（トクヤマボンドフォース、トクヤマデンタル社製）を歯科用マイクロブラシを使用し塗布し、２０秒間放置後、圧縮空気を約１０秒間吹き付けて乾燥し、歯科用可視光照射器（トクソーパワーライト、トクヤマ社製）にて１０秒間光照射した。さらにその上に歯科用コンポジットレジン（エステライトＰクイック、トクヤマデンタル社 製）を充填し、前記歯科用可視光照射器により１０秒間光照射した接着試料を得た。ビスタイトII（トクヤマデンタル社製）を接着剤として使用して、前記の接着試料のコンポジットレジン面上にステンレス棒を接着させ、接着試験片とした。接着試験片を３７℃の水中に２４時間浸漬した。次いで、引張り試験機（オートグラフ、島津製作所製）を用いてクロスヘッドスピード２ｍｍ/ｍｉｎにて引張り試験を行い、エナメル質及び象牙質への引張り接着強度を測定した。１試験当たり４本の接着試験片について引張り接着強さを測定し、その平均値を接着強度とした。
(2) Measuring method of adhesion test force to enamel and dentin Make the enamel plane or dentin plane of bovine anterior teeth within 24 hours after slaughter under water, and make it parallel to the lip with # 600 emery paper I carved out. Next, the surface was dried by blowing compressed air for about 10 seconds, and then a double-sided tape having a hole with a diameter of 3 mm was attached to the enamel plane or dentin plane. Next, a paraffin wax having a hole with a thickness of 0.5 mm and a diameter of 8 mm was fixed on the circular hole so as to have the same center, thereby forming a simulated cavity. The dental pretreatment agents of Examples and Comparative Examples shown in Table 1 are applied to the enamel plane or the dentin plane in the hole with a diameter of 3 mm in the simulated cavity using a dental microbrush and treated for 10 seconds. After washing with a dental water gun for 10 seconds, it was dried with compressed air for 10 seconds. Next, a dentin adhesive material for dentin (Tokuyama Bond Force, manufactured by Tokuyama Dental Co., Ltd.) is applied to the enamel or dentin dental pretreatment surface within the 3 mm diameter hole using a dental microbrush. After leaving for 20 seconds, compressed air was blown for about 10 seconds to dry, and irradiation was performed for 10 seconds with a dental visible light irradiator (Tokuso Power Light, manufactured by Tokuyama Corporation). Furthermore, a dental composite resin (Estellite P Quick, manufactured by Tokuyama Dental Co., Ltd.) was filled thereon, and an adhesive sample irradiated with the dental visible light irradiator for 10 seconds was obtained. A stainless steel rod was adhered on the composite resin surface of the above-mentioned adhesion sample using vis-tite II (manufactured by Tokuyama Dental Co., Ltd.) as an adhesive to obtain an adhesion test piece. The adhesion test piece was immersed in water at 37 ° C. for 24 hours. Next, a tensile test was performed at a crosshead speed of 2 mm / min using a tensile tester (Autograph, manufactured by Shimadzu Corporation), and tensile adhesion strength to enamel and dentin was measured. Tensile bond strength was measured for four adhesion test pieces per test, and the average value was defined as the bond strength.
(実施例１〜１２、比較例１〜４）
表１に示す歯科用前処理剤１〜１２および比較歯科用前処理剤１〜４を使用し、（２）エナメル質および象牙質への接着試験力の測定方法に従い歯質接着強度を評価した。評価結果を表１に示した。
(Examples 1-12, Comparative Examples 1-4)
Dental pretreatment agents 1-12 and comparative dental pretreatment agents 1-4 shown in Table 1 were used, and (2) tooth adhesion strength was evaluated according to a method for measuring adhesion test force to enamel and dentin. . The evaluation results are shown in Table 1.
実施例１〜１２のように、本発明の（Ｂ）アルキルスルホン酸アミド系界面活性剤を含有する歯科用前処理剤を使用した場合は、エナメル質及び象牙質共に高い接着強度が得られ、特に、比較例１〜３との比較から、界面活性剤を含有しない歯科用前処理剤を使用したり、アルキルスルホン酸アミド系以外の界面活性剤を含有する歯科用前処理剤を使用した歯科用前処理剤を使用した場合よりも、象牙質に対する接着強度が著しく上回る結果であった。また、比較例４との比較から、歯科用前処理剤の酸水溶液が、２３℃における水中でのｐＫａが２．５以下になるような強酸でないとエナメル質に対する接着性が大きく低下することが確認できた。 As in Examples 1 to 12, when the dental pretreatment agent containing the (B) alkyl sulfonic acid amide surfactant of the present invention was used, high adhesion strength was obtained for both enamel and dentin, In particular, from comparisons with Comparative Examples 1 to 3, a dental pretreatment agent that does not contain a surfactant or a dental pretreatment agent that contains a surfactant other than an alkylsulfonic acid amide type is used. Compared to the case where the pretreatment agent for use was used, the adhesion strength to the dentin was significantly exceeded. Further, from the comparison with Comparative Example 4, if the acid aqueous solution of the dental pretreatment agent is not a strong acid whose pKa in water at 23 ° C. is 2.5 or less, the adhesion to enamel may be greatly reduced. It could be confirmed.
さらに、実施例１〜３と実施例４、５の比較から、記式（１）の構造であるアルキルスルホン酸アミド系界面活性剤において、Ｒ３の炭素数が１５〜２０であるＳ１、Ｓ２およびＳ３を使用した場合は特に高い象牙質接着強度が得られた。実施例１１と実施例１の比較から、リン酸で処理した場合にはリン酸濃度が高いにも関わらず塩酸処理と比較して高い象牙質接着強度が得られた。 Furthermore, from the comparison between Examples 1 to 3 and Examples 4 and 5, in the alkylsulfonic acid amide surfactant having the structure of the formula (1), S 3 and S 2 in which R 3 has 15 to 20 carbon atoms When S3 and S3 were used, particularly high dentin bond strength was obtained. From a comparison between Example 11 and Example 1, when treated with phosphoric acid, high dentin bond strength was obtained compared with hydrochloric acid treatment despite the high phosphoric acid concentration.
Claims (6)
ＭＳＯ３−Ｒ１−Ｎ（Ｒ２）（Ｃ＝Ｏ）−Ｒ３・・・式（１）
（式中Ｍは、水素原子または１価の対カチオンであり、
Ｒ１は、炭素数５以下のアルキレン基であり、
Ｒ２は、水素原子、又は炭素数６以下のアルキル基若しくは炭素数３〜６のシクロアルキル基であり、
Ｒ３は、炭素数４〜３０のアルキル基、炭素数４〜３０のアルケニル基、炭素数４〜１０のシクロアルキル基、又は炭素数６〜３０の芳香族炭化水素基である） The dental pretreatment agent according to claim 1, wherein the (B) alkylsulfonic acid amide surfactant has a structure represented by the following formula (1).
MSO 3 -R 1 -N (R 2 ) (C = O) -R 3 ··· Equation (1)
(In the formula, M is a hydrogen atom or a monovalent counter cation,
R 1 is an alkylene group having 5 or less carbon atoms,
R 2 is a hydrogen atom, an alkyl group having 6 or less carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms,
R 3 is an alkyl group having 4 to 30 carbon atoms, an alkenyl group having 4 to 30 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 30 carbon atoms)
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| JPH048368A (en) * | 1990-04-26 | 1992-01-13 | Shiyoufuu:Kk | Primer composition |
| JPH08198723A (en) * | 1994-11-24 | 1996-08-06 | San Medical Kk | Dental pretreating agent |
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| JPH048368A (en) * | 1990-04-26 | 1992-01-13 | Shiyoufuu:Kk | Primer composition |
| JPH08198723A (en) * | 1994-11-24 | 1996-08-06 | San Medical Kk | Dental pretreating agent |
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