JPH0686367B2 - Tooth surface treatment agent - Google Patents
Tooth surface treatment agentInfo
- Publication number
- JPH0686367B2 JPH0686367B2 JP63246063A JP24606388A JPH0686367B2 JP H0686367 B2 JPH0686367 B2 JP H0686367B2 JP 63246063 A JP63246063 A JP 63246063A JP 24606388 A JP24606388 A JP 24606388A JP H0686367 B2 JPH0686367 B2 JP H0686367B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- tooth surface
- anhydride
- dentin
- organic carboxylic
- 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.)
- Expired - Lifetime
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Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は歯科医療分野において、歯質に対して接着性を
有する材料を用いて治療する場合に、歯の表面又は窩洞
内面を処理する歯面処理剤に関する。特に、コンポジツ
トレジンに代表される充填修復材料、小窩裂溝填塞材、
接着性セメント等を用いて虫歯等を治療する際に、これ
らの材料を歯質に強固に接着するために歯面を処理する
材料に関するものである。TECHNICAL FIELD The present invention relates to a tooth for treating the surface of the tooth or the inner surface of the cavity in the field of dentistry when treating with a material having an adhesive property to the tooth structure. The present invention relates to a surface treatment agent. In particular, filling restoration material represented by composites resin, pit fissure filling material,
The present invention relates to a material for treating a tooth surface in order to firmly bond these materials to tooth structure when treating dental caries or the like using an adhesive cement or the like.
（従来の技術） 虫歯の治療に用いられる有機材料（コンポジツトレジ
ン、グラスアイオノマーセメント、カルボキシレートセ
メント、コンポジツトレジンセメント、小窩裂溝填塞材
など）を歯面に接着させるため、エナメル質を酸水溶液
等で処理することが行われている。この処理材として
は、種々の濃度のリン酸やクエン酸の水溶液が歯面処理
剤として推奨されているが、処理効果の点から20〜60重
量％濃度のリン酸水溶液が最も一般的に使用されてい
る。(Prior art) To bond the organic materials used for the treatment of caries (composites resin, glass ionomer cement, carboxylate cement, composites resin cement, pit fissure filling material, etc.) to the tooth surface, enamel is applied. Treatment with an aqueous acid solution or the like is performed. Aqueous solutions of phosphoric acid and citric acid with various concentrations are recommended as tooth treatment agents for this treatment, but from the viewpoint of treatment effect, an aqueous solution of phosphoric acid with a concentration of 20-60 wt% is most commonly used. Has been done.
特に、う蝕部分の充填修復に用いられるコンポジツトレ
ジンは合成樹脂と無機質フイラーからなるが、歯質と接
着しにくいため接着性の改善方法が種々検討されてき
た。従来、最も効果的な修復方法として、う蝕部分を除
去した窩洞のエナメル質壁を酸水溶液（例えば、リン酸
水溶液）でエツチング処理し、コンポジツトレジンの合
成樹脂成分である重合性単量体からなる接着剤を該処理
面に塗布したのちコンポジツトレジンで充填修復する方
法が知られている。しかし、歯面はエナメル質および象
牙質から構成されており、特に充填修復する場合はう蝕
部分を除去して作成した窩洞にエナメル質および象牙質
の壁面が存在するため、コンポジツトレジンをエナメル
質及び象牙質の双方に強固に接着させることが望まし
い。このため、象牙質に接着する特別の重合性単量体を
含む接着剤が用いられるようになっている。In particular, the composite resin used for filling and repairing a carious part is composed of a synthetic resin and an inorganic filler, but various methods for improving the adhesiveness have been studied because they are difficult to adhere to the tooth structure. Conventionally, as the most effective repairing method, the enamel wall of the cavity in which the carious part has been removed is subjected to etching treatment with an acid aqueous solution (for example, phosphoric acid aqueous solution), and a polymerizable monomer that is a synthetic resin component of compositz resin. There is known a method in which an adhesive consisting of (1) is applied to the treated surface and then the filling and restoration is carried out with a composite resin. However, the tooth surface is composed of enamel and dentin, and especially when filling and repairing, the enamel and dentin walls are present in the cavity created by removing the carious part, so the composite resin is applied to the enamel. A strong bond to both the quality and the dentin is desirable. Therefore, an adhesive containing a special polymerizable monomer that adheres to dentin has been used.
ところで、歯質を研削具で削除すると切削屑が該接着表
面に付着する。この切削屑にはう蝕部分に存在した細菌
や口腔内に浮遊する細菌が取り込まれていると推定され
ている。仮に、この切削屑を残したまま複合レジン等で
修復すると、該複合レジンと該切削屑が強固に接着して
も、歯面と切削屑の間の接着が不十分なため、この間で
剥離を生ずることになる。また、切削屑の中に存在する
細菌による歯髄への刺激も懸念される。このため、コン
ポジツトレジンで充填修復する前に該切削屑を除去する
ことが望ましい。上述のリン酸水溶液により窩洞全面を
処理すれば、エナメル質及び象牙質表面に付着する切削
屑は完全に除去されるが、切削屑で封鎖されていた象牙
細管が開口するため、刺激物質が開口した象牙細管を通
つて歯髄に到達し、為害作用を及ぼすことを懸念する考
えもある。そこで、リン酸にかわる象牙質の歯面処理剤
として種々の有機カルボン酸を歯面処理剤とする研究が
進められ、クエン酸、シユウ酸、蟻酸等の水溶液、また
は／およびシユウ酸第２鉄、塩化鉄等の金属塩との使用
が象牙質の処理剤として有効との報告がある（例えば、
中林ら、歯科理工学雑誌、第23巻61号第29〜33頁（1982
年））。然るに、これらの公知の歯面処理剤でエナメル
質を処理しても、リン酸水溶液で処理する場合に比べて
コンポジツトレジンとエナメル質問の接着力が十分では
ない。このため、かかる歯面処理剤を用いる場合には、
前もつて有機カルボン酸等で象牙質を処理したのち、再
びリン酸水溶液等でエナメル質を処理しなければなら
ず、煩雑な操作となる。By the way, when the tooth substance is removed with a grinding tool, cutting waste adheres to the adhesive surface. It is presumed that the cutting debris incorporates bacteria existing in the carious part and bacteria floating in the oral cavity. If the composite resin and the cutting waste are firmly adhered to each other when the cutting waste is left, the adhesion between the tooth surface and the cutting waste is insufficient, so that peeling occurs between them. Will occur. In addition, there is a concern that the bacteria present in the cutting waste may stimulate the dental pulp. For this reason, it is desirable to remove the cutting waste before performing the filling restoration with the composite resin. If the entire surface of the cavity is treated with the above-mentioned phosphoric acid aqueous solution, the cutting debris adhering to the enamel and dentin surfaces will be completely removed, but the dentinal tubules blocked by the cutting debris will open, so the stimulating substance will open. There is a concern that it may reach the pulp through the dentin tubules and cause harmful effects. Therefore, studies have been conducted to use various organic carboxylic acids as tooth surface treatment agents instead of phosphoric acid as dentin surface treatment solutions, such as an aqueous solution of citric acid, oxalic acid, formic acid, etc., and / or ferric oxalate. , It has been reported that the use of metal salts such as iron chloride is effective as a treatment agent for dentin (for example,
Nakabayashi et al., Dental Science and Engineering, Vol. 23, No. 61, pp. 29-33 (1982
Year)). However, even if the enamel is treated with these known tooth surface treating agents, the adhesive force between the composite resin and the enamel question is not sufficient as compared with the case of treating with the phosphoric acid aqueous solution. Therefore, when using such a tooth surface treating agent,
After the dentin must be treated with an organic carboxylic acid or the like before, the enamel must be treated again with an aqueous solution of phosphoric acid or the like, which is a complicated operation.
（発明が解決しようとする課題） 上述のごとく、有機カルボン酸からなる歯面処理剤は象
牙質に対しては有効であるが、エナメル質に対しては十
分な処理効果を発揮できない。このため、かかる歯面処
理剤を用いる場合には、象牙質を処理したのち再びリン
酸水溶液等でエナメル質を処理しなければならず、臨床
上からも煩雑な操作が必要であり、歯面処理剤として一
般的に用いるには不適当である。(Problems to be Solved by the Invention) As described above, the tooth surface treating agent composed of an organic carboxylic acid is effective for dentin, but cannot sufficiently exert an effect for enamel. For this reason, when using such a tooth surface treating agent, it is necessary to treat the dentin and then treat the enamel again with an aqueous solution of phosphoric acid or the like, which requires a complicated operation from the clinical point of view. It is unsuitable for general use as a treating agent.
また、歯面処理剤の特性として、エナメル質および象牙
質に対する接着力増強のための処理効果が最も重要であ
るが、象牙質（特に、コラーゲン）の変性作用が少ない
ことも望ましい。Further, as a characteristic of the tooth surface treating agent, the treatment effect for enhancing the adhesive strength to enamel and dentin is the most important, but it is also desirable that the dentin (particularly collagen) has a small denaturing action.
（課題を解決するための手段） 本発明者はこの点に着目し、リン酸に代わるエナメル質
と象牙質を同時に処理できる歯面処理剤について鋭意検
討した結果、本発明に至つた。(Means for Solving the Problems) The present inventor has focused on this point and, as a result of extensive studies on a tooth surface treating agent capable of simultaneously treating enamel and dentin instead of phosphoric acid, the present invention has been accomplished.
すなわち、歯面処理剤の基質として象牙質表面を処理し
ても歯髄に対する為害作用がないとされている有機カル
ボン酸を用い、本有機カルボン酸のエナメル質に対する
処理効果を増強する特定の添加物とその濃度について鋭
意検討し、エナメル質と象牙質を同時に処理できる歯面
処理剤を発明するに至つた。That is, using an organic carboxylic acid, which is said to have no harmful effect on the pulp even if the dentin surface is treated as a substrate for the tooth surface treatment agent, a specific additive that enhances the treatment effect of the organic carboxylic acid on the enamel. The present invention has led to the invention of a tooth surface treating agent capable of treating enamel and dentin at the same time.
本発明の歯面処理剤は、有機カルボン酸、塩化カルシウ
ム及び水を主要成分としている。The tooth surface treating agent of the present invention contains organic carboxylic acid, calcium chloride and water as main components.
本発明の処理剤に使用できる有機カルボン酸としてはモ
ノカルボン酸、ジカルボン酸、トリカルボン酸、テトラ
カルボン酸およびそれらの酸無水物等が用いられる。モ
ノカルボン酸およびその酸無水物としてはギ酸、酢酸、
乳酸、酪酸、吉草酸、ノナン酸、ヘキサン酸、ヘプタン
酸、ラウリン酸、ピルビン酸、グリシン、メタクリル
酸、アクリル酸、クロトン酸、安息香酸、アミノ安息香
酸、サリチル酸、アミノサリチル酸、無水酢酸、無水酪
酸、無水吉草酸、無水ラウリン酸、無水グリシン、無水
クロトン酸、および無水安息香酸等が挙げられる。ジカ
ルボン酸およびその酸無水物としては、シユウ酸、コハ
ク酸、酒石酸、グルタル酸、フマル酸、マレイン酸、マ
ロン酸、シトラコン酸、イタコン酸、（o,m,p）フタル
酸、（α，β−）ナフタレン酸、2,3−ナフタレンジカ
ルボン酸、２−メタクリロイルオキシエチルトリメリツ
ト酸、および無水コハク酸、無水マレイン酸、無水シト
ラコン酸、無水イタコン酸、無水フタル酸、無水（α，
β−）ナフタレン酸、無水1,8−ナフタレンジカルボン
酸および２−メタクリロイルオキシエチルトリメリツト
酸無水物等があげられる。トリカルボン酸およびその酸
無水物としては、クエン酸、トリメリツト酸、トリメシ
ン酸、無水トリメリツト酸などが挙げられる。テトラカ
ルボン酸およびその酸無水物としてエチレンジアミン四
酢酸（EDTA）又はその塩、ピロメリツト酸および無水ピ
ロメリツト酸等が用いられる。また（メタ）アクリル酸
も用いられうる。さらに本発明における有機カルボン酸
は、その一部が塩であるものを含む。Examples of the organic carboxylic acid that can be used in the treating agent of the present invention include monocarboxylic acid, dicarboxylic acid, tricarboxylic acid, tetracarboxylic acid and their acid anhydrides. Monocarboxylic acid and its acid anhydride include formic acid, acetic acid,
Lactic acid, butyric acid, valeric acid, nonanoic acid, hexanoic acid, heptanoic acid, lauric acid, pyruvic acid, glycine, methacrylic acid, acrylic acid, crotonic acid, benzoic acid, aminobenzoic acid, salicylic acid, aminosalicylic acid, acetic anhydride, butyric anhydride , Valeric anhydride, lauric anhydride, glycine anhydride, crotonic anhydride, and benzoic anhydride. Examples of the dicarboxylic acid and its acid anhydride include oxalic acid, succinic acid, tartaric acid, glutaric acid, fumaric acid, maleic acid, malonic acid, citraconic acid, itaconic acid, (o, m, p) phthalic acid, and (α, β). -) Naphthalene acid, 2,3-naphthalenedicarboxylic acid, 2-methacryloyloxyethyl trimellitic acid, and succinic anhydride, maleic anhydride, citraconic anhydride, itaconic anhydride, phthalic anhydride, anhydrous (α,
Examples include β-) naphthalene acid, 1,8-naphthalenedicarboxylic acid anhydride and 2-methacryloyloxyethyl trimellitic anhydride. Examples of tricarboxylic acids and acid anhydrides thereof include citric acid, trimellitic acid, trimesic acid, and trimellitic anhydride. As the tetracarboxylic acid and its acid anhydride, ethylenediaminetetraacetic acid (EDTA) or its salt, pyromellitic acid, pyromellitic anhydride, etc. are used. (Meth) acrylic acid may also be used. Further, the organic carboxylic acid in the present invention includes one in which a part thereof is a salt.
これらの有機カルボン酸は単独で用いられてもよく、２
種以上混合されて用いられてもよい。これらの有機カル
ボン酸の内、クエン酸、コハク酸、シュウ酸、酒石酸、
またはエチレンジアミン四酢酸もしくはその塩、無水マ
レイン酸、無水コハク酸等が好ましい。有機カルボン
酸、金属塩化物および水からなる組成物中の有機カルボ
ン酸の濃度は、５〜50重量％であればよい。より好まし
くは、濃度５〜30重量％である。クエン酸の場合は５〜
30重量％が好ましい。上記の範囲外ではエツチング効果
が不十分となる。These organic carboxylic acids may be used alone or 2
You may use it in mixture of 2 or more types. Of these organic carboxylic acids, citric acid, succinic acid, oxalic acid, tartaric acid,
Alternatively, ethylenediaminetetraacetic acid or a salt thereof, maleic anhydride, succinic anhydride and the like are preferable. The concentration of the organic carboxylic acid in the composition consisting of the organic carboxylic acid, the metal chloride and water may be 5 to 50% by weight. More preferably, the concentration is 5 to 30% by weight. 5 for citric acid
30% by weight is preferred. If it is out of the above range, the etching effect becomes insufficient.
本発明の処理剤に使用する塩化カルシウムは、該組成物
中の濃度が５〜50重量％であればよい。なかでも、濃度
５〜30重量％の塩化カルシウムが好適である。The concentration of calcium chloride used in the treatment agent of the present invention may be 5 to 50% by weight in the composition. Among them, calcium chloride having a concentration of 5 to 30% by weight is suitable.
ところで、小島ら（歯科材料・器械、第１巻131頁（198
2））は、濃度10重量％のクエン酸水溶液に濃度が３重
量％になるように各種の金属塩化物を加えた溶液を歯面
処理剤として用いたときの歯面処理効果を報告している
が、金属塩化物として塩化亜鉛を用いる場合には、象牙
質に対する接着力は44kg/cm2と低く、歯面処理剤として
不適当であるとしている。By the way, Kojima et al. (Dental Materials and Instruments, Vol. 1, p. 131 (198
2)) reports the tooth surface treatment effect when a solution containing various metal chlorides added to a citric acid aqueous solution having a concentration of 10% by weight so that the concentration becomes 3% by weight is used as the tooth surface treatment agent. However, when zinc chloride is used as the metal chloride, the adhesive strength to dentin is as low as 44 kg / cm 2 , which is unsuitable as a tooth surface treating agent.
また、塩化第２鉄を用いる場合は、象牙質に対する接着
力はすぐれているが、鉄イオンが吸着し、褐色に着色す
るので治療御の審美性の面から問題である。然るに、本
発明の処理剤は、高濃度の金属塩化物を含むにもかかわ
らず、象牙質の着色がなく、審美性をそこなうことなく
歯面処理効果が著しく向上することは驚きである。な
お、金属塩化物の濃度が50重量％をこえるとエツチング
効果が不十分となる。Further, when ferric chloride is used, the adhesive force to dentin is excellent, but iron ions are adsorbed and colored brown, which is a problem from the viewpoint of aesthetic treatment. However, it is surprising that the treatment agent of the present invention does not cause coloration of dentin and has a significantly improved tooth surface treatment effect without impairing aesthetics, despite containing a high concentration of metal chloride. If the concentration of metal chloride exceeds 50% by weight, the etching effect will be insufficient.
なお、本発明の歯面処理剤に粘度調節剤を加えて、歯面
に塗布するときには流動性を有しているが、塗布後は速
やかに流動性を失う（チクソトロピー性）ようにし、局
所的塗布を可能とすることも可能である。また、食用色
素等で着色し、塗布部位の識別を容易にすることもでき
る。かかる粘度調節剤としてポリビニルピロリドン、カ
ルボキシルメチルセルロースなどに代表される高分子増
粘剤、高分散性シリカ等が挙げられる。また、着色材料
として食用色素等が挙げられる。The tooth surface treatment agent of the present invention is added with a viscosity modifier to have fluidity when applied to the tooth surface, but after application, the fluidity is rapidly lost (thixotropic property), and local It is also possible to enable coating. It is also possible to color with an edible dye or the like to facilitate the identification of the application site. Examples of such viscosity modifiers include polymer thickeners such as polyvinylpyrrolidone and carboxymethyl cellulose, and highly dispersible silica. In addition, food coloring and the like can be used as the coloring material.
以下、実施例により本発明の歯面処理剤について具体的
に説明する。Hereinafter, the tooth surface treating agent of the present invention will be specifically described with reference to Examples.
（実施例） 実施例１〜14 種々の有機カルボン酸および金属塩化物を用いて、表１
の組成とする歯面処理剤を調製した。歯面処理剤は、10
0mlのビーカーに所定量の有機カルボン酸と水を入れ、
所定量の金属塩化物を加えて十分に撹拌し、透明な液体
として調製した。同様に、比較例として表１に示す組成
の処理剤を調製した。各処理剤を用いた時の歯科用コン
ポジツトの歯質に対する接着力を下記の方法で測定し、
歯面処理効果をみた。Examples Examples 1-14 Using various organic carboxylic acids and metal chlorides, Table 1
A tooth surface treating agent having the above composition was prepared. Tooth surface treatment agent is 10
Put a predetermined amount of organic carboxylic acid and water in a 0 ml beaker,
A predetermined amount of metal chloride was added and sufficiently stirred to prepare a transparent liquid. Similarly, a treating agent having the composition shown in Table 1 was prepared as a comparative example. The adhesive force to the tooth substance of the dental composite when using each treatment agent was measured by the following method,
The tooth surface treatment effect was observed.
［接着力測定法］ 抜去後、直ちに冷凍保存した新鮮牛前歯の唇側面をシリ
コーンカーバイト紙で研磨して、平滑なエナメル質また
は象牙質表面を作成した。該表面に面積を規定した穴を
開けたスペーサーを置いた。所定濃度に調整した歯面処
理剤を該穴中のエナメル質または象牙質表面に塗布し、
40秒間放置し、水洗し、空気流で乾燥した。該表面に歯
科用コンポジツトレジン用リン酸エステル系ボンデイン
グ材（商品名：クリアフイルフオトボンド、クラレ社
製）を塗布し、30秒間放置し、空気流で揮発成分を蒸発
し、光照射器（クイツクライト、モリタ製作所製）で20
秒間光照射して重合させた。歯科用コンポジツトレジン
（商品名：クリアフイルフオトポステリア、クラレ社
製）を該穴に充填し、上記の光照射器で60秒間光照射し
て重合硬化させた。スペーサーを除去した後、硬化した
コンポジツトレジン上にリン酸エステル系歯科用接着性
セメント（パナビア、クラレ社製）でステンレス棒を接
着固定した。37℃の水中に24時間保管した後、万能試験
機を用いて2mm/分の速度で引つ張り接着力を測定した。
なお、硬化コンポジツトレジンとステンレス棒の間で破
壊することがないようにした。[Adhesive Force Measurement Method] Immediately after removal, the labial side of fresh bovine anterior teeth that had been frozen and stored was polished with silicone carbide paper to create a smooth enamel or dentin surface. A spacer having an area defined hole was placed on the surface. Apply the tooth surface treatment agent adjusted to a predetermined concentration to the enamel or dentin surface in the hole,
It was left for 40 seconds, washed with water and dried with a stream of air. A phosphoric acid ester-based bonding material (commercial name: Clear Film Photobond, manufactured by Kuraray Co., Ltd.) for dental composites resin is applied to the surface, left for 30 seconds, and volatile components are evaporated by an air flow, and a light irradiator ( 20 with Kikutsukulite, manufactured by Morita Manufacturing Co., Ltd.
It was irradiated with light for 2 seconds to be polymerized. Dental composites resin (trade name: clear film photoposteria, manufactured by Kuraray Co., Ltd.) was filled in the holes, and light was irradiated for 60 seconds by the above light irradiation device to polymerize and cure. After removing the spacers, a stainless steel rod was adhered and fixed onto the cured composite resin by using a phosphate ester-based dental adhesive cement (Panavia, Kuraray Co., Ltd.). After being stored in water at 37 ° C for 24 hours, the tensile adhesion was measured at a speed of 2 mm / min using a universal testing machine.
It should be noted that no breakage occurred between the cured composite resin and the stainless steel rod.
［歯面処理効果］ 本発明による処理剤は、エナメル質および象牙質の双方
にすぐれた接着力を示す。これに対して比較例の処理剤
はエナメル質の接着力は大きくても、象牙質の接着力が
不十分であつた。また、ウシ歯髄に由来するコラーゲン
線維に対する変性について、実施例５と比較例２の処理
剤の影響を電顕写真で比較すると、実施例による処理剤
の影響の小さいことが認められた。[Tooth surface treatment effect] The treatment agent according to the present invention exhibits excellent adhesive force to both enamel and dentin. On the other hand, in the case of the treatment agent of Comparative Example, the adhesive strength of dentin was insufficient even though the adhesive strength of enamel was large. Further, when the effects of the treatment agents of Example 5 and Comparative Example 2 were compared by electron micrographs with respect to the denaturation of collagen fibers derived from bovine dental pulp, it was found that the influence of the treatment agents of the Examples was small.
（発明の効果） 本発明により、エナメル質面と象牙質面の両方を処理で
きる歯面処理剤を得ることができた。 (Effect of the Invention) According to the present invention, a tooth surface treating agent capable of treating both an enamel surface and a dentin surface can be obtained.
Claims (3)
シウムおよび水を構成要素とするエナメル質面および／
または象牙質面を処理するための歯面処理剤であって、 （イ）該有機カルボン酸又はその無水物が、有機カルボ
ン酸又はその無水物、塩化カルシウムおよび水からなる
組成物に対し、その濃度が５〜50重量％であり、 （ロ）塩化カルシウムが、該組成物に対し、その濃度が
５〜50重量％であることを特徴とする歯面の処理剤。1. An enamel surface comprising an organic carboxylic acid or its anhydride, calcium chloride and water as constituent elements and / or
Or a tooth surface treating agent for treating a dentin surface, wherein (a) the organic carboxylic acid or its anhydride is a composition comprising an organic carboxylic acid or its anhydride, calcium chloride and water; A treatment agent for tooth surfaces, characterized in that the concentration is 5 to 50% by weight, and (b) calcium chloride is 5 to 50% by weight based on the composition.
シユウ酸、酒石酸、またはエチレンジアミン四酢酸もし
くはその塩である請求項第１項記載の歯面の処理剤。2. The organic carboxylic acid is citric acid, succinic acid,
The tooth surface treating agent according to claim 1, which is oxalic acid, tartaric acid, or ethylenediaminetetraacetic acid or a salt thereof.
該組成物に対して５〜30重量％含まれてなる請求項第１
項記載の歯面の処理剤。3. Citric acid and calcium chloride are each contained in an amount of 5 to 30% by weight based on the composition.
The tooth surface treatment agent according to the item.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63246063A JPH0686367B2 (en) | 1987-09-30 | 1988-09-29 | Tooth surface treatment agent |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24863187 | 1987-09-30 | ||
| JP62-248631 | 1987-09-30 | ||
| JP63-6603 | 1988-01-14 | ||
| JP660388 | 1988-01-14 | ||
| JP63246063A JPH0686367B2 (en) | 1987-09-30 | 1988-09-29 | Tooth surface treatment agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01279815A JPH01279815A (en) | 1989-11-10 |
| JPH0686367B2 true JPH0686367B2 (en) | 1994-11-02 |
Family
ID=27277244
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63246063A Expired - Lifetime JPH0686367B2 (en) | 1987-09-30 | 1988-09-29 | Tooth surface treatment agent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0686367B2 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06145020A (en) * | 1991-06-03 | 1994-05-24 | Shono Yasuo | Crystal-forming dentine pretreating agent and its production |
| TW403660B (en) * | 1992-07-13 | 2000-09-01 | Shiseido Corp | External skin treatment composition |
| EP0702948B1 (en) * | 1994-04-08 | 2001-03-07 | Kabushiki Kaisha Shofu | Tooth surface treating agent |
| US5925690A (en) * | 1995-11-20 | 1999-07-20 | Tokuyama Corproation | Dental primer composition and kit |
| DE112006003909B4 (en) | 2006-05-24 | 2017-05-11 | Kabushiki Kaisha Shofu | adhesive system |
| EP3496729A4 (en) | 2016-08-08 | 2020-10-07 | Launchpad Medical, Inc | Compositions and methods for adhesion to surfaces |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62231652A (en) * | 1986-04-01 | 1987-10-12 | 三井化学株式会社 | Dental adhesive surface treatment method |
-
1988
- 1988-09-29 JP JP63246063A patent/JPH0686367B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01279815A (en) | 1989-11-10 |
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