JP6831557B2 - 歯科用接着性組成物 - Google Patents
歯科用接着性組成物 Download PDFInfo
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- JP6831557B2 JP6831557B2 JP2016160396A JP2016160396A JP6831557B2 JP 6831557 B2 JP6831557 B2 JP 6831557B2 JP 2016160396 A JP2016160396 A JP 2016160396A JP 2016160396 A JP2016160396 A JP 2016160396A JP 6831557 B2 JP6831557 B2 JP 6831557B2
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- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
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- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- HUIHCQPFSRNMNM-UHFFFAOYSA-K scandium(3+);triiodide Chemical compound [Sc+3].[I-].[I-].[I-] HUIHCQPFSRNMNM-UHFFFAOYSA-K 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
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- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical class OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Description
本発明の歯科用接着性組成物は、酸性基含有重合性単量体を含む重合反応性成分100質量部と、常圧における沸点が50℃〜65℃である低沸点有機溶媒を200質量部〜400重量部と、常圧における沸点が75℃〜90℃である高沸点有機溶媒を25質量部〜120質量部と、水を5質量部〜50質量部と、化学重合開始剤と、を含むことを特徴とする。
<有機溶媒>
本実施形態の歯科用接着性組成物では、低沸点有機溶媒および高沸点有機溶媒を用い、低沸点有機溶媒は、重合反応性成分100質量部に対して、200質量部〜400重量部の範囲内で配合し、かつ、高沸点有機溶媒は、重合反応性成分100質量部に対して、25質量部〜120質量部の範囲内で配合する。
水は、重合反応性成分100質量部に対して、5質量部〜50質量部の範囲内で配合する。配合量は、20〜30質量部の範囲が好ましい。配合量を5質量部以上とすることにより、酸性基含有重合性単量体の存在下において、歯質の表面を脱灰することで、歯質に対する接着性を向上させ、接着不良を抑制できる。また、配合量を50質量部以下とすることにより、接着時に被膜中に揮発速度の相対的に遅い溶媒成分(高沸点有機溶媒および水)が過剰となり、被膜の強度が低下することによる接着不良を抑制できる。なお、水としては、貯蔵安定性、生体適合性及び接着性の観点で有害な不純物を実質的に含まない事が好ましく、例としては脱イオン水、蒸留水等が利用できる。
非溶媒成分は、低沸点有機溶媒、高沸点有機溶媒および水を少なくとも含む溶媒成分に溶解または分散可能な成分であり、本実施形態の歯科用接着性組成物においては、酸性基含有重合性単量体を含む重合反応性成分、および、化学重合開始剤が少なくとも用いられる。しかしながら、必要に応じてこれら以外のその他の非溶媒成分をさらに用いることもできる。なお、本願明細書において「重合反応性成分」には、重合性単量体、および、重合性単量体以外の重合性あるいは反応性を有する化合物が含まれる。重合性単量体としては、酸性基含有重合性単量体の他に、たとえば、後述する硫黄原子含有重合性単量体などが例示でき、重合性単量体以外の重合性あるいは反応性を有する化合物としては、たとえば、後述するシランカップリング剤が挙げられる。
1.重合性単量体
本実施形態の歯科用接着性組成物に用いられる重合性単量体は、少なくとも酸性基含有重合性単量体を含むものであればよいが、通常、重合性単量体としては、酸性基含有重合性単量体と、酸性基含有重合性単量体以外の重合性単量体とをブレンドして用いる。
酸性基含有重合性単量体は、上述したように歯質(象牙質、エナメル質)に対する接着性を向上させる以外にも、卑金属(鉄、ニッケル、クロム、コバルト、スズ、アルミニウム、銅、チタン等あるいはこれらを主成分として含む合金)、および、ジルコニウムなどの金属と酸素とを主成分として含む金属酸化物(ジルコニアセラミックスなど)に対する接着性も向上させる。このため、酸性基含有重合性単量体は、卑金属製あるいは金属酸化物製の補綴物を用いた修復を行う場合により好適である。
本実施形態の歯科用接着性組成物には、主に貴金属(金、白金、パラジウム、銀等あるいはこれらを主成分として含む合金)に対する接着性を向上させる観点から、硫黄原子含有重合性単量体をさらに用いることも好適である。この硫黄原子含有重合性単量体は、貴金属製の補綴物を用いた修復を行う場合に特に好適である。
本実施形態の歯科用接着性組成物には、歯質に対する接着性および接着耐久性の観点から酸性基含有重合性単量体および硫黄原子含有重合性単量体以外のその他の重合性単量体をさらに用いることがさらに好適である。
(iv)シランカップリング剤
本実施形態の歯科用接着性組成物には、重合性単量体以外の重合性あるいは反応性を有する化合物として、シランカップリング剤を用いることも好ましい。シランカップリング剤は、主にケイ素酸化物を成分として含むシリカ系酸化物(ポーセレン、シリカ粒子、シリカ系ガラスセラミックス、シリカ系ガラスなど)および複合樹脂材料(樹脂マトリックスと、シリカ粒子、ガラス繊維などのシリカ系酸化物を成分として含む無機充填材を複合化した材料)に対する接着性を向上させる。したがって、シランカップリング剤は、シリカ系酸化物あるいは複合樹脂材料製の補綴物や、シリカを主成分として含むシリカ系粒子を分散含有するコンポジットレジンなどの複合樹脂材料を用いた修復を行う場合に好適である。
本実施形態の歯科用接着性組成物に用いられる化学重合開始剤としては、公知の化学重合開始剤であればいずれも制限無く利用することができる。このような化学重合開始剤としては、たとえば、有機過酸化物及びアミン類の組み合わせ、有機過酸化物、アミン類及びスルフィン酸塩類の組み合わせ、酸性化合物及びアリールボレート化合物の組み合わせ、第4周期遷移金属化合物及び有機過酸化物の組み合わせ、有機過酸化物及びチオ尿素誘導体の組み合わせ、バルビツール酸、アルキルボラン等の化学重合開始剤等が挙げられる。
メチルエチルケトンパーオキサイド;
シクロヘキサノンパーオキサイド;
メチルシクロヘキサノンパーオキサイド;
メチルアセトアセテートパーオキサイド;
アセチルアセトンパーオキサイド;
1,1−ビス(t−ヘキシルパーオキシ)3,3,5−トリメチルシクロヘキサン;
1,1−ビス(t−ヘキシルパーオキシ)シクロヘキサン;
1,1−ビス(t−ブチルパーオキシ)3,3,5−トリメチルシクロヘキサン;
1,1−ビス(t−ブチルパーオキシ)シクロヘキサン;
1,1−ビス(t−ブチルパーオキシ)シクロドデカン;
2,2−ビス(t−ブチルパーオキシ)ブタン;
n−ブチル 4,4−ビス(t−ブチルパーオキシ)バレレート;
2,2−ビス(4,4−ジ−t−ブチルパーオキシシクロヘキシル)プロパン;
P−メンタンハイドロパーオキサイド;
ジイソプロピルベンゼンハイドロパーオキサイド;
1,1,3,3−テトラメチルブチルハイドロパーオキサイド;
クメンハイドロパーオキサイド;
t−ヘキシルハイドロパーオキサイド;
t−ブチルハイドロパーオキサイド;
α,α−ビス(t−ブチルパーオキシ)ジイソプロピルベンゼン;
ジクミルパーオキサイド;
2,5−ジメチル−2,5−ビス(t−ブチルパーオキシ)ヘキサン;
t−ブチルクミルパーオキサイド;
ジ−t−ブチルパーオキサイド;
2,5−ジメチル−2,5−ビス(t−ブチルパーオキシ)ヘキシン−3;
イソブチリルパーオキサイド;
2,4−ジクロロベンゾイルパーオキサイド;
3,5,5−トリメチルヘキサノイルパーオキサイド;
オクタノイルパーオキサイド;
ラウロイルパーオキサイド;
ステアリルパーオキサイド;
スクシニックアシッドパーオキサイド;
m−トルオイルベンゾイルパーオキサイド;
ベンゾイルパーオキサイド;
ジ−n−プロピルパーオキシジカーボネート;
ジイソプロピルパーオキシジカーボネート;
ビス(4−t−ブチルシクロヘキシル)パーオキシジカーボネート;
ジ−2−エトキシエチルパーオキシジカーボネート;
ジー2−エチルヘキシルパーオキシジカーボネート;
ジ−2−メトキシブチルパーオキシジカーボネート;
ジ(3−メチル−3−メトキシブチル)パーオキシジカーボネート;
α,α−ビス(ネオデカノイルパーオキシ)ジイソプロピルベンゼン;
クミルパーオキシネオデカノエート;
1,1,3,3−テトラメチルブチルパーオキシネオデカノエート;
1−シクロヘキシル−1−メチルエチルパーオキシネオデカノエート;
t−ヘキシルパーオキシネオデカノエート;
t−ブチルパーオキシネオデカノエート;
t−ヘキシルパーオキシピバレート;
t−ブチルパーオキシピバレート;
1,1,3,3−テトラメチルブチルパーオキシ−2−エチルヘキサノエート;
2,5−ジメチル−2,5−ビス(2−エチルヘキサノイルパーオキシ)ヘキサン;
1−シクロヘキシル−1−メチルエチルパーオキシ−2−エチルヘキサノエート;
t−ヘキシルパーオキシ2−エチルヘキサノエート;
t−ブチルパーオキシ2−エチルヘキサノエート;
t−ブチルパーオキシイソブチレート;
t−ヘキシルパーオキシイソプロピルモノカーボネート;
t−ブチルパーオキシマレイックアシッド;
t−ブチルパーオキシ3,5,5−トリメチルヘキサノエート;
t−ブチルパーオキシラウレート;
2,5−ジメチル−2,5−ビス(m−トルオイルパーオキシ)ヘキサン;
t−ブチルパーオキシイソプロピルモノカーボネート;
t−ブチルパーオキシ2−エチルヘキシルモノカーボネート;
t−ヘキシルパーオキシベンゾエート;
2,5−ジメチル−2,5−ビス(ベンゾイルパーオキシ)ヘキサン;
t−ブチルパーオキシアセテート;
t−ブチルパーオキシ−m−トルオイルベンゾエート;
t−ブチルパーオキシベンゾエート;
ビス(t−ブチルパーオキシ)イソフタレート;
その他の非溶媒成分としては、必要に応じて、ポリ低級アルキル(メタ)アクリレートなどを用いることも好適である。以下に本実施形態の歯科用接着性組成物に用いることができるその他の非溶媒成分について説明する。
被膜の粘度を高めて、被膜およびその硬化物である接着層の厚みをより均一化することで、接着不良をより一層抑制できる観点からは、非溶媒成分としてポリ低級アルキル(メタ)アクリレートをさらに用いることも好適である。また、ポリ低級アルキル(メタ)アクリレートは接着層の疎水性を向上させると共に、吸水性を下げる作用を有するため、結果として、長期間安定的に高い接着強度を確保することも容易になる。
光重合開始剤としては、公知の光重合開始剤を本発明の効果を阻害しない範囲で用いることができるが、たとえば、α−ジケトン類及び第三級アミン類の組み合わせ,アシルホスフィンオキサイド及び第三級アミン類の組み合わせ、チオキサントン類及び第三級アミン類の組み合わせ,α−アミノアセトフェノン類及び第三級アミン類の組み合わせ等の光重合開始剤が挙げられる。
また、充填材としては、シリカ粒子、シリカ−ジルコニア粒子、石英、フルオロアルミノシリケートガラスなどの無機充填材、ポリメチルメタクリレート、ポリメチルメタクリレート−ポリエチルメタクリレート共重合体、エチレン−酢酸ビニル共重合体、スチレン−ブタジエン共重合体などの有機高分子からなる粒子(有機充填材)、上述した無機粒子と重合反応性成分とを混合した後、重合させ、粉砕して得られる粒状の有機無機複合充填材などを用いることができる。充填材を用いる場合、その配合量は特に限定されるものではないが、たとえば、重合反応性成分100質量部に対して0.01質量部〜100質量部とすることが好ましく1質量部〜50質量部とすることがより好ましい。
本実施形態の歯科用接着性組成物は、歯牙の治療・修復に適宜用いることができるが、大別すると、コンポジットレジンも併用した修復、あるいは、補綴物も併用した修復に好適に利用できる。
以下に、表1および表2に示す各実施例および各比較例の歯科用接着性組成物において使用した物質の略称について説明する。
・IPA:イソプロピルアルコール(沸点:82.6℃)
・MDP:10−メタクリロイルオキシデシルジハイドロジェンホスフェート
・MTU−6:6−メタクリロイルオキシヘキシル 2−チオウラシル−5−カルボキシレート
・Bis−GMA:2.2’ ―ビス[4―(2―ヒドロキシ―3―メタクリルオキシプロポキシ)フェニル]プロパン
・3G:トリエチレングリコールジメタクリレート
・HEMA:2―ヒドロキシエチルメタクリレート
・γ−MPTES:γ−メタクリロキシプロピルトリエトキシシシラン
・BMOV:ビス(マルトラート)オキソバナジウム(IV)
・パーオクタH:1,1,3,3−テトラメチルブチルハイドロパーオキサイド
・Cu−AcAc:アセチルアセトン銅
・PhB−TEOA:テトラフェニルホウ素のトリエタノールアミン塩
・PhB−Na:テトラフェニルホウ素のナトリウム塩
<その他の非溶媒成分>
・PMMA:ポリメチルメタクリレート(重量平均分子量1000,000)
・HS:ヒュームドシリカ(平均1次粒径7nm、比表面積230m2/g、ジメチルジクロロシラン処理)
MDP(16.7質量部)
MTU−6(0.1質量部)
γーMPTES(11.1質量部)
Bis−GMA(33.3質量部)
3G(22.2質量部)
HEMA(27.7質量部)
硬化時間の測定は、各実施例および比較例の歯科用接着性組成物を構成する各成分のうち重合反応性成分の全量と化学重合開始剤の全量とを混合して実施した。その際、化学重合開始剤を構成する複数の成分のうち互いに反応する成分(例えば酸化剤と還元剤)を分けて、一方の成分を重合反応性成分の全量のうちの一部に混合・溶解させた第一液と、他方の成分を重合反応性成分の全量のうちの残部に混合・溶解させた第二液とを調製した。
その後、第一液および第二液を23℃で混合した混合物を調整し、混合直後に熱電対が取り付けられた試料皿中に投入した。そして、混合直後から混合物の硬化が完了するまでの硬化時間を測定した。なお、硬化の完了は、熱電対により検出される温度が極大値を示した時点とした。結果を表3および表4に示す。
操作時間の測定は以下の手順で実施した。まず、常温常湿環境下(温度23℃、湿度50%)において、各実施例および比較例の歯科用接着性組成物0.04mlを混和皿に採取した。続いて、採取時点を0秒として、所定の時間が経過した後に混和皿に採取された歯科用接着性組成物を、ミニブラシを用いて被着体サンプル(屠殺後24時間以内に抜去した牛前歯を、注水下、耐水研磨紙P600で研磨して唇面に平行かつ平坦になるように削り出したエナメル質平面)の表面に塗布した。この塗布テストは、混和皿への歯科用接着性組成物の採取1回に対してミニブラシによる塗布1回を1セットとし、採取から塗布までに要した時間を変える度に、新たに混和皿へ歯科用接着性組成物を採取して、ミニブラシによる塗布を実施した。そして、塗布した際に、ミニブラシにより被着体サンプルの表面上で歯科用接着性組成物をスムーズかつ十分に引き伸ばせるかどうかにより、塗布性が良好かどうかを判断し、良好な塗布性を示す最大時間を操作時間とした。結果を表3および表4に示す。なお、適正な操作時間の目安は60秒以上である。
補綴物の浮き上がり量は以下の手順で実施した。まず、窩洞内に顕著な隅角部を有する1級窩洞が形成された樹脂製の模型歯を用いて、窩洞内にコンポジットレジン(エステライトフロークイック、トクヤマデンタル製)を充填し、さらに光照射することでコンポジットレジンを硬化させた。次に、模型歯の窩洞の開口部が形成された側の面を、窩洞内にて硬化したコンポジットレジン(複合樹脂材料からなる補綴物)と共に研磨することで、窩洞内の補綴物の上部表面と、模型歯の窩洞開口部周辺の表面とが完全に面一(段差0μm)となるように研磨した。そして、研磨後、窩洞から補綴物を取り外した。
コンポジットレジンを用いた修復時の接着層厚みは、以下の手順で評価した。まず、屠殺後24時間以内に抜去した牛前歯を、注水下、耐水研磨紙P600で研磨し、唇面に平行かつ平坦になるように、象牙質平面を削り出した被着体を準備した。
屠殺後24時間以内に抜去した牛前歯を、注水下、耐水研磨紙P600で研磨し、唇面に平行かつ平坦になるように、エナメル質平面を削り出した被着体および象牙質平面を削り出した被着体を準備した。
屠殺後24時間以内に抜去した牛前歯を、注水下、耐水研磨紙P600で研磨し、唇面に平行かつ平坦になるように、エナメル質平面を削り出した被着体および象牙質平面を削り出した被着体を準備した。
Claims (8)
- 酸性基含有重合性単量体を含む重合反応性成分を100質量部と、
常圧における沸点が50℃〜65℃である低沸点有機溶媒を200質量部〜400重量部と、
常圧における沸点が75℃〜90℃である高沸点有機溶媒を25質量部〜120質量部と、
水を5質量部〜50質量部と、
化学重合開始剤と、
を含むことを特徴とする歯科用接着性組成物。 - 前記高沸点有機溶媒に対する前記低沸点有機溶媒の質量比が2〜12であることを特徴とする請求項1に記載の歯科用接着性組成物。
- 前記重合反応性成分が、硫黄原子含有重合性単量体をさらに含むことを特徴とする請求項1または2に記載の歯科用接着性組成物。
- 前記重合反応性成分が、シランカップリング剤をさらに含むことを特徴とする請求項1〜3のいずれか1つに記載の歯科用接着性組成物。
- 前記化学重合開始剤が、アリールボレート化合物を含むことを特徴とする請求項1〜4のいずれか1つに記載の歯科用接着性組成物。
- 前記化学重合開始剤が、有機過酸化物およびバナジウム化合物を含むことを特徴とする請求項1〜5のいずれか1つに記載の歯科用接着性組成物。
- 前記重合反応性成分100質量部に対して、前記酸性基含有重合性単量体を5質量部〜30質量部と、前記化学重合開始剤として、アリールボレート化合物を0.5質量部〜15質量部、有機過酸化物を0.5質量部〜10質量部およびバナジウム化合物を0.01質量部〜0.4質量部と、を含むことを特徴とする請求項1〜6のいずれか1つに記載の歯科用接着性組成物。
- 前記重合反応性成分の全量と、前記化学重合開始剤の全量とのみを、23℃で混合した混合物を調整した場合において、
混合直後から前記混合物の硬化が完了するまでの硬化時間が60秒以下であることを特徴とする請求項1〜7のいずれか1つに記載の歯科用接着性組成物。
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