JP4860788B2 - 1液型の歯科用接着材組成物 - Google Patents
1液型の歯科用接着材組成物 Download PDFInfo
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- JP4860788B2 JP4860788B2 JP2011537792A JP2011537792A JP4860788B2 JP 4860788 B2 JP4860788 B2 JP 4860788B2 JP 2011537792 A JP2011537792 A JP 2011537792A JP 2011537792 A JP2011537792 A JP 2011537792A JP 4860788 B2 JP4860788 B2 JP 4860788B2
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- 239000010935 stainless steel Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 210000004357 third molar Anatomy 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-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
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- XASAPYQVQBKMIN-UHFFFAOYSA-K ytterbium(iii) fluoride Chemical compound F[Yb](F)F XASAPYQVQBKMIN-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/62—Photochemical radical initiators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
Landscapes
- Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dental Preparations (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
Description
酸性基を有する重合性単量体(A)は、酸エッチング効果及びプライマー処理効果を有しており、組成物に脱灰作用及び浸透作用を与える成分である。また、酸性基を有する重合性単量体(A)は、重合可能であり、硬化作用も付与する。組成物が酸性基を有する重合性単量体(A)を含有することにより、1液型の歯科用接着材として機能することができ、また歯質に対する接着性と接着耐久性が向上する。
下記一般式(1)で表されるフルオロカーボン基を有する重合性単量体(B)は、組成物に硬化性を与え、また組成物の硬化物の吸水率及び寸法安定性を改善し、接着耐久性を向上させる成分である。フルオロカーボン基を有する重合性単量体の中でも下記一般式(1)で表されるフルオロカーボン基を有する重合性単量体(B)を、上記特定配合量の酸性基を有する重合性単量体(A)及び水(C)と組み合わせることにより、組成物の環境光安定性、接着性及び接着耐久性がバランスよく高くなる。
水(C)は、組成物の歯質に対する接着性と接着耐久性を向上させる成分である。水(C)としては、悪影響を及ぼすような不純物を含有していないことが好ましく、蒸留水又はイオン交換水が好ましい。上記水(C)は単独で用いてもよいし、水(C)と後述の有機溶媒(H)の混合溶媒として用いてもよい。
重合開始剤(D)は、組成物の重合硬化を促進する成分である。重合開始剤(D)は、一般工業界で使用されている重合開始剤から選択して使用でき、中でも歯科用途に用いられている重合開始剤が好ましく用いられる。特に、光重合及び化学重合の重合開始剤が、単独で又は2種以上適宜組み合わせて使用される。
本発明の組成物は、1個の重合性基と1個以上の水酸基とを有する重合性単量体(E)を含有してなることが好ましい。重合性単量体(E)は、水酸基を1個以上有するため親水性が良好であり、組成物の浸透作用を向上させ、接着性を向上させ、組成物の均一性にも貢献する成分である。重合性単量体(E)が1個の重合性基を有することによりラジカル重合が可能となるとともに、他の重合性単量体との共重合が可能となる。1個の重合性基と1個以上の水酸基とを有する重合性単量体(E)としては特に限定されず、重合性単量体(E)の重合性基は、重合性単量体(A)及び(B)の重合性基とラジカル共重合可能な基であることが好ましい。ラジカル重合が容易である観点からは、重合性単量体(E)の重合性基は(メタ)アクリル基、又は(メタ)アクリルアミド基が好ましい。重合性単量体(E)は歯科用接着材組成物の成分として用いられるが、口腔内は湿潤な環境であるため、加水分解などにより重合性基が脱離するおそれがある。脱離した重合性基の生体への刺激性を考慮した場合、重合性単量体(E)の重合性基は、メタクリル基、又はメタクリルアミド基であることが好ましい。
本発明の組成物は、上記一般式(2)で表される2個の重合性基と2個の水酸基を含む重合性単量体(F)を含有することが好ましい。
本発明の組成物は、前記一般式(2)で表される2個の重合性基と2個の水酸基を含む重合性単量体(F)以外の架橋性の重合性単量体(G)を含有してなることが好ましい。架橋性の重合性単量体(G)を含む組成物は、接着強さがさらに向上する等の利点を有する。
本発明の組成物は、重合性単量体の溶解性を向上させ、均一な組成物を得るために、有機溶媒(H)を含んでいてもよい。有機溶媒(H)は、単独で又は2種以上適宜組み合わせて使用することができる。有機溶媒(H)としては、メタノール、エタノール、1−プロパノール、2−プロパノール、1−ブタノール、2−メチル−2−プロパノール、アセトン、メチルエチルケトン、テトラヒドロフラン、ジエチルエーテル、ジイソプロピルエーテル、ヘキサン、トルエン、クロロホルム、酢酸エチル、酢酸ブチル等が挙げられる。これらの中でも、生体に対する安全性と、揮発性に基づく除去の容易さの双方を勘案した場合、有機溶媒(H)が水溶性有機溶媒であることが好ましく、具体的には、エタノール、2−プロパノール、2−メチル−2−プロパノール、アセトン、及びテトラヒドロフランが好ましく用いられる。前記有機溶媒(H)の配合量は特に限定されず、重合性単量体の全量100重量部に対して、1〜1000重量部が好ましく、5〜200重量部がより好ましい。
好ましい実施態様では、重合促進剤(I)が用いられる。本発明に用いられる重合促進剤(I)としては、アミン類、スルフィン酸及びその塩、ボレート化合物、バルビツール酸誘導体、トリアジン化合物、銅化合物、スズ化合物、バナジウム化合物、ハロゲン化合物、アルデヒド類、チオール化合物、亜硫酸塩、亜硫酸水素塩、チオ尿素化合物などが挙げられる。
本発明の組成物は、フィラー(J)を含有していてもよい。このようなフィラーは、通常、有機フィラー、無機フィラー及び有機−無機複合フィラーに大別される。有機フィラーの素材としては、例えばポリメタクリル酸メチル、ポリメタクリル酸エチル、メタクリル酸メチル−メタクリル酸エチル共重合体、架橋型ポリメタクリル酸メチル、架橋型ポリメタクリル酸エチル、ポリアミド、ポリ塩化ビニル、ポリスチレン、クロロプレンゴム、ニトリルゴム、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、アクリロニトリル−スチレン共重合体、アクリロニトリル−スチレン−ブタジエン共重合体等が挙げられ、これらは単独で又は2種以上の混合物として用いることができる。有機フィラーの形状は特に限定されず、フィラーの粒子径を適宜選択して使用することができる。得られる組成物のハンドリング性及び機械強度などの観点から、前記有機フィラーの平均粒子径は、0.001〜50μmであることが好ましく、0.001〜10μmであることがより好ましい。
本発明の組成物は、さらにフッ素イオン放出性物質を含んでいてもよい。フッ素イオン放出性物質を配合することによって、歯質に耐酸性を付与することができる組成物が得られる。かかるフッ素イオン放出性物質としては、フッ化ナトリウム、フッ化カリウム、モノフルオロリン酸ナトリウム、フッ化リチウム、フッ化イッテルビウム等の金属フッ化物類等を挙げることができる。
4−META:4−メタクリロイルオキシエチルトリメリテート
6−MHPA:6−メタクリロイルオキシヘキシルホスホノアセテート
HEMA:2−ヒドロキシエチルメタクリレート
4FMA:テトラフルオロプロピルメタクリレート
Bis−GMA:2,2−ビス〔4−(3−メタクリロイルオキシ)−2−ヒドロキシプロポキシフェニル〕プロパン
UDMA:2,2,4−トリメチルヘキサメチレンビス(2−カルバモイルオキシエチル)ジメタクリレート
TEGDMA:トリエチレングリコールジメタクリレート
GDMA:グリセロールジメタクリレート
TMDPO:2,4,6−トリメチルベンゾイルジフェニルホスフィンオキサイド
BAPO:ビス(2,4,6−トリメチルベンゾイル)フェニルホスフィンオキサイド
CQ:カンファーキノン
PDE:p−(N,N−ジメチルアミノ)安息香酸エチル
DEPT:N,N−ジ(2−ヒドロキシエチル)−p−トルイジン
TTA:トリエタノールアミン
無機フィラー1:日本アエロジル社製「R972」
表1〜3に記載の各成分を常温下で混合して1液型歯科用接着材組成物を作製した。これらの組成物を用い、後述の方法に従って、接着性試験(1)、接着性試験(2)、均一性評価、吸水性試験、耐着色試験及び環境光安定性試験を行った。組成及び評価結果を表1〜3に示す。
ウシ下顎前歯の唇面を流水下にて#80シリコン・カーバイド紙(日本研紙社製)で研磨して、象牙質の平坦面を露出させたサンプルを得た。得られたサンプルを流水下にて#1000のシリコン・カーバイド紙(日本研紙社製)でさらに研磨した。研磨終了後、表面の水をエアブローすることで乾燥した。乾燥後の平滑面に、直径3mmの丸穴を有する厚さ約150μmの粘着テープを貼着し、接着面積を規定した。
ヒト第三大臼歯歯冠部中央を精密低速切断機「アイソメット5000」(Buehler社製)を用いて歯軸に対して垂直に切断して、象牙質の平坦面を露出させたサンプルを得た。得られたサンプルを注水下にて#600のシリコン・カーバイド紙(日本研紙社製)で研磨した。
各成分を常温下で混合後、25℃で10分間静置し、1液型歯科用接着材の各成分が分離または沈降することなく、均一に分散しているかどうかを目視にて評価した。1液型歯科用接着材に含まれる重合性単量体、溶媒、重合開始剤、及び重合促進剤が相互に溶解しており、フィラーを配合した場合には該フィラーが分離、沈降することなく1液型歯科用接着材中に分散して存在しているものを均一とした。
前記1液型接着材にエアーを噴き付け、重量変化がなくなるまで水や有機溶媒を除去し、硬化物作製用サンプルを得た。得られたサンプルを、ポリエステル製フィルムを載置したスライドガラス上に置いたテフロン(登録商標)型(直径10mm、厚さ1mm)に入れ、上からポリエステル製フィルムを置いて、さらにガラス板を用いて軽く押し当てた。その上から前記照射器「JETライト3000」を用いて10秒間光照射を行った後、裏返して同様に10秒間光照射を行ってサンプルを硬化させ、1液型接着材の硬化物を得た。
吸水率=(重量A−重量B)÷重量B×100 (%)
ターメリック(0.005g)〔(株)ギャバン製〕を蒸留水(100mL)の中に入れ、黄色のターメリック懸濁液を作製した。その中に、前記吸水性試験と同様の方法で作製した1液型接着材の硬化物を浸漬した。37℃の恒温機に18時間保管した後、硬化物を取り出し、流水で1分間洗浄した後、硬化物の着色の度合いを目視にて観察した。
前記1液型接着材1滴(約20mg)を混和皿上に採取し、照度8,000ルクスに調整したデンタルライト下に所定時間放置した後、サンプルを筆ですくい上げ、ゲル状物の有無を確認した。測定は10秒間隔で行い、ゲル状物が認められなかった最長の時間を操作余裕時間とした。
Claims (11)
- 前記フルオロカーボン基を有する重合性単量体(B)の含有量が、重合性単量体の全量100重量部の内、0.5〜10重量部である請求項1に記載の1液型歯科用接着材組成物。
- 1個の重合性基と1個以上の水酸基を含む重合性単量体(E)を、重合性単量体の全量100重量部の内、10〜50重量部さらに含有する請求項1に記載の1液型歯科用接着材組成物。
- 前記重合性単量体(F)の含有量が、重合性単量体の全量100重量部の内、5〜20重量部である請求項4に記載の1液型歯科用接着材組成物。
- 前記重合開始剤(D)の含有量が、重合性単量体の全量100重量部に対して、0.001〜20重量部である請求項1に記載の1液型歯科用接着材組成物。
- 有機溶媒(H)を含む請求項1に記載の1液型歯科用接着材組成物。
- 重合促進剤(I)を含む請求項1に記載の1液型歯科用接着材組成物。
- フィラー(J)を含む請求項1に記載の1液型歯科用接着材組成物。
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CN106726623B (zh) * | 2016-12-28 | 2020-12-04 | 日照沪鸽生物材料有限公司 | 用于牙体修复具有氟离子释放特性的单组分光固化复合材料及其应用 |
JP6929097B2 (ja) * | 2017-03-30 | 2021-09-01 | 株式会社ジーシー | 歯科用プライマー及び歯科用補綴物接着用キット |
CN111714781B (zh) * | 2020-06-24 | 2022-08-05 | 北京夏禾科技有限公司 | 一种牙齿美白组合及其使用方法 |
WO2024043291A1 (ja) * | 2022-08-25 | 2024-02-29 | クラレノリタケデンタル株式会社 | 歯科用接着性組成物 |
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- 2011-03-25 WO PCT/JP2011/001792 patent/WO2011121966A1/ja active Application Filing
- 2011-03-25 US US13/636,167 patent/US9271901B2/en active Active
- 2011-03-25 CN CN201180016281.4A patent/CN102811695B/zh active Active
- 2011-03-25 JP JP2011537792A patent/JP4860788B2/ja active Active
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EP2554155A1 (en) | 2013-02-06 |
EP2554155B1 (en) | 2020-08-05 |
EP2554155A4 (en) | 2013-12-25 |
CN102811695B (zh) | 2015-01-07 |
CN102811695A (zh) | 2012-12-05 |
JPWO2011121966A1 (ja) | 2013-07-04 |
US9271901B2 (en) | 2016-03-01 |
US20130012615A1 (en) | 2013-01-10 |
WO2011121966A1 (ja) | 2011-10-06 |
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