JP5661040B2 - ジルコニア及びシリカナノ粒子を含む充填剤、並びにコンポジット材料 - Google Patents
ジルコニア及びシリカナノ粒子を含む充填剤、並びにコンポジット材料 Download PDFInfo
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- JP5661040B2 JP5661040B2 JP2011532156A JP2011532156A JP5661040B2 JP 5661040 B2 JP5661040 B2 JP 5661040B2 JP 2011532156 A JP2011532156 A JP 2011532156A JP 2011532156 A JP2011532156 A JP 2011532156A JP 5661040 B2 JP5661040 B2 JP 5661040B2
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- zirconia
- filler
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- silica
- typically
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims description 89
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- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000068 pit and fissure sealant Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 230000036346 tooth eruption Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical class [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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Description
「結晶ジルコニア」とは、X線回折において有意な結晶(単斜晶、正方晶、立方晶、又は偽立方晶)ピークを呈するジルコニアを意味する。典型的には、結晶ジルコニアは、全文を参照することにより本明細書に援用する、1999年10月28日出願の米国特許第6,376,590号(Kolbら)、又は2007年6月7日出願の米国特許第7,429,422号(Davidsonら)に記載されているジルコニアゾルの結晶化度パラメータを満たす。
本発明の歯科用組成物は、典型的には重合性成分が存在するため、硬化性である。幾つかの実施形態では、組成物は、口腔表面に塗布する前に硬化させ得る(例えば、従来の光重合及び/又は化学重合技術によって重合し得る)。他の実施形態では、組成物は、口腔表面に塗布された後に硬化させ得る(例えば、従来の光重合及び/又は化学重合技術によって重合し得る)。
重合性成分は、典型的には、酸官能基を有する又は有しない1種以上のエチレン性不飽和化合物を含む。有用なエチレン性不飽和化合物の例としては、アクリル酸エステル、メタクリル酸エステル、ヒドロキシ官能性アクリル酸エステル、ヒドロキシ官能性メタクリル酸エステル、及びこれらの組み合わせが挙げられる。
特定の実施形態では、本発明の組成物は光重合性である、即ち、この組成物は、化学線の照射時に、組成物の重合(又は硬化)を開始する光重合性成分及び光反応開始剤系を含有する。このような光重合性組成物は、フリーラジカル重合性又はカチオン重合性であってもよい。
本発明の組成物は、組成物に乳白光を付与するシリカ−ジルコニアナノクラスタ充填剤を含む。乳白光を発する効果は、少なくとも部分的に、シリカ−ジルコニアクラスタを形成するとき、予成形ナノジルコニア粒子の利用に起因すると考えられている。これら予成形粒子の使用は、例えば、酢酸塩等の他の前駆体から出発するときに得られるよりも優れた乳白光を有する充填剤を提供する。
シリカ−ジルコニアナノクラスタ充填剤に加えて、本発明の組成物は、所望により、1種以上の他の充填剤を含有し得る。これらの充填剤は、例えば、歯科修復組成物等において現在使用される充填剤のような、歯科用途に使用される組成物への組み込みに好適な多種多様な材料の中から1つ以上選択されてもよい。
所望により、本発明の組成物は、溶媒(例えば、アルコール(例えば、プロパノール、エタノール)、ケトン(例えば、アセトン、メチルエチルケトン)、エステル(例えば、酢酸エチル)、他の非水性溶媒(例えば、ジメチルホルムアミド、ジメチルアセトアミド、ジメチルスルホキシド、1−メチル−2−ピロロリジノン))、又はこれらの混合物を含有してもよい。
本発明の歯科用組成物は、従来の混合技術を使用して様々な成分を全て組み合わせて調製できる。得られる組成物は、所望により、充填剤、溶媒、水及び本発明で記載したような他の添加剤を含有してよい。典型的には、本発明の光重合性組成物は、「安全光(safe light)」の下で本発明の組成物の成分を単純に混合させて調製される。この混合物を処置する場合、必要に応じて、好適な不活性溶媒を取り入れてもよい。本発明の組成物の成分とはそれほど反応しない、いずれの溶媒を使用してよい。好適な溶媒の例には、アセトン、ジクロロメタン、アセトニトリル、及びラクトンが挙げられる。重合される液体材料を、重合される別の液体又は固体の材料に対する溶媒として使用できる。無溶媒組成物は、穏やかに加熱して溶解を促進して又はせずに、単に(任意の)ヨードニウム錯塩、増感剤、及び電子供与体を重合性樹脂に溶解させることにより調製できる。
「ビスGMA」は、2,2−ビス[4−(2−ヒドロキシ−3−メタクリロイルオキシプロポキシ)フェニル]プロパンを指し、
「TEGDMA」は、Sartomer Co.,Inc.,Exton,PAから入手したトリエチレングリコールジメタクリレートを指し、
「UDMA」は、Rohm America LLC,Piscataway,NJから商品名「ROHAMERE 6661−0」として入手した、ジウレタンジメタクリレートを指し、
「ビスEMA6」は、Sartomer Co.,Inc.,Exton,PAから入手した、エトキシ化ビスフェノールAジメタクリレートを指し、
「BHT」は、ブチル化ヒドロキシトルエンを指し、
「BZT」は、Ciba,Inc.,Tarrytown,NYから入手した2−(2−ヒドロキシ−5−メタクリルオキシエチルフェニル)−2H−ベンゾトリアゾールを指し;
「ENMAP」は、参照により本明細書に援用される、Adamsonら;JCSOA9;J.Chem.Soc.;1949;spl.144,152に記載のもの等の、既知の方法を用いて合成される、エチル−(N−メチル−N−フェニル)アミノプロピオネートを指し;
「CPQ」は、カンファーキノンを指し、
「Irgacure 819」は、Ciba,Inc.,Tarrytown,NYから入手したビス(2,4,6−トリメチルベンゾイル)フェニルホスフィンオキシドを指し、
「PEG 600 DM」は、Sartomer Co.,Inc.,Exton,PAから入手可能な、平均分子量〜600の、ポリエチレングリコールジメタクリレートを指し;
「GENIOSIL GF−31」又は「GF−31」は、Wacker Chemie AG,Munich,Germanyから入手可能な3−メタクリルオキシプロピルトリメトキシシラン組成物を指す。
105.24gのNALCO 1042シリカゾルを計量し、3.15gの70重量%HNO3溶液を添加し、これを45.16gの酸還元ジルコニアゾル(本質的に、2007年6月7日出願の米国特許第7,429,422号(Davidsonら)に記載の通り調製)に添加することにより、充填剤Aを調製した。これにより、酸化物の重量に基づいて、約73重量%のシリカと、27重量%のジルコニアとの酸化物混合物が生じた。この混合物に、100gの顆粒糖を添加した。得られたゾルを、セラミック容器に注ぎ、625℃で焼成して、揮発性物質及び有機物質を除去した。次いで、得られた焼成物質を乳鉢と乳棒で微粉化し、75マイクロメートルのナイロン篩を通して選別して、大きな粒塊を除去した。次いで、物質を、25.000gの得られた微粉酸化物、3.270gのGF−31シラン、27.4gの酢酸エチル、及び0.447gの30% NH4OH溶液と混合することによりシラン処理した。これを約4時間混合した後、パイレックス(登録商標)のトレイ内で酢酸エチルを蒸発分離(flashing off)させ、90℃で30分間加熱した。
45.16gの酸還元ジルコニアゾル(本質的に、2007年6月7日出願の米国特許第7,429,422号(Davidsonら)に記載の通り調製)を計量し、これに105.65gのNALCO 1042シリカゾル及び1.19gの70重量%の硝酸溶液の混合物を添加することにより、充填剤Bを調製した。この混合物を直接セラミック焼成容器に注ぎ、625℃で4時間焼成して、水及び有機揮発性物質を除去した。この得られた酸化物も、約73重量%がシリカ、27重量%がジルコニアであった。得られた充填剤を乳鉢と乳棒で微粉化し、75マイクロメートルのナイロン篩を通して選別して、大きな粒塊を除去した。40gのこの物質を6.02gのGF−31シラン、49gの酢酸エチル、及び0.76gの30% NH4OH溶液に添加した。それを3時間反応させ、溶媒をパイレックス(登録商標)のトレイ内で蒸発分離させ、物質を90℃で30分間焼成して最終充填剤を得た。
充填剤Cは、充填剤Bで上記したのと同じ比の物質を用いて調製した。充填剤を825℃で8時間(625℃の代わりに)加熱し、乳鉢と乳棒の代わりにボールミルで粉砕し、充填剤を、1−メトキシ−2−プロパノールに分散させることによりシラン処理し、充填剤の重量に対して11%のGF−31と共に、pH 8.75(NH4OHで調整)において、80℃で30分間加熱し、次いで物質をギャップ乾燥させた。
713℃で11時間粉砕した後、充填剤を再度か焼し、次いでシラン化して更なる残留物を除去したことを除いて、約73%のシリカと27%のジルコニアとの比を有する酢酸ジルコニルから誘導されるシラン処理シリカ/ジルコニア充填剤を、本質的に米国特許第6,730,156号の予備実施例A及びBに記載の通り調製した。
また、本発明は、たとえば、以下の態様の発明を含む。
[1]
コンポジット材料用の充填剤を作製する方法であって、
(a)約3nm〜約30nmの平均直径を有する、予め成形された結晶ジルコニアナノ粒子を含むジルコニアゾルを提供する工程と、
(b)約10nm〜約100nmの平均直径を有するシリカナノ粒子を含むシリカゾルを提供する工程と、
(c)前記ジルコニアゾルと前記シリカゾルとを組み合わせて、ジルコニア及びシリカナノ粒子の混合物を形成する工程と、
(d)前記混合物を約400℃〜約1000℃の温度に加熱する工程と、
(e)前記加熱された混合物を粉砕して、シリカ−ジルコニアナノクラスタを含む充填剤を形成する工程と、を含む、方法。
[2]
前記ナノクラスタが、約0.01〜約100マイクロメートルの平均体積直径を有する、[1]に記載の方法。
[3]
前記ナノクラスタが、約0.5〜約10マイクロメートルの平均体積直径を有する、[1]に記載の方法。
[4]
前記シリカナノ粒子が、約15nm〜約60nmの平均直径を有する、[1]〜[3]のいずれか一項に記載の方法。
[5]
前記ジルコニアナノ粒子が、約5nm〜約15nmの平均直径を有する、[1]〜[4]のいずれか一項に記載の方法。
[6]
前記シリカナノ粒子が、約15nm〜約35nmの平均直径を有し、前記ジルコニアナノ粒子が、約5nm〜約15nmの平均直径を有する、[1]に記載の方法。
[7]
前記シリカナノ粒子及び前記ジルコニアナノ粒子が、前記ナノクラスタ中に均一に分布している、[1]〜[6]のいずれか一項に記載の方法。
[8]
前記シリカゾルのpHを1.2未満に低下させた後、前記ジルコニアゾルと混合する工程を更に含む、[1]〜[7]のいずれか一項に記載の方法。
[9]
前記充填剤を表面処理する工程を更に含む、[1]〜[8]のいずれか一項に記載の方法。
[10]
前記充填剤が、シランカップリング剤で表面処理される、[9]に記載の方法。
[11]
前記シリカ−ジルコニア充填剤が、約1.44〜約1.65の屈折率を有する、[1]〜[10]のいずれか一項に記載の方法。
[12]
前記ジルコニアゾルが酸還元されている、[1]〜[11]のいずれか一項に記載の方法。
[13]
[1]〜[12]のいずれか一項に記載の方法に従って調製される充填剤。
[14]
[13]に記載の充填剤を含むコンポジット材料。
[15]
(a)重合性成分と、
(b)反応開始剤系と、
(c)ジルコニアナノ粒子及びシリカナノ粒子のナノクラスタを含む充填剤と、を含む硬化性歯科用組成物であって、
前記組成物が、乳白光試験方法に従って測定したとき、少なくとも15のCab値を有する、硬化性歯科用組成物。
[16]
前記ナノクラスタが、約0.01〜約100マイクロメートルの平均体積直径を有する、[15]に記載の組成物。
[17]
前記ナノクラスタが、約0.5〜約10マイクロメートルの平均体積直径を有する、[15]に記載の組成物。
[18]
前記シリカナノ粒子が、約15nm〜約60nmの平均直径を有する、[15]〜[17]のいずれか一項に記載の組成物。
[19]
前記ジルコニアナノ粒子が、約5nm〜約15nmの平均直径を有する、[15]〜[18]のいずれか一項に記載の組成物。
[20]
前記シリカナノ粒子が、約15nm〜約35nmの平均直径を有し、前記ジルコニアナノ粒子が、約5nm〜約15nmの平均直径を有する、[15]に記載の組成物。
[21]
前記シリカナノ粒子及び前記ジルコニアナノ粒子が、前記ナノクラスタ中に均一に分布している、[15]〜[20]のいずれか一項に記載の組成物。
[22]
前記組成物が、乳白光試験方法に従って測定したとき、少なくとも18のCab値を有する、[15]〜[21]のいずれか一項に記載の組成物。
[23]
前記組成物が、乳白光試験方法に従って測定したとき、少なくとも20のCab値を有する、[15]〜[21]のいずれか一項に記載の組成物。
[24]
前記組成物が、70ヘイズ未満の曇り度測定値を有する、[15]〜[23]のいずれか一項に記載の組成物。
[25]
前記曇り度測定値が60ヘイズ未満である、[24]に記載の組成物。
[26]
前記曇り度測定値が55ヘイズ未満である、[25]に記載の組成物。
[27]
前記ナノクラスタが表面処理されている、[15]〜[26]のいずれか一項に記載の組成物。
[28]
前記ナノクラスタが、シランで表面処理されている、[27]に記載の組成物。
[29]
前記重合性成分がエチレン性不飽和化合物を含む、[15]〜[28]のいずれか一項に記載の組成物。
[30]
前記重合性成分が(メタ)アクリレートを含む、[29]に記載の組成物。
[31]
前記組成物が、約1.44〜約1.65の屈折率を有する、[15]〜[30]のいずれか一項に記載の組成物。
[32]
前記充填剤が、[1]〜[12]のいずれか一項に記載の方法に従って調製された、[15]に記載の組成物。
[33]
[15]〜[31]のいずれか一項に記載の歯科用コンポジットを含む歯科用修復材。
[34]
前記材料が、充填材、予成形ブリッジ若しくはクラウン、流動性修復材、又は暫間修復材である、[33]に記載の歯科用修復材。
[35]
[15]に記載の組成物を含むミルブランク。
Claims (4)
- コンポジット材料用の充填剤を作製する方法であって、
(a)3nm〜30nmの平均直径を有する、予め成形された結晶ジルコニアナノ粒子を含むジルコニアゾルを提供する工程と、
(b)10nm〜100nmの平均直径を有する、非凝集粒子または非塊化粒子であるシリカナノ粒子を含むシリカゾルを提供する工程と、
(c)前記ジルコニアゾルと前記シリカゾルとを組み合わせて、ジルコニア及びシリカナノ粒子の混合物を形成する工程と、
(d)前記混合物を400℃〜1000℃の温度に加熱する工程と、
(e)前記加熱された混合物を粉砕して、シリカ−ジルコニアナノクラスタを含む充填剤を形成する工程と、を含む、方法。 - (a)重合性成分と、
(b)反応開始剤系と、
(c)ジルコニアナノ粒子及びシリカナノ粒子のナノクラスタを含む充填剤と、を含む硬化性歯科用組成物であって、ジルコニアナノ粒子は予め成形された結晶ジルコニアナノ粒子を含み、
前記組成物が、乳白光試験方法に従って測定したとき、少なくとも15のCab値を有する、硬化性歯科用組成物。 - 前記ジルコニアナノ粒子が5nm〜15nmの平均直径を有する、請求項1に記載の方法。
- 前記混合物の加熱が450℃〜950℃の温度で行われる、請求項1に記載の方法。
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-
2009
- 2009-10-09 EP EP09737304.7A patent/EP2370362B1/en active Active
- 2009-10-09 US US13/123,749 patent/US8722759B2/en active Active
- 2009-10-09 WO PCT/US2009/060104 patent/WO2010045105A1/en active Application Filing
- 2009-10-09 JP JP2011532156A patent/JP5661040B2/ja active Active
- 2009-10-09 BR BRPI0914426-9A patent/BRPI0914426B1/pt active IP Right Grant
- 2009-10-09 CN CN2009801472219A patent/CN102224106A/zh active Pending
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JP2012505823A (ja) | 2012-03-08 |
CN102224106A (zh) | 2011-10-19 |
RU2472708C2 (ru) | 2013-01-20 |
US8722759B2 (en) | 2014-05-13 |
EP2370362B1 (en) | 2013-11-27 |
BRPI0914426B1 (pt) | 2019-10-15 |
US20110196062A1 (en) | 2011-08-11 |
BRPI0914426A2 (pt) | 2015-10-20 |
RU2011114372A (ru) | 2012-10-20 |
EP2370362A1 (en) | 2011-10-05 |
WO2010045105A1 (en) | 2010-04-22 |
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