JP2006290803A - 未反応モノマーを軽減した医科歯科用材料 - Google Patents
未反応モノマーを軽減した医科歯科用材料 Download PDFInfo
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- JP2006290803A JP2006290803A JP2005114020A JP2005114020A JP2006290803A JP 2006290803 A JP2006290803 A JP 2006290803A JP 2005114020 A JP2005114020 A JP 2005114020A JP 2005114020 A JP2005114020 A JP 2005114020A JP 2006290803 A JP2006290803 A JP 2006290803A
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- 239000000178 monomer Substances 0.000 title claims abstract description 38
- 239000005548 dental material Substances 0.000 title abstract description 3
- 239000012567 medical material Substances 0.000 title abstract description 3
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- 239000003178 glass ionomer cement Substances 0.000 claims abstract description 14
- 239000000843 powder Substances 0.000 claims abstract description 12
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 239000003505 polymerization initiator Substances 0.000 claims abstract description 5
- 239000011521 glass Substances 0.000 claims abstract description 4
- 239000008213 purified water Substances 0.000 claims abstract description 3
- 239000005518 polymer electrolyte Substances 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 15
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 13
- 239000000203 mixture Substances 0.000 abstract description 10
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- 238000009835 boiling Methods 0.000 abstract description 4
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- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
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- NPZOFLLFFNIYON-UHFFFAOYSA-N n,n,4-trimethylbenzenesulfinamide Chemical compound CN(C)S(=O)C1=CC=C(C)C=C1 NPZOFLLFFNIYON-UHFFFAOYSA-N 0.000 description 2
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- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- PZGVVCOOWYSSGB-KWZUVTIDSA-L (z)-but-2-enedioate;dioctyltin(2+) Chemical class [O-]C(=O)\C=C/C([O-])=O.CCCCCCCC[Sn+2]CCCCCCCC PZGVVCOOWYSSGB-KWZUVTIDSA-L 0.000 description 1
- OZOSSJWZNHBBDV-UHFFFAOYSA-N 1,3,5-trimethyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound CC1C(=O)N(C)C(=S)N(C)C1=O OZOSSJWZNHBBDV-UHFFFAOYSA-N 0.000 description 1
- VVSASNKOFCZVES-UHFFFAOYSA-N 1,3-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound CN1C(=O)CC(=O)N(C)C1=O VVSASNKOFCZVES-UHFFFAOYSA-N 0.000 description 1
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- 231100000820 toxicity test Toxicity 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
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009777 vacuum freeze-drying Methods 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
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Abstract
【解決手段】レジンモディファイドグラスアイオノマーセメントにおいて、フルオロアルミノシリケートガラス粉末、重合開始材、重合促進材を含む粉成分と、液成分として未反応モノマー0.00001〜1質量%を含む酸性高分子電解質、精製水、ヒドロキシカルボン酸およびラジカル重合性単量体が挙げられ、これらを共存可能な組み合わせで使用することにより目的を達成できる。
【選択図】なし
Description
酸反応性フィラーとしては酸化アルミニウム−酸化ケイ素を基本骨格とし、修飾イオンンとしてカルシウム及び/またはストロンチウムを含むフルオロアルミノシリケート粉末が好適である。また該酸反応性フィラーは液材とのなじみ性や寿命性を共存させる目的でシランカップリング剤にて表面処理を施してもよい。
1.酸性高分子電解質の調整
株式会社松風製グラスアイオノマーCX-Plusの液材100mlに蒸留水900mlを加水し、ベーンポンプにて日本ミリポア製限外濾過膜(バイオマックス 分画分子量 濾過面積0.1m2)にて最終体積が100mlになるまで限外濾過を行った。その後、さらに蒸留水を400ml加え予備凍結し東京理科器械製フリーズドライヤーを使用し、凍結乾燥した。得られたポリアルケン酸粉末を蒸留水にて固形分濃度が45wt%になるように溶液調整した。この酸性高分子電解質溶液をリン酸緩衝液にて希釈しGPC測定を行ったが、未重合モノマーは認められなかった。この45wt%溶液を標準液1(実施例用液1)とする。
標準液1にアクリル酸モノマーを表1に示した濃度になるように添加した。
実施例用液又は比較例用液を用いて粉液型レジンモディファイドグラスアイオノマーセメントの液材を表2の調合組成で調整した。また粉材は表3の調合組成にて調整した。なお表3に記載した過硫酸カリウムおよびアスコルビン酸は市販薬品の結晶をアルミナ乳鉢にて50μm以下に微粉砕し株式会社松風製CX-PLUS粉材に均一混合した。
2-HEMA:2−ヒドロキシエチルメタクリレート
医科・歯科用硬化性組成物の実施例用液材又は比較例用液材から揮発するアクリル酸モノマーの定量分析を以下の分析方法にて行った。
試料50mgを石英製試料皿に秤量し、加熱炉に設置した加熱管(室温25℃)中央部に導入した。窒素ガスを50ml/minの流速で流し、追い出される揮発性成分を吸着管(Carbotrap400)に捕集した。捕集時間は20分とした。(気体採取量1L)
捕集した吸着管を熱脱離GC/MS分析システムのチャンバー部にセットした。チャンバー部(吸着管)を急速加熱して有機成分を離脱させ、GC/MSに導入し測定した。得られたトータルイオンクロマトグラム(TIC)で試料間の比較を行い、検出された成分のスペクトル同定を行った。なお、GC/MS測定条件は以下のとうりである。
(熱離脱条件)
装置 :スペルコ社製 熱離脱装置(TDU)
離脱条件 :300℃まで急速昇温し5分間保持
(GC/MS測定条件)
GC/MS :HP6890/HP5973
分離カラム:SPB-1(sulfur)30m×0.32mmI.D 4.0μm Film
GC温度 :‐30℃→300℃ 昇温10℃/min
GC注入口:TDU使用
キャリアー:ヘリウム 3ml/min
検出器 :質量分析計(MS)230℃
測定質量範囲:m/Z=33~600
上述した分析の結果を表4に記載する。
東洋紡績株式会社製三次元培養皮膚モデル「テストスキン」を用いて以下に記載した方法にて抽出した溶液を該細胞に10時間原液のまま作用させた後に細胞生存率を算出した。なお実験操作は「テストスキン」使用方法に従い行った。
実施例用液材1〜3は刺激臭をほとんど感じず、比較例用液材1,2は刺激臭が認められた。
Claims (1)
- レジンモディファイドグラスアイオノマーセメントにおいて、フルオロアルミノシリケートガラス粉末、重合開始材、重合促進材を含む粉成分と、液成分として未反応モノマー0.00001〜1質量%を含む酸性高分子電解質、精製水、ヒドロキシカルボン酸およびラジカル重合性単量体からなるレジンモディファイドグラスアイオノマーセメント。
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05117593A (ja) * | 1991-10-31 | 1993-05-14 | Nitto Denko Corp | 耐熱性にすぐれた感圧性接着剤およびその接着シ―ト類とこれらの製造方法 |
JPH05271624A (ja) * | 1992-03-27 | 1993-10-19 | Nitto Denko Corp | 耐熱性にすぐれた感圧性接着剤およびその接着シ―ト類とこれらの製造方法 |
JPH05279424A (ja) * | 1991-03-25 | 1993-10-26 | Mitsui Petrochem Ind Ltd | 歯質表面処理用アクリル系共重合体およびその用途 |
JPH0892025A (ja) * | 1994-09-28 | 1996-04-09 | Dainippon Toryo Co Ltd | 歯科セメント用ガラス粉末 |
JPH0948702A (ja) * | 1995-08-03 | 1997-02-18 | Dainippon Toryo Co Ltd | 歯科用セメント組成物 |
JP2869078B2 (ja) * | 1987-12-30 | 1999-03-10 | ミネソタ マイニング アンド マニユフアクチユアリング カンパニー | 光硬化性イオノマーセメント |
JP2001226425A (ja) * | 2000-02-16 | 2001-08-21 | Daikin Ind Ltd | フッ素系アイオノマーの精製・濃縮方法 |
-
2005
- 2005-04-11 JP JP2005114020A patent/JP4904015B2/ja active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2869078B2 (ja) * | 1987-12-30 | 1999-03-10 | ミネソタ マイニング アンド マニユフアクチユアリング カンパニー | 光硬化性イオノマーセメント |
JPH05279424A (ja) * | 1991-03-25 | 1993-10-26 | Mitsui Petrochem Ind Ltd | 歯質表面処理用アクリル系共重合体およびその用途 |
JPH05117593A (ja) * | 1991-10-31 | 1993-05-14 | Nitto Denko Corp | 耐熱性にすぐれた感圧性接着剤およびその接着シ―ト類とこれらの製造方法 |
JPH05271624A (ja) * | 1992-03-27 | 1993-10-19 | Nitto Denko Corp | 耐熱性にすぐれた感圧性接着剤およびその接着シ―ト類とこれらの製造方法 |
JPH0892025A (ja) * | 1994-09-28 | 1996-04-09 | Dainippon Toryo Co Ltd | 歯科セメント用ガラス粉末 |
JPH0948702A (ja) * | 1995-08-03 | 1997-02-18 | Dainippon Toryo Co Ltd | 歯科用セメント組成物 |
JP2001226425A (ja) * | 2000-02-16 | 2001-08-21 | Daikin Ind Ltd | フッ素系アイオノマーの精製・濃縮方法 |
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