JP2009280673A - 光重合性組成物 - Google Patents
光重合性組成物 Download PDFInfo
- Publication number
- JP2009280673A JP2009280673A JP2008132956A JP2008132956A JP2009280673A JP 2009280673 A JP2009280673 A JP 2009280673A JP 2008132956 A JP2008132956 A JP 2008132956A JP 2008132956 A JP2008132956 A JP 2008132956A JP 2009280673 A JP2009280673 A JP 2009280673A
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- JP
- Japan
- Prior art keywords
- group
- photopolymerizable composition
- fluorescent agent
- compound
- photopolymerization initiator
- Prior art date
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- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 58
- -1 aromatic amine compound Chemical class 0.000 claims abstract description 143
- 239000000178 monomer Substances 0.000 claims abstract description 51
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 43
- 239000012766 organic filler Substances 0.000 claims abstract description 39
- 239000003999 initiator Substances 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 125000003277 amino group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
- 239000010954 inorganic particle Substances 0.000 claims description 20
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- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 13
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
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- 229920005989 resin Polymers 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- 230000037048 polymerization activity Effects 0.000 abstract description 18
- 239000002253 acid Substances 0.000 abstract description 4
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- AMFGWXWBFGVCKG-UHFFFAOYSA-N Panavia opaque Chemical compound C1=CC(OCC(O)COC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 AMFGWXWBFGVCKG-UHFFFAOYSA-N 0.000 description 5
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- 150000002367 halogens Chemical class 0.000 description 5
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
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- 125000005843 halogen group Chemical group 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
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- QTUVQQKHBMGYEH-UHFFFAOYSA-N 2-(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC=NC=N1 QTUVQQKHBMGYEH-UHFFFAOYSA-N 0.000 description 3
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 239000005548 dental material Substances 0.000 description 3
- UQOUOXLHXPHDHF-UHFFFAOYSA-N diethyl 2,5-dihydroxybenzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC(O)=C(C(=O)OCC)C=C1O UQOUOXLHXPHDHF-UHFFFAOYSA-N 0.000 description 3
- DSSKDXUDARIMTR-UHFFFAOYSA-N dimethyl 2-aminobenzene-1,4-dicarboxylate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C(N)=C1 DSSKDXUDARIMTR-UHFFFAOYSA-N 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 239000007850 fluorescent dye Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
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- 239000001294 propane Substances 0.000 description 3
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- 238000010298 pulverizing process Methods 0.000 description 3
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- 229910052724 xenon Inorganic materials 0.000 description 3
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 3
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- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 2
- QZKVUSSYPPWURQ-UHFFFAOYSA-N 1-methylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C QZKVUSSYPPWURQ-UHFFFAOYSA-N 0.000 description 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
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- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 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
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
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Abstract
【解決手段】 上記光重合性組成物において、フタル酸エステル系蛍光剤、好ましくは
【化1】
(式中、R10及びR11は各々独立に、アルキル基であり、R12は水素原子、アミノ基、水酸基であり、R13はアミノ基、水酸基である。)
で示される蛍光剤を、有機フィラーに含有させた形態で配合させる。
【選択図】 なし
Description
齲蝕や破折等により損傷をうけた歯牙の修復においては、一般にコンポジットレジンと呼ばれるペースト状の光硬化性の複合充填修復材料が、操作の簡便さや審美性の高さから汎用されている。このようなコンポジットレジンは、通常、重合性単量体、充填材、及び光重合開始剤の各成分が配合されてなる。
(B)B1)α−ジケトン化合物、B2)光酸発生剤、及びB3)芳香族アミン化合物を含んでなる光重合開始剤、および
(C)フタル酸エステル系蛍光剤を含有する有機フィラー
を含有してなる光重合性組成物である。
〔(A)ラジカル重合性単量体〕
ラジカル重合性単量体としては、公知のものが特に制限なく使用できる。一般に好適に使用されるものを例示すれば、下記(I)〜(III)に示されるものが挙げられる。
(I)二官能重合性単量体
(i)芳香族化合物系のもの
2,2−ビス(メタクリロイルオキシフェニル)プロパン、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(以下、bis−GMAと略記する)、2,2−ビス(4−メタクリロイルオキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシポリエトキシフェニル)プロパン(以下、D−2.6Eと略記する)、2,2−ビス(4−メタクリロイルオキシジエトキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシテトラエトキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシペンタエトキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシジプロポキシフェニル)プロパン、2(4−メタクリロイルオキシジエトキシフェニル)−2(4−メタクリロイルオキシトリエトキシフェニル)プロパン、2(4−メタクリロイルオキシジプロポキシフェニル)−2−(4−メタクリロイルオキシトリエトキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシプロポキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシイソプロポキシフェニル)プロパン及びこれらのメタクリレートに対応するアクリレート;2−ヒドロキシエチルメタクリレート、2−ヒドロキシプロピルメタクリレート、3−クロロ−2−ヒドロキシプロピルメタクリレート等のメタクリレートあるいはこれらメタクリレートに対応するアクリレートのような−OH基を有するビニルモノマーと、ジイソシアネートメチルベンゼン、4,4‘−ジフェニルメタンジイソシアネートのような芳香族基を有するジイソシアネート化合物との付加から得られるジアダクト等。
(ii)脂肪族化合物系のもの
エチレングリコールジメタクリレート、ジエチレングリコールジメタクリレート、トリエチレングリコールジメタクリレート(以下、3Gと略記する)、テトラエチレングリコールジメタクリレート、ネオペンチルグリコールジメタクリレート、1,3−ブタンジオールジメタクリレート、1,4−ブタンジオールジメタクリレート、1,6−ヘキサンジオールジメタクリレートおよびこれらのメタクリレートに対応するアクリレート;2−ヒドロキシエチルメタクリレート、2−ヒドロキシプロピルメタクリレート、3−クロロ−2−ヒドロキシプロピルメタクリレート等のメタクリレートあるいはこれらのメタクリレートに対応するアクリレートのような−OH基を有するビニルモノマーと、ヘキサメチレンジイソシアネート、トリメチルヘキサメチレンジイソシアネート、ジイソシアネートメチルシクロヘキサン、イソフォロンジイソシアネート、メチレンビス(4−シクロヘキシルイソシアネート)のようなジイソシアネート化合物との付加体から得られるジアダクト;1,2−ビス(3−メタクリロイルオキシ−2−ヒドロキシプロポキシ)エチル等。
(II)三官能重合性単量体
トリメチロールプロパントリメタクリレート、トリメチロールエタントリメタクリレート、ペンタエリスリトールトリメタクリレート、トリメチロールメタントリメタクリレート等のメタクリレート及びこれらのメタクリレートに対応するアクリレート等。
(III)四官能重合性単量体
ペンタエリスリトールテトラメタクリレート、ペンタエリスリトールテトラアクリレート及びジイソシアネートメチルベンゼン、ジイソシアネートメチルシクロヘキサン、イソフォロンジイソシアネート、ヘキサメチレンジイソシアネート、トリメチルヘキサメチレンジイソシアネート、メチレンビス(4−シクロヘキシルイソシアネート)、4,4−ジフェニルメタンジイソシアネート、トリレン−2,4−ジイソシアネートのようなジイソシアネート化合物とグリシドールジメタクリレートとの付加体から得られるジアダクト等。
〔(B)光重合開始剤〕
〔B1)α−ジケトン化合物〕
本発明の光重合性組成物における光重合開始剤に用いる(B1)成分のα−ジケトン化合物としては公知の化合物が何ら制限なく使用できる。上記α−ジケトン化合物を具体的に例示すると、カンファーキノン、カンファーキノンカルボン酸、カンファーキノンスルホン酸等のカンファーキノン類;ジアセチル、アセチルベンゾイル、2,3−ペンタジオン、2,3−オクタジオン、9,10−フェナンスレンキノン、アセナフテンキノン等を挙げることができる。
〔B2)光酸発生剤〕
本発明の光重合性組成物における光重合開始剤の第二の成分は、(B2)光酸発生剤である。
上記一般式(1)中、Xで表されるハロゲン原子は、塩素、臭素、ヨウ素の各ハロゲン原子が好適に使用されるが、塩素原子が置換したトリクロロメチル基を有する化合物を用いるのが一般的である。
で示されるものが挙げられる。
〔B3)芳香族アミン化合物〕
本発明の光重合性組成物における光重合開始剤の第三の成分は、(B3)芳香族アミン化合物である。当該芳香族アミン化合物は、窒素原子に結合した有機基のうちの少なくとも一つが芳香族基であるアミン化合物であればよく、公知のものが特に制限なく使用できるが、より重合活性が高く、また揮発性が低いため臭気が少なく、さらには入手が容易な点で、第3級窒素原子に一つの芳香族基と、2つの脂肪族基が結合したアミン化合物(以下、「第3級芳香族アミン化合物」とも称す)であることが好ましい。代表的な第3級芳香族アミン化合物としては下記一般式(3)で表されるものが挙げられる。
R7及びR8で表されるアルキル基、又はR9で表されるアルキル基、アリール基、アルケニル基、アルコキシ基及びアルキルオキシカルボニル基は、それぞれ非置換のものの他、前記R1及びR2の基で説明したような置換基や水酸基で置換されたものであっても良い。上記アルキル基としては、メチル基、エチル基、n−プロピル基、i−プロピル基、n−ブチル基、n−ヘキシル基、n−オクチル基等の非置換のアルキル基;クロロメチル基、2−クロロエチル基等のハロゲンにより置換されたアルキル基;2−ヒドロキシエチル基等の水酸基により置換されたアルキル基等の炭素数1〜10のものが挙げられる。アリール基としては、フェニル基、p−アルコキシフェニル(例えば、p−メトキシフェニル)、p−アルキルルチオフェニル基(例えば、p−メチルチオフェニル基)、p−ハロフェニル基(例えば、p−クロロフェニル基)、4−ビフェニリル基等の炭素数6〜12のものが例示される。アルケニル基としては、ビニル基、アリル基、2−フェニルエテニル基等の炭素数2〜12のものが挙げられる。アルコキシ基としては、メトキシ基、エトキシ基、ブトキシ基、ヘキトキシ基、オクトキシ基等の炭素数1〜10のもの等が挙げられる。アルキルオキシカルボニル基としては、メトキシカルボニル基、エトキシカルボニル基、ブトキシカルボニル基、アミルオキシカルボニル基、イソアミルオキシカルボニル基等のアルキルオキシ基部分の炭素数が1〜10のものが例示される。
〔B4)第3級脂肪族アミン化合物〕
本発明の光重合性組成物における光重合開始剤としては、上記α−ジケトン、光酸発生剤、及び芳香族アミン化合物からなる光重合開始剤でも良いが、さらにB4)第3級脂肪族アミン化合物を併用すると、その重合活性を一層に向上させることができる。
〔(C)フタル酸エステル系蛍光剤を含有する有機フィラー〕
本発明の最大の特徴は、フタル酸エステル系蛍光剤を有機フィラーに配合させた点にある。それにより、光重合開始剤が前記したようなα−ジケトン化合物、光酸発生剤及び芳香族アミン化合物からなるものでありながら、該フタル酸エステル系蛍光剤による光酸発生剤の変性が生じることがなく、その高い重合活性を良好に保持することが可能になる。
上記アルキル基としては、メチル基、エチル基、n−プロピル基、i−プロピル基等の炭素数1〜3のものが好ましく、特に、炭素数1〜2のものがより好ましい。
(1)略称・略号
(A)ラジカル重合性単量体
・2,2−ビス[(3−メタクリロイルオキシ−2−ヒドロキシプロピルオキシ)フェニル]プロパン(bis−GMA)
・トリエチレングリコールジメタクリレート(3G)
(B)光重合開始剤
B1)α―ジケトン
・カンファーキノン(CQ)
B2−1)トリハロメチル基により置換されたs−トリアジン化合物
・2,4,6−トリス(トリクロロメチル)−s−トリアジン(TCT)
・2−フェニル−4,6−ビス(トリクロロメチル)−s−トリアジン(PBCT)
B2−2)ジフェニルヨードニウム塩化合物
・ジフェニルヨードニウムヘキサフルオロリン酸(IP)
・4−イソプロピル−4‘メチルジフェニルヨードニウムテトラキス(ペンタフルオロフェニル)ボラート(IB)
B3)芳香族アミン化合物
・N,N−ジメチルp−安息香酸エチル(DMBE)
・N,N−ジメチルp−トルイジン(DMPT)
B4)第3級脂肪族アミン
・トリエタノールアミン(TEOA)
・N−メチルジエタノールアミン(MDEOA)
B5)その他
・アゾビスイソブチロニトリル(AIBN)
(C)蛍光剤
〔フタル酸エステル系蛍光剤〕
・ジメチルアミノテレフタレート(DATP)
・2,5−ジヒドロキシテレフタル酸ジエチル(DHTP)
〔その他の蛍光剤〕
・2,5ビス(5’−tert−ブチルベンゾオキサゾリル(2))チオフェン(BOTh)
(D)その他の成分
・ハイドロキノンモノメチルエーテル(HQME)
・2−ヒドロキシ−4−メトキシベンゾフェノン(BP)
(E)無機粒子
・球状シリカジルコニアフィラー;一次粒子の平均粒子径=0.2μm、γ−メタクリロイルオキシプロピルトリメトキシシラン表面処理物(E−1)
また、光硬化性コンポジットレジンの調製方法、有機フィラー及び有機無機複合フィラーの調製方法及び硬化体の機械的強度の測定は以下の方法を用いた。
(1)光硬化性コンポジットレジンの調製方法
ラジカル重合性単量体に対し所定量の光重合開始剤と有機フィラー及びまたは、有機無機複合及びまたは、無機粒子を加え、赤色光下にて均一に攪拌して調製した。
(2)有機フィラーの製造方法
〔無機粒子非含有のもの〕
ラジカル重合性単量体(bis−GMA/3G=60/40)中に、蛍光剤を所定量(表1)、重合開始剤(AIBN)を質量比で0.5%予め溶解させた。これを、95℃窒素加圧下で一時間加熱することによって、重合硬化させた。この硬化体を、振動ボールミルを用いて粉砕し、平均粒径30μmの有機フィラーH−1,H−2,H−3、H−4,H−5,H−6,H−7を得た。
〔有機無機複合フィラー〕
ラジカル重合性単量体(bis−GMA/3G=60/40)中に、蛍光剤を所定量(表1)、重合開始剤(AIBN)を質量比で0.5%予め溶解させておき、無機粒子を所定量(表1)添加混合し、乳鉢でペースト化した。これを、95℃窒素加圧下で一時間加熱することによって、重合硬化させた。この硬化体を、振動ボールミルを用いて粉砕し、さらにγ-メタクリロイルオキシプロピルトリメトキシシラン0.02質量%によって、エタノール中、90℃で5時間還留することで表面処理を行い、平均粒径30μmの有機無機複合フィラーI−1,I−2,I−3,I−4,I−5を得た。
6mmφ×1.0mmの孔を有するポリテトラフルオロエチレン製のモールドにペーストを充填してポリプロピレンフィルムで圧接し、歯科用光照射器(LUX・O・MAX(以下LMとも略す)、アケダデンタル社;光出力密度137mW/cm2)をポリプロピレンフィルムに密着して10秒照射し、硬化体を調製した。得られた硬化体を微小硬度計(松沢精機製MHT−1型)にてヴィッカース圧子を用いて、荷重100gf、荷重保持時間30秒で試験片にできたくぼみの対角線長さにより求めた。
(4)保存安定性の評価
調製した光硬化性コンポジットレジンを50℃に設定したインキュベーター内に保管し、一定期間毎に(4)と同様な方法でヴィッカース硬度を測定し、得られたヴィッカース硬度値の経時変化から保存安定性を評価した。
(5)蛍光性の評価
7mmφ×3.0mmの孔を有するポリテトラフルオロエチレン製のモールドにペーストを充填してポリプロピレンフィルムで圧接し、歯科用光照射器(トクソーパワーライト、トクヤマデンタル社;光出力密度600mW/cm2)をポリプロピレンフィルムに密着して30秒照射し、硬化体を調製した。得られた硬化体を紫外光照射器(MINERALIGHT LAMP、フナコシ薬品社;最大吸収波長366nm)を用いて、その蛍光の発光状態を観察した。特に優れた蛍光が確認できたものを◎、良好な蛍光が確認できたものを○、蛍光が確認できなかったものを×で評価した。
bis−GMA(60質量部)、3G(40質量部)からなるラジカル重合性単量体100質量部、重合禁止剤としてHQMEを0.15質量部、及び表2に示す光重合開始剤、有機フィラー、及び蛍光剤からなる光硬化性コンポジットレジンを暗所下、メノウ乳鉢を用いて攪拌混合してペースト状の組成物を調製した。上記ペーストについて、光照射の所定時間を10秒間として得られた硬化体のヴィッカース硬度を測定した。また、保存安定性に関しても評価を行なった。結果を表2に示した。
表3に示したように有機フィラーの種類を変化させ、実施例1と同様にして光硬化性コンポジットレジンのペーストを調製した。得られた光硬化性コンポジットレジンの各種物性を測定した結果を表3に示した。
表4に示したように光重合開始剤として配合する各成分の種類を変化させ、実施例1と同様にして光硬化性コンポジットレジンのペーストを調製した。得られた光硬化性コンポジットレジンの各種物性を測定した結果を表4に示した。
Claims (6)
- (A)ラジカル重合性単量体、
(B)B1)α−ジケトン化合物、B2)光酸発生剤、及びB3)芳香族アミン化合物を含んでなる光重合開始剤、および
(C)フタル酸エステル系蛍光剤を含有する有機フィラー
を含有してなる光重合性組成物。 - (B)光重合開始剤におけるB2)光酸発生剤が、トリハロメチル基により置換されたs−トリアジン化合物、及びジアリールヨードニウム塩系化合物から選ばれる少なくとも1種である請求項1記載の光重合性組成物。
- (B)光重合開始剤として、さらにB4)3つの飽和脂肪族基が窒素原子に結合している第三級アミノ基を有しており、かつ、該飽和脂肪族基のうち少なくとも2つは電子吸引性基を置換基として有している第三級脂肪族アミン化合物を含んでなる請求項1または請求項2記載の光重合性組成物。
- (C)フタル酸エステル系蛍光剤を含有する有機フィラーが、有機樹脂100重量部に対して無機粒子を150〜600重量部配合した有機無機複合フィラーである請求項1〜4のいずれか一項に記載の光重合性組成物。
- 請求項1〜5のいずれか一項に記載の歯科用修復材料。
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EP09750591.1A EP2280032B1 (en) | 2008-05-21 | 2009-05-20 | Photopolymerizable compositions |
US12/991,251 US8394869B2 (en) | 2008-05-21 | 2009-05-20 | Photopolymerizable compositions useful as a dental restorative material |
CN2009801181711A CN102037024B (zh) | 2008-05-21 | 2009-05-20 | 光聚合性组合物 |
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JP2014024775A (ja) * | 2012-07-25 | 2014-02-06 | Tokuyama Dental Corp | 歯科用硬化性組成物 |
WO2021125246A1 (ja) | 2019-12-17 | 2021-06-24 | クラレノリタケデンタル株式会社 | 蛍光性を有する歯科用硬化性組成物及びその硬化物 |
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JP5683337B2 (ja) * | 2011-03-17 | 2015-03-11 | 株式会社トクヤマデンタル | 化学重合型歯科用接着性組成物 |
WO2012128167A1 (ja) * | 2011-03-18 | 2012-09-27 | 株式会社トクヤマデンタル | 象牙質用修復材料キット |
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US11779524B2 (en) | 2020-03-16 | 2023-10-10 | Kabushiki Kaisha Shofu | Photopolymerization initiator comprising an aryliodonium salt for dental photocurable compositions |
US20220287918A1 (en) | 2021-03-12 | 2022-09-15 | Shofu Inc. | Dental adhesive composition excellent in storage stability |
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CN102037024A (zh) | 2011-04-27 |
US20110172323A1 (en) | 2011-07-14 |
CN102037024B (zh) | 2013-01-23 |
EP2280032B1 (en) | 2015-01-07 |
EP2280032A1 (en) | 2011-02-02 |
US8394869B2 (en) | 2013-03-12 |
JP5435892B2 (ja) | 2014-03-05 |
EP2280032A4 (en) | 2014-04-02 |
WO2009142229A1 (ja) | 2009-11-26 |
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