JP6432983B2 - 医科歯科用硬化性組成物 - Google Patents
医科歯科用硬化性組成物 Download PDFInfo
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- JP6432983B2 JP6432983B2 JP2015084558A JP2015084558A JP6432983B2 JP 6432983 B2 JP6432983 B2 JP 6432983B2 JP 2015084558 A JP2015084558 A JP 2015084558A JP 2015084558 A JP2015084558 A JP 2015084558A JP 6432983 B2 JP6432983 B2 JP 6432983B2
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- bis
- diyl
- medical
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- propane
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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 4
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- LCKNZCHKSVSFHH-UHFFFAOYSA-N [3,5-bis(1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl)phenyl]boron Chemical compound [B]C1=CC(C(OC)(C(F)(F)F)C(F)(F)F)=CC(C(OC)(C(F)(F)F)C(F)(F)F)=C1 LCKNZCHKSVSFHH-UHFFFAOYSA-N 0.000 description 4
- AFJXJDKUWZPRQX-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]boron Chemical compound [B]C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 AFJXJDKUWZPRQX-UHFFFAOYSA-N 0.000 description 4
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- 159000000002 lithium salts Chemical class 0.000 description 4
- 159000000003 magnesium salts Chemical class 0.000 description 4
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- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
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- 238000003860 storage Methods 0.000 description 4
- 229910052712 strontium Inorganic materials 0.000 description 4
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 4
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 4
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- KCWWCWMGJOWTMY-UHFFFAOYSA-N 1-benzyl-5-phenyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1C(C=2C=CC=CC=2)C(=O)NC(=O)N1CC1=CC=CC=C1 KCWWCWMGJOWTMY-UHFFFAOYSA-N 0.000 description 3
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
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- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 3
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- ALTWGIIQPLQAAM-UHFFFAOYSA-N metavanadate Chemical compound [O-][V](=O)=O ALTWGIIQPLQAAM-UHFFFAOYSA-N 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- LKNDYQNNDRTHFP-UHFFFAOYSA-N n,n,3,4-tetramethylaniline Chemical compound CN(C)C1=CC=C(C)C(C)=C1 LKNDYQNNDRTHFP-UHFFFAOYSA-N 0.000 description 1
- NBFRQCOZERNGEX-UHFFFAOYSA-N n,n,3,5-tetramethylaniline Chemical compound CN(C)C1=CC(C)=CC(C)=C1 NBFRQCOZERNGEX-UHFFFAOYSA-N 0.000 description 1
- CWOMTHDOJCARBY-UHFFFAOYSA-N n,n,3-trimethylaniline Chemical compound CN(C)C1=CC=CC(C)=C1 CWOMTHDOJCARBY-UHFFFAOYSA-N 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- MJRUTYCVCLZWSR-UHFFFAOYSA-N n,n-dimethyl-4-propan-2-ylaniline Chemical compound CC(C)C1=CC=C(N(C)C)C=C1 MJRUTYCVCLZWSR-UHFFFAOYSA-N 0.000 description 1
- 239000004763 nomex Substances 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- OGUCKKLSDGRKSH-UHFFFAOYSA-N oxalic acid oxovanadium Chemical compound [V].[O].C(C(=O)O)(=O)O OGUCKKLSDGRKSH-UHFFFAOYSA-N 0.000 description 1
- MHHDXUNFNAZUGB-UHFFFAOYSA-N oxidovanadium(2+) Chemical compound [V+2]=O MHHDXUNFNAZUGB-UHFFFAOYSA-N 0.000 description 1
- BFYJDHRWCNNYJQ-UHFFFAOYSA-N oxo-(3-oxo-3-phenylpropoxy)-(2,4,6-trimethylphenyl)phosphanium Chemical compound CC1=CC(C)=CC(C)=C1[P+](=O)OCCC(=O)C1=CC=CC=C1 BFYJDHRWCNNYJQ-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 1
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 230000037048 polymerization activity Effects 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 1
- HPWMVNFJSFHJIW-UHFFFAOYSA-M potassium;2,4,6-tri(propan-2-yl)benzenesulfinate Chemical compound [K+].CC(C)C1=CC(C(C)C)=C(S([O-])=O)C(C(C)C)=C1 HPWMVNFJSFHJIW-UHFFFAOYSA-M 0.000 description 1
- NLZLDWFYQXFPSZ-UHFFFAOYSA-M potassium;2,4,6-triethylbenzenesulfinate Chemical compound [K+].CCC1=CC(CC)=C(S([O-])=O)C(CC)=C1 NLZLDWFYQXFPSZ-UHFFFAOYSA-M 0.000 description 1
- YVHWGMMGEAQQRT-UHFFFAOYSA-M potassium;4-methylbenzenesulfinate Chemical compound [K+].CC1=CC=C(S([O-])=O)C=C1 YVHWGMMGEAQQRT-UHFFFAOYSA-M 0.000 description 1
- LZSBNSVOXWMXLL-UHFFFAOYSA-M potassium;benzenesulfinate Chemical compound [K+].[O-]S(=O)C1=CC=CC=C1 LZSBNSVOXWMXLL-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000003829 resin cement Substances 0.000 description 1
- 238000012712 reversible addition−fragmentation chain-transfer polymerization Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
- VMMZJFAHOAKUQM-UHFFFAOYSA-N sodium;1,3,5-trimethyl-1,3-diazinane-2,4,6-trione Chemical compound [Na].CC1C(=O)N(C)C(=O)N(C)C1=O VMMZJFAHOAKUQM-UHFFFAOYSA-N 0.000 description 1
- KNHRGMOGYVTHPU-UHFFFAOYSA-M sodium;2,4,6-triethylbenzenesulfinate Chemical compound [Na+].CCC1=CC(CC)=C(S([O-])=O)C(CC)=C1 KNHRGMOGYVTHPU-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-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
- JIYXDFNAPHIAFH-UHFFFAOYSA-N tert-butyl 3-tert-butylperoxycarbonylbenzoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC(C(=O)OC(C)(C)C)=C1 JIYXDFNAPHIAFH-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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000004762 twaron Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- UUUGYDOQQLOJQA-UHFFFAOYSA-L vanadyl sulfate Chemical compound [V+2]=O.[O-]S([O-])(=O)=O UUUGYDOQQLOJQA-UHFFFAOYSA-L 0.000 description 1
- 229940041260 vanadyl sulfate Drugs 0.000 description 1
- 229910000352 vanadyl sulfate Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
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Description
なお、qとrの和はDの価数に等しく、rは1以上の正の整数であり、nは0〜3、aは1〜6である。以下に代表的な化合物の化学構造を具体的に一部記載する。
表1の調合で有機質繊維表面の官能化を行った。すなわち、冷却管、攪拌羽根、温度計を備えた500mL容量の4口セパラブルフラスコに凍結乾燥済セルロースナノファイバー(スギノマシン製IMa‐10002)5.0g、脱水ジメチルスルホキシド200mL、ジブチルチン(IV)ジラウレート20mgを計量し、十分に攪拌・均一化させた。セパラブルフラスコをオイルバスに浸け70℃に加温し、滴下ロートにて2‐イソシアネートエチルメタクリレート14.4gを80℃を超えない様に少しづつ滴下した。滴下終了後、さらに70℃にて8時間熟成させた。熟成後、反応溶液を多量のエタノール中に攪拌下にて投入し官能化させた有機質繊維を沈澱させた。沈澱はアセトン溶解/エタノール沈澱を数回繰り返し、未反応の2‐イソシアネートエチルメタクリレートとジメチルスルホキシドを除去した。
有機質繊維表面の官能化2〜4(官能基導入)
表1の調合で「有機質繊維表面の官能化1」同様の手順により官能化を行った。
重合性シランカップリング剤(信越シリコーン社製KBM‐503)を用いOX‐50(日本アエロジル社製)およびFuselex‐X(龍森社製)の表面改質をアセトン溶媒中で行った。その後、官能化した有機質繊維およびラジカル重合性モノマー等を加え医科歯科用硬化性組成物の調製を行った。具体的な調製方法を以下に記載する。表2に記載した量のKBM‐503をアセトン300mLに溶解し、OX‐50およびFuselex‐Xが入った500mLナスフラスコに加えた。その後、電磁攪拌子を入れ10分間攪拌し、さらに28KHz‐150Wの超音波分散機にて5分間分散させた。分散終了後、攪拌下にて蒸留水2.4gおよび1wt%燐酸水溶液1.2gを加え、フラスコを沸騰ウオーターバスに浸け5時間還流させた。還流終了後、内温を室温まで戻し遮光下にてラジカル重合性バインダー液(UDMA,2G)、有機質繊維および光重合開始剤を加え、均一に攪拌した後にエバポレータにてアセトンを留去した。その後、Thinky社製Planetary Vacuum mixer ARV‐310にて1000rpm‐5KPa‐15minの条件下にて完全に溶媒を除去し医科歯科用硬化性組成物を得た。この様にして得られた医科歯科用硬化性組成物をISO4049に従い、硬化体を作製しインストロン万能試験機(インストロン5567、インストロン社製)を用い曲げ強度を求めた。なお、光重合は株式会社松風製Griplight IIにて30秒間光照射することで行った。
表3記載の調合にて実施例1‐1〜1‐4同様に行った。
比較例1‐1(充填率70wt%),2‐1〜2‐2(充填率30wt%)
表4記載の調合にて実施例1‐1〜1‐4同様に行った。なお、比較例2‐2のR8200は表面が既にトリメチルシリル基で覆われているため、シランカップリング処理は行わずラジカル重合性モノマー添加時に加えた。
実施例2‐1〜2‐4,比較例2‐1〜2‐2で調製した医科歯科用硬化性組成物0.5gを10cm×10cmのガラス板に計り取り、地面に対して垂直に保持した。保持10分後に重力により垂れた長さを計測しチキソ性の尺度とした。
Claims (3)
- 有機質繊維を含有する医科歯科用硬化性組成物であって、
前記有機質繊維がセルロースナノファイバー、キチンナノファイバー、キトサンナノファイバーのいずれかであり、
前記有機質繊維の表面にアクリロイル基またはメタクリロイル基が導入されていることを特徴とする医科歯科用硬化性組成物。 - 請求項1に記載の医科歯科用硬化性組成物であって、
無機充填剤、ラジカル重合性モノマーを含み、
さらに重合開始剤または重合促進剤の少なくとも1種類以上を含むことを特徴とする、医科歯科用硬化性組成物。 - 前記有機質繊維のアスペクト比が100から10000の範囲である事を特徴とする請求項1記載の医科歯科用硬化性組成物。
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