JP2009209079A - モノマーによって色調変化を抑えた光硬化性歯科用組成物 - Google Patents
モノマーによって色調変化を抑えた光硬化性歯科用組成物 Download PDFInfo
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- JP2009209079A JP2009209079A JP2008052963A JP2008052963A JP2009209079A JP 2009209079 A JP2009209079 A JP 2009209079A JP 2008052963 A JP2008052963 A JP 2008052963A JP 2008052963 A JP2008052963 A JP 2008052963A JP 2009209079 A JP2009209079 A JP 2009209079A
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- acrylate
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- 239000000178 monomer Substances 0.000 title claims abstract description 30
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- -1 acrylate compound Chemical class 0.000 claims abstract description 40
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
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- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 11
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- NVYVSXAJBOHJPI-UHFFFAOYSA-N dodecane;2-(2-methylprop-2-enoyloxy)ethyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCC.CC(=C)C(=O)OCCOC(=O)C(C)=C NVYVSXAJBOHJPI-UHFFFAOYSA-N 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- WOXXJEVNDJOOLV-UHFFFAOYSA-N ethenyl-tris(2-methoxyethoxy)silane Chemical compound COCCO[Si](OCCOC)(OCCOC)C=C WOXXJEVNDJOOLV-UHFFFAOYSA-N 0.000 description 1
- HLBOJHQDGVDWPU-UHFFFAOYSA-N ethyl carbamate;[2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate;5-isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane Chemical compound CCOC(N)=O.CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1.C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HLBOJHQDGVDWPU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- APURLPHDHPNUFL-UHFFFAOYSA-M fluoroaluminum Chemical compound [Al]F APURLPHDHPNUFL-UHFFFAOYSA-M 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000002241 glass-ceramic Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- RGWXKIXBGUMRHV-UHFFFAOYSA-N heptadecane;2-(2-methylprop-2-enoyloxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C.CCCCCCCCCCCCCCCCC RGWXKIXBGUMRHV-UHFFFAOYSA-N 0.000 description 1
- IMQFKOJLUVZISM-UHFFFAOYSA-N hexacosane 2-(2-methylprop-2-enoyloxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C.CCCCCCCCCCCCCCCCCCCCCCCCCC IMQFKOJLUVZISM-UHFFFAOYSA-N 0.000 description 1
- DJXVGSFCGXAYGI-UHFFFAOYSA-N hexadecane;2-(2-methylprop-2-enoyloxy)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C.CCCCCCCCCCCCCCCC DJXVGSFCGXAYGI-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- YDLYQMBWCWFRAI-UHFFFAOYSA-N n-Hexatriacontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC YDLYQMBWCWFRAI-UHFFFAOYSA-N 0.000 description 1
- KUPLEGDPSCCPJI-UHFFFAOYSA-N n-Tetracontane Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC KUPLEGDPSCCPJI-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- LGWZGBCKVDSYPH-UHFFFAOYSA-N triacontane Chemical compound [CH2]CCCCCCCCCCCCCCCCCCCCCCCCCCCCC LGWZGBCKVDSYPH-UHFFFAOYSA-N 0.000 description 1
- OLTHARGIAFTREU-UHFFFAOYSA-N triacontane Natural products CCCCCCCCCCCCCCCCCCCCC(C)CCCCCCCC OLTHARGIAFTREU-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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- A61K6/60—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
- A61K6/20—Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish
-
- 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
- A61K6/80—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)
- Life Sciences & Earth Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biophysics (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Dental Preparations (AREA)
Abstract
Description
[1] 少なくとも1種以上の(a)可視光光重合触媒化合物0.01〜10重量部と、(b)1種以上の一般式(I):
[2] 可視光光重合触媒化合物(a)がアシルホスフィンオキサイド化合物である前記[1]に記載の歯科用組成物;
[3] 可視光光重合触媒化合物(a)が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である前記[1]または[2]に記載の歯科用組成物;
[4] さらに、(c)重合性官能基を3個以上有する多官能モノマーを含む前記[1]ないし[3]のいずれか1に記載の歯科用組成物;
[5] 多官能モノマー(c)がジペンタエリスルトールヘキサアクリレートである前記[4]に記載の歯科用組成物;および
[6] (b)ジ(メタ)アクリレート化合物を5〜70重量部、(c)多官能モノマーを30〜95重量部含む前記[4]または[5]に記載の歯科用組成物
を提供する。
本発明の歯科用組成物に用いる(a)可視光光触媒化合物の例としては、ジアセチル、ベンジル、4,4‘−ジメトキシベンジル、4,4‘−ジメトキシベンジル、4,4‘−オキシベンジル、4,4‘−クロルベンジル、カンファーキノン、カンファーキノンカルボン酸、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、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、2,6−ジメチルベンゾイルジフェニルホスフィンオキサイド、2,6−ジメトキシベンゾイルジフェニルホスフィンオキサイド、2,6−ジクロロベンゾイルジフェニルホスフィンオキサイド、2,3,5,6−テトラメチルベンゾイルジフェニルホスフィンオキサイド、2,4,6−トリメチルベンゾイルフェニルホスフィン酸メチル、2,4,6−トリメチルベンゾイルフェニルホスフィン酸エチルエステル、2,4,6−トリメチルベンゾイルフェニルホスフィン酸フェニルエステルなどが挙げられる。
この中でも特に、アシルホスフィンオキサイド化合物は、紫外あるいは近紫外領域では絶大な光重合性を示すため光重合の産業分野で広く普及している。また、硬化物の黄変が起こりにくく、内部硬化性も優れている。したがって透明な厚膜や隠ぺい力の大きい顔料を含有した材料の光硬化に利用され、最近では、歯科分野でも使用されている。また、アシルホスフィンオキサイド化合物から成る可視光線重合開始剤を用いた組成物は、薄層表面硬化性の向上効果も得られる。よってアシルホスフィンオキサイド化合物が好ましく、さらに好ましくは、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である。
本発明の組成物に用いる(c)多官能モノマーの例としては、ポリエチレン性不飽和カルバモイルイソシアヌレートを含む重合性多官能アクリレート;フェニルグリシジルエーテルアクリレートヘキサメチレンジイソシアネートウレタンプレポリマー、フェニルグリシジルエーテルトルエンジイソシアネートウレタンプレポリマー、ペンタエリスリトールトリアクリレートトルエンジイソシアネートウレタンプレポリマーおよびペンタエリスリトールトリアクリレートイソホロンジイソシアネートウレタンプレポリマーなどのウレタン結合を有する重合性多官能アクリレート;ジトリメチロールプロパンテトラアクリレート、エトキシ化ペンタエリスリトールテトラアクリレート、プロポキシ化ペンタエリスリトールテトラアクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールペンタ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレートなどを挙げることができる。
この中でも特に、安定性などが優れているジペンタエリスリトールヘキサアクリレートが好ましい。
この重合禁止剤の例としては、ハイドロキノンモノメチルエーテル、ブチル化ヒドロキシトルエン、ハイドロキノン、などを挙げることができ、その中でもハイドロキノンモノメチルエーテルおよびブチル化ヒドロキシトルエンが好ましい。
また、紫外線吸収剤の例としては、ベンゾフェノン系、シアノアクリレート系、ヒンダートアミン系、トリアジン系などを挙げることができる。
また、溶剤の例としては、水、エタノール、i−プロパノール、アセトン、ジメチルスルホキシド、ジメチルホルムアミド、酢酸エチル、酢酸ブチルなどを挙げることができる。
CQ:dl−カンファーキノン
APO: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
DMBE:4−N,Nジメチルアミノ安息香酸エチル
DPH:ジペンタエリスリトールヘキサアクリレート
UDMA:ジメタクリロキシエチル−2,2,4−トリメチルヘキサメチレンジウレタン
23G:トリコサンエチレングリコールジメタクリレート(繰り返し単位数n=23)
14G:テトラデカンエチレングリコールジメタクリレート(繰り返し単位数n=14)
9G:ノナエチレングリコールジメタクリレート(繰り返し単位数n=9)
3G:トリエチレングリコールジメタクリレート(繰り返し単位数n=3)
(1)薄層表面硬化性評価
調製した各種光硬化性組成物を練板紙上に1滴採取し、筆で薄く(厚さ約0.1mm)拡げた。ハロゲンランプ照射器ソリディライト[株式会社松風社製](1分間照射)で光照射し、手感により薄層表面硬化性を確認した。
◎:表面の未反応モノマー量が極めて少なく、極めて高い薄層表面硬化性を示す。
○:表面の未反応モノマー量が少なく、高い薄層表面硬化性を示す。
×:表面の未反応モノマー量が認められ、低い薄層表面硬化性を示す。
調製した各種光硬化性組成物をステンレス製リング(内径15mm、厚さ0.5mm)内に入れ、2枚のカバーガラスで上下方向から圧接し、分光測色計CM−2002(コニカミノルタ社)により測色(L*a*b*表色系)し、硬化前の色調とした。次に、光重合器(ソリディライト、株式会社松風社製)で表裏両面1分間ずつ光照射した後測色を行った。硬化前と硬化後の色差ΔE*およびΔb*を算出した。ΔE*とΔb*は以下のように算出される。
可視光線重合開始剤およびラジカル重合性モノマー(DPH、14G)からなる組成物を表1に示す組成で均一溶液に調整した。歯科用光照射器による薄層表面硬化性の評価、硬化前後の色調変化および硬化後色調の評価を測定した。結果を表1に示す。
Claims (6)
- 可視光光重合触媒化合物(a)がアシルホスフィンオキサイド化合物である請求項1に記載の歯科用組成物。
- 可視光光重合触媒化合物(a)が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である請求項1または2に記載の歯科用組成物。
- さらに、(c)重合性官能基を3個以上有する多官能モノマーを含む請求項1ないし3のいずれか1項に記載の歯科用組成物。
- 多官能モノマー(c)がジペンタエリスルトールヘキサアクリレートである請求項4に記載の歯科用組成物。
- (b)ジ(メタ)アクリレート化合物を5〜70重量部、(c)多官能モノマーを30〜95重量部含む請求項4または5に記載の歯科用組成物。
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JP2008052963A JP5702044B2 (ja) | 2008-03-04 | 2008-03-04 | モノマーによって色調変化を抑えた光硬化性歯科用組成物 |
CN2009101263465A CN101524313B (zh) | 2008-03-04 | 2009-03-03 | 通过单体抑制色调变化的光聚合性牙科用组合物 |
DE102009011537.4A DE102009011537B4 (de) | 2008-03-04 | 2009-03-03 | Photopolymerisierbare Dentalzusammensetzung mit unterdrückter Änderung im Farbton durch Monomer |
US12/379,925 US8013032B2 (en) | 2008-03-04 | 2009-03-04 | Photopolymerizable dental composition with suppressed change in color tone by monomer |
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JP2008052963A JP5702044B2 (ja) | 2008-03-04 | 2008-03-04 | モノマーによって色調変化を抑えた光硬化性歯科用組成物 |
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EP2439783B1 (en) * | 2009-06-05 | 2016-08-24 | Bridgestone Corporation | Sealing film for solar cell, and solar cell utilizing same |
JP5703230B2 (ja) * | 2009-10-23 | 2015-04-15 | サンメディカル株式会社 | 易除去性歯科用硬化性組成物 |
EP2436364B1 (de) | 2010-09-30 | 2017-05-31 | VOCO GmbH | Lackzusammensetzung umfassend ein Monomer mit einem polyalicyclischen Strukturelement |
DE102012212429A1 (de) | 2012-07-16 | 2014-01-16 | Voco Gmbh | Dentalhandgerät, Verfahren und Verwendung desselben zum Aushärten lichthärtbaren Materials |
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Also Published As
Publication number | Publication date |
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CN101524313B (zh) | 2012-07-04 |
JP5702044B2 (ja) | 2015-04-15 |
CN101524313A (zh) | 2009-09-09 |
DE102009011537A1 (de) | 2009-09-10 |
US20090227699A1 (en) | 2009-09-10 |
DE102009011537B4 (de) | 2019-03-21 |
US8013032B2 (en) | 2011-09-06 |
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