JP4494854B2 - 歯科用カチオン硬化性組成物 - Google Patents
歯科用カチオン硬化性組成物 Download PDFInfo
- Publication number
- JP4494854B2 JP4494854B2 JP2004131431A JP2004131431A JP4494854B2 JP 4494854 B2 JP4494854 B2 JP 4494854B2 JP 2004131431 A JP2004131431 A JP 2004131431A JP 2004131431 A JP2004131431 A JP 2004131431A JP 4494854 B2 JP4494854 B2 JP 4494854B2
- Authority
- JP
- Japan
- Prior art keywords
- dental
- compound
- oxetane
- curable composition
- cationic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000000203 mixture Substances 0.000 title claims description 55
- 125000002091 cationic group Chemical group 0.000 title claims description 26
- -1 alkenyl ether compound Chemical class 0.000 claims description 95
- 239000000178 monomer Substances 0.000 claims description 38
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000003566 oxetanyl group Chemical group 0.000 claims description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- 239000000945 filler Substances 0.000 claims description 19
- 239000003505 polymerization initiator Substances 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000001033 ether group Chemical group 0.000 claims description 16
- 238000011049 filling Methods 0.000 claims description 15
- 238000010538 cationic polymerization reaction Methods 0.000 claims description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 20
- 238000006116 polymerization reaction Methods 0.000 description 19
- 125000000524 functional group Chemical group 0.000 description 18
- 150000003254 radicals Chemical class 0.000 description 17
- 238000002156 mixing Methods 0.000 description 15
- 230000000704 physical effect Effects 0.000 description 10
- 101100278747 Caenorhabditis elegans dve-1 gene Proteins 0.000 description 9
- 210000000214 mouth Anatomy 0.000 description 9
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- 230000000052 comparative effect Effects 0.000 description 8
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- 150000001768 cations Chemical class 0.000 description 5
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
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- 150000001450 anions Chemical class 0.000 description 4
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
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- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 2
- AMKRBKSZCGCEJK-UHFFFAOYSA-N 1,2-dimethoxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(OC)C(OC)=CC=C3C(=O)C2=C1 AMKRBKSZCGCEJK-UHFFFAOYSA-N 0.000 description 2
- APQSQLNWAIULLK-UHFFFAOYSA-N 1,4-dimethylnaphthalene Chemical compound C1=CC=C2C(C)=CC=C(C)C2=C1 APQSQLNWAIULLK-UHFFFAOYSA-N 0.000 description 2
- LPHQUKCANLSJRU-UHFFFAOYSA-N 1,8-dimethylphenanthrene Chemical compound C1=CC2=C(C)C=CC=C2C2=C1C(C)=CC=C2 LPHQUKCANLSJRU-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical group CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- MXZKHBKVIJMSHZ-UHFFFAOYSA-N 5,12-dimethyltetracene Chemical compound C1=CC=C2C=C3C(C)=C(C=CC=C4)C4=C(C)C3=CC2=C1 MXZKHBKVIJMSHZ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 238000012644 addition polymerization Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000000805 composite resin Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 239000000386 donor Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical group C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- JERBUBCQUQOHIC-UHFFFAOYSA-N (1-acetyloxy-9,10-dioxoanthracen-2-yl) acetate Chemical compound C1=CC=C2C(=O)C3=C(OC(C)=O)C(OC(=O)C)=CC=C3C(=O)C2=C1 JERBUBCQUQOHIC-UHFFFAOYSA-N 0.000 description 1
- KOCUMXQOUWPSLK-SNAWJCMRSA-N (1e)-1-methoxybuta-1,3-diene Chemical compound CO\C=C\C=C KOCUMXQOUWPSLK-SNAWJCMRSA-N 0.000 description 1
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical compound CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 1
- NLQMSBJFLQPLIJ-UHFFFAOYSA-N (3-methyloxetan-3-yl)methanol Chemical compound OCC1(C)COC1 NLQMSBJFLQPLIJ-UHFFFAOYSA-N 0.000 description 1
- DSJDHQOKMCDBEW-UHFFFAOYSA-O (4,7-dihydroxynaphthalen-1-yl)-dimethylsulfanium Chemical compound C1=C(O)C=C2C([S+](C)C)=CC=C(O)C2=C1 DSJDHQOKMCDBEW-UHFFFAOYSA-O 0.000 description 1
- XLQMBODNBLKPIP-UHFFFAOYSA-O (4-hydroxynaphthalen-1-yl)-dimethylsulfanium Chemical compound C1=CC=C2C([S+](C)C)=CC=C(O)C2=C1 XLQMBODNBLKPIP-UHFFFAOYSA-O 0.000 description 1
- QAEDNLDMOUKNMI-UHFFFAOYSA-O (4-hydroxyphenyl)-dimethylsulfanium Chemical compound C[S+](C)C1=CC=C(O)C=C1 QAEDNLDMOUKNMI-UHFFFAOYSA-O 0.000 description 1
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- VCYQRZKSWZQERK-UHFFFAOYSA-N (9-oxofluoren-2-yl) acetate Chemical compound C1=CC=C2C(=O)C3=CC(OC(=O)C)=CC=C3C2=C1 VCYQRZKSWZQERK-UHFFFAOYSA-N 0.000 description 1
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- FTQWAZVZDZMKDA-UHFFFAOYSA-N 1-anthracen-9-ylethanethiol Chemical compound C1=CC=C2C(C(S)C)=C(C=CC=C3)C3=CC2=C1 FTQWAZVZDZMKDA-UHFFFAOYSA-N 0.000 description 1
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
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- 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
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- INRGAWUQFOBNKL-UHFFFAOYSA-N {4-[(Vinyloxy)methyl]cyclohexyl}methanol Chemical compound OCC1CCC(COC=C)CC1 INRGAWUQFOBNKL-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyethers (AREA)
- Dental Preparations (AREA)
- Dental Tools And Instruments Or Auxiliary Dental Instruments (AREA)
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| Application Number | Priority Date | Filing Date | Title |
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| JP2004131431A JP4494854B2 (ja) | 2004-04-27 | 2004-04-27 | 歯科用カチオン硬化性組成物 |
| US11/114,086 US7365106B2 (en) | 2004-04-27 | 2005-04-26 | Cationically curable composition for dental use |
| CNA2005100922749A CN1732883A (zh) | 2004-04-27 | 2005-04-27 | 用于牙科的可阳离子固化组合物 |
| EP05252619A EP1591098B1 (en) | 2004-04-27 | 2005-04-27 | Cationically curable composition for dental use |
| DE602005008805T DE602005008805D1 (de) | 2004-04-27 | 2005-04-27 | Kationisch härtbare Zusammensetzung für dentale Zwecke |
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| JP2004131431A JP4494854B2 (ja) | 2004-04-27 | 2004-04-27 | 歯科用カチオン硬化性組成物 |
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| JP4540409B2 (ja) * | 2004-06-29 | 2010-09-08 | 株式会社トクヤマ | 歯科用重合性組成物 |
| JP4749779B2 (ja) * | 2005-07-05 | 2011-08-17 | 株式会社トクヤマ | 歯科用カチオン硬化性組成物 |
| JP2007169627A (ja) * | 2005-11-28 | 2007-07-05 | Konica Minolta Medical & Graphic Inc | 光硬化性組成物、活性光線硬化型インク組成物及び画像形成方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2004149587A (ja) * | 2002-10-29 | 2004-05-27 | Tokuyama Corp | 光カチオン重合開始剤組成物 |
| JP2004520319A (ja) * | 2000-12-22 | 2004-07-08 | ロディア・シミ | 加熱プロセスによって架橋可能な及び／又は重合可能な官能化シリコーンを基材とする歯科用組成物 |
| JP2004196949A (ja) * | 2002-12-18 | 2004-07-15 | Tokuyama Corp | 光重合開始剤組成物および光重合組成物 |
| JP2004196775A (ja) * | 2002-11-12 | 2004-07-15 | Tokuyama Corp | 光カチオン重合開始剤組成物および光カチオン重合性組成物 |
| JP2005187385A (ja) * | 2003-12-25 | 2005-07-14 | Tokuyama Corp | 歯科用カチオン硬化性組成物 |
| JP2005298596A (ja) * | 2004-04-08 | 2005-10-27 | Tokuyama Corp | 硬化性組成物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2004520319A (ja) * | 2000-12-22 | 2004-07-08 | ロディア・シミ | 加熱プロセスによって架橋可能な及び／又は重合可能な官能化シリコーンを基材とする歯科用組成物 |
| JP2004149587A (ja) * | 2002-10-29 | 2004-05-27 | Tokuyama Corp | 光カチオン重合開始剤組成物 |
| JP2004196775A (ja) * | 2002-11-12 | 2004-07-15 | Tokuyama Corp | 光カチオン重合開始剤組成物および光カチオン重合性組成物 |
| JP2004196949A (ja) * | 2002-12-18 | 2004-07-15 | Tokuyama Corp | 光重合開始剤組成物および光重合組成物 |
| JP2005187385A (ja) * | 2003-12-25 | 2005-07-14 | Tokuyama Corp | 歯科用カチオン硬化性組成物 |
| JP2005298596A (ja) * | 2004-04-08 | 2005-10-27 | Tokuyama Corp | 硬化性組成物 |
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| CN1732883A (zh) | 2006-02-15 |
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