RU2573997C2 - Стоматологические композиции, содержащие этиленненасыщенный агент присоединения-фрагментации - Google Patents
Стоматологические композиции, содержащие этиленненасыщенный агент присоединения-фрагментации Download PDFInfo
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- RU2573997C2 RU2573997C2 RU2013136505/15A RU2013136505A RU2573997C2 RU 2573997 C2 RU2573997 C2 RU 2573997C2 RU 2013136505/15 A RU2013136505/15 A RU 2013136505/15A RU 2013136505 A RU2013136505 A RU 2013136505A RU 2573997 C2 RU2573997 C2 RU 2573997C2
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- dental composition
- meth
- monomer
- dental
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- 239000000203 mixture Substances 0.000 title claims abstract description 230
- 238000013467 fragmentation Methods 0.000 title claims abstract description 44
- 238000006062 fragmentation reaction Methods 0.000 title claims abstract description 44
- 239000000178 monomer Substances 0.000 claims abstract description 117
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 37
- 125000003118 aryl group Chemical group 0.000 claims abstract description 27
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 229910052809 inorganic oxide Inorganic materials 0.000 claims abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 56
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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 claims description 10
- 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 claims description 7
- 239000012634 fragment Substances 0.000 claims description 7
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- ULQMPOIOSDXIGC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)COC(=O)C(C)=C ULQMPOIOSDXIGC-UHFFFAOYSA-N 0.000 claims description 4
- UKMBKKFLJMFCSA-UHFFFAOYSA-N [3-hydroxy-2-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)OC(=O)C(C)=C UKMBKKFLJMFCSA-UHFFFAOYSA-N 0.000 claims description 4
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 4
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- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 2
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- ZQRXOCGXVFDJPG-UHFFFAOYSA-N n-(2-phenylethenyl)prop-2-enamide Chemical compound C=CC(=O)NC=CC1=CC=CC=C1 ZQRXOCGXVFDJPG-UHFFFAOYSA-N 0.000 claims 1
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
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- IEKWPPTXWFKANS-UHFFFAOYSA-K trichlorocobalt Chemical compound Cl[Co](Cl)Cl IEKWPPTXWFKANS-UHFFFAOYSA-K 0.000 description 1
- ZFZDWMXUMXACHS-IACGZSPGSA-N tricyclo[5.2.1.02,6]decane-4,8-dimethanol Chemical compound C([C@H]1C2)C(CO)[C@H]2C2C1CC(CO)C2 ZFZDWMXUMXACHS-IACGZSPGSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 125000005590 trimellitic acid group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- XASAPYQVQBKMIN-UHFFFAOYSA-K ytterbium(iii) fluoride Chemical compound F[Yb](F)F XASAPYQVQBKMIN-UHFFFAOYSA-K 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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- 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
- A61K6/61—Cationic, anionic or redox initiators
-
- 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
- A61K6/40—Primers
-
- 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)
- Oral & Maxillofacial Surgery (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Veterinary Medicine (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Dental Preparations (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| US201161443218P | 2011-02-15 | 2011-02-15 | |
| US61/443,218 | 2011-02-15 | ||
| US201161521134P | 2011-08-08 | 2011-08-08 | |
| US61/521,134 | 2011-08-08 | ||
| PCT/US2012/024222 WO2012112350A2 (en) | 2011-02-15 | 2012-02-08 | Dental compositions comprising ethylenically unsaturated addition-fragmentation agent |
Publications (2)
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| RU2013136505A RU2013136505A (ru) | 2015-03-27 |
| RU2573997C2 true RU2573997C2 (ru) | 2016-01-27 |
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| EP (2) | EP2965742B1 (enExample) |
| JP (1) | JP6077463B2 (enExample) |
| CN (1) | CN103370041B (enExample) |
| BR (1) | BR112013019702B1 (enExample) |
| RU (1) | RU2573997C2 (enExample) |
| WO (1) | WO2012112350A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2765824C1 (ru) * | 2018-08-13 | 2022-02-03 | Стик Тек Ой | Стоматологическая композиция |
| EP4048708A1 (de) * | 2019-10-31 | 2022-08-31 | Kulzer GmbH | Polymerisierbare zusammensetzung |
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| US10370322B2 (en) | 2011-02-15 | 2019-08-06 | 3M Innovative Properties Company | Addition-fragmentation agents |
| US20120208965A1 (en) * | 2011-02-15 | 2012-08-16 | 3M Innovative Properties Company | Addition-fragmentation agents |
| EP2675421A2 (en) | 2011-02-15 | 2013-12-25 | 3M Innovative Properties Company | Dental compositions comprising mixture of isocyanurate monomer and tricyclodecane monomer |
| RU2586743C2 (ru) | 2011-08-23 | 2016-06-10 | Зм Инновейтив Пропертиз Компани | Стоматологические композиции, содержащие агенты присоединения-фрагментации |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2318845A (en) * | 1940-03-23 | 1943-05-11 | Austenal Lab Inc | Dental resin |
| US6316519B1 (en) * | 1997-02-19 | 2001-11-13 | E. I. Du Pont De Nemours And Company | Molecular weight controlled polymers by photopolymerization |
| US6900280B2 (en) * | 2001-03-01 | 2005-05-31 | Ciba Specialty Chemicals Corp. | Acid macromonomers and their method of preparation |
| RU2275183C2 (ru) * | 2000-08-26 | 2006-04-27 | Дегусса Аг | Стоматологический материал с гибридными наполнителями и способ его получения |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4547323A (en) * | 1984-03-21 | 1985-10-15 | Scm Corporation | Synthesis of 2,2-dimethyl-4-methyleneglutaric acid and derivatives |
| US4503169A (en) | 1984-04-19 | 1985-03-05 | Minnesota Mining And Manufacturing Company | Radiopaque, low visual opacity dental composites containing non-vitreous microparticles |
| US4886861A (en) * | 1985-04-23 | 1989-12-12 | E. I. Dupont De Nemours And Company | Molecular weight control in free radical polymerizations |
| US5324879A (en) | 1985-12-03 | 1994-06-28 | Commonwealth Scientific And Industrial Research Organisation | Oligomerization process |
| CA1323949C (en) | 1987-04-02 | 1993-11-02 | Michael C. Palazzotto | Ternary photoinitiator system for addition polymerization |
| AU618772B2 (en) | 1987-12-30 | 1992-01-09 | Minnesota Mining And Manufacturing Company | Photocurable ionomer cement systems |
| US5444118A (en) * | 1989-06-30 | 1995-08-22 | Japan Synthetic Rubber Co., Ltd. | Process for producing copolymer latex and paper coating composition, carpet backing composition or adhesive composition comprising said latex |
| US5154762A (en) | 1991-05-31 | 1992-10-13 | Minnesota Mining And Manufacturing Company | Universal water-based medical and dental cement |
| US5264530A (en) * | 1992-05-01 | 1993-11-23 | E. I. Du Pont De Nemours And Company | Process of polymerization in an aqueous system |
| US5501727A (en) | 1994-02-28 | 1996-03-26 | Minnesota Mining And Manufacturing Company | Color stability of dental compositions containing metal complexed ascorbic acid |
| US6126922A (en) | 1995-11-17 | 2000-10-03 | 3M Innovative Properties Company | Fluorid-releasing compositions and compositions with improved rheology |
| US5770646A (en) * | 1996-10-29 | 1998-06-23 | E. I. Du Pont De Nemours And Company | Aqueous branched polymer dispersant for hydrophobic materials |
| US6001897A (en) | 1997-01-13 | 1999-12-14 | American Dental Association Health Foundation | Polymerizable conditioners for adhesive bonding to dentin and enamel |
| JP4083257B2 (ja) | 1997-03-19 | 2008-04-30 | 株式会社ジーシー | 歯科充填用レジン組成物 |
| US6096903A (en) | 1997-03-25 | 2000-08-01 | Ivoclar Ag | Hydrolysable and polymerizable oxetane silanes |
| US6506816B1 (en) | 1997-07-17 | 2003-01-14 | 3M Innovative Properties Company | Dental resin cements having improved handling properties |
| US6174953B1 (en) * | 1998-02-19 | 2001-01-16 | E. I. Du Pont De Nemours And Company | Low molecular weight (meth) acrylate copolymer emulsions |
| US6030606A (en) | 1998-06-22 | 2000-02-29 | 3M Innovative Properties Company | Dental restoratives comprising Bis-EMA6 |
| PT1123332E (pt) * | 1998-07-10 | 2004-08-31 | Du Pont | Microgeis e processos para a sua preparacao |
| DE19943712C1 (de) | 1999-09-08 | 2001-05-17 | Ivoclar Ag Schaan | Hydrolysierbare und polymerisierbare Silane auf der Basis von Methylendithiepan |
| DE60022667T2 (de) | 1999-10-28 | 2006-06-14 | 3M Innovative Properties Co | Dentalmaterialien mit siliciumdioxid-nanoteilchen |
| US6387981B1 (en) | 1999-10-28 | 2002-05-14 | 3M Innovative Properties Company | Radiopaque dental materials with nano-sized particles |
| US6730156B1 (en) | 1999-10-28 | 2004-05-04 | 3M Innovative Properties Company | Clustered particle dental fillers |
| US6572693B1 (en) | 1999-10-28 | 2003-06-03 | 3M Innovative Properties Company | Aesthetic dental materials |
| US20060009574A1 (en) * | 2001-01-26 | 2006-01-12 | Aert Huub V | Method of emulsion polymerization |
| DE10106372A1 (de) | 2001-02-12 | 2002-08-29 | Ivoclar Vivadent Ag | Thermochromer Dentalwerkstoff |
| CN100415198C (zh) | 2001-08-15 | 2008-09-03 | 3M创新有限公司 | 可硬化的自支撑结构和方法 |
| CN1319507C (zh) | 2002-01-31 | 2007-06-06 | 3M创新有限公司 | 牙科糊剂、牙科制品和方法 |
| US7649029B2 (en) | 2004-05-17 | 2010-01-19 | 3M Innovative Properties Company | Dental compositions containing nanozirconia fillers |
| US7090722B2 (en) | 2004-05-17 | 2006-08-15 | 3M Innovative Properties Company | Acid-reactive dental fillers, compositions, and methods |
| US7156911B2 (en) | 2004-05-17 | 2007-01-02 | 3M Innovative Properties Company | Dental compositions containing nanofillers and related methods |
| US7090721B2 (en) | 2004-05-17 | 2006-08-15 | 3M Innovative Properties Company | Use of nanoparticles to adjust refractive index of dental compositions |
| AU2005272808B8 (en) | 2004-08-11 | 2011-11-03 | 3M Deutschland Gmbh | Self-adhesive compositions including a plurality of acidic compounds |
| US7241437B2 (en) | 2004-12-30 | 2007-07-10 | 3M Innovative Properties Company | Zirconia particles |
| WO2006086646A2 (en) * | 2005-02-10 | 2006-08-17 | The Regents Of The University Of Colorado, A Body Corporate | Stress relaxation in crosslinked polymers |
| AU2006244182B2 (en) | 2005-05-09 | 2012-02-02 | 3M Innovative Properties Company | Dental compositions containing hybrid monomers |
| WO2007146210A2 (en) | 2006-06-09 | 2007-12-21 | Dentsply International Inc. | Low stress flowable dental compositions |
| WO2008082881A1 (en) | 2006-12-28 | 2008-07-10 | 3M Innovative Properties Company | (meth)acryloyl-containing materials, compositions, and methods |
| EP2231714B1 (en) | 2008-01-15 | 2012-08-29 | DENTSPLY International Inc. | Functional resin composition for regulated polymerization stress |
| US8545222B2 (en) * | 2008-10-21 | 2013-10-01 | Chan Qian Wang | Method of dental implant restoration |
| US9237990B2 (en) | 2010-03-31 | 2016-01-19 | 3M Innovative Properties Company | Polymerizable isocyanurate monomers and dental compositions |
| EP2401998A1 (en) | 2010-07-02 | 2012-01-04 | 3M Innovative Properties Company | Dental composition, kit of parts and use thereof |
| US20120208965A1 (en) | 2011-02-15 | 2012-08-16 | 3M Innovative Properties Company | Addition-fragmentation agents |
-
2012
- 2012-02-08 EP EP15175714.3A patent/EP2965742B1/en active Active
- 2012-02-08 JP JP2013553505A patent/JP6077463B2/ja active Active
- 2012-02-08 BR BR112013019702-1A patent/BR112013019702B1/pt active IP Right Grant
- 2012-02-08 CN CN201280008646.3A patent/CN103370041B/zh active Active
- 2012-02-08 RU RU2013136505/15A patent/RU2573997C2/ru not_active IP Right Cessation
- 2012-02-08 WO PCT/US2012/024222 patent/WO2012112350A2/en not_active Ceased
- 2012-02-08 US US13/978,557 patent/US9056043B2/en active Active
- 2012-02-08 EP EP12704603.5A patent/EP2675422B1/en active Active
-
2015
- 2015-05-08 US US14/707,096 patent/US9320685B2/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2318845A (en) * | 1940-03-23 | 1943-05-11 | Austenal Lab Inc | Dental resin |
| US6316519B1 (en) * | 1997-02-19 | 2001-11-13 | E. I. Du Pont De Nemours And Company | Molecular weight controlled polymers by photopolymerization |
| RU2275183C2 (ru) * | 2000-08-26 | 2006-04-27 | Дегусса Аг | Стоматологический материал с гибридными наполнителями и способ его получения |
| US6900280B2 (en) * | 2001-03-01 | 2005-05-31 | Ciba Specialty Chemicals Corp. | Acid macromonomers and their method of preparation |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2765824C1 (ru) * | 2018-08-13 | 2022-02-03 | Стик Тек Ой | Стоматологическая композиция |
| US12268762B2 (en) | 2018-08-13 | 2025-04-08 | Stick Tech Oy | Dental composition |
| EP4048708A1 (de) * | 2019-10-31 | 2022-08-31 | Kulzer GmbH | Polymerisierbare zusammensetzung |
Also Published As
| Publication number | Publication date |
|---|---|
| US20150238389A1 (en) | 2015-08-27 |
| CN103370041B (zh) | 2016-06-15 |
| WO2012112350A2 (en) | 2012-08-23 |
| CN103370041A (zh) | 2013-10-23 |
| EP2965742A1 (en) | 2016-01-13 |
| US9320685B2 (en) | 2016-04-26 |
| BR112013019702A2 (pt) | 2017-10-24 |
| BR112013019702B1 (pt) | 2018-05-22 |
| US20130316307A1 (en) | 2013-11-28 |
| WO2012112350A3 (en) | 2012-12-27 |
| JP2014505105A (ja) | 2014-02-27 |
| RU2013136505A (ru) | 2015-03-27 |
| JP6077463B2 (ja) | 2017-02-08 |
| EP2675422B1 (en) | 2020-09-30 |
| EP2965742B1 (en) | 2020-09-09 |
| US9056043B2 (en) | 2015-06-16 |
| EP2675422A2 (en) | 2013-12-25 |
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