KR102174015B1 - 부가-단편화제를 포함하는 치과용 조성물 - Google Patents
부가-단편화제를 포함하는 치과용 조성물 Download PDFInfo
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- KR102174015B1 KR102174015B1 KR1020207019365A KR20207019365A KR102174015B1 KR 102174015 B1 KR102174015 B1 KR 102174015B1 KR 1020207019365 A KR1020207019365 A KR 1020207019365A KR 20207019365 A KR20207019365 A KR 20207019365A KR 102174015 B1 KR102174015 B1 KR 102174015B1
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- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 1
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- 239000008241 heterogeneous mixture Substances 0.000 description 1
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- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 150000002632 lipids Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- NZRFSLMXTFGVGZ-UHFFFAOYSA-N n-[diethylamino(prop-2-enoxy)phosphoryl]-n-ethylethanamine Chemical compound CCN(CC)P(=O)(N(CC)CC)OCC=C NZRFSLMXTFGVGZ-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000013500 performance material Substances 0.000 description 1
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000005365 phosphate glass Substances 0.000 description 1
- XNQULTQRGBXLIA-UHFFFAOYSA-O phosphonic anhydride Chemical compound O[P+](O)=O XNQULTQRGBXLIA-UHFFFAOYSA-O 0.000 description 1
- 230000000886 photobiology Effects 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
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- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
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- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000002265 redox agent Substances 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 230000000395 remineralizing effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000011885 synergistic combination Substances 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
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 229950003937 tolonium Drugs 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- 230000036347 tooth sensitivity Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- XREXPQGDOPQPAH-QKUPJAQQSA-K trisodium;[(z)-18-[1,3-bis[[(z)-12-sulfonatooxyoctadec-9-enoyl]oxy]propan-2-yloxy]-18-oxooctadec-9-en-7-yl] sulfate Chemical compound [Na+].[Na+].[Na+].CCCCCCC(OS([O-])(=O)=O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O)COC(=O)CCCCCCC\C=C/CC(CCCCCC)OS([O-])(=O)=O XREXPQGDOPQPAH-QKUPJAQQSA-K 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000012991 xanthate Substances 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
- 229910052727 yttrium Inorganic materials 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
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
- A61K6/76—Fillers comprising silicon-containing compounds
-
- 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
-
- 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
- A61K6/889—Polycarboxylate cements; Glass ionomer cements
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
Landscapes
- Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Organic Chemistry (AREA)
- Dental Preparations (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261725077P | 2012-11-12 | 2012-11-12 | |
| US61/725,077 | 2012-11-12 | ||
| PCT/US2013/067638 WO2014074373A1 (en) | 2012-11-12 | 2013-10-31 | Dental compositions comprising addition-fragmentation agents |
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Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2861154B2 (ja) | 1989-12-04 | 1999-02-24 | 富士通株式会社 | Ａ／ｄ変換器入力信号のａｇｃ，ａｄｃ調整方式 |
| EP2747737B1 (en) * | 2011-08-23 | 2019-09-25 | 3M Innovative Properties Company | Dental compositions comprising addition-fragmentation agents |
| EP2931756B1 (en) | 2012-12-17 | 2018-08-08 | 3M Innovative Properties Company | Addition-fragmentation oligomers |
| JP6300899B2 (ja) | 2013-03-20 | 2018-03-28 | スリーエム イノベイティブ プロパティズ カンパニー | 高屈折率の付加−開裂剤 |
| WO2014172138A1 (en) | 2013-04-15 | 2014-10-23 | 3M Innovative Properties Company | Dental composition containing high refractive index monomers |
| WO2015041863A1 (en) * | 2013-09-20 | 2015-03-26 | 3M Innovative Properties Company | Trithiocarbonate-containing addition-fragmentation agents |
| CN105683257B (zh) | 2013-10-16 | 2018-02-13 | 3M创新有限公司 | 包含烯丙基二硫化物的加成‑断裂低聚物 |
| JP6647206B2 (ja) | 2014-02-18 | 2020-02-14 | スリーエム イノベイティブ プロパティズ カンパニー | 高屈折率基を有する付加開裂オリゴマー |
| EP2949311B1 (en) * | 2014-05-30 | 2019-10-16 | Shofu Inc. | Dental composition containing ion sustained-release glass |
| US10350297B2 (en) | 2014-10-31 | 2019-07-16 | 3M Innovative Properties Company | Dental materials and methods |
| WO2016069290A1 (en) | 2014-10-31 | 2016-05-06 | 3M Innovative Properties Company | Dental materials and methods |
| US10479848B2 (en) | 2015-02-20 | 2019-11-19 | 3M Innovative Properties Company | Addition-fragmentation oligomers |
| EP3504251B1 (en) | 2016-08-23 | 2026-03-25 | The Regents of the University of Colorado, a Body Corporate | Network polymers and methods of making and using same |
| US12071515B2 (en) | 2018-06-08 | 2024-08-27 | The Regents Of The University Of Colorado, A Body Corporate | High dynamic range two-stage photopolymers |
| CN112996472A (zh) * | 2018-11-14 | 2021-06-18 | 3M创新有限公司 | 储存稳定的双组分双固化牙科组合物 |
| US12391780B2 (en) * | 2019-02-18 | 2025-08-19 | The Regents Of The University Of Colorado, A Body Corporate | Network polymers and methods of making and using same |
| DE102019122174A1 (de) | 2019-08-19 | 2021-02-25 | Voco Gmbh | Dentale polymerisierbare Zusammensetzung auf der Basis kondensierter Silane |
| CN114929177A (zh) * | 2019-12-31 | 2022-08-19 | 3M创新有限公司 | 含有银和氟化物的可固化口腔护理组合物 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008510038A (ja) | 2004-08-11 | 2008-04-03 | スリーエム イノベイティブ プロパティズ カンパニー | 複数の酸性化合物を含む粘着性組成物 |
| US20090030110A1 (en) | 2004-05-26 | 2009-01-29 | Dentsply De Trey Gmbh | Dental cement composition containing composite particles with grafted polyacidic polymer chains |
| US20120208965A1 (en) | 2011-02-15 | 2012-08-16 | 3M Innovative Properties Company | Addition-fragmentation agents |
| WO2012112350A2 (en) * | 2011-02-15 | 2012-08-23 | 3M Innovative Properties Company | Dental compositions comprising ethylenically unsaturated addition-fragmentation agent |
Family Cites Families (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2801185A (en) | 1952-05-16 | 1957-07-30 | Du Pont | Silica hydrosol powder |
| US4522958A (en) | 1983-09-06 | 1985-06-11 | Ppg Industries, Inc. | High-solids coating composition for improved rheology control containing chemically modified inorganic microparticles |
| 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 |
| US5154762A (en) | 1991-05-31 | 1992-10-13 | Minnesota Mining And Manufacturing Company | Universal water-based medical and dental cement |
| US5506279A (en) | 1993-10-13 | 1996-04-09 | Minnesota Mining And Manufacturing Company | Acrylamido functional disubstituted acetyl aryl ketone photoinitiators |
| 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 |
| ES2166092T3 (es) | 1996-07-10 | 2002-04-01 | Du Pont | Polimerizacion con caracteristicas vivientes. |
| US6316519B1 (en) * | 1997-02-19 | 2001-11-13 | E. I. Du Pont De Nemours And Company | Molecular weight controlled polymers by photopolymerization |
| 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 |
| FR2764892B1 (fr) | 1997-06-23 | 2000-03-03 | Rhodia Chimie Sa | Procede de synthese de polymeres a blocs |
| CA2309279C (en) | 1997-12-18 | 2009-07-14 | E.I. Du Pont De Nemours And Company | Polymerization process with living characteristics and polymers made therefrom |
| CA2315914A1 (fr) | 1997-12-31 | 1999-07-15 | Xavier Franck | Procede de synthese de polymeres a blocs par polymerisation radicalaire controlee a partir de composes dithiocarbamates |
| DE19943712C1 (de) | 1999-09-08 | 2001-05-17 | Ivoclar Ag Schaan | Hydrolysierbare und polymerisierbare Silane auf der Basis von Methylendithiepan |
| 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 |
| DE60042038D1 (de) | 1999-10-28 | 2009-05-28 | 3M Innovative Properties Co | Siliziumdioxid-Nanoteilchen in Form eines trockenen Pulvers |
| US6572693B1 (en) | 1999-10-28 | 2003-06-03 | 3M Innovative Properties Company | Aesthetic dental materials |
| US6376590B2 (en) | 1999-10-28 | 2002-04-23 | 3M Innovative Properties Company | Zirconia sol, process of making and composite material |
| US6794317B2 (en) | 2000-04-26 | 2004-09-21 | Creare Inc. | Protective cover system including a corrosion inhibitor |
| US6586483B2 (en) | 2001-01-08 | 2003-07-01 | 3M Innovative Properties Company | Foam including surface-modified nanoparticles |
| 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 |
| EP2275077A3 (en) | 2001-08-15 | 2014-07-16 | 3M Innovative Properties Co. | Hardenable self-supporting structures and methods |
| AU2002356771A1 (en) | 2001-12-21 | 2003-07-09 | Siemens Aktiengesellschaft | Device for detecting and displaying movements |
| 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 |
| US7090721B2 (en) | 2004-05-17 | 2006-08-15 | 3M Innovative Properties Company | Use of nanoparticles to adjust refractive index of dental compositions |
| 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 |
| US7649029B2 (en) | 2004-05-17 | 2010-01-19 | 3M Innovative Properties Company | Dental compositions containing nanozirconia fillers |
| EP1600142B1 (en) * | 2004-05-26 | 2008-08-06 | DENTSPLY DETREY GmbH | Dental cement composition containing composite particles with grafted polyacidic polymer chains |
| US7241437B2 (en) | 2004-12-30 | 2007-07-10 | 3M Innovative Properties Company | Zirconia particles |
| US7943680B2 (en) | 2005-02-10 | 2011-05-17 | The Regents Of The University Of Colorado | Stress relaxation in crosslinked polymers |
| WO2006122081A1 (en) | 2005-05-09 | 2006-11-16 | 3M Innovative Properties Company | Dental compositions containing hybrid monomers |
| JP5260505B2 (ja) | 2006-06-09 | 2013-08-14 | デンツプライ インターナショナル インコーポレーテッド | 低応力流動性歯科用組成物 |
| WO2008082881A1 (en) | 2006-12-28 | 2008-07-10 | 3M Innovative Properties Company | (meth)acryloyl-containing materials, compositions, and methods |
| CN102112097B (zh) | 2007-11-01 | 2013-08-07 | 3M创新有限公司 | 牙科组合物以及具有颜色稳定的胺电子供体的引发剂系统 |
| JP2011510002A (ja) | 2008-01-15 | 2011-03-31 | デンツプライ インターナショナル インコーポレーテッド | 調節された重合応力のための機能性樹脂組成物 |
| EP2105419A1 (en) | 2008-03-28 | 2009-09-30 | Lafarge | Additives for cement |
| JP5661040B2 (ja) | 2008-10-15 | 2015-01-28 | スリーエム イノベイティブ プロパティズ カンパニー | ジルコニア及びシリカナノ粒子を含む充填剤、並びにコンポジット材料 |
| US7838110B2 (en) | 2008-12-02 | 2010-11-23 | 3M Innovative Properties Company | Aziridine-functional photoactive crosslinking compounds |
| WO2011126647A2 (en) | 2010-03-31 | 2011-10-13 | 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 |
| WO2012016052A1 (en) * | 2010-07-28 | 2012-02-02 | True Fit Corporation | Fit recommendation via collaborative inference |
| US9012531B2 (en) | 2011-02-15 | 2015-04-21 | 3M Innovative Properties Company | Dental compositions comprising mixture of isocyanurate monomer and tricyclodecane monomer |
| EP2747737B1 (en) | 2011-08-23 | 2019-09-25 | 3M Innovative Properties Company | Dental compositions comprising addition-fragmentation agents |
| JP6087355B2 (ja) * | 2011-08-23 | 2017-03-01 | スリーエム イノベイティブ プロパティズ カンパニー | 付加開裂剤 |
| JP6403679B2 (ja) | 2012-11-12 | 2018-10-10 | スリーエム イノベイティブ プロパティズ カンパニー | 付加開裂剤 |
-
2013
- 2013-10-31 US US14/437,200 patent/US9414996B2/en active Active
- 2013-10-31 KR KR1020207019365A patent/KR102174015B1/ko active Active
- 2013-10-31 EP EP13789448.1A patent/EP2916801B1/en active Active
- 2013-10-31 KR KR1020157015131A patent/KR20150082570A/ko not_active Ceased
- 2013-10-31 WO PCT/US2013/067638 patent/WO2014074373A1/en not_active Ceased
- 2013-10-31 JP JP2015541810A patent/JP6351608B2/ja not_active Expired - Fee Related
- 2013-10-31 CN CN201380058459.0A patent/CN104768519B/zh active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090030110A1 (en) | 2004-05-26 | 2009-01-29 | Dentsply De Trey Gmbh | Dental cement composition containing composite particles with grafted polyacidic polymer chains |
| JP2008510038A (ja) | 2004-08-11 | 2008-04-03 | スリーエム イノベイティブ プロパティズ カンパニー | 複数の酸性化合物を含む粘着性組成物 |
| US20120208965A1 (en) | 2011-02-15 | 2012-08-16 | 3M Innovative Properties Company | Addition-fragmentation agents |
| WO2012112350A2 (en) * | 2011-02-15 | 2012-08-23 | 3M Innovative Properties Company | Dental compositions comprising ethylenically unsaturated addition-fragmentation agent |
Also Published As
| Publication number | Publication date |
|---|---|
| US20150283039A1 (en) | 2015-10-08 |
| JP2016504278A (ja) | 2016-02-12 |
| CN104768519B (zh) | 2018-11-23 |
| US9414996B2 (en) | 2016-08-16 |
| CN104768519A (zh) | 2015-07-08 |
| JP6351608B2 (ja) | 2018-07-04 |
| EP2916801B1 (en) | 2017-02-22 |
| KR20150082570A (ko) | 2015-07-15 |
| KR20200084925A (ko) | 2020-07-13 |
| WO2014074373A1 (en) | 2014-05-15 |
| EP2916801A1 (en) | 2015-09-16 |
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