DE1495520C3 - - Google Patents
Info
- Publication number
- DE1495520C3 DE1495520C3 DE19641495520 DE1495520A DE1495520C3 DE 1495520 C3 DE1495520 C3 DE 1495520C3 DE 19641495520 DE19641495520 DE 19641495520 DE 1495520 A DE1495520 A DE 1495520A DE 1495520 C3 DE1495520 C3 DE 1495520C3
- Authority
- DE
- Germany
- Prior art keywords
- minutes
- acid
- dimethyl
- compounds
- peroxide
- 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
Links
- 238000000034 method Methods 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 5
- NFQAQKVFBFWVKQ-UHFFFAOYSA-N 1,3-dimethyl-5-(2-methylpropyl)-1,3-diazinane-2,4,6-trione Chemical compound CC(C)CC1C(=O)N(C)C(=O)N(C)C1=O NFQAQKVFBFWVKQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- XTXRWKRVRITETP-UHFFFAOYSA-N vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 4
- AMQCWPDDXYOEER-UHFFFAOYSA-N 3-cyano-2-butanone Chemical compound N#CC(C)C(C)=O AMQCWPDDXYOEER-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 229910001385 heavy metal Inorganic materials 0.000 claims description 3
- 150000001451 organic peroxides Chemical class 0.000 claims description 3
- 239000005749 Copper compound Substances 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001880 copper compounds Chemical class 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002577 pseudohalo group Chemical group 0.000 claims description 2
- QSQMLMUBVHLHFM-UHFFFAOYSA-N 2-methyl-3-oxo-3-phenylpropanenitrile Chemical compound N#CC(C)C(=O)C1=CC=CC=C1 QSQMLMUBVHLHFM-UHFFFAOYSA-N 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- OTSKHUNLOQPIGN-UHFFFAOYSA-N 1,3,5-trimethyl-1,3-diazinane-2,4,6-trione Chemical compound CC1C(=O)N(C)C(=O)N(C)C1=O OTSKHUNLOQPIGN-UHFFFAOYSA-N 0.000 description 10
- -1 hydrochlorides tertiary amines Chemical class 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- 150000002978 peroxides Chemical class 0.000 description 8
- 239000003999 initiator Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N 2-methyl-2-propenoic acid methyl ester Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (Z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N Barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- ODYNBECIRXXOGG-UHFFFAOYSA-N N-butylbutan-1-amine;hydron;chloride Chemical compound [Cl-].CCCC[NH2+]CCCC ODYNBECIRXXOGG-UHFFFAOYSA-N 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N Phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N benzohydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- OAUFZDJROJSXGE-UHFFFAOYSA-N dibutyl(2-phenylethyl)azanium;chloride Chemical compound Cl.CCCCN(CCCC)CCC1=CC=CC=C1 OAUFZDJROJSXGE-UHFFFAOYSA-N 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 150000002432 hydroperoxides Chemical class 0.000 description 2
- 125000005609 naphthenate group Chemical group 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 150000002898 organic sulfur compounds Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- JMYZLRSSLFFUQN-UHFFFAOYSA-N (2-chlorobenzoyl) 2-chlorobenzenecarboperoxoate Chemical compound ClC1=CC=CC=C1C(=O)OOC(=O)C1=CC=CC=C1Cl JMYZLRSSLFFUQN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ILIMOFAFBPEQAT-UHFFFAOYSA-N 1,5,5-trimethyl-1,3-diazinane-2,4,6-trione Chemical compound CN1C(=O)NC(=O)C(C)(C)C1=O ILIMOFAFBPEQAT-UHFFFAOYSA-N 0.000 description 1
- DCGGMHIZEAHUJL-UHFFFAOYSA-N 1-methyl-1,3-diazinane-2,4,6-trione Chemical compound CN1C(=O)CC(=O)NC1=O DCGGMHIZEAHUJL-UHFFFAOYSA-N 0.000 description 1
- JQVDAXLFBXTEQA-UHFFFAOYSA-N Dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M Dioctyl sodium sulfosuccinate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- LEHSOUZQZPUDEC-UHFFFAOYSA-N N-butyl-N-(2-phenylethyl)butan-1-amine Chemical compound CCCCN(CCCC)CCC1=CC=CC=C1 LEHSOUZQZPUDEC-UHFFFAOYSA-N 0.000 description 1
- 229920001225 Polyester resin Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical compound OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 229940027983 antiseptics and disinfectants Quaternary ammonium compounds Drugs 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000399 orthopedic Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED0044322 | 1964-05-02 | ||
| DED0044322 | 1964-05-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1495520A1 DE1495520A1 (de) | 1969-04-10 |
| DE1495520B2 DE1495520B2 (de) | 1970-06-25 |
| DE1495520C3 true DE1495520C3 (US20090130037A1-20090521-C00023.png) | 1976-09-16 |
Family
ID=7048237
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641495520 Granted DE1495520B2 (de) | 1964-05-02 | 1964-05-02 | Verfahren zum Polymerisieren |
Country Status (7)
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3488269A (en) * | 1965-09-15 | 1970-01-06 | Technical Operations Inc | Labile hydrogen initiators for visible light photopolymerization |
| DE2557502A1 (de) * | 1975-12-19 | 1977-06-30 | Bayer Ag | Stabilisierung von vernetzungsfaehigen polymerisaten |
| DE3107577A1 (de) * | 1981-02-27 | 1982-09-16 | ESPE Fabrik pharmazeutischer Präparate GmbH, 8031 Seefeld | 1,2-6-thiadiazin-3,5-dion-1,1-dioxide und ihre verwendung |
| JPS6335508A (ja) * | 1986-07-31 | 1988-02-16 | G C Dental Ind Corp | 義歯床用樹脂組成物 |
| JPH0655655B2 (ja) * | 1987-03-06 | 1994-07-27 | 而至陶歯工業株式会社 | 歯科用樹脂の硬化方法 |
| US6080389A (en) * | 1998-01-21 | 2000-06-27 | Esschem, Inc. | Materials and methods for reshaping of essentially rigid keratinaceous surfaces |
| US6015549A (en) * | 1998-04-17 | 2000-01-18 | Esschem, Inc. | Method of promoting adhesion to keratinaceous surface, use of same in reshaping surface, and kit therefor |
| EP1148862A4 (en) * | 1999-02-05 | 2006-01-04 | Esschem Inc | MATERIALS AND METHODS OF REPROCESSING MAINLY STIFF KERATINIC SURFACES |
| DE19961342B4 (de) | 1999-12-17 | 2004-02-19 | 3M Espe Ag | Radikalisch härtbare Urethanpräpolymere und deren Verwendung |
| DE10017188B4 (de) | 2000-04-07 | 2008-02-14 | 3M Espe Ag | Zweikomponentige Dentalmassen mit niedriger Abbindetemperatur und deren Verwendung |
| DE10058830B4 (de) | 2000-11-27 | 2005-01-27 | 3M Espe Ag | Verwendung von verzweigten Polysäuren in Dentalmassen und Dentalmassen enthaltend verzweigte Polysäuren |
| DE10124028B4 (de) | 2001-05-16 | 2010-02-18 | 3M Espe Ag | Selbstadhäsive Dentalmaterialien |
| DE10124029B4 (de) | 2001-05-16 | 2004-08-26 | 3M Espe Ag | Initiatorsystem für saure Dentalformulierungen |
| US7152576B2 (en) * | 2002-04-08 | 2006-12-26 | Richard Vanderpoel | Compact lost motion system for variable value actuation |
| US7025954B2 (en) * | 2002-05-20 | 2006-04-11 | Esstech, Inc. | Materials for reshaping of essentially rigid keratinaceous surfaces |
| DE102005012825B4 (de) † | 2005-03-17 | 2009-05-07 | Heraeus Kulzer Gmbh | Hochschlagzähe (High Impact) Prothesenkunststoffe und ihre Verwendung |
| EP2008636A1 (en) | 2007-06-29 | 2008-12-31 | 3M Innovative Properties Company | Dental composition containing a polyfunctional (meth)acrylate comprising urethane, urea or amide groups, method of production and use thereof |
| EP2042486A1 (en) * | 2007-09-26 | 2009-04-01 | 3M Innovative Properties Company | Methacrylate Based Monomers containing a Urethane Linkage, Process for Production and Use thereof |
| DE102010005956B4 (de) * | 2010-01-27 | 2011-09-01 | Heraeus Medical Gmbh | Dreikomponentenknochenzement und dessen Verwendung |
| DE102010003884A1 (de) | 2010-04-12 | 2011-10-13 | Voco Gmbh | Dualhärtende, mehrkomponentige dentale Zusammensetzung |
| DE102010024653B4 (de) | 2010-06-22 | 2012-06-21 | Heraeus Medical Gmbh | Kit zur Herstellung von Knochenzement und Verwendung dieses Kits |
| EP2401998A1 (en) | 2010-07-02 | 2012-01-04 | 3M Innovative Properties Company | Dental composition, kit of parts and use thereof |
| DE102010046697A1 (de) | 2010-09-28 | 2012-03-29 | Kettenbach Gmbh & Co. Kg | Polymerisierbares Dentalmaterial mit Reaktiv-Pastenbildner, gehärtetes Dentalmaterial und deren Verwendung |
| EP2436365B1 (de) | 2010-09-30 | 2017-03-08 | VOCO GmbH | Kompositmaterial umfassend ein Monomer mit einem polyalicyclischen Strukturelement |
| EP2436364B1 (de) | 2010-09-30 | 2017-05-31 | VOCO GmbH | Lackzusammensetzung umfassend ein Monomer mit einem polyalicyclischen Strukturelement |
| EP2436668B1 (de) | 2010-09-30 | 2012-09-12 | VOCO GmbH | Polymerisierbare Verbindungen umfassend ein polyalicyclisches Strukturelement |
| US8669302B2 (en) | 2010-09-30 | 2014-03-11 | Voco Gmbh | Composite material comprising a monomer with a polyalicyclic structure element as a sealing material |
| EP2436363B1 (de) | 2010-09-30 | 2017-01-18 | VOCO GmbH | Zusammensetzung umfassend ein Monomer mit einem polyalicyclischen Strukturelement zum Füllen und/oder Versiegeln eines Wurzelkanals |
| EP2450025B1 (de) | 2010-11-08 | 2012-11-28 | VOCO GmbH | Polymerisierbare Phosphorsäurederivate umfassend ein polyalicyclisches Strukturelement |
| DE102011003289A1 (de) | 2011-01-27 | 2012-08-02 | Voco Gmbh | Dentale provisorische Suprakonstruktionen sowie Materialien zu ihrer Herstellung und entsprechende Verfahren |
| EP2481390A1 (en) | 2011-01-31 | 2012-08-01 | 3M Innovative Properties Company | Dental composition, method of producing and use thereof |
| WO2012112321A2 (en) | 2011-02-15 | 2012-08-23 | 3M Innovative Properties Company | Dental compositions comprising mixture of isocyanurate monomer and tricyclodecane monomer |
| DE102011108574A1 (de) | 2011-07-27 | 2013-01-31 | Heraeus Medical Gmbh | Kit und Verfahren zur Herstellung von Knochenzement |
| US9173820B2 (en) | 2011-08-11 | 2015-11-03 | 3M Innovative Properties Company | Dental composition, method of producing and use thereof |
| EP2578200B1 (de) | 2011-10-04 | 2018-03-28 | VOCO GmbH | Zusammensetzungen zum Infiltrieren und/oder Versiegeln von Zahnhartsubstanz und entsprechende Verfahren |
| CA2797904C (en) | 2011-12-20 | 2015-01-27 | Heraeus Medical Gmbh | Paste-like bone cement |
| DE102012001978A1 (de) | 2012-02-02 | 2013-08-08 | Voco Gmbh | Dentale Kompositmaterialien enthaltend tricyclische Weichmacher |
| DE102012001979A1 (de) | 2012-02-02 | 2013-08-08 | Voco Gmbh | Härtbares Gemisch umfassend Weichmacher mit einem polyalicyclischen Strukturelement zur Anwendung bei der Herstellung dentaler Werkstoffe |
| JP6258874B2 (ja) | 2012-02-23 | 2018-01-10 | スリーエム イノベイティブ プロパティズ カンパニー | 構造用アクリル接着剤 |
| DE102012214540A1 (de) | 2012-08-15 | 2014-02-20 | Helmholtz-Zentrum für Infektionsforschung GmbH | Zahnfüllungsmaterialien und Zahnlacke zur Hemmung der Biofilmbildung von Streptococcus mutans und deren Herstellung |
| DE102013008176A1 (de) | 2012-10-05 | 2014-04-10 | Voco Gmbh | Kit und Verfahren zur indirekten chairside Herstellung von Kompositinlays |
| US9957408B2 (en) | 2013-03-19 | 2018-05-01 | 3M Innovative Properties Company | Free-radical polymerization methods and articles thereby |
| CN105358119A (zh) | 2013-07-08 | 2016-02-24 | 3M创新有限公司 | 包含凝聚和聚集的纳米粒子的混合物的可硬化牙科组合物、组件套盒及其用途 |
| CN106029045B (zh) | 2014-02-18 | 2020-04-03 | 3M创新有限公司 | 牙科组合物及其用途 |
| EP3107522B1 (en) | 2014-02-18 | 2018-10-17 | 3M Innovative Properties Company | Dental composition and use thereof |
| GB201412263D0 (en) | 2014-07-10 | 2014-08-27 | Lucite Internat Speciality Polymers And Resins Ltd | A multi-part acrylic cold-curing composition |
| CN106536578B (zh) * | 2014-07-22 | 2020-03-17 | 3M创新有限公司 | 自由基聚合方法和由此而得的制品 |
| CN107075001B (zh) | 2014-09-16 | 2020-04-03 | 3M创新有限公司 | 自由基聚合方法和由此而得的制品 |
| US10344169B2 (en) * | 2014-09-30 | 2019-07-09 | 3M Innovative Properties Company | Free-radical polymerization methods and articles thereby |
| EP3011949B1 (de) | 2014-10-23 | 2021-05-05 | VOCO GmbH | Härtbares dentalmaterial |
| DE102014116389A1 (de) | 2014-11-11 | 2016-05-12 | Voco Gmbh | Radikalisch härtbare dentale Zusammensetzungen |
| DE102014116402A1 (de) | 2014-11-11 | 2016-05-12 | Voco Gmbh | Verwendung radikalisch härtbarer Zusammensetzungen in generativen Fertigungsverfahren |
| CN108778229A (zh) | 2016-03-07 | 2018-11-09 | 3M创新有限公司 | 预成形复合牙冠、其生产方法和用途 |
| EP3338756B1 (de) | 2016-12-21 | 2020-02-26 | VOCO GmbH | Lagerstabiler kunststoffmodifizierter glasionomerzement |
| DE102017103084A1 (de) | 2017-02-15 | 2018-08-16 | Voco Gmbh | Dentaler Kompositblock zur Herstellung permanenter indirekter Restaurationen im CAD/CAM Verfahren |
| DE102017105841A1 (de) | 2017-03-17 | 2018-09-20 | Voco Gmbh | Fräsrohling zur Herstellung einer indirekten dentalen Restauration, entsprechende Verwendungen und Verfahren |
| CN111315341B (zh) | 2017-11-08 | 2021-06-04 | 3M创新有限公司 | 具有高e-模量的牙科用组合物 |
| WO2019152187A1 (en) | 2018-01-31 | 2019-08-08 | 3M Innovative Properties Company | Photolabile barbiturate compounds |
| EP3746775A1 (en) | 2018-01-31 | 2020-12-09 | 3M Innovative Properties Company | Virtual camera array for inspection of manufactured webs |
| TWI794400B (zh) | 2018-01-31 | 2023-03-01 | 美商3M新設資產公司 | 用於連續移動帶材的紅外光透射檢查 |
| CN111683974A (zh) | 2018-01-31 | 2020-09-18 | 3M创新有限公司 | 光不稳定的β-二羰基化合物 |
| DE102018103415A1 (de) | 2018-02-15 | 2019-08-22 | Voco Gmbh | Dentale Formkörper mit kontinuierlichem Farbverlauf |
| JP2022538528A (ja) | 2019-06-13 | 2022-09-05 | スリーエム イノベイティブ プロパティズ カンパニー | 架橋剤及びそれを含む硬化性組成物 |
| DE102019122174A1 (de) | 2019-08-19 | 2021-02-25 | Voco Gmbh | Dentale polymerisierbare Zusammensetzung auf der Basis kondensierter Silane |
| WO2021137091A1 (en) | 2019-12-30 | 2021-07-08 | 3M Innovative Properties Company | Light and redox curable compositions |
| CN116194541A (zh) | 2020-08-11 | 2023-05-30 | 3M创新有限公司 | (甲基)丙烯酸酯结构粘合剂和方法 |
| US20240076523A1 (en) | 2020-11-12 | 2024-03-07 | 3M Innovative Properties Company | Free-radically polymerizable crosslinker, curable composition, and adhesive therefrom |
| EP4244268A1 (en) | 2020-11-12 | 2023-09-20 | 3M Innovative Properties Company | Free-radically polymerizable crosslinker, curable composition, and adhesive therefrom |
| EP4251117A1 (en) | 2020-11-25 | 2023-10-04 | 3M Innovative Properties Company | Curable dental compositions and uses thereof |
| US11739172B2 (en) | 2020-12-17 | 2023-08-29 | 3M Innovative Properties Company | Composition including monomer with a carboxylic acid group, monomer with a hydroxyl group, and crosslinker and related articles and methods |
| CN116981705A (zh) | 2020-12-17 | 2023-10-31 | 3M创新有限公司 | 包含具有羧酸基团的丙烯酸类单体、具有羟基基团的丙烯酸类单体、(甲基)丙烯酸烷基酯单体和交联剂的组合物以及相关制品和方法 |
| CN116648488A (zh) | 2020-12-17 | 2023-08-25 | 3M创新有限公司 | 包含具有羧酸基团的单体、具有羟基基团的单体、环烷基单体和交联剂的组合物以及相关制品和方法 |
| WO2023007401A1 (en) | 2021-07-27 | 2023-02-02 | 3M Innovative Properties Company | Composition including monomer with a carboxylic acid group, monomer with a hydroxyl group, an alkyl monomer, and crosslinker and related article and method |
| WO2023031719A1 (en) * | 2021-09-01 | 2023-03-09 | 3M Innovative Properties Company | Free-radically polymerizable composition, method of polymerizing the same, and polymerized composition |
| EP4444809A1 (en) | 2021-12-06 | 2024-10-16 | 3M Innovative Properties Company | Adhesives comprising cyclic imide addition-fragmentation and adhesion agents |
| CN118355040A (zh) | 2021-12-15 | 2024-07-16 | 3M创新有限公司 | 用于(甲基)丙烯酸树脂的可降解的交联剂和其方法 |
| WO2023166342A1 (en) | 2022-03-02 | 2023-09-07 | 3M Innovative Properties Company | Polymerizable compositions including a polymerizable component and a redox initiation system containing a photolabile reducing agent, and a photolabile reducing agent |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE538514A (US20090130037A1-20090521-C00023.png) * | 1954-05-28 | |||
| DE1060590B (de) * | 1957-08-27 | 1959-07-02 | Basf Ag | Verfahren zur Herstellung von Formkoerpern und UEberzuegen |
| US3031301A (en) * | 1959-03-30 | 1962-04-24 | Gen Electric | Photosensitive resin compositions |
-
1964
- 1964-05-02 DE DE19641495520 patent/DE1495520B2/de active Granted
-
1965
- 1965-04-01 CH CH453265A patent/CH479633A/de not_active IP Right Cessation
- 1965-04-09 DK DK182965AA patent/DK129417B/da unknown
- 1965-04-27 US US451350A patent/US3347954A/en not_active Expired - Lifetime
- 1965-04-29 GB GB18137/65A patent/GB1110673A/en not_active Expired
- 1965-04-29 NL NL656505490A patent/NL143947B/xx unknown
- 1965-04-30 BE BE663329A patent/BE663329A/xx unknown
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