CA1206678A - Agent for retarding the polymerization of aziridine compounds - Google Patents
Agent for retarding the polymerization of aziridine compoundsInfo
- Publication number
- CA1206678A CA1206678A CA000442471A CA442471A CA1206678A CA 1206678 A CA1206678 A CA 1206678A CA 000442471 A CA000442471 A CA 000442471A CA 442471 A CA442471 A CA 442471A CA 1206678 A CA1206678 A CA 1206678A
- Authority
- CA
- Canada
- Prior art keywords
- imidazole
- substituted
- compound
- imidazolyl
- unsubstituted
- 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
- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 11
- 230000000979 retarding effect Effects 0.000 title claims abstract description 5
- 150000001541 aziridines Chemical class 0.000 title abstract description 15
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000001879 gelation Methods 0.000 claims abstract description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 46
- -1 aziridine compound Chemical class 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 37
- 239000003999 initiator Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 7
- 229920000570 polyether Polymers 0.000 claims description 7
- JMTFLSQHQSFNTE-UHFFFAOYSA-N 1-dodecylimidazole Chemical compound CCCCCCCCCCCCN1C=CN=C1 JMTFLSQHQSFNTE-UHFFFAOYSA-N 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- LVNIZHAEGQDEFX-UHFFFAOYSA-N 1-(10-imidazol-1-yldecyl)imidazole Chemical compound C1=CN=CN1CCCCCCCCCCN1C=CN=C1 LVNIZHAEGQDEFX-UHFFFAOYSA-N 0.000 claims description 4
- NUXHRJHNSNRMMO-UHFFFAOYSA-N 1-(2-ethoxyethyl)imidazole Chemical compound CCOCCN1C=CN=C1 NUXHRJHNSNRMMO-UHFFFAOYSA-N 0.000 claims description 4
- XNLOIFUGGCCEQX-UHFFFAOYSA-N 1-(4-methoxyphenyl)imidazole Chemical compound C1=CC(OC)=CC=C1N1C=NC=C1 XNLOIFUGGCCEQX-UHFFFAOYSA-N 0.000 claims description 4
- MCMFEZDRQOJKMN-UHFFFAOYSA-N 1-butylimidazole Chemical compound CCCCN1C=CN=C1 MCMFEZDRQOJKMN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 125000002905 alkanoylamido group Chemical group 0.000 claims description 4
- LFWSSKKRUZKNHM-UHFFFAOYSA-N n-benzyl-11-imidazol-1-ylundecanamide Chemical compound C=1C=CC=CC=1CNC(=O)CCCCCCCCCCN1C=CN=C1 LFWSSKKRUZKNHM-UHFFFAOYSA-N 0.000 claims description 4
- 239000004014 plasticizer Substances 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- PEPIOVUNFZBCIB-UHFFFAOYSA-N 1-Decylimidazole Chemical compound CCCCCCCCCCN1C=CN=C1 PEPIOVUNFZBCIB-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- YBXNRUYDSYXYFU-UHFFFAOYSA-N 1-(2-imidazol-1-ylethyl)imidazole Chemical compound C1=CN=CN1CCN1C=CN=C1 YBXNRUYDSYXYFU-UHFFFAOYSA-N 0.000 claims 3
- KKKDZZRICRFGSD-UHFFFAOYSA-N 1-benzylimidazole Chemical compound C1=CN=CN1CC1=CC=CC=C1 KKKDZZRICRFGSD-UHFFFAOYSA-N 0.000 claims 3
- VGZINEPOBWTUEH-UHFFFAOYSA-N 1-cyclohexylimidazole Chemical compound C1CCCCC1N1C=NC=C1 VGZINEPOBWTUEH-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 3
- 125000002560 nitrile group Chemical group 0.000 claims 1
- 239000003505 polymerization initiator Substances 0.000 claims 1
- 150000002460 imidazoles Chemical class 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 6
- 238000007792 addition Methods 0.000 description 5
- 210000000988 bone and bone Anatomy 0.000 description 5
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- BJQHLKABXJIVAM-BGYRXZFFSA-N 1-o-[(2r)-2-ethylhexyl] 2-o-[(2s)-2-ethylhexyl] benzene-1,2-dicarboxylate Chemical compound CCCC[C@H](CC)COC(=O)C1=CC=CC=C1C(=O)OC[C@H](CC)CCCC BJQHLKABXJIVAM-BGYRXZFFSA-N 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N Diethylhexyl phthalate Natural products CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000002825 nitriles Chemical group 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- QZCLKYGREBVARF-UHFFFAOYSA-N Acetyl tributyl citrate Chemical compound CCCCOC(=O)CC(C(=O)OCCCC)(OC(C)=O)CC(=O)OCCCC QZCLKYGREBVARF-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 238000010850 salt effect Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/90—Compositions for taking dental impressions
Landscapes
- Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dental Preparations (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823245052 DE3245052A1 (de) | 1982-12-06 | 1982-12-06 | Verzoegerer fuer die polymerisation von aziridinverbindungen |
| DEP3245052.4 | 1982-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1206678A true CA1206678A (en) | 1986-06-24 |
Family
ID=6179902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000442471A Expired CA1206678A (en) | 1982-12-06 | 1983-12-02 | Agent for retarding the polymerization of aziridine compounds |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4532268A (enExample) |
| EP (1) | EP0110429B1 (enExample) |
| JP (1) | JPS59115329A (enExample) |
| AT (1) | ATE49605T1 (enExample) |
| AU (1) | AU562068B2 (enExample) |
| CA (1) | CA1206678A (enExample) |
| DE (2) | DE3245052A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3702233A1 (de) * | 1987-01-27 | 1988-08-04 | Espe Stiftung | Eine aziridinverbindung enthaltendes praeparat fuer dentale zwecke |
| DE3932989A1 (de) * | 1989-10-03 | 1991-04-11 | Espe Stiftung | Polyalkylenoxidderivate enthaltende polyetherabformmassen |
| DE4306997A1 (de) * | 1993-03-05 | 1994-09-08 | Thera Ges Fuer Patente | Hydrophilierte Polyether |
| DE19618718B4 (de) * | 1996-05-09 | 2005-01-13 | 3M Espe Ag | Verfahren zur Anmischung von Abformmassen |
| DE19753461A1 (de) | 1997-12-02 | 1999-06-10 | Espe Dental Ag | Lagerstabile kationisch polymerisierende Zubereitungen mit verbessertem Härtungsverhalten |
| DE19753456B4 (de) * | 1997-12-02 | 2007-01-11 | 3M Espe Ag | Zweikomponente, kationisch aushärtende Zubereitungen auf der Basis von Aziridinopolyethern und deren Verwendung |
| DE19926728B4 (de) | 1999-06-11 | 2011-08-18 | 3M Espe Ag, 82229 | Verwendung von Trägermaterialien und diagnostisch nutzbaren Zusatzstoffen in Abbildungsverfahren für intraorale Diagnosezwecke |
| DE10001747C2 (de) * | 2000-01-17 | 2003-02-13 | 3M Espe Ag | Zubereitungen auf Polyetherbasis und deren Verwendung |
| DE10026852A1 (de) | 2000-05-31 | 2001-12-13 | 3M Espe Ag | N-Alkyl-Azirdinoblock Copolymere und deren Verwendung |
| DE10061195B4 (de) | 2000-12-08 | 2004-12-02 | 3M Espe Ag | Verwendung von Abformmassen zur Herstellung von Behandlungsvorrichtungen |
| DE10126476A1 (de) | 2001-05-31 | 2002-12-19 | 3M Espe Ag | N-Alkylaziridinoprepolymere |
| DE10235990A1 (de) | 2002-08-06 | 2004-02-26 | 3M Espe Ag | Zubereitungen auf Polyetherbasis und deren Verwendung |
| EP1748057A1 (en) * | 2005-07-29 | 2007-01-31 | 3M Innovative Properties Company | Sulfonium initiators, process for production and use in cationic polymerizable compositions |
| EP1820815A1 (en) | 2006-02-15 | 2007-08-22 | 3M Innovative Properties Company | Composition containing aziridino groups and use thereof |
| EP1865014A1 (en) | 2006-06-07 | 2007-12-12 | 3M Innovative Properties Company | Composition containing aziridino groups, method of production and use thereof |
| EP1882469A1 (en) | 2006-07-28 | 2008-01-30 | 3M Innovative Properties Company | Polyether-based preparations and use thereof |
| EP2072030A1 (en) | 2007-12-20 | 2009-06-24 | 3M Innovative Properties Company | Dental impression material containing rheological modifiers |
| WO2011016977A1 (en) | 2009-07-28 | 2011-02-10 | 3M Innovative Properties Company | Cationically hardenable dental composition, process of production and use thereof |
| EP2428199A1 (en) | 2010-09-09 | 2012-03-14 | 3M Innovative Properties Company | Curable composition, process of production and use thereof |
| US8752287B2 (en) | 2011-04-07 | 2014-06-17 | Melvin James Daniels | Method of sealing at least one engine gas leak |
| EP3883522B1 (en) | 2018-11-20 | 2025-01-08 | Solventum Intellectual Properties Company | Use of a polyether-modified polydimethyl siloxane for reducing the stickiness of a dental impression composition |
| US20240285476A1 (en) | 2021-05-26 | 2024-08-29 | 3M Innovative Properties Company | Dental composition comprising an isorbide component |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3751395A (en) * | 1962-06-20 | 1973-08-07 | Espe Pharm Praep | Casting materials for dental purposes containing a bis-ethylene-imene compound capable of being crosslinked |
| DE1745810B2 (de) * | 1963-05-29 | 1971-12-02 | Espe Fabrik pharmazeutischer Prapa rate GmbH, 8031 Seefeld | Verfahren zur herstellung von formkoerpern auf der basis von aethyleniminverbindungen |
| US4093555A (en) * | 1974-01-30 | 1978-06-06 | Espe Fabrik Pharmazeutischer Praparate Gmbh | Production of dental models and tooth replacement parts |
| CH606190A5 (enExample) * | 1974-04-19 | 1978-10-31 | Espe Pharm Praep | |
| US4167618A (en) * | 1975-04-15 | 1979-09-11 | Espe Fabrik Pharmazeutischer Praparate Gmbh | Polymerization process for aziridine compounds |
-
1982
- 1982-12-06 DE DE19823245052 patent/DE3245052A1/de not_active Withdrawn
-
1983
- 1983-10-31 AU AU20843/83A patent/AU562068B2/en not_active Ceased
- 1983-12-01 US US06/556,772 patent/US4532268A/en not_active Expired - Lifetime
- 1983-12-02 CA CA000442471A patent/CA1206678A/en not_active Expired
- 1983-12-05 JP JP58230476A patent/JPS59115329A/ja active Granted
- 1983-12-06 EP EP83112248A patent/EP0110429B1/de not_active Expired - Lifetime
- 1983-12-06 DE DE8383112248T patent/DE3381114D1/de not_active Expired - Lifetime
- 1983-12-06 AT AT83112248T patent/ATE49605T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE3381114D1 (de) | 1990-02-22 |
| JPH0447691B2 (enExample) | 1992-08-04 |
| AU2084383A (en) | 1984-06-14 |
| EP0110429A3 (en) | 1987-08-26 |
| EP0110429B1 (de) | 1990-01-17 |
| ATE49605T1 (de) | 1990-02-15 |
| AU562068B2 (en) | 1987-05-28 |
| JPS59115329A (ja) | 1984-07-03 |
| US4532268A (en) | 1985-07-30 |
| EP0110429A2 (de) | 1984-06-13 |
| DE3245052A1 (de) | 1984-06-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |