GB1591741A - Paste-like photopolymerizable dental restorative compositions - Google Patents
Paste-like photopolymerizable dental restorative compositions Download PDFInfo
- Publication number
- GB1591741A GB1591741A GB44077/77A GB4407777A GB1591741A GB 1591741 A GB1591741 A GB 1591741A GB 44077/77 A GB44077/77 A GB 44077/77A GB 4407777 A GB4407777 A GB 4407777A GB 1591741 A GB1591741 A GB 1591741A
- Authority
- GB
- United Kingdom
- Prior art keywords
- composition according
- composition
- aluminium silicate
- monomer
- ethylenically unsaturated
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 91
- 239000000178 monomer Substances 0.000 claims abstract description 58
- 239000003085 diluting agent Substances 0.000 claims abstract description 24
- 239000003999 initiator Substances 0.000 claims abstract description 24
- 239000000945 filler Substances 0.000 claims abstract description 16
- 239000011347 resin Substances 0.000 claims abstract description 3
- 229920005989 resin Polymers 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims description 33
- 238000006116 polymerization reaction Methods 0.000 claims description 21
- 239000005995 Aluminium silicate Substances 0.000 claims description 16
- 229910000323 aluminium silicate Inorganic materials 0.000 claims description 16
- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 claims description 16
- 235000012211 aluminium silicate Nutrition 0.000 claims description 16
- 229910052788 barium Inorganic materials 0.000 claims description 16
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 16
- 229910000502 Li-aluminosilicate Inorganic materials 0.000 claims description 14
- 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 14
- 230000005855 radiation Effects 0.000 claims description 13
- 150000001412 amines Chemical group 0.000 claims description 12
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 9
- DIAIBWNEUYXDNL-UHFFFAOYSA-N n,n-dihexylhexan-1-amine Chemical compound CCCCCCN(CCCCCC)CCCCCC DIAIBWNEUYXDNL-UHFFFAOYSA-N 0.000 claims description 8
- 238000011049 filling Methods 0.000 claims description 7
- 239000011256 inorganic filler Substances 0.000 claims description 7
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 claims description 6
- 238000007334 copolymerization reaction Methods 0.000 claims description 6
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000004615 ingredient Substances 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000003512 tertiary amines Chemical group 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052753 mercury Inorganic materials 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000012360 testing method Methods 0.000 claims description 3
- 208000005623 Carcinogenesis Diseases 0.000 claims description 2
- 206010042496 Sunburn Diseases 0.000 claims description 2
- 238000009825 accumulation Methods 0.000 claims description 2
- 238000007792 addition Methods 0.000 claims description 2
- 230000001580 bacterial effect Effects 0.000 claims description 2
- 230000036952 cancer formation Effects 0.000 claims description 2
- 231100000504 carcinogenesis Toxicity 0.000 claims description 2
- 230000007547 defect Effects 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 231100000760 phototoxic Toxicity 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 238000010186 staining Methods 0.000 claims description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims 4
- 230000001419 dependent effect Effects 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract 1
- 239000013589 supplement Substances 0.000 abstract 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- -1 alkyl methacrylates Chemical class 0.000 description 8
- 229940106691 bisphenol a Drugs 0.000 description 6
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
- 239000012965 benzophenone Substances 0.000 description 5
- 229920002799 BoPET Polymers 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 239000005041 Mylar™ Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000007767 bonding agent Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- MTHFROHDIWGWFD-UHFFFAOYSA-N n-butyl-n-methylbutan-1-amine Chemical compound CCCCN(C)CCCC MTHFROHDIWGWFD-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YNANGXWUZWWFKX-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethane-1,2-dione Chemical compound C1=CC(OC)=CC=C1C(=O)C(=O)C1=CC=C(OC)C=C1 YNANGXWUZWWFKX-UHFFFAOYSA-N 0.000 description 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 2
- 206010073306 Exposure to radiation Diseases 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 208000002925 dental caries Diseases 0.000 description 2
- 239000011350 dental composite resin Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- DIHKMUNUGQVFES-UHFFFAOYSA-N n,n,n',n'-tetraethylethane-1,2-diamine Chemical compound CCN(CC)CCN(CC)CC DIHKMUNUGQVFES-UHFFFAOYSA-N 0.000 description 2
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Chemical group OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
- JSYPRLVDJYQMAI-ODZAUARKSA-N (z)-but-2-enedioic acid;prop-2-enoic acid Chemical group OC(=O)C=C.OC(=O)\C=C/C(O)=O JSYPRLVDJYQMAI-ODZAUARKSA-N 0.000 description 1
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 1
- RXVBJUZEFSAYPW-UHFFFAOYSA-N 1,3-diphenylpropane-1,2,3-trione Chemical compound C=1C=CC=CC=1C(=O)C(=O)C(=O)C1=CC=CC=C1 RXVBJUZEFSAYPW-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- GXYNBAXTKOYFND-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethyl 3-methylbut-2-enoate Chemical compound CC(=CC(=O)OCCOCCOCCO)C GXYNBAXTKOYFND-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229920005822 acrylic binder Polymers 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 229940018560 citraconate Drugs 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000005548 dental material Substances 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical class CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000013038 hand mixing Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical group OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical group OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000068 pit and fissure sealant Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- MKWYFZFMAMBPQK-UHFFFAOYSA-J sodium feredetate Chemical compound [Na+].[Fe+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O MKWYFZFMAMBPQK-UHFFFAOYSA-J 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- JLZUZNKTTIRERF-UHFFFAOYSA-N tetraphenylethylene Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)=C(C=1C=CC=CC=1)C1=CC=CC=C1 JLZUZNKTTIRERF-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 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
-
- 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)
- Plastic & Reconstructive Surgery (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dental Preparations (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US74202376A | 1976-11-15 | 1976-11-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1591741A true GB1591741A (en) | 1981-06-24 |
Family
ID=24983191
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB44077/77A Expired GB1591741A (en) | 1976-11-15 | 1977-10-24 | Paste-like photopolymerizable dental restorative compositions |
Country Status (10)
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7811486B2 (en) | 2003-08-19 | 2010-10-12 | 3M Innovative Properties Company | Method of manufacturing a hardenable dental article |
US7816423B2 (en) | 2001-08-15 | 2010-10-19 | 3M Innovative Properties Company | Hardenable self-supporting structures and methods |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2850918A1 (de) * | 1978-11-24 | 1980-06-04 | Bayer Ag | Roentgenopake dentalwerkstoffe auf basis von organischen kunststoffen in pastoeser form |
JPS56120610A (en) * | 1980-02-27 | 1981-09-22 | Kuraray Co Ltd | Photopolymerizable dental material |
DE3174624D1 (en) * | 1980-08-29 | 1986-06-19 | Dentsply Int Inc | Visible light curable dental compositions |
IL65159A0 (en) * | 1981-03-04 | 1982-05-31 | Ici Plc | Polymerisable dental compositions |
USRE35264E (en) * | 1981-05-04 | 1996-06-04 | Dentsply Research & Development Corp. | Dental adhesive system |
US4388069A (en) * | 1982-04-15 | 1983-06-14 | Blendax-Werke R. Schneider Gmbh & Co. | Dental restorative material |
DE3403040A1 (de) * | 1984-01-30 | 1985-08-08 | Blendax-Werke R. Schneider Gmbh & Co, 6500 Mainz | Dentales fuellungsmaterial |
CA1292338C (en) * | 1985-01-29 | 1991-11-19 | Dentsply International Inc. | Non-toxic organic compositions and calcium hydroxide compositions thereof |
DE3536076A1 (de) * | 1985-10-09 | 1987-04-09 | Muehlbauer Ernst Kg | Polymerisierbare zementmischungen |
JPS6286003A (ja) * | 1985-10-11 | 1987-04-20 | Tokuyama Soda Co Ltd | 光重合用の複合組成物 |
JPH02191207A (ja) * | 1989-01-18 | 1990-07-27 | Sogo Shika Iryo Kenkyusho:Kk | 歯科矯正用接着剤 |
EP0773803A1 (en) * | 1994-07-25 | 1997-05-21 | Advanced Cardiovascular Systems, Inc. | Composite polyester material having a lubricous surface |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE442520A (enrdf_load_stackoverflow) * | 1940-10-05 | |||
US2335133A (en) * | 1942-05-30 | 1943-11-23 | Du Pont | Tooth reconstruction |
GB1113723A (en) * | 1964-05-21 | 1968-05-15 | Minnesota Mining & Mfg | Dental filling material |
US3759807A (en) * | 1969-01-28 | 1973-09-18 | Union Carbide Corp | Photopolymerization process using combination of organic carbonyls and amines |
US3911581A (en) * | 1970-02-17 | 1975-10-14 | Owens Illinois Inc | Tooth filling and facing composition comprising a radiopaque glass and method of using the same |
US3709866A (en) * | 1970-06-01 | 1973-01-09 | Dentsply Int Inc | Photopolymerizable dental products |
GB1408265A (en) * | 1971-10-18 | 1975-10-01 | Ici Ltd | Photopolymerisable composition |
GB1428672A (en) * | 1972-04-25 | 1976-03-17 | Amalgamated Dental Co Ltd | Polymerizable compositions suitable for dental use |
JPS4974235A (enrdf_load_stackoverflow) * | 1972-11-16 | 1974-07-17 | ||
GB1465897A (en) * | 1973-04-24 | 1977-03-02 | Ici Ltd | Dental compositions |
AR205444A1 (es) * | 1973-04-24 | 1976-05-07 | Ici Ltd | Composicion para relleno dental |
JPS50116539A (enrdf_load_stackoverflow) * | 1974-02-13 | 1975-09-11 | ||
GB1498421A (en) * | 1974-05-21 | 1978-01-18 | Ici Ltd | Dental compositions |
DE2506650A1 (de) * | 1975-02-17 | 1976-08-26 | Nath Guenther | Photopolymerisierbare substanz |
-
1977
- 1977-10-14 CA CA000288773A patent/CA1117685A/en not_active Expired
- 1977-10-18 SE SE7711708A patent/SE433037B/sv not_active IP Right Cessation
- 1977-10-24 GB GB44077/77A patent/GB1591741A/en not_active Expired
- 1977-11-03 BR BR7707395A patent/BR7707395A/pt unknown
- 1977-11-07 IT IT51722/77A patent/IT1091769B/it active
- 1977-11-08 FR FR7733591A patent/FR2370467A1/fr active Granted
- 1977-11-08 AU AU30439/77A patent/AU3043977A/en active Pending
- 1977-11-15 DE DE2751057A patent/DE2751057C2/de not_active Expired - Lifetime
- 1977-11-15 CH CH1394477A patent/CH634746A5/de not_active IP Right Cessation
- 1977-11-15 JP JP13636177A patent/JPS5362394A/ja active Granted
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7816423B2 (en) | 2001-08-15 | 2010-10-19 | 3M Innovative Properties Company | Hardenable self-supporting structures and methods |
US7811486B2 (en) | 2003-08-19 | 2010-10-12 | 3M Innovative Properties Company | Method of manufacturing a hardenable dental article |
US8136657B2 (en) | 2003-08-19 | 2012-03-20 | 3M Innovative Properties Company | Packaged hardenable dental article |
Also Published As
Publication number | Publication date |
---|---|
JPS5362394A (en) | 1978-06-03 |
SE433037B (sv) | 1984-05-07 |
AU3043977A (en) | 1979-05-17 |
DE2751057A1 (de) | 1978-05-24 |
CA1117685A (en) | 1982-02-02 |
DE2751057C2 (de) | 1993-07-29 |
FR2370467A1 (fr) | 1978-06-09 |
CH634746A5 (en) | 1983-02-28 |
FR2370467B1 (enrdf_load_stackoverflow) | 1983-02-04 |
SE7711708L (sv) | 1978-05-16 |
BR7707395A (pt) | 1978-06-20 |
IT1091769B (it) | 1985-07-06 |
JPH025723B2 (enrdf_load_stackoverflow) | 1990-02-05 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
PE20 | Patent expired after termination of 20 years |
Effective date: 19971023 |