DE4137076C2 - - Google Patents
Info
- Publication number
- DE4137076C2 DE4137076C2 DE4137076A DE4137076A DE4137076C2 DE 4137076 C2 DE4137076 C2 DE 4137076C2 DE 4137076 A DE4137076 A DE 4137076A DE 4137076 A DE4137076 A DE 4137076A DE 4137076 C2 DE4137076 C2 DE 4137076C2
- Authority
- DE
- Germany
- Prior art keywords
- group
- alkyl
- carbonyl
- alkoxy
- dental adhesive
- 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 - Fee Related
Links
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 239000003479 dental cement Substances 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 20
- 239000000853 adhesive Substances 0.000 claims abstract description 19
- 230000001070 adhesive effect Effects 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 5
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 125000005504 styryl group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical class C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 150000007970 thio esters Chemical group 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 10
- 230000008569 process Effects 0.000 abstract description 3
- 210000004268 dentin Anatomy 0.000 description 26
- -1 US 48 16 495 A Chemical class 0.000 description 11
- UACSZOWTRIJIFU-UHFFFAOYSA-N hydroxymethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCO UACSZOWTRIJIFU-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 5
- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- 239000002131 composite material Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- JXCDTORYGUGXIJ-UHFFFAOYSA-N 2-hydroxyethyl 2-methylprop-2-enoate;pentanedial Chemical compound O=CCCCC=O.CC(=C)C(=O)OCCO JXCDTORYGUGXIJ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000428456 Gluma Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000536 complexating effect Effects 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 239000005548 dental material Substances 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- QRIMLDXJAPZHJE-UHFFFAOYSA-N 2,3-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CO QRIMLDXJAPZHJE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241000252505 Characidae Species 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229920000604 Polyethylene Glycol 200 Polymers 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 208000002599 Smear Layer Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- SXMUXFDPJBTNRM-UHFFFAOYSA-N [2-hydroxy-3-[4-[2-[4-[2-hydroxy-3-(2-methylprop-2-enoyloxy)propoxy]phenyl]propan-2-yl]phenoxy]propyl] 2-methylprop-2-enoate;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.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 SXMUXFDPJBTNRM-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004154 testing of material Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dental Preparations (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4137076A DE4137076A1 (de) | 1991-11-12 | 1991-11-12 | Dentalklebstoff |
| AT92250312T ATE151628T1 (de) | 1991-11-12 | 1992-10-27 | Dentalklebstoff |
| EP92250312A EP0546648B1 (de) | 1991-11-12 | 1992-10-27 | Dentalklebstoff |
| DE59208355T DE59208355D1 (de) | 1991-11-12 | 1992-10-27 | Dentalklebstoff |
| AU27409/92A AU650580B2 (en) | 1991-11-12 | 1992-10-28 | Dental cement |
| CA002082132A CA2082132C (en) | 1991-11-12 | 1992-11-04 | Dental cement |
| JP4302711A JPH0825854B2 (ja) | 1991-11-12 | 1992-11-12 | 歯科用セメント |
| US08/394,198 US5519071A (en) | 1991-11-12 | 1995-02-24 | Dental cement |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4137076A DE4137076A1 (de) | 1991-11-12 | 1991-11-12 | Dentalklebstoff |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE4137076A1 DE4137076A1 (de) | 1993-05-13 |
| DE4137076C2 true DE4137076C2 (cg-RX-API-DMAC7.html) | 1993-08-12 |
Family
ID=6444554
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4137076A Granted DE4137076A1 (de) | 1991-11-12 | 1991-11-12 | Dentalklebstoff |
| DE59208355T Expired - Fee Related DE59208355D1 (de) | 1991-11-12 | 1992-10-27 | Dentalklebstoff |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59208355T Expired - Fee Related DE59208355D1 (de) | 1991-11-12 | 1992-10-27 | Dentalklebstoff |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5519071A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0546648B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JPH0825854B2 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE151628T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU650580B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2082132C (cg-RX-API-DMAC7.html) |
| DE (2) | DE4137076A1 (cg-RX-API-DMAC7.html) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4402766A1 (de) * | 1994-01-26 | 1995-07-27 | Ivoclar Ag | Verwendung einer thermisch härtbaren Zusammensetzung als Dentalmaterial |
| DE19749349A1 (de) * | 1997-11-07 | 1999-05-12 | Espe Dental Ag | Polymerisierbare Zusammensetzung und ihre Verwendung als Haftvermittler |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4339009C2 (de) * | 1993-11-10 | 1996-02-22 | Ivoclar Ag | Mehrkomponentendentalzement auf Calciumhydroxid-Basis |
| DE19544673C2 (de) * | 1995-11-30 | 2001-03-29 | Heraeus Kulzer Gmbh & Co Kg | Dentaladhäsive |
| US5965147A (en) * | 1997-12-03 | 1999-10-12 | Mycone Dental Inc. | Artificial fingernails |
| DE19841614A1 (de) * | 1998-09-11 | 2000-03-16 | Wieland Edelmetalle | Verfahren zur Herstellung eines Metall-Kunststoff-Verbundsystems und Metall-Kunststoff-Verbundsystem |
| DE102005022172A1 (de) | 2005-05-13 | 2006-11-16 | Voco Gmbh | Haftverbessernde Additive für polymerisierbare Zusammensetzungen |
| JP5203749B2 (ja) | 2008-03-04 | 2013-06-05 | 株式会社松風 | 硬化前後における色調変化の少ない光重合性歯科用組成物 |
| JP5702044B2 (ja) * | 2008-03-04 | 2015-04-15 | 株式会社松風 | モノマーによって色調変化を抑えた光硬化性歯科用組成物 |
| EP2450025B1 (de) | 2010-11-08 | 2012-11-28 | VOCO GmbH | Polymerisierbare Phosphorsäurederivate umfassend ein polyalicyclisches Strukturelement |
| US9029451B2 (en) | 2010-12-15 | 2015-05-12 | Eastman Chemical Company | Waterborne coating compositions that include 2,2,4-trimethyl-3-oxopentanoate esters as reactive coalescents |
| US8809447B2 (en) * | 2010-12-15 | 2014-08-19 | Eastman Chemical Company | Acetoacetate-functional monomers and their uses in coating compositions |
| US8809446B2 (en) * | 2010-12-15 | 2014-08-19 | Eastman Chemical Company | Substituted 3-oxopentanoates and their uses in coating compositions |
| CA2885996A1 (en) | 2011-10-03 | 2013-04-11 | Biomimedica, Inc. | Polymeric adhesive for anchoring compliant materials to another surface |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4408418A (en) * | 1980-01-21 | 1983-10-11 | Colt Industries Operating Corp. | Method of forming through-feed cylindrical thread rolling dies |
| US4340529A (en) * | 1980-04-11 | 1982-07-20 | Lee Pharmaceuticals, Inc. | No-mix orthodontic adhesive formulations |
| DE3149797C2 (de) * | 1981-12-16 | 1986-06-19 | Henkel KGaA, 4000 Düsseldorf | Reaktive (Meth)-acrylatklebstoffe mit Acetessigesterstrukturen |
| US4408018A (en) * | 1982-10-29 | 1983-10-04 | Rohm And Haas Company | Acetoacetate functionalized polymers and monomers useful for crosslinking formulations |
| DK155079C (da) * | 1983-10-25 | 1989-06-19 | Erik Chr Munksgaard | Adhaesionsfremmende middel for haerdende acrylat- eller methacrylatmaterialer til brug paa collagenholdige materialer, isaer dentin, og midlets anvendelse |
| JPS60202873A (ja) * | 1984-03-27 | 1985-10-14 | G C Dental Ind Corp | （メタ）アクリロキシアルキルナフタレントリカルボン酸無水物 |
| DE3510611A1 (de) * | 1985-03-23 | 1986-09-25 | Bayer Ag, 5090 Leverkusen | Beschichtungsmaterial fuer kollagenhaltige materialien |
| EP0244997A3 (en) * | 1986-05-02 | 1988-06-01 | Union Oil Company Of California | Pressure sensitive adhesives and manufactured articles |
| US4908403A (en) * | 1986-05-02 | 1990-03-13 | Union Oil Of California | Pressure sensitive adhesives of acetoacetoxy-alkyl acrylate polymers |
| DE3634354A1 (de) * | 1986-10-08 | 1988-04-21 | Muehlbauer Ernst Kg | Verbindungen, die aus aldehyd-, epoxid-, isocyanat- oder halotriazingruppen, polymerisierbaren gruppen und einem hoehermolekularen grundgeruest bestehen, dieselben enthaltenden mischungen und ihre verwendung |
| US4743668A (en) * | 1987-03-17 | 1988-05-10 | Nalco Chemical Company | N-acetoacetyl (meth)acrylamide polymers |
| JPH0753846B2 (ja) * | 1988-06-20 | 1995-06-07 | 株式会社クラレ | 含イオウ接着剤 |
| AU632605B2 (en) * | 1989-08-14 | 1993-01-07 | Mitsubishi Rayon Company Limited | Material for dentistry |
| DE3931418A1 (de) * | 1989-09-21 | 1991-04-04 | Bayer Ag | Alkandiyl-bis-carbonamide, adhaesivkomponenten zur behandlung kollagenhaltiger materialien, enthaltend diese verbindungen, sowie herstellung und anwendung dieser adhaesivkomponenten |
-
1991
- 1991-11-12 DE DE4137076A patent/DE4137076A1/de active Granted
-
1992
- 1992-10-27 EP EP92250312A patent/EP0546648B1/de not_active Expired - Lifetime
- 1992-10-27 AT AT92250312T patent/ATE151628T1/de not_active IP Right Cessation
- 1992-10-27 DE DE59208355T patent/DE59208355D1/de not_active Expired - Fee Related
- 1992-10-28 AU AU27409/92A patent/AU650580B2/en not_active Ceased
- 1992-11-04 CA CA002082132A patent/CA2082132C/en not_active Expired - Fee Related
- 1992-11-12 JP JP4302711A patent/JPH0825854B2/ja not_active Expired - Fee Related
-
1995
- 1995-02-24 US US08/394,198 patent/US5519071A/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4402766A1 (de) * | 1994-01-26 | 1995-07-27 | Ivoclar Ag | Verwendung einer thermisch härtbaren Zusammensetzung als Dentalmaterial |
| DE19749349A1 (de) * | 1997-11-07 | 1999-05-12 | Espe Dental Ag | Polymerisierbare Zusammensetzung und ihre Verwendung als Haftvermittler |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2082132C (en) | 1998-10-27 |
| DE4137076A1 (de) | 1993-05-13 |
| AU650580B2 (en) | 1994-06-23 |
| ATE151628T1 (de) | 1997-05-15 |
| US5519071A (en) | 1996-05-21 |
| JPH0825854B2 (ja) | 1996-03-13 |
| EP0546648B1 (de) | 1997-04-16 |
| JPH05255034A (ja) | 1993-10-05 |
| DE59208355D1 (de) | 1997-05-22 |
| CA2082132A1 (en) | 1993-05-13 |
| EP0546648A1 (de) | 1993-06-16 |
| AU2740992A (en) | 1993-05-13 |
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|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: IVOCLAR VIVADENT AG, SCHAAN, LI |
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| 8339 | Ceased/non-payment of the annual fee |