DE60005183T2 - Polymerisierbare sauere verbindungen und verfahren zur herstellung - Google Patents
Polymerisierbare sauere verbindungen und verfahren zur herstellung Download PDFInfo
- Publication number
- DE60005183T2 DE60005183T2 DE60005183T DE60005183T DE60005183T2 DE 60005183 T2 DE60005183 T2 DE 60005183T2 DE 60005183 T DE60005183 T DE 60005183T DE 60005183 T DE60005183 T DE 60005183T DE 60005183 T2 DE60005183 T2 DE 60005183T2
- Authority
- DE
- Germany
- Prior art keywords
- independently
- alkyl
- formula
- reaction
- alkyl group
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 38
- 239000002253 acid Substances 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 19
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 8
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 6
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 6
- 229920002939 poly(N,N-dimethylacrylamides) Polymers 0.000 claims description 5
- 235000019260 propionic acid Nutrition 0.000 claims description 5
- AHLWZBVXSWOPPL-RGYGYFBISA-N 20-deoxy-20-oxophorbol 12-myristate 13-acetate Chemical compound C([C@]1(O)C(=O)C(C)=C[C@H]1[C@@]1(O)[C@H](C)[C@H]2OC(=O)CCCCCCCCCCCCC)C(C=O)=C[C@H]1[C@H]1[C@]2(OC(C)=O)C1(C)C AHLWZBVXSWOPPL-RGYGYFBISA-N 0.000 claims description 4
- 241001602688 Pama Species 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 claims description 2
- SYRHIZPPCHMRIT-UHFFFAOYSA-N tin(4+) Chemical compound [Sn+4] SYRHIZPPCHMRIT-UHFFFAOYSA-N 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000178 monomer Substances 0.000 description 17
- 239000000463 material Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- SFUUDZYXHNYCTM-UHFFFAOYSA-N 2-methylprop-2-enamide;prop-2-enamide Chemical compound NC(=O)C=C.CC(=C)C(N)=O SFUUDZYXHNYCTM-UHFFFAOYSA-N 0.000 description 5
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 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 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 4
- 239000005548 dental material Substances 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000004568 cement Substances 0.000 description 3
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- 0 CC(C)**(NC(OC(C)(C)CC(C(O)O)N)=O)=C Chemical compound CC(C)**(NC(OC(C)(C)CC(C(O)O)N)=O)=C 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- -1 ZnF 2 Inorganic materials 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000002521 compomer Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 239000003479 dental cement Substances 0.000 description 2
- PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical compound C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 150000002221 fluorine Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000007306 functionalization reaction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003178 glass ionomer cement Substances 0.000 description 2
- 150000001261 hydroxy acids Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 1
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 1
- CMCOFAYLDYIEBR-UHFFFAOYSA-L 2-[carboxymethylsulfanyl(dioctyl)stannyl]sulfanylacetic acid Chemical compound [O-]C(=O)CS.[O-]C(=O)CS.CCCCCCCC[Sn+2]CCCCCCCC CMCOFAYLDYIEBR-UHFFFAOYSA-L 0.000 description 1
- IGMYAFRPSRRXNA-UHFFFAOYSA-L 2-[dibutyl(carboxymethylsulfanyl)stannyl]sulfanylacetic acid Chemical compound [O-]C(=O)CS.[O-]C(=O)CS.CCCC[Sn+2]CCCC IGMYAFRPSRRXNA-UHFFFAOYSA-L 0.000 description 1
- VPCAFPAKZIJBRH-UHFFFAOYSA-N 2-methylprop-2-enoic acid;oxiran-2-ylmethyl 2-methylprop-2-enoate Chemical group CC(=C)C(O)=O.CC(=C)C(=O)OCC1CO1 VPCAFPAKZIJBRH-UHFFFAOYSA-N 0.000 description 1
- ZRWNRAJCPNLYAK-UHFFFAOYSA-N 4-bromobenzamide Chemical compound NC(=O)C1=CC=C(Br)C=C1 ZRWNRAJCPNLYAK-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- 229910016569 AlF 3 Inorganic materials 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-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
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 229910008449 SnF 2 Inorganic materials 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- KYDGMZSIZYYJJJ-UHFFFAOYSA-L [dimethyl-(2-sulfanylacetyl)oxystannyl] 2-sulfanylacetate Chemical compound C[Sn+2]C.[O-]C(=O)CS.[O-]C(=O)CS KYDGMZSIZYYJJJ-UHFFFAOYSA-L 0.000 description 1
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- NSPSPMKCKIPQBH-UHFFFAOYSA-K bismuth;7,7-dimethyloctanoate Chemical compound [Bi+3].CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O.CC(C)(C)CCCCCC([O-])=O NSPSPMKCKIPQBH-UHFFFAOYSA-K 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- HGQSXVKHVMGQRG-UHFFFAOYSA-N dioctyltin Chemical compound CCCCCCCC[Sn]CCCCCCCC HGQSXVKHVMGQRG-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 229910001512 metal fluoride Inorganic materials 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- CYCFYXLDTSNTGP-UHFFFAOYSA-L octadecanoate;tin(2+) Chemical compound [Sn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CYCFYXLDTSNTGP-UHFFFAOYSA-L 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- OOCYPIXCHKROMD-UHFFFAOYSA-M phenyl(propanoyloxy)mercury Chemical compound CCC(=O)O[Hg]C1=CC=CC=C1 OOCYPIXCHKROMD-UHFFFAOYSA-M 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000003829 resin cement Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US314489 | 1999-05-18 | ||
| US09/314,489 US6143919A (en) | 1999-05-18 | 1999-05-18 | Polymerizable acidic compounds and methods of preparation |
| PCT/US2000/008319 WO2000069944A1 (en) | 1999-05-18 | 2000-03-29 | Polymerizable acidic compounds and methods of preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60005183D1 DE60005183D1 (de) | 2003-10-16 |
| DE60005183T2 true DE60005183T2 (de) | 2004-07-01 |
Family
ID=23220167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60005183T Expired - Lifetime DE60005183T2 (de) | 1999-05-18 | 2000-03-29 | Polymerisierbare sauere verbindungen und verfahren zur herstellung |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6143919A (enExample) |
| EP (1) | EP1185573B1 (enExample) |
| JP (1) | JP2002544290A (enExample) |
| AU (1) | AU4042700A (enExample) |
| CA (1) | CA2371572A1 (enExample) |
| DE (1) | DE60005183T2 (enExample) |
| WO (1) | WO2000069944A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008137948A (ja) * | 2006-12-01 | 2008-06-19 | Showa Denko Kk | 重合性単量体組成物および重合防止方法 |
| US8735463B2 (en) | 2007-05-31 | 2014-05-27 | Creighton University | Self-healing dental composites and related methods |
| JP6781062B2 (ja) * | 2017-01-31 | 2020-11-04 | 株式会社松風 | 高い機械的強度をもつ歯科用硬化性組成物 |
Family Cites Families (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1139430A (en) * | 1966-12-30 | 1969-01-08 | Nat Res Dev | Improvements relating to surgical cements |
| US3814717A (en) * | 1970-12-04 | 1974-06-04 | Dental Materials Section Labor | Poly(carboxylic acid)-fluoroalumino-silicate glass surgical cement |
| US4209434A (en) * | 1972-04-18 | 1980-06-24 | National Research Development Corporation | Dental cement containing poly(carboxylic acid), chelating agent and glass cement powder |
| GB1532954A (en) * | 1974-10-24 | 1978-11-22 | Nat Res Dev | Poly-(carboxylate)cements |
| US4144324A (en) * | 1976-10-08 | 1979-03-13 | Colgate Palmolive Company | Oral compositions for calculus retardation |
| US4208401A (en) * | 1977-08-19 | 1980-06-17 | Colgate-Palmolive Company | Quaternary ammonium alkylene diphosphonate anti-calculus agents |
| DE2929121A1 (de) * | 1979-07-18 | 1981-02-12 | Espe Pharm Praep | Calciumaluminiumfluorosilikatglas- pulver und seine verwendung |
| DE2932823A1 (de) * | 1979-08-13 | 1981-03-12 | Espe Pharm Praep | Anmischkomponente fuer glasionomerzemente |
| US4695251A (en) * | 1980-04-07 | 1987-09-22 | Minnesota Mining And Manufacturing Company | Orthodontic bracket adhesive and abrasive for removal thereof |
| DE3016289A1 (de) * | 1980-04-28 | 1981-10-29 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur herstellung von omega -amino-1-hydroxyalkyliden-1,1-bis-phosphonsaeuren |
| US4394494A (en) * | 1980-07-04 | 1983-07-19 | Lion Corporation | Dental filling material |
| JPS57106688A (en) * | 1980-12-20 | 1982-07-02 | Lion Corp | 1-methacryloxyethane-1,1-diphosphonic acid |
| US4503169A (en) * | 1984-04-19 | 1985-03-05 | Minnesota Mining And Manufacturing Company | Radiopaque, low visual opacity dental composites containing non-vitreous microparticles |
| GB8419489D0 (en) * | 1984-07-31 | 1984-09-05 | Leo Pharm Prod Ltd | Chemical compounds |
| US4639338A (en) * | 1984-08-06 | 1987-01-27 | Ciba-Geigy Corporation | Preparation of crystalline disodium 3-amino-1-hydroxypropane-1,1-diphosphonate pentahydrate |
| EP0243890A3 (en) * | 1986-04-30 | 1988-08-03 | EASTMAN KODAK COMPANY (a New Jersey corporation) | Novel diol monomers and polymers thereof |
| US5270431A (en) * | 1987-07-23 | 1993-12-14 | Basf Aktiengesellschaft | Preparation of oligomeric or polymeric radiation-reactive intermediates for solvent-structured layers |
| US4877603A (en) * | 1987-12-18 | 1989-10-31 | The Procter & Gamble Company | Oral compositions |
| AU618772B2 (en) * | 1987-12-30 | 1992-01-09 | Minnesota Mining And Manufacturing Company | Photocurable ionomer cement systems |
| US4877401A (en) * | 1988-03-09 | 1989-10-31 | University Of Utah | Method of preventing tooth decay by laser beam irradiation and chemical treatment |
| US5260483A (en) * | 1988-03-29 | 1993-11-09 | Drexel University | Preparation of n-aryl amides from isocyanates |
| US5258067A (en) * | 1988-06-25 | 1993-11-02 | Bayer Aktiengesellschaft | Liquid for conditioning tooth or bone substance |
| TW198039B (enExample) * | 1988-11-28 | 1993-01-11 | Ciba Geigy Ag | |
| US5015180A (en) * | 1989-03-01 | 1991-05-14 | Minnesota Mining And Manufacturing Company | Dental article containing light-curable paste |
| US5204426A (en) * | 1989-04-27 | 1993-04-20 | National Research Development Corporation | Command-curable composition |
| DE69022941T2 (de) * | 1989-08-24 | 1996-05-15 | Fukui Gyomo K K | Hitzehärtbare flüssige (meth)acrylate Harze und Zusammenfassungen, die diesen enthalten. |
| US5019651A (en) * | 1990-06-20 | 1991-05-28 | Merck & Co., Inc. | Process for preparing 4-amino-1-hydroxybutylidene-1,1-bisphosphonic acid (ABP) or salts thereof |
| US5096699A (en) * | 1990-12-20 | 1992-03-17 | Colgate-Palmolive Company | Anticalculus oral compositions |
| US5208009A (en) * | 1990-12-20 | 1993-05-04 | Colgate-Palmolive Company | Anticalculus oral compositions |
| US5218070A (en) * | 1991-02-11 | 1993-06-08 | Dentsply G.M.B.H. | Dental/medical composition and use |
| US5332429A (en) * | 1991-05-31 | 1994-07-26 | Minnesota Mining And Manufacturing Company | Method for treating fluoroaluminosilicate glass |
| US5354199A (en) * | 1991-08-02 | 1994-10-11 | Minnesota Mining And Manufacturing Company | Adhesive for packaged orthodontic appliance |
| JP2686684B2 (ja) * | 1991-08-27 | 1997-12-08 | 寅雄 大塚 | 水酸化アパタイトを充填し生体内溶解性繊維により編機されたチューブ網編成物 |
| US5270365A (en) * | 1991-12-17 | 1993-12-14 | Merck & Co., Inc. | Prevention and treatment of periodontal disease with alendronate |
| US5525648A (en) * | 1991-12-31 | 1996-06-11 | Minnesota Mining And Manufacturing Company | Method for adhering to hard tissue |
| JPH06298779A (ja) * | 1993-04-15 | 1994-10-25 | Hoechst Japan Ltd | ヘテロ環イミノビスメチレンビスホスホン酸誘導体 |
| US5451401A (en) * | 1993-09-29 | 1995-09-19 | The Procter & Gamble Company | Diphosphonic acid esters as tartar control agents |
| US5547379A (en) * | 1994-10-06 | 1996-08-20 | Hasel; Robert W. | Method of restoring a tooth |
| US5652227A (en) * | 1995-01-30 | 1997-07-29 | Teronen; Olli Pekka | Inhibition of the degradation of connective tissue matrix protein components in mammals |
| US6126922A (en) * | 1995-11-17 | 2000-10-03 | 3M Innovative Properties Company | Fluorid-releasing compositions and compositions with improved rheology |
| US6391286B1 (en) * | 1995-11-17 | 2002-05-21 | 3M Innovative Properties Company | Use of metallofluorocomplexes for dental compositions |
| JP4213207B2 (ja) * | 1995-11-17 | 2009-01-21 | スリーエム カンパニー | フッ化物を遊離する組成物 |
| JP2001521501A (ja) * | 1997-04-02 | 2001-11-06 | 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 | 歯科用修復材料および歯の修復方法 |
| US6506816B1 (en) * | 1997-07-17 | 2003-01-14 | 3M Innovative Properties Company | Dental resin cements having improved handling properties |
-
1999
- 1999-05-18 US US09/314,489 patent/US6143919A/en not_active Expired - Lifetime
-
2000
- 2000-03-29 EP EP00919805A patent/EP1185573B1/en not_active Expired - Lifetime
- 2000-03-29 JP JP2000618359A patent/JP2002544290A/ja not_active Withdrawn
- 2000-03-29 WO PCT/US2000/008319 patent/WO2000069944A1/en not_active Ceased
- 2000-03-29 AU AU40427/00A patent/AU4042700A/en not_active Abandoned
- 2000-03-29 CA CA002371572A patent/CA2371572A1/en not_active Abandoned
- 2000-03-29 DE DE60005183T patent/DE60005183T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US6143919A (en) | 2000-11-07 |
| EP1185573B1 (en) | 2003-09-10 |
| AU4042700A (en) | 2000-12-05 |
| DE60005183D1 (de) | 2003-10-16 |
| JP2002544290A (ja) | 2002-12-24 |
| CA2371572A1 (en) | 2000-11-23 |
| WO2000069944A1 (en) | 2000-11-23 |
| EP1185573A1 (en) | 2002-03-13 |
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| 8364 | No opposition during term of opposition |