JP5128748B2 - ホスホン酸含有歯科材料 - Google Patents
ホスホン酸含有歯科材料 Download PDFInfo
- Publication number
- JP5128748B2 JP5128748B2 JP2002506680A JP2002506680A JP5128748B2 JP 5128748 B2 JP5128748 B2 JP 5128748B2 JP 2002506680 A JP2002506680 A JP 2002506680A JP 2002506680 A JP2002506680 A JP 2002506680A JP 5128748 B2 JP5128748 B2 JP 5128748B2
- Authority
- JP
- Japan
- Prior art keywords
- dental material
- material according
- phosphonic acid
- aryl
- 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 - Fee Related
Links
- 239000005548 dental material Substances 0.000 title claims abstract description 30
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 title claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 150000003009 phosphonic acids Chemical class 0.000 claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- -1 alkaline earth metal salt Chemical class 0.000 claims description 6
- 239000004568 cement Substances 0.000 claims description 6
- 239000002521 compomer Substances 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 150000002500 ions Chemical group 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 6
- 239000004721 Polyphenylene oxide Substances 0.000 abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 229920000570 polyether Polymers 0.000 abstract description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052796 boron Inorganic materials 0.000 abstract description 3
- 229910003849 O-Si Inorganic materials 0.000 abstract description 2
- 229910003872 O—Si Inorganic materials 0.000 abstract description 2
- 125000002947 alkylene group Chemical group 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 17
- 239000000203 mixture Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 210000004268 dentin Anatomy 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000004809 Teflon Substances 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000011350 dental composite resin Substances 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 210000004283 incisor Anatomy 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- DSAYAFZWRDYBQY-UHFFFAOYSA-N 2,5-dimethylhexa-1,5-diene Chemical compound CC(=C)CCC(C)=C DSAYAFZWRDYBQY-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- OELQSSWXRGADDE-UHFFFAOYSA-N 2-methylprop-2-eneperoxoic acid Chemical compound CC(=C)C(=O)OO OELQSSWXRGADDE-UHFFFAOYSA-N 0.000 description 1
- 125000006058 4-methyl-4-pentenyl group Chemical group 0.000 description 1
- MNDPGMGRNPDFCC-UHFFFAOYSA-N 5-bromo-2-methylpent-1-ene Chemical compound CC(=C)CCCBr MNDPGMGRNPDFCC-UHFFFAOYSA-N 0.000 description 1
- UNXURIHDFUQNOC-UHFFFAOYSA-N 5-bromo-2-methylpent-2-ene Chemical compound CC(C)=CCCBr UNXURIHDFUQNOC-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 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
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- XQRLCLUYWUNEEH-UHFFFAOYSA-L diphosphonate(2-) Chemical compound [O-]P(=O)OP([O-])=O XQRLCLUYWUNEEH-UHFFFAOYSA-L 0.000 description 1
- GTZOYNFRVVHLDZ-UHFFFAOYSA-N dodecane-1,1-diol Chemical compound CCCCCCCCCCCC(O)O GTZOYNFRVVHLDZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- MTCMFVTVXAOHNQ-UHFFFAOYSA-N ethyl 2-(bromomethyl)prop-2-enoate Chemical compound CCOC(=O)C(=C)CBr MTCMFVTVXAOHNQ-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003178 glass ionomer cement Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3826—Acyclic unsaturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3821—Acyclic saturated acids which can have further substituents on alkyl substituted by B, Si, P or a metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Dental Preparations (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00114527A EP1169996A1 (de) | 2000-07-06 | 2000-07-06 | Phosphonsäuren enthaltendes Dentalmaterial |
| EP00114527.5 | 2000-07-06 | ||
| PCT/EP2001/007602 WO2002002057A1 (de) | 2000-07-06 | 2001-07-03 | Phosphonsäuren enthaltendes dentalmaterial |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012196901A Division JP5681848B2 (ja) | 2000-07-06 | 2012-09-07 | ホスホン酸含有歯科材料 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004501940A JP2004501940A (ja) | 2004-01-22 |
| JP2004501940A5 JP2004501940A5 (OSRAM) | 2008-05-22 |
| JP5128748B2 true JP5128748B2 (ja) | 2013-01-23 |
Family
ID=8169179
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002506680A Expired - Fee Related JP5128748B2 (ja) | 2000-07-06 | 2001-07-03 | ホスホン酸含有歯科材料 |
| JP2012196901A Expired - Fee Related JP5681848B2 (ja) | 2000-07-06 | 2012-09-07 | ホスホン酸含有歯科材料 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012196901A Expired - Fee Related JP5681848B2 (ja) | 2000-07-06 | 2012-09-07 | ホスホン酸含有歯科材料 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6902608B2 (OSRAM) |
| EP (2) | EP1169996A1 (OSRAM) |
| JP (2) | JP5128748B2 (OSRAM) |
| DE (1) | DE50107506D1 (OSRAM) |
| WO (1) | WO2002002057A1 (OSRAM) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4269010B2 (ja) * | 2001-07-09 | 2009-05-27 | 学校法人日本大学 | 歯科用セルフエッチングプライマー処理剤 |
| ATE348590T1 (de) | 2001-08-10 | 2007-01-15 | Dentsply Int Inc | Einteiliges selbstgrundierendes dentales haftmittel |
| US20040266906A1 (en) * | 2001-10-26 | 2004-12-30 | Joachim Klee | Hydrolysis stable self-etching,self-priming adhesive |
| FR2833266B1 (fr) | 2001-12-11 | 2004-10-22 | Mayoly Spindler Lab | Nouveaux derives phosphonates, leur procede de preparation, leur utilisation comme modulateurs de l'activite des lymphocytes tgamma9 delta2 |
| DE10206451A1 (de) | 2002-02-15 | 2003-08-28 | Dentsply Detrey Gmbh | Dentalkleber-Zusammensetzung |
| DE10234326B3 (de) * | 2002-07-26 | 2004-02-05 | Ivoclar Vivadent Ag | Dentalmaterialien auf der Basis von Acrylesterphosphonsäuren |
| US6900251B2 (en) | 2002-06-26 | 2005-05-31 | Ivoclar Vivadent Ag | Dental materials based on acrylic-ester phosphonic acids |
| DE10242106A1 (de) * | 2002-09-11 | 2004-04-15 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Phosphorgruppenhaltige Carbonsäurederivate mit organisch polymerisierbaren Gruppen |
| US20040206932A1 (en) * | 2002-12-30 | 2004-10-21 | Abuelyaman Ahmed S. | Compositions including polymerizable bisphosphonic acids and methods |
| EP1454911A1 (en) * | 2003-03-07 | 2004-09-08 | DENTSPLY DETREY GmbH | A polymerizable phosphoric acid ester derivative and a dental composition employing it |
| CA2535556C (en) | 2003-08-12 | 2014-01-07 | 3M Innovative Properties Company | Self-etching dental compositions and methods |
| ATE357450T1 (de) * | 2003-12-23 | 2007-04-15 | Dentsply Detrey Gmbh | In einem selbstätzendes, selbstgrundierendes dentales haftmittel |
| US9943465B2 (en) | 2006-12-13 | 2018-04-17 | 3M Innovative Properties Company | Methods of using a dental composition having an acidic component and a photobleachable dye |
| JP5362196B2 (ja) * | 2007-08-13 | 2013-12-11 | 株式会社松風 | 重合性ホスホン酸誘導体およびそれを含有する接着性組成物 |
| US7963769B2 (en) * | 2007-10-08 | 2011-06-21 | Kerr Corporation | Dental adhesive and method of use |
| US7946850B2 (en) | 2008-08-13 | 2011-05-24 | Kerr Corporation | Single-part, light-curable, self-adhering dental restorative composition and method of using the same |
| US8895775B2 (en) * | 2009-10-30 | 2014-11-25 | Rhodia Operations | Method for preparing conjugated diene phosphonate compounds |
| KR20120091252A (ko) * | 2009-10-30 | 2012-08-17 | 로디아 차이나 컴퍼니, 리미티드 | 공액 디엔 포스피네이트 화합물, 그의 제조 방법 및 용도 |
| US9120917B2 (en) | 2009-10-30 | 2015-09-01 | Solvay China Co., Ltd. | N-substituted acrylamides, preparation method and use thereof |
| WO2012145924A1 (en) * | 2011-04-29 | 2012-11-01 | Rhodia (China) Co., Ltd. | New coupling agents for elastomer compositions |
| ES2710891T3 (es) | 2011-12-06 | 2019-04-29 | Ivoclar Vivadent Ag | Materiales dentales a base de ácidos bisfosfónicos polimerizables fuertemente ácidos |
| EP2816049B8 (de) | 2013-06-20 | 2018-07-11 | Ivoclar Vivadent AG | ß-Ketophosphonsäuren und Dentalmateriallen auf deren Basis |
| CN106029044B (zh) * | 2014-02-18 | 2019-12-31 | 3M创新有限公司 | 粘合剂粘结组合物及其用途 |
| ES2721026T3 (es) | 2015-07-22 | 2019-07-26 | Ivoclar Vivadent Ag | Materiales dentales adhesivos con polímeros adhesivos muy ácidos |
| DE102015112602A1 (de) | 2015-07-31 | 2017-02-02 | Heraeus Kulzer Gmbh | Vernetzende Monomere mit mindestens einem Schwefelatom |
| DE102015217418A1 (de) * | 2015-09-11 | 2017-03-16 | Mühlbauer Technology Gmbh | Radikalisch polymerisierbares Dentalmaterial |
| EP3225228B1 (en) * | 2016-03-31 | 2018-06-13 | Ivoclar Vivadent AG | Acidic hybrid monomers and dental materials based thereon |
| EP3308765B1 (de) | 2016-10-17 | 2022-07-13 | Mühlbauer Technology GmbH | Radikalisch polymerisierbare verbindung |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE273846C (OSRAM) * | ||||
| US4272512A (en) * | 1980-01-31 | 1981-06-09 | Colgate-Palmolive Company | Antigingivitis composition |
| US4650847A (en) * | 1981-07-29 | 1987-03-17 | Kuraray Co., Ltd. | Adhesive composition |
| US4526728A (en) * | 1982-03-24 | 1985-07-02 | Hoechst Aktiengesellschaft | 2-Acrylamido- and 2-methacrylamido-2-methyl propanephosphonic acids and their salts, process for the preparation thereof, and use thereof for the manufacture of copolymers |
| DE3210775A1 (de) * | 1982-03-24 | 1983-09-29 | Hoechst Ag, 6230 Frankfurt | 2-acrylamido-2-methyl-propanphosphonsaeure und ihre salze, verfahren zu deren herstellung und ihre verwendung zur herstellung von copolymeren |
| JPS60197609A (ja) * | 1984-03-16 | 1985-10-07 | Kuraray Co Ltd | 歯科用組成物 |
| JP3658719B2 (ja) * | 1997-07-04 | 2005-06-08 | カシオ計算機株式会社 | 楽音発生装置 |
| DE19746708C2 (de) * | 1997-10-16 | 2000-02-17 | Ivoclar Ag Schaan | Hydrolysestabile und polymerisierbare Acrylphosphonsäuren |
| US6172131B1 (en) * | 1997-10-16 | 2001-01-09 | Ivoclar Ag | Hydrolysis-stable and polymerizable acrylphosphonic acids |
| DE19918974A1 (de) * | 1998-06-09 | 1999-12-16 | Degussa | Dentalwerkstoff mit polymerisierbaren Phosphonsäuren |
-
2000
- 2000-07-06 EP EP00114527A patent/EP1169996A1/de not_active Withdrawn
-
2001
- 2001-07-03 DE DE50107506T patent/DE50107506D1/de not_active Expired - Lifetime
- 2001-07-03 WO PCT/EP2001/007602 patent/WO2002002057A1/de not_active Ceased
- 2001-07-03 JP JP2002506680A patent/JP5128748B2/ja not_active Expired - Fee Related
- 2001-07-03 EP EP01957913A patent/EP1296634B1/de not_active Expired - Lifetime
- 2001-07-03 US US10/332,344 patent/US6902608B2/en not_active Expired - Lifetime
-
2012
- 2012-09-07 JP JP2012196901A patent/JP5681848B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004501940A (ja) | 2004-01-22 |
| EP1169996A1 (de) | 2002-01-09 |
| US6902608B2 (en) | 2005-06-07 |
| JP2013010784A (ja) | 2013-01-17 |
| WO2002002057A1 (de) | 2002-01-10 |
| EP1296634B1 (de) | 2005-09-21 |
| JP5681848B2 (ja) | 2015-03-11 |
| US20030167968A1 (en) | 2003-09-11 |
| EP1296634A1 (de) | 2003-04-02 |
| DE50107506D1 (de) | 2006-02-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5128748B2 (ja) | ホスホン酸含有歯科材料 | |
| Moszner et al. | Monomers for adhesive polymers, 2. Synthesis and radical polymerisation of hydrolytically stable acrylic phosphonic acids | |
| EP0115948B1 (en) | Adhesive composition | |
| CN1917845B (zh) | 单组份型牙科用粘接剂组合物 | |
| US5304585A (en) | Dentin and enamel adhesive | |
| EP0074708B1 (en) | Adhesive composition | |
| JP5630999B2 (ja) | 歯科用接着剤組成物 | |
| JP3154978B2 (ja) | 加水分解安定で重合可能なアクリルホスホン酸 | |
| EP0321683B1 (en) | Adhesive composition which bonds to collagen and calcium | |
| CN106535862B (zh) | 具有可控的网状结构的复合材料 | |
| WO2008047547A1 (fr) | Nouveau composé, composition le comprenant et procédé de fabrication d'un amide polymérisable | |
| JP2005517719A (ja) | 歯科用接着性組成物 | |
| AU2010300458A1 (en) | Novel multifunctional molecules for dental bonding applications having improved adhesion | |
| JP6995357B2 (ja) | 高誘電率を有する官能基を有する酸性基含有重合性単量体 | |
| JP3616346B2 (ja) | 加水分解安定性である重合可能なアクリロホスホン酸 | |
| JPH0825854B2 (ja) | 歯科用セメント | |
| TW200843797A (en) | Polymerizable monomer, polymerizable composition and dental material | |
| JP2865794B2 (ja) | 接着剤組成物 | |
| US4855475A (en) | (Meth)acrylic esters of phosphoric acid ester dihalides | |
| JP6615000B2 (ja) | 歯科用接着性組成物 | |
| JPH0372115B2 (OSRAM) | ||
| JP3612287B2 (ja) | 加水分解に安定であり、重合可能なアクリロホスホン酸モノエステル | |
| JP7090884B2 (ja) | 高誘電率を有する官能基を有する酸性基含有重合性単量体 | |
| US4028358A (en) | 6-Fluoro-9-perfluorobutyl purine | |
| JP5008852B2 (ja) | トリシクロデカン誘導体の異性体混合物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080403 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080403 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110726 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20111026 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20111122 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20120221 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20120228 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20120321 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20120328 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20120508 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120907 |
|
| A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20120924 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20121009 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20121101 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 5128748 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20151109 Year of fee payment: 3 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |