JP4629339B2 - 重合可能な還元剤を含有する組成物、キット、および方法 - Google Patents
重合可能な還元剤を含有する組成物、キット、および方法 Download PDFInfo
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- JP4629339B2 JP4629339B2 JP2003558095A JP2003558095A JP4629339B2 JP 4629339 B2 JP4629339 B2 JP 4629339B2 JP 2003558095 A JP2003558095 A JP 2003558095A JP 2003558095 A JP2003558095 A JP 2003558095A JP 4629339 B2 JP4629339 B2 JP 4629339B2
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- acid
- reducing agent
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 150000000996 L-ascorbic acids Chemical class 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- GMEHFXXZSWDEDB-UHFFFAOYSA-N N-ethylthiourea Chemical compound CCNC(N)=S GMEHFXXZSWDEDB-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
- MNOILHPDHOHILI-UHFFFAOYSA-N Tetramethylthiourea Chemical compound CN(C)C(=S)N(C)C MNOILHPDHOHILI-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- 238000012724 UV-induced polymerization Methods 0.000 description 1
- ASFHYIAIHXYBEN-UHFFFAOYSA-N [2-(2-methylprop-2-enoyloxy)-3-phosphonooxypropyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(COP(O)(O)=O)OC(=O)C(C)=C ASFHYIAIHXYBEN-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940091181 aconitic acid Drugs 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 229960001748 allylthiourea Drugs 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229940009827 aluminum acetate Drugs 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000007656 barbituric acids Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000002902 bimodal effect Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000005385 borate glass Substances 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 230000000248 cariostatic effect Effects 0.000 description 1
- VZDYWEUILIUIDF-UHFFFAOYSA-J cerium(4+);disulfate Chemical compound [Ce+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VZDYWEUILIUIDF-UHFFFAOYSA-J 0.000 description 1
- 229910000355 cerium(IV) sulfate Inorganic materials 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 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
- 229940018557 citraconic acid Drugs 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- 239000011350 dental composite resin Substances 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000012955 diaryliodonium Substances 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 235000021463 dry cake Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000007496 glass forming Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000037427 ion transport Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 229910000358 iron sulfate Inorganic materials 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012633 leachable Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 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
- 239000003550 marker Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- HNEGQIOMVPPMNR-NSCUHMNNSA-N mesaconic acid Chemical compound OC(=O)C(/C)=C/C(O)=O HNEGQIOMVPPMNR-NSCUHMNNSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000000051 modifying effect Effects 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000005365 phosphate glass Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001444 polymaleic acid Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- IEKWPPTXWFKANS-UHFFFAOYSA-K trichlorocobalt Chemical compound Cl[Co](Cl)Cl IEKWPPTXWFKANS-UHFFFAOYSA-K 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/10—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
-
- 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
-
- 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
-
- 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
- A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61K6/893—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
- C08F290/14—Polymers provided for in subclass C08G
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dental Preparations (AREA)
- Polymerization Catalysts (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
樹脂システムの成分は、硬化性組成物のその他の成分と混和性であるように選択される。すなわち好ましくは、樹脂システムの成分は、少なくとも十分に混和性であるので、組成物のその他の成分(例えば還元剤および酸化剤)と組み合わせたときに、実質的な(substantial)量の沈降を起こさない。好ましくは樹脂システムの成分は、水と混和性である。樹脂システムの成分は、モノマー、オリゴマー、ポリマー、またはそれらの組み合わせであることができる。
本発明の硬化性組成物は、充填材も含有できる。充填材は、歯科用修復組成物中で現在使用されている充填材など、医用または歯科用用途で使用される組成物への組み込みに適切な、1つ以上の種々多様な材料から選択しても良い。充填材は好ましくは微細である。充填材は、単峰性(unimodial)または多峰性(polymodial)(例えば二峰性の(bimodal))粒度分布を有することができる。好ましくは充填材の最大粒度(粒子の最大寸法、典型的に直径)は、約10μm未満、そしてより好ましくは約2.0μm未満である。好ましくは充填材の平均粒度は約3.0μm未満、そしてより好ましくは約0.6μm未満である。
還元および酸化剤は、都合良く一緒に考察される。それらは相互に反応し、あるいは別のやり方で協力して、樹脂システム(例えばエチレン性不飽和成分)の重合を開始できるフリーラジカルを生じるべきである。このタイプの硬化は暗反応で、すなわちそれは光の存在に依存せず、光不在下で進行できる。還元および酸化剤は、好ましくは十分に保存安定性があって望ましくないカラー化がなく、典型的歯科用条件下での保存と使用を可能にする。それらは樹脂システムと十分に混和性(そして好ましくは水溶性)であって、硬化性組成物のその他の成分中への容易な溶解を可能にする(そしてそれからの分離を阻止する)べきである。好ましくは本発明の還元剤は、室温で少なくとも約2重量%の水への溶解度を有する。
硬化性組成物には光重合開始剤も添加できるが、必要ではない。光重合開始剤は、適切な波長と強度の光への曝露時に、エチレン性不飽和成分のフリーラジカル架橋を促進できるべきである。それはまた好ましくは、十分に保存安定性があって望ましくない着色を含まず、典型的な歯科用条件下での保存と使用を可能にする。可視光光重合開始剤が好ましい。光重合開始剤は好ましくは樹脂システムと混和性であり、より好ましくは水溶性または水混和性である。極性基を持つ光重合開始剤は、通常十分な程度の水溶性または水混和性を有する。光重合開始剤は頻繁に単独で使用できるが、典型的に適切な供与体化合物または適切な促進剤(例えばアミン、ペルオキシド、リン化合物、ケトンおよびα−ジケトン化合物)と組み合わせて使用される。
本発明の組成物は、特に酸官能性成分が含まれる場合、好ましくは水を含有する。水は販売形態の製品中に存在でき、または歯科医によって使用直前に添加でき、または口内の水との接触の結果含まれることができる。水は、蒸留、脱イオン、または普通の水道水であることができる。概して脱イオン水が好ましい。
本発明の組成物は、凝固反応中および組成物硬化後の双方において、硬化性組成物中の特性の適度なバランスを提供するように調節される。これらの特性としては、硬化性組成物の成分の保存安定性に並んで、硬化した組成物の色安定性、毒性、および反応時間(「スナップセット」)が挙げられる。例えば硬化性組成物は歯科用用途のためには、好ましくは約2分間以下のスナップセットを有するべきである。組成物の全工作時間または硬化時間(すなわち口腔内に類似した湿度と温度条件下で、硬化性樹脂が液体またはペースト状態から固形材料に硬化する時間)は、好ましくは約6分未満、そしてより好ましくは約4分未満である。
AA:ITA :ミトラ(Mitra)の(特許文献8)の実施例3に従って調製された、モル比4:1のアクリル酸:イタコン酸からできたコポリマー。MW(平均)=106,000、多分散性ρ=4.64。
AA:IA:IEM :(特許文献8)実施例11の乾燥ポリマーの調製に従って、AA:ITAコポリマーと、コポリマーの酸性基の16モル%をペンダントのメタクリレート基に転換するのに十分な2−イソシアナトエチルメタクリレートとを反応させてできるポリマー。
AHTU:ミズーリ州セントルイスのシグマ・アルドリッチからの(Sigma−Aldrich(St.Louis,MO))1−アリル−3−(2−ヒドロキシエチル)−2−チオ尿素。
ATU:シグマ・アルドリッチ(Sigma−Aldrich)からのアリルチオ尿素。
BHT:ニュージャージー州フォーズのPCMスペシャリティズ(PMC Specialties(Fords,NJ))からのブチル化ヒドロキシトルエン。
ビスGMA:2,2−ビス[4−(2−ヒドロキシ−3−メタクリロイルオキシプロポキシ)フェニル]プロパン(CAS No.1565−94−2)。
GDMA:ドイツ国ダルムシュタットのローム・アンド・テック(Rhom and Tech,Inc.(Darmstadt,Germany))からのグリセリルジメタクリレート。
HEMA:ローム・アンド・テック(Rhom and Tech,Inc.)からの2−ヒドロキシエチルメタクリレート。150ppmの4−メトキシフェノールを阻害剤として含有する。
IEM:シグマ・アルドリッチ(Sigma−Aldrich)からの2−イソシアナトエチルメタクリレート。
KPS:シグマ・アルドリッチ(Sigma−Aldrich)からの過硫酸カリウム。
FG−KPS:シグマ・アルドリッチ(Sigma−Aldrich)からの細かく粉砕された過硫酸カリウム。
MEC−KPS:(特許文献8)の実施例3に従って調製された、マイクロカプセル化された過硫酸カリウム。
TBDMA:シグマ・アルドリッチ(Sigma−Aldrich)からの4−tert−ブチルジメチルアニリン。
FAS I:ミトラ(Mitraら)の(特許文献7)実施例1の「制御ガラス」のようなフルオロアルミナシリケート(FAS)ガラス粉末(ただし、表面積2.8m2/gを有する)を液体処理溶液でシラン処理した。処理溶液は、コネチカット州グリニッチのCKウィトコ(CK Witco Corp.(Greenwich,CT))からのA174γ−メタクリロキシプロピルトリメトキシシラン4部と水40部を合わせ、氷酢酸を添加してpH3.01を得て、0.5時間撹拌して調製した。得られた透明処理溶液を100部のガラス粉末と、さらに67部の水に混合し、スラリーを得た。5%水酸化アンモニウムを添加して、スラリーのpHを7.0に調節した。さらに30分間撹拌した後、混合物をデラウェア州ウィルミントンのデュポン(DuPont(Wilmington,DE))からのテフロン(TEFLON)ポリテトラフルオロエチレンで被覆されたトレーに注ぎ95℃で24時間乾燥させた。得られた乾燥ケーキを60−μmのふるいに通過させて粉砕した。
FAS II:乾燥ケーキを74μmふるいに通過させて、FAS I類似のFASガラスを調製した。
FAS III:(特許文献7)実施例1の「制御ガラス」を表面積84m2/gに磨砕して、液体処理溶液でシラン処理した。8部のA174γ−メタクリロキシプロピルトリメトキシシランを使用したこと以外は、シラン処理とそれに続く乾燥ガラスを分離する過程は、FAS Iについて述べたように実施した。得られた乾燥ケーキを74μmふるいに通過させて粉砕した。
FAS IV:FAS IVはFAS Iに類似しているがシラン処理がない。
FAS V:FAS IIとFAS IVとの50/50配合物。
FAS VI:ショット(Schott)ガラス(製品番号G 018−117、ドイツ国ランツフートのショット・ガラス・エキスポート(Schott Glas Export GmbH)(Landshut,Germany))をFAS IIIについて述べたようにシラン処理した。
Zr−Si充填材:ランドクレブ(Randklev)の(特許文献5)に述べられるようにして、放射線不透過性ジルコニア−シリカ(Zr−Si)充填材を調製した。
圧縮強さ(CS):最初に混合セメントサンプルを4mmの内径を有するガラス管に注入して、圧縮強さを評価した。ガラス管の両端をシリコーンプラグで塞いだ。充填した管に0.275MPaの圧力を5分間かけて、37℃で90%を超える相対湿度(RH)のチャンバーに入れて1時間静置した。次に硬化したサンプルを37℃の水に1日間入れてから8mmの長さに切断した。クロスヘッド速度1mm/分で作動する、マサチューセッツ州カントンのインストロン(Instron Corp.(Canton,MA))からのインストロン(INSTRON)万能試験機を使用して、ISO基準7489に従って圧縮強さを測定した。
液体樹脂A:AA:ITA(14.4部)、AA:ITA:IEM(35.6部)、HEMA(17.1部)、水(32.9部)、およびBHT(0.06部)を混合して、液体樹脂Aを作った。得られた硬化性樹脂の溶液を液体樹脂Aと命名した。
酸化剤との種々の組み合わせで異なる還元剤を調合し、硬化性樹脂への薬剤の添加に続くゲル化時間を評価して、ゲル化調査を実施し、異なる重合可能な還元剤システムの有効性を判定した。具体的には種々の還元剤をKPS酸化剤と組み合わせ、次に室温で5〜10秒間撹拌しながら液体樹脂Aに添加した。混合薬剤を樹脂に添加した時点から混合物が液体から粘稠なゲルに転換するまでのゲル化時間を測定した。成分使用量、ゲル化時間、およびゲル外観を表1に示す。
硬化時間調査を実施して、酸化剤および異なるフルオロアルミナシリケート(FAS)ガラス充填材との種々の組み合わせにおける重合可能な還元剤の有効性を判定した。エチレン性不飽和カルボン酸のポリマーを含有する硬化性樹脂への薬剤および充填材の添加に続いて硬化時間を測定した。エチレン性不飽和カルボン酸のポリマー、FASガラス充填材、および水を含有するこのような硬化性システムは、ガラスイオノマーセメントとして一般に知られている。具体的には、(様々な量の酸化剤FG−KPSを含有する)FASガラス充填材と、(様々な量の重合可能な還元剤ATUを含有する)液体樹脂Aとを室温で15〜30秒間ヘラで混合して組み合わせた。硬化時間をここで述べた試験方法に従って求めた。成分の使用量および硬化時間を表2に示す。
液体樹脂A(2%のATU添加)を37℃および90%のRHでそれぞれ1週間、2週間、4週間、および8週間エージングさせたこと以外は、実施例5Dで述べたようにして硬化性樹脂(実施例7〜10)を調製した。成分の混合および引き続く硬化に続いて、ここで述べた試験方法に従って、得られた固形樹脂をエナメル接着(EA)、圧縮強さ(CS)、および直径引張強さ(DTS)について評価した。結果を表3に示す。
重合可能な還元剤ATUを最初に液体樹脂Aでなく充填材に添加したこと以外は、実施例3〜6に類似したやり方で、充填材(粉末)/液体組成物を配合した。具体的には充填材は、FAS V(4.65部)、MEC−KPS(0.5部)、およびATU(0.2部)から成った。充填材を2.5:1の比率で液体樹脂Aに添加し、得られた硬化時間は2分5秒であった。ここで述べた試験方法に従って、物理的特性を求めたところ次のようであった。CSは115MPa、DTSは22.1MPa、そしてEA(調節なし)は6.08MPa。
ペースト75A(1.4g)とペースト75B(1.0g)をヘラを使用して25秒間混合して、ペースト/ペースト組成物(ガラスイオノマーセメントシステム)を配合し、硬化後に硬化した樹脂セメント(実施例12)を得た。同様にペースト77A(1.7g)とペースト77B(1.0g)とを混合して、硬化後に硬化した樹脂セメント(実施例13)を得た。ペースト75A/77Aおよびペースト75B/77Bの成分は、それぞれ表4および表5に示される。硬化した樹脂セメントの硬化時間、工作時間、および種々の物理的特性をここで述べる試験方法に従って求め、表6に結果を示す。
AHTU(8.01g、0.05モル)を丸底フラスコ内の乾燥THF(100ml)に溶解し、ジブチルスズジラウレート(0.20ml、シグマ・アルドリッチ(Sigma−Aldrich))を添加した。ドライライト(DRIERITE)乾燥剤を含有する乾燥管で栓をした還流冷却器にフラスコを取り付けた。IEM(7.75g、0.05モル)を室温で10分間にわたり滴下して添加した。次に反応混合物を40℃で15時間撹拌した。フラスコの加熱を止めて、ロータリーエバポレータで溶剤を除去して無色の粘稠な液体を得た。生成物の赤外線特性決定は、メタクリレート化AHTU(M−AHTU)化学構造に一致した。
Claims (3)
- エチレン性不飽和成分を含む硬化性樹脂、
式、
酸化剤を含む、硬化性組成物。 - 式
- 二次還元剤をさらに含む請求項1に記載の硬化性組成物であって、前記二次還元剤が三級アミンである、硬化性組成物。
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-
2002
- 2002-12-18 JP JP2003558095A patent/JP4629339B2/ja not_active Expired - Fee Related
- 2002-12-18 CA CA2471877A patent/CA2471877C/en not_active Expired - Fee Related
- 2002-12-18 EP EP02795950A patent/EP1458831B1/en not_active Expired - Lifetime
- 2002-12-18 AU AU2002360672A patent/AU2002360672B2/en not_active Ceased
- 2002-12-18 CN CNB028264959A patent/CN100558775C/zh not_active Expired - Fee Related
- 2002-12-18 WO PCT/US2002/040682 patent/WO2003057792A2/en active Application Filing
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2006
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Also Published As
Publication number | Publication date |
---|---|
CA2471877A1 (en) | 2003-07-17 |
AU2002360672A1 (en) | 2003-07-24 |
WO2003057792A3 (en) | 2004-04-01 |
US20070088096A1 (en) | 2007-04-19 |
CA2471877C (en) | 2011-03-08 |
EP1458831A2 (en) | 2004-09-22 |
JP2005514490A (ja) | 2005-05-19 |
EP1458831B1 (en) | 2011-11-23 |
US7541393B2 (en) | 2009-06-02 |
WO2003057792A2 (en) | 2003-07-17 |
AU2002360672B2 (en) | 2008-05-01 |
CN1610732A (zh) | 2005-04-27 |
CN100558775C (zh) | 2009-11-11 |
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