CN1073961A - With metal filled cementing compositions and method - Google Patents
With metal filled cementing compositions and method Download PDFInfo
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- CN1073961A CN1073961A CN92111811A CN92111811A CN1073961A CN 1073961 A CN1073961 A CN 1073961A CN 92111811 A CN92111811 A CN 92111811A CN 92111811 A CN92111811 A CN 92111811A CN 1073961 A CN1073961 A CN 1073961A
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- composition
- amalgam
- unsaturated compound
- compound
- tooth
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- 239000000203 mixture Substances 0.000 title claims abstract description 98
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 34
- 239000002184 metal Substances 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 229910000497 Amalgam Inorganic materials 0.000 claims abstract description 54
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 39
- 239000000126 substance Substances 0.000 claims abstract description 22
- 239000003351 stiffener Substances 0.000 claims abstract description 4
- -1 phosphorus compound Chemical class 0.000 claims description 16
- 239000011159 matrix material Substances 0.000 claims description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims description 12
- 230000026731 phosphorylation Effects 0.000 claims description 12
- 238000006366 phosphorylation reaction Methods 0.000 claims description 12
- 239000011574 phosphorus Substances 0.000 claims description 10
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- 239000002245 particle Substances 0.000 claims description 6
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- 239000000460 chlorine Substances 0.000 claims description 4
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
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- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
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- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
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- 238000006243 chemical reaction Methods 0.000 description 3
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- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- RIUQHCOQTXZANT-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCCCCO Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCCCCO RIUQHCOQTXZANT-UHFFFAOYSA-N 0.000 description 2
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- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 2
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- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 2
- 229920006223 adhesive resin Polymers 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
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- 230000035935 pregnancy Effects 0.000 description 2
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- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
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- 239000004575 stone Substances 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- OUOHOJDXEPUCDT-UHFFFAOYSA-N (2-ethylphenyl) prop-2-enoate Chemical compound CCC1=CC=CC=C1OC(=O)C=C OUOHOJDXEPUCDT-UHFFFAOYSA-N 0.000 description 1
- PQUXFUBNSYCQAL-UHFFFAOYSA-N 1-(2,3-difluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1F PQUXFUBNSYCQAL-UHFFFAOYSA-N 0.000 description 1
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 1
- RMCCONIRBZIDTH-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 1,3-dioxo-2-benzofuran-5-carboxylate Chemical compound CC(=C)C(=O)OCCOC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 RMCCONIRBZIDTH-UHFFFAOYSA-N 0.000 description 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YIUOAAUFVBZQPM-UHFFFAOYSA-N 2-methyl-1,3,5-triazine Chemical compound CC1=NC=NC=N1 YIUOAAUFVBZQPM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 240000004160 Capsicum annuum Species 0.000 description 1
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- WPGUUPJOAVPZBQ-UHFFFAOYSA-N [Cl].OP(O)(O)=O Chemical compound [Cl].OP(O)(O)=O WPGUUPJOAVPZBQ-UHFFFAOYSA-N 0.000 description 1
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- LGVWZIPWNLYURF-UHFFFAOYSA-N [decoxy(hydroxy)phosphoryl] prop-2-eneperoxoate Chemical compound C(C=C)(=O)OOP(OCCCCCCCCCC)(O)=O LGVWZIPWNLYURF-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000004523 agglutinating effect Effects 0.000 description 1
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
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- 239000004411 aluminium Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- 230000003078 antioxidant effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 238000005266 casting Methods 0.000 description 1
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- 210000000080 chela (arthropods) Anatomy 0.000 description 1
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- CVRPVRHBAOPDIG-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;2-(2-methylprop-2-enoyloxy)ethyl 1,3-dioxo-2-benzofuran-5-carboxylate Chemical compound COC(=O)C(C)=C.CC(=C)C(=O)OCCOC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 CVRPVRHBAOPDIG-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- NJPPVKZQTLUDBO-UHFFFAOYSA-N novaluron Chemical compound C1=C(Cl)C(OC(F)(F)C(OC(F)(F)F)F)=CC=C1NC(=O)NC(=O)C1=C(F)C=CC=C1F NJPPVKZQTLUDBO-UHFFFAOYSA-N 0.000 description 1
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- TWSRVQVEYJNFKQ-UHFFFAOYSA-N pentyl propanoate Chemical compound CCCCCOC(=O)CC TWSRVQVEYJNFKQ-UHFFFAOYSA-N 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
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- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- GBUDNGCDDQUCJV-UHFFFAOYSA-N prop-2-enoic acid;silver Chemical compound [Ag].OC(=O)C=C GBUDNGCDDQUCJV-UHFFFAOYSA-N 0.000 description 1
- SEZALEWRXURRKG-UHFFFAOYSA-N prop-2-enoic acid;zirconium Chemical compound [Zr].OC(=O)C=C SEZALEWRXURRKG-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- VJAUIANVVMMDII-UHFFFAOYSA-M sodium 2-(N-[2-hydroxy-3-(2-methylprop-2-enoyloxy)propyl]-4-methylanilino)acetate [4-[2-[4-(2-methylprop-2-enoyloxy)phenyl]propan-2-yl]phenyl] 2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C(=O)OCC(O)CN(CC([O-])=O)c1ccc(C)cc1.CC(=C)C(=O)Oc1ccc(cc1)C(C)(C)c1ccc(OC(=O)C(C)=C)cc1 VJAUIANVVMMDII-UHFFFAOYSA-M 0.000 description 1
- 229940047670 sodium acrylate Drugs 0.000 description 1
- MKWYFZFMAMBPQK-UHFFFAOYSA-J sodium feredetate Chemical compound [Na+].[Fe+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O MKWYFZFMAMBPQK-UHFFFAOYSA-J 0.000 description 1
- SRJQTHAZUNRMPR-UYQKXTDMSA-N spinosyn A Chemical compound O([C@H]1CCC[C@@H](OC(=O)C[C@H]2[C@@H]3C=C[C@@H]4C[C@H](C[C@H]4[C@@H]3C=C2C(=O)[C@@H]1C)O[C@H]1[C@@H]([C@H](OC)[C@@H](OC)[C@H](C)O1)OC)CC)[C@H]1CC[C@H](N(C)C)[C@@H](C)O1 SRJQTHAZUNRMPR-UYQKXTDMSA-N 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
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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
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- 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
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- 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
- A61K6/84—Preparations for artificial teeth, for filling teeth or for capping teeth comprising metals or alloys
- A61K6/847—Amalgams
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- Oral & Maxillofacial Surgery (AREA)
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- Public Health (AREA)
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Abstract
A kind of cementing compositions, comprising a kind of alkylene unsaturated compound, a kind of micropartical metal charge, and a kind of stiffening agent, also disclose simultaneously a kind of reconstituted substance of a kind of bonding, as amalgam, extremely as the method in the sclerous tissueses such as dentine or enamel, comprising using a kind of cementing compositions of the present invention as the middle layer between reconstituted substance and sclerous tissues.
Description
The invention relates to the cementing compositions that comprises a kind of alkylene unsaturated compound.In on the other hand, the invention relates to the cementing compositions that comprises a kind of micropartical metal filler.The present invention also is about the method for a kind of reconstituted substance to a kind of matrix that bond, and on the other hand, is about boning a kind of tooth reconstituted substance, as amalgam, to as the method in the sclerous tissueses such as dentine or enamel.
Tooth amalgam and reconstruction sets compound are widely used in inherent crown and external coronal and restore.Yet amalgam can not be bonded on the tooth structure, and the dentist must put the tooth cavity in order with dovetail and different slots in advance so that the amalgam mechanical type be fixed in the cavity in.Yet this type of arrangement but causes must digging the more tooth structure of cutter than having good adhesive person between tooth structure and the amalgam.In addition, amalgam and hole wall seepage situation (known as " little seepage ") at the interface also will take place, this little seepage tolerable bacterium, solvability salt and saliva penetrate into any space between amalgam and tooth structure.This will cause inflammation, stimulate the tooth marrow, the non-mineralization of tooth, the corrosion of amalgam, and other complication of following.A kind of adhesive/sealant between amalgam and tooth structure can reduce as far as possible or avoid little seepage, and owing to dig the less tooth material of cutter, and the stronger recovery situation of tolerable.
Can obtain to declare to bond the product of amalgam to tooth structure.A kind of this series products system is with trade mark AMALGAMBOND
TM(Parkell Co.) the complete sale of running after fame, this product is a kind of liquid adhesive, can directly connect and coat on the tooth structure thing.Activeconstituents in this adhesive comprises 4-META(4-first acrylyl oxy-ethyl benzene first three acid anhydrides) and the TBB(tri-n-butyl borane).Other obtainable like product comprises a kind of specific hardenable resin of direct coating to tooth structure, so that amalgam bonding person, its trade name is PANAVIA
TMDental Adhesive(Kuraray Company) and SUPERBOND
TMAdhesive(Sun Medical Co., Ltd., Kyoto, Japan).Back one series products uses and has any problem, because of it must have some preparation work programs, in order to its application and sclerosis.
Explanation is applied to tooth in advance with alkylene unsaturated bonding resin, to comprise M.Staninec and M.Holt in conjunction with amalgam to the paper on the tooth structure, Journal of Prosthetic Dentistry(1988), Vol.59, pp.397-402, A.Lacey and M.Staninec, Quintessence International(1989), Vol.20, pp.521-524, Y.Aboush and C.Jenkins, Br.Dent.J.(1989), Vol, 166, pp.255-257, Y.Aboush and R.Elderton, Br.Dent.J.(1991), Vol, 170, pp.219-222, with Y.Aboush and R.Elderton, Dent.Mater, (1991), Vol, 7, pp, 130-132.Above-mentioned last piece paper porism and being bonded to before, yet other paper porism and being bonded on the fresh amalgam through the hardened amalgam.Simultaneously, A, Ben-Amar, J.Am.Dent.Assoc.(1989) Vol.119, pp.725-728, system's explanation before using amalgam, is used " SCOTCHBOND " Dual Cure Dental Adhesive resin to empty edge in advance, then can reduce little seepage in amalgam restorative edge, and M.Mitrosky, Jr., Quintessence International(1981), Vol.9, pp.871-874 is to be illustrated under amalgam and the combination reconstruction, uses a kind of cyanacrylate as binding agent.People such as H.J.Staehle, Dtsch.Zahnartzt(1988) Vol.43, pp.952-957 is that explanation uses different tooth adhesive and varnish bonding amalgam to dentine.
Application contains can being caused and the cementing compositions of polymeric compounds sees also following report by free radical of inferior phosphorus base, for example, and M.Buonocore, W.Wileman and F.Brudevold, J, Dent.Res., 35,846(1956), M.Buonocore, and M.Quigley, J.Amer.Dent.Assoc., 57,807(1958), M.Anbar and E.Farley, J.Dent.Res.53,879(1974), E.Farley, R.Jones, and M.Anbar, J.Dent, Res., 56,1943(1977), U.S.Pat.Nos.3,882,600,3,997,504,4,222,780,4,235,633,4,259,075,4,259,117,4,368,043,4,383,052,4,499,251,4,514,342,4,515,930,4,537,940,4,539,382, and 4,544,467, european patent application No.058 483, and Japanese Patent Application Publication (Kokai) Nos.57-143372 and 57-167364.
U.S.Pat.No.3,513, be a kind of being incorporated in the amalgam of explanation 123(Saffir), to utilize the hardened epoxy composite on the amalgam adhesive tooth toothing.This epoxy composite that can harden comprises a kind of resin and a kind of polyamine stiffening agent of the glyceryl ether form that contracts.
U.S.Pat.No.4,064,629(Stoner) be a kind of application amalgam restorative method of explanation.This method is included in the surperficial substrate compositions of going up precoating layer a kind of " matrix metal " in cavity in the moth erosion tooth.The metal of this substrate compositions is the amalgamation with the tooth amalgam weighting material diffusion mercury of institute's application of known thereafter.It is said, should can improve the erosion resistance of tooth amalgam weighting material by " matrix metal " substrate compositions, and also promote the bonding between amalgam reconstruction and empty surface.
U.S.Pat.No.4,001,483(Lee, Jr. etc.) be the tooth composite of explanation in order to the edge between sealing tooth structure and the amalgam reconstruction, said composition contains (a) a kind of aklylene glycol dimethyl acrylate and/or its oligopolymer, (b) a kind of polymkeric substance effect initiator, (c) a kind of polymerization promotor reaches (d) a kind of secondary monomer addition agent.
U.S.Pat.No.3,574, be a kind of method of restoring moth erosion tooth of explanation 943(Stark), by being to dig forced hole, serve as a contrast a kind of polysiloxane pressure sensing type adhesive polymer that is dissolved in fluorocarbon with one deck, then with amalgam fill.It is said that this silicone layer is the barrier of seepage.
Japnese Kokai 63-175085 is a kind of cementing compositions of explanation, its composition comprises a kind of monomer of acid function, polymkeric substance, or multipolymer, the vinyl monomer of this acid function composition of a kind of solubilized, a kind of organo-peroxide and a kind of aromatic amine or-sulfinic acid salt.It is said that said composition is that bonding live body dental tissue is to composition and amalgam.
French Patent 2,561,521st illustrates a kind of intermediate cementing compositions that seals tooth cavity and chemoproection amalgam, and its composition comprises a kind of metal-powder that is scattered in the bonding lacquer.This composition contains metal-powder, cellulose lacquer, ethyl acetate, amyl propionate, fluorochemical and pimento oil.
Japanese Kokai 63-250310 is that explanation contains (a) ether of cellulose, (b) a kind of vinyl monomer, (c) a kind of organo-peroxide, and (d) the tooth cementing compositions of a kind of aromatic amine or a kind of-sulfinic acid.It is said that said composition can be widely used in reconstituted substance, comprises combination resin, amalgam, aluminum oxide, gold, alloy, poly-first methyl acrylate, polycarbonate etc.
The present invention provides a kind of cementing compositions, and its composition comprises:
(ⅰ) a kind of alkylene unsaturated compound;
(ⅱ) a kind of this alkylene unsaturated compound hardened micropartical metal charge that do not disturb, compare to using a kind of similar composition that does not have the micropartical metal filler, when this combination was to use to the middle layer between amalgam and tooth structure, the content of this micropartical metal charge must be able to effectively increase the cohesiveness between amalgam and tooth structure.
(ⅲ) a kind of polymerization initiator, its content must can be enough to the said composition of effectively hardening.
The present invention also provides a kind of cementing compositions, and its composition comprises:
(ⅰ) a kind of alkylene unsaturated compound;
(ⅱ) a kind of little metal charge of this alkylene unsaturated compound hardened particulate that do not disturb, its content is in the alkylene unsaturated compound of 100 parts of weight ratios, adds about 50 to about 4000 parts of weight ratios; And
(ⅲ) a kind of polymerization initiator, its content must be enough to the said composition of effectively hardening.
The present invention also provides a kind of method of a kind of reconstituted substance to a kind of matrix that bond.Its step comprises:
(ⅰ) mix the composition of addressing the present composition as mentioned;
(ⅱ) on one of paired reconstituted substance/matrix member, place the middle layer of one deck step (ⅰ) composition;
(ⅲ) this middle layer of optionally can hardening; And
(ⅳ) by this middle layer, on another member to the first member of the paired reconstituted substance/matrix that bonds.
In a kind of composition of the present invention, be applicable to that material as the alkylene unsaturated compound comprises that this skill understands habitually, tool is bonded to as dentine, enamel, the material of the ability in the sclerous tissueses such as bone.This compound is a kind of monomer, oligopolymer, or polymkeric substance (or mixture), the person that is applicable to the oral environment be with its without polymerization and through polymerization state the two.All applicable through phosphorylation and without phosphorus alkylene unsaturated compound the two and its mixture.
That the without phosphorus alkylene unsaturated compound of using comprises is single-or poly--(for example, two-, three-or four-functional group) propylene ester class and first propylene ester class, as methyl acrylate, the 2-hydroxyethyl acrylate, triethylene glycol diacrylate, neopentylglycol diacrylate, the pregnancy omega-diol diacrylate, three vinylformic acid trimethylammoniums alcohol propyl ester, five butyleneglycol tetraacrylate, poly-alkyl diol list-or two-esters of acrylic acid, the own ester list of carboxylamine-or pluralistic function base esters of acrylic acid, bisphenol a diacrylate class, and the relevant first esters of acrylic acid of above-claimed cpd, also have acrylic amide and first acrylic amide, vinyl compound, distyryl compound, and other is applicable to the alkenes unsaturated compound of oral environment.U.S.Pat.Nos, 4,499,251,4,515,930,4,537,940 and 4,539,382 all have this compounds of the vast scope of tabular.
The unsaturated tooth adhesive of representational without phosphorus alkene comprises that " SCOTCHBOND 2
TM" Dental Adhesive(3M), " CONCISE
TM" Enamel Bond(3M), " TENURE
TM" Solution Dentin Bonding System(Den-Mat Corp.), " GLUMA
TM" Bonding System(Columbus Dental Miles, Inc.) reach " MIRAGE-BOND
TM" Dentin-Enanel Bonding System(Chameleon Dental Products, Inc. consults U.S.Pat.Nos.4, and 514,527,4,521,550,4,588,756 and 4,659,751).
Unsaturated its composition of phosphorylation compound of alkylene that is suitable for comprises one or more phosphorus atom by a carbon, and nitrogen, oxygen or sulphur atom are bonded on the free radical that contains one or more alkylene unsaturated group.Preferable alkylene is unsaturated to be to lay respectively on acrylate and the first acrylate group as vinyl and the 2-propenyl of finding with group.One or more phosphorus atom can be incorporated into one or more hydrogen atom, active hydrogen atom, or on the alkyl that is unsubstituted or is substituted (for example, a kind of alkyl, aryl, alkaryl or aralkyl).A kind of special classification of the P contained compound that is suitable for is to be illustrated in european patent application No.0058 483 and U.S.Pat.No.4,515,930.This type of P contained compound comprises the organic ester by one or more phosphorous acids, the classification that this organic free radical that contains at least a alkylene unsaturated group ester is formed, wherein on the phosphorus of this ester, direct bond chlorine or bromine (being called " fontanel phosphoric acid ester " hereinafter).The preferable subclass of this type of fontanel phosphoric acid ester comprises the fontanel phosphoric acid ester of the 2-glycidyl first acrylate of dihydroxyphenyl propane (" Bis-GMA "), and it is with Bis-GMA and a kind of fontanel phosphatase reaction and prepare.Can comprise POCl with the phosphoric acid fontanelle compound of Bis-GMA reaction
3, PCl
3, PBr
3, R ' is Cl OP(O)
2, (R ' O)
2R(O) Cl, wherein R ' is an alkyl radical, the preferably be in the reaction of hydroxy-containing compounds and phosphoric acid fontanelle compound from hydroxy-containing compounds, as 2-first hydroxyethyl acrylate, ethylene glycol, polyoxyethylene glycol, five butyleneglycols etc. are removed one or more hydroxyl and are got.A good classification of spy of phosphorylation compound comprises the chlorine phosphoric acid ester of Bis-GMA.
Another kind of suitable phosphorylation compounds category comprises the phosphoric acid ester that is illustrated in following patent documentation, as U.S.Pat.Nos.3, and 882,600,3,997,504,4,222,780,4,235,633,4,259,075,4,259,117,4,368,043,4,442,239,4,499,251,4,514,342,4,537,940,4,539,382 and Japanese patent application (Koho) No.85-17235.This type of other demonstration member compound is 2-first acrylyl oxy-ethyl phenyl phosphide and 10-first acryloyl-oxy decyl dihydrogen phosphoric acid ester.
The phosphorylation compound of another suitable class comprises and is illustrated in U.S.Pat.Nos, 4,383,052 and 4,404,150 with the phosphate derivative of Japanese Kokai 57-143372 and 57-167364.Be illustrated in Buonocore mentioned above, the dimethyl acrylamide acid glycerol phosphoric acid ester of Wileman and Brudevold publication is also applicable.
Other is suitable for and contains the polymkeric substance of phosphorylation compound and/or tool acrylate or first acrylate functional group for the tooth adhesive of alkylene unsaturated compound comprises those.In this type of tooth adhesive, the mixture of single phosphorylation compound or phosphorylation compound all can use.The tooth adhesive that is suitable for comprises: " SCOTCHBOND
TM" Dual Cure Dental Adhesive(3M), " ALL-BOND2
TM" Universal Dental Adhesive System(Bisco, Inc.), " CLEARFIL
TM" Photo Bond Light-Cured Dental Bonding Agent(Kuraray Co., Ltd.), " RESTOBOMD3
TM" Dual Dentin/Enamel Bonding Agent(Lee Pharmaceuticals, consult U.S.Pat.Nos.4,524,527 and 4,521,550), " PRISMA UNIVERSAL BOND3
TM" Dentin/Enamel Bonding Agent(L.D.Caulk Division of Dentsply International, Inc. consults U.S.Pat.No.4, and 814,423), " BONDLITE
TM" Dental Adhesive(Sybron Corp.), " Johnson ﹠amp; Johnson " Dentin Bonding Agent and " Johnson ﹠amp; Johnson " Light-Curing Bonding Agent(Johnson ﹠amp; Johnson Co.), " PLAFIQUE Bonding Agent(Tokuyama Soda Co., Ltd), " SHOFU
TM" Bonding Base(Shofu, Inc.), and " SINTERBOND
TM" Dental Adhesive(Teledyne Getz).
In the preferable specific embodiments of the mixture that comprises a kind of alkylene unsaturated compound, the suitable relative content of every kind of compound can be set easily according to those skilled in the art.
Composition of the present invention also comprises a kind of alkylene unsaturated compound hardened micropartical metal charge that can not disturb.The metal charge of particularly suitable can based on composition in the specific alkylene unsaturated compound that exists and the chemical compatibility of specific aggregation effect initiator, and select by those skilled in the art.Also can be via the interference of measuring alkylene unsaturated compound sclerosis, for example, by adding the selected metal charge of a kind of warp to the mixture of a kind of alkylene unsaturated compound and polymerization initiator, and this mixture then can reach gratifying hardenability as no metal charge.When attempting the metallic mixture of sclerosis, any because the sclerosis that metal charge causes is disturbed all can observe easily.The selection of this weighting material is that it can be a kind of pure metal, as IV A, V A, VI A according to itself of alkylene unsaturated compound and polymerization initiator, VII A, V I I I I, I B or I I B family metal, aluminium, indium, the thallium of I I I B family, with the tin and the lead of IV B family, or its alloy.Traditional tooth amalgam powder and typical silver, tin, the mixture of copper and zinc is also applicable.The preferable average particle size particle size of this micropartical metal charge is about 1 micron to about 100 microns, and better person is about 1 micron to about 50 microns.
In some preferred embodiment, compare to using a kind of similar composition that does not have metal charge, when composition is the middle layer of regarding between tooth structure and amalgam, the content that metal charge exists is that the cohesiveness with effective raising amalgam and tooth structure is benchmark, in this type of preferred embodiment, the decision effective content is according to the method in the following example.In other preferred embodiment, the content that the micropartical metal charge exists is benchmark with the alkylene unsaturated compound of per 100 parts of weight ratios, is 50 to about 4000 parts of weight ratios, and the preferably is about 200 to about 3000 weight ratios.
A kind of composition of the present invention also comprises that a kind of content is enough to the polymkeric substance effect initiator of effective hardening composition.Suitable polymerization initiator comprises self-hardening and slight hardened polymerization initiator, as in U.S.Pat.No.4, the mentioned persons of 539,382 the 28th and 29 row, fontanelle methyl-s-triazine through the chromophoric group replacement, as in U.S.Pat.No.3,954,475 shown persons, reach the Xin Jia oxadiazole that replaces through chromophoric group, as in U.S.Pat.No.4,212,970 shown persons.
The preferable content of polymerization initiator is benchmark with the alkylene unsaturated compound of per 100 parts of weight ratios, is about 0.01 to about 20 parts of weight ratios, and better person is about 0.1 to 10 part of weight ratio.
Other can be incorporated in compound (except that alkylene unsaturated compound discussed above) in the present composition according to proper content, can be easy to by those skilled in the art selectedly, and provides required character.That suitable compound comprises is single-or poly--acrylic acid or the like and first acrylate, as methyl acrylate, vinylformic acid 2-hydroxyl ethyl ester, triethylene glycol diacrylate, neopentylglycol diacrylate, the pregnancy omega-diol diacrylate, three vinylformic acid, three methyl alcohol propyl ester, five butyleneglycol tetraacrylate, polyalkylene glycol mono-or the diacrylate class, the list of urethanum-or many-functional group esters of acrylic acid, bisphenol a diacrylate class, and the corresponding first esters of acrylic acid of above-claimed cpd, and acrylamide and first acrylamide, vinyl compound, distyryl compound and other are applicable to the alkenes unsaturated compound of oral environment.This compounds be tabular in U.S.Pat.Nos.4,499,251,4,515,930,4,537,940 and 4,539,382.
Composition of the present invention also can contain known assistant agent, as promotor, and inhibitor, tranquilizer, dyestuff, pigment, viscosity modifier extends or the reinforcement weighting material surface tension inhibitor, wetting agent auxiliary agent, known composition in antioxidant and other present technique.
Composition of the present invention can mix and pack different compositions being prepared according to method known in the field.For example, when using a kind of stiffening agent of redox form, suitable packaged form can keep oxidation and reductive agent to separate, to guarantee the stability in storage of composition.The example of packaged form comprises (a) a kind of alkylene unsaturated compound, and a kind of metal charge and a kind of reductive agent are in a kind of alkylene unsaturated compound and a kind of oxide compound are packed in two portions of another part with a part and (b).In the example of a kind of organic-sulfinic acid (or its esters)/amine (or its esters)/superoxide three-level system, also can use a kind of three parts packing, wherein-sulfinic acid is to separate packing with amine.
If the composition of polymerization initiator comprises a kind of light trigger, then the alkylene unsaturated compound preferably separates with light trigger and packs or be loaded in the lighttight container.If when using a kind of thermal initiator of the initiated polymerization that contacts with unsaturatedization of alkylene thing (as tributyl methyl esters alkane), then alkylene unsaturated compound and initiator must be separated packing, the short period of time mixing before this kind separate type packing only must be used gets final product.
Composition of the present invention can use between a kind of matrix and reconstituted substance as a kind of middle layer, matrix such as sclerous tissues are (as bone, enamel or dentine) or pottery, reconstituted substance such as pure metal or alloy, amalgam, ceramic composition, or a kind of composition that comprises bonding polymer (or polymer mixture) and a kind of micropartical weighting material.A kind of initial thing can be used, also good cohesiveness can be do not obtained but there is initial thing.Common composition of the present invention is comparable only to use alkylene unsaturated compound person that better cohesiveness is provided.
In order to be beneficial to a kind of reconstituted substance is bonded on a kind of matrix, the composition of the present composition at first must mix with proper content.As discussed above, according to the particular form of use stiffening agent, composition can mixing maybe can be packaged into the system of two or three parts before packing, and mixes before using.In case after composition mixed, the present composition of gained can place on reconstituted substance or the matrix by thin layer form (for example brushing).Then, depending on the circumstances or the needs of the situation, can proper method (for example, comprising being exposed under the room temperature visible light, the inferior type of heating of UV-light) hardened.Afterwards, if desired, can prepare other member (for example mixing) of paired reconstituted substance/matrix, and it is positioned on the tack coat.
In order to accord with the above factor of background of invention, so expectation can make the amalgam bonds well on tooth structure.Therefore, a kind of use of the present composition is to be included in one in the cavity of preparation, and the tooth amalgam is bonded on the tooth structure.
Preferable mode is to use a kind of amalgam through upgrading, in order to suitably being bonded on the tooth structure.This kind can mix with known amalgam powder and make through the amalgam of upgrading by the micropartical addition agent.Then, according to known method, in amalgamator, grind powdered alloy, and make amalgam through upgrading through upgrading with mercury.
Preferable micropartical addition agent is to be selected from following family group: the 1) polymkeric substance of acrylate or first acrylate functional group, 2) vinylformic acid or the acrylic acid metallic salt of first, 3) nonmetal weighting material, 4) oxygenant and 5) reductive agent.The micropartical addition agent can be applicable to the known amalgam powder of all scopes and the weight ratio of known mercury and amalgam powder.
Representational acrylate or first acrylate functionalized polymer comprise poly-(paraffinic acid) powder.Representational vinylformic acid or first acrylate metal salt class comprise dimethyl acrylamide acid zinc, first vinylformic acid zirconium, first vinylformic acid silver, first sodium acrylate and first vinylformic acid magnesium.Nonmetal weighting material comprise undressed organic weighting material and surface treated weighting material the two.Representational nonmetal weighting material, also organic as is well known weighting material comprises the OX-50 through silane treatment
TMPyrogenic silica (Degussa Company), TEG dimethyl acrylate (" TEGDMA ") (Rohm Tech Co.), and bisphenol A diglycidyl ether dimethyl acrylate are with the mixture of 60: 17: 17 weight ratios.Other representational nonmetal weighting material comprises and is illustrated in U.S.Pat.No.4,503,169, and zirconium white/silica-filled thing unprocessed or that handle through γ-methacryloyl oxygen propyl trimethoxy silicane.Preferable oxygenant comprises benzoyl peroxide.Preferable reductive agent comprises benzene sulfinic acid sodium salt.
Amalgam is as follows to agglutinating appraisal procedure through etched enamel: the ox tooth of similar age and outward appearance is embedded in the acrylic disk, so that enamel exposes to the open air.120 grade the silicon carbide abrasion paper of using appts on the stone wheel is exposed to outer part with every tooth and polishes, and is parallel to this acrylic disk.Carry out further tooth grinding and polishing with 320 grades the silicon carbide mill silicon erosion paper that is installed on the stone wheel.During grinding and polishing step, clean tooth with water continuously.Tooth after the polishing is stored in the distilled water, and after polishing, is used for test in two hours.
Yu Shuizhong takes out the tooth through polishing, and with the compressed air stream drying.Phosphoric acid etch glue is imposed on enamel last 15 second, clean with water, and after drying.With brush cementing compositions is imposed on the whole enamel surface, and it is blown out thin film, according to the indication of manufacturers, with its sclerosis with pressurized air.
With a thick TEFLON of 2mm that has diameter 5mm round tube hole on it
TMThe mold of tetrafluoroethylene clamps together in every tooth through polishing, so that in the mold, the central shaft in hole is perpendicular to the dental surface through polishing.Fill up the hole of each mold with ready amalgam, and make it under room temperature, left standstill about 15 minutes, be stored in then in 37 ℃ the distilled water 24 hours.Then carefully take out mold, stay the amalgam pearl that is linked to every tooth of casting.
The assessment cohesive force be with this acrylic device for disc on a fixer, this fixer is to clamp together in an INSTRON
TMOn the working clamp of tension test instrument, and will be through the dental surface of polishing toward the direction of parallel pulling force.Place an orthodontics coil (diameter 0.44mm) around contiguous amalgam pearl pedestal through the polishing dental surface.The end of orthodontics line is clamped together on the Pulling force pincer of tension test instrument, this binding part is placed shear stress.The cross connecting rod speed of use 2mm/min stresses on this binding part to its (or amalgam pearl) and ruptures.
It is to help to understand the present invention that following example is provided, and does not limit its scope with this.Unless otherwise indicated, otherwise all umbers and per-cent are all weight ratio.
Example 1-12 and comparative example C-1 to C-6
Use the as above program of explanation, assess several cementing compositions in the bonding shear bonding force on the etching enamel.Employed amalgam is DISPERSALLOY
TMThe double overflow shape capsule of amalgam.Commercial obtainable adhesive is the indication assessment according to manufacturers.Prepare composition of the present invention and be in advance in weighing metal addition agent to a skip-cage combination shaft.Alkylene unsaturated compound (the SCOTCHBOND that adds (about 0.03 a gram) phosphorylation
TMDual Cure Dental Adhesive resin) and (about 0.02 a gram) polymerization initiator (SCOTCHBOND
TMDuel Cure DentalAdhesive liquid) to this metal addition agent.
Preparation is another kind of forms the replacement method for compositions that comprises a kind of without phosphorus alkylene unsaturated compound and comprises: be weighed in advance in metal addition agent to a skip-cage combination shaft, and add each one: (ⅰ) a kind of without phosphorus alkylene unsaturated compound and dihydroxy ethyl-p-Tolylamine reductive agent (CONCISE
TMEnamel Bond A) mixture; Reach (ⅱ) a kind of without phosphorus alkylene unsaturated compound and benzoyl peroxide oxygenant (CONCISE
TMEnamel Bond B) mixture.
Then in each example,, and coat on etched enamel with brush with each composition short mix.Then, before placing amalgam, according to the indication of manufacturers, will be through the adhesive sclerosis of coating.
List in as being example number in the following table I alkylene unsaturated compound, metal charge, and the average bonding shear bonding force value of various different test composition.
The result of table I is that the example compositions comprise a kind of alkylene unsaturated compound and a kind of metal charge is formed in explanation, with respect to without the alkylene unsaturated compound of filling, can provide shear cohesive force through improving to sclerous tissues and amalgam.The average shear clinging power value that several compositions of the present invention provides is better than the value that commercially available sclerous tissues/the amalgam adhesive is obtained.Simultaneously, in comparative example C-6, can be observed, when using SCOTCHBOND
TMWhen Dual Cure Dental Adhesive liquid was polymerization initiator, zinc can disturb SCOTCHBOND
TMDual Cure Dental Adhesive hardening of resin.
Example 13-14 and comparative example C-7 to C-11
Use the program of explanation as mentioned, assess several cementing compositions in the shear adhesive bond power on the etching enamel.Employed amalgam is DISPERSALLOY
TMAmalgam (Johnson ﹠amp; Johnson) double overflow type capsule or contain the organic weighting material of various different amounts through the upgrading version.List in as being example number in the following table II alkylene unsaturated compound, metal charge, amalgam, amalgam addition agent, and the average bonding shear bonding force value of test different compositions.
The result of table II shows, can obtain maximum average bonding shear bonding force value through metal filled adhesive and through the amalgam powder of upgrading.
Claims (9)
1, a kind of cementing compositions, its composition comprises:
(i) a kind of alkylene unsaturated compound;
(ii) a kind of this alkylene unsaturated compound hardened micropartical metal charge that can not disturb, its consumption is when composition is used as one deck middle layer between amalgam and tooth structure, comparing to a kind of similar composition that uses no micropartical metal charge, is benchmark with the cohesiveness that can effectively increase amalgam and tooth structure; And
(iii) a kind of content is enough to the stiffening agent of effectively hard composition.
2, according to the composition of claim 1, wherein the composition of this alkylene unsaturated compound comprises a kind of compound of phosphorylation.
3, according to the composition of claim 2, wherein the composition of this phosphorylation compound comprises the chlorine carbonic ether of a kind of Bis-GMA.
4, according to the composition of claim 1, wherein the composition of this alkylene unsaturated compound comprises a kind of no phosphorus compound.
5, according to the composition of claim 1, wherein the composition of this alkylene unsaturated compound comprises the mixture of at least a phosphorylation compound and at least a without phosphorus compound formation.
6, according to the composition of claim 1, wherein the average particle size particle size of this micropartical metal charge is about 1 micron to about 100 microns.
7, according to the composition of claim 1, wherein the average particle size particle size of this micropartical metal charge is about 1 micron to about 50 microns.
8, according to the composition of claim 1, a kind of tooth amalgam of the metal filled system of this micropartical powder wherein.
9, a kind of method of a kind of reconstituted substance to a kind of matrix that bond, its step comprises:
(ⅰ) mixing is according to the composition of the composition of claim 1;
(ⅱ) placement derives from one deck middle layer of step (ⅰ) composition on one of paired reconstituted substance/matrix member;
(ⅲ) this middle layer of optionally hardening; And
(ⅳ) by the middle layer, on another member to the first member of the paired reconstituted substance/matrix that bonds.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US815,172 | 1977-07-13 | ||
| US81517291A | 1991-12-31 | 1991-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1073961A true CN1073961A (en) | 1993-07-07 |
Family
ID=25217081
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN92111811A Pending CN1073961A (en) | 1991-12-31 | 1992-12-30 | With metal filled cementing compositions and method |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0623016A1 (en) |
| CN (1) | CN1073961A (en) |
| AU (1) | AU3233493A (en) |
| BR (1) | BR9207010A (en) |
| CA (1) | CA2117347A1 (en) |
| IL (1) | IL104008A0 (en) |
| MX (1) | MX9207423A (en) |
| WO (1) | WO1993012757A1 (en) |
| ZA (1) | ZA9210019B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1081923C (en) * | 1994-07-19 | 2002-04-03 | 阿斯特拉公司 | Use of chitosan and polysaccharides immobilized thereon for the production of hard tissue stimulants |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4064629A (en) * | 1976-01-26 | 1977-12-27 | The University Of Virginia | Cavity liner for dental restorations |
| JPS59137404A (en) * | 1983-01-27 | 1984-08-07 | Kuraray Co Ltd | Dental adhesive |
| US5662886A (en) * | 1991-01-08 | 1997-09-02 | Minnesota Mining And Manufacturing Company | Adhesive amalgam system |
-
1992
- 1992-12-02 WO PCT/US1992/010371 patent/WO1993012757A1/en not_active Ceased
- 1992-12-02 CA CA002117347A patent/CA2117347A1/en not_active Abandoned
- 1992-12-02 EP EP93900802A patent/EP0623016A1/en not_active Withdrawn
- 1992-12-02 BR BR9207010A patent/BR9207010A/en not_active Application Discontinuation
- 1992-12-02 AU AU32334/93A patent/AU3233493A/en not_active Abandoned
- 1992-12-07 IL IL104008A patent/IL104008A0/en unknown
- 1992-12-18 MX MX9207423A patent/MX9207423A/en unknown
- 1992-12-23 ZA ZA9210019A patent/ZA9210019B/en unknown
- 1992-12-30 CN CN92111811A patent/CN1073961A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1081923C (en) * | 1994-07-19 | 2002-04-03 | 阿斯特拉公司 | Use of chitosan and polysaccharides immobilized thereon for the production of hard tissue stimulants |
Also Published As
| Publication number | Publication date |
|---|---|
| BR9207010A (en) | 1995-12-05 |
| ZA9210019B (en) | 1994-06-23 |
| WO1993012757A1 (en) | 1993-07-08 |
| IL104008A0 (en) | 1993-05-13 |
| EP0623016A1 (en) | 1994-11-09 |
| AU3233493A (en) | 1993-07-28 |
| CA2117347A1 (en) | 1993-07-08 |
| MX9207423A (en) | 1993-06-01 |
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