AU740495B2 - Photopolymerizable dental compositions - Google Patents
Photopolymerizable dental compositions Download PDFInfo
- Publication number
- AU740495B2 AU740495B2 AU96817/98A AU9681798A AU740495B2 AU 740495 B2 AU740495 B2 AU 740495B2 AU 96817/98 A AU96817/98 A AU 96817/98A AU 9681798 A AU9681798 A AU 9681798A AU 740495 B2 AU740495 B2 AU 740495B2
- Authority
- AU
- Australia
- Prior art keywords
- functional group
- active functional
- photopolymerizable composition
- modifier
- polymerization
- 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.)
- Ceased
Links
- 239000000203 mixture Substances 0.000 title claims description 164
- 125000000524 functional group Chemical group 0.000 claims description 142
- 239000003607 modifier Substances 0.000 claims description 117
- 238000010538 cationic polymerization reaction Methods 0.000 claims description 101
- 230000000977 initiatory effect Effects 0.000 claims description 93
- 238000006116 polymerization reaction Methods 0.000 claims description 78
- -1 diphenyliodonium hexafluoroantimonate Chemical compound 0.000 claims description 67
- 230000006698 induction Effects 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 46
- 238000006243 chemical reaction Methods 0.000 claims description 43
- 238000010526 radical polymerization reaction Methods 0.000 claims description 36
- 230000005855 radiation Effects 0.000 claims description 33
- 229920005989 resin Polymers 0.000 claims description 32
- 239000011347 resin Substances 0.000 claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 20
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 claims description 17
- 229930006711 bornane-2,3-dione Natural products 0.000 claims description 17
- 229920000647 polyepoxide Polymers 0.000 claims description 17
- 239000003822 epoxy resin Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000012086 standard solution Substances 0.000 claims description 13
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 11
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 10
- 230000000379 polymerizing effect Effects 0.000 claims description 10
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 claims description 9
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 239000003504 photosensitizing agent Substances 0.000 claims description 7
- NEGFNJRAUMCZMY-UHFFFAOYSA-N 3-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC(C(O)=O)=C1 NEGFNJRAUMCZMY-UHFFFAOYSA-N 0.000 claims description 6
- 229920005862 polyol Polymers 0.000 claims description 6
- YNUWMOWRRKMPRE-UHFFFAOYSA-N 2-tert-butyl-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1C(C)(C)C YNUWMOWRRKMPRE-UHFFFAOYSA-N 0.000 claims description 5
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 5
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 5
- 150000003077 polyols Chemical class 0.000 claims description 5
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 150000008431 aliphatic amides Chemical class 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 239000003479 dental cement Substances 0.000 claims description 3
- 239000011350 dental composite resin Substances 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000005594 diketone group Chemical group 0.000 claims description 2
- 239000012966 redox initiator Substances 0.000 claims description 2
- 239000000565 sealant Substances 0.000 claims description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 238000005065 mining Methods 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 150000003455 sulfinic acids Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 description 53
- 239000004593 Epoxy Substances 0.000 description 45
- 239000011550 stock solution Substances 0.000 description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 34
- 239000000126 substance Substances 0.000 description 27
- 239000000523 sample Substances 0.000 description 21
- 239000013068 control sample Substances 0.000 description 18
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 16
- 125000002091 cationic group Chemical group 0.000 description 14
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 11
- 230000009977 dual effect Effects 0.000 description 11
- 239000003999 initiator Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 238000000113 differential scanning calorimetry Methods 0.000 description 9
- 150000002118 epoxides Chemical class 0.000 description 9
- 125000003700 epoxy group Chemical group 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 229920001451 polypropylene glycol Polymers 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002131 composite material Substances 0.000 description 6
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- 229920000909 polytetrahydrofuran Polymers 0.000 description 6
- 239000012085 test solution Substances 0.000 description 6
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000012955 diaryliodonium Substances 0.000 description 5
- 125000005520 diaryliodonium group Chemical group 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 230000003111 delayed effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 210000000214 mouth Anatomy 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 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 4
- XCBBNTFYSLADTO-UHFFFAOYSA-N 2,3-Octanedione Chemical compound CCCCCC(=O)C(C)=O XCBBNTFYSLADTO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Natural products NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 3
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 2
- FJPGAMCQJNLTJC-UHFFFAOYSA-N 2,3-Heptanedione Chemical compound CCCCC(=O)C(C)=O FJPGAMCQJNLTJC-UHFFFAOYSA-N 0.000 description 2
- IFPDWCHTHGPOKN-UHFFFAOYSA-N 2,3-dimethylbutane-1,3-diamine Chemical compound NCC(C)C(C)(C)N IFPDWCHTHGPOKN-UHFFFAOYSA-N 0.000 description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- KQGHTOZUPICELS-UHFFFAOYSA-N 2-[4-(dimethylamino)phenyl]acetic acid Chemical compound CN(C)C1=CC=C(CC(O)=O)C=C1 KQGHTOZUPICELS-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical class OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- LBCCPKFTHIBIKU-UHFFFAOYSA-N 3,4-Heptanedione Chemical compound CCCC(=O)C(=O)CC LBCCPKFTHIBIKU-UHFFFAOYSA-N 0.000 description 2
- KVFQMAZOBTXCAZ-UHFFFAOYSA-N 3,4-Hexanedione Chemical compound CCC(=O)C(=O)CC KVFQMAZOBTXCAZ-UHFFFAOYSA-N 0.000 description 2
- IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical compound C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 2
- CDSULTPOCMWJCM-UHFFFAOYSA-N 4h-chromene-2,3-dione Chemical class C1=CC=C2OC(=O)C(=O)CC2=C1 CDSULTPOCMWJCM-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
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- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 238000012644 addition polymerization Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- IDSLNGDJQFVDPQ-UHFFFAOYSA-N bis(7-oxabicyclo[4.1.0]heptan-4-yl) hexanedioate Chemical compound C1CC2OC2CC1OC(=O)CCCCC(=O)OC1CC2OC2CC1 IDSLNGDJQFVDPQ-UHFFFAOYSA-N 0.000 description 2
- LMMDJMWIHPEQSJ-UHFFFAOYSA-N bis[(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl] hexanedioate Chemical compound C1C2OC2CC(C)C1COC(=O)CCCCC(=O)OCC1CC2OC2CC1C LMMDJMWIHPEQSJ-UHFFFAOYSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000005548 dental material Substances 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
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- 150000002170 ethers Chemical class 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
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- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
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- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 2
- KHLYPCDHQMQXET-UHFFFAOYSA-N n,n-dihydroxy-4-methylaniline Chemical compound CC1=CC=C(N(O)O)C=C1 KHLYPCDHQMQXET-UHFFFAOYSA-N 0.000 description 2
- 125000000466 oxiranyl group Chemical group 0.000 description 2
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000068 pit and fissure sealant Substances 0.000 description 2
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- 229920001610 polycaprolactone Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000002000 scavenging effect Effects 0.000 description 2
- KHDBMTLGTSGEEG-UHFFFAOYSA-M sodium;2-methylbenzenesulfinate Chemical compound [Na+].CC1=CC=CC=C1S([O-])=O KHDBMTLGTSGEEG-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- ZWAJLVLEBYIOTI-OLQVQODUSA-N (1s,6r)-7-oxabicyclo[4.1.0]heptane Chemical group C1CCC[C@@H]2O[C@@H]21 ZWAJLVLEBYIOTI-OLQVQODUSA-N 0.000 description 1
- LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-UHFFFAOYSA-N 0.000 description 1
- OAKFFVBGTSPYEG-UHFFFAOYSA-N (4-prop-2-enoyloxycyclohexyl) prop-2-enoate Chemical compound C=CC(=O)OC1CCC(OC(=O)C=C)CC1 OAKFFVBGTSPYEG-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- DSZTYVZOIUIIGA-UHFFFAOYSA-N 1,2-Epoxyhexadecane Chemical compound CCCCCCCCCCCCCCC1CO1 DSZTYVZOIUIIGA-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical class OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000001016 thiazine dye Substances 0.000 description 1
- 239000001017 thiazole dye Substances 0.000 description 1
- 239000011043 treated quartz Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- SXPUVBFQXJHYNS-UHFFFAOYSA-N α-furil Chemical compound C=1C=COC=1C(=O)C(=O)C1=CC=CO1 SXPUVBFQXJHYNS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/20—Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
- C08G65/105—Onium compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S522/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S522/908—Dental utility
Landscapes
- Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Dental Preparations (AREA)
- Polymerisation Methods In General (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/092550 | 1998-06-05 | ||
| US09/092,550 US6187836B1 (en) | 1998-06-05 | 1998-06-05 | Compositions featuring cationically active and free radically active functional groups, and methods for polymerizing such compositions |
| PCT/US1998/020836 WO1999062460A1 (en) | 1998-06-05 | 1998-10-02 | Photopolymerizable dental compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU9681798A AU9681798A (en) | 1999-12-20 |
| AU740495B2 true AU740495B2 (en) | 2001-11-08 |
Family
ID=22233774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU96817/98A Ceased AU740495B2 (en) | 1998-06-05 | 1998-10-02 | Photopolymerizable dental compositions |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6187836B1 (enExample) |
| EP (1) | EP1083859B1 (enExample) |
| JP (1) | JP4369051B2 (enExample) |
| KR (1) | KR20010052534A (enExample) |
| CN (1) | CN1102846C (enExample) |
| AU (1) | AU740495B2 (enExample) |
| BR (1) | BR9815890B1 (enExample) |
| CA (1) | CA2332496C (enExample) |
| DE (1) | DE69807756T2 (enExample) |
| ES (1) | ES2178849T3 (enExample) |
| WO (1) | WO1999062460A1 (enExample) |
Families Citing this family (92)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19753461A1 (de) * | 1997-12-02 | 1999-06-10 | Espe Dental Ag | Lagerstabile kationisch polymerisierende Zubereitungen mit verbessertem Härtungsverhalten |
| WO1999048945A1 (en) * | 1998-03-20 | 1999-09-30 | Nippon Soda Co., Ltd. | Photocurable composition containing iodonium salt compound |
| US6287748B1 (en) * | 1998-07-10 | 2001-09-11 | Dsm N.V. | Solid imaging compositions for preparing polyethylene-like articles |
| US6762002B2 (en) | 1998-07-10 | 2004-07-13 | Dsm Desotech, Inc. | Solid imaging compositions for preparing polypropylene-like articles |
| US6379866B2 (en) | 2000-03-31 | 2002-04-30 | Dsm Desotech Inc | Solid imaging compositions for preparing polypropylene-like articles |
| US20060154175A9 (en) * | 1998-07-10 | 2006-07-13 | Lawton John A | Solid imaging compositions for preparing polypropylene-like articles |
| US6306926B1 (en) * | 1998-10-07 | 2001-10-23 | 3M Innovative Properties Company | Radiopaque cationically polymerizable compositions comprising a radiopacifying filler, and method for polymerizing same |
| EP1143915B1 (en) * | 1999-01-08 | 2004-12-01 | 3M Innovative Properties Company | Dental mill blanks |
| DE19937093A1 (de) * | 1999-08-06 | 2001-02-08 | Espe Dental Ag | Adhäsivsysteme III |
| US6800671B1 (en) * | 2000-04-21 | 2004-10-05 | Britesmile, Inc. | Low peak exotherm curable compositions |
| CN1326683C (zh) | 2000-09-11 | 2007-07-18 | 陶氏环球技术公司 | 制造轮胎支承件的方法和装置 |
| DE10108381A1 (de) | 2001-02-21 | 2002-09-05 | Delo Industrieklebstoffe Gmbh | Verfahren und Vorrichtung zur Voraktivierung kationisch polymerisierender Massen |
| US7160941B2 (en) * | 2001-05-01 | 2007-01-09 | Pentron Clinical Technologies, Llc | Dental composite materials and method of manufacture thereof |
| US7241856B2 (en) * | 2003-06-02 | 2007-07-10 | Pentron Clinical Technologies Llc | Dental resins, dental composite materials, and method of manufacture thereof |
| US7470728B2 (en) * | 2001-05-01 | 2008-12-30 | Pentron Clinical Technologies Llc | Dental glazes and method of manufacture and use thereof |
| US7589132B2 (en) * | 2001-05-01 | 2009-09-15 | Pentron Clinical Technologies, Llc | Dental resins, dental composite materials, and method of manufacture thereof |
| WO2003015720A1 (en) * | 2001-08-15 | 2003-02-27 | 3M Innovative Properties Company | Hardenable self-supporting structures and methods |
| US6765036B2 (en) * | 2002-01-15 | 2004-07-20 | 3M Innovative Properties Company | Ternary photoinitiator system for cationically polymerizable resins |
| US6713535B2 (en) * | 2002-02-28 | 2004-03-30 | Turbine Controls, Inc. | Low-friction chromate-free coating of epoxy resins and sulfonyldianiline |
| JP4485117B2 (ja) * | 2002-06-27 | 2010-06-16 | 日東電工株式会社 | 保護剥離用フィルム |
| US6773261B2 (en) * | 2002-06-28 | 2004-08-10 | 3M Innovative Properties Company | Processes for forming dental materials |
| US7134875B2 (en) * | 2002-06-28 | 2006-11-14 | 3M Innovative Properties Company | Processes for forming dental materials and device |
| US20040120901A1 (en) * | 2002-12-20 | 2004-06-24 | Dong Wu | Dental compositions including enzymes and methods |
| DE10261241A1 (de) * | 2002-12-20 | 2004-07-15 | 3M Espe Ag | Dentalmaterial mit bakteriostatischen und/oder bakteriziden Substanzen |
| US20040122126A1 (en) * | 2002-12-20 | 2004-06-24 | Dong Wu | Free-radical initiator systems containing enzymes, compositions, and methods |
| US20040206932A1 (en) * | 2002-12-30 | 2004-10-21 | Abuelyaman Ahmed S. | Compositions including polymerizable bisphosphonic acids and methods |
| US7084182B2 (en) * | 2003-03-13 | 2006-08-01 | Tokuyama Corporation | Photopolymerization initiator |
| CA2535556C (en) * | 2003-08-12 | 2014-01-07 | 3M Innovative Properties Company | Self-etching dental compositions and methods |
| US20050042577A1 (en) * | 2003-08-19 | 2005-02-24 | Kvitrud James R. | Dental crown forms and methods |
| US20050042576A1 (en) * | 2003-08-19 | 2005-02-24 | Oxman Joel D. | Dental article forms and methods |
| US20050040551A1 (en) * | 2003-08-19 | 2005-02-24 | Biegler Robert M. | Hardenable dental article and method of manufacturing the same |
| US7030169B2 (en) * | 2003-09-26 | 2006-04-18 | 3M Innovative Properties Company | Arylsulfinate salts in initiator systems for polymeric reactions |
| US20050165127A1 (en) * | 2003-12-31 | 2005-07-28 | Dsm Desotech, Inc. | Solid imaging compositions for preparing polyethylene-like articles |
| ATE554740T1 (de) | 2004-06-15 | 2012-05-15 | Dentsply Int Inc | Dentalzusammensetzungen mit geringer schwindung und geringer spannung |
| EP1778164B1 (en) * | 2004-06-15 | 2010-04-21 | Dentsply International, Inc. | Radical polymerizable macrocyclic resin compositions with low polymerization stress |
| JP5214242B2 (ja) * | 2004-07-08 | 2013-06-19 | スリーエム イノベイティブ プロパティズ カンパニー | 歯科用の方法、組成物、および酸感受性色素を含むキット |
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| EP1784155B1 (en) * | 2004-08-11 | 2011-09-28 | 3M Innovative Properties Company | Self-adhesive compositions including a plurality of acidic compounds |
| US7704643B2 (en) * | 2005-02-28 | 2010-04-27 | Inphase Technologies, Inc. | Holographic recording medium with control of photopolymerization and dark reactions |
| US20060205838A1 (en) * | 2005-03-10 | 2006-09-14 | Velamakanni Bhaskar V | Hardenable antimicrobial dental compositions and methods |
| US20060204452A1 (en) * | 2005-03-10 | 2006-09-14 | Velamakanni Bhaskar V | Antimicrobial film-forming dental compositions and methods |
| DE102005016762A1 (de) * | 2005-04-11 | 2006-10-19 | Kettenbach Gmbh & Co. Kg | Photopolymerisierbares Einkomponenten-Kronen- und Brückenmaterial |
| EP1787627A1 (en) * | 2005-11-17 | 2007-05-23 | 3M Innovative Properties Company | Anti-microbial dental impression material |
| US7896650B2 (en) * | 2005-12-20 | 2011-03-01 | 3M Innovative Properties Company | Dental compositions including radiation-to-heat converters, and the use thereof |
| US7776940B2 (en) * | 2005-12-20 | 2010-08-17 | 3M Innovative Properties Company | Methods for reducing bond strengths, dental compositions, and the use thereof |
| US8026296B2 (en) | 2005-12-20 | 2011-09-27 | 3M Innovative Properties Company | Dental compositions including a thermally labile component, and the use thereof |
| US20070142498A1 (en) * | 2005-12-20 | 2007-06-21 | Brennan Joan V | Dental compositions including thermally responsive additives, and the use thereof |
| JP4890872B2 (ja) * | 2006-01-30 | 2012-03-07 | ルネサスエレクトロニクス株式会社 | 光半導体封止用透明エポキシ樹脂組成物及びそれを用いた光半導体集積回路装置 |
| US7545145B2 (en) * | 2006-05-03 | 2009-06-09 | Baker Hughes Incorporated | Method and apparatus for tensorial micro-resistivity imaging in oil-based muds |
| US20080076848A1 (en) * | 2006-06-09 | 2008-03-27 | Xiaoming Jin | Low stress flowable compositions |
| US20080023131A1 (en) * | 2006-07-28 | 2008-01-31 | Pressley Mark W | Dual cure adhesive formulations |
| ATE516794T1 (de) | 2006-09-13 | 2011-08-15 | 3M Innovative Properties Co | Dentalzusammensetzungen mit organogelatoren, produkte und verfahren |
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| US20080096150A1 (en) | 2006-10-23 | 2008-04-24 | 3M Innovative Properties Company | Dental articles, methods, and kits including a compressible material |
| WO2008053552A1 (fr) * | 2006-11-01 | 2008-05-08 | Fujitsu Limited | Appareil de communication sans fil et procédé de communication sans fil |
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| ES2547303T3 (es) * | 2007-01-19 | 2015-10-05 | Ardea Biosciences, Inc. | Inhibidores de MEK |
| WO2009045752A2 (en) | 2007-10-01 | 2009-04-09 | 3M Innovative Properties Company | Orthodontic composition with polymeric fillers |
| GB0809545D0 (en) * | 2008-05-28 | 2008-07-02 | 3M Innovative Properties Co | Device for dispensing a dental composition |
| CN102046108B (zh) | 2008-06-03 | 2013-09-11 | 3M创新有限公司 | 用于混合牙科用组合物的混合机 |
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| RU2709201C1 (ru) | 2016-03-09 | 2019-12-17 | Токуяма Дентал Корпорейшн | Инициатор фотополимеризации и фотоотверждаемая композиция |
| EP3510058A4 (en) * | 2016-08-23 | 2020-04-22 | The University of Massachusetts | Polymerizing composition, method of manufacture thereof and articles comprising the same |
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| CN111961150B (zh) * | 2020-07-22 | 2021-06-18 | 福州大学 | 一种光控制阳离子聚合制备乙烯基醚类聚合物的方法 |
| CN116490337A (zh) * | 2020-08-31 | 2023-07-25 | 阿莱恩技术有限公司 | 相分离材料的3d打印复合物 |
| US20240065809A1 (en) | 2020-12-30 | 2024-02-29 | 3M Innovative Properties Company | Bondable orthodontic assemblies and methods for bonding |
| US11622916B2 (en) | 2021-03-12 | 2023-04-11 | Shofu Inc. | Photocurable composition excellent in curing depth |
| US20220387264A1 (en) | 2021-03-12 | 2022-12-08 | Shofu Inc. | Dental photocurable composition excellent in storage stability |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0290133A2 (en) * | 1987-04-02 | 1988-11-09 | Minnesota Mining And Manufacturing Company | Ternary photoinitiator system for addition polymerization |
Family Cites Families (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1408265A (en) * | 1971-10-18 | 1975-10-01 | Ici Ltd | Photopolymerisable composition |
| DE2403211C3 (de) | 1974-01-23 | 1981-12-24 | Etablissement Dentaire Ivoclar, Schaan | Werkstoff für Dentalzwecke |
| US4256828A (en) * | 1975-09-02 | 1981-03-17 | Minnesota Mining And Manufacturing Company | Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials |
| US4318766A (en) | 1975-09-02 | 1982-03-09 | Minnesota Mining And Manufacturing Company | Process of using photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials |
| US4228062A (en) | 1978-05-02 | 1980-10-14 | Lee Pharmaceuticals | Rapid setting high bond strength adhesive |
| US4156035A (en) * | 1978-05-09 | 1979-05-22 | W. R. Grace & Co. | Photocurable epoxy-acrylate compositions |
| US4221698A (en) | 1978-05-18 | 1980-09-09 | Lee Pharmaceuticals | Carvable dental restorative compositions |
| US4428807A (en) * | 1978-06-30 | 1984-01-31 | The Dow Chemical Company | Composition containing polymerizable entities having oxirane groups and terminal olefinic unsaturation in combination with free-radical and cationic photopolymerizations means |
| DE3029276A1 (de) * | 1980-08-01 | 1982-02-18 | Etablissement Dentaire Ivoclar, Schaan | Photopolymerisierbare masse, insbesondere fuer dentalzwecke |
| JPS6072918A (ja) * | 1983-09-30 | 1985-04-25 | Toshiba Corp | 光重合性エポキシ樹脂組成物 |
| JPS60197609A (ja) * | 1984-03-16 | 1985-10-07 | Kuraray Co Ltd | 歯科用組成物 |
| US4694029A (en) * | 1985-04-09 | 1987-09-15 | Cook Paint And Varnish Company | Hybrid photocure system |
| DE3546113A1 (de) | 1985-12-24 | 1987-06-25 | Santrade Ltd | Verbundpulverteilchen, verbundkoerper und verfahren zu deren herstellung |
| US4719149A (en) | 1986-02-28 | 1988-01-12 | Minnesota Mining And Manufacturing Company | Method for priming hard tissue |
| US4751138A (en) * | 1986-08-11 | 1988-06-14 | Minnesota Mining And Manufacturing Company | Coated abrasive having radiation curable binder |
| DE3634354A1 (de) | 1986-10-08 | 1988-04-21 | Muehlbauer Ernst Kg | Verbindungen, die aus aldehyd-, epoxid-, isocyanat- oder halotriazingruppen, polymerisierbaren gruppen und einem hoehermolekularen grundgeruest bestehen, dieselben enthaltenden mischungen und ihre verwendung |
| US4828583A (en) * | 1987-04-02 | 1989-05-09 | Minnesota Mining And Manufacturing Company | Coated abrasive binder containing ternary photoinitiator system |
| US4735632A (en) * | 1987-04-02 | 1988-04-05 | Minnesota Mining And Manufacturing Company | Coated abrasive binder containing ternary photoinitiator system |
| US4933376A (en) * | 1987-05-06 | 1990-06-12 | Mitsubishi Rayon Company Limited | Photopolymerizable dental composition |
| US4950696A (en) * | 1987-08-28 | 1990-08-21 | Minnesota Mining And Manufacturing Company | Energy-induced dual curable compositions |
| JPH01174523A (ja) | 1987-12-28 | 1989-07-11 | Mitsubishi Rayon Co Ltd | 光重合性組成物 |
| DE3801511C2 (de) | 1988-01-20 | 1996-11-14 | Espe Stiftung | Verwendung von Photoinitiatoren zur Herstellung von in zwei Schritten härtbaren Dentalmassen |
| JPH01213330A (ja) | 1988-02-22 | 1989-08-28 | Mitsubishi Rayon Co Ltd | 光重合性組成物 |
| US4985340A (en) | 1988-06-01 | 1991-01-15 | Minnesota Mining And Manufacturing Company | Energy curable compositions: two component curing agents |
| US5266609A (en) | 1989-01-27 | 1993-11-30 | Hall Neil R | Dental restorative adhesive having improved fracture toughness |
| DE3924308A1 (de) | 1989-07-22 | 1991-01-31 | Bayer Ag | Mehrstufig haertende kunststoffe |
| CA2028259A1 (en) | 1989-11-20 | 1991-05-21 | Stefan Weigl | Tacky photopolymerizable adhesive compositions |
| DE69006472T2 (de) | 1989-12-21 | 1994-09-01 | Minnesota Mining & Mfg | Zahnärztliche Zusammensetzungen, Verfahren zur Herstellung von geformten, zahnärztlichen Artikeln via "photoiniferte Polymerisation" von zahnärztlichen Zusammensetzungen und dadurch erzeugte geformte, zahnärztliche Artikel. |
| US5639802A (en) * | 1991-05-20 | 1997-06-17 | Spectra Group Limited, Inc. | Cationic polymerization |
| JPH0533250A (ja) | 1991-07-29 | 1993-02-09 | Mitsubishi Rayon Co Ltd | 不織布の製法 |
| US5256170A (en) | 1992-01-22 | 1993-10-26 | Minnesota Mining And Manufacturing Company | Coated abrasive article and method of making same |
| RU2057522C1 (ru) | 1992-03-09 | 1996-04-10 | Московский энергетический институт | Быстроотверждающаяся композиция |
| DE4220958C2 (de) | 1992-06-25 | 1994-04-28 | Ivoclar Ag Schaan | Dentalmaterial |
| US5624976A (en) | 1994-03-25 | 1997-04-29 | Dentsply Gmbh | Dental filling composition and method |
| US5453450A (en) | 1993-06-16 | 1995-09-26 | Minnesota Mining And Manufacturing Company | Stabilized curable adhesives |
| US5494943A (en) | 1993-06-16 | 1996-02-27 | Minnesota Mining And Manufacturing Company | Stabilized cationically-curable compositions |
| CA2146816A1 (en) | 1994-04-22 | 1995-10-23 | Joachim E. Klee | Process and composition for preparing a dental polymer product |
| DE4439485C2 (de) | 1994-10-26 | 1998-04-09 | Ivoclar Ag | Bicycloaliphatische 2-Methylen-1,3-dioxepane und deren Verwendung |
| US5856373A (en) * | 1994-10-31 | 1999-01-05 | Minnesota Mining And Manufacturing Company | Dental visible light curable epoxy system with enhanced depth of cure |
| WO1996013538A2 (en) | 1994-10-31 | 1996-05-09 | Minnesota Mining And Manufacturing Company | Visible-light curable epoxy system with enhanced depth of cure |
| US5721289A (en) | 1994-11-04 | 1998-02-24 | Minnesota Mining And Manufacturing Company | Stable, low cure-temperature semi-structural pressure sensitive adhesive |
| US5658963A (en) * | 1995-02-02 | 1997-08-19 | Bisco, Inc. | One-component primer/bonding-resin systems |
| US5750590A (en) * | 1995-02-22 | 1998-05-12 | Heraeus Kulzer Gmbh | Polymerizable material |
| DE19506222B4 (de) * | 1995-02-22 | 2004-11-25 | Heraeus Kulzer Gmbh & Co. Kg | Verwendung von polymerisierbaren Verbindungen für medizinische und dentale Zwecke |
| US5571297A (en) | 1995-06-06 | 1996-11-05 | Norton Company | Dual-cure binder system |
| DE19608313C2 (de) * | 1996-02-22 | 2000-08-31 | Ivoclar Ag Schaan | Polymerisierbare Hybridmonomere, Verfahren zu deren Herstellung und deren Verwendung |
-
1998
- 1998-06-05 US US09/092,550 patent/US6187836B1/en not_active Expired - Lifetime
- 1998-10-02 EP EP98950892A patent/EP1083859B1/en not_active Expired - Lifetime
- 1998-10-02 JP JP2000551720A patent/JP4369051B2/ja not_active Expired - Fee Related
- 1998-10-02 CA CA002332496A patent/CA2332496C/en not_active Expired - Fee Related
- 1998-10-02 CN CN98814105A patent/CN1102846C/zh not_active Expired - Fee Related
- 1998-10-02 BR BRPI9815890-2A patent/BR9815890B1/pt not_active IP Right Cessation
- 1998-10-02 DE DE69807756T patent/DE69807756T2/de not_active Expired - Lifetime
- 1998-10-02 KR KR1020007013680A patent/KR20010052534A/ko not_active Withdrawn
- 1998-10-02 ES ES98950892T patent/ES2178849T3/es not_active Expired - Lifetime
- 1998-10-02 AU AU96817/98A patent/AU740495B2/en not_active Ceased
- 1998-10-02 WO PCT/US1998/020836 patent/WO1999062460A1/en not_active Ceased
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0290133A2 (en) * | 1987-04-02 | 1988-11-09 | Minnesota Mining And Manufacturing Company | Ternary photoinitiator system for addition polymerization |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1083859B1 (en) | 2002-09-04 |
| CN1102846C (zh) | 2003-03-12 |
| DE69807756D1 (de) | 2002-10-10 |
| JP4369051B2 (ja) | 2009-11-18 |
| CA2332496A1 (en) | 1999-12-09 |
| CN1295455A (zh) | 2001-05-16 |
| KR20010052534A (ko) | 2001-06-25 |
| JP2002516830A (ja) | 2002-06-11 |
| US6187836B1 (en) | 2001-02-13 |
| ES2178849T3 (es) | 2003-01-01 |
| DE69807756T2 (de) | 2003-05-28 |
| WO1999062460A1 (en) | 1999-12-09 |
| AU9681798A (en) | 1999-12-20 |
| BR9815890B1 (pt) | 2010-07-13 |
| CA2332496C (en) | 2008-02-12 |
| BR9815890A (pt) | 2001-10-09 |
| EP1083859A1 (en) | 2001-03-21 |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |