CH621702A5 - Polymerisable dental filling composition - Google Patents
Polymerisable dental filling composition Download PDFInfo
- Publication number
- CH621702A5 CH621702A5 CH1033576A CH1033576A CH621702A5 CH 621702 A5 CH621702 A5 CH 621702A5 CH 1033576 A CH1033576 A CH 1033576A CH 1033576 A CH1033576 A CH 1033576A CH 621702 A5 CH621702 A5 CH 621702A5
- Authority
- CH
- Switzerland
- Prior art keywords
- weight
- group
- methacrylate monomer
- dental filling
- substituted
- Prior art date
Links
- 238000011049 filling Methods 0.000 title claims abstract description 51
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- 239000000178 monomer Substances 0.000 claims abstract description 54
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims abstract description 35
- -1 chloro- Chemical class 0.000 claims abstract description 32
- 239000007800 oxidant agent Substances 0.000 claims abstract description 28
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 23
- 150000003585 thioureas Chemical class 0.000 claims abstract description 16
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims abstract description 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000002252 acyl group Chemical class 0.000 claims abstract description 5
- 125000003710 aryl alkyl group Chemical class 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 25
- 239000000463 material Substances 0.000 claims description 21
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 15
- IPCRBOOJBPETMF-UHFFFAOYSA-N N-acetylthiourea Chemical compound CC(=O)NC(N)=S IPCRBOOJBPETMF-UHFFFAOYSA-N 0.000 claims description 15
- 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 claims description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 8
- HTKFORQRBXIQHD-UHFFFAOYSA-N allylthiourea Chemical compound NC(=S)NCC=C HTKFORQRBXIQHD-UHFFFAOYSA-N 0.000 claims description 8
- 229960001748 allylthiourea Drugs 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 claims description 6
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000864 peroxy group Chemical group O(O*)* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- XSZYESUNPWGWFQ-UHFFFAOYSA-N 1-(2-hydroperoxypropan-2-yl)-4-methylcyclohexane Chemical compound CC1CCC(C(C)(C)OO)CC1 XSZYESUNPWGWFQ-UHFFFAOYSA-N 0.000 claims description 2
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000005395 methacrylic acid group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001867 hydroperoxy group Chemical group [*]OO[H] 0.000 abstract description 2
- 238000004806 packaging method and process Methods 0.000 abstract description 2
- 125000005466 alkylenyl group Chemical group 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
- AMFGWXWBFGVCKG-UHFFFAOYSA-N Panavia opaque Chemical compound C1=CC(OCC(O)COC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 AMFGWXWBFGVCKG-UHFFFAOYSA-N 0.000 description 22
- 235000012239 silicon dioxide Nutrition 0.000 description 15
- 239000000377 silicon dioxide Substances 0.000 description 14
- 239000012456 homogeneous solution Substances 0.000 description 8
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 5
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 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 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000010419 fine particle Substances 0.000 description 3
- 210000000214 mouth Anatomy 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- CFJYNSNXFXLKNS-UHFFFAOYSA-N trans-p-menthane Natural products CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021486 amorphous silicon dioxide Inorganic materials 0.000 description 2
- UCGFRIAOVLXVKL-UHFFFAOYSA-N benzylthiourea Chemical compound NC(=S)NCC1=CC=CC=C1 UCGFRIAOVLXVKL-UHFFFAOYSA-N 0.000 description 2
- GMEGXJPUFRVCPX-UHFFFAOYSA-N butylthiourea Chemical compound CCCCNC(N)=S GMEGXJPUFRVCPX-UHFFFAOYSA-N 0.000 description 2
- CJOBVZJTOIVNNF-UHFFFAOYSA-N cadmium sulfide Chemical compound [Cd]=S CJOBVZJTOIVNNF-UHFFFAOYSA-N 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 210000003074 dental pulp Anatomy 0.000 description 2
- 229910000174 eucryptite Inorganic materials 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002432 hydroperoxides Chemical class 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229930004008 p-menthane Natural products 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- POXAIQSXNOEQGM-UHFFFAOYSA-N propan-2-ylthiourea Chemical compound CC(C)NC(N)=S POXAIQSXNOEQGM-UHFFFAOYSA-N 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000012966 redox initiator Substances 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VDTKXIMDQWHJSA-UHFFFAOYSA-N (2,3-dimethylphenyl)thiourea Chemical compound CC1=CC=CC(NC(N)=S)=C1C VDTKXIMDQWHJSA-UHFFFAOYSA-N 0.000 description 1
- HXCHZMHFZXNFIX-UHFFFAOYSA-N (2-methoxyphenyl)thiourea Chemical compound COC1=CC=CC=C1NC(N)=S HXCHZMHFZXNFIX-UHFFFAOYSA-N 0.000 description 1
- BHJYKFUCQNISJA-UHFFFAOYSA-N (3-hydroxyphenyl)thiourea Chemical compound NC(=S)NC1=CC=CC(O)=C1 BHJYKFUCQNISJA-UHFFFAOYSA-N 0.000 description 1
- SIKMRDUGDBMIIC-UHFFFAOYSA-N (4-methylbenzoyl)sulfonylthiourea Chemical compound C1(=CC=C(C=C1)C(=O)S(=O)(=O)NC(=S)N)C SIKMRDUGDBMIIC-UHFFFAOYSA-N 0.000 description 1
- OVRQXQSDQWOJIL-UHFFFAOYSA-N 1,1-dibutylthiourea Chemical compound CCCCN(C(N)=S)CCCC OVRQXQSDQWOJIL-UHFFFAOYSA-N 0.000 description 1
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 1
- DZZWKUMHMSNBSG-UHFFFAOYSA-N 1,3-bis(prop-2-enyl)thiourea Chemical compound C=CCNC(=S)NCC=C DZZWKUMHMSNBSG-UHFFFAOYSA-N 0.000 description 1
- 125000005655 1,3-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([*:2])C1([H])[H] 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- UKOJOHPYEVWPNN-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-methylthiourea Chemical compound CNC(=S)NC1=CC=C(Cl)C=C1 UKOJOHPYEVWPNN-UHFFFAOYSA-N 0.000 description 1
- JCJDOHYMJAOYPV-UHFFFAOYSA-N 1-methyl-3-pentylthiourea Chemical compound CCCCCNC(=S)NC JCJDOHYMJAOYPV-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
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- 229930185605 Bisphenol Natural products 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- VKOUCJUTMGHNOR-UHFFFAOYSA-N Diphenolic acid Chemical compound C=1C=C(O)C=CC=1C(CCC(O)=O)(C)C1=CC=C(O)C=C1 VKOUCJUTMGHNOR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical group CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
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- KFFQABQEJATQAT-UHFFFAOYSA-N N,N'-dibutylthiourea Chemical compound CCCCNC(=S)NCCCC KFFQABQEJATQAT-UHFFFAOYSA-N 0.000 description 1
- FLVIGYVXZHLUHP-UHFFFAOYSA-N N,N'-diethylthiourea Chemical compound CCNC(=S)NCC FLVIGYVXZHLUHP-UHFFFAOYSA-N 0.000 description 1
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- NOZAQBYNLKNDRT-UHFFFAOYSA-N [diacetyloxy(ethenyl)silyl] acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)C=C NOZAQBYNLKNDRT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
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- 239000012190 activator Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- 229920005601 base polymer Polymers 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 125000006267 biphenyl group Chemical group 0.000 description 1
- XVPDXVZSKZRXGF-UHFFFAOYSA-N bis[2-(2-methylprop-2-enoyloxy)ethyl] benzene-1,3-dicarboxylate Chemical compound CC(=C)C(=O)OCCOC(=O)C1=CC=CC(C(=O)OCCOC(=O)C(C)=C)=C1 XVPDXVZSKZRXGF-UHFFFAOYSA-N 0.000 description 1
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- LEEHHPPLIOFGSC-UHFFFAOYSA-N cyclohexylthiourea Chemical compound NC(=S)NC1CCCCC1 LEEHHPPLIOFGSC-UHFFFAOYSA-N 0.000 description 1
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- VAVFWTOVXLDJFG-UHFFFAOYSA-N n-(butylcarbamothioyl)butanamide Chemical compound CCCCNC(=S)NC(=O)CCC VAVFWTOVXLDJFG-UHFFFAOYSA-N 0.000 description 1
- DBOBDMZHSHKLSJ-UHFFFAOYSA-N n-(phenylcarbamothioyl)acetamide Chemical compound CC(=O)NC(=S)NC1=CC=CC=C1 DBOBDMZHSHKLSJ-UHFFFAOYSA-N 0.000 description 1
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- GKRZNOGGALENQJ-UHFFFAOYSA-N n-carbamoylacetamide Chemical group CC(=O)NC(N)=O GKRZNOGGALENQJ-UHFFFAOYSA-N 0.000 description 1
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QAKUNEDFMJPMGO-UHFFFAOYSA-N octylthiourea Chemical compound CCCCCCCCNC(N)=S QAKUNEDFMJPMGO-UHFFFAOYSA-N 0.000 description 1
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- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- NARVIWMVBMUEOG-UHFFFAOYSA-N prop-1-en-2-ol Chemical group CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000005628 tolylene group Chemical group 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- CIOXFKGQNIJXKF-UHFFFAOYSA-N tris(2-methoxyethoxy)silane Chemical compound COCCO[SiH](OCCOC)OCCOC CIOXFKGQNIJXKF-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/40—Redox systems
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F122/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F122/10—Esters
- C08F122/1006—Esters of polyhydric alcohols or polyhydric phenols, e.g. ethylene glycol dimethacrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K13/00—Use of mixtures of ingredients not covered by one single of the preceding main groups, each of these compounds being essential
- C08K13/02—Organic and inorganic ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/14—Peroxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing 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
- Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S528/92—Polymers useful for replacing hard animal tissues, e.g. dentures, bones
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Plastic & Reconstructive Surgery (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Materials Engineering (AREA)
- Dental Preparations (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/496,769 US3991008A (en) | 1974-08-12 | 1974-08-12 | Dental compositions having improved color stability |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621702A5 true CH621702A5 (en) | 1981-02-27 |
Family
ID=23974056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1033576A CH621702A5 (en) | 1974-08-12 | 1976-08-13 | Polymerisable dental filling composition |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3991008A (en, 2012) |
| JP (1) | JPS5332994A (en, 2012) |
| AT (1) | AT346497B (en, 2012) |
| AU (1) | AU513692B2 (en, 2012) |
| BE (1) | BE845122A (en, 2012) |
| CA (1) | CA1069639A (en, 2012) |
| CH (1) | CH621702A5 (en, 2012) |
| DE (1) | DE2635595C2 (en, 2012) |
| FR (1) | FR2361096A1 (en, 2012) |
| GB (1) | GB1566125A (en, 2012) |
| NL (1) | NL185982C (en, 2012) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4256603A (en) * | 1977-04-15 | 1981-03-17 | Den-Mat, Inc. | Composition for repair of porcelain dental prostheses |
| US4141877A (en) * | 1977-09-06 | 1979-02-27 | Corning Glass Works | Processing organic polymers with hydrated glasses |
| JPS5579312A (en) * | 1978-12-13 | 1980-06-14 | Denki Kagaku Kogyo Kk | Filler for synthetic resin for dental use |
| JPS55137178A (en) * | 1979-04-11 | 1980-10-25 | Kanebo Ltd | Adhesive material for rigid living tissue |
| US4327014A (en) * | 1979-04-11 | 1982-04-27 | Kanebo Ltd. | Resin-forming material, implant material and compositions for restorative material suitable for medical or dental use |
| US4292236A (en) * | 1979-11-16 | 1981-09-29 | Den-Mat, Inc. | Composition for repair of porcelain fixtures |
| EP0040232B2 (de) * | 1979-11-22 | 1993-09-29 | ESPE Stiftung & Co Produktions- und Vertriebs KG | Verwendung von kieselsäuregranulaten als füllstoffe für dentalmassen |
| ZA812567B (en) * | 1980-04-29 | 1982-11-24 | Colgate Palmolive Co | Dental compositions |
| EP0097864B1 (de) * | 1982-06-21 | 1986-11-12 | Hoechst Aktiengesellschaft | Photopolymerisierbares Gemisch und damit hergestelltes photopolymerisierbares Kopiermaterial |
| US4515910A (en) * | 1983-01-26 | 1985-05-07 | Rawls Henry R | Interpolymeric resin for treatment of teeth |
| US4536523A (en) * | 1983-12-23 | 1985-08-20 | The United States Of America As Represented By The Secretary Of The Department Of Health & Human Services | Dental composite formulation from acrylate monomer and polythiol accelerator |
| US4616073A (en) * | 1984-08-09 | 1986-10-07 | The United States Of America As Represented By The Department Of Health And Human Services | Hydrophobic dental composites based on a polyfluorinated dental resin |
| US4783491A (en) * | 1984-12-12 | 1988-11-08 | Sankin Kogyo Kabushiki Kaisha | Dental materials having X-ray contrastability |
| US5034433A (en) * | 1990-04-10 | 1991-07-23 | Essential Dental Systems, Inc. | Composite dental cement composition containing titanium |
| DE19818210C5 (de) | 1998-04-24 | 2007-02-08 | Ivoclar Vivadent Ag | Radikalisch polymerisierbarer Dentalwerkstoff |
| US6545052B2 (en) | 2000-05-10 | 2003-04-08 | Fan Tech, Ltd. | Methods and compositions for inhibiting free radical polymerization in skin and hair |
| US6586628B2 (en) | 2000-05-10 | 2003-07-01 | The United States Of America, As Represented By The Secretary Of Agriculture | 3-Methoxybenzyl thiourea derivatives and improved lipid compositions containing same |
| US20080003542A1 (en) * | 2000-08-11 | 2008-01-03 | Shuhua Jin | Self-Curing System For Endodontic Sealant Applications |
| US7275932B2 (en) * | 2001-09-20 | 2007-10-02 | Pentron Clinical Technologies, Llc | Self-curing system for endodontic sealant applications |
| US6787584B2 (en) * | 2000-08-11 | 2004-09-07 | Pentron Corporation | Dental/medical compositions comprising degradable polymers and methods of manufacture thereof |
| US7173074B2 (en) * | 2001-12-29 | 2007-02-06 | 3M Innovative Properties Company | Composition containing a polymerizable reducing agent, kit, and method |
| CN100558775C (zh) * | 2001-12-29 | 2009-11-11 | 3M创新有限公司 | 包含可聚合还原剂的组合物、试剂盒及其制备方法 |
| US6982288B2 (en) * | 2002-04-12 | 2006-01-03 | 3M Innovative Properties Company | Medical compositions containing an ionic salt, kits, and methods |
| DE10249518B3 (de) * | 2002-10-23 | 2004-02-19 | Heraeus Kulzer Gmbh & Co. Kg | Dentales Formteil, insbesondere künstlicher Zahn |
| US7166651B2 (en) * | 2003-05-19 | 2007-01-23 | Kerr Corporation | Two-part self-adhering dental compositions |
| US7214726B2 (en) * | 2003-07-17 | 2007-05-08 | Kerr Corporation | Methods of using two-part self-adhering dental compositions |
| US20050154081A1 (en) * | 2004-01-09 | 2005-07-14 | Bisco, Inc. | Opacity and color change polymerizable dental materials |
| US7498367B2 (en) | 2005-02-21 | 2009-03-03 | Kerr Corporation | Acid-tolerant dental composition |
| JP4758662B2 (ja) * | 2005-03-07 | 2011-08-31 | 株式会社トクヤマ | 歯冠修復用光硬化性組成物 |
| JP2007023106A (ja) * | 2005-07-13 | 2007-02-01 | Japan U-Pica Co Ltd | 常温硬化性樹脂組成物 |
| KR100704904B1 (ko) * | 2005-07-25 | 2007-04-06 | (주)아모레퍼시픽 | 치아미백용 치약 조성물 |
| US20070100019A1 (en) * | 2005-08-02 | 2007-05-03 | Fuming Sun | Catalyst system for dental compositions |
| US7855242B2 (en) * | 2005-09-01 | 2010-12-21 | Pentron Clinical Technologies Llc | Dental resin composition, method of manufacture, and method of use thereof |
| EP1849449A1 (en) * | 2006-04-26 | 2007-10-31 | 3M Innovative Properties Company | Filler containing composition and process for production and use thereof |
| WO2008134024A2 (en) * | 2007-04-25 | 2008-11-06 | Dentsply International Inc. | Self-adhesive dental cement |
| US8785514B2 (en) * | 2007-11-29 | 2014-07-22 | The Board Of Regents Of The University Of Texas System | Dual-cure dental resins and adhesives with increased cure and color stability and low color |
| JP2009144054A (ja) * | 2007-12-14 | 2009-07-02 | Gc Corp | 重合性組成物 |
| US8551457B2 (en) | 2008-11-25 | 2013-10-08 | The Procter & Gamble Company | Oral care compositions comprising spherical fused silica |
| US8221722B2 (en) * | 2008-11-25 | 2012-07-17 | The Procter & Gamble Company | Antibacterial oral care compositions with fused silica |
| US9365750B2 (en) | 2012-06-27 | 2016-06-14 | Henkel IP & Holding GmbH | Accelerators for curable compositions |
| US9371473B2 (en) | 2012-06-27 | 2016-06-21 | Henkel IP & Holding GmbH | Accelerators for two step adhesive systems |
| US10590311B2 (en) * | 2012-06-27 | 2020-03-17 | Henkel IP & Holding GmbH | Accelerators for two part curable compositions |
| RU2608129C2 (ru) | 2012-11-05 | 2017-01-13 | Дзе Проктер Энд Гэмбл Компани | Термически обработанная осажденная двуокись кремния |
| EP2921156B1 (de) | 2014-03-20 | 2019-10-02 | Ivoclar Vivadent AG | Monomermischung zur Herstellung von Dentalwerkstoffen |
| EP2921154B1 (de) * | 2014-03-20 | 2017-03-08 | Ivoclar Vivadent AG | Photopolymerisierbare und dualhärtende Dentalwerkstoffe auf der Basis von Thioharnstoffderivaten und Bisacyldialkylgermanium-Verbindungen |
| US9676922B2 (en) | 2014-06-11 | 2017-06-13 | IPS, Corporation—Weld-On Division | Heat and moisture resistant acrylic adhesive composition |
| AU2016218284A1 (en) | 2015-02-09 | 2017-07-27 | Zest Ip Holdings, Llc | Dental compositions and methods of use |
| EP3692974B1 (de) * | 2019-02-07 | 2021-08-25 | Ivoclar Vivadent AG | Dentalmaterialien mit verbesserten mechanischen eigenschaften |
| EP3692975B1 (de) * | 2019-02-07 | 2022-05-18 | Ivoclar Vivadent AG | Dentalmaterialien mit verbessertem abbindeverhalten |
| CA3128005A1 (en) | 2019-02-07 | 2020-08-13 | Ips Corporation | Gasketed pipe joint formed in place and method of making same |
| ES2879378T3 (es) | 2019-02-07 | 2021-11-22 | Ivoclar Vivadent Ag | Materiales dentales a base de sistemas rédox con derivados de hidroperóxido de cumeno de olor reducido |
| ES2941670T3 (es) | 2021-01-21 | 2023-05-24 | Ivoclar Vivadent Ag | Material dental para la producción de coronas y puentes provisionales |
| EP4039220B1 (de) | 2021-02-05 | 2022-12-28 | Ivoclar Vivadent AG | Dentalmaterialien auf der basis von polymerisationsfähigen thioharnstoff-derivaten |
| EP4094748B1 (de) | 2021-05-26 | 2023-09-20 | Ivoclar Vivadent AG | Dentalwerkstoffe auf basis von redoxsystemen mit oligomeren cumolhydroperoxid-derivaten |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2558139A (en) * | 1947-08-26 | 1951-06-26 | L D Caulk Company | Dental material and method |
| GB715382A (en) * | 1950-10-10 | 1954-09-15 | Dunlop Rubber Co | Improvements in or relating to the polymerisation of unsaturated compounds |
| US3066112A (en) * | 1959-01-30 | 1962-11-27 | Rafael L Bowen | Dental filling material comprising vinyl silane treated fused silica and a binder consisting of the reaction product of bis phenol and glycidyl acrylate |
| US3591438A (en) * | 1968-03-04 | 1971-07-06 | Loctite Corp | Polymerizable acrylate composition and curing accelerator therefor |
| US3539533A (en) * | 1968-06-14 | 1970-11-10 | Johnson & Johnson | Dental filling material |
| US3625916A (en) * | 1968-07-03 | 1971-12-07 | Ortho International Services I | Synthetic plastic dental adhesive |
| US3709866A (en) * | 1970-06-01 | 1973-01-09 | Dentsply Int Inc | Photopolymerizable dental products |
| US3751399A (en) * | 1971-05-24 | 1973-08-07 | Lee Pharmaceuticals | Polyacrylate resin compositions |
| US3832326A (en) * | 1972-06-01 | 1974-08-27 | Nat Distillers Chem Corp | Flame retardant compositions |
| US3845009A (en) * | 1972-02-03 | 1974-10-29 | Johnson & Johnson | Cement compositions employing novel methacrylate monomer |
| CA1030695A (en) * | 1973-01-15 | 1978-05-02 | Loctite Corporation | Polymerizable anaerobic compositions |
-
1974
- 1974-08-12 US US05/496,769 patent/US3991008A/en not_active Expired - Lifetime
-
1975
- 1975-04-28 CA CA225,965A patent/CA1069639A/en not_active Expired
-
1976
- 1976-08-07 DE DE2635595A patent/DE2635595C2/de not_active Expired
- 1976-08-10 FR FR7624402A patent/FR2361096A1/fr active Granted
- 1976-08-10 AU AU16728/76A patent/AU513692B2/en not_active Ceased
- 1976-08-10 AT AT591176A patent/AT346497B/de not_active IP Right Cessation
- 1976-08-12 BE BE169755A patent/BE845122A/xx not_active IP Right Cessation
- 1976-08-13 CH CH1033576A patent/CH621702A5/de not_active IP Right Cessation
- 1976-08-30 NL NLAANVRAGE7609611,A patent/NL185982C/xx not_active IP Right Cessation
- 1976-09-03 JP JP10571076A patent/JPS5332994A/ja active Granted
- 1976-10-11 GB GB42171/76A patent/GB1566125A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2361096B1 (en, 2012) | 1982-08-20 |
| AU513692B2 (en) | 1980-12-18 |
| DE2635595C2 (de) | 1986-01-23 |
| NL7609611A (nl) | 1978-03-02 |
| CA1069639A (en) | 1980-01-08 |
| JPS5332994A (en) | 1978-03-28 |
| JPS6210964B2 (en, 2012) | 1987-03-10 |
| US3991008A (en) | 1976-11-09 |
| GB1566125A (en) | 1980-04-30 |
| NL185982C (nl) | 1990-09-03 |
| FR2361096A1 (fr) | 1978-03-10 |
| AT346497B (de) | 1978-11-10 |
| NL185982B (nl) | 1990-04-02 |
| AU1672876A (en) | 1978-02-16 |
| BE845122A (fr) | 1976-12-01 |
| ATA591176A (de) | 1978-03-15 |
| DE2635595A1 (de) | 1978-02-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |