NO862197L - (met)-akrylsyrederivater av tricyklodekaner og deres anvendelse. - Google Patents
(met)-akrylsyrederivater av tricyklodekaner og deres anvendelse.Info
- Publication number
- NO862197L NO862197L NO862197A NO862197A NO862197L NO 862197 L NO862197 L NO 862197L NO 862197 A NO862197 A NO 862197A NO 862197 A NO862197 A NO 862197A NO 862197 L NO862197 L NO 862197L
- Authority
- NO
- Norway
- Prior art keywords
- tricyclodecanes
- acrylic acid
- meth
- group
- acid derivatives
- Prior art date
Links
- 150000001252 acrylic acid derivatives Chemical class 0.000 title 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 238000011049 filling Methods 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 19
- 238000006116 polymerization reaction Methods 0.000 abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000000178 monomer Substances 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 9
- 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 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- -1 Methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, pentoxy, isopentoxy, hexoxy Chemical group 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000002241 glass-ceramic Substances 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 150000002978 peroxides Chemical class 0.000 description 5
- 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 description 4
- 229930006711 bornane-2,3-dione Natural products 0.000 description 4
- 239000005548 dental material Substances 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000011814 protection agent Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 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 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 3
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 239000011256 inorganic filler Substances 0.000 description 3
- 229910003475 inorganic filler Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 208000002925 dental caries Diseases 0.000 description 2
- 210000003074 dental pulp Anatomy 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VNQXSTWCDUXYEZ-LDWIPMOCSA-N (+/-)-Camphorquinone Chemical compound C1C[C@@]2(C)C(=O)C(=O)[C@@H]1C2(C)C VNQXSTWCDUXYEZ-LDWIPMOCSA-N 0.000 description 1
- SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XDIIOLIFZDMGHX-UHFFFAOYSA-N 1-(n,3,5-trimethylanilino)propan-2-yl n-methylcarbamate Chemical compound CNC(=O)OC(C)CN(C)C1=CC(C)=CC(C)=C1 XDIIOLIFZDMGHX-UHFFFAOYSA-N 0.000 description 1
- HYQASEVIBPSPMK-UHFFFAOYSA-N 12-(2-methylprop-2-enoyloxy)dodecyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCCCCOC(=O)C(C)=C HYQASEVIBPSPMK-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- XXJWUZQJPJLUNE-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl 3-methylbut-2-enoate Chemical compound CC(=CC(=O)OCCOCCOCCOCCO)C XXJWUZQJPJLUNE-UHFFFAOYSA-N 0.000 description 1
- JWQRYFYKHVZIDQ-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-3,5-dimethylanilino]ethanol Chemical compound CC1=CC(C)=CC(N(CCO)CCO)=C1 JWQRYFYKHVZIDQ-UHFFFAOYSA-N 0.000 description 1
- JUVSRZCUMWZBFK-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-4-methylanilino]ethanol Chemical compound CC1=CC=C(N(CCO)CCO)C=C1 JUVSRZCUMWZBFK-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- SWZOQAGVRGQLDV-UHFFFAOYSA-N 4-[2-(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]-4-oxobutanoic acid Chemical compound CC1(C)CC(O)CC(C)(C)N1CCOC(=O)CCC(O)=O SWZOQAGVRGQLDV-UHFFFAOYSA-N 0.000 description 1
- LZAIWKMQABZIDI-UHFFFAOYSA-N 4-methyl-2,6-dioctadecylphenol Chemical compound CCCCCCCCCCCCCCCCCCC1=CC(C)=CC(CCCCCCCCCCCCCCCCCC)=C1O LZAIWKMQABZIDI-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone 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
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- MWPIIMNHWGOFBL-UHFFFAOYSA-N dichloromethane;toluene Chemical compound ClCCl.CC1=CC=CC=C1 MWPIIMNHWGOFBL-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 235000015927 pasta Nutrition 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007717 redox polymerization reaction Methods 0.000 description 1
- 239000011034 rock crystal Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
- C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61K6/893—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/02—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of urea, its salts, complexes or addition compounds
-
- 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
- C08F20/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F20/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Dental Preparations (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853522006 DE3522006A1 (de) | 1985-06-20 | 1985-06-20 | (meth)-acrylsaeure-derivate von tricyclodecanen und ihre verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO862197D0 NO862197D0 (no) | 1986-06-03 |
| NO862197L true NO862197L (no) | 1986-12-22 |
Family
ID=6273693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO862197A NO862197L (no) | 1985-06-20 | 1986-06-03 | (met)-akrylsyrederivater av tricyklodekaner og deres anvendelse. |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4744827A (ko) |
| EP (1) | EP0209700B1 (ko) |
| JP (1) | JPS61293961A (ko) |
| KR (1) | KR870000289A (ko) |
| CN (1) | CN86104081A (ko) |
| AT (1) | ATE55114T1 (ko) |
| AU (1) | AU595209B2 (ko) |
| DE (2) | DE3522006A1 (ko) |
| DK (1) | DK287786A (ko) |
| ES (1) | ES8801195A1 (ko) |
| FI (1) | FI862620A (ko) |
| GR (1) | GR861572B (ko) |
| HU (1) | HUT41979A (ko) |
| IL (1) | IL79127A0 (ko) |
| NO (1) | NO862197L (ko) |
| ZA (1) | ZA864570B (ko) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3522005A1 (de) * | 1985-06-20 | 1987-01-02 | Bayer Ag | (meth)-acrylsaeureester und ihre verwendung |
| DE3801511C2 (de) * | 1988-01-20 | 1996-11-14 | Espe Stiftung | Verwendung von Photoinitiatoren zur Herstellung von in zwei Schritten härtbaren Dentalmassen |
| JP2517753B2 (ja) * | 1988-12-28 | 1996-07-24 | 株式会社ジーシーデンタルプロダクツ | 人工歯とその製造方法 |
| US5093386A (en) * | 1989-05-16 | 1992-03-03 | Stamicarbon B.V. | Liquid curable plastic composition |
| DE3917320A1 (de) * | 1989-05-27 | 1990-12-20 | Bayer Ag | Harnstoffgruppen enthaltende (meth)-acrylsaeure-derivate von triisocyanaten und ihre verwendung |
| JP2683435B2 (ja) * | 1989-12-14 | 1997-11-26 | キヤノン株式会社 | インクジェットノズル製造用接着剤 |
| DE4439485C2 (de) * | 1994-10-26 | 1998-04-09 | Ivoclar Ag | Bicycloaliphatische 2-Methylen-1,3-dioxepane und deren Verwendung |
| DE19608316C2 (de) * | 1996-02-22 | 2000-11-09 | Ivoclar Ag Schaan | Funktionalisierte bicyclische (Meth)acrylate, Verfahren zu deren Herstellung und deren Verwendung #### |
| DE19742981B4 (de) * | 1997-09-29 | 2013-07-25 | 3M Deutschland Gmbh | Durch ROMP härtbare Dentalmassen |
| US20030215588A1 (en) * | 2002-04-09 | 2003-11-20 | Yeager Gary William | Thermoset composition, method, and article |
| JP4727173B2 (ja) * | 2003-07-24 | 2011-07-20 | サンメディカル株式会社 | 歯科用修復材組成物 |
| US7226980B2 (en) | 2003-08-07 | 2007-06-05 | General Electric Company | Thermoset composition, method for the preparation thereof, and articles prepared therefrom |
| US20050124721A1 (en) * | 2003-12-03 | 2005-06-09 | Arthur Samuel D. | Bulky monomers leading to resins exhibiting low polymerization shrinkage |
| US8727775B2 (en) | 2004-04-28 | 2014-05-20 | The Regents Of The University Of Colorado, A Body Corporate | Dimer acid-derived dimethacrylates and use in dental restorative compositions |
| CA2571207C (en) * | 2004-06-15 | 2014-08-05 | Dentsply International Inc. | Low shrinkage and low stress dental compositions |
| DE602005020806D1 (de) * | 2004-06-15 | 2010-06-02 | Dentsply Int Inc | Mensetzungen mit geringer polymerisationsspannung |
| US7173075B2 (en) | 2004-08-30 | 2007-02-06 | Ultradent Products, Inc. | Gas releasing sealing and filling compositions |
| DE102004060286A1 (de) * | 2004-12-15 | 2006-06-22 | Degussa Ag | Radikalisch homo- oder copolymerisierbare Verbindungen, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
| JP4790275B2 (ja) * | 2005-01-11 | 2011-10-12 | サンメディカル株式会社 | 歯科用修復材キットおよびその使用方法 |
| EP2042486A1 (en) * | 2007-09-26 | 2009-04-01 | 3M Innovative Properties Company | Methacrylate Based Monomers containing a Urethane Linkage, Process for Production and Use thereof |
| DE102010003883A1 (de) | 2010-04-12 | 2011-10-13 | Voco Gmbh | Lichthärtbares Kompositmaterial |
| DE102010003881A1 (de) | 2010-04-12 | 2011-10-13 | Voco Gmbh | Dentale Abdeckmasse |
| DE102010003884A1 (de) | 2010-04-12 | 2011-10-13 | Voco Gmbh | Dualhärtende, mehrkomponentige dentale Zusammensetzung |
| EP2401998A1 (en) * | 2010-07-02 | 2012-01-04 | 3M Innovative Properties Company | Dental composition, kit of parts and use thereof |
| EP2436363B1 (de) | 2010-09-30 | 2017-01-18 | VOCO GmbH | Zusammensetzung umfassend ein Monomer mit einem polyalicyclischen Strukturelement zum Füllen und/oder Versiegeln eines Wurzelkanals |
| EP2436668B1 (de) | 2010-09-30 | 2012-09-12 | VOCO GmbH | Polymerisierbare Verbindungen umfassend ein polyalicyclisches Strukturelement |
| EP2436365B1 (de) | 2010-09-30 | 2017-03-08 | VOCO GmbH | Kompositmaterial umfassend ein Monomer mit einem polyalicyclischen Strukturelement |
| US8669302B2 (en) | 2010-09-30 | 2014-03-11 | Voco Gmbh | Composite material comprising a monomer with a polyalicyclic structure element as a sealing material |
| EP2436364B1 (de) | 2010-09-30 | 2017-05-31 | VOCO GmbH | Lackzusammensetzung umfassend ein Monomer mit einem polyalicyclischen Strukturelement |
| EP2450025B1 (de) | 2010-11-08 | 2012-11-28 | VOCO GmbH | Polymerisierbare Phosphorsäurederivate umfassend ein polyalicyclisches Strukturelement |
| EP2481390A1 (en) | 2011-01-31 | 2012-08-01 | 3M Innovative Properties Company | Dental composition, method of producing and use thereof |
| WO2012112321A2 (en) | 2011-02-15 | 2012-08-23 | 3M Innovative Properties Company | Dental compositions comprising mixture of isocyanurate monomer and tricyclodecane monomer |
| US9173820B2 (en) | 2011-08-11 | 2015-11-03 | 3M Innovative Properties Company | Dental composition, method of producing and use thereof |
| JP2013060373A (ja) * | 2011-09-12 | 2013-04-04 | Idemitsu Kosan Co Ltd | アダマンタン誘導体 |
| EP2578200B1 (de) | 2011-10-04 | 2018-03-28 | VOCO GmbH | Zusammensetzungen zum Infiltrieren und/oder Versiegeln von Zahnhartsubstanz und entsprechende Verfahren |
| DE102013008176A1 (de) | 2012-10-05 | 2014-04-10 | Voco Gmbh | Kit und Verfahren zur indirekten chairside Herstellung von Kompositinlays |
| EP2823801B1 (de) | 2013-07-12 | 2017-04-19 | Ivoclar Vivadent AG | Dentalmaterialien auf der Basis von harnstoffgruppenhaltigen Monomeren |
| CN106029045B (zh) | 2014-02-18 | 2020-04-03 | 3M创新有限公司 | 牙科组合物及其用途 |
| EP3107522B1 (en) | 2014-02-18 | 2018-10-17 | 3M Innovative Properties Company | Dental composition and use thereof |
| JP6425048B2 (ja) * | 2014-03-25 | 2018-11-21 | 日産化学株式会社 | 重合性基と架橋性基とを有する化合物及びその製造方法 |
| EP3011949B1 (de) | 2014-10-23 | 2021-05-05 | VOCO GmbH | Härtbares dentalmaterial |
| EP3338756B1 (de) | 2016-12-21 | 2020-02-26 | VOCO GmbH | Lagerstabiler kunststoffmodifizierter glasionomerzement |
| DE102017103084A1 (de) | 2017-02-15 | 2018-08-16 | Voco Gmbh | Dentaler Kompositblock zur Herstellung permanenter indirekter Restaurationen im CAD/CAM Verfahren |
| DE102017105841A1 (de) | 2017-03-17 | 2018-09-20 | Voco Gmbh | Fräsrohling zur Herstellung einer indirekten dentalen Restauration, entsprechende Verwendungen und Verfahren |
| DE102017123009A1 (de) * | 2017-10-04 | 2019-04-04 | Kulzer Gmbh | Dentales Kompositmaterial sowie Fräsrohlinge dieses Kompositmaterials |
| DE102018103415A1 (de) | 2018-02-15 | 2019-08-22 | Voco Gmbh | Dentale Formkörper mit kontinuierlichem Farbverlauf |
| DE102018114690A1 (de) | 2018-06-19 | 2019-12-19 | Voco Gmbh | Thermowirksame dentale Kompositzusammensetzung |
| DE102019129551A1 (de) * | 2019-10-31 | 2021-05-06 | Kulzer Gmbh | Polymerisierbare Zusammensetzung |
| DE102019129550A1 (de) * | 2019-10-31 | 2021-05-06 | Kulzer Gmbh | Dentales Kompositmaterial |
| DE102021134260A1 (de) | 2021-12-22 | 2023-06-22 | Voco Gmbh | Dentale lichthärtbare Zusammensetzung sowie entsprechende Restaurationen, Herstellverfahren und Verwendungen |
| WO2023209463A1 (en) | 2022-04-26 | 2023-11-02 | 3M Innovative Properties Company | Dental composition containing a resorcinol or catechol moiety containing component and use thereof |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2714538C3 (de) * | 1977-04-01 | 1979-11-15 | Henkel Kgaa, 4000 Duesseldorf | Methacrylsäureester von auf tricyclischen Decanolen aufgebauten Verbindungen |
| CH629664A5 (en) * | 1977-04-19 | 1982-05-14 | Espe Pharm Praep | Polymerisable composition for dental purposes |
| US4131729A (en) * | 1978-04-21 | 1978-12-26 | Espe Fabrik Pharmazeutischer Praparate Gmbh | Dental compositions comprising acrylic esters of tricyclo [5.2.1.02,6 ] decane polymers |
| DE2931926A1 (de) * | 1979-08-07 | 1981-02-26 | Bayer Ag | Dentalmassen |
| DE2931925A1 (de) * | 1979-08-07 | 1981-02-26 | Bayer Ag | (meth)acrylsaeureester von ethergruppen enthaltenden tricyclischen decandiolen |
| GB2074590B (en) * | 1980-04-29 | 1984-02-22 | Kuraray Co | Acrylate urethane binders in dental cement compositions |
| US4379695A (en) * | 1980-06-02 | 1983-04-12 | Scientific Pharmaceuticals, Inc. | Dental material comprising dimethyacrylate adducts of glycidyl methacrylate with diesters of bis(hydroxymethyl) tricyclo[5.2.1.02,6 ]decane and dicarboxylic acids |
| ATE11909T1 (de) * | 1980-07-23 | 1985-03-15 | Blendax Werke Schneider Co | Addukte aus diisocyanaten und methacryloylalkylethern, -alkoxybenzolen bzw. alkoxycycloalkanen und deren verwendung. |
| DE3135115A1 (de) * | 1981-09-04 | 1983-03-24 | Bayer Ag, 5090 Leverkusen | Photopolymerisationsverfahren und hierfuer geeignete photoaktivatoren |
| US4420306A (en) * | 1982-06-24 | 1983-12-13 | Blendax-Werke R. Schneider Gmbh & Co. | Tetraacrylic and tetramethacrylic esters and dental materials containing same |
| DE3338077A1 (de) * | 1983-10-20 | 1985-05-09 | Bayer Ag, 5090 Leverkusen | Ungesaettigte esterisocyanate, ein verfahren zu ihrer herstellung und ihre verwendung bei der herstellung von olefinisch ungesaettigten oligourethanen |
| DE3563061D1 (en) * | 1984-08-17 | 1988-07-07 | Akzo Nv | Liquid, curable coating composition based on a hydroxyl groups-containing addition polymer as binder |
| DE3522005A1 (de) * | 1985-06-20 | 1987-01-02 | Bayer Ag | (meth)-acrylsaeureester und ihre verwendung |
-
1985
- 1985-06-20 DE DE19853522006 patent/DE3522006A1/de not_active Withdrawn
-
1986
- 1986-06-03 NO NO862197A patent/NO862197L/no unknown
- 1986-06-04 US US06/870,609 patent/US4744827A/en not_active Expired - Fee Related
- 1986-06-09 EP EP86107841A patent/EP0209700B1/de not_active Expired - Lifetime
- 1986-06-09 AT AT86107841T patent/ATE55114T1/de not_active IP Right Cessation
- 1986-06-09 DE DE8686107841T patent/DE3673094D1/de not_active Expired - Lifetime
- 1986-06-17 IL IL79127A patent/IL79127A0/xx unknown
- 1986-06-18 GR GR861572A patent/GR861572B/el unknown
- 1986-06-18 AU AU58980/86A patent/AU595209B2/en not_active Ceased
- 1986-06-18 FI FI862620A patent/FI862620A/fi not_active Application Discontinuation
- 1986-06-19 ES ES556289A patent/ES8801195A1/es not_active Expired
- 1986-06-19 HU HU862582A patent/HUT41979A/hu unknown
- 1986-06-19 ZA ZA864570A patent/ZA864570B/xx unknown
- 1986-06-19 DK DK287786A patent/DK287786A/da not_active Application Discontinuation
- 1986-06-19 KR KR1019860004880A patent/KR870000289A/ko not_active IP Right Cessation
- 1986-06-20 JP JP61143148A patent/JPS61293961A/ja active Pending
- 1986-06-20 CN CN198686104081A patent/CN86104081A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| ES8801195A1 (es) | 1987-12-16 |
| AU5898086A (en) | 1986-12-24 |
| GR861572B (en) | 1986-10-17 |
| EP0209700A3 (en) | 1988-01-13 |
| US4744827A (en) | 1988-05-17 |
| DE3522006A1 (de) | 1987-01-02 |
| HUT41979A (en) | 1987-06-29 |
| AU595209B2 (en) | 1990-03-29 |
| EP0209700B1 (de) | 1990-08-01 |
| ZA864570B (en) | 1987-02-25 |
| JPS61293961A (ja) | 1986-12-24 |
| CN86104081A (zh) | 1987-01-21 |
| FI862620A0 (fi) | 1986-06-18 |
| DE3673094D1 (de) | 1990-09-06 |
| EP0209700A2 (de) | 1987-01-28 |
| NO862197D0 (no) | 1986-06-03 |
| KR870000289A (ko) | 1987-02-17 |
| DK287786D0 (da) | 1986-06-19 |
| FI862620A (fi) | 1986-12-21 |
| IL79127A0 (en) | 1986-09-30 |
| DK287786A (da) | 1986-12-21 |
| ES556289A0 (es) | 1987-12-16 |
| ATE55114T1 (de) | 1990-08-15 |
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