DE19961342B4 - Radikalisch härtbare Urethanpräpolymere und deren Verwendung - Google Patents
Radikalisch härtbare Urethanpräpolymere und deren Verwendung Download PDFInfo
- Publication number
- DE19961342B4 DE19961342B4 DE19961342A DE19961342A DE19961342B4 DE 19961342 B4 DE19961342 B4 DE 19961342B4 DE 19961342 A DE19961342 A DE 19961342A DE 19961342 A DE19961342 A DE 19961342A DE 19961342 B4 DE19961342 B4 DE 19961342B4
- Authority
- DE
- Germany
- Prior art keywords
- meth
- weight
- acrylate
- urethane prepolymers
- component
- 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.)
- Expired - Fee Related
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- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 16
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 7
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 7
- 150000002009 diols Chemical class 0.000 claims abstract description 6
- 229920000193 polymethacrylate Polymers 0.000 claims abstract description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 13
- 239000000945 filler Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 5
- 239000005548 dental material Substances 0.000 claims description 5
- 239000003999 initiator Substances 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 239000004814 polyurethane Substances 0.000 claims description 5
- 229920002635 polyurethane Polymers 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000004568 cement Substances 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- 125000005442 diisocyanate group Chemical group 0.000 claims description 4
- 238000011049 filling Methods 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 238000004026 adhesive bonding Methods 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
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- 238000006243 chemical reaction Methods 0.000 abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 12
- 239000012948 isocyanate Substances 0.000 description 9
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- 238000009472 formulation Methods 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
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- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-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
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 3
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- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 239000012966 redox initiator Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ALRQPMSJKLMRHS-UHFFFAOYSA-N 1,1-dioxo-1,2,6-thiadiazinane-3,5-dione Chemical class O=C1CC(=O)NS(=O)(=O)N1 ALRQPMSJKLMRHS-UHFFFAOYSA-N 0.000 description 2
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 2
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 150000007656 barbituric acids Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- FGUUNXDRMVKHCF-UHFFFAOYSA-N bis(hydroxymethyl)tricyclo[5.2.1.0(2,6)]decane Chemical compound C12CCCC2(CO)C2(CO)CC1CC2 FGUUNXDRMVKHCF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
- AGKBXKFWMQLFGZ-UHFFFAOYSA-N (4-methylbenzoyl) 4-methylbenzenecarboperoxoate Chemical compound C1=CC(C)=CC=C1C(=O)OOC(=O)C1=CC=C(C)C=C1 AGKBXKFWMQLFGZ-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- JWTGRKUQJXIWCV-UHFFFAOYSA-N 1,2,3-trihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(O)C(O)CO JWTGRKUQJXIWCV-UHFFFAOYSA-N 0.000 description 1
- QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- 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 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- 125000004098 2,6-dichlorobenzoyl group Chemical group O=C([*])C1=C(Cl)C([H])=C([H])C([H])=C1Cl 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- GULWNZGRHZEYDH-UHFFFAOYSA-N 3-[4-[[6-[4-(2-carboxyprop-1-enoxy)butanoylamino]-3,5,5-trimethylhexyl]amino]-4-oxobutoxy]-2-methylprop-2-enoic acid Chemical compound OC(=O)C(C)=COCCCC(=O)NCCC(C)CC(C)(C)CNC(=O)CCCOC=C(C)C(O)=O GULWNZGRHZEYDH-UHFFFAOYSA-N 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
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- GEHDMHDFJOLWCL-UHFFFAOYSA-N CCCP(=O)C1=CC=CC=C1 Chemical compound CCCP(=O)C1=CC=CC=C1 GEHDMHDFJOLWCL-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
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- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- 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 1
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- 238000010521 absorption reaction Methods 0.000 description 1
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- 230000000996 additive effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 150000001279 adipic acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
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- 239000000378 calcium silicate Substances 0.000 description 1
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- 150000001718 carbodiimides Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
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- 125000004386 diacrylate group Chemical group 0.000 description 1
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical group CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 1
- DROMNWUQASBTFM-UHFFFAOYSA-N dinonyl benzene-1,2-dicarboxylate Chemical class CCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCC DROMNWUQASBTFM-UHFFFAOYSA-N 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
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- MHCLJIVVJQQNKQ-UHFFFAOYSA-N ethyl carbamate;2-methylprop-2-enoic acid Chemical compound CCOC(N)=O.CC(=C)C(O)=O MHCLJIVVJQQNKQ-UHFFFAOYSA-N 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
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- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
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- 230000002940 repellent Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229940105963 yttrium fluoride Drugs 0.000 description 1
- RBORBHYCVONNJH-UHFFFAOYSA-K yttrium(iii) fluoride Chemical compound F[Y](F)F RBORBHYCVONNJH-UHFFFAOYSA-K 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 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
- 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
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61K6/893—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6245—Polymers having terminal groups containing active hydrogen
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/671—Unsaturated compounds having only one group containing active hydrogen
- C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Dental Preparations (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Materials For Medical Uses (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19961342A DE19961342B4 (de) | 1999-12-17 | 1999-12-17 | Radikalisch härtbare Urethanpräpolymere und deren Verwendung |
| AT00985164T ATE251650T1 (de) | 1999-12-17 | 2000-12-15 | Radikalisch härtbare urethanpräpolymere und deren verwendung in dentalmassen |
| EP00985164A EP1242493B1 (de) | 1999-12-17 | 2000-12-15 | Radikalisch härtbare urethanpräpolymere und deren verwendung in dentalmassen |
| PCT/EP2000/012775 WO2001044338A1 (de) | 1999-12-17 | 2000-12-15 | Radikalisch härtbare urethanpräpolymere und deren verwendung in dentalmassen |
| DE50004033T DE50004033D1 (de) | 1999-12-17 | 2000-12-15 | Radikalisch härtbare urethanpräpolymere und deren verwendung in dentalmassen |
| US10/149,607 US7141616B2 (en) | 1999-12-17 | 2000-12-15 | Radically curable urethane prepolymers and their use in dental materials |
| AU21664/01A AU769994B2 (en) | 1999-12-17 | 2000-12-15 | Radically curable urethane prepolymers and their use in dental materials |
| JP2001544823A JP2003517066A (ja) | 1999-12-17 | 2000-12-15 | ラジカル的に硬化可能なウレタンプレポリマー類及びそれらの使用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19961342A DE19961342B4 (de) | 1999-12-17 | 1999-12-17 | Radikalisch härtbare Urethanpräpolymere und deren Verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE19961342A1 DE19961342A1 (de) | 2001-07-12 |
| DE19961342B4 true DE19961342B4 (de) | 2004-02-19 |
Family
ID=7933341
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19961342A Expired - Fee Related DE19961342B4 (de) | 1999-12-17 | 1999-12-17 | Radikalisch härtbare Urethanpräpolymere und deren Verwendung |
| DE50004033T Expired - Lifetime DE50004033D1 (de) | 1999-12-17 | 2000-12-15 | Radikalisch härtbare urethanpräpolymere und deren verwendung in dentalmassen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE50004033T Expired - Lifetime DE50004033D1 (de) | 1999-12-17 | 2000-12-15 | Radikalisch härtbare urethanpräpolymere und deren verwendung in dentalmassen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7141616B2 (enExample) |
| EP (1) | EP1242493B1 (enExample) |
| JP (1) | JP2003517066A (enExample) |
| AT (1) | ATE251650T1 (enExample) |
| AU (1) | AU769994B2 (enExample) |
| DE (2) | DE19961342B4 (enExample) |
| WO (1) | WO2001044338A1 (enExample) |
Families Citing this family (75)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001234117A (ja) * | 2000-02-21 | 2001-08-28 | Arakawa Chem Ind Co Ltd | コーティング剤組成物 |
| ATE324856T1 (de) | 2003-07-14 | 2006-06-15 | 3M Espe Ag | Klebstoffzusammensetzung mit verringerter polarität nach der polymerisation |
| EP1706440A1 (en) * | 2004-01-14 | 2006-10-04 | Cytec Surface Specialties, S.A. | Adhesives |
| DE602004022551D1 (de) * | 2004-09-24 | 2009-09-24 | 3M Espe Ag | Dentalklebstoffzusammensetzung |
| DE102005018451B4 (de) * | 2005-04-20 | 2008-07-24 | Heraeus Kulzer Gmbh | Verwendung von dendritischen Verbindungen in Dentalmaterialien |
| DE102005025915A1 (de) * | 2005-06-06 | 2006-12-07 | Wacker Chemie Ag | Vernetzbare Zusammensetzungen auf der Basis von Organosiliciumverbindungen |
| ES2526547T3 (es) * | 2005-08-10 | 2015-01-13 | Dentsply International Inc. | Procedimientos para preparar coronas dentales en la consulta |
| WO2007024652A2 (en) * | 2005-08-19 | 2007-03-01 | Premier Dental Products Company | Dental compositions based on nanofiber reinforcement |
| EP1849449A1 (en) * | 2006-04-26 | 2007-10-31 | 3M Innovative Properties Company | Filler containing composition and process for production and use thereof |
| US20080286724A1 (en) * | 2007-05-18 | 2008-11-20 | Ormco Corporation | Orthodontic adhesives |
| WO2009001826A1 (ja) * | 2007-06-27 | 2008-12-31 | Nippon Polyurethane Industry Co., Ltd. | 有機ポリイソシアネート組成物、並びにそれを用いた塗料組成物及び接着剤組成物 |
| EP2009039A1 (en) * | 2007-06-27 | 2008-12-31 | Universiteit Gent | Functionalised polyurethanes |
| EP2008636A1 (en) * | 2007-06-29 | 2008-12-31 | 3M Innovative Properties Company | Dental composition containing a polyfunctional (meth)acrylate comprising urethane, urea or amide groups, method of production and use thereof |
| 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 |
| DE102009058638A1 (de) | 2009-12-16 | 2011-06-22 | Ernst Mühlbauer GmbH & Co. KG, 25870 | Mehrkomponentensystem zur Herstellung eines Dentalmaterials |
| EP2401998A1 (en) | 2010-07-02 | 2012-01-04 | 3M Innovative Properties Company | Dental composition, kit of parts and use thereof |
| US8292625B2 (en) | 2010-07-23 | 2012-10-23 | Pulpdent Corporation | Radically curable urethane dimethacrylates and compositions thereof for tougher dental prosthetics |
| EP2412361A1 (en) | 2010-07-29 | 2012-02-01 | 3M Innovative Properties Company | Kit of parts, method of producing and use thereof |
| EP2481390A1 (en) | 2011-01-31 | 2012-08-01 | 3M Innovative Properties Company | Dental composition, method of producing and use thereof |
| EP2675421A2 (en) | 2011-02-15 | 2013-12-25 | 3M Innovative Properties Company | Dental compositions comprising mixture of isocyanurate monomer and tricyclodecane monomer |
| DE102011077254B3 (de) | 2011-06-09 | 2012-09-20 | Hilti Aktiengesellschaft | Verwendung einer Inhibitorkombination, Harzmischung, Reaktionsharzmörtel, Zweikomponenten - Mörtelsystem und dessen Verwendung sowie Patrone, Kartusche oder Folienbeutel enthaltend ein Zweikomponenten - Mörtelsystem |
| DE102011077248B3 (de) | 2011-06-09 | 2012-09-27 | Hilti Aktiengesellschaft | Verwendung eines Inhibitors, Harzmischung, Reaktionsharzmörtel, Zweikomponenten - Mörtelsystem und dessen Verwendung sowie Patrone, Kartusche oder Folienbeutel enthaltend ein Zweikomponenten - Mörtelsystem |
| DE102011078785B4 (de) | 2011-07-07 | 2013-03-07 | Hilti Aktiengesellschaft | Härterzusammensetzung, diese enthaltendes Mehrkomponenten-Mörtelsystem, dessen Verwendung sowie Patrone, Kartusche oder Folienbeutel enthaltend ein Mehrkomponenten - Mörtelsystem |
| WO2013023138A1 (en) | 2011-08-11 | 2013-02-14 | 3M Innovative Properties Company | Dental composition, method of producing and use thereof |
| US10544449B2 (en) * | 2013-06-14 | 2020-01-28 | Pacific Biosciences Of California, Inc. | Bis-biotinylation tags |
| EP3019141B1 (en) | 2013-07-08 | 2022-08-31 | 3M Innovative Properties Company | Hardenable dental composition containing a mixture of agglomerated and aggregated nanoparticles, kit of parts and use thereof |
| JP2015043793A (ja) * | 2013-08-27 | 2015-03-12 | ディーダブルエス エス・アール・エル | 人工歯の製造方法 |
| EP2862899A1 (de) | 2013-10-21 | 2015-04-22 | HILTI Aktiengesellschaft | Harzmischung auf Basis eines Vinylesterurethanharzes, Verfahren zu deren Herstellung und deren Verwendung |
| JP6599346B2 (ja) | 2014-02-18 | 2019-10-30 | スリーエム イノベイティブ プロパティズ カンパニー | 歯科用組成物及びその使用 |
| WO2015126666A1 (en) | 2014-02-18 | 2015-08-27 | 3M Innovative Properties Company | Dental composition and use thereof |
| ES2916205T5 (en) | 2015-01-09 | 2025-06-23 | Ivoclar Vivadent Ag | Dental composites with improved storage stability |
| DE102015104440A1 (de) * | 2015-03-24 | 2016-09-29 | Heraeus Kulzer Gmbh | Verfahren zur Herstellung dentaler Prothesen sowie gebrauchsfertiges Dentalmaterial und Kit enthaltend das Dentalmaterial |
| ITUB20160408A1 (it) | 2016-01-28 | 2017-07-28 | Dws Srl | Composizione di resina fotoindurente per produzioni stereolitografiche, articoli tridimensionali prodotti con detta composizione e relativo metodo di produzione |
| KR102757173B1 (ko) | 2016-03-07 | 2025-01-17 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 예비성형된 치과용 복합재 크라운, 이의 제조 방법 및 용도 |
| CN106202781B (zh) * | 2016-07-19 | 2019-06-25 | 广州大学 | 一种桥梁挠度温度效应和长期挠度的分离方法 |
| WO2018231583A1 (en) | 2017-06-14 | 2018-12-20 | 3M Innovative Properties Company | Curable composition for producing a dental composite crown and process of production |
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| EP3838863A1 (de) | 2019-12-18 | 2021-06-23 | Hilti Aktiengesellschaft | Verwendung einer reaktivharz-zusammensetzung für die chemische befestigung eines verankerungsmittels in einem bohrloch |
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| US12636234B2 (en) * | 2020-01-28 | 2026-05-26 | Tokuyama Dental Corporation | Method of producing polyurethane-based composite material, polyurethane-based composite material, and material for dental cutting work |
| US11998417B2 (en) | 2020-07-03 | 2024-06-04 | Solventum Intellectual Properties Company | Process for producing a surface-modified dental article |
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| WO2023275637A1 (en) | 2021-06-28 | 2023-01-05 | 3M Innovative Properties Company | Dental cement composition, kit of parts and use thereof |
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| CN120187382A (zh) | 2022-11-25 | 2025-06-20 | 舒万诺知识产权公司 | 在处理患者口腔中的牙齿状况的方法中使用的可固化组合物 |
| WO2024121658A1 (en) | 2022-12-06 | 2024-06-13 | Solventum Intellectual Properties Company | Surface-treated filler, dental composition containing such a filler, process of production and use thereof |
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| EP4570772A1 (en) | 2023-12-15 | 2025-06-18 | Hilti Aktiengesellschaft | Multi-component resin system suitable for chemical dowels having a high filling degree |
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| EP4574876A1 (en) | 2023-12-21 | 2025-06-25 | Hilti Aktiengesellschaft | Resin compositions comprising isocyanurates for improving pull out performance of chemical anchors |
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| EP4678620A1 (en) | 2024-07-12 | 2026-01-14 | Hilti Aktiengesellschaft | Fast-curing anchor system with optimized hardener distribution |
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| EP4714927A1 (en) | 2024-09-20 | 2026-03-25 | Hilti Aktiengesellschaft | A reactive resin composition comprising a peroxide-free initiator system with a sulfinate and a tertiary amine |
| EP4714925A1 (en) | 2024-09-20 | 2026-03-25 | Hilti Aktiengesellschaft | A reactive resin composition comprising a peroxide-free initiator system |
| EP4775555A1 (de) | 2025-01-13 | 2026-07-15 | Hilti Aktiengesellschaft | Härterzusammensetzung mit einem thiol für radikalisch härtbare verbindungen und deren verwendung |
| EP4775554A1 (de) | 2025-01-13 | 2026-07-15 | Hilti Aktiengesellschaft | Härterzusammensetzung mit einem bi- oder höherfunktionellen aliphatischen amin für radikalisch härtbare verbindungen und deren verwendung |
| EP4775556A1 (de) | 2025-01-13 | 2026-07-15 | Hilti Aktiengesellschaft | Härterzusammensetzung mit einer thioharnstoffverbindung für radikalisch härtbare verbindungen und deren verwendung |
| EP4775557A1 (de) | 2025-01-13 | 2026-07-15 | Hilti Aktiengesellschaft | Härterzusammensetzung für radikalisch härtbare verbindungen und deren verwendung |
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| DE2312559A1 (de) * | 1972-03-15 | 1973-09-27 | Amalgamated Dental Co Ltd | Zahnfuellmaterial |
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| EP0205846B1 (de) * | 1985-05-24 | 1991-10-02 | Teroson GmbH | Verfahren zur Herstellung von niedermolekularen hydroxyfunktionellen (Meth)acrylatpolymeren, deren Verwendung zur Herstellung von Isocyanat-Endgruppen enthaltenden Prepolymeren sowie daraus hergestellte Dicht- und Klebstoffe |
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| DE293487C (enExample) | ||||
| 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 |
| DE1495520B2 (de) | 1964-05-02 | 1970-06-25 | Deutsche Gold- U. Silber-Scheideanstalt, Vorm. Roessler, 6000 Frankfurt | Verfahren zum Polymerisieren |
| US3541068A (en) | 1968-07-12 | 1970-11-17 | Minnesota Mining & Mfg | Dental restorative compositions having enhanced stability |
| DE2658530C3 (de) | 1976-12-23 | 1985-08-22 | Siemens AG, 1000 Berlin und 8000 München | Vorrichtung zur Verarbeitung von auf einem Magnetband gespeicherter Signalinformation |
| US4206206A (en) * | 1977-03-24 | 1980-06-03 | Kowa Company, Ltd. | Antibiotics of the KA-6606 series and pharmaceutical compositions thereof |
| CH629664A5 (en) | 1977-04-19 | 1982-05-14 | Espe Pharm Praep | Polymerisable composition for dental purposes |
| US4206205A (en) | 1977-10-03 | 1980-06-03 | Merck & Co., Inc. | Monosaccharide and aglycone derivatives of C-076 |
| DE2909994A1 (de) | 1979-03-14 | 1980-10-02 | Basf Ag | Acylphosphinoxidverbindungen, ihre herstellung und verwendung |
| EP0007508B1 (de) | 1978-07-14 | 1983-06-01 | BASF Aktiengesellschaft | Acylphosphinoxidverbindungen, ihre Herstellung und ihre Verwendung |
| DE3034697A1 (de) | 1980-09-15 | 1982-05-06 | Basf Ag, 6700 Ludwigshafen | Acylphosphinsulfidverbindungen, ihre herstellung und verwendung |
| DE3107577A1 (de) | 1981-02-27 | 1982-09-16 | ESPE Fabrik pharmazeutischer Präparate GmbH, 8031 Seefeld | 1,2-6-thiadiazin-3,5-dion-1,1-dioxide und ihre verwendung |
| DE3133419A1 (de) | 1981-08-24 | 1983-03-10 | Basf Ag, 6700 Ludwigshafen | Acylphosphinoxidverbindungen und ihre verwendung |
| DE3316592A1 (de) | 1983-05-06 | 1984-11-08 | Basf Ag, 6700 Ludwigshafen | Verwendung zur herstellung von (meth) acrylsaeureestern und deren verwendung |
| DE3443221A1 (de) | 1984-11-27 | 1986-06-05 | ESPE Fabrik pharmazeutischer Präparate GmbH, 8031 Seefeld | Bisacylphosphinoxide, ihre herstellung und verwendung |
| CA1289394C (en) * | 1986-08-25 | 1991-09-24 | Duncan E. Waller | Method for making a dental impression |
| DE3704098A1 (de) | 1987-02-11 | 1988-08-25 | Basf Ag | Strahlungshaertbare acrylate |
| CA2005912A1 (en) | 1988-12-19 | 1990-06-19 | Peter Jochum | Dental compounds which contain bifunctional acrylic-acid esters or methacrylic-acid esters |
| DE4010176A1 (de) * | 1990-03-30 | 1991-10-02 | Basf Lacke & Farben | Verfahren zur herstellung einer mehrschichtigen lackierung und waessriger lack |
| DE4018183A1 (de) * | 1990-06-07 | 1991-12-12 | Bayer Ag | Lichthaertende abformmaterialien |
| DE4040290C2 (de) | 1990-12-17 | 1996-05-15 | Synthopol Chemie Dr Koch | Verfahren zur Herstellung von strahlungshärtbaren Polyesteracrylat-Bindemitteln |
| DE4314111A1 (de) * | 1993-04-29 | 1994-11-03 | Goldschmidt Ag Th | alpha,omega-Polymethacrylatdiole, Verfahren zu ihrer Herstellung und deren Verwendung zur Herstellung von Polymeren, insbesondere Polyurethanen und Polyestern |
| DE4445266A1 (de) | 1994-12-19 | 1996-06-20 | Thera Ges Fuer Patente | Fluoridabgebende Composite-Massen |
| DE19618446A1 (de) * | 1996-05-08 | 1997-11-13 | Basf Lacke & Farben | Aus mindestens 3 Komponenten bestehendes Beschichtungsmittel |
| DE19813353A1 (de) * | 1998-03-26 | 1999-09-30 | Bayer Ag | Verfahren zur Herstellung von Telechelen, so hergestellte Telechele und ihre Verwendung |
| DE19928238A1 (de) | 1999-06-21 | 2000-12-28 | Espe Dental Ag | Polymerisierbare Dentalmasse |
-
1999
- 1999-12-17 DE DE19961342A patent/DE19961342B4/de not_active Expired - Fee Related
-
2000
- 2000-12-15 DE DE50004033T patent/DE50004033D1/de not_active Expired - Lifetime
- 2000-12-15 WO PCT/EP2000/012775 patent/WO2001044338A1/de not_active Ceased
- 2000-12-15 US US10/149,607 patent/US7141616B2/en not_active Expired - Lifetime
- 2000-12-15 EP EP00985164A patent/EP1242493B1/de not_active Expired - Lifetime
- 2000-12-15 AT AT00985164T patent/ATE251650T1/de not_active IP Right Cessation
- 2000-12-15 AU AU21664/01A patent/AU769994B2/en not_active Ceased
- 2000-12-15 JP JP2001544823A patent/JP2003517066A/ja not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2312559A1 (de) * | 1972-03-15 | 1973-09-27 | Amalgamated Dental Co Ltd | Zahnfuellmaterial |
| EP0205846B1 (de) * | 1985-05-24 | 1991-10-02 | Teroson GmbH | Verfahren zur Herstellung von niedermolekularen hydroxyfunktionellen (Meth)acrylatpolymeren, deren Verwendung zur Herstellung von Isocyanat-Endgruppen enthaltenden Prepolymeren sowie daraus hergestellte Dicht- und Klebstoffe |
| DD293487A5 (de) * | 1989-03-09 | 1991-09-05 | Friedrich-Schiller-Universitaet,De | Dentalkomposite |
Also Published As
| Publication number | Publication date |
|---|---|
| US20030008967A1 (en) | 2003-01-09 |
| EP1242493B1 (de) | 2003-10-08 |
| WO2001044338A1 (de) | 2001-06-21 |
| DE50004033D1 (de) | 2003-11-13 |
| EP1242493A1 (de) | 2002-09-25 |
| AU2166401A (en) | 2001-06-25 |
| DE19961342A1 (de) | 2001-07-12 |
| US7141616B2 (en) | 2006-11-28 |
| AU769994B2 (en) | 2004-02-12 |
| JP2003517066A (ja) | 2003-05-20 |
| ATE251650T1 (de) | 2003-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8127 | New person/name/address of the applicant |
Owner name: 3M ESPE AG, 82229 SEEFELD, DE |
|
| 8181 | Inventor (new situation) |
Free format text: HECHT, REINHOLD, DR., 86916 KAUFERING, DE LECHNER, GUENTHER, DR., 82237 WOERTHSEE, DE LEHMANN, THOMAS, DR., 82229 SEEFELD, DE ECKHARDT, GUNTHER, DR., 82346 ANDECHS, DE GANGNUS, BERND, DR., 82346 ANDECHS, DE |
|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |