CS199730B2 - Method of preparing materials for copies,available especially for dental use - Google Patents
Method of preparing materials for copies,available especially for dental use Download PDFInfo
- Publication number
- CS199730B2 CS199730B2 CS783387A CS338778A CS199730B2 CS 199730 B2 CS199730 B2 CS 199730B2 CS 783387 A CS783387 A CS 783387A CS 338778 A CS338778 A CS 338778A CS 199730 B2 CS199730 B2 CS 199730B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- weight
- diisocyanate
- parts
- compounds
- glycol
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title abstract description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 14
- 229920000728 polyester Polymers 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 229920000570 polyether Polymers 0.000 claims description 13
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 20
- 239000007795 chemical reaction product Substances 0.000 abstract description 6
- -1 cycloaliphatic Chemical group 0.000 description 35
- 239000000203 mixture Substances 0.000 description 32
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000011347 resin Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 10
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 9
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 8
- 239000000945 filler Substances 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000004814 polyurethane Substances 0.000 description 6
- 229920002635 polyurethane Polymers 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000012763 reinforcing filler Substances 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 5
- 235000011037 adipic acid Nutrition 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 150000002334 glycols Chemical class 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 229950000688 phenothiazine Drugs 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 5
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000010440 gypsum Substances 0.000 description 4
- 229910052602 gypsum Inorganic materials 0.000 description 4
- 235000019589 hardness Nutrition 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920006295 polythiol Polymers 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000004982 aromatic amines Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical class OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000007788 liquid Substances 0.000 description 3
- UDKSLGIUCGAZTK-UHFFFAOYSA-N phenyl pentadecane-1-sulfonate Chemical compound CCCCCCCCCCCCCCCS(=O)(=O)OC1=CC=CC=C1 UDKSLGIUCGAZTK-UHFFFAOYSA-N 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- MQUUQPKBOFIRRS-UHFFFAOYSA-N 1,4,6-trimethylcyclohexa-2,4-dien-1-amine Chemical compound CC1C=C(C)C=CC1(C)N MQUUQPKBOFIRRS-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 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
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 2
- 239000000378 calcium silicate Substances 0.000 description 2
- 229910052918 calcium silicate Inorganic materials 0.000 description 2
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920005749 polyurethane resin Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 150000003606 tin compounds Chemical class 0.000 description 2
- 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 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- BOOBDAVNHSOIDB-UHFFFAOYSA-N (2,3-dichlorobenzoyl) 2,3-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC=CC(C(=O)OOC(=O)C=2C(=C(Cl)C=CC=2)Cl)=C1Cl BOOBDAVNHSOIDB-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DWHJJLTXBKSHJG-HWKANZROSA-N (e)-5-hydroxy-2-methylpent-2-enoic acid Chemical compound OC(=O)C(/C)=C/CCO DWHJJLTXBKSHJG-HWKANZROSA-N 0.000 description 1
- OYWRDHBGMCXGFY-UHFFFAOYSA-N 1,2,3-triazinane Chemical class C1CNNNC1 OYWRDHBGMCXGFY-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- XKFROYFCCQEOKV-UHFFFAOYSA-N 1,4,5,6-tetramethylcyclohexa-2,4-dien-1-amine Chemical group CC1(N)C(C(=C(C=C1)C)C)C XKFROYFCCQEOKV-UHFFFAOYSA-N 0.000 description 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-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
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- FWWWRCRHNMOYQY-UHFFFAOYSA-N 1,5-diisocyanato-2,4-dimethylbenzene Chemical compound CC1=CC(C)=C(N=C=O)C=C1N=C=O FWWWRCRHNMOYQY-UHFFFAOYSA-N 0.000 description 1
- RCRYERQRZNATJP-UHFFFAOYSA-N 1-(4-hydroxyphenyl)pentylphosphonic acid Chemical compound CCCCC(P(O)(O)=O)C1=CC=C(O)C=C1 RCRYERQRZNATJP-UHFFFAOYSA-N 0.000 description 1
- VUPPFTQPSRNUJO-UHFFFAOYSA-N 1-N,4-N-bis(1-methylcyclohexa-2,4-dien-1-yl)benzene-1,4-diamine Chemical compound CC1(CC=CC=C1)NC1=CC=C(C=C1)NC1(CC=CC=C1)C VUPPFTQPSRNUJO-UHFFFAOYSA-N 0.000 description 1
- SZBXTBGNJLZMHB-UHFFFAOYSA-N 1-chloro-2,4-diisocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1N=C=O SZBXTBGNJLZMHB-UHFFFAOYSA-N 0.000 description 1
- AOGDNNLIBAUIIX-UHFFFAOYSA-N 1-n,4-n-dinaphthalen-1-ylbenzene-1,4-diamine Chemical compound C1=CC=C2C(NC=3C=CC(NC=4C5=CC=CC=C5C=CC=4)=CC=3)=CC=CC2=C1 AOGDNNLIBAUIIX-UHFFFAOYSA-N 0.000 description 1
- TWNLLIFNDPYUTQ-UHFFFAOYSA-N 1-tert-butyl-2,4-diisocyanatobenzene Chemical compound CC(C)(C)C1=CC=C(N=C=O)C=C1N=C=O TWNLLIFNDPYUTQ-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-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
- UJAWGGOCYUPCPS-UHFFFAOYSA-N 4-(2-phenylpropan-2-yl)-n-[4-(2-phenylpropan-2-yl)phenyl]aniline Chemical compound C=1C=C(NC=2C=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C=CC=1C(C)(C)C1=CC=CC=C1 UJAWGGOCYUPCPS-UHFFFAOYSA-N 0.000 description 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/06—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyurethanes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/90—Compositions for taking dental impressions
-
- 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)
- Oral & Maxillofacial Surgery (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Dental Preparations (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Dental Tools And Instruments Or Auxiliary Dental Instruments (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2724260A DE2724260C2 (de) | 1977-05-28 | 1977-05-28 | Abformmaterialien für die Zahnheilkunde |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199730B2 true CS199730B2 (en) | 1980-07-31 |
Family
ID=6010149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS783387A CS199730B2 (en) | 1977-05-28 | 1978-05-24 | Method of preparing materials for copies,available especially for dental use |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4182829A (de) |
| JP (1) | JPS53148890A (de) |
| AR (1) | AR215307A1 (de) |
| AT (1) | AT376988B (de) |
| AU (1) | AU3628878A (de) |
| BE (1) | BE867527A (de) |
| BR (1) | BR7803361A (de) |
| CA (1) | CA1142684A (de) |
| CH (1) | CH635598A5 (de) |
| CS (1) | CS199730B2 (de) |
| DD (1) | DD138148A5 (de) |
| DE (1) | DE2724260C2 (de) |
| DK (1) | DK235378A (de) |
| ES (1) | ES470181A1 (de) |
| FI (1) | FI781666A7 (de) |
| FR (1) | FR2391705A1 (de) |
| GB (1) | GB1602414A (de) |
| GR (1) | GR73553B (de) |
| HU (1) | HU177288B (de) |
| IE (1) | IE46980B1 (de) |
| IT (1) | IT1109195B (de) |
| NL (1) | NL7805763A (de) |
| NO (1) | NO151528C (de) |
| PL (2) | PL113841B1 (de) |
| PT (1) | PT68066B (de) |
| SE (1) | SE442949B (de) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS543189A (en) * | 1977-06-08 | 1979-01-11 | Nhk Spring Co Ltd | Polymerizable composition and its polymer and preparation |
| ZA80393B (en) * | 1979-02-17 | 1981-08-26 | Dunlop Ltd | Cellular elastomeric compositions |
| US4246391A (en) * | 1979-06-26 | 1981-01-20 | Union Carbide Corporation | Procedure for production of lower viscosity radiation-curable acrylated urethanes |
| DE3161404D1 (en) | 1980-03-27 | 1983-12-22 | British Petroleum Co Plc | Surface coatings, compositions therefor, and methods of preparing them |
| CA1163410A (en) * | 1980-05-01 | 1984-03-13 | Robert F. Navin | Method for making coated molded articles |
| EP0076126B1 (de) * | 1981-09-29 | 1986-01-22 | Olin Corporation | Modifiziertes Polyurethan enthaltende flüssige Polymer-Zusammensetzungen |
| BR8303781A (pt) * | 1982-07-28 | 1984-04-24 | Goodyear Tire & Rubber | Poliuretana insaturada e processo para sua producao |
| US4452964A (en) * | 1983-02-07 | 1984-06-05 | The Goodyear Tire & Rubber Company | Peroxide cured urethanes for application to rim and adhesives |
| US4439600A (en) * | 1983-06-03 | 1984-03-27 | Loctite Corporation | Cure to elastomers compositions |
| CA1312402C (en) * | 1984-07-31 | 1993-01-05 | Dentsply International Inc. | Chain extended urethane diacrylate and dental impression formation |
| US5177120A (en) * | 1984-07-31 | 1993-01-05 | Dentsply Research & Development Corp. | Chain extended urethane diacrylate and dental impression formation |
| US4813875A (en) * | 1984-07-31 | 1989-03-21 | Dentsply Research & Development Corp. | Chain extended urethane diacrylate and dental impression formation |
| US5137448A (en) * | 1984-07-31 | 1992-08-11 | Dentsply Research & Development Corp. | Dental impression method with photocuring of impression material in light transmissive tray |
| US4584325A (en) * | 1985-04-26 | 1986-04-22 | Thermocell Development, Ltd. | Modified aliphatic polyurethane polymers and method of preparing and using same |
| US4761136A (en) * | 1986-07-28 | 1988-08-02 | Kerr Manufacturing Company | Visible light cured impression material |
| CA1311574C (en) * | 1986-07-28 | 1992-12-15 | Robert L. Probst | Visible light cured impression material |
| DE3632215A1 (de) * | 1986-09-23 | 1988-03-24 | Dentaire Ivoclar Ets | Reaktiver organischer fuellstoff sowie dessen verwendung |
| CA1302659C (en) * | 1986-10-24 | 1992-06-09 | Hans-Peter K. Gribi | Dental impression material |
| US5709548A (en) * | 1990-02-23 | 1998-01-20 | Minnesota Mining And Manufacturing Company | Dental crown liner composition and methods of preparing provisional applications |
| ES2060075T3 (es) * | 1990-02-23 | 1994-11-16 | Minnesota Mining & Mfg | Composicion semi-termoplastica para moldeo que tiene memoria de forma "a la medida", termicamente estable. |
| DE4018183A1 (de) * | 1990-06-07 | 1991-12-12 | Bayer Ag | Lichthaertende abformmaterialien |
| US6126528A (en) * | 1995-09-18 | 2000-10-03 | 3M Innovative Properties Company | Preformed ophthalmic lens base block with textured surface |
| US5763075A (en) * | 1996-09-13 | 1998-06-09 | Minnesota Mining And Manufacturing Company | Polycaprolactone lens blocking material |
| EP0851800B1 (de) * | 1995-09-18 | 2002-06-05 | Minnesota Mining And Manufacturing Company | Thermoplastisches linsenhaltematerial |
| US5885700A (en) * | 1995-09-18 | 1999-03-23 | Minnesota Mining And Manufacturing Company | Thermoplastic lens blocking material |
| DE19601924B4 (de) * | 1996-01-12 | 2005-01-13 | Ivoclar Vivadent Ag | Stabile organische Radikale enthaltendes, lichthärtendes Kompositmaterial und dessen Verwendung sowie die Verwendung eines stabilen organischen Radikals zur Herstellung eines Dentalmaterials |
| US6196840B1 (en) | 1998-08-14 | 2001-03-06 | Dentsply Research & Development Corp. | Custom fitting variable dimension dental impression tray, product and method |
| DE19941738B4 (de) * | 1999-09-02 | 2004-02-19 | 3M Espe Ag | Füllstoff zur Kunststoff-Formulierungen auf Polyurethan-Basis |
| US8026295B2 (en) | 2000-02-17 | 2011-09-27 | Dentsply International, Inc. | Dental composition with improved light stability |
| US9101436B2 (en) * | 2005-10-21 | 2015-08-11 | Ada Foundation | Dental and endodontic filling materials and methods |
| US9259439B2 (en) * | 2005-10-21 | 2016-02-16 | Ada Foundation | Dual-phase cement precursor systems for bone repair |
| US8455566B2 (en) * | 2006-10-18 | 2013-06-04 | E I Du Pont De Nemours And Company | Materials leading to improved dental composites and dental composites made therefrom |
| EP2072030A1 (de) * | 2007-12-20 | 2009-06-24 | 3M Innovative Properties Company | Zahnabdruckmaterial mit rheologischen Modifikationen |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3297745A (en) * | 1962-04-05 | 1967-01-10 | Robertson Co H H | Ethylenically unsaturated di-and tetra-urethane monomers |
| US3509234A (en) * | 1965-08-13 | 1970-04-28 | Ford Motor Co | Radiation curable paint binders containing vinyl monomers and a hydroxylated polymer reacted with a polyisocyanate and an hydroxyl alkyl acrylate |
| US3553174A (en) * | 1967-11-27 | 1971-01-05 | Amicon Corp | Reaction product of a hydroxyacrylate and an aliphatic isocyanate and transparent article made therefrom |
| US3644569A (en) * | 1968-11-19 | 1972-02-22 | American Cyanamid Co | Two-part adhesives comprising an isocyanate terminated prepolymer an isocyanate reactive monomer and an unsaturated polyester |
| US3641199A (en) * | 1969-07-07 | 1972-02-08 | Rohm & Haas | Urethane elastomer with active hydrogen containing monoethylenical unsaturated monomer |
| GB1321372A (en) * | 1970-01-19 | 1973-06-27 | Dainippon Ink & Chemicals | Photopolymerisable polyurethane compositions |
| US3878036A (en) * | 1970-05-06 | 1975-04-15 | Ppg Industries Inc | Safety glass prepared by curing a b-stage polyurethane sheet |
| US3709866A (en) * | 1970-06-01 | 1973-01-09 | Dentsply Int Inc | Photopolymerizable dental products |
| GB1388859A (en) * | 1971-11-10 | 1975-03-26 | Ici Ltd | Moulding compositions |
| US3862920A (en) * | 1972-03-15 | 1975-01-28 | Amalgamated Dental Co Ltd | Dental filling materials |
| GB1401805A (en) * | 1972-03-15 | 1975-07-30 | Amalgamated Dental Co Ltd | Dental filling materials |
| GB1441108A (en) * | 1973-01-23 | 1976-06-30 | Redfarn C A | Cross linked polymers |
| DE2320038A1 (de) * | 1973-04-19 | 1974-11-07 | Bayer Ag | Verwendung von uv-licht-haertenden harzmassen in der zahntechnik |
| GB1498421A (en) * | 1974-05-21 | 1978-01-18 | Ici Ltd | Dental compositions |
-
1977
- 1977-05-28 DE DE2724260A patent/DE2724260C2/de not_active Expired
-
1978
- 1978-05-08 US US05/904,071 patent/US4182829A/en not_active Expired - Lifetime
- 1978-05-12 NO NO781698A patent/NO151528C/no unknown
- 1978-05-15 GB GB19541/78A patent/GB1602414A/en not_active Expired
- 1978-05-19 AU AU36288/78A patent/AU3628878A/en active Pending
- 1978-05-22 PT PT68066A patent/PT68066B/de unknown
- 1978-05-24 ES ES470181A patent/ES470181A1/es not_active Expired
- 1978-05-24 AR AR272309A patent/AR215307A1/es active
- 1978-05-24 CS CS783387A patent/CS199730B2/cs unknown
- 1978-05-24 CH CH566978A patent/CH635598A5/de not_active IP Right Cessation
- 1978-05-25 DD DD78205586A patent/DD138148A5/de unknown
- 1978-05-25 FI FI781666A patent/FI781666A7/fi not_active Application Discontinuation
- 1978-05-25 SE SE7806007A patent/SE442949B/sv unknown
- 1978-05-26 DK DK235378A patent/DK235378A/da not_active Application Discontinuation
- 1978-05-26 NL NL7805763A patent/NL7805763A/xx not_active Application Discontinuation
- 1978-05-26 CA CA000304155A patent/CA1142684A/en not_active Expired
- 1978-05-26 HU HU78BA3655A patent/HU177288B/hu unknown
- 1978-05-26 BE BE188072A patent/BE867527A/xx not_active IP Right Cessation
- 1978-05-26 FR FR7815706A patent/FR2391705A1/fr active Granted
- 1978-05-26 IT IT23892/78A patent/IT1109195B/it active
- 1978-05-26 JP JP6240878A patent/JPS53148890A/ja active Pending
- 1978-05-26 BR BR7803361A patent/BR7803361A/pt unknown
- 1978-05-26 IE IE1050/78A patent/IE46980B1/en unknown
- 1978-05-26 AT AT0385478A patent/AT376988B/de not_active IP Right Cessation
- 1978-05-27 PL PL1978220118A patent/PL113841B1/pl unknown
- 1978-05-27 GR GR56355A patent/GR73553B/el unknown
- 1978-05-27 PL PL1978207128A patent/PL110798B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE46980B1 (en) | 1983-11-16 |
| DE2724260C2 (de) | 1985-06-05 |
| PL207128A1 (pl) | 1979-03-12 |
| JPS53148890A (en) | 1978-12-25 |
| FI781666A7 (fi) | 1978-11-29 |
| DK235378A (da) | 1978-11-29 |
| FR2391705B1 (de) | 1983-11-18 |
| CH635598A5 (de) | 1983-04-15 |
| IT1109195B (it) | 1985-12-16 |
| HU177288B (en) | 1981-09-28 |
| ATA385478A (de) | 1984-06-15 |
| PL110798B1 (en) | 1980-07-31 |
| NO781698L (no) | 1978-11-29 |
| BR7803361A (pt) | 1979-01-02 |
| DE2724260A1 (de) | 1978-12-07 |
| PT68066A (de) | 1978-06-01 |
| ES470181A1 (es) | 1979-09-16 |
| DD138148A5 (de) | 1979-10-17 |
| NO151528C (no) | 1985-05-02 |
| CA1142684A (en) | 1983-03-08 |
| PL113841B1 (en) | 1981-01-31 |
| SE442949B (sv) | 1986-02-10 |
| FR2391705A1 (fr) | 1978-12-22 |
| GB1602414A (en) | 1981-11-11 |
| IT7823892A0 (it) | 1978-05-26 |
| AT376988B (de) | 1985-01-25 |
| NL7805763A (nl) | 1978-11-30 |
| PT68066B (de) | 1979-10-26 |
| AU3628878A (en) | 1979-11-22 |
| BE867527A (fr) | 1978-11-27 |
| IE781050L (en) | 1978-11-28 |
| GR73553B (de) | 1984-03-14 |
| SE7806007L (sv) | 1978-11-29 |
| US4182829A (en) | 1980-01-08 |
| AR215307A1 (es) | 1979-09-28 |
| NO151528B (no) | 1985-01-14 |
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