DE19853569A1 - Neue Urethanacrylate, Verfahren zu ihrer Herstellung sowie ihre Verwendung - Google Patents
Neue Urethanacrylate, Verfahren zu ihrer Herstellung sowie ihre VerwendungInfo
- Publication number
- DE19853569A1 DE19853569A1 DE19853569A DE19853569A DE19853569A1 DE 19853569 A1 DE19853569 A1 DE 19853569A1 DE 19853569 A DE19853569 A DE 19853569A DE 19853569 A DE19853569 A DE 19853569A DE 19853569 A1 DE19853569 A1 DE 19853569A1
- Authority
- DE
- Germany
- Prior art keywords
- meth
- isocyanate
- component
- acrylic acid
- urethane
- 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.)
- Withdrawn
Links
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 238000000034 method Methods 0.000 title abstract description 7
- 239000012948 isocyanate Substances 0.000 claims abstract description 21
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 18
- 239000000047 product Substances 0.000 claims abstract description 18
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 238000000576 coating method Methods 0.000 claims abstract description 12
- 239000011248 coating agent Substances 0.000 claims abstract description 11
- 230000005855 radiation Effects 0.000 claims abstract description 11
- PJMDLNIAGSYXLA-UHFFFAOYSA-N 6-iminooxadiazine-4,5-dione Chemical compound N=C1ON=NC(=O)C1=O PJMDLNIAGSYXLA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000013638 trimer Substances 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 5
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims abstract description 3
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 16
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 14
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000005442 diisocyanate group Chemical group 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 8
- 239000003973 paint Substances 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 claims description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 3
- HXSACZWWBYWLIS-UHFFFAOYSA-N oxadiazine-4,5,6-trione Chemical group O=C1ON=NC(=O)C1=O HXSACZWWBYWLIS-UHFFFAOYSA-N 0.000 claims description 2
- 238000003848 UV Light-Curing Methods 0.000 claims 1
- -1 uretedione Chemical compound 0.000 abstract description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract 2
- QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical group N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 description 22
- 239000000243 solution Substances 0.000 description 14
- 239000005056 polyisocyanate Substances 0.000 description 11
- 229920001228 polyisocyanate Polymers 0.000 description 11
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000008199 coating composition Substances 0.000 description 8
- 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 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 6
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 6
- 239000012975 dibutyltin dilaurate Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000000976 ink Substances 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 4
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 3
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 3
- JYFHYPJRHGVZDY-UHFFFAOYSA-N Dibutyl phosphate Chemical compound CCCCOP(O)(=O)OCCCC JYFHYPJRHGVZDY-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000006384 oligomerization reaction Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
- 241001550224 Apha Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 1
- XSCLFFBWRKTMTE-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCC(CN=C=O)C1 XSCLFFBWRKTMTE-UHFFFAOYSA-N 0.000 description 1
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical class CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 1
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 1
- OQYKKQQLTKPGSG-UHFFFAOYSA-N 2,5-dimethylhexane-1,6-diol Chemical compound OCC(C)CCC(C)CO OQYKKQQLTKPGSG-UHFFFAOYSA-N 0.000 description 1
- FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical compound CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
- WMYINDVYGQKYMI-UHFFFAOYSA-N 2-[2,2-bis(hydroxymethyl)butoxymethyl]-2-ethylpropane-1,3-diol Chemical compound CCC(CO)(CO)COCC(CC)(CO)CO WMYINDVYGQKYMI-UHFFFAOYSA-N 0.000 description 1
- IUGOPULVANEDRX-UHFFFAOYSA-N 2-ethylhexane-1,1-diol Chemical compound CCCCC(CC)C(O)O IUGOPULVANEDRX-UHFFFAOYSA-N 0.000 description 1
- FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical class OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- WRXSIZPUSNRUGA-UHFFFAOYSA-N 2-phenylundecan-2-ol Chemical compound CCCCCCCCCC(C)(O)C1=CC=CC=C1 WRXSIZPUSNRUGA-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- CCTFMNIEFHGTDU-UHFFFAOYSA-N 3-methoxypropyl acetate Chemical compound COCCCOC(C)=O CCTFMNIEFHGTDU-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical class CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 240000003085 Quassia amara Species 0.000 description 1
- 241000158147 Sator Species 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical class CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 1
- 125000000687 hydroquinonyl group Chemical class C1(O)=C(C=C(O)C=C1)* 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- HLJDOURGTRAFHE-UHFFFAOYSA-N isocyanic acid;3,5,5-trimethylcyclohex-2-en-1-one Chemical compound N=C=O.N=C=O.CC1=CC(=O)CC(C)(C)C1 HLJDOURGTRAFHE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229960004592 isopropanol Drugs 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical class CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 1
- 229920002601 oligoester Polymers 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- XRVCFZPJAHWYTB-UHFFFAOYSA-N prenderol Chemical compound CCC(CC)(CO)CO XRVCFZPJAHWYTB-UHFFFAOYSA-N 0.000 description 1
- 229950006800 prenderol Drugs 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000006120 scratch resistant coating Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- HJBZFPLBRXFZNE-UHFFFAOYSA-M tetrabutylphosphanium fluoride hydrofluoride Chemical compound F.[F-].CCCC[P+](CCCC)(CCCC)CCCC HJBZFPLBRXFZNE-UHFFFAOYSA-M 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
- C09D175/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853569A DE19853569A1 (de) | 1998-11-20 | 1998-11-20 | Neue Urethanacrylate, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| US09/433,854 US6191181B1 (en) | 1998-11-20 | 1999-11-04 | Urethane acrylates and their use in coating compositions |
| DE59911363T DE59911363D1 (de) | 1998-11-20 | 1999-11-08 | Neue Urethanacrylate, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| ES99121940T ES2235421T3 (es) | 1998-11-20 | 1999-11-08 | Nuevos uretanoacrilatos, procedimiento para su preparacion, asi como su uso. |
| EP99121940A EP1002818B1 (de) | 1998-11-20 | 1999-11-08 | Neue Urethanacrylate, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| AT99121940T ATE286089T1 (de) | 1998-11-20 | 1999-11-08 | Neue urethanacrylate, verfahren zu ihrer herstellung sowie ihre verwendung |
| CA002290176A CA2290176C (en) | 1998-11-20 | 1999-11-15 | New urethane acrylates and their use in coating compositions |
| AU59441/99A AU752939B2 (en) | 1998-11-20 | 1999-11-16 | New urethane acrylates and their use in coating compositions background of the invention |
| JP11328229A JP2000154230A (ja) | 1998-11-20 | 1999-11-18 | 新規なウレタンアクリレ―トおよび被覆組成物におけるその使用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853569A DE19853569A1 (de) | 1998-11-20 | 1998-11-20 | Neue Urethanacrylate, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19853569A1 true DE19853569A1 (de) | 2000-05-25 |
Family
ID=7888449
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19853569A Withdrawn DE19853569A1 (de) | 1998-11-20 | 1998-11-20 | Neue Urethanacrylate, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
| DE59911363T Expired - Lifetime DE59911363D1 (de) | 1998-11-20 | 1999-11-08 | Neue Urethanacrylate, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59911363T Expired - Lifetime DE59911363D1 (de) | 1998-11-20 | 1999-11-08 | Neue Urethanacrylate, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6191181B1 (enExample) |
| EP (1) | EP1002818B1 (enExample) |
| JP (1) | JP2000154230A (enExample) |
| AT (1) | ATE286089T1 (enExample) |
| AU (1) | AU752939B2 (enExample) |
| CA (1) | CA2290176C (enExample) |
| DE (2) | DE19853569A1 (enExample) |
| ES (1) | ES2235421T3 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002048230A1 (de) * | 2000-12-14 | 2002-06-20 | Bayer Aktiengesellschaft | Blockierte polyisocyanate auf hdi-basis |
| WO2007063026A1 (de) | 2005-12-01 | 2007-06-07 | Basf Se | Strahlungshärtbare wasseremulgierbare polyisocyanate |
| US7943682B2 (en) | 2005-12-01 | 2011-05-17 | Basf Aktiengesellschaft | Radiation-curable water-emulsifiable polyisocyanates |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6383322B1 (en) * | 2000-05-12 | 2002-05-07 | Wen Ping Wang | Method for manufacturing knockdown board material |
| US20030110205A1 (en) * | 2001-12-07 | 2003-06-12 | Leith Johnson | Virtualized resources in a partitionable server |
| DE10208395B4 (de) * | 2002-02-27 | 2004-03-25 | Ivoclar Vivadent Ag | (Meth)acrylatsubstituierte Iminooxadiazindion-Derivate |
| DE10208396B4 (de) * | 2002-02-27 | 2006-05-18 | Ivoclar Vivadent Ag | Dentalmaterialien auf der Basis von substituierten Iminooxadiazindion-Derivaten |
| DE10246512A1 (de) * | 2002-10-04 | 2004-04-15 | Bayer Ag | Niedrigviskose strahlenhärtende und thermisch härtende Polyisocyanate |
| DE10339912B4 (de) * | 2003-08-29 | 2016-07-21 | Ivoclar Vivadent Ag | Dentale Beschichtungsmaterialien, deren Verwendung sowie Verfahren zur Beschichtung einer Substratoberfläche |
| DE102004012902A1 (de) * | 2004-03-17 | 2005-10-06 | Bayer Materialscience Ag | Herstellung von neuen strahlenhärtenden Bindemitteln |
| DE102004012903A1 (de) * | 2004-03-17 | 2005-10-06 | Bayer Materialscience Ag | Niedrigviskose Allophanate mit aktinisch härtbaren Gruppen |
| CA2495596A1 (en) | 2005-02-07 | 2006-08-07 | Resin Systems Inc. | Method of modular pole construction and modular pole assembly |
| CA2623577C (en) | 2005-08-11 | 2014-01-28 | Basf Se | Copolymers for cosmetic applications |
| CN100419152C (zh) * | 2006-09-13 | 2008-09-17 | 合肥安大天辐新材料有限公司 | 环保型涂料印花粘合剂及其制备方法 |
| EP2144942A1 (en) * | 2007-04-11 | 2010-01-20 | Bayer MaterialScience AG | Radiation-crosslinking and thermally crosslinking pu systems comprising iminooxadiazinedione |
| ES2691398T3 (es) * | 2008-05-30 | 2018-11-27 | Red Spot Paint & Varnish Co., Inc. | Composiciones de revestimiento curables por UV que contienen resinas de acrilato de uretano alifático |
| US9109139B2 (en) | 2008-05-30 | 2015-08-18 | Red Spot Paint & Varnish Co., Inc. | UV curable coating compositions containing aliphatic urethane acrylate resins |
| KR101488848B1 (ko) | 2008-05-30 | 2015-02-02 | 레드스포트페인트앤드바니쉬캄파니,인코포레이티드 | 지방족 우레탄 아크릴레이트 수지를 함유하는 ｕｖ 경화성피복 조성물 |
| KR101001656B1 (ko) * | 2008-08-26 | 2010-12-15 | 에스에스씨피 주식회사 | 광중합형 수지 조성물 및 이를 사용하여 제조되는 광섬유 |
| KR100961940B1 (ko) | 2010-03-12 | 2010-06-10 | 주식회사 신광화학산업 | 자외선 경화형 수지, 이의 제조방법 및 이를 이용한 휴대용 단말기의 키패드 제조방법 |
| WO2012102299A1 (ja) | 2011-01-27 | 2012-08-02 | 株式会社オートネットワーク技術研究所 | 連鎖移動剤、感光性組成物、感光性組成物の硬化物、及び感光性組成物の硬化方法 |
| WO2013144095A1 (de) | 2012-03-27 | 2013-10-03 | Bayer Intellectual Property Gmbh | Verwendung von uv-strahlenhärtbaren polyurethanharzen zur herstellung von solarlaminaten |
| CN102964566B (zh) * | 2012-11-08 | 2014-05-21 | 万华化学集团股份有限公司 | 一种制备含亚氨代噁二嗪二酮的多异氰酸酯的方法 |
| JP5758958B2 (ja) * | 2013-08-07 | 2015-08-05 | 株式会社オートネットワーク技術研究所 | 紫外線硬化性組成物及びこれを用いた硬化物 |
| JP2014210924A (ja) * | 2014-06-03 | 2014-11-13 | レッド・スポット・ペイント・アンド・ヴァーニッシュ・カンパニー・インコーポレーテッド | 脂肪族ウレタンアクリレート樹脂を含むｕｖ硬化性被覆組成物 |
| JP6983491B2 (ja) * | 2016-04-04 | 2021-12-17 | 大日本印刷株式会社 | レーザ印字用多層積層フィルム並びにそれよりなる包装体及び印字体、並びにこれらに用いられるレーザ印字用インキ組成物 |
| JP6413130B2 (ja) * | 2016-08-25 | 2018-10-31 | レッド・スポット・ペイント・アンド・ヴァーニッシュ・カンパニー・インコーポレーテッド | 脂肪族ウレタンアクリレート樹脂を含むｕｖ硬化性被覆組成物 |
| US11643479B2 (en) | 2016-12-05 | 2023-05-09 | Covestro Deutschland Ag | Method for producing an article by layer-by-layer buildup with separately patterned resin and initiator wherein the resin has a storage modulus greater than loss modulus at 20 C |
| EP3548522B1 (de) * | 2016-12-05 | 2022-07-06 | Covestro Deutschland AG | Verfahren zur herstellung eines gegenstandes aus einem vorläufer und verwendung eines radikalisch vernetzbaren harzes in einem additiven fertigungsverfahren |
| WO2019030267A1 (de) | 2017-08-09 | 2019-02-14 | Covestro Deutschland Ag | Verfahren zur herstellung eines dreidimensionalen objektes mit individualisiertem und über 3d-druck erzeugtem objektabschnitt |
| US11384168B2 (en) | 2017-12-21 | 2022-07-12 | Covestro Deutschland Ag | Two-phase 3D printing method |
| CN110305294B (zh) * | 2019-07-15 | 2021-04-20 | 万华化学集团股份有限公司 | 一种存储稳定的含有脲二酮基团的多异氰酸酯的制备方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5034964B1 (enExample) | 1970-03-30 | 1975-11-12 | ||
| DE2729990A1 (de) * | 1977-07-02 | 1979-01-18 | Bayer Ag | Verfahren zur herstellung von isocyanatgruppen aufweisenden allophanaten |
| GB2203159B (en) * | 1987-04-03 | 1990-12-12 | Asahi Chemical Ind | An isocyanurate polyisocyanate and its use as a curing agent for a two-component polyurethane composition |
| DE3737244A1 (de) | 1987-11-03 | 1989-05-18 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen und olefinische doppelbindungen aufweisenden verbindungen und ihre verwendung als bindemittel |
| DE3814167A1 (de) * | 1988-04-27 | 1989-11-09 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung |
| DE3827596A1 (de) * | 1988-08-13 | 1990-02-15 | Bayer Ag | Neue katalysatoren, ein verfahren zu ihrer hertstellung und ihre verwendung zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten |
| DE3902078A1 (de) * | 1989-01-25 | 1990-07-26 | Bayer Ag | Verfahren zur herstellung von modifizierten, isocyanuratgruppen aufweisenden polyisocyanaten und ihre verwendung |
| DE4027743A1 (de) | 1990-09-01 | 1992-03-05 | Bayer Ag | Acryloylgruppen enthaltende, aliphatische polyurethane, ein verfahren zu ihrer herstellung und ihre verwendung |
| US5298431A (en) * | 1991-09-30 | 1994-03-29 | Olin Corporation | Process for producing low viscosity isocyanate trimers |
| DE19532060A1 (de) * | 1995-08-31 | 1997-03-06 | Bayer Ag | Polycyclische Iminooxadiazindione, deren Herstellung und Verwendung |
| DE19611849A1 (de) | 1996-03-26 | 1997-10-02 | Bayer Ag | Neue Isocyanattrimerisate und Isocyanattrimerisatmischungen, deren Herstellung und Verwendung |
| DE19734048A1 (de) | 1997-08-06 | 1999-02-11 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten, damit hergestellte Polyisocyanate und deren Verwendung |
| DK0962454T3 (da) * | 1998-06-02 | 2002-10-28 | Bayer Ag | Fremgangsmåde til fremstilling af iminooxadiazindiongruppeholdige polyisocyanater |
-
1998
- 1998-11-20 DE DE19853569A patent/DE19853569A1/de not_active Withdrawn
-
1999
- 1999-11-04 US US09/433,854 patent/US6191181B1/en not_active Expired - Lifetime
- 1999-11-08 ES ES99121940T patent/ES2235421T3/es not_active Expired - Lifetime
- 1999-11-08 EP EP99121940A patent/EP1002818B1/de not_active Expired - Lifetime
- 1999-11-08 AT AT99121940T patent/ATE286089T1/de active
- 1999-11-08 DE DE59911363T patent/DE59911363D1/de not_active Expired - Lifetime
- 1999-11-15 CA CA002290176A patent/CA2290176C/en not_active Expired - Fee Related
- 1999-11-16 AU AU59441/99A patent/AU752939B2/en not_active Ceased
- 1999-11-18 JP JP11328229A patent/JP2000154230A/ja active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002048230A1 (de) * | 2000-12-14 | 2002-06-20 | Bayer Aktiengesellschaft | Blockierte polyisocyanate auf hdi-basis |
| WO2007063026A1 (de) | 2005-12-01 | 2007-06-07 | Basf Se | Strahlungshärtbare wasseremulgierbare polyisocyanate |
| US7888402B2 (en) | 2005-12-01 | 2011-02-15 | Basf Aktiengesellschaft | Radiation-curable water-emulsifiable polyisocyanates |
| US7943682B2 (en) | 2005-12-01 | 2011-05-17 | Basf Aktiengesellschaft | Radiation-curable water-emulsifiable polyisocyanates |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1002818A1 (de) | 2000-05-24 |
| EP1002818B1 (de) | 2004-12-29 |
| ES2235421T3 (es) | 2005-07-01 |
| ATE286089T1 (de) | 2005-01-15 |
| CA2290176A1 (en) | 2000-05-20 |
| AU5944199A (en) | 2000-05-25 |
| CA2290176C (en) | 2008-07-15 |
| AU752939B2 (en) | 2002-10-03 |
| JP2000154230A (ja) | 2000-06-06 |
| DE59911363D1 (de) | 2005-02-03 |
| US6191181B1 (en) | 2001-02-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1002818B1 (de) | Neue Urethanacrylate, Verfahren zu ihrer Herstellung sowie ihre Verwendung | |
| EP2410971B1 (de) | Strahlungshärtbare hochfunktionelle polyurethan(meth)acrylate | |
| DE602004008856T2 (de) | Acrylatfunktionelles blockiertes Polyisocyanatharz für dual cure Beschichtungen | |
| EP1134247B1 (de) | Hochfunktionelle Polyisocyanate | |
| DE69811967T2 (de) | Niedrigviskose, ethylenisch ungesättigte Polyurethane mit Allophanatgruppen | |
| DE69837957T2 (de) | Verfahren zur Herstellung niedrigviskoser, ethylenisch ungesättigter, Allophanatgruppen enthaltender Polyurethane | |
| DE69527430T2 (de) | Uretdion- und allophanatgruppen aufweisende polyisocyanate | |
| EP3055339A1 (de) | Polyfunktionelle urethan(meth)acrylate aus monomer armen diisocyanat-monoaddukten | |
| EP1138710A1 (de) | Beschichtungssystem enthaltend UV-härtbare, Isocyanatgruppen aufweisende Urethan (meth) acrylate und Hydroxylgruppen aufweisende Urethan (meth) acrylate | |
| EP1551897B1 (de) | Niedrigviskose strahlenhärtende und thermisch härtende polyisocyanate enthaltend oxadiazintrionguppen | |
| EP2367864B1 (de) | Monomerarme 1 : 1 monoaddukte aus reaktiven olefinischen verbindungen und diisocyanaten unter verwendung einbaubarer inhibitoren | |
| EP1578835B1 (de) | Neue dual cure-systeme | |
| EP0315020B1 (de) | Verfahren zur Herstellung von Isocyanuratgruppen und olefinische Doppelbindungen aufweisenden Verbindungen und ihre Verwendung als Bindemittel | |
| US5300615A (en) | Polyurethanes containing acryloyl groups, a process for their preparation and their use as binders for coating compositions | |
| EP1541609B1 (de) | Härter | |
| EP0868463B1 (de) | Verbindungen mit isocyanatgruppen und verkappten gegenüber isocyanaten reaktiven gruppen | |
| DE102004043539A1 (de) | Niedrigviskose Allophanate mit aktinisch härtbaren Gruppen | |
| EP0447845B1 (de) | Strahlungshärtbare Amin- und Harnstoffgruppen enthaltende Urethanacrylatverbindungen | |
| EP0547462B1 (de) | Verfahren zur Herstellung von Acryloylgruppen enthaltenden, aliphatischen Polyurethanen. | |
| DE69934568T2 (de) | Beschichtungszusammensetzungen, die eine Mischung von ethylenisch ungesättigten Polyurethanen enthalten | |
| EP4234602A1 (de) | Verwendung spezieller katalysatoren für die herstellung von polyurethanbeschichtungen | |
| DE102004057224A1 (de) | BOE-und/oder Polyorthoestergruppenhaltige Bindemittelgemische | |
| DE19860049A1 (de) | Härtbare Zubereitungen | |
| EP1712600A1 (en) | Coating compositions containing ethylenically unsaturated polyurethanes as binders | |
| DE10033697A1 (de) | Mit UV-Strahlung und thermisch härtbare wässrige Polyurethandispersionen sowie deren Verwendung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |