CA2522423C - Radiation curable compositions - Google Patents
Radiation curable compositions Download PDFInfo
- Publication number
- CA2522423C CA2522423C CA 2522423 CA2522423A CA2522423C CA 2522423 C CA2522423 C CA 2522423C CA 2522423 CA2522423 CA 2522423 CA 2522423 A CA2522423 A CA 2522423A CA 2522423 C CA2522423 C CA 2522423C
- Authority
- CA
- Canada
- Prior art keywords
- weight
- component
- composition
- meth
- unsaturated
- 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
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 106
- 230000005855 radiation Effects 0.000 title claims abstract description 38
- 239000002904 solvent Substances 0.000 claims abstract description 28
- 239000000758 substrate Substances 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 9
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 28
- -1 acrylate polyol Chemical class 0.000 claims description 28
- 229920000570 polyether Polymers 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 22
- 229920005862 polyol Polymers 0.000 claims description 20
- 229920000058 polyacrylate Polymers 0.000 claims description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 239000004593 Epoxy Substances 0.000 claims description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 13
- 150000008064 anhydrides Chemical class 0.000 claims description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 150000003077 polyols Chemical class 0.000 claims description 10
- 239000005056 polyisocyanate Substances 0.000 claims description 9
- 229920001228 polyisocyanate Polymers 0.000 claims description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 5
- 150000002894 organic compounds Chemical class 0.000 claims description 5
- 150000003673 urethanes Chemical class 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- 239000008199 coating composition Substances 0.000 claims description 4
- 125000001033 ether group Chemical group 0.000 claims description 4
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- 150000002924 oxiranes Chemical group 0.000 claims 5
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical class C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 abstract description 11
- 229920000642 polymer Polymers 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 description 37
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- 238000001723 curing Methods 0.000 description 19
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- 239000000049 pigment Substances 0.000 description 13
- 230000003595 spectral effect Effects 0.000 description 13
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- 238000003756 stirring Methods 0.000 description 11
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- 238000006243 chemical reaction Methods 0.000 description 10
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
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- 238000005516 engineering process Methods 0.000 description 8
- 229910001507 metal halide Inorganic materials 0.000 description 8
- 150000005309 metal halides Chemical class 0.000 description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 7
- 239000004606 Fillers/Extenders Substances 0.000 description 7
- 201000006747 infectious mononucleosis Diseases 0.000 description 7
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 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 6
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 6
- 229910052742 iron Inorganic materials 0.000 description 6
- 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 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 229940043232 butyl acetate Drugs 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- 239000002023 wood Substances 0.000 description 5
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 4
- 239000004925 Acrylic resin Substances 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000002318 adhesion promoter Substances 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-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
- 125000003118 aryl group Chemical group 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 229940106691 bisphenol a Drugs 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910017464 nitrogen compound Inorganic materials 0.000 description 3
- 150000002830 nitrogen compounds Chemical class 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 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
- 238000003848 UV Light-Curing Methods 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- IHWUGQBRUYYZNM-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-3,4-dicarboxylic acid Chemical compound C1CC2(C(O)=O)C(C(=O)O)=CC1C2 IHWUGQBRUYYZNM-UHFFFAOYSA-N 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 229940043237 diethanolamine Drugs 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- ZRIPJJWYODJTLH-UHFFFAOYSA-N (4-benzylphenyl)-(4-chlorophenyl)methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C(C=C1)=CC=C1CC1=CC=CC=C1 ZRIPJJWYODJTLH-UHFFFAOYSA-N 0.000 description 1
- SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-UHFFFAOYSA-N 0.000 description 1
- OZCRKDNRAAKDAN-HNQUOIGGSA-N (e)-but-1-ene-1,4-diol Chemical compound OCC\C=C\O OZCRKDNRAAKDAN-HNQUOIGGSA-N 0.000 description 1
- OFOLOJQCCJFHNG-UHFFFAOYSA-N 1,1-bis(isocyanatomethyl)-4-methylcyclohexane Chemical class N(=C=O)CC1(CCC(CC1)C)CN=C=O OFOLOJQCCJFHNG-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-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
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-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
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-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
- 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
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- 239000002562 thickening agent Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229920006305 unsaturated polyester Polymers 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
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/10—Homopolymers or copolymers of methacrylic acid esters
-
- 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
- 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
- C08G18/675—Low-molecular-weight compounds
- C08G18/6755—Unsaturated carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/10—Epoxy resins modified by unsaturated compounds
-
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/10—Homopolymers or copolymers of methacrylic acid esters
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/062—Copolymers with monomers not covered by C08L33/06
- C08L33/066—Copolymers with monomers not covered by C08L33/06 containing -OH groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/062—Copolymers with monomers not covered by C08L33/06
- C08L33/068—Copolymers with monomers not covered by C08L33/06 containing glycidyl groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
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)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/966,790 | 2004-10-15 | ||
| US10/966,790 US7268172B2 (en) | 2004-10-15 | 2004-10-15 | Radiation curable compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2522423A1 CA2522423A1 (en) | 2006-04-15 |
| CA2522423C true CA2522423C (en) | 2013-07-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2522423 Expired - Fee Related CA2522423C (en) | 2004-10-15 | 2005-10-05 | Radiation curable compositions |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7268172B2 (enExample) |
| EP (1) | EP1647585B1 (enExample) |
| JP (2) | JP2006117934A (enExample) |
| KR (1) | KR101232424B1 (enExample) |
| CN (1) | CN1770011B (enExample) |
| AT (1) | ATE382668T1 (enExample) |
| CA (1) | CA2522423C (enExample) |
| DE (1) | DE602005004091T2 (enExample) |
| DK (1) | DK1647585T3 (enExample) |
| ES (1) | ES2297584T3 (enExample) |
| MX (1) | MXPA05011003A (enExample) |
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| US7858696B2 (en) * | 2003-03-10 | 2010-12-28 | Dic Corporation | Conductive resin composition, process for production thereof, and fuel cell separators |
| US20050238815A1 (en) * | 2004-04-27 | 2005-10-27 | Dvorchak Michael J | UV curable coating composition |
| CA2491308A1 (en) * | 2004-12-29 | 2006-06-30 | The Sherwin-Williams Company | Method of applying automotive primer-surfacer using a squeegee |
| US20070022625A1 (en) * | 2005-07-28 | 2007-02-01 | Garmat Usa, Inc. | UV curing structure and process |
| RU2434914C2 (ru) | 2006-12-14 | 2011-11-27 | ДСМ Ай Пи ЭССЕТС Б.В. | Отверждаемое излучением первичное покрытие d 1368 cr для оптического волокна |
| JP5167562B2 (ja) | 2006-12-14 | 2013-03-21 | ディーエスエム アイピー アセッツ ビー．ブイ． | Ｄ１３６４ｂｔ光ファイバの二次被覆 |
| EP2091884B1 (en) * | 2006-12-14 | 2011-06-01 | DSM IP Assets B.V. | D1370 r radiation curable secondary coating for optical fiber |
| US20080226912A1 (en) * | 2006-12-14 | 2008-09-18 | Norlin Tyson Dean | D1365 bj radiation curable primary coating for optical fiber |
| WO2008133668A2 (en) * | 2006-12-14 | 2008-11-06 | Dsm Ip Assets B.V. | D1369 d radiation curable secondary coating for optical fiber |
| US20080226915A1 (en) * | 2006-12-14 | 2008-09-18 | Xiaosong Wu | D1379 p radiation curable primary coating on optical fiber |
| JP2010509451A (ja) | 2006-12-14 | 2010-03-25 | ディーエスエム アイピー アセッツ ビー．ブイ． | Ｄ１３６３ｂｔ光ファイバ上の放射線硬化性一次被覆 |
| CN101535196A (zh) * | 2006-12-14 | 2009-09-16 | 帝斯曼知识产权资产管理有限公司 | 光纤上的d1363bt可辐射固化初级涂层 |
| EP2089332B1 (en) * | 2006-12-14 | 2011-06-29 | DSM IP Assets B.V. | D1381 supercoatings for optical fiber |
| TW200903160A (en) * | 2007-04-27 | 2009-01-16 | Sumitomo Chemical Co | Photosensitive resin composition |
| CN101382727B (zh) * | 2007-09-04 | 2011-06-08 | 四川大学 | 光学热敏材料及其制备方法和由其构成的光学器件 |
| US20090156251A1 (en) * | 2007-12-12 | 2009-06-18 | Alan Cannistraro | Remote control protocol for media systems controlled by portable devices |
| US20090176907A1 (en) | 2008-01-08 | 2009-07-09 | Ramesh Subramanian | Direct-to-metal radiation curable compositions |
| JP4921439B2 (ja) * | 2008-09-11 | 2012-04-25 | 富士フイルム株式会社 | 画像データ処理装置および画像データ処理プログラム |
| KR20100053094A (ko) * | 2008-11-12 | 2010-05-20 | 삼성전자주식회사 | 금속 질감을 표현한 사출 모재 및 제조방법 |
| US8735506B2 (en) * | 2009-04-03 | 2014-05-27 | Ashland Licensing And Intellectual Property Llc | Ultraviolet radiation curable pressure sensitive acrylic adhesive |
| US9701802B2 (en) * | 2009-04-08 | 2017-07-11 | Allnex Ip S.A.R.L. | Reinforced UV-A curable composite compositions and methods |
| WO2011075550A2 (en) * | 2009-12-17 | 2011-06-23 | Dsm Ip Assets B.V. | D1417 bt radiation curable coatings for aerospace applications |
| US20120196122A1 (en) * | 2009-12-17 | 2012-08-02 | Timothy Bishop | Led curing of radiation curable optical fiber coating compositions |
| JP2011132322A (ja) * | 2009-12-24 | 2011-07-07 | Tokyo Ohka Kogyo Co Ltd | 感光性組成物、ハードコート材、及び画像表示装置 |
| US9617444B2 (en) * | 2010-05-21 | 2017-04-11 | Allnex Ip S.A.R.L. | Low gloss radiation-curable compositions |
| US8513321B2 (en) | 2010-11-05 | 2013-08-20 | Ppg Industries Ohio, Inc. | Dual cure coating compositions, methods of coating a substrate, and related coated substrates |
| US8647471B2 (en) * | 2010-12-22 | 2014-02-11 | Bayer Materialscience Llc | Process for the production of sized and/or wet-strength papers, paperboards and cardboards |
| EP2548901A1 (en) * | 2011-07-19 | 2013-01-23 | Cytec Surface Specialties, S.A. | Process for the preparation of radiation curable compositions |
| US10100223B2 (en) * | 2013-03-14 | 2018-10-16 | Allnex Netherlands B.V. | Methods for making elastomers, elastomer compositions and related elastomers |
| KR102299794B1 (ko) | 2013-03-29 | 2021-09-09 | 앳슈랜드 라이센싱 앤드 인텔렉츄얼 프라퍼티 엘엘씨 | 자외선 경화성 감압성 접착제 |
| EP2808361A1 (en) | 2013-05-28 | 2014-12-03 | Allnex Belgium, S.A. | Composite Composition containing a Polycyclic Ether Polyol |
| EP2821436A1 (en) | 2013-07-01 | 2015-01-07 | Allnex Belgium, S.A. | Transparent composite composition |
| KR102093759B1 (ko) * | 2013-07-19 | 2020-03-26 | 동우 화인켐 주식회사 | 투명화소 형성용 감광성 수지조성물 |
| ES2879637T3 (es) * | 2015-03-23 | 2021-11-22 | Dow Global Technologies Llc | Composiciones fotocurables para impresión tridimensional |
| GB201508178D0 (en) * | 2015-05-13 | 2015-06-24 | Photocentric Ltd | Method for making an object |
| EP3184565A1 (en) * | 2015-12-22 | 2017-06-28 | Allnex IP S.à.r.l. | Radiation-curable urethane (meth)acrylates with residual isocyanate groups |
| EP3455264B1 (en) | 2016-05-13 | 2025-08-06 | MSI Coatings Inc. | Method for using a voc free low radiant flux led uv curable composition |
| JP7005940B2 (ja) * | 2017-05-30 | 2022-01-24 | Dic株式会社 | 変性（メタ）アクリレート樹脂及びソルダーレジスト用樹脂材料 |
| US12157831B1 (en) | 2017-07-26 | 2024-12-03 | MSI Coatings Inc. | Energy curable composition and method of using the same |
| BR112020009488A2 (pt) * | 2017-11-17 | 2020-09-15 | Actega North America Technologies, Inc. | marcações adesivas de película fina e métodos para fazer as mesmas |
| US11338320B1 (en) | 2018-02-03 | 2022-05-24 | MSI Coatings Inc. | Composition for aerosol cans, method of making and using the same |
| WO2020131185A2 (en) * | 2018-09-26 | 2020-06-25 | Dvorchak Enterprises Llc | One component uv curable compositions and methods for making same |
| CN109776756A (zh) * | 2019-01-21 | 2019-05-21 | 深圳市道尔顿电子材料有限公司 | 一种双重改性环氧丙烯酸酯及其光刻胶 |
| US12031055B2 (en) * | 2019-12-16 | 2024-07-09 | Illinois Tool Works Inc. | Filled composition with rapid UV cure to form thick coating |
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| FR2361450A1 (fr) * | 1976-08-13 | 1978-03-10 | Basf Ag | Matiere de revetement durcissable |
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| JPS61162501A (ja) | 1985-01-10 | 1986-07-23 | Nippon Paint Co Ltd | 高エネルギ−線硬化樹脂組成物 |
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| US5013631A (en) | 1989-03-03 | 1991-05-07 | Westinghouse Electric Corp. | Ultraviolet curable conformal coatings |
| DE4228713A1 (de) | 1992-08-28 | 1994-03-03 | Hoechst Ag | Wäßrige, strahlenhärtbare Bindemitteldispersionen |
| TW418346B (en) * | 1993-03-05 | 2001-01-11 | Ciba Sc Holding Ag | Photopolymerisable compositions containing tetraacrylates |
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| TW385328B (en) * | 1995-06-14 | 2000-03-21 | Ciba Sc Holding Ag | Corrosion inhibitors in powder coatings |
| DE19525489A1 (de) | 1995-07-13 | 1997-01-16 | Wolff Walsrode Ag | Strahlenhärtbare, wäßrige Dispersionen, deren Herstellung und Verwendung |
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| DE19718948A1 (de) | 1997-05-05 | 1998-11-12 | Basf Ag | Wässrige, strahlungshärtbare Beschichtungsmassen |
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| TR200101135T2 (tr) | 1998-10-26 | 2001-09-21 | Akzo Nobel N.V. | Bir poliüretan dispersiyonları karışımını içeren sulu kaplama bileşimi |
| DE19930961A1 (de) | 1999-07-05 | 2001-01-11 | Bayer Ag | Polyurethan-Dispersionen |
| DE19933826A1 (de) | 1999-07-20 | 2001-02-01 | Basf Ag | Wässrige Dispersion einer Mischung eines Polyurethans mit einem strahlungshärtbaren (Meth)acrylat-Präpolymer |
| US6509389B1 (en) | 1999-11-05 | 2003-01-21 | Uv Specialties, Inc. | UV curable compositions for producing mar resistant coatings and method for depositing same |
| DE19957604A1 (de) | 1999-11-30 | 2001-05-31 | Bayer Ag | Polyurethan-Emulsionen |
| CA2396978C (en) | 2000-01-13 | 2009-04-07 | Uv Specialties, Inc. | Uv curable transparent conductive compositions |
| GB0007728D0 (en) | 2000-03-31 | 2000-05-17 | Ppg Ind Ohio Inc | Coating composition |
| DE10016548A1 (de) | 2000-04-03 | 2001-10-11 | Bayer Ag | Polyurethan-Dispersionen |
| DE10054933A1 (de) | 2000-11-06 | 2002-05-08 | Bayer Ag | Verfahren zur Beschichtung von Substraten |
| JP2002200913A (ja) * | 2000-12-28 | 2002-07-16 | Calsonic Kansei Corp | 自動車用空気調和装置 |
| US6596787B1 (en) * | 2001-02-02 | 2003-07-22 | Henkel Loctite Corporation | Non-yellowing fast cure speed UV\visible curable liquid acrylic ester adhesives for glass bonding |
| US20030045598A1 (en) | 2001-07-31 | 2003-03-06 | General Electric Company | Radiation curable coating compositions |
| DE10143630A1 (de) | 2001-09-06 | 2003-03-27 | Bayer Ag | Strahlenhärtende Beschichtungsmittel |
-
2004
- 2004-10-15 US US10/966,790 patent/US7268172B2/en not_active Expired - Lifetime
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2005
- 2005-10-01 EP EP20050021576 patent/EP1647585B1/en not_active Expired - Lifetime
- 2005-10-01 ES ES05021576T patent/ES2297584T3/es not_active Expired - Lifetime
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- 2005-10-01 AT AT05021576T patent/ATE382668T1/de active
- 2005-10-01 DE DE200560004091 patent/DE602005004091T2/de not_active Expired - Lifetime
- 2005-10-05 CA CA 2522423 patent/CA2522423C/en not_active Expired - Fee Related
- 2005-10-13 MX MXPA05011003A patent/MXPA05011003A/es active IP Right Grant
- 2005-10-14 KR KR1020050096798A patent/KR101232424B1/ko not_active Expired - Fee Related
- 2005-10-14 CN CN2005101137375A patent/CN1770011B/zh not_active Expired - Lifetime
- 2005-10-17 JP JP2005301416A patent/JP2006117934A/ja active Pending
-
2014
- 2014-07-23 JP JP2014149457A patent/JP2014237832A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP1647585A1 (en) | 2006-04-19 |
| JP2014237832A (ja) | 2014-12-18 |
| KR101232424B1 (ko) | 2013-02-12 |
| DE602005004091T2 (de) | 2009-01-02 |
| ES2297584T3 (es) | 2008-05-01 |
| JP2006117934A (ja) | 2006-05-11 |
| US20060084713A1 (en) | 2006-04-20 |
| MXPA05011003A (es) | 2006-04-27 |
| HK1091907A1 (en) | 2007-01-26 |
| EP1647585B1 (en) | 2008-01-02 |
| CN1770011A (zh) | 2006-05-10 |
| DK1647585T3 (da) | 2008-04-14 |
| DE602005004091D1 (de) | 2008-02-14 |
| CN1770011B (zh) | 2010-08-18 |
| KR20060053276A (ko) | 2006-05-19 |
| US7268172B2 (en) | 2007-09-11 |
| CA2522423A1 (en) | 2006-04-15 |
| ATE382668T1 (de) | 2008-01-15 |
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