CA2098642A1 - Radiation curable hardcoat compositions - Google Patents
Radiation curable hardcoat compositionsInfo
- Publication number
- CA2098642A1 CA2098642A1 CA002098642A CA2098642A CA2098642A1 CA 2098642 A1 CA2098642 A1 CA 2098642A1 CA 002098642 A CA002098642 A CA 002098642A CA 2098642 A CA2098642 A CA 2098642A CA 2098642 A1 CA2098642 A1 CA 2098642A1
- Authority
- CA
- Canada
- Prior art keywords
- component
- parts
- inclusive
- mixture
- composition according
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 128
- 230000005855 radiation Effects 0.000 title claims abstract description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 50
- 239000008119 colloidal silica Substances 0.000 claims abstract description 30
- 239000000178 monomer Substances 0.000 claims abstract description 24
- 239000000654 additive Substances 0.000 claims abstract description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000001412 amines Chemical class 0.000 claims abstract description 14
- 239000004611 light stabiliser Substances 0.000 claims abstract description 14
- 125000005250 alkyl acrylate group Chemical group 0.000 claims abstract description 10
- ZYMKZMDQUPCXRP-UHFFFAOYSA-N fluoro prop-2-enoate Chemical compound FOC(=O)C=C ZYMKZMDQUPCXRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 6
- 239000004305 biphenyl Substances 0.000 claims abstract description 6
- 125000006267 biphenyl group Chemical group 0.000 claims abstract description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 6
- WSPKNABEPXUODZ-UHFFFAOYSA-N phosphono 2,4,6-trimethylbenzoate Chemical compound CC1=CC(C)=C(C(=O)OP(O)(O)=O)C(C)=C1 WSPKNABEPXUODZ-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- -1 acrylate modified 2,4-dihydroxy benzophenone Chemical class 0.000 claims description 25
- 239000006096 absorbing agent Substances 0.000 claims description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- GRJISGHXMUQUMC-UHFFFAOYSA-N silyl prop-2-enoate Chemical compound [SiH3]OC(=O)C=C GRJISGHXMUQUMC-UHFFFAOYSA-N 0.000 claims description 18
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 claims description 14
- 230000007062 hydrolysis Effects 0.000 claims description 14
- 238000006460 hydrolysis reaction Methods 0.000 claims description 14
- LHENQXAPVKABON-UHFFFAOYSA-N 1-methoxypropan-1-ol Chemical compound CCC(O)OC LHENQXAPVKABON-UHFFFAOYSA-N 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 229920000728 polyester Polymers 0.000 claims description 3
- FDSUVTROAWLVJA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)COCC(CO)(CO)CO FDSUVTROAWLVJA-UHFFFAOYSA-N 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- FWLDHHJLVGRRHD-UHFFFAOYSA-N decyl prop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C=C FWLDHHJLVGRRHD-UHFFFAOYSA-N 0.000 claims 2
- 229940065472 octyl acrylate Drugs 0.000 claims 2
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims 2
- XHIKSLHIZYVEQI-UHFFFAOYSA-N CC1=C(C(=O)[PH2]=O)C(=CC(=C1)C)C Chemical compound CC1=C(C(=O)[PH2]=O)C(=CC(=C1)C)C XHIKSLHIZYVEQI-UHFFFAOYSA-N 0.000 claims 1
- 239000004205 dimethyl polysiloxane Substances 0.000 claims 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims 1
- 239000003039 volatile agent Substances 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 26
- 239000000377 silicon dioxide Substances 0.000 abstract description 8
- 239000003999 initiator Substances 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 description 57
- 239000011248 coating agent Substances 0.000 description 38
- 150000003254 radicals Chemical class 0.000 description 16
- 239000008199 coating composition Substances 0.000 description 15
- 238000009472 formulation Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 238000007792 addition Methods 0.000 description 7
- 238000001723 curing Methods 0.000 description 7
- 125000004386 diacrylate group Chemical group 0.000 description 7
- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 6
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 5
- 238000005299 abrasion Methods 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 4
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 4
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000004927 fusion Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 2
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 2
- 229920004142 LEXAN™ Polymers 0.000 description 2
- 239000004418 Lexan Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JOCBASBOOFNAJA-UHFFFAOYSA-N N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid Chemical compound OCC(CO)(CO)NCCS(O)(=O)=O JOCBASBOOFNAJA-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004880 explosion Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920006380 polyphenylene oxide Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- SYJPAKDNFZLSMV-HYXAFXHYSA-N (Z)-2-methylpropanal oxime Chemical compound CC(C)\C=N/O SYJPAKDNFZLSMV-HYXAFXHYSA-N 0.000 description 1
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 1
- MPFAYMDFVULHEW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-octylphenol Chemical compound CCCCCCCCC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MPFAYMDFVULHEW-UHFFFAOYSA-N 0.000 description 1
- FBEHFRAORPEGFH-UHFFFAOYSA-N Allyxycarb Chemical compound CNC(=O)OC1=CC(C)=C(N(CC=C)CC=C)C(C)=C1 FBEHFRAORPEGFH-UHFFFAOYSA-N 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- 235000013175 Crataegus laevigata Nutrition 0.000 description 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000005041 Mylar™ Substances 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N Na2O Inorganic materials [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 239000004697 Polyetherimide Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 229920004738 ULTEM® Polymers 0.000 description 1
- 239000012963 UV stabilizer Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 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 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- PODOEQVNFJSWIK-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethoxyphenyl)methanone Chemical compound COC1=CC(OC)=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 PODOEQVNFJSWIK-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- GDESWOTWNNGOMW-UHFFFAOYSA-N resorcinol monobenzoate Chemical compound OC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 GDESWOTWNNGOMW-UHFFFAOYSA-N 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229940024463 silicone emollient and protective product Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
- B05D3/061—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation using U.V.
- B05D3/065—After-treatment
- B05D3/067—Curing or cross-linking the coating
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Plasma & Fusion (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90491892A | 1992-06-25 | 1992-06-25 | |
| US904,918 | 1992-06-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2098642A1 true CA2098642A1 (en) | 1993-12-26 |
Family
ID=25419972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002098642A Abandoned CA2098642A1 (en) | 1992-06-25 | 1993-06-17 | Radiation curable hardcoat compositions |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5708048A (en, 2012) |
| EP (1) | EP0576247B1 (en, 2012) |
| JP (1) | JP3616118B2 (en, 2012) |
| KR (1) | KR940000538A (en, 2012) |
| AU (1) | AU4123993A (en, 2012) |
| CA (1) | CA2098642A1 (en, 2012) |
| DE (1) | DE69322442T2 (en, 2012) |
| TW (1) | TW252144B (en, 2012) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4417141C2 (de) * | 1993-05-25 | 2001-12-13 | Gen Electric | Verfahren zum Herstellen einer gelfreien härtbaren Überzugs-Zusammensetzung und Verfahren zum Härten derselben |
| DE4319199A1 (de) | 1993-06-09 | 1994-12-15 | Roehm Gmbh | Kratzfeste antisoiling- und antigraffity-Beschichtung für Formkörper |
| US5677050A (en) * | 1995-05-19 | 1997-10-14 | Minnesota Mining And Manufacturing Company | Retroreflective sheeting having an abrasion resistant ceramer coating |
| EP0798599B9 (en) * | 1996-03-27 | 2002-08-07 | Canon Kabushiki Kaisha | Electrophotographic photosensitive member, and electrophotographic apparatus and process cartridge including same |
| US5990188A (en) * | 1996-08-15 | 1999-11-23 | General Electric Company | Radiation curable coatings with improved weatherability |
| FR2752582B1 (fr) * | 1996-08-21 | 2003-06-13 | Rhone Poulenc Chimie | Compositions a base de polyorganosiloxanes a groupements fonctionnels reticulables et leur utilisation pour la realisation de revetements anti-adherents |
| DE69826342T2 (de) * | 1997-02-06 | 2005-10-06 | Shin-Etsu Chemical Co., Ltd. | Beschichtungszusammensetzungen, hydrophiler Film und mit hydrophilem Film beschichtete Gegenstände |
| US5907000A (en) * | 1997-03-07 | 1999-05-25 | The Walman Optical Company | Adjustable refractive index coating composition |
| WO1998054255A1 (fr) * | 1997-05-30 | 1998-12-03 | Shiseido, Co., Ltd. | Copolymere contenant des groupes silyles reactifs, compositions contenant ce copolymere et methode de traitement afferente |
| US6210808B1 (en) | 1997-10-27 | 2001-04-03 | Rexam Graphics Inc. | Ink jet recording sheet comprising a chromophore-grafted polyvinyl alcohol |
| US6265061B1 (en) | 1998-05-04 | 2001-07-24 | 3M Innovative Properties Company | Retroflective articles including a cured ceramer composite coating having abrasion and stain resistant characteristics |
| US6245833B1 (en) | 1998-05-04 | 2001-06-12 | 3M Innovative Properties | Ceramer composition incorporating fluoro/silane component and having abrasion and stain resistant characteristics |
| WO1999057205A1 (en) * | 1998-05-04 | 1999-11-11 | 3M Innovative Properties Company | Ceramer composition having abrasion and stain resistant characteristics |
| US6132861A (en) * | 1998-05-04 | 2000-10-17 | 3M Innovatives Properties Company | Retroreflective articles including a cured ceramer composite coating having a combination of excellent abrasion, dew and stain resistant characteristics |
| US6352758B1 (en) | 1998-05-04 | 2002-03-05 | 3M Innovative Properties Company | Patterned article having alternating hydrophilic and hydrophobic surface regions |
| US6210790B1 (en) | 1998-07-15 | 2001-04-03 | Rensselaer Polytechnic Institute | Glass-like composites comprising a surface-modified colloidal silica and method of making thereof |
| WO2000024786A1 (en) * | 1998-10-28 | 2000-05-04 | Rexam Graphics Inc. | Method of stabilizing a radiation curable, water insoluble monomer/prepolymer in an aqueous medium |
| US6238798B1 (en) * | 1999-02-22 | 2001-05-29 | 3M Innovative Properties Company | Ceramer composition and composite comprising free radically curable fluorochemical component |
| WO2000058024A1 (en) | 1999-03-26 | 2000-10-05 | Lapoint David A | Articles coated with abrasion resistant coating |
| US6299799B1 (en) * | 1999-05-27 | 2001-10-09 | 3M Innovative Properties Company | Ceramer compositions and antistatic abrasion resistant ceramers made therefrom |
| JP3846342B2 (ja) * | 2002-03-22 | 2006-11-15 | Ｊｓｒ株式会社 | 硬化性組成物、その硬化物及び積層体 |
| DE10304127A1 (de) * | 2003-02-03 | 2004-08-12 | Basf Coatings Ag | Härtbare Stoffgemische, Verfahren zu ihrer Herstellung und ihre Verwendung |
| JP2004269644A (ja) * | 2003-03-07 | 2004-09-30 | Jsr Corp | 硬化性組成物、その硬化物及び積層体 |
| US6905770B2 (en) * | 2003-03-15 | 2005-06-14 | Cpfilms, Inc | Fade protector |
| US7504156B2 (en) * | 2004-04-15 | 2009-03-17 | Avery Dennison Corporation | Dew resistant coatings |
| US10041176B2 (en) * | 2005-04-07 | 2018-08-07 | Momentive Performance Materials Inc. | No-rinse pretreatment methods and compositions |
| KR100612960B1 (ko) * | 2005-04-20 | 2006-08-16 | 한국화학연구원 | 가교 가능한 포스핀옥사이드 화합물 및 이를 이용한광중합성 조성물 |
| DE102006016642A1 (de) * | 2006-04-08 | 2007-10-18 | Bayer Materialscience Ag | UV-härtende Schutzschicht für thermoplastische Substrate |
| JP2008001870A (ja) * | 2006-06-26 | 2008-01-10 | Harada Toso Kogyosho:Kk | シリコン含有樹脂コーティング組成物 |
| FR2925912B1 (fr) * | 2007-12-26 | 2010-01-22 | Toray Plastics Europ | Film polyester enroulable comprenant sur au moins l'une de ses faces, un revetement reticule resistant aux rayures, procede d'obtention de ce film polyester |
| WO2009129359A2 (en) * | 2008-04-18 | 2009-10-22 | 3M Innovative Properties Company | Dental filling composition comprising hyperbranched compound |
| JP5307511B2 (ja) * | 2008-11-07 | 2013-10-02 | ディーエイチ・マテリアル株式会社 | 被膜形成用ラジカル重合性樹脂組成物 |
| DE102009020934A1 (de) | 2009-05-12 | 2010-11-18 | Bayer Materialscience Ag | UV-härtende Schutzschicht für thermoplastische Substrate |
| WO2012105297A1 (ja) * | 2011-01-31 | 2012-08-09 | モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 | 機能性コロイダルシリカ溶液の製造方法およびそれを用いた紫外線硬化型ハードコート用樹脂組成物とその硬化物 |
| KR101333812B1 (ko) * | 2011-05-11 | 2013-11-29 | 단국대학교 산학협력단 | 경화 가능한 초소수성 코팅을 위한 조성물 및 이를 이용한 초소수성 막을 구비한 기판의 제조방법 |
| JP6174674B2 (ja) | 2012-03-22 | 2017-08-02 | スリーエム イノベイティブ プロパティズ カンパニー | ポリメチルメタクリレート系ハードコート組成物及びコーティングされた物品 |
| EP3582974B1 (en) | 2017-02-15 | 2021-03-24 | 3M Innovative Properties Company | Dry erase article |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4455205A (en) * | 1981-06-01 | 1984-06-19 | General Electric Company | UV Curable polysiloxane from colloidal silica, methacryloyl silane, diacrylate, resorcinol monobenzoate and photoinitiator |
| US4491508A (en) * | 1981-06-01 | 1985-01-01 | General Electric Company | Method of preparing curable coating composition from alcohol, colloidal silica, silylacrylate and multiacrylate monomer |
| US4486504A (en) * | 1982-03-19 | 1984-12-04 | General Electric Company | Solventless, ultraviolet radiation-curable silicone coating compositions |
| GR852068B (en, 2012) * | 1984-08-30 | 1985-12-24 | Johnson & Johnson Dental Prod | |
| EP0331087A3 (en) * | 1988-02-29 | 1990-03-07 | Mitsubishi Rayon Co., Ltd. | Ultraviolet-curing coating composition and production process of molded plastic article having hardened coating of modified surface characteristics |
| NL8800748A (nl) * | 1988-03-25 | 1989-10-16 | Stamicarbon | Samenstelling die met ultraviolet licht uithardbare onverzadigde monomeren en/of oligomeren, een fotoinitiator en colloidaal silica met een organosilaanverbinding bevat en de toepassing van deze samenstelling in bekledingsmiddelen. |
| CA2018237C (en) * | 1989-07-14 | 2000-05-09 | Antony P. Wright | Radiation curable acryloxyfunctional silicone coating composition |
| US5126394A (en) * | 1989-10-18 | 1992-06-30 | Dow Corning Corporation | Radiation curable abrasion resistant coatings from colloidal silica and acrylate monomer |
| DE69004776T2 (de) * | 1989-10-18 | 1994-06-09 | Dow Corning | Keine flüchtigen organischen Verbindungen enthaltende strahlungshärtbare Silikonüberzüge. |
| CA2033960A1 (en) * | 1990-01-24 | 1991-07-25 | Levi J. Cottington | Alkoxy-functional silane compositions for unprimed adhesion to polycarbonate |
| US5162390A (en) * | 1990-03-05 | 1992-11-10 | General Electric Company | UV curable coating compositions, abrasion resistant UV stabilized thermoplastic composites and method |
| JP2873855B2 (ja) * | 1990-03-26 | 1999-03-24 | 三菱レイヨン株式会社 | 被覆材組成物及びそれを用いた耐摩耗性合成樹脂成形品の製造方法 |
| US5318850A (en) * | 1991-11-27 | 1994-06-07 | General Electric Company | UV curable abrasion-resistant coatings with improved weatherability |
-
1993
- 1993-06-11 AU AU41239/93A patent/AU4123993A/en not_active Abandoned
- 1993-06-17 CA CA002098642A patent/CA2098642A1/en not_active Abandoned
- 1993-06-18 TW TW082104771A patent/TW252144B/zh active
- 1993-06-22 DE DE69322442T patent/DE69322442T2/de not_active Expired - Fee Related
- 1993-06-22 EP EP93304854A patent/EP0576247B1/en not_active Expired - Lifetime
- 1993-06-23 JP JP15169493A patent/JP3616118B2/ja not_active Expired - Fee Related
- 1993-06-24 KR KR1019930011577A patent/KR940000538A/ko not_active Withdrawn
-
1996
- 1996-08-08 US US08/694,224 patent/US5708048A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0576247A2 (en) | 1993-12-29 |
| DE69322442D1 (de) | 1999-01-21 |
| EP0576247A3 (en, 2012) | 1994-04-27 |
| DE69322442T2 (de) | 1999-08-05 |
| US5708048A (en) | 1998-01-13 |
| TW252144B (en, 2012) | 1995-07-21 |
| AU4123993A (en) | 1994-01-06 |
| EP0576247B1 (en) | 1998-12-09 |
| JP3616118B2 (ja) | 2005-02-02 |
| KR940000538A (ko) | 1994-01-03 |
| JPH06100797A (ja) | 1994-04-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2098642A1 (en) | Radiation curable hardcoat compositions | |
| US4455205A (en) | UV Curable polysiloxane from colloidal silica, methacryloyl silane, diacrylate, resorcinol monobenzoate and photoinitiator | |
| EP0408047B1 (en) | Radiation curable acryloxyfunctional silicone coating composition | |
| US4491508A (en) | Method of preparing curable coating composition from alcohol, colloidal silica, silylacrylate and multiacrylate monomer | |
| US4439494A (en) | Silyl-polyacrylates for polycarbonate substrates | |
| US5242719A (en) | Abrasion resistant UV-curable hardcoat compositions | |
| JP2512673B2 (ja) | 耐候性が改良された耐摩耗性塗料組成物 | |
| JP4775543B2 (ja) | オルガノシリコーンレジンエマルジョン組成物及びその製造方法、ならびに該組成物の被膜が形成された物品 | |
| EP0424006A2 (en) | Silane free radiation curable abrasion resistant coatings | |
| JPH05117545A (ja) | 放射線硬化性コーテイング組成物 | |
| US5232964A (en) | Tintable abrasion resistant coating compositions | |
| US5607729A (en) | Method for making curable coatings | |
| EP0424645B1 (en) | Radiation curable transparent coating compositions containing basic colloidal silica | |
| EP0430583A2 (en) | Silane free radiation curable abrasion resistant coating composition containing an unsaturated organic compound | |
| US6037394A (en) | Primer composition and article obtained using the same | |
| EP0424007A2 (en) | Zero volatile organic content radiation curable silicone coatings | |
| JPH04214021A (ja) | プライマーを使わないポリカーボネート用アルコキシ官能シラン含有塗料組成物 | |
| HK1002114A (en) | Radiation curable hardcoat compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |