FI68241B - Fotopolymeriserbar massa - Google Patents
Fotopolymeriserbar massa Download PDFInfo
- Publication number
- FI68241B FI68241B FI792196A FI792196A FI68241B FI 68241 B FI68241 B FI 68241B FI 792196 A FI792196 A FI 792196A FI 792196 A FI792196 A FI 792196A FI 68241 B FI68241 B FI 68241B
- Authority
- FI
- Finland
- Prior art keywords
- group
- parts
- light
- carbon atoms
- polymerizable
- Prior art date
Links
- -1 2,4,6-trimethylphenyl Chemical group 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000002966 varnish Substances 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 8
- 125000004076 pyridyl group Chemical class 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 239000000976 ink Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001544 thienyl group Chemical class 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 4
- 239000012965 benzophenone Substances 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 150000008365 aromatic ketones Chemical class 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 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 claims 1
- IMDHDEPPVWETOI-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-2,2,2-trichloroethanone Chemical compound CC(C)(C)C1=CC=C(C(=O)C(Cl)(Cl)Cl)C=C1 IMDHDEPPVWETOI-UHFFFAOYSA-N 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 14
- 239000003999 initiator Substances 0.000 description 14
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000011521 glass Substances 0.000 description 10
- 230000009257 reactivity Effects 0.000 description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 238000001723 curing Methods 0.000 description 8
- 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 8
- OAADXJFIBNEPLY-UHFFFAOYSA-N methoxy(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(OC)C1=CC=CC=C1 OAADXJFIBNEPLY-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
- LMZLQYYLELWCCW-UHFFFAOYSA-N dimethoxy(phenyl)phosphane Chemical compound COP(OC)C1=CC=CC=C1 LMZLQYYLELWCCW-UHFFFAOYSA-N 0.000 description 7
- 239000004922 lacquer Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000012188 paraffin wax Substances 0.000 description 5
- SUEDCWGEKSLKOM-UHFFFAOYSA-N (2,6-dimethoxyphenyl)-diphenylphosphorylmethanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 SUEDCWGEKSLKOM-UHFFFAOYSA-N 0.000 description 4
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229920006305 unsaturated polyester Polymers 0.000 description 4
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 3
- UKRQMDIFLKHCRO-UHFFFAOYSA-N 2,4,6-trimethylbenzoyl chloride Chemical compound CC1=CC(C)=C(C(Cl)=O)C(C)=C1 UKRQMDIFLKHCRO-UHFFFAOYSA-N 0.000 description 3
- MYISVPVWAQRUTL-UHFFFAOYSA-N 2-methylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3SC2=C1 MYISVPVWAQRUTL-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- OVSFXKCTADOYFM-UHFFFAOYSA-N benzhydryloxyphosphane Chemical compound C=1C=CC=CC=1C(OP)C1=CC=CC=C1 OVSFXKCTADOYFM-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- IMDXZWRLUZPMDH-UHFFFAOYSA-N dichlorophenylphosphine Chemical compound ClP(Cl)C1=CC=CC=C1 IMDXZWRLUZPMDH-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- HZWAUDKTZOUQPD-UHFFFAOYSA-N diphenylphosphoryl-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 HZWAUDKTZOUQPD-UHFFFAOYSA-N 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000003605 opacifier Substances 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 125000003944 tolyl group Chemical group 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
- 238000004383 yellowing Methods 0.000 description 3
- IIZNFZIITMBLRY-UHFFFAOYSA-N (3,4-dimethylphenyl)-diphenylphosphorylmethanone Chemical compound C1=C(C)C(C)=CC=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 IIZNFZIITMBLRY-UHFFFAOYSA-N 0.000 description 2
- ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical group OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 description 2
- ROGMVTGBFVTARY-UHFFFAOYSA-N 2-ethyl-1-[methoxy(phenyl)phosphoryl]hexan-1-one Chemical compound CCCCC(CC)C(=O)P(=O)(OC)C1=CC=CC=C1 ROGMVTGBFVTARY-UHFFFAOYSA-N 0.000 description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- VDQQXEISLMTGAB-UHFFFAOYSA-N chloramine T Chemical compound [Na+].CC1=CC=C(S(=O)(=O)[N-]Cl)C=C1 VDQQXEISLMTGAB-UHFFFAOYSA-N 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 2
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- LDNCAOOMUMJYTN-UHFFFAOYSA-N phenyl-di(propan-2-yloxy)phosphane Chemical compound CC(C)OP(OC(C)C)C1=CC=CC=C1 LDNCAOOMUMJYTN-UHFFFAOYSA-N 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000003678 scratch resistant effect Effects 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229920006337 unsaturated polyester resin Polymers 0.000 description 2
- 238000009423 ventilation Methods 0.000 description 2
- RYUDULQOARIGFC-UHFFFAOYSA-N (2,4-dichlorophenyl)-diphenylphosphorylmethanone Chemical compound ClC1=CC(Cl)=CC=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 RYUDULQOARIGFC-UHFFFAOYSA-N 0.000 description 1
- SQWIEBKHVLRDRG-UHFFFAOYSA-N (2,6-dimethylphenyl)-diphenylphosphorylmethanone Chemical compound CC1=CC=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 SQWIEBKHVLRDRG-UHFFFAOYSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- WNBXQARBPBWRFD-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)naphthalene Chemical compound C1=CC=CC2=C(Cl)C(CCl)=CC=C21 WNBXQARBPBWRFD-UHFFFAOYSA-N 0.000 description 1
- RPMLFEYJLCDKFM-UHFFFAOYSA-N 1-diethoxyphosphoryl-2,2-dimethylpropan-1-one Chemical compound CCOP(=O)(OCC)C(=O)C(C)(C)C RPMLFEYJLCDKFM-UHFFFAOYSA-N 0.000 description 1
- ZFIVBGXETFWLQL-UHFFFAOYSA-N 1-diphenylphosphoryl-2-ethyl-2-methylhexan-1-one Chemical compound C=1C=CC=CC=1P(=O)(C(=O)C(C)(CC)CCCC)C1=CC=CC=C1 ZFIVBGXETFWLQL-UHFFFAOYSA-N 0.000 description 1
- REHQLKUNRPCYEW-UHFFFAOYSA-N 1-methylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1(C)CCCCC1 REHQLKUNRPCYEW-UHFFFAOYSA-N 0.000 description 1
- DSKGWFQMJHBHRT-UHFFFAOYSA-N 2,2-diethoxyacetamide Chemical compound CCOC(C(N)=O)OCC DSKGWFQMJHBHRT-UHFFFAOYSA-N 0.000 description 1
- BKYWPNROPGQIFZ-UHFFFAOYSA-N 2,4-dimethylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(C)=C1 BKYWPNROPGQIFZ-UHFFFAOYSA-N 0.000 description 1
- NDXRPDJVAUCBOH-UHFFFAOYSA-N 2,6-dimethoxybenzoyl chloride Chemical compound COC1=CC=CC(OC)=C1C(Cl)=O NDXRPDJVAUCBOH-UHFFFAOYSA-N 0.000 description 1
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- MPCHQYWZAVTABQ-UHFFFAOYSA-N 2-(chloromethyl)naphthalene Chemical compound C1=CC=CC2=CC(CCl)=CC=C21 MPCHQYWZAVTABQ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- WFSGQBNCVASPMW-UHFFFAOYSA-N 2-ethylhexanoyl chloride Chemical compound CCCCC(CC)C(Cl)=O WFSGQBNCVASPMW-UHFFFAOYSA-N 0.000 description 1
- GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 1
- SYEZSRFAWVLENF-UHFFFAOYSA-N 3,3-dimethyloctanoyl chloride Chemical compound CCCCCC(C)(C)CC(Cl)=O SYEZSRFAWVLENF-UHFFFAOYSA-N 0.000 description 1
- LVDPKZXCRUHXJB-UHFFFAOYSA-N 3,3-diphenylpropoxyphosphane Chemical compound C=1C=CC=CC=1C(CCOP)C1=CC=CC=C1 LVDPKZXCRUHXJB-UHFFFAOYSA-N 0.000 description 1
- MCLMZMISZCYBBG-UHFFFAOYSA-N 3-ethylheptanoic acid Chemical compound CCCCC(CC)CC(O)=O MCLMZMISZCYBBG-UHFFFAOYSA-N 0.000 description 1
- CRIDYGZAYHPVKK-UHFFFAOYSA-N 4,4-diphenylbutoxyphosphane Chemical compound C=1C=CC=CC=1C(CCCOP)C1=CC=CC=C1 CRIDYGZAYHPVKK-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical class COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
- KBIWNQVZKHSHTI-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,4-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C1=CC=C(N)C=C1 KBIWNQVZKHSHTI-UHFFFAOYSA-N 0.000 description 1
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 description 1
- WNLMYNASWOULQY-UHFFFAOYSA-N 4-tert-butylbenzoyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)C=C1 WNLMYNASWOULQY-UHFFFAOYSA-N 0.000 description 1
- CIBUJWKYOLGNLI-UHFFFAOYSA-N COC1=C(C(=CC=C1)OC)C(=O)C2=C(C(=C(C=C2)P(=O)(C3=CC=CC=C3)C4=CC=CC=C4)C5=CC=CC=C5)C6=CC=CC=C6 Chemical compound COC1=C(C(=CC=C1)OC)C(=O)C2=C(C(=C(C=C2)P(=O)(C3=CC=CC=C3)C4=CC=CC=C4)C5=CC=CC=C5)C6=CC=CC=C6 CIBUJWKYOLGNLI-UHFFFAOYSA-N 0.000 description 1
- CJPVDFOIZMUDKE-UHFFFAOYSA-N Clc1cccc(Cl)c1C(=O)P(=O)c1ccccc1 Chemical compound Clc1cccc(Cl)c1C(=O)P(=O)c1ccccc1 CJPVDFOIZMUDKE-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 101150054274 Hnrnpd gene Proteins 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 206010039587 Scarlet Fever Diseases 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- IEWRMZSVIVEQCP-UHFFFAOYSA-N [methoxy(phenyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound C=1C=CC=CC=1P(=O)(OC)C(=O)C1=C(C)C=C(C)C=C1C IEWRMZSVIVEQCP-UHFFFAOYSA-N 0.000 description 1
- ZHOUIYODXNAKRZ-UHFFFAOYSA-N [methoxy(phenyl)phosphoryl]-(4-methylphenyl)methanone Chemical compound C=1C=CC=CC=1P(=O)(OC)C(=O)C1=CC=C(C)C=C1 ZHOUIYODXNAKRZ-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- KDONFNVMZBKJTJ-UHFFFAOYSA-N diethoxyphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CCOP(=O)(OCC)C(=O)C1=C(C)C=C(C)C=C1C KDONFNVMZBKJTJ-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- QCASTONPZLJEOJ-UHFFFAOYSA-N diphenyl(propan-2-yloxy)phosphane Chemical compound C=1C=CC=CC=1P(OC(C)C)C1=CC=CC=C1 QCASTONPZLJEOJ-UHFFFAOYSA-N 0.000 description 1
- UTZDKCFZGDSBGI-UHFFFAOYSA-N diphenylphosphoryl-(1-methylcyclohexyl)methanone Chemical compound C=1C=CC=CC=1P(=O)(C=1C=CC=CC=1)C(=O)C1(C)CCCCC1 UTZDKCFZGDSBGI-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000002872 norbornadienyl group Chemical group C12=C(C=C(CC1)C2)* 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
- 230000019612 pigmentation Effects 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5337—Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3247—Esters of acids containing the structure -C(=X)-P(=X)(R)(XH) or NC-P(=X)(R)(XH), (X = O, S, Se)
- C07F9/3252—Esters of acids containing the structure -C(=X)-P(=X)(R)(XH) or NC-P(=X)(R)(XH), (X = O, S, Se) containing the structure -C(=X)-P(=X)(R)(XR), (X = O, S, Se)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4062—Esters of acids containing the structure -C(=X)-P(=X)(XR)2 or NC-P(=X)(XR)2, (X = O, S, Se)
- C07F9/4065—Esters of acids containing the structure -C(=X)-P(=X)(XR)2, (X = O, S, Se)
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/46—Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/4841—Aromatic acids or derivatives (P-C aromatic linkage)
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Inorganic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Polymerisation Methods In General (AREA)
- Manufacturing Of Printed Circuit Boards (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Claims (11)
1. I fotopolymeriserbara ytbeläggningar, lack och tryckfärger använd fotopolymeriserbar massa, kännetecknad därav, att den som fotoinitiator innehäller en acylfosfinoxidförening med den allmänna formeln I, R1 2 3 0 ^Ρ-ϊ-R3 (I) R2 6 väri R^" är en rak eller förgrenad alkylgrupp med 1-6 kolatomer, en cyklohexyl-, cyklopentyl-, fenyl- eller naftyl-, halogen-, alkyl-eller alkoxisubstituerad fenyl- eller naftyl-, pyridyl- eller tienylgrupp; 2 112 R har samma betydelse som R , varvid R och R kan vara 2 sinsemellan lika eller olika, eller R är en alkoxigrupp med 1-6 1 2 kolatomer, en fenoxi- eller bensyloxigrupp, eller R och R bildar tillsammans en o-fenylendioxigrupp; 3 R är en rak eller förgrenad alkylgrupp med 2-18 kolatomer, en cykloalifatisk grupp med 3-12 kolatomer, en alkyl-, alkoxi-eller alkyltiosubstituerad fenyl- eller naftylgrupp, pyridyl-, 3 furyl- eller tienylgrupp, eller R är gruppen O R1 Il ^ -X-C-P ll\ 2 0 R II 2 väri R och R har samma betydelse som ovan och X är fenylen eller en 2-6 kolatomer innehällande alifatisk eller en 3-6 kolatomer innehällande cykloalifatisk tvävärd grupp; och varvid eventuelit en eller flera av grupperna R^-R^ är olefinskt omättad. 2
2. Fotopolymeriserbar massa enligt patentkravet 1, kännetecknad därav, att i den som fotoinitiator använda 3 acylfosfinoxidföreningen är R en tertiär alifatisk grupp.
3. Fotopolymeriserbar massa enligt patentkravet 1, kännetecknad därav, att i den som fotoinitiator använda acyl- 68241 fosfinoxidföreningen är en mono-, di- eller triaikylsubstituerad fenylgrupp, varvid alkylgruppen eller -grupperna har 1-8 kolatomer.
4. Fotopolymeriserbar massa enligt patentkravet 1, k ä n n e -t e c k n a d därav, att i den som fotoinitiator använda acyl- 3 fosfinoxidföreningen är R en ätminstone tvä substituenter innehällande fenyl-, pyridyl-, furyl- eller tienylgrupp, vilken ätminstone vid de bäda tili karbonylgruppens bindningsställe angränsande kolatomerna har substituenterna A och B, som kan vara sinsemellan lika eller olika, och är 1-6 kolatomer innehällande alkyl-, alkoxi- eller alkyltiogrupper, 5-7 kolatomer innehällande O cykloalkylgrupper, fenylgrupper eller halogenatomer, eller R är en <*-naf tylgrupp, som ätminstone i 2,8-positionerna har substituenterna A och B, eller en p-naftylgrupp, som ätminstone i 1,3-positionerna har substituenterna A och B.
5. Fotopolymeriserbar massa enligt patentkravet 4, k ä n n e -t e c k n a d därav, att i den som fotoinitiator använda acyl- 3 fosfinoxidföreningen är R en 2,4,6-trimetylfenyl-, 2,3,6-tri-metylfenyl-, 2,6-dimetoxifenyl-, 2,6-diklorfenyl-, 2,6-bis(metyl-tio)fenyl- eller 2,3,5,6-tetrametylfenylgrupp.
6. Fotopolymeriserbar massa enligt patentkravet 4 eller 5, kännetecknad därav, att i den som fotoinitiator an- 1 2 vända acylfosfinoxidföreningen är R och R fenyl- eller C,-C - 1 6 alkylsubstituerade fenylgrupper.
7. Fotopolymeriserbar massa enligt nägot av de föregäende patentkraven, kännetecknad därav, att den innehäller en acylfosfinoxidförening tillsammans med en sekundär och/eller tertiär amin.
8. Fotopolymeriserbar massa enligt nägot av de föregäende patentkraven, kännetecknad därav, att den innehäller en som fotoinitiator använd acylfosfinoxidförening 0,001-20 %, fördelaktigt 0,01-4 %.
9. Fotopolymeriserbar massa enligt nägot av de föregäende patentkraven, kännetecknad därav, att den som fotoinitiator använda acylfosfinoxidföreningen förekommer i ytbe-läggningar, lack och tryckfärger i blandningsförhällandet acylfosf inoxidförening raromatisk keton 10:1-1:30, fördelaktigt 1:1-1:10.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FI840240A FI69085C (fi) | 1978-07-14 | 1984-01-20 | Fotopolymeriserbar registreringsmassa isynnerhet foer framstaellning av tryckplattor och reliefformar |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19782830927 DE2830927A1 (de) | 1978-07-14 | 1978-07-14 | Acylphosphinoxidverbindungen und ihre verwendung |
DE2830927 | 1978-07-14 | ||
DE19792909994 DE2909994A1 (de) | 1979-03-14 | 1979-03-14 | Acylphosphinoxidverbindungen, ihre herstellung und verwendung |
DE2909994 | 1979-03-14 | ||
DE19792909992 DE2909992A1 (de) | 1979-03-14 | 1979-03-14 | Photopolymerisierbare aufzeichnungsmassen, insbesondere zur herstellung von druckplatten und reliefformen |
DE2909992 | 1979-03-14 |
Publications (3)
Publication Number | Publication Date |
---|---|
FI792196A FI792196A (fi) | 1980-01-15 |
FI68241B true FI68241B (fi) | 1985-04-30 |
FI68241C FI68241C (fi) | 1985-08-12 |
Family
ID=27187601
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI792196A FI68241C (fi) | 1978-07-14 | 1979-07-12 | Fotopolymeriserbar massa |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0007508B1 (sv) |
DE (1) | DE2965566D1 (sv) |
DK (1) | DK171353B1 (sv) |
ES (1) | ES482450A1 (sv) |
FI (1) | FI68241C (sv) |
NO (1) | NO160215C (sv) |
Families Citing this family (105)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3020092A1 (de) * | 1980-05-27 | 1981-12-10 | Basf Ag, 6700 Ludwigshafen | Acylphosphinverbindungen und ihre verwendung |
DE3023486A1 (de) * | 1980-06-24 | 1982-01-07 | Bayer Ag, 5090 Leverkusen | Photopolymerisierbare mischungen mit aroylphosphonsaeureestern als photoinitiatoren |
DE3114341A1 (de) * | 1981-04-09 | 1982-11-11 | Basf Ag, 6700 Ludwigshafen | Acylphosphinverbindungen, ihre herstellung und verwendung |
DE3133419A1 (de) * | 1981-08-24 | 1983-03-10 | Basf Ag, 6700 Ludwigshafen | Acylphosphinoxidverbindungen und ihre verwendung |
DE3236026A1 (de) * | 1982-09-29 | 1984-03-29 | Basf Ag, 6700 Ludwigshafen | Photopolymerisierbare massen und ihre verwendung |
DE3424182A1 (de) * | 1984-06-30 | 1986-01-09 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von chlor-phenyl-phosphanen |
JP2653458B2 (ja) * | 1988-03-26 | 1997-09-17 | 旭化成工業株式会社 | 凸版印刷版用感光性樹脂組成物 |
DE59010615D1 (de) * | 1989-08-04 | 1997-02-06 | Ciba Geigy Ag | Mono- und Diacylphosphinoxide |
DE4033215A1 (de) * | 1990-10-19 | 1992-04-23 | Hoechst Ag | Acyl-(2'-hydroxybiphenyl-2-yl)-phosphinsaeuresalze, ihre herstellung und verwendung |
EP0487453B1 (de) * | 1990-11-21 | 1996-05-22 | Ciba-Geigy Ag | Silylierte Acylphosphinoxide |
DE4230555A1 (de) * | 1992-09-12 | 1994-03-17 | Basf Ag | Verfahren zur Herstellung von alpha-Carbonylphosphinoxiden |
EP0600373A1 (de) * | 1992-12-03 | 1994-06-08 | Hoechst Aktiengesellschaft | Arylphosphonsäurealkyl-arylester, Verfahren zu ihrer Herstellung und ihre Verwendung |
DE4240964A1 (de) * | 1992-12-05 | 1994-06-09 | Basf Ag | Arenbisphosphinoxide |
DE4302123A1 (de) * | 1993-01-27 | 1994-07-28 | Herberts Gmbh | Verfahren zum Bedrucken von Glashohlkörpern |
DE19502913C1 (de) * | 1995-01-31 | 1996-11-21 | Hoechst Ag | Verfahren zur Herstellung von Arylphosphinigsäurealkylestern |
EP0725072A1 (de) * | 1995-01-31 | 1996-08-07 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Arylphosphinigsäurealkylestern |
DE19502911C2 (de) * | 1995-01-31 | 1996-12-05 | Hoechst Ag | Verfahren zur Herstellung von Arylphosphinigsäurealkylestern |
EP0825201B2 (en) † | 1996-08-23 | 2006-11-29 | Showa Denko Kabushiki Kaisha | Photocurable composition and curing process therefor |
SG53043A1 (en) * | 1996-08-28 | 1998-09-28 | Ciba Geigy Ag | Molecular complex compounds as photoinitiators |
DE19650562A1 (de) | 1996-12-05 | 1998-06-10 | Basf Ag | Photoinitiatorgemische, enthaltend Acylphosphinoxide und Benzophenonderivate |
EE04350B1 (et) | 1998-03-13 | 2004-08-16 | Akzo Nobel N.V. | Oksüdatiivselt kuivaval alküüdvaigul ja fotoinitsiaatoril põhinev mittevesikatte kompositsioon |
DE19812859A1 (de) * | 1998-03-24 | 1999-09-30 | Basf Ag | Photoinitiatorgemische |
DE19961342B4 (de) | 1999-12-17 | 2004-02-19 | 3M Espe Ag | Radikalisch härtbare Urethanpräpolymere und deren Verwendung |
DE10058830B4 (de) | 2000-11-27 | 2005-01-27 | 3M Espe Ag | Verwendung von verzweigten Polysäuren in Dentalmassen und Dentalmassen enthaltend verzweigte Polysäuren |
DE10124028B4 (de) | 2001-05-16 | 2010-02-18 | 3M Espe Ag | Selbstadhäsive Dentalmaterialien |
DE10206117A1 (de) | 2002-02-13 | 2003-08-14 | Basf Ag | Acyl- und Bisacylphosphinderivate |
ATE402183T1 (de) * | 2002-06-11 | 2008-08-15 | Ciba Holding Inc | Multimere formen von mono- und bis- acylphosphinoxiden |
DE10241299A1 (de) | 2002-09-04 | 2004-03-25 | Basf Ag | Strahlungshärtbare Polyurethane mit verkappten Aminogrupppen |
DE10244684A1 (de) | 2002-09-24 | 2004-04-01 | Basf Ag | Verfahren zur Herstellung von Acylphosphinoxiden |
DE10315671A1 (de) | 2003-04-04 | 2004-10-14 | Basf Ag | Verfahren zur Herstellung von Acylphosphinoxid-Feststoffen |
DE10318698A1 (de) * | 2003-04-24 | 2004-11-18 | Basf Ag | Verfahren zur Herstellung von Acylphosphinen |
DE10348463A1 (de) | 2003-10-14 | 2005-05-25 | Basf Ag | Hyperverzweigte Polyester mit ethylenisch ungesättigten Gruppen |
DE102004063102A1 (de) | 2004-12-22 | 2006-07-13 | Basf Ag | Strahlungshärtbare Verbindungen |
US20080260959A1 (en) | 2005-02-10 | 2008-10-23 | Basf Aktiengesellschaft Patents, Trademarks And Licences | Use of Dithiophosphinic Acid and/or Its Salts for Producing Anti-Corrosion Coatings that are Devoid of Chrome |
WO2006089935A1 (de) | 2005-02-24 | 2006-08-31 | Basf Aktiengesellschaft | Strahlungshärtbare wässrige polyurethandispersionen |
DE102005010109A1 (de) | 2005-03-02 | 2006-09-07 | Basf Ag | Modifizierte Polyolefinwachse |
WO2007018287A1 (ja) | 2005-08-11 | 2007-02-15 | Kyowa Hakko Chemical Co., Ltd. | 樹脂組成物 |
DE102005057683A1 (de) | 2005-12-01 | 2007-06-06 | Basf Ag | Strahlungshärtbare wasserelmulgierbare Polyisocyanate |
CN101616946B (zh) | 2007-02-15 | 2012-07-18 | 巴斯夫欧洲公司 | 聚氨酯分散体及其制备和用途 |
DE102007026196A1 (de) | 2007-06-04 | 2008-12-11 | Basf Se | Verfahren zur Herstellung wasseremulgierbarer Polyurethanacrylate |
DE102008002008A1 (de) | 2007-06-04 | 2008-12-11 | Basf Se | Verfahren zur Herstellung wasseremulgierbarer Polyurethanacrylate |
DE102008041654A1 (de) | 2007-08-31 | 2009-03-05 | Basf Se | Neue Beschichtungsmittel |
DE102010001956A1 (de) | 2009-02-17 | 2010-08-19 | Basf Se | Verfahren zur Herstellung wasseremulgierbarer Polyurethanacrylate |
DE102010003308A1 (de) | 2009-03-31 | 2011-01-13 | Basf Se | Strahlungshärtbare wasseremulgierbare Polyurethan(meth)acrylate |
DE102009016025B4 (de) | 2009-04-02 | 2014-12-11 | Voco Gmbh | Kunststoffmodifizierter Glasionomerzement, seine Verwendung sowie Verfahren zu seiner Herstellung |
EP2350154B1 (de) | 2009-08-05 | 2012-09-19 | Basf Se | (meth)acrylierte melamin-formaldehyd-harze |
DE102010044204A1 (de) | 2009-11-25 | 2011-05-26 | Basf Se | Verfahren zur Herstellung von strahlungshärtbaren (Meth)Acrylaten |
DE102010044206A1 (de) | 2009-11-25 | 2011-05-26 | Basf Se | Verfahren zur Herstellung von strahlungshärtbaren (Meth)Acrylaten |
DE102010003881A1 (de) | 2010-04-12 | 2011-10-13 | Voco Gmbh | Dentale Abdeckmasse |
DE102010003883A1 (de) | 2010-04-12 | 2011-10-13 | Voco Gmbh | Lichthärtbares Kompositmaterial |
DE102010003884A1 (de) | 2010-04-12 | 2011-10-13 | Voco Gmbh | Dualhärtende, mehrkomponentige dentale Zusammensetzung |
DE102010026490A1 (de) | 2010-07-07 | 2012-01-12 | Basf Se | Verfahren zur Herstellung von feinstrukturierten Oberflächen |
DE102010046697A1 (de) | 2010-09-28 | 2012-03-29 | Kettenbach Gmbh & Co. Kg | Polymerisierbares Dentalmaterial mit Reaktiv-Pastenbildner, gehärtetes Dentalmaterial und deren Verwendung |
EP2436365B1 (de) | 2010-09-30 | 2017-03-08 | VOCO GmbH | Kompositmaterial umfassend ein Monomer mit einem polyalicyclischen Strukturelement |
EP2436366B1 (de) | 2010-09-30 | 2015-07-29 | VOCO GmbH | Kompositmaterial umfassend ein Monomer mit einem polyalicyclischen Strukturelement als Versiegelungsmaterial |
US8915736B2 (en) | 2010-09-30 | 2014-12-23 | Voco Gmbh | Composition comprising a monomer with a polyalicyclic structure element for filling and/or sealing a root canal |
US9079828B2 (en) | 2010-09-30 | 2015-07-14 | Voco Gmbh | Polymerizable compounds comprising a polyalicylic structure element |
EP2436364B1 (de) | 2010-09-30 | 2017-05-31 | VOCO GmbH | Lackzusammensetzung umfassend ein Monomer mit einem polyalicyclischen Strukturelement |
EP2450025B1 (de) | 2010-11-08 | 2012-11-28 | VOCO GmbH | Polymerisierbare Phosphorsäurederivate umfassend ein polyalicyclisches Strukturelement |
DE102011003289A1 (de) | 2011-01-27 | 2012-08-02 | Voco Gmbh | Dentale provisorische Suprakonstruktionen sowie Materialien zu ihrer Herstellung und entsprechende Verfahren |
CN103608375B (zh) | 2011-06-14 | 2015-09-09 | 巴斯夫欧洲公司 | 可辐射固化聚氨酯水分散体 |
DE102012001978A1 (de) | 2012-02-02 | 2013-08-08 | Voco Gmbh | Dentale Kompositmaterialien enthaltend tricyclische Weichmacher |
DE102012001979A1 (de) | 2012-02-02 | 2013-08-08 | Voco Gmbh | Härtbares Gemisch umfassend Weichmacher mit einem polyalicyclischen Strukturelement zur Anwendung bei der Herstellung dentaler Werkstoffe |
EP2828311A1 (de) | 2012-03-19 | 2015-01-28 | Basf Se | Strahlungshärtbare wässrige dispersionen |
US9193888B2 (en) | 2012-03-19 | 2015-11-24 | Basf Se | Radiation-curable aqueous dispersions |
EP2649981B1 (de) | 2012-04-11 | 2018-11-21 | Ivoclar Vivadent AG | Polymerisierbare Zusammensetzungen mit hoher Polymerisationstiefe |
KR101745447B1 (ko) | 2012-05-30 | 2017-06-14 | 아이지엠 그룹 비.브이. | 방사선-경화성 화합물 |
US9296907B2 (en) | 2012-05-30 | 2016-03-29 | Basf Se | Radiation-curable compounds |
DE102012212429A1 (de) | 2012-07-16 | 2014-01-16 | Voco Gmbh | Dentalhandgerät, Verfahren und Verwendung desselben zum Aushärten lichthärtbaren Materials |
US20150191620A1 (en) | 2012-07-20 | 2015-07-09 | Basf Se | Fast-Drying, Radiation-Curable Coating Compounds |
WO2014023639A1 (de) | 2012-08-09 | 2014-02-13 | Basf Se | Strahlungshärtbare formulierungen mit hoher haftung |
DE102012214540A1 (de) | 2012-08-15 | 2014-02-20 | Helmholtz-Zentrum für Infektionsforschung GmbH | Zahnfüllungsmaterialien und Zahnlacke zur Hemmung der Biofilmbildung von Streptococcus mutans und deren Herstellung |
WO2014033280A2 (de) | 2012-08-31 | 2014-03-06 | Kettenbach Gmbh & Co. Kg | Radikalisch polymerisierbares dentalmaterial, gehärtetes produkt und verwendung |
DE102013008176A1 (de) | 2012-10-05 | 2014-04-10 | Voco Gmbh | Kit und Verfahren zur indirekten chairside Herstellung von Kompositinlays |
US9752056B2 (en) | 2012-10-24 | 2017-09-05 | Basf Se | Radiation-curing, water-dispersible polyurethane (meth)acrylates |
KR20150085044A (ko) | 2012-11-16 | 2015-07-22 | 바스프 에스이 | 폴리우레탄, 이의 분산액, 이들의 제조 방법 및 이들의 용도 |
WO2014090647A2 (en) | 2012-12-14 | 2014-06-19 | Basf Se | (meth)acrylated amino resins |
WO2014161817A1 (de) | 2013-04-03 | 2014-10-09 | Basf Se | Verfahren zur reduzierung der restmonomerenmenge in einer wässrigen polymerisatdispersion |
JP6436996B2 (ja) | 2013-08-26 | 2018-12-12 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 放射線硬化性で水分散性のポリウレタン(メタ)アクリレート |
RU2656392C2 (ru) | 2013-10-16 | 2018-06-06 | Басф Се | Способ получения водоэмульгируемых полиуретанакрилатов |
CA2927948C (en) | 2013-11-05 | 2022-04-26 | Construction Research & Technology Gmbh | Novel binding agent systems |
DE102013112468A1 (de) | 2013-11-13 | 2015-05-13 | Heraeus Kulzer Gmbh | Zahnprothese als nicht-invasive, transmuköse Darreichungsform zur Behandlung chronischer Erkrankungen, Verfahren zu Ihrer Herstellung sowie deren Verwendung |
CN114030259A (zh) | 2014-01-14 | 2022-02-11 | 扎伊罗技术股份公司 | 用于室内和室外的层状建筑板 |
EP2942361A1 (en) | 2014-05-06 | 2015-11-11 | Basf Se | Grain enhancement with surfactants in water-based uv-radiation curable polyurethane dispersions |
DK3201261T3 (en) | 2014-10-01 | 2019-04-08 | Basf Se | PROCEDURE FOR Curing HARDWARE COMPOSITIONS |
DE102014116389A1 (de) | 2014-11-11 | 2016-05-12 | Voco Gmbh | Radikalisch härtbare dentale Zusammensetzungen |
DE102014116402A1 (de) | 2014-11-11 | 2016-05-12 | Voco Gmbh | Verwendung radikalisch härtbarer Zusammensetzungen in generativen Fertigungsverfahren |
KR20170095233A (ko) | 2014-12-17 | 2017-08-22 | 바스프 에스이 | 쇄-연장되고 가교-결합된 폴리우레탄을 기초로 한 복사선 경화성 코팅 조성물 |
US11566153B2 (en) | 2015-07-06 | 2023-01-31 | Elkem Silicones France Sas | Self-adhesive multi-layer item and method for the production thereof |
KR20180041165A (ko) | 2015-08-17 | 2018-04-23 | 바스프 에스이 | 폴리우레탄 (메트)아크릴레이트를 포함하는 수성 중합체 조성물 |
EP3173449A1 (de) | 2015-11-27 | 2017-05-31 | BASF Coatings GmbH | Verbund aus zwei festkörpern |
CA3033081C (en) | 2016-08-19 | 2023-12-05 | Xylo Technologies Ag | Coated panel and method for manufacturing a coated panel |
DE102017103084A1 (de) | 2017-02-15 | 2018-08-16 | Voco Gmbh | Dentaler Kompositblock zur Herstellung permanenter indirekter Restaurationen im CAD/CAM Verfahren |
DE102017105841A1 (de) | 2017-03-17 | 2018-09-20 | Voco Gmbh | Fräsrohling zur Herstellung einer indirekten dentalen Restauration, entsprechende Verwendungen und Verfahren |
DE102018103415A1 (de) | 2018-02-15 | 2019-08-22 | Voco Gmbh | Dentale Formkörper mit kontinuierlichem Farbverlauf |
DE102018114690A1 (de) | 2018-06-19 | 2019-12-19 | Voco Gmbh | Thermowirksame dentale Kompositzusammensetzung |
EP3820927B1 (en) | 2018-07-13 | 2024-07-17 | Miwon Austria Forschung und Entwicklung GmbH | Water-dispersible polyurethane (meth)acrylates for actinic radiation curable coatings |
EP3870618B1 (de) | 2018-10-26 | 2023-07-12 | Basf Se | Wässrige bindemittelformulierung auf basis von funktioalisierten polyurethanen |
DE102019122174A1 (de) | 2019-08-19 | 2021-02-25 | Voco Gmbh | Dentale polymerisierbare Zusammensetzung auf der Basis kondensierter Silane |
ES2971221T3 (es) | 2019-10-08 | 2024-06-04 | Basf Se | Composiciones de revestimiento de dos componentes térmicamente curables |
DE102020132126A1 (de) | 2020-12-03 | 2022-06-09 | Leibniz-Institut Für Neue Materialien Gemeinnützige Gesellschaft Mit Beschränkter Haftung | Strukturiertes Material |
EP4274856A1 (fr) | 2021-01-08 | 2023-11-15 | Elkem Silicones France SAS | Composition silicone réticulable par irradiation comprenant un modulateur d'adhérence |
WO2023025554A1 (en) | 2021-08-26 | 2023-03-02 | Basf Se | Curable composition and 3d-printed object formed therefrom and process for forming the same |
WO2023156441A1 (en) | 2022-02-17 | 2023-08-24 | Basf Coatings Gmbh | Uv-curable coating compositions |
WO2024141320A1 (en) | 2022-12-29 | 2024-07-04 | Basf Se | Radiation curable liquid composition, process of forming 3d-printed object and 3d-printed object |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE125488C (sv) * | ||||
DE1010965B (de) * | 1956-05-08 | 1957-06-27 | Henkel & Cie Gmbh | Verfahren zur Herstellung von sauren Estern der Acylphosphonsaeuren bzw. ihrer Salze |
CH471535A (de) * | 1964-12-15 | 1969-04-30 | Ciba Geigy | Schädlingsbekämpfungsmittel |
CH573461A5 (en) * | 1971-01-05 | 1976-03-15 | Hoechst Ag | Photochemically polymerisable polyester moulding composn |
US3668093A (en) * | 1971-05-06 | 1972-06-06 | Du Pont | Photoinitiation of vinyl polymerization by triaroylphosphines |
DE2556830A1 (de) * | 1974-12-24 | 1976-07-08 | Ciba Geigy Ag | Neue phosphonate |
-
1979
- 1979-07-09 DE DE7979102347T patent/DE2965566D1/de not_active Expired
- 1979-07-09 EP EP79102347A patent/EP0007508B1/de not_active Expired
- 1979-07-12 ES ES482450A patent/ES482450A1/es not_active Expired
- 1979-07-12 FI FI792196A patent/FI68241C/fi not_active IP Right Cessation
- 1979-07-13 DK DK295979A patent/DK171353B1/da not_active IP Right Cessation
-
1984
- 1984-03-16 NO NO84841029A patent/NO160215C/no unknown
Also Published As
Publication number | Publication date |
---|---|
FI68241C (fi) | 1985-08-12 |
NO160215B (no) | 1988-12-12 |
EP0007508A2 (de) | 1980-02-06 |
NO841029L (no) | 1980-01-15 |
ES482450A1 (es) | 1980-04-01 |
NO160215C (no) | 1989-03-22 |
DK171353B1 (da) | 1996-09-16 |
EP0007508A3 (en) | 1980-10-29 |
EP0007508B1 (de) | 1983-06-01 |
DE2965566D1 (en) | 1983-07-07 |
DK295979A (da) | 1980-01-15 |
FI792196A (fi) | 1980-01-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
FI68241B (fi) | Fotopolymeriserbar massa | |
US4324744A (en) | Acylphosphine oxide compounds | |
FI71322C (fi) | Acylfosfinoxidfoereningar och deras anvaendning | |
AU700479B2 (en) | Alkoxyphenyl-substituted bisacylphosphine oxides | |
US4522693A (en) | Photopolymerizable composition with acylphosphine sulfide photoinitiator and method | |
JP4171073B2 (ja) | 不揮発性フェニルグリオキシル酸エステル | |
US6020528A (en) | Alkylphenylbisacylphosphine oxides and photoinitiator mixtures | |
US6251963B1 (en) | Photoinitiator combinations | |
RU2320641C2 (ru) | Внедряемый фотоинициатор | |
US4795766A (en) | Propiophenone derivatives as photoinitiators for photopolymerization | |
KR20010111021A (ko) | 유기 금속성 모노아실알킬포스핀 | |
JPH07278215A (ja) | 二量体ビスアシルホスフィン、ビスアシルホスフィンオキシドおよびビスアシルホスフィンスルフィド | |
EP0304886B1 (de) | Oligomere Benzilketale und ihre Verwendung als Photoinitiatoren | |
US4251341A (en) | Photoinitiators for UV-curable systems | |
US4088554A (en) | Initiators for photopolymerization | |
JPH04316588A (ja) | シリル化アシルホスフィンオキシド | |
FI69085C (fi) | Fotopolymeriserbar registreringsmassa isynnerhet foer framstaellning av tryckplattor och reliefformar | |
DK172228B1 (da) | Fotopolymeriserbar masse til fotopolymeriserbare overtræksmidler, lakker og trykfarver | |
NO792333L (no) | Acylfosfinoksydforbindelser og anvendelse av slike i fotopolymeriserbar oppmerkingsmasse | |
NO160214B (no) | Fotopolymeriserbare masser. |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MA | Patent expired |
Owner name: BASF AKTIENGESELLSCHAFT |