CA1113638A - Photopolymerizable composition containing a sensitized aromatic iodonium or sulfonium compound - Google Patents
Photopolymerizable composition containing a sensitized aromatic iodonium or sulfonium compoundInfo
- Publication number
- CA1113638A CA1113638A CA349,909A CA349909A CA1113638A CA 1113638 A CA1113638 A CA 1113638A CA 349909 A CA349909 A CA 349909A CA 1113638 A CA1113638 A CA 1113638A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- sensitized
- photoinitiator
- groups
- phenyl
- 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
Links
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 title claims abstract description 16
- -1 sulfonium compound Chemical class 0.000 title claims description 78
- 125000003118 aryl group Chemical group 0.000 title claims description 27
- 239000000203 mixture Substances 0.000 title description 24
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 10
- 150000001450 anions Chemical class 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 5
- 235000001671 coumarin Nutrition 0.000 claims description 5
- 150000004775 coumarins Chemical class 0.000 claims description 5
- 239000003822 epoxy resin Substances 0.000 claims description 5
- 229920000647 polyepoxide Polymers 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229920000412 polyarylene Polymers 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000007850 fluorescent dye Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract description 8
- 230000001235 sensitizing effect Effects 0.000 abstract description 8
- 239000000975 dye Substances 0.000 abstract description 6
- 230000003595 spectral effect Effects 0.000 abstract description 4
- 238000001228 spectrum Methods 0.000 abstract 2
- 230000035945 sensitivity Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 description 21
- 239000000243 solution Substances 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 125000003545 alkoxy group Chemical group 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000011550 stock solution Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 5
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical class C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- LTYMSROWYAPPGB-UHFFFAOYSA-O diphenylsulfanium Chemical compound C=1C=CC=CC=1[SH+]C1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-O 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000001699 photocatalysis Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000005504 styryl group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 2
- 239000012953 triphenylsulfonium Substances 0.000 description 2
- JCXLYAWYOTYWKM-UHFFFAOYSA-N (2,3,4-triphenylcyclopenta-1,3-dien-1-yl)benzene Chemical compound C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JCXLYAWYOTYWKM-UHFFFAOYSA-N 0.000 description 1
- XXCQVFAKDMZVLF-UHFFFAOYSA-M (4-methoxyphenyl)-phenyliodanium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.C1=CC(OC)=CC=C1[I+]C1=CC=CC=C1 XXCQVFAKDMZVLF-UHFFFAOYSA-M 0.000 description 1
- FBWNQGQXSIOOTF-UHFFFAOYSA-N 1,2,4-tris[2-(4-methoxyphenyl)ethenyl]benzene Chemical compound C1=CC(OC)=CC=C1C=CC(C=C1C=CC=2C=CC(OC)=CC=2)=CC=C1C=CC1=CC=C(OC)C=C1 FBWNQGQXSIOOTF-UHFFFAOYSA-N 0.000 description 1
- DQJYXWVSPPYNAA-UHFFFAOYSA-N 1,2,5-triphenylpyrrole Chemical compound C=1C=CC=CC=1N1C(C=2C=CC=CC=2)=CC=C1C1=CC=CC=C1 DQJYXWVSPPYNAA-UHFFFAOYSA-N 0.000 description 1
- XEPLAIYZZPDJQT-UHFFFAOYSA-N 1,3,5,6-tetraphenyl-2-benzofuran Chemical compound C1=CC=CC=C1C1=C2C=C(C=3C=CC=CC=3)C(C=3C=CC=CC=3)=CC2=C(C=2C=CC=CC=2)O1 XEPLAIYZZPDJQT-UHFFFAOYSA-N 0.000 description 1
- LJECMQUXHNGQJM-UHFFFAOYSA-N 1,3-bis[2-(4-methoxyphenyl)ethenyl]naphthalene Chemical compound C1=CC(OC)=CC=C1C=CC1=CC(C=CC=2C=CC(OC)=CC=2)=C(C=CC=C2)C2=C1 LJECMQUXHNGQJM-UHFFFAOYSA-N 0.000 description 1
- ZKSVYBRJSMBDMV-UHFFFAOYSA-N 1,3-diphenyl-2-benzofuran Chemical compound C1=CC=CC=C1C1=C2C=CC=CC2=C(C=2C=CC=CC=2)O1 ZKSVYBRJSMBDMV-UHFFFAOYSA-N 0.000 description 1
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 1
- XLHSIACSHBDRSU-UHFFFAOYSA-N 1-chloro-2-(4-phenylbuta-1,3-dienyl)benzene Chemical compound ClC1=CC=CC=C1C=CC=CC1=CC=CC=C1 XLHSIACSHBDRSU-UHFFFAOYSA-N 0.000 description 1
- CAWFCZIEFIQKRV-ONEGZZNKSA-N 1-methoxy-4-[(e)-2-(4-methoxyphenyl)ethenyl]benzene Chemical compound C1=CC(OC)=CC=C1\C=C\C1=CC=C(OC)C=C1 CAWFCZIEFIQKRV-ONEGZZNKSA-N 0.000 description 1
- OTJAKIZOANJRSA-UHFFFAOYSA-N 1-methoxy-4-[4-(4-methoxyphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(OC)=CC=C1C=CC=CC1=CC=C(OC)C=C1 OTJAKIZOANJRSA-UHFFFAOYSA-N 0.000 description 1
- KGLYHHCCIBZMLN-GGWOSOGESA-N 1-methyl-4-[(1e,3e)-4-(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1\C=C\C=C\C1=CC=C(C)C=C1 KGLYHHCCIBZMLN-GGWOSOGESA-N 0.000 description 1
- RTCXQMFXAWOHKN-UHFFFAOYSA-N 1-phenyl-4-(2-phenylethenyl)benzene Chemical group C=1C=CC=CC=1C=CC(C=C1)=CC=C1C1=CC=CC=C1 RTCXQMFXAWOHKN-UHFFFAOYSA-N 0.000 description 1
- IEZVMRGFNUNABR-UHFFFAOYSA-N 2,3,4,5-tetraphenyl-1h-pyrrole Chemical compound C1=CC=CC=C1C1=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 IEZVMRGFNUNABR-UHFFFAOYSA-N 0.000 description 1
- PAIKLRCZBDBOTL-UHFFFAOYSA-N 2,3,4,5-tetraphenyl-3,4-dihydropyrazole Chemical compound C1=CC=CC=C1C1N(C=2C=CC=CC=2)N=C(C=2C=CC=CC=2)C1C1=CC=CC=C1 PAIKLRCZBDBOTL-UHFFFAOYSA-N 0.000 description 1
- FHWBAFNKDXAKOW-PHEQNACWSA-N 2,5-bis[(e)-2-phenylethenyl]furan Chemical compound C=1C=C(\C=C\C=2C=CC=CC=2)OC=1/C=C/C1=CC=CC=C1 FHWBAFNKDXAKOW-PHEQNACWSA-N 0.000 description 1
- NHJZSMMHVFJBED-PHEQNACWSA-N 2,5-bis[(e)-2-phenylethenyl]thiophene Chemical compound C=1C=C(\C=C\C=2C=CC=CC=2)SC=1/C=C/C1=CC=CC=C1 NHJZSMMHVFJBED-PHEQNACWSA-N 0.000 description 1
- RJCRXUOYULQDPG-UHFFFAOYSA-N 2,5-diphenyl-1h-pyrrole Chemical compound C=1C=C(C=2C=CC=CC=2)NC=1C1=CC=CC=C1 RJCRXUOYULQDPG-UHFFFAOYSA-N 0.000 description 1
- ZWCZPVMIHLKVLD-UHFFFAOYSA-N 2,5-diphenyl-3,4-dihydropyrazole Chemical compound C1CC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 ZWCZPVMIHLKVLD-UHFFFAOYSA-N 0.000 description 1
- VUPDHIIPAKIKAB-UHFFFAOYSA-N 2,5-diphenylfuran Chemical compound C=1C=C(C=2C=CC=CC=2)OC=1C1=CC=CC=C1 VUPDHIIPAKIKAB-UHFFFAOYSA-N 0.000 description 1
- HWKZNRABKQDKTC-UHFFFAOYSA-N 2,5-diphenylthiophene Chemical compound C=1C=C(C=2C=CC=CC=2)SC=1C1=CC=CC=C1 HWKZNRABKQDKTC-UHFFFAOYSA-N 0.000 description 1
- MMPWFAXINROIDQ-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-(2,4-dimethoxyphenyl)-3,4-dihydropyrazole Chemical compound COC1=CC(OC)=CC=C1C1=NN(C=2C=C(Cl)C=CC=2)CC1 MMPWFAXINROIDQ-UHFFFAOYSA-N 0.000 description 1
- FMZMWKZBEPVRTO-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-phenyl-3,4-dihydropyrazole Chemical compound C1=CC(OC)=CC=C1N1N=C(C=2C=CC=CC=2)CC1 FMZMWKZBEPVRTO-UHFFFAOYSA-N 0.000 description 1
- IDWIWJGDLZJTEZ-UHFFFAOYSA-N 2-(4-phenylbuta-1,3-dienyl)naphthalene Chemical compound C=1C=C2C=CC=CC2=CC=1C=CC=CC1=CC=CC=C1 IDWIWJGDLZJTEZ-UHFFFAOYSA-N 0.000 description 1
- RSUHHHQRLYRPQR-UHFFFAOYSA-N 2-[5-[1-(diethylamino)-2-phenylethenyl]-2-phenyl-3,4-dihydropyrazol-3-yl]-n,n-diethylaniline Chemical compound N=1N(C=2C=CC=CC=2)C(C=2C(=CC=CC=2)N(CC)CC)CC=1C(N(CC)CC)=CC1=CC=CC=C1 RSUHHHQRLYRPQR-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- AKEBXQRDSUBABJ-UHFFFAOYSA-N 2-naphthalen-1-yl-5-phenyl-3,4-dihydropyrazole Chemical compound N=1N(C=2C3=CC=CC=C3C=CC=2)CCC=1C1=CC=CC=C1 AKEBXQRDSUBABJ-UHFFFAOYSA-N 0.000 description 1
- BMYOQZQFKPCFNQ-UHFFFAOYSA-N 2-phenyl-5-(2-phenylethenyl)-3,4-dihydropyrazole Chemical compound N=1N(C=2C=CC=CC=2)CCC=1C=CC1=CC=CC=C1 BMYOQZQFKPCFNQ-UHFFFAOYSA-N 0.000 description 1
- YEGBWHMQQAHSME-UHFFFAOYSA-N 3-methyl-2,5-diphenylfuran Chemical compound CC=1C=C(C=2C=CC=CC=2)OC=1C1=CC=CC=C1 YEGBWHMQQAHSME-UHFFFAOYSA-N 0.000 description 1
- JQWZMXNLCJLCOJ-UHFFFAOYSA-N 3-naphthalen-1-yl-2,5-diphenyl-3,4-dihydropyrazole Chemical compound C1C(C=2C3=CC=CC=C3C=CC=2)N(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 JQWZMXNLCJLCOJ-UHFFFAOYSA-N 0.000 description 1
- AZPXELGXAFZFPC-UHFFFAOYSA-N 3-phenyl-4,5-dihydro-1h-pyrazole Chemical compound N1CCC(C=2C=CC=CC=2)=N1 AZPXELGXAFZFPC-UHFFFAOYSA-N 0.000 description 1
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 1
- AIELZBQKZTXOON-UHFFFAOYSA-N 4-(2-phenyl-3,4-dihydropyrazol-5-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=NN(C=2C=CC=CC=2)CC1 AIELZBQKZTXOON-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- LBASRTOKVSTSJC-UHFFFAOYSA-N 5,6-dimethyl-1,3-diphenyl-2-benzofuran Chemical compound C=12C=C(C)C(C)=CC2=C(C=2C=CC=CC=2)OC=1C1=CC=CC=C1 LBASRTOKVSTSJC-UHFFFAOYSA-N 0.000 description 1
- RHWPEOUEWCKBTJ-UHFFFAOYSA-N 7-(dimethylamino)-3-phenylchromen-2-one Chemical compound O=C1OC2=CC(N(C)C)=CC=C2C=C1C1=CC=CC=C1 RHWPEOUEWCKBTJ-UHFFFAOYSA-N 0.000 description 1
- UDFPKNSWSYBIHO-UHFFFAOYSA-N 7-methoxy-4-methyl-1-benzopyran-2-one Chemical compound CC1=CC(=O)OC2=CC(OC)=CC=C21 UDFPKNSWSYBIHO-UHFFFAOYSA-N 0.000 description 1
- LHFIAMMRYGQCJH-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OC1CC2OC2CC1 LHFIAMMRYGQCJH-UHFFFAOYSA-N 0.000 description 1
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 206010073306 Exposure to radiation Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- ZENGMMQJMCPHTK-FPPPDJHPSA-N [(1e,3e,5e,7e)-8-phenylocta-1,3,5,7-tetraenyl]benzene Chemical compound C=1C=CC=CC=1\C=C\C=C\C=C\C=C\C1=CC=CC=C1 ZENGMMQJMCPHTK-FPPPDJHPSA-N 0.000 description 1
- 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 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 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
- 239000012965 benzophenone Substances 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- JKZGATLOUUUDDG-UHFFFAOYSA-N bis(4-ethoxyphenyl)methanethiol Chemical compound C1=CC(OCC)=CC=C1C(S)C1=CC=C(OCC)C=C1 JKZGATLOUUUDDG-UHFFFAOYSA-N 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- KDTAEYOYAZPLIC-UHFFFAOYSA-N coumarin 152 Chemical compound FC(F)(F)C1=CC(=O)OC2=CC(N(C)C)=CC=C21 KDTAEYOYAZPLIC-UHFFFAOYSA-N 0.000 description 1
- AFYCEAFSNDLKSX-UHFFFAOYSA-N coumarin 460 Chemical compound CC1=CC(=O)OC2=CC(N(CC)CC)=CC=C21 AFYCEAFSNDLKSX-UHFFFAOYSA-N 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- OWZDULOODZHVCQ-UHFFFAOYSA-N diphenyl-(4-phenylsulfanylphenyl)sulfanium Chemical compound C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 OWZDULOODZHVCQ-UHFFFAOYSA-N 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting 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
- 238000005649 metathesis reaction Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- FBCPAUQAXBOKHD-UHFFFAOYSA-N n-[4-(2,5-diphenyl-3,4-dihydropyrazol-3-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1N(C=2C=CC=CC=2)N=C(C=2C=CC=CC=2)C1 FBCPAUQAXBOKHD-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 150000004010 onium ions Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- KTNLYTNKBOKXRW-UHFFFAOYSA-N phenyliodanium Chemical compound [IH+]C1=CC=CC=C1 KTNLYTNKBOKXRW-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 208000017983 photosensitivity disease Diseases 0.000 description 1
- 231100000434 photosensitization Toxicity 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical compound C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 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
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16K—VALVES; TAPS; COCKS; ACTUATING-FLOATS; DEVICES FOR VENTING OR AERATING
- F16K11/00—Multiple-way valves, e.g. mixing valves; Pipe fittings incorporating such valves
- F16K11/02—Multiple-way valves, e.g. mixing valves; Pipe fittings incorporating such valves with all movable sealing faces moving as one unit
- F16K11/06—Multiple-way valves, e.g. mixing valves; Pipe fittings incorporating such valves with all movable sealing faces moving as one unit comprising only sliding valves, i.e. sliding closure elements
- F16K11/078—Multiple-way valves, e.g. mixing valves; Pipe fittings incorporating such valves with all movable sealing faces moving as one unit comprising only sliding valves, i.e. sliding closure elements with pivoted and linearly movable closure members
-
- 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
- Y10T137/00—Fluid handling
- Y10T137/8593—Systems
- Y10T137/86493—Multi-way valve unit
- Y10T137/86549—Selective reciprocation or rotation
-
- 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
- Y10T137/00—Fluid handling
- Y10T137/8593—Systems
- Y10T137/87917—Flow path with serial valves and/or closures
- Y10T137/87981—Common actuator
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- General Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Mechanical Engineering (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Polymerisation Methods In General (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Sealing Material Composition (AREA)
- Polyethers (AREA)
- Epoxy Resins (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/040,645 US4250053A (en) | 1979-05-21 | 1979-05-21 | Sensitized aromatic iodonium or aromatic sulfonium salt photoinitiator systems |
| US40,645 | 1979-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1113638A true CA1113638A (en) | 1981-12-01 |
Family
ID=21912128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA349,909A Expired CA1113638A (en) | 1979-05-21 | 1980-04-15 | Photopolymerizable composition containing a sensitized aromatic iodonium or sulfonium compound |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4250053A (en:Method) |
| JP (1) | JPS55155018A (en:Method) |
| KR (1) | KR840000122B1 (en:Method) |
| AU (1) | AU521591B2 (en:Method) |
| BE (1) | BE883404A (en:Method) |
| CA (1) | CA1113638A (en:Method) |
| DE (1) | DE3019211A1 (en:Method) |
| ES (1) | ES8106967A1 (en:Method) |
| FR (1) | FR2457511B1 (en:Method) |
| GB (1) | GB2053243B (en:Method) |
| IT (1) | IT1133014B (en:Method) |
| SE (1) | SE446780B (en:Method) |
| ZA (1) | ZA802991B (en:Method) |
Families Citing this family (249)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4351708A (en) * | 1980-02-29 | 1982-09-28 | Ciba-Geigy Corporation | Photochemically or thermally polymerizable mixtures |
| US4383025A (en) * | 1980-07-10 | 1983-05-10 | Ciba-Geigy Corporation | Photopolymerization by means of sulfoxonium salts |
| US4398014A (en) * | 1980-11-04 | 1983-08-09 | Ciba-Geigy Corporation | Sulfoxonium salts and their use as polymerization catalysts |
| US4386154A (en) * | 1981-03-26 | 1983-05-31 | Minnesota Mining And Manufacturing Company | Visible light sensitive, thermally developable imaging systems |
| US4491628A (en) * | 1982-08-23 | 1985-01-01 | International Business Machines Corporation | Positive- and negative-working resist compositions with acid generating photoinitiator and polymer with acid labile groups pendant from polymer backbone |
| AU569084B2 (en) * | 1983-06-27 | 1988-01-21 | Stauffer Chemical Company | Photopolymerizable composition |
| US4537854A (en) * | 1983-09-14 | 1985-08-27 | General Electric Company | Photoresist compositions and method |
| JPS6078443A (ja) * | 1983-10-05 | 1985-05-04 | Agency Of Ind Science & Technol | 光不溶性樹脂組成物 |
| DE3565013D1 (en) * | 1984-02-10 | 1988-10-20 | Ciba Geigy Ag | Process for the preparation of a protection layer or a relief pattern |
| US4554238A (en) * | 1984-03-20 | 1985-11-19 | Minnesota Mining And Manufacturing Company | Spectrally-sensitized imaging system |
| US4717605A (en) * | 1984-05-16 | 1988-01-05 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Radiation curable adhesives |
| US4579837A (en) * | 1984-10-22 | 1986-04-01 | Kms Fusion, Inc. | Solid phase photosensitizer for generation of singlet oxygen |
| CA1289803C (en) * | 1985-10-28 | 1991-10-01 | Robert J. Cox | Photoresist composition and printed circuit boards and packages made therewith |
| CA1312040C (en) * | 1985-12-19 | 1992-12-29 | Joseph Victor Koleske | Conformal coatings cured with actinic radiation |
| EP0243159A3 (en) * | 1986-04-22 | 1988-11-30 | Minnesota Mining And Manufacturing Company | Photopolymerizable compositions |
| JPH0721646B2 (ja) * | 1986-06-05 | 1995-03-08 | 高砂香料工業株式会社 | 電子写真感光体 |
| JPS6327830A (ja) * | 1986-07-21 | 1988-02-05 | Daicel Chem Ind Ltd | 蛍光性光硬化組成物 |
| US4751138A (en) * | 1986-08-11 | 1988-06-14 | Minnesota Mining And Manufacturing Company | Coated abrasive having radiation curable binder |
| US4836832A (en) * | 1986-08-11 | 1989-06-06 | Minnesota Mining And Manufacturing Company | Method of preparing coated abrasive having radiation curable binder |
| JPS6353539A (ja) * | 1986-08-25 | 1988-03-07 | Daicel Chem Ind Ltd | 蛍光性光硬化膜積層体 |
| JPS6356649A (ja) * | 1986-08-28 | 1988-03-11 | Daicel Chem Ind Ltd | 蛍光性光硬化膜 |
| US4828583A (en) * | 1987-04-02 | 1989-05-09 | Minnesota Mining And Manufacturing Company | Coated abrasive binder containing ternary photoinitiator system |
| CA1323949C (en) * | 1987-04-02 | 1993-11-02 | Michael C. Palazzotto | Ternary photoinitiator system for addition polymerization |
| EP0294333B1 (de) * | 1987-06-05 | 1993-03-17 | Ciba-Geigy Ag | Kationisch polymerisierbare Gemische enthaltend ausgewählte Härter |
| US4952612A (en) * | 1987-08-28 | 1990-08-28 | Minnesota Mining And Manufacturing Company | Energy-induced curable compositions |
| US5147900A (en) * | 1987-08-28 | 1992-09-15 | Minnesosta Mining And Manufacturing Company | Energy-induced dual curable compositions |
| US5086086A (en) * | 1987-08-28 | 1992-02-04 | Minnesota Mining And Manufacturing Company | Energy-induced curable compositions |
| US4950696A (en) * | 1987-08-28 | 1990-08-21 | Minnesota Mining And Manufacturing Company | Energy-induced dual curable compositions |
| US4889792A (en) * | 1987-12-09 | 1989-12-26 | Minnesota Mining And Manufacturing Company | Ternary photoinitiator system for addition polymerization |
| US4959297A (en) * | 1987-12-09 | 1990-09-25 | Minnesota Mining And Manufacturing Company | Ternary photoinitiator system for addition polymerization |
| US4933377A (en) * | 1988-02-29 | 1990-06-12 | Saeva Franklin D | Novel sulfonium salts and the use thereof as photoinitiators |
| US4985340A (en) * | 1988-06-01 | 1991-01-15 | Minnesota Mining And Manufacturing Company | Energy curable compositions: two component curing agents |
| US5047568A (en) * | 1988-11-18 | 1991-09-10 | International Business Machines Corporation | Sulfonium salts and use and preparation thereof |
| US4954416A (en) * | 1988-12-21 | 1990-09-04 | Minnesota Mining And Manufacturing Company | Tethered sulfonium salt photoinitiators for free radical polymerization |
| US6180317B1 (en) | 1988-12-30 | 2001-01-30 | International Business Machines Corporation | Composition for photoimaging |
| US5439766A (en) * | 1988-12-30 | 1995-08-08 | International Business Machines Corporation | Composition for photo imaging |
| US5264325A (en) * | 1988-12-30 | 1993-11-23 | International Business Machines Corporation | Composition for photo imaging |
| US5747223A (en) * | 1988-12-30 | 1998-05-05 | International Business Machines Corporation | Composition for photoimaging |
| US5026624A (en) * | 1989-03-03 | 1991-06-25 | International Business Machines Corporation | Composition for photo imaging |
| US5304457A (en) * | 1989-03-03 | 1994-04-19 | International Business Machines Corporation | Composition for photo imaging |
| US5278010A (en) * | 1989-03-03 | 1994-01-11 | International Business Machines Corporation | Composition for photo imaging |
| US4988607A (en) * | 1989-05-30 | 1991-01-29 | Minnesota Mining And Manufacturing Company | High speed photopolymerizable element with initiator in a topcoat |
| EP0410606B1 (en) | 1989-07-12 | 1996-11-13 | Fuji Photo Film Co., Ltd. | Siloxane polymers and positive working light-sensitive compositions comprising the same |
| JP2829054B2 (ja) * | 1989-09-28 | 1998-11-25 | 株式会社東芝 | レジスト組成物 |
| CA2032630C (en) * | 1989-12-28 | 1996-04-23 | Ichiro Yoshihara | Visible radiation sensitive composition |
| DE4009700A1 (de) * | 1990-03-27 | 1991-10-02 | Hoechst Ag | Photopolymerisierbares gemisch und daraus hergestelltes aufzeichnungsmaterial |
| US5045431A (en) * | 1990-04-24 | 1991-09-03 | International Business Machines Corporation | Dry film, aqueous processable photoresist compositions |
| DE69131158T2 (de) * | 1990-11-22 | 1999-12-16 | Canon K.K., Tokio/Tokyo | Photoempfindliches Aufzeichnungsmedium enthaltendes Volumen-Phasenhologram und Verfahren zum Herstellen von einem Volumen-Phasenhologram mit diesem Medium |
| DE4110793C1 (en) * | 1991-04-04 | 1992-04-02 | Th. Goldschmidt Ag, 4300 Essen, De | Organo:polysiloxane - used as photoinitiator in cationically curable organo:polysiloxane compsn. esp. contg. epoxy¨ or vinyl¨ gps. |
| JP2873126B2 (ja) * | 1991-04-17 | 1999-03-24 | 日本ペイント株式会社 | 体積ホログラム記録用感光性組成物 |
| US5422204A (en) * | 1991-07-19 | 1995-06-06 | Canon Kabushiki Kaisha | Photo-crosslinkable resin composition and hologram recording medium |
| CA2070354A1 (en) * | 1991-08-26 | 1993-02-27 | Melville R. Sahyun | Sensitization of photopolymerizable compositions |
| US5439779A (en) * | 1993-02-22 | 1995-08-08 | International Business Machines Corporation | Aqueous soldermask |
| JP2849021B2 (ja) * | 1993-04-12 | 1999-01-20 | 日本ペイント株式会社 | 体積ホログラム記録用感光性組成物 |
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| US5856373A (en) * | 1994-10-31 | 1999-01-05 | Minnesota Mining And Manufacturing Company | Dental visible light curable epoxy system with enhanced depth of cure |
| US5593812A (en) * | 1995-02-17 | 1997-01-14 | International Business Machines Corporation | Photoresist having increased sensitivity and use thereof |
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| US5707780A (en) * | 1995-06-07 | 1998-01-13 | E. I. Du Pont De Nemours And Company | Photohardenable epoxy composition |
| US6025406A (en) * | 1997-04-11 | 2000-02-15 | 3M Innovative Properties Company | Ternary photoinitiator system for curing of epoxy resins |
| US5998495A (en) | 1997-04-11 | 1999-12-07 | 3M Innovative Properties Company | Ternary photoinitiator system for curing of epoxy/polyol resin compositions |
| US6001936A (en) | 1997-10-24 | 1999-12-14 | 3M Innovative Properties Company | Dye enhanced durability through controlled dye environment |
| US6085004A (en) * | 1998-02-03 | 2000-07-04 | 3M Innovative Properties Company | Optical fiber connector using photocurable adhesive |
| US6518362B1 (en) | 1998-02-18 | 2003-02-11 | 3M Innovative Properties Company | Melt blending polyphenylene ether, polystyrene and curable epoxy |
| ID26627A (id) | 1998-02-23 | 2001-01-25 | B F Goodrich Company Cs | Komposisi-komposisi penahan polisiklik dengan tahanan etsa yang ditingkatkan |
| US6274643B1 (en) | 1998-05-01 | 2001-08-14 | 3M Innovative Properties Company | Epoxy/thermoplastic photocurable adhesive composition |
| US6077601A (en) | 1998-05-01 | 2000-06-20 | 3M Innovative Properties Company | Coated abrasive article |
| US6136398A (en) * | 1998-05-01 | 2000-10-24 | 3M Innovative Properties Company | Energy cured sealant composition |
| US6057382A (en) * | 1998-05-01 | 2000-05-02 | 3M Innovative Properties Company | Epoxy/thermoplastic photocurable adhesive composition |
| US6228133B1 (en) | 1998-05-01 | 2001-05-08 | 3M Innovative Properties Company | Abrasive articles having abrasive layer bond system derived from solid, dry-coated binder precursor particles having a fusible, radiation curable component |
| US7005394B1 (en) | 1998-07-10 | 2006-02-28 | 3M Innovative Properties Company | Tackified thermoplastic-epoxy pressure sensitive adhesives |
| US6331080B1 (en) | 1998-07-15 | 2001-12-18 | 3M Innovative Properties Company | Optical fiber connector using colored photocurable adhesive |
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Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3991049A (en) * | 1967-07-14 | 1976-11-09 | Ciba-Geigy Ag | Aromatic compounds containing ethylene double bonds, processes for their manufacture and use |
| US3879463A (en) * | 1973-05-10 | 1975-04-22 | Upjohn Co | Substituted butadiene and hexatriene photosensitizers |
| US3947337A (en) * | 1973-05-10 | 1976-03-30 | The Upjohn Company | α,ω-Diarylpolyene photosensitizers for sulfonylazide polymers |
| US4058400A (en) * | 1974-05-02 | 1977-11-15 | General Electric Company | Cationically polymerizable compositions containing group VIa onium salts |
| US4058401A (en) * | 1974-05-02 | 1977-11-15 | General Electric Company | Photocurable compositions containing group via aromatic onium salts |
| US4026705A (en) * | 1975-05-02 | 1977-05-31 | General Electric Company | Photocurable compositions and methods |
| US4069054A (en) * | 1975-09-02 | 1978-01-17 | Minnesota Mining And Manufacturing Company | Photopolymerizable composition containing a sensitized aromatic sulfonium compound and a cationacally polymerizable monomer |
| US4090936A (en) * | 1976-10-28 | 1978-05-23 | Minnesota Mining And Manufacturing Company | Photohardenable compositions |
-
1979
- 1979-05-21 US US06/040,645 patent/US4250053A/en not_active Expired - Lifetime
-
1980
- 1980-04-15 CA CA349,909A patent/CA1113638A/en not_active Expired
- 1980-05-14 SE SE8003647A patent/SE446780B/sv not_active IP Right Cessation
- 1980-05-19 ES ES491604A patent/ES8106967A1/es not_active Expired
- 1980-05-20 IT IT48736/80A patent/IT1133014B/it active
- 1980-05-20 DE DE19803019211 patent/DE3019211A1/de not_active Ceased
- 1980-05-20 GB GB8016641A patent/GB2053243B/en not_active Expired
- 1980-05-20 FR FR8011217A patent/FR2457511B1/fr not_active Expired
- 1980-05-20 ZA ZA00802991A patent/ZA802991B/xx unknown
- 1980-05-20 AU AU58559/80A patent/AU521591B2/en not_active Ceased
- 1980-05-20 KR KR1019800001984A patent/KR840000122B1/ko not_active Expired
- 1980-05-21 JP JP6768780A patent/JPS55155018A/ja active Granted
- 1980-05-21 BE BE0/200695A patent/BE883404A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2457511B1 (fr) | 1987-01-30 |
| US4250053A (en) | 1981-02-10 |
| SE446780B (sv) | 1986-10-06 |
| JPS612081B2 (en:Method) | 1986-01-22 |
| KR840000122B1 (ko) | 1984-02-16 |
| ES491604A0 (es) | 1981-09-01 |
| IT8048736A0 (it) | 1980-05-20 |
| JPS55155018A (en) | 1980-12-03 |
| AU521591B2 (en) | 1982-04-22 |
| IT1133014B (it) | 1986-07-09 |
| ES8106967A1 (es) | 1981-09-01 |
| AU5855980A (en) | 1980-11-27 |
| GB2053243B (en) | 1983-11-16 |
| DE3019211A1 (de) | 1980-11-27 |
| GB2053243A (en) | 1981-02-04 |
| SE8003647L (sv) | 1980-11-22 |
| KR830002827A (ko) | 1983-05-30 |
| FR2457511A1 (fr) | 1980-12-19 |
| BE883404A (fr) | 1980-11-21 |
| ZA802991B (en) | 1981-08-26 |
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