JP5697992B2 - ラジカル硬化性配合物のレドックス硬化のための光潜在性アミジン塩基 - Google Patents
ラジカル硬化性配合物のレドックス硬化のための光潜在性アミジン塩基 Download PDFInfo
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- JP5697992B2 JP5697992B2 JP2010544653A JP2010544653A JP5697992B2 JP 5697992 B2 JP5697992 B2 JP 5697992B2 JP 2010544653 A JP2010544653 A JP 2010544653A JP 2010544653 A JP2010544653 A JP 2010544653A JP 5697992 B2 JP5697992 B2 JP 5697992B2
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- alkyl
- phenyl
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- compound
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- 239000000203 mixture Substances 0.000 title claims description 140
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- 238000009472 formulation Methods 0.000 title description 26
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- 229940126062 Compound A Drugs 0.000 claims 1
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- 230000000379 polymerizing effect Effects 0.000 claims 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 82
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- 229910052760 oxygen Inorganic materials 0.000 description 35
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 35
- 239000003999 initiator Substances 0.000 description 34
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 23
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- 125000003118 aryl group Chemical group 0.000 description 19
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 15
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- 239000011248 coating agent Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 13
- 150000002009 diols Chemical class 0.000 description 13
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- 239000001301 oxygen Substances 0.000 description 13
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- 239000012965 benzophenone Substances 0.000 description 12
- 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 12
- 125000001424 substituent group Chemical group 0.000 description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 11
- 125000002947 alkylene group Chemical group 0.000 description 11
- 239000000178 monomer Substances 0.000 description 11
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
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- 125000004432 carbon atom Chemical group C* 0.000 description 10
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 125000003545 alkoxy group Chemical group 0.000 description 9
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 9
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
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- 239000002904 solvent Substances 0.000 description 9
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 8
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 8
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 8
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 8
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 7
- 0 Cc1c(*)c(I)c(*)c(*)c1* Chemical compound Cc1c(*)c(I)c(*)c(*)c1* 0.000 description 7
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- 239000004305 biphenyl Substances 0.000 description 7
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- 125000005442 diisocyanate group Chemical group 0.000 description 7
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- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 6
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- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
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- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
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- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
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- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- HDMGAZBPFLDBCX-UHFFFAOYSA-M potassium;sulfooxy sulfate Chemical compound [K+].OS(=O)(=O)OOS([O-])(=O)=O HDMGAZBPFLDBCX-UHFFFAOYSA-M 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000002987 primer (paints) Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
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- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- INCIMLINXXICKS-UHFFFAOYSA-M pyronin Y Chemical compound [Cl-].C1=CC(=[N+](C)C)C=C2OC3=CC(N(C)C)=CC=C3C=C21 INCIMLINXXICKS-UHFFFAOYSA-M 0.000 description 1
- RQGPLDBZHMVWCH-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole Chemical compound C1=NC2=CC=NC2=C1 RQGPLDBZHMVWCH-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229940043267 rhodamine b Drugs 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- VQQDHBUBOPTRBY-UHFFFAOYSA-N st50307358 Chemical compound C1CC(C)(C)C2=C(OC(C(C(=O)OCC)=C3)=O)C3=CC3=C2N1CCC3(C)C VQQDHBUBOPTRBY-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid 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
- 239000004575 stone Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- YEOUFHBJWTZWCZ-UHFFFAOYSA-M sulforhodamine G Chemical compound [Na+].C=12C=C(C)C(NCC)=CC2=[O+]C=2C=C(NCC)C(C)=CC=2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O YEOUFHBJWTZWCZ-UHFFFAOYSA-M 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000988 sulfur dye Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-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
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- KKFOMYPMTJLQGA-UHFFFAOYSA-N tribenzyl phosphite Chemical compound C=1C=CC=CC=1COP(OCC=1C=CC=CC=1)OCC1=CC=CC=C1 KKFOMYPMTJLQGA-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- NRWCNEBHECBWRJ-UHFFFAOYSA-M trimethyl(propyl)azanium;chloride Chemical compound [Cl-].CCC[N+](C)(C)C NRWCNEBHECBWRJ-UHFFFAOYSA-M 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Classifications
-
- 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
-
- 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
- G03F7/031—Organic compounds not covered by group G03F7/029
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Health & Medical Sciences (AREA)
- Polymerisation Methods In General (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Dental Preparations (AREA)
- Polymerization Catalysts (AREA)
- Paints Or Removers (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
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|---|---|---|---|
| EP08150721.2 | 2008-01-28 | ||
| EP08150721 | 2008-01-28 | ||
| PCT/EP2009/050066 WO2009095282A2 (en) | 2008-01-28 | 2009-01-06 | Photolatent amidine bases for redox curing of radically curable formulations |
Publications (3)
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|---|---|
| JP2011514393A JP2011514393A (ja) | 2011-05-06 |
| JP2011514393A5 JP2011514393A5 (OSRAM) | 2013-03-14 |
| JP5697992B2 true JP5697992B2 (ja) | 2015-04-08 |
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| US (1) | US20110190412A1 (OSRAM) |
| EP (1) | EP2238178B1 (OSRAM) |
| JP (1) | JP5697992B2 (OSRAM) |
| CN (1) | CN101925616A (OSRAM) |
| WO (1) | WO2009095282A2 (OSRAM) |
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| TWI572690B (zh) * | 2011-09-14 | 2017-03-01 | Denka Company Ltd | The composition and the temporary fixation of the components using it |
| EP2882808B1 (de) * | 2012-08-09 | 2016-10-12 | Basf Se | Strahlungshärtbare formulierungen mit hoher haftung |
| JP5725515B2 (ja) * | 2012-11-15 | 2015-05-27 | 学校法人東京理科大学 | 光塩基発生剤及び当該光塩基発生剤を含有する感光性樹脂組成物 |
| US9650526B2 (en) * | 2014-09-09 | 2017-05-16 | 3D Systems, Inc. | Method of printing a three-dimensional article |
| KR20170068475A (ko) * | 2014-10-06 | 2017-06-19 | 다우 글로벌 테크놀로지스 엘엘씨 | 금속 무함유 광제어 조절 라디칼 중합을 달성하기 위한 유기 광산화환원 촉매의 사용 |
| FR3030526B1 (fr) * | 2014-12-18 | 2018-06-15 | Arkema France | Polymerisation radicalaire d'alcoxyamines a basse temperature |
| EP3288999B1 (en) | 2015-04-29 | 2020-08-12 | 3M Innovative Properties Company | Composition including a polythiol and a polyepoxide and methods relating to the composition |
| WO2018085190A1 (en) | 2016-11-03 | 2018-05-11 | 3M Innovative Properties Company | Polythiol sealant compositions |
| WO2018085550A1 (en) | 2016-11-03 | 2018-05-11 | 3M Innovative Properties Company | Method of applying a sealant to an aircraft component |
| WO2018085534A1 (en) | 2016-11-03 | 2018-05-11 | 3M Innovative Properties Company | Compositions including a photolatent amine, camphorquinone, and a coumarin and related methods |
| JP6873417B2 (ja) * | 2016-11-10 | 2021-05-19 | 学校法人東京理科大学 | 光反応性組成物 |
| JP7109438B2 (ja) * | 2016-12-05 | 2022-07-29 | アーケマ・インコーポレイテッド | 重合開始剤ブレンド物、およびそのような重合開始剤ブレンド物を含む３ｄプリンティングに有用な光硬化性組成物 |
| WO2018160667A1 (en) * | 2017-02-28 | 2018-09-07 | Basf Se | Curable sealant composition |
| WO2018160691A1 (en) * | 2017-02-28 | 2018-09-07 | Basf Se | Curable sealant composition |
| GB2567242B (en) * | 2017-10-09 | 2021-08-11 | Henkel IP & Holding GmbH | Anaerobically curable compositions comprising 1, 2, 3, 4-tetrahydro benzo(h)quinolin-3-ol or derivatives thereof |
| CN112752803A (zh) | 2018-09-27 | 2021-05-04 | 3M创新有限公司 | 包含氨基官能硅烷的组合物以及将密封剂施用到基材的方法 |
| CN111040644A (zh) * | 2018-10-15 | 2020-04-21 | 烟台德邦科技有限公司 | 一种可光催化聚合的丙烯酸酯结构胶 |
| WO2020153269A1 (ja) * | 2019-01-21 | 2020-07-30 | 三井化学株式会社 | 光重合開始剤、光硬化性組成物、硬化物、及び、歯科材料 |
| WO2020202076A1 (en) | 2019-04-04 | 2020-10-08 | 3M Innovative Properties Company | Method of irradiating a composition through a substrate |
| WO2023167201A1 (ja) * | 2022-03-02 | 2023-09-07 | 株式会社カネカ | 活性エネルギー線硬化性組成物、及び硬化物の製造方法 |
| KR20250169219A (ko) * | 2023-03-30 | 2025-12-02 | 닛토 신코 가부시키가이샤 | 코팅용 경화성 조성물, 및 그의 경화물 |
| TWI885621B (zh) * | 2023-11-30 | 2025-06-01 | 國家中山科學研究院 | 乙烯基酯樹脂之固化方法 |
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| US3018266A (en) * | 1960-07-29 | 1962-01-23 | American Cyanamid Co | Polymerizable elastomer-vinyl aromatic compound composition containing a catalyst promoter system and method of polymerizing same |
| DE3612442A1 (de) * | 1986-04-12 | 1987-10-22 | Bayer Ag | Verfahren zur herstellung von uv-gehaerteten deckend pigmentierten beschichtungen |
| JPH1149835A (ja) * | 1997-08-05 | 1999-02-23 | Showa Highpolymer Co Ltd | コンクリート構築物用プライマー組成物及びその硬化方法 |
| EP0898202B1 (en) * | 1997-08-22 | 2000-07-19 | Ciba SC Holding AG | Photogeneration of amines from alpha-aminoacetophenones |
| TW436491B (en) * | 1997-08-22 | 2001-05-28 | Ciba Sc Holding Ag | Compositions for use in base-catalysed reactions, a process for curing said compostions and a process for photochemically generating bases in base catalysed polymeriaztion reactions |
| AU6032501A (en) * | 2000-05-26 | 2001-12-11 | Akzo Nobel Nv | Photoactivatable coating composition |
| ATE360629T1 (de) * | 2001-10-17 | 2007-05-15 | Ciba Sc Holding Ag | Photoaktivierbare stickstoffbasen |
| US6664357B1 (en) * | 2003-01-21 | 2003-12-16 | National Starch And Chemical Investment Holding Corporation | Method for the preparation of a stable anaerobic/UV/visible light curable adhesive |
| JP2008506826A (ja) * | 2004-07-21 | 2008-03-06 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 光活性化方法及び逆転した２段階工程による触媒の使用 |
| DE102005010327A1 (de) * | 2005-03-03 | 2006-09-07 | Basf Ag | Ratikalisch härtbare Beschichtungsmassen |
| JP4967276B2 (ja) * | 2005-08-09 | 2012-07-04 | 日立化成工業株式会社 | 回路接続材料並びに回路端子の接続構造体及び接続方法 |
| CN101522745B (zh) * | 2006-09-29 | 2013-06-19 | 西巴控股有限公司 | 以封闭异氰酸酯为基础的体系的光潜碱 |
-
2009
- 2009-01-06 EP EP09706026.3A patent/EP2238178B1/en not_active Not-in-force
- 2009-01-06 CN CN2009801032825A patent/CN101925616A/zh active Pending
- 2009-01-06 US US12/812,795 patent/US20110190412A1/en not_active Abandoned
- 2009-01-06 JP JP2010544653A patent/JP5697992B2/ja not_active Expired - Fee Related
- 2009-01-06 WO PCT/EP2009/050066 patent/WO2009095282A2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| US20110190412A1 (en) | 2011-08-04 |
| WO2009095282A3 (en) | 2009-11-12 |
| JP2011514393A (ja) | 2011-05-06 |
| CN101925616A (zh) | 2010-12-22 |
| EP2238178A2 (en) | 2010-10-13 |
| EP2238178B1 (en) | 2014-09-10 |
| WO2009095282A4 (en) | 2010-01-14 |
| WO2009095282A2 (en) | 2009-08-06 |
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