DE2520489C2 - Photopolymerisierbare Massen - Google Patents
Photopolymerisierbare MassenInfo
- Publication number
- DE2520489C2 DE2520489C2 DE2520489A DE2520489A DE2520489C2 DE 2520489 C2 DE2520489 C2 DE 2520489C2 DE 2520489 A DE2520489 A DE 2520489A DE 2520489 A DE2520489 A DE 2520489A DE 2520489 C2 DE2520489 C2 DE 2520489C2
- Authority
- DE
- Germany
- Prior art keywords
- epoxy
- iodonium
- compounds
- groups
- aromatic
- 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
- 239000000203 mixture Substances 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 28
- 150000002894 organic compounds Chemical class 0.000 claims description 20
- MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 230000001235 sensitizing effect Effects 0.000 claims description 8
- -1 aromatic radicals Chemical class 0.000 description 53
- 150000001875 compounds Chemical class 0.000 description 48
- 239000004593 Epoxy Substances 0.000 description 38
- 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 18
- 230000005855 radiation Effects 0.000 description 14
- 238000000576 coating method Methods 0.000 description 13
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 10
- 229920000647 polyepoxide Polymers 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 125000003700 epoxy group Chemical group 0.000 description 8
- 239000003822 epoxy resin Substances 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229920006267 polyester film Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000003595 spectral effect Effects 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 150000001491 aromatic compounds Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 150000002118 epoxides Chemical class 0.000 description 5
- 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 5
- 150000002921 oxetanes Chemical class 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- SURWYRGVICLUBJ-UHFFFAOYSA-N 2-ethyl-9,10-dimethoxyanthracene Chemical compound C1=CC=CC2=C(OC)C3=CC(CC)=CC=C3C(OC)=C21 SURWYRGVICLUBJ-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
- 125000005520 diaryliodonium group Chemical group 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- BCQKUSCWNFMCKI-UHFFFAOYSA-M diphenyliodanium;hydrogen sulfate Chemical compound OS([O-])(=O)=O.C=1C=CC=CC=1[I+]C1=CC=CC=C1 BCQKUSCWNFMCKI-UHFFFAOYSA-M 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000003504 photosensitizing agent Substances 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000012955 diaryliodonium Substances 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 125000000466 oxiranyl group Chemical group 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- DNJRKFKAFWSXSE-UHFFFAOYSA-N 1-chloro-2-ethenoxyethane Chemical compound ClCCOC=C DNJRKFKAFWSXSE-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- XAYDWGMOPRHLEP-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C=C XAYDWGMOPRHLEP-UHFFFAOYSA-N 0.000 description 1
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical compound OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 description 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- ZIHQUWYJSTVYAT-UHFFFAOYSA-N [NH-][N+]([O-])=O Chemical compound [NH-][N+]([O-])=O ZIHQUWYJSTVYAT-UHFFFAOYSA-N 0.000 description 1
- CNSNSKYRRVETLB-UHFFFAOYSA-N [O-]C(C1=CC=CC([I+]C2=CC=CC(C(O)=O)=C2)=C1)=O Chemical compound [O-]C(C1=CC=CC([I+]C2=CC=CC(C(O)=O)=C2)=C1)=O CNSNSKYRRVETLB-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005396 acrylic acid ester 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
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005138 alkoxysulfonyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- YIQHETKPLWWHBD-UHFFFAOYSA-N bis(2,4-dichlorophenyl)iodanium Chemical compound ClC1=CC(Cl)=CC=C1[I+]C1=CC=C(Cl)C=C1Cl YIQHETKPLWWHBD-UHFFFAOYSA-N 0.000 description 1
- QINJTTKCPKYTNV-UHFFFAOYSA-N bis(3-methoxysulfonylphenyl)iodanium Chemical compound COS(=O)(=O)C1=CC=CC([I+]C=2C=C(C=CC=2)S(=O)(=O)OC)=C1 QINJTTKCPKYTNV-UHFFFAOYSA-N 0.000 description 1
- MWPUSWNISCYUNR-UHFFFAOYSA-N bis(3-nitrophenyl)iodanium Chemical compound [O-][N+](=O)C1=CC=CC([I+]C=2C=C(C=CC=2)[N+]([O-])=O)=C1 MWPUSWNISCYUNR-UHFFFAOYSA-N 0.000 description 1
- XVMXWJBAJDJTRN-UHFFFAOYSA-O bis(4-acetamidophenyl)iodanium Chemical compound C1=CC(NC(=O)C)=CC=C1[I+]C1=CC=C(NC(C)=O)C=C1 XVMXWJBAJDJTRN-UHFFFAOYSA-O 0.000 description 1
- RKJMYAKRQZRZCW-UHFFFAOYSA-N bis(4-bromophenyl)iodanium Chemical compound C1=CC(Br)=CC=C1[I+]C1=CC=C(Br)C=C1 RKJMYAKRQZRZCW-UHFFFAOYSA-N 0.000 description 1
- AMOIIGKEMUQPPZ-UHFFFAOYSA-N bis(4-heptylphenyl)iodanium Chemical compound C1=CC(CCCCCCC)=CC=C1[I+]C1=CC=C(CCCCCCC)C=C1 AMOIIGKEMUQPPZ-UHFFFAOYSA-N 0.000 description 1
- DWBJZABVMXQFPV-UHFFFAOYSA-N bis(4-methoxyphenyl)iodanium Chemical compound C1=CC(OC)=CC=C1[I+]C1=CC=C(OC)C=C1 DWBJZABVMXQFPV-UHFFFAOYSA-N 0.000 description 1
- NUPCNQQASBREGM-UHFFFAOYSA-N bis(4-phenoxyphenyl)iodanium Chemical compound C=1C=C([I+]C=2C=CC(OC=3C=CC=CC=3)=CC=2)C=CC=1OC1=CC=CC=C1 NUPCNQQASBREGM-UHFFFAOYSA-N 0.000 description 1
- DBAVIPITSXUODT-UHFFFAOYSA-N bis[4-(trifluoromethyl)phenyl]iodanium Chemical compound C1=CC(C(F)(F)F)=CC=C1[I+]C1=CC=C(C(F)(F)F)C=C1 DBAVIPITSXUODT-UHFFFAOYSA-N 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical group C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- UBBLLAWOTYUCQO-UHFFFAOYSA-N dinaphthalen-1-yliodanium Chemical compound C1=CC=C2C([I+]C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 UBBLLAWOTYUCQO-UHFFFAOYSA-N 0.000 description 1
- RSJLWBUYLGJOBD-UHFFFAOYSA-M diphenyliodanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[I+]C1=CC=CC=C1 RSJLWBUYLGJOBD-UHFFFAOYSA-M 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000001227 electron beam curing Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- ZCRZCMUDOWDGOB-UHFFFAOYSA-N ethanesulfonimidic acid Chemical group CCS(N)(=O)=O ZCRZCMUDOWDGOB-UHFFFAOYSA-N 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- JLUCVDLESNBWQK-UHFFFAOYSA-N iodyl hydrogen sulfate Chemical compound I(=O)(=O)OS(O)(=O)=O JLUCVDLESNBWQK-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical compound ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- YPNZYYWORCABPU-UHFFFAOYSA-N oxiran-2-ylmethyl 2-methylprop-2-enoate;styrene Chemical compound C=CC1=CC=CC=C1.CC(=C)C(=O)OCC1CO1 YPNZYYWORCABPU-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000002989 phenols Chemical class 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
- RKNCUZWOCPWMAU-UHFFFAOYSA-N phenyl(thiophen-2-yl)iodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CS1 RKNCUZWOCPWMAU-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 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
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 239000011787 zinc oxide Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/83—Chemically modified polymers
-
- 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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- General Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US46789974A | 1974-05-08 | 1974-05-08 | |
| US05/564,421 US4394403A (en) | 1974-05-08 | 1975-04-02 | Photopolymerizable compositions |
| CA000224450A CA1291760C (en) | 1974-05-08 | 1975-04-11 | Aromatic iodonium complex salt photoinitiators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2520489A1 DE2520489A1 (de) | 1976-10-14 |
| DE2520489C2 true DE2520489C2 (de) | 1983-05-05 |
Family
ID=27163902
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2520489A Expired DE2520489C2 (de) | 1974-05-08 | 1975-05-07 | Photopolymerisierbare Massen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4394403A (enExample) |
| JP (1) | JPS50158680A (enExample) |
| AU (1) | AU497960B2 (enExample) |
| BE (1) | BE828841A (enExample) |
| CH (1) | CH617711A5 (enExample) |
| DE (1) | DE2520489C2 (enExample) |
| FR (1) | FR2270269B1 (enExample) |
| GB (2) | GB1491540A (enExample) |
Families Citing this family (227)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1516352A (en) * | 1974-05-02 | 1978-07-05 | Gen Electric | Halonium salts |
| US4256828A (en) * | 1975-09-02 | 1981-03-17 | Minnesota Mining And Manufacturing Company | Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials |
| AU517415B2 (en) * | 1976-07-09 | 1981-07-30 | General Electric Company | Curable polymer composition |
| US4108747A (en) * | 1976-07-14 | 1978-08-22 | General Electric Company | Curable compositions and method for curing such compositions |
| US4090936A (en) | 1976-10-28 | 1978-05-23 | Minnesota Mining And Manufacturing Company | Photohardenable compositions |
| US4101513A (en) * | 1977-02-02 | 1978-07-18 | Minnesota Mining And Manufacturing Company | Catalyst for condensation of hydrolyzable silanes and storage stable compositions thereof |
| US4130690A (en) * | 1977-09-12 | 1978-12-19 | Minnesota Mining And Manufacturing Company | Abrasion resistant coatings cured in the presence of PF5, SbF5, or HSbF6 |
| GB2013208B (en) * | 1977-12-16 | 1982-11-24 | Gen Electric | Heat curable compositions |
| NL7812075A (nl) * | 1977-12-16 | 1979-06-19 | Gen Electric | Hardbare, harsbevattende materialen en werkwijze voor het opschuimen hiervan. |
| DE2854011C2 (de) * | 1978-12-14 | 1983-04-21 | General Electric Co., Schenectady, N.Y. | Hitzehärtbare Masse und Verfahren zu deren Herstellung |
| US4231886A (en) * | 1979-01-29 | 1980-11-04 | Minnesota Mining And Manufacturing Company | Ester solutions of complex salts |
| US4240131A (en) * | 1979-03-14 | 1980-12-16 | Minnesota Mining And Manufacturing Company | Sealed lighting element assembly |
| US4356050A (en) * | 1979-12-11 | 1982-10-26 | General Electric Company | Method of adhesive bonding using visible light cured epoxies |
| US4314917A (en) * | 1980-02-12 | 1982-02-09 | General Electric Company | High-solids epoxy prepolymer coating composition |
| US4351708A (en) | 1980-02-29 | 1982-09-28 | Ciba-Geigy Corporation | Photochemically or thermally polymerizable mixtures |
| US4336366A (en) | 1980-02-29 | 1982-06-22 | Ciba-Geigy Corporation | Thermally polymerizable mixtures and processes for the thermally-initiated polymerization of cationically polymerizable compounds |
| DE3107087A1 (de) * | 1980-02-29 | 1981-12-24 | CIBA-GEIGY AG, 4002 Basel | "photopolymerisierbare gemische und verfahren zur photopolymerisation von kationisch polymerisierbaren verbindungen" |
| US4518676A (en) * | 1982-09-18 | 1985-05-21 | Ciba Geigy Corporation | Photopolymerizable compositions containing diaryliodosyl salts |
| US4482679A (en) * | 1982-09-18 | 1984-11-13 | Ciba-Geigy Corporation | Heat-curable epoxy compositions containing diaryliodosyl salts |
| US4537725A (en) * | 1982-09-18 | 1985-08-27 | Ciba-Geigy Corporation | Diaryliodosyl salts |
| JPS5974103A (ja) * | 1982-10-19 | 1984-04-26 | Mitsubishi Electric Corp | 紫外線硬化型樹脂組成物 |
| US4683317A (en) * | 1983-05-23 | 1987-07-28 | General Electric Company | Photopolymerizable organic compositions and diaryliodonium salts used therein |
| US4882245A (en) * | 1985-10-28 | 1989-11-21 | International Business Machines Corporation | Photoresist composition and printed circuit boards and packages made therewith |
| US4937159A (en) * | 1985-11-20 | 1990-06-26 | The Mead Corporation | Photosensitive materials and compositions containing ionic dye compounds as initiators and thiols as autooxidizers |
| US4772530A (en) * | 1986-05-06 | 1988-09-20 | The Mead Corporation | Photosensitive materials containing ionic dye compounds as initiators |
| USRE33211E (en) * | 1986-08-19 | 1990-05-08 | Allied-Signal Inc. | Vinyl ether terminated urethane resins |
| US4751103A (en) * | 1986-11-13 | 1988-06-14 | Ashland Oil, Inc. | Epoxy primers for polyurethane structural adhesives |
| US4874450A (en) * | 1987-01-29 | 1989-10-17 | The Mead Corporation | Laminating transparent or translucent materials using ionic dye-counter ion complexes |
| US4997717A (en) * | 1987-03-27 | 1991-03-05 | Ciba-Geigy Corporation | Photocurable abrasives |
| 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 |
| US4801392A (en) * | 1987-07-02 | 1989-01-31 | The Mead Corporation | Magnetic recording compositions containing ionic dye compounds as initiators |
| GB2243365B (en) * | 1987-10-01 | 1992-04-29 | Gen Electric | Carboxy iodonium bisulfate salts |
| US4959297A (en) * | 1987-12-09 | 1990-09-25 | Minnesota Mining And Manufacturing Company | Ternary photoinitiator system for addition polymerization |
| US4889792A (en) * | 1987-12-09 | 1989-12-26 | Minnesota Mining And Manufacturing Company | Ternary photoinitiator system for addition polymerization |
| US4975300A (en) * | 1987-12-31 | 1990-12-04 | Minnesota Mining And Manufacturing Company | Method for curing an organic coating using condensation heating and radiation energy |
| US4882201A (en) * | 1988-03-21 | 1989-11-21 | General Electric Company | Non-toxic aryl onium salts, UV curable coating compositions and food packaging use |
| US5015180A (en) * | 1989-03-01 | 1991-05-14 | Minnesota Mining And Manufacturing Company | Dental article containing light-curable paste |
| CA2015894A1 (en) * | 1989-05-30 | 1990-11-30 | Mohammad Z. Ali | High sensitivity photopolymerizable compositions containing hydrogen donating mercaptans |
| DE69029104T2 (de) | 1989-07-12 | 1997-03-20 | Fuji Photo Film Co Ltd | Polysiloxane und positiv arbeitende Resistmasse |
| DE4023247C1 (enExample) * | 1990-07-21 | 1991-11-21 | Th. Goldschmidt Ag, 4300 Essen, De | |
| DE4023556A1 (de) * | 1990-07-25 | 1992-01-30 | Goldschmidt Ag Th | Haertbare epoxygruppen aufweisende organopolysiloxane, verfahren zu ihrer herstellung und ihre verwendung als haertbare beschichtungsmittel mit abhaesiven eigenschaften |
| US5262232A (en) * | 1992-01-22 | 1993-11-16 | Minnesota Mining And Manufacturing Company | Vibration damping constructions using acrylate-containing damping materials |
| US5463084A (en) * | 1992-02-18 | 1995-10-31 | Rensselaer Polytechnic Institute | Photocurable silicone oxetanes |
| US5362769A (en) * | 1992-05-07 | 1994-11-08 | Ormco Corporation | Orthodontic adhesives |
| GB9309275D0 (en) * | 1993-05-05 | 1993-06-16 | Smith & Nephew | Orthopaedic material |
| DE59409385D1 (de) * | 1993-09-16 | 2000-07-06 | Ciba Sc Holding Ag | Vinyletherverbindungen mit zusätzlichen von Vinylethergruppen verschiedenen funktionellen Gruppen und deren Verwendung zur Formulierung härtbarer Zusammensetzungen |
| US5856373A (en) * | 1994-10-31 | 1999-01-05 | Minnesota Mining And Manufacturing Company | Dental visible light curable epoxy system with enhanced depth of cure |
| US5877229A (en) * | 1995-07-26 | 1999-03-02 | Lockheed Martin Energy Systems, Inc. | High energy electron beam curing of epoxy resin systems incorporating cationic photoinitiators |
| WO1998012232A1 (fr) | 1996-09-19 | 1998-03-26 | Nippon Soda Co., Ltd. | Composition phytocatalytique |
| JPH1087963A (ja) * | 1996-09-20 | 1998-04-07 | Japan Synthetic Rubber Co Ltd | 樹脂組成物および繊維質材料成形型 |
| JP3786480B2 (ja) * | 1996-10-14 | 2006-06-14 | Ｊｓｒ株式会社 | 光硬化性樹脂組成物 |
| JP3626302B2 (ja) * | 1996-12-10 | 2005-03-09 | Ｊｓｒ株式会社 | 光硬化性樹脂組成物 |
| JP3765896B2 (ja) * | 1996-12-13 | 2006-04-12 | Ｊｓｒ株式会社 | 光学的立体造形用光硬化性樹脂組成物 |
| US6254954B1 (en) | 1997-02-28 | 2001-07-03 | 3M Innovative Properties Company | Pressure-sensitive adhesive tape |
| BR9808222A (pt) * | 1997-03-07 | 2000-05-16 | Henkel Kgaa | Sistemas de adesivo para um processo de encadernação adesiva de um ou mais estágios, progesso para a encadernação adesiva de improssos |
| US5998495A (en) * | 1997-04-11 | 1999-12-07 | 3M Innovative Properties Company | Ternary photoinitiator system for curing of epoxy/polyol resin compositions |
| US6025406A (en) * | 1997-04-11 | 2000-02-15 | 3M Innovative Properties Company | Ternary photoinitiator system for curing of epoxy resins |
| FR2762001B1 (fr) * | 1997-04-11 | 1999-07-02 | Rhodia Chimie Sa | Amorceurs non toxiques, resines a groupements organofonctionnels reticulables comprenant les amorceurs, et leur utilisation pour la preparation de polymeres stables et non toxiques |
| US6085004A (en) * | 1998-02-03 | 2000-07-04 | 3M Innovative Properties Company | Optical fiber connector using photocurable adhesive |
| US6331080B1 (en) | 1998-07-15 | 2001-12-18 | 3M Innovative Properties Company | Optical fiber connector using colored photocurable adhesive |
| US6306926B1 (en) | 1998-10-07 | 2001-10-23 | 3M Innovative Properties Company | Radiopaque cationically polymerizable compositions comprising a radiopacifying filler, and method for polymerizing same |
| CA2353506A1 (en) | 1998-11-02 | 2000-05-11 | 3M Innovative Properties Company | Transparent conductive oxides for plastic flat panel displays |
| US7418993B2 (en) | 1998-11-20 | 2008-09-02 | Rolls-Royce Corporation | Method and apparatus for production of a cast component |
| US6932145B2 (en) | 1998-11-20 | 2005-08-23 | Rolls-Royce Corporation | Method and apparatus for production of a cast component |
| JP4142258B2 (ja) * | 1999-01-08 | 2008-09-03 | スリーエム イノベイティブ プロパティズ カンパニー | 歯科用ミルブランク |
| CN1203150C (zh) * | 1999-08-12 | 2005-05-25 | 三井化学株式会社 | 密封剂用光固化型树脂组合物及密封方法 |
| US6730156B1 (en) | 1999-10-28 | 2004-05-04 | 3M Innovative Properties Company | Clustered particle dental fillers |
| US6387981B1 (en) | 1999-10-28 | 2002-05-14 | 3M Innovative Properties Company | Radiopaque dental materials with nano-sized particles |
| US6572693B1 (en) | 1999-10-28 | 2003-06-03 | 3M Innovative Properties Company | Aesthetic dental materials |
| CA2387215C (en) * | 1999-10-28 | 2010-02-09 | 3M Innovative Properties Company | Dental materials with nano-sized silica particles |
| US6376590B2 (en) | 1999-10-28 | 2002-04-23 | 3M Innovative Properties Company | Zirconia sol, process of making and composite material |
| US6444725B1 (en) | 2000-01-21 | 2002-09-03 | 3M Innovative Properties Company | Color-changing dental compositions |
| JP2001207150A (ja) * | 2000-01-26 | 2001-07-31 | Sony Chem Corp | 接着剤組成物 |
| KR100754813B1 (ko) * | 2000-06-15 | 2007-09-04 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 다중통과 다광자 흡수 방법 및 장치 |
| KR100810547B1 (ko) * | 2000-06-15 | 2008-03-18 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 캡슐화 광학 부재의 제작방법, 광학소자 및 이의 커플링 방법 |
| US7118845B2 (en) * | 2000-06-15 | 2006-10-10 | 3M Innovative Properties Company | Multiphoton photochemical process and articles preparable thereby |
| US7265161B2 (en) * | 2002-10-02 | 2007-09-04 | 3M Innovative Properties Company | Multi-photon reactive compositions with inorganic particles and method for fabricating structures |
| US7026103B2 (en) * | 2000-06-15 | 2006-04-11 | 3M Innovative Properties Company | Multicolor imaging using multiphoton photochemical processes |
| US7381516B2 (en) * | 2002-10-02 | 2008-06-03 | 3M Innovative Properties Company | Multiphoton photosensitization system |
| US7005229B2 (en) * | 2002-10-02 | 2006-02-28 | 3M Innovative Properties Company | Multiphoton photosensitization method |
| US6852766B1 (en) | 2000-06-15 | 2005-02-08 | 3M Innovative Properties Company | Multiphoton photosensitization system |
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Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3074869A (en) * | 1960-12-23 | 1963-01-22 | Minnesota Mining & Mfg | Photo-sensitive compositions and articles therefrom |
| US3205157A (en) * | 1962-03-13 | 1965-09-07 | North American Aviation Inc | Electromagnetic radiation polymerization |
| GB1071652A (en) | 1962-11-14 | 1967-06-07 | British Industrial Plastics | Polymeric compositions |
| NL135320C (enExample) | 1964-07-31 | British Industrial Plastics | ||
| US3373221A (en) * | 1964-11-04 | 1968-03-12 | Shell Oil Co | Reaction products of unsaturated esters of polyepoxides and unsaturated carboxylic acids, and polyisocyanates |
| US3567453A (en) * | 1967-12-26 | 1971-03-02 | Eastman Kodak Co | Light sensitive compositions for photoresists and lithography |
| US3826650A (en) * | 1968-08-20 | 1974-07-30 | American Can Co | Epoxy photopolymer duplicating stencil |
| US3691133A (en) * | 1971-03-25 | 1972-09-12 | Union Carbon Corp | Polyepoxide compositions containing dicyandiamide and an iodonium, phosphonium, or sulfonium salt |
| US3711390A (en) * | 1971-05-18 | 1973-01-16 | J Feinberg | Photopolymerizable epoxy systems containing substituted cyclic amides or substituted ureas as gelation inhibitors |
| US3816280A (en) * | 1971-05-18 | 1974-06-11 | American Can Co | Photopolymerizable epoxy systems containing cyclic amide gelation inhibitors |
| BE792102A (fr) * | 1971-12-01 | 1973-05-30 | Ciba Geigy | Derives du thiadiazole-1,2,4 ayant une action anthelminthique |
| US3729313A (en) * | 1971-12-06 | 1973-04-24 | Minnesota Mining & Mfg | Novel photosensitive systems comprising diaryliodonium compounds and their use |
| US3808006A (en) * | 1971-12-06 | 1974-04-30 | Minnesota Mining & Mfg | Photosensitive material containing a diaryliodium compound, a sensitizer and a color former |
-
1975
- 1975-03-05 AU AU80917/75A patent/AU497960B2/en not_active Expired
- 1975-04-02 US US05/564,421 patent/US4394403A/en not_active Expired - Lifetime
- 1975-05-06 CH CH584375A patent/CH617711A5/de not_active IP Right Cessation
- 1975-05-07 GB GB6289/77A patent/GB1491540A/en not_active Expired
- 1975-05-07 BE BE156157A patent/BE828841A/xx not_active IP Right Cessation
- 1975-05-07 JP JP50055372A patent/JPS50158680A/ja active Pending
- 1975-05-07 GB GB19228/75A patent/GB1491539A/en not_active Expired
- 1975-05-07 FR FR7514387A patent/FR2270269B1/fr not_active Expired
- 1975-05-07 DE DE2520489A patent/DE2520489C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU497960B2 (en) | 1979-01-25 |
| BE828841A (fr) | 1975-11-07 |
| FR2270269B1 (enExample) | 1978-10-13 |
| US4394403A (en) | 1983-07-19 |
| GB1491539A (en) | 1977-11-09 |
| GB1491540A (en) | 1977-11-09 |
| CH617711A5 (enExample) | 1980-06-13 |
| FR2270269A1 (enExample) | 1975-12-05 |
| AU8091775A (en) | 1976-11-11 |
| JPS50158680A (enExample) | 1975-12-22 |
| DE2520489A1 (de) | 1976-10-14 |
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| 8126 | Change of the secondary classification |
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Free format text: TAUCHNER, P., DIPL.-CHEM. DR.RER.NAT. HEUNEMANN, D., DIPL.-PHYS. DR.RER.NAT. RAUH, P., DIPL.-CHEM. DR.RER.NAT. HERMANN, G., DIPL.-PHYS. DR.RER.NAT. SCHMIDT, J., DIPL.-ING. JAENICHEN, H., DIPL.-BIOL. DR.RER.NAT., PAT.-ANWAELTE, 8000 MUENCHEN |