CA1291760C - Photoinitiateurs a base de sel du complexe aromatique iodonium - Google Patents

Photoinitiateurs a base de sel du complexe aromatique iodonium

Info

Publication number: CA1291760C
Authority: CA; Canada
Prior art keywords: groups; group; accordance; weight; photopolymerizable composition
Prior art date: 1974-05-08
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 - Lifetime

Application number

CA000224450A

Other languages

English (en)

Other versions

CA224450S (en

Inventor

George H. Smith

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

3M Co

Original Assignee

Minnesota Mining and Manufacturing Co

Priority date (The priority date 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 date listed.)

1974-05-08

Filing date

1975-04-11

Publication date

1991-11-05

1975-03-05 Priority to AU80917/75A priority Critical patent/AU497960B2/en

1975-04-02 Priority to US05/564,421 priority patent/US4394403A/en

1975-04-11 Application filed by Minnesota Mining and Manufacturing Co filed Critical Minnesota Mining and Manufacturing Co

1975-04-11 Priority to CA000224450A priority patent/CA1291760C/fr

1975-04-28 Priority to SE7504888A priority patent/SE423716B/xx

1975-05-06 Priority to CH584375A priority patent/CH617711A5/de

1975-05-07 Priority to GB19228/75A priority patent/GB1491539A/en

1975-05-07 Priority to FR7514387A priority patent/FR2270269B1/fr

1975-05-07 Priority to DE2520489A priority patent/DE2520489C2/de

1975-05-07 Priority to BE156157A priority patent/BE828841A/fr

1975-05-07 Priority to GB6289/77A priority patent/GB1491540A/en

1975-05-07 Priority to JP50055372A priority patent/JPS50158680A/ja

1978-03-10 Priority to US06/885,207 priority patent/US4378277A/en

1991-11-05 Application granted granted Critical

1991-11-05 Publication of CA1291760C publication Critical patent/CA1291760C/fr

2008-11-05 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

125000003118 aryl group Chemical group 0.000 title claims description 50
150000003839 salts Chemical class 0.000 title claims description 44
MGFYSGNNHQQTJW-UHFFFAOYSA-N iodonium Chemical compound [IH2+] MGFYSGNNHQQTJW-UHFFFAOYSA-N 0.000 title claims description 32
-1 aromatic iodonium salt Chemical class 0.000 claims abstract description 92
239000000203 mixture Substances 0.000 claims abstract description 84
239000011368 organic material Substances 0.000 claims abstract description 23
239000000758 substrate Substances 0.000 claims abstract description 13
238000000034 method Methods 0.000 claims abstract description 10
239000004593 Epoxy Substances 0.000 claims description 28
125000004432 carbon atom Chemical group C* 0.000 claims description 19
238000000576 coating method Methods 0.000 claims description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000001257 hydrogen Substances 0.000 claims description 15
239000011248 coating agent Substances 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
230000005855 radiation Effects 0.000 claims description 13
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 12
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 claims description 11
229920000647 polyepoxide Polymers 0.000 claims description 11
125000001544 thienyl group Chemical group 0.000 claims description 10
150000001450 anions Chemical class 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
238000010894 electron beam technology Methods 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 7
125000002541 furyl group Chemical group 0.000 claims description 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
125000004185 ester group Chemical group 0.000 claims description 5
229920001577 copolymer Polymers 0.000 claims description 4
230000001235 sensitizing effect Effects 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 3
FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000003368 amide group Chemical group 0.000 claims description 3
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
229920003986 novolac Polymers 0.000 claims description 3
125000005396 acrylic acid ester group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
229910052787 antimony Inorganic materials 0.000 claims description 2
229910052785 arsenic Inorganic materials 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000000945 filler Substances 0.000 claims description 2
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 2
150000002894 organic compounds Chemical class 0.000 claims description 2
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
229910052698 phosphorus Inorganic materials 0.000 claims description 2
229920002635 polyurethane Polymers 0.000 claims description 2
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125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
125000005037 alkyl phenyl group Chemical group 0.000 claims 1
238000011065 in-situ storage Methods 0.000 claims 1
239000000463 material Substances 0.000 abstract description 28
150000002500 ions Chemical class 0.000 abstract description 2
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
239000000243 solution Substances 0.000 description 11
KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 9
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WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
239000011521 glass Substances 0.000 description 5
150000002921 oxetanes Chemical class 0.000 description 5
125000003700 epoxy group Chemical group 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
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 4
150000002596 lactones Chemical class 0.000 description 4
230000003595 spectral effect Effects 0.000 description 4
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 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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001491 aromatic compounds Chemical class 0.000 description 3
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238000010168 coupling process Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000002184 metal Substances 0.000 description 3
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239000003504 photosensitizing agent Substances 0.000 description 3
229920006267 polyester film Polymers 0.000 description 3
239000000126 substance Substances 0.000 description 3
ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 2
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 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
UDLBSRQHKWDKQA-UHFFFAOYSA-N acetyl acetate;sulfuric acid Chemical compound OS(O)(=O)=O.CC(=O)OC(C)=O UDLBSRQHKWDKQA-UHFFFAOYSA-N 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
LMMDJMWIHPEQSJ-UHFFFAOYSA-N bis[(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl] hexanedioate Chemical compound C1C2OC2CC(C)C1COC(=O)CCCCC(=O)OCC1CC2OC2CC1C LMMDJMWIHPEQSJ-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
230000007423 decrease Effects 0.000 description 2
125000005520 diaryliodonium group Chemical group 0.000 description 2
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 2
230000000694 effects Effects 0.000 description 2
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VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000000466 oxiranyl group Chemical group 0.000 description 2
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239000001301 oxygen Substances 0.000 description 2
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GYZLOYUZLJXAJU-WDSKDSINSA-N (2r)-2-[[(2r)-oxiran-2-yl]methoxymethyl]oxirane Chemical compound C([C@@H]1OC1)OC[C@H]1CO1 GYZLOYUZLJXAJU-WDSKDSINSA-N 0.000 description 1
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
LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-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
SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
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XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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150000004982 aromatic amines Chemical class 0.000 description 1
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125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
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125000001246 bromo group Chemical group Br* 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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238000009833 condensation Methods 0.000 description 1
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ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical group C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
238000005034 decoration Methods 0.000 description 1
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239000012955 diaryliodonium Substances 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
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150000002009 diols Chemical class 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
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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
238000007689 inspection Methods 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
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000002346 iodo group Chemical group I* 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
239000004922 lacquer Substances 0.000 description 1
238000001459 lithography Methods 0.000 description 1
238000005649 metathesis reaction Methods 0.000 description 1
229940063557 methacrylate Drugs 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
KOARAHKGQSHYGJ-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;oxiran-2-ylmethyl prop-2-enoate Chemical compound COC(=O)C(C)=C.C=CC(=O)OCC1CO1 KOARAHKGQSHYGJ-UHFFFAOYSA-N 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
238000003801 milling Methods 0.000 description 1
239000000178 monomer Substances 0.000 description 1
238000000465 moulding Methods 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 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
150000007524 organic acids Chemical class 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
125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 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
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
229940116254 phosphonic acid Drugs 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
125000003367 polycyclic group Polymers 0.000 description 1
229920000728 polyester 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
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
238000004382 potting Methods 0.000 description 1
239000012255 powdered metal Substances 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
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000007142 ring opening reaction Methods 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
239000000377 silicon dioxide Substances 0.000 description 1
229920002050 silicone resin Polymers 0.000 description 1
125000005373 siloxane group Chemical group [SiH2](O*)* 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
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 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
230000001960 triggered effect Effects 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
239000004034 viscosity adjusting agent Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000002023 wood Substances 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

Landscapes

Epoxy Resins (AREA)
Polymerisation Methods In General (AREA)

CA000224450A 1974-04-11 1975-04-11 Photoinitiateurs a base de sel du complexe aromatique iodonium Expired - Lifetime CA1291760C (fr)

Priority Applications (12)

Application Number	Priority Date	Filing Date	Title
AU80917/75A AU497960B2 (en)	1974-04-11	1975-03-05	Photopolymerizable compositions
US05/564,421 US4394403A (en)	1974-05-08	1975-04-02	Photopolymerizable compositions
CA000224450A CA1291760C (fr)	1974-05-08	1975-04-11	Photoinitiateurs a base de sel du complexe aromatique iodonium
SE7504888A SE423716B (sv)	1974-05-08	1975-04-28	Fotopolymeriserbar komposition samt aromatiskt jodoniumkomplexsalt for anvendning som initiator i kompositionen
CH584375A CH617711A5 (fr)	1974-05-08	1975-05-06
FR7514387A FR2270269B1 (fr)	1974-05-08	1975-05-07
GB19228/75A GB1491539A (en)	1974-05-08	1975-05-07	Photopolymerizable compositions
DE2520489A DE2520489C2 (de)	1974-05-08	1975-05-07	Photopolymerisierbare Massen
BE156157A BE828841A (fr)	1974-05-08	1975-05-07	Compositions photopolymerisables
GB6289/77A GB1491540A (en)	1974-05-08	1975-05-07	Aromatic iodonium complex salts
JP50055372A JPS50158680A (fr)	1974-05-08	1975-05-07
US06/885,207 US4378277A (en)	1974-05-08	1978-03-10	Photopolymerizable epoxy-containing compositions

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US46789974A	1974-05-08	1974-05-08
CA000224450A CA1291760C (fr)	1974-05-08	1975-04-11	Photoinitiateurs a base de sel du complexe aromatique iodonium

Publications (1)

Publication Number	Publication Date
CA1291760C true CA1291760C (fr)	1991-11-05

Family

ID=25667909

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000224450A Expired - Lifetime CA1291760C (fr)	1974-04-11	1975-04-11	Photoinitiateurs a base de sel du complexe aromatique iodonium

Country Status (1)

Country	Link
CA (1)	CA1291760C (fr)

1975
- 1975-04-11 CA CA000224450A patent/CA1291760C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
1994-05-07	MKLA	Lapsed

Publication	Publication Date	Title
US4394403A (en)	1983-07-19	Photopolymerizable compositions
US4378277A (en)	1983-03-29	Photopolymerizable epoxy-containing compositions
US4318766A (en)	1982-03-09	Process of using photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials
CA1114089A (fr)	1981-12-08	Substances photopolymerisables contenant des matieres organiques comportant des fonctions epoxy et hydroxyle et contenant des photo- initiateurs a base de sels de sulfonium ou d'iodonium aromatiques
US4090936A (en)	1978-05-23	Photohardenable compositions
US4231951A (en)	1980-11-04	Complex salt photoinitiator
US4173476A (en)	1979-11-06	Complex salt photoinitiator
US4734444A (en)	1988-03-29	Curable mixtures containing N-sulfonylaminosulfonium salts as cationically active catalysts
US4058400A (en)	1977-11-15	Cationically polymerizable compositions containing group VIa onium salts
US4069055A (en)	1978-01-17	Photocurable epoxy compositions containing group Va onium salts
US4058401A (en)	1977-11-15	Photocurable compositions containing group via aromatic onium salts
US4138255A (en)	1979-02-06	Photo-curing method for epoxy resin using group VIa onium salt
US4069054A (en)	1978-01-17	Photopolymerizable composition containing a sensitized aromatic sulfonium compound and a cationacally polymerizable monomer
US4175963A (en)	1979-11-27	Method of exposing and curing an epoxy composition containing an aromatic onium salt
US4371605A (en)	1983-02-01	Photopolymerizable compositions containing N-hydroxyamide and N-hydroxyimide sulfonates
US4175972A (en)	1979-11-27	Curable epoxy compositions containing aromatic onium salts and hydroxy compounds
EP1625447B1 (fr)	2014-04-23	Generateurs de photoacides comprenant des anions multifonctionnels perfluores
TWI404699B (zh)	2013-08-11	鹽起始劑
US4161405A (en)	1979-07-17	Method of cationally polymerizing oxirane free materials with group VIa onium salts
US4193799A (en)	1980-03-18	Method of making printing plates and printed circuit
US4835193A (en)	1989-05-30	Photopolymerizable epoxy resin composition
CA1164710A (fr)	1984-04-03	Compositions photosensibles phototropes contenant un agent colorant a base de fluoranne
JP3942202B2 (ja)	2007-07-11	光重合開始剤、これを含有するエネルギー線硬化性組成物及びその硬化物
US4175973A (en)	1979-11-27	Curable compositions
JPH10287643A (ja)	1998-10-27	新規オニウム塩、光重合開始剤、これを含有するエネルギー線硬化性組成物及びその硬化物