CA1300307C - Photopolymerisation by means of organometallic salts - Google Patents
Photopolymerisation by means of organometallic saltsInfo
- Publication number
- CA1300307C CA1300307C CA000428303A CA428303A CA1300307C CA 1300307 C CA1300307 C CA 1300307C CA 000428303 A CA000428303 A CA 000428303A CA 428303 A CA428303 A CA 428303A CA 1300307 C CA1300307 C CA 1300307C
- Authority
- CA
- Canada
- Prior art keywords
- group
- compositions according
- carbon atoms
- atom
- formula
- 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 - Lifetime
Links
- 125000002524 organometallic group Chemical group 0.000 title description 6
- -1 hexafluorophosphate Chemical compound 0.000 claims abstract description 93
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 78
- 229910052742 iron Inorganic materials 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 239000011572 manganese Substances 0.000 claims abstract description 15
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 13
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
- 229910052751 metal Inorganic materials 0.000 claims abstract description 6
- 239000002184 metal Substances 0.000 claims abstract description 6
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 229910052752 metalloid Inorganic materials 0.000 claims abstract description 3
- 150000002738 metalloids Chemical class 0.000 claims abstract description 3
- 230000007704 transition Effects 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 79
- 229920000647 polyepoxide Polymers 0.000 claims description 47
- 239000003822 epoxy resin Substances 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000004429 atom Chemical group 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 238000013007 heat curing Methods 0.000 claims description 11
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052802 copper Inorganic materials 0.000 claims description 10
- 239000010949 copper Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229910052804 chromium Inorganic materials 0.000 claims description 7
- 239000011651 chromium Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 229910052787 antimony Inorganic materials 0.000 claims description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052759 nickel Inorganic materials 0.000 claims description 4
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical compound NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 239000010937 tungsten Substances 0.000 claims description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- LLASZDGDPGWOKL-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1C[C+]=CC=C1 LLASZDGDPGWOKL-UHFFFAOYSA-N 0.000 claims description 3
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
- 239000010936 titanium Substances 0.000 claims description 3
- 229910052719 titanium Inorganic materials 0.000 claims description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052720 vanadium Inorganic materials 0.000 claims description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims description 2
- 229910052741 iridium Inorganic materials 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052758 niobium Inorganic materials 0.000 claims description 2
- 239000010955 niobium Substances 0.000 claims description 2
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- 239000010948 rhodium Substances 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 229910052715 tantalum Inorganic materials 0.000 claims description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims description 2
- KJTDQPVKVGMNNR-UHFFFAOYSA-N 2-methoxy-5-methylcyclohexa-1,3-diene Chemical compound COC1=CC[C+](C)C=C1 KJTDQPVKVGMNNR-UHFFFAOYSA-N 0.000 claims 1
- AKUSIRLPJRWWRN-UHFFFAOYSA-N 3-O-(3-acetyloxy-2-cyclohexa-1,3-dien-1-ylpropyl) 1-O-methyl propanedioate Chemical compound C(C)(=O)OCC(COC(CC(=O)OC)=O)[C+]1C=CC=CC1 AKUSIRLPJRWWRN-UHFFFAOYSA-N 0.000 claims 1
- BGEUHVSTFDAKJZ-UHFFFAOYSA-N 5-methylcyclohexa-1,3-diene Chemical compound C[C+]1CC=CC=C1 BGEUHVSTFDAKJZ-UHFFFAOYSA-N 0.000 claims 1
- NXUHNIPIWGJICS-UHFFFAOYSA-N 8-methoxy-1,2,3,4,4a,7-hexahydronaphthalen-7-ylium Chemical compound COC=1[C+]2CCCCC2C=CC=1 NXUHNIPIWGJICS-UHFFFAOYSA-N 0.000 claims 1
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 230000005855 radiation Effects 0.000 abstract description 15
- 238000000034 method Methods 0.000 description 18
- 238000010438 heat treatment Methods 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 238000000576 coating method Methods 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 14
- 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 12
- 238000001723 curing Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 150000002118 epoxides Chemical class 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000012779 reinforcing material Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000002131 composite material Substances 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
- 229910052753 mercury Inorganic materials 0.000 description 5
- 239000005028 tinplate Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 230000002787 reinforcement Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene group Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- VOYNOJWTOMQQAS-UHFFFAOYSA-N cyclopentadienylium Chemical compound [CH+]1C=CC=C1 VOYNOJWTOMQQAS-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 238000004804 winding Methods 0.000 description 3
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LTEQMZWBSYACLV-UHFFFAOYSA-N Hexylbenzene Chemical compound CCCCCCC1=CC=CC=C1 LTEQMZWBSYACLV-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 239000003677 Sheet moulding compound Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- 238000009730 filament winding Methods 0.000 description 2
- DWYMPOCYEZONEA-UHFFFAOYSA-L fluoridophosphate Chemical compound [O-]P([O-])(F)=O DWYMPOCYEZONEA-UHFFFAOYSA-L 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 229910001507 metal halide Inorganic materials 0.000 description 2
- 150000005309 metal halides Chemical class 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
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- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 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
- 238000001029 thermal curing Methods 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 150000003658 tungsten compounds Chemical class 0.000 description 1
- 125000002348 vinylic group Chemical group 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
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
- 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
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
- C08G65/105—Onium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8214609 | 1982-05-19 | ||
| GB8214609 | 1982-05-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1300307C true CA1300307C (en) | 1992-05-05 |
Family
ID=10530464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000428303A Expired - Lifetime CA1300307C (en) | 1982-05-19 | 1983-05-17 | Photopolymerisation by means of organometallic salts |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0094914B1 (Direct) |
| JP (1) | JPS58213019A (Direct) |
| CA (1) | CA1300307C (Direct) |
| DE (1) | DE3366408D1 (Direct) |
| HK (1) | HK58689A (Direct) |
| SG (1) | SG20789G (Direct) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7553670B2 (en) | 2004-04-28 | 2009-06-30 | 3M Innovative Properties Company | Method for monitoring a polymerization in a three-dimensional sample |
| US9896599B2 (en) | 2013-04-30 | 2018-02-20 | 3M Innovative Properties Company | Process for preparing poly(benzoxazines) |
| US10040905B2 (en) | 2013-10-16 | 2018-08-07 | 3M Innovative Properties Company | Benzoxazine polymerization |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5191101A (en) * | 1982-11-22 | 1993-03-02 | Minnesota Mining And Manufacturing Company | Energy polymerizable compositions containing organometallic initiators |
| US5089536A (en) * | 1982-11-22 | 1992-02-18 | Minnesota Mining And Manufacturing Company | Energy polmerizable compositions containing organometallic initiators |
| EP0152377B1 (de) * | 1984-02-10 | 1987-12-09 | Ciba-Geigy Ag | Härtbare Zusammensetzung und deren Verwendung |
| DE3565013D1 (en) * | 1984-02-10 | 1988-10-20 | Ciba Geigy Ag | Process for the preparation of a protection layer or a relief pattern |
| US4677137A (en) * | 1985-05-31 | 1987-06-30 | Minnesota Mining And Manufacturing Company | Supported photoinitiator |
| US4707432A (en) * | 1985-09-23 | 1987-11-17 | Ciba-Geigy Corporation | Ferrocenium/alpha-cleavage photoinitiator systems for free radical polymerizable compositions |
| JPH0675194B2 (ja) * | 1986-03-31 | 1994-09-21 | キヤノン株式会社 | 重合性薄膜 |
| US4740577A (en) * | 1987-08-28 | 1988-04-26 | Minnesota Mining And Manufacturing Company | Energy polymerizable polyurethane precursors |
| US4950696A (en) * | 1987-08-28 | 1990-08-21 | Minnesota Mining And Manufacturing Company | Energy-induced dual curable compositions |
| US4952612A (en) * | 1987-08-28 | 1990-08-28 | Minnesota Mining And Manufacturing Company | Energy-induced curable compositions |
| US5086086A (en) * | 1987-08-28 | 1992-02-04 | Minnesota Mining And Manufacturing Company | Energy-induced curable compositions |
| JPH01118564A (ja) * | 1987-10-30 | 1989-05-11 | Toshiba Chem Corp | 一液性エポキシ樹脂組成物 |
| US4985340A (en) * | 1988-06-01 | 1991-01-15 | Minnesota Mining And Manufacturing Company | Energy curable compositions: two component curing agents |
| US5215860A (en) * | 1988-08-19 | 1993-06-01 | Minnesota Mining And Manufacturing Company | Energy-curable cyanate compositions |
| US5667934A (en) * | 1990-10-09 | 1997-09-16 | International Business Machines Corporation | Thermally stable photoimaging composition |
| JP3268532B2 (ja) * | 1992-01-22 | 2002-03-25 | ミネソタ マイニング アンド マニファクチャリング カンパニー | 光活性化可能な熱硬化性エポキシ組成物 |
| US5212210A (en) * | 1992-03-18 | 1993-05-18 | Minnesota Mining And Manufacturing Company | Energy curable compositions having improved cure speeds |
| US5667893A (en) * | 1992-10-09 | 1997-09-16 | Minnesota Mining And Manufacturing Company | Substrate coated or impregnated with flexible epoxy composition |
| US5514728A (en) * | 1993-07-23 | 1996-05-07 | Minnesota Mining And Manufacturing Company | Catalysts and initiators for polymerization |
| ES2147777T3 (es) | 1993-09-16 | 2000-10-01 | Ciba Sc Holding Ag | Compuestos vinileter con grupos funcionales adicionales, distintos de vinileter, y su utilizacion en la formulacion de compuestos reticulables. |
| DE4340949A1 (de) * | 1993-12-01 | 1995-06-08 | Thera Ges Fuer Patente | Lichtinitiiert kationisch härtende Epoxidmasse und ihre Verwendung |
| US5670590A (en) * | 1994-05-06 | 1997-09-23 | Minnesota Mining And Manufacturing Company | Energy polymerizable compositions, homopolymers and copolymers of oxazolines |
| TW418215B (en) | 1995-03-13 | 2001-01-11 | Ciba Sc Holding Ag | A process for the production of three-dimensional articles in a stereolithography bath comprising the step of sequentially irradiating a plurality of layers of a liquid radiation-curable composition |
| ATE191090T1 (de) * | 1996-07-29 | 2000-04-15 | Ciba Sc Holding Ag | Flüssige, strahlungshärtbare zusammensetzung, insbesondere für die stereolithographie |
| US5789333A (en) * | 1997-03-05 | 1998-08-04 | Iowa State University Research Foundation, Inc. | Catalyst system comprising a first catalyst system tethered to a supported catalyst |
| US6133335A (en) | 1998-12-31 | 2000-10-17 | 3M Innovative Properties Company | Photo-polymerizable compositions and articles made therefrom |
| US6265459B1 (en) | 1998-12-31 | 2001-07-24 | 3M Innovative Properties Company | Accelerators useful for energy polymerizable compositions |
| 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 |
| JP4800535B2 (ja) | 1999-10-28 | 2011-10-26 | スリーエム イノベイティブ プロパティズ カンパニー | ナノサイズシリカ粒子を含有する歯科材料 |
| US6730156B1 (en) | 1999-10-28 | 2004-05-04 | 3M Innovative Properties Company | Clustered particle dental fillers |
| US6635689B1 (en) | 2000-06-26 | 2003-10-21 | 3M Innovative Properties Company | Accelerators for cationic polymerization catalyzed by iron-based catalysts |
| WO2003063804A1 (en) | 2002-01-31 | 2003-08-07 | 3M Innovative Properties Company | Dental pastes, dental articles, and methods |
| JP2005529200A (ja) | 2002-05-03 | 2005-09-29 | ディーエスエム アイピー アセッツ ビー．ブイ． | 照射硬化可能な樹脂組成物及びそれを用いるラピッドプロトタイピング法 |
| US6989225B2 (en) | 2002-07-18 | 2006-01-24 | 3D Systems, Inc. | Stereolithographic resins with high temperature and high impact resistance |
| US7449146B2 (en) | 2002-09-30 | 2008-11-11 | 3M Innovative Properties Company | Colorimetric sensor |
| US20040062682A1 (en) | 2002-09-30 | 2004-04-01 | Rakow Neal Anthony | Colorimetric sensor |
| US6841333B2 (en) | 2002-11-01 | 2005-01-11 | 3M Innovative Properties Company | Ionic photoacid generators with segmented hydrocarbon-fluorocarbon sulfonate anions |
| CN101775197B (zh) | 2003-07-23 | 2012-09-26 | 帝斯曼知识产权资产管理有限公司 | 可降低粘度的辐射固化树脂组合物 |
| US8287611B2 (en) | 2005-01-28 | 2012-10-16 | Saint-Gobain Abrasives, Inc. | Abrasive articles and methods for making same |
| US7591865B2 (en) | 2005-01-28 | 2009-09-22 | Saint-Gobain Abrasives, Inc. | Method of forming structured abrasive article |
| SE529306C2 (sv) | 2005-03-18 | 2007-06-26 | Perstorp Specialty Chem Ab | Ultravioletthärdande hartskomposition |
| US8871335B2 (en) | 2005-08-31 | 2014-10-28 | Kuraray America Inc. | Solar control laminate |
| US8435098B2 (en) | 2006-01-27 | 2013-05-07 | Saint-Gobain Abrasives, Inc. | Abrasive article with cured backsize layer |
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| CA2672243C (en) | 2006-12-21 | 2012-04-03 | Saint-Gobain Abrasives, Inc. | Low corrosion abrasive articles and methods for forming same |
| US20100190881A1 (en) | 2009-01-28 | 2010-07-29 | 3D Systems, Incorporated | Radiation Curable Compositions Useful in Solid Freeform Fabrication Systems |
| EP2406318B1 (en) | 2009-03-13 | 2021-04-21 | DSM IP Assets B.V. | Radiation curable resin composition and rapid three-dimensional imaging process using the same |
| CN102858738B (zh) | 2009-12-17 | 2015-07-22 | 帝斯曼知识产权资产管理有限公司 | 用于加成法制造的包含三芳基锍硼酸盐阳离子光引发剂的液体可辐射固化树脂 |
| AU2011207304B2 (en) | 2010-01-22 | 2014-07-17 | Stratasys, Inc. | Liquid radiation curable resins capable of curing into layers with selective visual effects and methods for the use thereof |
| US9176377B2 (en) | 2010-06-01 | 2015-11-03 | Inpria Corporation | Patterned inorganic layers, radiation based patterning compositions and corresponding methods |
| EP2502728B1 (en) | 2011-03-23 | 2017-01-04 | DSM IP Assets B.V. | Lightweight and high strength three-dimensional articles producible by additive fabrication processes |
| EP2938652B1 (en) | 2012-12-27 | 2021-03-31 | 3M Innovative Properties Company | Polymerizable composition including a benzoxazine and an acid-forming peroxide catalyst, article, and method |
| US9310684B2 (en) | 2013-08-22 | 2016-04-12 | Inpria Corporation | Organometallic solution based high resolution patterning compositions |
| JP6195552B2 (ja) * | 2014-02-21 | 2017-09-13 | 富士フイルム株式会社 | 感活性光線性又は感放射線性樹脂組成物、レジスト膜、及び、パターン形成方法、並びに、これらを用いた電子デバイスの製造方法 |
| EP3307807A1 (en) | 2015-06-09 | 2018-04-18 | 3M Innovative Properties Company | Ammonium salt catalyzed benzoxazine polymerization |
| WO2017174545A1 (en) | 2016-04-08 | 2017-10-12 | Solvay Specialty Polymers Usa, Llc | Photocurable polymers, photocurable polymer compositions and lithographic processes including the same |
| CN113667280A (zh) * | 2021-08-28 | 2021-11-19 | 林州致远电子科技有限公司 | 一种具有uv遮蔽作用的树脂组合物及在覆铜板中的应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3709861A (en) * | 1970-12-14 | 1973-01-09 | Shell Oil Co | Process for light-induced curing of epoxy resins in presence of cyclopentadienylmanganese tricarbonyl compounds |
-
1983
- 1983-05-13 DE DE8383810206T patent/DE3366408D1/de not_active Expired
- 1983-05-13 EP EP19830810206 patent/EP0094914B1/de not_active Expired
- 1983-05-17 CA CA000428303A patent/CA1300307C/en not_active Expired - Lifetime
- 1983-05-18 JP JP8601083A patent/JPS58213019A/ja active Granted
-
1989
- 1989-04-01 SG SG20789A patent/SG20789G/en unknown
- 1989-07-20 HK HK58689A patent/HK58689A/xx not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7553670B2 (en) | 2004-04-28 | 2009-06-30 | 3M Innovative Properties Company | Method for monitoring a polymerization in a three-dimensional sample |
| US9896599B2 (en) | 2013-04-30 | 2018-02-20 | 3M Innovative Properties Company | Process for preparing poly(benzoxazines) |
| US10040905B2 (en) | 2013-10-16 | 2018-08-07 | 3M Innovative Properties Company | Benzoxazine polymerization |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0094914B1 (de) | 1986-09-24 |
| EP0094914A2 (de) | 1983-11-23 |
| DE3366408D1 (en) | 1986-10-30 |
| SG20789G (en) | 1989-09-22 |
| JPH0261973B2 (Direct) | 1990-12-21 |
| EP0094914A3 (en) | 1984-02-08 |
| JPS58213019A (ja) | 1983-12-10 |
| HK58689A (en) | 1989-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |