CA1268034A - Photochromic composition resistant to fatigue - Google Patents
Photochromic composition resistant to fatigueInfo
- Publication number
- CA1268034A CA1268034A CA000499989A CA499989A CA1268034A CA 1268034 A CA1268034 A CA 1268034A CA 000499989 A CA000499989 A CA 000499989A CA 499989 A CA499989 A CA 499989A CA 1268034 A CA1268034 A CA 1268034A
- Authority
- CA
- Canada
- Prior art keywords
- lower alkyl
- hydrogen
- nickel
- photochromic
- hindered amine
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 28
- 150000001412 amines Chemical class 0.000 claims abstract description 25
- 239000004611 light stabiliser Substances 0.000 claims abstract description 19
- 239000000326 ultraviolet stabilizing agent Substances 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 239000003381 stabilizer Substances 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 229910052759 nickel Inorganic materials 0.000 claims description 10
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
- -1 Ni2+ ion Chemical class 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 7
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- 239000004033 plastic Substances 0.000 claims description 6
- 229920003023 plastic Polymers 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- PGHVFXYMFJCNJE-UHFFFAOYSA-K cobalt(3+) N,N-dibutylcarbamodithioate Chemical compound C(CCC)N(C([S-])=S)CCCC.[Co+3].C(CCC)N(C([S-])=S)CCCC.C(CCC)N(C([S-])=S)CCCC PGHVFXYMFJCNJE-UHFFFAOYSA-K 0.000 claims description 3
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 claims description 3
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical group CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 claims description 2
- LXRZJOUAIRAIPX-UHFFFAOYSA-N 3-[1-(3,5-ditert-butyl-4-hydroxyphenyl)-5,5-bis(1,2,2,6,6-pentamethylpiperidin-4-yl)pentoxy]-3-oxopropanoic acid Chemical compound C1C(C)(C)N(C)C(C)(C)CC1C(C1CC(C)(C)N(C)C(C)(C)C1)CCCC(OC(=O)CC(O)=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 LXRZJOUAIRAIPX-UHFFFAOYSA-N 0.000 claims 2
- STEYNUVPFMIUOY-UHFFFAOYSA-N 4-Hydroxy-1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CC(O)CC(C)(C)N1CCO STEYNUVPFMIUOY-UHFFFAOYSA-N 0.000 claims 2
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 claims 2
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 claims 2
- ZVRLGOKQDHVWSZ-UHFFFAOYSA-L cobalt(2+);n,n-di(propan-2-yl)carbamodithioate Chemical compound [Co+2].CC(C)N(C(C)C)C([S-])=S.CC(C)N(C(C)C)C([S-])=S ZVRLGOKQDHVWSZ-UHFFFAOYSA-L 0.000 claims 2
- JIJSLRQORTUOBN-UHFFFAOYSA-L nickel(2+);oxido-propan-2-yloxy-propan-2-ylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound [Ni+2].CC(C)OP([O-])(=S)SC(C)C.CC(C)OP([O-])(=S)SC(C)C JIJSLRQORTUOBN-UHFFFAOYSA-L 0.000 claims 2
- 239000013110 organic ligand Substances 0.000 claims 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 230000005281 excited state Effects 0.000 abstract description 8
- IAHPADQGUAKOQZ-UHFFFAOYSA-N spiro[1,3-dihydroindole-2,3'-benzo[f][1,4]benzoxazine] Chemical compound C1=CC=CC2=C(N=CC3(NC4=CC=CC=C4C3)O3)C3=CC=C21 IAHPADQGUAKOQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 150000002500 ions Chemical class 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- 239000012963 UV stabilizer Substances 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- SWZOQAGVRGQLDV-UHFFFAOYSA-N 4-[2-(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]-4-oxobutanoic acid Chemical compound CC1(C)CC(O)CC(C)(C)N1CCOC(=O)CCC(O)=O SWZOQAGVRGQLDV-UHFFFAOYSA-N 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013068 control sample Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 150000003254 radicals Chemical group 0.000 description 3
- 125000003003 spiro group Chemical group 0.000 description 3
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 2
- JHQVCQDWGSXTFE-UHFFFAOYSA-N 2-(2-prop-2-enoxycarbonyloxyethoxy)ethyl prop-2-enyl carbonate Chemical compound C=CCOC(=O)OCCOCCOC(=O)OCC=C JHQVCQDWGSXTFE-UHFFFAOYSA-N 0.000 description 2
- 101000654316 Centruroides limpidus Beta-toxin Cll2 Proteins 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000006303 photolysis reaction Methods 0.000 description 2
- 229940116351 sebacate Drugs 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 2
- WPRMJBJYCFNTKE-UHFFFAOYSA-L (3,5-ditert-butyl-4-hydroxyphenyl)methyl-ethoxyphosphinate;nickel(2+) Chemical compound [Ni+2].CCOP([O-])(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1.CCOP([O-])(=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WPRMJBJYCFNTKE-UHFFFAOYSA-L 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 102100033041 Carbonic anhydrase 13 Human genes 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 101000867860 Homo sapiens Carbonic anhydrase 13 Proteins 0.000 description 1
- 229920004142 LEXAN™ Polymers 0.000 description 1
- 239000004418 Lexan Substances 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 241000428533 Rhis Species 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 150000001565 benzotriazoles Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
- G03C1/00—Photosensitive materials
- G03C1/685—Compositions containing spiro-condensed pyran compounds or derivatives thereof, as photosensitive substances
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Glass Compositions (AREA)
- Heat Sensitive Colour Forming Recording (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
- Medicinal Preparation (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69645285A | 1985-01-31 | 1985-01-31 | |
| US696,452 | 1985-01-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1268034A true CA1268034A (en) | 1990-04-24 |
Family
ID=24797122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000499989A Expired - Lifetime CA1268034A (en) | 1985-01-31 | 1986-01-21 | Photochromic composition resistant to fatigue |
Country Status (6)
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU616650B2 (en) * | 1987-02-02 | 1991-11-07 | Toray Industries, Inc. | Spirooxazine photochromic compounds and resins |
| JPH0794657B2 (ja) * | 1987-10-16 | 1995-10-11 | 日産自動車株式会社 | フォトクロミック感光性材料 |
| IT1223067B (it) * | 1987-11-05 | 1990-09-12 | Enichem Sintesi | Composto fotocromatico ed articoli fotocromatici che lo contengono |
| US5180524A (en) * | 1987-11-05 | 1993-01-19 | Enichem Synthesis S.P.A. | Photochromatic composition and photochromatic articles which contain it |
| US5017225A (en) * | 1987-12-02 | 1991-05-21 | Japan Capsular Products Inc. | Microencapsulated photochromic material, process for its preparation and a water-base ink composition prepared therefrom |
| JP2545606B2 (ja) * | 1988-07-05 | 1996-10-23 | 呉羽化学工業株式会社 | フォトクロミック化合物およびフォトクロミック組成物 |
| GB8828091D0 (en) * | 1988-12-01 | 1989-01-05 | Traqson Ltd | Security marking |
| US5225113A (en) * | 1989-02-10 | 1993-07-06 | Enichem Synthesis S.P.A. | Photochromatic composition endowed with light fatigue resistance and photochromatic articles which contain it |
| IT1230711B (it) * | 1989-02-10 | 1991-10-29 | Enichem Sintesi | Composizione fotocromatica dotata di resistenza a fatica alla luce e articoli fotocromatici che la contengono. |
| JP2755444B2 (ja) * | 1989-09-28 | 1998-05-20 | 株式会社トクヤマ | クロメン組成物 |
| AU637868B2 (en) * | 1990-07-04 | 1993-06-10 | Lintec Corporation | Photochromic composition |
| EP0612796A1 (en) * | 1993-02-23 | 1994-08-31 | Ciba-Geigy Ag | Stabilisation of organic pigments |
| EP0612816B1 (en) * | 1993-02-23 | 1999-11-17 | Ciba SC Holding AG | Stabilisation of pyrrolopyrrole pigments |
| WO2008043848A2 (en) * | 2006-10-12 | 2008-04-17 | Opco Gmbh | Protective film |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD156372A1 (de) * | 1981-02-13 | 1982-08-18 | Manfred Reichenbaecher | Photochrome medien unter verwendung von 1,4-2h-oxazinen und spirophenanthro-1,4-2h-oxazinen |
| US4440672A (en) * | 1982-03-22 | 1984-04-03 | American Optical Corporation | Photochromic composition resistant to fatigue |
-
1986
- 1986-01-21 CA CA000499989A patent/CA1268034A/en not_active Expired - Lifetime
- 1986-01-30 BR BR8600381A patent/BR8600381A/pt not_active IP Right Cessation
- 1986-01-31 EP EP86101289A patent/EP0195898B1/en not_active Expired
- 1986-01-31 JP JP61020026A patent/JPS61241383A/ja active Granted
- 1986-01-31 AT AT86101289T patent/ATE38391T1/de active
- 1986-01-31 DE DE8686101289T patent/DE3661076D1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3661076D1 (en) | 1988-12-08 |
| JPS61241383A (ja) | 1986-10-27 |
| JPH0343315B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-07-02 |
| EP0195898B1 (en) | 1988-11-02 |
| EP0195898A1 (en) | 1986-10-01 |
| ATE38391T1 (de) | 1988-11-15 |
| BR8600381A (pt) | 1986-10-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed | ||
| MKEC | Expiry (correction) |
Effective date: 20121205 |