CA2049869C - Matiere polarisant la lumiere a base de derives de l'acide ethylenediaminepolyacetique - Google Patents

Matiere polarisant la lumiere a base de derives de l'acide ethylenediaminepolyacetique Download PDF

Info

Publication number: CA2049869C
Authority: CA; Canada
Prior art keywords: acid; light; disodium; ethylene diamine; polarizing
Prior art date: 1990-07-30
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 - Fee Related

Application number

CA002049869A

Other languages

English (en)

Other versions

CA2049869A1 (fr

Inventor

Joseph Aloysius Check, Iii

Robert L. Saxe

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.)

Research Frontiers Inc

Original Assignee

Research Frontiers Inc

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.)

1990-07-30

Filing date

1991-08-26

Publication date

2001-05-29

1990-07-30 Priority to US07/559,727 priority Critical patent/US5093041A/en

1990-07-30 Priority claimed from US07/559,727 external-priority patent/US5093041A/en

1991-08-26 Application filed by Research Frontiers Inc filed Critical Research Frontiers Inc

1991-08-26 Priority to CA002049869A priority patent/CA2049869C/fr

1991-09-16 Priority to EP91402451A priority patent/EP0532809B1/fr

1992-04-07 Priority to CA002065500A priority patent/CA2065500C/fr

1992-04-28 Priority to JP10970892A priority patent/JP3209566B2/ja

1993-02-27 Publication of CA2049869A1 publication Critical patent/CA2049869A1/fr

2001-05-29 Application granted granted Critical

2001-05-29 Publication of CA2049869C publication Critical patent/CA2049869C/fr

2011-08-26 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

239000000463 material Substances 0.000 title claims abstract description 35
239000002253 acid Substances 0.000 title claims description 21
239000000725 suspension Substances 0.000 claims abstract description 25
239000006194 liquid suspension Substances 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims description 31
239000002245 particle Substances 0.000 claims description 28
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 27
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 14
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 12
150000001340 alkali metals Chemical class 0.000 claims description 11
KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 claims description 11
IFQUWYZCAGRUJN-UHFFFAOYSA-N ethylenediaminediacetic acid Chemical class OC(=O)CNCCNCC(O)=O IFQUWYZCAGRUJN-UHFFFAOYSA-N 0.000 claims description 11
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 11
229960001484 edetic acid Drugs 0.000 claims description 10
150000004820 halides Chemical class 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000007788 liquid Substances 0.000 claims description 7
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 6
229910001508 alkali metal halide Inorganic materials 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
229910052783 alkali metal Inorganic materials 0.000 claims description 5
GFVMLYBCWPLMTF-UHFFFAOYSA-N disodiomagnesium Chemical class [Na][Mg][Na] GFVMLYBCWPLMTF-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
230000006872 improvement Effects 0.000 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 4
150000001805 chlorine compounds Chemical group 0.000 claims 4
150000001342 alkaline earth metals Chemical class 0.000 claims 1
230000000717 retained effect Effects 0.000 claims 1
229910052740 iodine Inorganic materials 0.000 description 24
239000011630 iodine Substances 0.000 description 24
239000013078 crystal Substances 0.000 description 14
238000000034 method Methods 0.000 description 13
-1 nitrogen-containing organic compound Chemical class 0.000 description 10
150000001450 anions Chemical class 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002609 medium Substances 0.000 description 6
UNMYWSMUMWPJLR-UHFFFAOYSA-L Calcium iodide Chemical compound [Ca+2].[I-].[I-] UNMYWSMUMWPJLR-UHFFFAOYSA-L 0.000 description 4
239000000020 Nitrocellulose Substances 0.000 description 4
229910001640 calcium iodide Inorganic materials 0.000 description 4
229940046413 calcium iodide Drugs 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
239000012530 fluid Substances 0.000 description 4
229920001220 nitrocellulos Polymers 0.000 description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
230000008569 process Effects 0.000 description 4
230000005855 radiation Effects 0.000 description 4
OCLTZILENWBWIY-HKPQTANOSA-N (r)-[(2s,4s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;molecular iodine;sulfuric acid;dihydroiodide Chemical compound I.I.II.II.OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.C([C@H]([C@H](C1)C=C)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 OCLTZILENWBWIY-HKPQTANOSA-N 0.000 description 3
WFJNHVWTKZUUTR-KODHJQJWSA-N (r)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol Chemical compound C1=CC=C2C([C@@H](O)[C@@H]3C[C@@H]4CCN3C[C@@H]4CC)=CC=NC2=C1 WFJNHVWTKZUUTR-KODHJQJWSA-N 0.000 description 3
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
229940093475 2-ethoxyethanol Drugs 0.000 description 3
239000004372 Polyvinyl alcohol Substances 0.000 description 3
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical class C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
WFJNHVWTKZUUTR-UHFFFAOYSA-N dihydrocinchonidine Natural products C1=CC=C2C(C(O)C3CC4CCN3CC4CC)=CC=NC2=C1 WFJNHVWTKZUUTR-UHFFFAOYSA-N 0.000 description 3
239000011521 glass Substances 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
229920002451 polyvinyl alcohol Polymers 0.000 description 3
235000019422 polyvinyl alcohol Nutrition 0.000 description 3
239000002243 precursor Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
230000005540 biological transmission Effects 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910001424 calcium ion Inorganic materials 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
229920002301 cellulose acetate Polymers 0.000 description 2
230000008859 change Effects 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
230000007613 environmental effect Effects 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
238000003475 lamination Methods 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
229960001463 quinine bisulfate Drugs 0.000 description 2
RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
KEVRVUAKQLMNFS-UHFFFAOYSA-N 2,2-dimethylpropyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)COC(=O)C(C)(C)C KEVRVUAKQLMNFS-UHFFFAOYSA-N 0.000 description 1
MGDKBCNOUDORNI-UHFFFAOYSA-N 2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]acetic acid;potassium Chemical compound [K].[K].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O MGDKBCNOUDORNI-UHFFFAOYSA-N 0.000 description 1
YGDVXSDNEFDTGV-UHFFFAOYSA-N 2-[6-[bis(carboxymethyl)amino]hexyl-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CCCCCCN(CC(O)=O)CC(O)=O YGDVXSDNEFDTGV-UHFFFAOYSA-N 0.000 description 1
BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
239000004382 Amylase Substances 0.000 description 1
102000013142 Amylases Human genes 0.000 description 1
108010065511 Amylases Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229920002160 Celluloid Polymers 0.000 description 1
235000001258 Cinchona calisaya Nutrition 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
241000013355 Mycteroperca interstitialis Species 0.000 description 1
CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
BDOGHYSOSXQHCL-UHFFFAOYSA-N [K].[K].CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.NCCN Chemical compound [K].[K].CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.NCCN BDOGHYSOSXQHCL-UHFFFAOYSA-N 0.000 description 1
XKPMDXAYDXOODD-UHFFFAOYSA-N [Na].[Na].[Mg].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O Chemical compound [Na].[Na].[Mg].OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O XKPMDXAYDXOODD-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
229930013930 alkaloid Natural products 0.000 description 1
150000003797 alkaloid derivatives Chemical class 0.000 description 1
235000019418 amylase Nutrition 0.000 description 1
238000009835 boiling Methods 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
229910052791 calcium Inorganic materials 0.000 description 1
GVHRTAKEBFEMFD-UHFFFAOYSA-L calcium;diiodide;hexahydrate Chemical compound O.O.O.O.O.O.[Ca+2].[I-].[I-] GVHRTAKEBFEMFD-UHFFFAOYSA-L 0.000 description 1
KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 1
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000002612 dispersion medium Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000005684 electric field Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
229910001505 inorganic iodide Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
CMUCGJHILMSIQX-UHFFFAOYSA-N quinoline-2-carbonyl quinoline-2-carboxylate Chemical compound C1=CC=CC2=NC(C(OC(=O)C=3N=C4C=CC=CC4=CC=3)=O)=CC=C21 CMUCGJHILMSIQX-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
239000013049 sediment Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Landscapes

Nitrogen Condensed Heterocyclic Rings (AREA)
Polarising Elements (AREA)

CA002049869A 1990-07-30 1991-08-26 Matiere polarisant la lumiere a base de derives de l'acide ethylenediaminepolyacetique Expired - Fee Related CA2049869C (fr)

Priority Applications (5)

Application Number	Priority Date	Filing Date	Title
US07/559,727 US5093041A (en)	1990-07-30	1990-07-30	Light-polarizing material based on ethylenediamine polyacetic acid derivatives
CA002049869A CA2049869C (fr)	1990-07-30	1991-08-26	Matiere polarisant la lumiere a base de derives de l'acide ethylenediaminepolyacetique
EP91402451A EP0532809B1 (fr)	1990-07-30	1991-09-16	Matériel polarisant la lumière à base de dérivés d'acides ethylenediamine polyacétiques
CA002065500A CA2065500C (fr)	1990-07-30	1992-04-07	Produits a base de derives de l'acide quinaldique polarisant la lumiere
JP10970892A JP3209566B2 (ja)	1990-07-30	1992-04-28	偏光物質

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US07/559,727 US5093041A (en)	1990-07-30	1990-07-30	Light-polarizing material based on ethylenediamine polyacetic acid derivatives
CA002049869A CA2049869C (fr)	1990-07-30	1991-08-26	Matiere polarisant la lumiere a base de derives de l'acide ethylenediaminepolyacetique
JP10970892A JP3209566B2 (ja)	1990-07-30	1992-04-28	偏光物質

Publications (2)

Publication Number	Publication Date
CA2049869A1 CA2049869A1 (fr)	1993-02-27
CA2049869C true CA2049869C (fr)	2001-05-29

Family

ID=27168945

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002049869A Expired - Fee Related CA2049869C (fr)	1990-07-30	1991-08-26	Matiere polarisant la lumiere a base de derives de l'acide ethylenediaminepolyacetique

Country Status (1)

Country	Link
CA (1)	CA2049869C (fr)

1991
- 1991-08-26 CA CA002049869A patent/CA2049869C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2049869A1 (fr)	1993-02-27

Legal Events

Date	Code	Title	Description
1998-03-19	EEER	Examination request
2010-08-26	MKLA	Lapsed
2023-05-26	MKLA	Lapsed	Effective date: 20100826

Publication	Publication Date	Title
EP0532809B1 (fr)	1996-02-28	Matériel polarisant la lumière à base de dérivés d'acides ethylenediamine polyacétiques
US4877313A (en)	1989-10-31	Light-polarizing materials and suspensions thereof
CA2027349C (fr)	2001-02-06	Matieres photopolarisantes et substances contenant ces matieres en suspension
US4422963A (en)	1983-12-27	Light valve polarizing materials and suspensions thereof
US5130057A (en)	1992-07-14	Light polarizing materials and suspensions thereof
US4270841A (en)	1981-06-02	Light valve containing suspension of perhalide of alkaloid acid salt
CA2049869C (fr)	2001-05-29	Matiere polarisant la lumiere a base de derives de l'acide ethylenediaminepolyacetique
KR100365576B1 (ko)	2002-12-26	편광 재료, 이의 액체 현탁액 및 필름과, 이들을 함유하는 광 밸브
EP0403711B1 (fr)	1993-12-08	Matières polarisant la lumière et suspensions de telles matières
EP0564676B1 (fr)	1998-12-30	Matériaux de polarisation de la lumière basés sur des dérivés de l'acide quinaldique
JP2798426B2 (ja)	1998-09-17	偏光材料及びその懸濁物
AU737670B2 (en)	2001-08-30	Light-polarizing particles of improved particle size distribution
JP3187874B2 (ja)	2001-07-16	エチレンジアミンポリ酢酸をベースとする光−偏光性物質
CA1336858C (fr)	1995-09-05	Matieres polarisant la lumiere et suspensions de ces matieres
KR100255249B1 (ko)	2000-05-01	에틸렌디아민 폴리아세트산 유도체를 기초로한 편광물질
US4131334A (en)	1978-12-26	Light polarizing materials, suspensions thereof, and process for manufacturing such suspensions
KR0153272B1 (ko)	1998-12-15	광편광체 및 이의 현탁액
DE69117507T2 (de)	1996-09-26	Lichtpolarisierendes Material auf Basis von Äthylendiaminpolyessigsäurederivaten
US5256337A (en)	1993-10-26	Photochromic polymer membrane
US6334967B1 (en)	2002-01-01	Light-polarizing particles of improved particle size distribution
US6517746B1 (en)	2003-02-11	Polyhalide particles and light valves comprising same
CA2080899A1 (fr)	1991-10-18	Membrane de polymere photochromique
CA2336347C (fr)	2004-11-23	Particules de polyhalogenure et modulateurs de lumiere renfermant de telles particules
GB1586125A (en)	1981-03-18	Light polarizing materials suspensions thereof and use thereof in light valves