CA2536437A1 - Novel reactive yellow dyes useful for ocular devices - Google Patents
Novel reactive yellow dyes useful for ocular devices Download PDFInfo
- Publication number
- CA2536437A1 CA2536437A1 CA002536437A CA2536437A CA2536437A1 CA 2536437 A1 CA2536437 A1 CA 2536437A1 CA 002536437 A CA002536437 A CA 002536437A CA 2536437 A CA2536437 A CA 2536437A CA 2536437 A1 CA2536437 A1 CA 2536437A1
- Authority
- CA
- Canada
- Prior art keywords
- ocular device
- compositions
- intraocular lens
- blue light
- polymeric compositions
- 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.)
- Abandoned
Links
- 239000001043 yellow dye Substances 0.000 title abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 230000031700 light absorption Effects 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims description 25
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 11
- 229920002554 vinyl polymer Polymers 0.000 claims description 11
- 229920001296 polysiloxane Polymers 0.000 claims description 10
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 238000007334 copolymerization reaction Methods 0.000 claims description 8
- -1 vinylacetyl Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 101100439662 Arabidopsis thaliana CHR5 gene Proteins 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims description 2
- 229910052710 silicon Inorganic materials 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 238000005266 casting Methods 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 210000001525 retina Anatomy 0.000 abstract description 7
- 230000000903 blocking effect Effects 0.000 abstract description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000007943 implant Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 208000002177 Cataract Diseases 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 210000004087 cornea Anatomy 0.000 description 3
- 230000000254 damaging effect Effects 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000003780 insertion Methods 0.000 description 3
- 230000037431 insertion Effects 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- NBNGEWSXRJTUOZ-UHFFFAOYSA-N n-[2-(4-hydroxyphenyl)ethyl]but-3-enamide Chemical compound OC1=CC=C(CCNC(=O)CC=C)C=C1 NBNGEWSXRJTUOZ-UHFFFAOYSA-N 0.000 description 3
- 239000012264 purified product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 2
- 208000002847 Surgical Wound Diseases 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- OKOSPWNNXVDXKZ-UHFFFAOYSA-N but-3-enoyl chloride Chemical compound ClC(=O)CC=C OKOSPWNNXVDXKZ-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001356 surgical procedure Methods 0.000 description 2
- RCTZKJGLWRCHMI-UHFFFAOYSA-N (2-ethylphenyl) 2-methylprop-2-eneperoxoate Chemical compound CCC1=CC=CC=C1OOC(=O)C(C)=C RCTZKJGLWRCHMI-UHFFFAOYSA-N 0.000 description 1
- HYZJSTPCAKOIHY-UHFFFAOYSA-N (2-ethylphenyl) prop-2-eneperoxoate Chemical compound CCC1=CC=CC=C1OOC(=O)C=C HYZJSTPCAKOIHY-UHFFFAOYSA-N 0.000 description 1
- UFEHZTGKQGVALB-UHFFFAOYSA-N (2-ethylsulfanylphenyl) 2-methylprop-2-enoate Chemical compound CCSC1=CC=CC=C1OC(=O)C(C)=C UFEHZTGKQGVALB-UHFFFAOYSA-N 0.000 description 1
- PAXZRCDQHAXYCI-UHFFFAOYSA-N (2-ethylsulfanylphenyl) prop-2-enoate Chemical compound CCSC1=CC=CC=C1OC(=O)C=C PAXZRCDQHAXYCI-UHFFFAOYSA-N 0.000 description 1
- AOUAMFARIYTDLK-UHFFFAOYSA-N (4-methylphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(C)C=C1 AOUAMFARIYTDLK-UHFFFAOYSA-N 0.000 description 1
- ZALFZMYXGFDRIW-UHFFFAOYSA-N (4-methylphenyl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=C(C)C=C1 ZALFZMYXGFDRIW-UHFFFAOYSA-N 0.000 description 1
- IYYYCBNVZMXIOM-UHFFFAOYSA-N 1-[2-[4-hydroxy-3-[(2-methylphenyl)diazenyl]phenyl]ethyl]pyrrole-2,5-dione Chemical compound Cc1ccccc1N=Nc1cc(CCN2C(=O)C=CC2=O)ccc1O IYYYCBNVZMXIOM-UHFFFAOYSA-N 0.000 description 1
- ITKPEKLPFWJSOJ-UHFFFAOYSA-N 2-(2-chlorophenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1Cl ITKPEKLPFWJSOJ-UHFFFAOYSA-N 0.000 description 1
- CAWQOFMAJKVFII-UHFFFAOYSA-N 2-(3-chlorophenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC(Cl)=C1 CAWQOFMAJKVFII-UHFFFAOYSA-N 0.000 description 1
- ACZLUEDVQBUFQM-UHFFFAOYSA-N 2-(3-phenylphenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC(C=2C=CC=CC=2)=C1 ACZLUEDVQBUFQM-UHFFFAOYSA-N 0.000 description 1
- XUXKNMQGQVAAJA-UHFFFAOYSA-N 2-(4-benzylphenyl)ethyl 2-methylprop-2-enoate Chemical compound C1=CC(CCOC(=O)C(=C)C)=CC=C1CC1=CC=CC=C1 XUXKNMQGQVAAJA-UHFFFAOYSA-N 0.000 description 1
- XHMBRNYBXTUYJN-UHFFFAOYSA-N 2-(4-bromophenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(Br)C=C1 XHMBRNYBXTUYJN-UHFFFAOYSA-N 0.000 description 1
- DANPNQMLVGTTRA-UHFFFAOYSA-N 2-(4-chlorophenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(Cl)C=C1 DANPNQMLVGTTRA-UHFFFAOYSA-N 0.000 description 1
- WRAODFTZIJZVJH-UHFFFAOYSA-N 2-(4-cyclohexylphenyl)ethyl 2-methylprop-2-enoate Chemical compound C1=CC(CCOC(=O)C(=C)C)=CC=C1C1CCCCC1 WRAODFTZIJZVJH-UHFFFAOYSA-N 0.000 description 1
- IOFBPLNRQQDCSU-UHFFFAOYSA-N 2-(4-methoxyphenyl)ethyl 2-methylprop-2-enoate Chemical compound COC1=CC=C(CCOC(=O)C(C)=C)C=C1 IOFBPLNRQQDCSU-UHFFFAOYSA-N 0.000 description 1
- XKTDLXROKPMKQF-UHFFFAOYSA-N 2-(4-phenylphenyl)ethyl 2-methylprop-2-enoate Chemical compound C1=CC(CCOC(=O)C(=C)C)=CC=C1C1=CC=CC=C1 XKTDLXROKPMKQF-UHFFFAOYSA-N 0.000 description 1
- VZHXURTZSGZTOY-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)ethyl 2-methylprop-2-enoate Chemical compound CC(C)C1=CC=C(CCOC(=O)C(C)=C)C=C1 VZHXURTZSGZTOY-UHFFFAOYSA-N 0.000 description 1
- WIGVBGZTCYJIIS-UHFFFAOYSA-N 2-(4-propylphenyl)ethyl 2-methylprop-2-enoate Chemical compound CCCC1=CC=C(CCOC(=O)C(C)=C)C=C1 WIGVBGZTCYJIIS-UHFFFAOYSA-N 0.000 description 1
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 description 1
- RXXZODOCQIRRQA-UHFFFAOYSA-N 3-phenylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCC1=CC=CC=C1 RXXZODOCQIRRQA-UHFFFAOYSA-N 0.000 description 1
- QPQKUYVSJWQSDY-UHFFFAOYSA-N 4-phenyldiazenylaniline Chemical compound C1=CC(N)=CC=C1N=NC1=CC=CC=C1 QPQKUYVSJWQSDY-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- LCOOBIOTZJNTKU-UHFFFAOYSA-N N-[2-[4-hydroxy-3-[(2-methylphenyl)diazenyl]phenyl]ethyl]but-3-enamide Chemical compound C(=C)CC(=O)NCCC1=CC(=C(C=C1)O)N=NC1=C(C=CC=C1)C LCOOBIOTZJNTKU-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 208000035965 Postoperative Complications Diseases 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- WJQBPCWUWOVPCP-UHFFFAOYSA-N [2-(ethylamino)phenyl] 2-methylprop-2-enoate Chemical compound CCNC1=CC=CC=C1OC(=O)C(C)=C WJQBPCWUWOVPCP-UHFFFAOYSA-N 0.000 description 1
- FSKSDAZAWNBWFW-UHFFFAOYSA-N [2-(ethylamino)phenyl] prop-2-enoate Chemical compound CCNC1=CC=CC=C1OC(=O)C=C FSKSDAZAWNBWFW-UHFFFAOYSA-N 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 210000002159 anterior chamber Anatomy 0.000 description 1
- 201000009310 astigmatism Diseases 0.000 description 1
- 125000005615 azonium group Chemical group 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- ABBZJHFBQXYTLU-UHFFFAOYSA-N but-3-enamide Chemical compound NC(=O)CC=C ABBZJHFBQXYTLU-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 208000002780 macular degeneration Diseases 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- BHVOXWAUNMHESP-UHFFFAOYSA-N n-[2-(2-hydroxyphenyl)ethyl]prop-2-enamide Chemical compound OC1=CC=CC=C1CCNC(=O)C=C BHVOXWAUNMHESP-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000007779 soft material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/106—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an azo dye
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61F—FILTERS IMPLANTABLE INTO BLOOD VESSELS; PROSTHESES; DEVICES PROVIDING PATENCY TO, OR PREVENTING COLLAPSING OF, TUBULAR STRUCTURES OF THE BODY, e.g. STENTS; ORTHOPAEDIC, NURSING OR CONTRACEPTIVE DEVICES; FOMENTATION; TREATMENT OR PROTECTION OF EYES OR EARS; BANDAGES, DRESSINGS OR ABSORBENT PADS; FIRST-AID KITS
- A61F2/00—Filters implantable into blood vessels; Prostheses, i.e. artificial substitutes or replacements for parts of the body; Appliances for connecting them with the body; Devices providing patency to, or preventing collapsing of, tubular structures of the body, e.g. stents
- A61F2/02—Prostheses implantable into the body
- A61F2/14—Eye parts, e.g. lenses or corneal implants; Artificial eyes
- A61F2/16—Intraocular lenses
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Ophthalmology & Optometry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- General Physics & Mathematics (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Optics & Photonics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Prostheses (AREA)
- Materials For Medical Uses (AREA)
- Eyeglasses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/657,495 | 2003-09-08 | ||
| US10/657,495 US7098283B2 (en) | 2003-09-08 | 2003-09-08 | Reactive yellow dyes useful for ocular devices |
| PCT/US2004/027008 WO2005026266A1 (en) | 2003-09-08 | 2004-08-19 | Novel reactive yellow dyes useful for ocular devices |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2536437A1 true CA2536437A1 (en) | 2005-03-24 |
Family
ID=34226569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002536437A Abandoned CA2536437A1 (en) | 2003-09-08 | 2004-08-19 | Novel reactive yellow dyes useful for ocular devices |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US7098283B2 (https=) |
| EP (1) | EP1664205A1 (https=) |
| JP (1) | JP2007505170A (https=) |
| KR (1) | KR20060076767A (https=) |
| CN (1) | CN1849375A (https=) |
| AU (1) | AU2004272525A1 (https=) |
| CA (1) | CA2536437A1 (https=) |
| TW (1) | TW200526744A (https=) |
| WO (1) | WO2005026266A1 (https=) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8403478B2 (en) | 2001-11-02 | 2013-03-26 | High Performance Optics, Inc. | Ophthalmic lens to preserve macular integrity |
| US8500274B2 (en) | 2000-11-03 | 2013-08-06 | High Performance Optics, Inc. | Dual-filter ophthalmic lens to reduce risk of macular degeneration |
| JP4896737B2 (ja) | 2003-12-29 | 2012-03-14 | アボット・メディカル・オプティクス・インコーポレイテッド | 可視光選択的透過領域を有する眼内レンズ |
| US7278737B2 (en) | 2004-04-30 | 2007-10-09 | Advanced Medical Optics, Inc. | Ophthalmic devices having a highly selective violet light transmissive filter and related methods |
| EP2261696B1 (en) * | 2004-11-22 | 2012-03-14 | Abbott Medical Optics Inc. | Copolymerizable azo compounds and articles containing them |
| US20060115516A1 (en) | 2004-11-22 | 2006-06-01 | Pearson Jason C | Copolymerizable methine and anthraquinone compounds and articles containing them |
| JP4291296B2 (ja) * | 2005-04-08 | 2009-07-08 | 株式会社メニコン | 新規重合性染料およびそれを含む眼用レンズ |
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| US5470932A (en) * | 1993-10-18 | 1995-11-28 | Alcon Laboratories, Inc. | Polymerizable yellow dyes and their use in opthalmic lenses |
| US6015842A (en) * | 1997-08-07 | 2000-01-18 | Alcon Laboratories, Inc. | Method of preparing foldable hydrophilic ophthalmic device materials |
| US5891931A (en) * | 1997-08-07 | 1999-04-06 | Alcon Laboratories, Inc. | Method of preparing foldable high refractive index acrylic ophthalmic device materials |
| US6353069B1 (en) * | 1998-04-15 | 2002-03-05 | Alcon Manufacturing, Ltd. | High refractive index ophthalmic device materials |
| JP4225612B2 (ja) | 1998-09-09 | 2009-02-18 | スター・ジャパン株式会社 | 眼用レンズ材料 |
| JP4210719B2 (ja) * | 2001-09-14 | 2009-01-21 | スター・ジャパン株式会社 | 眼用レンズ |
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- 2003-09-08 US US10/657,495 patent/US7098283B2/en not_active Expired - Lifetime
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- 2004-08-19 EP EP04781650A patent/EP1664205A1/en not_active Withdrawn
- 2004-08-19 WO PCT/US2004/027008 patent/WO2005026266A1/en not_active Ceased
- 2004-08-19 AU AU2004272525A patent/AU2004272525A1/en not_active Abandoned
- 2004-08-19 CN CNA2004800257161A patent/CN1849375A/zh active Pending
- 2004-08-19 CA CA002536437A patent/CA2536437A1/en not_active Abandoned
- 2004-08-19 KR KR1020067004657A patent/KR20060076767A/ko not_active Withdrawn
- 2004-08-19 JP JP2006525353A patent/JP2007505170A/ja active Pending
- 2004-09-07 TW TW093127062A patent/TW200526744A/zh unknown
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2006
- 2006-06-21 US US11/472,235 patent/US7304117B2/en not_active Expired - Lifetime
- 2006-06-21 US US11/471,990 patent/US20060241263A1/en not_active Abandoned
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| WO2005026266A1 (en) | 2005-03-24 |
| TW200526744A (en) | 2005-08-16 |
| JP2007505170A (ja) | 2007-03-08 |
| US20050054797A1 (en) | 2005-03-10 |
| EP1664205A1 (en) | 2006-06-07 |
| AU2004272525A1 (en) | 2005-03-24 |
| KR20060076767A (ko) | 2006-07-04 |
| CN1849375A (zh) | 2006-10-18 |
| US20060241263A1 (en) | 2006-10-26 |
| US20060241264A1 (en) | 2006-10-26 |
| US7304117B2 (en) | 2007-12-04 |
| US7098283B2 (en) | 2006-08-29 |
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