CA2379249C - Hydrophilic biomedical compositions - Google Patents
Hydrophilic biomedical compositions Download PDFInfo
- Publication number
- CA2379249C CA2379249C CA2379249A CA2379249A CA2379249C CA 2379249 C CA2379249 C CA 2379249C CA 2379249 A CA2379249 A CA 2379249A CA 2379249 A CA2379249 A CA 2379249A CA 2379249 C CA2379249 C CA 2379249C
- Authority
- CA
- Canada
- Prior art keywords
- range
- macromonomer
- modulus
- kpa
- lens
- 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 - Fee Related
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- 239000000203 mixture Substances 0.000 title description 17
- 239000000178 monomer Substances 0.000 claims abstract description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- 238000011065 in-situ storage Methods 0.000 claims abstract description 6
- 229920000642 polymer Polymers 0.000 claims description 24
- 239000002775 capsule Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 150000003926 acrylamides Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 229920001400 block copolymer Polymers 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 201000010041 presbyopia Diseases 0.000 claims description 3
- 229920005604 random copolymer Polymers 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 229920000249 biocompatible polymer Polymers 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 210000004087 cornea Anatomy 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 210000000695 crystalline len Anatomy 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 11
- 238000004132 cross linking Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- -1 polyethylene Polymers 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- QKPKBBFSFQAMIY-UHFFFAOYSA-N 2-ethenyl-4,4-dimethyl-1,3-oxazol-5-one Chemical compound CC1(C)N=C(C=C)OC1=O QKPKBBFSFQAMIY-UHFFFAOYSA-N 0.000 description 4
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 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 3
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 3
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 230000005855 radiation Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 208000002177 Cataract Diseases 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 150000008062 acetophenones Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- QRWAIZJYJNLOPG-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) acetate Chemical compound C=1C=CC=CC=1C(OC(=O)C)C(=O)C1=CC=CC=C1 QRWAIZJYJNLOPG-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- YIYBRXKMQFDHSM-UHFFFAOYSA-N 2,2'-Dihydroxybenzophenone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1O YIYBRXKMQFDHSM-UHFFFAOYSA-N 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 1
- LNBMZFHIYRDKNS-UHFFFAOYSA-N 2,2-dimethoxy-1-phenylethanone Chemical compound COC(OC)C(=O)C1=CC=CC=C1 LNBMZFHIYRDKNS-UHFFFAOYSA-N 0.000 description 1
- IFOWXFUNZNAQJJ-UHFFFAOYSA-N 2,4-dihydroxy-2,4-dimethylpentan-3-one Chemical compound CC(C)(O)C(=O)C(C)(C)O IFOWXFUNZNAQJJ-UHFFFAOYSA-N 0.000 description 1
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical compound O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- UMWZLYTVXQBTTE-UHFFFAOYSA-N 2-pentylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(CCCCC)=CC=C3C(=O)C2=C1 UMWZLYTVXQBTTE-UHFFFAOYSA-N 0.000 description 1
- AXYQEGMSGMXGGK-UHFFFAOYSA-N 2-phenoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)C(C=1C=CC=CC=1)OC1=CC=CC=C1 AXYQEGMSGMXGGK-UHFFFAOYSA-N 0.000 description 1
- YTPSFXZMJKMUJE-UHFFFAOYSA-N 2-tert-butylanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(C(C)(C)C)=CC=C3C(=O)C2=C1 YTPSFXZMJKMUJE-UHFFFAOYSA-N 0.000 description 1
- WHNPOQXWAMXPTA-UHFFFAOYSA-N 3-methylbut-2-enamide Chemical compound CC(C)=CC(N)=O WHNPOQXWAMXPTA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- HLJYBXJFKDDIBI-UHFFFAOYSA-N O=[PH2]C(=O)C1=CC=CC=C1 Chemical class O=[PH2]C(=O)C1=CC=CC=C1 HLJYBXJFKDDIBI-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- ZNZDJSGUWLGTLA-UHFFFAOYSA-N [(1-oxo-1-phenylpropan-2-ylidene)amino] benzoate Chemical compound C=1C=CC=CC=1C(=O)C(C)=NOC(=O)C1=CC=CC=C1 ZNZDJSGUWLGTLA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 description 1
- 210000001367 artery Anatomy 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
- 150000008366 benzophenones Chemical class 0.000 description 1
- 239000000560 biocompatible material Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- JVASZXZJOJUKDT-UHFFFAOYSA-N bis(1-aminocyclohexa-2,4-dien-1-yl)methanone Chemical class C1C=CC=CC1(N)C(=O)C1(N)CC=CC=C1 JVASZXZJOJUKDT-UHFFFAOYSA-N 0.000 description 1
- CQAIBOSCGCTHPV-UHFFFAOYSA-N bis(1-hydroxycyclohexa-2,4-dien-1-yl)methanone Chemical class C1C=CC=CC1(O)C(=O)C1(O)CC=CC=C1 CQAIBOSCGCTHPV-UHFFFAOYSA-N 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 229930006711 bornane-2,3-dione Natural products 0.000 description 1
- KFKPWTFHOVSSSI-UHFFFAOYSA-N butyl 2-hydroxyprop-2-enoate Chemical compound CCCCOC(=O)C(O)=C KFKPWTFHOVSSSI-UHFFFAOYSA-N 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000012377 drug delivery Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 210000003709 heart valve Anatomy 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229920001480 hydrophilic copolymer Polymers 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000012633 leachable Substances 0.000 description 1
- 210000001542 lens epithelial cell Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000001791 phenazinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000002407 tissue scaffold Substances 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/16—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/56—Acrylamide; Methacrylamide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2430/00—Materials or treatment for tissue regeneration
- A61L2430/16—Materials or treatment for tissue regeneration for reconstruction of eye parts, e.g. intraocular lens, cornea
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Ophthalmology & Optometry (AREA)
- Veterinary Medicine (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Transplantation (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Polymers & Plastics (AREA)
- Vascular Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Prostheses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Medical Uses (AREA)
- Eyeglasses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPQ1977 | 1999-08-02 | ||
| AUPQ1977A AUPQ197799A0 (en) | 1999-08-02 | 1999-08-02 | Hydrophilic biomedical compositions |
| PCT/AU2000/000916 WO2001008604A1 (en) | 1999-08-02 | 2000-08-02 | Hydrophilic biomedical compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2379249A1 CA2379249A1 (en) | 2001-02-08 |
| CA2379249C true CA2379249C (en) | 2010-10-12 |
Family
ID=3816157
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2379249A Expired - Fee Related CA2379249C (en) | 1999-08-02 | 2000-08-02 | Hydrophilic biomedical compositions |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US6774197B1 (enExample) |
| EP (1) | EP1210034A4 (enExample) |
| JP (1) | JP4975920B2 (enExample) |
| AU (1) | AUPQ197799A0 (enExample) |
| CA (1) | CA2379249C (enExample) |
| HK (1) | HK1047689A1 (enExample) |
| WO (1) | WO2001008604A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPQ197899A0 (en) * | 1999-08-02 | 1999-08-26 | Commonwealth Scientific And Industrial Research Organisation | Biomedical compositions |
| SE0102543D0 (sv) | 2001-07-16 | 2001-07-16 | Pharmacia Groningen Bv | Compositions capable of forming hydrogels in the eye |
| US6747090B2 (en) | 2001-07-16 | 2004-06-08 | Pharmacia Groningen Bv | Compositions capable of forming hydrogels in the eye |
| AU2002950469A0 (en) * | 2002-07-30 | 2002-09-12 | Commonwealth Scientific And Industrial Research Organisation | Improved biomedical compositions |
| US20060251795A1 (en) * | 2005-05-05 | 2006-11-09 | Boris Kobrin | Controlled vapor deposition of biocompatible coatings for medical devices |
| US8029515B2 (en) * | 2005-01-31 | 2011-10-04 | Yichieh Shiuey | Corneal implants and methods and systems for placement |
| US20070197681A1 (en) * | 2006-02-22 | 2007-08-23 | Advanced Medical Optics | Lens surface enhancement |
| WO2007128051A1 (en) * | 2006-05-03 | 2007-11-15 | Vision Crc Limited | Biological polysiloxanes |
| WO2007128055A1 (en) | 2006-05-03 | 2007-11-15 | Vision Crc Limited | Eye treatment |
| AU2012231774A1 (en) | 2011-03-21 | 2013-08-01 | Adventus Technology, Inc. | Restoration of accommodation by lens refilling |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4777217A (en) * | 1987-02-26 | 1988-10-11 | Minnesota Mining And Manufacturing Company | Methacrylamide functional polymers and method |
| US4874822A (en) * | 1988-04-07 | 1989-10-17 | Minnesota Mining And Manufacturing Company | Process for the acrylamidoacylation of alcohols |
| US5310779A (en) * | 1991-11-05 | 1994-05-10 | Bausch & Lomb Incorporated | UV curable crosslinking agents useful in copolymerization |
| US5292514A (en) * | 1992-06-24 | 1994-03-08 | Minnesota Mining And Manufacturing Company | Azlactone-functional substrates, corneal prostheses, and manufacture and use thereof |
| US5480950A (en) | 1992-09-28 | 1996-01-02 | Kabi Pharmacia Ophthalmics, Inc. | High refractive index hydrogels and uses thereof |
| US5316704B1 (en) | 1992-09-28 | 1996-05-21 | Kabi Pharmacia Ophthalmics Inc | Process for fabricating full sized expansible hydrogel intraocular lenses |
| US5468246A (en) | 1993-07-02 | 1995-11-21 | Iovision, Inc. | Intraocular lens injector |
| US5425734A (en) * | 1993-07-02 | 1995-06-20 | Iovision, Inc. | Intraocular lens injector |
| SE9403392D0 (sv) | 1994-10-06 | 1994-10-06 | Pharmacia Ab | Intraocular lens materials |
| AU4438696A (en) * | 1995-02-03 | 1996-08-21 | Novartis Ag | Crosslinked polymers |
| WO1996024075A1 (en) * | 1995-02-03 | 1996-08-08 | Novartis Ag | Crosslinked polymers containing ester or amide groups |
| JP2967093B2 (ja) | 1995-02-23 | 1999-10-25 | ホーヤ株式会社 | 軟性眼内レンズ |
| US5647409A (en) | 1995-04-04 | 1997-07-15 | Allergan | On-site syringe filling apparatus for viscoelastic materials, and corresponding method for on-site syringe filling |
| AR009439A1 (es) * | 1996-12-23 | 2000-04-12 | Novartis Ag | Un articulo que comprende un sustrato con un recubrimiento polimerico primario que porta grupos reactivos predominantemente en su superficie, unmetodo para preparar dicho articulo, un articulo que posee un recubrimiento de tipo hibrido y una lente de contacto |
| JPH1180274A (ja) * | 1997-09-12 | 1999-03-26 | Menicon Co Ltd | 光学材料 |
| SE9800853D0 (sv) | 1998-03-16 | 1998-03-16 | Pharmacia & Upjohn Bv | Intraocular lens |
| JP4291452B2 (ja) * | 1998-03-27 | 2009-07-08 | 大日本印刷株式会社 | 熱転写シート |
| SE9900935D0 (sv) | 1999-03-16 | 1999-03-16 | Pharmacia & Upjohn Bv | Macromolecular compounds |
| DE60104191T2 (de) | 2000-04-21 | 2005-07-14 | Advanced Medical Optics, Inc., Santa Ana | Methode zur herstellung einer akkomodierfähigen intraokularlinse |
| JP4686839B2 (ja) | 2000-10-23 | 2011-05-25 | 東レ株式会社 | モノマー、ポリマーおよびそれを用いた眼用レンズ |
-
1999
- 1999-08-02 AU AUPQ1977A patent/AUPQ197799A0/en not_active Abandoned
-
2000
- 2000-08-02 US US10/048,312 patent/US6774197B1/en not_active Expired - Fee Related
- 2000-08-02 EP EP00947679A patent/EP1210034A4/en not_active Withdrawn
- 2000-08-02 CA CA2379249A patent/CA2379249C/en not_active Expired - Fee Related
- 2000-08-02 JP JP2001513341A patent/JP4975920B2/ja not_active Expired - Fee Related
- 2000-08-02 HK HK02107590.7A patent/HK1047689A1/zh unknown
- 2000-08-02 WO PCT/AU2000/000916 patent/WO2001008604A1/en not_active Ceased
-
2004
- 2004-07-22 US US10/897,302 patent/US7138471B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP4975920B2 (ja) | 2012-07-11 |
| JP2003505585A (ja) | 2003-02-12 |
| AUPQ197799A0 (en) | 1999-08-26 |
| US20050004255A1 (en) | 2005-01-06 |
| CA2379249A1 (en) | 2001-02-08 |
| EP1210034A4 (en) | 2005-02-02 |
| EP1210034A1 (en) | 2002-06-05 |
| US6774197B1 (en) | 2004-08-10 |
| US7138471B2 (en) | 2006-11-21 |
| WO2001008604A1 (en) | 2001-02-08 |
| HK1047689A1 (zh) | 2003-03-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20140804 |