CA2408938A1 - Coated articles - Google Patents
Coated articles Download PDFInfo
- Publication number
- CA2408938A1 CA2408938A1 CA002408938A CA2408938A CA2408938A1 CA 2408938 A1 CA2408938 A1 CA 2408938A1 CA 002408938 A CA002408938 A CA 002408938A CA 2408938 A CA2408938 A CA 2408938A CA 2408938 A1 CA2408938 A1 CA 2408938A1
- Authority
- CA
- Canada
- Prior art keywords
- radical
- alkyl
- substituted
- alkylene
- solution
- 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
- 239000013590 bulk material Substances 0.000 claims abstract description 53
- 238000000576 coating method Methods 0.000 claims abstract description 42
- 229920000831 ionic polymer Polymers 0.000 claims abstract description 40
- 239000011248 coating agent Substances 0.000 claims abstract description 37
- 239000000463 material Substances 0.000 claims abstract description 37
- 239000000178 monomer Substances 0.000 claims abstract description 28
- 239000002131 composite material Substances 0.000 claims abstract description 26
- 239000003999 initiator Substances 0.000 claims abstract description 12
- 230000005660 hydrophilic surface Effects 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 9
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 7
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 5
- -1 polysiloxane Polymers 0.000 claims description 113
- 239000001257 hydrogen Substances 0.000 claims description 82
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 69
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 24
- 229920000083 poly(allylamine) Polymers 0.000 claims description 22
- 229920001577 copolymer Polymers 0.000 claims description 21
- 229920002125 Sokalan® Polymers 0.000 claims description 17
- 229920006318 anionic polymer Polymers 0.000 claims description 17
- 229920006317 cationic polymer Polymers 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 16
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 150000001720 carbohydrates Chemical class 0.000 claims description 11
- 239000004584 polyacrylic acid Substances 0.000 claims description 11
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims description 10
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims description 9
- 229920002873 Polyethylenimine Polymers 0.000 claims description 9
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 229920001296 polysiloxane Polymers 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 229920000570 polyether Polymers 0.000 claims description 7
- 229920002845 Poly(methacrylic acid) Polymers 0.000 claims description 6
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 4
- 229920000388 Polyphosphate Polymers 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 210000004087 cornea Anatomy 0.000 claims description 4
- 125000003010 ionic group Chemical group 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- 239000001205 polyphosphate Substances 0.000 claims description 4
- 235000011176 polyphosphates Nutrition 0.000 claims description 4
- 230000009471 action Effects 0.000 claims description 3
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 2
- 239000001530 fumaric acid Substances 0.000 claims description 2
- 229920000620 organic polymer Polymers 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 4
- 230000035699 permeability Effects 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 description 154
- 239000000243 solution Substances 0.000 description 93
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 40
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 28
- 125000001424 substituent group Chemical group 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 125000000129 anionic group Chemical group 0.000 description 22
- 150000003839 salts Chemical class 0.000 description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 18
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 229910052786 argon Inorganic materials 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 13
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000002091 cationic group Chemical group 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 230000002209 hydrophobic effect Effects 0.000 description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 description 11
- 229920001222 biopolymer Polymers 0.000 description 10
- 229910021642 ultra pure water Inorganic materials 0.000 description 10
- 239000012498 ultrapure water Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 9
- 125000004956 cyclohexylene group Chemical group 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 239000003607 modifier Substances 0.000 description 9
- 229920000867 polyelectrolyte Polymers 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 238000004630 atomic force microscopy Methods 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 8
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 8
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 229920001542 oligosaccharide Polymers 0.000 description 7
- 150000002482 oligosaccharides Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 6
- 239000003505 polymerization initiator Substances 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 5
- 239000004809 Teflon Substances 0.000 description 5
- 229920006362 Teflon® Polymers 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 235000014633 carbohydrates Nutrition 0.000 description 5
- 238000007598 dipping method Methods 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 5
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 235000000346 sugar Nutrition 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229920001661 Chitosan Polymers 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
- 229920002674 hyaluronan Polymers 0.000 description 4
- 229960003160 hyaluronic acid Drugs 0.000 description 4
- 229960004592 isopropanol Drugs 0.000 description 4
- 210000004379 membrane Anatomy 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000009832 plasma treatment Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000004448 titration Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 229920000858 Cyclodextrin Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 108010038807 Oligopeptides Proteins 0.000 description 3
- 102000015636 Oligopeptides Human genes 0.000 description 3
- 241001085205 Prenanthella exigua Species 0.000 description 3
- 239000003929 acidic solution Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 230000027455 binding Effects 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 3
- 239000000919 ceramic Substances 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000011491 glass wool Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- 229920000962 poly(amidoamine) Polymers 0.000 description 3
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- 239000010453 quartz Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000001223 reverse osmosis Methods 0.000 description 3
- 239000012487 rinsing solution Substances 0.000 description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 3
- 230000002792 vascular Effects 0.000 description 3
- 125000002348 vinylic group Chemical group 0.000 description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 2
- UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 description 2
- DBTMGCOVALSLOR-UHFFFAOYSA-N 32-alpha-galactosyl-3-alpha-galactosyl-galactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(C(CO)OC(O)C2O)O)OC(CO)C1O DBTMGCOVALSLOR-UHFFFAOYSA-N 0.000 description 2
- YSYRISKCBOPJRG-UHFFFAOYSA-N 4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC1=C(F)OC(C(F)(F)F)(C(F)(F)F)O1 YSYRISKCBOPJRG-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 241001264766 Callistemon Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920002101 Chitin Polymers 0.000 description 2
- RXVWSYJTUUKTEA-UHFFFAOYSA-N D-maltotriose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 RXVWSYJTUUKTEA-UHFFFAOYSA-N 0.000 description 2
- 229920002307 Dextran Polymers 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 229920002683 Glycosaminoglycan Polymers 0.000 description 2
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- 229910003849 O-Si Inorganic materials 0.000 description 2
- 229910003872 O—Si Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- OCIBBXPLUVYKCH-QXVNYKTNSA-N alpha-maltohexaose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)O[C@H](O[C@@H]2[C@H](O[C@H](O[C@@H]3[C@H](O[C@H](O[C@@H]4[C@H](O[C@H](O[C@@H]5[C@H](O[C@H](O)[C@H](O)[C@H]5O)CO)[C@H](O)[C@H]4O)CO)[C@H](O)[C@H]3O)CO)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O OCIBBXPLUVYKCH-QXVNYKTNSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 150000002016 disaccharides Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 210000000744 eyelid Anatomy 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229960002897 heparin Drugs 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000017 hydrogel Substances 0.000 description 2
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
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- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 1
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- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
- C08J7/16—Chemical modification with polymerisable compounds
-
- 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
- A61L27/28—Materials for coating prostheses
- A61L27/34—Macromolecular materials
-
- 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
- G02B1/041—Lenses
- G02B1/043—Contact lenses
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/21—Circular sheet or circular blank
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
- Y10T428/31928—Ester, halide or nitrile of addition polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31935—Ester, halide or nitrile of addition polymer
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Public Health (AREA)
- General Physics & Mathematics (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Transplantation (AREA)
- Optics & Photonics (AREA)
- Materials For Medical Uses (AREA)
- Paints Or Removers (AREA)
- Laminated Bodies (AREA)
- Eyeglasses (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- General Preparation And Processing Of Foods (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00111526.0 | 2000-05-30 | ||
| EP00111526 | 2000-05-30 | ||
| US22802200P | 2000-08-24 | 2000-08-24 | |
| US60/228,022 | 2000-08-24 | ||
| PCT/EP2001/006082 WO2001092924A1 (en) | 2000-05-30 | 2001-05-28 | Coated articles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2408938A1 true CA2408938A1 (en) | 2001-12-06 |
Family
ID=32523988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002408938A Abandoned CA2408938A1 (en) | 2000-05-30 | 2001-05-28 | Coated articles |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1299753B1 (enExample) |
| JP (1) | JP4776863B2 (enExample) |
| CN (1) | CN1432136A (enExample) |
| AR (1) | AR030282A1 (enExample) |
| AT (1) | ATE266873T1 (enExample) |
| AU (1) | AU2001267488A1 (enExample) |
| BR (1) | BR0111395A (enExample) |
| CA (1) | CA2408938A1 (enExample) |
| DE (1) | DE60103278T2 (enExample) |
| MX (1) | MXPA02011857A (enExample) |
| WO (1) | WO2001092924A1 (enExample) |
| ZA (1) | ZA200209630B (enExample) |
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| US6451871B1 (en) | 1998-11-25 | 2002-09-17 | Novartis Ag | Methods of modifying surface characteristics |
| US6428839B1 (en) * | 2000-06-02 | 2002-08-06 | Bausch & Lomb Incorporated | Surface treatment of medical device |
| CA2415871A1 (en) * | 2000-08-24 | 2002-02-28 | Novartis Ag | Process for surface modifying substrates and modified substrates resulting therefrom |
| TW200407367A (en) * | 2001-11-13 | 2004-05-16 | Novartis Ag | Method for modifying the surface of biomedical articles |
| US7402318B2 (en) | 2001-11-14 | 2008-07-22 | Novartis Ag | Medical devices having antimicrobial coatings thereon |
| TWI255224B (en) * | 2002-01-09 | 2006-05-21 | Novartis Ag | Polymeric articles having a lubricious coating and method for making the same |
| JP2003277691A (ja) * | 2002-03-26 | 2003-10-02 | Nippon Paint Co Ltd | 水中摩擦低減塗膜及び水中摩擦低減方法 |
| US7101947B2 (en) | 2002-06-14 | 2006-09-05 | Florida State University Research Foundation, Inc. | Polyelectrolyte complex films for analytical and membrane separation of chiral compounds |
| US6926965B2 (en) | 2002-09-11 | 2005-08-09 | Novartis Ag | LbL-coated medical device and method for making the same |
| US6896926B2 (en) | 2002-09-11 | 2005-05-24 | Novartis Ag | Method for applying an LbL coating onto a medical device |
| US8172395B2 (en) * | 2002-12-03 | 2012-05-08 | Novartis Ag | Medical devices having antimicrobial coatings thereon |
| US8309117B2 (en) | 2002-12-19 | 2012-11-13 | Novartis, Ag | Method for making medical devices having antimicrobial coatings thereon |
| AU2003297323A1 (en) * | 2002-12-23 | 2004-07-22 | Bausch And Lomb Incorporated | Surface treatment utilizing microwave radiation |
| US20060251795A1 (en) | 2005-05-05 | 2006-11-09 | Boris Kobrin | Controlled vapor deposition of biocompatible coatings for medical devices |
| US20070197681A1 (en) * | 2006-02-22 | 2007-08-23 | Advanced Medical Optics | Lens surface enhancement |
| US8044112B2 (en) | 2006-03-30 | 2011-10-25 | Novartis Ag | Method for applying a coating onto a silicone hydrogel lens |
| JP5567337B2 (ja) | 2006-08-18 | 2014-08-06 | コモンウェルス サイエンティフィック アンドインダストリアル リサーチ オーガナイゼーション | ポリマー被膜及びそれらを形成させる方法 |
| US8795782B2 (en) | 2006-08-18 | 2014-08-05 | Commonwealth Scientific And Industrial Research Organisation | Polymeric coatings and methods for forming them |
| CA2667781C (en) | 2006-10-30 | 2015-12-01 | Novartis Ag | Method for applying a coating onto a silicone hydrogel lens |
| JP5473605B2 (ja) | 2006-12-21 | 2014-04-16 | ノバルティス アーゲー | 生物医学的物品のコーティング方法 |
| HUE047093T2 (hu) | 2008-03-18 | 2020-04-28 | Novartis Ag | Bevonatoló eljárás szemészeti lencsékhez |
| SG183390A1 (en) | 2010-02-16 | 2012-09-27 | Toray Industries | Soft ocular lens having low moisture content and method for producing same |
| KR102159909B1 (ko) * | 2010-07-30 | 2020-09-25 | 알콘 인코포레이티드 | 수분이 풍부한 표면을 갖는 실리콘 히드로겔 렌즈 |
| WO2012170603A1 (en) * | 2011-06-09 | 2012-12-13 | Novartis Ag | Silicone hydrogel lenses with nano-textured surfaces |
| CN103917899B (zh) | 2011-10-12 | 2018-04-03 | 诺华股份有限公司 | 通过涂布制备uv吸收性眼用透镜的方法 |
| WO2013090808A1 (en) * | 2011-12-14 | 2013-06-20 | Semprus Biosciences Corp. | High ionic strength process for contact lens modification |
| JP2013235034A (ja) * | 2012-05-02 | 2013-11-21 | Menicon Co Ltd | 表面処理樹脂成形体の製造方法及び表面処理樹脂成形体 |
| US9395468B2 (en) | 2012-08-27 | 2016-07-19 | Ocular Dynamics, Llc | Contact lens with a hydrophilic layer |
| US10338408B2 (en) | 2012-12-17 | 2019-07-02 | Novartis Ag | Method for making improved UV-absorbing ophthalmic lenses |
| EP3570093B1 (en) | 2013-11-15 | 2021-09-15 | Tangible Science, Inc. | Contact lens with a hydrophilic layer |
| CN107206119B (zh) | 2014-12-09 | 2021-01-29 | 实体科学公司 | 具有生物相容性层的医疗设备涂层 |
| CN109475658A (zh) * | 2016-07-28 | 2019-03-15 | 东丽株式会社 | 医疗器械、医疗器械的制造方法 |
| EP3542193A1 (en) | 2016-11-18 | 2019-09-25 | Novartis AG | Method for making ophthalmic lenses |
| WO2019151265A1 (ja) * | 2018-02-01 | 2019-08-08 | Ａｇｃ株式会社 | 基材および共重合体 |
| CN115003345B (zh) * | 2019-11-30 | 2026-01-27 | 智能反应堆服务有限公司 | 用于医疗器械的涂层 |
| GB202008098D0 (en) | 2020-05-29 | 2020-07-15 | Uea Enterprises Ltd | A method of coating an ocular prosthetic device and other prosthetics |
| EP4285949A4 (en) * | 2021-03-02 | 2024-11-27 | Toray Industries, Inc. | COATED MEDICAL DEVICE AND METHOD OF MANUFACTURING SAME |
| JP7800028B2 (ja) * | 2021-09-01 | 2026-01-16 | 東レ株式会社 | 共重合体の製造方法並びにその共重合体を含む材料 |
| CN116397136A (zh) * | 2022-12-05 | 2023-07-07 | 南京同曦大圣环保科技有限公司 | 一种自愈合铝合金及其制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5700559A (en) * | 1994-12-16 | 1997-12-23 | Advanced Surface Technology | Durable hydrophilic surface coatings |
| TW434456B (en) * | 1994-12-30 | 2001-05-16 | Novartis Ag | A compound as functionalized photoinitiator, its production process, its corresponding oligomers or polymers and its application in coating a substrate |
| TW353086B (en) * | 1994-12-30 | 1999-02-21 | Novartis Ag | Method for multistep coating of a surface |
| JP4634603B2 (ja) * | 1998-01-09 | 2011-02-16 | ノバルティス アーゲー | ポリマーのコーティング |
| TW473488B (en) * | 1998-04-30 | 2002-01-21 | Novartis Ag | Composite materials, biomedical articles formed thereof and process for their manufacture |
| EP1095711B1 (en) * | 1999-10-27 | 2004-01-28 | Novartis AG | Process for coating a material surface |
| EP1095966B1 (en) * | 1999-10-27 | 2006-01-11 | Novartis AG | Process for the modification of a material surface |
-
2001
- 2001-05-28 MX MXPA02011857A patent/MXPA02011857A/es not_active Application Discontinuation
- 2001-05-28 CA CA002408938A patent/CA2408938A1/en not_active Abandoned
- 2001-05-28 AT AT01945203T patent/ATE266873T1/de not_active IP Right Cessation
- 2001-05-28 AU AU2001267488A patent/AU2001267488A1/en not_active Abandoned
- 2001-05-28 BR BR0111395-0A patent/BR0111395A/pt not_active Application Discontinuation
- 2001-05-28 DE DE60103278T patent/DE60103278T2/de not_active Expired - Lifetime
- 2001-05-28 JP JP2002501079A patent/JP4776863B2/ja not_active Expired - Lifetime
- 2001-05-28 CN CN01810445A patent/CN1432136A/zh active Pending
- 2001-05-28 WO PCT/EP2001/006082 patent/WO2001092924A1/en not_active Ceased
- 2001-05-28 AR ARP010102539 patent/AR030282A1/es unknown
- 2001-05-28 EP EP01945203A patent/EP1299753B1/en not_active Expired - Lifetime
-
2002
- 2002-11-27 ZA ZA200209630A patent/ZA200209630B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP4776863B2 (ja) | 2011-09-21 |
| WO2001092924A1 (en) | 2001-12-06 |
| CN1432136A (zh) | 2003-07-23 |
| AR030282A1 (es) | 2003-08-20 |
| EP1299753A1 (en) | 2003-04-09 |
| JP2003534860A (ja) | 2003-11-25 |
| ATE266873T1 (de) | 2004-05-15 |
| DE60103278T2 (de) | 2004-09-23 |
| BR0111395A (pt) | 2003-06-03 |
| ZA200209630B (en) | 2003-10-20 |
| EP1299753B1 (en) | 2004-05-12 |
| MXPA02011857A (es) | 2003-04-10 |
| AU2001267488A1 (en) | 2001-12-11 |
| DE60103278D1 (de) | 2004-06-17 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |