CA2314078C - Coating of polymers - Google Patents
Coating of polymers Download PDFInfo
- Publication number
- CA2314078C CA2314078C CA002314078A CA2314078A CA2314078C CA 2314078 C CA2314078 C CA 2314078C CA 002314078 A CA002314078 A CA 002314078A CA 2314078 A CA2314078 A CA 2314078A CA 2314078 C CA2314078 C CA 2314078C
- Authority
- CA
- Canada
- Prior art keywords
- lens
- polyionic
- coating
- contacting
- polyionic material
- 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
Links
- 238000000576 coating method Methods 0.000 title claims abstract description 121
- 239000011248 coating agent Substances 0.000 title claims abstract description 112
- 229920000642 polymer Polymers 0.000 title claims description 32
- 239000000463 material Substances 0.000 claims abstract description 209
- 229920000831 ionic polymer Polymers 0.000 claims abstract description 152
- 238000000034 method Methods 0.000 claims abstract description 86
- 238000005507 spraying Methods 0.000 claims abstract description 19
- 238000001035 drying Methods 0.000 claims abstract description 15
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 13
- 239000000243 solution Substances 0.000 claims description 57
- 239000011162 core material Substances 0.000 claims description 55
- -1 poly(allylamine hydrochloride) Polymers 0.000 claims description 47
- 229920002873 Polyethylenimine Polymers 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 19
- 229920000083 poly(allylamine) Polymers 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 18
- 229920002125 Sokalan® Polymers 0.000 claims description 16
- 229920000867 polyelectrolyte Polymers 0.000 claims description 15
- 239000012487 rinsing solution Substances 0.000 claims description 15
- 239000012778 molding material Substances 0.000 claims description 13
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 9
- 238000012546 transfer Methods 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- 229920000767 polyaniline Polymers 0.000 claims description 6
- 229920002845 Poly(methacrylic acid) Polymers 0.000 claims description 5
- 229920000128 polypyrrole Polymers 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 4
- PHOQVHQSTUBQQK-SQOUGZDYSA-N D-glucono-1,5-lactone Chemical compound OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O PHOQVHQSTUBQQK-SQOUGZDYSA-N 0.000 claims description 3
- 229920002518 Polyallylamine hydrochloride Polymers 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 125000002091 cationic group Chemical group 0.000 claims description 3
- 235000012209 glucono delta-lactone Nutrition 0.000 claims description 3
- 229960003681 gluconolactone Drugs 0.000 claims description 3
- 239000004584 polyacrylic acid Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 10
- 239000001301 oxygen Substances 0.000 abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 abstract description 10
- BALXUFOVQVENIU-KXNXZCPBSA-N pseudoephedrine hydrochloride Chemical group [H+].[Cl-].CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 BALXUFOVQVENIU-KXNXZCPBSA-N 0.000 abstract 1
- 210000000695 crystalline len Anatomy 0.000 description 145
- 238000004519 manufacturing process Methods 0.000 description 14
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 238000007654 immersion Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 125000003277 amino group Chemical group 0.000 description 9
- 238000004381 surface treatment Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 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 7
- 229920002674 hyaluronan Polymers 0.000 description 7
- 229960003160 hyaluronic acid Drugs 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- 239000012634 fragment Substances 0.000 description 6
- 230000005660 hydrophilic surface Effects 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000013256 coordination polymer Substances 0.000 description 5
- 238000003618 dip coating Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 230000001965 increasing effect Effects 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 125000005529 alkyleneoxy group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- 230000035699 permeability Effects 0.000 description 4
- 238000009832 plasma treatment Methods 0.000 description 4
- 229920000447 polyanionic polymer Polymers 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 229910003849 O-Si Inorganic materials 0.000 description 3
- 229910003872 O—Si Inorganic materials 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000012937 correction Methods 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000013590 bulk material Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000010261 cell growth Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 210000004087 cornea Anatomy 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 2
- 229940023490 ophthalmic product Drugs 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 description 1
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003732 agents acting on the eye Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 210000002159 anterior chamber Anatomy 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000032798 delamination Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000007688 edging Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000572 ellipsometry Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 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 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000011344 liquid material Substances 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
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000002669 organ and tissue protective effect Effects 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000010399 physical interaction Effects 0.000 description 1
- 229920002851 polycationic polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000009718 spray deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000013271 transdermal drug delivery Methods 0.000 description 1
- 150000003673 urethanes Chemical group 0.000 description 1
Classifications
-
- 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
- G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
-
- 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
-
- 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
- C08J7/04—Coating
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
- G02C7/04—Contact lenses for the eyes
- G02C7/049—Contact lenses having special fitting or structural features achieved by special materials or material structures
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Eyeglasses (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
- Materials For Medical Uses (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Apparatuses And Processes For Manufacturing Resistors (AREA)
- Electrotherapy Devices (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US531798A | 1998-01-09 | 1998-01-09 | |
| US09/005,317 | 1998-01-09 | ||
| US19960998A | 1998-11-25 | 1998-11-25 | |
| US09/199,609 | 1998-11-25 | ||
| PCT/EP1999/000058 WO1999035520A1 (en) | 1998-01-09 | 1999-01-07 | Coating of polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2314078A1 CA2314078A1 (en) | 1999-07-15 |
| CA2314078C true CA2314078C (en) | 2009-09-08 |
Family
ID=26674205
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002314078A Expired - Fee Related CA2314078C (en) | 1998-01-09 | 1999-01-07 | Coating of polymers |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1046068B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4634603B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR20010033969A (cg-RX-API-DMAC7.html) |
| CN (1) | CN1287620A (cg-RX-API-DMAC7.html) |
| AR (1) | AR014269A1 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE241151T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU745472B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR9906836A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2314078C (cg-RX-API-DMAC7.html) |
| DE (1) | DE69908084T2 (cg-RX-API-DMAC7.html) |
| DK (1) | DK1046068T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2200496T3 (cg-RX-API-DMAC7.html) |
| HU (1) | HUP0100553A2 (cg-RX-API-DMAC7.html) |
| IL (1) | IL136516A0 (cg-RX-API-DMAC7.html) |
| NO (1) | NO325172B1 (cg-RX-API-DMAC7.html) |
| PL (1) | PL341346A1 (cg-RX-API-DMAC7.html) |
| TW (1) | TW403841B (cg-RX-API-DMAC7.html) |
| WO (1) | WO1999035520A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (82)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6451871B1 (en) | 1998-11-25 | 2002-09-17 | Novartis Ag | Methods of modifying surface characteristics |
| US6793973B2 (en) | 2000-02-04 | 2004-09-21 | Novartis Ag | Single-dip process for achieving a layer-by-layer-like coating |
| WO2001078906A1 (en) * | 2000-04-14 | 2001-10-25 | Virginia Tech Intellectual Properties, Inc. | Self-assembled thin film coating to enhance the biocompatibility of materials |
| US6689480B2 (en) | 2000-05-10 | 2004-02-10 | Toray Industries, Inc. | Surface-treated plastic article and method of surface treatment |
| JP4834916B2 (ja) * | 2000-05-10 | 2011-12-14 | 東レ株式会社 | 表面処理プラスチック成形品 |
| AR030282A1 (es) * | 2000-05-30 | 2003-08-20 | Novartis Ag | Material compuesto, proceso para su fabricacion, dispositivo biomedico, y uso del material compuesto para la fabricacion de un dispositivo oftalmico |
| US6589665B2 (en) | 2000-05-30 | 2003-07-08 | Novartis Ag | Coated articles |
| WO2002016974A2 (en) * | 2000-08-24 | 2002-02-28 | Novartis Ag | Process for surface modifying substrates and modified substrates resulting therefrom |
| US6774178B2 (en) | 2001-01-05 | 2004-08-10 | Novartis Ag | Tinted, high Dk ophthalmic molding and a method for making same |
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-
1999
- 1999-01-07 ES ES99902524T patent/ES2200496T3/es not_active Expired - Lifetime
- 1999-01-07 DK DK99902524T patent/DK1046068T3/da active
- 1999-01-07 JP JP2000527849A patent/JP4634603B2/ja not_active Expired - Lifetime
- 1999-01-07 BR BR9906836-2A patent/BR9906836A/pt not_active IP Right Cessation
- 1999-01-07 WO PCT/EP1999/000058 patent/WO1999035520A1/en not_active Ceased
- 1999-01-07 KR KR1020007007554A patent/KR20010033969A/ko not_active Withdrawn
- 1999-01-07 AR ARP990100047A patent/AR014269A1/es unknown
- 1999-01-07 DE DE69908084T patent/DE69908084T2/de not_active Expired - Lifetime
- 1999-01-07 PL PL99341346A patent/PL341346A1/xx not_active Application Discontinuation
- 1999-01-07 TW TW088100168A patent/TW403841B/zh not_active IP Right Cessation
- 1999-01-07 CN CN99802027A patent/CN1287620A/zh active Pending
- 1999-01-07 AU AU22784/99A patent/AU745472B2/en not_active Ceased
- 1999-01-07 EP EP99902524A patent/EP1046068B1/en not_active Expired - Lifetime
- 1999-01-07 AT AT99902524T patent/ATE241151T1/de not_active IP Right Cessation
- 1999-01-07 IL IL13651699A patent/IL136516A0/xx unknown
- 1999-01-07 CA CA002314078A patent/CA2314078C/en not_active Expired - Fee Related
- 1999-01-07 HU HU0100553A patent/HUP0100553A2/hu unknown
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| Publication number | Publication date |
|---|---|
| BR9906836A (pt) | 2000-10-17 |
| KR20010033969A (ko) | 2001-04-25 |
| EP1046068A1 (en) | 2000-10-25 |
| ATE241151T1 (de) | 2003-06-15 |
| NO20003486D0 (no) | 2000-07-06 |
| DE69908084D1 (de) | 2003-06-26 |
| AR014269A1 (es) | 2001-02-07 |
| EP1046068B1 (en) | 2003-05-21 |
| JP4634603B2 (ja) | 2011-02-16 |
| CN1287620A (zh) | 2001-03-14 |
| TW403841B (en) | 2000-09-01 |
| DK1046068T3 (da) | 2003-09-01 |
| ES2200496T3 (es) | 2004-03-01 |
| PL341346A1 (en) | 2001-04-09 |
| NO325172B1 (no) | 2008-02-11 |
| IL136516A0 (en) | 2001-06-14 |
| NO20003486L (no) | 2000-09-05 |
| AU745472B2 (en) | 2002-03-21 |
| CA2314078A1 (en) | 1999-07-15 |
| DE69908084T2 (de) | 2003-11-27 |
| JP2002501211A (ja) | 2002-01-15 |
| AU2278499A (en) | 1999-07-26 |
| HUP0100553A2 (hu) | 2001-06-28 |
| WO1999035520A1 (en) | 1999-07-15 |
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