DE69921813T2 - Organische Gegenstände mit hydrophiler Beschichtung - Google Patents
Organische Gegenstände mit hydrophiler Beschichtung Download PDFInfo
- Publication number
- DE69921813T2 DE69921813T2 DE69921813T DE69921813T DE69921813T2 DE 69921813 T2 DE69921813 T2 DE 69921813T2 DE 69921813 T DE69921813 T DE 69921813T DE 69921813 T DE69921813 T DE 69921813T DE 69921813 T2 DE69921813 T2 DE 69921813T2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- radical
- substituted
- formula
- hydrogen
- 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 - Lifetime
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- 238000000576 coating method Methods 0.000 title claims description 38
- 239000011248 coating agent Substances 0.000 title claims description 32
- 150000003254 radicals Chemical class 0.000 claims description 147
- 229910052739 hydrogen Inorganic materials 0.000 claims description 122
- -1 benzylene Chemical group 0.000 claims description 121
- 239000001257 hydrogen Substances 0.000 claims description 109
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 73
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000002131 composite material Substances 0.000 claims description 37
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
- 239000000178 monomer Substances 0.000 claims description 30
- 125000002947 alkylene group Chemical group 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 239000013590 bulk material Substances 0.000 claims description 25
- 230000009021 linear effect Effects 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 238000006116 polymerization reaction Methods 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 16
- 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 12
- 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 12
- 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 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 12
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 230000002209 hydrophobic effect Effects 0.000 claims description 9
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical group 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 claims description 9
- 150000001450 anions Chemical class 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 150000001720 carbohydrates Chemical class 0.000 claims description 8
- 229920001577 copolymer Chemical class 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000003505 polymerization initiator Substances 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 6
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 claims description 6
- 230000005660 hydrophilic surface Effects 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 230000005855 radiation Effects 0.000 claims description 6
- 238000010526 radical polymerization reaction Methods 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 241001264766 Callistemon Species 0.000 claims description 5
- 102000015636 Oligopeptides Human genes 0.000 claims description 5
- 108010038807 Oligopeptides Proteins 0.000 claims description 5
- 210000004087 cornea Anatomy 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 229920005613 synthetic organic polymer Polymers 0.000 claims description 4
- UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical group C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 claims description 3
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 claims description 3
- 229910003849 O-Si Inorganic materials 0.000 claims description 3
- 229910003872 O—Si Inorganic materials 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 229940099563 lactobionic acid Drugs 0.000 claims description 3
- 229920005615 natural polymer Polymers 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 3
- 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 group 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 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims description 2
- 230000009471 action Effects 0.000 claims description 2
- SQVRNKJHWKZAKO-UHFFFAOYSA-N beta-N-Acetyl-D-neuraminic acid Chemical group CC(=O)NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO SQVRNKJHWKZAKO-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 claims description 2
- 229920002674 hyaluronan Chemical group 0.000 claims description 2
- 229960003160 hyaluronic acid Drugs 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 229960002591 hydroxyproline Drugs 0.000 claims description 2
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims description 2
- 229920000620 organic polymer Polymers 0.000 claims description 2
- SQVRNKJHWKZAKO-OQPLDHBCSA-N sialic acid Chemical group CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)OC1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-OQPLDHBCSA-N 0.000 claims description 2
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 241000219739 Lens Species 0.000 description 85
- 239000000243 solution Substances 0.000 description 85
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 31
- 229910052786 argon Inorganic materials 0.000 description 23
- 238000004448 titration Methods 0.000 description 19
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 18
- 239000000758 substrate Substances 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 125000000524 functional group Chemical group 0.000 description 14
- 125000003277 amino group Chemical group 0.000 description 13
- 229920000642 polymer Polymers 0.000 description 13
- XLPJNCYCZORXHG-UHFFFAOYSA-N 1-morpholin-4-ylprop-2-en-1-one Chemical compound C=CC(=O)N1CCOCC1 XLPJNCYCZORXHG-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 125000004956 cyclohexylene group Chemical group 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 8
- 238000002389 environmental scanning electron microscopy Methods 0.000 description 8
- 239000012948 isocyanate Substances 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 239000004809 Teflon Substances 0.000 description 7
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- 125000000129 anionic group Chemical group 0.000 description 7
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 238000002360 preparation method Methods 0.000 description 6
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- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- 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
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- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/04—Polymers provided for in subclasses C08C or C08F
-
- 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
-
- 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]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
-
- 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]
- Y10T428/31678—Of metal
- Y10T428/31692—Next to 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- General Chemical & Material Sciences (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Eyeglasses (AREA)
- Materials For Medical Uses (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Polymerisation Methods In General (AREA)
- Paints Or Removers (AREA)
- Prostheses (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98810385 | 1998-04-30 | ||
| EP98810385 | 1998-04-30 | ||
| PCT/EP1999/002880 WO1999057581A1 (en) | 1998-04-30 | 1999-04-28 | Organic articles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69921813D1 DE69921813D1 (de) | 2004-12-16 |
| DE69921813T2 true DE69921813T2 (de) | 2005-12-01 |
Family
ID=8236062
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69921813T Expired - Lifetime DE69921813T2 (de) | 1998-04-30 | 1999-04-28 | Organische Gegenstände mit hydrophiler Beschichtung |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US6447920B1 (enExample) |
| EP (1) | EP1084428B1 (enExample) |
| JP (1) | JP4699607B2 (enExample) |
| CN (1) | CN1298489A (enExample) |
| AR (1) | AR015040A1 (enExample) |
| AT (1) | ATE282214T1 (enExample) |
| AU (1) | AU3824899A (enExample) |
| BR (1) | BR9910056A (enExample) |
| CA (1) | CA2327743C (enExample) |
| DE (1) | DE69921813T2 (enExample) |
| NO (1) | NO20005446D0 (enExample) |
| TW (1) | TW473488B (enExample) |
| WO (1) | WO1999057581A1 (enExample) |
| ZA (1) | ZA200005329B (enExample) |
Families Citing this family (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW473488B (en) * | 1998-04-30 | 2002-01-21 | Novartis Ag | Composite materials, biomedical articles formed thereof and process for their manufacture |
| US6715874B1 (en) * | 1999-02-08 | 2004-04-06 | Novartis Ag | Organic polymers |
| CA2317179A1 (en) | 1999-09-01 | 2001-03-01 | Affymetrix, Inc. | Macromolecular arrays on polymeric brushes and methods for preparing the same |
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-
1999
- 1999-03-29 TW TW088104971A patent/TW473488B/zh active
- 1999-04-28 CA CA002327743A patent/CA2327743C/en not_active Expired - Lifetime
- 1999-04-28 BR BR9910056-8A patent/BR9910056A/pt not_active Application Discontinuation
- 1999-04-28 DE DE69921813T patent/DE69921813T2/de not_active Expired - Lifetime
- 1999-04-28 AT AT99920810T patent/ATE282214T1/de not_active IP Right Cessation
- 1999-04-28 EP EP99920810A patent/EP1084428B1/en not_active Expired - Lifetime
- 1999-04-28 AR ARP990101980A patent/AR015040A1/es unknown
- 1999-04-28 CN CN99805513.1A patent/CN1298489A/zh active Pending
- 1999-04-28 WO PCT/EP1999/002880 patent/WO1999057581A1/en not_active Ceased
- 1999-04-28 JP JP2000547494A patent/JP4699607B2/ja not_active Expired - Lifetime
- 1999-04-28 AU AU38248/99A patent/AU3824899A/en not_active Abandoned
-
2000
- 2000-10-02 ZA ZA200005329A patent/ZA200005329B/xx unknown
- 2000-10-27 US US09/697,860 patent/US6447920B1/en not_active Expired - Lifetime
- 2000-10-27 NO NO20005446A patent/NO20005446D0/no not_active Application Discontinuation
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2002
- 2002-06-20 US US10/175,656 patent/US6734321B2/en not_active Expired - Lifetime
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| Publication number | Publication date |
|---|---|
| WO1999057581A1 (en) | 1999-11-11 |
| JP4699607B2 (ja) | 2011-06-15 |
| CN1298489A (zh) | 2001-06-06 |
| US6734321B2 (en) | 2004-05-11 |
| US6447920B1 (en) | 2002-09-10 |
| AR015040A1 (es) | 2001-04-11 |
| CA2327743A1 (en) | 1999-11-11 |
| ATE282214T1 (de) | 2004-11-15 |
| EP1084428A1 (en) | 2001-03-21 |
| DE69921813D1 (de) | 2004-12-16 |
| AU3824899A (en) | 1999-11-23 |
| TW473488B (en) | 2002-01-21 |
| NO20005446L (no) | 2000-10-27 |
| ZA200005329B (en) | 2001-11-28 |
| CA2327743C (en) | 2008-06-10 |
| BR9910056A (pt) | 2001-01-09 |
| US20020197414A1 (en) | 2002-12-26 |
| EP1084428B1 (en) | 2004-11-10 |
| JP2002513668A (ja) | 2002-05-14 |
| NO20005446D0 (no) | 2000-10-27 |
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