CA2446722A1 - Oxime ester photoinitiators having a combined structure - Google Patents
Oxime ester photoinitiators having a combined structure Download PDFInfo
- Publication number
- CA2446722A1 CA2446722A1 CA002446722A CA2446722A CA2446722A1 CA 2446722 A1 CA2446722 A1 CA 2446722A1 CA 002446722 A CA002446722 A CA 002446722A CA 2446722 A CA2446722 A CA 2446722A CA 2446722 A1 CA2446722 A1 CA 2446722A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- substituted
- nr5r6
- halogen
- group
- 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
- -1 Oxime ester Chemical class 0.000 title claims description 178
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 261
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 69
- 239000001257 hydrogen Substances 0.000 claims abstract description 68
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 50
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 21
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims description 159
- 229910052736 halogen Inorganic materials 0.000 claims description 145
- 150000002367 halogens Chemical class 0.000 claims description 144
- 125000001624 naphthyl group Chemical group 0.000 claims description 83
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 75
- 239000000758 substrate Substances 0.000 claims description 75
- 239000000049 pigment Substances 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 60
- 238000000576 coating method Methods 0.000 claims description 53
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 50
- 125000001424 substituent group Chemical group 0.000 claims description 49
- 239000000463 material Substances 0.000 claims description 47
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 43
- 229920005989 resin Polymers 0.000 claims description 43
- 239000011347 resin Substances 0.000 claims description 43
- 238000004519 manufacturing process Methods 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 39
- 229920001577 copolymer Polymers 0.000 claims description 35
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 30
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 26
- 239000000178 monomer Substances 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 23
- 230000003287 optical effect Effects 0.000 claims description 22
- 239000011230 binding agent Substances 0.000 claims description 21
- 229920002120 photoresistant polymer Polymers 0.000 claims description 19
- 239000000843 powder Substances 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 19
- 238000007639 printing Methods 0.000 claims description 17
- 125000004957 naphthylene group Chemical group 0.000 claims description 16
- 101100533888 Hypocrea jecorina (strain QM6a) sor4 gene Proteins 0.000 claims description 14
- 101100533877 Hypocrea jecorina (strain QM6a) sor8 gene Proteins 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 13
- 239000000654 additive Substances 0.000 claims description 12
- 239000003999 initiator Substances 0.000 claims description 11
- 239000000976 ink Substances 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 239000012965 benzophenone Substances 0.000 claims description 9
- 229910000679 solder Inorganic materials 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- 239000003365 glass fiber Substances 0.000 claims description 7
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 7
- 238000007650 screen-printing Methods 0.000 claims description 7
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 6
- 238000003384 imaging method Methods 0.000 claims description 6
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 5
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 5
- 239000002131 composite material Substances 0.000 claims description 5
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 5
- 238000010894 electron beam technology Methods 0.000 claims description 5
- 238000009713 electroplating Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000003973 paint Substances 0.000 claims description 5
- 238000007747 plating Methods 0.000 claims description 5
- 239000002491 polymer binding agent Substances 0.000 claims description 5
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims description 4
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 239000003094 microcapsule Substances 0.000 claims description 4
- 229920000620 organic polymer Polymers 0.000 claims description 4
- 239000003504 photosensitizing agent Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 4
- 230000000996 additive effect Effects 0.000 claims description 3
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- VWBYXJRDIQCSLW-UHFFFAOYSA-N O=[P](c1ccccc1)c1ccccc1 Chemical group O=[P](c1ccccc1)c1ccccc1 VWBYXJRDIQCSLW-UHFFFAOYSA-N 0.000 claims description 2
- 229960000956 coumarin Drugs 0.000 claims description 2
- 230000005670 electromagnetic radiation Effects 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 10
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 6
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 235000019571 color Nutrition 0.000 claims 1
- 238000001393 microlithography Methods 0.000 claims 1
- 229940048053 acrylate Drugs 0.000 description 77
- 239000010410 layer Substances 0.000 description 77
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 49
- 239000010408 film Substances 0.000 description 43
- 239000011248 coating agent Substances 0.000 description 34
- 239000002904 solvent Substances 0.000 description 31
- 239000000306 component Substances 0.000 description 30
- 150000003254 radicals Chemical class 0.000 description 30
- 239000004973 liquid crystal related substance Substances 0.000 description 29
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 25
- 125000006850 spacer group Chemical group 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 239000002253 acid Substances 0.000 description 22
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- 238000009740 moulding (composite fabrication) Methods 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 229940117913 acrylamide Drugs 0.000 description 19
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 16
- 239000011521 glass Substances 0.000 description 16
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 15
- 239000011159 matrix material Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 14
- 229940044603 styrene Drugs 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- 238000011161 development Methods 0.000 description 11
- 230000018109 developmental process Effects 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
- 230000000875 corresponding effect Effects 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
- 229920005862 polyol Polymers 0.000 description 10
- 230000035945 sensitivity Effects 0.000 description 10
- 229920003002 synthetic resin Polymers 0.000 description 10
- 239000000057 synthetic resin Substances 0.000 description 10
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- 150000001412 amines Chemical class 0.000 description 9
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 239000004642 Polyimide Substances 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 8
- 238000003491 array Methods 0.000 description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 8
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 8
- 239000011229 interlayer Substances 0.000 description 8
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- 238000009472 formulation Methods 0.000 description 7
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- 230000005855 radiation Effects 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
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- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 4
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- 239000007789 gas Substances 0.000 description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
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- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
- C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
- C07C251/66—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with the esterifying carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Polymerisation Methods In General (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pyrane Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Holo Graphy (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01810559.3 | 2001-06-11 | ||
| EP01810559 | 2001-06-11 | ||
| PCT/EP2002/006107 WO2002100903A1 (en) | 2001-06-11 | 2002-06-04 | Oxime ester photoinitiators having a combined structure |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2446722A1 true CA2446722A1 (en) | 2002-12-19 |
Family
ID=8183958
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002446722A Abandoned CA2446722A1 (en) | 2001-06-11 | 2002-06-04 | Oxime ester photoinitiators having a combined structure |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7189489B2 (enExample) |
| EP (1) | EP1395615B1 (enExample) |
| JP (2) | JP3860170B2 (enExample) |
| KR (1) | KR100801457B1 (enExample) |
| CN (1) | CN100528838C (enExample) |
| AT (1) | ATE446322T1 (enExample) |
| CA (1) | CA2446722A1 (enExample) |
| DE (1) | DE60234095D1 (enExample) |
| TW (1) | TW593357B (enExample) |
| WO (1) | WO2002100903A1 (enExample) |
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-
2002
- 2002-06-04 CA CA002446722A patent/CA2446722A1/en not_active Abandoned
- 2002-06-04 EP EP02778878A patent/EP1395615B1/en not_active Expired - Lifetime
- 2002-06-04 KR KR1020037016235A patent/KR100801457B1/ko not_active Expired - Lifetime
- 2002-06-04 US US10/480,146 patent/US7189489B2/en not_active Expired - Lifetime
- 2002-06-04 DE DE60234095T patent/DE60234095D1/de not_active Expired - Lifetime
- 2002-06-04 WO PCT/EP2002/006107 patent/WO2002100903A1/en not_active Ceased
- 2002-06-04 CN CNB028116755A patent/CN100528838C/zh not_active Expired - Lifetime
- 2002-06-04 AT AT02778878T patent/ATE446322T1/de not_active IP Right Cessation
- 2002-06-04 JP JP2003503669A patent/JP3860170B2/ja not_active Expired - Lifetime
- 2002-06-10 TW TW091112531A patent/TW593357B/zh not_active IP Right Cessation
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2006
- 2006-06-14 JP JP2006164492A patent/JP2006342166A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE60234095D1 (de) | 2009-12-03 |
| JP2004534797A (ja) | 2004-11-18 |
| EP1395615B1 (en) | 2009-10-21 |
| WO2002100903A1 (en) | 2002-12-19 |
| US20040170924A1 (en) | 2004-09-02 |
| CN1514845A (zh) | 2004-07-21 |
| EP1395615A1 (en) | 2004-03-10 |
| US7189489B2 (en) | 2007-03-13 |
| CN100528838C (zh) | 2009-08-19 |
| ATE446322T1 (de) | 2009-11-15 |
| KR100801457B1 (ko) | 2008-02-11 |
| TW593357B (en) | 2004-06-21 |
| JP3860170B2 (ja) | 2006-12-20 |
| JP2006342166A (ja) | 2006-12-21 |
| KR20040007700A (ko) | 2004-01-24 |
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