DE602004009771T2 - Photoiniferter mit geöffneter azlacton-ringstruktur für die radikalische polymerisation - Google Patents
Photoiniferter mit geöffneter azlacton-ringstruktur für die radikalische polymerisation Download PDFInfo
- Publication number
- DE602004009771T2 DE602004009771T2 DE602004009771T DE602004009771T DE602004009771T2 DE 602004009771 T2 DE602004009771 T2 DE 602004009771T2 DE 602004009771 T DE602004009771 T DE 602004009771T DE 602004009771 T DE602004009771 T DE 602004009771T DE 602004009771 T2 DE602004009771 T2 DE 602004009771T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- photoiniferter
- arenyl
- aryl
- alkyl
- 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
Links
- 238000010526 radical polymerization reaction Methods 0.000 title abstract description 20
- 229920001577 copolymer Polymers 0.000 claims abstract description 38
- IEJPPSMHUUQABK-UHFFFAOYSA-N 2,4-diphenyl-4h-1,3-oxazol-5-one Chemical compound O=C1OC(C=2C=CC=CC=2)=NC1C1=CC=CC=C1 IEJPPSMHUUQABK-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000178 monomer Substances 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 238000006116 polymerization reaction Methods 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 23
- -1 thiuram compound Chemical class 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical group NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000002837 carbocyclic group Chemical group 0.000 claims description 9
- 125000005647 linker group Chemical group 0.000 claims description 6
- 125000002560 nitrile group Chemical group 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000962 organic group Chemical group 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001905 inorganic group Chemical group 0.000 claims description 4
- 239000012990 dithiocarbamate Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 229960002447 thiram Drugs 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 239000011133 lead Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 239000011135 tin Substances 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- 239000000047 product Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
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- 150000003254 radicals Chemical class 0.000 description 11
- 125000006413 ring segment Chemical group 0.000 description 11
- 238000005227 gel permeation chromatography Methods 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229920001400 block copolymer Polymers 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 230000000269 nucleophilic effect Effects 0.000 description 8
- 229920005862 polyol Polymers 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 229920000768 polyamine Polymers 0.000 description 7
- 150000003077 polyols Chemical class 0.000 description 7
- 150000003573 thiols Chemical group 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 230000005855 radiation Effects 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
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- 229920001971 elastomer Polymers 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000007306 functionalization reaction Methods 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000012876 carrier material Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229920000193 polymethacrylate Polymers 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical class CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000013033 iniferter Substances 0.000 description 3
- 230000002427 irreversible effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002736 metal compounds Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 238000005192 partition Methods 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 3
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- 150000003141 primary amines Chemical group 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- STELDKFCHUATHX-UHFFFAOYSA-N 2-(chloromethyl)-4,4-dimethyl-1,3-oxazol-5-one Chemical compound CC1(C)N=C(CCl)OC1=O STELDKFCHUATHX-UHFFFAOYSA-N 0.000 description 2
- PSFZNYTZFAOCFH-UHFFFAOYSA-N 2-[(2-chloroacetyl)amino]-2-methylpropanoic acid Chemical compound OC(=O)C(C)(C)NC(=O)CCl PSFZNYTZFAOCFH-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical group OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
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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
- 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
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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
- 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
- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S522/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S522/904—Monomer or polymer contains initiating group
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/393,551 US6908952B2 (en) | 2003-03-21 | 2003-03-21 | Ring-opened azlactone photoiniferters for radical polymerization |
| US393551 | 2003-03-21 | ||
| PCT/US2004/004506 WO2004094485A1 (en) | 2003-03-21 | 2004-02-13 | Ring-opened azlactone photoiniferters for radical polymerization |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE602004009771D1 DE602004009771D1 (de) | 2007-12-13 |
| DE602004009771T2 true DE602004009771T2 (de) | 2008-08-28 |
Family
ID=32988176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE602004009771T Expired - Lifetime DE602004009771T2 (de) | 2003-03-21 | 2004-02-13 | Photoiniferter mit geöffneter azlacton-ringstruktur für die radikalische polymerisation |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US6908952B2 (https=) |
| EP (1) | EP1606322B1 (https=) |
| JP (1) | JP2006520846A (https=) |
| AT (1) | ATE377030T1 (https=) |
| DE (1) | DE602004009771T2 (https=) |
| WO (1) | WO2004094485A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6992217B2 (en) * | 2002-12-11 | 2006-01-31 | 3M Innovative Properties Company | Ring-opened azlactone initiators for atom transfer radical polymerization |
| US6908952B2 (en) * | 2003-03-21 | 2005-06-21 | 3M Innovative Properties Company | Ring-opened azlactone photoiniferters for radical polymerization |
| WO2007068453A2 (en) * | 2005-12-14 | 2007-06-21 | Novartis Ag | Method for preparing silicone hydrogels |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4304705A (en) * | 1980-01-02 | 1981-12-08 | Minnesota Mining And Manufacturing Company | Radiation-curable polymers containing pendant unsaturated peptide groups derived from azlactone polymers |
| KR910002473B1 (ko) * | 1984-07-05 | 1991-04-23 | 이 아이 듀우판 디 네모아 앤드 캄파니 | 아크릴 별모양 중합체 |
| US5314962A (en) * | 1987-04-07 | 1994-05-24 | Mitsubishi Petrochemical Company Limited | ABA type block copolymers |
| JP2553134B2 (ja) | 1987-04-07 | 1996-11-13 | 三菱化学株式会社 | Ａｂａ型ブロック共重合体 |
| AU614140B2 (en) | 1988-06-28 | 1991-08-22 | Minnesota Mining And Manufacturing Company | Pressure-sensitive adhesive |
| MX173261B (es) | 1988-06-28 | 1994-02-14 | Minnesota Mining & Mfg | Copolimeros acrilicos y metodo para su fabricacion |
| JP2845973B2 (ja) * | 1989-09-04 | 1999-01-13 | 三菱化学株式会社 | ジチオカーバメート基含有ポリエステル |
| US5093385A (en) | 1989-12-21 | 1992-03-03 | Minnesota Mining And Manufacturing Company | Method of accelerating photoiniferter polymerization, polymer produced thereby, and product produced therewith |
| CA2038117A1 (en) * | 1990-03-29 | 1991-09-30 | Mahfuza B. Ali | Controllable radiation curable photoiniferter prepared adhesives for attachment of microelectronic devices and a method of attaching microelectronic devices therewith |
| US5763548A (en) | 1995-03-31 | 1998-06-09 | Carnegie-Mellon University | (Co)polymers and a novel polymerization process based on atom (or group) transfer radical polymerization |
| US5807937A (en) | 1995-11-15 | 1998-09-15 | Carnegie Mellon University | Processes based on atom (or group) transfer radical polymerization and novel (co) polymers having useful structures and properties |
| FR2764892B1 (fr) | 1997-06-23 | 2000-03-03 | Rhodia Chimie Sa | Procede de synthese de polymeres a blocs |
| US6143848A (en) | 1997-10-23 | 2000-11-07 | The B.F.Goodrich Company | End-functionalized polymers by controlled free-radical polymerization process and polymers made therefrom |
| CA2309279C (en) * | 1997-12-18 | 2009-07-14 | E.I. Du Pont De Nemours And Company | Polymerization process with living characteristics and polymers made therefrom |
| AU4363999A (en) * | 1998-05-29 | 1999-12-20 | Ciba Specialty Chemicals Holding Inc. | Novel photoinitiators and their applications |
| JP2002534499A (ja) * | 1999-01-15 | 2002-10-15 | アトフィナ | 界面活性剤と重合開始剤の両方の役目をする化合物を用いた乳化重合 |
| WO2001002452A1 (en) * | 1999-07-02 | 2001-01-11 | Symyx Technologies, Inc. | Polymer brushes for immobilizing molecules to a surface or substrate, where the polymers have water-soluble or water-dispersible segments and probes bonded thereto |
| TW574236B (en) | 2000-09-25 | 2004-02-01 | Ciba Sc Holding Ag | Process for controlled radical polymerization in aqueous dispersion |
| US6569969B2 (en) | 2000-09-28 | 2003-05-27 | Symyx Technologies, Inc. | Control agents for living-type free radical polymerization, methods of polymerizing and polymers with same |
| JP4823436B2 (ja) * | 2001-05-29 | 2011-11-24 | リンテック株式会社 | 紫外線架橋型感圧接着剤組成物、感圧接着剤シート及び感圧接着剤シートの製造方法 |
| US6894133B2 (en) | 2002-12-11 | 2005-05-17 | 3M Innovative Properties Company | Azlactone initiators for atom transfer radical polymerization |
| US6992217B2 (en) * | 2002-12-11 | 2006-01-31 | 3M Innovative Properties Company | Ring-opened azlactone initiators for atom transfer radical polymerization |
| US6677413B1 (en) * | 2003-02-05 | 2004-01-13 | 3M Innovative Properties Company | Azlactone initiators for nitroxide-mediated polymerization |
| US6680362B1 (en) | 2003-02-05 | 2004-01-20 | 3M Innovative Properties Company | Ring-opened azlactone initiators for nitroxide-mediated polymerization |
| US6908952B2 (en) * | 2003-03-21 | 2005-06-21 | 3M Innovative Properties Company | Ring-opened azlactone photoiniferters for radical polymerization |
| US6747104B1 (en) * | 2003-03-21 | 2004-06-08 | 3M Innovative Properties Company | Azlactone photoiniferters for radical polymerization |
| US6762257B1 (en) * | 2003-05-05 | 2004-07-13 | 3M Innovative Properties Company | Azlactone chain transfer agents for radical polymerization |
| US6753391B1 (en) * | 2003-05-05 | 2004-06-22 | 3M Innovative Properties Company | Ring-opened azlactone chain transfer agents for radical polymerization |
-
2003
- 2003-03-21 US US10/393,551 patent/US6908952B2/en not_active Expired - Lifetime
-
2004
- 2004-02-13 JP JP2006508748A patent/JP2006520846A/ja not_active Ceased
- 2004-02-13 EP EP04711278A patent/EP1606322B1/en not_active Expired - Lifetime
- 2004-02-13 WO PCT/US2004/004506 patent/WO2004094485A1/en not_active Ceased
- 2004-02-13 DE DE602004009771T patent/DE602004009771T2/de not_active Expired - Lifetime
- 2004-02-13 AT AT04711278T patent/ATE377030T1/de not_active IP Right Cessation
-
2005
- 2005-03-16 US US11/081,197 patent/US7041755B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US6908952B2 (en) | 2005-06-21 |
| US7041755B2 (en) | 2006-05-09 |
| DE602004009771D1 (de) | 2007-12-13 |
| US20040186196A1 (en) | 2004-09-23 |
| EP1606322A1 (en) | 2005-12-21 |
| WO2004094485A1 (en) | 2004-11-04 |
| ATE377030T1 (de) | 2007-11-15 |
| EP1606322B1 (en) | 2007-10-31 |
| JP2006520846A (ja) | 2006-09-14 |
| US20050182209A1 (en) | 2005-08-18 |
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| 8364 | No opposition during term of opposition |