ES2249289T3 - (met)acrilatos de naftiloxialquilo con indices de refraccion elevados y temperaturas de transicion vitrea bajas. - Google Patents
(met)acrilatos de naftiloxialquilo con indices de refraccion elevados y temperaturas de transicion vitrea bajas.Info
- Publication number
- ES2249289T3 ES2249289T3 ES00953920T ES00953920T ES2249289T3 ES 2249289 T3 ES2249289 T3 ES 2249289T3 ES 00953920 T ES00953920 T ES 00953920T ES 00953920 T ES00953920 T ES 00953920T ES 2249289 T3 ES2249289 T3 ES 2249289T3
- Authority
- ES
- Spain
- Prior art keywords
- monomer
- formula
- polymer
- meth
- acrylate
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 title description 5
- 241001300078 Vitrea Species 0.000 title 1
- 230000007704 transition Effects 0.000 title 1
- 239000000178 monomer Substances 0.000 claims abstract description 57
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 22
- 230000009477 glass transition Effects 0.000 claims abstract description 16
- 229920001519 homopolymer Polymers 0.000 claims abstract description 16
- 239000000203 mixture Substances 0.000 claims description 33
- 229920000642 polymer Polymers 0.000 claims description 33
- 230000003287 optical effect Effects 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000000758 substrate Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 230000004313 glare Effects 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 6
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 4
- 239000000463 material Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000008367 deionised water Substances 0.000 description 11
- 229910021641 deionized water Inorganic materials 0.000 description 11
- 239000000853 adhesive Substances 0.000 description 9
- 230000001070 adhesive effect Effects 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- -1 6- (2-Naphthyloxy) -1-hexyl Chemical group 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000005429 oxyalkyl group Chemical group 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- UAGGAZHJHUTMJP-UHFFFAOYSA-N 6-naphthalen-1-yloxyhexan-1-ol Chemical compound C1=CC=C2C(OCCCCCCO)=CC=CC2=C1 UAGGAZHJHUTMJP-UHFFFAOYSA-N 0.000 description 2
- YDFAJMDFCCJZSI-UHFFFAOYSA-N 8-chlorooctan-1-ol Chemical compound OCCCCCCCCCl YDFAJMDFCCJZSI-UHFFFAOYSA-N 0.000 description 2
- HRHCWEBFUBVXOE-UHFFFAOYSA-N 8-naphthalen-1-yloxyoctan-1-ol Chemical compound C1=CC=C2C(OCCCCCCCCO)=CC=CC2=C1 HRHCWEBFUBVXOE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000001023 inorganic pigment Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- JNTPTNNCGDAGEJ-UHFFFAOYSA-N 6-chlorohexan-1-ol Chemical compound OCCCCCCCl JNTPTNNCGDAGEJ-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010408 sweeping Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000013638 trimer 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- 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
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/30—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety
- C08F220/301—Esters containing oxygen in addition to the carboxy oxygen containing aromatic rings in the alcohol moiety and one oxygen in the alcohol moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Dental Preparations (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/605,462 US6376704B1 (en) | 2000-06-28 | 2000-06-28 | Naphthyoxyalkyl(meth)acrylates with high refractive indices and low glass transition temperatures |
| US605462 | 2000-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2249289T3 true ES2249289T3 (es) | 2006-04-01 |
Family
ID=24423755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00953920T Expired - Lifetime ES2249289T3 (es) | 2000-06-28 | 2000-08-10 | (met)acrilatos de naftiloxialquilo con indices de refraccion elevados y temperaturas de transicion vitrea bajas. |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6376704B1 (enExample) |
| EP (1) | EP1294674B1 (enExample) |
| JP (1) | JP2004501889A (enExample) |
| KR (1) | KR100712582B1 (enExample) |
| AT (1) | ATE309191T1 (enExample) |
| AU (1) | AU2000266285A1 (enExample) |
| DE (1) | DE60023954T2 (enExample) |
| ES (1) | ES2249289T3 (enExample) |
| WO (1) | WO2002000594A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6663978B1 (en) * | 2000-06-28 | 2003-12-16 | 3M Innovative Properties Company | High refractive index pressure-sensitive adhesives |
| US7166686B2 (en) * | 2000-06-28 | 2007-01-23 | 3M Innovative Properties Company | High refractive index pressure-sensitive adhesives |
| WO2002067020A2 (en) * | 2001-02-19 | 2002-08-29 | Koninklijke Philips Electronics N.V. | Optical element and method of manufacturing such an optical element |
| US7289202B2 (en) | 2004-09-10 | 2007-10-30 | 3M Innovative Properties Company | Methods for testing durable optical elements |
| US7074463B2 (en) | 2003-09-12 | 2006-07-11 | 3M Innovative Properties Company | Durable optical element |
| US7282272B2 (en) | 2003-09-12 | 2007-10-16 | 3M Innovative Properties Company | Polymerizable compositions comprising nanoparticles |
| JP2008514764A (ja) * | 2004-09-28 | 2008-05-08 | ブルーワー サイエンス アイ エヌ シー． | 光電子用途に用いる硬化性高屈折率樹脂 |
| US7326448B2 (en) | 2005-02-17 | 2008-02-05 | 3M Innovative Properties Company | Polymerizable oligomeric urethane compositions comprising nanoparticles |
| US7400445B2 (en) * | 2005-05-31 | 2008-07-15 | 3M Innovative Properties Company | Optical filters for accelerated weathering devices |
| JP2010507361A (ja) | 2006-07-31 | 2010-03-11 | キュアバック ゲーエムベーハー | 具体的には免疫刺激剤／アジュバントとしての、一般式（Ｉ）：ＧｌＸｍＧｎ、または一般式（ＩＩ）：ＣｌＸｍＣｎで表される核酸 |
| WO2009030254A1 (en) | 2007-09-04 | 2009-03-12 | Curevac Gmbh | Complexes of rna and cationic peptides for transfection and for immunostimulation |
| CN101932707B (zh) | 2008-01-31 | 2013-08-21 | 库瑞瓦格有限责任公司 | 作为免疫刺激剂/佐剂的式(I)(NuGlXmGnNv)a的核酸及其衍生物 |
| WO2010037408A1 (en) | 2008-09-30 | 2010-04-08 | Curevac Gmbh | Composition comprising a complexed (m)rna and a naked mrna for providing or enhancing an immunostimulatory response in a mammal and uses thereof |
| WO2010113600A1 (ja) * | 2009-03-31 | 2010-10-07 | Dic株式会社 | （メタ）アクリル酸エステル誘導体 |
| US20110053829A1 (en) | 2009-09-03 | 2011-03-03 | Curevac Gmbh | Disulfide-linked polyethyleneglycol/peptide conjugates for the transfection of nucleic acids |
| US8968746B2 (en) | 2010-07-30 | 2015-03-03 | Curevac Gmbh | Complexation of nucleic acids with disulfide-crosslinked cationic components for transfection and immunostimulation |
| KR101255759B1 (ko) * | 2011-04-04 | 2013-04-17 | 한양대학교 에리카산학협력단 | 고굴절율을 갖는 아크릴레이트 유도체 및 그 제조방법 |
| WO2013113326A1 (en) | 2012-01-31 | 2013-08-08 | Curevac Gmbh | Pharmaceutical composition comprising a polymeric carrier cargo complex and at least one protein or peptide antigen |
| CA2915728A1 (en) | 2013-08-21 | 2015-02-26 | Thomas Kramps | Respiratory syncytial virus (rsv) vaccine |
| CA2936286A1 (en) | 2014-04-01 | 2015-10-08 | Curevac Ag | Polymeric carrier cargo complex for use as an immunostimulating agent or as an adjuvant |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3479651D1 (en) | 1983-05-20 | 1989-10-12 | Showa Denko Kk | Naphthalene derivative, polymerizable composition containing the same and polymer obtainable by polymerizing this composition |
| US4683169A (en) | 1985-11-04 | 1987-07-28 | General Electric Company | Methyl methacrylic coatings on thermoplastic film |
| US5290892A (en) | 1990-11-07 | 1994-03-01 | Nestle S.A. | Flexible intraocular lenses made from high refractive index polymers |
| US5602221A (en) | 1993-11-10 | 1997-02-11 | Minnesota Mining And Manufacturing Company | Pressure sensitive adhesives with good low energy surface adhesion |
| JP3876299B2 (ja) | 1994-11-22 | 2007-01-31 | スリーエム カンパニー | 振動性固体物品に付着された粘弾性材料の少なくとも１層を含む制動構造物 |
| JP4913930B2 (ja) | 1998-09-24 | 2012-04-11 | 日東電工株式会社 | 熱接着性組成物とその接着シ―ト類 |
-
2000
- 2000-06-28 US US09/605,462 patent/US6376704B1/en not_active Expired - Lifetime
- 2000-08-10 KR KR1020027017796A patent/KR100712582B1/ko not_active Expired - Fee Related
- 2000-08-10 JP JP2002505344A patent/JP2004501889A/ja not_active Withdrawn
- 2000-08-10 EP EP00953920A patent/EP1294674B1/en not_active Expired - Lifetime
- 2000-08-10 DE DE60023954T patent/DE60023954T2/de not_active Expired - Fee Related
- 2000-08-10 AT AT00953920T patent/ATE309191T1/de not_active IP Right Cessation
- 2000-08-10 ES ES00953920T patent/ES2249289T3/es not_active Expired - Lifetime
- 2000-08-10 WO PCT/US2000/021814 patent/WO2002000594A1/en not_active Ceased
- 2000-08-10 AU AU2000266285A patent/AU2000266285A1/en not_active Abandoned
-
2001
- 2001-12-17 US US10/024,058 patent/US6433216B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004501889A (ja) | 2004-01-22 |
| WO2002000594A1 (en) | 2002-01-03 |
| WO2002000594A9 (en) | 2002-03-14 |
| AU2000266285A1 (en) | 2002-01-08 |
| DE60023954T2 (de) | 2006-08-31 |
| US6376704B1 (en) | 2002-04-23 |
| US6433216B1 (en) | 2002-08-13 |
| DE60023954D1 (de) | 2005-12-15 |
| KR100712582B1 (ko) | 2007-05-16 |
| US20020058773A1 (en) | 2002-05-16 |
| KR20030014398A (ko) | 2003-02-17 |
| EP1294674B1 (en) | 2005-11-09 |
| EP1294674A1 (en) | 2003-03-26 |
| ATE309191T1 (de) | 2005-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6433216B1 (en) | Naphthyloxyalkyl(meth)acrylates with high refractive indices and low glass transition temperatures | |
| KR100477187B1 (ko) | 화학 조성물, 그리고 이것으로부터 유도된 중합체 및중합체 물질 | |
| KR100727501B1 (ko) | 고굴절률의 마이크로복제 수지 | |
| JP5212577B1 (ja) | ラジカル重合性組成物、その硬化物及びプラスチックレンズ | |
| US20160272888A1 (en) | Polymerizable liquid crystal composition, and anisotropic optical body, retardation film, antireflective film, and liquid crystal, display element fabricated using composition | |
| JP2012082386A (ja) | 光学材料用高屈折組成物およびその硬化物 | |
| JP5315829B2 (ja) | 硬化型ハードコート剤組成物 | |
| CN103080162A (zh) | 自由基聚合性组合物、固化物和塑料透镜 | |
| TW201311639A (zh) | （甲基）丙烯酸酯化合物、自由基聚合性組成物、硬化物及塑膠透鏡 | |
| CN101547894B (zh) | 聚合性光学活性化合物及含有该聚合性光学活性化合物的聚合性组合物 | |
| EP0795765B1 (en) | Photopolymerizable composition and transparent cured product thereof | |
| JP2017179083A (ja) | 硬化性組成物、硬化物及び積層体 | |
| ES2329223T3 (es) | Soluciones de poliacrilatos que pueden ser reticulados por medio de rayos uv. | |
| KR101648041B1 (ko) | 중합성 화합물 | |
| JP2009073923A (ja) | 親水性化合物およびこれからなる親水性材料 | |
| JP2008512282A (ja) | 調光フィルム並びにその製造及び使用 | |
| EP1109776B1 (en) | Brominated materials | |
| JP4822751B2 (ja) | 共重合体およびその製造方法 | |
| JP2716451B2 (ja) | エネルギー線硬化性材料 | |
| JPH08188625A (ja) | 硬化性樹脂 | |
| JP4520377B2 (ja) | 含フッ素共重合体およびその製造方法 | |
| JP3543359B2 (ja) | チオアセタール化合物、単量体組成物及び光学用材料 | |
| JPH11174201A (ja) | プラスチックレンズ用組成物およびプラスチックレンズ | |
| JPH11174203A (ja) | 高屈折率プラスチックレンズ用組成物およびプラスチックレンズ | |
| JPH08217878A (ja) | スチレンプレポリマーおよび光学用材料 |