JP2004501889A - 高い屈折率および低いガラス転移温度を有するナフチロキシアルキル（メタ）アクリレート - Google Patents
高い屈折率および低いガラス転移温度を有するナフチロキシアルキル（メタ）アクリレート Download PDFInfo
- Publication number
- JP2004501889A JP2004501889A JP2002505344A JP2002505344A JP2004501889A JP 2004501889 A JP2004501889 A JP 2004501889A JP 2002505344 A JP2002505344 A JP 2002505344A JP 2002505344 A JP2002505344 A JP 2002505344A JP 2004501889 A JP2004501889 A JP 2004501889A
- Authority
- JP
- Japan
- Prior art keywords
- monomer
- refractive index
- acrylate
- meth
- carbon atoms
- 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.)
- Withdrawn
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 22
- 230000009477 glass transition Effects 0.000 title claims abstract description 16
- 239000000178 monomer Substances 0.000 claims abstract description 60
- 229920001519 homopolymer Polymers 0.000 claims abstract description 16
- 229920000642 polymer Polymers 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 230000003287 optical effect Effects 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 18
- 230000004313 glare Effects 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 6
- 239000000463 material Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000008367 deionised water Substances 0.000 description 14
- 229910021641 deionized water Inorganic materials 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 238000000576 coating method Methods 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 8
- 230000001070 adhesive effect Effects 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000004817 gas chromatography Methods 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
- 238000002310 reflectometry Methods 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- -1 polyethylene terephthalate Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 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
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 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
- 239000012074 organic phase Substances 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 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
- WNJWHQIMUOWKLD-UHFFFAOYSA-N 6-naphthalen-1-yloxyhexyl prop-2-enoate Chemical compound C1=CC=C2C(OCCCCCCOC(=O)C=C)=CC=CC2=C1 WNJWHQIMUOWKLD-UHFFFAOYSA-N 0.000 description 3
- HVWJYTCIAJYLBV-UHFFFAOYSA-N 8-naphthalen-1-yloxyoctyl prop-2-enoate Chemical group C1=CC=C2C(OCCCCCCCCOC(=O)C=C)=CC=CC2=C1 HVWJYTCIAJYLBV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 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
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 3
- 125000005429 oxyalkyl group Chemical group 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 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
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound 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
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 230000005670 electromagnetic radiation Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 238000004809 thin layer chromatography Methods 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
- 0 *C(C(OIOCC1CC(CCCC2)C2CC1)=O)=C Chemical compound *C(C(OIOCC1CC(CCCC2)C2CC1)=O)=C 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
- KHVSYYOPPZRKLM-UHFFFAOYSA-N 6-naphthalen-2-yloxyhexyl prop-2-enoate Chemical group C1=CC=CC2=CC(OCCCCCCOC(=O)C=C)=CC=C21 KHVSYYOPPZRKLM-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
- XDTMQSROBMDMFD-UHFFFAOYSA-N C1CCCCC1 Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 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 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
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- 239000012985 polymerization agent Substances 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
- 238000010926 purge Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 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 |
| PCT/US2000/021814 WO2002000594A1 (en) | 2000-06-28 | 2000-08-10 | Naphthyloxyalkyl (meth) acrylates with high refractive indices and low glass transition temperatures |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004501889A true JP2004501889A (ja) | 2004-01-22 |
| JP2004501889A5 JP2004501889A5 (enExample) | 2007-07-26 |
Family
ID=24423755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002505344A Withdrawn JP2004501889A (ja) | 2000-06-28 | 2000-08-10 | 高い屈折率および低いガラス転移温度を有するナフチロキシアルキル（メタ）アクリレート |
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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Families Citing this family (19)
| 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 |
| BR0204165A (pt) * | 2001-02-19 | 2002-12-31 | Koninkl Philips Electronics Nv | Elemento óptico, método para fabricar um elemento óptico, e, tela de exibidor de um dispositivo exibidor |
| US7282272B2 (en) | 2003-09-12 | 2007-10-16 | 3M Innovative Properties Company | Polymerizable compositions comprising nanoparticles |
| US7074463B2 (en) | 2003-09-12 | 2006-07-11 | 3M Innovative Properties Company | Durable optical element |
| US7289202B2 (en) | 2004-09-10 | 2007-10-30 | 3M Innovative Properties Company | Methods for testing durable optical elements |
| EP1815273A2 (en) * | 2004-09-28 | 2007-08-08 | Brewer Science, Inc. | Curable high refractive index resins for optoelectronic applications |
| 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 |
| MX2010008468A (es) | 2008-01-31 | 2010-08-30 | Curevac Gmbh | Acidos nucleicos de la formula (i) (nug1xmgnnv)a y derivados de los mismos como un agente/adyuvante inmunoestimulante. |
| 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 |
| US20110053829A1 (en) | 2009-09-03 | 2011-03-03 | Curevac Gmbh | Disulfide-linked polyethyleneglycol/peptide conjugates for the transfection of nucleic acids |
| CA2801523C (en) | 2010-07-30 | 2021-08-03 | 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 |
| ES2747762T3 (es) | 2013-08-21 | 2020-03-11 | Curevac Ag | Vacuna contra el virus respiratorio sincitial (RSV) |
| WO2015149944A2 (en) | 2014-04-01 | 2015-10-08 | Curevac Gmbh | 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 |
|---|---|---|---|---|
| EP0126397B1 (en) | 1983-05-20 | 1989-09-06 | Showa Denko Kabushiki Kaisha | 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 |
| AU694287B2 (en) | 1994-11-22 | 1998-07-16 | Minnesota Mining And Manufacturing Company | Pressure sensitive adhesives and damping constructions |
| 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 EP EP00953920A patent/EP1294674B1/en not_active Expired - Lifetime
- 2000-08-10 AU AU2000266285A patent/AU2000266285A1/en not_active Abandoned
- 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 JP JP2002505344A patent/JP2004501889A/ja not_active Withdrawn
- 2000-08-10 KR KR1020027017796A patent/KR100712582B1/ko not_active Expired - Fee Related
- 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
-
2001
- 2001-12-17 US US10/024,058 patent/US6433216B1/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP4645925B2 (ja) * | 2009-03-31 | 2011-03-09 | Ｄｉｃ株式会社 | （メタ）アクリル酸エステル誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1294674B1 (en) | 2005-11-09 |
| US6376704B1 (en) | 2002-04-23 |
| WO2002000594A1 (en) | 2002-01-03 |
| WO2002000594A9 (en) | 2002-03-14 |
| DE60023954D1 (de) | 2005-12-15 |
| AU2000266285A1 (en) | 2002-01-08 |
| KR100712582B1 (ko) | 2007-05-16 |
| ATE309191T1 (de) | 2005-11-15 |
| KR20030014398A (ko) | 2003-02-17 |
| EP1294674A1 (en) | 2003-03-26 |
| US6433216B1 (en) | 2002-08-13 |
| DE60023954T2 (de) | 2006-08-31 |
| ES2249289T3 (es) | 2006-04-01 |
| US20020058773A1 (en) | 2002-05-16 |
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