JP4567000B2 - 可塑剤フリーのコポリマーを含むイオン検出センサー - Google Patents
可塑剤フリーのコポリマーを含むイオン検出センサー Download PDFInfo
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- JP4567000B2 JP4567000B2 JP2006533539A JP2006533539A JP4567000B2 JP 4567000 B2 JP4567000 B2 JP 4567000B2 JP 2006533539 A JP2006533539 A JP 2006533539A JP 2006533539 A JP2006533539 A JP 2006533539A JP 4567000 B2 JP4567000 B2 JP 4567000B2
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- Prior art keywords
- ion
- ionophore
- copolymer
- plasticizer
- alkyl group
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- 229920001577 copolymer Polymers 0.000 title claims description 61
- 238000001514 detection method Methods 0.000 title claims description 20
- 150000002500 ions Chemical class 0.000 claims description 158
- 239000002555 ionophore Substances 0.000 claims description 100
- 230000000236 ionophoric effect Effects 0.000 claims description 90
- 150000001450 anions Chemical class 0.000 claims description 40
- 239000000178 monomer Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 29
- 239000011159 matrix material Substances 0.000 claims description 28
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 125000000524 functional group Chemical group 0.000 claims description 22
- 239000000126 substance Substances 0.000 claims description 19
- 229920000578 graft copolymer Polymers 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000010409 thin film Substances 0.000 claims description 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
- 239000002245 particle Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- 239000003505 polymerization initiator Substances 0.000 claims description 3
- 238000004132 cross linking Methods 0.000 claims description 2
- 239000012528 membrane Substances 0.000 description 64
- 229920000642 polymer Polymers 0.000 description 61
- 239000010408 film Substances 0.000 description 46
- 230000004044 response Effects 0.000 description 38
- -1 polysiloxane Polymers 0.000 description 24
- 239000011734 sodium Substances 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 20
- 150000001768 cations Chemical class 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 239000000523 sample Substances 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 229920000915 polyvinyl chloride Polymers 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 239000004800 polyvinyl chloride Substances 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 238000005259 measurement Methods 0.000 description 11
- 239000004014 plasticizer Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 238000005342 ion exchange Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 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 9
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 9
- 239000011575 calcium Substances 0.000 description 9
- CJAONIOAQZUHPN-KKLWWLSJSA-N ethyl 12-[[2-[(2r,3r)-3-[2-[(12-ethoxy-12-oxododecyl)-methylamino]-2-oxoethoxy]butan-2-yl]oxyacetyl]-methylamino]dodecanoate Chemical compound CCOC(=O)CCCCCCCCCCCN(C)C(=O)CO[C@H](C)[C@@H](C)OCC(=O)N(C)CCCCCCCCCCCC(=O)OCC CJAONIOAQZUHPN-KKLWWLSJSA-N 0.000 description 8
- 238000002474 experimental method Methods 0.000 description 8
- 238000002386 leaching Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 229920012485 Plasticized Polyvinyl chloride Polymers 0.000 description 6
- 238000002835 absorbance Methods 0.000 description 6
- 229910052792 caesium Inorganic materials 0.000 description 6
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 6
- 239000003710 calcium ionophore Substances 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- 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 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 150000003983 crown ethers Chemical class 0.000 description 5
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229920005597 polymer membrane Polymers 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- NBQXYAJLUDQSNV-UHFFFAOYSA-N 1-[(4-methylphenyl)methyl]-5-oxopyrrolidine-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1CN1C(=O)CC(C(O)=O)C1 NBQXYAJLUDQSNV-UHFFFAOYSA-N 0.000 description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 235000011148 calcium chloride Nutrition 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 4
- 230000003834 intracellular effect Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000004005 microsphere Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- UGXRFLXVVYNTTQ-UHFFFAOYSA-N 2-chloro-2,3,3,3-tetrafluoropropanoyl fluoride Chemical compound FC(=O)C(F)(Cl)C(F)(F)F UGXRFLXVVYNTTQ-UHFFFAOYSA-N 0.000 description 3
- GVMYIKFDEAQVBP-UHFFFAOYSA-N 2-ethoxyethane-1,1-diamine Chemical compound CCOCC(N)N GVMYIKFDEAQVBP-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000001110 calcium chloride Substances 0.000 description 3
- 229910001628 calcium chloride Inorganic materials 0.000 description 3
- 229910001424 calcium ion Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000005595 deprotonation Effects 0.000 description 3
- 238000010537 deprotonation reaction Methods 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
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- 230000009477 glass transition Effects 0.000 description 3
- 230000002452 interceptive effect Effects 0.000 description 3
- 239000012633 leachable Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- UONHCVYLDTWLAR-JXHUONGFSA-M nitrite ionophore i Chemical compound O.[Co+2].N#[C-].[O-]Cl(=O)(=O)=O.C([C@@H]1\C=2\N=C(C1(C)C)\C=C1/N/C([C@@]([C@@H]1CCC(=O)OCCC=1C=CC=CC=1)(C)CC(=O)OCCC=1C=CC=CC=1)=C(C1=N[C@@]([C@@]([C@@H]1CCC(=O)OCCC=1C=CC=CC=1)(C)CC(=O)OCCC=1C=CC=CC=1)(C)C1N=C([C@]([C@H]1CC(=O)OCCC=1C=CC=CC=1)(C)CCC(=O)OCCC=1C=CC=CC=1)/C=2C)/C)CC(=O)OCCC1=CC=CC=C1 UONHCVYLDTWLAR-JXHUONGFSA-M 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 239000007793 ph indicator Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- DSFHXKRFDFROER-UHFFFAOYSA-N 2,5,8,11,14,17-hexaoxabicyclo[16.4.0]docosa-1(22),18,20-triene Chemical compound O1CCOCCOCCOCCOCCOC2=CC=CC=C21 DSFHXKRFDFROER-UHFFFAOYSA-N 0.000 description 2
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
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- MYWBZQJIXVRCJC-UHFFFAOYSA-N n-[9-(diethylamino)benzo[a]phenoxazin-5-ylidene]octadecanamide Chemical compound C12=CC=CC=C2C(=NC(=O)CCCCCCCCCCCCCCCCC)C=C2C1=NC1=CC=C(N(CC)CC)C=C1O2 MYWBZQJIXVRCJC-UHFFFAOYSA-N 0.000 description 2
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- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
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- CRWZWBQWZASLBK-UHFFFAOYSA-N 1,4,8,12-tetraoxacyclopentadecane Chemical compound C1COCCCOCCOCCCOC1 CRWZWBQWZASLBK-UHFFFAOYSA-N 0.000 description 1
- BJZNEZSUNWJHQQ-UHFFFAOYSA-N 2,2-bis(2-ethylhexyl)decanedioic acid Chemical compound CCCCC(CC)CC(C(O)=O)(CC(CC)CCCC)CCCCCCCC(O)=O BJZNEZSUNWJHQQ-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
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- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
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- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MXOSTENCGSDMRE-UHFFFAOYSA-N butyl-chloro-dimethylsilane Chemical compound CCCC[Si](C)(C)Cl MXOSTENCGSDMRE-UHFFFAOYSA-N 0.000 description 1
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- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical compound [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 1
- RFVPNGJIVTUOSZ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate;methyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.CCCCCCCCCCOC(=O)C(C)=C RFVPNGJIVTUOSZ-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
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- PHDAZHGCTGTQAS-UHFFFAOYSA-M dimethyl-tetradecyl-(3-trimethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OC)(OC)OC PHDAZHGCTGTQAS-UHFFFAOYSA-M 0.000 description 1
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- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
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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
- 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
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
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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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
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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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
Landscapes
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47367703P | 2003-05-28 | 2003-05-28 | |
| PCT/US2004/017226 WO2004106893A2 (en) | 2003-05-28 | 2004-05-28 | Ion-detecting sensors comprising plasticizer-free copolymers |
Publications (3)
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| JP2007503005A JP2007503005A (ja) | 2007-02-15 |
| JP2007503005A5 JP2007503005A5 (OSRAM) | 2007-07-12 |
| JP4567000B2 true JP4567000B2 (ja) | 2010-10-20 |
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| US (1) | US7226563B2 (OSRAM) |
| EP (1) | EP1634051A4 (OSRAM) |
| JP (1) | JP4567000B2 (OSRAM) |
| WO (1) | WO2004106893A2 (OSRAM) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US7247489B2 (en) * | 2002-03-11 | 2007-07-24 | Auburn University | Ion-detecting microspheres and methods of use thereof |
| WO2005118648A2 (en) * | 2004-06-02 | 2005-12-15 | Auburn University | Non-crystalline cellulose and production thereof |
| EP1864114A1 (en) * | 2005-01-31 | 2007-12-12 | Beckman Coulter, Inc. | Doped silica microsphere optical ion sensors |
| US7678252B2 (en) * | 2005-06-14 | 2010-03-16 | Auburn University | Long lived anion-selective sensors based on a covalently attached metalloporphyrin as anion receptor |
| EP1915400A4 (en) * | 2005-08-04 | 2009-12-16 | Univ Colorado | CATALYSTS FOR RADICAL POLYMERIZATION |
| JP2009508534A (ja) | 2005-09-16 | 2009-03-05 | ザ・チャールズ・スターク・ドレイパー・ラボラトリー・インコーポレイテッド | 生細胞における反応の検出 |
| US8242203B2 (en) * | 2005-11-10 | 2012-08-14 | Eric Bakker | Covalently attached nile blue derivatives for optical sensors |
| US20070111072A1 (en) * | 2005-11-14 | 2007-05-17 | Ryan Wayne | Indicator fixed ion-exchange membrane |
| WO2007131042A2 (en) * | 2006-05-03 | 2007-11-15 | Opti Medical Systems, Inc | Chromoionophore and method of determining potassium ions |
| US20080044879A1 (en) * | 2006-08-17 | 2008-02-21 | The Charles Stark Draper Laboratory, Inc. | Systems and methods of voltage-gated ion channel assays |
| WO2009023287A1 (en) * | 2007-08-16 | 2009-02-19 | Beckman Coulter, Inc. | Polymerized nile blue derivatives for plasticizer-free fluorescent ion optode microsphere sensors |
| US8470300B2 (en) | 2008-09-08 | 2013-06-25 | The Charles Stark Draper Laboratory, Inc. | Coated sensors and methods related thereto |
| ES2334748B1 (es) * | 2008-09-12 | 2011-01-10 | Consejo Superior De Investigaciones Cientificas(Csic) | Sensores potenciometricos basados en clusters de boro anionicos. |
| PT104313A (pt) | 2008-12-31 | 2010-07-01 | Univ Aveiro | MICROELECTRODO SELECTIVO DE IŽES DE CONTACTO SËLIDO E O SEU MéTODO DE PRODUÃÇO |
| US9181375B2 (en) | 2011-02-14 | 2015-11-10 | Arizona Board Of Regents, A Body Corporate Of The State Of Arizona Acting For And On Behalf Of Arizona State University | Fluorescent potassium ion sensors |
| US10294131B2 (en) | 2011-03-23 | 2019-05-21 | Mespilus Inc. | Polarized electrode for flow-through capacitive deionization |
| MY155723A (en) | 2011-07-25 | 2015-11-17 | Mimos Berhad | Self-plasticized sensing membrane |
| US10419544B2 (en) * | 2015-12-22 | 2019-09-17 | Ribbon Communications Operating Company, Inc. | Methods and apparatus for managing the use of IP addresses |
| CN108517023B (zh) * | 2017-12-19 | 2020-07-31 | 湖南科技大学 | 一种可比率荧光检测次氯酸的聚合物纳米粒子的制备及应用 |
| CN109096431B (zh) * | 2018-08-21 | 2020-11-27 | 湖南工业大学 | 一种纳米发电机与自驱动传感器用聚丙烯酸丁酯-聚甲基丙烯酸丁酯共聚物及其制备方法 |
| US11567030B2 (en) * | 2019-07-29 | 2023-01-31 | Rosemount Inc. | Electrochemical sensor |
| CN119757494A (zh) * | 2025-03-07 | 2025-04-04 | 中国科学院烟台海岸带研究所 | 双功能聚合物膜及在制备电位型传感器中的应用 |
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| JPS4838789B1 (OSRAM) * | 1970-07-31 | 1973-11-20 | ||
| US3716506A (en) * | 1970-12-22 | 1973-02-13 | Du Pont | Process for preparing aziridinyl alkyl-acrylate or methacrylate graft copolymers |
| US4162282A (en) | 1976-04-22 | 1979-07-24 | Coulter Electronics, Inc. | Method for producing uniform particles |
| US4302166A (en) | 1976-04-22 | 1981-11-24 | Coulter Electronics, Inc. | Droplet forming apparatus for use in producing uniform particles |
| GB1577998A (en) * | 1977-09-28 | 1980-10-29 | Kansai Paint Co Ltd | Low temperature curing high solid acrylic copolymer-aminoplast resin coating compositions |
| US4174531A (en) * | 1977-11-14 | 1979-11-13 | Rca Corporation | Printed circuit board with increased arc track resistance |
| JPS5915325B2 (ja) | 1981-03-26 | 1984-04-09 | 工業技術院長 | クラウンエ−テル環をもつポリオレフィンのフイルム又は繊維の製造方法 |
| DE3150730A1 (de) * | 1981-12-22 | 1983-06-30 | Röhm GmbH, 6100 Darmstadt | Verfahren zur herstellung blockfester, weicher polymerperlen |
| US4828359A (en) * | 1986-01-09 | 1989-05-09 | Sumitomo Electric Industries, Ltd. | Alkyl methacrylate homo - or copolymer optical waveguide for illumination and production of the same |
| IE893986A1 (en) | 1989-12-13 | 1991-06-19 | Loctite Ireland Ltd | Polymerisable calixarene and oxacalixarene derivatives,¹polymers thereof, and use of such derivatives and polymers¹for sequestration of metals |
| US5132345A (en) | 1990-12-10 | 1992-07-21 | Harris Stephen J | Ion-selective electrodes |
| US5260195A (en) * | 1991-01-03 | 1993-11-09 | Boehringer Mannheim Corporation | Nonaqueous polymeric reagent compositions and applications thereof |
| US5198301A (en) * | 1991-05-17 | 1993-03-30 | Minnesota Mining And Manufacturing Company | Flexible and conformable ionomeric resin based films |
| NL194838C (nl) * | 1991-05-17 | 2003-04-03 | Priva Agro Holding Bv | Metaalion-selectief membraan en sensor met daarin opgenomen dit membraan. |
| JP3032677B2 (ja) * | 1994-03-24 | 2000-04-17 | アヴェンティス・リサーチ・ウント・テクノロジーズ・ゲーエムベーハー・ウント・コー・カーゲー | 燃料蒸気判別方法及び装置 |
| EP0758450B1 (en) * | 1994-03-25 | 1998-08-05 | Novartis AG | Optical sensor for the determination of ions |
| WO1996031519A1 (en) * | 1995-04-05 | 1996-10-10 | Board Of Regents Of The University Of Colorado | Weakly nucleophilic anions |
| US5747349A (en) * | 1996-03-20 | 1998-05-05 | University Of Washington | Fluorescent reporter beads for fluid analysis |
| AU2636697A (en) * | 1996-04-16 | 1997-11-07 | Novartis Ag | Covalently immobilized fluoroionophores as optical ion sensors |
| EP0929803B1 (en) * | 1996-09-30 | 2002-04-03 | Celanese Ventures GmbH | Optical sensor for detecting chemical substances dissolved or dispersed in water |
| US6143558A (en) | 1997-07-08 | 2000-11-07 | The Regents Of The University Of Michigan | Optical fiberless sensors for analyzing cellular analytes |
| US6601828B2 (en) * | 2001-01-31 | 2003-08-05 | Otis Elevator Company | Elevator hoist machine and related assembly method |
| US6548310B1 (en) * | 1999-07-08 | 2003-04-15 | Jsr Corporation | Particle for diagnostic agent and turbidmetric immunoassay using the same |
| AU781697B2 (en) * | 1999-10-11 | 2005-06-09 | Inventio Ag | Cable elevator |
| KR100400085B1 (ko) * | 2001-07-04 | 2003-09-29 | 학교법인 포항공과대학교 | 수용성 및 지용성 쿠커비투릴 유도체, 그 제조방법, 그분리방법 및 용도 |
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- 2004-05-28 EP EP04753947A patent/EP1634051A4/en not_active Withdrawn
- 2004-05-28 WO PCT/US2004/017226 patent/WO2004106893A2/en not_active Ceased
- 2004-05-28 US US10/856,665 patent/US7226563B2/en not_active Expired - Fee Related
- 2004-05-28 JP JP2006533539A patent/JP4567000B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US7226563B2 (en) | 2007-06-05 |
| US20050011760A1 (en) | 2005-01-20 |
| WO2004106893A3 (en) | 2005-07-21 |
| JP2007503005A (ja) | 2007-02-15 |
| EP1634051A2 (en) | 2006-03-15 |
| EP1634051A4 (en) | 2009-03-25 |
| WO2004106893A2 (en) | 2004-12-09 |
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