CS213944B1 - Calcium/ii/-selective polymeric diaphragm - Google Patents
Calcium/ii/-selective polymeric diaphragm Download PDFInfo
- Publication number
- CS213944B1 CS213944B1 CS802865A CS286580A CS213944B1 CS 213944 B1 CS213944 B1 CS 213944B1 CS 802865 A CS802865 A CS 802865A CS 286580 A CS286580 A CS 286580A CS 213944 B1 CS213944 B1 CS 213944B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- calcium
- advantageously
- ions
- carbon atoms
- alkyl
- Prior art date
Links
- 239000011575 calcium Substances 0.000 title claims description 9
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title description 5
- 229910052791 calcium Inorganic materials 0.000 title description 5
- 239000012528 membrane Substances 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 229920003023 plastic Polymers 0.000 claims abstract description 4
- 239000004033 plastic Substances 0.000 claims abstract description 4
- 229920000915 polyvinyl chloride Polymers 0.000 claims abstract description 4
- 239000004800 polyvinyl chloride Substances 0.000 claims abstract description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 150000002891 organic anions Chemical class 0.000 claims abstract description 3
- 239000000463 material Substances 0.000 claims abstract 3
- 239000000203 mixture Substances 0.000 claims description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
- 239000000920 calcium hydroxide Substances 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229920001577 copolymer Polymers 0.000 claims 1
- 239000004005 microsphere Substances 0.000 claims 1
- -1 calcium (II) ions Chemical class 0.000 abstract description 8
- 230000007935 neutral effect Effects 0.000 abstract description 6
- 239000004014 plasticizer Substances 0.000 abstract description 3
- 239000007787 solid Substances 0.000 abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000004044 response Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229910001424 calcium ion Inorganic materials 0.000 description 4
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000003446 memory effect Effects 0.000 description 2
- CFPFMAGBHTVLCZ-UHFFFAOYSA-N (4-chlorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=C(Cl)C=C1 CFPFMAGBHTVLCZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- ZKIBBIKDPHAFLN-UHFFFAOYSA-N boronium Chemical compound [H][B+]([H])([H])[H] ZKIBBIKDPHAFLN-UHFFFAOYSA-N 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000002555 ionophore Substances 0.000 description 1
- 230000000236 ionophoric effect Effects 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012086 standard solution Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/20—Manufacture of shaped structures of ion-exchange resins
- C08J5/22—Films, membranes or diaphragms
- C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
- C08J5/2218—Synthetic macromolecular compounds
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
- G01N27/26—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating electrochemical variables; by using electrolysis or electrophoresis
- G01N27/28—Electrolytic cell components
- G01N27/30—Electrodes, e.g. test electrodes; Half-cells
- G01N27/333—Ion-selective electrodes or membranes
- G01N27/3335—Ion-selective electrodes or membranes the membrane containing at least one organic component
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Electrochemistry (AREA)
- Inorganic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Physics & Mathematics (AREA)
- Molecular Biology (AREA)
- Materials Engineering (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
Vynález se týká polymerní membrány selektivní na vápenaté ionty v literatuře popsané ionselektivní elektrody na vápník používají různé typy funkčních membrán. Jsou to především pevné membrány z anorganických krystalů jako CaF£ + ЬаР^ /Farren G.M., Ger. 2101339/ nebo CaWO^ /Velely J.f Jindra J., Czech 163358/ a PVC membrány, které mají jako aktivní složku vápenatou sůl kyseliny oktylfenylfosforěčné /Tjell J.C., Růžička J., Ger.Offen. 2,349299/ nebo/1,1,3,3-tetramethylbutyl/ fenylfosforečné /Cosgrove R.E.,US 3729401/. Čidl^ založená na monokrystalech, nedoznala většího rozšíření zejména pro nízkou selektivitu a neideální odezvy. Podstatnou nevýhodou elektrod, používajících vápenaté soli kyselin alkylfosforečných je značná závislost jejich odezvy na pH, což komplikuje jejich analytické využití. Nedostatky obou typů zmíněných membrán odstraňují membrány s neutrálními nosiči. Řadu necyklických neutrálních ionoforů pro membrány selektivní na vápník popsal Simon se spolupracovníky /Helv. Chim. Acta 58, 1535, /1975/. Určitým nedostatkem sensorů založených na těchto neutrálních nosičích jsou pamětové efekty membrán, které zhoršují jejich odezvu při přechodu od koncentrovanějších ke zředěnéjším roztokům.
Podstata membrány selektivní na vápenaté ionty, která je tvořena pevným filmem plastické hmoty, s výhodou polyvinylchloridu, obsahujícím aktivní neutrální nosič ve zmekčovadle použité plastické hmoty, spočívá podle vynálezu v tom, že aktivním neutrálním nosičem je komplex makrocykliokých polyetherdiamidů obecného vzorce
kde Rp ^2» R3> ^4 jsou H nebo alkyl obsahující 1-4 atomy uhlíku, s výhodou methyl, R^ a značí alkyl s 6 - 10 atomy uhlíku, s výhodou benzyl, přičemž obecné složení komplexu je polyetherdiamid . Ca · 2A* kde A je lipofilní organický anion, s výhodou tetrafenyl nebo tetra(p-chlorfenyl) borátový anion.
Jako změkčovadel lze s výhodou použít takových, která mají dielektrickou konstantu vyšší než 10, jako jsou například nitrované alkylarylethery, s výhodou nitrované fenyl-n-alkylethery, kde alkyl obsahuje v) řetězci více než 6 atomů uhlíku.
Vápníkové elektrody založené na uvedeném komplexu mají výhodu v přesně definovaném složení aktivní komponenty, Lineární odezvě в teoretickým průběhem
-1 -5 2+ v širokém koncentračním rozmezí 10 M - 10 M Ca . Odezva elektrody na aktivitu vápenatých iontů je prakticky okamžitá, bez pamětových efektů. Elektrody vykazují vysokou selektivitu pro vápenaté ionty, zejména vzhledem к iontům Na, Mg, K, Rbv a Ca.
V dalším je vynález blíže objasněn na příkladech provedení.
Příklad 1
К roztokuO,55 g polyetherdiamidů I ( Rp R2, Rp R^ « CH^ t Rp Rg « benzyl) a 0,07 g CaíSClOg v 5 ml methanolu se přidá roztok 0,5 g tetra(p-ohlorofenyl) borkalia v 3 ml methanolu. Vyloučená bílá sraženina se po odsátí překrystaluje z nitromethanu a vysuší při 110° C. Získá se 0,7 g komplexu o b.t. 218 - 220°C.
Jeho složení dle elementární analýzy je 2 polyetherdiamid, Ca . 2(01CgH^)^B Příklad 2 mg komplexu z příkladu 1 se rozpustí v 1 ml o-nitro-fenyl-oktyletheru a smíchá s 10 ml 5% roztoku vysokomolekulárního póly vinyl chloridu v cyklhexanonu. Roztok se nalije na vodorovnou skleněnou desku 7 x 15 cm. Odpařením cyklohexanonu za normální teploty se získá fólie síly cca 0,15 mm. Z této folie se vyřízne kroužek a upevní v elektrodovém tělese. Po nalití vnitřního stndartního roztoku á
se-elektroda zkompletuje -zasunutím svodné-argent-chloridové elektrody. S takto připravenou elektrodou byly naměřeny nesledující selektivní koeficienty log kQaM pro tyto ionty M:
Mg = -3,77; Sr « -0,93; Ba = -2,10; li = -2,44; Na =.-3,73;
K - = -3,66; Rb - -4,09; -Cs « -4,30.
Claims (2)
- P^I.ype^:L membrána selektivní na vápenaté hmooy, s výhodou polyvinylchloridu, která zmPkkovadle p<^L^j^j-'té plastické - hmpoy, vyznačené t!., že aktivním nosičem je komplex -mkrooykkic.kýeh polyethexdiamidd obecného vzorc^e ionty, tvořená pevným fiPmem - plastické obsahuje aktivní neutrální nosič va kde Rp R, Rp Rjaou H nebo -alkyl, obe^nuící 1 až 4 atomy uhlíku , s výhodou methyl, R a Rg značí alkyl s 6 až 10 atomy uhlíku, в výhodou benzyl, přičemž obecné složení ko^ip.exu je
- 2 polyetherdičmid .- - Ca ,2A^· kde A- je lipofilní organický anion , s výhodou tetrafenyl nebo tetIa(l-ehlooofenyl) borátový anion.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS802865A CS213944B1 (en) | 1980-04-24 | 1980-04-24 | Calcium/ii/-selective polymeric diaphragm |
| US06/250,019 US4379041A (en) | 1980-04-24 | 1981-04-01 | Polymeric membrane selective to calcium (II) ions |
| GB8111134A GB2086925B (en) | 1980-04-24 | 1981-04-09 | Polymeric membrane selective to calcium (ii) ions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS802865A CS213944B1 (en) | 1980-04-24 | 1980-04-24 | Calcium/ii/-selective polymeric diaphragm |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS213944B1 true CS213944B1 (en) | 1982-04-09 |
Family
ID=5366989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS802865A CS213944B1 (en) | 1980-04-24 | 1980-04-24 | Calcium/ii/-selective polymeric diaphragm |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4379041A (cs) |
| CS (1) | CS213944B1 (cs) |
| GB (1) | GB2086925B (cs) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4432904A (en) * | 1982-09-29 | 1984-02-21 | E. I. Du Pont De Nemours And Company | Phosphine azacrown ether compounds |
| JPS59137851A (ja) * | 1983-01-28 | 1984-08-08 | Hitachi Ltd | 液膜形陰イオン選択性電極 |
| US4561962A (en) * | 1983-04-06 | 1985-12-31 | Fluilogic Systems Oy | Ion-selective electrode and procedure for manufacturing same |
| JPH01501618A (ja) * | 1985-06-27 | 1989-06-08 | ウィリス，ジョン・ピ− | イオノホアおよびそれを含むイオン選択性膜 |
| US4743352A (en) * | 1986-09-17 | 1988-05-10 | The University Of Michigan | Sodium ion-selective electrode system and method for making an ion-selective electrode |
| US4793942A (en) * | 1987-01-08 | 1988-12-27 | Ecolab Inc. | Detersive systems with a dispersed aqueous-organic softening agent for hardness removal |
| US4948473A (en) * | 1987-10-13 | 1990-08-14 | The Clorox Company | Surfactant sensing electrode for potentiometric titrations |
| US4810331A (en) * | 1987-10-13 | 1989-03-07 | The Clorox Company | Surfactant sensing electrode for potentiometric titrations |
| US4911856A (en) * | 1988-11-30 | 1990-03-27 | Ecolab Inc. | Low acid, soluble salt containing aqueous-organic softening agents for detersive systems |
| US4971714A (en) * | 1988-11-30 | 1990-11-20 | Ecolab Inc. | Detersive system with an improved hardness ion complexing agent |
| JP2804588B2 (ja) * | 1990-03-03 | 1998-09-30 | 株式会社日立製作所 | カルシウムイオン測定電極 |
| DE69123774D1 (de) * | 1990-04-12 | 1997-02-06 | Hitachi Ltd | Vorrichtung zur Bestimmung mindestens einer gasförmigen Komponente in einer gasförmigen oder flüssigen Probe und Bestimmungsverfahren |
| NL194838C (nl) * | 1991-05-17 | 2003-04-03 | Priva Agro Holding Bv | Metaalion-selectief membraan en sensor met daarin opgenomen dit membraan. |
| US5342490A (en) * | 1992-06-10 | 1994-08-30 | Alfred B. P. Lever | Electrolytic detection of sulfur |
| EP0792454B1 (en) * | 1994-11-14 | 2002-04-10 | Bayer Corporation | RANDOMLY SEGMENTED THERMOPLASTIC POLYURETHANES AS MATRIX FOR ELECTROCHEMICAL ANALYSIS OF Ca++ IONS |
| WO2003067286A2 (en) * | 2002-02-07 | 2003-08-14 | Covalent Partners, Llc | Nanofilm and membrane compositions |
| US20040034223A1 (en) * | 2002-02-07 | 2004-02-19 | Covalent Partners, Llc. | Amphiphilic molecular modules and constructs based thereon |
| US20040106741A1 (en) * | 2002-09-17 | 2004-06-03 | Kriesel Joshua W. | Nanofilm compositions with polymeric components |
| EP1999468A2 (en) * | 2005-09-16 | 2008-12-10 | The Charles Stark Draper Laboratory, Inc. | Reaction sensing in living cells |
| US20080044879A1 (en) * | 2006-08-17 | 2008-02-21 | The Charles Stark Draper Laboratory, Inc. | Systems and methods of voltage-gated ion channel assays |
| US8470300B2 (en) | 2008-09-08 | 2013-06-25 | The Charles Stark Draper Laboratory, Inc. | Coated sensors and methods related thereto |
| ITUB20155007A1 (it) * | 2015-10-29 | 2017-04-29 | Everflow Srl | apparecchiatura per il trattamento del sangue |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3843505A (en) * | 1970-06-26 | 1974-10-22 | T Higuchi | Ion-selective electrodes for organic ions |
| US3706649A (en) * | 1970-06-29 | 1972-12-19 | Beckman Instruments Inc | Electrochemical electrode |
| US3729401A (en) * | 1972-03-01 | 1973-04-24 | Beckman Instruments Inc | Calcium ion measuring electrode |
| CH589096A5 (cs) * | 1972-04-24 | 1977-06-30 | Moeller W Glasblaeserei | |
| GB1437091A (en) * | 1972-10-02 | 1976-05-26 | Radiometer As | Calcium electrode and membrane and composition for use therein |
| US4251470A (en) * | 1979-10-26 | 1981-02-17 | University Of Utah | Process for preparing di[p-(1,1,3,3-tetramethylbutyl)phenyl] phosphoric acid ester |
-
1980
- 1980-04-24 CS CS802865A patent/CS213944B1/cs unknown
-
1981
- 1981-04-01 US US06/250,019 patent/US4379041A/en not_active Expired - Fee Related
- 1981-04-09 GB GB8111134A patent/GB2086925B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US4379041A (en) | 1983-04-05 |
| GB2086925A (en) | 1982-05-19 |
| GB2086925B (en) | 1983-12-14 |
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