WO1979000661A1 - Organic compounds of tin as membrane components - Google Patents
Organic compounds of tin as membrane components Download PDFInfo
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- WO1979000661A1 WO1979000661A1 PCT/CH1979/000030 CH7900030W WO7900661A1 WO 1979000661 A1 WO1979000661 A1 WO 1979000661A1 CH 7900030 W CH7900030 W CH 7900030W WO 7900661 A1 WO7900661 A1 WO 7900661A1
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- 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
Definitions
- the present invention relates to a liquid membrane which has selectivity towards bicarbonate.
- bicarbonate anions in aqueous systems is of great importance, especially in biological systems, such as. B. in body fluids or in the blood, where in addition to the bicarbonate anions there are relatively high amounts of chloride anions.
- organic tin compounds namely lipophilic organic tin compounds
- the present invention therefore relates to a liquid membrane with selectivity towards bicarbonate, which is characterized in that it contains an organic tin compound as a component.
- the preferred organic tin compounds are tetravalent tin compounds.
- Such compounds in which four organic radicals are bonded directly to the tin atom can also be used as a membrane component for the production of membranes which are selective towards bicarbonate, it has been shown that in general such compounds in which only three organic radicals and also one electronegatvie group or only two organic radicals and also two electronegative groups are bonded to the tin atom, have better selectivity towards bicarbonate ions than those tetravalent tin compounds in which four organic radicals are bonded to the tin atom.
- the electronegative groups bonded to the tin atom in addition to the organic radicals are preferably small groups, in particular halogen atoms, etherified hydroxyl groups or hydroxyl groups.
- the organic groups bonded to the tin atom should be free of strongly polar substituents, such as carboxyl groups or amino groups, and such organic radicals are particularly preferred. which carry relatively non-polar groups as substituents, such as halogen atoms or carbonyl groups, or which represent unsubstituted hydrocarbon radicals at all. Saturated or unsaturated aliphatic, cycloaliphatic, aromatic and araliphatic groups are preferred as organic groups, with alkyl groups having 3-12 carbon atoms being particularly preferred.
- Polyvinyl chloride is generally used as the basic component of the membrane, because an extensive literature on ion-selective membranes in which the basic component is polyvinyl chloride, which may contain plasticizers, is already available (in this connection, reference should be made to the cation-selective membranes, which are described in the following publications by the applicant: WEMorf, P.Wuhrmann, W.Simon. Anal.Chem. Volume 48, page 31, 1976, and GJ Moody, RB Oke, JDR Thomas, Analyst, London, Volume 95, page 910 , 1970).
- esters of ⁇ ⁇ -dicarboxylic acids have been found to be particularly suitable, in particular the diesters of ⁇ o-dicarboxylic acids with 8-14 carbon atoms in the dicarboxylic acid component of these esters.
- dicarboxylic acid esters of the corresponding ⁇ -dicarboxylic acid with a total of 10 carbon atoms that is to say the diesters of sebacic acid
- dibutyl sebacate and di (1H, 1H-perfluorobutyl) sebacate of the following formula are special examples called. The invention will now be explained in more detail by means of examples.
- a liquid membrane was produced in which the organic tin compound sensitive to bicarbonate is the di (-n-octyl) tin dichloride of the formula
- the liquid membrane had the following composition:
- Polyvinylchloride 29 This membrane had a selectivity of bicarbonate anions over chloride anions of about 20. The other values of this membrane were as follows:
- the tin compound of the liquid membrane was the di (-n-octyl) tin dichloride.
- the di (1H, 1H-perfluorobutyl) sebacate of the following formula was now used as a further organic component in this membrane in addition to the dibutyl sebacate used.
- the liquid membrane has the following composition:
- This membrane had a selectivity of bicarbonate over chloride anions of 300.
- a liquid membrane was produced in which tri (n-butyl) tin chloride was used as the organic tin compound.
- the liquid membrane had the following composition: constituent amount in% by weight
- This liquid membrane was about 10 times more sensitive to bicarbonate than to chloride.
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Abstract
A liquid membrane having a selectivity with respect to bicarbonate anions contains as ionoselective component and lipophilic compound of tin, particularly a quadrivalent tin compound having the structure SnR4, SnXR3, SnX2R2; in these formulae R is organic remainings, particularly hydrocarbonic remainings and X is an electronegative group, for example an atom of halogen or an etherified hydroxyl group. Such membranes have an excellent selectivity with respect to bicarbonate in presence of chloride, which is highly important when proceeding to the analysis of biological systems.
Description
Organische ZinnVerbindungen als Membrankomponente Organic tin compounds as a membrane component
Die vorliegende Erfindung betrifft eine Flüssigmembran, welche eine Selektivität gegenüber Bicarbonat besitzt.The present invention relates to a liquid membrane which has selectivity towards bicarbonate.
Die Bestimmung von Bicarbonat-Anionen in wässrigen Systemen ist von grosser Wichtigkeit, und zwar insbesondere in biologischen Systemen , wie z . B . in Körperflüs sigkeiten oder im Blut, wo neben den Bicarbonat-Anionen relativ hohe Mengen an Chlorid-Anionen vorliegen.The determination of bicarbonate anions in aqueous systems is of great importance, especially in biological systems, such as. B. in body fluids or in the blood, where in addition to the bicarbonate anions there are relatively high amounts of chloride anions.
Bisher erfolgte die Bestimmung von Bicarbonat dadurch, dass in der Probe der CO2 Partialdruck und auch der pH-Wert bestimmt wurde, und dass daraus dann der Bicarbonatgehalt berechnet wurde. Dieses Verfahren ist nicht nur langwierig, sondern dadurch, dass zwei Werte bestimmt werden müssen, auch sehr fehleranfällig. In der US-Patentschrift Nr. 3 723 281 aus demSo far, bicarbonate has been determined by determining the CO 2 partial pressure and also the pH in the sample, and then calculating the bicarbonate content. This procedure is not only lengthy, but also very prone to errors due to the fact that two values have to be determined. U.S. Patent No. 3,723,281 issued to
Jahr 1973 wird gesagt, dass quaternäre Alkylammoniumverbindungen eine Selektivität gegenüber Bicarbonationen besitzen und als Komponente in Bicarbonat-empfindlichen
Flüssigkeitsmembranen eingesetzt werden können. Diese Membranen wurden bisher jedoch praktisch noch nicht verwendet.1973 is said to have selectivity towards bicarbonate ions and as a component in bicarbonate-sensitive quaternary alkylammonium compounds Liquid membranes can be used. However, these membranes have so far not been used practically.
Es wurde nun überraschenderweise gefunden, dass organische Zinnverbindungen, nämlich lipophile organische Zinnverbindungen eine Selektivität gegenüber Bicarbonat besitzen und als Komponente von Flüssigmembranen eingesetzt werden können, die zur Bestimmung der Bicarbonatkonzentration in Anwesenheit relativ grosser Chloridmengen geeignet sind. Gegenstand der vorliegenden Erfindung ist daher eine Flüssigmembran mit Selektivität gegenüber Bicarbonat, die dadurch gekennzeichnet ist, dass sie als Komponente eine organische ZinnVerbindung enthält. Die bevorzugten organischen Zinnverbindungen sind Verbindungen des vierwertigen Zinns. Obwohl auch solche Verbindungen, bei denen vier organische Reste direkt an das Zinnatom gebunden sind, als Membrankomponente zur Herstellung von gegenüber Bicarbonat selektiver Membranen herangezogen werden können, hat es sich gezeigt, dass im allgemeinen solche Verbindungen, bei denen nur drei organische Reste und ausserdem eine elektronegatvie Gruppe oder nur zwei organische Reste und ausserdem zwei elektronegative Gruppen an das Zinr-atom gebunden sind, eine bessere Selektivität gegenüber Bicarbonationen aufweisen, als solche vierwertige Zinnverbindungen, bei denen vier organische Reste an das Zinnatom gebunden sind. Die zusätzlich zu den organischen Resten an das Zinnatom gebundenen elektronegativen Gruppen sind vorzugsweise kleine Gruppen, insbesondere Halogenatome, verätherte Hydroxylgruppen oder Hydroxylgruppen. Um zu erreichen, dass die Zinnverbindungen lipophile Eigenschaften besitzen, sollen die an das Zinnatom gebundenen organischen Gruppen frei von stark polaren Sub¬stituenten, wie z.B. Carboxylgruppen oder Aminogruppen sein und speziell bevorzugt sind solche organische Reste,
welche als Substituenten relativ unpolare Gruppierungen, wie z.B. Halogenatome oder Carbonylgruppen tragen, oder welche überhaupt unsubstituierte Kohlenwasserstoffreste darstellen. Als organische Gruppen sind gesättigte oder ungesättigte aliphatische, cycloaliphatische, aromatische und araliphatische Gruppen bevorzugt, wobei speziell bevorzugt Alkylgruppen mit 3-12 Kohlenstoffatomen sind. Als Grundkomponente der Membran wird im allgemeinen Polyvinylchlorid verwendet, und zwar deshalb, weil bereits eine ausgedehnte Literatur über ionenselektive Membranen, in welchen die Grundkomponente Polyvinylchlorid ist, welches gegebenenfalls Weichmacher enthält, vorhanden ist (es sei in diesem Zusammenhang auf die kationselektiven Membranen hingewiesen, die in den folgenden Veröffentlichungen des Anmelders beschrieben sind: W.E.Morf, P.Wuhrmann, W.Simon. Anal.Chem. Band 48 , Seite 31, 1976, sowie G.J. Moody, R.B. Oke, J.D.R. Thomas, Analyst, London, Band 95, Seite 910, 1970).It has now surprisingly been found that organic tin compounds, namely lipophilic organic tin compounds, have a selectivity towards bicarbonate and can be used as a component of liquid membranes which are suitable for determining the bicarbonate concentration in the presence of relatively large amounts of chloride. The present invention therefore relates to a liquid membrane with selectivity towards bicarbonate, which is characterized in that it contains an organic tin compound as a component. The preferred organic tin compounds are tetravalent tin compounds. Although such compounds in which four organic radicals are bonded directly to the tin atom can also be used as a membrane component for the production of membranes which are selective towards bicarbonate, it has been shown that in general such compounds in which only three organic radicals and also one electronegatvie group or only two organic radicals and also two electronegative groups are bonded to the tin atom, have better selectivity towards bicarbonate ions than those tetravalent tin compounds in which four organic radicals are bonded to the tin atom. The electronegative groups bonded to the tin atom in addition to the organic radicals are preferably small groups, in particular halogen atoms, etherified hydroxyl groups or hydroxyl groups. In order to ensure that the tin compounds have lipophilic properties, the organic groups bonded to the tin atom should be free of strongly polar substituents, such as carboxyl groups or amino groups, and such organic radicals are particularly preferred. which carry relatively non-polar groups as substituents, such as halogen atoms or carbonyl groups, or which represent unsubstituted hydrocarbon radicals at all. Saturated or unsaturated aliphatic, cycloaliphatic, aromatic and araliphatic groups are preferred as organic groups, with alkyl groups having 3-12 carbon atoms being particularly preferred. Polyvinyl chloride is generally used as the basic component of the membrane, because an extensive literature on ion-selective membranes in which the basic component is polyvinyl chloride, which may contain plasticizers, is already available (in this connection, reference should be made to the cation-selective membranes, which are described in the following publications by the applicant: WEMorf, P.Wuhrmann, W.Simon. Anal.Chem. Volume 48, page 31, 1976, and GJ Moody, RB Oke, JDR Thomas, Analyst, London, Volume 95, page 910 , 1970).
Es hat sich ferner gezeigt, dass es vorteilhaft ist der Membran ausser der organischen Zinnverbindung noch eine organische Komponente einzuverleiben, welche ein lipophiles Grundgerüst und ausserdem zusätzlich polare Gruppen, insbesondere Estergruppen, besitzt. Zu diesem Zweck haben sich die Ester von α ω-Dicarbonsäuren besonders gut geeignet herausgestellt, insbesondere die Diester von αo-Dicarbonsäuren mit 8-14 Kohlenstoffatomen in der Dicarbonsäurekomponente dieser Ester. Speziell vorteilhaft sind dabei die Dicarbonsäure-ester der entsprechenden αω-Dicarbonsäure mit insbesamt 10 Kohlenstoffatomen, also die Diester der Sebacinsäure, und als spezielle Beispiele seien das Dibutylsebacat und das Di-(1H,1H-perfluorbutyl)sebacat der folgenden Formel
genannt.
Die Erfindung sei nun anhand von Beispielen näher erläutert.It has also been shown that it is advantageous to incorporate an organic component into the membrane in addition to the organic tin compound, which has a lipophilic backbone and also additional polar groups, in particular ester groups. For this purpose, the esters of α ω-dicarboxylic acids have been found to be particularly suitable, in particular the diesters of αo-dicarboxylic acids with 8-14 carbon atoms in the dicarboxylic acid component of these esters. The dicarboxylic acid esters of the corresponding αω-dicarboxylic acid with a total of 10 carbon atoms, that is to say the diesters of sebacic acid, are particularly advantageous, and dibutyl sebacate and di (1H, 1H-perfluorobutyl) sebacate of the following formula are special examples called. The invention will now be explained in more detail by means of examples.
Beispiel 1example 1
Es wurde eine Flüssigmembran hergestellt, in weleher die gegenüber Bicarbonat empfindliche organische Zinnverbindung das Di(-n-octyl)-zinndichlorid der FormelA liquid membrane was produced in which the organic tin compound sensitive to bicarbonate is the di (-n-octyl) tin dichloride of the formula
Cl2 Sn(n-Oct) war.Cl 2 Sn (n-Oct).
Die Flüssigmembran wies die folgende Zusammensetzung auf:The liquid membrane had the following composition:
Bestandteil Gew.-%Component weight%
Octyl-zinndichlorid 3Octyl tin dichloride 3
Dibutylsebacat 68Dibutyl sebacate 68
Polyvinylchlorid 29 Diese Membran wies eine Selektivität von Bicarbonat-Anionen gegenüber Chloridanionen von etwa 20 auf. Die weiteren Werte dieser Membran waren die folgenden:Polyvinylchloride 29 This membrane had a selectivity of bicarbonate anions over chloride anions of about 20. The other values of this membrane were as follows:
Steilheit = 52 mV 10- 2 + 10-4M HCO-Slope = 52 mV 10 - 2 + 10 -4 M HCO-
= 1 , 3 log kHCO3-Cl= 1.3 l and k HCO 3 -Cl
Beispiel 2Example 2
Auch in diesem Beispiel war die Zinnverbindung der Flüssigmembran das Di(-n-octyl)-zinndichlord. Im Unterschied zum Beispiel 1 wurde jedoch jetzt als weitere organische Komponente in dieser Membran zusätzlich zu dem Dibutylsebacat auch das Di(1H,1H-perfluor-butyl)sebacat der folgenden Formel
verwendet. Die Flüssigmembran hatt die folgende Zusammensetzung:In this example too, the tin compound of the liquid membrane was the di (-n-octyl) tin dichloride. In contrast to Example 1, however, the di (1H, 1H-perfluorobutyl) sebacate of the following formula was now used as a further organic component in this membrane in addition to the dibutyl sebacate used. The liquid membrane has the following composition:
Bestandteil Menge in Gew.-%Component amount in% by weight
Cl2 Sn(n-Oct)2 7Cl 2 Sn (n-Oct) 2 7
Dibutylsebacat 54 Di-(1H,1H-perfluorbutyl)sebacat 13Dibutyl sebacate 54 di- (1H, 1H-perfluorobutyl) sebacate 13
Polyvinylchlorid 26Polyvinyl chloride 26
Diese Membran hatte eine Selektivität von Bicarbonat gegenüber Chloridanionen von 300.This membrane had a selectivity of bicarbonate over chloride anions of 300.
Die weiteren Eigenschaften der Membran waren die folgenden:The other properties of the membrane were as follows:
Steilheit = -42,0 mVSlope = -42.0 mV
10-1 - 10-3M HCO3 ¬ log KHCO3-Cl = 2,5 - 2,110 -1 - 10 -3 M HCO 3 ¬ log K HCO 3 -Cl = 2.5 - 2.1
Beispiel 3Example 3
Es wurde eine Flüssigmembran hergestellt, in welcher als organische Zinnverbindung Tri(n-butyl)-zinnchlorid verwendet wurde. Die Flüssigmembran hatte die folgende Zusammensetzung: Bestandteile Menge in Gew.-%A liquid membrane was produced in which tri (n-butyl) tin chloride was used as the organic tin compound. The liquid membrane had the following composition: constituent amount in% by weight
(n-Butyl)3SnCl 69(n-butyl) 3 SnCl 69
Di-(1H,1H-perfluorbutyl)sebacat 5Di- (1H, 1H-perfluorobutyl) sebacate 5
Polyvinylchlorid 26Polyvinyl chloride 26
Diese Flüssigmembran war gegenüber Bicarbonat etwa 10-mal so empfindlich wie gegenüber Chlorid.
This liquid membrane was about 10 times more sensitive to bicarbonate than to chloride.
Claims
1. Flüssigmembran mit Selektivität gegenüber Bicarbonat, dadurch gekennzeichnet, dass sie als Komponente eine organische Zinnverbindung enthält.1. Liquid membrane with selectivity to bicarbonate, characterized in that it contains an organic tin compound as a component.
2. Flüssigmembran gemäss Anspruch 1, dadurch gekennzeichnet, dass sie als Komponente eine organische Zinnverbindung des vierwertigen Zinns enthält, bei der vorzugsweise neben den organischen Resten noch 1 bis 3 elektronegative Gruppen, insbesondere Halogen oder gegebenenfalls verätherte Hydroxylgruppen an das Zinnatom gebunden sind. 2. Liquid membrane according to claim 1, characterized in that it contains as component an organic tin compound of tetravalent tin, in which 1 to 3 electronegative groups, in particular halogen or optionally etherified hydroxyl groups, are preferably bonded to the tin atom in addition to the organic radicals.
3. Flüssigmembran gemäss Anspruch 1 oder 2, dadurch gekennzeichnet, dass die an das Zinnatom gebundenen organischen Gruppen aliphatische oder cycloaliphatische Gruppen oder aromatische Gruppen sind. 3. Liquid membrane according to claim 1 or 2, characterized in that the organic groups bonded to the tin atom are aliphatic or cycloaliphatic groups or aromatic groups.
4. Flüssigmembran nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass die organischen Gruppen frei von polaren Substituenten sind und vorzugsweise Kohlenwasserstoffgruppen darstellen.4. Liquid membrane according to one of claims 1 to 3, characterized in that the organic groups are free of polar substituents and preferably represent hydrocarbon groups.
5. Flüssigmembran nach Anspruch 4, dadurch gekennzeichnet, dass die organischen Gruppen der Verbindung des vierwertigen Zinns Alkylgruppen mit 3-12 Kohlenstoffatomen sind.5. Liquid membrane according to claim 4, characterized in that the organic groups of the compound of tetravalent tin are alkyl groups with 3-12 carbon atoms.
6. Flüssigmembran nach Anspruch 5, dadurch gekennzeichnet, dass die organische Zinnverbindung die Formel Cl2 Sn(n-Oct)2 in welcher n-Oct die Bedeutung von n-Octylresten besitzt oder die Formel6. Liquid membrane according to claim 5, characterized in that the organic tin compound has the formula Cl 2 Sn (n-oct) 2 in which n-oct has the meaning of n-octyl radicals or the formula
Cl - Sn(n-But)3 in welcher n-But die Bedeutung von n-Butylresten besitzt, aufweist .Cl - Sn (n-but) 3 in which n-but has the meaning of n-butyl radicals, having .
7. Flüssigmembran nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass sie zusätzlich zu der organischen ZinnVerbindung eine Komponente enthält, welche ein lipophiles Grundgerüst und ausserdem polare Gruppen, z.B. Estergruppen, aufweist und gegebenenfalls fluoriert ist.7. Liquid membrane according to one of claims 1 to 6, characterized in that it contains, in addition to the organic tin compound, a component which has a lipophilic backbone and also polar groups, e.g. Ester groups, and is optionally fluorinated.
8. Flüssigmembran nach Anspruch 7, dadurch gekennzeichnet, dass die zusätzliche Komponente ein Diester einer αω-Dicarbonsäure, wobei die Dicarbonsäurekomponente dieses Esters vorzugsweise 8-14 Kohlenstoffatome aufweist, ist.8. Liquid membrane according to claim 7, characterized in that the additional component is a diester of an αω-dicarboxylic acid, the dicarboxylic acid component of this ester preferably having 8-14 carbon atoms.
9. Flüssigmembran nach Anspruch 8, dadurch gegekennzeichnet, dass die zusätzliche Komponente ein Sebacinsäure-diester, vorzugsweise Dibutylsebacat oder Di(1H,1H- perfluor-butyl) sebacat der folgenden Formel9. Liquid membrane according to claim 8, characterized in that the additional component is a sebacic acid diester, preferably dibutyl sebacate or di (1H, 1H-perfluorobutyl) sebacate of the following formula
( 
ist.( is.
10. Flüssigmembran nach einem der Ansprüche 1 bis 9, dadurch gekennzeichnet, dass sie als weitere Komponente Polyvinylchlorid enthält. 10. Liquid membrane according to one of claims 1 to 9, characterized in that it contains polyvinyl chloride as a further component.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2053/78 | 1978-02-24 | ||
| CH205378A CH636451A5 (en) | 1978-02-24 | 1978-02-24 | FLUESSIGMEMBRAN CONTAINING organotin compounds AS A COMPONENT. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1979000661A1 true WO1979000661A1 (en) | 1979-09-06 |
Family
ID=4224822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CH1979/000030 WO1979000661A1 (en) | 1978-02-24 | 1979-02-22 | Organic compounds of tin as membrane components |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0009501A1 (en) |
| CH (1) | CH636451A5 (en) |
| WO (1) | WO1979000661A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0312348A2 (en) * | 1987-10-14 | 1989-04-19 | EASTMAN KODAK COMPANY (a New Jersey corporation) | The use of organotin compounds as anionic ionophores |
| EP0560137A1 (en) * | 1992-03-12 | 1993-09-15 | Firma Willi Möller | Mercury containing complexing agents for anions (halogenides and pseudohalogenides) and method for the determination of halogenides and pseudohalogenides in aqueous media |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3406102A (en) * | 1965-04-07 | 1968-10-15 | Corning Glass Works | Ion-sensitive electrode with organometallic liquid ion-exchanger |
| FR2069636A5 (en) * | 1969-11-20 | 1971-09-03 | Miles Lab |
-
1978
- 1978-02-24 CH CH205378A patent/CH636451A5/en not_active IP Right Cessation
-
1979
- 1979-02-22 WO PCT/CH1979/000030 patent/WO1979000661A1/en unknown
- 1979-09-11 EP EP19790900227 patent/EP0009501A1/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3406102A (en) * | 1965-04-07 | 1968-10-15 | Corning Glass Works | Ion-sensitive electrode with organometallic liquid ion-exchanger |
| FR2069636A5 (en) * | 1969-11-20 | 1971-09-03 | Miles Lab |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0312348A2 (en) * | 1987-10-14 | 1989-04-19 | EASTMAN KODAK COMPANY (a New Jersey corporation) | The use of organotin compounds as anionic ionophores |
| EP0312348A3 (en) * | 1987-10-14 | 1991-04-10 | EASTMAN KODAK COMPANY (a New Jersey corporation) | The use of organotin compounds as anionic ionophores |
| EP0560137A1 (en) * | 1992-03-12 | 1993-09-15 | Firma Willi Möller | Mercury containing complexing agents for anions (halogenides and pseudohalogenides) and method for the determination of halogenides and pseudohalogenides in aqueous media |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0009501A1 (en) | 1980-04-16 |
| CH636451A5 (en) | 1983-05-31 |
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