US4476007A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Hemispherands and sodium-selective compositions and electrodes containing same
Assignee: Clinical Diagnostic Systems Inc
•
Filing: 1983-05-20
•
Granted: 1984-10-09
•
Expires: 2003-05-20
Abstract
Abstract Ion-selective compositions which comprise an ion carrier, a compound capable of solvating the ion carrier, and a supporting matrix are disclosed. The ion carriers of this invention are hemispherand compounds represented by the formula ##STR1## wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aryl or a heterocyclic group; and X is benzyl or an electron donating group capable of forming at least one coordinating site for sodium ions. A preferred hemispherand according to this invention is 2'-benzyloxy-3,3"-[2,6-pyridylenebis(methyleneoxymethylene)]-2,2"-tetramethylenedioxy-5,5',5"-trimethyl-1,1':3',1"-terphenyl. These compounds and the compositions containing same are particularly useful in ion-selective electrodes. Such an electrode is capable of selectively transporting sodium ions in preference to other cations. Dry-operative electrodes using these ion-selective compositions as membranes are also disclosed.
Inventors
- 👤 John L. Toner
- 👤 Daniel S. Daniel
- 👤 Susan M. Geer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 23:23
CPC Classifications
C; C07; C07D; C07D498/00; C07D498/22; G; G01; G01N; G01N27/00; G01N27/26; G01N27/28; G01N27/30; G01N27/333; G01N27/3335
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
52 words
A lipophilic hemispherand compound represented by the structure: ##STR6## wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aryl or a heterocyclic group; and X is benzyl or an electron donating group capable of forming at least one coordinating site for sodium ions.
Claim 2
Dependent Claim
52 words
A lipophilic hemispherand compound represented by the structure: ##STR6## wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aryl or a heterocyclic group; and X is benzyl or an electron donating group capable of forming at least one coordinating site for sodium ions.
Claim 3
Dependent Claim
23 words
The compound of claim 1 wherein each of R 1 , R 2 , R 3 and R 4 is hydrogen or alkyl.
Claim 4
Dependent Claim
34 words
The compound of claim 1 wherein X is benzyl, pyridylalkylene, or alkyl of 1 to 6 carbon atoms substituted with a carbonyl, thiono, amino, alkoxy, thio, sulfinyl, phosphinyl, phosphinyl oxide, tetrahydrofuryl or furyl group.
Claim 5
Dependent Claim
10 words
The hemispherand of claim 3, wherein said benzyl is unsubstituted.
Claim 6
Dependent Claim
3 words
The hemispherand 2'-benzyloxy-3,3"-[2,6-pyridylenebis(methyleneoxymethylene)]-2,2"-tetramethylenedioxy-5,5',5"-trimethyl-1,1'-3',1"-terphenyl.
Claim 7
Dependent Claim
3 words
The hemispherand 2'-benzyloxy-3,3"-[2,6-pyridylenebis(methyleneoxymethylene)]-2,2"-tetramethylenedioxy-5,5',5"-trimethyl-1,1'-3',1"-terphenyl.
Claim 8
Dependent Claim
65 words
A sodium ion-selective composition comprising a lipophilic hemispherand compound represented by the structure: ##STR7## wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aryl or a heterocyclic group; and X is benzyl or an electron donating group capable of forming at least one coordinating site for sodium ions; and a compound capable of solvating said hemispherand.
Claim 9
Dependent Claim
65 words
A sodium ion-selective composition comprising a lipophilic hemispherand compound represented by the structure: ##STR7## wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aryl or a heterocyclic group; and X is benzyl or an electron donating group capable of forming at least one coordinating site for sodium ions; and a compound capable of solvating said hemispherand.
Claim 10
Dependent Claim
9 words
The composition of claim 6 comprising a supporting matrix.
Claim 11
Dependent Claim
14 words
The composition of claim 6 wherein said solvating compound is a hydrophobic carrier solvent.
Claim 12
Dependent Claim
34 words
The composition of claim 8, wherein said carrier solvent is selected from the group consisting of phthalates, sebacates, aromatic and aliphatic ethers, phosphates, mixed aromatic-aliphatic phosphonates, adipates, nitrated ethers or esters, and mixtures thereof.
Claim 13
Dependent Claim
7 words
A composition comprising 2'-benzyloxy-3,3"-[2,6-pyridylenebis(methyleneoxymethylene)]-2,2"-tetramethylenedioxy-5,5',5"-trimethyl-1,1':3',1"-terphenyl and diisodecyl phthalate.
Claim 14
Dependent Claim
7 words
A composition comprising 2'-benzyloxy-3,3"-[2,6-pyridylenebis(methyleneoxymethylene)]-2,2"-tetramethylenedioxy-5,5',5"-trimethyl-1,1':3',1"-terphenyl and diisodecyl phthalate.
Claim 15
Dependent Claim
9 words
The composition of claim 10 comprising carboxylated poly(vinyl chloride).
Claim 16
Dependent Claim
78 words
A sodium ion-selective electrode having an ion selective membrane composition comprising an ionophore which is a lipophilic hemispherand compound represented by the structure: ##STR8## wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aryl or a heterocyclic group; and X is benzyl or an electron donating group capable of forming at least one coordinating site for sodium ions, a compound capable of solvating said hemispherand and a supporting matrix.
Claim 17
Dependent Claim
78 words
A sodium ion-selective electrode having an ion selective membrane composition comprising an ionophore which is a lipophilic hemispherand compound represented by the structure: ##STR8## wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aryl or a heterocyclic group; and X is benzyl or an electron donating group capable of forming at least one coordinating site for sodium ions, a compound capable of solvating said hemispherand and a supporting matrix.
Claim 18
Dependent Claim
94 words
A sodium ion-selective electrode comprising: (a) a reference electrode in contact with (b) a reference composition which is, in turn, in contact with one side of (c) an ion-selective membrane composition comprising a lipophilic hemispherand represented by the structure: ##STR9## wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aryl or a heterocyclic group; and X is benzyl or an electron donating group capable of forming at least one coordinating site for sodium ions, a compound capable of solvating said hemispherand and a supporting matrix.
Claim 19
Dependent Claim
94 words
A sodium ion-selective electrode comprising: (a) a reference electrode in contact with (b) a reference composition which is, in turn, in contact with one side of (c) an ion-selective membrane composition comprising a lipophilic hemispherand represented by the structure: ##STR9## wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aryl or a heterocyclic group; and X is benzyl or an electron donating group capable of forming at least one coordinating site for sodium ions, a compound capable of solvating said hemispherand and a supporting matrix.
Claim 20
Dependent Claim
34 words
The electrode of claim 13, wherein said solvating compound is selected from the group consisting of phthalates, sebacates, aromatic and aliphatic ethers, phosphates, mixed aromatic-aliphatic phosphonates, adipates, nitrated ethers or esters, and mixtures thereof.
Claim 21
Dependent Claim
12 words
The electrode of claim 13, wherein said supporting matrix is porous glass.
Claim 22
Dependent Claim
13 words
The electrode of claim 13, wherein said supporting matrix is a hydrophobic polymer.
Claim 23
Dependent Claim
8 words
The electrode of claim 13, comprising a surfactant.
Claim 24
Dependent Claim
71 words
The dry-operative sodium ion-selective electrode comprising a lipopholic hemispherand ionophore dissolved in a compound capable of solvating said hemispherand compound, said hemispherand compound represented by the structure: ##STR10## wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aryl or a heterocyclic group; and X is benzyl or an electron donating group capable of forming at least one coordinating site for sodium ion.
Claim 25
Dependent Claim
71 words
The dry-operative sodium ion-selective electrode comprising a lipopholic hemispherand ionophore dissolved in a compound capable of solvating said hemispherand compound, said hemispherand compound represented by the structure: ##STR10## wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aryl or a heterocyclic group; and X is benzyl or an electron donating group capable of forming at least one coordinating site for sodium ion.
Claim 26
Dependent Claim
17 words
The electrode of claim 18 wherein said ionophore and solvating compound are distributed within a hydrophobic binder.
Claim 27
Dependent Claim
141 words
A dry-operative sodium ion-selective electrode comprising: (a) a dried internal reference element comprising the dried residue of a solution of a salt and a hydrophilic polymeric binder in a solvent for the polymer and the salt and, (b) in contact with said reference element, a hydrophobic ion-selective membrane of predetermined uniform thickness in regions thereof intended for contact with a sample for analysis, the membrane comprising a hydrophobic polymeric binder having distributed therein a hemispherand compound represented by the structure: ##STR11## wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aryl or a heterocyclic group; and X is benzyl or an electron donating group capable of forming at least one coordinating site for sodium ions, dissolved in a compound capable of solvating said hemispherand, which solvating compound is a hydrophobic carrier solvent.
Claim 28
Dependent Claim
141 words
A dry-operative sodium ion-selective electrode comprising: (a) a dried internal reference element comprising the dried residue of a solution of a salt and a hydrophilic polymeric binder in a solvent for the polymer and the salt and, (b) in contact with said reference element, a hydrophobic ion-selective membrane of predetermined uniform thickness in regions thereof intended for contact with a sample for analysis, the membrane comprising a hydrophobic polymeric binder having distributed therein a hemispherand compound represented by the structure: ##STR11## wherein R 1 , R 2 , R 3 and R 4 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aryl or a heterocyclic group; and X is benzyl or an electron donating group capable of forming at least one coordinating site for sodium ions, dissolved in a compound capable of solvating said hemispherand, which solvating compound is a hydrophobic carrier solvent.
Claim 29
Dependent Claim
23 words
The electrode of claim 20 wherein each of R 1 , R 2 , R 3 and R 4 is hydrogen or alkyl.
Claim 30
Dependent Claim
34 words
The electrode of claim 20 wherein X is benzyl, pyridylalkylene, or alkyl of 1 to 6 carbon atoms substituted with a carbonyl, thiono, amino, alkoxy, thio, sulfinyl, phosphinyl, phosphinyl oxide, tetrahydrofuryl or furyl group.
Claim 31
Dependent Claim
10 words
The electrode of claim 22 wherein X is unsubstituted benzyl.
Claim 32
Dependent Claim
34 words
The electrode of claim 20, wherein said carrier solvent is selected from the group consisting of phthalates, sebacates, aromatic and aliphatic ethers, phosphates, mixed aromatic-aliphatic phosphonates, adipates, nitrated ethers and esters, and mixtures thereof.
Claim 33
Dependent Claim
78 words
A dry operative sodium ion-selective electrode comprising: (a) a dried internal reference element comprising the dried residue of a solution of a salt and a hydrophilic polymeric binder in a solvent for the polymer and the salt and, (b) in contact with said reference element, a hydrophobic ion-selective membrane of predetermined uniform thickness in regions thereof intended for contact with a sample for analysis, the membrane comprising a supporting matrix having distributed therein 2'-benzyloxy-3,3"-[2,6-pyridylenebis(methyleneoxymethylene)]-2,2"-tetramethylenedioxy-5,5',5"-trimethyl-1,1':3',1"-terphenyl, dissolved in diisodecyl phthalate.
Claim 34
Dependent Claim
78 words
A dry operative sodium ion-selective electrode comprising: (a) a dried internal reference element comprising the dried residue of a solution of a salt and a hydrophilic polymeric binder in a solvent for the polymer and the salt and, (b) in contact with said reference element, a hydrophobic ion-selective membrane of predetermined uniform thickness in regions thereof intended for contact with a sample for analysis, the membrane comprising a supporting matrix having distributed therein 2'-benzyloxy-3,3"-[2,6-pyridylenebis(methyleneoxymethylene)]-2,2"-tetramethylenedioxy-5,5',5"-trimethyl-1,1':3',1"-terphenyl, dissolved in diisodecyl phthalate.
References Cited (Backward Citations)
US3562129A
Cited
US3598868A
Cited
US3753887A
Cited
US3657095A
Cited
US3743588A
Cited
US3957607A
Cited
US3856649A
Cited
US4001279A
Cited
US4043979A
Cited
US4080337A
Cited
US3965116A
Cited
US4128556A
Cited
US4113959A
Cited
JPS53137080A
Cited
US4236987A
Cited
US4134798A
Cited
US4214968A
Cited
JPS54151994A
Cited
US4227003A
Cited
DE2924285A1
Cited
US4271002A
Cited
JPS5613502A
Cited
JPS5624571A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-10-09 | 1988-04-09 | 1988-10-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-10-09 | 1992-04-09 | 1992-10-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-10-09 | 1996-04-09 | 1996-10-09 | $7700.00 | Window Closed / Lapsed |