US5591400A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Method for producing an ionic sensor
Assignee: Terumo Cardiovascular Systems Corp
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Filing: 1994-10-31
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Granted: 1997-01-07
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Expires: 2014-10-31
Abstract
Abstract The present invention provides processes for the preparation of ionic sensors that include a matrix material, such as ion-permeable cellulose, having a sensing component included therein, such as a fluorescent dye, and an opaque overcoat material. For example, the present invention provides a method of making an ionic sensor comprising: contacting a water-swellable ion-permeable matrix material with an aqueous-based bath of a sensing component, or precursor thereof, under conditions effective to covalently attach the sensing component, or precursor thereof, to the water-swellable ion-permeable matrix material; wherein the aqueous-based bath comprises water and an organic solvent in an amount effective to solubilize the sensing component, or precursor thereof; contacting the water-swellable ion-permeable matrix material having covalently attached sensing component, or precursor thereof, with an aqueous solution having a pH of at least about 10 and an ionic strength of at least about that of a 5% aqueous sodium chloride solution to form a sensing element; and covering the sensing element with an opaque overcoat material. Also provided is a method of making a precursor to a preferred sensing component, i.e., acetoxypyrenetris(sulfonyl)chloride, which is made using a thionyl chloride method. If the sensing component is attached to the matrix material using amine groups, any unreacted amine groups can be capped by contacting them with a solution comprising an acetylating agent, an organic amine, and an ethereal solvent.
Inventors
- 👤 John L. Dektar
- 👤 Sanjay L. Patil
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 16:10
CPC Classifications
G; G01; G01N; G01N21/00; G01N21/75; G01N21/62; G01N21/63; G01N21/64; G01N21/6428; G01N2021/6434; G01N21/77; G01N21/7703; G01N2021/7706; G01N2021/773; G01N2021/7769; G01N2021/7786
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
125 words
A method of making an ionic sensor comprising: (a) contacting a water-swellable ion-permeable matrix material with an aqueous-based bath of a sensing component, or precursor thereof, under conditions effective to covalently attach the sensing component, or precursor thereof, to the water-swellable ion-permeable matrix material; wherein the aqueous-based bath comprises water and an organic solvent in an amount effective to solubilize the sensing component, or precursor thereof; (b) contacting the water-swellable ion-permeable matrix material having covalently attached sensing component, or precursor thereof, with an aqueous solution having a pH of at least about 10 and an ionic strength of at least about that of a 5% aqueous sodium chloride solution to form a sensing element; and (c) coveting the sensing element with an opaque overcoat material.
Claim 2
Independent Claim
125 words
A method of making an ionic sensor comprising: (a) contacting a water-swellable ion-permeable matrix material with an aqueous-based bath of a sensing component, or precursor thereof, under conditions effective to covalently attach the sensing component, or precursor thereof, to the water-swellable ion-permeable matrix material; wherein the aqueous-based bath comprises water and an organic solvent in an amount effective to solubilize the sensing component, or precursor thereof; (b) contacting the water-swellable ion-permeable matrix material having covalently attached sensing component, or precursor thereof, with an aqueous solution having a pH of at least about 10 and an ionic strength of at least about that of a 5% aqueous sodium chloride solution to form a sensing element; and (c) coveting the sensing element with an opaque overcoat material.
Claim 3
Dependent Claim
49 words
The method of claim 1 wherein the aqueous solution used in step (b) comprises: (a) a base selected from the group consisting of sodium carbonate, sodium hydroxide, and mixtures thereof; and (b) a salt selected from the group consisting of sodium chloride, sodium acetate, sodium sulfate, and mixtures thereof.
Claim 4
Dependent Claim
41 words
The method of claim 1 wherein the sensing component precursor is acetoxypyrenetris(sulfonyl)chloride, which is made by a method comprising: (a) converting hydroxypyrenetrisulfonate to acetoxypyrenetrisulfonate; and (b) reacting acetoxypyrenetrisulfonate with thionyl chloride and a catalytic amount of disubstituted formamide to form acetoxypyrenetris(sulfonyl)chloride.
Claim 5
Dependent Claim
11 words
The method of claim 1 wherein the aqueous-based bath is buffered.
Claim 6
Dependent Claim
35 words
The method of claim 4 wherein the aqueous-based bath is buffered with a salt selected from the group consisting of sodium carbonate, sodium bicarbonate, sodium monobasic phosphate, sodium dibasic phosphate, sodium borate, and mixtures thereof.
Claim 7
Dependent Claim
72 words
The method of claim 1, prior to the step of covalently attaching the sensing component, or precursor thereof, to the matrix, further including: (a) reacting the water-swellable ion-permeable matrix material with an epoxide having at least two epoxy groups per molecule to form an epoxy-modified matrix material; and (b) reacting the epoxy-modified matrix material with an organic amine having at least two amine groups per molecule to form an amine-modified matrix material.
Claim 8
Dependent Claim
49 words
The method of claim 6 further including a step of capping any unreacted amine groups on the matrix material having the sensing component, or precursor thereof, covalently attached thereto, by contacting the unreacted amine groups with a solution comprising an acetylating agent, an organic amine, and an ethereal solvent.
Claim 9
Dependent Claim
20 words
The method of claim 7 wherein the organic amine is a tertiary amine and the solution further includes a catalyst.
Claim 10
Dependent Claim
12 words
The method of claim 8 wherein the catalyst is a substituted pyridine.
Claim 11
Independent Claim
79 words
A method of making an ionic sensor comprising: (a) reacting acetoxypyrenetris(sulfonyl)chloride with an amine-modified polymeric ion-permeable matrix material to form bound acetoxypyrenesulfonamide; wherein the acetoxypyrenetris(sulfonyl)chloride is made by a method comprising: (i) converting hydroxypyrenetrisulfonate to acetoxypyrenetrisulfonate; and (ii) reacting acetoxypyrenetrisulfonate with thionyl chloride and a catalytic amount of disubstituted formamide to form acetoxypyrenetris(sulfonyl) chloride; (b) converting the bound acetoxypyrenesulfonamide to the hydroxy form to form a sensing element; and (c) covering the sensing element with an opaque overcoat material.
Claim 12
Independent Claim
79 words
A method of making an ionic sensor comprising: (a) reacting acetoxypyrenetris(sulfonyl)chloride with an amine-modified polymeric ion-permeable matrix material to form bound acetoxypyrenesulfonamide; wherein the acetoxypyrenetris(sulfonyl)chloride is made by a method comprising: (i) converting hydroxypyrenetrisulfonate to acetoxypyrenetrisulfonate; and (ii) reacting acetoxypyrenetrisulfonate with thionyl chloride and a catalytic amount of disubstituted formamide to form acetoxypyrenetris(sulfonyl) chloride; (b) converting the bound acetoxypyrenesulfonamide to the hydroxy form to form a sensing element; and (c) covering the sensing element with an opaque overcoat material.
Claim 13
Dependent Claim
13 words
The method of claim 10 wherein the polymeric ion-permeable matrix material is cellulose.
Claim 14
Dependent Claim
41 words
The method of claim 10 wherein the step of reacting acetoxypyrenetris(sulfonyl)chloride with the amine-modified polymeric ion-permeable matrix material comprises reacting them in an aqueous-based bath comprising water, an organic solvent in an amount effective to solubilize the acetoxypyrenetris(sulfonyl)chloride, and buffer salts.
Claim 15
Dependent Claim
49 words
The method of claim 10 further including a step of capping any unreacted amine groups on the matrix material having the sensing component, or precursor thereof, covalently attached thereto, by contacting the unreacted amine groups with a solution comprising an acetylating agent, an organic amine, and an ethereal solvent.
Claim 16
Dependent Claim
51 words
The method of claim 10 wherein the step of converting the bound acetoxypyrenesulfonamide to the bound hydroxy form comprises combining the bound acetoxypyrenesulfonamide with an aqueous solution having a pH of at least about 10 and an ionic strength of at least about that of a 5% aqueous sodium chloride solution.
Claim 17
Dependent Claim
45 words
The method of claim 14 wherein the aqueous solution comprises: (a) a base selected from the group consisting of sodium carbonate, sodium hydroxide, and mixtures thereof; and (b) a salt selected from the group consisting of sodium chloride, sodium acetate, sodium sulfate, and mixtures thereof.
Claim 18
Independent Claim
186 words
A method of making an ionic sensor comprising: (a) applying to a surface of a first polymeric ion-permeable matrix material, a second polymeric ion-permeable matrix material having mixed therein an opaque agent; (b) reacting both matrix materials with an epoxide having at least two epoxy groups per molecule to covalently bond the two matrix materials together and form pendant epoxy groups; (c) reacting the epoxy groups with an organic amine having at least two amine groups per molecule to form pendant amine groups; (d) reacting acetoxypyrenetris(sulfonyl)chloride with the pendant amine groups in an aqueous-based bath comprising water, an organic solvent in an amount effective to solubilize the acetoxypyrenetris(sulfonyl)chloride, and buffer salts, to form bound acetoxypyrenesulfonamide; wherein the acetoxypyrenetris(sulfonyl)chloride is made by a method comprising: (i) converting hydroxypyrenetrisulfonate to acetoxypyrenetrisulfonate; and (ii) reacting acetoxypyrenetrisulfonate with thionyl chloride and a catalytic amount of a disubstituted formamide to form acetoxypyrenetris(sulfonyl) chloride; (e) converting the bound acetoxypyrenesulfonamide to the bound hydroxy form; and (f) capping any unreacted amine groups on the matrix material by contacting them with a solution comprising an acetylating agent, an organic amine, and an ethereal solvent.
Claim 19
Independent Claim
186 words
A method of making an ionic sensor comprising: (a) applying to a surface of a first polymeric ion-permeable matrix material, a second polymeric ion-permeable matrix material having mixed therein an opaque agent; (b) reacting both matrix materials with an epoxide having at least two epoxy groups per molecule to covalently bond the two matrix materials together and form pendant epoxy groups; (c) reacting the epoxy groups with an organic amine having at least two amine groups per molecule to form pendant amine groups; (d) reacting acetoxypyrenetris(sulfonyl)chloride with the pendant amine groups in an aqueous-based bath comprising water, an organic solvent in an amount effective to solubilize the acetoxypyrenetris(sulfonyl)chloride, and buffer salts, to form bound acetoxypyrenesulfonamide; wherein the acetoxypyrenetris(sulfonyl)chloride is made by a method comprising: (i) converting hydroxypyrenetrisulfonate to acetoxypyrenetrisulfonate; and (ii) reacting acetoxypyrenetrisulfonate with thionyl chloride and a catalytic amount of a disubstituted formamide to form acetoxypyrenetris(sulfonyl) chloride; (e) converting the bound acetoxypyrenesulfonamide to the bound hydroxy form; and (f) capping any unreacted amine groups on the matrix material by contacting them with a solution comprising an acetylating agent, an organic amine, and an ethereal solvent.
Claim 20
Dependent Claim
29 words
The method of claim 16 wherein the first polymeric ion-permeable matrix material is cellulose, the second polymeric ion-permeable matrix material is dextran, and the opaque agent is carbon black.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 2000-01-07 | 2000-07-08 | 2001-01-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-01-07 | 2004-07-08 | 2005-01-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-01-07 | 2008-07-08 | 2009-01-07 | $7700.00 | Window Closed / Lapsed |