US4813973A
Expired / Lapsed
US
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Modified, water-soluble polymers containing amide groups reacted with xanthydrol and other dyes
Assignee: University of Toronto Innovations Foundation
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Filing: 1988-01-11
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Granted: 1989-03-21
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Expires: 2008-01-11
Abstract
Abstract Water-soluble, amide group containing polymers such as polyacrylamide are modified, to render them easy to detect, by reacting the polymer in aqueous solution with organic dye molecules which can form stable carbo-cations reversibly in water. The labelled polymers can then be detected spectrophotometrically. An example of a suitable dye molecule is 9-xanthydrol.
Inventors
- 👤 Mitchell A. Winnik
- 👤 Robert M. Borg
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 19:15
CPC Classifications
C; C09; C09B; C09B69/00; C09B69/10; C08; C08F; C08F8/00
Claims Analysis
Total Claims: 30
Claim 1
Independent Claim
55 words
A process of preparing modified, water-soluble polymers containing pendant amide groups, said process comprising reacting organic dye molecules which can form carbocations reversibly in water, with said polymers in an aqueous solution to attach said dye molecules to said amide groups; wherein the pK R+ value of the dye molecules is from -6 to +7.
Claim 2
Dependent Claim
55 words
A process of preparing modified, water-soluble polymers containing pendant amide groups, said process comprising reacting organic dye molecules which can form carbocations reversibly in water, with said polymers in an aqueous solution to attach said dye molecules to said amide groups; wherein the pK R+ value of the dye molecules is from -6 to +7.
Claim 3
Dependent Claim
18 words
The process of claim 1 wherein the pK R+ value of said molecules is from -4 to +4.
Claim 4
Dependent Claim
32 words
The process of claim 1 wherein said dye molecules comprise dye groups and carbocation-forming groups; said carbocation-forming groups being selected from the group comprising alcohols, ethers, chlorides, bromides, iodides, tosylates and esters.
Claim 5
Dependent Claim
25 words
The process of claim 3 wherein said carbocation-forming groups are selected from xanthyl, tropylium, benzo- and dibenzotropylium, triarylmethyl, alkyldiarylcyclopropenyl, aryldialkylcyclopropenyl, trialkylcyclopropenyl, diarylcyclopropenyl, alkylarylcyclopropenyl and dialkylcyclopropenyl.
Claim 6
Dependent Claim
11 words
The process of claim 3 wherein said dye groups are fluorescent.
Claim 7
Dependent Claim
58 words
The process of claim 3 wherein said dye groups are selected from polynuclear aromatic hydrocarbons and derivatives thereof, azo dyes and derivatives thereof, coumarins and derivatives thereof chromones and derivatives thereof, polyenes and derivatives thereof, benzoxazines and derivatives thereof, cyanines and derivatives thereof, xanthenes and derivatives thereof, acridines and derivatives thereof, fluorescein and rhodamine dyes and indigoid dyes.
Claim 8
Dependent Claim
23 words
The process of claim 1 wherein said dye molecules are selected from 9-xanthydrol, xanthydrol, dibenzosuberenol, 9-anthryl-di-(4-methoxyphenyl)methanol, other polynuclear aromatic hydrocarbons, and scintillator dyes.
Claim 9
Dependent Claim
29 words
The process of claim 1 wherein from 1 to 15 parts by weight of dye molecule per 100 parts by weight of said polymer are reacted with said polymer.
Claim 10
Dependent Claim
18 words
The process of claim 1 wherein said polymer is selected from polyamides, polyacrylamides, polyacrylamide copolymers, and polyacrylamide derivatives.
Claim 11
Dependent Claim
46 words
The process of claim 9 wherein said polyacrylamide copolymers include partially hydrolyzed polyacrylamide, polyacrylamide modified by Hoffmann Degradation, polyacrylamide modified by the Mannich Reaction, copolymers with acrylic acid and its salts or derivatives, copolymers with N-alkyl or N-aryl acrylamide, copolymers with N,N-dialkyl, N,N-diaryl, and N-aryl-N-alkyl acrylamides.
Claim 12
Dependent Claim
19 words
The process of claim 9 wherein said derivatives contain groups selected from anionic groups, cationic groups and hydrophobic groups.
Claim 13
Dependent Claim
14 words
The process of claim 11 wherein said anionic groups include sulphate, sulphonate and carboxylate.
Claim 14
Dependent Claim
14 words
The process of claim 11 wherein said cationic groups include ammonium and alkyl ammonium.
Claim 15
Dependent Claim
17 words
The process of claim 1 further including the step of detecting said polymers by UV absorption measurement.
Claim 16
Dependent Claim
16 words
The process of claim 5 further including the step of detecting said polymers by fluorescence measurements.
Claim 17
Dependent Claim
28 words
The process of claim 1 wherein the reaction is carried out in a solvent selected from water, acetic acid, formic acid, water-acetic acid mixtures, and water-formic acid mixtures.
Claim 18
Dependent Claim
22 words
The process of claim 16 wherein said solvent is selected from 5-90% acetic acid in water and 5-90% formic acid in water.
Claim 19
Dependent Claim
14 words
The process of claim 1 wherein the reaction is carried out at 0°-40° C.
Claim 20
Dependent Claim
14 words
The process of claim 18 wherein the reaction is carried out at 10°-30° C.
Claim 21
Dependent Claim
27 words
The process of claim 1 wherein the reaction is carried out in the presence of an acid catalyst selected from mineral acids and water miscible organic acids.
Claim 22
Dependent Claim
33 words
The process of claim 20 wherein the reaction is carried out in the presence of an acid catalyst selected from sulfuric acid, hydrochloric acid, formic acid, acetic acid and water miscible organic acids.
Claim 23
Dependent Claim
18 words
The process of claim 1 wherein from 0.1 to 20% by weight polymer is present in said solution.
Claim 24
Dependent Claim
17 words
The process of claim 23 wherein 0.5 to 2% by weight polymer is present in said solution.
Claim 25
Dependent Claim
26 words
The process of claim 1 wherein following reaction of said polymer and said dye molecule, a polymer precipitant is added to precipitate the polymer from solution.
Claim 26
Dependent Claim
20 words
The process of claim 24 wherein said precipitant is selected from ethanol, methanol, isopropyl alcohol, acetone, tetrahydrofuran, dioxan and acetonitrile.
Claim 27
Dependent Claim
18 words
The process of claim 24 wherein 5 to 30 times the volume of solution of precipitant is added.
Claim 28
Dependent Claim
18 words
The process of claim 26 wherein 5 to 10 times the volume of solution of precipitant is added.
Claim 29
Dependent Claim
13 words
The process of claim 7 wherein said scintillator dyes comprise terphenyl and 1,4-bis(2-(5-phenyloxazolyl))benzene.
Claim 30
Dependent Claim
40 words
The process of claim 9 wherein said polyacrylamide copolymers include polymethacrylamide, copolymers of methacrylamide with acrylic acid and its salts or derivatives, copolymers of methacrylamide with N-alkyl or N-aryl acrylamide and copolymers of methacrylamide with N,N-dialkyl, N,N-diaryl, and N-aryl-N-alkyl acrylamides.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-03-20 | 1992-09-19 | 1993-03-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-03-20 | 1996-09-19 | 1997-03-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-03-20 | 2000-09-19 | 2001-03-21 | $7700.00 | Window Closed / Lapsed |