US4743673A
Expired / Lapsed
US
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Hydrophilic carboxy polyurethanes
Assignee: Tyndale Plains Hunter Ltd
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Filing: 1986-12-19
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Granted: 1988-05-10
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Expires: 2006-12-19
Abstract
Abstract Hydrophilic polyurethane polymers having carboxy groups in the polymer backbone are prepared by reacting a polyol component, an ester of a carboxylic acid and a polyisocyanate to form a polyurethane intermediate. The intermediate is then saponified and the saponified product neutralized to form free carboxy groups. The water absorption of the intermediates and saponified polymers is above 10% and the polyurethanes may range from rigid solids to gel-like, high water absorptive polymers. Neutralization of the carboxy group with ammonium hydroxide produces a water soluble polyurethane which becomes water insoluble when the ammonia is driven off. The carboxy groups introduced into the polymeric chain provide reactive sites for attachment of various side-groups and also allow for various curing procedures. The polymers exhibit excellent adhesion to various substrates, and are suitable for use as light sensitive photographic layers on films, paper or glass; as boat and pipe coatings for decreasing hydrodynamic drag; as drug delivery systems; as burn and wound dressings; in cosmetic applications; in body implants; as coatings on cannulae; and a host of other applications.
Inventors
- 👤 Christian W. Johnston
- 👤 John M. Teffenhart
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 20:54
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/83; C08G18/831; C08G18/832; A; A61; A61K; A61K47/00; A61K47/30; A61K47/34; A61K8/00; A61K8/18; A61K8/72; A61K8/84; A61K8/87; A61L; A61L15/00; A61L15/16; A61L15/22; A61L15/26; A61L27/00; A61L27/14; A61L27/18; A61L29/00; A61L29/04; A61L29/06; A61L29/08; A61L29/085; A61Q; A61Q3/00; A61Q3/02; C08G18/08; C08G18/0804; C08G18/0819; C08G18/0823; C08G18/28; C08G18/30; C08G18/34; C08G18/65; C08G18/66; C08G18/6625; Y; Y10; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31551; Y10T428/31605
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
147 words
A hydrophilic polyurethane ester intermediate consisting essentially of the reaction product of (A) a polyol component comprising at least one of (a) an alkylene glycol, (b) a long chain polyoxyalkylene glycol, and (c) a linear polyester diol derived from the condensation of one or more diols with one or more dibasic acids; (B) a carboxylic acid ester component comprising at least one of (a) a hydroxy carboxylic acid ester selected from at least one of ##STR3## wherein R is an aliphatic group, m and p independently are integers of from 0 to 12, and n is an integer of from 1 to 12; and (b) an amino acid ester having at least two active hydrogen atoms; and (C) an organic isocyanate or isocyanate precursor containing at least two NCO groups; the ratio of NCO to active hydrogen atoms in the reaction mixture being from 0.5/1 to 1/1.
Claim 2
Dependent Claim
147 words
A hydrophilic polyurethane ester intermediate consisting essentially of the reaction product of (A) a polyol component comprising at least one of (a) an alkylene glycol, (b) a long chain polyoxyalkylene glycol, and (c) a linear polyester diol derived from the condensation of one or more diols with one or more dibasic acids; (B) a carboxylic acid ester component comprising at least one of (a) a hydroxy carboxylic acid ester selected from at least one of ##STR3## wherein R is an aliphatic group, m and p independently are integers of from 0 to 12, and n is an integer of from 1 to 12; and (b) an amino acid ester having at least two active hydrogen atoms; and (C) an organic isocyanate or isocyanate precursor containing at least two NCO groups; the ratio of NCO to active hydrogen atoms in the reaction mixture being from 0.5/1 to 1/1.
Claim 3
Dependent Claim
31 words
The hydrophilic polyurethane intermediate of claim 1 wherein the carboxylic acid ester component (B) reacted with said polyol component (A) comprises at least one of said hydroxy carboxylic acid esters (a).
Claim 4
Dependent Claim
24 words
The hydrophilic polyurethane intermediate of claim 1 wherein the carboxylic acid ester component (B) comprises at least one of said amino acid esters (b).
Claim 5
Dependent Claim
34 words
The hydrophilic polyurethane intermediate of claim 2 wherein said polyol component (A) reacted with said carboxylic acid ester comprises at least one of said alkylene glycols (a) and said long chain polyoxyalkylene glycols (b).
Claim 6
Dependent Claim
25 words
The hydrophilic polyurethane intermediate of claim 4 wherein said alkylene glycols (a) are selected from one or a mixture of ethylene glycol and diethylene glycol.
Claim 7
Dependent Claim
24 words
The hydrophilic polyurethane intermediate of claim 2 wherein said polyol component (A) comprises a polyoxyethylene glycol and said organic polyisocynate (C) comprises methylene bis(cyclohexyl-4,4-isocyanate).
Claim 8
Dependent Claim
27 words
The hydrophilic polyurethane intermediate of claim 2 wherein said polyol component (A) comprises diethylene glycol and a polyoxyethylene glycol, and said organic diisocyanate (C) comprises methylene bis(cyclohexyl-4-isocyanate).
Claim 9
Dependent Claim
21 words
The hydrophilic polyurethane intermediate of claim 2 wherein the carboxylic acid ester component (B) comprises a butyl ester of malic acid.
Claim 10
Dependent Claim
21 words
The hydrophilic polyurethane intermediate of claim 2 wherein the carboxylic acid ester component (B) comprises a dibutyl ester of tartaric acid.
Claim 11
Dependent Claim
21 words
The hydrophilic polyurethane intermediate of claim 2 wherein the carboxylic acid ester component (B) comprises a diethyl ester of tartaric acid.
Claim 12
Dependent Claim
11 words
A hydrophilic polyurethane prepared by saponifying the intermediate of claim 1.
Claim 13
Dependent Claim
11 words
A hydrophilic polyurethane prepared by saponifying the intermediate of claim 2.
Claim 14
Dependent Claim
11 words
A hydrophilic polyurethane prepared by saponifying the intermediate of claim 3.
Claim 15
Dependent Claim
11 words
A hydrophilic polyurethane prepared by saponifying the intermediate of claim 4.
Claim 16
Dependent Claim
11 words
A hydrophilic polyurethane prepared by saponifying the intermediate of claim 5.
Claim 17
Dependent Claim
11 words
A hydrophilic polyurethane prepared by saponifying the intermediate of claim 6.
Claim 18
Dependent Claim
11 words
A hydrophilic polyurethane prepared by saponifying the intermediate of claim 7.
Claim 19
Dependent Claim
11 words
A hydrophilic polyurethane prepared by saponifying the intermediate of claim 8.
Claim 20
Dependent Claim
11 words
A hydrophilic polyurethane prepared by saponifying the intermediate of claim 9.
Claim 21
Dependent Claim
11 words
A hydrophilic polyurethane prepared by saponifying the intermediate of claim 10.
Claim 22
Dependent Claim
14 words
A hydrophilic polyurethane prepared by saponifying and then neutralizing the intermediate of claim 1.
Claim 23
Dependent Claim
14 words
A hydrophilic polyurethane prepared by saponifying and then neutralizing the intermediate of claim 2.
Claim 24
Dependent Claim
14 words
A hydrophilic polyurethane prepared by saponifying and then neutralizing the intermediate of claim 4.
Claim 25
Dependent Claim
14 words
A hydrophilic polyurethane prepared by saponifying and then neutralizing the intermediate of claim 7.
Claim 26
Dependent Claim
14 words
A hydrophilic polyurethane prepared by saponifying and then neutralizing the intermediate of claim 8.
Claim 27
Dependent Claim
14 words
A hydrophilic polyurethane prepared by saponifying and then neutralizing the intermediate of claim 9.
Claim 28
Dependent Claim
14 words
A hydrophilic polyurethane prepared by saponifying and then neutralizing the intermediate of claim 10.
Claim 29
Dependent Claim
16 words
An article of manufacture comprising a shaped body formed of the hydrophilic polyurethane of claim 11.
Claim 30
Dependent Claim
12 words
The article of claim 28 wherein the shaped body is a film.
Claim 31
Dependent Claim
12 words
The article of claim 28 wherein the shaped body is a catheter.
Claim 32
Dependent Claim
17 words
An article of manufacture comprising a substrate carrying a layer of the hydrophilic polyurethane of claim 11.
Claim 33
Dependent Claim
17 words
A body implant comprising the combination of a solid hydrophilic polyurethane of claim 11 and a medicament.
Claim 34
Dependent Claim
21 words
An oral delivery system comprising a pharmacologically active agent and as a carrier vehicle therefor, a hydrophilic polyurethane of claim 11.
Claim 35
Dependent Claim
15 words
A cannula, the walls of which are formed of a hydrophilic polyurethane of claim 11.
Claim 36
Dependent Claim
15 words
An article of manufacture comprising a substrate coated with the hydrophilic polyurethane of claim 11.
Claim 37
Dependent Claim
12 words
The article of claim 37 wherein the substrate is a boat hull.
Claim 38
Dependent Claim
20 words
A method of reducing hydrostatic friction on a substrate, comprising coating the substrate with the hydrophilic polyurethane of claim 11.
References Cited (Backward Citations)
US4156067A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-05-10 | 1991-11-09 | 1992-05-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-05-10 | 1995-11-09 | 1996-05-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-05-10 | 1999-11-09 | 2000-05-10 | $7700.00 | Window Closed / Lapsed |