US5091205A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Hydrophilic lubricious coatings
Assignee: Union Carbide Chemicals and Plastics Technology LLC
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Filing: 1989-12-22
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Granted: 1992-02-25
•
Expires: 2009-12-22
Abstract
Abstract A new method is provided to impart a hydrophilic lubricious coating onto articles such as medical devices. A device, for example a catheter, is first contacted with a polyisocyanate solution, to provide coupling, then contacted with a poly(carboxylic acid) solution to give a coating, and is then finally oven dried. These coatings have lubricity that only becomes manifest upon exposure to water or body fluids, and moreover, are also long lasting and have good abrasion resistance. This combination of properties is not available from other currently used or proposed coatings such as Teflon.
Inventors
- 👤 You-Ling Fan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-22 23:25
CPC Classifications
B; B05; B05D; B05D5/00; B05D5/04; A; A61; A61L; A61L29/00; A61L29/08; A61L29/085; B05D3/00; B05D3/10; B05D3/101; C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/62; C08G18/6216; C08G18/625; C08G18/70; C08G18/703; C08G18/705; C08J; C08J7/00; C08J7/04; C08J7/042; C08J7/0427; C08J7/043; C08J7/046; C08J7/056; C08J7/06; C08J7/065; B05D2201/00; B05D5/08; C08J2375/00; C08J2375/04; C08J2375/12; C08J2433/00; C08J2433/04; C08J2433/06; C08J2433/08
Claims Analysis
Total Claims: 55
Claim 1
Independent Claim
192 words
A method of covering at least a portion of a substrate with a hydrophilic coating which coating exhibits good abrasion resistance and an increased lubricity when contacted with an aqueous-containing fluid, said method comprising the steps of: (1) contacting said substrate with polyisocyanate contained in at least one first inert solvent to provide at least a partially coated substrate; (2) contacting said coated substrate with a poly(acrylic acid) polymer of the formula: ##STR2## where n=0-0.95 mole fraction of neutralized acid moieties, m=0.05-1.0 mole fraction of acid moieties with the proviso that n+m=1, X 1 , X 2 , X 3 are each a hydrogen atom or a monovalent organic radical, Y is a single bond or a divalent organic radical, Z is a metallic ion or a tertiary ammonium ion, and p is a number such that the polymer has a molecular weight between about 200,000 and about 5,000,000, said poly(acrylic acid) polymer contained in at least one second solvent to provide a multiple coated substrate; and (3) thereafter drying said multiple coated substrate to provide a hydrophillic, lubricious coating which contains free carboxylic acid groups or partially neutralized carboxylic acid groups.
Claim 2
Independent Claim
192 words
A method of covering at least a portion of a substrate with a hydrophilic coating which coating exhibits good abrasion resistance and an increased lubricity when contacted with an aqueous-containing fluid, said method comprising the steps of: (1) contacting said substrate with polyisocyanate contained in at least one first inert solvent to provide at least a partially coated substrate; (2) contacting said coated substrate with a poly(acrylic acid) polymer of the formula: ##STR2## where n=0-0.95 mole fraction of neutralized acid moieties, m=0.05-1.0 mole fraction of acid moieties with the proviso that n+m=1, X 1 , X 2 , X 3 are each a hydrogen atom or a monovalent organic radical, Y is a single bond or a divalent organic radical, Z is a metallic ion or a tertiary ammonium ion, and p is a number such that the polymer has a molecular weight between about 200,000 and about 5,000,000, said poly(acrylic acid) polymer contained in at least one second solvent to provide a multiple coated substrate; and (3) thereafter drying said multiple coated substrate to provide a hydrophillic, lubricious coating which contains free carboxylic acid groups or partially neutralized carboxylic acid groups.
Claim 3
Dependent Claim
12 words
The method of claim 1 wherein said substrate is a medical device.
Claim 4
Dependent Claim
12 words
The method of claim 2 wherein said medical device is a catheter.
Claim 5
Dependent Claim
26 words
The method of claim 1 wherein said substrate coated with said polyisocyanate is dried at a temperature of up to about 150° C. before step (2).
Claim 6
Dependent Claim
23 words
The method of claim 4 wherein said multiple coated substrate is dried at a temperature of from about 25° to about 150° C.
Claim 7
Dependent Claim
13 words
The method of claim 1 wherein said first solvent is methyl ethyl ketone.
Claim 8
Dependent Claim
12 words
The method of claim 1 wherein said first solvent is ethyl acetate.
Claim 9
Dependent Claim
17 words
The method of claim 1 wherein said first solvent is a mixture of at least two solvents.
Claim 10
Dependent Claim
11 words
The method of claim 8 wherein said mixture contains mineral oil.
Claim 11
Dependent Claim
13 words
The method of claim 8 wherein said mixture contains at least one surfactant.
Claim 12
Dependent Claim
21 words
The method of claim 1 wherein said second solvent is at least one organic solvent inert to said poly(acrylic acid) polymer.
Claim 13
Dependent Claim
11 words
The method of claim 1 wherein said second solvent is dimethylformamide.
Claim 14
Dependent Claim
11 words
The method of claim 1 wherein said second solvent is dimethylsulfoxide.
Claim 15
Dependent Claim
18 words
The method of claim 1 wherein said second solvent is a mixture of dimethylformamide and methyl ethyl ketone.
Claim 16
Dependent Claim
20 words
The method of claim 1 wherein said second solvent is a mixture of dimethylformamide, methyl ethyl ketone and t-butyl alcohol.
Claim 17
Dependent Claim
11 words
The method of claim 1 wherein said polyisocyanate is a diisocyanate.
Claim 18
Dependent Claim
16 words
The method of claim 16 wherein said diisocyanate is a mixture of toluene 2,4- and 2,6-diisocyanate.
Claim 19
Dependent Claim
12 words
The method of claim 16 wherein said diisocyanate is a diphenylmethane diisocyanate.
Claim 20
Dependent Claim
17 words
The method of claim 16 wherein said diisocyanate is an adduct of diphenylmethane diisocyanate and a polyol.
Claim 21
Dependent Claim
15 words
The method of claim 1 wherein said polyisocyanate is an isocyanate end-capped polyfunctional aliphatic adduct.
Claim 22
Dependent Claim
15 words
The method of claim 1 wherein said polyisocyanate is an isocyanate end-capped polyfunctional aromatic adduct.
Claim 23
Dependent Claim
14 words
The method of claim 1 wherein said coated substrate is thermoformed to different shapes.
Claim 24
Dependent Claim
18 words
The method of claim 22 wherein said coated substrate is first treated with an alkaline bath before thermoforming.
Claim 25
Dependent Claim
20 words
The method of claim 22 wherein said coated substrate is first treated with an alkali metal salt bath before thermoforming.
Claim 26
Dependent Claim
20 words
The method of claim 22 wherein said coated substrate is first treated with an alkali metal phosphate bath before thermoforming.
Claim 27
Dependent Claim
21 words
The method of claim 1 wherein said polyisocyanate is a reaction product of a polyfunctional isocyanate with an aliphatic polyester polyol.
Claim 28
Dependent Claim
21 words
The method of claim 1 wherein said polyisocyanate is a reaction product of a polyfunctional isocyanate with an aromatic polyester polyol.
Claim 29
Dependent Claim
20 words
The method of claim 1 wherein said polyisocyanate is a mixture of a diisocyanate and an isocyanate end-capped polyfunctional adduct.
Claim 30
Dependent Claim
17 words
The method of claim 1 wherein said poly(acrylic acid) polymer is a colloidal dispersion of a homopolymer.
Claim 31
Dependent Claim
21 words
The method of claim 1 wherein said poly(acrylic acid) polymer has a molecular weight of from about 200,000 to about 5,000,000.
Claim 32
Dependent Claim
17 words
The method of claim 30 wherein said poly(acrylic acid) polymer has a molecular weight of about 3,000,000.
Claim 33
Dependent Claim
13 words
The method of claim 1 wherein said carboxylic acid-containing polymer is a copolymer.
Claim 34
Dependent Claim
22 words
The method of claim 1 wherein said carboxylic acid containing polymer is partially cross-linked, and contains at least some water insoluble units.
Claim 35
Dependent Claim
12 words
The method of claim 1 wherein said polyisocyanate applied as a dispersion.
Claim 36
Dependent Claim
14 words
The method of claim 1 wherein said poly(isocyanate) is applied as an oil-in-water emulsion.
Claim 37
Dependent Claim
15 words
The method of claim 1 wherein said poly(acrylic acid) polymer is applied as an emulsion.
Claim 38
Dependent Claim
15 words
The method of claim 1 wherein said poly(acrylic acid) polymer is applied as a dispersion.
Claim 39
Independent Claim
184 words
A method of covering at least a portion of a substrate with a hydrophilic coating having good abrasion resistance, and which exhibits an increased lubricity when contacted with an aqueous-containing fluid, said method comprising the steps of: (1) contacting said substrate with a polyisocyanate contained in at least one first inert organic solvent to provide at least a partially coated substrate; (2) contacting said coated substrate with a poly(acrylic acid) polymer of the formula: ##STR3## where n=0-0.95 mole fraction of neutralized acid moieties; m=0.05-1.0 mole fraction of acid moieties with the proviso that n+m=1; X 1 , X 2 , X 3 are each a hydrogen atom or a monovalent organic radical; Y is a single bond or a divalent organic radical; Z is a metallic ion or a tertiary ammonium ion; and p is a number such that the polymer has a molecular weight between about 200,000 and about 5,000,000; said carboxylic acid-containing polymer contained in at least one second inert organic solvent to provide a multiple coated substrate; and (3) thereafter drying said multiple coated substrate to provide a hydrophilic, lubricious coating.
Claim 40
Independent Claim
184 words
A method of covering at least a portion of a substrate with a hydrophilic coating having good abrasion resistance, and which exhibits an increased lubricity when contacted with an aqueous-containing fluid, said method comprising the steps of: (1) contacting said substrate with a polyisocyanate contained in at least one first inert organic solvent to provide at least a partially coated substrate; (2) contacting said coated substrate with a poly(acrylic acid) polymer of the formula: ##STR3## where n=0-0.95 mole fraction of neutralized acid moieties; m=0.05-1.0 mole fraction of acid moieties with the proviso that n+m=1; X 1 , X 2 , X 3 are each a hydrogen atom or a monovalent organic radical; Y is a single bond or a divalent organic radical; Z is a metallic ion or a tertiary ammonium ion; and p is a number such that the polymer has a molecular weight between about 200,000 and about 5,000,000; said carboxylic acid-containing polymer contained in at least one second inert organic solvent to provide a multiple coated substrate; and (3) thereafter drying said multiple coated substrate to provide a hydrophilic, lubricious coating.
Claim 41
Dependent Claim
13 words
The method of claim 38 wherein the first solvent is methyl ethyl ketone.
Claim 42
Dependent Claim
11 words
The method of claim 38 wherein the second solvent is dimethylformamide.
Claim 43
Dependent Claim
18 words
The method of claim 38 wherein said second solvent is a mixture of dimethylformamide and methyl ethyl ketone.
Claim 44
Dependent Claim
26 words
The method of claim 38 wherein said substrate coated with said polyisocyanate is dried at a temperature of up to about 150° C. before step (2).
Claim 45
Dependent Claim
18 words
The method of claim 38 wherein at least one of said first or second solvents contains a surfactant.
Claim 46
Dependent Claim
15 words
The method of claim 1 wherein at least one additive is incorporated into said coating.
Claim 47
Dependent Claim
15 words
The method of claim 38 wherein at least one additive is incorporated into said coating.
Claim 48
Dependent Claim
11 words
The method of claim 44 wherein said additive is an antithrombogenic.
Claim 49
Dependent Claim
10 words
The method of claim 44 wherein said additive is heparin.
Claim 50
Independent Claim
215 words
A method of covering at least a portion of a substrate with a hydrophilic coating which coating exhibits good abrasion resistance and an increased lubricity when contacted with an aqueous-containing fluid, said method comprising the steps of: (1) contacting said substrate with polyisocyanate contained in at least one first inert solvent to provide at least a partially coated substrate; (2) drying said coated substrate to provide a primer coat of the polyisocyanate on the substrate; (3) contacting said coated substrate with a poly(acrylic acid) polymer of the formula: ##STR4## where n=0-0.95 mole fraction of neutralized acid moieties, m=0.05-1.0 mole fraction of acid moieties with the proviso that n+m=1, X 1 , X 2 , X 3 are each a hydrogen atom or a monovalent organic radical, Y is a single bond or a divalent organic radical, Z is a metallic ion or a tertiary ammonium ion, and p is a number such that the polymer has a molecular weight between about 200,000 and about 5,000,000, said poly(acrylic acid) polymer contained in at least one second solvent to provide a multiple coated substrate; (4) thereafter drying said multiple coated substrate to provide a hydrophillic, lubricious coating which contains free carboxylic acid groups or partially neutralized carboxylic acid groups; and (5) optionally neutralizing the multiple coated substrate.
Claim 51
Independent Claim
215 words
A method of covering at least a portion of a substrate with a hydrophilic coating which coating exhibits good abrasion resistance and an increased lubricity when contacted with an aqueous-containing fluid, said method comprising the steps of: (1) contacting said substrate with polyisocyanate contained in at least one first inert solvent to provide at least a partially coated substrate; (2) drying said coated substrate to provide a primer coat of the polyisocyanate on the substrate; (3) contacting said coated substrate with a poly(acrylic acid) polymer of the formula: ##STR4## where n=0-0.95 mole fraction of neutralized acid moieties, m=0.05-1.0 mole fraction of acid moieties with the proviso that n+m=1, X 1 , X 2 , X 3 are each a hydrogen atom or a monovalent organic radical, Y is a single bond or a divalent organic radical, Z is a metallic ion or a tertiary ammonium ion, and p is a number such that the polymer has a molecular weight between about 200,000 and about 5,000,000, said poly(acrylic acid) polymer contained in at least one second solvent to provide a multiple coated substrate; (4) thereafter drying said multiple coated substrate to provide a hydrophillic, lubricious coating which contains free carboxylic acid groups or partially neutralized carboxylic acid groups; and (5) optionally neutralizing the multiple coated substrate.
Claim 52
Dependent Claim
43 words
The method of claim 48 wherein the polyisocyanate is diphenylmethane diisocyanate or an adduct thereof, wherein the first inert solvent is either methyl ethyl ketone or toluene, wherein the second inert solvent is a mixture of methyl ethyl ketone, dimethylformamide and t-butyl alcohol.
Claim 53
Dependent Claim
59 words
The method of claim 49 wherein the polyisocyanate is diphenylmethane diioscyanate or an adduct thereof in the first inert solvent is present in a concentration of from about 0.5 to about 20 percent by weight and the poly(acrylic acid) in the second inert solvent is present in a concentration of from about 0.1 to about 10 percent by weight.
Claim 54
Dependent Claim
59 words
The method of claim 50 wherein the polyisocyanate is diphenylmethane diisocyanate or an adduct thereof in the first inert solvent is present in a concentration of from about 1 to about 5 percent by weight and the poly(acrylic acid) in the second inert solvent is present in a concentration of from about 0.5 to about 2 percent by weight.
Claim 55
Dependent Claim
42 words
The method of claim 48 wherein the polyisocyanate is a mixture of different polyisocyanates, wherein the first inert solvent is either methyl ethyl ketone or toluene, wherein the second inert solvent is a mixture of methyl ethyl ketone, dimethylformamide and t-butyl alcohol.
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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) | 1995-02-24 | 1995-08-26 | 1996-02-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-02-24 | 1999-08-26 | 2000-02-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-02-24 | 2003-08-26 | 2004-02-25 | $7700.00 | Window Closed / Lapsed |