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US5120816A Expired / Lapsed US ⏱️ 0.0 years remaining

Hydrophilic polyurethanes of improved strength

Assignee: Tyndale Plains Hunter Ltd
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Filing: 1990-07-24
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Granted: 1992-06-09
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Expires: 2010-07-24
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Abstract

Abstract The strength and integrity of hydrophilic polyurethane resins prepared by reacting a diol component, an organic chain extender and an organic diisocyanate are improved by critical selection of the diol component, the amount of water in the reaction mixture and the mole rations of the reactants. The diol component is at least one of (1) a long chain poly(oxyethylene) glycol of molecular weight above 2500 and (2) a medium chain poly(oxyethylene) glycol or polyester glycol of 250-2500 molecular weight. The chain extender is a difunctional compound having a molecular weight of less than 250. The amount of water in the reaction mixture is 0.5 to 2.5 weight % and the urea content of the resins is from about 13.6 to 33.7 weight %.

Inventors

  • 👤 Francis E. Gould
  • 👤 Christian W. Johnston

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-23 13:11
CPC Classifications
G; G02; G02B; G02B1/00; G02B1/04; G02B1/041; G02B1/043; A; A61; A61L; A61L15/00; A61L15/16; A61L15/22; A61L15/26; A61L27/00; A61L27/14; A61L27/18; A61L29/00; A61L29/08; A61L29/085; A61L31/00; A61L31/04; A61L31/06; C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/302; C08G18/40; C08G18/48; C08G18/4833; C08G18/65; C08G18/66; C08G18/6666; C08G18/667; C08G18/6674; C08G2210/00; Y; Y10; Y10S; Y10S623/00; Y10S623/924

Claims Analysis

Total Claims: 22
Claim 1
Independent Claim 232 words
A substantially noncovalently crosslinked hydrophilic, substantially nonfoaming polyurethane resin having improved tear strength and a urea content of from about 13.6 to 33.7 weight percent, consisting essentially of the reaction product of a mixture of: A. a diol component selected from at least one of (1) a long chain poly(oxyethylene) glycol, having a molecular weight of from about 2500 to about 12000, (2) a medium chain poly(oxyethylene) glycol or polyester glycol, having a molecular weight of from about 250 to about 2500, B. at least one organic chain extender having a molecular weight of less than 250; C. water; and D. an organic diisocyanate; wherein alternative mole ratios of the diol component A and water per mole of chain extender B are as follows: (i) 0.4 to 0.5 of diol component (1), 1.5 to 10.0 of water; (ii) 0.1 to 0.25 of diol component (2), 0.05 to 0.72 of water; (iii) 0.25 to 0.50 of diol component (2), 0.25 to 1.00 of water; (iv) 0.5 to 0.75 of diol component (2), 0.3 to 3.3 of water; or (v) 0.06 to 0.07 of diol component (1), 0.1 to 0.2 of diol component (2) and 0.25 to 1.25 of water; wherein the effective NCO:OH ratio is in the range of 0.85:1 to 1.1:1 and the amount of water in the reaction mixture is in the range of about 1 to about 2.5 wt. %.
Claim 2
Dependent Claim 232 words
A substantially noncovalently crosslinked hydrophilic, substantially nonfoaming polyurethane resin having improved tear strength and a urea content of from about 13.6 to 33.7 weight percent, consisting essentially of the reaction product of a mixture of: A. a diol component selected from at least one of (1) a long chain poly(oxyethylene) glycol, having a molecular weight of from about 2500 to about 12000, (2) a medium chain poly(oxyethylene) glycol or polyester glycol, having a molecular weight of from about 250 to about 2500, B. at least one organic chain extender having a molecular weight of less than 250; C. water; and D. an organic diisocyanate; wherein alternative mole ratios of the diol component A and water per mole of chain extender B are as follows: (i) 0.4 to 0.5 of diol component (1), 1.5 to 10.0 of water; (ii) 0.1 to 0.25 of diol component (2), 0.05 to 0.72 of water; (iii) 0.25 to 0.50 of diol component (2), 0.25 to 1.00 of water; (iv) 0.5 to 0.75 of diol component (2), 0.3 to 3.3 of water; or (v) 0.06 to 0.07 of diol component (1), 0.1 to 0.2 of diol component (2) and 0.25 to 1.25 of water; wherein the effective NCO:OH ratio is in the range of 0.85:1 to 1.1:1 and the amount of water in the reaction mixture is in the range of about 1 to about 2.5 wt. %.
Claim 3
Dependent Claim 60 words
The hydrophilic polyurethane resin of claim 1 wherein the long chain poly(oxyethylene) glycol (1) has a number average molecular weight of about 3000 to 12000, the medium chain poly(oxyethylene) glycol or polyester glycol (2) has a number average molecular weight of about 500 to 2000, and the chain extender (B) is at least one of ethylene glycol and diethylene glycol.
Claim 4
Dependent Claim 25 words
The hydrophilic polyurethane resin of claim 2 wherein the long chain poly(oxyethylene) glycol (1) has a number average molecular weight of about 5000 t 9000.
Claim 5
Dependent Claim 19 words
The hydrophilic polyurethane resin of claim 1 wherein the diol component (A) comprises a medium chain poly(oxyethylene) glycol (2).
Claim 6
Dependent Claim 19 words
The hydrophilic polyurethane resin of claim 1 wherein the diol component (A) comprises a long chain poly(oxyethylene) glycol (1).
Claim 7
Dependent Claim 26 words
The hydrophilic polyurethane resin of claim 1 wherein the diol component (A) comprises a mixture of long chain and medium chain poly(oxyethylene) glycols (1) and (2).
Claim 8
Dependent Claim 15 words
The hydrophilic polyurethane resin of claim 1 wherein the chain extender (B) is diethylene glycol.
Claim 9
Dependent Claim 36 words
The hydrophilic polyurethane of claim 1 wherein the diol component (A) comprises a long chain poly(oxyethylene) glycol having a number average molecular weight of about 5000 to 9000, and the chain extender (B) is diethylene glycol.
Claim 10
Dependent Claim 25 words
The hydrophilic polyurethane of claim 1 wherein the diol component (A) comprises a medium chain poly(oxyethylene) glycol and the chain extender (B) is diethylene glycol.
Claim 11
Dependent Claim 45 words
The hydrophilic polyurethane of claim 1 wherein the diol component (A) comprises a mixture of a long chain poly(oxyethylene) glycol having a number average molecular weight of about 5000 to 9000 and a medium chain poly(oxyethylene) glycol, and the chain extender (B) is diethylene glycol.
Claim 12
Dependent Claim 18 words
An article of manufacture comprising a shaped body or film formed of the hydrophilic polyurethane of claim 1.
Claim 13
Dependent Claim 18 words
An article of manufacture comprising a shaped body or film formed of the hydrophilic polyurethane of claim 8.
Claim 14
Dependent Claim 18 words
An article of manufacture comprising a shaped body or film formed of the hydrophilic polyurethane of claim 9.
Claim 15
Dependent Claim 18 words
An article of manufacture comprising a shaped body or film formed of the hydrophilic polyurethane of claim 10.
Claim 16
Dependent Claim 39 words
The article of claim 11 wherein the shaped body or film is selected from cannulae, contact lenses, intraocular lenses, Seton strips, corneal grafts, boluses for animals, intrauterine devices, valves, gloves, condoms, wound and burn dressings, membranes and denture liners.
Claim 17
Dependent Claim 32 words
The article of claim 11 wherein the shaped body comprises a body implant selected from vascular grafts, esophageal and urethral prosthetic devices, mammary implants, reconstructive surgery implants, tendon sheaths and tissue extenders.
Claim 18
Dependent Claim 15 words
An article of manufacture comprising a substrate coated with the hydrophilic polyurethane of claim 1.
Claim 19
Dependent Claim 15 words
An article of manufacture comprising a substrate coating with the hydrophilic polyurethane of claim 8.
Claim 20
Dependent Claim 15 words
An article of manufacture comprising a substrate coating with the hydrophilic polyurethane of claim 9.
Claim 21
Dependent Claim 15 words
An article of manufacture comprising a substrate coating with the hydrophilic polyurethane of claim 10.
Claim 22
Dependent Claim 25 words
The article of claim 17 wherein the substrate is selected from a boat hull, a catheter, a guide wire, a valve and an industrial conduit.

References Cited (Backward Citations)

US2977330A Cited
US3539482A Cited
US4459309A Cited
US4355119A Cited
US4359558A Cited
US4454309A Cited
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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) 1995-06-09 1995-12-09 1996-06-09 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1999-06-09 1999-12-09 2000-06-09 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2003-06-09 2003-12-09 2004-06-09 $7700.00 Window Closed / Lapsed

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