US4485227A
Expired / Lapsed
US
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Biocompatible poly-(ether-urethane-urea) and process for its preparation
Assignee: MTG Divestitures LLC
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Filing: 1983-06-16
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Granted: 1984-11-27
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Expires: 2003-06-16
Abstract
Abstract An improved biocompatible and hemocompatible segmented poly-(ether-urethane-urea) is prepared by a process which comprises condensing an alkylene polyether diol of molecular weight of 500 to 6000 with substantially two equivalents of an aryl, aralkyl, or alkyl diisocyanate of 6 to 20 carbon atoms; condensing the thus-formed α,Ω-diisocyanato poly-(ether-urethane) with a substantially equivalent proportion of a primary alkyl diamine of 2 to 6 carbon atoms until a degree of condensation of about 5 to 20 is achieved; condensing the resulting poly-(ether-urethane-urea) with a primary alkyl amine or diamine of up to 6 carbon atoms in an amount substantially equivalent to the free isocyanate content of the poly-(ether-urethane-urea); and condensing the amine-treated poly-(ether-urethane-urea) with an amine-reacting agent in an amount substantially equivalent to the free amine content of the amine-treated poly-(ether-urethane-urea). The polymer is especially suitable for fabricating replacements for damaged cardiovascular and urinary tract vessels.
Inventors
- 👤 Adrian S. Fox
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 18:36
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/83; C08G18/831; A; A61; A61L; A61L27/00; A61L27/14; A61L27/18; C08G18/08; C08G18/10
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
107 words
A biocompatible and hemocompatible segmented poly-(ether-urethane-urea) of the formula I: ##STR2## wherein R=arylene, aralkylene or alkylene each having from 6 to 20 carbons, R 1 =alkylene having from 2 to 6 carbons, R 2 =alkylene having from 2 to 6 carbons, R 3 =alkyl having up to 4 carbons or R 5 CONHR 4 or R 6 NHCONHR 4 wherein R 4 =alkylene having from 2 to 6 carbons, R 5 =aryl or alkyl each having up to 16 carbons and R 6 =aryl or alkyl each hving up to 12 carbons, n=a number from about 7 to 35, and m=a number from about 5 to 20.
Claim 2
Dependent Claim
107 words
A biocompatible and hemocompatible segmented poly-(ether-urethane-urea) of the formula I: ##STR2## wherein R=arylene, aralkylene or alkylene each having from 6 to 20 carbons, R 1 =alkylene having from 2 to 6 carbons, R 2 =alkylene having from 2 to 6 carbons, R 3 =alkyl having up to 4 carbons or R 5 CONHR 4 or R 6 NHCONHR 4 wherein R 4 =alkylene having from 2 to 6 carbons, R 5 =aryl or alkyl each having up to 16 carbons and R 6 =aryl or alkyl each hving up to 12 carbons, n=a number from about 7 to 35, and m=a number from about 5 to 20.
Claim 3
Dependent Claim
38 words
The poly-(ether-urethane-urea) of claim 1 wherein R=4,4'-diphenylmethane; R 1 =1-methyl ethylene; R 2 =ethylene; R 3 =R 5 CONHR 4 ; R 4 =ethylene; R 5 =methyl; n=from about 13 to 15; and m=from about 8 to 16.
Claim 4
Dependent Claim
138 words
A process for the preparation of a biocompatible and hemocompatible segmented poly-(ether-urethane-urea), which comprises: (a) condensing an alkylene polyether diol of molecular weight of from about 500 to 6000 with substantially two equivalents of an aryl, aralkyl, or alkyl diisocyanate each of from 6 to 20 carbon atoms; (b) condensing the thus-formed α,Ω-diisocyanato poly-(ether-urethane) with a substantially equivalent proportion of a primary alkyl diamine of from 2 to 6 carbon atoms until a degree of condensation of from about 5 to 20 is achieved; (c) condensing the resulting poly-(ether-urethane-urea) with a primary alkyl amine of up to 6 carbon atoms in an amount substantially equivalent to the free isocyanate content of said poly-(ether-urethane-urea); and (d) condensing the resulting amine-treated poly-(ether-urethane-urea) with an amine-reacting agent in an amount substantially equivalent to the free amine content of said amine-treated poly-(ether-urethane-urea).
Claim 5
Dependent Claim
138 words
A process for the preparation of a biocompatible and hemocompatible segmented poly-(ether-urethane-urea), which comprises: (a) condensing an alkylene polyether diol of molecular weight of from about 500 to 6000 with substantially two equivalents of an aryl, aralkyl, or alkyl diisocyanate each of from 6 to 20 carbon atoms; (b) condensing the thus-formed α,Ω-diisocyanato poly-(ether-urethane) with a substantially equivalent proportion of a primary alkyl diamine of from 2 to 6 carbon atoms until a degree of condensation of from about 5 to 20 is achieved; (c) condensing the resulting poly-(ether-urethane-urea) with a primary alkyl amine of up to 6 carbon atoms in an amount substantially equivalent to the free isocyanate content of said poly-(ether-urethane-urea); and (d) condensing the resulting amine-treated poly-(ether-urethane-urea) with an amine-reacting agent in an amount substantially equivalent to the free amine content of said amine-treated poly-(ether-urethane-urea).
Claim 6
Dependent Claim
22 words
The process of claim 3 wherein said diol is selected from the group consisting of polyethylene glycol, poly-(1,2-propylene glycol) and poly-(1,4-butylene glycol).
Claim 7
Dependent Claim
24 words
The process of claim 3 wherein said diisocyanate is selected from the group consisting of 4,4'-diphenylmethane diisocyanate, toluene 2,4-diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate and isophorone diisocyanate.
Claim 8
Dependent Claim
28 words
The process of claim 3 wherein said primary alkyl amine is a monoamine of from 1 to 4 carbons or a diamine of from 2 to 6 carbons.
Claim 9
Dependent Claim
31 words
The process of claim 3 wherein said amine-reacting agent is selected from the group consisting of aryl or alkyl acid anhydrides, acid chlorides and monoisocyanates of up to 16 carbon atoms.
Claim 10
Dependent Claim
15 words
The process of claim 3 wherein said condensations are conducted in nonreactive, aprotic, water-miscible solvent.
Claim 11
Dependent Claim
42 words
The process of claim 8 wherein the temperature of said condensations is from about 60° to 100° C. in step (a), from about 15° to 30° C. in steps (b) and (c) and from about 20° to 80° C. in step (d).
Claim 12
Dependent Claim
26 words
The process of claim 3 wherein said diol includes up to about 15 mole percent of an alkylene triol of from 3 to 8 carbon atoms.
Claim 13
Dependent Claim
27 words
The process of claim 3 wherein said diol includes up to about 50 mole percent of an unsaturated alkylene diol of from 6 to 12 carbon atoms.
Claim 14
Dependent Claim
9 words
The segmented poly-(ether-urethane-urea) of the process of claim 3.
Claim 15
Dependent Claim
122 words
A process for preparing a biocompatible and hemocompatible segmented poly-(ether-urethane-urea), which comprises: (a) contacting poly-(1,2-propylene glycol) of nominal molecular weight of 950 to 1050 with substantially two equivalents of 4,4'-diphenylmethane diisocyanate in dimethyl sulfoxide/diglyme solvent at a temperature of from about 80° to 85° C.; (b) contacting the thus-formed α,Ω-diisocyanato poly-(ether-urethane) with a substantially equivalent proportion of ethylenediamine in said solvent at a temperature of from about 25° to 30° C.; (c) contacting the resulting poly-(ether-urethane-urea) in said solvent at a temperature of from about 20° to 25° C. with about 8 mole percent additional ethylenediamine; and (d) contacting the amine-treated poly-(ether-urethane-urea) in said solvent at a temperature of from about 20° to 60° C. with about 16 mole percent acetic anhydride.
Claim 16
Dependent Claim
122 words
A process for preparing a biocompatible and hemocompatible segmented poly-(ether-urethane-urea), which comprises: (a) contacting poly-(1,2-propylene glycol) of nominal molecular weight of 950 to 1050 with substantially two equivalents of 4,4'-diphenylmethane diisocyanate in dimethyl sulfoxide/diglyme solvent at a temperature of from about 80° to 85° C.; (b) contacting the thus-formed α,Ω-diisocyanato poly-(ether-urethane) with a substantially equivalent proportion of ethylenediamine in said solvent at a temperature of from about 25° to 30° C.; (c) contacting the resulting poly-(ether-urethane-urea) in said solvent at a temperature of from about 20° to 25° C. with about 8 mole percent additional ethylenediamine; and (d) contacting the amine-treated poly-(ether-urethane-urea) in said solvent at a temperature of from about 20° to 60° C. with about 16 mole percent acetic anhydride.
Claim 17
Dependent Claim
9 words
The segmented poly-(ether-urethane-urea) of the process of claim 13.
Claim 18
Dependent Claim
33 words
A method of repairing a duct in a living body, which comprises replacing the defective portion of said duct with its equivalent in size and shape fabricated from the poly-(ether-urethane-urea) of claim 1.
Claim 19
Dependent Claim
17 words
The method of claim 15 wherein said duct is a blood vessel, a ureter or a urethra.
References Cited (Backward Citations)
US4173689A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-11-27 | 1988-05-28 | 1988-11-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-11-27 | 1992-05-28 | 1992-11-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-11-27 | 1996-05-28 | 1996-11-27 | $7700.00 | Window Closed / Lapsed |