US5118779A
Expired / Lapsed
US
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Hydrophilic polyurethane elastomers
Assignee: Polymedica Industries Inc
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Filing: 1989-10-10
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Granted: 1992-06-02
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Expires: 2009-10-10
Abstract
Abstract A non-toxic hydrophilic polyurethane elastomer having less than about 0.5% by weight extractables and which is curable in the absence of heat is disclosed. The elastomers are prepared from suitable hydrophilic polyurethane oligomers in combination with suitable ultraviolet light absorbers which become chemically bound into the elastomer during the polymerization (curing) thereof and thus become essentially non-extractable therefrom.
Inventors
- 👤 Michael Szycher
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 18:00
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/67; C08G18/671; C08G18/672; A; A61; A61K; A61K9/00; A61K9/20; A61K9/2004; A61K9/2022; A61K9/2031; A61K9/70; A61K9/7007; C08G18/40; C08G18/48; C08G18/4833; Y; Y10; Y10S; Y10S525/00; Y10S525/92; Y10S528/00; Y10S528/904
Claims Analysis
Total Claims: 51
Claim 1
Independent Claim
50 words
A hydrophilic polyurethane elastomer which has been cured by exposure to actinic radiation in the presence of at least one photoinitiator containing a polymerizable group said cured elastomer containing less than about 0.5 weight % extractables as prepared without the need to perform a leaching operation on the cured elastomer.
Claim 2
Dependent Claim
50 words
A hydrophilic polyurethane elastomer which has been cured by exposure to actinic radiation in the presence of at least one photoinitiator containing a polymerizable group said cured elastomer containing less than about 0.5 weight % extractables as prepared without the need to perform a leaching operation on the cured elastomer.
Claim 3
Dependent Claim
15 words
The elastomer of claim 1 wherein it contains less than about 0.1 weight % extractables.
Claim 4
Dependent Claim
15 words
The elastomer of claim 1 which has been non-exothermically cured by exposure to ultraviolet radiation.
Claim 5
Dependent Claim
17 words
The elastomer of claim 3 wherein the ultraviolet radiation exposure is for less than about 120 seconds.
Claim 6
Dependent Claim
17 words
The elastomer of claim 3 wherein the ultraviolet radiation exposure is for less than about 60 seconds.
Claim 7
Dependent Claim
75 words
The elastomer of claim 1 comprising a cured reaction product having at least about 5 weight percent poly(ethyleneoxide) groups of the formula --CH 2 CH 2 O-- and prepared from an oligomer of an aliphatic diisocyanate, a bifunctional component having two terminal groups each of which contains an active hydrogen, and a chain capping monomer which contains both an active hydrogen and a polymerizable vinyl group, and a photoinitiator which contains a polymerizable vinyl group.
Claim 8
Dependent Claim
26 words
The elastomer of claim 6 wherein the bifunctional component is a polyethylene glycol having a molecular weight of about 500 to less than about 3000 Daltons.
Claim 9
Dependent Claim
20 words
The elastomer of claim 7 wherein the polyethylene glycol has a molecular weight of about 750 to about 2500 Daltons.
Claim 10
Dependent Claim
20 words
The elastomer of claim 7 wherein the polyethylene glycol has a molecular weight of about 900 to about 1500 Daltons.
Claim 11
Dependent Claim
17 words
The elastomer of claim 7 wherein at least 20% by weight of the elastomer is polyethylene glycol.
Claim 12
Dependent Claim
39 words
The elastomer of claim 6 wherein the aliphatic diisocyanate is of the formula OCN--R--NCO wherein R is selected from the group consisting essentially of aliphatic, aliphatic-alicyclic and aliphatic-aromatic hydrocarbon compounds containing from about 4 to about 26 carbon atoms.
Claim 13
Dependent Claim
45 words
The elastomer of claim 11 wherein the aliphatic diisocyanate is selected from the group consisting essentially of tetramethylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, dimer acid diisocyanate, isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, methylene di(cyclohexyl isocyanate), metaxylene diisocyanate, diethylbenzene diisocyanate, decamethylene 1,10-diisocyanate, cyclohexylene 1,2-diisocyanate, and cyclohexylene 1,4-diisocyanate.
Claim 14
Dependent Claim
14 words
The elastomer of claim 6 wherein the chain capping monomer contains one vinyl group.
Claim 15
Dependent Claim
16 words
The elastomer of claim 6 wherein the chain capping monomer is hydroxyethyl acrylate or hydroxyethyl methacrylate.
Claim 16
Dependent Claim
23 words
The elastomer of claim 6 wherein the photoinitiator comprises about 1 to about 5 weight percent based on the weight of the oligomer.
Claim 17
Dependent Claim
23 words
The elastomer of claim 15 wherein the photoinitiator comprises about 1.5 to about 4 weight percent based on the weight of the oligomer.
Claim 18
Dependent Claim
32 words
The elastomer of claim 1 wherein the photoinitiator is selected from the group consisting of benzil ketals, benzoin ethers, and aromatic ketones, which have been modified to contain a polymerizable vinyl group.
Claim 19
Dependent Claim
24 words
The elastomer of claim 1 wherein the photoinitiator is selected from the group consisting essentially of (i) 4-(2-acryloyloxyethoxy)-phenyl-2-hydroxy-2-propylketone, (ii) 4-[2-(3-triethoxysilylpropoxy)]phenyl-2-hydroxy-2-propylketone, (iii) 4-(2-azidoethoxy)phenyl-2-hydroxy-2-propylketone, (iv) 4-(2-aminoethoxy)phenyl-2-hydroxy-2-propylketone.
Claim 20
Dependent Claim
10 words
The elastomer of claim 15 wherein the photoinitiator is 4-(2-acryloyl-oxyethoxy)-phenyl-2-hydroxy-2-propylketone.
Claim 21
Dependent Claim
18 words
The elastomer of claim 1 wherein the elastomer is cured through terminal vinyl groups on a polyurethane oligomer.
Claim 22
Dependent Claim
38 words
The elastomer of claim 1 wherein said elastomer is cured by incorporation of about 1 to about 5 weight percent of a photoinitiator containing a hydroxyl group and a vinyl group and then exposing it to ultraviolet radiation.
Claim 23
Dependent Claim
20 words
The elastomer of claim 21 wherein the photoinitiator is used in amount of about 1.5 to about 4 weight percent.
Claim 24
Dependent Claim
10 words
The elastomer of claim 21 wherein the photoinitiator is 4-(2-acryloyl-oxyethoxy-)-phenyl-2-hydroxy-2-propylketone.
Claim 25
Dependent Claim
17 words
A hydrophilic polyurethane elastomer according to claim 1, wherein the elastomer is cured at about room temperature.
Claim 26
Dependent Claim
138 words
A process for preparing a drug delivery system capable of delivering a drug through the unbroken skin or mucosa of a patient which comprises: (A) preparing an --NCO-free reaction product having at least about 5 weight percent poly(ethyleneoxide) groups of the formula --CH 2 CH 2 O-- from an aliphatic diisocyanate, a bifunctional component having two terminal groups each of which contains an active hydrogen, and a chain capping monomer which contains both an active hydrogen and a polymerizable vinyl group; (B) admixing said reaction product with (i) a photoinitiator which contains a polymerizable vinyl group and (ii) a drug; (C) forming the admixture into a film having a thickness of about 0.010 to about 0.050 inches; and (D) curing said film at about room temperature by exposing it to ultraviolet radiation for less than about 2 minutes.
Claim 27
Dependent Claim
138 words
A process for preparing a drug delivery system capable of delivering a drug through the unbroken skin or mucosa of a patient which comprises: (A) preparing an --NCO-free reaction product having at least about 5 weight percent poly(ethyleneoxide) groups of the formula --CH 2 CH 2 O-- from an aliphatic diisocyanate, a bifunctional component having two terminal groups each of which contains an active hydrogen, and a chain capping monomer which contains both an active hydrogen and a polymerizable vinyl group; (B) admixing said reaction product with (i) a photoinitiator which contains a polymerizable vinyl group and (ii) a drug; (C) forming the admixture into a film having a thickness of about 0.010 to about 0.050 inches; and (D) curing said film at about room temperature by exposing it to ultraviolet radiation for less than about 2 minutes.
Claim 28
Dependent Claim
26 words
The process of claim 25 wherein the bifunctional component comprises a polyethylene glycol having a molecular weight of about 500 to less than about 3000 Daltons.
Claim 29
Dependent Claim
20 words
The process of claim 26 wherein the polyethylene glycol has a molecular weight of about 750 to about 2500 Daltons.
Claim 30
Dependent Claim
39 words
The process of claim 25 wherein the aliphatic diisocyanate is of the formula OCN--R--NCO wherein R is selected from the group consisting essentially of aliphatic, aliphatic-alicyclic and aliphatic-aromatic hydrocarbon compounds containing from about 4 to about 26 carbon atoms.
Claim 31
Dependent Claim
45 words
The process of claim 28 wherein the aliphatic diisocyanate is selected from the group consisting essentially of tetramethylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, dimer acid diisocyanate, isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, methylene di(cyclohexyl isocyanate), metaxylene diisocyanate, diethylbenzene diisocyanate, decamethylene 1,10-diisocyanate, cyclohexylene 1,2-diisocyanate, and cyclohexylene 1,4-diisocyanate.
Claim 32
Dependent Claim
16 words
The process of claim 25 wherein the chain capping monomer is hydroxyethyl acrylate or hydroxyethyl methacrylate.
Claim 33
Dependent Claim
32 words
The process of claim 25 wherein the photoinitiator is selected from the group consisting of benzil ketals, benzoin ethers, and aromatic ketones, which have been modified to contain a polymerizable vinyl group.
Claim 34
Dependent Claim
10 words
The process of claim 31 wherein the photoinitiator is 4-(2-acryloyl-oxyethoxy)-phenyl-2-hydroxy-2-propylketone.
Claim 35
Dependent Claim
34 words
The process of claim 25 wherein said drug is selected from the group consisting essentially of pharmaceuticals, bacteriostats, viruscides, antibiotics, antifungal agents, topical anaesthetics, growth factors, skin softeners, anti-acne medications, external anaesthetics, and cosmetics.
Claim 36
Dependent Claim
18 words
The process of claim 25 further comprising coating one surface of said film with a pressure sensitive adhesive.
Claim 37
Dependent Claim
68 words
A drug delivery system suitable for delivering a medication to a patient through its unbroken skin or mucosa which is prepared by (i) preparing a mixture of a medication, a liquid oligomer having two terminal vinyl groups, and a photoinitiator having a polymerizable vinyl group, (ii) forming the mixture into a shaped body, and (iii) exposing the shaped body to ultraviolet radiation for less than about 2 minutes.
Claim 38
Dependent Claim
68 words
A drug delivery system suitable for delivering a medication to a patient through its unbroken skin or mucosa which is prepared by (i) preparing a mixture of a medication, a liquid oligomer having two terminal vinyl groups, and a photoinitiator having a polymerizable vinyl group, (ii) forming the mixture into a shaped body, and (iii) exposing the shaped body to ultraviolet radiation for less than about 2 minutes.
Claim 39
Dependent Claim
65 words
The drug delivery system of claim 35 wherein the liquid oligomer comprises at least about 5 weight percent poly(ethyleneoxide) groups of the formula --CH 2 CH 2 O-- and is prepared from an aliphatic diisocyanate, a bifunctional component having two terminal groups each of which contains an active hydrogen, and a chain capping monomer which contains both an active hydrogen and a polymerizable vinyl group.
Claim 40
Dependent Claim
28 words
The drug delivery system of claim 36 wherein the bifunctional component is a polyethylene glycol having a molecular weight of about 500 to less than about 3000 Daltons.
Claim 41
Dependent Claim
22 words
The drug delivery system of claim 37 wherein the polyethylene glycol has a molecular weight of about 750 to about 2500 Daltons.
Claim 42
Dependent Claim
22 words
The drug delivery system of claim 37 wherein the polyethylene glycol has a molecular weight of about 900 to about 1500 Daltons.
Claim 43
Dependent Claim
20 words
The drug delivery system of claim 37 wherein at least 20% by weight of the liquid oligomer is polyethylene glycol.
Claim 44
Dependent Claim
40 words
The drug delivery system of claim 36 wherein the diisocyanate is of the formula OCN--R--NCO wherein R is selected from the group consisting essentially of aliphatic, aliphatic-alicyclic and aliphatic-aromatic hydrocarbon compounds containing from about 4 to about 26 carbon atoms.
Claim 45
Dependent Claim
46 words
The drug delivery system of claim 41 wherein the diisocyanate is selected from the group consisting essentially of tetramethylene diisocyanate, hexamethylene diisocyanate, trimethylhexamethylene diisocyanate, dimer acid diisocyanate, isophorone diisocyanate, hydrogenated diphenylmethane diisocyanate, methylene di(cyclohexyl isocyanate), metaxylene diisocyanate, diethylbenzene diisocyanate, decamethylene 1,10-diisocyanate, cyclohexylene 1,2-diisocyanate, and cyclohexylene 1,4-diisocyanate.
Claim 46
Dependent Claim
16 words
The drug delivery system of claim 36 wherein the chain capping monomer contains one vinyl group.
Claim 47
Dependent Claim
18 words
The drug delivery system of claim 36 wherein the chain capping monomer is hydroxyethyl acrylate or hydroxyethyl methacrylate.
Claim 48
Dependent Claim
21 words
The drug delivery system of claim 36 wherein the photoinitiator comprises about 1 to about 5 weight percent of the oligomer.
Claim 49
Dependent Claim
21 words
The drug delivery system of claim 35 wherein the photoinitiator comprises about 1.5 to about 4 weight percent of the oligomer.
Claim 50
Dependent Claim
34 words
The drug delivery system of claim 35 wherein the photoinitiator is selected from the group consisting of benzil ketals, benzoin ethers, and aromatic ketones, which have been modified to contain a polymerizable vinyl group.
Claim 51
Dependent Claim
12 words
The drug delivery system of claim 35 wherein the photoinitiator is 4-(2-acryloyl-oxyethoxy)-phenyl-2-hydroxy-2-propylketone.
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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) | 1995-06-02 | 1995-12-02 | 1996-06-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-06-02 | 1999-12-02 | 2000-06-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-06-02 | 2003-12-02 | 2004-06-02 | $7700.00 | Window Closed / Lapsed |