IP Library Granted Patent US 7,932,343
Granted Patent B2
US 7,932,343 · App. 12/488,047 · Granted Apr 26, 2011

Biomaterial

Assignee: Vysera Biomedical Limited
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Quick Facts
Patent No.
US 7,932,343
App. No.
12/488,047
Granted
Apr 26, 2011
Kind
B2
Abstract

The present invention provides a triblock copolymer and a viscoelastic biostable foam comprising the same.

Claims (40)

1. A viscoelastic biostable foam comprising a triblock copolymer of formula residue I

wherein:

each represents a point of attachment to a urethane or urea linkage;

each of X and Y is independently an ether, an ester, a carbonate, or a fluorohydrocarbon, or mixture thereof;

each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is independently selected from one or more of R, OR, —CO 2 R, a fluorinated hydrocarbon, a polyether, a polyester or a fluoropolymer

each R is independently hydrogen, an optionally substituted C 1-20 aliphatic group, or an optionally substituted group selected from phenyl, 8-10 membered bicyclic aryl, a 4-8 membered monocyclic saturated or partially unsaturated heterocyclic ring having 1-2 heteroatoms independently selected from nitrogen, oxygen, or sulphur, or 5-6 membered monocyclic or 8-10 membered bicyclic heteroaryl group having 1-4 heteroatoms independently selected from nitrogen, oxygen, or sulfur;

each of m n and p is independently 2 to 100; and

each of L 1 and L 2 is independently a bivalent C 1-20 hydrocarbon chain wherein 1-4 methylene units of the hydrocarbon chain are optionally and independently replaced by —O—, —S—, —N(R)—, —C(O)—, —C(O)N(R)—, —N(R)C(O)—, —SO 2 — —SO 2 N(R)—, —N(R)SO 2 —, —OC(O)—, —C(O)O—, or a bivalent cycloalkylene, arylene, heterocyclene, or heteroarylene, provided that neither of L 1 nor L 2 comprises a urea or urethane moiety.

2. The viscoelastic biostable film according to claim 1 wherein the triblock copolymer residue is selected from:

3. The viscoelastic biostable foam according to claim 1 , wherein at least one of (a), (b), (c), (d), (e), (f), (g) or (h) applies:

(a) said foam is stable to gastric fluid for at least 3 months, for at least 4 months, for at least 5 months, for at least 6 months, for at least 7 months, for at least 8 months, for at least 9 months, for at least 10 months, for at least 11 months, or for at least one year,

(b) said foam takes up less than about 5%, less than about 10%, less than about 15%, less than about 20%, less than about 25%, or less than about 30% by weight of water at equilibrium,

(c) said foam has an elongation capacity of about 200-1200%,

(d) said foam has a tensile strength of about 0.1 to about 1.0 MPa,

(e) said foam has a density of 0.1 to 1.5 g/cm 3 ,

(f) said foam has a density of 0.3 to 1.2 g/cm 3 ,

(g) said foam has a density of 0.8 to 0.9 g/cm 3 , or

(h) said foam has a density of 0.5 to 0.6 g/cm 3 .

4. The viscoelastic biostable foam according to claim 1 , wherein X is selected from ethylene oxide, difluoromethyl ethylene oxide, trifluoromethyl ethylene oxide, propylene oxide, difluoromethyl propylene oxide, propylene oxide, trifluoromethyl propylene oxide, butylene oxide, tetramethylene ether glycol, tetrahydrofuran, oxymethylene, ether ketone, etherether ketone, dimethylsiloxane, diethylsiloxane, methyl phenyl siloxane, diphenyl siloxane, methyl di-fluoroethyl siloxane, methyl tri-fluoroethyl siloxane, phenyl di-fluoroethyl siloxane, phenyl tri-fluoroethyl siloxane, ethylene terephthalate, ethylene terephthalate ionomer, ethylene naphthalate, methylene naphthalate, butylene teraphalate, butylene naphthalate, or polycarbonate.

5. The viscoelastic biostable foam according to claim 4 , wherein Y is selected from ethylene oxide, difluoromethyl ethylene oxide, trifluoromethyl ethylene oxide, propylene oxide, difluoromethyl propylene oxide, propylene oxide, trifluoromethyl propylene oxide, butylene oxide, tetramethylene ether glycol, tetrahydrofuran, oxymethylene, ether ketone, etherether ketone, dimethylsiloxane, diethylsiloxane, methyl phenyl siloxane, diphenyl siloxane, methyl di-fluoroethyl siloxane, methyl tri-fluoroethyl siloxane, phenyl di-fluoroethyl siloxane, phenyl tri-fluoroethyl siloxane, ethylene terephthalate, ethylene terephthalate ionomer, ethylene naphthalate, methylene naphthalate, butylene teraphalate, butylene naphthalate, or polycarbonate.

6. The viscoelastic biostable foam according to claim 5 , wherein X and Y are the same and selected from ethylene oxide, difluoromethyl ethylene oxide, trifluoromethyl ethylene oxide, propylene oxide, difluoromethyl propylene oxide, propylene oxide, trifluoromethyl propylene oxide, butylene oxide, tetramethylene ether glycol, tetrahydrofuran, oxymethylene, ether ketone, etherether ketone, dimethylsiloxane, diethylsiloxane, methyl phenyl siloxane, diphenyl siloxane, methyl di-fluoroethyl siloxane, methyl tri-fluoroethyl siloxane, phenyl di-fluoroethyl siloxane, phenyl tri-fluoroethyl siloxane, ethylene terephthalate, ethylene terephthalate ionomer, ethylene naphthalate, methylene naphthalate, butylene teraphalate, butylene naphthalate, or polycarbonate.

7. The viscoelastic biostable foam according to claim 1 , wherein X and Y are both the same.

8. The viscoelastic biostable foam according to claim 1 wherein X and Y are both an ether.

9. The viscoelastic biostable foam according to claim 1 , wherein X and Y are both propylene oxide.

10. The viscoelastic biostable foam according to claim 1 , wherein

(a) m and p are each independently between 2 and 50 and n is between 2 and 20,

(b) m and p are each independently between 2 and 30 and n is between 2 and 20, or

(c) each of m, n, and p are 8-16.

11. The viscoelastic biostable foam according to claim 1 , wherein

(a) one or more of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is independently an optionally substituted C 1-6 alkyl,

(b) each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is independently methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, isobutyl, or cyclobutyl,

(c) each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is independently mono-, di-, tri, or perfluorinated methyl, ethyl, propyl, butyl, or phenyl, or

(d) each of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 is independently methyl, ethyl, propyl, trifluoromethyl, trifluoroethyl, or trifluoropropyl.

12. The viscoelastic biostable foam according to claim 1 wherein at least one of (a), (b), (c), (d), (e) or (f) applies:

(a) each of L 1 and L 2 is independently a bivalent C 1-20 alkylene chain,

(b) each of L 1 and L 2 is independently a bivalent C 1-10 alkylene chain,

(c) each of L 1 and L 2 is independently a bivalent methylene, ethylene, propylene, or butylene chain,

(d) each of L 1 and L 2 is independently —OCH 2 —, —OCH 2 CH 2 —, —OCH 2 CH 2 CH 2 —, or —OCH 2 CH 2 CH 2 CH 2 —,

(e) each of L 1 and L 2 is independently a bivalent C 1-6 alkylene chain wherein at least one methylene unit of the chain is replaced by —O— and at least one methylene unit of the chain is replaced by a bivalent arylene, or

(f) each of L 1 and L 2 is independently —OCH 2 -phenylene-, —OCH 2 CH 2 -phenylene-, —OCH 2 CH 2 -phenylene-CH 2 —, or —OCH 2 CH 2 CH 2 CH 2 -phenylene-.

Assignments (4)
CORRECTIVE ASSIGNMENT TO CORRECT THE CITY OF THE ASSIGNEE FROM HUMELBAEK TO HUMLEBAEK AS CORRECTLY INDICATED ON THE ASSIGNMENT PREVIOUSLY RECORDED ON REEL 037917 FRAME 0992. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNEE'S CITY TO BE HUMLEBAEK. Recorded Mar 17, 2016
From: VYSERA BIOMEDICAL LIMITED
To: COLOPLAST A/S
Reel/Frame 038131/0012 →
CORRECTIVE ASSIGNMENT TO CORRECT THE CITY OF THE ASSIGNEE PREVIOUSLY RECORDED ON REEL 037917 FRAME 0992. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Mar 10, 2016
From: VYSERA BIOMEDICAL LIMITED
To: COLOPLAST A/S
Reel/Frame 038053/0797 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 8, 2016
From: VYSERA BIOMEDICAL LIMITED
To: COLOPLAST A/S
Reel/Frame 037917/0992 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 20, 2009
From: BEHAN, NIALL; KUMAR, ASHUTOSH
To: VYSERA BIOMEDICAL LIMITED
Reel/Frame 023397/0132 →
Continuity (3)
Provisional Application 61074400 · Jun 20, 2008
Provisional Application 61181043 · May 26, 2009
Related Publication 20100120934A1 · May 13, 2010