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US 8,551,511 B2Granted
Phase-separated biocompatible polymer compositions for medical uses
AssigneeRutgers, The State University of New Jersey
InventorsDon K. Brandom, Durgadas Bolikal, Lioubov Kabalnova, James E. McGrath, Joachim Kohn
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Abstract
A variety of phase-separated biocompatible polymer compositions are described. In preferred embodiments the polymers are bioresorbable and/or biodegradable, and have desirable mechanical properties, such as fracture and/or fatigue toughness, that have previously not been a primary design criteria for such polymers. The polymer compositions are useful in a variety of medical applications, such as in the fabrication of medical devices.
Claims61
A biocompatible polymer composition, comprising at least a first polymer phase and a second polymer phase;
- the first polymer phase having at least one first wet thermal transition temperature selected from a first wet glass transition temperature and a first wet melting point, the first wet thermal transition temperature being at least 38° C.;
- the first polymer phase comprising a number (n) of first recurring units of the formula (I):
- wherein:
- X1 and X2 are each independently selected from the group consisting of halogen, halomethyl, halomethoxy, methyl, methoxy, thiomethyl, nitro, sulfoxide, and sulfonyl;
- y1 and y2 indicate the number of X1 and X2 groups, respectively, and are each independently zero or an integer in the range of 1 to 4;
- q and r are each independently zero or one, where q+r=1 or 2;
- each Al is independently selected from the group consisting of
- each R3 is independently selected from the group consisting of C1-C30 alkyl, C1-C30 heteroalkyl, C5-C30 aryl, C6-C30 alkylaryl, and C2-C30 heteroaryl;
- each R4 independently selected from the group consisting of H, C1-C30 alkyl, and C1-C30 heteroalkyl;
- each R1 is independently selected from the group consisting of
- provided that when R1 is
- Q1 is COOR4 and when R1 is
- r=0;
- R5 is selected from the group consisting of —CH═CH—, —CHJ1-CHJ2-, —(CH2)a—, optionally ring-halogenated
- and optionally ring-halogenated
- wherein q=0 when R5 is
- R6 is selected from the group consisting of —CH═CH—, —CHJ1-CHJ2-, —(CH2)a—, optionally ring-halogenated
- and optionally ring-halogenated
- wherein r=0 when R6 is;
- each a is independently zero or an integer in the range of 1 to 8;
- J1 and J2 are each independently selected from the group consisting of Br and I;
- each Z is independently an O or an S;
- and
- Q1 and Q4 are each independently H, CH2—R4, COOR4 or a crystallizable group comprising from about 6 to about 30 carbon atoms;
- Q2 and Q3 are each independently H, CH2—R4, or a crystallizable group comprising from about 6 to about 30 carbon atoms;
- the second polymer phase having at least one second wet thermal transition temperature selected from a second wet glass transition temperature and a second wet melting point, the second wet thermal transition temperature being 36° C. or lower, the second polymer phase comprising a number (m) of second recurring units of the formula (IId):
- wherein D1 is C1-C24 alkylene and g and h are selected so that the formula (IId) structure has a molecular weight in the range of about 2,000 to about 40,000;
- wherein the number (n) and the number (m) are selected to control the relative amounts of the first polymer phase and the second polymer phase so that (a) the polymer composition is phase-separated over at least the temperature range of about 25° C. to about 50° C., (b) the polymer composition has a water content of 4.5% or less as measured after soaking for 24 hours at 37° C. in 0.1 M phosphate buffered saline (PBS) at pH 7.4;
- and (c) the volume fraction of the second polymer phase in the polymer composition is in the range of about 6% to about 40%, based on total volume.
26 more elements
A biocompatible polymer composition, comprising:
- a number (n) of first polymer recurring units of formula (I):
- wherein:
- X1 and X2 are each independently selected from the group consisting of halogen, halomethyl, halomethoxy, methyl, methoxy, thiomethyl, nitro, sulfoxide, and sulfonyl;
- y1 and y2 indicate the number of X1 and X2 groups, respectively, and are each independently zero or an integer in the range of 1 to 4;
- q and r are each independently zero or one, where q+r=1 or 2;
- each A1 is independently selected from the group consisting of
- each R3 is independently selected from the group consisting of C1-C30 alkyl, C1-C30 heteroalkyl, C5-C30 aryl, C6-C30 alkylaryl, and C2-C30 heteroaryl;
- each R4 independently selected from the group consisting of H, C1-C30 alkyl, C1-C30 heteroalkyl,
- each R1 is independently selected from the group consisting of
- provided that when R1 is
- Q1 is COOR4 and when R1 is
- r=0;
- R5 is selected from the group consisting of —CH═CH—, —CHJ1-CHJ2-, —(CH2)a—, optionally ring-halogenated
- and optionally ring-halogenated
- wherein q=0 when R5 is
- R6 is selected from the group consisting of —CH═CH—, —CHJ1-CHJ2-, —(CH2)a—, optionally
- ring-halogenated
- and optionally ring-halogenated
- wherein r=0 when R6 is
- each a is independently zero or an integer in the range of 1 to 8;
- J1 and J2 are each independently selected from the group consisting of Br and I;
- each Z is independently an O or an S;
- and
- Q1 and Q4 are each independently H, CH2—R4, COOR4 or a crystallizable group comprising from about 6 to about 30 carbon atoms;
- Q2 and Q3 are each independently H, CH2—R4, or a crystallizable group comprising from about 6 to about 30 carbon atoms;
- and
- a number (m) of second polymer recurring units of the formula (IId):
- wherein D1 is C1-C24 alkylene and g and h are selected so that the formula (IId) structure has a molecular weight in the range of about 2,000 to about 40,000;
- and the number (m) of second polymer recurring units is effective to result in phase separation of said polymer composition into first and second polymer phases, wherein said second phase comprises said second polymer recurring units;
- wherein the polymer composition has a water content of 4.5% or less as measured after soaking for 24 hours at 37° C. in 0.1 M phosphate buffered saline (PBS) at pH 7.4;
- and the second polymer recurring units and the number values for (n) and (m) are selected so that said polymer composition remains intact for at least about 15 minutes when tested under fatigue test conditions that comprise (i) providing a fatigue test strip having measurements of 5.0 mm wide, a gauge length of 15 mm and a thickness of 0.1 mm, (ii) aging the fatigue test strip for 7 days at 37° C. in 0.1 M phosphate buffered saline (PBS) at pH 7.4, and (iii) subjecting the aged fatigue test strip to oscillating deformation at a frequency of 1.2 Hz under a stress of 10 MPa in single frequency stress mode while submerged in water at 37° C.
28 more elements
Dependencies are inferred from the claim text.