Polysiloxane-containing polyurethane elastomeric compositions
First Claim
1. A polyurethane elastomeric composition comprising a hard segment and a soft segment, wherein the soft segment is formed from (a) about 2 wt. % to about 40 wt. % of at least one polyether, about 2 wt. % to about 40 wt. % of at least one polycarbonate macrodiol, or about 2 wt. % to about 40 wt. % of a combination of at least one polyether macrodiol and at least one polycarbonate macrodiol, wherein the polyether macrodiol is a compound of the formula:
-
whereinm is an integer of 4 or more; and
n is an integer from 2 to 50; and
(b) about 60 wt. % to about 98 wt. % of at least one polysiloxane macrodiol of formula (I);
wherein R1, R2, R3, R4, R5, and R6 are each independently an optionally substituted straight chain, branched or cyclic, saturated or unsaturated hydrocarbon radical; and
n is an integer from 1 to 100;
wherein the hard segment is present in about 30 wt. % to about 60 wt. % of the polyurethane elastomeric composition and wherein the soft segment is present in about 40 wt. % to about 70 wt. % of the polyurethane elastomeric composition.
5 Assignments
0 Petitions
Accused Products
Abstract
The present invention relates to a material having improved mechanical properties, clarity, processability and/or degradation resistance comprising a polyurethane elastomeric composition which includes a soft segment derived from at least one polysiloxane macrodiol and at least one polyether and/or polycarbonate macrodiol. This material can function as a degradation resistant material or biomaterial and is particularly useful in the manufacture of medical devices, articles or implants which contact living tissues or bodily fluids. The present invention also provides a polyurethane elastomeric composition which includes a soft segment derived from about 60 to 98 wt % of at least one polysiloxane macrodiol and about 2 to 40 wt % of at least one polyether and/or polycarbonate macrodiol and processes for its preparation.
-
Citations
49 Claims
-
1. A polyurethane elastomeric composition comprising a hard segment and a soft segment, wherein the soft segment is formed from (a) about 2 wt. % to about 40 wt. % of at least one polyether, about 2 wt. % to about 40 wt. % of at least one polycarbonate macrodiol, or about 2 wt. % to about 40 wt. % of a combination of at least one polyether macrodiol and at least one polycarbonate macrodiol, wherein the polyether macrodiol is a compound of the formula:
-
wherein m is an integer of 4 or more; and
n is an integer from 2 to 50; and
(b) about 60 wt. % to about 98 wt. % of at least one polysiloxane macrodiol of formula (I);
whereinR1, R2, R3, R4, R5, and R6 are each independently an optionally substituted straight chain, branched or cyclic, saturated or unsaturated hydrocarbon radical; and
n is an integer from 1 to 100;
wherein the hard segment is present in about 30 wt. % to about 60 wt. % of the polyurethane elastomeric composition and wherein the soft segment is present in about 40 wt. % to about 70 wt. % of the polyurethane elastomeric composition. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14)
-
-
15. A polyurethane elastomeric composition comprising a hard segment and a soft segment wherein the soft segment is formed from about (a) 60 wt. % to about 98 wt. % of at least one polysiloxane macrodiol;
- and (b) about 2 wt. % to about 40 wt. % of at least one polyether macrodiol, about 2 wt. % to about 40 wt. % of at least one polycarbonate macrodiol, or about 2 wt. % to about 40 wt. % of a combination of at least one polyether macrodiol and at least one polycarbonate macrodiol, wherein the polyether macrodiol is a compound of the formula;
wherein m is an integer of 4 or more; and
n is an integer from 2 to 50; and
wherein the hard segment is present in about 30 wt. % to about 60 wt. % of the polyurethane elastomeric composition and wherein the soft segment is present in about 40 wt. % to about 70 wt. % of the polyurethane elastomeric composition. - View Dependent Claims (16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29)
- and (b) about 2 wt. % to about 40 wt. % of at least one polyether macrodiol, about 2 wt. % to about 40 wt. % of at least one polycarbonate macrodiol, or about 2 wt. % to about 40 wt. % of a combination of at least one polyether macrodiol and at least one polycarbonate macrodiol, wherein the polyether macrodiol is a compound of the formula;
-
30. A device or article comprising an amount of a polyurethane elastomeric composition effective to render the device biocompatible, the polyurethane elastomeric composition comprising a hard segment and a soft segment, wherein the soft segment is formed from (a) about 2 wt. % to about 40 wt. % of at least one polyether macrodiol, about 2 wt. % to about 40 wt. % of at least one polycarbonate macrodiol, or about 2 wt. % to about 40 wt. % of a combination of at least one polyether macrodiol and at least one polycarbonate macrodiol, wherein the polyether macrodiol is a compound of the formula:
-
wherein m is an integer of 4 or more; and
n is an integer from 2 to 50; and
(b) about 60 wt. % to about 98 wt. % of at least one polysiloxane macrodiol of formula (I);
whereinR1, R2, R3, R4, R5, and R6 are each independently an optionally substituted straight chain, branched or cyclic, saturated or unsaturated hydrocarbon radical; and
n is an integer from 1 to 100;
wherein the hard segment is present in about 30 wt. % to about 60 wt. % of the polyurethane elastomeric composition and wherein the soft segment is present in about 40 wt. % to about 70 wt. % of the polyurethane elastomeric composition. - View Dependent Claims (31, 32)
-
-
33. A device or article comprising a polyurethane elastomeric composition comprising a hard segment and a soft segment, wherein the soft segment is formed from (a) about 2 wt. % to about 40 wt. % of at least one polyether macrodiol, about 2 wt. % to about 40 wt. % of at least one polycarbonate macrodiol, or about 2 wt. % to about 40 wt. % of a combination of at least one polyether macrodiol and at least one polycarbonate macrodiol, wherein the polyether macrodiol is a compound of the formula:
-
wherein m is an integer of 4 or more; and
n is an integer from 2 to 50; and
(b) about 60 wt. % to about 98 wt. % of polysiloxane macrodiol of formula (I);
whereinR1, R2, R3, R4, R5, and R6 are each independently an optionally substituted straight chain, branched or cyclic, saturated or unsaturated hydrocarbon radical; and
n is an integer from 1 to 100;
wherein the hard segment is present in about 30 wt. % to about 60 wt. % of the polyurethane elastomeric composition and wherein the soft segment is present in about 40 wt. % to about 70 wt. % of the polyurethane elastomeric composition; and
wherein the device is artificial leather, a shoe sole, a cable sheathing, varnish, a coating, a structural component for a pump or vehicle, a mining ore screen, a conveyor belt, a laminating compound, a textile, a separation membrane, a sealant or an adhesive component.
-
-
34. A process for preparing a polyurethane elastomeric composition comprising:
-
a) mixing a polysiloxane macrodiol;
a polyether macrodiol, a polycarbonate macrodiol, or a mixture thereof; and
a chain extender; and
b) reacting the mixture with a diisocyanate to yield a polyurethane elastomeric composition comprising a hard segment derived from a diisocyanate and a chain extender; and
a soft segment derived from;
about 60 wt. % to about 98 wt. % of at least one polysiloxane macrodiol; and
about 2 wt. % to about 40 wt. % of at least one polyether macrodiol, about 2 wt. % to about 40 wt. % of at least one polycarbonate macrodiol, or about 2 wt. % to about 40 wt. % of a combination of at least one polyether macrodiol and at least one polycarbonate macrodiol, wherein the polyether macrodiol is a compound of the fornula;
wherein m is an integer of 4 or more; and
n is an integer from 2 to 50; and
wherein the hard segment is present in about 30 wt. % to about 60 wt. % of the polyurethane elastomeric composition and wherein the soft segment is present in about 40 wt. % to about 70 wt. % of the polyurethane elastomeric composition. - View Dependent Claims (35, 36, 37)
-
-
38. A process for preparing a polyurethane elastomeric composition comprising:
-
b) reacting a diisocyanate a polysiloxate macrodiol; and
a polyether macrodiol, a polycarbonate macrodiol, or a mixture thereof;
to form a prepolymer having terminally reactive diisocyanate groups; and
a) reacting the prepolymer with a chain extender to yield a polyurethane elastomeric composition comprising a soft segment derived from (a) about 60 wt. % to about 98 wt. % of at least one polysiloxane macrodiol; and
(b) about 2 wt. % to about 40 wt. % of at least one polyether macrodiol, about 2 wt. % to about 40 wt. % of at least one polycarbonate macrodiol, or about 2 wt. % to about 40 wt. % of a combination of at least one polyether macrodiol and at least one polycarbonate macrodiol, wherein the polyether macrodiol is a compoind of the formula;
wherein m is an integer of 4 or more; and
n is an integer from 2 to 50; and
wherein the polyurethane elalstomeric composition comprises a hard segment derived from a diisocyante and a chain extender;
wherein the hard segment is present in abut 30 wt. % to about 60 wt. % of the polyurethane elastomeric composition and wherein the soft segment is present in about 40 wt. % to about 70 wt. % of the polyurethane elastomeric composition. - View Dependent Claims (39, 40, 41, 42, 43)
wherein R1, R2, R3, R4, R5, and R6 are each independently an optionally substituted straight chain, branched or cyclic, saturated or unsaturated hydrocarbon radical; and
n is an integer from 1 to 100.
-
-
41. The process of claim 38 wherein the polyether macrodiol is polytetramethylene oxide, polypentamethylene oxide, polyhexamethylene oxide, polyheptamethylene oxide, polyoctamethylene oxide, or polydecamethylene oxide.
-
42. The process of claim 38 wherein the polycarbonate macrodiol is a poly(alkylene carbonate), a polycarbonate prepared by reacting an alkylene carbonate with an alkane diol, or a silicon-based polycarbonate.
-
43. The process of claim 38 wherein the chain extender is 1,4-butanediol;
- 1,6-hexanediol;
1,8-octanediol;
1,9-nonanediol;
1,10-decanediol;
1,12-dodecanediol;
1,4-cyclohexane dimethanol;
p-xyleneglycol;
or 1,4-bis(2-hydroxyethoxy) benzene.
- 1,6-hexanediol;
-
44. A polyurethane elastomeric composition comprising a hard segment and a soft segment, wherein the soft segment is formed from (a) about 2 wt. % to about 40 wt. % of at least one polycarbonate macrodiol, or about 2 wt. % to about 40 wt. % of a copolymer of at least one polyether macrodiol and at least one polycarbonate macrodiol;
- and (b) about 60 wt. % to about 98 wt. % of at least one polysiloxane macrodiol of formula (I);
wherein R1, R2, R3, R4, R5, and R6 are each independently an optionally substituted straight chain, branched or cyclic, saturated or unsaturated hydrocarbon radical; and
n is an integer from 1 to 100;
wherein the hard segment is present in about 30 wt. % to about 60 wt. % of the polyurethane elastomeric composition and wherein the soft segment is present in about 40 wt. % to about 70 wt. % of the polyurethane elastomeric composition. - View Dependent Claims (49)
- and (b) about 60 wt. % to about 98 wt. % of at least one polysiloxane macrodiol of formula (I);
-
45. A polyurethane elastomeric composition comprising a hard segment and a soft segment wherein the soft segment is formed from about (a) 60 wt. % to about 98 wt. % of at least one polysiloxane macrodiol;
- and (b) about 2 wt. % to about 40 wt. % of at least one polycarbonate macrodiol, or about 2 wt. % to about 40 wt. % of a copolymer of at least one polyether macrodiol and at least one polycarbonate macrodiol;
wherein the hard segment is present in about 30 wt. % to about 60 wt. % of the polyurethane elastomeric composition and wherein the soft segment is present in about 40 wt. % to about 70 wt. % of the polyurethane elastomeric composition.
- and (b) about 2 wt. % to about 40 wt. % of at least one polycarbonate macrodiol, or about 2 wt. % to about 40 wt. % of a copolymer of at least one polyether macrodiol and at least one polycarbonate macrodiol;
-
46. A device or article comprising an amount of a polyurethane elastomeric composition effective to render the device biocompatible, the polyurethane elastomeric composition comprising a hard segment and a soft segment, wherein the soft segment is formed from (a) about 2 wt. % to about 40 wt. % of at least one polycarbonate macrodiol, or about 2 wt. % to about 40 wt. % of a copolymer of at least one polyether macrodiol and at least one polycarbonate macrodiol;
- and (b) about 60 wt. % to about 98 wt. % of at least one polysiloxane macrodiol of formula (I);
wherein R1, R2, R3, R4, R5, and R6 are each independently an optionally substituted straight chain, branched or cyclic, saturated or unsaturated hydrocarbon radical; and
n is an integer from 1 to 100;
wherein the hard segment is present in about 30 wt. % to about 60 wt. % of the polyurethane elastomeric composition and wherein the soft segment is present in about 40 wt. % to about 70 wt. % of the polyurethane elastomeric composition.
- and (b) about 60 wt. % to about 98 wt. % of at least one polysiloxane macrodiol of formula (I);
-
47. A process for preparing a polyurethane elastomeric composition comprising:
-
a) mixing a polysiloxane macrodiol;
a polyether macrodiol, a polycarbonate macrodiol, or a mixture thereof; and
a chain extender; and
b) reacting the mixture with a diisocyanate to yield a polyurethane elastomeric composition comprising a hard segment derived from a diisocyanate and a chain extender; and
a soft segment derived from;
about 60 wt. % to about 98 wt. % of at least one polysiloxane macrodiol; and
about 2 wt. % to about 40 wt. % of at least one polycarbonate macrodiol, or about 2 wt. % to about 40 wt. % of a copolymer of at least one polyether macrodiol and at least one polycarbonate macrodiol;
wherein the hard segment is present in about 30 wt. % to about 60 wt. % of the polyurethane elastomeric composition and wherein the soft segment is present in about 40 wt. % to about 70 wt. % of the polyurethane elastomeric composition.
-
-
48. A process for preparing a polyurethane elastomeric composition comprising:
-
a) reacting a diisocyanate with a polysiloxane macrodiol; and
a polyether macrodiol, a polycarbonate macrodiol, or a mixture thereof;
to form a prepolymer having terminally reactive diisocyanate groups; and
b) reacting the prepolymer with a chain extender to yield a polyurethane elastomeric composition comprising a soft segment derived from (a) about 60 wt. % to about 98 wt. % of at least one polysiloxane macrodiol; and
(b) about 2 wt. % to about 40 wt. % of at least one polycarbonate macrodiol, or about 2 wt. % to about 40 wt. % of a copolymer of at least one polyether macrodiol and at least one polycarbonate macrodiol;
wherein the polyurethane elastomeric composition comprises a hard segment derived from a diisocyanate and a chain extender;
wherein the hard segment is present in about 30 wt. % to about 60 wt. % of the polyurethane elastomeric composition and wherein the soft segment is present in about 40 wt. % to about 70 wt. % of the polyurethane elastomeric composition.
-
Specification