High strength polyisobutylene polyurethanes
First Claim
1. A polyisobutylene-based thermoplastic polyurethane, comprising:
- (1) a hard segment in the amount of 10% to 60% by weight of the polyisobutylene-based thermoplastic polyurethane, wherein the hard segment includes a urethane, urea, or urethaneurea, and is the product of a reaction of a diisocyanate with a chain extender; and
(2) a soft segment in the amount of 40% to 90% by weight of the polyisobutylene-based thermoplastic polyurethane, wherein the soft segment consists essentially of a polyisobutylene macrodiol;
wherein the number average molecular weight of the polyisobutylene-based thermoplastic polyurethane is greater than or equal to about 40 kilodaltons; and
wherein the polydispersity index of the hard segment is between 2.04 and 2.29, inclusive.
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Accused Products
Abstract
An elastomeric polymer, comprising (1) a hard segment in the amount of 10% to 60% by weight of the elastomeric polymer, wherein the hard segment includes a urethane, urea, or urethaneurea; and (2) a soft segment in the amount of 40% to 90% by weight of the elastomeric polymer, wherein the soft segment includes a polyisobutylene macrodiol and/or diamine. Additionally disclosed is a method of forming a polyisobutylene-based thermoplastic urethane, comprising the steps of (a) reacting a polyisobutylene macrodiol and/or diamine with a diisocyanate to form a first reaction mixture; (b) combining a metal catalyst and a chain extender with the first reaction mixture to create a second reaction mixture, a molar ratio of the metal catalyst to the diisocyanate being greater than 0.0:1 and less than or equal to 0.4:1; and (c) reacting the second reaction mixture for a period of time sufficient to form the polyisobutylene-based thermoplastic urethane.
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Citations
15 Claims
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1. A polyisobutylene-based thermoplastic polyurethane, comprising:
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(1) a hard segment in the amount of 10% to 60% by weight of the polyisobutylene-based thermoplastic polyurethane, wherein the hard segment includes a urethane, urea, or urethaneurea, and is the product of a reaction of a diisocyanate with a chain extender; and (2) a soft segment in the amount of 40% to 90% by weight of the polyisobutylene-based thermoplastic polyurethane, wherein the soft segment consists essentially of a polyisobutylene macrodiol; wherein the number average molecular weight of the polyisobutylene-based thermoplastic polyurethane is greater than or equal to about 40 kilodaltons; and wherein the polydispersity index of the hard segment is between 2.04 and 2.29, inclusive. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15)
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4. The polyurethane of claim 1, wherein the hard segment is present in the amount of from about 30% to about 50% by weight of the elastomeric polymer.
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5. The polyurethane of claim 1, wherein the polyisobutylene macrodiol is hydroxyallyl telechelic polyisobutylene.
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6. The polyurethane of claim 1, wherein the polyisobutylene macrodiol is hydroxyalkyl telechelic polyisobutylene.
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7. The polyurethane of claim 6, wherein the polyisobutylene macrodiol is hydroxypropyl telechelic polyisobutylene.
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8. The polyurethane of claim 1, wherein the polyisobutylene macrodiamine is aminoallyl telechelic polyisobutylene.
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9. The polyurethane of claim 1, wherein the number average molecular weight of the polyisobutylene macrodiol is about 400 Da to about 6000 Da.
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10. The polyurethane of claim 1, wherein the number average molecular weight of the polyisobutylene macrodiol is about 1000 Da to about 3000 Da.
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11. The polyurethane of claim 1, wherein the diisocyanate includes at least one member selected from the group consisting of 4,4′
- -methylenephenyl diisocyanate;
methylene diisocyanate;
p-phenylene diisocyanate;
cis-cyclohexane-1,4-diisocyanate;
trans-cyclohexane-1,4-diisocyanate;
a mixture of cis-cyclohexane-1,4-diisocyanate and trans-cyclohexane-1,4-diisocyanate;
1,6-hexamethylene diisocyanate;
2,4-toluene diisocyanate;
cis-2,4-toluene diisocyanate;
trans-2,4-toluene diisocyanate;
a mixture of cis-2,4-toluene diisocyanate and trans-2,4-toluene diisocyanate;
p-tetramethylxylene diisocyanate; and
m-tetramethylxylene diisocyanate.
- -methylenephenyl diisocyanate;
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12. The polyurethane of claim 1, wherein the chain extender includes at least one member selected from the group consisting of 1,4-bunatediol;
- 1,5-pentanediol;
1,6-hexanediol;
1,8-octanediol;
1,9-nonanediol;
1,10-decanediol;
1,12-dodecanediol;
1,4-cyclohexane dimethanol;
p-xyleneglycol; and
1,4-bis(2-hydroxyethoxy)benzene.
- 1,5-pentanediol;
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13. The polyurethane of claim 1, wherein the chain extender includes at least one member selected from the group consisting of 1,4-diaminobutane;
- 1,5-diaminopentane;
1,6-diaminohexane;
1,8-diaminooctane;
1,9-diaminononane;
1,10-diaminodecane;
1,12-diaminododecane;
1,4-diaminocyclohexane;
2,5-diaminoxylene; and
isophoronediamine.
- 1,5-diaminopentane;
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14. The polyurethane of claim 1, wherein the diisocyanate is 4,4′
- -methylenephenyl diisocyanate and wherein the chain extender is 1,4-butanediol.
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15. The polyurethane of claim 1, wherein:
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the polyisobutylene macrodiol is hydroxyallyl telechelic polyisobutylene; and the hard segment includes a product of a reaction of 4,4′
-methylenephenyl diisocyanate and 1,4-butanediol.
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Specification