Granted Patent B2

US 8,604,077 · App. 12/674,322 · Granted Dec 10, 2013

Inventors: Douglas Alan Wicks (Plymouth, MN); Charles Todd Williams (Pittsburgh, PA); Sergey A. Selifonov (Plymouth, MN)

Assignee: Segetis, Inc.

Abstract

Claims (118)

1. A polyester having a structure corresponding to (1):

wherein

the polyester is derived from

wherein in formulas (1) and (1 a ),

p is an integer of at least 2,

a is 0 or 1,

b is 0 or 1,

R 3 is methyl;

R 4 is hydrogen, methyl, or ethyl, and

X is hydrogen or a lower alkyl.

2. The polyester of claim 1 wherein p is 10 or greater.

3. The polyester of claim 1 wherein p is 100 or greater.

4. A material comprising a compound having a structure corresponding structures (2), (3), or a mixture thereof:

wherein

a equals 0 or 1;

b equals 0 or 1;

R 2 represents an alkylene, cycloalkylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and optionally comprises halogen, ether, ester, carbonate, amide or urethane groups;

R 3 is methyl; and

R 4 is hydrogen, methyl, or ethyl.

5. The material of claim 4 wherein R 2 is a residue of diethylene glycol or 1,6-hexanediol.

6. A polyurethane comprising the reaction product of one or more material of claim 4 and one or more organic diisocyanates.

7. A polyhydroxy compound having a structure corresponding to (4):

wherein

a equals 0 or 1;

b equals 0 or 1;

R 2 represents an alkylene, cycloalkylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and may contain halogen, ether, ester, carbonate, amide or urethane groups;

R 3 is methyl;

R 4 is hydrogen, methyl, or ethyl;

α is an integer of about 1to 100; and

β is an integer of at least 2.

8. The polyhydroxy compound of claim 7 having an average hydroxyl equivalent weight of between about 200 and 5000.

9. The polyhydroxy compound of claim 7 wherein β is between 2 and 10.

10. A polyurethane comprising the reaction product of one or more polyhydroxy compounds of claim 7 and one or more organic diisocyanates.

11. An isocyanate prepolymer having a structure corresponding to (5):

wherein

a equals 0 or 1;

b equals 0 or 1;

R 2 represents an alkylene, cycloalkylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and may contain halogen, ether, ester, carbonate, amide or urethane groups;

R 3 is methyl;

R 4 is hydrogen, methyl, or ethyl;

R 5 is the residue of an organic diisocyanate having a molecular weight of about 100 to 1,000 g/mol;

α is an integer of about 1to 100; and

β is an integer of at least 2.

12. The isocyanate prepolymer of claim 11 wherein R 5 is the residue of an organic diisocyanate having a molecular weight of about 140 to 400 g/mol.

13. The isocyanate prepolymer of claim 11 wherein β is between 2 and 10.

14. A polyurethane comprising the reaction product of one or more isocyanate prepolymers of claim 11 and one or more polyols.

15. A copolyester having a structure corresponding to (6)):

wherein

a equals 0 or 1;

b equals 0 or 1;

R 2 represents an alkylene, cycloalkylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and may contain halogen, ether, ester, carbonate, amide or urethane groups;

R 3 is methyl;

R 4 is hydrogen, methyl, or ethyl;

R 5 is the residue of an organic diacid having a molecular weight of about 100 to 1,000 g/mol;

α is an integer of about 1to 100; and

x, y and z represent molar fractions of the indicated residue in the copolymer, such that the sum of (x+y+z) equals 1.

16. The copolyester of claim 15 wherein R 5 is the residue of an organic diacid having a molecular weight of about 120 to 400 g/mol.

17. The copolyester of claim 15 comprising two or more hydroxyl endgroups.

18. A polyurethane comprising the reaction product of one or more copolyesters of claim 17 and one or more organic diisocyanates.

19. A polyester having a structure corresponding to (7):

wherein

the polyester is derived from

wherein in formulas (7) and (7 a ),

p is an integer of at least 2,

R 3 is methyl;

R 4 is hydrogen, methyl, or ethyl, and

X is hydrogen or a lower alkyl.

20. The compound of claim 19 wherein p is 10 or greater.

21. The compound of claim 19 wherein p is 100 or greater.

22. A material comprising a compound having a structure corresponding structures (8), (9), or a mixture thereof:

wherein

R 2 represents an alkylene, cycloalkylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and may contain halogen, ether, ester, carbonate, amide or urethane groups;

R 3 is methyl; and

R 4 is hydrogen, methyl, or ethyl.

23. The material of claim 22 wherein R 2 is a residue of diethylene glycol or 1,6-hexanediol.

24. A polyurethane comprising the reaction product of one or more of the compounds of claim 22 and one or more organic diisocyanates.

25. A polyhydroxy compound having a structure corresponding to (10):

wherein

R 2 represents an alkylene, cycloalkylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and may contain halogen, ether, ester, carbonate, amide or urethane groups;

R 3 is methyl;

R 4 is hydrogen, methyl, or ethyl;

α is an integer of about 1to 100; and

β is an integer of at least 2.

26. The polyhydroxy compound of claim 25 having an average hydroxyl equivalent weight of between about 200 and 5000.

27. The polyhydroxy compound of claim 25 wherein β is between 2 and 10.

28. A polyurethane comprising the reaction product of one or more polyhydroxy compounds of claim 25 and one or more organic diisocyanates.

29. An isocyanate prepolymer having a structure corresponding to (11):

wherein

R 2 represents an alkylene, cycloalkylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and may contain halogen, ether, ester, carbonate, amide or urethane groups;

R 3 is methyl;

R 4 is hydrogen, methyl, or ethyl;

R 5 is the residue of an organic diisocyanate having a molecular weight of about 100 to 1,000 g/mol;

α is an integer of about 1to 100; and

β is an integer of at least 2.

30. The isocyanate prepolymer of claim 29 wherein R 5 is the residue of an organic diisocyanate having a molecular weight of about 140 to 400 g/mol.

31. The isocyanate prepolymer of claim 29 wherein β is between 2 and 10.

32. A polyurethane comprising the reaction product of one or more isocyanate prepolymers of claim 29 and one or more polyols.

33. A copolyester having a structure corresponding to (12):

wherein

R 2 represents an alkylene, cycloalkylene or aralkylene group of 2-36 carbons, with the hydroxyl groups attached to saturated carbons, and may contain halogen, ether, ester, carbonate, amide or urethane groups;

R 3 is methyl;

R 4 is hydrogen, methyl, or ethyl;

R 5 is the residue of an organic diacid having a molecular weight of about 100 to 1,000 g/mol;

α is an integer of about 1to 100; and

x, y and z represent molar fractions of the indicated residue in the copolymer, such that the sum of (x+y+z) equals 1.

34. The copolyester of claim 33 wherein R 5 is the residue of an organic diacid having a molecular weight of about 120 to 400 g/mol.

35. The copolyester of claim 33 comprising two or more hydroxyl endgroups.

36. A polyurethane comprising the reaction product of one or more copolyesters of claim 35 and one or more organic diisocyanates.

37. The polyurethane of claim 6 , wherein the diisocyanate is at least one selected from 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethyl-1,6-hexamethylene diisocyanate, 1,12-dodecamethylene diisocyanate, cyclohexane-1,3-diisocyanate, cyclohexane-1,4-diisocyanate, 1-isocyanato-2-isocyanatomethylcyclopentane, 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl-cyclohexane, bis-(4-isocyanatocyclohexyl)methane, 2,4′-dicyclohexylmethane diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 1,3-bis-(isocyanatomethyl)cyclohexane, 1,4-bis-(isocyanatomethyl)cyclohexane,bis-(4-isocyanato-3-methyl-cyclohexyl)methane, α,α,α′,α′-tetramethyl-1,3-xylylene diisocyanate, α,α,α′,α′-tetramethyl-1,4-xylylene diisocyanate, 1-isocyanato-l-methyl-4(3)-isocyanatomethyl cyclohexane, 2,4-hexahydrotolylene diisocyanate, 2,6-hexahydrotolylene diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,2′-diphenylmethane diisocyanate, 2,4′-diphenylmethane diisocyanate, 4,4′-diphenylmethane diisocyanate, and 1,5-diisocyanato naphthalene.

38. The polyurethane of claim 10 , wherein the diisocyanate is at least one selected from 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethyl-1,6-hexamethylene diisocyanate, 1,12-dodecamethylene diisocyanate, cyclohexane-1,3-diisocyanate, cyclohexane-1,4-diisocyanate, 1-isocyanato-2-isocyanatomethylcyclopentane, 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl-cyclohexane, bis-(4-isocyanatocyclohexyl)methane, 2,4′-dicyclohexylmethane diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 1,3-bis-(isocyanatomethyl)cyclohexane, 1,4-bis-(isocyanatomethyl)cyclohexane, bis-(4-isocyanato-3-methyl-cyclohexyl)methane, α,α,α′,α′-tetramethyl-1,3-xylylene diisocyanate, α,α,α′,α′-tetramethyl-1,4-xylylene diisocyanate, 1-isocyanato-1-methyl-4(3)-isocyanatomethyl cyclohexane, 2,4-hexahydrotolylene diisocyanate, 2,6-hexahydrotolylene diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,2′-diphenylmethane diisocyanate, 2,4′-diphenylmethane diisocyanate, 4,4′-diphenylmethane diisocyanate, and 1,5-diisocyanato naphthalene.

39. The polyurethane of claim 11 , wherein the diisocyanate is at least one selected from 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethyl-1,6-hexamethylene diisocyanate, 1,12-dodecamethylene diisocyanate, cyclohexane-1,3-diisocyanate, cyclohexane-1,4-diisocyanate, 1-isocyanato-2-isocyanatomethylcyclopentane, 1-isocyanato-3 -isocyanatomethyl-3,5,5-trimethyl-cyclohexane, bis-(4-isocyanatocyclohexyl)methane, 2,4′-dicyclohexylmethane diisocyanate,4,4′-dicyclohexylmethane diisocyanate,1,3-bis-(isocyanatomethyl)cyclohexane, 1,4-bis-(isocyanatomethyl)cyclohexane, bis-(4-isocyanato-3-methyl-cyclohexyl)methane, α,α,α′,α′-tetramethyl-1,3-xylylene diisocyanate, α,α,α′,α′-tetramethyl-1,4-xylylene diisocyanate, 1-isocyanato-1-methyl-4(3)-isocyanatomethyl cyclohexane, 2,4-hexahydrotolylene diisocyanate, 2,6-hexahydrotolylene diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,2′-diphenylmethane diisocyanate, 2,4′-diphenylmethane diisocyanate, 4,4′-diphenylmethane diisocyanate, and 1,5-diisocyanato naphthalene.

40. The polyurethane of claim 18 , wherein the diisocyanate is at least one selected from 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethyl-1,6-hexamethylene diisocyanate, 1,12-dodecamethylene diisocyanate, cyclohexane-1,3-diisocyanate, cyclohexane-1,4-diisocyanate,1-isocyanato-2-isocyanatomethylcyclopentane, 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl-cyclohexane, bis-(4-isocyanatocyclohexyl)methane, 2,4′-dicyclohexylmethane diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 1,3-bis-(isocyanatomethyl)cyclohexane, 1,4-bis-(isocyanatomethyl)cyclohexane, bis-(4-isocyanato-3-methyl-cyclohexyl)methane, α,α,α′,α′-tetramethyl-1,3-xylylene diisocyanate, α,α,α′,α′-tetramethyl-1,4-xylylene diisocyanate, 1-isocyanato-1-methyl-4(3)-isocyanatomethyl cyclohexane, 2,4-hexahydrotolylene diisocyanate, 2,6-hexahydrotolylene diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,2′-diphenylmethane diisocyanate, 2,4′-diphenylmethane diisocyanate, 4,4′-diphenylmethane diisocyanate, and 1,5-diisocyanato naphthalene.

41. The polyurethane of claim 24 , wherein the diisocyanate is at least one selected from 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethyl-1,6-hexamethylene diisocyanate, 1,12-dodecamethylene diisocyanate, cyclohexane-1,3-diisocyanate, cyclohexane-1,4-diisocyanate,1-isocyanato-2-isocyanatomethylcyclopentane, 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl-cyclohexane, bis-(4-isocyanatocyclohexyl)methane, 2,4′-dicyclohexylmethane diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 1,3-bis-(isocyanatomethyl)cyclohexane, 1,4-bis-(isocyanatomethyl)cyclohexane, bis-(4-isocyanato-3-methyl-cyclohexyl)methane, α,α,α′,α′-tetramethyl-1,3-xylylene diisocyanate, α,α,α′,α′-tetramethyl-1,4-xylylene diisocyanate, 1-isocyanato-1-methyl-4(3)-isocyanatomethyl cyclohexane, 2,4-hexahydrotolylene diisocyanate, 2,6-hexahydrotolylene diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,2′-diphenylmethane diisocyanate, 2,4′-diphenylmethane diisocyanate, 4,4′-diphenylmethane diisocyanate, and 1,5-diisocyanato naphthalene.

42. The polyurethane of claim 28 , wherein the diisocyanate is at least one selected from 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethyl-1,6-hexamethylene diisocyanate, 1,12-dodecamethylene diisocyanate, cyclohexane-1,3-diisocyanate, cyclohexane-1,4-diisocyanate,1-isocyanato-2-isocyanatomethylcyclopentane, 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl-cyclohexane, bis-(4-isocyanatocyclohexyl)methane, 2,4′-dicyclohexylmethane diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 1,3-bis-(isocyanatomethyl)cyclohexane, 1,4-bis-(isocyanatomethyl)cyclohexane, bis-(4-isocyanato-3-methyl-cyclohexyl)methane, α,α,α′,α′-tetramethyl-1,3-xylylene diisocyanate, α,α,α′,α′-tetramethyl-1,4-xylylene diisocyanate, 1-isocyanato-1-methyl-4(3)-isocyanatomethyl cyclohexane, 2,4-hexahydrotolylene diisocyanate, 2,6-hexahydrotolylene diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,2′-diphenylmethane diisocyanate, 2,4′-diphenylmethane diisocyanate, 4,4′-diphenylmethane diisocyanate, and 1,5-diisocyanato naphthalene.

43. The polyurethane of claim 29 , wherein the diisocyanate is at least one selected from 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethyl-1,6-hexamethylene diisocyanate, 1,12-dodecamethylene diisocyanate, cyclohexane-1,3-diisocyanate, cyclohexane-1,4-diisocyanate,1-isocyanato-2-isocyanatomethylcyclopentane, 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl-cyclohexane, bis-(4-isocyanatocyclohexyl)methane, 2,4′-dicyclohexylmethane diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 1,3-bis-(isocyanatomethyl)cyclohexane, 1,4-bis-(isocyanatomethyl)cyclohexane, bis-(4-isocyanato-3-methyl-cyclohexyl)methane, α,α,α′,α′-tetramethyl-1,3-xylylene diisocyanate, α,α,α′,α′-tetramethyl-1,4-xylylene diisocyanate, 1-isocyanato-1-methyl-4(3)-isocyanatomethyl cyclohexane, 2,4-hexahydrotolylene diisocyanate, 2,6-hexahydrotolylene diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,2′-diphenylmethane diisocyanate, 2,4′-diphenylmethane diisocyanate, 4,4′-diphenylmethane diisocyanate, and 1,5-diisocyanato naphthalene.

44. The polyurethane of claim 36 , wherein the diisocyanate is at least one selected from 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethyl-1,6-hexamethylene diisocyanate, 1,12-dodecamethylene diisocyanate, cyclohexane-1,3-diisocyanate, cyclohexane-1,4-diisocyanate,1-isocyanato-2-isocyanatomethylcyclopentane, 1-isocyanato-3-isocyanatomethyl-3,5,5-trimethyl-cyclohexane, bis-(4-isocyanatocyclohexyl)methane, 2,4′-dicyclohexylmethane diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 1,3-bis-(isocyanatomethyl)cyclohexane, 1,4-bis-(isocyanatomethyl)cyclohexane, bis-(4-isocyanato-3-methyl-cyclohexyl)methane, α,α,α′,α′-tetramethyl-1,3-xylylene diisocyanate, α,α,α′,α′-tetramethyl-1,4-xylylene diisocyanate, 1-isocyanato-1-methyl-4(3)-isocyanatomethyl cyclohexane, 2,4-hexahydrotolylene diisocyanate, 2,6-hexahydrotolylene diisocyanate, 1,3-phenylene diisocyanate, 1,4-phenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,2′-diphenylmethane diisocyanate, 2,4′-diphenylmethane diisocyanate, 4,4′-diphenylmethane diisocyanate, and 1,5-diisocyanato naphthalene.

45. The copolyester of claim 15 , wherein the organic diacid is at least one selected from succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, nonanedicarboxylic acid, decanedicarboxylic acid, terephthalic acid, isophthalic acid, o-phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, maleic acid, fumaric acid, naphthalene dioc acid, dimerized fatty acids, and hydrogenated dimerized fatty acid.

46. The copolyester of claim 33 , wherein the organic diacid is at least one selected from succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, nonanedicarboxylic acid, decanedicarboxylic acid, terephthalic acid, isophthalic acid, o-phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, maleic acid, fumaric acid, naphthalene dioc acid, dimerized fatty acids, and hydrogenated dimerized fatty acid.

Assignments (2)

Continuity (10)