Application US20190092898

DYNAMIC UREA BONDS WITH FAST HYDROLYTIC KINETICS FOR POLYMERS
[+] Show Details

US20190092898

1. A hydrolysable polymer comprising a hindered urea bond functional group corresponding to the following Formula (I) (17) (4)

wherein R¹, R², and R³are independently selected from —(C₁-C₂₀)alkyl, —(C₃-C₁₀)cyclolalkyl, —(C₁-C₂₀)alkyl(C₃-C₁₀)cycloalkyl, —(C₃-C₁₀)cycloalkyl(C₁-C₂₀)alkyl, —Ar², —(C₁-C₂₀)alkyl-Ar², —C₂-C₂₀)alkyl-PEG-(C₂-C₂₀)alkyl, and H;

R⁴is selected from H and —(C₁-C₂₀)alkyl;

Ar¹and Ar²are independently selected from phenyl, naphthyl, a 5 or 6-membered heteroaromatic ring containing one or more heteroatoms selected from nitrogen, oxygen, sulfur, and combinations thereof, and a 7 to 10-membered fused bicyclic heteroaromatic ring containing one or more heteroatoms selected from nitrogen, oxygen, sulfur, and combinations thereof, wherein each Ar¹or Ar²is optionally substituted with one or more substituents selected from F, Cl, Br, I, —(C₁-C₈)alkyl, —(C₃-C₈)cycloalkyl, —OR⁵, —CN, —SR⁵, —SOR⁵, —SO₂R⁵, —COOR⁵, —COR⁵, —CONR⁵R⁵, and —NR⁵COR⁵—, wherein

R⁵is selected from H and —(C₁-C₈)alkyl.

2. A hydrolysable polymer according to claim 1 wherein R¹, R², R³, are each methyl. (3) (0)

6. A hydrolysable polymer according to claim 1 wherein Ar¹is selected from phenyl, naphthyl, furyl, benzofuryl, oxazolyl, isoxazolyl, oxadiazolyl, benzoxazolyl, benzoxadiazolyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, indolyl, isoindolyl, indolizinyl, benzimidazolyl, indazolyl, benzotriazolyl, tetrazolopyridazinyl, carbazolyl, purinyl, quinolinyl, isoquinolinyl, and imidazopyridyl. (1) (0)

10. A hydrolysable polymer according to claim 1 wherein the hindered urea bond functional group has a Keg that is greater than or equal to 1×10⁴M⁻¹and less than or equal to 1×10⁸M⁻¹at 25° C. (0)

11. A hydrolysable polymer according to claim 1 wherein the hindered urea bond functional group has a k₋₁that is greater than or equal to 0.05 h⁻¹at 25° C. (0)

14. A hydrolysable polymer according to claim 1 wherein the hindered urea bond functional group has a k₁that is greater than or equal to 1×10⁴M⁻¹h⁻¹at 25° C. (0)

15. A hydrolysable polymer according to claim 1 wherein the polymer exhibits at least 10% hydrolysis of the hindered urea bond functional groups at 24 hours at 37° C. (0)

16. A hydrolysable polymer according to claim 1 wherein the polymer exhibits a hindered urea bond functional group hydrolysis half-life of less than or equal to 24 hours at 37° C. (0)

18. A hydrolysable polymer according to claim 1 that is hydrolysable over the pH range from about 2 to about 11. (0)

19. A biodegradable packaging material comprising a hydrolysable polymer according to claim 1. (0)

20. A drug delivery system comprising a hydrolysable polymer according to claim 1. (0)

21. A medical device comprising a hydrolysable polymer according to claim 1. (1) (0)

23. A surgical suture comprising a hydrolysable polymer according to claim 1. (0)

24. A scaffold for tissue regeneration comprising a hydrolysable polymer according to claim 1. (0)

25. An environmentally degradable packaging, coating, or film comprising a hydrolysable polymer according to claim 1. (0)

30. A hydrolysable polymer according to claim 1 wherein the hindered urea bond of Formula (I) is in the main polymer chain. (0)

31. A hydrolysable polymer according to claim 1 wherein the polymer comprises one or more side chains and the hindered urea bond of Formula (I) is in a side chain of the polymer. (0)

32. A hydrolysable polymer according to claim 1 wherein the polymer is a self-healing polymer (0)

8. (canceled) (0)

9. (canceled) (0)

12. (canceled) (0)

13. (canceled) (0)

17. (canceled) (0)

26. A hydrolysable hindered urea bond-containing polymer comprising recurring units from: (1) (2)

(a) a hindered amine monomer containing two or more hindered amine functional groups, and

(b) an aromatic isocyante monomer containing two or more aromatic isocyanate groups.

27. A hydrolysable hindered urea bond-containing polymer according to claim 26 wherein the hindered amine monomer corresponds to the following Formula (II) (0) (8)

Ar²is selected from phenyl, naphthyl, a 5 or 6-membered heteroaromatic ring containing one or more heteroatoms selected from nitrogen, oxygen, sulfur, and combinations thereof, and a 7 to 10-membered heteroaromatic ring or fused bicyclic heteroaromatic ring containing one or more heteroatoms selected from nitrogen, oxygen, sulfur, and combinations thereof, wherein each Ar¹and Ar²is optionally substituted with one or more substituents selected from F, Cl, Br, I, —(C₁-C₈)alkyl, —(C₃-C₈)cycloalkyl, —OR⁵, —CN, —SR⁵, —SOR⁵, —SO₂R⁵, —COOR⁵, —COR⁵, —CONR⁵R⁵, and —NR⁵COR⁵—, wherein

R⁵is selected from H and —(C₁-C₅)alkyl,

and n is an integer from 2 to 100; and

wherein the aromatic isocyante monomer corresponds to the following Formula (III)

wherein Ar¹is selected from phenyl, naphthyl, a 5 or 6-membered heteroaromatic ring containing one or more heteroatoms selected from nitrogen, oxygen, sulfur, and combinations thereof, and a 7 to 10-membered heteroaromatic ring or fused bicyclic heteroaromatic ring containing one or more heteroatoms selected from nitrogen, oxygen, sulfur, and combinations thereof, wherein each Ar is optionally substituted with one or more substituents selected from F, Cl, Br, I, —(C₁-C₈)alkyl, —(C₃-C₈)cycloalkyl, —OR⁵, —CN, —SR⁵, —SOR⁵, —SO₂R⁵, —COOR⁵, —COR⁵, —CONR⁵R⁵, and —NR⁵COR⁵—, wherein

R⁵is selected from H and —(C₁-C₈)alkyl.

and m is an integer from 0 to 100.

28. A hydrolysable hindered urea bond-containing polymer made by a process comprising; (1) (2)

(a) reacting a hindered amine monomer containing two or more hindered amine functional groups, and

(b) an aromatic isocyante monomer containing two or more aromatic isocyanate groups.

29. A hydrolysable hindered urea bond-containing polymer according to claim 28 wherein the hindered amine monomer corresponds to the following Formula (II) (0) (6)

Ar²is selected from phenyl, naphthyl, a 5 or 6-membered heteroaromatic ring containing one or more heteroatoms selected from nitrogen, oxygen, sulfur, and combinations thereof, and a 7 to 10-membered heteroaromatic ring or fused bicyclic heteroaromatic ring containing one or more heteroatoms selected from nitrogen, oxygen, sulfur, and combinations thereof, wherein each Ar is optionally substituted with one or more substituents selected from F, Cl, Br, I, —(C₁-C₈)alkyl, —(C₃-C₅)cycloalkyl, —OR⁵, —CN, —SR⁵, —SOR⁵—SO₂R⁵, —COOR⁵, —COR⁵, —CONR⁵R⁵, and —NR⁵COR⁵—, wherein R⁵is selected from H and —(C₁-C₅)alkyl,

and n is an integer from 2 to 100; and

wherein the aromatic isocyante monomer corresponds to the following Formula (III)

wherein Ar¹is selected from phenyl, naphthyl, a 5 or 6-membered heteroaromatic ring containing one or more heteroatoms selected from nitrogen, oxygen, sulfur, and combinations thereof, and a 7 to 10-membered heteroaromatic ring or fused bicyclic heteroaromatic ring containing one or more heteroatoms selected from nitrogen, oxygen, sulfur, and combinations thereof, wherein each Ar is optionally substituted with one or more substituents selected from F, Cl, Br, I, —(C₁-C₈)alkyl, —(C₃-C₈)cycloalkyl, —OR⁵, —CN, —SR⁵, —SOR⁵, —SO₂R, —COOR⁵, —OR⁵, —CONR⁵R⁵, and —NR⁵COR⁵—, wherein R⁵is selected from H and —(C₁-C₈)alkyl.

and m is an integer from 0 to 100.

View Abstract and Specification Size

PDF with Images and Document Face >

Full Text Publication >

Application US20190092898

DYNAMIC UREA BONDS WITH FAST HYDROLYTIC KINETICS FOR POLYMERS

Patent Matrix® Search