Poly (alkyl carbonate) adhesives

Patent metadata

Field	Value
Publication number	US-11401374-B2
Application number	US-201916544174-A
Country	US
Kind code	B2
Filing date	Aug 19, 2019
Priority date	Aug 20, 2018
Publication date	Aug 2, 2022
Grant date	Aug 2, 2022

Abstract

The invention provides polymer compositions, compounds, processes, and methods of use of the polymers for biodegradable consumer plastics, adhesives, e.g., bioadhesives, pressure sensitive adhesives and thermos-responsive adhesives.

First claim

What is claimed is:

1. A polymer of comprising:
(i) a repeating unit represented by Formula (I); and
(ii) a repeating unit represented by Formula (II)
where:

wherein:
X 11 , X 12 , X 13 , X 14 , X 15 , X 21 , X 22 , X 23 , X 24 and X 25 are independently selected from the group consisting of O, S, Se, and NH;
R 11 and R 21 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aryl, heterocyclyl, heteroaryl, silyl, alkylsilyl, arylsilyl, alkylaryl, arylalkyl, poly(ethylene glycol), poly(ethylene oxide), poly(hydroxyacid), a carbohydrate, a protein, a polypeptide, an amino acid, a nucleic acid, a nucleotide, a lipid, an oligosaccharide, a polysaccharide, an antibody, a pharmaceutical agent, an imaging agent, an epitope for a biological receptor, a photocrosslinkable group, or an ionically crosslinkable group, wherein alkyl, alkenyl, cycloalkyl, aryl, heterocyclyl, heteroaryl, silyl, alkylsilyl, arylsilyl, alkylaryl, and arylalkyl is optionally substituted by one or more substituents selected independently from the group consisting of hydroxyl, hydroxyether, carboxyl, carboxyester, carboxyamide, amino, mono- or di-substituted amino, thiol, thioester, sulfate, phosphate, phosphonate, and halogen;
R 12 and R 22 are independently unsubstituted alkyl;
provided that R 12 and R 22 are different, and
wherein a mol/mol ratio of Formula (I) to Formula (II) is from about 5:95 to about 30:70.

2. The polymer of claim 1 , wherein X 11 , X 12 , X 13 , X 14 and X 15 are O.

3. The polymer of claim 1 , wherein R 11 is hydrogen or C 1 -C 10 alkyl, wherein C 1 -C 10 alkyl is optionally substituted with one, two, three, four, five or six substituents selected independently from the group consisting of hydroxyl, hydroxyether, carboxyl, amino, mono- or di-substituted amino, thiol, thioester, and halogen.

4. The polymer of claim 1 , wherein X 21 , X 22 , X 23 , X 24 and X 25 are O.

5. The polymer of claim 1 , wherein R 21 is hydrogen or C 1 -C 10 alkyl, wherein C 1 -C 10 alkyl is optionally substituted with one, two, three, four, five or six substituents selected independently from the group consisting of hydroxyl, hydroxyether, carboxyl, amino, mono- or di-substituted amino, thiol, thioester, and halogen.

6. A composition comprising a polymer of claim 1 .

7. The composition of claim 6 , wherein the composition is in form of a solution, polymeric film, sheet, mesh, foam, fiber or particle.

8. An adhesive composition comprising a polymer of claim 1 .

9. The adhesive composition of claim 8 , wherein the adhesive is pressure-sensitive and/or thermo-responsive.

10. The adhesive composition of claim 8 , wherein the adhesive has a minimum peel force of at least 1 N/cm.

11. The adhesive composition of claim 8 , wherein the adhesive has a minimum tack strength of at least 20N.

12. A method for bonding at least two sites together, the method comprising applying a polymer of 32 to at least one site and contacting the at least two sites together.

13. The method of claim 12 , where at least one site is a biological surface.

14. The method of claim 12 , wherein at least one site is a synthetic surface.

15. The method of claim 14 , wherein the synthetic surface is a surface of a medical device.

16. A method of forming an adhesive composition, the method comprising preparing an adhesive polymer of claim 1 .

17. The polymer of claim 1 , wherein R 12 and R 22 are independently unsubstituted C 1 -C 10 alkyl.

18. The polymer of claim 1 , wherein R 12 and R 22 are independently methyl, ethyl, propyl, iso-propyl, butyl, but-2-yl, 2-methylpropyl, t-butyl, pentyl or hexyl.

19. The polymer of claim 1 , wherein X 11 , X 12 , X 13 , X 14 , X 15 , X 21 , X 22 , X 23 , X 24 and X 25 are O; R 11 and R 21 are independently hydrogen or C 1 -C 10 alkyl; and R 12 and R 22 are independently unsubstituted C 1 -C 10 alkyl.

20. The polymer of claim 1 , wherein X 11 , X 12 , X 13 , X 14 , X 15 , X 21 , X 22 , X 23 , X 24 and X 25 are O; and R 11 and R 21 are independently hydrogen; and R 12 and R 22 are independently methyl, ethyl, propyl, iso-propyl, butyl, but-2-yl, 2-methylpropyl, t-butyl, pentyl or hexyl.

21. The polymer of claim 1 , wherein more than 50% of adjacent stereocenters in the polymer have the same stereochemistry or greater than 50% of the stereocenters are of the same stereochemistry.

22. The polymer of claim 1 , wherein the polymer is prepared by terpolymerization of CO 2 with glycidyl esters.

23. A polymer comprising:
(i) a repeating unit represented by Formula (I); and
(ii) a repeating unit represented by Formula (II)
where:

wherein:
X 11 , X 12 , X 13 , X 14 , X 15 , X 21 , X 22 , X 23 , X 24 and X 25 are independently selected from the group consisting of O, S, Se, and NH;
R 11 and R 21 are independently hydrogen, alkyl, alkenyl, cycloalkyl, aryl, heterocyclyl, heteroaryl, silyl, alkylsilyl, arylsilyl, alkylaryl, arylalkyl, poly(ethylene glycol), poly(ethylene oxide), poly(hydroxyacid), a carbohydrate, a protein, a polypeptide, an amino acid, a nucleic acid, a nucleotide, a lipid, an oligosaccharide, a polysaccharide, an antibody, a pharmaceutical agent, an imaging agent, an epitope for a biological receptor, a photocrosslinkable group, or an ionically crosslinkable group, wherein alkyl, alkenyl, cycloalkyl, aryl, heterocyclyl, heteroaryl, silyl, alkylsilyl, arylsilyl, alkylaryl, and arylalkyl is optionally substituted by one or more substituents selected independently from the group consisting of hydroxyl, hydroxyether, carboxyl, carboxyester, carboxyamide, amino, mono- or di-substituted amino, thiol, thioester, sulfate, phosphate, phosphonate, and halogen;
R 12 is methyl; and
R 22 is propyl;
and
wherein:
a mol/mol ratio of Formula (I) to Formula (II) is from about 5:95 to about 45:55.

24. The polymer of claim 23 , wherein X 11 , X 12 , X 13 , X 14 and X 15 are O.

25. The polymer of claim 23 , wherein R 11 is hydrogen or C 1 -C 10 alkyl, wherein C 1 -C 10 alkyl is optionally substituted with one, two, three, four, five or six substituents selected independently from the group consisting of hydroxyl, hydroxyether, carboxyl, amino, mono- or di-substituted amino, thiol, thioester, and halogen.

26. The polymer of claim 23 , wherein X 21 , X 22 , X 23 , X 24 and X 25 are O.

27. The polymer of claim 23 , wherein R 21 is hydrogen or C 1 -C 10 alkyl, wherein C 1 -C 10 alkyl is optionally substituted with one, two, three, four, five or six substituents selected independently from the group consisting of hydroxyl, hydroxyether, carboxyl, amino, mono- or di-substituted amino, thiol, thioester, and halogen.

28. The polymer of claim 23 , wherein X 11 , X 12 , X 13 , X 14 , X 15 , X 21 , X 22 , X 23 , X 24 and X 25 are O; and R 11 and R 21 are independently hydrogen or C 1 -C 10 alkyl.

29. The polymer of claim 23 , wherein X 11 , X 12 , X 13 , X 14 , X 15 , X 21 , X 22 , X 23 , X 24 and X 25 are O; and R 11 and R 21 are independently hydrogen.

30. The polymer of claim 23 , wherein more t

Assignees

• Univ Boston

Inventors

• Grinstaff Mark W
• Beharaj Anjeza

Classifications

• C09J7/38

  Pressure-sensitive adhesives [PSA] · CPC title

• C08L69/00

  Compositions of polycarbonates; Compositions of derivatives of polycarbonates · CPC title

• C08G64/32

  using carbon dioxide · CPC title

• C08G64/34 Primary

  and cyclic ethers · CPC title

• C08G64/0208

  saturated · CPC title