Substituted phenacyl molecules and photoresponsive polymers

Patent metadata

Field	Value
Publication number	US-9353214-B2
Application number	US-201214359693-A
Country	US
Kind code	B2
Filing date	Dec 17, 2012
Priority date	Dec 16, 2011
Publication date	May 31, 2016
Grant date	May 31, 2016

Abstract

Substituted phenacyl molecules are provided and employed to create molecules and polymers/copolymers that exhibit photoresponsiveness. In some instances, the substituted phenacyl molecule is incorporated into the polymer/copolymer backbone, and photoirradiation of the polymer/copolymer causes the substituted phenacyl group to break down and the polymer/copolymer to undergo degradation. In other instances, the substituted phenacyl molecules extend as a side chain from the polymer/copolymer backbone. In yet other instances the substituted phenacyl molecules extend as a side chain from the polymer/copolymer backbone, and a drug or polymer additive is linked to the photoresponsive substituted phenacyl group such that photoirradiation releases the drug or additive. In yet other embodiments the substituted phenacyl molecules extend as a side chain from the polymer/copolymer backbone, and serve to link the polymer/copolymer to another polymer/copolymer backbone, and photoirradiation breaks the links.

First claim

What is claimed is:

1. A substituted phenacyl composition of matter according to the following structure:

wherein R 1 is an alkyl chain of from C1 to C10; R 2 is —COOH; R 3 through R 9 are hydrogen, and Z 1 is at the para-position and is O; or
wherein R1 is an alkyl chain of from C1 to C10; R 2 is a group of atoms containing at least one functional group; R 3 through R 8 are selected from H, Cl, Br, F, alkyl, vinyl, alkynyl, aryl, or alkoxy groups, O—R 9 is selected from an ester group, a carbonate group, a phosphate group, a sulfate group and sulfinate group, and Z 1 may be at the ortho-, meta- or para-position and is selected from O, S, HNC═O or R 10 NC═O, wherein R 10 is selected from any atom or group of atoms.

2. The composition of claim 1 , wherein R 1 an alkyl chain of from C1 to C10, R 2 is —COOH, and Z 1 is oxygen.

3. The composition of claim 2 , wherein R 1 is CH 2 .

4. The composition of claim 1 , wherein R 3 through R 8 are selected from H, Cl, Br, F, alkyl, vinyl, alkynyl, aryl, or alkoxy groups, O—R 9 is selected from an ester group, a carbonate group, a phosphate group, a sulfate group and sulfinate group.

5. A polymer, macromolecule, copolymer, oligomer, dendrimer, dendron, or macrocycle that includes one or more following structural unit(s):

wherein R 1 is a bond or an alkyl chain of from C1 to C10; R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 may be any atom or group of atoms; Z 1 may be at the ortho, meta or para position and is selected from O, S, HNC═O or R 10 NC═O, wherein R 10 is selected from any atom or group of atoms; and wherein
(a) R 9 is selected from RC═O, wherein R represents any substitution, or
(b) O—R9 is selected from an ester group, a carbonate group, a phosphate group, a sulfate group and sulfinate group.

6. The composition of matter of claim 5 , wherein R 9 is selected from RC═O, wherein R represents any substitution.

7. The composition of matter of claim 5 , wherein O—R 9 is selected from an ester group, a carbonate group, a phosphate group, a sulfate group and sulfinate group.

8. The composition of matter of claim 7 , wherein R 3 through R 8 are hydrogen, and Z 1 is oxygen and is at the para position.

9. The composition of matter of claim 5 , wherein R 1 is a bond, R 9 is the next repeating unit, and the composition is a polycarbonate homopolymer having the following structure:

wherein R 3 through R 8 may be any atom or group of atoms and n is any number of repeating units.

10. The polycarbonate polymer of claim 9 , wherein R 3 through R 8 are hydrogen.

11. The composition of matter of claim 5 , wherein the composition is a polycarbonate polymer having the following structure:

wherein R 1 is alkyl chain of from C1 to C10; R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 may be any atom or group of atoms, n is any number of repeating units.

12. The polycarbonate polymer of claim 11 , wherein R 1 is a propylene chain (C 3 H 6 ) and R 3 through R 8 are hydrogen.

13. The composition of matter of claim 5 , wherein the composition is a polycarbonate copolymer having the following structure:

wherein R 1 is alkyl chain of from C1 to C10; R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 may be any atom or group of atoms; n is any number of repeating units; “Repeating Unit” is a repeating unit contributed by a comonomer or copolymer; m is any number of repeating units; wherein the n and m repeating units are in statistical arrangement.

14. The polycarbonate copolymer of claim 13 , wherein R 1 is a propylene chain (C 3 H 6 ) and R 3 through R 8 are hydrogen.

15. The composition of matter of claim 5 , wherein the composition is a polyester polymer comprising the following structure:

wherein R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 may be any atom or group of atoms, R 1 is an alkyl chain of from C1 or more to C10 or less, and n represents any number of repeating units.

16. The polyester polymer of claim 15 , wherein R 3 through R 8 are hydrogen and R 1 is methylene (CH 2 ).

17. The polyester polymer of claim 15 , wherein the polymer is a copolymer comprising the structure thereof as part of the polymer.

18. The composition of matter of claim 5 , wherein the composition is a polyester polymer comprising the following structure:

wherein R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 may be any atom or group of atoms, R 1 is an alkyl chain of from C1 to C10, R 12 is either a bond between the two carbonyl groups or is an alkyl chain of from C1 to C10, and n is any number of repeating units.

19. The polyester polymer of claim 18 , wherein R 3 through R 8 are hydrogen, R 1 is a propylene chain (C 3 H 6 ) and R 12 is a butylene chain (C 4 H 8 ).

20. The polyester polymer of claim 18 , wherein the polymer is a copolymer comprising the structure thereof as part of the polymer.

21. The composition of matter of claim 5 , wherein R 1 links the structural unit thereof to a polymer chain, and R 9 is part of a drug molecule, part of an additive, or part of a sensitizer.

22. The composition of matter of claim 5 , wherein R 1 and R 9 individually links the structural unit thereof to a polymer chain, and the structural unit thereof serves as a linker of the polymer chains, wherein the polymer chains could be same or different.

Assignees

• Univ Akron

Inventors

• Joy Abraham
• Sun Shuangyi

Classifications

• C08G63/06 Primary

  derived from hydroxycarboxylic acids · CPC title

• C08G63/664 Primary

  derived from hydroxy carboxylic acids · CPC title

• C08F26/06

  by a heterocyclic ring containing nitrogen · CPC title

• C08G64/04

  Aromatic polycarbonates · CPC title

• C08G64/16

  Aliphatic-aromatic or araliphatic polycarbonates · CPC title