Schiff base oligomers

Patent metadata

Field	Value
Publication number	US-12098250-B2
Application number	US-202318338413-A
Country	US
Kind code	B2
Filing date	Jun 21, 2023
Priority date	Mar 5, 2020
Publication date	Sep 24, 2024
Grant date	Sep 24, 2024

Abstract

Aspects of the present disclosure relate to Schiff base oligomers and uses thereof. In at least one aspect, an oligomer is represented by Formula (IV) wherein each instance of R 9 is independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and ether. Each instance of R 28 and R 29 of Formula (IV) is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, and aryl. Each instance of R 33 of Formula (IV) is independently selected from the group consisting of alkyl, cycloalkyl, aryl, heterocyclyl, and a bond. Each instance of R 41 of Formula (IV) is independently —NH— or a bond and each instance of R 40 is independently —NH— or —NH—NH—. Each instance of R 42 of Formula (IV) is independently —NH— or a bond and each instance of R 43 is independently —NH— or —NH—NH—.

First claim

What is claimed is:

1. An oligomer consisting of:
two or more repeating units of a Schiff base monomeric unit having at least one thiocarbonyl group, wherein the two or more repeating units comprise:
a first repeating unit obtained from a thiosemicarbazide, thiocarbazide, or thiocarbonyl-containing compound having two or more terminal (—NH 2 ) groups;
a second repeating unit obtained from a thiosemicarbazide, thiocarbazide, or thiocarbonyl-containing compound having two or more terminal (—NH 2 ) groups;

a linking unit having a hydroxyl group or a urea-containing unit, wherein the linking unit is configured to link the two or more repeating units of the Schiff base monomeric unit, and
a silyl end cap on at least one of the two or more repeating units, wherein the silyl is represented by the formula:

wherein each of R 45 , R 46 , and R 47 is independently selected from the group consisting of hydrogen and C 1 -C 20 alkyl; and R 48 is selected from the group consisting of alkyl, cycloalkyl, ether, and aryl.

2. The oligomer of claim 1 , wherein the end cap is on the two or more repeating units.

3. The oligomer of claim 1 , wherein the oligomer is represented by formula (IV):

wherein:
each instance of R 9 is independently selected from the group consisting of alkyl, cycloalkyl, aryl, heteroaryl, and ether;
each instance of R 28 and R 29 is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, and aryl;
each instance of R 33 is independently selected from the group consisting of alkyl, cycloalkyl, aryl, heterocyclyl, and a bond;
each instance of R 41 is independently —NH— or a bond and each instance of R 40 is independently —NH— or —NH—NH—;
each instance of R 42 is independently —NH— or a bond and each instance of R 43 is independently —NH— or —NH—NH—;
each instance of z and t is an integer of 1 to 50;
R 44 is hydroxyl or decarboxylated derivative thereof, or is represented by the structure:

wherein:
R 1 is hydrogen or the silyl end cap;
R 2 and R 3 are independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, and aryl;
R 31 is selected from the group consisting of alkyl, cycloalkyl, aryl, heterocyclyl, and a bond;
R 50 is —NH— or a bond and R 32 is —NH— or —NH—NH—;
R 34 is —NH— or a bond and R 35 is —NH— or —NH—NH—; and
x is an integer of 1 to 50; and

R 30 is the silyl end cap.

4. The oligomer of claim 3 , wherein each instance of R 28 or R 29 is independently selected from the group consisting of hydrogen and C 1 -C 5 alkyl.

5. The oligomer of claim 4 , wherein each instance of R 28 or R 29 is hydrogen.

6. The oligomer of claim 3 , wherein:
if R 41 is —NH—, then R 40 is —NH—, and if R 41 is a bond, then R 40 is —NH—NH—; and
if R 42 is —NH—, then R 43 is —NH—, and if R 42 is a bond, then R 43 is —NH—NH—.

7. The oligomer of claim 3 , wherein each instance of R 9 is independently C 1 -C 10 alkyl or an aryl.

8. The oligomer of claim 3 , wherein each instance of R 9 is independently a phenyl represented by the formula:

wherein R 60 , R 61 , R 62 , and R 63 are independently selected from the group consisting of hydrogen and C 1 -C 10 alkyl.

9. The oligomer of claim 8 , wherein each of R 60 , R 61 , R 62 , and R 63 is hydrogen.

10. The oligomer of claim 3 , wherein each instance of R 9 is cycloalkyl.

11. The oligomer of claim 3 , wherein each instance of R 33 is a bond.

12. The oligomer of claim 3 , wherein each instance of R 33 is independently selected from C 1 -C 10 alkyl.

13. The oligomer of claim 3 , wherein each instance of R 33 is independently selected from a phenyl represented by the formula:

where R 60 , R 61 , R 62 , and R 63 are independently selected from hydrogen and C 1 -C 10 alkyl.

14. The oligomer of claim 13 , wherein each of R 60 , R 61 , R 62 , and R 63 is hydrogen.

15. The oligomer of claim 11 , wherein the silyl end cap is derived from a glycidyl ether silyl.

16. The oligomer of claim 1 , wherein each of R 45 , R 46 , and R 47 is hydrogen.

17. The oligomer of claim 1 , wherein each of R 45 , R 46 , and R 47 is ethyl.

18. The oligomer of claim 17 , wherein R 48 is ether.

19. The oligomer of claim 1 , wherein the silyl end cap is

Assignees

• Boeing Co

Inventors

• Zweig Andrew M
• Schuette Waynie M

Classifications

• C08G12/12

  Ureas; Thioureas · CPC title

• C08G18/54

  Polycondensates of aldehydes · CPC title

• C09D175/02

  Polyureas · CPC title

• C08G18/7621

  being toluene diisocyanate including isomer mixtures · CPC title

• C23F11/173

  Macromolecular compounds · CPC title