Schiff base oligomers

Patent metadata

Field	Value
Publication number	US-11713374-B2
Application number	US-202117191024-A
Country	US
Kind code	B2
Filing date	Mar 3, 2021
Priority date	Mar 5, 2020
Publication date	Aug 1, 2023
Grant date	Aug 1, 2023

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 (I) wherein each instance of R 4 , R 5 , R 6 , R 7 , R 8 , R 10 , R 11 , R 12 , R 13 , and R 14 is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkoxyl, aryloxyl, ether, and heterocyclyl. Each instance of R 9 of Formula (I) is independently selected from the group consisting of alkyl, cycloalkyl, aryl, heterocyclyl, and ether. Each instance of R 28 and R 29 of Formula (I) is independently selected from the group consisting of hydrogen, alkyl, and aryl. Each instance of R 33 of Formula (I) is independently selected from the group consisting of alkyl, cycloalkyl, aryl, heterocyclyl, and a bond. Each instance of R 41 of Formula (I) is independently —NH— or a bond and each instance of R 40 is independently —NH— or —NH—NH—.

First claim

What is claimed is:

1. An oligomer represented by Formula (I):

wherein:
each instance of R 4 , R 5 , R 6 , R 7 , R 8 , R 10 , R 11 , R 12 , R 13 , and R 14 is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkoxyl, aryloxyl, ether, and heterocyclyl;
each instance of R 9 is independently selected from the group consisting of alkyl, cycloalkyl, aryl, heterocyclyl, and ether;
each instance of R 28 and R 29 is independently selected from the group consisting of hydrogen, alkyl, 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 Q is independently —CH 2 — or oxygen;
each instance of n, m, z and t is an integer of 1 to 50;
R 44 is hydroxyl, hydroxy-substituted alkyl, or is represented by the structure:

where:
R 1 is hydrogen or silyl;
R 2 and R 3 are independently selected from the group consisting of hydrogen, alkyl, 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 hydrogen, silyl, or is represented by the structure:

where:
each of R 4′ , R 5′ , R 6′ , R 7′ , R 8′ , R 10′ , R 11′ , R 12′ , R 13′ , and R 14′ is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, alkoxyl, aryloxyl, ether, and heterocyclyl;
R 9′ selected from the group consisting of alkyl, cycloalkyl, heterocyclyl, and ether;
R 44′ is hydroxyl or hydroxy-substituted alkyl;
each instance of Q′ is independently —CH 2 — or oxygen; and
each of n′ and m′ is an integer of 1 to 50.

2. The oligomer of claim 1 , wherein each instance of R 4 , R 5 , R 6 , R 7 , R 8 , R 10 , R 11 , R 12 , R 13 , and R 14 is independently selected from the group consisting of hydrogen and C 1 -C 5 alkyl.

3. The oligomer of claim 1 , wherein each instance of R 4 , R 5 , R 6 , R 7 , R 8 , R 10 , R 11 , R 12 , R 13 , and R 14 is hydrogen.

4. The oligomer of claim 1 , wherein each instance of R 28 and 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 and R 29 is hydrogen.

6. The oligomer of claim 1 , wherein each instance of Q is oxygen.

7. The oligomer of claim 6 , 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—.

8. The oligomer of claim 6 , wherein each instance of R 9 is independently C 1 -C 10 alkyl or a polyether.

9. The oligomer of claim 8 , wherein each instance of R 9 is a polyether.

10. The oligomer of claim 8 , wherein the polyether has a molecular weight of about 400 g/mol to about 700 g/mol.

11. The oligomer of claim 6 , wherein each instance of R 33 is a bond.

12. The oligomer of claim 6 , wherein each instance of R 33 is independently selected from C 1 -C 10 alkyl.

13. The oligomer of claim 6 , wherein each instance of R 33 is independently selected from a phenyl represented by the formula:

wherein 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 6 , wherein each of R 30 and R 1 are hydrogen.

15. The oligomer of claim 6 , wherein R 30 is silyl.

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

17. The oligomer of claim 15 , wherein the silyl is represented by the formula:

wherein each of R 45 , R 46 , and R 47 are 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.

18. The oligomer of claim 17 , wherein each of R 45 , R 46 , and R 47 is hydrogen.

19. The oligomer of claim 17 , wherein each of R 45 , R 46 , and R 47 is C 1 -C 5 alkyl.

20. The oligomer of claim 17 , wherein the silyl is selected from the group consisting of:

Assignees

• Boeing Co

Inventors

• Zweig Andrew Michael
• Schuette Waynie M

Classifications

• C08G75/00 Primary

  Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule · CPC title

• C08G59/1483

  containing sulfur · CPC title

• C08L61/32

  Modified amine-aldehyde condensates · CPC title

• C09D163/00

  Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins · CPC title

• C09D5/08 Primary

  Anti-corrosive paints · CPC title