Schiff base oligomers

Patent metadata

Field	Value
Publication number	US-2021284801-A1
Application number	US-202117191024-A
Country	US
Kind code	A1
Filing date	Mar 3, 2021
Priority date	Mar 5, 2020
Publication date	Sep 16, 2021
Grant date	—

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 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

• C08G59/504

  containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen · CPC title

• C09D5/08 Primary

  Anti-corrosive paints · CPC title

• C08G59/22

  Di-epoxy compounds · CPC title

• C23F11/173

  Macromolecular compounds · CPC title

• C08G12/40

  Chemically modified polycondensates · CPC title