Oxindole compounds and compositions comprising the same

Patent metadata

Field	Value
Publication number	US-9718775-B2
Application number	US-201514613910-A
Country	US
Kind code	B2
Filing date	Feb 4, 2015
Priority date	Mar 14, 2014
Publication date	Aug 1, 2017
Grant date	Aug 1, 2017

Abstract

Compounds that are derivatives of oxindole conform to the general structure of Formula (I)

These compounds are believed to exhibit antioxidant properties. A composition comprises an organic material and a compound conforming to the structure of Formula (I).

First claim

What is claimed is:

1. A compound conforming to the structure of Formula (I)

wherein R 1 is selected from the group consisting of hydrogen, alkyl groups, hydroxyalkyl groups, alkoxyalkyl groups, aryl groups, and R 20 ; R 2 , R 3 , R 4 , and R 5 are independently selected from the group consisting of hydrogen, halogen atoms, alkyl groups, hydroxyalkyl groups, alkoxy groups, and aryl groups; R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from the group consisting of hydrogen, alkyl groups, alkoxy groups, aryl groups, R 14 , R 15 , —SR 16 , —NR 17 R 18 , and —OR 20 ; provided if R 1 is selected from the group consisting of hydrogen, alkyl groups, hydroxyalkyl groups, alkoxyalkyl groups, aryl groups, alkanoyl groups, alkenoyl groups, and aryloyl groups, then at least one of R 6 , R 7 , R 8 , R 9 , and R 10 is selected from the group consisting of R 14 , R 15 , —SR 16 , —NR 17 R 18 , and —OR 20 ; R 14 is a group conforming to the structure of Formula (II)

R 15 is a group conforming to the structure of Formula (III)

X is selected from the group consisting of —N(H)—, —O—C(O)—, and —N(H)—C(O)—; R 50 is selected from the group consisting of a bond and alkanediyl groups; R 51 , R 52 , R 53 , and R 54 are independently selected from the group consisting of hydrogen and alkyl groups; R 16 is selected from the group consisting of hydrogen, alkyl groups, hydroxyalkyl groups, alkoxyalkyl groups, aryl groups, R 19 , and R 20 ; R 19 is a group conforming to a structure selected from the group consisting of Formula (IVA), (IVB), and (IVC)

R 17 and R 18 are independently selected from the group consisting of hydrogen, alkyl groups, hydroxyalkyl groups, alkoxyalkyl groups, aryl groups, and R 20 ; and R 20 is selected from the group consisting of:
(a) alkanoyl groups, alkenoyl groups, and aryloyl groups;
(b) —R 21 —O—R 22 , where R 21 is selected from the group consisting of alkanediyl groups, and R 22 is selected from the group consisting of alkyl groups, alkanoyl groups, alkenoyl groups, and aryloyl groups;
(c) groups conforming to the structure of Formula (V)

where R 23 is selected from the group consisting of alkanediyl groups, R 24 and R 25 are independently selected from the group consisting of hydrogen, alkyl groups, —R 21 —O—R 22 , —R 30 —O—R 31 —R 32 , and —R 31 —R 32 ;
(d) —R 30 —O—R 31 —R 32 , where R 30 is selected from the group consisting of alkanediyl groups; and
(e) —R 31 —R 32 , where R 32 is selected from the group consisting of hydrogen, alkyl groups, alkanoyl groups, alkenoyl groups, and aryloyl groups; and R 31 is a divalent substituent selected from the group consisting of:
(i) divalent substituents comprising two or more divalent repeating units independently selected from repeating units conforming to the structure of Formula (C)

wherein R 101 and R 102 are independently selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, aryl, alkoxyalkyl, and aryloxyalkyl;
(ii) divalent substituents conforming to the structure of Formula (CX)

wherein R 111 and R 112 are independently selected from the group consisting of hydrogen, hydroxyl, and C 1 -C 10 alkyl, c is an integer from 1 to 12, and d is a positive integer;
(iii) divalent substituents conforming to the structure of Formula (CXX)

wherein R 121 and R 122 are independently selected from the group consisting of hydrogen, hydroxyl, and C 1 -C 10 alkyl, e is an integer from 1 to 12, and f is a positive integer;
(iv) divalent substituents conforming to the structure of Formula (CXXX)

wherein R 131 , R 132 , and R 133 are independently selected from alkyl and hydroxyalkyl, and h is a positive integer; and
(v) divalent substituents comprising two or more substituents selected from the group consisting of substituents conforming to a structure of Formula (C), (CX), (CXX), or (CXXX).

2. The compound of claim 1 , wherein at least one of R 6 , R 7 , R 8 , R 9 , and R 10 is —OR 20 .

3. The compound of claim 2 , wherein R 20 is selected from the group consisting of —R 30 —O—R 31 —R 32 , and —R 31 —R 32 .

4. The compound of claim 3 , wherein R 31 is a divalent substituent conforming to a structure selected from the group consisting of Formulae (CI), (CII), and (CIII)

wherein s, t, and v are selected from the group consisting of zero and positive integers; and the sum of s, t, and v is 2 or more.

5. The compound of claim 4 , wherein the sum of s, t, and v is from 2 to about 50.

6. The compound of claim 5 , wherein R 31 is a divalent substituent conforming to the structure of Formula (CI), s is an integer from 2 to about 50, v is 0, and t is 0.

7. The compound of claim 6 , wherein R 8 is —OR 20 , and R 6 , R 7 , R 9 , and R 10 are each hydrogen.

8. The compound of claim 7 , wherein R 1 , R 2 , R 3 , R 4 , and R 5 are each hydrogen.

9. The compound of claim 8 , wherein R 32 is hydrogen.

10. A composition comprising an organic material and a compound conforming to the structure of Formula (I)

wherein R 1 is selected from the group consisting of hydrogen, alkyl groups, hydroxyalkyl groups, alkoxyalkyl groups, aryl groups, and R 20 ; R 2 , R 3 , R 4 , and R 5 are independently selected from the group consisting of hydrogen, halogen atoms, alkyl groups, hydroxyalkyl groups, alkoxy groups, and aryl groups; R 6 , R 7 , R 8 , R 9 , and R 10 are independently selected from the group consisting of hydrogen, hydroxy, alkyl groups, alkoxy groups, aryl groups, R 14 , R 15 , —SR 16 , —NR 17 R 18 , and —OR 20 ; R 14 is a group conforming to the structure of Formula (II)

R 15 is a group conforming to the structure of Formula (III)

X is selected from the group consisting of —N(H)—, —O—C(O)—, and —N(H)—C(O)—; R 50 is selected from the group consisting of a bond and alkanediyl groups; R 51 , R 52 , R 53 , and R 54 are independently selected from the group consisting of hydrogen and alkyl groups; R 16 is selected from the group consisting of hydrogen, alkyl groups, hydroxyalkyl groups, alkoxyalkyl groups, aryl groups, R 19 , and R 20 ; R 19 is a group conforming to the structure of Formula (IVA), (IVB), or (IVC)

R 17 and R 18 are independently selected from the group con

Assignees

• Milliken & Co

Inventors

• Dey Sanjeev K
• Torres Eduardo
• Datta Suchitra
• Mason Mary E
• Harris Philip G

Classifications

• C08L75/04

  Polyurethanes · CPC title

• C08K5/3417

  condensed with carbocyclic rings · CPC title

• C07D209/34 Primary

  in position 2 · CPC title