3-phenyl-3H-1-benzofuran-2-one compounds and compositions comprising the same

Patent metadata

Field	Value
Publication number	US-11739200-B2
Application number	US-202117181048-A
Country	US
Kind code	B2
Filing date	Feb 22, 2021
Priority date	Jan 22, 2018
Publication date	Aug 29, 2023
Grant date	Aug 29, 2023

Abstract

A 3-phenyl-3H-1-benzofuran-2-one compound is substituted with one or more acyloxy groups comprising 26 or more carbon atoms. A compound comprises two or more 3-phenyl-3H-1-benzofuran-2-one moieties and a second moiety selected from the group consisting of divalent and polyvalent C4-C60 hydrocarbon moieties. Each 3-phenyl-3H-1-benzofuran-2-one moiety is covalently bound to an open valence of the second moiety through a linking group selected from the group consisting of a carboxy group and oxyalkylene ester moieties. A composition comprises the 3-phenyl-3H-1-benzofuran-2-one compound described above or the compound described above comprising two or more 3-phenyl-3H-1-benzofuran-2-one moieties.

First claim

What is claimed is:

1. A compound comprising two or more 3-phenyl-3H-1-benzofuran-2-one moieties and a second moiety selected from the group consisting of divalent and polyvalent C 4 -C 60 hydrocarbon moieties, wherein each 3-phenyl-3H-1-benzofuran-2-one moiety is covalently bound to an open valence of the second moiety through a linking group selected from the group consisting of a carboxy group and oxyalkylene ester moieties, and the compound conforms to Formula (LI) or (LII)

wherein R 51 , R 52 , R 53 , and R 54 are independently selected from the group consisting of hydrogen, hydroxy, halogens, alkyl groups, substituted alkyl groups, alkoxy groups, substituted alkoxy groups, aralkyl groups, substituted aralkyl groups, alkaryl groups, substituted alkaryl groups, cycloalkyl groups, substituted cycloalkyl groups, alkylamino groups, substituted alkylamino groups, acyloxy groups, and substituted acyloxy groups, provided adjacent pairs of R 51 , R 52 , R 53 , and R 54 can be linked to form a fused benzene ring; R 56 , R 57 , R 58 , R 59 , and R 69 are independently selected from the group consisting of hydrogen, halogens, alkyl groups, substituted alkyl groups, alkoxy groups, and substituted alkoxy groups; the variables bb, cc, and dd are integers independently selected from the group consisting of zero and the positive natural numbers; the variable ee is an integer selected from the group consisting of 2 and 3; and R 55 is selected from the group consisting of (i) hydrocarbylene groups having 18 or more carbon atoms and (ii) hydrocarbtriyl groups having 17 or more carbon atoms.

2. The compound of claim 1 , wherein R 51 and R 53 are independently selected from the group consisting of alkyl groups, and R 52 and R 54 are hydrogen.

3. The compound of claim 1 , wherein R 51 and R 53 are each tert-butyl.

4. The compound of claim 1 , wherein R 56 , R 57 , R 58 , R 59 , and R 69 are hydrogen.

5. The compound of claim 1 , wherein the variables bb, cc, and dd are independently selected from the group consisting of zero and the positive natural numbers from 1 to 100.

6. The compound of claim 1 , wherein the variable bb is 1, and the variables cc and dd are zero.

7. The compound of claim 1 , wherein R 55 is selected from the group consisting of (i) hydrocarbylene groups having 28 or more carbon atoms and (ii) hydrocarbtriyl groups having 27 or more carbon atoms.

8. The compound of claim 1 , wherein R 55 is a hydrocarbylene group comprising a first C 9 -C 20 linear hydrocarbyl group and a second C 9 -C 20 linear hydrocarbyl group, the first C 9 -C 20 linear hydrocarbyl group and the second C 9 -C 20 linear hydrocarbyl group being linked by one or more carbon-carbon single bonds between a carbon atom in the first C 9 -C 20 linear hydrocarbyl group and a carbon atom in the second C 9 -C 20 linear hydrocarbyl group.

9. The compound of claim 8 , wherein the first C 9 -C 20 linear hydrocarbyl group and the second C 9 -C 20 linear hydrocarbyl group are each saturated hydrocarbyl groups.

10. The compound of claim 8 , wherein the first C 9 -C 20 linear hydrocarbyl group is a C 17 linear hydrocarbyl group and the second C 9 -C 20 linear hydrocarbyl group is a C 17 linear hydrocarbyl group.

11. The compound of claim 1 , wherein R 55 is a group of Formula (LX), (LXI), (LXII), LXIII), (LXIV), (LXV), (LXVI), (LXVII), (LXVIII), (LXIX), or (LXX)

12. A composition comprising a compound of claim 1 and a second component selected from the group consisting of fillers, ultraviolet light absorbers, antioxidants, acid scavengers, and mixtures thereof.

13. The composition of claim 12 , wherein second component is an antioxidant selected from the group consisting of hindered phenols, aromatic amines, phosphites, and mixtures thereof.

14. The composition of claim 13 , wherein the composition comprises a hindered phenol and a phosphite.

15. The composition of claim 12 , wherein the composition comprises an acid scavenger, and the acid scavenger is a metal salt of a fatty acid.

16. The composition of claim 15 , wherein the second component is a metal salt of a C 4 -C 28 fatty acid.

17. The composition of claim 15 , wherein the second component is a metal salt of a C 12 -C 24 fatty acid.

18. The composition of claim 15 , wherein the second component is a metal salt of stearic acid.

19. The composition of claim 15 , wherein the metal salt of a fatty acid comprises a cation selected from the group consisting of alkali metal cations, alkaline earth metal cations, and zinc cations.

20. The composition of claim 15 , wherein the second component is zinc stearate.

21. A composition comprising an organic polymer and a compound of claim 1 .

22. The composition of claim 21 , wherein the organic polymer is a polyolefin.

23. The composition of claim 22 , wherein the polyolefin is a polypropylene.

24. The composition of claim 22 , wherein the polyolefin is a polyethylene.

Assignees

• Milliken & Co

Inventors

• Xu Xiaoyou
• Keller Keith A
• Datta Suchitra
• Meador Matthew D

Classifications

• C08L23/06 Primary

  Polyethylene · CPC title

• C07D307/83 Primary

  Oxygen atoms · CPC title

• C08K5/05

  Alcohols; Metal alcoholates · CPC title

• C08K5/07

  Aldehydes; Ketones · CPC title

• C08K5/098

  Metal salts of carboxylic acids · CPC title