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

Patent metadata

Field	Value
Publication number	US-10947370-B2
Application number	US-201916248929-A
Country	US
Kind code	B2
Filing date	Jan 16, 2019
Priority date	Jan 22, 2018
Publication date	Mar 16, 2021
Grant date	Mar 16, 2021

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 C 4 -C 60 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 3-phenyl-3H-1-benzofuran-2-one compound, wherein the 3-phenyl group is substituted with one or more acyloxy groups comprising 26 or more carbon atoms and the compound conforms to Formula (I)

wherein R 1 , R 2 , R 3 , and R 4 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 1 , R 2 , R 3 , and R 4 can be linked to form a fused benzene ring; R 6 , R 7 , R 8 , R 9 , and R 19 are independently selected from the group consisting of hydrogen, halogens, alkyl groups, substituted alkyl groups, alkoxy groups, substituted alkoxy groups, and —OR 5 , provided at least one of R 6 , R 8 , and R 19 is —OR 5 ; R 5 is selected from the group consisting of —R 11 —C(O)—R 12 and —C(O)—R 12 , R 11 is —(C 2 H 4 O) a (C 3 H 6 O) b (C 2 H 4 O) c —, the variables a, b, and c are integers independently selected from the group consisting of zero and the positive natural numbers, provided at least one of a, b, and c is a positive natural number, and R 12 is selected from the group consisting of hydrocarbyl groups having 25 or more carbon atoms.

2. The compound of claim 1 , wherein the acyloxy group comprises 30 or more carbon atoms.

3. The compound of claim 1 , wherein R 1 and R 3 are independently selected from the group consisting of alkyl groups, and R 2 and R 4 are hydrogen.

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

5. The compound of claim 1 , wherein R 6 , R 7 , R 9 , and R 10 are hydrogen, and R 8 is —OR 5 .

6. The compound of claim 1 , wherein the variables a, b, and c are independently selected from the group consisting of zero and the positive natural numbers from 1 to 100.

7. The compound of claim 1 , wherein R 5 is —R 11 —C(O)—R 12 .

8. The compound of claim 1 , wherein the variable a is 1, and the variables b and c are zero.

9. The compound of claim 1 , wherein R 12 is selected from the group consisting of saturated hydrocarbyl groups.

10. 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.

11. The composition of claim 10 , wherein second component is an antioxidant selected from the group consisting of hindered phenols, aromatic amines, phosphites, and mixtures thereof.

12. The composition of claim 11 , wherein the composition comprises a hindered phenol and a phosphite.

13. The composition of claim 10 , wherein the composition comprises an acid scavenger, and the acid scavenger is a metal salt of a fatty acid.

14. The composition of claim 13 , wherein the second component is a metal salt of a C 4 -C 28 fatty acid.

15. The composition of claim 13 , wherein the second component is a metal salt of a C 12 -C 24 fatty acid.

16. The composition of claim 13 , wherein the second component is a metal salt of stearic acid.

17. The composition of claim 13 , 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.

18. The composition of claim 13 , wherein the second component is zinc stearate.

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

20. The composition of claim 19 , wherein the organic polymer is a polyolefin.

21. The composition of claim 20 , wherein the polyolefin is a polypropylene.

22. The composition of claim 20 , wherein the polyolefin is a polyethylene.

Assignees

• Milliken & Co

Inventors

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

Classifications

• Y02W30/62

  Plastics recycling; Rubber recycling · CPC title

• C07D307/83 Primary

  Oxygen atoms · CPC title

• C08K5/1345

  Carboxylic esters of phenolcarboxylic acids · CPC title

• C08K5/526

  with hydroxyaryl compounds · CPC title

• C08K5/005

  Stabilisers against oxidation, heat, light, ozone · CPC title