Polymer composition containing diarylamine-based compound

Patent metadata

Field	Value
Publication number	US-2022127430-A1
Application number	US-202217646866-A
Country	US
Kind code	A1
Filing date	Jan 4, 2022
Priority date	Mar 3, 2017
Publication date	Apr 28, 2022
Grant date	—

Abstract

The present invention provides a polymer composition comprising a polymer and an antioxidant comprising a diarylamine-based compound represented by General Formula (1):

where, in General Formula (1), A 1 and A 2 each independently represent a C 6 to C 18 arylene group which may have a substituent, and A 3 and A 4 each independently represent an organic group having a cyclic imide structure which may have a substituent.

First claim

1 . A polymer composition comprising a polymer and an antioxidant comprising a diarylamine-based compound represented by General Formula (1):

where, in General Formula (1), A 1 and A 2 each independently represent a C 6 to C 18 arylene group which may have a substituent, and A 3 and A 4 each independently represent an organic group having a cyclic imide structure which may have a substituent.

2 . The polymer composition according to claim 1 , wherein A 3 and A 4 each independently are an organic group represented by General Formula (2) or (3):

where, in General Formula (2), D represents a C 6 to C 18 ring which may have a substituent; “m” represents 0 or 1; in General Formula (3), R 1 and R 2 each independently represent a hydrogen atom, a C 1 to C 30 alkyl group which may have a substituent, or a C 1 to C 30 alkenyl group which may have a substituent; and “n” represents 0 or 1.

3 . The polymer composition according to claim 2 , wherein A 3 and A 4 each independently are any of organic groups represented by General Formulae (4) to (9):

where, in General Formulae (4) to (9), R 3 to R 8 each independently represent a hydrogen atom, a C 1 to C 30 alkyl group, a C 1 to C 30 alkenyl group, —O—R 9 , —O—C(═O)—R 9 , —C(═O)—O—R 9 , —C(═O)—NR 9 (R 10 ), —NR 9 —C(═O)—R 10 , —CN, —SR 9 , —S(═O)—R 9 , or —S(═O) 2 —R 9 ; R 9 and R 10 each independently represent a C 1 to C 30 alkyl group, a C 1 to C 30 alkenyl group, or a C 6 to C 12 aromatic group; and when two or more R 3 to R 8 are present, these may be the same or may be different.

4 . The polymer composition according to claim 3 , wherein the diarylamine-based compound is any of compounds represented by General Formulae (10) to (13):

where, in General Formulae (10) to (13), R 11 to R 22 each independently represent a hydrogen atom, a C 1 to C 30 alkyl group, a C 1 to C 30 alkenyl group, —OR 23 , —O—C(═O)—R 23 , —C(═O)—OR 23 , —C(═O)—NR 23 (R 24 ), —NR 23 —C(═O)—R 24 , —CN, —SR 23 , —S(═O)—R 23 , or —S(═O) 2 —R 23 ; R 23 and R 24 each independently represent a C 1 to C 30 alkyl group, a C 1 to C 30 alkenyl group, or a C 6 to C 12 aromatic group; and A 1 and A 2 are the same as those in General Formula (1).

5 . The polymer composition according to claim 1 , wherein A 1 and A 2 are a 1,4-phenylene group.

6 . The polymer composition according to claim 1 , wherein the diarylamine-based compound is any of compounds represented by General Formulae (14) to (18):

7 . The polymer composition according to claim 1 further comprising a condensed heterocyclic compound represented by General Formula (19):

where, in the formula, Y 1 represents a chemical single bond, —S(═O)—, or —SO 2 —;
R a and R b each independently represent a C 1 to C 30 organic group which may have a substituent;
Z a and Z b each independently represent a chemical single bond or —SO 2 —;
X 1 and X 2 each independently represent a hydrogen atom, a halogen atom, a C 1 to C 10 alkyl group which may have a substituent, a cyano group, a nitro group, —OR 25 , —O—C(═O)—R 25 , —C(═O)—OR 25 , —O—C(═O)—OR 25 , —NR 26 (R 27 ), —NR 26 —C(═O)—R 25 , —C(═O)—NR 26 (R 27 ), or —O—C(═O)—NR 26 (R 27 ), where R 25 , R 26 and R 27 each independently represent a hydrogen atom or a C 1 to C 20 organic group which may have a substituent;
“n” and “m” each independently represent an integer of 0 to 2, and one of “n” and “m” is not 0; and
when “n” and/or “m” is 2, two R a and two R b each may be the same or different.

8 . The polymer composition according to claim 7 , wherein R a and R b each independently represent a linear or branched C 1 to C 20 alkyl group which may have a substituent, or a phenyl group which may have a substituent.

9 . The polymer composition according to claim 7 , wherein the condensed heterocyclic compound represented by General Formula (19) is a compound represented by General Formula (20) or (21):

10 . The polymer composition according to claim 7 , wherein a weight ratio of the diarylamine-based compound to the condensed heterocyclic compound is 30:1 to 1:30 as “diarylamine-based compound:condensed heterocyclic compound”.

11 . The polymer composition according to claim 1 , wherein the polymer is a synthetic resin.

12 . The polymer composition according to claim 1 , wherein the polymer is a rubber.

13 . The polymer composition according to claim 12 , wherein the rubber is an acrylic rubber.

14 . The polymer composition according to claim 1 , wherein a content of the antioxidant is 0.05 to 30 parts by weight relative to 100 parts by weight of the polymer.

Assignees

• Zeon Corp

Inventors

• Sugawara Mitsuru
• Kiriki Satoshi
• Ejiri Kazuhiro

Classifications

• C08K5/3417 Primary

  condensed with carbocyclic rings · CPC title

• C08K5/005

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

• C08L7/00

  Compositions of natural rubber · CPC title

• C09D133/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C07D209/48 Primary

  with oxygen atoms in positions 1 and 3, e.g. phthalimide · CPC title