5h-furan-2-one derivatives stabilization of organic material

Patent metadata

Field	Value
Publication number	US-2016362535-A1
Application number	US-201615248953-A
Country	US
Kind code	A1
Filing date	Aug 26, 2016
Priority date	May 2, 2011
Publication date	Dec 15, 2016
Grant date	—

Abstract

A composition, which comprises a) an organic material susceptible to oxidative, thermal or light-induced degradation; and b) a compound of formula I (Formula I) (I) where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are independently from each other H, C 1 -C 8 -alkyl, C 4 -C 8 -cycloalkyl, phenyl, C 1 -C 4 -alkoxy or halogen; n is 1, 2, 3, or 4; and when n is 1 A is —C(=0)-OR′ 1 , —C(=0)-N(R ′2 )(R′ 3 ), —CN, phenyl, which is unsubstituted or substituted by one or more C 1 -C 8 -alkyl, C 4 -C 8 -alkoxy, C 5 -C 7 -cycloalkyl or halogen, —H or —S0 2 -phenyl; when n is 2 A is —C(=0)-0-Z 1 —O—C(=0)-, —C(=0)-N(R″ 1 )—Z 2 —N(R″ 2 )—C(=0)- or piperazine-N,N′-biscarbonyl.

First claim

1 . A composition, which comprises
a) a polyolefin, a polyether polyol, or a polyurethane; and b) a compound of formula I

wherein
n is 1 or 2;
when n is 1,
A is —C(═O)—OR′ 1 , —C(═O)—N(R′ 2 )(R′ 3 ), —CN, phenyl which is unsubstituted or substituted by one or more C 1 -C 8 -alkyl, C 1 -C 4 -alkoxy, C 5 -C 7 -cycloalkyl or halogen, —H or —SO 2 -phenyl; and
when n is 2,
A is —C(═O)—O—Z 1 —O—C(═O)—, —C(═O)—N(R″ 1 )—Z 2 —N(R″ 2 )—C(═O)— or piperazine-N,N′-biscarbonyl;
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are independently from each other H, C 1 -C 8 -alkyl, C 4 -C 8 -cycloalkyl, phenyl, C 1 -C 4 -alkoxy or halogen;
R′ 1 is H, C 1 -C 22 -alkyl, C 2 -C 18 -alkenyl, C 3 -C 12 -alkine-yl, C 4 -C 8 -cycloalkyl which is unsubstituted or substituted by one to three C 1 -C 4 -alkyl, C 4 -C 8 -cycloalkyl-C 1 -C 4 -alkyl bicyclic or tricyclic C 5 -C 20 -alkyl, C 6 -C 14 -aryl-C 1 -C 4 -alkyl, C 2 -C 12 -alkyl which is substituted by one or more hydroxyl groups, C 4 -C 12 -alkyl which is interrupted by one or more oxygen atoms, C 4 -C 18 -alkyl which is interrupted by one sulfur atom, 2,2,6,6-tetramethylpiperidine-4-yl, 1-(C 1 -C 8 -alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or 1-(C 1 -C 8 -alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl;
R′ 2 and R′ 3 are independently from each other H, C 1 -C 22 -alkyl, C 2 -C 18 -alkenyl, C 4 -C 8 -cycloalkyl which is unsubstituted or substituted by one to three C 1 -C 4 -alkyl, C 6 -C 10 -aryl, C 4 -C 8 -cycloalkyl-C 1 -C 4 -alkyl, C 6 -C 14 -aryl-C 1 -C 4 -alkyl, C 2 -C 8 -alkyl which is substituted by one hydroxyl group, 2,2,6,6-tetramethylpiperidine-4-yl, 1-(C 1 -C 8 -alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or 1-(C 1 -C 8 -alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′ 2 and R′ 3 form together with the nitrogen atom to which they are attached a 5-, 6- or 7-membered saturated heterocycle;
R″ 1 and R″ 2 are independently from each other H, C 1 -C 22 -alkyl, C 2 -C 18 -alkenyl, C 4 -C 8 -cycloalkyl which is unsubstituted or substituted by one to three C 1 -C 4 -alkyl, C 4 -C 8 -cycloalkyl-C -C 4 -alkyl or C 6 -C 14 -aryl-C 1 -C 4 -alkyl;
Z 1 is C 2 -C 12 -alkylene, C 4 -C 8 -cycloalkylene, C 4 -C 8 -cycloalkane-bis-(C 1 -C 4 -alkylene), C 6 -C 14 -arene-bis-(C 1 -C 4 -alkylene), C 3 -C 6 -alkylene which is substituted by one or more hydroxyl groups, C 4 -C 12 -alkylene which is interrupted by one or more oxygen atoms, hexahydro-furo[3,2-b]furane-3,6-diyl, C 4 -C 8 -alkylene which is interrupted by a sulfur atom, 3-(C 1 -C 8 -alkyl)-3-azapentane-1,5-diyl, 4-(C 1 -C 8 -alkyl)-4-azaheptane-1,7-diyl or 1-ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl; and
Z 2 is C 2 -C 12 -alkylene, C 4 -C 8 -cycloalkylene, C 6 -C 14 -arylene, C 4 -C 8 -cycloalkane-bis(C 1 -C 4 -alkylene), C 6 -C 14 -arene-bis-(C 1 -C 4 -alkylene), C 4 -C 12 -alkylene which is interrupted by one or more oxygen atoms, 3-(C 1 -C 8 -alkyl)-3-azapentane-1,5-diyl or 4-(C 1 -C 8 -alkyl)-4-azaheptane-1,7-diyl.

2 . A composition according to claim 1 , where in the compound of formula I,
n is 1 or 2 when n is 1, A is —C(═O)—OR′ 1 , —C(═O)—N(R′ 2 )(R′ 3 ), —CN, phenyl which is unsubstituted or substituted by one to three C 1 -C 8 -alkyl or C 1 -C 4 -alkoxy, —H or —SO 2 -phenyl; when n is 2, A is —C(═O)—O—Z 1 —O—C(═O)—, —C(═O)—N(R″ 1 )—Z 2 —N(R″ 2 )—C(═O)— or piperazine-N,N′-biscarbonyl; R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are independently from each other H, C 1 -C 8 -alkyl, phenyl or C 1 -C 4 -alkoxy with the proviso that at least R 1 or R 5 is H and at least R 6 or R 10 is H; R′ 1 is H, C 1 -C 22 -alkyl, C 2 -C 18 -alkenyl, C 5 -C 7 -cycloalkyl which is unsubstituted or substituted by one C 1 -C 4 -alkyl, C 5 -C 7 -cycloalkyl-C 1 -C 4 -alkyl, C 6 -C 10 -aryl-C 1 -C 4 -alkyl, C 4 -C 12 -alkyl which is interrupted by one or more oxygen atoms, 2,2,6,6-tetramethylpiperidine-4-yl, 1-(C 1 -C 6 -alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or 1-(C 1 -C 6 -alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl; R′ 2 and R′ 3 are independently from each other H, C 1 -C 22 -alkyl, C 2 -C 18 -alkenyl, C 5 -C 7 -cycloalkyl which is unsubstituted or substituted by one C 1 -C 4 -alkyl, C 6 -C 10 -aryl, C 5 -C 7 -cycloalkyl-C 1 -C 4 -alkyl, C 6 -C 10 -aryl-C 1 -C 4 -alkyl, 2,2,6,6-tetramethylpiperidine-4-yl, 1-(C 1 -C 6 -alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or 1-(C 1 -C 6 -alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′ 2 and R′ 3 form together with the nitrogen atom to which they are attached a pyrrolidine, a piperidine or a morpholine; R″ 1 and R″ 2 independently from each other H, C 1 -C 22 -alkyl, C 2 -C 18 -alkenyl, C 5 -C 7 -cycloalkyl which is unsubstituted or substituted by one C 1 -C 4 -alkyl, C 5 -C 7 -cycloalkyl-C 1 -C 4 -alkyl or C 6 -C 10 -aryl-C 1 -C 4 -alkyl; Z 1 is C 2 -C 12 -alkylene, C 5 -C 7 -cycloalkylene, C 5 -C 7 -cycloalkane-bis-(C 1 -C 4 -alkylene), C 6 -C 10 -arene-bis-(C 1 -C 4 -alkylene), C 3 -C 6 -alkylene which is substituted by one or more hydroxyl groups, C 4 -C 12 -alkylene which is interrupted by one or more oxygen atoms, C 4 -C 8 -alkylene which is interrupted by a sulfur atom, 3-(C 1 -C 4 -alkyl)-3-azapentane-1,5-diyl, 4-(C 1 -C 4 -alkyl)-4-azaheptane-1,7-diyl or 1-ethyl-2,2,6,6-tetramethylpiperidine-4,2′-diyl; and Z 2 is C 2 -C 12 -alkylene, C 5 -C 7 -cycloalkylene, C 6 -C 14 -arylene, C 5 -C 7 -cycloalkane-bis(C 1 -C 4 -alkylene), C 6 -C 10 -arene-bis-(C 1 -C 4 -alkylene), C 4 -C 12 -alkylene which is interrupted by one or more oxygen atoms, 3-(C 1 -C 4 -alkyl)-3-azapentane-1,5-diyl or 4-(C 1 -C 4 -alkyl)-4-azaheptane-1,7-diyl.

3 . A composition according to claim 1 , where in the compound of formula I,
n is 1 or 2; when n is 1, A is —C(═O)—OR′ 1 , —C(═O)—N(R′ 2 )(R′ 3 ), —CN, phenyl, —H or —SO 2 -phenyl; when n is 2, A is —C(═O)—O—Z 1 —O—C(═O)—; n is 1 or 2; R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 9 and R 10 are H; R 3 and R 8 are independently from each other H or C 1 -C 4 -alkoxy; R′ 1 is H, C 1 -C 12 -alkyl, C 5 -C 7 -cycloalkyl which is unsubstituted, phenyl-C 1 -C 4 -alkyl, 1-(C 1 -C 6 -alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or 1-(C 1 -C 6 -alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl; R′ 2 and R′ 3 are independently from each other H, C 1 -C 12 -alkyl, C 5 -C 7 -cycloalkyl which is unsubstituted, C 6 -C 10 -aryl, phenyl-C 1 -C 4 -alkyl, 1-(C 1 -C 6 -alkyl)-2,2,6,6-tetramethylpiperidine-4-yl or 1-(C 1 -C 6 -alkoxy)-2,2,6,6-tetramethylpiperidine-4-yl, or R′ 2 and R′ 3 form together with the nitrogen atom to which they are attached a pyrrolidine, a piperidine or a morpholine; and Z 1 is C 5 -C 7 -cycloalkylene.

4 .- 6 . (canceled)

7 . A composition according to claim 1 , wherein component b) is contained in an amount of 0.005% to 10% based on the weight of component a).

8 . A composition according to claim 1 , c) a further additive.

9 . A composition according to claim 8 , which comprises c) an additive selected from the group consisting of a phosphite, a phosphonite, an acid scavenger, a phenolic antioxidant, and an aminic antioxidant.

10 . A composition according to claim 8 , wherein the weight ratio of b) to c) is from 4:1 to 1:20.

11 . A composition according to claim 9 , which comprises d) a second further additive selected from the group consisting of a phosphite, a phosphonite, an acid scavenger, a phenolic antioxidant and an aminic antioxidant.

12 . A process for protection of a polyolefin, a polyether polyol, or a polyurethane susceptible to oxidative, thermal or light-induced degradation, w

Assignees

• Basf Se

Inventors

• Fischer Walter
• Basbas Abdel-Ilah
• Schoning Kai-Uwe
• Tartarini Cinzia
• Hölzl Werner
• Rotzinger Bruno

Classifications

• C09K15/12

  containing sulfur and oxygen · CPC title

• C09K15/20

  containing nitrogen and oxygen · CPC title

• C08K5/1535 Primary

  Five-membered rings · CPC title

• C08K5/13

  Phenols; Phenolates · CPC title

• C08K5/526

  with hydroxyaryl compounds · CPC title