Isoindolo[2, 1-A]quinazoline derivatives for stabilization of organic materials

Patent metadata

Field	Value
Publication number	US-9321902-B2
Application number	US-201314381387-A
Country	US
Kind code	B2
Filing date	Mar 19, 2013
Priority date	Mar 20, 2012
Publication date	Apr 26, 2016
Grant date	Apr 26, 2016

Abstract

The present invention relates to a composition, which comprises a) an organic material susceptible to oxidative, thermal or light-induced degradation, which is a polymer, an oligohydroxy compound, a wax, a fat or a mineral oil, with the proviso that the polymer is not a polypeptide, agar-agar or a component of agar-agar and the oligohydroxy compound is not glucose or a component of agar-agar; and b) a compound of formula (I) n is 1, 2, 3 or 4; when n is 1, R 5 is H, C 1 -C 30 -alkyl, C 3 -C 10 -cycloalkyl, C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 7 -C 13 -aralkyl, C 2 -C 22 -alkenyl, C 3 -C 12 -alkinyl, OH, C 1 -C 30 -alkyloxy, C 3 -C 10 -cycloalkyloxy, C 6 -C 12 -aryloxy, C 7 -C 13 -aralkyloxy, hydroxy-C 1 -C 8 -alkyl, carboxy-C 1 -C 12 -alkyl, C 1 -C 12 -alkoxycarbonyl-C 1 -C 12 -alkyl, C 2 -C 30 -alkyl, which is interrupted by one or more oxygen atoms, C 2 -C 16 -alkyl, which is interrupted by one sulfur atom, or NR′ 1 R′ 2 ; when n is 2, R 5 is C 1 -C 12 -alkane-diyl, 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 24 -alkane-diyl, which is interrupted by one or more oxygen atoms, C 4 -C 20 -alkane-diyl, which is interrupted by one or more —NH—, —N(C 1 -C 8 -alkyl)- or —N(hydroxy-C 1 -C 8 -alkyl)-, piperazine-N,N′-bis-(C 1 -C 4 -alkylene) or C 2 -C 10 -alkane-diyl, which is interrupted by one sulfur atom; R 1 to R 4 and R 6 to R 9 are each independently from each other H, C 1 -C 12 -alkyl, C 3 -C 10 -cycloalkyl, C 3 -C 22 -alkenyl, C 1 -C 12 -alkoxy, C 1 -C 12 -alkylsulfanyl, hydroxy- C 1 -C 8 -alkyl, halogen, NR″ 1 R″ 2 , NO 2 , CN, phenyl, phenyloxy or R 1 and R 2 or R 2 and R 3 or R 3 and R 4 or R 6 and R 7 or R 7 and R 8 or R 8 and R 9 are linked together to form a five- or 6-membered alicylic, aromatic or heterocyclic ring together with their 2 corresponding carbons atoms, to which they are attached.

First claim

The invention claimed is:

1. A composition, which comprises
a) an organic material susceptible to oxidative, thermal or light-induced degradation, said material is one or more selected from the group consisting of a polymer, an oligohydroxy compound, a wax, a fat and a mineral oil,
with the proviso that the polymer is not a polypeptide, agar-agar or a component of agar-agar and the oligohydroxy compound is not glucose or a component of agar-agar; and
b) a compound of formula I

wherein
when n is 1,
R 5 is H, C 1 -C 30 -alkyl, C 3 -C 10 -cycloalkyl, C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 7 -C 13 -aralkyl, C 2 -C 22 -alkenyl, C 3 -C 12 -alkinyl, OH, C 1 -C 30 -alkyloxy, C 3 -C 10 -cycloalkyloxy, C 6 -C 12 -aryloxy, C 7 -C 13 -aralkyloxy, hydroxy-C 1 -C 8 -alkyl, carboxy-C 1 -C 12 -alkyl, C 1 -C 12 -alkoxycarbonyl-C 1 -C 12 -alkyl, C 2 -C 30 -alkyl, which is interrupted by one or more oxygen atoms, C 2 -C 16 -alkyl, which is interrupted by one sulfur atom, or NR′ 1 R′ 2 ;
when n is 2,
R 5 is C 1 -C 12 -alkane-diyl, 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 24 -alkane-diyl, which is interrupted by one or more oxygen atoms, C 4 -C 20 -alkane-diyl, which is interrupted by one or more —NH—, —N(C 1 -C 8 -alkyl)- or —N(hydroxy-C 1 -C 8 -alkyl)-, piperazine-N,N′-bis-(C 1 -C 4 -alkylene) or C 2 -C 10 -alkane-diyl, which is interrupted by one sulfur atom;
when n is 3,
R 5 is C 5 -C 12 -alkane-triyl, C 5 -C 24 -alkane-triyl, which is interrupted by one or more oxygen atoms, C 5 -C 24 -alkane-triyl, which is interrupted by one or more —NH—, —N(C 1 -C 8 -alkyl)- or —N(hydroxy-C 1 -C 8 -alkyl)-;
when n is 4,
R 5 is C 5 -C 24 -alkane-tetrayl, C 6 -C 24 -alkane-tetrayl, which is interrupted by one or more oxygen atoms, or C 6 -C 24 -alkane-tetrayl, which is interrupted by one or more —NH—, —N(C 1 -C 8 -alkyl)- or —N(hydroxy-C 1 -C 8 -alkyl)-;
n is 1, 2, 3 or 4;
R 1 to R 4 and R 6 to R 9 are each independently from each other H, C 1 -C 12 -alkyl, C 3 -C 10 -cycloalkyl, C 3 -C 22 -alkenyl, C 1 -C 12 -alkoxy, C 1 -C 12 -alkylsulfanyl, hydroxy-C 1 -C 8 -alkyl, halogen, NR″ 1 R″ 2 , NO 2 , CN, phenyl, phenyloxy or R 1 and R 2 or R 2 and R 3 or R 3 and R 4 or R 6 and R 7 or R 7 and R 8 or R 8 and R 9 are linked together to form a five- or 6-membered alicylic, aromatic or heterocyclic ring together with their 2 corresponding carbons atoms, to which they are attached; and
R′ 1 , R′ 2 , R″ 1 and R″ 2 are each independently from each other H, C 1 -C 12 -alkyl, C 3 -C 10 -cycloalkyl, hydroxy-C 1 -C 8 -alkyl, C 3 -C 22 -alkenyl, C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 7 -C 12 -aralkyl, carboxy-C 1 -C 12 -alkyl, C 1 -C 12 -alkoxycarbonyl-C 1 -C 12 -alkyl, or carboxy-C 6 -C 10 -aryl, or R′ 1 and R′ 2 or R″ 1 and R″ 2 form together with the nitrogen atom, to which they are attached, a 5- or 6-membered alicyclic, aromatic or heterocyclic ring.

2. The composition according to claim 1 , wherein the organic material is a polyolefin or a copolymer thereof, a polystyrene or a copolymer thereof, a polyurethane or a copolymer thereof, a polyether, which is obtainable by the polycondensation of an expoxide, an oxetane or tetrahydrofuran, or a copolymer thereof, a polyol, a polyester or a copolymer thereof, a polycarbonate or a copolymer thereof, a polyvinyl chloride or a copolymer thereof, a polyvinylidene chloride or a copolymer thereof, a polysulfone or a copolymer thereof, a polybutadiene or a copolymer thereof, a polyvinylacetate or a copolymer thereof, a polyvinylalcohol or a copolymer thereof, polyvinylacetale or a copolymer thereof, a polyamide, which is obtainable by polycondensation of a diamine and a dicarboxylic acid, or a copolymer thereof, a polyamide, which is obtainable by polycondensation of H 2 N—(CH 2 ) x —CH 2 —COOH with x=1 to 10, or a copolymer thereof, an oligohydroxy compound, a wax, a fat or a mineral oil.

3. The composition according to claim 1 , wherein in formula I
when n is 1,
R 5 is H, C 1 -C 30 -alkyl, C 3 -C 10 -cycloalkyl, C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 7 -C 13 -aralkyl, C 2 -C 22 -alkenyl, C 3 -C 12 -alkinyl, OH, C 1 -C 30 -alkyloxy, C 3 -C 10 -cycloalkyloxy, C 6 -C 12 -aryloxy, C 7 -C 13 -aralkyloxy, hydroxy-C 1 -C 8 -alkyl, carboxy-C 1 -C 12 -alkyl, C 1 -C 12 -alkoxycarbonyl-C 1 -C 12 -alkyl, C 2 -C 30 -alkyl, which is interrupted by one or more oxygen atoms, C 2 -C 16 -alkyl, which is interrupted by one sulfur atom, or NR′ 1 R′ 2 ;
when n is 2,
R 5 is C 1 -C 12 -alkane-diyl, 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 24 -alkane-diyl, which is interrupted by one or more oxygen atoms, C 4 -C 20 -alkane-diyl, which is interrupted by one or more —NH—, —N(C 1 -C 8 -alkyl)- or —N(hydroxy-C 1 -C 8 -alkyl)-, piperazine-N.N′-bis-(C 1 -C 4 -alkylene) or C 2 -C 10 -alkane-diyl, which is interrupted by one sulfur atom;
n is 1 or 2;
R 1 to R 4 and R 6 to R 9 are each independently from each other H, C 1 -C 12 -alkyl, C 3 -C 10 -cycloalkyl, C 3 -C 22 -alkenyl, C 1 -C 12 -alkoxy, C 1 -C 12 -alkylsulfanyl, hydroxy-C 1 -C 8 -alkyl, halogen, NR″ 1 R″ 2 , NO 2 , CN, phenyl, phenyloxy or R 1 and R 2 or R 2 and R 3 or R 3 and R 4 or R 6 and R 7 or R 7 and R 8 or R 8 and R 9 are linked together to form a five- or 6-membered alicylic, aromatic or heterocyclic ring together with their 2 corresponding carbons atoms; and
R′ 1 , R′ 2 , R″ 1 and R″ 2 are each independently from each other H, C 1 -C 12 -alkyl, C 3 -C 10 -cycloalkyl, hydroxy-C 1 -C 8 -alkyl, C 3 -C 22 -alkenyl, C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen or one phenyl, C 7 -C 12 -aralkyl, carboxy-C 1 -C 12 -alkyl, C 1 -C 12 -alkoxycarbonyl-C 1 -C 12 -alkyl, or carboxy-C 6 -C 10 -aryl, or R′ 1 and R′ 2 or R″ 1 and R″ 2 form together with the nitrogen atom, to which they are attached, a 5- or 6-membered alicyclic, aromatic or heterocyclic ring.

4. The composition according to claim 1 , wherein in formula I
when n is 1,
R 5 is H, C 1 -C 30 -alkyl, C 3 -C 10 -cycloalkyl, C 6 -C 10 -aryl, which is unsubstituted or substituted by C 1 -C 8 -alkyl, C 1 -C 5 alkoxy, halogen or one phenyl, C 7 -C 13 -aralkyl, C 2 -C 22 -alkenyl, C 3 -C 12 -alkinyl, OH, C 1 -C 30 -alkyloxy, C 3 -C 10 -cycloalkyloxy, C 6 -C 12 -aryloxy, C 7 -C 13 -aralkyloxy, hydroxy-C 1 -C 8 -alkyl, carboxy-C 1 -C 12 -alkyl, C 1 -C 12 -alkoxycarbonyl-C 1 -C 12 -alkyl, C 2 -C 30 -alkyl, which is interrupted by one or more oxygen atoms, C 2 -C 16 -alkyl, which is interrupted by one sulfur atom, or NR′ 1 R′ 2 ;
when n is 2,
R 5 is C 1 -C 12 -alkane-diyl, C 4 -C 24 -alkane-diyl, which is interrupted by one or more oxygen atoms, C 4 -C 20 -alkane-diyl, which is interrupted by one or more —NH—, —N(C 1 -C 8 -alkyl)- or —N(hydroxy-C 1 -C 8 -alkyl)-, piperazine-N,N′-bis-(C 1 -C 4 -alkylene) or C 2 -C 10 -alkane-diyl, which is interrupted by one sulfur atom;
n is 1 or 2;
2 substituents out of R 1 to R 4 and 2 substituents out of R 6 to R 9 are H and the other remaining 4 substituents out of R 1 to R 4 and R 6 to R 9 are each independently from each other H, C 1 -C 12 -alkyl, C 3 -C 10 -cycloalkyl, C 3 -C 22 -alkenyl, C 1 -C 12 -alkoxy, C 1 -C 12 -alkylsulfanyl, hydroxy-C 1 -C 8 -alkyl, halogen, NR″ 1 R″ 2 , NO 2 , CN, phenyl, phenyloxy; and

Assignees

• Basf Se

Inventors

• Hoelzl Werner
• Rotzinger Bruno

Classifications

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• C08K5/3465 Primary

  condensed with carbocyclic rings · CPC title

• C08K5/52

  Phosphorus bound to oxygen only · CPC title

• C07D401/00

  Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom · CPC title

• C07D403/04

  directly linked by a ring-member-to-ring-member bond · CPC title