Antioxidant for thermoplastic resin and thermoplastic resin composition containing same

An antioxidant for a thermoplastic resin represented by any of General Formulae (2) to (4) below:

• wherein a ring A2 is a six-membered hydrocarbon ring, aromatic ring, or heterocycle,
• R2 represents an unsubstituted or substituted alkyl group having 1 to 20 carbon atoms, an unsubstituted or substituted alkenyl group having 2 to 20 carbon atoms, an unsubstituted or substituted aryl group having 6 to 30 carbon atoms, an unsubstituted or substituted arylalkyl group having 7 to 30 carbon atoms, an unsubstituted or substituted heterocycle-containing group having 3 to 35 carbon atoms, or a trialkylsilyl group,
• a methylene group in the alkyl group, alkoxy group or arylalkyl group represented by R2 is optionally replaced with one or more groups selected from a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—O—, —S—CO—, —CO—S—, —S—CO—O—, —O—CO—S—, —CO—NH—, —NH—CO—, —NH—CO—O—, —NR′—, —S—S—, and —SO2-(provided that oxygen atoms are not adjacent to each other when the methylene group is replaced with two or more groups),
• R′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,
• R11, R12, R13, R14, and R15 represent a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, carboxyl group, an unsubstituted or substituted alkyl group having 1 to 40 carbon atoms, an unsubstituted or substituted alkoxy group having 1 to 8 carbon atoms, an unsubstituted or substituted aryl group having 6 to 30 carbon atoms, an unsubstituted or substituted arylalkyl group having 7 to 30 carbon atoms, an unsubstituted or substituted heterocycle-containing group having 3 to 20 carbon atoms, or —O—R2,
• a methylene group in the alkyl group or arylalkyl group represented by R11, R12, R13, R14, and R15 is optionally replaced with one or more groups selected from —O—, —CO—, —OC—, —O—CO—, and —CO—O— (provided that oxygen atoms are not adjacent to each other when the methylene group is replaced with two or more groups), and
• at least one of R11, R12, R13, R14, and R15 is not a hydrogen atom;
• wherein X11 represents a group represented by General Formula (3-1) below,
• R16, R17, R18, and R19 represent a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an unsubstituted or substituted alkyl group having 1 to 40 carbon atoms, an unsubstituted or substituted alkoxy group having 1 to 8 carbon atoms, an unsubstituted or substituted aryl group having 6 to 30 carbon atoms, an unsubstituted or substituted arylalkyl group having 7 to 30 carbon atoms, or an unsubstituted or substituted heterocycle-containing group having 3 to 20 carbon atoms,
• at least one of R16, R17, R18, and R19 is not a hydrogen atom, and
• R2 and a ring A2 are the same as R2 and the ring A2 in General Formula (2),
• *—Z1—X1—Z2—* (3-1)
• wherein X1 represents —CR30R31—, —NR32—, an unsubstituted or substituted divalent aliphatic hydrocarbon group having 1 to 120 carbon atoms, an unsubstituted or substituted divalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, an unsubstituted or substituted divalent heterocycle-containing group having 3 to 35 carbon atoms, or a substituent represented by one of formulae (3-2) to (3-5) below,
• the aliphatic hydrocarbon group is optionally interrupted by —O—, —S—, —CO—, —COO—, —OCO—, or —NH—, or a linking group in which these groups are used in combination in a state in which oxygen atoms are not adjacent to each other,
• R30 and R31 represent a hydrogen atom, an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, an unsubstituted or substituted alkoxy group having 1 to 8 carbon atoms, an unsubstituted or substituted aryl group having 6 to 30 carbon atoms, or an unsubstituted or substituted arylalkyl group having 7 to 30 carbon atoms,
• Z1 and Z2 independently represent a direct bond, —O—, —S—, >CO, —CO—O—, —O—CO—, —SO2—, —SS—, —SO—, >NR33, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 35 carbon atoms, an unsubstituted or substituted aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or an unsubstituted or substituted heterocycle-containing group having 3 to 35 carbon atoms, and
• R32 and R33 represent a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 35 carbon atoms, an unsubstituted or substituted aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or an unsubstituted or substituted heterocycle-containing group having 3 to 35 carbon atoms,
• wherein R21 represents a hydrogen atom, an unsubstituted or substituted phenyl group, or an unsubstituted or substituted cycloalkyl group having 3 to 10 carbon atoms,
• R22 represents an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, an unsubstituted or substituted alkoxy group having 1 to 8 carbon atoms, an unsubstituted or substituted alkenyl group having 2 to 10 carbon atoms, or a halogen atom, and
• a is an integer from 0 to 5,
• wherein R23 and R24 independently represent an unsubstituted or substituted alkyl group having 1 to 10 carbon atoms, an unsubstituted or substituted alkoxy group having 1 to 8 carbon atoms, an unsubstituted or substituted aryl group having 6 to 30 carbon atoms, an unsubstituted or substituted aryloxy group having 6 to 30 carbon atoms, an unsubstituted or substituted arylthio group having 6 to 30 carbon atoms, an unsubstituted or substituted arylalkenyl group having 6 to 30 carbon atoms, an unsubstituted or substituted arylalkyl group having 7 to 30 carbon atoms, an unsubstituted or substituted heterocyclic group having 3 to 20 carbon atoms, or a halogen atom,
• a methylene group in the alkyl group, the alkoxy group, or the arylalkyl group is optionally replaced with an unsaturated bond, —O—, or —S—,
• R23 optionally forms a ring together with adjacent R23,
• b represents a number from 0 to 4,
• c represents a number from 0 to 8,
• g represents a number from 0 to 4,
• h represents a number from 0 to 4, and
• a total number of g and h is 2 to 4, and
• wherein Y1 and Y2 independently represent an alkylene group having 1 to 8 carbon atoms, and a methylene group in the alkylene group is optionally replaced with one or more groups selected from —O—, —CO—, —OC—, —O—CO—, and —CO—O—;
• and
• wherein m=2 to 6,
• X3 is a group represented by General Formula (3-1) when m=2, X3 is a group represented by General Formula (4-1) when m=3, X3 is a group represented by General Formula (4-2) when m=4, X3 is a group represented by General Formula (4-3) when m=5, and X3 is a group represented by General Formula (4-4) when m=6,
• R25, R26, R27, and R28 represent a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, an unsubstituted or substituted alkyl group having 1 to 40 carbon atoms, an unsubstituted or substituted alkoxy group having 1 to 8 carbon atoms, an unsubstituted or substituted aryl group having 6 to 30 carbon atoms, an unsubstituted or substituted arylalkyl group having 7 to 30 carbon atoms, or an unsubstituted or substituted heterocycle-containing group having 3 to 20 carbon atoms,
• at least one of R25, R26, R27, and R28 is not a hydrogen atom, and
• R2 and a ring A2 are the same as R2 and the ring A2 in General Formula (2),
• wherein Y11 represents an unsubstituted or substituted trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an unsubstituted or substituted trivalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or an unsubstituted or substituted trivalent heterocycle-containing group having 3 to 35 carbon atoms,
• Z1, Z2, and Z3 independently represent a direct bond, —O—, —S—, >CO, —CO—O—, —O—CO—, —SO2—, —SS—, —SO—, >NR34, >PR34, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 35 carbon atoms, an unsubstituted or substituted aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or an unsubstituted or substituted heterocycle-containing group having 3 to 35 carbon atoms,
• R34 represents a hydrogen atom, an unsubstituted or substituted aliphatic hydrocarbon group having 1 to 35 carbon atoms, an unsubstituted or substituted aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or an unsubstituted or substituted heterocycle-containing group having 3 to 35 carbon atoms, and
• the aliphatic hydrocarbon group is optionally interrupted by a carbon-carbon double bond, —O—, —CO—, —O—CO—, —CO—O—, or —SO2—,
• wherein Y12 represents a carbon atom, an unsubstituted or substituted tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an unsubstituted or substituted tetravalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or an unsubstituted or substituted tetravalent heterocycle-containing group having 3 to 35 carbon atoms,
• the aliphatic hydrocarbon group is optionally interrupted by —COO—, —O—, —OCO—, —NHCO—, —NH—, or —CONH—, and
• Z1 to Z4 independently represent the same group as the group represented by Z1 to Z3 in General Formula (4-1),
• wherein Y13 represents an unsubstituted or substituted pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an unsubstituted or substituted pentavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or an unsubstituted or substituted pentavalent heterocycle-containing group having 3 to 35 carbon atoms,
• the aliphatic hydrocarbon group is optionally interrupted by —COO—, —O—, —OCO—, —NHCO—, —NH—, or —CONH—, and
• Z1 to Z5 independently represent the same group as the group represented by Z1 to Z3 in General Formula (4-1),
• wherein Y14 represents an unsubstituted or substituted hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an unsubstituted or substituted hexavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, or an unsubstituted or substituted hexavalent heterocycle-containing group having 3 to 35 carbon atoms,
• the aliphatic hydrocarbon group is optionally interrupted by —COO—, —O—, —OCO—, —NHCO—, —NH—, or —CONH—, and
• Z1 to Z6 independently represent the same group as the group represented by Z1 to Z3 in General Formula (4-1).