Tris(piperidylaminotriazylamino) compounds, their preparation and their use as polymer stabilizers

Claim 2

Compounds of formula (I): [in which: the groups represented by X are the same and have the formula (II): (in which: R 1 represents a hydrogen atom, a C 1 -C 18 alkyl group, a C 2 -C 22 alkoxyalkyl group, a C 1 -C 18 acyl group, an aralkyl group optionally having at least one C 1 -C 4 alkyl or halogen substituent or a group of formula (III): and R 2 and R are the same or different and each represents a hydrogen atom, a C 1 -C 18 alkyl group, a C 1 -C 18 acyl group or an aralkyl group optionally having at least one C 1 -C 4 alkyl or halogen substituent); and Y represents a hydrogen atom, a C 1 -C 18 alkyl group, a C 1 -C 18 acyl group, an aralkyl group optionally having at least one C 1 -C 4 alkyl or halogen substituent or a group of formula (IV): in which R 4 has any of the meanings defined for R 2 ]: and acid addition salts thereof.

Claim 3

Compounds as claimed in Claim 1, in which: where R 1 and Y both represent acyl groups, these acyl groups are the same; where one of R 1 and Y represents an acyl group, the other does not represent a hydrogen atom; where two or three of R , R and R represent acyl groups, these acyl groups are the same; and where one or two of R 2 , R and R represent acyl groups, the other or others do not represent hydrogen atoms.

Claim 4

Compounds as claimed in Claim 2, in which: where two or more of R , R 2 , R 3 , Rand Y represent acyl groups, these acyl groups are the same: and where one or more of R 1 , R 2 , R 3 , R 4 and Y represent acyl groups, the other or others do not represent hydrogen atoms.

Claim 5

Compounds as claimed in any one of Claims 1 to 3, in which: R 1 represents a hydrogen atom, a C 1 -C 18 alkyl group, a C 3 -C 22 alkoxyalkyl group, a C 2 -C 18 acyl group, said optionally substituted aralkyl group or said group of formula (III); R 2 , R and R 4 are the same or different and each represents a hydrogen atom, a C 1 -C 18 alkyl group, a C 2 -C 18 acyl group or said optionally substituted aralkyl group; and Y represents a hydrogen.atom, a C 1 -C 18 alkyl group, a C 2 -C 18 acyl group, said optionally substituted aralkyl group or said group of formula (IV).

Claim 6

Compounds as claimed in Claim 4, in which Y represents a hydrogen atom, a C 1 -C 18 alkyl group, a C 2 -C 18 acyl group or an aralkyl group optionally having a C 1 -C 4 alkyl or halogen substituent.

Claim 7

Compounds as claimed in any one of Claims 1 to 5, in which Y represents a hydrogen atom, a methyl group or an acetyl group.

Claim 8

Compounds as claimed in any one of Claims 1 to 6, in which R 2 and R are the same and each represents a hydrogen atom, a methyl group or an acetyl group.

Claim 9

Compounds as claimed in Claim 7, in which Y , R 2 and R 3 are the same and each represents a hydrogen atom, a methyl group or an acetyl group.

Claim 10

Compounds as claimed in any one of Claims 1 to 3, in which Y and R , which may be the same or different, each represents a hydrogen atom or a methyl group, and R 1 represents a hydrogen atom, a C 1 -C 18 alkyl group or a C 3 -C 22 alkoxyalkyl group.

Claim 11

Compounds as claimed in Claim 9, in which Y and R 2 , which may be the same or different, each represents a hydrogen atom or a methyl group, and R represents a hydrogen atomn or a C 4 -C 8 alkyl group.

Claim 12

1,8-Bis[N-(2,4-bis[N-butyl-N-(2,2,6,6-tetramethyl- piperid-4-yl)amino]-1,3,5-triazin-6-yl)amino]-4-[N-(2,4- bis[N-butyl-N-(2,2,6,6-tetramethylpiperid-4-yl)amino]-1,3,5-triazin-6-yl)aminomethyl]octane, 1,8-bis[N-methyl-N-(2,4-bis[N-butyl-N-(1.2.2.6.6-pentamethylgiperid-4-yl)amino]-1,3,5-triazin-6-yl)amino]-4-[N-methyl-N-(2,4-bis[N-butyl-N-(1,2,2,6,6-pentamethyl- piperid-4-yl)amino]-1,3,5-triazin-6-yl)aminomethyl]octane, 1,8-bis[N-(2,4-bis[N-octyl-N-(2,2,6,6-tetramethyl- piperid-4-yl)amino]-1,3,5-triazin-6-yl)amino]-4-[N-(2,4- bis[N-octyl-N-(2,2,6,6-tetramethylpiperid-4-yl)amino]-1,3,5-triazin-6-yl)aminomethyl]octane and acid addition salts thereof.

Claim 13

1,8-Bis[N-(2,4-bis[N-butyl-N-(2,2,6,6-tetramethyl- piperid-4-yl)amino]-1,3,5-triazin-6-yl)amino]-4-[N-(2,4- bis[N-butyl-N-(2,2,6,6-tetramethylpiperid-4-yl)amino]-1,3,5-triazin-6-yl)aminomethyl]octane, 1,8-bis[N-methyl-N-(2,4-bis[N-butyl-N-(1.2.2.6.6-pentamethylgiperid-4-yl)amino]-1,3,5-triazin-6-yl)amino]-4-[N-methyl-N-(2,4-bis[N-butyl-N-(1,2,2,6,6-pentamethyl- piperid-4-yl)amino]-1,3,5-triazin-6-yl)aminomethyl]octane, 1,8-bis[N-(2,4-bis[N-octyl-N-(2,2,6,6-tetramethyl- piperid-4-yl)amino]-1,3,5-triazin-6-yl)amino]-4-[N-(2,4- bis[N-octyl-N-(2,2,6,6-tetramethylpiperid-4-yl)amino]-1,3,5-triazin-6-yl)aminomethyl]octane and acid addition salts thereof.

Claim 14

A synthetic polymer composition comprising a synthetic polymer stabilized against the effects of light by the incorporation of a polymer stabilizer, wherein the stabilizer comprises at least one compound as claimed in any one of Claims 1 to 11.

Claim 15

A composition as claimed in Claim 12, wherein said stabilizer is present in an amount of from 0.01 to 5% by weight of the polymer.

Claim 16

A composition as claimed in Claim 13, wherein said polymer is an olefin, diene or styrene polymer and said stabilizer is present in an amount of from 0.01 to 2.0% by weight of the polymer.

Claim 17

A composition as claimed in Claim 13, wherein said polymer is a vinyl chloride or vinylidene chloride polymer and said stabilizer is present in an amount of from 0.01 to 1.0% by weight of the polymer.

Claim 18

A composition as claimed in Claim 13, wherein said polymer is a polyurethane or polyamide and said stabilizer is present in an amount of from 0.01 to 5.0% by weight of the polymer.

Claim 19

A process for preparing a compound as claimed in any one of Claims 1 to 11, which process comprises: (a) reacting a compound of formula (VIII): (in which Q represents a halogen atom) with a compound of formula (VII): and with a compound of formula (X): in any order: in the above formulae: R 1' represents a hydrogen atom, a C 1 -C 18 alkyl group, a C 2 -C 22 alkoxyalkyl group, an aralkyl group optionally having at least one C 1 -C 4 alkyl or halogen substituent, or a group of formula (IIIa): Y' represents a hydrogen atom, a C 1 -C 18 alkyl group, an aralkyl group optionally having at least one C 1 -C 4 alkyl or halogen substituent, or a group of formula (IVa): 2' 3' 4' R , R and R are the same or different and each represents a hydrogen atom, a C 1 -C 18 alkyl group or an aralkyl group optionally having at least one C l -C 4 alkyl or halogen substituent; and (b) if necessary, subjecting the product to one or more of the reactions: alkylation, acylation and salification.

Claim 20

A process as claimed in Claim 17, in which, in said compound of formula (VII), R 1' represents a butyl group and R 21 represents a hydrogen atom, and, in said compound of formula (X), Y' represents a hydrogen atom, to prepare 1,8-bis[N-(2,4-bis[N-butyl-N-(2,2,6,6-tetramethylpiperid-4-yl)amino]-1,3,5-triazin-6-yl)amino]-4-[N-(2,4-bis[N-butyl-N-(2,2,6,6-tetramethylpiperid-4-yl)amino]-1,3,5-triazin-6-yl)aminomethyl]octane.

Claim 21

A process as claimed in Claim 17, in which, in said compound of formula (VII), R 1' represents a butyl group and R 21 represents a hydrogen atom or a methyl group, and, in said compound of formula (X), Y' represents a hydrogen atom or a methyl group, and, if necessary, the resulting compound of formula (I) in which R 2 and/or Y represents a hydrogen atom is methylated, to prepare 1,8-bis[N-methyl-N-(2,4-bis[N-butyl-N-(1,2,2,6,6-pentamethylpiperid-4-yl)amino]-1,3,5-triazin-6-yl)amino]-4-[N-methyl-N-(2.4-bis[N-butyl-N-(1,2,2,6,6-pentamethylpiperid-4-yl)amino]-1,3,5-triazin-6-yl)aminomethyl]octane.

Claim 22

A process as claimed in Claim 17, in which, in said compound of formula (VII), R 1' represents an octyl group and R 2' represents a hydrogen atom, and, in said compound of formula (X), Y' represents a hydrogen atom, to prepare 1,8-bis[N-(2,4-bis[N-octyl-N-(2,2,6,6-tetramethylpiperid-4-yl)amino)-1,3,5-triazin-6-yl)amino]-4-[N-(2,4-bis[N-octyl-N-(2,2,6,6-tetramethylpiperid-4-yl)amino]-1,3,5-triazin-6-yl)aminomethyl]octane.

Claim 23

A process as claimed in any one of Claims 17 to 20, in which said compound of formula (VII) is first reacted with said compound of formula (VIII) and then the product is reacted with said compound of formula (X).