Compositions stabilized with ethers of di- and tri-substituted hydroxylamines

Claim 2

A composition of matter comprising a, polymer or lubricating oil subject to oxidative, thermal and actinic degradation stabilized with an effective stabilizing amount of a compound selecting from the group consisting of α,α'-bis (benzyloxyamino)-p-xylene and compounds having the formula ##STR3## wherein R 1 is hydrogen, alkyl of 1 to 36 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 9 carbon atoms or said aralkyl substituted by alkyl of 1 to 36 carbon atoms; R 2 is alkyl of 1 to 36 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 9 carbon atoms or said aralkyl substituted by alkyl of 1 to 36 carbon atoms; n is 1-4; X, when n is 1, is the same as R 2 ; X, when n is 2, is alkylene of 2 to 12 carbon atoms, cycloalkylene of 6 to 10 carbon atoms or alkylenearylenealkylene of 8 to 10 carbon atoms; X, when n is 3, is alkanetriyl of 3 to 6 carbon atoms or ##STR4## and X, when n is 4, is alkanetetrayl of 4 to 6 carbon atoms.

Claim 3

The composition of claim 1, wherein R 1 and R 2 in said compound are independently alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, benzyl α-methylbenzyl or α,α-dimethylbenzyl.

Claim 4

The composition of claim 2, wherein R 1 and R 2 are benzyl.

Claim 5

The compostion of claim 1, wherein R 1 is hydrogen and R 2 is alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, benzyl, α, methylbenzyl or α,α-dimethylbenzyl.

Claim 6

The composition of claim 1, wherein n is 1.

Claim 7

The composition of claim 5, wherein X is alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, benzyl,α-methylbenzyl or α,α-dimethylbenzyl.

Claim 8

The composition of claim 1, wherein n is 2.

Claim 9

The composition of claim 7, wherein X is alkylene of 2 to 12 carbon atoms, cyclohexylene and xylylene.

Claim 10

The composition of claim 5 containing O-methyl-N,N-dibenzylhydroxylamine.

Claim 11

The composition of claim 5, containing N,N,O-tribenzylhydroxylamine.

Claim 12

The composition of claim 5, containing N,N,O-tris[m-methylbenzyl]hydroxylamine.

Claim 13

The composition of claim 5, containing N-dodecyl-O-benzylhydroxylamine.

Claim 14

The composition of claim 5, containing N,N-didodecyl-O-benzylhydroxylamine.

Claim 15

The composition of claim 5, containing N,O-dibenzylhydroxylamine.

Claim 16

The composition of claim 5, containing O-methyl-N-benzylhydroxylamine.

Claim 17

The composition of claim 7, containing 1,8-bis[N,N-dibenzylaminoxy]octane.

Claim 18

The composition of claim 1, wherein the polymer is a synthetic polymer.

Claim 19

The composition of claim 17, wherein the synthetic polymer is a polyolefin monopolymer or copolymer.

Claim 20

The composition of claim 18 which also contains a metal salt of a higher fatty acid.

Claim 21

The composition of claim 1 which also contains a phenolic antioxidant.

Claim 22

The composition of claim 19 which also contains a phenolic antioxidant.

Claim 23

The composition of claim 20, wherein said phenolic antioxidant is selected from the group consisting of n-octadecyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate, neopentanetetrayl tetrakis-(3,5-di-tert-butyl-4-hydroxylhydrocinnamate), di-n-octadecyl 3,5-di-tert-butyl-4-hydroxybenzyl-phosphonate, 1,3,5-tris(3,5-di-tert-butyl-4hydroxy-benzyl)isocyanurate, thiodiethylene bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate), 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 3,6-di-oxaocta-methylene bis(3-methyl-5-tert-butyl-4-hydroxyhydro-cinnamate), 2,6-di-tert-butyl-p-cresol, 2,2'-ethylidene-bis(4,6-di-tert-butylphenol), 1,3,5-tris(2,6-di-methyl-4-tert-butyl-3-hydroxybenzyl)isocyanurate, 1,1,3-tris-(2-methyl-4-hydroxy-5-tert-butylphenyl)butane, 1,3,5-tris-[2-(3,5-di-tert-butyl-4-hydroxyhydro-cinnamoyl-oxy)-ethyl]-isocyanurate, 3,5-di-(3,5-di-tert-butyl-4-hydroxybenzyl)-mesitol, hexa-methylene bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate), 1-(3,5-di-tert-butyl-4-hydroxyanilino)-3,5-di(octylthio)-s-triazine, N,N'-hexamethylene-bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamamide), calcium bis(ethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate), ethylene bis[3,3-di(3-tert-butyl-4-hydroxyphenyl)butyrate], octyl 3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate, bis(3,5-di-tert-butyl-4-hydroxyhydrocinnamoyl)hydrazide, and N,N'-bis[2-(3,5-tert-butyl-4-hydroxyhydroxo-cinnamoyloxy)ethyl]oxamide.

Claim 24

The composition of claim 22, wherein said phonolic antioxidant is neopentanetetrayl tetrakis(3,5-di-tert-butyl-4-hydroxyhydrocinnamate), n-octadecyl 3,5-di-tert-butyl-4-hydroxyhydrocinnamate, 1,3,5-trimethyl-2,4,6-tris(3,5-tert-butyl-4-hydroxybenzylbenzene, 1,3,5-tris(3,5-di-tert-butyl-4-hydroxybenzyl)isocyanurate, 2,6-di-tert-butyl-p-cresol or 2,2'-ethylidene-bis(4,6-di-tert-butylphenol).

Claim 25

A method for stabilizing a polymer or lubricating oil against oxidative, thermal and actinic degradation which comprises incorporating into said organic material an effective stabilizing amount of a compound of claim 1.

Claim 26

A compound of the formula ##STR5## wherein m is 2-4; R 1 is hydrogen, alkyl of 1 to 36 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 9 carbon atoms or said aralkyl substituted by alkyl of 1 to 36 carbon atoms; R 2 is alkyl of 1 to 36 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 9 carbon atoms or said aralkyl substituted by alkyl of 1 to 36 carbon atoms; at least one of R 1 and R 2 being said aralkyl or said substituted aralkyl when m is 2; X, when m is 2, is alkylene of 2 to carbon atoms, cycloalkylene of 6 to 10 carbon atoms or alkylenearylenealkylene of 8 to 10 carbon atoms; X, when m is 3, is alkanetriyl of 3 to 6 carbon atoms or ##STR6## and X, when m is 4, is alkanetetrayl of 4 to 6 carbon atoms.

Claim 27

A compound of the formula ##STR5## wherein m is 2-4; R 1 is hydrogen, alkyl of 1 to 36 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 9 carbon atoms or said aralkyl substituted by alkyl of 1 to 36 carbon atoms; R 2 is alkyl of 1 to 36 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, aralkyl of 7 to 9 carbon atoms or said aralkyl substituted by alkyl of 1 to 36 carbon atoms; at least one of R 1 and R 2 being said aralkyl or said substituted aralkyl when m is 2; X, when m is 2, is alkylene of 2 to carbon atoms, cycloalkylene of 6 to 10 carbon atoms or alkylenearylenealkylene of 8 to 10 carbon atoms; X, when m is 3, is alkanetriyl of 3 to 6 carbon atoms or ##STR6## and X, when m is 4, is alkanetetrayl of 4 to 6 carbon atoms.

Claim 28

The compound of claim 25, wherein R 1 and R 2 are independently alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, benzyl, α-methylbenzyl or α,α-dimethylbenzyl, with at least one of R 1 and R 2 being benzyl, α-methylbenzyl or α,α-dimethylbenzyl when m is 2.

Claim 29

The compound of claim 26, wherein m is 2.

Claim 30

The compound of claim 27, wherein X is alkylene of 2 to 12 carbon atoms, cyclohexylene or xylylene.

Claim 31

The compound of claim 26, wherein R 1 and R 2 are benzyl.

Claim 32

The compound of claim 25, wherein R 1 is hydrogen and R 2 is alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 6 carbon atoms, benzyl, α-methylbenzyl or α,α-dimethylbenzyl, with R 2 being benzyl, α-methylbenzyl or α,α-dimethylbenzyl when m is 2.

Claim 33

1,8-Bis[N,N-dibenzylaminoxy]octane according to claim 27.

Claim 34

α,α'-bis[benzyloxyamino]-p-xylene.

Claim 35

α,α'-bis[benzyloxyamino]-p-xylene.