Polyalkylenepolyamine having pendant substituted oxo-piperazinyltriazines and UV light stabilized compositions

Claim 2

A class of compounds comprising acyclic polyalkylenepolyamines ("PAPA") having a pendant substituent at each N atom to form a PAPA with a pendant triazine nucleus at each nitrogen atom to form a pendant piperazinone-triazine ("P[PIP-T]") having the structure ##STR27## wherein p' is an integer in the range from 2 to 8; R 9 represents H, C 1 -C 24 alkyl, C 4 -C 7 cycloalkyl; C 1 -C 12 cyanoalkyl or hydroxyalkyl, and phenyl; n' is an integer in the range from 2 to 12; (PIP-T) is represented by the residue of ##STR28## wherein, PSP is a substituent having the formula ##STR29## wherein, R 1 represents alkyl having 1 to about 24 carbon atoms (C 1 -C 24 ), C 5 -C 7 cycloalkyl, C 7 -C 20 aralkyl, C 1 -C 24 azaalkyl, and C 6 -C 20 azacycloalkyl; R 2 , R 3 , R 4 and R 5 independently represent C 1 -C 24 alkyl, and C 4 -C 7 polymethylene which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperazinone ring; R 6 represents hydrogen or oxygen, C 1 -C 24 alkyl, C 1 -C 12 hydroxyalkyl, benzyl, allyl, and C 1 -C 12 haloalkyl; Y may be the same as (PSP) or Z; Z represents a radical selected from the group consisting of Cl, OH, ##STR30## R 7 and R 8 represent C 2 -C 24 alkyl; Ar represents aryl; p represents an integer in the range from 2 to 20; and, Y and Z may be the same, or the same as X provided one of the substituents furnishes a leaving group.

Claim 3

The compounds of claim 1 wherein PIP-T is represented by the structure: ##STR31## wherein Z represents Cl.

Claim 4

The compounds of claim 1 wherein: PIP-T is represented by the structure ##STR32## wherein Z represents Cl; and, Y is selected from the group consisting of OH, NHC n H 2n+1 , N(C n H 2n+1 ) 2 , N--[CH 2 CH(Et)C 4 H 9 ] 2 , N--(CH 2--CH ═CH 2 ) 2 , NHCH 2 CH(Et)C 4 H 9 N--(C 3 H 7 ) 2 ##STR33## wherein n represents an integer in the range from 2 to about 6.

Claim 5

The compounds of claim 1 wherein: PSP is the residue of a polysubstituted piperazinone selected from the group consisting of compounds having the structures: ##STR34##

Claim 6

The compounds of claim 1 including: ##STR35##

Claim 7

1',1", 1'"-[[[4,6-bis[(1-methylpropyl)[2-(3,5,5-trimethyl-3-ethyl-2-oxoD-1-piperazinyl)ethyl]amino]-1,3,5-triazin-2-yl]imino]bis[2,1-ethanediylimino-1,3,5-triazine-6,2,4-triylbis[[(1-methylpropyl)imino]-2,1-ethanediyl]]]tetrakis[3,5,5-trimethyl-3-ethylpiperazinone]; ##STR36##

Claim 8

1',1", 1'"-[[[4,6-bis[(1-methylpropyl)[2-(3,5,5-trimethyl-3-ethyl-2-oxoD-1-piperazinyl)ethyl]amino]-1,3,5-triazin-2-yl]imino]bis[2,1-ethanediylimino-1,3,5-triazine-6,2,4-triylbis[[(1-methylpropyl)imino]-2,1-ethanediyl]]]tetrakis[3,5,5-trimethyl-3-ethylpiperazinone]; ##STR36##

Claim 9

1',1", 1'"-[[[4,6-bis[cyclohexyl[2-(3,3,5,5,-tetramethyl-2-oxo-1-piperazinyl)ethyl]amino]-1,3,5-triazin-2-yl]-imino]bis[2,1-ethanediylimino-1,3,5-triazine-6,2,4-triylbis[[(cyclohexyl)imino]-2,1-ethanediyl]]]tetrakis[3,-3,5,5-tetramethylpiperazinone]; ##STR37##

Claim 10

1',1", 1'"-[[[4,6-bis[cyclohexyl[2-(3,3,5,5,-tetramethyl-2-oxo-1-piperazinyl)ethyl]amino]-1,3,5-triazin-2-yl]-imino]bis[2,1-ethanediylimino-1,3,5-triazine-6,2,4-triylbis[[(cyclohexyl)imino]-2,1-ethanediyl]]]tetrakis[3,-3,5,5-tetramethylpiperazinone]; ##STR37##

Claim 11

1',1", 1'"-[1,2-ethanediylbis[[[2-[[4,6-bis[cyclohexyl[3-(3,-3,5,5-tetramethyl-2-oxo-1-piperazinyl)propyl]-amino]-1,3,5-triazin-2-yl]amino]ethyl]imino][1,3,5-triazine-6,2,4-triyl]bis[(cyclohexylimino)-3,1-propanediyl]]]tetrakis[3,-3,5,5-tetramethylpiperazinone]; ##STR38##

Claim 12

1',1", 1'"-[1,2-ethanediylbis[[[2-[[4,6-bis[cyclohexyl[3-(3,-3,5,5-tetramethyl-2-oxo-1-piperazinyl)propyl]-amino]-1,3,5-triazin-2-yl]amino]ethyl]imino][1,3,5-triazine-6,2,4-triyl]bis[(cyclohexylimino)-3,1-propanediyl]]]tetrakis[3,-3,5,5-tetramethylpiperazinone]; ##STR38##

Claim 13

1',1", 1'"-[[[4,6-bis[cyclohexyl[3-(3,3,5,5-tetramethyl-2-oxo-1-piperazinyl)propyl]amino]-1,3,5-triazin-2-yl]imino]bis[3,1-propanediylimino-1,3,5-triazine-6,2,4-triylbis[[(cyclohexyl)imino]-3,1-propanediyl]]]-tetrakis[3,3,5,5-tetramethylpiperazinone]; ##STR39##

Claim 14

1',1", 1'"-[[[4,6-bis[cyclohexyl[3-(3,3,5,5-tetramethyl-2-oxo-1-piperazinyl)propyl]amino]-1,3,5-triazin-2-yl]imino]bis[3,1-propanediylimino-1,3,5-triazine-6,2,4-triylbis[[(cyclohexyl)imino]-3,1-propanediyl]]]-tetrakis[3,3,5,5-tetramethylpiperazinone]; ##STR39##

Claim 15

1',1", 1'"-[[[4,6-bis[cyclohexyl[3-(3,3,5,5-tetramethyl-2-oxo-1-piperazinyl)propyl]amino]-1,3,5-triazin-2-yl]imino]bis[2,1-ethanediylimino-1,3,5-triazine-6,2,4-triylbis[[(cyclohexyl)imino]-3,1-propanediyl]]]tetrakis[3,3,5,5-tetramethylpiperazinone]; ##STR40##

Claim 16

1',1", 1'"-[[[4,6-bis[cyclohexyl[3-(3,3,5,5-tetramethyl-2-oxo-1-piperazinyl)propyl]amino]-1,3,5-triazin-2-yl]imino]bis[2,1-ethanediylimino-1,3,5-triazine-6,2,4-triylbis[[(cyclohexyl)imino]-3,1-propanediyl]]]tetrakis[3,3,5,5-tetramethylpiperazinone]; ##STR40##

Claim 17

1'-[[[4-(cyclohexylamino)-6-[cyclohexyl[3-(3,3,5,5-tetramethyl-2-oxo-1-piperazinyl)propyl]amino]-1,3,5-triazin-2-yl]imino]bis[2,1-ethanediylimino[6-(cyclohexylamino)-1,3,5-triazine-4,2,-diyl]cyclohexylimino(3,1-propanediyl)]]bis[3,3,5,5-tetramethylpiperazinone]; and, ##STR41##

Claim 18

1'-[[[4-(cyclohexylamino)-6-[cyclohexyl[3-(3,3,5,5-tetramethyl-2-oxo-1-piperazinyl)propyl]amino]-1,3,5-triazin-2-yl]imino]bis[2,1-ethanediylimino[6-(cyclohexylamino)-1,3,5-triazine-4,2,-diyl]cyclohexylimino(3,1-propanediyl)]]bis[3,3,5,5-tetramethylpiperazinone]; and, ##STR41##

Claim 19

1',1",1'"-[[[4,6-bis[(1,3-dimethylbutyl)[2-(3,3,5,5-tetramethyl-2-oxo-1-piperazinyl)ethyl]amino]-1,3,5-triazin-2-yl]imino]bis[2,1-ethanediylimino-1,3,5-triazine-6,2,4-triylbis[[1,3-dimethylbutyl)imino]-2,1-ethanediyl]]]tetrakis[3,3,5,5-tetramethylpiperazinone].

Claim 20

1',1",1'"-[[[4,6-bis[(1,3-dimethylbutyl)[2-(3,3,5,5-tetramethyl-2-oxo-1-piperazinyl)ethyl]amino]-1,3,5-triazin-2-yl]imino]bis[2,1-ethanediylimino-1,3,5-triazine-6,2,4-triylbis[[1,3-dimethylbutyl)imino]-2,1-ethanediyl]]]tetrakis[3,3,5,5-tetramethylpiperazinone].

Claim 21

An organic polymeric composition of matter resistant to degradation by ultraviolet light said composition having dispersed therein from about 0.01 part to about 5 parts by weight of a stabilizer compound consisting of an acyclic polyalkylene polyamine having substituted at the N atoms thereof a polysubstituted piperazinone distally linked to a triazine nucleus, per 100 parts of said organic material, said stabilizer compound being represented by the structural formula ##STR42## wherein p' is an integer in the range from 2 to 8; R 9 represents H, C 1 -C 24 alkyl, C 4 -C 7 cycloalkyl; C 1 -C 12 cyanoalkyl or hydroxyalkyl, and phenyl; n' is an integer in the range from 2 to 12; (PIP-T) is represented by the residue of ##STR43## wherein, PSP is a substituent having the formula ##STR44## wherein, R 1 represents alkyl having 1 to about 24 carbon atoms (C 1 -C 24 ), C 5 -C 7 cycloalkyl, C 7 -C 20 aralkyl, C 1 -C 24 azaalkyl, and C 6 -C 20 azacycloalkyl; R 2 , R 3 , R 4 and R 5 independently represent C 1 -C 24 alkyl, and C 4 -C 7 polymethylene which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperazinone ring; R 6 represents hydrogen or oxygen, C 1 -C 24 alkyl, C 1 -C 12 hydroxyalkyl, benzyl, allyl, and C 1 -C 12 haloalkyl; Z represents a radical selected from the group Z consisting of Cl, OH, ##STR45## R 7 and R 8 represent C 2 -C 24 alkyl; Ar represents aryl; p represents an integer in the range from 2 to 20; and, Y and Z may be the same, or the same as X, provided one of the substituents furnishes a leaving group.

Claim 22

An organic polymeric composition of matter resistant to degradation by ultraviolet light said composition having dispersed therein from about 0.01 part to about 5 parts by weight of a stabilizer compound consisting of an acyclic polyalkylene polyamine having substituted at the N atoms thereof a polysubstituted piperazinone distally linked to a triazine nucleus, per 100 parts of said organic material, said stabilizer compound being represented by the structural formula ##STR42## wherein p' is an integer in the range from 2 to 8; R 9 represents H, C 1 -C 24 alkyl, C 4 -C 7 cycloalkyl; C 1 -C 12 cyanoalkyl or hydroxyalkyl, and phenyl; n' is an integer in the range from 2 to 12; (PIP-T) is represented by the residue of ##STR43## wherein, PSP is a substituent having the formula ##STR44## wherein, R 1 represents alkyl having 1 to about 24 carbon atoms (C 1 -C 24 ), C 5 -C 7 cycloalkyl, C 7 -C 20 aralkyl, C 1 -C 24 azaalkyl, and C 6 -C 20 azacycloalkyl; R 2 , R 3 , R 4 and R 5 independently represent C 1 -C 24 alkyl, and C 4 -C 7 polymethylene which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperazinone ring; R 6 represents hydrogen or oxygen, C 1 -C 24 alkyl, C 1 -C 12 hydroxyalkyl, benzyl, allyl, and C 1 -C 12 haloalkyl; Z represents a radical selected from the group Z consisting of Cl, OH, ##STR45## R 7 and R 8 represent C 2 -C 24 alkyl; Ar represents aryl; p represents an integer in the range from 2 to 20; and, Y and Z may be the same, or the same as X, provided one of the substituents furnishes a leaving group.