Substituted oxo-piperazinyl-triazines and UV light stabilized compositions

Claim 2

A class of compounds comprising polysubstituted piperzinones distally linked to a triazine nucleus ("PIP-T"), and bis compounds and oligomers of said PIP-T compounds represented by the structural formula ##STR57## wherein, n is an integer in the range from 1 to about 10, said compound having functional end groups selected from H, OH and Cl when n is greater than 1; X is a substituent having the following formula (II): ##STR58## wherein, R 2 , R 3 , R 4 and R 5 independently represent C 1 -C 24 alkyl and polymethylene having from 4 to about 7 C atoms which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperazinone ring, R 1 represents hydrogen or oxygen, C 1 -C 24 alkyl, C 1 -C 12 hydroxyalkyl, benzyl, allyl, and C 1 -C 12 haloalkyl; R 8 and R 9 independently represent C 1 -C 24 alkyl, and polymethylene having from 4 to about 7 C atoms which are cyclizable; R 10 represents H, C 1 -C 6 alkyl and phenyl; Y may be the same as X or M; M may be Z or Z', wherein Z represents a radical selected from the group consisting of Cl, OH, ##STR59## R 6 , R 7 represent alkyl having from 2 to about 24 carbon atoms; and C 4 -C 7 cycloalkyl; Ar represents aryl; Z' represents a radical selected from the group consisting of ##STR60## p represents an integer in the range from 2 to about 20; x represents an integer in the range from 1 to about 50; m represents an integer in the range from 2 to about 4 and, when n=1, Y and M may be the same as X.

Claim 3

The compounds of claim 1 having the structural formula ##STR61##

Claim 4

The compounds of claim 1 having the structural formula ##STR62##

Claim 5

The compounds of claim 1 having the structural formula ##STR63##

Claim 6

The compounds of claim 1 having the structural formula ##STR64##

Claim 7

A class of compounds comprising acyclic polyalkylenepolyamines ("PAPA") having a pendant substituent at each nitrogen 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 ##STR65## wherein p' is an integer in the range from 2 to 8; R 10 represents H, C 1 -C 6 alkyl and phenyl; n" is an integer in the range from 2 to 12; Y and M may be the same or different and is selected from the group consisting of PSP, ##STR66## PSP is a substituent having the formula ##STR67## wherein, R 2 , R 3 , R 4 and R 5 independently represent C 1 -C 24 alkyl and polymethylene having from 4 to about 7 C atoms which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperazinone ring, R 1 represents hydrogen of oxygen, C 1 -C 24 alkyl, C 1 -C 12 hydroxyalkyl, benzyl, allyl, and C 1 -C 12 haloalkyl; R 8 and R 9 independently represent C 1 -C 24 alkyl, and polymethylene having from 4 to about 7 C atoms which are cyclizable; Y may be the same as M; M may be Z or Z', wherein Z represents a radical selected from the group consisting of Cl, OH, ##STR68## R 6 , R 7 represent alkyl having from 2 to about 24 carbon atoms; and C 4 -C 7 cycloalkyl; Ar represents aryl; Z' represents a radical selected from the group consisting of ##STR69## p represents an integer in the range from 2 to about 20; x represents an integer in the range from 1 to about 50; m represents an integer in the range from 2 to about 4 and, Y and M may be the same.

Claim 8

A class of compounds comprising acyclic polyalkylenepolyamines ("PAPA") having a pendant substituent at each nitrogen 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 ##STR65## wherein p' is an integer in the range from 2 to 8; R 10 represents H, C 1 -C 6 alkyl and phenyl; n" is an integer in the range from 2 to 12; Y and M may be the same or different and is selected from the group consisting of PSP, ##STR66## PSP is a substituent having the formula ##STR67## wherein, R 2 , R 3 , R 4 and R 5 independently represent C 1 -C 24 alkyl and polymethylene having from 4 to about 7 C atoms which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperazinone ring, R 1 represents hydrogen of oxygen, C 1 -C 24 alkyl, C 1 -C 12 hydroxyalkyl, benzyl, allyl, and C 1 -C 12 haloalkyl; R 8 and R 9 independently represent C 1 -C 24 alkyl, and polymethylene having from 4 to about 7 C atoms which are cyclizable; Y may be the same as M; M may be Z or Z', wherein Z represents a radical selected from the group consisting of Cl, OH, ##STR68## R 6 , R 7 represent alkyl having from 2 to about 24 carbon atoms; and C 4 -C 7 cycloalkyl; Ar represents aryl; Z' represents a radical selected from the group consisting of ##STR69## p represents an integer in the range from 2 to about 20; x represents an integer in the range from 1 to about 50; m represents an integer in the range from 2 to about 4 and, Y and M may be the same.

Claim 9

The compounds of claim 1 wherein X is a residue of a polysubstituted piperazinone ("PSP") said "PSP" residue having a structure selected from the group consisting of ##STR70## and M and Y are independently selected from the group consisting of ##STR71##

Claim 10

The compounds of claim 7 including: 1,1'-[(6-cyclohexylamino-1,3,5-triazine-2,4-diyl)bis-[imino(2,2-dimethyl-2,1-ethanediyl)]]bis[3,3,5,5-tetramethylpiperazinone]; 1,1'-[6-(2-ethylhexyl)amino-1,3,5-triazine-2,4-diyl]bis[imino(2,2-dimethyl-2,1-ethanediyl)]]bis[3,3,5,5-tetramethylpiperazinone]; and, 1-[2-[[4,6-di(cyclohexylamino)-1,3,5-triazin-2-yl]-amino]-2-methylpropyl]-3,3,5,5-tetramethylpiperazinone.

Claim 11

The compounds of claim 4 including: poly[[6-[[1,1-dimethyl-2-(3,3,5,5-tetramethyl-2-oxo-1-piperazinyl)ethyl]amino]-1,3,5-triazine-2,4-diyl]imino-1,2 ethanediyl-1,4-piperazinediyl].

Claim 12

An organic polymeric composition of matter resistant to degradation by ultraviolet light said composition having dispersed therein from about 0.01 parts to about 5 parts by weight of a stabilizer compound consisting of 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 ##STR72## wherein, n is an integer in the range from 1 to about 10, said compound having functional end groups selected from H, OH and Cl when n is greater than 1; X is a substituent having the following formula (II): ##STR73## wherein, R 2 , R 3 , R 4 and R 5 independently represent C 1 -C 24 alkyl and polymethylene having from 4 to about 7 C atoms which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperazinone ring, R 1 represents hydrogen or oxygen, C 1 -C 24 alkyl, C 1 -C 12 hydroxyalkyl, benzyl, allyl, and C 1 -C 12 haloalkyl; R 8 and R 9 independently represent C 1 -C 24 alkyl, and polymethylene having from 4 to about 7 C atoms which are cyclizable; R 10 represents H, C 1 -C 6 alkyl and phenyl; Y may be the same as X or M; M may be Z or Z', wherein Z represents a radical selected from the group consisting of Cl, OH, ##STR74## R 6 , R 7 represent alkyl having from 2 to about 24 carbon atoms; and C 4 -C 7 cycloalkyl; Ar represents aryl; Z' represents a radical selected from the group consisting of ##STR75## p represents an integer in the range from 2 to about 20; x represents an integer in the range from 1 to about 50; m represents an integer in the range from 2 to about 4 and, when n=1, Y and M may be the same as X.

Claim 13

An organic polymeric composition of matter resistant to degradation by ultraviolet light said composition having dispersed therein from about 0.01 parts to about 5 parts by weight of a stabilizer compound consisting of 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 ##STR72## wherein, n is an integer in the range from 1 to about 10, said compound having functional end groups selected from H, OH and Cl when n is greater than 1; X is a substituent having the following formula (II): ##STR73## wherein, R 2 , R 3 , R 4 and R 5 independently represent C 1 -C 24 alkyl and polymethylene having from 4 to about 7 C atoms which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperazinone ring, R 1 represents hydrogen or oxygen, C 1 -C 24 alkyl, C 1 -C 12 hydroxyalkyl, benzyl, allyl, and C 1 -C 12 haloalkyl; R 8 and R 9 independently represent C 1 -C 24 alkyl, and polymethylene having from 4 to about 7 C atoms which are cyclizable; R 10 represents H, C 1 -C 6 alkyl and phenyl; Y may be the same as X or M; M may be Z or Z', wherein Z represents a radical selected from the group consisting of Cl, OH, ##STR74## R 6 , R 7 represent alkyl having from 2 to about 24 carbon atoms; and C 4 -C 7 cycloalkyl; Ar represents aryl; Z' represents a radical selected from the group consisting of ##STR75## p represents an integer in the range from 2 to about 20; x represents an integer in the range from 1 to about 50; m represents an integer in the range from 2 to about 4 and, when n=1, Y and M may be the same as X.

Claim 14

The composition of claim 10 wherein said stabilizer compound has the structural formula ##STR76##

Claim 15

The composition of claim 10 wherein said stabilizer compound has the structural formula ##STR77##

Claim 16

The composition of claim 10 wherein said stabilizer compound has the structural formula ##STR78##

Claim 17

The composition of claim 10 wherein said stabilizer compound has the structural formula ##STR79##

Claim 18

The composition of claim 10 wherein said X is a residue of a polysubstituted piperazinone ("PSP") said "PSP" residue having a structure selected from the group consisting of ##STR80## and M and Y are independently selected from the group consisting of ##STR81##

Claim 19

The composition of claim 10 wherein said stabilizer compound is selected from the group consisting of 1,1'-[(6-cyclohexylamino-1,3,5-triazine-2,4-diyl)bis[imino(2,2-dimethyl-2,1-ethanediyl)]]bis[3,3,5,5-tetramethylpiperazinone]; 1,1'-[6-(2-ethylhexyl)amino-1,3,5-triazine-2,4-diyl]bis[imino(2,2-dimethyl-2,1-ethanediyl)]]bis[3,3,5,5-tetramethylpiperazinone]; 1-[2-[[4,6-di(cyclohexylamino)-1,3,5-triazin-2-yl]-amino]-2-methylpropyl]-3,3,5,5-tetramethylpiperazinone; and, poly[[6-[[1,1-dimethyl-2-(3,3,5,5-tetramethyl-2-oxo-1-piperazinyl)ethyl]amino]-1,3,5-triazine-2,4-diyl]imino-1,2 ethanediyl-1,4-piperazinediyl].

Claim 20

A composition of matter resistant to degradation by ultraviolet light comprising an organic material subject to ultraviolet light degradation 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 ##STR82## wherein (PIP-T) is represented by the residue of ##STR83## wherein, n is an integer in the range from 1 to about 10, said compound having functional end groups selected from H, OH and Cl when n is greater than 1; X is a substituent having the following formula (II): ##STR84## wherein, R 2 , R 3 , R 4 and R 5 independently represent C 1 -C 24 alkyl and polymethylene having from 4 to about 7 C atoms which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperazinone ring, R 1 represents hydrogen or oxygen, C 1 -C 24 alkyl, C 1 -C 12 hydroxyalkyl, benzyl, allyl, and C 1 -C 12 halcalkyl; R 8 and R 9 independently represent C 1 -C 24 alkyl, and polymethylene having from 4 to about 7 C atoms which are cyclizable; R 10 represents H, C 1 -C 6 alkyl and phenyl; Y may be the same as X or M; M may be Z or Z', wherein Z represents a radical selected from the group consisting of Cl, OH, ##STR85## R 6 , R 7 represent alkyl having from 2 to about 24 carbon atoms; and C 4 -C 7 cycloalkyl; Ar represents aryl; Z' represents a radical selected from the group consisting of ##STR86## p represents an integer in the range from 2 to about 20; x represents an integer in the range from 1 to about 50; m represents an integer in the range from 2 to about 4 and, when n=1, Y and M may be the same as X.

Claim 21

A composition of matter resistant to degradation by ultraviolet light comprising an organic material subject to ultraviolet light degradation 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 ##STR82## wherein (PIP-T) is represented by the residue of ##STR83## wherein, n is an integer in the range from 1 to about 10, said compound having functional end groups selected from H, OH and Cl when n is greater than 1; X is a substituent having the following formula (II): ##STR84## wherein, R 2 , R 3 , R 4 and R 5 independently represent C 1 -C 24 alkyl and polymethylene having from 4 to about 7 C atoms which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperazinone ring, R 1 represents hydrogen or oxygen, C 1 -C 24 alkyl, C 1 -C 12 hydroxyalkyl, benzyl, allyl, and C 1 -C 12 halcalkyl; R 8 and R 9 independently represent C 1 -C 24 alkyl, and polymethylene having from 4 to about 7 C atoms which are cyclizable; R 10 represents H, C 1 -C 6 alkyl and phenyl; Y may be the same as X or M; M may be Z or Z', wherein Z represents a radical selected from the group consisting of Cl, OH, ##STR85## R 6 , R 7 represent alkyl having from 2 to about 24 carbon atoms; and C 4 -C 7 cycloalkyl; Ar represents aryl; Z' represents a radical selected from the group consisting of ##STR86## p represents an integer in the range from 2 to about 20; x represents an integer in the range from 1 to about 50; m represents an integer in the range from 2 to about 4 and, when n=1, Y and M may be the same as X.

Claim 22

The composition of claim 17 wherein said residue has the structural formula ##STR87## wherein, X is a residue of a polysubstituted piperazinone ("PSP") said "PSP" residue having a structure selected from the group consisting of ##STR88## M is selected from the group consisting of ##STR89## and, M may be the same as X.

Claim 23

The composition of claim 18 wherein said stabilizer compound is identified as 1,1'-[[[4-(cyclohexylamino)-6-[[1,1-dimethyl-2-(3,3,5,5-tetramethyl-2-oxo-1-piperazinyl)ethyl]amino]-1,3,5-triazin-2-yl]imino]bis[2,1-ethanediylimino[6-(cyclohexylamino)-1,3,5-triazine-4,2-diyl]imino(2,2-dimethyl-2,1-ethanediyl]]bis[3,3,5,5-tetramethylpiperazinone].

Claim 24

A process for preparing a branched bridge polysubstituted piperazinone ("PSP") having the structure ##STR90## wherein, R 2 , R 3 , R 4 and R 5 independently represent C 1 -C 24 alkyl and polymethylene having from 4 to about 7 C atoms which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperazinone ring, R 1 represents hydrogen or oxygen, C 1 -C 24 alkyl, C 1 -C 12 hydroxyalkyl, benzyl, allyl, and C 1 -C 12 haloalkyl; R 8 and R 9 independently represent C 1 -C 24 alkyl, and polymethylene having from 4 to about 7 C atoms which are cyclizable; R 10 represents H, C 1 -C 6 alkyl and phenyl; comprising, contacting a polyalkyleneamine having terminal free primary amine groups, represented by the structure ##STR91## wherein, R 4 , R 5 , R 8 , R 9 and R 10 have the same connotation as that set forth above; with sufficient amounts of chloroform and a ketone, optionally in the presence of a phase transfer catalyst, at a temperature in the range from about -10° C. to about 30° C., to yield said PSP.

Claim 25

A process for preparing a branched bridge polysubstituted piperazinone ("PSP") having the structure ##STR90## wherein, R 2 , R 3 , R 4 and R 5 independently represent C 1 -C 24 alkyl and polymethylene having from 4 to about 7 C atoms which are cyclizable forming a spiro cycloalkylene substituent with the C atom of the piperazinone ring, R 1 represents hydrogen or oxygen, C 1 -C 24 alkyl, C 1 -C 12 hydroxyalkyl, benzyl, allyl, and C 1 -C 12 haloalkyl; R 8 and R 9 independently represent C 1 -C 24 alkyl, and polymethylene having from 4 to about 7 C atoms which are cyclizable; R 10 represents H, C 1 -C 6 alkyl and phenyl; comprising, contacting a polyalkyleneamine having terminal free primary amine groups, represented by the structure ##STR91## wherein, R 4 , R 5 , R 8 , R 9 and R 10 have the same connotation as that set forth above; with sufficient amounts of chloroform and a ketone, optionally in the presence of a phase transfer catalyst, at a temperature in the range from about -10° C. to about 30° C., to yield said PSP.