Modified piperidines as ultraviolet light stabilizers

Claim 2

A composition of matter which comprises a material formed from the reaction of: (a) a methylol or alkoxy alkyl-containing material, and (b) an alkyl substituted piperidine-containing material having at least one group selected from hydroxyl, carboxyl, amido, and ureido.

Claim 3

The composition of Claim 1 wherein the methylol or alkoxy alkyl-containing material is represented by the structural formula wherein Y is a radical derived from a material capable of reacting with formaldehyde to form at least one methylol group; and R is hydrogen, C 1 to C 6 alkyl, or C 6 to C 18 aryl; and R 10 is hydrogen or methyl.

Claim 4

The composition of Claim 2 wherein Y is a radical derived from a material selected from the group consisting of amino substituted 0 triazines, ureas, glycolurils, phenols, and amides of the formula R-C-NHR' wherein R' is hydrogen or C 1 to C 12 alkyl and R is an aliphatic, cycloaliphatic, or olefinic radical, or an acrylic polymeric moiety.

Claim 5

The composition of Claim 3 wherein Y is derived from melamine or benzoguanamine.

Claim 6

The composition of Claim 3 wherein Y is derived from urea.

Claim 7

The composition of Claim 3 wherein Y is derived from glcpluril.

Claim 8

The composition of Claim 1 wherein the alkyl substituted piperidine-containing material having at least one group selected from hydroxyl, carboxyl, amido, and ureido is represented by the following structural formula: wherein B is oxygen or wherein R 11 is hydrogen, C 1 to C 4 alkyl, -(A)y-H, or R 1 , R 2 , R 3 , R 4 are the same or different C 1 to C 6 alkyl, and R 1 and R 2 when joined together form a C 3 to C 12 cycloaliphatic ring; R 5 is hydrogen or methyl; A is or wherein R 9 and R 12 are independently hydrogen or C 1 to C 10 alkyl; m is an integer from 1 to 10; p is an integer from 1 to 5; r is an integer from 2 R 11 to 3; and y is 0 or 1 with the proviso that when B is - N -, y is 1.

Claim 9

The composition of Claim 7 wherein N is substituted with R 6 wherein R 6 is hydrogen, 0, C 1 to C 12 alkyl, hydroxyl, C 2 to C 18 alkenyl or alkynyl, C 7 to C 18 aralkyl, acyl, carbamoyl, benzyl, or a group wherein R 7 is hydrogen, methyl, ethyl, phenyl, or CH 2 OR 8 , q is an integer from 1 to 3 and w is an integer from 1 to 10 and Rg is C 1 to C 6 alkyl or phenyl.

Claim 10

A composition of matter which comprises a material having the following structural formula: wherein: Y is a radical derived from a material which is capable of reacting with formaldehyde to form methylol groups; R 1 , R 2 , R 3 , R 4 are the same or different C 1 to C 6 alkyl; and R 1 and R 2 when joined together form a C 3 to C 12 cycloaliphatic ring; R 5 is hydrogen or methyl; R 10 is hydrogen or methyl; B is oxygen or wherein R 11 is hydrogen, C 1 to C 4 alkyl, -(A)y-H, or A is or wherein Rg and R 12 are independently hydrogen or C 1 to C 10 alkyl; m is an integer from 1 to 10; p is an integer from 1 to 5; r is an integer from 2 to 3; n is an integer from 1 to 6; and y is 0 or 1, with the proviso that when B is y is 1.

Claim 11

A composition of matter which comprises a material having the following structural formula: wherein: Y is a radical derived from a material which is capable of reacting with formaldehyde to form methylol groups; R 1 , R 2 , R 3 , R 4 are the same or different C 1 to C 6 alkyl; and R 1 and R 2 when joined together form a C 3 to C 12 cycloaliphatic ring; R 5 is hydrogen or methyl; R 10 is hydrogen or methyl; B is oxygen or wherein R 11 is hydrogen, C 1 to C 4 alkyl, -(A)y-H, or A is or wherein Rg and R 12 are independently hydrogen or C 1 to C 10 alkyl; m is an integer from 1 to 10; p is an integer from 1 to 5; r is an integer from 2 to 3; n is an integer from 1 to 6; and y is 0 or 1, with the proviso that when B is y is 1.

Claim 12

The composition of Claim 9 wherein N is substituted with R 6 wherein R 6 is hydrogen, 0, C 1 to C 12 alkyl, hydroxyl, C 2 to C 18 alkenyl or alkynyl, C 7 to C 18 aralkyl, acyl, carbamoyl, benzyl, or a group wherein R 7 is hydrogen, methyl, ethyl, phenyl, or CH 2 OR 8 , q is an integer from 1 to 3 and w is an integer from 1 to 10, and Rg is C 1 to C 6 alkyl or phenyl.

Claim 13

The composition of Claim 10 wherein R 1 , R 2 , R 3 , R 4 are each methyl, R 5 is hydrogen, R 6 is methyl and B is oxygen.

Claim 14

The composition of Claim 10 wherein R 1 , R 2 , R 3 , R 4 are each methyl, R 5 is hydrogen, R 6 is hydrogen, and B is oxygen.

Claim 15

The composition of Claim 10 wherein Y is a radical derived from a material selected from the group consisting of amino substituted 0 triazines, ureas, glycolurils, phenols, and amides of the formula R-C-NHR' wherein R' is hydrogen or C 1 to C 12 alkyl and R is an aliphatic, cycloaliphatic, or olefinic radical or an acrylic polymeric moiety.

Claim 16

The composition of Claim 13 wherein Y is a radical derived from melamine or benzoguanamine.

Claim 17

The composition of Claim 13 wherein Y is derived from urea.

Claim 18

The composition of Claim 13 wherein Y is derived from glycoluril.

Claim 19

A process for the preparation of a hindered amine stabilizer, comprising: contacting a methylol or alkoxy alkyl containing material with an alkyl substituted piperidine-containing material of the structure: under conditions sufficient to transetherify and eliminate water or alcohol, thereby forming a hindered amine stabilizer having the following structural formula: wherein: Y is a radical derived from a material which is capable of reacting with formaldehyde to form methylol groups; R 1 , R 2 , R 3 , R 4 are the same or different C 1 to C 6 alkyl, and R 1 and R 2 when joined together form a C 3 to C 12 cycloaliphatic ring; R 5 is hydrogen or methyl; R 10 is hydrogen or methyl; B is oxygen or wherein R 11 is hydrogen, C 1 to C4 alkyl, -(A)y-H, or A is or wherein R 9 and R 12 are independently hydrogen or C 1 to C 10 alkyl; m is an integer from 1 to 10; p is an integer from 1 to 5; r is an integer from 2 to 3; n is an integer from 1 to 6; and y is 0 or 1, with the proviso that when B is y is 1.

Claim 20

A process for the preparation of a hindered amine stabilizer, comprising: contacting a methylol or alkoxy alkyl containing material with an alkyl substituted piperidine-containing material of the structure: under conditions sufficient to transetherify and eliminate water or alcohol, thereby forming a hindered amine stabilizer having the following structural formula: wherein: Y is a radical derived from a material which is capable of reacting with formaldehyde to form methylol groups; R 1 , R 2 , R 3 , R 4 are the same or different C 1 to C 6 alkyl, and R 1 and R 2 when joined together form a C 3 to C 12 cycloaliphatic ring; R 5 is hydrogen or methyl; R 10 is hydrogen or methyl; B is oxygen or wherein R 11 is hydrogen, C 1 to C4 alkyl, -(A)y-H, or A is or wherein R 9 and R 12 are independently hydrogen or C 1 to C 10 alkyl; m is an integer from 1 to 10; p is an integer from 1 to 5; r is an integer from 2 to 3; n is an integer from 1 to 6; and y is 0 or 1, with the proviso that when B is y is 1.

Claim 21

The process of Claim 17 wherein the methylol or alkoxy alkyl-containing material is represented by the following structure: wherein Y is a radical derived from a material capable of reacting with formaldehyde to form at least one methylol group; and R is hydrogen, C 1 to C 6 alkyl, or C 6 to C 18 aryl; and R 10 is hydrogen or methyl.

Claim 22

The process of Claim 17 wherein Y is a radical derived from a material selected from the group consisting of amino substituted triazines, ureas, glycolurils, phenols and amides of the formula 1 wherein R' is hydrogen or C 1 to C 12 alkyl and R is an aliphatic, cycloaliphatic, or olefinic radical, or an acrylic polymeric moiety.

Claim 23

The process of Claim 17 wherein the alkyl substituted piperidine-containing material has the following structure and is a component of a reaction mixture prepared by a method which comprises contacting an ester having at least one group of the structure: with a polyol or amino alcohol under conditions sufficient or cobodyse or aminolyze the ester and form the reaction mixture; wherein R 1 , R 2 , R 3 , R 4 are the same or different C 1 to C 6 alkyl; and R 5 is hydrogen or methyl.

Claim 24

The process of Claim 17 wherein the hindered amine stabilizer which is formed has the following structural formula: wherein Y is a radical derived from a material which is capable of reacting with formaldehyde to form methylol groups; R 1 , R 2 , R 3 , R 4 are the same or different C 1 to C 6 alkyl, and R 1 and R 2 when joined together form a C 3 to C 12 cycloaliphatic ring; R 5 is hydrogen or methyl; R 10 is hydrogen or methyl; B is oxygen or wherein R 11 is hydrogen, C 1 to C 4 alkyl, -(A)y-H, or A is or wherein Rg and R 12 are independently hydrogen or c 1 to C 10 alkyl; m is an integer from 1 to 10; p is an integer from 1 to 5; r is an integer from 2 to 3; n is an integer from 1 to 6; and y is 0 or 1, with the proviso that when B is y is 1.

Claim 25

The process of Claim 20 wherein the ester is represented by the following structural formula: wherein R is alkylene, alkenylene, alkynlene, arylene, or phenylene.

Claim 26

In a thermosetting resinous composition comprising an active hydrogen-containing material and a curing agent reactive with the active hydrogens to form a cured product, the improvement comprising including in the composition a hindered amine of the structure: wherein: Y is a radical derived from a material which is capable of reacting with formaldehyde to form methylol groups; R 1 , R 2 , R 3 , R 4 are the same or different C 1 to C 6 alkyl; and R 1 and R 2 when joined together form a C 3 to C 12 cycloaliphatic ring; R 5 is hydrogen or methyl; x 10 is hydrogen or methyl; B is oxygen or wherein R 11 is hydrogen, C 1 to C 4 alkyl, -(A)y-H, or A is or wherein R 9 and R 12 are independently hydrogen or C 1 to C 10 alkyl; m is an integer from 1 to 10; p is an integer from 1 to 5; r is an integer from 2 to 3; n is an integer from 1 to 6; and y is 0 or 1, with the proviso that when B is y is 1.

Claim 27

In a thermosetting resinous composition comprising an active hydrogen-containing material and a curing agent reactive with the active hydrogens to form a cured product, the improvement comprising including in the composition a hindered amine of the structure: wherein: Y is a radical derived from a material which is capable of reacting with formaldehyde to form methylol groups; R 1 , R 2 , R 3 , R 4 are the same or different C 1 to C 6 alkyl; and R 1 and R 2 when joined together form a C 3 to C 12 cycloaliphatic ring; R 5 is hydrogen or methyl; x 10 is hydrogen or methyl; B is oxygen or wherein R 11 is hydrogen, C 1 to C 4 alkyl, -(A)y-H, or A is or wherein R 9 and R 12 are independently hydrogen or C 1 to C 10 alkyl; m is an integer from 1 to 10; p is an integer from 1 to 5; r is an integer from 2 to 3; n is an integer from 1 to 6; and y is 0 or 1, with the proviso that when B is y is 1.

Claim 28

The composition of Claim 27 wherein N is substituted with R 6 wherein R 6 is hydrogen, 0, C 1 to C 12 alkyl, hydroxyl, C 2 to C 18 alkenyl or alkynyl, C 7 to C 18 aralkyl, acyl, carbamoyl, benzyl, or a group wherein R 7 is hydrogen, methyl, ethyl, phenyl, or CH 2 OR 8 , q is an integer from from 1 to 3 and w is an integer from 1 to 10, and Rg is C 1 to C 6 alkyl or phenyl.

Claim 29

The composition of Claim 23 wherein the hindered amine is present in an amount ranging from 0.1 to 5 percent by weight based on the resinous components of the composition.