Stabilized polyester compositions suitable for outdoor applications

Claim 2

A polyester composition having a 264 psi heat deflection temperature greater than 60° C. comprising A. a dicarboxylic acid component wherein at least a major portion of which is 1,4-cyclohexanedicarboxylic acid having a trans isomer content of at least 65%, B. a glycol component, wherein at least a major portion of which is 2,2,4,4-tetramethyl-1,3-cyclobutanediol, C. a stabilizing effective amount of the combination of 1. at least one ultraviolet light stabilizing compound compatible with said polyester, and 2. at least one hindered amine light stabilizing compound having the formulae ##STR4## wherein m and n are each integers of from 1 to 20, R 1 , R 2 , R 3 and R 4 are each independently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, aryl having 6 to 22 carbon atoms, alkylene having 1 to 20 carbon atoms, cycloalkylene having 3 to 12 carbon atoms, hydroxyalkyl having 1 to 18 carbon atoms, and esters of said hydroxyalkyl; and alkylenecarboxylic acid having 2 to 18 carbon atoms and esters, amides and metal salts of said alkylenecarboxylic acid.

Claim 3

A polyester composition according to claim 1 wherein at least one of said hindered amine light stabilizing compounds is employed in an amount of about 0.05 to about 2.0 weight percent and at least one of said ultraviolet light stabilizing compounds is employed in an amount of about 0.05 to about 5.0 weight percent, based on the weight of said polyester.

Claim 4

A polyester composition according to claim 2 wherein said ultraviolet light stabilizing compound is selected from the group consisting of a compound having the formula ##STR5## wherein R 5 , R 6 , and R 7 are each independently selected from hydrogen, hydroxyl, branched or unbranched, substituted or unsubstituted alkyl or alkoxy radicals containing from 1 to 18 carbon atoms, aryl, and alkylenearyl containing from 7 to 22 carbon atoms; R 7 is also chlorine or fluorine; a compound having the formula ##STR6## wherein R 8 , R 9 and R 10 are each independently selected from hydrogen, branched or unbranched, substituted or unsubstituted alkyl having 1 to 18 carbon atoms, and alkylenecarbonyloxyalkyl having 3 to 18 carbon atoms; a compound having the formula ##STR7## wherein R 11 , R 12 and R 13 are each independently selected from hydrogen and substituted or unsubstituted, branched or unbranched alkyl radicals containing from 1 to 10 carbon atoms; a compound of the formula ##STR8## wherein R 14 and R 16 are each independently selected from substituted or unsubstituted alkyl containing from 1 to 18 carbon atoms, R 15 is hydrogen, methyl, or substituted or unsubstituted aryl having 6 to 22 carbon atoms, and R 16 is also substituted or unsubstituted alkoxy having 1 to 18 carbon atoms; a compound having the formula ##STR9## wherein R 17 and R 18 are each independently selected from substituted or unsubstituted, branched or unbranched alkyl having 1 to 18 carbon atoms and R 19 is hydrogen or methyl; a compound having the formula ##STR10## wherein R 20 is hydrogen, substituted or unsubstituted branched or unbranched alkyl or alkoxy having 1 to 18 carbon atoms.

Claim 5

A polyester composition according to claim 3 wherein said hindered amine light stabilizing compound is selected from the group consisting of bis(1,2,2,6,6-pentamethyl-4-piperidinyl)sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidinyl)2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-2-butylpropanedioate, dimethylsuccinate polymer with 4-hydroxy-2,2,6,6-tetramethyl-1-piperdine-ethanol, and poly[(2,2,6,6-tetramethyl-4-piperidinyl)iminomethylene-2,2,6,6-tetramethyl-4-piperdinyl)imino[6-(octylamino)-1,3,5-triazine-4,2-diyl]]; and said ultraviolet light stabilizing compound is selected from the group consisting of 2-[2-hydroxy-3,5-di(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole, 2-ethoxy-2'-ethyloxanilide, and 2-ethylhexyl-2-cyano-3,3-diphenylacrylate.

Claim 6

A polyester composition according to claim 4 wherein said glycol component comprises about 70-100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol, and about 30-0 mole % of a second glycol selected from the group consisting of polymethylene glycols having about 2 to about 10 carbon atoms.

Claim 7

A polyester composition according to claim 5 wherein said second glycol is selected from the group consisting of 1,3-propanediol; 2,2-dimethyl-1,3-propanediol; 1,4-butanediol, 1,6-hexanediol; 1,4-cyclohexanedimethanol; and 1,4-cyclohexanediol.

Claim 8

A polyester composition according to claim 6 wherein said acid component comprises about 80-100 mole % 1,4-cyclohexanedicarboxylic acid and about 20-0 mole % of a second acid selected from the group consisting of aliphatic dicarboxylic acids having about 2 to about 10 carbon atoms.

Claim 9

A polyester composition according to claim 7 wherein said second acid is selected from the group consisting of malonic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, and sebacic acid.

Claim 10

A polyester composition according to claim 1 wherein said acid component comprises about 80-100 mole % 1,4-cyclohexanedicarboxylic acid and about 20-0 mole % of a second acid selected from the group consisting of aliphatic dicarboxylic acids having about 2 to about 10 carbon atoms and said glycol component comprises about 70-100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol, and about 30-0 mole % of a second glycol selected from the group consisting of polymethylene glycols having about 2 to about 10 carbon atoms.

Claim 11

A polyester composition according to claim 5 wherein 1,4-cyclohexanedicarboxylic acid has a 100% trans isomer content.

Claim 12

A polyester composition having an inherent viscosity of at least 0.4 and a 264 psi heat deflection temperature greater than 60° C. comprising A. a dicarboxylic acid component wherein at least a major portion of which is 1,4-cyclohexanedicarboxylic acid having a trans isomer content of at least 65%, B. a glycol component wherein at least a major portion of which is 2,2,4,4-tetramethyl-1,3-cyclobutanediol, and C. a stabilizing effective amount of the combination of 1. at least one hindered amine light stabilizing compound having the formulae ##STR11## wherein m and n are each integers of from 1 to 20, R 1 , R 2 , R 3 and R 4 are each independently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, aryl having 6 to 22 carbon atoms, alkylene having 1 to 20 carbon atoms, cycloalkylene having 3 to 12 carbon atoms, hydroxyalkyl having 1 to 18 carbon atoms, and esters of said hydroxyalkyl; and alkylenecarboxylic acid having 2 to 18 carbon atoms and esters, amides and metal salts of said alkylenecarboxylic acid;

Claim 13

A polyester composition having an inherent viscosity of at least 0.4 and a 264 psi heat deflection temperature greater than 60° C. comprising A. a dicarboxylic acid component wherein at least a major portion of which is 1,4-cyclohexanedicarboxylic acid having a trans isomer content of at least 65%, B. a glycol component wherein at least a major portion of which is 2,2,4,4-tetramethyl-1,3-cyclobutanediol, and C. a stabilizing effective amount of the combination of 1. at least one hindered amine light stabilizing compound having the formulae ##STR11## wherein m and n are each integers of from 1 to 20, R 1 , R 2 , R 3 and R 4 are each independently selected from hydrogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, aryl having 6 to 22 carbon atoms, alkylene having 1 to 20 carbon atoms, cycloalkylene having 3 to 12 carbon atoms, hydroxyalkyl having 1 to 18 carbon atoms, and esters of said hydroxyalkyl; and alkylenecarboxylic acid having 2 to 18 carbon atoms and esters, amides and metal salts of said alkylenecarboxylic acid;

Claim 14

at least one ultraviolet light stabilizing compound selected from the group consisting of a compound having the formula ##STR12## wherein R 5 , R 6 , and R 7 are each independently selected from hydrogen, hydroxyl, branched or unbranched, substituted or unsubstituted alkyl or alkoxy radicals containing from 1 to 18 carbon atoms, aryl, and alkylenearyl containing from 7 to 22 carbon atoms; and R 7 is also chlorine or fluorine; a compound having the formula ##STR13## wherein R 8 , R 9 and R 10 are each independently selected from hydrogen, branched or unbranched, substituted or unsubstituted alkyl having 1 to 18 carbon atoms, and alkylenecarbonyloxyalkyl having 3 to 18 carbon atoms; a compound having the formula ##STR14## wherein R 11 , R 12 and R 13 are each independently selected from hydrogen and substituted or unsubstituted, branched or unbranched alkyl radicals containing from 1 to 10 carbon atoms; a compound of the formula ##STR15## wherein R 14 and R 16 are each independently selected from substituted or unsubstituted alkyl containing from 1 to 18 carbon atoms, R 15 is hydrogen, methyl, or substituted or unsubstituted aryl having 6 to 22 carbon atoms, and R 16 is also substituted or unsubstituted alkoxy having 1 to 18 carbon atoms; a compound having the formula ##STR16## wherein R 17 and R 18 are each independently selected from substituted or unsubstituted, branched or unbranched alkyl having 1 to 18 carbon atoms and R 19 is hydrogen or methyl; a compound having the formula ##STR17## wherein R 20 is hydrogen, substituted or unsubstituted branched or unbranched alkyl or alkoxy having 1 to 18 carbon atoms.

Claim 15

at least one ultraviolet light stabilizing compound selected from the group consisting of a compound having the formula ##STR12## wherein R 5 , R 6 , and R 7 are each independently selected from hydrogen, hydroxyl, branched or unbranched, substituted or unsubstituted alkyl or alkoxy radicals containing from 1 to 18 carbon atoms, aryl, and alkylenearyl containing from 7 to 22 carbon atoms; and R 7 is also chlorine or fluorine; a compound having the formula ##STR13## wherein R 8 , R 9 and R 10 are each independently selected from hydrogen, branched or unbranched, substituted or unsubstituted alkyl having 1 to 18 carbon atoms, and alkylenecarbonyloxyalkyl having 3 to 18 carbon atoms; a compound having the formula ##STR14## wherein R 11 , R 12 and R 13 are each independently selected from hydrogen and substituted or unsubstituted, branched or unbranched alkyl radicals containing from 1 to 10 carbon atoms; a compound of the formula ##STR15## wherein R 14 and R 16 are each independently selected from substituted or unsubstituted alkyl containing from 1 to 18 carbon atoms, R 15 is hydrogen, methyl, or substituted or unsubstituted aryl having 6 to 22 carbon atoms, and R 16 is also substituted or unsubstituted alkoxy having 1 to 18 carbon atoms; a compound having the formula ##STR16## wherein R 17 and R 18 are each independently selected from substituted or unsubstituted, branched or unbranched alkyl having 1 to 18 carbon atoms and R 19 is hydrogen or methyl; a compound having the formula ##STR17## wherein R 20 is hydrogen, substituted or unsubstituted branched or unbranched alkyl or alkoxy having 1 to 18 carbon atoms.

Claim 16

A polyester composition according to claim 11 wherein at least one of said hindered amine light stabilizing compounds is employed in an amount of about 0.05 to about 2.0 weight percent and at least one of said ultraviolet light stabilizing compounds is employed in an amount of about 0.05 to about 5.0 weight percent, based on the weight of said polyester.

Claim 17

A polyester composition according to claim 11 wherein said hindered amine light stabilizing compound is selected from the group consisting of bis(1,2,2,6,6-pentamethyl-4-piperidinyl)sebacate, bis(1,2,2,6,6-pentamethyl-4-piperidinyl)2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methyl]-2-butylpropanedioate, dimethylsuccinate polymer with 4-hydroxy-2,2,6,6-tetramethyl-1-piperdine-ethanol, and poly[(2,2,6,6-tetramethyl-4-piperidinyl)iminomethylene2,2,6,6-tetra-methyl-4-piperidinyl)imino[6-(octylamino)-1,3,5-triazine-4,2-diyl]]; and said ultraviolet light stabilizing compound is selected from the group consisting of 2-[2-hydroxy-3,5-di(α,α-dimethylbenzyl)phenyl]-2H-benzotriazole, 2-ethoxy-2'-ethyloxanilide, and 2-ethylhexyl-2-cyano-3,3-diphenylacrylate.

Claim 18

A polyester composition according to claim 11 wherein said glycol component comprises about 70-100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol, and about 30-0 mole % of a second glycol selected from the group consisting of polymethylene glycols having about 2 to about 10 carbon atoms.

Claim 19

A polyester composition according to claim 11 wherein said acid component comprises about 80-100 mole % 1,4-cyclohexanedicarboxylic acid and about 20-0 mole % of a second acid selected from the group consisting of aliphatic dicarboxylic acids having about 2 to about 10 carbon atoms.

Claim 20

A polyester composition according to claim 11 wherein said acid component comprises about 80-100 mole % 1,4-cyclohexanedicarboxylic acid and about 20-0 mole % of a second acid selected from the group consisting of aliphatic dicarboxylic acids having about 2 to about 10 carbon atoms and said glycol component comprises about 70-100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol, and about 30-0 mole % of a second glycol selected from the group consisting of polymethylene glycols having about 2 to about 10 carbon atoms.

Claim 21

A polyester composition according to claim 11 wherein 1,4-cyclohexanedicarboxylic acid has a 100% trans isomer content.

Claim 22

A polyester composition according to claim 11 wherein said inherent viscosity is at least 0.6 to about 1.6.

Claim 23

A polyester composition having an inherent viscosity of at least 0.4 and a 264 psi heat deflection temperature greater than 60° C. comprising A. a dicarboxylic acid component wherein at least a major portion of which is 1,4-cyclohexanedicarboxylic acid having a trans isomer content of at least 65%, B. a glycol component wherein at least a major portion of which is 2,2,4,4-tetramethyl-1,3-cyclobutanediol, C. the combination of about 0.25 to about 0.5 weight percent of a polyester of succinic acid and (N-β-hydroxyethyl-2,2,6,6-tetramethyl-4-hydroxypiperidine, and about 0.5 to about 1.0 weight percent of 2-ethoxy-2'-ethyloxanilide.

Claim 24

A polyester composition having an inherent viscosity of at least 0.4 and a 264 psi heat deflection temperature greater than 60° C. comprising A. a dicarboxylic acid component wherein at least a major portion of which is 1,4-cyclohexanedicarboxylic acid having a trans isomer content of at least 65%, B. a glycol component wherein at least a major portion of which is 2,2,4,4-tetramethyl-1,3-cyclobutanediol, C. the combination of about 0.25 to about 0.5 weight percent of a polyester of succinic acid and (N-β-hydroxyethyl-2,2,6,6-tetramethyl-4-hydroxypiperidine, and about 0.5 to about 1.0 weight percent of 2-ethoxy-2'-ethyloxanilide.

Claim 25

A polyester composition according to claim 19 wherein said glycol component comprises about 70-100 mole % 2,2,4,4-tetramethyl-1,3-cyclobutanediol and about 30-0 mole % 1,4-cyclohexanedimethanol, based on a total glycol content of 100 mole %.

Claim 26

A polyester composition according to claim 20 wherein 1,4-cyclohexanedimethanol has a trans isomer content of about 70%.

Claim 27

An article of manufacture produced from the polyester according to claim 1.

Claim 28

An article of manufacture produced from the polyester according to claim 11.

Claim 29

An article of manufacture produced from the polyester according to claim 19.