Biheterocyclic ultraviolet stabilizers and their use in organic compositions

Claim 2

A composition of matter comprising biheterocyclic compounds having the formula: A--B--C wherein A is a group having the formula: ##STR8## wherein X is a carbon atom or a nitrogen atom; Z is an oxygen atom, a sulfur atom, a nitrogen atom, or a nitrogen atom containing a hydrogen atom or a lower alkyl group containing 1 to 12 carbon atoms; R 1 , R 2 , R 3 and R 4 are hydrogen, lower alkyl, cyclohexyl, phenyl, lower alkyl phenyl, phenyl-substituted-phenyl, chloro, bromo, lower alkoxy, lower alkyl substituted amino, cyano, and the substituents R 1 and R 2 , R 2 and R 3 , and R 3 and R 4 , combined with the carbon atoms to which they are attached, are joined lower alkylene groups completing a carbocyclic ring, which ring can also be substituted with one or more of the substituents listed above for R 1 , R 2 , R 3 and R 4 ; wherein B is a linking group connecting A and C and can be carbonyloxy, oxycarbonylalkyleneoxy, oxycarbonyl, alkyleneoxycarbonyloxy, oxyalkylenecarbonyl, oxycarbonyloxy, alkyleneoxy, oxyalkylene, alkyleneoxyalkyleneoxy, thio, thioalkyleneoxy, sulfinyldioxy, oxy(alkoxy)phosphinooxy, alkyloxyphosphinylidene, aryloxyphosphinylidene, oxy(alkyl)phosphinyloxy, aminocarbonyl, N-alkylaminocarbonyl, N-arylaminocarbonyl, aminocarbonylalkyleneoxy, N-alkylaminocarbonylalkyleneoxy, N-arylaminocarbonylalkyleneoxy, aminocarbonylamino, N-alkylaminocarbonylamino, N,N-dialkylaminocarbonyl, N,N-diarylaminocarbonyl, N-alkylaminoalkyleneoxy, N-arylaminoalkyleneoxy, oxyalkyleneoxy, oxyaryleneoxy, alkyleneaminoalkylene, aryleneaminoarylene, aryleneaminoalkylene and alkyleneaminoarylene; with the proviso that in the above definitions of B, alkyl indicates loweralkyl, alkylene indicates lower alkylene, alkoxy indicates lower alkoxy, aryl indicates phenyl, naphthyl or lower alkyl substituted phenyl or naphthyl and arylene indicates phenylene or naphthylene; and wherein C is a group having the formula ##STR9## R 5 and R 6 are each alkyl having 1-6 carbons; R 7 and R 8 are each alkyl having 1-6 carbons or together with the carbon to which they are bound form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; and R 9 is hydrogen, oxy, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or lower alkyl substituted benzyl.

Claim 3

A composition of matter according to claim 1 wherein X is a carbon atom.

Claim 4

A composition of matter according to claim 1 wherein X is a nitrogen atom.

Claim 5

A composition of matter according to claim 2 wherein Z is a nitrogen atom.

Claim 6

A composition of matter according to claim 3 wherein Z is a sulfur atom.

Claim 7

A composition of matter according to claim 3 wherein Z is a nitrogen atom.

Claim 8

A composition of matter according to claim 3 wherein Z is a nitrogen atom containing hydrogen or a lower alkyl group containing 1 to 12 carbon atoms.

Claim 9

A composition of matter according to claim 3 wherein Z is an oxygen atom.

Claim 10

A composition of matter according to claim 8 having the formula: ##STR10## wherein E is a member selected from the group consisting of a branched or unbranched alkylene group containing 1 to 8 carbon atoms, carbonyl lower alkylene, lower alkylenecarbonyl; R 1 , R 2 , R 3 and R 4 are hydrogen, hydroxy, chloro, bromo, lower alkyl, cyclohexyl, phenyl, lower alkyl phenyl, lower alkoxy, amino, lower alkyl substituted amino, cyano, carboxy and the substituents R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , combined with the carbon atoms to which they are attached, are joined lower alkylene groups completing a carbocyclic ring, which ring can also be substituted with one or more of the substituents listed above for R 1 , R 2 , R 3 and R 4 ; R 5 and R 6 are each alkyl having 1-6 carbons; R 7 and R 8 are each alkyl having 1-6 carbons or together with the carbon to which they are bound form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; and R 9 is hydrogen, oxy, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 to 4 carbon atoms, propargyl, benzyl or lower alkyl substituted benzyl.

Claim 11

A composition of matter according to claim 1 having the formula: ##STR11##

Claim 12

A composition of matter according to claim 1 having the formula: ##STR12##

Claim 13

A composition of matter according to claim 1 having the formula: ##STR13##

Claim 14

A composition of matter according to claim 1 having the formula: ##STR14##

Claim 15

An organic composition susceptible to ultraviolet light degradation stabilized against such degradation with a stabilizing amount of at least one biheterocyclic compound having the formula: A--B--C wherein A is a group having the structure ##STR15## wherein X is a carbon atom or a nitrogen atom; Z is an oxygen atom, a sulfur atom, a nitrogen atom, or a nitrogen atom containing a hydrogen atom or a lower alkyl group containing 1 to 12 carbon atoms; R 1 , R 2 , R 3 and R 4 are hydrogen, lower alkyl, cyclohexyl, phenyl, lower alkyl phenyl, phenyl-substituted-phenyl, chloro, bromo, lower alkoxy, lower alkyl substituted amino, cyano, and the substituents R 1 and R 2 , R 2 and R 3 , and R 3 and R 4 , combined with the carbon atoms to which they are attached, are joined lower alkylene groups completing a carbocyclic ring, which ring can also be substituted with one or more of the substituents listed above for R 1 , R 2 , R 3 and R 4 ; B is a linking group connecting A and C and can be alkylene, arylene, carbonyloxy, oxycarbonylalkyleneoxy, oxycarbonyl, alkyleneoxycarbonyloxy, oxyalkylenecarbonyl, oxycarbonyloxy, alkyleneoxy, oxyalkylene, alkyleneoxyalkyleneoxy, thio, thioalkyleneoxy, sulfinyldioxy, oxy(alkoxy)phosphinooxy, alkyloxyphosphinylidene, aryloxyphosphinylidene, oxy(alkyl)phosphinyloxy, aminocarbonyl, N-alkylaminocarbonyl, N-arylaminocarbonyl, aminocarbonylalkyleneoxy, N-alkylaminocarbonylalkyleneoxy, N-arylaminocarbonylalkyleneoxy, aminocarbonylamino, N-alkylaminocarbonylamino, N,N-dialkylaminocarbonyl, N,N-diarylaminocarbonyl, N-alkylaminoalkyleneoxy, N-arylaminoalkyleneoxy, oxyalkyleneoxy, oxyaryleneoxy, alkyleneaminoalkylene, aryleneaminoarylene, aryleneaminoalkylene and alkyleneaminoarylene; with the proviso that in the above definitions of B, alkyl indicates loweralkyl, alkylene indicates lower alkylene, alkoxy indicates lower alkoxy, aryl indicates phenyl, naphthyl or lower substituted phenyl or naphthyl and arylene indicates phenylene or naphthylene; and wherein C is a group having the formula ##STR16## R 5 and R 6 are each alkyl having 1-6 carbons; R 7 and R 8 are each alkyl having 1-6 carbons or together with the carbon to which they are bound form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; and R 9 is hydrogen, oxy, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or lower alkyl substituted benzyl.

Claim 16

An organic composition susceptible to ultraviolet light degradation stabilized against such degradation with a stabilizing amount of at least one biheterocyclic compound having the formula: A--B--C wherein A is a group having the structure ##STR15## wherein X is a carbon atom or a nitrogen atom; Z is an oxygen atom, a sulfur atom, a nitrogen atom, or a nitrogen atom containing a hydrogen atom or a lower alkyl group containing 1 to 12 carbon atoms; R 1 , R 2 , R 3 and R 4 are hydrogen, lower alkyl, cyclohexyl, phenyl, lower alkyl phenyl, phenyl-substituted-phenyl, chloro, bromo, lower alkoxy, lower alkyl substituted amino, cyano, and the substituents R 1 and R 2 , R 2 and R 3 , and R 3 and R 4 , combined with the carbon atoms to which they are attached, are joined lower alkylene groups completing a carbocyclic ring, which ring can also be substituted with one or more of the substituents listed above for R 1 , R 2 , R 3 and R 4 ; B is a linking group connecting A and C and can be alkylene, arylene, carbonyloxy, oxycarbonylalkyleneoxy, oxycarbonyl, alkyleneoxycarbonyloxy, oxyalkylenecarbonyl, oxycarbonyloxy, alkyleneoxy, oxyalkylene, alkyleneoxyalkyleneoxy, thio, thioalkyleneoxy, sulfinyldioxy, oxy(alkoxy)phosphinooxy, alkyloxyphosphinylidene, aryloxyphosphinylidene, oxy(alkyl)phosphinyloxy, aminocarbonyl, N-alkylaminocarbonyl, N-arylaminocarbonyl, aminocarbonylalkyleneoxy, N-alkylaminocarbonylalkyleneoxy, N-arylaminocarbonylalkyleneoxy, aminocarbonylamino, N-alkylaminocarbonylamino, N,N-dialkylaminocarbonyl, N,N-diarylaminocarbonyl, N-alkylaminoalkyleneoxy, N-arylaminoalkyleneoxy, oxyalkyleneoxy, oxyaryleneoxy, alkyleneaminoalkylene, aryleneaminoarylene, aryleneaminoalkylene and alkyleneaminoarylene; with the proviso that in the above definitions of B, alkyl indicates loweralkyl, alkylene indicates lower alkylene, alkoxy indicates lower alkoxy, aryl indicates phenyl, naphthyl or lower substituted phenyl or naphthyl and arylene indicates phenylene or naphthylene; and wherein C is a group having the formula ##STR16## R 5 and R 6 are each alkyl having 1-6 carbons; R 7 and R 8 are each alkyl having 1-6 carbons or together with the carbon to which they are bound form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; and R 9 is hydrogen, oxy, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or lower alkyl substituted benzyl.

Claim 17

An organic composition according to claim 14 wherein X of said biheterocyclic compound is a carbon atom.

Claim 18

An organic composition according to claim 14 wherein X of said biheterocyclic compound is a nitrogen atom.

Claim 19

An organic composition according to claim 15 wherein Z of said biheterocyclic compound is a nitrogen atom.

Claim 20

An organic composition according to claim 16 wherein Z of said biheterocyclic compound is a sulfur atom.

Claim 21

An organic composition according to claim 16 wherein Z of said biheterocyclic compound is a nitrogen atom.

Claim 22

An organic composition according to claim 16 wherein Z of said biheterocyclic compound is a nitrogen atom containing hydrogen or a lower alkyl group containing 1 to 12 carbon atoms.

Claim 23

An organic composition according to claim 16 wherein Z of said biheterocyclic compound is an oxygen atom.

Claim 24

An organic composition according to claim 21 wherein said biheterocyclic compound has the formula: ##STR17## wherein E is a member selected from the group consisting of a branched or unbranched alkylene group containing 1 to 8 carbon atoms, carbonyl lower alkylene, lower alkylenecarbonyl; R 1 , R 2 , R 3 and R 4 are hydrogen, hydroxy, chloro, bromo, lower alkyl, cyclo lower alkyl, phenyl, naphthyl or lower alkylphenyl or naphthyl, lower alkoxy, amino, lower alkyl amino, cyano, carboxy and the substituents R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , combined with the carbon atoms to which they are attached, are joined lower alkylene groups completing a carbocyclic ring, which ring can also be substituted with one or more of the substituents listed above for R 1 , R 2 , R 3 and R 4 ; R 5 and R 6 are each alkyl having 1-6 carbons; R 7 and R 8 are each alkyl having 1-6 carbons or together with the carbon to which they are bound form a cyclopentyl or cyclohexyl ring, which is unsubstituted or substituted with a methyl group; and R 9 is hydrogen, oxy, alkyl having 1 to 12 carbon atoms, β-methoxyethyl, alkenyl having 3 or 4 carbon atoms, propargyl, benzyl or lower alkyl substituted benzyl.

Claim 25

An organic composition according to claim 14 wherein said biheterocyclic compound has the formula: ##STR18##

Claim 26

An organic composition according to claim 14 wherein said biheterocyclic compound has the formula: ##STR19##

Claim 27

An organic composition according to claim 14 wherein said biheterocyclic compound has the formula: ##STR20##

Claim 28

An organic composition according to claim 14 wherein said biheterocyclic compound has the formula: ##STR21##