Benzotriazole/hals molecular combinations and compositions stabilized therewith

A compound of formula A, C or D

• 11
• wherein
• G1 and G1′ are independently hydrogen or halogen,
• G2 and G2′ are independently hydrogen, halogen, nitro, cyano, R3SO—, R3SO2—, —COOG3, perfluoroalkyl of 1 to 12 carbon atoms, —P(O)(C6H5)2, —CO—G3, —CO—NH—G3, —CO—N(G3)2, —N(G3)—CO—G3, phenyl substituted by 2,2,6,6-tetramethylpiperidin-1-yloxy,
• 12
• G3 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight of branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms;
• or G3 is a group formula I, II or III
• 13
• wherein
• M is a direct bond, —NG9—, —O—, —S—, —SO—, —SO2—, —SO2NG9—, —CONG9—, —COO— or —OCO—;
• L1 is a direct bond, alkylene of 1 to 18 carbon atoms, alkenylene of 3 to 18 carbon atoms, cycloalkylene of 5 to 12 carbon atoms, cycloalkenylene of 5 to 12 carbon atoms or said alkylene interrupted by 1 to 4 oxygen atoms;
• X1 is a direct bond, —COO—, —CONG9—, —O— or —NG9—;
• G9 is hydrogen or alkyl of 1 to 18 carbon atoms;
• E1 to E4 are independently alkyl of 1 to 8 carbon atoms, or E1 and E2 together are pentamethylene or E3 and E4 together are pentamethylene;
• E5 is hydrogen, oxyl, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 3 to 24 carbon atoms, benzyl, acetyl, —CH2CH(OH)—E8, —OE9, —OE10(OH)b,
• E8 is hydrogen, methyl, ethyl or phenyl,
• E9 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, straight or branched chain alkenyl of 3 to 24 carbon atoms, cycloalkenyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, a radical of a saturated or unsaturated bicyclic or tricyclic hydrocarbon of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one to three alkyl of 1 to 4 carbon atoms;
• or a group of formula IV
• 14
• E10 is a straight or branched chain alkyl of 1 to 24 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, cycloalkenyl of 5 to 12 carbon atoms, straight or branched chain alkenyl of 3 to 24 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl or said phenyl substituted by one to three alkyl of 1 to 4 carbon atoms;
• b is 1, 2 or 3 with the restriction that b cannot exceed the number of carbon atoms in E10, and if b is 2 or 3, each hydroxyl group is attached to a different carbon atom of E10;
• E11 to E15 are independently hydrogen, halogen, nitro, cyano, alkyl of 1 to 18 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms, hydroxyl, carboxyl, alkylthio of 1 to 18 carbon atoms, alkoxy or 1 to 18 carbon atoms, phenylalkoxy of 7 to 15 carbon atoms, aryloxy of 6 to 10 carbon atoms, alkylcarbonyloxy of 2 to 18 carbon atoms, alkylsulfonyl of 1 to 18 carbon atoms, arylsulfonyl of 6 to 15 carbon atoms, sulfo or phosphono, or any two vicinal substituents connected together to form a mono- or polycyclic ring;
• R1 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight of branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms;
• or R1 is a group I, II, III, V or VI
• 15
• where
• E27 and E28 are independently alkyl of 1 to 18 carbon atoms, or cycloalkyl of 5 to 12 carbon atoms;
• E22, E23, E24, E25 and E26 are independently hydrogen, halogen, straight or branched alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, said alkyl or said alkenyl substituted by one or more halogen, —OCOR11, —OR4, —NCO, —NHCOR11 or —NR7R8, or mixtures thereof, where R4 is straight or branched chain alkyl of 1 to 24 carbon atoms or straight or branched chain alkenyl of 2 to 18 carbon atoms;
• or said alkyl or said alkenyl interrupted by one or more —O—, —NH— or —NR4— groups or mixtures thereof and which can be unsubstituted or substituted by one or more —OH, —OR4 or —NH2, or mixtures thereof;
• or
• E22, E23, B24, E25 and E26 are independently phenyl, —OH, —OCOR11, —OE29, —NCO, —NHCOR11, or —NR7R8, cyano, nitro, perfluoroalkyl of 1 to 12 carbon atoms, —COG3, —COOG3, —CON(G3)2, —CONHG3, R3S—, R3SO—, R3SO2—, —P(O)(C6H5)2, —P(O))OG3)2, —SO2—X2—E29;
• X2 is —O—, —NH— or —NR4—;
• E29 is straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, said alkyl or said alkenyl substituted by one or more —OH, —OCOR11, —OR4, —NCO, —NHCOR11, —NR7R8, phthalimido,
• 16
• or mixtures thereof, where R4 is straight or branched chain alkyl of 1 to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms;
• or said alkyl or said alkenyl interrupted by one or more —O—, —NH— or —NR4— groups or mixtures thereof and which can be unsubstituted or substituted by one or more —OH, —OR4 or —NH2, or mixtures thereof;
• or E29 is phenyl or phenylalkyl of 7 to 15 carbon atoms, or said phenyl or said phenylalkyl substituted by one to three alkyl groups of 1 to 4 carbon atoms;
• R2 and R2′ are independently straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 3 alkyl of 1 to 4 carbon atoms;
• or R2 is hydroxyl or —OR4 where R4 is straight or branched chain alkyl of 1 to 24 carbon atoms;
• or said alkyl substituted by one or more —OH, —OCO—R11, —OR4, —NCO or —NH2 groups or mixtures thereof;
• or said alkyl or said alkenyl interrupted by one or more —O—, —NH— or —NR4— groups or mixtures thereof and which can be unsubstituted or substituted by one or more —OH, —OR4 or —NH2 groups or mixtures thereof;
• or R2 and R2′ are independently —SR3, —NHR3 or —N(R3)2;
• or R2 or R2′ is a group I, II, III, V or VI defined above;
• or R2 or R2′ is
• —(CH2)m—CO—X—(Z)p—Y—R15
• wherein
• X is —O— or —N(R16)—,
• Y is —O— or —N(R17)—,
• Z is C2-C12-alkylene, C4-C12-alkylene interrupted by one to three nitrogen atoms, oxygen atoms or a mixture thereof, or is C3-C12-alkylene, butenylene, butynylene, cyclohexylene or phenylene, each substituted by a hydroxyl group,
• m is zero, 1 or 2,
• p is 1, or p is also zero when X and Y are —N(R16)— and —N(R17)—, respectively,
• R15 is a group —CO—C(R18)═C(H)R19 or, when Y is —N(R17)—, forms together with R17 a group —CO—CH═CH—CO—, wherein R18 is hydrogen or methyl, and R19 is hydrogen, methyl or —CO—X—R20, wherein R20 is hydrogen, C1-C12-alkyl or a group of the formula.
• 17
• wherein the symbols R1, R3, X, Z, m and p have the meanings defined above, and R16 and R17 independently of one another are hydrogen, C1-C12-alkyl, C3-C12-alkyl interrupted by 1 to 3 oxygen atoms, or is cyclohexyl or C7-C15aralkyl, and R16 together with R17 in the case where Z is ethylene, also forms ethylene,
• n is 1 or 2,
• when n is 1, R5 is —OR6 or —NR7R8, or
• R5 is —PO(OR12)2, —OSi(R11)3 or —OCO—R11, a group I, II or III, or straight or branched chain C1-C24alkyl which is interrupted by —O—, —S— or —NR11, and which can be unsubstituted or substituted by —OH or —OCO—R11, C5-C12 cycloalkyl which is unsubstituted or substituted by —OH, straight chain or branched C2-C18alkenyl which is unsubstituted or substituted by —OH, C7-C15aralkyl, —CH2—CHOH—R13 or glycidyl,
• R6 is hydrogen, straight or branched chain C1-C24alkyl which is unsubstituted or substituted by one or more OH, OR4 or NH2 groups, or —OR6 is —(OCH2CH2)wOH or —(OCH2CH2)wOR21where w is 1 to 12 and R21 is alkyl of 1 to 12 carbon atoms,
• R7 and R8 are independently hydrogen, alkyl of 1 to 18 carbon atoms, straight or branched chain C3-C18alkyl which is interrupted by —O—, —S— or —NR11—, C5-C12 cycloalkyl, C6-C14aryl or C1-C3hydroxylalkyl, or R7 and R8 together with the N atom are a pyrrolidine, piperidine, piperazine or morpholine ring,
• when n is 2, R5 is one of divalent radicals —O—R9—O— or —N(R11)—R 10 —N(R11)—,
• R9 is C2-C8alkylene, C4-C8alkenylene, C4alkynylene, cyclohexylene, straight or branched chain C4-C10alkylene which is interrupted by —O— or by —CH2—CHOH—CH2—O—R14—O—CH2—CHOH—CH2—,
• R10 being straight or branched chain C2-C12alkylene which may be interrupted by —O—, cyclohexylene, or
• 18
• or R10 and R11with the two nitrogen atoms form a piperazine ring,
• R14 is straight or branched chain C2-C8alkylene, straight or branched chain C4-C10alkylene which is interrupted by —O—, cycloalkylene, arylene or
• 19
• where R7 and R8 are independently hydrogen, alkyl of 1 to 18 carbon atoms or R7 and R8 together are alkylene of 4 to 6 carbon atoms, 3-oxapentamethylene, 3-iminopentamethylene or 3-methyliminopentamethylene,
• R11 is hydrogen, straight or branched chain C1-C18alkyl, C5-C12cycloalkyl, straight or branched chain C3-C8alkenyl, C6-C14aryl or C7-C15aralkyl,
• R12 is straight or branched chain C1-C18alkyl, straight or branched chain C3-C18alkenyl, C5-C10cycloalkyl, C6-C16aryl or C7-C15aralkyl,
• R13 is H, straight chain or branched C1-C18alkyl which is substituted by —PO(R12)2, phenyl which is unsubstituted or substituted by OH, C7-C15aralkyl or —CH2OR12,
• R3 is alkyl of 1 to 20 carbon atoms, hydroxyalkyl of 2 to 20 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one or two alkyl of 1 to 4 carbon atoms or 1,1,2,2-tetrahydroperfluoroalkyl where the perfluoroalkyl moiety is of 6 to 16 carbon atoms, and
• L is alkylene of 1 to 12 carbon atoms, alkylidene of 2 to 12 carbon atoms, benzylidene, p-xylylene or cycloalkylidene;
• and
• with the proviso that at least one of G2, G2′, G3, R1, R2 or R5 contains a hindered amine moiety, and
• with the further provisos that
• (a) when G2 of formula A is hydrogen or halogen, then E5 of group I is not OE9;
• (b) when G2 of formula A is hydrogen or halogen, then E5 of group I is not hydrogen, oxyl, C1-C12alkyl, C3-C8alkenyl, benzyl, acetyl, or a group —CH2—CH(OH)—E8;
• (c) when G2 is —COOG3 and G3 is of group I, then E5 of group I is not hydrogen, oxyl, C1-C12alkyl, C3-C8alkenyl, benzyl, acetyl, or a group —CH2—CH(OH)—E8;
• and
• (d) when G2 of formula A is hydrogen, halogen or cyano, then R1 is not a substituted or unsubstituted hydantoin-3-ylmethyl group.