Triazine UV absorbers and a process for the preparation thereof

A compound of formula (A),

• wherein Ar1 and Ar2 are independently of each other a moiety of the formula (B) or a moiety of the formula (J),
• wherein
• wherein R1 is selected from the group consisting of hydrogen, halogen, substituted or unsubstituted, linear or branched C1-C24 alkyl, substituted or unsubstituted C6-C24 aryl, —C(═O)—R and OR;
• R2 is selected from the group consisting of hydrogen, halogen, substituted or unsubstituted, linear or branched C1-C24 alkyl, substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C7-C24 arylalkyl, —C(═O)—R, —OR, —S(═O)2OH and —S(═O)2OM;
• wherein M is an alkali metal;
• R3 is selected from the group consisting of hydrogen, halogen, substituted or unsubstituted, linear or branched C1-C24 alkyl, substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C7-C24 arylalkyl, —C(═O)—R, —S(═O)2OH and —S(═O)2OM;
• wherein M is an alkali metal;
• R4 is selected from the group consisting of hydrogen, halogen, substituted or unsubstituted, linear or branched C1-C24 alkyl, substituted or unsubstituted, linear or branched C2-C24 alkenyl, substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C7-C24 arylalkyl, —C(═O)—R, —OR, —S(═O)2—OH and —S(═O)2—OM;
• wherein M is an alkali metal;
• and
• R5 is selected from the group consisting of hydrogen, halogen, substituted or unsubstituted, linear or branched C1-C24 alkyl, substituted or unsubstituted, linear or branched C2-C24 alkenyl, substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C7-C24 arylalkyl, —C(═O)—R, —OR, —S(═O)2OH and —S(═O)2OM;
• wherein M is an alkali metal;
• R and R′ are independently selected from the group consisting of hydrogen, substituted or unsubstituted, linear or branched C1-C24 alkyl, substituted or unsubstituted, linear or branched C2-C24 alkenyl, substituted or unsubstituted C5-C24 cycloalkyl, substituted or unsubstituted C5-C24 cycloalkenyl, substituted or unsubstituted C6-C24 aryl and substituted or unsubstituted C7-C24 arylalkyl;
• wherein, in case of substitution, C1-C24 alkyl and C2-C24 alkenyl are substituted with 1, 2 or 3 substituents selected from the group consisting of —CN, NH2,—N(C1-C5 alkyl)2,—N(C1-C5-alkyl)(phenyl), —N(C1-C5 alkyl)(CH2phenyl), —N(C1-C5-alkyl)(CH2-CH2-phenyl), —O—CF3,—SH, —C(═O)—H, —C(═O)—C1-C5-alkyl, —C(═O)-phenyl, —C(═O)—OH, —C(═O)—O—(C1-C5-alkyl), —C(═O)—O-phenyl, —C(═O)—NH2,—C(═O)—NH—(C1-C5-alkyl), —C(═O)—N(C1-C5-alkyl)2, and unsubstituted C6-C24 aryl;
• C5-C24 cycloalkyl and C5-C24 cycloalkenyl are substituted with 1, 2 or 3 substituents selected from the group consisting of unsubstituted, linear or branched C1-C24 alkyl, unsubstituted, linear or branched C2-C24 alkenyl, CN, NH2,—N(C1-C5 alkyl)2,—N(C1-C5-alkyl)(phenyl), —N(C1-C5alkyl)(CH2phenyl), —N(C1-C5-alkyl)(CH2-CH2-phenyl), —O—CF3,—SH, —C(═O)—H, —C(═O)—C1-C5-alkyl, —C(═O)-phenyl, —C(═O)—OH, —C(═O)—O—(C1-C5-alkyl), —C(═O)—O-phenyl, —C(═O)—NH2,—C(═O)—NH—(C1-C5-alkyl), —C(═O)—N(C1-C5-alkyl)2, and unsubstituted C6-C24 aryl and unsubstituted C6-C24 aryl;
• C6-C24 aryl and C7-C24 arylalkyl are substituted with 1, 2 or 3 substituents selected from the group consisting of halogens, —CN, —S(═O)2OH, —OH, —O(C1-C5 alkyl), —O-(phenyl), —O—(CH2phenyl), —O—(CH2-CH2-phenyl), —S(═O)2OM, CH3, C2H5, C3H7, C8H17, C15H31,—NH2,—O—CF3, —SH, —N(C1-C5 alkyl)2, —N(C1-C5 alkyl, —(═O)—NH—(C1-C5alkyl), —C5-alkyl)(CH2-CH2-phenyl), —C(═O)—H, —C(═O)—C1-C5-alkyl, —C(═O)-phenyl, —C(═O)—OH, —C(═O)—O—(C1-C5-alkyl), —C(═O)—O-phenyl, —C(═O)—NH2,—C(═O)—NH—(C1-C5-alkyl), —C(═O)—N(C1-C5-alkyl)2, and unsubstituted C6-C24 aryl;
• R20 is selected from the group consisting of linear or branched C12-C16 alkyl and linear or branched C12-C16 alkenyl;
• which are in each case unsubstituted or substituted with 1, 2 or 3 substituents selected from the group consisting of —OR, —S(═O)2OH, —S(═O)2OM, and —O—C(═O)—R,
• wherein M is an alkali metal;
• R is selected from the group consisting of hydrogen, unsubstituted, linear or branched C1-C24 alkyl, unsubstituted, linear or branched C2-C24 alkenyl, unsubstituted C5-C24 cycloalkyl, unsubstituted C5-C24 cycloalkenyl, unsubstituted C6-C24aryl and unsubstituted C7-C24 arylalkyl;
• R21 is selected from the group consisting of hydrogen, linear or branched C12-C16 alkyl and linear or branched C12-C16 alkenyl;
• which are in each case unsubstituted or substituted with 1, 2 or 3 substituents selected from the group consisting of —OR, —S(═O)2OH, —S(═O)2OM, and —O—C(═O)—R, moieties of formula (c1) and moieties of formula (c2),
• wherein M is an alkali metal;
• R, R16, R17 and R18 are independently selected from the group consisting of hydrogen, unsubstituted, linear or branched C1-C24 alkyl, unsubstituted, linear or branched C2-C24 alkenyl, unsubstituted C5-C24 cycloalkyl, unsubstituted C5-C24 cycloalkenyl, unsubstituted C6-C24 aryl and unsubstituted C7-C24 arylalkyl;
• R22 is selected from the group consisting of hydrogen and substituted or unsubstituted, linear or branched C1-C4 alkyl;
• or
• R20 and R21 together with the carbon atoms to which they are bonded form a saturated or unsaturated, 5- to 20-membered carbocyclic ring that is unsubstituted or substituted with 1, 2 or 3 substituents selected from the group consisting of halogen, unsubstituted, linear or branched C1-C24 alkyl, unsubstituted, linear or branched C2-C24 alkenyl and unsubstituted C6-C24 aryl, and that optionally contains 1, 2 or 3 heteroatom(s) selected from O, N or S as ring member(s),
• wherein the following compounds of formula (A) are excluded:
• 2-[4,6-bis(2-hydroxy-4-pentadecyl-phenyl)-1,3,5-triazin-2-yl]-5-pentadecyl-phenol and 2-4,6-diphenyl-1,3,5-triazin-2-yl)-5-pentadecylphenol.