Long wavelength shifted benzotriazole uv-absorbers and their use

A compound of formula (I) or formula (IV)

• wherein
• Q is a heterocyclic radical forming a 5 or 6-membered ring together with the annealed phenyl-ring, which radical is selected from the group consisting of
• wherein
• X10 is O═C, S═C, R101N, S(O)n where n is 0, 1 or 2;
• Y10 is NR101, O, S(O)n where n is 0, 1 or 2;
• Z10 is O═C, S═C, R101N, O, S(O)n where n is 0, 1 or 2;
• wherein
• X11 is R101, N(R101)2, OR101, S(O)nR101 where n is 0, 1 or 2;
• X11′ is R101, N(R101)2, S(O)nR101 where n is 0, 1 or 2;
• Y11 is C═O, NR101, O, or S(O)n where n is 0, 1 or 2;
• wherein
• X12 is C═O or C═S;
• Y12 is NR101, O or S;
• wherein
• X13 and Y13 are independently NR101, O or S;
• each Z10 is independently from each other O or S;
• R101 is hydrogen, straight or branched chain C1-C24alkyl, straight or branched chain C2-C18alkenyl, C2-C6 alkinyl, C5-C12cycloalkyl, phenyl, naphthyl or C7-C15phenylalkyl;
• or said straight or branched chain C1-C24 alkyl, straight or branched chain C2-C24 alkenyl, C5-C12 cycloalkyl, C2-C6 alkinyl substituted by one or more -halogen, —OH, —OR22, —NH2, —NHR22, —N(R22)2, —NHCOR23, —NR22COR23, —OCOR24, —COR25, —SO2R26,
• —SO3−M+, —PO(R27)n(R28)2-n;
• —Si(R29)n(R30)3-n, —Si(R22)3, —N+(R22)3 A−, —S+(R22)2 A− or combinations thereof;
• said straight or branched chain unsubstituted or substituted C1-C24 alkyl, straight or branched chain unsubstituted or substituted C2-C24 alkenyl, C5-C12 cycloalkyl or C2-C6 alkinyl interrupted by one or more —O—, —S—, —NH— or —NR22— groups or combinations thereof;
• said phenyl, naphthyl or C7-C15phenylalkyl can also be substituted by one or more -halogen, —CF3, —NO2, —NHR22, —N(R22)2, —SO2R26, —PO(R27)n(R28)2-n, —OH, —OR22, —COR25, —R25;
• wherein
• n is 0, 1 or 2;
• R22 is straight or branched chain C1-C18 alkyl, straight or branched chain C2-C18 alkenyl, C5-C10 cycloalkyl, phenyl or naphthyl, C1-C15 phenylalkyl, or two R22 when attached to an N or Si atom can form together with the atom to which they are bonded a pyrrolidine, piperidine or morpholine ring;
• R23 is hydrogen, OR22, NHR22, N(R22)2 or has the same meaning as R22,
• R24 is OR22, NHR22, N(R22)2 or has the same meaning as R22,
• R25 is hydrogen, OH, OR22, NHR22 or N(R22)2, or has the same meaning as R22,
• R26 is OH, OR22, NHR22 or N(R22)2,
• R27 is NH2, NHR22 or N(R22)2,
• R28 is OH or OR22,
• R29 is C1 or OR22,
• R30 is straight or branched chain C1-C18 alkyl;
• or
• R101 can be a bridging group of straight or branched C1-C18alkylene, C6-C10cycloalkylene, para-phenylene or a group
• wherein * denotes a bond where the bridge connects two compounds of formula I, said C1-C12alkylene, C6-C10cycloalkylene can also be interrupted by one or more —O—, —S—, —NH— or —NR22— groups or combinations thereof;
• or when Y is a direct bond, Z can additionally also be a direct bond;
• R102 is hydrogen, —CN, —COR24 straight or branched chain C1-C24alkyl, straight or branched chain C2-C18alkenyl, C2-C6alkylnyl, C5-C12cycloalkyl, phenyl, naphthyl or C7-C15phenylalkyl;
• or
• if two substituents R101/R102 or R102/R102 are in vicinal position, they can form together with the atoms to which they are bonded an aliphatic, 5 to 8-membered ring;
• R1 is hydrogen, straight or branched chain alkyl 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 4 alkyl of 1 to 4 carbon atoms;
• or
• R1 is a group
• wherein
• L is alkylene of 1 to 12 carbon atoms, alkylidene of 2 to 12 carbon atoms, benzylidene, p-xylylene or cycloalkylene of 5 to 7 carbon atoms;
• R2 is straight or branched chain alkyl 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
• said alkyl substituted by one or more —OH, —OCO—R11, —OR14, —NCO or —NH2 groups or mixtures thereof, or said alkyl or said alkenyl interrupted by one or more —O—, —NH— or —NR14— groups or mixtures thereof and which can be unsubstituted or substituted by one or more —OH, —OR14 or —NH2 groups or mixtures thereof;
• where
• R11 is hydrogen, straight or branched chain C1-C18alkyl, C8-C12cycloalkyl, straight or branched chain C3-C8alkenyl, phenyl, naphthyl or C7-C15phenylalkyl;
• and
• R14 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms;
• or
• R2 is —OR14, a group —C(O)—O—R14, —C(O)—NHR14 or —C(O)—NR14R′14 wherein R′14 has the same meaning as R14;
• or
• R2 is —SR13, —NHR13 or —N(R13)2;
• or
• R2 is —(CH2)m—CO—X1—(Z)p—Y—R15 wherein
• X1 is —O— or —N(R16)—,
• Y is —O— or —N(R17)— or a direct bond,
• Z is C2-C12-alkylene, C4-C12alkylene interrupted by one to three nitrogen atoms, oxygen atoms or a mixture thereof, or is C3-C12alkylene, butenylene, butynylene, cyclohexylene or phenylene, each of which may be additionally substituted by a hydroxyl group;
• or a group
• wherein * denotes a bond
• or when Y is a direct bond, Z can additionally also be a direct bond;
• 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 hydrogen, C1-C12alkyl, a group
• or 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—X1—R20, wherein
• R20 is hydrogen, C1-C12alkyl or a group of formulae
• R5 and R6 are independently hydrogen or C1-C18alkylene;
• R13 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, phenyl or naphthyl, which both may be substituted by one or two alkyl of 1 to 4 carbon atoms;
• 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-C15phenylalkyl, and R16 together with R17 in the case where Z is ethylene, also forms ethylene, wherein a large shift of the absorption maximum of approximately 20-40 nm is observed, when benzo ring of benzotriazole compound of formula (I) or formula (IV) is part of a heterocyclic system.