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US 2008/0157025 A1Published application
Long Wavelength Shifted Benzotriazole Uv-Absorbers And Their Use
AssigneeCiba Specialty Chemicals Corporation
InventorsKatharina Fritzsche, Adalbert Braig, Markus Frey, Walter Fischer
Life of this patent
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Abstract
The invention relates to novel benzotriazole UV-absorbers having a long wavelength shifted absorption spectrum with significant absorbance up to 410-420 nm. Further aspects of the invention are a process for their preparation, a UV stabilized composition containing the new UV-absorbers and the use of the new compounds as UV-light stabilizers for organic materials.
Claims20
A compound of formulae (I) or (II)
- wherein
- 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
- 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, C5-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, R6, R7 and R8 are independently hydrogen, halogen, CN, NO2 or NH2;
- 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;
- X is O or NE1 wherein
- E1 is hydrogen, straight or branched chain C1-C24alkyl, straight or branched chain C2-C18alkenyl, C2-C6alkyinyl, C5-C12cycloalkyl, phenyl, naphthyl or C7-C15phenylalkyl;
- or said straight or branched chain C1-C24alkyl, straight or branched chain C2-C24alkenyl, C5-C12 cycloalkyl, C2-C6 alkinyl can be substituted by one or more —F, —OH, —OR22, —NH2, —NHR22, —N(R22)2, —NHCOR23, —NR22COR23, —OCOR24, —COR25, —SO2R26, —PO(R27)n(R28)2-n, —Si(R29)n(R30)3-n, —Si(R22)3, —N+(R22)3A−, —S+(R22)2A−, -oxiranyl groups or mixtures thereof;
- said straight or branched chain C1-C24 alkyl, straight or branched chain unsubstituted or substituted C2-C24alkenyl, C5-C12 cycloalkyl or C2-C6 alkinyl can also be 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, —CN, —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-C18alkyl, straight or branched chain C2-C18alkenyl, C5-C10 cycloalkyl, phenyl or naphthyl, C7-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, O-glycidyl 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 Cl or OR22,
- R30 is straight or branched chain C1-C18alkyl;
- or
- E1 is a group
- R1 to R8 have the meanings as defined above and
- Q is straight or branched C2-C12alkylene, C2-C12alkylene, which is interrupted by one or more —O—, NH or NR14 atoms, C5-C10cycloalkylene, para-phenylene or a group
- wherein * denotes a bond.
49 more elements
(canceled)
Dependencies are inferred from the claim text.