US 6,387,992 B1Granted

Substituted 5-heteroaryl-2-(2-hydroxyphenyl)-2h-benzotriazole UV absorbers, a process for preparation thereof and compositions stabilized therewith

AssigneeCiba Specialty Chemicals Corporation

InventorsStephen D. Pastor, Anthony DeBellis, Mervin G. Wood, Joseph Suhadolnik, Deborah DeHessa, Ramanathan Ravichandran

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Abstract

Compounds of formula I or II where R is a heteroaryl moiety, such as 3-pyridyl, or T is a heteroaryl moiety, such as thien-2,5-diyl, and E1 and E2 are independently hydrogen, alkyl, aralkyl and the like, are prepared by reaction of a benzotriazole substituted on the 5-position of the benzo ring by a halogen atom with a heteroarylboronic acid or ester in the presence of a transition-metal catalyst, such as palladium (II) diacetate. The benzotriazole compounds of formula I are particularly efficacious as stabilizers for automotive coatings and candle wax.

Claims24

Dependent claims

A compound of formula I or II

wherein
R is 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyrrolyl, 3-pyrrolyl, 3-thianaphthenyl, 8-quinolyl, 5-indolyl, 2-selenophenyl, or said pyridyl, thienyl, furyl, pyrrolyl, thianaphthenyl, quinolyl, indolyl or selenophenyl moiety substituted by one to five moieties selected from the group consisting of straight or branched chain alkyl of 1 to 18 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, R3S—, R3SO—, R3SO2, aryl of 6 to 10 carbon atoms, perfluoroalkyl of 1 to 12 carbon atoms, halogen, nitro, cyano, carboxyl, triisopropylsilyl, formyl, acetyl, alkoxycarbonyl of 2 to 19 carbon atoms, hydroxyl, alkoxy of 1 to 18 carbon atoms, aryloxy of 6 to 10 carbon atoms, sulfato or phosphato, or where any two substituents from a benzo ring with the heteroaryl moiety to which they are attached,
T is thien-2,5-diyl,
R3 is alkyl of 1 to 18 carbon atoms, phenylalkyl of 7 to 15 carbon atoms or aryl of 6 to 10 carbon atoms,
E1 is hydrogen, straight or branched chain alkyl of 1 to 24 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,
E2 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 E2 is alkyl of 1 to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms substituted by one or more —OH, —OCOE3, —NH2, —NHCOE3 or —COOE3, or mixtures thereof;
or said alkyl or said alkenyl interrupted by one or more —O— which can be unsubstituted or substituted by one or more —OH groups;
where E3 is hydrogen or alkyl of 1 to 24 carbon atoms, and where said alkyl is interrupted by one or more —O— and which can be substituted by one or more —OH, or —OR21 groups where R21 is alkyl of 1 to 12 carbon atoms;
and
with the proviso that, when E1 is hydrogen, methyl or ethyl and E2 is methyl or ethyl, R is not 2-pyridyl.

8 more elements

A composition stabilized against thermal, oxidative or light-induced degradation which comprises,

(a) an organic material subject to thermal, oxidative or light-induced degradation, and
(b) an effective stabilizing amount of a compound of formula I or II
wherein
R is 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-thienyl, 3-thienyl, 2-furyl, 3-furyl, 2-pyrrolyl, 3-pyrrolyl, 3-thianaphthenyl, 8-quinolyl, 5-indolyl, 2-selenophenyl, or said pyridyl, thienyl, furyl, pyrrolyl, thianaphthenyl, quinolyl, indolyl or selenophenyl moiety substituted by one to five moieties selected from the group consisting of straight or branched chain alkyl of 1 to 18 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, R3S—, R3SO—, R3SO2, aryl of 6 to 10 carbon atoms, perfluoroalkyl of 1 to 12 carbon atoms, halogen, nitro, cyano, carboxyl, triisopropylsilyl, formyl, acetyl, alkoxycarbonyl of 2 to 19 carbon atoms, hydroxyl, alkoxy of 1 to 18 carbon atoms, aryloxy of 6 to 10 carbon atoms, sulfato or phosphato, or where any two substituents from a benzo ring with the heteroaryl moiety to which they are attached,
T is thien-2,5-diyl,
R3 is alkyl of 1 to 18 carbon atoms, phenylalkyl of 7 to 15 carbon atoms or aryl of 6 to 10 carbon atoms,
E1 is hydrogen, straight or branched chain alkyl of 1 to 24 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,
E2 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 E2 is alkyl of 1 to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms substituted by one or more —OH, —OCOE3, —NH2, —NHCOE3 or —COOE3, or mixtures thereof;
or said alkyl or said alkenyl interrupted by one or more —O— which can be unsubstituted or substituted by one or more —OH groups;
where E3 is hydrogen or alkyl of 1 to 24 carbon atoms, and where said alkyl is interrupted by one or more —O— and which can be substituted by one or more —OH or —OR21 groups where R21 is alkyl of 1 to 12 carbon atoms.

8 more elements

Dependencies are inferred from the claim text.