Asymmetrical bisbenzotriazoles substituted by a perfluoroalkyl moiety and compositions stabilized therewith
First Claim
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1. 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
- wherein G1 and G1′
are independently hydrogen or halogen;
G2 is halogen, nitro, cyano, —
COOG3, —
P(O)(C6H5)2, —
CO—
G3, —
CO—
NH—
G3, —
CO—
N(G3)2, —
N(G3)—
CO—
G3, E3S—
, E3SO—
or E3SO2—
;
G2′
is perfluoroalkyl of 1 to 12 carbon atoms;
G3 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;
E2 and E2′
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 one to three alkyl of 1 to 4 carbon atoms;
or E2 and E2′
are independently said alkyl of 1 to 24 carbon atoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more —
OH, —
OCOE11, —
OE4, —
NCO, —
NH2, —
NHCOE11, —
NHE4 or —
N(E4)2, or mixtures thereof, where E4 is straight or branched chain alkyl of 1 to 24 carbon atoms;
or said alkyl or said alkenyl interrupted by one or more —
O—
, —
NH—
or —
NE4—
groups or mixtures thereof and which can be unsubstituted or substituted by one or more —
OH, —
OE4 or —
NH2 groups or mixtures thereof;
or E2 and E2′
are independently —
(CH2)m—
CO-E5;
or E2 and E2′
are independently a group of the formula
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Abstract
Asymmetrical bisbenzotriazoles of the formula I
where G2′ is perfluoroalkyl of 1 to 12 carbon atoms, preferably CF3, and where G2 does not contain said group are red-shifted and due to the asymmetry are particularly soluble and useful in a host of applications including automotive coatings, thermoplastics and especially in adhesive compositions, themselves useful in solar panels and other laminate structures.
73 Citations
18 Claims
-
1. 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 - wherein
G1 and G1′
are independently hydrogen or halogen;
G2 is halogen, nitro, cyano, —
COOG3, —
P(O)(C6H5)2, —
CO—
G3, —
CO—
NH—
G3, —
CO—
N(G3)2, —
N(G3)—
CO—
G3, E3S—
, E3SO—
or E3SO2—
;
G2′
is perfluoroalkyl of 1 to 12 carbon atoms;
G3 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;
E2 and E2′
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 one to three alkyl of 1 to 4 carbon atoms;
or E2 and E2′
are independently said alkyl of 1 to 24 carbon atoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more —
OH, —
OCOE11, —
OE4, —
NCO, —
NH2, —
NHCOE11, —
NHE4 or —
N(E4)2, or mixtures thereof, where E4 is straight or branched chain alkyl of 1 to 24 carbon atoms;
or said alkyl or said alkenyl interrupted by one or more —
O—
, —
NH—
or —
NE4—
groups or mixtures thereof and which can be unsubstituted or substituted by one or more —
OH, —
OE4 or —
NH2 groups or mixtures thereof;
or E2 and E2′
are independently —
(CH2)m—
CO-E5;
or E2 and E2′
are independently a group of the formula - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18)
- wherein
Specification