Benzotriazoles containing &agr;-cumyl groups substituted by...

Details Benzotriazoles containing &agr;-cumyl groups substituted by... Benzotriazoles containing &agr;-cumyl groups substituted by...

2000-08-03

2002-09-17

Hoke, Veronica P. (Department: 1714)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

C548S259000, C548S260000, C548S261000

Reexamination Certificate

active

06451887

ABSTRACT:

The instant invention pertains to 2H-benzotriazole UV absorbers substituted at the 3-position and/or the 5-position of the phenyl ring by &agr;-cumyl moiety which is substituted by a group containing a heteroatom.
BACKGROUND OF THE INVENTION
One of the most important classes of UV absorbers are the 2H-benzotriazoles. There are a myriad of patents and other references to these materials and their compositions. Indeed, several of the 2H-benzotriazole UV absorbers have achieved great commercial importance for a host of end-use applications. Several of these commerical compounds are substituted by one or more unsubstituted &agr;-cumyl moieties.
Benzotriazole UV absorbers which are substituted at the 5-position of the benzo ring by an electron withdrawing group exhibit enhanced durability and very low loss rates when incorporated into automotive coatings. This is particularly the case when the 3-position of the phenyl ring is also substituted by phenyl or phenylalkyl such as &agr;-cumyl. Compounds where the 5-position of the benzo ring are substituted by perfluoroalkyl such as trifluoromethyl are particularly of interest for both their enhanced durability and for their excellent solubility and excellent color properties in some thermoplastic compositions when the phenyl ring is substituted at the 3-position by hydrogen or tert-alkyl.
It is well known that the stabilization and other physical properties exhibited by the 2H-benzotriazole UV absorbers can be markedly altered depending on the nature and location of the various substituents used to modify the basic 2H-benzotriazole structure.
Although there has been some generic disclosure of substituted &agr;-cumyl groups on benzotriazoles, none of these compounds have ever been exemplified nor prepared and their properities evaluated.
U.S. Pat. Nos. 4,727,158 and 4,904,712 describe 2H-benzotriazole compounds which are substituted at the 5-position on the benzo ring by higher alkyl groups of 8 to 18 carbon atoms. While it is generically disclosed that these compounds could be substituted on the 3- and/or 5-positions of the phenyl ring by &agr;-cumyl or &agr;-cumyl substituted by alkyl of 1 to 4 carbon atoms or by halogen, none of such compounds were actually prepared nor tested.
U.S. Pat. No. 5,097,041 teaches that benzotriazole UV absorbers can be substituted on the 5-position of the phenyl ring by phenyl substituted by chloro, but this patent does not teach &agr;-cumyl substituted by chloro at any point in the benzotriazole molecule.
WO 98/41186 is directed to hair dye compositions and the various components which may be included therein. This reference contains a host of generic structures for such components including 2H-benzotriazoles. This reference in that regards is similar to U.S. Pat. Nos. 4,727,158 and 4,904,712 and does not exemplify nor describe specifically any benzotriazole substituted by an &agr;-cumyl group itself substituted by a heteroatom.
U.S. Pat. No. 5,097,041 describes the purification of benzotriazoles where the group at the 5-position of the phenyl ring can be phenyl substituted by chloro.
DETAILED DISCLOSURE
The instant invention pertains to novel benzotriazole UV absorbers having enhanced stability and durability and a low loss rate when incorporated into automotive coatings. These new benzotriazole UV absorbers are also soluble in a variety of substrates including thermoplastic polymers and often are essentially colorless even though absorbing in the 350-390 nm range.
More specifically, the instant invention pertains to new benzotriazole compounds of formula I, II or III:
wherein
G
1
is hydrogen or halogen,
G
2
is hydrogen, cyano, perfluoroalkyl of 1 to 12 carbon atoms, halogen, —CO—G
3
, —COOG
3
, —CONHG
3
, —CON(G
3
)
2
, E
3
SO—, E
3
SO
2
—, nitro, —P(O)(C
6
H
5
)
2
, —P(O)(OG
3
)
2
,
G
3
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,
E
1
is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 24 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 E
1
is alkyl of 1 to 24 carbon atoms substituted by one or two hydroxy groups;
or E
1
is alkyl of 1 to 24 carbon atoms, alkenyl of 2 to 18 carbon atoms, said alkyl or said alkenyl substituted by one or more —OCOE
11
, —OE
4
, —NCO, —NHCOE
11
, or —NE
7
E
8
, or mixtures thereof, where E
4
is straight or branched chain alkyl of 1 to 24 carbon atoms or straight or branched chain alkenyl of 2 to 18 carbon atoms; or said alkyl or said alkenyl interrupted by one or more —O—, —NH— or —NE
4
— groups or mixtures thereof and which can be unsubstituted or substituted by one or more —OH, —OE
4
or —NH
2
, or mixtures thereof,
or E
1
is a group of formula IV or V:
where
E
27
and E
28
are independently alkyl of 1 to 18 carbon atoms, or cycloalkyl of 5 to 12 carbon atoms;
E
22
, E
23
, E
24
, E25 and E26 are independently hydrogen, halogen, straight or branched alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, said alkyl or said alkenyl substituted by one or more halogen, —OCOE
11
, —OE
4
, —NCO, —NHCOE
11
or —NE
7
E
8
, or mixtures thereof, where E
4
is straight or branched chain alkyl of 1 to 24 carbon atoms or straight or branched chain alkenyl of 2 to 18 carbon atoms; or said alkyl or said alkenyl interrupted by one or more —O—, —NH— or —NE
4
— groups or mixtures thereof and which can be unsubstituted or substituted by one or more —OH, —OE
4
or —NH
2
, or mixtures thereof; or
E
22
, E
23
, E
24
, E
25
and E
26
are independently phenyl, —OH, —OCOE
11
, —OE
29
, —NCO, —NHCOE
11
or —NE
7
E
8
, cyano, nitro, perfluoroalkyl of 1 to 12 carbon atoms, —COG
3
, —COOG
3
, —CON(G
3
)
2
, —CONHG
3
, E
3
S—, E
3
SO—, E
3
SO
2
—, —P(O)(C
6
H
5
)
2
, —P(O))OG
3
)
2
, —SO
2
—X
1
—E
29
;
X
1
is —O—, —NH— or —NE
4
—;
E
29
is straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, said alkyl or said alkenyl substituted by one or more —OH, —OCOE
11
, —OE
4
, —NCO, —NHCOE
11
, —NE
7
E
8
, phthalimido,
or mixtures thereof, where E
4
is straight or branched chain alkyl of 1 to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms; or said alkyl or said alkenyl interrupted by one or more —O—, —NH— or —NE
4
— groups or mixtures thereof and which can be unsubstituted or substituted by one or more —OH, —OE
4
or —NH
2
, or mixtures thereof; or E
29
is phenyl or phenylalkyl of 7 to 15 carbon atoms, or said phenyl or said phenylalkyl substituted by one to three alkyl groups of 1 to 4 carbon atoms;
E
2
is 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 E
2
is alkyl of 1 to 24 carbon atoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more —OH, —OCOE
11
, —OE
4
, —NCO, —NHCOE
11
or —NE
7
E
8
, or mixtures thereof, where E
4
is straight or branched chain alkyl of 1 to 24 carbon atoms or aLkenyl of 2 to 18 carbon atoms; or said alkyl or said alkenyl interrupted by one or more —O—, —NH— or —NE
4
— groups or mixtures thereof and which can be unsubstituted or substituted by one or more —OH, —OE
4
or —NH
2
groups or mixtures thereof, or E
2
is a group of formula IV or formula V as described above;
n is 1 or 2,
when n is 1, E
5
is OE
6
or NE
7
E
8
, or
E
5
is —PO(OE
12
)
2
, —OSi(E
11
)
3
or —OCO—E
11
,
or straight or branched chain C
1
-C
24
alkyl which is interrupted by —O—, —S—or —NE
11
and which can be unsubstituted or substituted by —OH or —OCO—E

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