2H-benzotriazole UV absorders substituted with...

Details 2H-benzotriazole UV absorders substituted with... 2H-benzotriazole UV absorders substituted with...

2000-08-03

2002-05-21

Morris, Patricia L. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C548S113000, C548S261000

Reexamination Certificate

active

06392056

ABSTRACT:

The instant invention pertains to 2H-benzotriazoles substituted on the phenyl ring at the 3-position or at the 5-position by a 1,1-diphenylalkyl moiety.
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.
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. The use of the substituent 1,1-diphenylalkyl (particularly 1,1-diphenylethyl) on the basic benzotriazole molecule is unknown.
U.S. Pat. No. 5,438,142 and D. Kuila et al. in Chemical Materials, 1999 (11), 109 do describe tris(hydroxyphenyl)ethane benzotriazoles as copolymerizable UV absorbers. The product described in these references is 1-[3-(benzotriazol-2-yl)-4-hydroxyphenyl]-1,1-bis(4-hydroxyphenyl)ethane. The purpose of the two hydroxyphenyl groups at the 4position of the hydroxylphenyl ring of the 2H-benzotriazole moiety is to provide reactive hydroxy groups that can be copolymerized into condensation polymer systems to provide a non-migrating UV absorbing moiety. The 4-hydroxyphenyl moieties of these compounds are substituted at the 5-position rather than at the 3-position of the hydroxyphenyl ring of the 2H-benzotriazole molecules. As seen from the discussion above, the exact location of the substituent is important when considerations of long term photostability is concerned.
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 chloro,
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
 where
E
22
, E
23
, E
24
, E
25
, E
26
, E
28
, E
29
, E
30
, E
31
and E
32
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
, E
26
, E
28
, E
29
, E
30
, E
31
and E
32
are independently phenyl, —OH, —OCOE
11
, —OE
33
, —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
33
;
X
1
is —O—, —NH— or —NE
4
—;
E
27
is alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms or phenyl,
E
33
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
33
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, —NH
2
, —NHCOE
11
, —NHE
4
or —N(E
4
)
2
, or mixtures thereof, where E
4
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 —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 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
11
, C
5
-C
12
cycloalkyl which is unsubstituted or substituted by —OH, straight chain or branched C
2
-C
18
alkenyl which is unsubstituted or substituted by —OH, C
7
-C
15
aralkyl, —CH
2
—CHOH—E
13
or glycidyl,
E
6
is hydrogen, straight or branched chain C
1
-C
24
alkyl which is unsubstituted or substituted by one or more OH, OE
4
or NH
2
groups, or —OE
6
is —(OCH
2
CH
2
)
w
OH or —(OCH
2
CH
2
)
w
OE
21 where w is
1 to 12 and E
21
, is alkyl of 1 to 12 carbon atoms,
E
7
and E
8
are independently hydrogen, alkyl of 1 to 18 carbon atoms, straight or branched chain C
3
-C
18
alkyl which is interrupted by —O—, —S— or —

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