Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
2002-02-13
2004-10-05
Szekely, Peter (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
06800676
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 a phenyl 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 phenyl ring by phenyl substituted by alkyl.
U.S. Pat. No. 5,977,219 discloses highly stable benzotriazole UV absorbers.
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.
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Jozef Lusto{haeck over (n)}, Developments in Polymer Stabilisation-2, Edited by Gerald Scott, Chapter 5, Physical Loss of Stabilisers from Polymers, pp. 185-241, (1980).
DiFazio Michael
Lau Jacqueline
Pastor Stephen D.
Suhadolnik Joseph
Wood Mervin G.
Ciba Specialty Chemicals Corporation
Stevenson Tyler A.
Szekely Peter
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