Stabilized adhesive compositions containing highly soluble, red-shifted, photostable benzotriazole UV absorbers and laminated articles derived therefrom

Adhesive compositions are rendered stable against degradation caused by ultraviolet light through the incorporation of selected highly soluble, red-shifted, photostable benzotriazole UV absorbers which absorb light strongly in the 350 to 400 nm range. These UV absorbers exhibit excellent photostability and are highly soluble in adhesive formulations. The laminated articles derived from these compositions include, for example, solar control films, films and glazings, UV absorbing glasses and glass coatings, windscreens, retroreflective sheetings and signs, solar reflectors, optical films and the like.

This invention pertains to stabilized adhesive compositions containing an
 effective amount of a benzotriazole UV absorber having enhanced
 solubility, durability and absorption in the 350 to 400 nm range.
 BACKGROUND OF THE INVENTION
 Adhesives are made up of various components such as polymers, tackifiers,
 waxes and oils. Adhesive formulations based on these ingredients are
 susceptible to degradation. The consequences of degradation are
 discoloration, loss of elongation, loss of tensile strength, loss of tack
 and change in viscosity, molecular weight and molecular weight
 distribution. Degradation can be caused by prolonged exposure to sunlight.
 Sunlight contains invisible ultraviolet (UV) radiation with wavelengths
 between 290 and 400 nm. This radiation is responsible for the initiation
 of photodegradation.
 Absorption of UV light by chromophores present in the adhesive formulation
 transforms the chromophores into their excited states which can undergo
 further undesired reactions. Some polymers contain strongly absorbing
 chromophores as a major part of their structures. Other polymers contain
 unintentional impurities such as ketones and hydroperoxide moieties and
 catalyst residues which act as chromophores. Absorption of UV radiation by
 these chromophores eventually results in bond cleavage, chain scission
 and/or crosslinking reactions.
 Photostabilization of adhesives can be achieved by the addition of UV
 absorbers which convert the absorbed energy into harmless heat. An ideal
 UV absorber should be extremely photostable and have strong absorption
 over the UV range from 290 to 400 nm, but particularly the range of 350 to
 400 nm. Classes of UV absorbers include the salicylates, cyanoacrylates,
 malonates, oxanilides, benzophenones, s-tiazines and benzotriazoles.
 Salicylates, cyanoacrylates, malonates and oxanilides absorb UV light
 primarily at the lower wavelengths of the UV range. These compounds have
 little to no absorption in the range of 350 to 400 nm which make them
 unsuitable for the instant applications. Benzophenones absorb over the
 lower half of the UV range, and they tend to be prone to yellowing upon
 light exposure due to photodegradation. Recently, it has been shown
 photochemically that benzophenones decompose prematurely in ethylene-vinyl
 acetate encapsulants which lead to the production of polyenic
 chromophores. This color generation from light yellow to brown is not only
 highly undesirable and unsightly in adhesive systems, but also can results
 in a loss of adhesive properties. By contrast, selected benzotriazole UV
 absorbers are particularly useful because of their increased
 photostability.
 Some polymers such as polycarbonates, polyesters and aromatic polyurethanes
 contain strongly absorbing chromophores as a major and integral part of
 their structures. Poly(ethylene terephthalate) (PET) and poly(ethylene
 2,6-naphthalenedicarboxylate) (PEN) are particular examples the latter of
 which absorbs into the red UV region and especially need red-shifted
 benzotriazoles for UV protection. U.S. Pat. No. 5,294,473 and WO 98/34981
 teach the use of coatings containing UV absorbers including some
 benzotriazoles in stabilizing PEN films. Adding an adhesive UV screening
 layer containing the benzotriazoles, especially those described in the
 instant invention, further protects such polymers in multilayered
 constructions and articles.
 The description, preparation and uses of the 2H-benzotriazole UV absorbers
 are described in U.S. Pat. Nos. 3,004,896; 3,055,896; 3,072,585;
 3,074,910; 3,189,615; 3,230,194; 4,127,586; 4,226,763; 4,278,589;
 4,315,848; 4,383,863; 4,675,352; 4,681,905 and 4,853,471.
 Although benzotriazoles with just hydrogen at the 5-position of the benzo
 ring are photostable and useful in adhesive formulations, they lack a
 red-shifted absorbance toward longer UV wavelengths which would be most
 useful in giving added protection to the substrates. U.S. Pat. Nos.
 5,319,091 and 5,410,071 described the preparation of benzotriazoles
 substituted at the 5-position of the benzo ring with alkyl- or
 aryl-sulfonyl moieties. It is taught in U.S. Pat. No. 5,280,124 that by
 introducing a higher alkyl or aryl sulfoxide or sulfone at the 5-position
 of the benzo ring of the benzotriazole, the resulting benzotriazole
 exhibits enhanced absorption in the near visible range (over 350 nm). Such
 sulfone substituted products were shown to be useful in automotive
 coatings applications. Copending patent applications Ser. Nos. 08/961,127
 and 09/234,880 teach that an electron withdrawing moiety at the 5-position
 of the benzo ring of the benzotriazole is advantageous for similar
 reasons. Additionally, these copending patent applications teach that such
 an electron withdrawing group dramatically increases the photostability of
 these benzotriazole UV absorbers in automotive coatings. Quite
 surprisingly, these red-shifted benzotriazoles are amazingly soluble in
 adhesives making them especially well-suited for the instant applications.
 It is known in the art that the concomitant use of a hindered amine light
 stabilizer with a UV absorber such as a benzotriazole provides excellent
 stabilization in many polymer compositions as summarized by G. Berner and
 M. Rembold, "New Light Stabilizers for High Solids Coatings", Organic
 Coatings and Science and Technology, Vol. 6, Dekkar, New York, pp 55-85.
 The benzotriazole UV absorbers represent a special class of commercial UV
 absorbers as described above. Only a few references refer to substitution
 on the benzo ring by an aryl or alkyl sulfoxide or sulfonyl moiety.
 U.S. Pat. No. 3,218,332 discloses benzotriazoles substituted at the
 5-position of the benzo ring by a lower alkyl sulfonyl moiety. However,
 this patent deals with putting reactable groups, namely alkenyl groups, at
 the 3-position on the phenyl ring and is of little relevance to the
 instant application. U.S. Pat. Nos. 5,268,450 and 5,319,091 disclose
 polymer compositions and a process for the production of substituted aryl
 thio and aryl sulfonyl benzotriazoles which are covalently bound to
 polymers, such as poly(phenylene sulfide), RYTON.RTM., Phillips Petroleum.
 U.S. Pat. No. 5,280,124 discloses benzotriazoles with only higher alkyl or
 aryl sulfonyl or sulfonyl moieties at the 5-position of the benzo ring
 which are useful for protecting thermoset automotive coatings. The
 copending patent applications mentioned above teach the use of certain
 electron withdrawing groups including some sulfonyl groups at the
 5-position of the benzo ring for the stabilization of automotive coatings.
 Japanese Patent No. 92-352228 discloses the use of 5-ethylsulfonyl
 benzotriazoles with the 3-position of the phenyl ring being unsubstituted
 or substituted by methyl for the UV protection of dust proof poly(vinyl
 chloride) resin films. These compounds when studied in the instant
 adhesive compositions were found to be quite insoluble and totally useless
 for the instant adhesive compositions. By contrast, when a tertiary alkyl
 group is inserted at the 3-position of the phenyl ring, the solubility of
 the thus substituted benzotriazole in adhesive composition is surprisingly
 enhanced.
 The instant compounds exhibit enhanced broadened absorption characteristics
 particularly in the long wavelength UV region (over 350 nm) when compared
 with compounds of the prior art. Additionally, the instant compounds have
 surprising and unexpectedly high solubility in adhesives making them
 especially well suited for use in adhesive formulations.
 The effect of UV light on laminated articles that are exposed to the sun or
 other sources of UV light are of great concern to the manufacturers of
 such articles. Over time, constant or repeated exposure to UV light can
 result in dye and/or pigment fade for dyes and/or pigments used in such
 articles and in the degradation or breakdown of the adhesives, polymers or
 other materials used in the construction of the articles. The
 aforementioned fading and degradation shorten the useful life of the
 articles in question, making protection from UV light exposure an issue of
 great importance to the manufacturers of such articles.
 Molecules known as UV absorbers are generally known in the art. However,
 due to the differences discussed above between the various UV absorber
 classes, it is the benzotriazoles and articles containing them which will
 be discussed here. Due to the incompatibility and low solubility of
 certain benzotriazoles, a need exists for selected benzotriazoles that are
 highly soluble and which would provide added protection in the 350 to 400
 nm region of the ultraviolet. T. Nagashima et al., J. Non-Cryst. Solids,
 178 (1994), 182, report "Recently ultraviolet light (UV) shielding glass,
 which is UV absorbing over the range of long wavelengths (320-400 nm) to
 avoid sunburn effects, has become an important issue because of the
 possible hazard of skin cancer due to depletion of the ozone layer."
 In addition, articles which incorporate the selected benzotriazoles of the
 instant invention are useful in protecting interior structures, textiles
 and fabrics from UV induced photodegradation such as in automotive
 applications.
 International application WO 97/32225 describes the use of PEN films having
 reflective and polarizing elements for use as optical films.
 U.S. Pat. No. 5,770,114 discloses stabilized compositions containing
 soluble benzotriazoles that are used in electrochromic devices. However,
 these benzotriazoles lack the red-shifted absorption at the 350 to 400 nm
 region.
 Articles which would benefit from the incorporation of the instant, highly
 soluble, photostable and red-shifted benzotriazoles include, but are not
 limited to:
 (a) Retroreflective Sheets and Signs and Conformable Marketing Sheets as
 seen in WO 97/42261; and U.S. Pat. No. 5,387,458 which is incorporated
 herein by reference;
 (b) Solar Control Films of Various Construction as seen in British
 2,012,668; European 355,962; and U.S. Pat. Nos. 3,290,203; 3,681,179;
 3,776,805 and 4,095,013 which are incorporated herein by reference;
 (c) Corrosion Resistant Silver Mirrors and Solar Reflectors as seen in U.S.
 Pat. No. 4,645,714 which is incorporated herein by reference;
 (d) Reflective Print Labels as seen in U.S. Pat. No. 5,564,843 which is
 incorporated herein by reference;
 (e) UV Absorbing Glasses and Glass Coatings as seen in U.S. Pat. Nos.
 5,372,889; 5,426,204; 5,683,804 and 5,618,626 which are incorporated
 herein by reference;
 (f) Electrochromic Devices as seen in European 752,612 Al; and U.S. Pat.
 Nos. 5,239,406; 5,523,877 and 5,770,114 which are incorporated herein by
 reference;
 (g) Films/Glazings as seen in WO 92/01557; Japanese Nos. 75-33286;
 93-143668; 95-3217 and 96-143831; and U.S. Pat. No. 5,643,676 which is
 incorporated herein by reference;
 (h) Windscreens and Intermediate Layers as seen in Japanese Nos. 80-40018;
 90-192118; 90-335037; 90-335038; 92-110128 and 94-127591; and U.S. Pat.
 No. 5,618,863 which is incorporated herein by reference; and
 (i) Optical Films as seen in WO 97/32225; and U.S. Pat. Nos. 4,871,784 and
 5,217,794 which are incorporated herein by reference.
 DETAILED DISCLOSURE
 The general embodiment of the instant invention is to a stabilized adhesive
 composition, suitable for use as an adhesive layer in a laminated article
 or multilayer construction, which comprises
 (a) an adhesive; and
 (b) an effective stabilizing amount of a highly soluble, red-shifted,
 photostable benzotriazole.
 More particularly, the adhesive of component (a) is selected from the group
 consisting of the pressure sensitive adhesives, the rubber-based
 adhesives, the solvent or emulsion based adhesives, the hot melt adhesives
 and natural-product based adhesives. These adhesives are selected from the
 group consisting of the polyurethanes, polyacrylics, epoxys, phenolics,
 polyimides, poly(vinyl butyral), polycyanoacrylates, polyacrylates,
 ethylene/acrylic acid copolymers and their salts (ionomers), silicon
 polymers, poly(ethylene/vinyl acetate), atatic polypropylene,
 styrene-diene copolymers, polyamides, hydroxyl-terminated polybutadiene,
 polychloroprene, poly(vinyl acetate), carboxylated styrene/butadiene
 copolymers and poly(vinyl alcohol).
 More particularly, the highly soluble, red-shifted, photostable
 benzotriazole is of formula I, II or III
 ##STR1##
 wherein
 G.sub.1 and G.sub.1 ' are independently hydrogen or halogen, G.sub.2 and
 G.sub.2 ' are independently halogen, nitro, cyano, perfluoroalkyl of 1 to
 12 carbon atoms, --COOG.sub.3, --P(O)(C.sub.6 H.sub.5).sub.2,
 --CO--G.sub.3, --CO--NH--G.sub.3, --CO--N(G.sub.3).sub.2,
 --N(G.sub.3)--CO--G.sub.3, E.sub.3 SO-- or E.sub.3 SO.sub.2 --; or G.sub.2
 ' is also hydrogen,
 G.sub.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,
 G.sub.6 is perfluoroalkyl of 1 to 12 carbon atoms,
 G.sub.7 is hydrogen or perfluoroalkyl of 1 to 12 carbon atoms,
 E.sub.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.sub.1 is alkyl of 1 to 24
 carbon atoms substituted by one or two hydroxy groups,
 E.sub.2 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 E.sub.2 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, --OCOE.sub.11,
 --OE.sub.4, --NCO, --NH.sub.2, --NHCOE.sub.11, --NHE.sub.4 or
 --N(E.sub.4).sub.2, or mixtures thereof, where E.sub.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.sub.4 -- groups
 or mixtures thereof and which can be unsubstituted or substituted by one
 or more --OH, --OE.sub.4 or --NH.sub.2 groups or mixtures thereof;
 n is 1 or 2,
 when n is 1, E.sub.5 is OE.sub.6 or NE.sub.7 E.sub.8, or
 E.sub.5 is --PO(OE.sub.12).sub.2, --OSi(E.sub.11).sub.3 or --OCO--E.sub.11,
 or straight or branched chain C.sub.1 -C.sub.24 alkyl which is interrupted
 by --O--, --S-- or --NE.sub.11 and which can be unsubstituted or
 substituted by --OH or --OCO--E.sub.11, C.sub.5 -C.sub.12 cycloalkyl which
 is unsubstituted or substituted by --OH, straight chain or branched
 C.sub.2 -C.sub.18 alkenyl which is unsubstituted or substituted by --OH,
 C.sub.7 -C.sub.15 aralkyl, --CH.sub.2 --CHOH--E.sub.13 or glycidyl,
 E.sub.6 is hydrogen, straight or branched chain C.sub.1 -C.sub.24 alkyl
 which is unsubstituted or substituted by one or more OH, OE.sub.4 or
 NH.sub.2 groups, or --OE.sub.6 is --(OCH.sub.2 CH.sub.2).sub.w OH or
 --(OCH.sub.2 CH.sub.2).sub.w OE.sub.21 where w is 1 to 12 and E.sub.21 is
 alkyl of 1 to 12 carbon atoms,
 E.sub.7 and E.sub.8 are independently hydrogen, alkyl of 1 to 18 carbon
 atoms, straight or branched chain C.sub.3 -C.sub.18 alkyl which is
 interrupted by --O--, --S-- or --NE.sub.11 --, C.sub.5 -C.sub.12
 cycloalkyl, C.sub.6 -C.sub.14 aryl or C.sub.1 -C.sub.3 hydroxylalkyl, or
 E.sub.7 and E.sub.8 together with the N atom are a pyrrolidine,
 piperidine, piperazine or morpholine ring,
EQU E.sub.5 is --X--(Z).sub.p --Y--E.sub.15
 wherein
 X is --O-- or --N(E.sub.16)--,
 Y is --O-- or --N(E.sub.17)--,
 Z is C.sub.2 -C.sub.12 -alkylene, C.sub.4 -C.sub.12 -alkylene interrupted
 by one to three nitrogen atoms, oxygen atoms or a mixture thereof, or is
 C.sub.3 -C.sub.12 -alkylene, butenylene, butynylene, cyclohexylene or
 phenylene, each substituted by a hydroxyl group,
 m is zero, 1 or 2,
 p is 1, or p is also zero when X and Y are --N(E.sub.16)-- and
 --N(E.sub.17)--, respectively,
 E.sub.15 is a group --CO--C(E.sub.18).dbd.C(H)E.sub.19 or, when Y is
 --N(E.sub.17)--, forms together with E.sub.17 a group
 --CO--CH.dbd.CH--CO--, wherein E.sub.18 is hydrogen or methyl, and
 E.sub.19 is hydrogen, methyl or --CO--X--E.sub.20, wherein E.sub.20 is
 hydrogen, C.sub.1 -C.sub.12 -alkyl or a group of the formula
 ##STR2##
 wherein the symbols E.sub.1, G.sub.2, X, Z, m and p have the meanings
 defined above, and E.sub.16 and E.sub.17 independently of one another are
 hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 alkyl interrupted by
 1 to 3 oxygen atoms, or is cyclohexyl or C.sub.7 -C.sub.15 aralkyl, and
 E.sub.16 together with E.sub.17 in the case where Z is ethylene, also
 forms ethylene,
 when n is 2, E.sub.5 is one of divalent radicals --O--E.sub.9 --O-- or
 --N(E.sub.11)--E.sub.10 --N(E.sub.11)--,
 E.sub.9 is C.sub.2 -C.sub.8 alkylene, C.sub.4 -C.sub.8 alkenylene, C.sub.4
 alkynylene, cyclohexylene, straight or branched chain C.sub.4 -C.sub.10
 alkylene which is interrupted by --O -- or by --CH.sub.2 --CHOH--CH.sub.2
 --O--E.sub.14 --O----CH.sub.2 --CHOH--CH.sub.2 --,
 E.sub.10 being straight or branched chain C.sub.2 -C.sub.12 alkylene which
 may be interrupted by --O--, clohexylene, or
 ##STR3##
 or E.sub.10 and E.sub.11 with the two nitrogen atoms form a piperazine
 ring,
 E.sub.14 is straight or branched chain C.sub.2 -C.sub.8 alkylene, straight
 or branched chain C.sub.4 -C.sub.10 alkylene which is interrupted by
 --O--, cycloalkylene, arylene or
 ##STR4##
 where E.sub.7 and E.sub.8 are independently hydrogen, alkyl of 1 to 18
 carbon atoms or E.sub.7 and E.sub.8 together are alkylene of 4 to 6 carbon
 atoms, 3-oxapentamethylene, 3-iminopentamethylene or
 3-methyliminopentamethylene,
 E.sub.11 is hydrogen, straight or branched chain C.sub.1 -C.sub.18 alkyl,
 C.sub.5 -C.sub.12 cycloalkyl, straight or branched chain C.sub.2 -C.sub.18
 alkenyl, C.sub.6 -C.sub.14 aryl or C.sub.7 -C.sub.15 aralkyl,
 E.sub.12 is straight or branched chain C.sub.1 -C.sub.18 alkyl, straight or
 branched chain C.sub.3 -C.sub.18 alkenyl, C.sub.5 -C.sub.10 cycloalkyl,
 C.sub.6 -C.sub.16 aryl or C.sub.7 -C.sub.15 aralkyl,
 E.sub.13 is H, straight chain or branched C.sub.1 -C.sub.18 alkyl which is
 substituted by --PO(OE.sub.12).sub.2, phenyl which is unsubstituted or
 substituted by OH, C.sub.7 -C.sub.15 aralkyl or --CH.sub.2 OE.sub.12,
 E.sub.3 is alkyl of 1 to 20 carbon atoms, hydroxyalkyl of 2 to 20 carbon
 atoms, alkyl substituted by alkoxycarbonyl of 2 to 9 carbon atoms, alkenyl
 of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl
 of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl
 substituted by one or two alkyl of 1 to 4 carbon atoms or
 1,1,2,2-tetrahydroperfluoroalkyl where the perfluoroalkyl moiety is of 6
 to 16 carbon atoms, and
 L is alkylene of 1 to 12 carbon atoms, aikylidene of 2 to 12 carbon atoms,
 benzylidene, p-xylylene,
 .alpha.,.alpha.,.alpha.',.alpha.'-tetramethyl-m-xylylene or
 cycloalkylidene; and
 with the proviso that formula I does not represent
 5-ethylsulfonyl-2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole;
 5-fluoro-2-(2-hydroxy-3-a-cumyl-5-tert-octylphenyl)-2H-benzotriazole;
 5-fluoro-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-butylphenyl)-2H-benzotriazole
 ;
 5-chloro-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benzotriazole
 ;
 5-chloro-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-butylphenyl)-2H-benzotriazole
 ; 5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole; or
 5-chloro-2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-2H-benzotriazole; and
 with the further proviso that the benzotiazole of formula I, II or mH
 exhibits enhanced durability and low loss of absorbance when exposed to
 actinic radiation as witnessed by an absorbance loss of less than 0.5
 absorbance units after exposure for 893 hours or less than 0.8 absorbance
 units after exposure for 1338 hours in a Xenon Arc Weather-Ometer.
 More particularly, the compound of formula I is
 ##STR5##
 wherein
 G.sub.1 is hydrogen,
 G.sub.2 is cyano, chloro, fluoro, CF.sub.3 --, --CO--G.sub.3, E.sub.3 SO--
 or E.sub.3 SO.sub.2 --,
 G.sub.3 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 4 alkyl
 of 1 to 4 carbon atoms,
 E.sub.1 is 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.sub.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 1 to 3 alkyl
 of 1 to 4 carbon atoms; or E.sub.2 is said alkyl of 1 to 24 carbon atoms
 or said alkenyl of 2 to 18 carbon atoms substituted by one or more --OH,
 --OCOE.sub.11, --OE.sub.4, --NCO, --NH.sub.2, --NHCOE.sub.11, --NHE.sub.4
 or --N(E.sub.4).sub.2, or mixtures thereof, where E.sub.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.sub.4 -- groups
 or mixtures thereof and which can be unsubstituted or substituted by one
 or more --OH, --OE.sub.4 or --NH.sub.2 groups or mixtures thereof;
 E.sub.3 is alkyl of 1 to 20 carbon atoms, hydroxyalkyl of 2 to 20 carbon
 atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon
 atoms, phenylalkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms
 or said aryl substituted by one or two alkyl of 1 to 4 carbon atoms or
 1,1,2,2-tetrahydroperfluoroalkyl where the perfluoroalkyl moiety is of 6
 to 16 carbon atoms; or
 is a compound of formula I wherein,
 G.sub.1 is hydrogen,
 G.sub.2 is chloro, fluoro, CF.sub.3 --, E.sub.3 SO-- or E.sub.3 SO.sub.2
 --,
 E.sub.1 is hydrogen or straight or branched alkyl of 1 to 24 carbon atoms,
 E.sub.2 is as defined above, and
 E.sub.3 is straight or branched chain alkyl of 1 to 7 carbon atoms; and
 with the proviso that formula I does not represent
 5-ethylsulfonyl-2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole;
 5-fluoro-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benzotriazole
 ;
 5-fluoro-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-butylphenyl)-2H-benzotriazole
 ;
 5-chloro-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benzotriazole
 ;
 5-chloro-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-butylphenyl)-2H-benzotiiazole
 ; 5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole; or
 5-chloro-2-(2-hydroxy-3-tert-butyl-5-methylphenyl)-2H-benzotriazole; and
 with the further proviso that the benzotriazole of formula I exhibits
 enhanced durability and low loss of absorbance when exposed to actinic
 radiation as witnessed by an absorbance loss of less than 0.5 absorbance
 units after exposure for 893 hours or less than 0.8 absorbance units after
 exposure for 1338 hours in a Xenon Arc Weather-Ometer.
 Another preferred embodiment is where the benzotriazole is of formula IIA
 ##STR6##
 wherein
 G.sub.1 is hydrogen,
 G.sub.2 is CF.sub.3 -- or fluoro,
 E.sub.1 is hydrogen, straight or branched alkyl of 1 to 24 carbon atoms or
 phenylalkyl of 7 to 15 carbon atoms,
 E.sub.5 is --OE.sub.6 or --NE.sub.7 E.sub.8, or
 E.sub.5 is
EQU --X--(Z).sub.p --Y--E.sub.15
 wherein
 X is --O-- or --N(E.sub.16)--,
 Y is --O-- or --N(E.sub.17)--,
 Z is C.sub.2 -C.sub.12 -alkylene, C.sub.4 -C.sub.12 -alkylene interrupted
 by one to three nitrogen atoms, oxygen atoms or a mixture thereof, or is
 C.sub.3 -C.sub.12 -alkylene, butenylene, butynylene, cyclohexylene or
 phenylene, each substituted by a hydroxyl group,
 m is 0, 1, 2 or 3,
 p is 1, or p is also zero when X and Y are --N(E.sub.16)-- and
 --N(E.sub.17)--, respectively,
 E.sub.15 is a group --CO--C(E.sub.18).dbd.C(H)E.sub.19 or, when Y is
 --N(E.sub.17)--, forms together with E.sub.17 a group
 --CO--CH.dbd.CH--CO--, wherein E.sub.18 is hydrogen or methyl, and
 E.sub.19 is hydrogen, methyl or --CO--X--E.sub.20, wherein E.sub.20 is
 hydrogen, C.sub.1 -C.sub.12 -alkyl or a group of the formula.
 ##STR7##
 Still another preferred embodiment is a benzotriazole of formula IIIA
 ##STR8##
 wherein
 G.sub.6 is CF.sub.3,
 G.sub.7 is hydrogen or CF.sub.3,
 E.sub.2 and E.sub.2 ' 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 1 to 3 alkyl of 1 to 4 carbon atoms; and
 L is alkylene of 1 to 12 carbon atoms, alkylidene of 2 to 12 carbon atoms,
 benzylidene, p-xylylene,
 .alpha.,.alpha.,.alpha.',.alpha.'-tetramethyl-m-xylylene or
 cycloalkylidene.
 In a more preferred embodiment, the benzotriazole is of formula I
 ##STR9##
 wherein
 G.sub.6 is hydrogen,
 G.sub.2 is CF.sub.3 --,
 E.sub.1 is 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.sub.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 1 to 3 alkyl
 of 1 to 4 carbon atoms; or E.sub.2 is said alkyl of 1 to 24 carbon atoms
 or said alkenyl of 2 to 18 carbon atoms substituted by one or more --OH,
 --OCOE.sub.11, --NH.sub.2 or --NHCOE.sub.11, or mixtures thereof, or said
 alkyl or said alkenyl interrupted by one or more --O -- and which can be
 unsubstituted or substituted by one or more --OH, or
 is a compound of formula I wherein,
 G.sub.1 is hydrogen,
 G.sub.2 is CF.sub.3 --,
 E.sub.1 is hydrogen, straight or branched alkyl of 4 to 24 carbon atoms or
 phenylalkyl of 7 to 15 carbon atoms, and
 E.sub.2 is as defined above.
 In another preferred embodiment, the benzotriazole is of formula IIA
 ##STR10##
 wherein
 G.sub.1 is hydrogen,
 G.sub.2 is CF.sub.3 --,
 E.sub.1 is hydrogen, straight or branched alkyl of 4 to 24 carbon atoms or
 phenylalkyl of 7 to 15 carbon atoms,
 E.sub.5 is --OE.sub.6 or --NE.sub.7 E.sub.8 where
 E.sub.6 is hydrogen, straight or branched chain C.sub.1 -C.sub.24 alkyl
 which is unsubstituted or substituted by one or more OH groups, or
 --OE.sub.6 is --(OCH.sub.2 CH.sub.2).sub.w OH or --(OCH.sub.2
 CH.sub.2).sub.w OE.sub.21 where w is 1 to 12 and E.sub.21 is alkyl of 1 to
 12 carbon atoms, and
 E.sub.7 and E.sub.8 are independently hydrogen, alkyl of 1 to 18 carbon
 atoms, straight or branched chain C.sub.3 -C.sub.18 alkyl which is
 interrupted by --O--, --S-- or --NE.sub.11 --, C.sub.5 -C.sub.12
 cycloalkyl, C.sub.6 -C.sub.14 aryl or C.sub.1 -C.sub.3 hydroxylalkyl, or
 E.sub.7 and E.sub.8 together with the N atom are a pyrrolidine,
 piperidine, piperazine or morpholine ring.
 In an especially preferred embodiment, the benzotriazole is of formula IIIA
 ##STR11##
 wherein
 G.sub.6 is CF.sub.3,
 G.sub.7 is hydrogen or CF.sub.3,
 E.sub.2 and E.sub.2 ' 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 1 to 3 alkyl of 1 to 4 carbon atoms; and
 L is methylene.
 Preferably, the benzotriazole is a compound which is
 (a)
 5-trifluoromethyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benz
 o-triazole;
 (b) 5-trifluoromethyl-2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole;
 (c)
 5-trifluoromethyl-2-(2-hydroxy-3,5-di-tert-octylphenyl)-2H-benzotriazole;
 (d)
 2,2'-methylene-bis[6-(5-trifluoromethyl-2H-benzotriazol-2-yl)-4-tert-octyl
 -phenol];
 (e)
 methylene-2-[4-tert-octyl-6-(2H-benzotriazol-2-yl)phenol]2'-[4-tert-octyl-
 6-(5-trifluoromethyl-2H-benzotriazol-2-yl)phenol];
 (f)
 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-hydrocin
 namic acid;
 (g) methyl
 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-hydrocin
 namate;
 (h) isooctyl
 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-hydrocin
 namate;
 (i)
 5-trifluoromethyl-2-[2-hydroxy-5-(3-hydroxypropyl)phenyl]-2H-benzotriazole
 ;
 (j)
 5-butylsulfonyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benzot
 riazole;
 (k)
 5-octylsulfonyl-2-(2-hydroxy-3,5-di-.alpha.-cumylphenyl)-2H-benzotriazole;
 (l)
 5-dodecylsulfonyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole;
 (m) 5-octylsulfonyl-2-(2-hydroxy-3,5-di-tert-octylphenyl)-2H-benzotriazole;
 (n)
 5-trifluorometbyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-butylphenyl)-2H-benz
 o-triazole;
 (o)
 5-trifluoromethyl-2-(2-hydroxy-3-.alpha.-cumyl-5-nonylphenyl)-2H-benzotria
 zole;
 (p)
 5-trifluoromethyl-2-[2-hydroxy-3-.alpha.-cumyl-5-(2-hydroxyethyl)phenyl]-2
 H-benzotriazole;
 (q)
 5-trifluoromethyl-2-[2-hydroxy-3-.alpha.-cumyl-5-(3-hydroxypropyl)phenyl]-
 2H-benzotriazole;
 (r)
 5-trifluoromethyl-2-(2-hydroxy-3,5-di-tert-amylphenyl)-2H-benzotriazole;
 (s)
 5-trifluoromethyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole;
 (t)
 5-trifluoromethyl-2-(2-hydroxy-3-dodecyl-5-methylphenyl)-2H-benzotriazole;
 (u)
 5-trifluoromethyl-2-[2-hydroxy-3-tert-butyl-5-(3-hydroxypropyl)phenyl)-2H-
 benzotriazole;
 (v)
 5-trifluoromethyl-2-[2-bydroxy-3-tert-butyl-5-(2-bydroxyethyl)phenyl]-2H-b
 enzotriazole;
 (w)
 5-trifluoromethyl-2-[2-hydroxy-5-(2-hydroxyethyl)phenyl]-2H-benzotriazole;
 (x)
 5-trifluoromethyl-2-(2-hydroxy-3,5-di-.alpha.-cumylphenyl)-2H-benzotriazol
 e;
 (y) 5-fluoro-2-(2-bydroxy-3,5-di-.alpha.-cumylphenyl)-2H-benzotriazole;
 (z)
 5-butylsulfonyl-2-(2-hydroxy-3,5-di-.alpha.-cumylphenyl)-2H-benzotriazole;
 (aa)
 5-butylsulfonyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole;
 (bb)
 5-butylsulfonyl-2-(2-bydroxy-3,5-di-tert-octylphenyl)-2H-benzotriazole;
 (cc)
 5-phenylsulfonyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole;
 and
 (dd) 5-chloro-2-(2-hydroxy-3,5-di-.alpha.-cumylphenyl)-2H-benzotriazole.
 Most preferably, the benzotriazoles of especial interest are
 (a)
 5-trifluoromethyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benz
 o-triazole;
 (b) 5-trifluoromethyl-2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole;
 (c)
 5-trifluoromethyl-2-(2-hydroxy-3,5-di-tert-octylphenyl)-2H-benzotriazole;
 (g) methyl
 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxy-hydrocin
 namate;
 (j)
 5-butylsulfonyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tent-octylphenyl)-2H-benzot
 riazole;
 (n)
 5-trifluoromethyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-butylphenyl)-2H-benz
 o-triazole;
 (s)
 5-trifluoromethyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole;
 (x)
 5-trifluoromethyl-2-(2-hydroxy-3,5-di-.alpha.-cumylphenyl)-2H-benzotriazol
 e;
 (aa)
 5-butylsulfonyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole;
 and
 (cc)
 5-phenylsulfonyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole.
 The effective stabilizing amount of a benzotriazole of formula I, II or III
 is 0.1 to 20% by weight based on the adhesive.
 The instant adhesive stabilized by a benzotriazole of formula I, II or III
 may also optionally contain from 0.01 to 10% by weight; preferably from
 0.025 to 5% by weight, and most preferably from 0.1 to 3% by weight of
 additional coadditives such as antioxidants, other UV absorbers, hindered
 amines, phosphites or phosphonites, hydroxylamines, nitrones,
 benzofuran-2-ones, thiosynergists, polyamide stabilizers, metal stearates,
 nucleating agents, fillers, reinforcing agents, lubricants, emulsifiers,
 dyes, pigments, optical brighteners, flame retardants, antistatic agents,
 blowing agents and the like.
 The stabilizers of the instant invention may readily be incorporated into
 the adhesive compositions by conventional techniques, at any convenient
 stage prior to the manufacture of shaped articles therefrom. For example,
 the stabilizer may be mixed with the polymer in dry powder form, or a
 suspension or emulsion of the stabilizer may be mixed with a solution,
 suspension, or emulsion of the polymer. The resulting stabilized adhesive
 compositions of the invention may optionally also contain from about 0.01
 to about 10%, preferably from about 0.025 to about 5%, and especially from
 about 0.1 to about 3% by weight of various conventional stabilizer
 coadditives, such as the materials listed below, or mixtures thereof.
 1. Antioxidants
 1.1. Alkylated monophenols, for example,
 2,6-di-tert-butyl-4-methylphenol
 2-tert-butyl-4,6-dimethylphenol
 2,6-di-tert-butyl-4-ethylphenol
 2,6-di-tert-butyl-4n-butylphenol
 2,6-di-tert-butyl-4i-butylphenol
 2,6-di-cyclopentyl-4-methylphenol
 2-(.alpha.-methylcyclohexyl)-4,6-dimethylphenol
 2,6-di-octadecyl-4-methylphenol
 2,4,6-tri-cyclohexylphenol
 2,6-di-tert-butyl-4-methoxymethylphenol
 1.2. Alkylated hydroguinones, for example,
 2,6-di-tert-butyl-4-methoxyphenol
 2,5-di-tert-butyl-hydroquinone
 2,5-di-tert-amyl-hydroquinone
 2,6-diphenyl-4-octadecyloxyphenol
 1.3. Hydroxylated thiodiphenyl ethers, for example,
 2,2'-thio-bis-(6-tert-butyl-4-methylphenol)
 2,2'-thio-bis-(4-octylphenol)
 4,4'-thio-bis-(6-tert-butyl-3-methylphenol)
 4,4'-thio-bis-(6-tert-butyl-2-methylphenol)
 1.4. Alkylidene-bisphenols, for example,
 2,2'-methylene-bis-(6-tert-butyl-4-methylphenol)
 2,2'-methylene-bis-(6-tert-butyl-4-ethylphenol)
 2,2'-methylene-bis-[4-methyl-6-(.alpha.-methylcyclohexyl)-phenol]
 2,2'-methylene-bis-(4-methyl-6-cyclohexylphenol)
 2,2'-methylene-bis-(6-nonyl-4-methylphenol)
 2,2'-methylene-bis-[6-(.alpha.-methylbenzyl)-4-nonylphenol]
 2,2'-methylene-bis-[6-(.alpha.,.alpha.-dimethylbenzyl)-4-nonylphenol]
 2,2'-methylene-bis-(4,6-di-tert-butylphenol)
 2,2'-ethylidene-bis-(4,6-di-tert-butylphenol)
 2,2'-ethylidene-bis-(6-tert-butyl-4-isobutylphenol)
 4,4'-methylene-bis-(2,6-di-tert-butylphenol)
 4,4'-methylene-bis-(6-tert-butyl-2-methylphenol)
 1,1-bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-butane
 2,6-di-(3-tert-butyl-5-methyl-2-hydroxybenzyl)-4-methylphenol
 1,1,3-tris-(5-tert-butyl-4-hydroxy-2-methylphenyl)-butane
 1,1-bis-(5-tert-butyl-4-hydroxy-2-methylphenyl)-3-n-dodecylmercaptobutane
 ethyleneglycol bis-[3,3-bis-(3'-tert-butyl-4'-hydroxyphenyl)-butyrate]
 di-(3-tert-butyl-4-hydroxy-5-methylphenyl)-dicyclopentadiene
 di-[2-(3'-tert-butyl-2'-hydroxy-5'-methyl-benzyl)-6-tert-butyl-4-methylphe
 nyl] terephthalate.
 1.5. Benzyl compounds, for example,
 1,3,5-tri-(3,5-di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzene
 di-(3,5-di-tert-butyl-4-hydroxybenzyl) sulfide
 3,5-di-tert-butyl-4-hydroxybenzyl-mercapto-acetic acid isooctyl ester
 bis-(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithiol terephthalate
 1,3,5-tris-(3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate
 1,3,5-tris-(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate
 3,5-di-tert-butyl-4-hydroxybenzyl-phosphoric acid dioctadecyl ester
 3,5-di-tert-butyl-4-hydroxybenzyl-phosphoric acid monoethyl ester,
 calcium-salt
 1.6. Acylaminophenols, for example,
 4-hydroxy-lauric acid anilide
 4-hydroxy-stearic acid anilide
 2,4-bis-octylmercapto-6-(3,5-tert-butyl-4-hydroxyanilino)-s-triazine
 octyl-N-(3,5-di-tert-butyl-4-hydroxyphenyl)-carbamate
 1.7. Esters of .beta.-(3,5-di-tert-butyl-4-hydroxyphenyl)-propionic acid
 with monohydric or polyhydric alcohols, for example,

The following examples are for illustrative purposes only and are not to be
 construed to limit the instant invention in any manner whatsoever.
 EXAMPLE 1
 UV Absorption Spectra
 The instant benzotriazoles having different electron withdrawing groups in
 the 5-position of the benzo ring of the benzotriazole and with the
 remaining portion of the molecule being the same (substituted on the
 phenyl ring with a 3-.alpha.-cumyl moiety and a 5-tert-octyl group) are
 clearly red-shifted as seen by the wavelength at their maximum absorbance
 value. The UV spectra are measured in ethyl acetate solution at ca. 20
 mg/L concentration.

absorbance
 Compound* .lambda.max (nm) at 375 (nm)
 A 345 0.28
 B 348 0.33
 C 362 0.50
 D 358 0.42
 *A is 2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benzotriazole.
 B is
 5-trifluoromethyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benz
 otriazole.
 C is
 5-phenylsulfonyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benzo
 triazole.
 D is
 5-methoxycarbonyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benz
 otriazole.
 EXAMPLE 2
 UV Absorption Spectra
 The instant benzotriazoles having different electron withdrawing groups in
 the 5-position of the benzo ring of the benzotriazole and with the
 different substitutions on the phenyl ring at the 3- and 5-positions. The
 UV absorption spectra are measured in ethyl acetate at approximately 20
 mg/L concentration. The instant compounds are clearly red-shifted as
 compared to the compound having only a hydrogen at the 5-position of the
 hbenzo ring.

absorbance
 Compound* .lambda.max (nm) at 375 (nm)
 A 345 0.28
 E 357 0.59
 F 354 0.41
 *A is 2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benzotriazole.
 E is
 5-butylsulfonyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole.
 F is methyl
 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinn
 amate.
 EXAMPLE 3
 Benzotriazole Solubility in Adhesive
 To measure this solubility a number of structurally different
 benzotriazoles are added to a typical adhesive GELVA.RTM. 263 (Solutia)
 which is a 44.5% solution of a polyacrylate in a mixture of ethyl acetate
 and hexane. The polyacrylate is a copolymer of methyl methacrylate,
 2-ethylhexyl methacrylate and glycidyl methacrylate.
 The test benzotriazole is dissolved in 5 mL of ethyl acetate, toluene or a
 mixture of ethyl acetate and toluene. To the solution is added 5 g of
 GELVA.RTM. 263 and 2-3 mL of the resulting solution is placed into
 individual watch glasses. Solubility is then evaluated based upon observed
 crystallization once the solvent has evaporated. Observations start after
 several hours and then continue over a period of several weeks.
 The solubility values given in the table below are approximate maximum
 concentrations where no sign of subsequent crystallization is evident.
 Solubilities are reported in weight of total benzotriazole added to
 GELVA.RTM. 263 as is. From these data it clear that the instant
 benzotriazoles are considerably more soluble in adhesives (in this case
 GELVA.RTM. 263) than many benzotriazoles of the prior art. The use of many
 benzotriazoles in adhesives has been limited in the past by the limited
 solubility and compatibility of some benzotriazole compounds. By using the
 instant benzotriazoles, the use levels can be increased substantially to
 add greatly increased stabilization protection which is further augmented
 by the photostability and the red-shiftedness of the instant
 benzotriazoles.

Solubility without
 Compound* Trade Name or Class Crystallization (%)
 A 5-ethylsulfonyl &lt;1
 B TINUVIN .RTM. 900 2.0
 C TINUVIN .RTM. 327 2.0
 D 5-butylsulfonyl 4.0
 E 5-CF.sub.3 4.0
 F 5,5'-CF.sub.3 4.0
 G 5-butylsulfonyl 8.0
 H 5-CF.sub.3 8.0
 I 5-CF.sub.3 8.0
 J 5-methoxycarbonyl- 8.0
 methylsulfinyl
 K 5-phenylsulfonyl 11.3
 L 5-phenylsulfonyl 11.3
 M 5-CF.sub.3 22.6
 N 5-CF.sub.3 22.6
 O 5-CF.sub.3 22.6
 *A is 5-ethylsulfonyl-2-(2-hydroxy-5-methylphenyl)-2H-benzotriazole.
 B is 2-(2-hydroxy-3,5-di-.alpha.-cumylphenyl)-2H-benzotriazole.
 C is 5-chloro-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole.
 D is 5-butylsulfonyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotrizole.
 E is
 5-trifluoromethyl-2-(2-hydroxy-3,5-di-.alpha.-cumylphenyl)-2H-benzotriazol
 e.
 F is
 2,2'-methylene-bis[6-(5-trifluoromethyl-2H-benzotriazol-2-yl)-4-tert-octyl
 phenol].
 G is
 5-butylsulfonyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benzot
 riazole;
 H is 5-trifluoromethyl-2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole;
 I is methyl
 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinn
 amate.
 J is
 5-methoxycarbonylmethylsulfinyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-b
 enzotriazole.
 K is methyl
 3-(5-phenylsulfonyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinna
 mate.
 L is
 5-phenylsulfonyl-2-(2-hydroxy-3,5-di-tert-butylphenyl)-2H-benzotriazole.
 M is
 5-trifluoromethyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benz
 otriazole.
 N is
 5-trifluoromethyl-2-(2-hydroxy-3,5-di-tert-octylphenyl)-2H-benzotriazole.
 O is
 5-trifluoromethyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-butylphenyl)-2H-benz
 otriazole.
 EXAMPLE 4
 Weathering Experiments
 To ascertain the effect of durability and loss rate of benzotriazoles, the
 following tests are carried out on adhesive compositions in selected
 articles.
 GELVA.RTM. 263 (Solutia) adhesive is described in Example 3. A biaxially
 oriented poly(ethylene terephthalate) (PET) film is obtained from United
 States Plastics.
 The GELVA.RTM. 263 is reduced 50% by dilution with ethyl acetate to a final
 resin solids content of 23%. The test stabilizer is dissolved in the
 GELVA.RTM. 263 solution and samples are prepared in duplicate. The
 formulations seen in the table below are based on total coating solids.
 Approximately 8 micron coatings are applied to 1.5 inch glass discs for
 each formulation using a Headway Research Inc. Photo Resist Spinner (Model
 EC101DT) operating at 5000 rpm for 10 seconds. All formulations receive
 the same 80.degree. C..times.3 minute bake in a Hereaus model LUT 6050F
 oven operating at 3 air changes/minute.
 Since the adhesive remains tacky even after baking a direct thickness
 measurement is not possible. Indirect film thickness is determined by
 creating an adhesive sandwich between to layers of PET film and comparing
 its thickness versus two PET sheets without adhesive using magnetic
 induction methodology.
 The spin coating conditions are thus obtained. Further, since the spin
 coating conditions are not changed for applying the adhesive onto the
 glass, very little if any thickness variations are expected. After curing
 it in an oven, a layer of PET (ca 2 mils) is placed over the adhesive and
 pressed down.
 Absorbance spectra are collected using a Perkin Elmer Lambda 19
 Spectrophotometer running UVWINLAB software. Absorbance data are collected
 from 400-300 nm every half nanometer at a speed of 240 nm/minute and a
 slit width of 2 nm.
 Weathering is done at a controlled irradiance at 6500 W. The cycle is as
 follows: 3.8 hours straight irradiance with no water spray, followed by
 one hour darkness. In the light cycle, the black panel temperature is
 controlled at 89.degree. C. The chamber (dry bulb) temperature is
 62.degree. C. in the light cycle. The relative humidity in the light cycle
 is in the range of 50-55% and in the dark cycle 95%. The chamber (dry
 bulb) temperature is 38.degree. C. in the dark cycle.
 The test samples are placed in a Xenon Arc Weather-O-meter with the glass
 facing the Xenon lamp to emulate articles such as solar films. UV spectra
 are obtained at about 250 hour intervals. UV spectra are obtained at 500
 hours and the samples are rotated to insure that all samples receive
 similar weathering conditions.
 To follow the loss of UV absorbers from the adhesive composition, UV
 spectra measured initially and after weathering. The UV spectrophotometer
 measure absorbance linearly up to 5.5 absorbance units using a reference
 beam attenuation technique.
 It is assumed that the degradation products for the UV absorber do not
 contribute to the UV spectrum. This is tested by following the ratio of
 absorbance of the band at 300 nm and the band at about 340 nm. The ratio
 does not change upon weathering the sample. This suggests that the UV
 spectrum of the weathered films correspond to the amount of UV absorber
 remaining in the film with very little if any contribution to the spectrum
 by the photodegradants.
 The results after 893 hours exposure are given in the table below.

Initial Final
 Compound (%)* Absorbance Absorbance Absorbance Loss
 I (8%) 2.998 2.048 0.950
 II (10%) 2.810 2.013 0.797
 III (10%) 2.181 1.904 0.277
 III (10%) + 2.088 1.974 0.114
 IV (0.5%)
 *% is the weight amount in formulation.
 I is 2,2'-dihydroxy-4-methoxybenzophenone.
 II is octyl 3-(2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinnamate.
 III is
 5-trifluoromethyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benz
 otriazole.
 IV is bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate.
 These data clearly show that the instant benzotriazoles substituted at the
 5-position of the benzo ring with an electron withdrawing moiety are
 especially durable in adhesives as measured by the low loss rate of
 absorbance values after exposure to actinic radiation. Additionally, it is
 seen that the red-shifted benzotriazoles are far superior to the
 benzophenones in adhesive compositions. Furthermore, the combination of
 the red-shifted benzotriazoles with a hindered amine stabilizer offers
 quite superior performance. In summary, the instant red-shifted
 benzotriazoles combine both great photostability and unexpectedly high
 solubility in adhesive systems.
 EXAMPLE 5
 Weathering Experiments
 In an experiment similar to Example 4, GELVA.RTM. 263 (Solutia) adhesive
 described in Example 3, which contains 8% by weight of a test compound, is
 placed between a sheet of glass and a biaxially oriented film of
 poly(ethylene terephthalate) (PET) described in Example 4. The structure
 is then exposed to weathering for 947 hours as described in Example 4.
 The results are seen in the table below. Each test sample also contains
 0.5% of the hindered amine
 bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4-yl) sebacate.

Initial Final
 Compound (%)* Absorbance Absorbance Absorbance Loss
 I (8%) 2.88 2.12 0.76
 II (8%) 1.73 1.55 0.18
 III (8%) 1.46 1.45 0.01
 *% is the weight amount in formulation.
 I is 2,2'-dihydroxy-4-methoxybenzophenone.
 II is methyl
 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinn
 amate.
 III is
 5-trifluoromethyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benz
 otriazole.
 These data clearly show that the instant benzotriazoles substituted at the
 5-position of the benzo ring with an electron withdrawing moiety are
 especially durable in adhesives as measured by the low loss rate of
 absorbance values after exposure to actinic radiation. Additionally, it is
 seen that the red-shifted benzotriazoles are far superior to the
 benzophenones in adhesive compositions. Furthermore, the combination of
 the red-shifted benzotriazoles with a hindered amine stabilizer offers
 quite superior performance. In summary, the instant red-shifted
 benzotriazoles combine both great photostability and unexpectedly high
 solubility in adhesive systems.
 EXAMPLE 6
 Windshield Interlayer Assembly
 When an adhesive composition containing a benzotriazole UV absorber is
 placed between two sheets of glass, the assembly resembles a typical
 windshield. In this confined environment, there is no chance that the
 benzotriazole stabilizer can escape by volatility since the glass sheets
 provide a impervious container for the adhesive interlayer. The
 photostability and durability of the soluble benzotriazole stabilizer is
 now paramount. Benzotriazole UV absorbers whose structures causes them to
 be volatile and which precludes their use in other types of applications
 can be used in such windshield interlayer assemblies with impunity to
 achieve long lasting and stable windshield structures.
 A windshield or windscreen prototype structure is exposed to weathering
 according to the procedure described in Example 4. The GELVA.RTM. 263
 (Solutia) adhesive is placed between two sheets of glass and additionally
 contains 8% by weight of selected test UV absorbers. The structure is then
 exposed to weathering for 1338 hours as described in Example 4.
 The results are seen in the table below. Each test sample contains only a
 UV absorber and no hindered amine coadditive.

Initial Final
 Compound (%)* Absorbance Absorbance Absorbance Loss
 I (8%) 2.69 0.85 1.84
 II (8%) 2.24 1.54 0.70
 III (8%) 1.81 1.02 0.79
 *% is the weight amount in formulation.
 I is 2,2'-dihydroxy-4-methoxybenzophenone.
 II is 5-trifluoromethyl-2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole.
 III is methyl
 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinn
 amate.
 These data clearly show that the instant benzotriazoles substituted at the
 5-position of the benzo ring with an electron withdrawing moiety are
 especially durable in adhesives as measured by the low loss rate of
 absorbance values after exposure to actinic radiation. Additionally, it is
 seen that the red-shifted benzotriazoles are far superior to the
 benzophenones in adhesive compositions. In summary, the instant
 red-shifted benzotriazoles combine both great photostability and
 unexpectedly high solubility in adhesive systems.
 EXAMPLE 7
 A windshield or windscreen prototype structure as described in Example 6 is
 exposed to weathering according to the procedure described in Example 4.
 The GELVA.RTM. 263 (Solutia) adhesive is placed between two sheets of
 glass and additionally contains 8% by weight of selected test UV
 absorbers. The structure is then exposed to weathering for 1338 hours as
 described in Example 4.
 The results are seen in the table below. Each test sample also contains
 0.5% of the hindered amine
 bis(1-octyloxy-2,2,6,6-tetramethylpiperidin-4yl) sebacate.

Initial Final
 Compound (%)* Absorbance Absorbance Absorbance Loss
 I (8%) 3.69 2.89 0.80
 II (8%) 2.06 1.85 0.21
 III (8%) 1.45 l.21 0.24
 IV (8%) 1.84 1.61 0.23
 V (8%) 1.34 1.02 0.32
 *% is the weight amount in formulation.
 I is 2,2'-dihydroxy-4-methoxybenzophenone.
 II is 5-trifluoromethyl-2-(2-hydroxy-5-tert-octylphenyl)-2H-benzotriazole.
 III is
 5-trifluoromethyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benz
 otriazole.
 IV is methyl
 3-(5-trifluoromethyl-2H-benzotriazol-2-yl)-5-tert-butyl-4-hydroxyhydrocinn
 amate.
 V is
 5-n-butylsulfonyl-2-(2-hydroxy-3-.alpha.-cumyl-5-tert-octylphenyl)-2H-benz
 otriazole.
 These data clearly show that the instant benzotriazoles substituted at the
 5-position of the benzo ring with an electron withdrawing moiety are
 especially durable in adhesives as measured by the low loss rate of
 absorbance values after exposure to actinic radiation. Additionally, it is
 seen that the red-shifted benzotriazoles are far superior to the
 benzophenones in adhesive compositions. Furthermore, the combination of
 the red-shifted benzotriazoles with a hindered amine stabilizer offers
 quite superior performance. In summary, the instant red-shifted
 benzotriazoles combine both great photostability and unexpectedly high
 solubility in adhesive systems.
 EXAMPLE 8
 The instant benzotriazole UV absorbers can be used in film and rigid
 plastic protective overlaminates for printed matter and photographs
 providing excellent photostability.
 EXAMPLE 9
 The instant benzotriazole UV absorbers can be used in backlit displays to
 provide excellent long term stabilization.
 EXAMPLE 10
 The instant benzotriazole UV absorbers can be used in semi-transparent and
 opaque window displays, signs and decals wherein a film or rigid plastic
 graphic is laminated to window glass to provide excellent long term
 stabilization.
 EXAMPLE 11
 The instant benzotriazole UV absorbers can be used in clear/tinted
 anti-graffiti films used over class, metal or plastic substrates to
 provide excellent long term stabilization.
 EXAMPLE 12
 The instant benzotriazoleUV absorbers can be used in clear anti-lacerative
 or "security" films used over or between layers of glass or polycarbonate
 to provide long term stabilization.
 EXAMPLE 13
 The instant benzotriazole UV absorbers can be used in decorative and
 protective films and dec als for painted surfaces such as on automobiles,
 buses, equipment and other exterior products to provide long term
 stabilization.