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

A stabilized adhesive composition, suitable for use as an adhesive layer in a laminated article or multilayer construction, which comprises

• (a) an adhesive resin selected from the group consisting of the
• (i) polyurethanes;
• (ii) polyacrylics;
• (vi) poly(vinyl butyral);
• (viii) polyacrylates;
• (xi) poly(ethylenelvinyl acetate);
• (xvii) polytvinyl acetate);
• and
• (xx) polyesters;
• and
• (b) an effective stabilizing amount of a benzotriazole of formula I, II or III
• wherein
• G1 and G1′ are independently hydrogen or halogen, G2 and G2′ are independently perfluoroalkyl of 1 to 12 carbon atoms;
• or G2′ is also hydrogen,
• E1 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 E1 is alkyl of 1 to 24 carbon atoms substituted by one or two hydroxy groups,
• 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;
• n is 1 or 2,
• when n is 1, E5 is OE6 or NE7E8, or
• E5 is —PO(OE12)2, —OSi(E11)3 or —OCO—E11, or straight or branched chain C1-C24alkyl which is interrupted by —O—, —S—or —NE11, and which can be unsubstituted or substituted by —OH or —OCO—E11, C5-C12 cycloalkyl which is unsubstituted or substituted by —OH, straight chain or branched C2-C18alkenyl which is unsubstituted or substituted by —OH, C7-C15aralkyl, —CH2—CHOH—E13 or glycidyl,
• E6 is hydrogen, straight or branched chain C1-C24alkyl which is unsubstituted or substituted by one or more OH, OE4 or NH2 groups, or —OE6 is —(OCH2CH2)wOH or —(OCH2CH2) wOE21where w is 1 to 12 and E21 is alkyl of 1 to 12 carbon atoms,
• E7 and E8 are independently hydrogen, alkyl of 1 to 18 carbon atoms, straight or branched chain C3-C18alkyl which is interrupted by —O—, —S—or —NE11—, C5-C12cycloalkyl, C6-C14aryl or C1-C3hydroxylalkyl, or E7 and E8 together with the N atom are a pyrrolidine, piperidine, piperazine
• or morpholine ring,
• E5 is —X—(Z)P—Y—E15
• wherein
• X is —O—or —N(E16)—,
• Y is —O—or —N(E17)—,
• Z is C2-C12-alkylene, C4-C12-alkylene interrupted by one to three nitrogen atoms, oxygen atoms or a mixture thereof, or is C3-C12-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(E16)—and —N(E17)—, respectively,
• E15 is a group —CO—C(E18)═C(H)E19 or, when Y is —N(E17)—, forms together with E17 a group —CO—CH═CH—CO—, wherein E18 is hydrogen or methyl, and E19 is hydrogen, methyl or —CO—X—E20, wherein E20 is hydrogen, C1-C12-alkyl or a group of the formula
• wherein the symbols E1, G2, X, Z, m and p have the meanings defined above, and E16 and E17 independently of one another are hydrogen, C1-C12-alkyl, C3-C12-alkyl interrupted by 1 to 3 oxygen atoms, or is cyclohexyl or C7-C15aralkyl, and E16 together with E17 in the case where Z is ethylene, also forms ethylene,
• when n is 2, E5 is one of divalent radicals —O—E9—O—or —N(E11)—E10—N(E11)—,
• E9 is C2-C8alkylene, C4-C8alkenylene, C4alkynylene, cyclohexylene, straight or branched chain C4-C10alkylene which is interrupted by —O—or by —CH2—CHOH—CH2—O—E14—O—CH2—CHOH—CH2—,
• E10 being straight or branched chain C2-C12alkylene which may be interrupted by —O—, cyclohexylene, or
• or E10 and E11 with the two nitrogen atoms form a piperazine ring,
• E14 is straight or branched chain C2-C8alkylene, straight or branched chain C4-C10alkylene which is interrupted by —O—, cycloalkylene, arylene or
• where E7 and E8 are independently hydrogen, alkyl of 1 to 18 carbon atoms or E7 and E8 together are alkylene of 4 to 6 carbon atoms, 3-oxapentamethylene, 3-iminopentamethylene or 3-methyliminopentamethylene,
• E11 is hydrogen, straight or branched chain C1-C18alkyl, C5-C12cycloalkyl, straight or branched chain C2-C18alkenyl, C6-C14aryl or C7-C15aralkyl,
• E12 is straight or branched chain C1-C18alkyl, straight or branched chain C3-C18alkenyl, C5-C10cycloalkyl, C6-C16aryl or C7-C15aralkyl,
• E13 is H, straight chain or branched C1-C18alkyl which is substituted by —PO(OE12)2, phenyl which is unsubstituted or substituted by OH, C7-C15aralkyl —r -CH2OE12, and
• L is alkylene of 1 to 12 carbon atoms, alkylidene of 2 to 12 carbon atoms, benzylidene, p-xylylene, α,α,α′,α′-tetramethyl-m-xylylene or cycloalkylidene.