Stabilized adhesive compositions containing highly soluble, high extinction photostable hydroxyphenyl-s-triazine 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;
• and
• (b) an effective stabilizing amount of a highly soluble, high molar extinction and photostable s-triazine UV absorber of formula I, II, III, IV V or VI
• wherein
• X and Y are independently phenyl, naphthyl, or said phenyl or said naphthyl substituted by one to three alkyl of 1 to 6 carbon atoms, by halogen, by hydroxy or by alkoxy of 1 to 6 carbon atoms or by mixtures thereof;
• or X and Y are independently Z1 or Z2;
• R1 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, halogen, —SR3, —SOR3 or —SO2R3;
• or said alkyl, said cycloalkyl or said phenylalkyl substituted by one to three halogen, —R4, —OR5, —N(R5)2, —COR5, —COOR5, —OCOR5, —CN, —NO2, —SR5, —SOR5, —SO2R5 or —P(O)(OR5)2, morpholinyl, piperidinyl, 2,2,6,6-tetramethylpiperidinyl, piperazinyl or N-methylpiperidinyl groups or combinations thereof;
• or said alkyl or said cycloalkyl interrupted by one to four phenylene, —O—, —NR5—, —CONR5—, —COO—, —OCO— or —CO groups or combinations thereof;
• or said alkyl or said cycloalkyl both substituted and interrupted by combinations of the groups mentioned above;
• R3 is alkyl of 1 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;
• R4 is aryl of 6 to 10 carbon atoms or said aryl substituted by one to three halogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms or combinations thereof;
• cycloalkyl of 5 to 12 carbon atoms;
• phenylalkyl of 7 to 15 carbon atoms or said phenylalkyl substituted on the phenyl ring by one to three halogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms or combinations thereof;
• or straight or branched chain alkenyl of 2 to 18 carbon atoms;
• R5 is defined as is R4;
• or R5 is also hydrogen or straight or branched chain alkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms;
• or R5 is a group for formula
• T is hydrogen, oxyl, hydroxyl, —OT1, alkyl of 1 to 24 carbon atoms, said alkyl substituted by one to three hydroxy;
• benzyl or alkanoyl of 2 to 18 carbon atoms;
• T1 is alkyl of 1 to 24 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, alkenyl of 2 to 24 carbon atoms, cycloalkenyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, a radical of a saturated or unsaturated bicyclic or tricyclic hydrocarbon of 7 to 12 carbon atoms or aryl of 6 o 10 carbon atoms or said aryl substituted by one to three alkyl of 1 to 4 carbon atoms;
• R2 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms or cycloalkyl of 5 to 12 carbon atoms;
• or said alkyl or said cycloalkyl substitute by one to four halogen, epoxy, glycidyloxy, furyloxy, —R4, —OR5, —N(R5)2, —CON(R5)2, —COR5, —COOR5, —OCOR5, —OCOC(R5)═C(R5)2, —C(R5)═CCOOR5, —CN, —NCO, or
• or combinations thereof;
• or said alkyl or said cycloalkyl interrupted by one to four epoxy, —O—, —NR5—, —CONR5—, —COO—, —OCO—, —CO—, —C(R5)═C(R5)COO—, —OCOC(R5)═C(R5)—, —C(R5)═C(R5)—, phenylene or phenylene-G-phenylene in which G is —O—, —S—, —SO2—, —CH2— or —C(CH3)2— or combinations thereof, or said alkyl or said cycloalkyl both substituted and interrupted by combinations of the groups mentioned above;
• or R2 is —SO2R3 or —COR6;
• R6 is straight or branched chain alkyl of 1 to 18 carbon atoms, straight or branched chain alkenyl of 2 to 12 carbon atoms, phenoxy, alkylamino of 1 to 12 carbon atoms, arylamino of 6 to 12 carbon atoms, —R7COOH or —NH—R8—NCO;
• R7 is alkylene of 2 to 14 carbon atoms or phenylene;
• R8 is alkylene of 2 to 24 carbon atoms, phenylene, tolylene, diphenylmethane or a group
• R1, R1′ and R1″ are the same or different and are as defined for R1;
• R2, R2′ and R2″ are the same or different and are as defined for R2;
• X, X′, Y and Y′ are the same or different and are as defined for X and Y;
• t is 0 to 9;
• L is straight or branched alkylene of 1 to 12 carbon atoms, cycloalkylene of 5 to 12 carbon atoms or alkylene substituted or interrupted by cyclohexylene or phenylene;
• or L is benzylidene;
• or L is —S—, —S—S—, —S—E—S—, —SO—, —SO2—, —SO—E—SO—, —SO2—E—SO2—, —CH2—NH—E—NH—CH2— or
• E is alkylene of 2 to 12 carbon atoms, cycloalkylene of 5 to 12 carbon atoms or alkylene interrupted or terminated by cycloalkylene of 5 to 12 carbon atoms;
• n is 2, 3 or 4;
• when n is 2;
• Q is straight or branched alkylene of 2 to 16 carbon atoms;
• or said alkylene substituted by one to three hydroxy groups;
• or said alkylene interrupted by one to three —CH═CH— or —O—;
• or said alkylene both substituted and interrupted by combinations of the groups mentioned above;
• or Q is xylylene or a group —CONH—R8—NHCO—, —CH2CH(OH)CH2O—R9—OCH2CH(OH)CH2—, —CO—R10—CO—, or —(CH2)m—COO—R11—OOC—(CH2)m—, where m is 1 to 3;
• or Q is
• R9 is alkylene of 2 to 50 carbon atoms;
• or said alkylene interrupted by one to ten —O—, phenylene or a group -phenylene-G-phenylene in which G is —O—, —S—, —SO2—, —CH2— or —C(CH3)2—;
• R10 is alkylene of 2 to 10 carbon atoms, or said alkylene interrupted by one to four —O—, —S— or —CH═CH—;
• or R10 is arylene of 6 to 12 carbon atoms;
• R11 is alkylene of 2 to 20 carbon atoms or said alkylene interrupted by one to eight —O—;
• when n is 3, Q is a group —[(CH2)mCOO]3—R12 where m is 1 to 3, and R12 is an alkanetriyl of 3 to 12 carbon atoms;
• when n is 4, Q is a group —[(CH2)mCOO]4—R13 where m is 1 to 3, and R14 is an alkanetetrayl of 4 to 12 carbon atoms;
• Z1 is a group of formula
• Z2 is a group of formula
• where
• r1 and r2 are independently of each other 0 or 1;
• R14, R15, R16, R17, R18, R19, R20, R21, R22 and R23 are independently hydrogen, hydroxy, cyano, alkyl of 1 to 20 carbon atoms, alkoxy of 1 to 20 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, cycloalkoxy of 5 to 12 carbon atoms, halogen, haloalkyl of 1 to 5 carbon atoms, sulfo, carboxy, acylamino of 2 to 12 carbon atoms, acyloxy of 2 to 12 carbon atoms, alkoxycarbonyl of 2 to 12 carbon atoms or aminocarbonyl;
• or R17 and R18 or R22 and R23 together with the phenyl radical to which they are attached are a cyclic radical interrupted by one to three —O— or —NR5—;
• and
• with the proviso that the s-triazine of formula I, II, III, IV, V or VI 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 1050 hours or less than 0.7 absorbance units after exposure for 1338 hours in a Xenon Arc Weather-Ometer.