Patent ID: 6225384
Filing Date: 2001-05-01
Classification: B32B,C09J

Abstract:
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 or a mixture thereof, ##STR19## ##STR20##whereinX 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 Z.sub.1 or Z.sub.2 ;R.sub.1 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, --SR.sub.3, --SOR.sub.3 or --SO.sub.2 R.sub.3 ; or said alkyl, said cycloalkyl or said phenylalkyl substituted by one to three halogen, --R.sub.4, --OR.sub.5, --N(R.sub.5).sub.2, --COR.sub.5, --COOR.sub.5, --OCOR.sub.5, --CN, --NO.sub.2, --SR.sub.5, --SOR.sub.5, --SO.sub.2 R.sub.5 or --P(O)(OR.sub.5).sub.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--, --NR.sub.5 --, --CONR.sub.5 --, --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;R.sub.3 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;R.sub.4 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;R.sub.5 is defined as is R.sub.4 ; or R.sub.5 is also hydrogen or straight or branched chain alkyl of 1 to 24 carbon atoms, alkenyl of 2 to 24 carbon atoms; or R.sub.5 is a group for formula ##STR21##T is hydrogen, oxyl, hydroxyl, --OT.sub.1, alkyl of 1 to 24 carbon atoms, said alkyl substituted by one to three hydroxy; benzyl or alkanoyl of 2 to 18 carbon atoms;T.sub.1 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;R.sub.2 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, --R.sub.4, --OR.sub.5, --N(R.sub.5).sub.2, --CON(R.sub.5).sub.2, --COR.sub.5, --COOR.sub.5, --OCOR.sub.5, --OCOC(R.sub.5).dbd.C(R.sub.5).sub.2, --C(R.sub.5).dbd.CCOOR.sub.5, --CN, --NCO, or ##STR22##or combinations thereof; or said alkyl or said cycloalkyl interrupted by one to four epoxy, --O--, --NR.sub.5 --, --CONR.sub.5 --, --COO--, --OCO--, --CO--, --C(R.sub.5).dbd.C(R.sub.5)COO--, --OCOC(R.sub.5).dbd.C(R.sub.5)--, --C(R.sub.5).dbd.C(R.sub.5)--, phenylene or phenylene-G-phenylene in which G is --O--, --S--, --SO.sub.2 --, --CH.sub.2 -- or --C(CH.sub.3).sub.2 -- or combinations thereof, or said alkyl or said cycloalkyl both substituted and interrupted by combinations of the groups mentioned above; or R.sub.2 is --SO.sub.2 R.sub.3 or --COR.sub.6 ;R.sub.6 is straight or branched chain alkyl of 1 to 18 carbon atoms, straight or branched chain alkenyl of 2 to 12 carbon atoms, phenoxy, alkyl amino of 1 to 12 carbon atoms, arylamino of 6 to 12 carbon atoms, --R.sub.7 COOH or --NH--R.sub.8 --NCO;R.sub.7 is alkylene of 2 to 14 carbon atoms or phenylene;R.sub.8 is alkylene of 2 to 24 carbon atoms, phenylene, tolylene, diphenylmethane or a group ##STR23##R.sub.1, R.sub.1 ' and R.sub.1 "" are the same or different and are as defined for R.sub.1 ;R.sub.2, R.sub.2 ' and R.sub.2 "" are the same or different and are as defined for R.sub.2 ;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--, --SO.sub.2 --, --SO--E--SO--, --SO.sub.2 --E--SO.sub.2 --, --CH.sub.2 --NH--E--NH--CH.sub.2 -- or ##STR24##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.dbd.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--R.sub.8 --NHCO--, --CH.sub.2 CH(OH)CH.sub.2 O--R.sub.9 --OCH.sub.2 CH(OH)CH.sub.2 --, --CO--R.sub.10 --CO--, or --(CH.sub.2).sub.m --COO--R.sub.11 --OOC--(CH.sub.2).sub.m --, where m is 1 to 3; or Q is ##STR25##R.sub.9 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--, --SO.sub.2 --, --CH.sub.2 -- or --C(CH.sub.3).sub.2 --;R.sub.10 is alkylene of 2 to 10 carbon atoms, or said alkylene interrupted by one to four --O--, --S-- or --CH.dbd.CH--; or R.sub.10 is arylene of 6 to 12 carbon atoms;R.sub.11 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 --[(CH.sub.2).sub.m COO].sub.3 --R.sub.12 where m is 1 to 3, and R.sub.12 is an alkanetriyl of 3 to 12 carbon atoms;when n is 4, Q is a group --[(CH.sub.2).sub.m COO].sub.4 --R.sub.13 where m is 1 to 3, and R.sub.14 is an alkanetetrayl of 4 to 12 carbon atoms;Z.sub.1 is a group of formula ##STR26##Z.sub.2 is a group of formula ##STR27##wherer.sub.1 and r.sub.2 are independetly of each other 0 or 1;R.sub.14, R.sub.15, R.sub.16, R.sub.17, R.sub.18, R.sub.19, R.sub.20, R.sub.21, R.sub.22 and R.sub.23 are independently of one another 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 R.sub.17 and R.sub.18 or R.sub.22 and R.sub.23 together with the phenyl radical to which they are attached are a cyclic radical interrupted by one to three --O-- or --NR.sub.5 --; andwith the proviso that the s-triazine of formula I, II, III, IV, V or VI or a mixture thereof 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.