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US 5,675,004 AGranted
Red-shifted tris-aryl-S-triazines
AssigneeCiba-Geigy Corporation
InventorTyler Arthur Stevenson
Life of this patent
Estimating the term…
Abstract
Tris-aryl-s-triazines of formula V ##STR1## which contain from one one to three resorcinol derived moieties with at least one of said moieties substituted in the 5-position with a group such as, for example, alkyl or phenylalkyl have UV spectra which are red-shifted to the near UV range and provide excellent stabilization to polymeric substrates against the deleterious effects of actinic light.
Claims3
A compound of formula V ##STR18## wherein for the compound of formula V:
- X and Y are the same or different and are phenyl or phenyl substituted by one to three lower alkyl, halogen, hydroxy or alkoxy;
- R.sub.1 is straight or branched chain alkyl of 3 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 24 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, halogen, --SR.sub.3, --SOR.sub.3, or --SO.sub.2 R.sub.3 ;
- said alkyl or cycloalkyl substituted by one to eight halogen, --R.sub.4, --OR.sub.5, --N(R.sub.5).sub.2, .dbd.NR.sub.5, .dbd.O, --CON(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, --P(O)(OR.sub.5).sub.2, morpholinyl, piperidinyl, 2,2,6,6-tetramethylpiperidinyl, piperazinyl or N-methylpiperazinyl groups or combinations thereof;
- or said alkyl or cycloalkyl interrupted by one to six phenylene, --O--, --NR.sub.5 --, --CONR.sub.5 --, --COO--, --OCO--, --C(R.sub.5).dbd.C(R.sub.5)-- or --CO-- groups or combinations thereof;
- or said alkyl or 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;
- or 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 R.sub.4, or R.sub.5 is also hydrogen or straight or branched chain alkyl of 1 to 24 carbon atoms;
- or R.sub.5 is a group of the formula ##STR19## where T is hydrogen, oxyl, hydroxyl, alkyl of 1 to 12 carbon atoms, said alkyl substituted by at least one hydroxyl or lower alkoxy, benzyl or alkanoyl of 2 to 18 carbon atoms;
- n=2 to 4;
- when n=2, Q is straight or branched chain alkylene of 2 to 16 carbon atoms;
- or said alkylene substituted by one to eight --OH;
- or said alkylene interrupted by one to eight --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)m--COO--R.sub.11 --OOC--(CH.sub.2)m--,
- where m=1 to 3;
- or Q is ##STR20## R.sub.8 as defined below;
- R.sub.9 is alkylene of 2 to 50 carbon atoms;
- or said alkylene interrupted by 1 to 10 --O--, phenylene, or a group -phenylene-G-phenylene- in which G is --O--, --S--, --SO.sub.2 --, --CH.sub.2 --, or --C(CH.sub.2).sub.2 ;
- R.sub.10 is alkylene of 2 to 10 carbon atoms, or said alkylene interrupted by 1 to 4 --O--, --S--, or --CH--CH--;
- or R.sub.10 is arylene of 6 to 12 carbon atoms;
- R.sub.11 is alkylene of 4 to 20 carbon atoms, or said alkylene interrupted by 1 to 8 --O--;
- when n=3, Q is a group --(CH.sub.2).sub.m COO!.sub.3 --R.sub.12 where m=1 to 3 and R.sub.12 is an alkanetriyl of 3 to 12 carbon atoms;
- when n=4, Q is a group --(CH.sub.2).sub.m COO!.sub.4 --R.sub.13 where m=1 to 3 and R.sub.13 is an alkanetetryl of 4 to 12 carbon atoms;
- and
- X and Y are as defined above;
- t is 0 to 9;
- L is straight or branched chain alkylene of 1 to 12 carbon atoms, cycloalkylene of 5 to 12 carbon atoms, alkylene substituted by 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 ##STR21## where E is alkylene of 2 to 12 carbon atoms, cycloalkylene of 5 to 12 carbon atoms, or alkylene interrupted or terminated by cyclohexylene of 8 to 12 carbon atoms;
- with the proviso that at least one L linkage is attached to the phenyl ring in the 5-position;
- 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 cycloalkyl substituted by one to eight 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## combinations thereof;
- or said alkyl or cycloalkyl interrupted by one to six 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)--, --(R.sub.5)C.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 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 18 carbon atoms, phenyl, alkoxy of 1 to 12 carbon atoms, phenoxy, alkylamino of 1 to 12 carbon atoms, arylamino of 6 to 12 carbon atoms or a group --R.sub.7 COOH or --NH--R.sub.8 --NCO;
- R.sub.7 is alkylene of 2 to 14 carbon atoms or o-phenylene;
- R.sub.8 is alkylene of 2 to 10 carbon atoms, phenylene, tolylene, diphenylenemethane or a group ##STR23## with R.sub.4 and R.sub.5 as defined above.
39 more elements
Dependencies are inferred from the claim text.