Stabilization
AssigneeCiba-Geigy Corporation
InventorLaurent Chassot
Life of this patent
Estimating the term…
Abstract
Pigment compositions comprising a) at least one organic pigment chosen from the group comprising azo pigments, quinacridones, phthalocyanines, indanthrones, flavanthrones, pyranthrones, anthraquinones, perylenes, dioxazines, perinones, thioindigo, isoindolines, isoindolinones and metal complexes and b) 1 to 100% by weight, based on the pigment, of a nitroxyl compound consisting of at least one unsubstituted or substituted 5-, 6- or 7-membered heterocyclic ring containing a divalent group of the formula ##STR1## in which R.sub.1 and R.sub.2 independently of one another are methyl, ethyl or phenyl, or together form a 4- to 12-membered aliphatic ring, L is an aromatic radical and Y is O., or of an acid addition salt thereof. These pigment compositions are distinguished by an outstanding resistance to light and weathering.
Claims12
A light-stabilised pigment composition consisting essentially of
- a) at least one organic pigment chosen from the group consisting of azo pigments, quinacridones, phthalocyanines, indanthrones, flavanthrones, pyranthrones, anthraquinones, perylenes, dioxazines, perinones, thioindigo, isoindolines, isoindolinones and metal complexes;
- and
- b) 1 to 100% by weight, based on the pigment, of a nitroxyl compound of the formula ##STR82## wherein R.sub.3 is C.sub.1 -C.sub.18 alkyl or C.sub.1 1.varies.C.sub.18 alkoxy;
- G is a divalent group of the formula --CR.sub.4 =CH-- or --CHR.sub.4 --CH.sub.2 --;
- R.sub.4 is C.sub.1 -C.sub.18 alkyl;
- Q is a group of the formula ##STR83## in which the bond labelled * is the bond leading to T;
- T is a direct bond or a group of the formula ##STR84## in which R.sub.5 is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl, or --(CH.sub.2).sub.I --,
- in which r is 1 or 2;
- m is the number 1, 2, 3, 4 or 6;
- X, when m=1, is hydrogen, C.sub.1 -C.sub.18 alkyl, phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, phenyl or halogen, or, under the condition that T, if bonded to a nitrogen atom, is not a direct bond, is a group of the formula --OCO--NR.sub.6 R.sub.7, --OSO.sub.2 --NR.sub.6 R.sub.7, --OCO--R.sub.7, --COOR.sub.7, --CONR.sub.6 R.sub.7, --NR.sub.6 --COR.sub.7, --NR.sub.6 --CONR.sub.6 R.sub.7, --OR.sub.7, --NR.sub.6 R.sub.7 or ##STR85## in which R.sub.6 is hydrogen or C.sub.1 -C.sub.18 alkyl, R.sub.7 is C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.12 alkenyl, C.sub.5 -C.sub.12 cycloalkyl, or phenyl or naphthyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, phenyl or nitro, or a group --(CH.sub.2).sub.S --CHR.sub.8 R.sub.9, s is zero, 1, 2, or 3, R.sub.8 is hydrogen, methyl or phenyl and R.sub.9 is --OH, halogen or a group --COOCH.sub.3 or --COOC.sub.2 H.sub.5 ;
- X, when m=2, is a group of the formula --(CH.sub.2).sub.p or, under the condition that T, if bonded to a nitrogen atom, is not a direct bond, is a group of the formula --O--(CH.sub.2).sub.p --O--, --NR.sub.6 --(CH.sub.2).sub.p --NR.sub.6 --, --OCO--M--COO--, --NR.sub.6 --CO--M--CO--NR.sub.6 --, --OCO--NH--M--NH--COO-- or --NR.sub.6 --CONH--NHCO--NR.sub.6 --, in which M is --(CH.sub.2).sub.p --, ##STR86## and p is a number between 2 and 10;
- X, when m=3, is a group ##STR87## X, when m=4, is a group ##STR88## X, when m=6, is a group ##STR89## X.sub.2 is C.sub.1 -C.sub.18 alkyl;
- n is the number 1 or 2;
- V, when n=1, is C.sub.2 -C.sub.8 alkylene or hydroxyalkylene or C.sub.4 -C.sub.22 acyloxyalkylene;
- or
- V, when n=2, is the group (--CH.sub.2).sub.2 C(CH.sub.2 --).sub.2 or ##STR90## Z is a group of the formula ##STR91## in which the bond labelled with * is the bond leading to W;
- W, when n=1, is a group --OCOR.sub.10, in which R.sub.10 is C.sub.1 -C.sub.18 alkyl, or phenyl or naphthyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;
- or
- W, when n=2, is a group of the formula --OCO--(CH.sub.2).sub.p --COO-- or ##STR92## and Y is O.
A process for light- and weather-stabilisation of pigments chosen from the group consisting of azo pigments, quinacridones, phthalocyanines, indanthrones, flavanthrones, pyranthrones, anthraquinones, perylenes, dioxazines, perinones, thioindigo, isoindolines, isoindolinones and metal complexes, which process consists essentially of mixing or coating the pigment particles with 1 to 100% by weight, based on the pigment, of a nitroxyl compound of the formula ##STR98## is used, in which R.sub.3 is C.sub.1 -C.sub.18 alkyl or C.sub.1 -C.sub.18 alkoxy;
- G is a divalent group of the formula --CR.sub.4 .dbd.CH-- or --CHR.sub.4 -CH.sub.2 -;
- R.sub.4 is C.sub.1 -C.sub.18 alkyl;
- Q is a group of the formula ##STR99## in which the bond labelled * is the bond leading to T;
- T is a direct bond or a group of the formula ##STR100## in which R.sub.5 is hydrogen, halogen or C.sub.1 -C.sub.4 alkyl, or --(CH.sub.2).sub.r --,
- in which r is 1 or 2;
- m is the number 1, 2, 3, 4 or 6;
- X, when m=1, is hydrogen, C.sub.1 -C.sub.18 alkyl, phenyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, phenyl or halogen, or, under the condition that T, if bonded to a nitrogen atom, is not a direct bond, is a group of the formula --OCO--NR.sub.6 R.sub.7, --OSO.sub.2 --NR.sub.6 R.sub.7, --OCO--R.sub.7 , --COOR.sub.7, --CONR.sub.6 R.sub.7, --NR.sub.6 --COR.sub.7, --NR.sub.6 --CONR.sub.6 R.sub.7, --OR.sub.7, --NR.sub.6 R.sub.7 or ##STR101## in which R.sub.6 is hydrogen or C.sub.1 -C.sub.18 alkyl, R.sub.7 is C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.12 alken yl, C.sub.5 -C.sub.12 cycloalkyl, or phenyl or naphthyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, phenyl or nitro, or a group --(CH.sub.2).sub.s --CHR.sub.8 R.sub.9, s is zero, 1,2 or 3, R.sub.8 is hydrogen, methyl or phenyl and R.sub.9 is --OH, halogen or a group --COOCH.sub.3 or --COOC.sub.2 H.sub.5 ;
- X, when m=2, is a group of the formula --(CH.sub.2).sub.p or, under the condition that T, if bonded to a nitrogen atom, is not a direct bond, is a group of the formula --O--(CH.sub.2).sub.p --O--, --NR.sub.6 --(CH.sub.2).sub.p --NR.sub.6 --, --OCO--M--COO--, --NR.sub.6 --CO--M--CO--NR.sub.6 --, --OCO--NH--M--NH--COO-- or --NR.sub.6, --CONH --M--NHCO--NR.sub.6 --, in which M is --(CH.sub.2).sub.p --, ##STR102## and p is a number between 2 and 10;
- X, when m=3, is a group ##STR103## X, when m=4, is a group ##STR104## X, when m=6, is a group ##STR105## X.sub.2 is C.sub.1 -C.sub.18 alkyl;
- n is the number 1 or 2;
- V, when n=1, is C.sub.2 -C.sub.8 alkylene or hydroxyalkylene or C.sub.4 -C.sub.22 -acyloxyalkylene;
- or
- V, when n=2, is the group (--CH.sub.2).sub.2 C(CH.sub.2 --).sub.2 or ##STR106## Z is a group of the formula ##STR107## in which the bond labelled with * is the bond leading to W;
- W, when n=1, is a group --OCOR.sub.10, in which R.sub.10 is C.sub.1 -C.sub.18 alkyl, or phenyl or naphthyl which is unsubstituted or substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halogen;
- or
- W, when n=2, is a group of the formula --OCO--(CH.sub.2).sub.p --COO-- or ##STR108## and Y is O.
Dependencies are inferred from the claim text.