US 4,072,672 AGranted

Cationic dyes containing an aryloxy group linked through a bridging radical to a quaternized nitrogen atom

AssigneeSandoz Ltd.

InventorBeat Henzi

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Abstract

Disclosed are basic dyes, e.g., azo dyes and anthraquinone dyes free from sulphonic acid groups and which contain, as characteristic group, a group of the formula ##STR1## in which R and R.sub.1, independently, are substituted or unsubstituted C.sub.1-4 alkyl or are linked to form a ring, or One of R and R.sub.1 is --NH.sub.2 or C.sub.1-4 alkoxy, the other substituted or unsubstituted alkyl, R.sub.2 and R.sub.3, independently, are hydrogen or C.sub.1-4 alkyl, Y is a bridging group, Q is unsubstituted or substituted phenyl, biphenylyl, naphthyl or ##STR2## in which R.sub.7 is ##STR3## where R.sub.8 ic C.sub.1-4 alkyl, and A.sup.- is an anion. These dyes are useful for the dyeing and printing of polymers and copolymers of acrylonitrile and asymmetrical dicyanoethylene as well as polyesters and polyamides modified to contain acid groups. The dyes build-up well and exhibit good pH stability and stability to boiling. The obtained dyeings are level and possess good fastness to light, wet treatments, solvents, heat treatments and cross-dyeing.

Claims62

Dependent claims

A dye of the formula

wherein
G is the residue of a carbocylic monoazodye
R is alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by hydroxy or phenyl, amino or alkoxy of 1 to 4 carbon atoms,
R.sub.1 is alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by hydroxy or phenyl,
R.sub.2 is hydrogen or alkyl of 1 to 4 carbon atoms,
R.sub.3 is hydrogen or alkyl of 1 to 4 carbon atoms,
Q is ##STR190## wherein n R.sub.7 is ##STR191## wherein each R.sub.8 is independently alkyl of 1 to 4 carbon atoms, each R.sub.9 is independently hydroxy, halo, alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl or phenoxy, alkoxy of 1to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl or phenoxy, cycloalkyl of 5 or 6 carbon atoms, cycloalkyl of 5 or 6 carbon atoms substituted by alkyl of 1 to 4 carbon atoms, trifluoromethyl, cyano, nitro, phenoxy, naphthyloxy, -CO-Ro, --CO-O-Ro, --O-CO-Ro, --CO-NH-Ro, --CO-N(Ro).sub.2, --O-CO-N(Ro).sub.2, -NH-CO-Ro, --SO.sub.2 -Ro, -SO.sub.2 -NH-Ro or -O-SO.sub.2 -N(Ro).sub.2, wherein each Ro is independently alkyl of 1 to 4 carbon atoms or phenyl,
R.sub.10 is hydrogen, halo or alkyl of 1to 4 carbon atoms,
R.sub.11 is hydrogen alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, phenyl, phenoxy, halo, trifluoromethyl, nitro, cyano, -CO-Ro, --CO-O-Ro, --O-CO-Ro, --CO-NH-Ro, --NH-CO-Ro, -SO.sub.2 -Ro --SO.sub.2 --NH-Ro or -SO.sub.2 -N)Ro).sub.2,
wherein each Ro is independently alkyl of 1 to 4 carbon atoms or phenyl, and
a is 0, 1, 2, 3, 4, or 5, with the proviso that when a is 4 or 5 each R.sub.9 must be halo,
Y is ##STR192## wherein each R.sub.4 is independently hydrogen or alkyl of 1 to 4 carbon atoms,
R.sub.5 is ##STR193## --SO--, --SO.sub.2 --or --CO--, wherein R.sub.6 is hydrogen or alkyl of 1 to 4 carbon atoms, and
x is 1 to 6, and
A.sup.- is an anion,
wherein each halo is independently chloro, bromo or iodo, with the proviso that the molecule is free of sulfo groups.

13 more elements

A compound of the formula ##STR199## wherein R.sub.16 is hydrogen, phenyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl, phenoxy, alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, benzoyloxy, --CO-N-(Ra).sub.2 or --O-CO-N(Ra).sub.2, wherein each Ra is independently hydrogen or alkyl of 1 to 4 carbon atoms,

R.sub.17 is ##STR200## wherein R.sub.25 is hydrogen or alkyl of 1 to 4 carbon atoms, R.sub.19 is hydrogen, nitro, halo, cyano, trifluoromethyl, alkylsulfonyl of 1 to 4 carbon atoms, phenylsulfonyl, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, -CO-Ro, --COORo, --CO--NHRo or -SO.sub.2 -N(R.sub.21).sub.2,
wherein each R.sub.21 is independently alkyl of 1 to 4 carbon atoms, and
Ro is alkyl of 1 to 4 carbon atoms or phenyl,
each of
R.sub.119 and R'.sub.119 is independently hydrogen, nitro, halo, cyano, alkyl of 1 to 4 carbon atoms, trifluoromethyl, alkylsulfonyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms,
R.sub.219 is hydrogen, halo, nitro or cyano, with the proviso that at least one of R.sub.19, R.sub.119, R'.sub.119 and R.sub.219 is hydrogen or halo
K' is ##STR201## wherein R.sub.18 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halo,
Ka' is ##STR202## wherein each of R.sub.18 ' and R.sub.19 ' is independently hydrogen, phenyl, cyclohexyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, benzoyloxy, phenoxy, halo, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms or N,N-dialkylamino wherein each alkyl independently has 1 to 4 carbon atoms, with the proviso that when one of R.sub.18 ' and R.sub.19 ' is phenyl or cyclohexyl, the other is other than phenyl or cyclohexyl, R.sub.21 ' is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halo, R.sub.24 ' is hydroxy, amino or anilino, and
each of
R.sub.181 and R.sub.191 is independently hydrogen, phenyl, cyclohexyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, benzoyloxy, phenoxy, halo, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms or N,N-dialkylamino wherein each alkyl independently has 1 to 4 carbon atoms, with the proviso that at least one of R.sub.181 and R.sub.191 is hydrogen or alkyl of 1 to 4 carbon atoms,
Ka" is ##STR203## wherein each of R.sub.18 ' and R.sub.19 ' is independently hydrogen, phenyl, cyclohexyl, alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by alkoxycarbonyl wherein the alkoxy moiety has 1 to 4 carbon atoms, benzoyloxy, phenoxy, halo, hydroxy, cyano, alkoxy of 1 to 4 carbon atoms, alkylcarbonyloxy wherein the alkyl moiety has 1 to 4 carbon atoms or N,N-dialkylamino wherein each alkyl independently has 1 to 4 carbon atoms, with the proviso that when one of R.sub.18 ' and R.sub.19 ' is phenyl or cyclohexyl, the other is other than phenyl or cyclohexyl, and
R.sub.21 ' is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halo,
Z is --CO- or --SO.sub.2,
t is 1 or 2, Hal is halo, and
T" is ##STR204## wherein R is alkyl of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms substituted by hydroxy or phenyl, amino or alkoxy of 1 to 4 carbon atoms,
R.sub.1 is alkyl of 1 to 4 carbon atoms or alkyl of 1 to 4 carbon atoms substituted by hydroxy or phenyl,
R.sub.2 is hydrogen or alkyl of 1 to 4 carbon atoms,
R.sub.3 is hydrogen or alkyl of 1 to 4 carbon atoms,
Q is ##STR205## wherein R.sub.7 is ##STR206## wherein each R.sub.8 is independently alkyl of 1 to 4 carbon atoms,
each
R.sub.9 is independently hydroxy;
halo;
alkyl of 1 to 4 carbon atoms;
alkyl of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl or phenoxy;
alkoxy of 1 to 4 carbon atoms;
alkoxy of 1 to 4 carbon atoms substituted by halo, hydroxy, cyano, phenyl or phenoxy;
cycloalkyl of 5 or 6 carbon atoms;
cycloalkyl of 5 or 6 carbon atoms substituted by alkyl of 1 to 4 carbon atoms;
trifluoromethyl;
cyano;
nitro;
phenoxy;
naphthyloxy;
--CO--Ro;
--CO--O--Ro;
--O--CO--Ro;
--CO--NH--Ro;
--CO--N(Ro).sub.2 ;
--O--CO--N(Ro).sub.2 ;
--NH--CO--Ro;
--SO.sub.2 --Ro;
--SO.sub.2 --NH--Ro or --O--SO.sub.2 --N(Ro).sub.2,
wherein each
Ro is independently alkyl of 1 to 4 carbon atoms or phenyl,
R.sub.10 is hydrogen, halo or alkyl of 1 to 4 carbon atoms,
R.sub.11 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, phenyl, phenoxy, halo, trifluoromethyl, nitro, cyano, --CO--Ro, --CO--O--Ro, --O--CO--Ro, --CO--NH--Ro, --NH--CO--Ro, --SO.sub.2 --Ro, --SO.sub.2 --NH--Ro or --SO.sub.2 --N(Ro).sub.2,
wherein each Ro is independently alkyl of 1 to 4 carbon atoms or phenyl, and
a is 0, 1. 2, 3, 4, or 5, with the proviso that when a is 4 or 5 each R.sub.9 must be halo,
Y is ##STR207## wherein each R.sub.4 is independently hydrogen or alkyl of 1 to 4 carbon atoms,
R.sub.5 is ##STR208## --SO--, --SO.sub.2 -- or --CO--, wherein R.sub.6 is hydrogen or alkyl of 1 to 4 carbon atoms, and
x is 1 to 6, and
A.sup.- is an anion,
wherein each halo is independently chloro, bromo or iodo.

50 more elements

Dependencies are inferred from the claim text.

Facts

Application: 05/635,600Filed 28 Nov 1975 · continuation
Priority: CH 11354/7231 Jul 1972
Granted: 7 Feb 1978
Term ends: Not estimatedThe source records don’t support an estimate.

Classification17 codes

C07D 307/91
Ortho- or peri-condensed with carbocyclic rings or ring systems: dibenzofurans; Hydrogenated dibenzofurans
C07D 209/14
With substituted hydrocarbon radicals attached to carbon atoms of the hetero ring: radicals substituted by nitrogen atoms, not forming part of a…
C07D 249/08
Not condensed with other rings: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
C07D 277/82
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…