Anthraquinone dyestuffs, processes for their preparation, their use, and liquid-crystalline materials containing anthraquinone dyestuffs

Claim 2

An anthraquinone dyestuff of the formula ##STR46## wherein R 1 , R 2 denote hydrogen; C 1 -C 6 -alkyl; C 3 -C 7 -cycloalkyl; unsubstituted phenyl; phenyl which is substituted by C 1 -C 4 -alkyl, cyclohexyl, C 1 -C 4 -alkoxy, (C 1 -C 4 -alkoxy)-carbonyl and (C 1 -C 4 -alkyl)-carbonyl; naphthyl; benzyl; phenethyl and Q denotes an --OR', --SR', --CH═N--R', ##STR47## --CHO or --SO 2 --O--R' radical, wherein R' represents unsubstituted phenyl or phenyl which is substituted by C 1 -C 10 -alkyl, C 1 -C 6 -alkoxy, cyclohexyl, chlorine, bromine, cyano-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio, phenoxy, phenylthio, hydroxyl, cyano, mono- and di-C 1 -C 4 -alkylamino, phenylamino, mono- and di-C 1 -C 4 -alkylaminosulphonyl, phenylaminosulphonyl and hydroxyphenylaminosulphonyl; naphthyl; benzyl, phenethyl; an unsubstituted 5-membered or 6-membered heterocyclic ring, containing one to three heteroatoms from the group consisting of O, N and S, which ring can be substituted by C 1 -C 4 -alkyl or phenyl, and to which ring one or two benzene rings can be fused; such dyestuff excluding the formula in which R 1 and R 2 denote hydrogen and Q denotes phenoxy.

Claim 3

An anthraquinone dyestuff according to claim 1, of the formula ##STR48## in which R 1 ', R 2 ' denote hydrogen, C 1 -C 4 -alkyl, or optionally cyclohexyl-, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-, (C 1 -C 4 -alkoxy)-carbonyl- and (C 1 -C 4 -alkyl)-carbonyl-substituted phenyl and Q 1 denotes --OR', --SR', --CH═N--R', ##STR49## --CHO or SO 2 --O--R', such dyestuff excluding the formula in which R 1 ' and R 2 ' denote hydrogen and Q 1 denotes phenoxy.

Claim 4

An anthraquinone dyestuff according to claim 1, in which R 1 and R 2 represent hydrogen, C 1 -C 4 -alkyl, or optionally cyclohexyl-, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-, (C 1 -C 4 -alkyl)-carbonyl- and (C 1 -C 4 -alkoxy)-carbonyl-substituted phenyl.

Claim 5

An anthraquinone dyestuff according to claim 2, in which R 1 ' and R 2 ' denote hydrogen.

Claim 6

An anthraquinone dyestuff of the formula ##STR50## in which R 1 ' and R 2 ' denote hydrogen, 4-cyclohexylphen 4-methylphenyl, dimethylphenyl, ethylphenyl, 4-methoxyphenyl, 2,6-diethoxy-4-methylphenyl, 4-ethoxycarbonyl-phenyl and Q 2 denotes formyl, phenoxycarbonyl, phenoxy, 2-chlorophenoxy, 4-methylphenoxy, 2-ethoxyphenoxy, 4-methoxyphenoxy, 4-(β-cyanomethyl)-phenoxy, 3-chlorophenoxy, 4-phenylphenoxy, 3-methylphenoxy, 4-chlorophenoxy, p-(2-phenyl-prop-2-yl)-phenoxy, 2-methylphenoxy, 2-methoxyphenoxy, 4-methylthiophenoxy, 4-t.-butylphenoxy, 3-methoxyphenoxy, 4-(4'-hydroxyphenylaminosulphonyl)-phenoxy, 2-ethylphenoxy, 4-hydroxyphenoxy, 3-cyanophenoxy, 4-phenylthiophenoxy, 1,1,3,3-tetramethylbut-1-yl-phenoxy, cyclohexylphenyloxy, 4-phenylaminosulphonylphenoxy, 2-chlorophenoxysulphonyl, 1-naphthyloxy, phenoxy-carbonyl, phenethyloxy, N-(4-methylphenyl)-formimidoyl, N-(dibenzofuran-2-yl)-formimidoyl, N-(4-cyclothexylphenyl)-formimidoyl, N-(4-phenylamino-phenyl)-formimidoyl, N-(4-phenylthiazol-2-yl)-formimidoyl and N-(4-methoxyphenyl)-formimidoyl, such dyestuff excluding the formula in which R 1 ' and R 2 ' denote hydrogen and Q 2 denotes phenoxy.

Claim 7

An anthraquinone dyestuff of the formula ##STR50## in which R 1 ' and R 2 ' denote hydrogen, 4-cyclohexylphen 4-methylphenyl, dimethylphenyl, ethylphenyl, 4-methoxyphenyl, 2,6-diethoxy-4-methylphenyl, 4-ethoxycarbonyl-phenyl and Q 2 denotes formyl, phenoxycarbonyl, phenoxy, 2-chlorophenoxy, 4-methylphenoxy, 2-ethoxyphenoxy, 4-methoxyphenoxy, 4-(β-cyanomethyl)-phenoxy, 3-chlorophenoxy, 4-phenylphenoxy, 3-methylphenoxy, 4-chlorophenoxy, p-(2-phenyl-prop-2-yl)-phenoxy, 2-methylphenoxy, 2-methoxyphenoxy, 4-methylthiophenoxy, 4-t.-butylphenoxy, 3-methoxyphenoxy, 4-(4'-hydroxyphenylaminosulphonyl)-phenoxy, 2-ethylphenoxy, 4-hydroxyphenoxy, 3-cyanophenoxy, 4-phenylthiophenoxy, 1,1,3,3-tetramethylbut-1-yl-phenoxy, cyclohexylphenyloxy, 4-phenylaminosulphonylphenoxy, 2-chlorophenoxysulphonyl, 1-naphthyloxy, phenoxy-carbonyl, phenethyloxy, N-(4-methylphenyl)-formimidoyl, N-(dibenzofuran-2-yl)-formimidoyl, N-(4-cyclothexylphenyl)-formimidoyl, N-(4-phenylamino-phenyl)-formimidoyl, N-(4-phenylthiazol-2-yl)-formimidoyl and N-(4-methoxyphenyl)-formimidoyl, such dyestuff excluding the formula in which R 1 ' and R 2 ' denote hydrogen and Q 2 denotes phenoxy.

Claim 8

An anthraquinone dyestuff of the formula ##STR51## in which R 3 and R 4 denote hydrogen, optionally C 1 -C 4 -alkyl- or cyclohexyl-substituted phenyl or cyclohexyl, and Q 3 represents phenoxy or phenylthio, which can be substituted by C 1 -C 8 -alkyl, cyclohexyl, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkoxy, chlorine and bromine, or a formimidoyl radical which is optionally N-substituted by phenyl, C 1 -C 8 -alkylphenyl, cyclohexyl, C 1 -C 4 -alkoxyphenyl and (hydroxy-C 1 -C 4 -alkoxy)-phenyl, or represents a benzthiazolyl radical, such dyestuff excluding the formula in which R 3 and R 4 denote hydrogen and Q 3 denotes phenoxy.

Claim 9

An anthraquinone dyestuff of the formula ##STR51## in which R 3 and R 4 denote hydrogen, optionally C 1 -C 4 -alkyl- or cyclohexyl-substituted phenyl or cyclohexyl, and Q 3 represents phenoxy or phenylthio, which can be substituted by C 1 -C 8 -alkyl, cyclohexyl, C 1 -C 4 -alkoxy, hydroxy-C 1 -C 4 -alkoxy, chlorine and bromine, or a formimidoyl radical which is optionally N-substituted by phenyl, C 1 -C 8 -alkylphenyl, cyclohexyl, C 1 -C 4 -alkoxyphenyl and (hydroxy-C 1 -C 4 -alkoxy)-phenyl, or represents a benzthiazolyl radical, such dyestuff excluding the formula in which R 3 and R 4 denote hydrogen and Q 3 denotes phenoxy.

Claim 10

A liquid-crystalline material having a positive dielectric anisotropy containing a dyestuff according to claim 10.

Claim 11

A liquid-crystalline material having a positive dielectric anisotropy containing 1,4,5,8-tetraamino-2-6-diphenoxy-anthraquinone.

Claim 12

A liquid-crystalline material having a positive dielectric anisotropy containing 1,4,5,8-tetraamino-2-6-diphenoxy-anthraquinone.

Claim 13

A liquid-crystalline material having a positive dielectric anisotropy containing a dyestuff of the formula ##STR52## wherein I, J and K are selected so that the degree of order S is >0.74 in a liquid-crystalline material having positive dielectric anisotropy calculated from the formula ##EQU2## taking a base value of 0.95 for the case where I=J=K=hydrogen, to which base value are added the increments mentioned, taking into account the sign, the thus determined value y then being inserted in formula (A), from which, using the limiting condition S>0.74, the amount of the particularly preferred compounds is deduced, the possible meanings of the substituents being as follows: ______________________________________ Incre- ment ______________________________________ I, J: ##STR53## with X = n-C.sub.1 -C.sub.4alkyl 0.05 ##STR54## with X = n-C.sub.1 -C.sub.4alkyl and X.sub.1 = X.sub.2 = H with X = X.sub.1 = n-C.sub.1 -C.sub.4alkyl and X.sub.2 = H with X = branched C.sub.1 -C.sub.4alkyl and X.sub.1 = X.sub.2 = H -0.18 -0.26 -0.26 NH.sub.2 0.24 ##STR55## 0.24 ##STR56## with R = n-C.sub.1 -C.sub.4 alkyl -0.20 HNR with R = -0.26 n-C.sub.1 -C.sub.4alkyl with R = branched -0.31 C.sub.1 -C.sub.4alkyl K: ##STR57## 0.64 ##STR58## 0.65 ##STR59## 0.56 ##STR60## 0.40 ##STR61## 0.28 ##STR62## 0.32 ##STR63## 0.08 ##STR64## 0.36 ##STR65## 0.20 ##STR66## 0.16 CHO 0.20 ______________________________________

Claim 14

A liquid-crystalline material having a positive dielectric anisotropy containing a dyestuff of the formula ##STR52## wherein I, J and K are selected so that the degree of order S is >0.74 in a liquid-crystalline material having positive dielectric anisotropy calculated from the formula ##EQU2## taking a base value of 0.95 for the case where I=J=K=hydrogen, to which base value are added the increments mentioned, taking into account the sign, the thus determined value y then being inserted in formula (A), from which, using the limiting condition S>0.74, the amount of the particularly preferred compounds is deduced, the possible meanings of the substituents being as follows: ______________________________________ Incre- ment ______________________________________ I, J: ##STR53## with X = n-C.sub.1 -C.sub.4alkyl 0.05 ##STR54## with X = n-C.sub.1 -C.sub.4alkyl and X.sub.1 = X.sub.2 = H with X = X.sub.1 = n-C.sub.1 -C.sub.4alkyl and X.sub.2 = H with X = branched C.sub.1 -C.sub.4alkyl and X.sub.1 = X.sub.2 = H -0.18 -0.26 -0.26 NH.sub.2 0.24 ##STR55## 0.24 ##STR56## with R = n-C.sub.1 -C.sub.4 alkyl -0.20 HNR with R = -0.26 n-C.sub.1 -C.sub.4alkyl with R = branched -0.31 C.sub.1 -C.sub.4alkyl K: ##STR57## 0.64 ##STR58## 0.65 ##STR59## 0.56 ##STR60## 0.40 ##STR61## 0.28 ##STR62## 0.32 ##STR63## 0.08 ##STR64## 0.36 ##STR65## 0.20 ##STR66## 0.16 CHO 0.20 ______________________________________

Claim 15

A liquid-crystalline material having a positive dielectric anisotropy containing a dyestuff according to claim 3.

Claim 16

A liquid-crystalline material having a positive dielectric anisotropy containing a dyestuff according to claim 5.

Claim 17

A liquid-crystalline material having a positive dielectric anisotropy containing a dyestuff according to claim 6.

Claim 18

A liquid-crystalline material according to claim 7 which further comprises mixtures of two or more of alkylcyanobiphenyls, alkoxycyanobiphenyls, alkylcyanoterphenyls, phenylcyclohexane, bicyclohexyls, azoxy compounds, Schiff bases, phenyl benzoates, phenyl thiobenzoates and terpyrimidines.

Claim 19

A liquid-crystalline material according to claim 7, wherein said material has positive dielectric anisotropy.

Claim 20

An anthraquinone dyestuff according to claim 1, wherein said dyestuff is of the formula ##STR67##

Claim 21

An anthraquinone dyestuff according to claim 1, wherein said dyestuff is of the formula ##STR68##

Claim 22

A liquid-crystalline material having a positive dielectric anisotropy, wherein the dyestuff is of the formula in claim 15.

Claim 23

A liquid-crystalline material having a positive dielectric anisotropy, wherein the dyestuff is of the formula in claim 16.

Claim 24

An anthraquinone dyestuff according to claim 1, wherein said dyestuff is selected from the group consisting of 1,4,5,8-Tetraamino-2,6-(4-tert.-butylphenoxy)anthraquinone; 1,4,5,8-Tetraamino-2,6-(4-cyclohexylphenoxy)anthraquinone; 1,4,5,8-Tetraamino-2,6-(2-methoxyphenoxy)anthraquinone; 1,4,5,8-Tetraamino-2,6-(4-n-butoxyphenoxy)anthraquinone; 1,4,5,8-Tetraamino-2,6-(4-β-hydroxyethoxyphenoxy)anthraquinone; 1,4,5,8-Tetraamino-2,6-(4-chlorophenoxy)anthraquinone; 1,4,5,8-Tetraamino-2,6-(3-bromophenoxy)anthraquinone; 1,4,5,8-Tetra-(4-cyclohexylphenylamino)-2,6-di(4-methylphenoxyanthraquinone); 1,4,5,8-Tetra-(4-cyclohexylphenylamino)-2,6-di(4-tert.-butylphenoxy)-anthraquinone; 1,4,5,8-Tetra-(4-cyclohexylphenylamino)-2,6-di(3-methoxyphenoxy)-anthraquinone; 1,5-Di-(p-toluidino)-4,8-di-(4-cyclohexylphenylamino)-2,6-di-(4-tert.-butylphenoxy)anthraquinone;

Claim 25

5-Di-(p-toluidino)-4,8-di-(4-cyclohexylphenylamino)-2,6-di-(4-n-propoxyphenoxy)-anthraquinone; 1,5-Di-(p-toluidino)-4,8-(cyclohexylphenylamino)-2,6-di-(2-chlorophenoxy)-anthraquinone; 1,4,5,8-Tetraamino-2,6-di-(4-methylphenylthio)anthraquinone; 1,4,5,8-Tetraamino-2,6-di-(4-tert.-butylphenylthio)-anthraquinone; 1,4,5,8-Tetraamino-2,6-di-(4-chlorophenylthio)anthraquinone; and 1,4,5,8-Tetraamino-2,6-di-(3-methoxyphenylthio)anthraquinone.

Claim 26

5-Di-(p-toluidino)-4,8-di-(4-cyclohexylphenylamino)-2,6-di-(4-n-propoxyphenoxy)-anthraquinone; 1,5-Di-(p-toluidino)-4,8-(cyclohexylphenylamino)-2,6-di-(2-chlorophenoxy)-anthraquinone; 1,4,5,8-Tetraamino-2,6-di-(4-methylphenylthio)anthraquinone; 1,4,5,8-Tetraamino-2,6-di-(4-tert.-butylphenylthio)-anthraquinone; 1,4,5,8-Tetraamino-2,6-di-(4-chlorophenylthio)anthraquinone; and 1,4,5,8-Tetraamino-2,6-di-(3-methoxyphenylthio)anthraquinone.

Claim 27

A liquid-crystalline material having a positive dielectric anisotropy, wherein the dyestuff is as defined in claim 19.

Claim 28

An anthraquinone dyestuff of the formula ##STR69## wherein R 1 , R 2 and Q are defined below: __________________________________________________________________________ R.sub.1 R.sub.2 Q __________________________________________________________________________ 4-Cyclohexylphenyl 2,6-Diethyl-4-methylphenyl 2-Chlorophenoxy " 4-t.-Butylphenyl 2-Chlorophenoxy " Methyl 2-Chlorophenoxy Amino 2,6-Diethyl-4-methylphenyl 2-Chlorophenoxy " 4-t.-Butylphenyl 2-Chlorophenoxy ##STR70## ##STR71## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy ##STR72## " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " " p-(2-Phenyl-prop-2-yl)-phenoxy ##STR73## ##STR74## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " " p-(2-Phenyl-prop-2-yl)-phenoxy " " 2-Methyl-phenoxy " " 2-Methoxy-phenoxy " " 4-Methylthio-phenoxy " " 4-t.-Butyl-phenoxy " " 3-Methoxy-phenoxy " " Phenoxy " " 4-(4'-Hydroxyphenyl-amino-sulphonyl)-phenoxy " " 2-Ethyl-phenoxy " " 4-Hydroxy-phenoxy " " 3-Cyano-phenoxy " " 4-Phenylthio-phenoxy " " 1,1,3,3-Tetramethyl-but-1-yl-phenoxy " " Cyclohexyl-phenoxy " " 4-Phenylamino-sulphonyl-phenoxy " " 2-Chlorophenoxy-sulphonyl ##STR75## ##STR76## 2-Chlorophenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " " p-(2-Phenyl-prop-2-yl)-phenoxy " " 2-Methyl-phenoxy " " 2-Methoxy-phenoxy ##STR77## " 4-Methylthio-phenoxy " " 4-t.-Butyl-phenoxy " " 3-Methoxy-phenoxy " " Phenoxy " " 4-(4'-Hydroxyphenyl-aminosulphonyl)-phenoxy " " 2-Ethyl-phenoxy " " 4-Hydroxy-phenoxy " " 3-Cyano-phenoxy " " 4-Phenylthio-phenoxy ##STR78## ##STR79## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " " p-(2-Phenyl-prop-2-yl)-phenoxy ##STR80## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy ##STR81## " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy ##STR82## ##STR83## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " ##STR84## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy ##STR85## 4-Ethoxycarbonyl-phenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 4-Methylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl H ##STR86## N(4-Methylphenyl)-formimidoyl " ##STR87## N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " " Phenyl " " N(4-Phenylamino-phenyl)-formimidoyl " " 4-Methoxyphenyl " " N(4-Phenyl-thiazol-2-yl)-formimidoyl " " N(4-Methoxyphenyl)-formimidoyl ##STR88## H 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " " p-(2-Phenyl-prop-2-yl)-phenoxy " " 2-Methyl-phenoxy " " 2-Methoxy-phenoxy " " 4-Methylthio-phenoxy " " 4-t.-Butyl-phenoxy " " 3-Methoxy-phenoxy " " Phenoxy " " 4-(4'-Hydroxyphenyl-aminosulphonyl)-phenoxy " " 2-Ethyl-phenoxy " " 4-Hydroxy-phenoxy " " 3-Cyano-phenoxy " " 4-Phenylthio-phenoxy " " 1,1,3,3-Tetramethyl-but-1-yl-phenoxy " " 4-Cyclohexyl-phenoxy " " 4-Phenylamino-sulphonyl-phenoxy " " 2-Chlorophenoxy-sulphonyl H ##STR89## 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " " p-(2-Phenyl-prop-2-yl)-phenoxy " " 2-Methyl-phenoxy " " 2-Methoxy-phenoxy " " 4-Methylthio-phenoxy " " 4-t.-Butyl-phenoxy " " 3-Methoxy-phenoxy " " Phenoxy " " 4-(4'-Hydroxyphenyl-aminosulphonyl)-phenoxy " " 2-Ethyl-phenoxy " " 4-Hydroxy-phenoxy " " 3-Cyano-phenoxy " " 4-Phenylthio-phenoxy " ##STR90## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " ##STR91## 2-Ethoxy-phenoxy " ##STR92## 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " CH.sub.3 p-(2-Phenyl-prop-2-yl)-phenoxy " ##STR93## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " ##STR94## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanomethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " ##STR95## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanomethyl)-phenoxy " H N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " " Phenyl " " N(4-Phenylamino-phenyl)-formimidoyl " " 4-Methoxyphenyl " " N(4-Phenyl-thiazol-2-yl)-formimidoyl " " N(4-Methoxyphenyl)-formimidoyl " " Phenethyloxy " " Formyl " " 1-Naphthyloxy " " Phenoxycarbonyl " " 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " " p-(2-Phenylprop-2-yl)-phenoxy " " 2-Methyl-phenoxy " " 2-Methoxy-phenoxy " " 4-Methylthio-phenoxy " " 4-t.-Butyl-phenoxy " " 3-Methoxy-phenoxy " " 4-(4'-Hydroxyphenyl-aminosulphonyl)-phenoxy " " 2-Ethyl-phenoxy " " 4-Hydroxy-phenoxy " " 3-Cyano-phenoxy " " 4-Phenylthio-phenoxy " " 1,1,3,3-Tetramethyl-but-1-yl-phenoxy " " 4-Cyclohexyl-phenoxy " " 4-Phenylamino-sulphonyl-phenoxy " " 2-Chlorophenoxy-sulphonyl " 4-Methylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 4-Ethylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " Dimethylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 4-Methoxyphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 2,6-Diethyl-4-methylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 4-t.-Butylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " Methyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " i-Butyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl ##STR96## 4-Cyclohexylphenyl N(4-Methylphenyl)-formimidoyl " " N(4-Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " " Phenyl " " N(4-Phenylamino-phenyl)-formimidoyl " " N(4-Methoxyphenyl) " " N(4-Phenyl-thiazol-2-yl)-formimidoyl " " N(4-Methylphenyl)-formimidoyl " " Phenethyloxy " " Formyl " " 1-Naphthyloxy " " Phenoxycarbonyl " Amino N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " " Phenyl " " N(4-Phenylamino-phenyl)-formimidoyl " " 4-Methoxyphenyl " " N(4-Phenylthiazol-2-yl)-formimidoyl " " N(4-Methoxyphenyl)-formimidoyl " " Phenethyloxy " " Formyl " " 1-Naphthyloxy " " Phenoxycarbonyl " 4-Ethoxycarbonylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " " Phenyl " " N(4-Phenylamino-phenyl)-formimidoyl " " 4-Methoxyphenyl " " N(4-Phenyl-thiazol-2-yl)-formimidoyl " " N(4-Methoxyphenyl)-formimidoyl " 4-Methylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " " Phenyl " 4-Ethylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " Dimethylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 4-Methoxyphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 2,6-Diethyl-4-methylphenyl N (4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 4-t.-butylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " Methyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " i-Butyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl. __________________________________________________________________________

Claim 29

An anthraquinone dyestuff of the formula ##STR69## wherein R 1 , R 2 and Q are defined below: __________________________________________________________________________ R.sub.1 R.sub.2 Q __________________________________________________________________________ 4-Cyclohexylphenyl 2,6-Diethyl-4-methylphenyl 2-Chlorophenoxy " 4-t.-Butylphenyl 2-Chlorophenoxy " Methyl 2-Chlorophenoxy Amino 2,6-Diethyl-4-methylphenyl 2-Chlorophenoxy " 4-t.-Butylphenyl 2-Chlorophenoxy ##STR70## ##STR71## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy ##STR72## " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " " p-(2-Phenyl-prop-2-yl)-phenoxy ##STR73## ##STR74## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " " p-(2-Phenyl-prop-2-yl)-phenoxy " " 2-Methyl-phenoxy " " 2-Methoxy-phenoxy " " 4-Methylthio-phenoxy " " 4-t.-Butyl-phenoxy " " 3-Methoxy-phenoxy " " Phenoxy " " 4-(4'-Hydroxyphenyl-amino-sulphonyl)-phenoxy " " 2-Ethyl-phenoxy " " 4-Hydroxy-phenoxy " " 3-Cyano-phenoxy " " 4-Phenylthio-phenoxy " " 1,1,3,3-Tetramethyl-but-1-yl-phenoxy " " Cyclohexyl-phenoxy " " 4-Phenylamino-sulphonyl-phenoxy " " 2-Chlorophenoxy-sulphonyl ##STR75## ##STR76## 2-Chlorophenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " " p-(2-Phenyl-prop-2-yl)-phenoxy " " 2-Methyl-phenoxy " " 2-Methoxy-phenoxy ##STR77## " 4-Methylthio-phenoxy " " 4-t.-Butyl-phenoxy " " 3-Methoxy-phenoxy " " Phenoxy " " 4-(4'-Hydroxyphenyl-aminosulphonyl)-phenoxy " " 2-Ethyl-phenoxy " " 4-Hydroxy-phenoxy " " 3-Cyano-phenoxy " " 4-Phenylthio-phenoxy ##STR78## ##STR79## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " " p-(2-Phenyl-prop-2-yl)-phenoxy ##STR80## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy ##STR81## " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy ##STR82## ##STR83## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " ##STR84## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy ##STR85## 4-Ethoxycarbonyl-phenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 4-Methylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl H ##STR86## N(4-Methylphenyl)-formimidoyl " ##STR87## N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " " Phenyl " " N(4-Phenylamino-phenyl)-formimidoyl " " 4-Methoxyphenyl " " N(4-Phenyl-thiazol-2-yl)-formimidoyl " " N(4-Methoxyphenyl)-formimidoyl ##STR88## H 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " " p-(2-Phenyl-prop-2-yl)-phenoxy " " 2-Methyl-phenoxy " " 2-Methoxy-phenoxy " " 4-Methylthio-phenoxy " " 4-t.-Butyl-phenoxy " " 3-Methoxy-phenoxy " " Phenoxy " " 4-(4'-Hydroxyphenyl-aminosulphonyl)-phenoxy " " 2-Ethyl-phenoxy " " 4-Hydroxy-phenoxy " " 3-Cyano-phenoxy " " 4-Phenylthio-phenoxy " " 1,1,3,3-Tetramethyl-but-1-yl-phenoxy " " 4-Cyclohexyl-phenoxy " " 4-Phenylamino-sulphonyl-phenoxy " " 2-Chlorophenoxy-sulphonyl H ##STR89## 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " " p-(2-Phenyl-prop-2-yl)-phenoxy " " 2-Methyl-phenoxy " " 2-Methoxy-phenoxy " " 4-Methylthio-phenoxy " " 4-t.-Butyl-phenoxy " " 3-Methoxy-phenoxy " " Phenoxy " " 4-(4'-Hydroxyphenyl-aminosulphonyl)-phenoxy " " 2-Ethyl-phenoxy " " 4-Hydroxy-phenoxy " " 3-Cyano-phenoxy " " 4-Phenylthio-phenoxy " ##STR90## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " ##STR91## 2-Ethoxy-phenoxy " ##STR92## 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " CH.sub.3 p-(2-Phenyl-prop-2-yl)-phenoxy " ##STR93## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " ##STR94## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanomethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " ##STR95## 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanomethyl)-phenoxy " H N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " " Phenyl " " N(4-Phenylamino-phenyl)-formimidoyl " " 4-Methoxyphenyl " " N(4-Phenyl-thiazol-2-yl)-formimidoyl " " N(4-Methoxyphenyl)-formimidoyl " " Phenethyloxy " " Formyl " " 1-Naphthyloxy " " Phenoxycarbonyl " " 2-Chloro-phenoxy " " 4-Methyl-phenoxy " " 2-Ethoxy-phenoxy " " 4-Methoxy-phenoxy " " 4-(β-Cyanoethyl)-phenoxy " " 3-Chloro-phenoxy " " 4-Phenyl-phenoxy " " 3-Methyl-phenoxy " " 4-Chloro-phenoxy " " p-(2-Phenylprop-2-yl)-phenoxy " " 2-Methyl-phenoxy " " 2-Methoxy-phenoxy " " 4-Methylthio-phenoxy " " 4-t.-Butyl-phenoxy " " 3-Methoxy-phenoxy " " 4-(4'-Hydroxyphenyl-aminosulphonyl)-phenoxy " " 2-Ethyl-phenoxy " " 4-Hydroxy-phenoxy " " 3-Cyano-phenoxy " " 4-Phenylthio-phenoxy " " 1,1,3,3-Tetramethyl-but-1-yl-phenoxy " " 4-Cyclohexyl-phenoxy " " 4-Phenylamino-sulphonyl-phenoxy " " 2-Chlorophenoxy-sulphonyl " 4-Methylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 4-Ethylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " Dimethylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 4-Methoxyphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 2,6-Diethyl-4-methylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 4-t.-Butylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " Methyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " i-Butyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl ##STR96## 4-Cyclohexylphenyl N(4-Methylphenyl)-formimidoyl " " N(4-Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " " Phenyl " " N(4-Phenylamino-phenyl)-formimidoyl " " N(4-Methoxyphenyl) " " N(4-Phenyl-thiazol-2-yl)-formimidoyl " " N(4-Methylphenyl)-formimidoyl " " Phenethyloxy " " Formyl " " 1-Naphthyloxy " " Phenoxycarbonyl " Amino N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " " Phenyl " " N(4-Phenylamino-phenyl)-formimidoyl " " 4-Methoxyphenyl " " N(4-Phenylthiazol-2-yl)-formimidoyl " " N(4-Methoxyphenyl)-formimidoyl " " Phenethyloxy " " Formyl " " 1-Naphthyloxy " " Phenoxycarbonyl " 4-Ethoxycarbonylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " " Phenyl " " N(4-Phenylamino-phenyl)-formimidoyl " " 4-Methoxyphenyl " " N(4-Phenyl-thiazol-2-yl)-formimidoyl " " N(4-Methoxyphenyl)-formimidoyl " 4-Methylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " " Phenyl " 4-Ethylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " Dimethylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 4-Methoxyphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 2,6-Diethyl-4-methylphenyl N (4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " 4-t.-butylphenyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " Methyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl " " N(4-Cyclohexyl-phenyl)-formimidoyl " i-Butyl N(4-Methylphenyl)-formimidoyl " " N(Dibenzofuran-2-yl)-formimidoyl. __________________________________________________________________________

Claim 30

A liquid-crystalline material, wherein the dyestuff is as defined in claim 21.