Mono aryl azo-mono-iminoisoindolinone dyestuffs

Abstract

Iminoisoindolinone dyestuffs of the formula ##STR1## wherein X is halogen, Y halogen, alkoxy, cycloalkoxy, aralkoxy or aryloxy, Y.sub.1 hydrogen, halogen, alkyl or alkoxy having 1 - 4 c-atoms, Y.sub.2 alkyl, alkoxy or alkanoylamino having 1 - 4 c-atoms or benzoylamino, Z chlorine or methyl and R alkyl having 1 - 4 c-atoms or aryl which are useful for pigmenting high molecular organic material.It has been found that new, valuable iminoisindolinone dyestuffs of the formula ##STR2## wherein the X denote halogen atoms, especially chlorine atoms, Y denotes a halogen atom or an alkoxy, cycloalkoxy, aralkoxy or aryloxy group, Y.sub.1 denotes a hydrogen or halogen atom or an alkyl or alkoxy group containing 1 - 4 carbon atoms, Y.sub.2 denotes an alkyl, alkoxy or alkanoylamino group containing 1 - 4 carbon atoms or a benzoylamino group which is optionally substituted, for example by halogen atoms or alkyl or alkoxy groups containing 1 - 4 carbon atoms, the Z denote chlorine atoms or methyl groups and R denotes an alkyl group containing 1 -4 carbon atoms or an aryl radical, preferably a phenyl radical which is optionally substituted by halogen atoms, or alkyl or alkoxy groups containing 1 - 4 carbon atoms, are obtained when a trihalogenoisoindolinone-1 or tetrahalogenoisoindolinone-1, which contains, in the 3-position, one or two easily replaceable substituents which in total require two bonds and are more mobile than the oxygen in the 1-position, is condensed with an amine of the formula ##STR3##Starting substances used are, for example, 4,5,6,7-tetrabromo-, 4,5,6-trichloro-6-methoxy- and preferably 4,5,6,7-tetrachloro-isoindolinone-1 containing easily replaceable substituents in the 3-position.As examples of easily replaceable substituents in the 3-position there may be mentioned two halogen atoms, especially chlorine atoms, two secondary amino groups, for example containing 1 to 4 carbon atoms, for example piperidino or morpholino groups, an imino or a thio group or especially two alkoxy groups, for example containing 1 to 4 carbon atoms, especially methoxy groups. These starting substances are known.The isoindolinones mentioned must be condensed with the amines of the formula (II).The following amines may be mentioned as examples: 4-amino-2-methyl-3', 5'dichloro-4'-acetylamino-azobenzene, 4-amino-2-methoxy-3',5'-dichloro-4'-acetylamino-azobenzene, 4-amino-2,5-dimethyl-3',5'-dichloro-4'-acetylamino-azobenzene, 4-amino-2-methyl-5-chloro-3',5'-dichloro-4'-acetylaminoazobenzene, 4-amino-2-methyl-5-methoxy-3',5'-dichloro-4'-acetylamino-azobenzene, 4-amino-2-methoxy-5-methyl-3',5'-dichloro-4'-acetylamino-azobenzene, 4-amino-2,5-dimethoxy-3',5'-dichloro-4'-acetylamino-azobenzene, 4-amino-2-acetylamino-3',5'-dichloro-4'-acetylamino-azobenzene, 4-amino-5-chloro-2-acetylamino-3',5'dichloro-4'-acetylamino-azobenzene, 4-amino-5-methyl-2-acetylamino-3',5'-dichloro-4'-acetylamino-azobenzene, 4-amino-5-methoxy-2-acetylamino-3',5'-dichloro-4'-acetylamino-azobenzene, 4-amino-2-propionylamino-3',5'-dichloro-4'-acetylamino-azobenzene, 4-amino-5-methyl-2-propionylamino-3',5'-dichloro-4'-acetylamino-azobenzene, 4-amino-5-methyl-2-butyrylamino-3',5'-dichloro-4'-acetylamino-azobenzene, 4-amino-2-benzoylamino-3',5'-dichloro-4'-acetylamino-azobenzene, 4-amino-2-benzoylamino-3',5'-dimethyl-4'-acetylamino-azobenzene, 4-amino-2-methoxy-3',5'-dimethyl-4'-acetylamino-azobenzene, 4-amino-2,5-3',5'-tetramethyl-4'-acetylamino-azobenzene, 4-amino-5-chloro-2,3',5'trimethyl-4'-acetylamino-azobenzene, 4-amino-2-3',5'-trimethyl-5-methoxy-4'-acetylamino-azobenzene, 4-amino-2,5-dimethoxy-3',5'-dimethyl-4'-acetylamino-azobenzene, 4-amino-2-4'-di-acetylamino-3',5'-dimethyl-azobenzene, 4-amino-5-chloro-2,4'-diacetylamino-3',5'-dimethyl-azobenzene, 4-amino-3',5-5'-trimethyl-2,4'-diacetylamino-azobenzene, 4-amino-5-methoxy-2,4'-diacetylamino-3',5'-dimethyl-azobenzene, 4-amino-2,-4'-dipropionylamino-3',5'-dimethyl-azobenzene, 4-amino-3',5'-trimethyl-2-4'-dipropionylamino-azobenzene, 4-amino-2-3',5'-trimethyl-4'-benzoylamino-azobenzene, 4-amino-2-,3',5'-trimethyl-4'-p-chlorobenzoylamino-azobenzene, 4-amino-2-,3',5'-trimethyl-4'-p-methylbenzoylamino-azobenzene and 4-amino-2-,3',5'-trimethyl-4'-p-methoxybenzoylaminoazobenzene.The condensation of the trihalogenoisoindolinone or tetrahalogenoisoindolinone with the aminoazobenzene is in some cases carried out in the cold but if necessary with warming of the intimately mixed components, and particularly advantageously in the presence of inert organic solvents, that is to say solvents which do not participate in the reaction.If starting from 3-imino-, 3-thio- or 3,3-bis-sec. amino-4,5,6,7-tetrachloroisoindolin-1-ones or from alkali metal salts of 3,3-dialkoxy-4,5,6,7-tetrachloroisolindolin1-ones, water-miscible organic solvents are advantageously used, for example lower aliphatic alcohols, such as lower alkanols, for example methanol, isopropanol or butanol, lower cyclic ethers, such as dioxane, ethylene glycol monomethyl ether or lower aliphatic ketones, such as acetone. The condensation in these cases takes place even at relatively low temperatures. It is advantageously carried out in the presence of agents which bind bases; as examples of such agents there may be mentioned lower fatty acids which then simultaneously serve as solvents, especially acetic acid.When using 3,3-dihalogenoindolin-1-ones, organic solvents free of hydroxyl groups are preferred, such as hydrocarbons, for example aromatic hydrocarbons, such as benzene, toluene, xylene, tetrahdronaphthalene or diphenyl, or cycloaliphatic hydrocarbons, for example cyclohexane, but also halogenated hydrocarbons, such as aliphatic halogenated hydrocarbons, for example caron tetrachloride or tetrachlorethylene, or aromatic halogenated hydrocarbons, such as chlorobenzene or dichlorobenzenes and trichlorobenzenes, and also aromatic nitro-hydrocarbons, such as nitrobenzenes, ethers, in particular aliphatic ethers, such as dibutyl ether, aromatic ethers, such as diphenyl ether, or cyclic ethers, such as dioxane, ketones, such as acetone, or esters, especially esters of lower fatty acids with lower alkanols, such as ethyl acetate, in the presence of acid-binding agents.The new pigment precipitates from the reaction medium immediately after its formation. For certain purposes, it can be used directly as crude pigment; however, it can also be improved further in its properties, especially with regard to purity, form and hiding power, in accordance with methods which are in themselves known, for example by extraction with organic solvents or by grinding with grinding auxiliaries which can subsequently be removed again, for example salts.The new dyestuffs are valuable pigments which can be used, in a finely divided form, for pigmenting high molecular organic material for example cellulose ethers and cellulose esters, such as ethylcellulose, acetylcellulose and nitrocellulose, polyamides or polyurethanes or polyesters, natural resins or synthetic resins, for example aminoplasts, especially urea-formaldehyde and melamine-formaldehyde resins, alkyd resins, phenoplasts, polycarbonates, polyolefines, such as polystyrene, polyvinyl chloride, polyethylene, polypropylene, polyacrylonitrile and polyacrylic acid esters, thermoplastic or thermosetting acrylic resins, rubber, casein, silicone and silicone resins, individually or as mixtures. It is immaterial whether the high molecular compounds mentioned are in the form of plastic masses or melts or in the form of spinning solutions, lacquers or printing inks. Depending on the end use it proves advantageous to use the new pigments as toners or in the form of preparations. The great depth of colour, and the excellent fastness to migration and overlacquering, are particularly surprising in view of the fact that the dyestuffs only contain one isoindolinone group in the molecule.

Description

Claims

1. An iminoisoindolinone dyestuff of the formula ##STR4##wherein X is chloro or bromo, Y is chloro, bromo or methoxy, Y.sub.1 is hydrogen, chloro, alkyl containing 1-4 carbon atoms or alkoxy containing 1-4 carbon atoms, Y.sub.2 is alkyl containing 1-4 carbon atoms, alkoxy containing 1-4 carbon atoms, alkanoylamino containing 1-4 carbon atoms, benzoylamino, benzoylamino substituted by chloro, alkyl containing 1-4 carbon atoms, or alkoxy containing 1-4 carbon atoms, Z is chloro or methyl, and R is alkyl containing 1-4 carbon atoms, phenyl, or phenyl substituted by chloro, alkyl containing 1-4 carbon atoms, or alkoxy containing 1-4 carbon atoms, or alkoxycontaining 1-4 carbon atoms.

2. Iminoisoindolinone dyestuff according to claim 1, wherein X is chlorine.