Claims
- 1. A compound of the formula ##STR39## wherein X is methyl or methoxy.
- 2. The compound according to claim 1 of the formula ##STR40##
- 3. The compound according to claim 1 of the formula ##STR41##
Priority Claims (1)
| Number |
Date |
Country |
Kind |
| 14052/71 |
Sep 1971 |
CH |
|
Parent Case Info
This is a continuation-in-part of our copending application Ser. No. 287,314 filed Sept. 8, 1972 now abandoned.
It has been found that new, valuable iminoisoindolinone dyestuffs of the formula ##STR2## wherein X denotes chlorine or bromine atoms, X.sub.1 denotes a halogen atom or an alkyl, alkoxy, nitrile, trifluoromethyl or alkylsulphonyl group, Y.sub.1 denotes a hydrogen or halogen atom or an alkyl or alkoxy group, X.sub.2 denotes a hydrogen or halogen atom or an alkyl or alkoxy group and Y.sub.2 denotes a hydrogen or halogen atom or an alkyl or alkoxy group, or the radicals X.sub.2 and Y.sub.2 together form a fused benzene ring, and wherein, in the benzene rings A and B, a hydrogen atom is present in at least one o-position relative to the azomethine group, are obtained if an azo compound of the formula ##STR3## wherein X.sub.1, Y.sub.1, X.sub.2 and Y.sub.2 have the indicated meaning, is condensed in a molar ratio of 1:2 with a 4,5,6,7 -tetrahalogenoisoindolinone-1 which contains, in the 3 -position, easily replaceable substituents which, depending on the type or number, require two bonds and are more mobile than the oxygen located in the 1 -position.
The dyestuffs according to the invention preferably correspond to the formula ##STR4## wherein V.sub.1 and V.sub.2 denote hydrogen or halogen atoms, or alkyl or alkoxy groups containing 1 to 4 carbon atoms and Z.sub.1 and Z.sub.2 denote hydrogen atoms or alkyl or alkoxy groups containing 1 to 4 carbon atoms, with at least one of the substituents V.sub.1 and Z.sub.2 denoting an alkyl or alkoxy group.
Examples of starting substances used are 4,5,6,7-tetrabromo-isoindolinones, but preferably 4,5,6,7-tetrachloroisoindolinones. As easily replaceable substituents in the 3-position they contain, for example, two halogen atoms, especially chlorine atoms, two tertiary amino groups, for example piperidino or morpholino groups, an imino group or a thioxo group or, in particular, 2 alkoxy groups, preferably those containing 1 to 4 carbon atoms, especially methoxy groups. These starting substances are known.
The azo compounds preferably used are those of the formula ##STR5## wherein V.sub.1 and V.sub.2 denote hydrogen or halogen atoms or alkyl or alkoxy groups containing 1 to 4 carbon atoms, Z.sub.1 and Z.sub.2 denote hydrogen atoms or alkyl or alkoxy groups containing 1 to 4 carbon atoms, with at least one of the substituents V.sub.1 and Z.sub.2 denoting an alkyl or alkoxy group.
The diazoamino compounds used are known substances which are obtained, for example, by coupling the diazo compound of a monoacylated diaminobenzene with an aminobenzene and deacylating the resulting azo dyestuff, or by coupling the diazo compound of a nitroaniline with an aminobenzene and reducing the nitro group in the resulting azo dyestuff. The following diaminoazo compound may be mentioned as examples: 2-chloro-4,4'-diaminoazobenzene, 3-chloro-4,4'-diaminoazobenzene, 2-methyl-4,4'-diaminoazobenzene, 3-methyl-4,4'-diaminoazobenzene, 2-methoxy-4,4'-diaminoazobenzene, 3-methoxy-4,4'-diaminoazobenzene, 2,5-dimethyl-4,4'-diaminoazobenzene, 2,3-dimethyl-4,4'-diaminoazobenzene, 5,2',5'-trimethyl-4,4'-diaminoazobenzene, 2,5-2'-trimethyl-4,4'-diaminoazobenzene, 2,5,2',5'-tetramethyl-4,4'-diaminoazobenzene, 3-methyl-2'-methoxy-4,4'-diaminoazobenzene, 2-chloro-2'-methyl-4,4'-diaminoazobenzene, 3-chloro-2'-methyl-4,4'-diaminoazobenzene, 3-chloro- 5-2'-dimethyl-4,4'-diaminoazobenzene, 2-chloro-5-2'-dimethyl-4,4'-diaminoazobenzene, 3-chloro-5-2'-dimethoxy-4,4'-diaminoazobenzene, 3-chloro-2',5'-diethoxy-4,4'-diaminoazobenzene, 2,5-dimethyl-2'-methoxy-4,4'-diaminoazobenzene, 2,5-dimethyl-2'-methyl-5'-methoxy-4,4'-diaminoazobenzene, 2,5-dimethyl-2',5'-dimethoxy-4,4'-diaminoazobenzene, 2,5,2',5'-tetramethoxy-4,4'-diaminoazobenzene, 2,5,2',5'-tetraethoxy-4,4'-diaminoazobenzene, 2,5-diethoxy-2'-methoxy-4,4'-diaminoazobenzene, 2,5,5'-trimethoxy-2'-methyl-4,4'-diaminoazobenzene, 2-cyano-4,4'-diaminoazobenzene, 2-cyano-2'-methyl-4,4'-diaminoazobenzene, 2-cyano-2',5'-dimethyl-4,4'-diaminoazobenzene, 2-cyano-2'-methyl-5'-methoxy-4,4'-diaminoazobenzene, 2-cyano-2',5'-dimethoxy-4,4'-diaminoazobenzene, 2-trifluoromethyl-4,4'-diaminoazobenzene, 2-trifluoromethyl-2'-methyl-4,4'-diaminoazobenzene, 2-trifluoromethyl-2',5'-dimethyl-4,4'-diaminoazobenzene, 2-trifluoromethyl- 2'-methyl-5'-methoxy-4,4'-diaminoazobenzene, 2-methylsulphonyl-4,4'-diaminoazobenzene, 2-methylsulphonyl-2'-methyl-4,4'-diaminoazobenzene, 2-methylsulphonyl-2',5'-dimethyl-4,4'-diaminoazobenzene, 2-methylsulphonyl-2'-methyl-5'-methoxy-4,4'-diaminoazobenzene, 4-chloro-3,4'-diaminoazobenzene, 2-chloro-4,3'-diaminoazobenzene, 2-methyl-4,3'-diaminoazobenzene, 2-methoxy-4,3'-diaminoazobenzene and 4,4'-diaminobenzene-1-azonaphthalene-1'.
The condensation in part already takes place cold but, if necessary, with warming of the intimately mixed components and particularly advantageously in the presence of organic solvents which are inert, that is to say which do not participate in the reaction.
If starting from 3-imino-, 3-thioxo- or 3,3-bis-tert. amino-4,5,6,7-tetrachloroisoindolin-1-ones or from alkali salts of the 3,3-dialkoxy-4,5,6,7-tetrachloroisoindolin-1-ones, organic solvents which are miscible with water, for example lower aliphatic alcohols, such as lower alkanols, for example methanol, isopropanol or butanol, lower cyclic ethers, such as dioxane or ethylene glycol monomethyl ether or lower aliphatic ketones, such as acetone, are advantageously used. In this case the condensation already takes place at relatively low temperatures. It is advantageously carried out in the presence of agents which bind bases; as examples of such, lower fatty acids, which then simultaneously act as solvents, especially acetic acid, may be mentioned.
If using 3,3-dihalogeno-4,5,6,7-tetrachloroisoindolin-1-ones, organic solvents which are free of hydroxyl groups are preferred, such as hydrocarbons, for example aromatic hydrocarbons, such as benzene, toluene, xylene, tetrahydronaphthalene or diphenyl, or cycloaliphatic hydrocarbons, for example cyclohexane, and also halogenated hydrocarbons, such as aliphatic halogenated hydrocarbons, for example carbon tetrachloride or tetrachloroethylene, or aromatic halogenated hydrocarbons, such as chlorobenzene or dichlorobenzenes and trichlorobenzenes, and also aromatic nitro-hydrocarbons, such as nitrobenzene, ethers, namely aliphatic ethers, such as dibutyl ether, aromatic ethers, such as diphenyl ether, or cyclic ethers, such as dioxane, and also ketones, such as acetone, or esters, especially esters of lower fatty acids with lower alkanols, such as acetic acid ethyl ester, in the presence of acid-binding agents.
Immediately after its formation, the new pigment precipitates from the reaction medium. It can be directly used as a crude pigment for certain purposes; it can however also be improved yet further in its properties, especially as regards purity, form and covering 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 salt.
The new dyestuffs are valuable pigments which, in a finely divided form, can be used for pigmenting high molecular organic material, for example cellulose ethers and cellulose esters, such as ethylcellulose, acetylcellulose or nitrocellulose, polyamides, polyurethanes or polyesters, natural resins or synthetic resins, for example aminoplasts, and especially thermoplastic and thermosetting acrylic resins, urea-formaldehydes and melamine-formaldehyde resins and also alkyd resins, phenoplasts, polycarbonates, polyolefines, such as polystyrene, polyvinyl chloride, polyethylene, polypropylene, polyacrylonitrile, polyacrylic acid ester, rubber, casein, silicone and silicone resins, individually or as mixtures. Here it does not matter whether the high molecular compounds mentioned are present as plastic masses or melts or in the form of spinning solutions, lacquers, paints or printing inks. Depending on the end use, it proves advantageous to employ the new pigments as toners or in the form of preparations. The new pigments are distinguished by high fastness properties, especially by outstanding fastness to light, migration weathering and heat, a high tinting strength and good dispersability.
The present invention permits economical and ecologically unobjectionable manufacture of very fast strongly coloured orange pigments.
US Referenced Citations (1)
| Number |
Name |
Date |
Kind |
|
2973358 |
Pugin |
Feb 1961 |
|
Continuation in Parts (1)
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Number |
Date |
Country |
| Parent |
287314 |
Sep 1972 |
|
Patent Grant
4043999
