New azole compounds

摘要

The invention comprises compounds of the formula where R1 represents a benzene residue, R2 represents a benzene residue or naphthylene radical condensed with the axole ring in the manner indicated by the valency lines, and X represents an oxygen or sulphur atom or a group -N(A)-, A standing for a hydrogen atom, a lower alkyl, alkenyl or hydroxyalkyl group containing at most 4 carbon atoms, or a benzyl group, and the acid addition and quaternary ammonium salts of the compounds in which X stands for -N(A)-; the benzene residues R1 and R2 may be further substituted by alkyl radicals such as methyl, ethyl, isopropyl, tertiary butyl, alkoxy groups such as methoxy or ethoxy, a phenyl group, or a cycloalkyl group such as a cyclohexyl group. The compounds may be prepared (i) by the action of a reducing agent capable of eliminating water on a compound of the formula in which R1 and X have the above meanings, and R2 represents a benzene residue or naphthylene radical to which the groups O2N- and -CO-X- are bound in vicinal position: (ii) by eliminating water from a compound of the formula in which R1 and X have the above meanings, and R2 represents a benzene residue or naphthylene radical to which the -HN- and -X-groups are bound in vicinal position, or if the substituent of R2 bound to hydrogen contains nitrogen, from an acid addition salt of the compound of formula (6):(iii) by heating together a compound of the formula and a compound of the formula where R1, R2 and X have the above meanings, in the presence of pyrophosphoric or polyphosphoric acid, the intermediates of formula (6) above not being isolated. The compounds of formula (3) above are prepared by reacting a carboxylic halide of the formula where R1 has the above meaning, with the appropriate hydroxy-, mercapto- or amino-benzene or -naphthalene containing a nitro group in vicinal position to the above-mentioned substituent. The acid halides of formula (4) above can be prepared in the usual manner from the appropriate carboxylic acids. The compounds of formula (6) above can be prepared by conventional methods, for example from acid halides of the formula (4) above, or the corresponding acids, and aminoaryl compounds of formula (11) above; esterification of the hydroxyl or mercapto groups takes place preferably under mild, acidic reactive conditions, whereas under energetic conditions the amino groups are as a rule arylated. Imidazole compounds of the formula (2) above in which A = hydrogen may be treated with alkylating, alkenylating, hydroxy-alkylating or benzylating agents to give compounds of formula (2) above in which A is not hydrogen, and they may be converted into acid addition or quaternary ammonium salts. Examples are given. The compounds of the invention may be used as optical brightening agents (see Divisions C2, C5 and D1). ALSO: Detergents may incorporate a brightening agent of the formula where R1 represents a benzene residue, R2 represents a benzene residue or naphthylene radical condensed with the azole ring in the manner indicated by the valency lines, and X represents an oxygen or sulphur atom or a group -N(A)-, A standing for a hydrogen atom, a lower alkyl, alkenyl or hydroxyalkyl group containing at most 4 carbon atoms, or a benzyl group, or the acid addition or quaternary ammonium salts of the compounds in which X stands for -N(A)-; the benzene residues R1 and R2 may be further substituted by alkyl, alkoxy or cycloalkyl groups or by a phenyl group (see Division C2). Suitable detergents specified are soaps, salts of sulphonate detergents such, for example, as salts of sulphonated benzimidazoles substituted on the carbon atom 2 by higher alkyl radicals, salts of monocarboxylic acid esters of 4-sulphophthalic acid with higher fatty alcohols, salts of fatty alcohol sulphonates, alkyl-arylsulphonic acids or condensation products of higher fatty acids with aliphatic hydroxysulphonic or aminosulphonic acids, and non-ionic detergents such as polyglycol ethers, derived from ethylene oxide and higher fatty alcohols, alkylphenols or fatty amines. In Example 12 there is described a solution of 5 parts of soap per litre of water, the soap containing 0.1% of the compound of the formula ALSO: Fibres and fabrics may be brightened with a compound of the formula where R1 represents a benzene residue, R2 represents a benzene residue or naphthylene radical condensed with the azole ring in the manner indicated by the valency lines, and X represents an oxygen or sulphur atom or a group-N(A)-, A standing for a hydrogen atom, a lower alkyl, alkenyl or hydroxyalkyl group containing at most 4 carbon atoms, or a benzyl group, or the acid addition or quaternary ammonium salts of the compounds in which X stands for - N(A) -; the benzene residues R1 and R2 may be further substituted by alkyl; alkoxy or cycloalkyl groups or by a phenyl group (see Division C2). Specified fibres and fabrics are polyesters, polyamides, polyacrylonitrile, polyolefins, polyvinyl chloride, cotton and acetate rayon. In examples: (10) a fabric of polyester fibres from terephthalic acid and ethylene glycol is treated with an aqueous bath containing formic acid and the compound of the formula (11) a polyacrylonitrile fibre fabric is treated with an aqueous bath containing formic acid and one of the following compounds: or yarns made from thermostable polyvinyl chloride fibres may be similarly brightened: (12) cotton, acetate rayon or polyamide fibres are washed with a solution containing soap and the compound of formula (23) above, rinsed and dried.