Patent GB-190215659-A (GB)
Title: Improvements in the Manufacture of Acridine Dyestuffs.
Inventor: IMRAY OLIVER
Filed: 1902-07-14
Granted: 1902-12-11
Abstract: 15,659. Imray, O., [Society of Chemical Industry in Basle]. July 14. Dyes, artificial.-Relates to the following improvements in the production of yellow to orange and brownish-red acridine dyes. (1) An improvement in the process described in Specification No. 18,589, A.D. 1894, consisting in treating acridineyellow or benzoflavine, or other amido- or albylamido-acridine, such as amidotolunaphthacridine, diamidotolumethylacridinium, diamidotolumethylacridine, and symmetrical dialkyltoluacridine, with a mixture of sulphuric acid and an alcohol, or with an alkyl-sulphuric acid, in an open vessel without pressure and at a high temperature. (2) An improvement in the process described in Specification No. 5114, A.U. 1895, consisting in heating with an alkyl-sulphuric acid, or a mixture of sulphuric acid and an alcohol, or a mixture of an alcohol and any condensing-agent which acts in presence of an alcohol both as an alkylizing-agent and an agent for eliminating ammonia, in an open vessel, a tetramidodiphenylmethane derivative, such as tetramidoditolylmethane and tetramidcditolylmethylmethane, obtained by condensing one molecular proportion of an aliphatic or aromatic aldehyde with two molecular proportions of the same or of two different metadiamines, or a mixture of an aldehyde and a metadiamine, or a mixture of a methylene or benzylidene derivative and a metadiamine. (3) New easily-soluble dyes are produced by acting upon amidoacridines or amidoacridinium derivatives, such as those mentioned under (1) above, or their leuco compounds, with acetic aldehyde and an acid under pressure or not. (4) New soluble acridine dyes are also produced by condensing one molecular proportion of acetic aldehyde with two molecular proportions of the same or two different metadiamines in aqueous or alcoholic solution in presence of an acid, and then heating the product with hydrochloric or sulphuric acid, or other agent capable of eliminating ammonia at a high temperature with or without pressure. An example is given in which a dyestuff of the constitution which dyes leather and tannin-mordanted cotton greenish-yellow tints, is obtained by this process from m-toluylenediamine. m-Phenylenediamine or m-amidodimethylaniline may be similarly employed. (5) The dyes produced as described in the preceding section are converted into alkylized alkylamido acridines by heating them with a mixture of a mineral acid and an alcohol at a high temperature under pressure or not. (6) The dyes obtained as described in sections (4) and (5) are further converted into acridinium compounds alkylized at the acridine nitrogen by acting upon the colour bases with alkyl halides, alphyl sulphonic acids, or dimethyl sulphate, with or without a suitable indifferent solvent, according to the processes described in Specifications No. 18,589, A.D. 1894, and No. 8872, A.D. 1900. (7) New acridine dyes are produced by heating a condensation product obtained from equimolecular proportions of a metadiamine and an aldehyde with an acid or similar condensing-agent under pressure or not. The condensation products employed have the constitution in which formulµ X and Y ropresent hydrogen or an alkyl, and R represents hydrogen, an alkyl, or an alphyl. They are obtained, for example, from m-toluylenediamine, m-phenylenediamine, or mamido-mono- or dialkylaniline and formaldehyde, acetic aldehyde, or benzaldehyde. The dyes yield brownish-orange to brownish-red shades on tanninmordanted cotton and leather.