Patent GB-472699-A (GB)
Title: Manufacture of coloured condensation products
IPC: C09B23/14
Filed: 1936-04-06
Abstract: Dyestuffs are manufactured by condensing a compound of the general formula R.SO2.CH2.CN (where R is alkyl, aralkyl or aryl) with an aldehyde of the general formula <FORM:0472699/IV/1> (where R1 is alkyl, oxyalkyl or an etherified or esterified oxyalkyl group and R2 is oxyalkyl or an etherified or esterified oxyalkyl group, obtainable from the appropriate dialkylaminobenzenes substituted in one or both of the alkyl groups by a hydroxy or etherified or esterified hydroxy group by a process analogous to that of Specification 17135/98, [Class 2]). Suitable starting materials are: on the one hand alkyl and aralkylsulphoneacetonitriles, e.g. methyl-, ethyl-, propyl-, butyl-, allyl- or benzylsulphoneacetonitrile, arylsulphoneacetonitriles, e.g. phenylsulphoneacetonitrile, halogenbenzenesulphoneacetonitriles, e.g. p-chloro-, bromo-, or iodobenzenesulphoneacetonitrile, alkoxybenzenesulphoneacetonitriles, e.g. p-methoxybenzenesulphoneacetonitrile, toluene-, xylene-, nitrobenzene- or naphthylsulphoneacetonitrile, or cyclohexylsulphoneacetonitrile (the aryl and aralkyl compounds containing, if desired, further nuclear substituents, e.g. oxy, amino or substituted amino groups); on the other hand N - alkyl - N - oxyalkylaminobenzaldehydes, e.g. N - methyl - N - oxyethyl -, N - ethyl - N - oxyethyl-or -oxypropyl-, or N-propyl-N-oxyethyl-p - aminobenzaldehyde, N - dioxyalkyl - p - aminobenzaldehydes, e.g. N - dioxyethyl - or N - dioxypropyl - p - aminobenzaldehyde, N - alkyl - N - alkoxyalkyl - p - aminobenzaldehydes, e.g. N - methyl - N - methoxyethyl -, N - ethyl - N - methoxy - or - ethoxyethyl - or N - propyl - N - ethoxyethyl - p - aminobenzaldehyde; N - dialkoxyalkyl - p - aminobenzaldehydes, e.g. N - dimethoxyethyl - p - aminobenzaldehyde, N - alkyl - N - acyloxyethyl - p - aminobenzaldehydes, e.g. N - methyl - N - acetoxyethyl- or N - ethyl - N - acetoxy - or - propionyloxyethyl - p - aminobenzaldehyde, N - diacetoxyethyl - p - aminobenzaldehyde, N - oxyalkyl - N - alkoxyalkyl - p - aminobenzaldehydes, e.g. N - oxyethyl- N - methoxyethyl - p - aminobenzaldehyde, N - bis - dioxypropyl - p - aminobenzaldehyde, N - oxyethyl - N - oxychloropropyl - p - aminobenzaldehyde, N - methoxyethyl - N - oxychloropropyl - p - aminobenzaldehyde, N - methoxyethyl - N - g -methoxy - b  - oxypropyl - p - aminobenzaldehyde and N - oxyethyl - N - g  - methoxy - b  - oxypropyl - p - aminobenzaldehyde.  The products may be used for colouring lacquers from natural or artificial resins, nitrocellulose or acetylcellulose, or for dyeing artificial materials, e.g. phenol- or urea-aldehyde condensation products, or cellulose esters and ethers, e.g. acetate artificial silk.  In examples: (1) benzenesulphoneacetonitrile is refluxed with N - ethyl - N - methoxyethyl - p - aminobenzaldehyde in alcoholic solution with the addition of a strong base, e.g. piperidine, alkali or a sodium alcoholate; the product, after suitable suspension, e.g. by p grinding with dispersing agents, such as sulphite cellulose liquor or sulphonated residues from benzaldehyde manufacture, and water, dyes acetate artificial silk green-yellow shades; (2) benzenesulphoneacetonitrile is refluxed in alcoholic solution with N - ethyl - N - oxyethyl - p - aminobenzaldehyde and piperidine; the product dyes acetate artificial silk green-yellow shades; methyl-, ethyl- or other alkylsulphoneacetonitriles may be similarly reacted. Methyl-, ethyl-, propyl-, butyl-, allyl-, cyclohexyl- and benzylsulphoneacetonitriles are obtainable by condensing the corresponding sulphinic acid salts with chloracetonitrile.