Patent GB-190018726-A (GB)
Title: Improvements in the Manufacture of Derivatives of Aromatic Amines Including New Colouring Matters
Inventor: WILLCOX Benjamin
Filed: 1900-10-19
Granted: 1901-08-24
Abstract: 18,726. Willcox, B., [Badische Anilin & Soda Fabrik]. Oct. 19. Amines; phenols; sulphonic acids; dyes, artificial.-Relates to further applications of the invention described in Specification No. 1387, A.D. 1900. (1) Alkyl derivatives of aromatic amines are produced by' acting upon sulphurous acid esters of phenolic bodies with fatty mono- or di-alkylamines, or by acting upon phenolic bodies capable of forming a sulphurous acid ester with a fatty mono- or di-alkylamine and the sulphite of the said amine. Examples are given in which monomethylnaphthionic acid and monomethyl-#- naphthylamine sulphonic acid are respectively produced from 1-naphthol-4-sulphonic acid and 2 : 6-naphthol sulphonic acid by heating these compounds with monomethylamine sulphite and monomethylamine ; and dimethyl-m-amidophenol is obtained from resorcinol by treatment with dimethylamine sulphite and dimethylamine. (2) Alphylated aromatic amines are produced by heating sulphurous acid esters of phenolic bodies with aromatic amines. Examples are given in which phenyl-#-naphthylamine sulphonic acid is produced from 2 : 6-naphthol sulphonic acid by heating it with sodium bisulphite and aniline ; 2-phenylamido-5-naphthol-7-sulphonic acid is produced by heating 2 : 5-dihydroxynaphthalene-7-sulphonic acid with ammonium sulphite and aniline ; phenylamidonaphthol sulphonic acid, 2-o-tolylamido-8- naphthol-6-sulphonic acid, 2-o-xylylamido-5-naphthol-7-sulphonic acid, hydroxvphenylamidonaphthol sulphonic acid, phenylnaphthylamine sulphonic acid, and amidophenylnaphthylamine sulphonic acid are respectively produced by heating in presence of sodium bisulphite 2 : 8-amidonaphthol- 6-sulphonic acid, with aniline, 2 :8-amidonaphthol- 6-sulphonic acid with o-toluidine, 2 : 5 : 7-amidonaphthol sulphonic acid with o-xylidine, 2 : 8 : 6- amidonaphthol sulphonic acid with p-amidophenol, 2 : 6-naphthylamine sulphonic acid with aniline, and 2 : 6-naphthol sulphonic acid with p-phenylenediamine. (3) Fuchsine derivatives of aromatic amines are similarly produced. Examples are given in which a fuchsine derivative of #-naphthylamine sulpbonic acid is produced by heating fuchsine with 2 : 6-naphthol sulphonic acid or 2 :6-naphthylamine sulphonic acid and sodium bisulphite solution. Theproduct dyes wool bright blue. In a similar manner dyes may be produced from fuchsine and 2-naphthol-6 : 8-disulphonic acid, 2 : 7 - dihydroxynaphthalene, 2-amido-5- naphthol-7-sulphonic acid, or other naphthol or naphthylamine derivative. In these cases the sulphurous acid ester of the phenolic body may be first prepared and then acted upon with fuchsine. (4) Symmetrical #-dinaphthylamine derivatives are produced by treating a #-naphthol body, or a sulphurous acid ester thereof, with neutral ammonium sulphite. Examples are given in which #-dinaphthylamine disulphonic acid is thus abtained from 2 : 6-naphtbol sulphonic acid, and dihydroxydinaphthylamine disulphonic acid is obtained from 2 : 5-dihydroxynaphthalene-7-sulphonic acid.