Patent GB-191117129-A (GB)
Title: Manufacture and Production of New Aryl Ethers of Meta-oxybenzaldehydes Substituted in the Nucleus and of New Triphenylmethane Dyes therefrom and from the Alkyl Ethers of Meta Oxybenzaldehydes Substituted in the Nucleus.
Inventor: NEWTON PHILIP ARTHUR
IPC: C07C205/38
Filed: 1911-07-26
Granted: 1912-05-30
Abstract: 17,129. Newton, P. A., [Farbenfabriken vorm. F. Bayer & Co.]. July 26. m-Oxybenzaldehyde derivatives.-Aryl ethers of m-oxybenzaldehydes substituted in the nucleus are obtained by condensing salts of m-oxybenzaldehydes substituted in the nucleus with halogenized aromatic compounds of the benzene series. The following products are described:- o-nitrophenyl-3-oxy-2:6-dichlorbenzaldehyde, pchlor-o-nitrophenyl-3-oxy-2:6-dichlorbenzalde, phyde, o-chlor-p-nitrophenyl-3-oxy-2:6-dichlorbenzaldehyde, o-p-dinitrophenyl-3-oxy-2:6-dichlorbenzaldehyde, o-nitro-p-sulphophenyl-3-oxy- 2:6-dichlorbenzaldehyde, p-chlor-o-nitrophenyl- 3-oxy-6-sulphobenzaldehyde, dinitrophenylenebis- 3-oxy--2: 6-dichlorbenzaldehyde from 1:3-dichlor- 4:6-dinitrobenzene and two molecules of 3-oxy- 2:6-dichlorbenzaldehyde, nitrosulphophenylenebis-3-oxy-2:6-dichlorbenzaldehyde from 1:3-dichlor-4-nitrobenzene-6-sulphonic acid and two molecules of 3-oxy-2:6-dichlorbenzaldehyde, dinitrophenylenebis - 3 - oxy-2: 4: 6-trichlorbenzaldehyde from 1:3-dichlor-4:6-dinitrobenzene and two molecules of 3-oxy-2:4:6-trichlorbenzaldehyde. The following parent materials are also specified: -2-chlor-5-oxybenzaldehyde, brom and sulphonic derivatives of m-oxybenzaldehyde; pnitrochlorbenzene, o-chlorbenzoic acid, p-p<1>-dichlorbenzophenone, p-p<1>-dichlorbenzosulphone. When the halogen compound contains several replaceable halogen atoms, one or more oxyaldehydes can be combined with it. Solvents or diluents may be used in the process, for example, water, nitrobenzene, amyl alcohol, glycerine, or the oxyaldehyde itself. The following other derivatives of m-oxybenzaldehyde are also described : -3-methoxy-2:6-dichlorbenzaldehyde, 3-methoxy-2:6-dibrombenzaldehyde, 3-methoxy - 2: 4: 6-trichlorbenzaldehyde, 3-ethoxy-2: 4:6-trichlorbenzaldehyde, 3-carboxymethoxy-2: 4:6-trichlorbenzaldehyde from chloracetic acid and 3-oxy-2:4:6-trichlorbenzaldehyde, ethylenebis-3-oxy-2:4:6-trichlorbenzaldehyde from ethylenedibromide and trichlor-m-oxybenzaldehyde. The Provisional .Specification refers also to pnitrobenzoyl-3-oxy-2:4:6-trichlorbenzaldehyde, carbonylbis-3-oxy-2 : 4 : 6 - trichlorbenzaldehyde, and to the use of m-oxybenzaldehyde itself in the process described above. Triarylmethane dyes are obtained by condensing the alkyl or aryl ethers of m-oxybenzaldehyde substituted in the aldehyde nucleus with o-oxycarboxylic acids of the benzene series, or mixtures thereof, and oxidizing the leuco compounds thus produced. Products are described from the alkyl and aryl ethers specified above and salicylic or o-cresotinic acid or a mixture of o- and p-cresotinic acid; the bisoxyaldehyde compounds specified above are condensed with four molecules of the oxycarboxylic acid. The products give on wool, when afterchromed, blue to violet shades. Specification 15,204/07 is referred to. The Provisional Specification describes also similar dyes from the nitrobenzoyl and carbonyl derivatives specified above.