Patent GB-974136-A (GB)
Title: Reactive mono- and dis-azo dyestuffs
Inventor: BARBEN IAN KNOWLES
IPC: C09B62/026
Filed: 1962-05-15
Abstract: The invention comprises azo dyes which in the form of the free acids are of formula <FORM:0974136/C4-C5/1> wherein one L is a group of formula D-N = N-wherein D is a benzene, naphthalene or stilbene radical which may be substituted, e.g. by arylazo groups and the other L is a hydroxy group, n is 1, 2 or 3, and P which is attached to the 5-, 6- or 7-position of the naphthalene ring is a group of formula <FORM:0974136/C4-C5/2> wherein m and p are 1 or 2, V is a phenylene or sulphophenylene radical, R is a hydrogen atom or an alkyl radical, R1 and R2 are methyl groups and R3 and R4 are hydrogen atoms or methyl groups, or when R3 and R4 are both hydrogen R1 and R2 are joined to form a tetra- or pentamethylene radical or R1 and R3 and R2 and R4 are joined together to form in each case a trimethylene radical, X is a mono- or di-chloropyrimidyl, 5-cyano-chloropyrimidyl, or a divalent 1,3,5-triazinyl radical substituted in the 6-position by a hydrogen atom or an alkyl, alkoxy, phenyl, phenoxy, amino or substituted amino group.  The dyes are prepared (a) by reacting a dye of the above formula but wherein P is a group of formula <FORM:0974136/C4-C5/3> with a hydrazine of formula <FORM:0974136/C4-C5/4> or (b) by coupling a diazo compound of an amine D-NH2 with a coupling component of formula <FORM:0974136/C4-C5/5> wherein one L1 is a hydrogen atom and the other is a hydroxy group.  Specified hydrazines are N,N,N1 - trimethylhydrazine, N,N,N1,N1-tetramethylhydrazine, N - aminopiperidine, N - aminopyrrolidine - 1,5 - diazabicyclo - (0,3,3) - octane and preferably N,N-dimethylhydrazine. The dyes may be used to colour wool, silk and polyamides but are preferably used to dye cellulose textile materials in the presence of an acid-binding agent in orange, red, blue and brown shades. Examples are given.  The Provisional Specification specifies dyes of the above formula but wherein X is a 1,3,5-triazinyl radical substituted in 6-position by a halogen atom, thioether or thiocyano group, or a methyl- or nitro-halopyrimidyl, mono- or dibromopyrimidyl, cyano - bromopyrimidyl, methyl-nitropyrimidyl or carbomethoxypyrimidyl radical.  A wider range of hydrazine and diamine compounds is specified including N-amino - morpholine, N - methyl - N1 - aminopiperazine, N - methyl - N - phenylhydrazine, N : N - dimethyl - N1 - phenylhydrazine, N,N,N1 - trimethyl - N1 - phenylhydrazine, N - methyl - N - ethylhydrazine, N - methyl - N - b  - hydroxyethyl - hydrazine, N - methyl - N - allyl - hydrazine, tetramethylurea, tetramethylthiourea, N : N : N1 : N1 - tetramethylguanidine, pentamethylguanidine, a  : a  - dimethylsemi-, carbazide, a  : a  - dimethylthiosemicarbazide-N - (dimethylamino) - guanidine, N : N1 - di - (dimethylamino) - urea or - thiourea or - guanidine or -ethylenediamine or -propylenediamine N,N - dimethyl - N1 - acetyl - or - formyl - hydrazine, N : N : N1 - trimethyl - N - formylhydrazine, N - methyl - N - phenyl - N1 - acetyl - hydrazine, N,N - dimethylhydrazine - N1 - sulphonic acid N - (dimethylamino)dithiocarbamate and N-methylhexahydropyridazine. No additional examples are specified.  Specifications 822,047, 859,989 and 872,249 are referred to.