Patent GB-716007-A (GB)
Title: Acid monoazo dyestuffs and a process for their manufacture
IPC: C09B29/30
Filed: 1952-08-21
Abstract: The invention comprises acid monoazo dyestuffs of formula: <FORM:0716007/IV(c)/1> where acyl is a saturated fatty acid radicle containing 8-12 carton atoms, X is H or any substituent except NO2, SO3H or COOH, one Y is H or alkyl and the other Y H or alkyl and if one Y is H the other may be joined to the unsubstituted position X by the chain CH2-CH2-CH2-CH2.  They may be made by coupling a diazo compound of an amino benzene sulphonic acid of formula: <FORM:0716007/IV(c)/2> with a 1-hydroxynaphthalene-3-sulphonic acid of formula:  <FORM:0716007/IV(c)/3> Representative of many groups mentioned for X are halogen, alkyl, alkoxy, -NH-acyl, -SO2-alkyl, -SO2- <FORM:0716007/IV(c)/4> or O-SO2-alkyl.  Representative of aminobenzene-sulphonic acids used are 1-aminobenzene-2-sulphonic acid, 1-amino-5-chloro- or ethyl- or methoxy- or N-formyl or N-chlorobenzoyl-2-sulphonic acid, 1-amino-5-propyl-sulphonbenzene-2-sulphonic acid, 1-amino-2-sulpho-benzene-5-sulphonic acid-N-propyl amide, 1-amino-2-sulpho-benzene-5-sulphonic acid-N : N-methyl-benzylamide, 1-amino- 2-sulpho-benzene-5-sulphonic acid - N : N-benzyl-cyclohexylamide, 1-amino-2-sulpho-benzene-5-sulphonic acid-chlorophenyl ester, 1-amino-5-methyl-sulphonyl-hydroxybenzene-2-sulphonic acid, 1-amino-4, 6-dimethylbenzene-2-sulphonic acid, 1-amino-5, 6, 7, 8-tetrahydro-naphthalene-2-sulphonic acid. 1-hydroxy-6-N-octanoyl-, -decanoyl or -do-decanoyl-aminonaphthalene-3-sulphonic acids are specified 1-hydroxynaphthalene-3-sulphonic acids.  Coupling is effected in a medium of pH varying from weakly alkaline to that of acetic acid preferably in the presence of sodium carbonate or acetate.  The dyestuffs dye fibres e.g. wool, nylon and silk, from neutral or weakly acid baths in orange tints.  In examples (1) 1-aminobenzene-2-sulphonic acid is diazotized and coupled with 1-hydroxy-6-N-octanoylamino-naphthalene-3-sulphonic acid, (2) 1-amino - 5 - methylsulphonbenzene-2-sulphonic acid is diazotized and coupled with 1-hydroxy-6-N-decanoylaminonaphthalene - 3 - sulphonic acid, (3) 1 - amino-2-sulphobenzene-5-sulphonic acid phenyl ester is diazotized and coupled with 1-hydroxy-6-N-dodecanoylamino-naphthalene-3-sulphonic acid (4) 1-aminobenzene-2-sulphonic acid is diazotized and coupled with 1-hydroxy-6-N-decanoylamino-naphthalene-3-sulphonic acid, (5) 1-amino-5-methyl-sulphonbenzene-2-sulphonic acid is diazotized and coupled with 1-hydroxy-6-N-dodecanoylamino-naphthalene - 3-sulphonic acid.  (6) 1 - amino-5-N-acetylamino-benzene-2-sulphonic acid is diazotized and coupled with 1-hydroxy-6-N-decanoylamino-naphthalene-3-sulphonic acid, (7) 1-amino-4-methyl-5-chlorobenzene-2-sulphonic acid is diazotized and coupled with 1-hydroxy-6-N-octanoylamino-naphthalene-3-sulphonic acid, (8) 2-amino-5, 6, 7, 8-tetrahydronaphthalene-3-sulphonic acid is diazotized and coupled with 1-hydroxy-6-N-decanoylamino-naphthalene-3-sulphonic acid (9) 1-amino-4, 5-dimethylbenzene-2-sulphonic acid is diazotized and coupled with 1-hydroxy-6-N-dodecanoylamino-naphthalene-3-sulphonic acid and in (10) a dyestuff obtained in Examples (1)-(9) is used to dye wool from a bath containing acetic and formic acids and sodium sulphate.  A variety of alternative reagents is also specified for Examples (1)-(9).  Specification 432,020 is referred to.