Patent GB-599562-A (GB)
Title: Improvements in or relating to coloured fibres and the like
IPC: C09B69/00
Filed: 1945-07-20
Abstract: Fibres coloured with a dye which contains two monovalent aliphatic radicles each of which contains at least eight carbon atoms united by carbon to carbon linkages are obtained by spinning a solution of a fibre-forming material in an organic liquid, said solution being coloured with a dye of the type defined, or by applying to the spun fibres a solution of such a dye in an organic liquid as described in Specification 550,659.  Fibre-forming materials specified are cellulose acetate, propionate, butyrate, aceto-propionate, aceto-butyrate, or nitro-acetate, also methyl, ethyl and benzyl celluloses, and polymerized vinyl compounds.  The dye may be of the azo, anthraquinone, or nitrodiarylamine series, and the aliphatic radicles may be present in the form of a group -CO.NR1R2 or -SO2, NR,R2 attached to the aryl dye nucleus, wherein R1 and R2 are the radicles, or may be attached according to one of the following formul , X p  being the aryl dye nucleus <FORM:0599562/IV/1> The radicles may be primary, secondary, or tertiary, and may be attached to the same carbon atom, which may itself be attached to a carboxyamide group as in the dioctylacetylamino radical. Radicles specified are n-octyl, 2 - ethyl - n - hexyl, n - undecyl, n - dodecyl, secondary dodecyl, n-pentadecyl-, n-hexadecyl, n-heptadecyl, n-octadecyl, decenyl, undecenyl, heptadecenyl, octadecenyl, 8.9-dibromheptadecyl, 9.10 - dibromoctadecyl, di - (n - octyl) methyl, di - (n - octyl) - ethyl, di - (sec. - octyl)-methyl, di - (n - dodecyl) - methyl, n - dodecyl - n-butyl-methyl.  The acetone solutions of the fibre-forming material may be spun by wet or dry methods and the coloured fibres may be topped with other dyes, e.g. nitro, azo, or anthraquinone dyes.  A list of dyes given is as follows:-(1) 4 - diethylamino - azobenzene-41 - carboxylic acid di - octyl - amide (golden orange); (2) 4-(alpha : alpha-di-n-octyl-acetylamino) - 41 - dimethylamino - azo - benzene (yellow); (3) 4 - stearoylamino - 21 - hydroxy - 51 - dodecyl - azo - benzene (yellow); (4) 4-(alpha : alpha - di - n - octyl - acetylamino) - 21 - hydroxy - 51 - phenyl - azo - benzene (yellow); (5) 2 : 6-dichlor-4-nitro-41-diethylamino-21-(alpha : alpha - di - n - octyl - acetylamino) - azo-benzene (Rubine); (6) 4-nitro-41-diethylamino-21 - (alpha - alpha - di - n - octyl - acetylamino) azo-benzene (red); (7) 4-(benzeneazo)-41-di-ethylamino - 21 - (alpha - alpha - di - n - octyl - acetylamino)-azo-benzene (red); (8) Azo dye from diazotized p-nitraniline and 2 : 3-hydroxy-naphthoic acid anilide-31-sulpho-dioctyl amide (red); (9) 1-amino-4-p-anisidino-anthraquinone-2-carboxylic di-octyl-amide (blue); (10) 1-amino - 4 - o - anisidino - anthraquinone - 2 - carboxylic di-octyl-amide (blue); (11) 1-amino- or 1 - methylamino - 4 - p - toluido- or 4-anilido anthraquinone-2-carboxylic di-octyl amide (all blue); (12-17) 1-amino-4-(o- or p-anisidino- or anilido -) anthraquinone - 2 - carboxylic di (dodecylamide or 2-ethylhexylamide) (blue); (18) 1 - phenylamino - anthraquinone - 2 - carboxylic di - octyl - amide (bluish red); (19) 1 - cyclohexylamino - anthraquinone - 2 - carboxylic di - octyl - amide (bright bluish red); (20) 1 - methylamino - anthraquinone - 2 - carboxylic di-octyl-amide (bright bluish red); (21-24) 1-phenylamino- or cyclohexylamino-anthraquinone - 2 - carboxylic - di(dodecylamide or 2 - ethyl - hexylamide); (25-26) 2-nitro-diphenylamino-4- or 21-carboxylic acid di-octylamide (yellow); (27) 2-nitro-41-methoxy-diphenylamine-4-carboxylic acid di-octyl-amide (golden yellow); (28) 2 : 4-dinitro-diphenyl amine-41-carboxylic acid di-octyl-amide (lemon yellow); (29-30) 2-nitrodiphenylamine-4-carboxylic - didoceylamide, and - di - (2 - ethyl-hexylamide) (yellow); (31) 2 : 4-dinitro-41 - (alpha : alpha - di - n - octyl-acetylamino) diphenylamine (yellow); (32) 1-cyclohexyamino - 2 - nitro - benzene - 4 - carboxylic acid di-(n-octyl)-amide (greenish yellow); (33) 2-nitro - diphenylamine - 4 - sulpho - di(n-octyl)-amide (pure yellow); (34) 2-nitro-41-methoxydiphenylamine - 4 - sulpho - di(n - octyl) - amide (golden yellow); (35) 2-nitrodiphenylamine-4-sulpho-didodecylamide (yellow); (36) 2-nitro-41-methoxy-diphenylamine - 4 - sulpho - didodecylamide (golden-yellow).  The azo dyes may be prepared by coupling, e.g. phenols, amines, or pyrazolones with diazo compounds of amines, including diazotized aminoazo compounds, one or other reactant containing a group -NHCOCHR1R2 or -CO.NR1R2 or -SO2.NR1R2, where R1 and R2 are aliphatic radicles of at least eight carbon atoms.  The nitrodiarylamine dyes may be made by interaction of a halogenaryl and an aminoaryl compound at least one of which carries a nitro group and one or both of which carry the requisite aliphatic radicles, e.g. attached to the nitrogen atom of a carboxylic amide or sulphonamide group.  The dyes generally may be made by methods comprising alkylation or acidylation of hydroxy, mercapto, or amino groups, by esterification of carboxylic or sulphonic groups, by reacting carboxylic chloride or sulphochloride groups with secondary amines, or e.g. by reacting a halogenanthraquinone containing a carboxylic amide or sulphonamide group with ammonia or an amine. Specifications 282,036, 313,451, [both in Class 2 (ii)], 460,575 and 551,435 also are referred to.