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    Water-soluble dyes of the tetrazaporphin series
    4.
    发明专利
    Water-soluble dyes of the tetrazaporphin series 未知

    公开(公告)号：GB924533A

    公开(公告)日：1963-04-24

    申请号：GB575261

    申请日：1961-02-16

    Applicant: BASF AG

    Inventor： TARTTER ARNOLD ,  LANGE GUENTER ,  STEUERLE HELMUT

    Abstract: p(g -Sulphato-b - hydroxy-propoxy) aniline and m-(g -sulphato-b - hydroxy-propoxy)-acetanilide are made by esterifying with sulphuric acid p(b :g -dihydroxy-propoxy) aniline and m(b :g -dihydroxy-propoxy) acetanilide. 2-Methyl- 5-(g - p-toluenesulphonyloxy-b -hydroxy-propoxy) aniline is prepared by reacting 2:3- epoxypropyl- (3-formylamino-4-methylphenyl) ether with p-toluene sulphonic acid in acetone. 2-Methyl-5-glycidyloxy-formanilide is made by reacting 2-methyl-5-hydroxy-formanilide with epichlorhydrin.ALSO:The invention comprises water-soluble dyes of the tetrazaporphin series which contain at least one ionic water-solubilizing group and at least one b :g -dihydroxypropyl radical attached to a carbon atom by way of an oxygen or sulphur atom or an amino or sulphone group or attached to a carbonyl or sulphonyl group by way of an amino group, which radical is esterified at the g -position by sulphuric acid, phosphoric acid or an organic sulphonic acid. The dyes are made by suitably esterifying a tetrazaporphin containing at least one b :g -dihydroxypropyl radical attached as indicated above, or by treating a tetrazaporphin containing at least one appropriately attached b :g -epoxypropyl radical with sulphuric, phosphoric or an organic sulphonic acid, or by reacting a tetrazaporphin sulphonic or carboxylic acid halide or a halo-triazinyl tetrazaporphin with an aliphatic or aromatic amine containing the esterified b :g -dihydroxypropyl radical described above. The tetrazaporphin starting materials containing the b :g -dihydroxypropyl or b :g -epoxypropyl radicals are made by reacting tetrazaporphin sulphinic acids, mercaptans, hydroxy compounds or amines with a 1-halo-2:3-dihydroxy-propane or with glycide or by reacting them with an epihalohydrin or a glycerol dihalohydrin and converting the halohyadrins obtained to the epoxides and thence if desired to the dihydroxy compounds, or by condensing tetrazaporphin sulphonic or carboxylic acid halides or a halotriazinyl tetrazaporphin with primary or secondary aliphatic or aromatic amines containing the b :g -dihydroxy- or -epoxypropyl radicals. Examples are given. The dyes dye and print leather, wool, silk and materials of polycaprolactam and condensation products of adipic acid and hexamethylene diamine and especially of natural or regenerated cellulose in conjunction with an alkali and heat treatment. Specifications 854,962, 868,285 and 879,244 are referred to.

    Water-soluble azo dyestuffs containing esterified dihydroxypropyloxy groups
    5.
    发明专利
    Water-soluble azo dyestuffs containing esterified dihydroxypropyloxy groups 未知

    公开(公告)号：GB901546A

    公开(公告)日：1962-07-18

    申请号：GB4164359

    申请日：1959-12-08

    Applicant: BASF AG

    Inventor： LANGE GUENTER ,  STEUERLE HELMUT ,  SCHROEDEL RUDOLF ,  MUELLER ROLAND ,  FEDERKIEL WILHELM

    Abstract: The invention comprises azo dyes derived from a benzenic diazo component and a naphtholic or enolic coupling component which contain at least one b ,g -dihydroxypropyl radical, combined by way of oxygen, which is esterified in the g -position with sulphuric acid or an organic sulphonic acid and which contains altogether at least one of the groups sulphonic, carboxy and sulphuric acid ester. The dyes may be made by treating appropriate dyes, or intermediates, containing a b ,g -dihydroxypropyl group with sulphuric acid or a halide, anhydride, acid sulphate or pyrosulphate thereof, or those containing a sulphonic and/or a carboxylic group and a b ,g -dihydroxypropyl group with an organic sulphonic acid or a halide or anhydride thereof, or by treating appropriate dyes or intermediates containing a b ,g -epoxypropyl group with sulphuric or a sulphonic acid, and, if necessary, the dye is formed by known methods from the intermediates. Preferred dyes are those of formula (D-N=N-E)-(OCH2CHOH.CH2OY)p1 which may have up to 3 sulphonic and/or carboxy groups, where D is a benzene residue, E the coupling component residue, Y a residue of sulphuric or a sulphonic acid and p1 or 2, and where D and E may contain neutral substituents such as methyl, phenyl, ethoxy, chlorine, amino, mono- and di-ethylamino, benzoylamino, cyano, nitro, trifluoromethyl, sulphonamide, carboxylic acid amide and alkylsulphone groups. D or E may also contain additional azo groups. Especially preferred are dyes of formula where A is the dye residue, R an organic radical, X a sulphonic or carboxy group, Z+ a cationic radical, e.g. H, NH4 or K, m O, 1 and 2, n 1 or 2 and q 1 or 2. Dyes with especially valuable tinctorial properties are obtained from diazo components which contain the oxypropyl group but no sulphonic or carboxy groups. Specified sulphonic acids include ethane, vinyl, b -chloroethyl, p-toluene, o-chlorobenzene, naphthalene-2- and diphenyl-p1p1-di-sulphonic acids. When disulphonic acids are used two diazo components may be combined to give a tetrazo component. Acylation of the b hydroxy group takes place to a slight extent. The dyes colour natural and synthetic substances containing carbonamide groups, e.g. leather, wool, silk, polycaprolactam and condensation products of adipic acid and hexamethylene diamine. They are particularly of use on native and regenerated cellulose, e.g. cotton, linen, viscose rayon, hemp and jute. The dyeing of cellulosic materials is preferably effected in conjunction with an alkaline treatment and a thickening agent. Numerous examples are provided for the preparation of the dyes and their use in colouring cotton in red and yellow shades representative of the coupling components used for monoazo dyes being, 2-naphthol, 1-naphthol-4-sulphonic acid, 2-amino-8-naphthol-6-sulphonic acid, 1-acetylamino-8-naphthol-4,6-disulphonic acid, 2-naphthol-3-carboxylic acid p-sulphoanilide, acetoacetate acid anilide and 1-(3-sulphophenyl)-3-methyl-5-pyrazolone and the disazo dye 4-aniline sulphonic acid --> 3-aminophenyl-(b ,g -dihydroxypropyl) ether (sulphuric acid ester) --> 1-(4-sulphophenyl)-3-methyl-5-pipazolone, is also prepared.

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