Production of dyes of the anthraquinone series

    公开(公告)号:GB1044740A

    公开(公告)日:1966-10-05

    申请号:GB4822764

    申请日:1964-11-27

    Applicant: BASF AG

    Abstract: Anthraquinone dyestuffs of the general formula wherein X is OH and/or NHR1; Y is OH or NHR1; A is hydrogen, chlorine or bromine; B is oxygen or =NR1; R, R1 and R11 are hydrogen or are alkyl, cycloalkyl aryl or aralkyl groups which may be substituted and n is 1 or 2 are prepared by reacting a compound of the general formula wherein Z is hydrogen, a cyano, carbonyl, carboxylic acid ester, RHN-CO- or R2NCO-group and X, Y, A, R and n are as above; with an ionic cyanide or an a -hydroxynitrile, if desired in the presence of a primary amine, and the mixture to be reacted or the reaction product is treated with an oxidizing agent. The reaction preferably takes place at 30-230 DEG C. in presence of an inert solvent, e.g. water, alcohols, ethers, acid amides, organic bases, sulphoxide or sulfones, and melts or aqueous solutions of sodium and potassium salts. Oxidizing agents used in amounts of at least two oxidation equivalents include atmospheric oxygen, salts of peroxy acids, alkali metal chlorates and nitro compounds. When atmospheric oxygen is used ammonium vanadate is added to the reaction mixture. Ionic cyanides used are sodium, potassium, ammonium, magnesium and calcium cyanides which may be in admixture and the a -hydroxynitriles used include acetocyanohydrin or mandelonitrile. The ionic cyanides and a -hydroxynitriles are preferably used in molar excess of the anthraquinone compounds. The primary amine which may be present include C1-C4 aliphatic amines, cyclo-alkylamines and araliphatic amines all of which may be substituted by hydroxy, alkoxy, amino, alkylamino, dialkylamino, cyano and heterocyclic rings. Many examples are given.

    Dyes of the anthraquinone series
    6.
    发明专利

    公开(公告)号:GB914453A

    公开(公告)日:1963-01-02

    申请号:GB2935560

    申请日:1960-08-25

    Applicant: BASF AG

    Abstract: Polysryrene or linear polyamides, possibly with the addition of titanium dioxide are dyed in bulk with a dye of the anthraquinone series containing at least one para-(arylcarbonyl)-phenylamino radical attached to the nucleus. For dyeing polystyrene, dyes are preferred of the formula where D is a group of the formula and each of X1, Y1 and Z1 is hydrogen, a group D or a group of the formula Red, violet and blue dyeings are obtained.ALSO:The invention comprises anthraquinone dyes containing at least one phenylaryl ketone radical, free from carboxylic acid groups, attached to the anthraquinone nucleus via an amino group in the position of the phenyl ring para to the keto group, and a process for making them by reacting at elevated temperatures an anthraquinone derivative containing at least one primary or secondary amino group directly attached to the nucleus with a p-halo-phenyl aryl ketone. Anthraquinone derivatives include aminophthaloylacridones, aminoanthrapyrimidines and amino-anthraquinones substituted by hydroxy, methoxy, acylamino, bromo and nitro groups. Aryl radicals may be substituted by hydroxy, alkyl or alkoxy but those specified are naphthyl, diphenyl and phenyl. Examples are given. The dyes are pigments for cellulose acetate, viscose, polyacrylonitrile, copolymers of acrylonitrile and polystyrene, giving red, violet and blue shades (see Group IV(a)).

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