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    Production of 1,4-diamino-2-aryloxy-anthraquinone-3-sulphonic acid
    3.
    发明授权
    Production of 1,4-diamino-2-aryloxy-anthraquinone-3-sulphonic acid 失效
    生产1,4-二氨基-2-芳氧基 - 蒽醌-3-磺酸

    公开(公告)号：US2001221A

    公开(公告)日：1935-05-14

    申请号：US66365433

    申请日：1933-03-30

    申请人： GEN ANILINE WORKS INC

    发明人： BERTHOLD STEIN ,  FRITZ BAUMANN

    IPC分类号： C09B1/54

    CPC分类号： C09B1/547 ,  C09B1/22

    摘要： 1 . 4 - diamino - 2 - aryloxyanthraquinone - 3 - sulphonic acids are prepared by reacting 1 . 4 - diamino - 2 . 3 - dihalogenanthraquinones with phenols or naphthols and salts, preferably water-soluble inorganic salts, of sulphurous acid in the presence of metal compounds having acid-binding properties but the alkalinity of which is neither sufficient to split off or replace by hydroxy groups the halogen atoms present in the molecule of the initial material nor sufficient to have a saponifying action on the aryloxy group introduced. Such acid-binding agents are incapable of forming salts with phenols or naphthols; in addition to these properties they may possess oxidising properties. Suitable metal compounds are alkali metal perborates, oxides and hydroxides of metals other than alkali metals or alkaline earth metals, such as pyrolusite, lead peroxide, magnesium oxide, zinc oxide. Advantageously about 10 molar proportions of the phenol and 2--3 molar proportions of the sulphurous acid salt is reacted with 1 molar proportion of the anthraquinone compound; increased pressure and temperatures of 120--160 DEG C. are favoured. In examples (1) 1 . 4 - diamino - 2 . 3 - dichloranthraquinone is heated in an autoclave with phenol, sodium sulphite and pyrolusite at 130 DEG C.; pyrolusite may be replaced by lead peroxide, or magnesia when a reacting temperature of 140 DEG C. is employed; 1 . 4 - diamino - 2 . 3 - dibromanthraquinone may be similarly treated; (2) 1 . 4 - diamino - 2 - 3 - dichloranthraquinone is heated in an autoclave with m-cresol, sodium sulphite and pyrolusite to 140 DEG C.; m-cresol may be replaced by p-chlorphenol or b -naphthol.

    Anthraquinone dyestuffs
    4.
    发明授权
    Anthraquinone dyestuffs 失效
    蒽醌染料

    公开(公告)号：US1957858A

    公开(公告)日：1934-05-08

    申请号：US55794331

    申请日：1931-08-18

    申请人： GEN ANILINE WORKS INC

    发明人： BERTHOLD STEIN

    IPC分类号： C09B1/54

    CPC分类号： C09B1/547 ,  C09B1/22

    摘要： 1 : 4-Diamino-2-aryloxy-3-sulphoanthraquinones are prepared by heating 1 : 4-diamino-2 : 3-dichloranthraquinones under atmospheric pressure with a phenol and a sulphite of a strong, preferably inorganic, base in the presence of water. In examples 1 : 4-diamino-2 : 3-dichloranthraquinone is boiled with phenol and aqueous sodium sulphite to give 1 : 4-diamino-2-phenoxy-3-sulphoanthraquinone; this product is saponified to the corresponding 2-oxy derivative by warming with dilute soda and it dyes wool from a faintly acid bath in blue-violet shades. The sodium sulphite may be replaced by the methylamine salt of sulphurous acid, and homologues and substitution products of phenol may replace the latter; thus when m-cresol is used 1 : 4-diamino-2-cresoxy-3-sulphoanthraquinone which dyes wool violet-blue shades is obtained. The dyestuffs produced from halogenphenols also yield violet dyeings on wool.

    Acid wool dyestuff of the anthraquinone series and process of making same
    7.
    发明授权
    Acid wool dyestuff of the anthraquinone series and process of making same 失效
    蒽醌系列酸羊毛染料及其制作方法

    公开(公告)号：US1968178A

    公开(公告)日：1934-07-31

    申请号：US60465232

    申请日：1932-04-11

    申请人： GEN ANILINE WORKS INC

    发明人： BERTHOLD STEIN ,  ERNST HONOLD

    IPC分类号： C09B1/24 ,  C09B1/54

    CPC分类号： C09B1/24 ,  C09B1/22 ,  C09B1/547

    摘要： Aminoanthraquinone derivatives are prepared by replacing in either sequence one halogen atom of a 1,4-diamino-2,3-dihalogenanthraquinone by a mercapto or disulphide group by means of an alkali metal sulphide followed by oxidation of this mercapto or disulphide group to a sulphonic acid group, and replacing the other halogen atom by an aryloxy group by treatment with a phenol. The resulting products, 1,4-diamino - 2 - aryloxyanthraquinone-3-sulphonic acids are similar to but purer than the products of Specification 363,027 and they may be further sulphonated. The oxidation of the mercapto or disulphide group is effected in acid or alkaline medium by means of hydrogen peroxide or alkali metal peroxide, perborate or persulphate. The introduction of the aryloxy group is effected by heating in presence of an acid-binding agent and advantageously at about 100 DEG C. In examples, (1) 1,4-diamino-2,3-dichloranthraquinone is boiled with excess sodium disulphide to give 1,4-diamino-3-chloro-2-mercaptoanthraquinone, this is oxidized by hydrogen peroxide to the corresponding 2-sulphonic acid, and the latter boiled with phenol in presence of sodium carbonate; sulphonation of this dyestuff by means of concentrated sulphuric acid gives a soluble, blue wool dye; (2) 1,4-diamino-2,3-dichloranthraquinone is heated with sodium phenolate in phenol to give 1,4-diamino-3-phenoxy-2-chloranthraquinone; treatment of this with excess sodiumdisulphide in alcohol replaces the 2-chloro atom by a mercapto residue, which product is oxidized by hydrogen peroxide (or alkali peroxides or perborates) to the 2-sulpho derivative; (3) 1,4-diamino-3-chloro - 2 - mercaptoanthraquinone (cf. 1) is oxidized to the 2-sulpho derivative by means of concentrated sulphuric acid and potassium persulphate, or the starting material is first converted to its zinc salt or the disulphide by zinc chloride and air oxidation respectively, and p then oxidized; a 1,4-diamino-3-bromo-2-sulphoanthraquinone is similarly prepared from 1,4-diamino-2,3-dibromanthraquinone, and both products on heating with p-cresol yield an acid wool dye (navy-blue); (4) if phenol is replaced in (1) by resorcinol a blueish-violet acid wool dye is obtained and similar shades are also obtained by using guaiacol, m-hydroxybenzoic acid, or xylenols; (5) 1,4-diamino-3-chloranthraquinone - 2 - sulphonic acid (cf. 1) is heated with an alkaline solution of a - or b -naphthol; a navy-blue acid wool dye is obtained; (6) 1,4-diamino-3-b -naphthoxyanthraquinone-2-mercaptan (prepared in an analogous manner to the phenoxy derivative--cf. 2) is oxidized with hydrogen peroxide to give the same product as in (5). The products are dyes for acetate silk as well as wool.