GB605701A - Manufacture of vat dyestuffs - Google Patents

Manufacture of vat dyestuffs

Info

Publication number
GB605701A
GB605701A GB21345/44A GB2134544A GB605701A GB 605701 A GB605701 A GB 605701A GB 21345/44 A GB21345/44 A GB 21345/44A GB 2134544 A GB2134544 A GB 2134544A GB 605701 A GB605701 A GB 605701A
Authority
GB
United Kingdom
Prior art keywords
amino
acid
chloroanthraquinone
phenylsulphonebenzene
carboxylic acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB21345/44A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Gesellschaft fuer Chemische Industrie in Basel CIBA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Gesellschaft fuer Chemische Industrie in Basel CIBA
Publication of GB605701A publication Critical patent/GB605701A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16Amino-anthraquinones
    • C09B1/20Preparation from starting materials already containing the anthracene nucleus
    • C09B1/36Dyes with acylated amino groups
    • C09B1/42Dyes with acylated amino groups the acyl groups being residues of an aromatic carboxylic acid

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

4 - (41 - Chloro- and 41 - methoxy - phenylsul - phone)-benzene-3-carboxylic acids are obtained by condensing p-toluenesulphochloride with chlorobenzene or anisole respectively, in the presence of aluminium chloride, and oxidizing the methyl group with permanganate. 3 - Phenylsulphonebenzene - 1 - carboxylic acid is obtainable by condensing benzoic acid-m-sulphochloride with benzene, in excess of benzene as solvent, in the presence of aluminium chloride. Specification 580,642 is referred to.ALSO:Vat dyestuffs, which are 1 : 4-diaroylaminoanthraquinones in which at least one (but preferably only one) of the aroyl groups is the residue of a phenylsulphonebenzenecarboxylic acid, and which may contain further substituents (e.g. halogen atoms), are manufactured by aroylating a 1 : 4-diaminoanthraquinone or a 1-aroylamino-4-aminoanthraquinone with a phenylsulphonebenzenecarboxylic acid or a reactive derivative thereof, or, in the case of a 1 - phenylsulphonebenzoylamino-4-aminoanthraquinone, with any aroylating agent, or by condensing a 1 : 4-dihalogenanthraquinone or a 1 - aroylamino - 4 - halogenanthraquinone with a phenylsulphonebenzenecarboxylic acid amide, or, in the case of a 1-phenylsulphonebenzoylamino-4-halogenanthraquinone, with any aromatic acid amide. The products may be used for dyeing or printing animal fibres and especially vegetable fibres such as cotton or linen, and regenerated cellulose artificial silk and staple fibres, and also superpolyamide fibres, for which purposes the dyestuffs are advantageously employed in the form of their sulphuric acid leuco-ester salts. In examples: (1) 4-phenylsulphonebenzene-1-carboxylic acid is stirred with thionyl chloride and a trace of pyridine in o-dichlorobenzene, the excess thionyl chloride and some solvent are distilled off, and the mixture is heated with 1-amino-4-benzoylaminoanthraquinone; the 4-phenylsulphonebenzenecarboxylic acid may be replaced by its 41-chloro- or 41-methoxy-derivative or by 3 - phenylsulphonebenzene - 1 - carboxylic acid; (2) 4-phenylsulphonebenzene-1-carboxylic acid or its 41-chloro-derivative is similarly reacted with 1 : 4-diaminoanthraquinone (in the molecular proportions of 2 : 1); (3) 1-(41-phenylsulphonebenzoylamino) -4-benzoylaminoanthraquinone is vatted with sodium hydrosulphite and caustic soda solution and cotton is dyed in the vat with the addition of sodium chloride, and then squeezed, oxidised in the air, rinsed, acidified, again rinsed, and soaped at the boil, yielding a pink dyeing. Specification 580,642 is referred to. Samples have been furnished under Sect. 2(5) of the products obtained by treating (A) 1-chloro-4-benzoylaminoanthraquinone with 4-phenylsulphonebenzene - 1 - carboxylic acid amide; (B) 1-amino-4-(p-chlorobenzoyl)-aminoanthraquinone with 4-phenylsulphonebenzene-1-carboxylic acid chloride; (C) 1-benzoylamino - 4 - amino - 6 - chloroanthraquinone similarly; (D) 1-amino-4-(p-phenylsulphonebenzoylamino)-7-chloroanthraquinone with benzoyl chloride. 1-Benzoylamino - 4 - amino - 3 - chloroanthraquinone is obtainable by benzoylating 1-amino-4- nitro-6-chloroanthraquinone and reducing the nitro group. 1 - Amino - 4 - (p - phenylsulphonebenzoylamino)-7-chloroanthraquinone is obtainable by treating 1-amino-4-nitro-6-chloroanthraquinone with 4 - phenylsulphonebenzene - 1 - carboxylic acid chloride and reducing the nitro group, e.g. with phenylhydrazine in o-dichlorobenzene. 1-Amino-4-nitro-3-chloroanthraquinone is obtainable by heating 1-amino-6-chloroanthraquinone with oxalic acid and nitrating the resulting oxaminic acid in concentrated sulphuric acid. The Specification as open to inspection under Sect. 91 comprises also the manufacture of products containing other aryl-sulphone-aroylamino groups, with or without other acylamino groups which may be non-aromatic. This subject-matter does not appear in the Specification as accepted.
GB21345/44A 1943-11-01 1944-11-01 Manufacture of vat dyestuffs Expired GB605701A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH605701X 1943-11-01

Publications (1)

Publication Number Publication Date
GB605701A true GB605701A (en) 1948-07-29

Family

ID=4523069

Family Applications (1)

Application Number Title Priority Date Filing Date
GB21345/44A Expired GB605701A (en) 1943-11-01 1944-11-01 Manufacture of vat dyestuffs

Country Status (1)

Country Link
GB (1) GB605701A (en)

Similar Documents

Publication Publication Date Title
GB605701A (en) Manufacture of vat dyestuffs
GB790082A (en) New dyestuff compositions of the anthraquinone series
GB449010A (en) New anthraquinone dyestuffs
GB459770A (en) Manufacture of 1:4:5-tribenzoylamino-8-oxyanthraquinone
GB549640A (en) New anthraquinone vat dyes
GB699781A (en) Process for the production of acid fulling dyestuffs of the anthraquinone series
GB733458A (en) Anthraquinone dyestuffs
GB885681A (en) New anthraquinone dyestuffs and their manufacture and use
GB733372A (en) Manufacture of new anthraquinone vat dyestuffs
GB627078A (en) Manufacture of vat dyestuffs
GB1001063A (en) New water-soluble reactive monoazo dyestuffs, their preparation and use
GB580642A (en) Manufacture of vat dyestuffs
GB737016A (en) Manufacture of vat dyestuffs of the anthraquinone series
DE1917921A1 (en) Anthraquinone dyes, their manufacture and use
GB791304A (en) Vat dyestuffs of the anthraquinone series
GB704013A (en) Manufacture of vat dyestuffs of the anthraquinone series
GB448654A (en) Manufacture of indigoid dyestuffs
GB854162A (en) New vat dyestuffs of the anthraquinone series and process for their manufacture
GB898912A (en) Process for dyeing or printing fibrous materials of aromatic polyesters
GB292741A (en) Manufacture of vat-dyestuffs
GB332579A (en) Manufacture of vat dyestuffs of the dibenzopyrenequinone series
GB630592A (en) Process for the manufacture of new acid dyestuffs of the anthraquinone series
GB745072A (en) New dyestuffs of the dioxazine series and process for making them
GB678523A (en) New vat dyestuffs of the acedianthrone series
GB333992A (en) The manufacture of anthraquinone intermediates and dyestuffs therefrom