GB720795A - Manufacture of vat dyestuffs of the anthraquinone series - Google Patents

Manufacture of vat dyestuffs of the anthraquinone series

Info

Publication number
GB720795A
GB720795A GB6532/53A GB653253A GB720795A GB 720795 A GB720795 A GB 720795A GB 6532/53 A GB6532/53 A GB 6532/53A GB 653253 A GB653253 A GB 653253A GB 720795 A GB720795 A GB 720795A
Authority
GB
United Kingdom
Prior art keywords
carboxylic acid
aminoanthraquinone
metoxazone
acid chloride
anthraquinone
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
GB6532/53A
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 SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB720795A publication Critical patent/GB720795A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Dyes are made by treating with ammonia or primary amines at elevated temperature metoxazones of the formula: <FORM:0720795/IV (c)/1> which may be substituted, e.g. in position X, preferably by halogen, nitro, or amino. The reaction may be carried out under increased pressure. The ring oxygen is stated to be replaced by imino, giving the pyrimidone, and the products containing unsubstituted imino groups may be alkylated. The metoxazones may be prepared according to French Specification 847,152 from o-aminoanthraquinone carboxylic acid chlorides alone or with another anthraquinone carboxylic acid. The products dye cotton various shades. In examples: (1) the metoxazone from 1-aminoanthraquinone-2-carboxylic acid chloride or its 4-nitro derivative or from 2-aminoanthraquinone-3-carboxylic acid chloride, is heated with aqueous ammonia, followed by methylation with p-toluene sulphonic acid methyl ester; (2) similar treatment is applied to the metoxazones from anthraquinone-2-carboxylic acid chloride and 1 - aminoanthraquinone - 2 - carboxylic acid or 2-aminoanthraquinone 3 or 1-carboxylic acid, that from anthraquinone-1-carboxylic acid chloride and 2-aminoanthraquinone-3-carboxylic acid, that from 2-chloranthraquinone-3-carboxylic acid chloride and 1-aminoanthraquinone-2-carboxylic acid or 2-aminoanthraquinone-3-carboxylic acid, or that from 1-chloranthraquinone-2-carboxylic acid and 2-aminoanthraquinone-3-carboxylic acid; (3) the metoxazone from 1-aminoanthraquinone-2-carboxylic acid chloride is reacted with methylamine, butylamine, cyclohexylamine, dodecylamine, stearylamine, aniline or its halogen, alkyl, nitro, hydroxy, or methoxy derivatives; (4) the metoxazone from 2-aminoanthraquinone-3-carboxylic acid is reacted with methylamine; (5) the metoxazone from anthraquinone-2-carboxylic acid chloride and 2-aminoanthraquinone-3-carboxylic acid is reacted with dodecylamine or with aniline or substitution products thereof; (6) the metoxazone from anthraquinone-2-carboxylic acid chloride and 1 - aminoanthraquinone - 2 - carboxylic acid is reacted with methylamine; (7) the metoxazone from 1-nitroanthraquinone-2-carboxylic acid chloride and 2-aminoanthraquinone-3-carboxylic acid is reacted with gaseous ammonia in nitrobenzene and the product is methylated with p-toluene sulphonic acid methyl ester.
GB6532/53A 1952-03-25 1953-03-10 Manufacture of vat dyestuffs of the anthraquinone series Expired GB720795A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE720795X 1952-03-25

Publications (1)

Publication Number Publication Date
GB720795A true GB720795A (en) 1954-12-29

Family

ID=6628645

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6532/53A Expired GB720795A (en) 1952-03-25 1953-03-10 Manufacture of vat dyestuffs of the anthraquinone series

Country Status (1)

Country Link
GB (1) GB720795A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3012031A (en) * 1959-10-12 1961-12-05 American Cyanamid Co Anthraquinone oxadiazines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3012031A (en) * 1959-10-12 1961-12-05 American Cyanamid Co Anthraquinone oxadiazines

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