GB483313A - Manufacture of dyestuffs of the anthraquinone series - Google Patents

Manufacture of dyestuffs of the anthraquinone series

Info

Publication number
GB483313A
GB483313A GB2802736A GB2802736A GB483313A GB 483313 A GB483313 A GB 483313A GB 2802736 A GB2802736 A GB 2802736A GB 2802736 A GB2802736 A GB 2802736A GB 483313 A GB483313 A GB 483313A
Authority
GB
United Kingdom
Prior art keywords
amino
acid
hydroxy
sulphobenzoic
reacted
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
GB2802736A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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
Priority to DEI51261D priority Critical patent/DE638835C/en
Priority to US54938A priority patent/US2081359A/en
Priority to FR799569D priority patent/FR799569A/en
Priority to DEI56033D priority patent/DE677860C/en
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to GB2802736A priority patent/GB483313A/en
Priority to US161160A priority patent/US2159506A/en
Priority to FR48844D priority patent/FR48844E/en
Publication of GB483313A publication Critical patent/GB483313A/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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • C09B1/34—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated
    • C09B1/346—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups sulfonated only sulfonated in a substituent
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/52—Amino-hydroxy-anthraquinones; Ethers and esters thereof sulfonated
    • C09B1/523—N-substituted amino and hydroxy anthraquinone
    • C09B1/525—N-aryl derivatives

Landscapes

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

Abstract

One mol. of an unsulphonated a .a 1-dihalogenanthraquinone containing in 1.5 - or 1.8-positions hydroxyl-, amino-, alkylamino-, or arylamino-groups is reacted with 2 mols. of a sulphonated aromatic amino - o - hydroxycarboxylic acid or with 2 mols. of an unsulphonated aromatic amino - o hydroxycarboxylic acid followed by sulphonation. Alternatively, an a .a 1-dihalogenanthraquinone containing sulphonic groups in b -position may be used, the b -sulphonic groups being split off by reduction in a neutral or alkaline medium, preferably with sodium hydrosulphite, after reaction with the hydroxycarboxylic acid, followed by sulphonation if the hydroxy-carboxylic acid contains no sulpho group. The products dye wool blue, grey, or green tints, and can be transformed into chromium lakes. In examples: (1) 1.5-dihydroxy-4.8-dichloroanthraquinone is reacted with 3 - amino - 2 - hydroxy - 5 - sulphobenzoic acid in presence of potassium and copper acetates, copper powder, water and either methanol or glycol; (2) 1.5-dihydroxy-4.8-dichloranthraquinone is condensed with 5-amino-2-hydroxy-3-sulphobenzoic acid as in (1); (3) 4.8 - dibromanthrarufin - 2.6 - disulphonic acid is condensed with 5-amino-2-hydroxybenzoic acid in presence of water, sodium carbonate and bicarbonate, and cuprous chloride and the 1.5 - dihydroxy - 4.8 - di - (41-hydroxy - 31 - carboxyphenyl) - aminoanthraquinone-2.6-disulphonic acid so obtained is reduced with alkaline hydrosulphite to split off the 2.6-sulphonic groups, followed by sulphonation; (4) 4.5 - dichlor - 1.8 - dihydroxyanthraquinone is condensed with 3-amino-2-hydroxy - 5 - sulphobenzoic or 5 - amino - 2-hydroxy - 3 - sulphobenzoic acid; (5) 1.5-dichloro-4.8-diaminoanthraquinone is reacted with 3 - amino - 2 - hydroxy - 5 - sulphobenzoic acid or 5-amino-2-hydroxy-3-sulphobenzoic acid; (6) 1.5-diamino-2.4.6.8-tetrachloranthraquinone is reacted with 3-amino-2-hydroxy-5-sulphobenzoic acid or 5-amino-2-hydroxy-3-sulphobenzoic acid; (7) 4.8-dibromo-1.5-didimethylaminoanthraquinone is reacted with 3 - amino - 2 - hydroxy - 5 - sulphobenzoic acid. Specification 452,424 is referred to.
GB2802736A 1934-12-19 1936-10-15 Manufacture of dyestuffs of the anthraquinone series Expired GB483313A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
DEI51261D DE638835C (en) 1934-12-19 1934-12-19 Process for the preparation of chromating dyes of the anthraquinone series
US54938A US2081359A (en) 1934-12-19 1935-12-17 Anthraquinone dyestuffs capable of being chromed
FR799569D FR799569A (en) 1934-12-19 1935-12-18 New chromatable anthraquinone dyes and their preparation process
DEI56033D DE677860C (en) 1934-12-19 1936-09-27 Process for the production of chromating dyes of the anthraquinone series
GB2802736A GB483313A (en) 1936-10-15 1936-10-15 Manufacture of dyestuffs of the anthraquinone series
US161160A US2159506A (en) 1934-12-19 1937-08-26 Anthraquinone dyestuffs capable of being chromed
FR48844D FR48844E (en) 1934-12-19 1937-09-27 New chromatable anthraquinone dyes and their preparation process

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2802736A GB483313A (en) 1936-10-15 1936-10-15 Manufacture of dyestuffs of the anthraquinone series

Publications (1)

Publication Number Publication Date
GB483313A true GB483313A (en) 1938-04-19

Family

ID=10269079

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2802736A Expired GB483313A (en) 1934-12-19 1936-10-15 Manufacture of dyestuffs of the anthraquinone series

Country Status (1)

Country Link
GB (1) GB483313A (en)

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