GB743220A - Process for the manufacture of dyestuffs of the anthraquinone series suitable for dyeing cellulose acetate artificial silk - Google Patents

Process for the manufacture of dyestuffs of the anthraquinone series suitable for dyeing cellulose acetate artificial silk

Info

Publication number
GB743220A
GB743220A GB14516/53A GB1451653A GB743220A GB 743220 A GB743220 A GB 743220A GB 14516/53 A GB14516/53 A GB 14516/53A GB 1451653 A GB1451653 A GB 1451653A GB 743220 A GB743220 A GB 743220A
Authority
GB
United Kingdom
Prior art keywords
leuco
anthraquinone
sodium
dihydroxyanthraquinone
nitrobenzene
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
GB14516/53A
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 Schweiz AG
Original Assignee
Ciba 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 Ciba AG filed Critical Ciba AG
Publication of GB743220A publication Critical patent/GB743220A/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
    • C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
    • C09B1/285—Dyes with no other substituents than the amino groups
    • 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
    • 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
    • C09B1/262—Dyes with no other substituents than the substituted amino groups

Landscapes

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

Abstract

Dyestuff mixtures are made by reacting an aliphatic amine and ammonia simultaneously with 1.4-dihydroxyanthraquinone in presence of a leuco compound of an anthraquinone containing a hydroxyl, an amino, or an alkylamino group in each of the 1- and 4-positions and, if desired, oxidizing the leuco body in the resulting reaction mixture. The leuco-compound may be formed in the reaction mixture from the 1.4-dihydroxy-anthraquinone by addition of a reducing agent. The reactions may be conducted in an aqueous medium in presence of a water-soluble organic solvent. In examples (1) a mixture of 1.4-dihydroxyanthraquinone and its leuco-body is heated with methanol, isobutyl alcohol or xylene, aqueous or alcoholic ammonia, and one of the following: b -oxyethylamine, g -oxypropylamine, b g -dioxypropylamine, isopropylamine, methylamine, ethylamine, n-propylamine, n - butylamine, secondary butylamine; followed by oxidation with sodium 3-nitrobenzene-1-sulphonate, sodium chlorate, a stream of air in presence of copper acetate and piperidine, or nitrobenzene. Also in examples (2) 1.4-dihydroxyanthraquinone and leuco -1-hydroxy or amino -4-isopropylamino or leuco -1.4-di-(b - oxyethylamino) - anthraquinone are heated with methanol, aqueous ammonia, and isopropylamine, followed by oxidation with sodium-3-nitrobenzene-1-sulphonate; (3) 1.4-dihydroxy-anthraquinone is reacted with methanol, methylamine, aqueous ammonia, and sodium hydrosulphite or zinc dust, with or without sodium bicarbonate. The products dye cellulose esters (e.g., acetate), nylon and superpolymethanes blue-violet shades.
GB14516/53A 1952-05-30 1953-05-22 Process for the manufacture of dyestuffs of the anthraquinone series suitable for dyeing cellulose acetate artificial silk Expired GB743220A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH743220X 1952-05-30

Publications (1)

Publication Number Publication Date
GB743220A true GB743220A (en) 1956-01-11

Family

ID=4533311

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14516/53A Expired GB743220A (en) 1952-05-30 1953-05-22 Process for the manufacture of dyestuffs of the anthraquinone series suitable for dyeing cellulose acetate artificial silk

Country Status (6)

Country Link
BE (1) BE520324A (en)
CH (4) CH307977A (en)
DE (1) DE1016387B (en)
FR (1) FR1077295A (en)
GB (1) GB743220A (en)
NL (1) NL92298C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1364993A1 (en) * 2002-05-21 2003-11-26 Bayer Aktiengesellschaft Process for the preparation of N,N'-disubstituted diaminoanthraquinones
CN103084073A (en) * 2011-10-31 2013-05-08 中国科学院合肥物质科学研究院 Porous membrane composed of cellulose doped with 1,4-dihydroxy anthraquinone and bivalent copper ion and preparation method and application thereof

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE716046C (en) * 1936-12-24 1942-01-12 Ig Farbenindustrie Ag Process for the preparation of dyes of the anthraquinone series
GB507206A (en) * 1937-12-08 1939-06-08 Henry Charles Olpin Manufacture of compounds of the anthraquinone series
US2335680A (en) * 1941-09-25 1943-11-30 Du Pont Arylaminoanthraquinone compounds

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1364993A1 (en) * 2002-05-21 2003-11-26 Bayer Aktiengesellschaft Process for the preparation of N,N'-disubstituted diaminoanthraquinones
CN103084073A (en) * 2011-10-31 2013-05-08 中国科学院合肥物质科学研究院 Porous membrane composed of cellulose doped with 1,4-dihydroxy anthraquinone and bivalent copper ion and preparation method and application thereof
CN103084073B (en) * 2011-10-31 2015-06-03 中国科学院合肥物质科学研究院 Porous membrane composed of cellulose doped with 1,4-dihydroxy anthraquinone and bivalent copper ion and preparation method and application thereof

Also Published As

Publication number Publication date
CH311503A (en) 1955-11-30
DE1016387B (en) 1957-09-26
BE520324A (en)
CH322877A (en) 1957-06-30
CH307977A (en) 1955-06-30
NL92298C (en)
CH317768A (en) 1956-11-30
FR1077295A (en) 1954-11-05

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