GB678983A - Process for the preparation of bright violet dyestuffs of the anthraquinone series - Google Patents

Process for the preparation of bright violet dyestuffs of the anthraquinone series

Info

Publication number
GB678983A
GB678983A GB13196/50A GB1319650A GB678983A GB 678983 A GB678983 A GB 678983A GB 13196/50 A GB13196/50 A GB 13196/50A GB 1319650 A GB1319650 A GB 1319650A GB 678983 A GB678983 A GB 678983A
Authority
GB
United Kingdom
Prior art keywords
phenol
amino
tert
sulpho
sodium salt
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
GB13196/50A
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.)
Sandoz AG
Original Assignee
Sandoz 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 Sandoz AG filed Critical Sandoz AG
Publication of GB678983A publication Critical patent/GB678983A/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
    • C09B1/50—Amino-hydroxy-anthraquinones; Ethers and esters thereof
    • C09B1/54—Amino-hydroxy-anthraquinones; Ethers and esters thereof etherified
    • C09B1/547—Anthraquinones with aromatic ether 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
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups

Landscapes

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

Abstract

The invention comprises bright violet dyes which are fast to fulling consisting of sulphonation products of compounds of formula <FORM:0678983/IV (c)/1> where A is H or Me, B is H or, when A is Me B may also be Me and R is a saturated aliphatic or cycloaliphatic hydrocarbon radical containing 4 to 8 C atoms. They are made by heating a compound of formula <FORM:0678983/IV (c)/2> where A and B are as above and X is Br or SO3H or an alkali metal salt of SO3H, with phenols which are substituted by a saturated aliphatic or cycloaliphatic hydrocarbon radical containing 4 to 8 C atoms, in the presence of acid binding agents, and sulphonating the ensuing dyestuff. Phenols specified are p-tert. butyl-, p-sec. amyl, p-tert. amyl, p-cyclohexyl and p-isooctyl phenol. Diluents such as nitrobenzene, di-p-tert.-butyl-p-cresol or methylhexaline may be present. Acid binding agents specified are hydroxides, carbonates and acetates of alkali metals advantageously those of sodium or potassium. Temperatures for completion of the condensation are about 200 DEG C. although lower temperatures, e.g. 140 DEG C. may be used. When 2-bromo compounds are reacted the formation of higher molecular weight compounds is obviated by an increased concentration of alkali. The dye bases are isolated on dilution with alcohol or on pouring into warm dilute caustic soda solution. Sulphonation is effected in sulphuric acid monohydrate at 20-50 DEG C. In examples the bases from the following condensations are sulphonated: (1) p-tert.-butyl phenol and the condensation product of 1-amino-2-sulpho-4-brom-anthraquinone with mesidine; (2) p-isooctyl phenol and 1-amino-2-brom-4-mesidino-anthraquinone; (3) p-isooctyl phenol and the sodium salt of 1-amino-2-sulpho-4-mesidinoanthraquinone; (4) p-tert.-amyl phenol and the condensation product of 1-amino-2-sulpho-4-brom-anthraquinone and vic.-m-xylidine; (5) p-sec. amyl phenol and the sodium salt of 1-amino - 2 - sulpho - 4 - vic. - m - xylidinoanthraquinone; (6) p-cyclohexyl phenol and the sodium salt of (5); (7) p-tert.-butyl phenol and the condensation product of 1-amino-2-sulpho-4-brom-anthraquinone with isoduridine; (8) p-tert.-amyl phenol and the sodium salt of 1-amino - 2 - sulpho - 4 - isoduridino - anthraquinone; (9) p-tert.-amyl phenol and 1-amino - 2 - brom - 4 - mesidino - anthraquinone; (10) p-tert.-butyl phenol and the sodium salt of 1 - amino - 2 - sulpho - 4 - vic. - m - xylidinoanthraquinone; (11) p(isooctyl phenol and the sodium salt of (10); (12) p-cyclohexyl phenol and the sodium salt of 1-amino-2-sulpho-4-mesidino-anthraquinone, and (13) p-sec.-amyl phenol and the sodium salt of (12). Specifications 26944/11, [Class 2 (iii)], 477,535 and 483,950 are referred to.
GB13196/50A 1949-06-03 1950-05-25 Process for the preparation of bright violet dyestuffs of the anthraquinone series Expired GB678983A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH678983X 1949-06-03

Publications (1)

Publication Number Publication Date
GB678983A true GB678983A (en) 1952-09-10

Family

ID=4528328

Family Applications (1)

Application Number Title Priority Date Filing Date
GB13196/50A Expired GB678983A (en) 1949-06-03 1950-05-25 Process for the preparation of bright violet dyestuffs of the anthraquinone series

Country Status (1)

Country Link
GB (1) GB678983A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2392081A1 (en) * 1977-05-26 1978-12-22 Ciba Geigy Ag NEW WATER-SOLUBLE ANTHRAQUINONE DYES, THEIR PREPARATION PROCESS AND THEIR USE FOR DYING AND PRINTING TEXTILES
FR2392082A1 (en) * 1977-05-26 1978-12-22 Ciba Geigy Ag NEW ANTHRAQUINONIC COLORANTS SOLUBLE IN WATER
FR2408586A1 (en) * 1977-11-14 1979-06-08 Ciba Geigy Ag NEW ANTHRAQUINONE DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR USE AS COLORANTS
EP0012111A2 (en) * 1978-11-24 1980-06-11 Ciba-Geigy Ag Water-soluble dyes of the 1-amino-2-phenoxy-4-phenylamino anthraquinone series; process for their preparation and their application

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2392081A1 (en) * 1977-05-26 1978-12-22 Ciba Geigy Ag NEW WATER-SOLUBLE ANTHRAQUINONE DYES, THEIR PREPARATION PROCESS AND THEIR USE FOR DYING AND PRINTING TEXTILES
FR2392082A1 (en) * 1977-05-26 1978-12-22 Ciba Geigy Ag NEW ANTHRAQUINONIC COLORANTS SOLUBLE IN WATER
FR2408586A1 (en) * 1977-11-14 1979-06-08 Ciba Geigy Ag NEW ANTHRAQUINONE DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR USE AS COLORANTS
EP0012111A2 (en) * 1978-11-24 1980-06-11 Ciba-Geigy Ag Water-soluble dyes of the 1-amino-2-phenoxy-4-phenylamino anthraquinone series; process for their preparation and their application
EP0012111A3 (en) * 1978-11-24 1980-08-06 Ciba-Geigy Ag Water-soluble dyes of the 1-amino-2-phenoxy-4-phenylamino anthraquinone series; process for their preparation and their application and intermediates

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