GB633481A - Manufacture of leuco sulphuric ester derivatives of vat dyestuffs - Google Patents

Manufacture of leuco sulphuric ester derivatives of vat dyestuffs

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Publication number
GB633481A
GB633481A GB2519746A GB2519746A GB633481A GB 633481 A GB633481 A GB 633481A GB 2519746 A GB2519746 A GB 2519746A GB 2519746 A GB2519746 A GB 2519746A GB 633481 A GB633481 A GB 633481A
Authority
GB
United Kingdom
Prior art keywords
leuco
compound
anthraquinone
specified
compounds
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
GB2519746A
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.)
DAVID ALEXANDER WHYTE FAIRWEAT
Imperial Chemical Industries Ltd
Original Assignee
DAVID ALEXANDER WHYTE FAIRWEAT
Imperial Chemical Industries Ltd
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 DAVID ALEXANDER WHYTE FAIRWEAT, Imperial Chemical Industries Ltd filed Critical DAVID ALEXANDER WHYTE FAIRWEAT
Priority to GB2519746A priority Critical patent/GB633481A/en
Publication of GB633481A publication Critical patent/GB633481A/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
    • C09B9/00Esters or ester-salts of leuco compounds of vat dyestuffs

Landscapes

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

Abstract

Leuco-sulphuric esters of vat dyes and anthraquinone dye intermediates and salts thereof are made by reacting the corresponding leuco compound, or a metal salt of the corresponding leuco compound, or a complex compound comprising the metal salt of the corresponding leuco compound, in the presence of an organic amide as defined below, with or without the addition of diluents, with sulphur trioxide or with an addition compound of sulphur trioxide with an organic amide or tertiary base, or with any substance known to be capable of forming sulphuric esters from vat dyestuffs in the presence of metals, or from leuco compounds, or metal salts thereof, or complex compounds comprising the metal salts thereof. The amides are compounds of the formula R.CO.NR1R2 or R.SO2.NR1R2, where R stands for a hydrogen atom or an organic radical or, when the compound is of the formula R.CO.NR1R2, for a hydrogen atom and R1 and R2 stand for hydrocarbon radicals or substituted hydrocarbon radicals which may be the same or different and which may be connected with each other to form together with the nitrogen atom a closed ring. Amides specified are dimethylformamide, diethylformamide, dimethylacetamide, formylpiperidide, tetramethylurea, and diethyltoluenesulphonamide. Alternatives to sulphur trioxide specified are the addition compounds thereof with dimethylformamide or picoline, or an ester of chlorsulphonic acid. Metals specified are zinc, iron, and copper, and catalysts for the formation of the metal salt specified are potassium ethyl sulphate, sodium - 2 - naphthol - 6 - sulphonate, calcium naphthalene-2.6-disulphonate, sodium-naphthalene-sulphonate, ferric chloride, and magnesium chloride. In examples, the following substances are converted to their leuco compound metal salts (if not already in that form) and then to their leuco-sulphuric esters, using amides of the type defined: (1) 1.4-dibenzoylaminoanthraquinone; (2) 16.17-dimethoxydibenzanthrane; (3) 5.51 - diethoxythioindigo; (4) 2 - (1 - amino - 2 - anthraquinonyl) - antraquinone-21.31-oxazole; (5) 3-chloro-2-acetylamino - anthraquinone; (6) 2 - chloro-anthraquinone; (7) anthraquinone; (8) 9.10-dihydroxyanthracene; (9) leuco-indigo; (10) leuco - 16.17 - dimethoxydibenzanthrone; (11) 4.10 - dibromoanthanthrone; (12) 16.17 - dimethoxydibenzanthrone; (13) 1 : 11 : 4 : 111 - trianthrimide - 2.21.3.211 - dicarbazole; (14)2 - (1 - amino - 2 - anthraquinonyl) - anthraquinone - 21.31-oxazole; (15) anthraquinonyl-1-urethane; (16) 1.11-dianthrimide; (17) leuco-16.17-dimethoxydibenzanthrone; (18) leuco-flavanthrone. Specifications 186,057, 274,156, [both in Class 2 (iii)], 633,478 and 633,480, [both in Group IV (c)], are referred to.ALSO:Leuco-sulphuric esters of vat dyes and anthraquinone dye intermediates and salts thereof are made by reacting the corresponding leuco compound, or a metal salt of the corresponding leuco compound, or a complex compound comprising the metal salt of the corresponding leuco compound, in the presence of an organic amide as defined below, with or without the addition of diluents, with sulphur trioxide or with an addition compound of sulphur trioxide with an organic amide or tertiary base, or with any substance known to be capable of forming sulphuric esters from vat dyestuffs in the presence of metals or from leuco compounds, or metal salts thereof, or complex compounds comprising the metal salts thereof. The amides are compounds of the formula R.CO.NR1R2 or R.SO2.NR1R2, where R stands for a hydrogen atom or an organic radical or, when the compound is of the formula R.CO.NR1R2, for a hydrogen atom and R1 and R2 stand for hydrocarbon radicals or substituted hydrocarbon radicals which may be the same or different and which may be connected with each other to form together with the nitrogen atom a closed ring. Amides specified are dimethylformamide, p diethylformamide, dimethylacetamide, formylpiperidide, tetramethylurea, and diethyl-p-toluenesulphonamide. Alternatives to sulphur trioxide specified are the addition compounds thereof with dimethylformamide or picoline, or an ester of chlorsulphonic acid. Metals specified are zinc, iron, and copper, and catalysts for the formation of the metal salt specified are potassium ethyl sulphate, sodium - 2 - naphthol - 6 - sulphonate, calcium naphthalene - 2 : 6 - disulphonate, sodium b -naphthalene-sulphonate, ferric chloride, and magnesium chloride. In examples, the following substances are converted to their leuco compound metal salts (if not already in that form) and then to their leuco-sulphuric esters, using amides of the type defined: (1) 1.4-dibenzoylaminoanthraquinone; (2) 16.17-dimethoxydibenzanthrone; (3) 5.51-diethoxythioindigo; (4) 2-(1-amino-2-anthraquinonyl)-anthraquinone - 21.31 - oxazole; (5) 3 - chloro-2 - acetylamino - anthraquinone; (6) 2 - chloroanthraquinone; (7) anthraquinone; (8) 9.10-dihydroxyanthracene; (9) leuco-indigo; (10) leuco - 16.17 - dimethoxydibenzonthrone; (11) 4.10-dibromoanthanthrone; (12) 16.17-dimethoxydibenzanthrone; (13) 1 : 11 : 4 : 111 - trianthrimide - 2.21.3.211 - dicarbozole; (14) 2-(1 - amino - 2 - anthraquinonyl) - anthraquinone-21.31-oxazole; (15) anthraquinonyl-1-urethane; (16) 1.11-dianthrimide; (17) leuco-16.17-dimethoxydibenzanthrone; (18) leuco-flavanthrone. Specifications 186,057, 274,156, [both in Class 2 (iii)], 633,478 and 633,480 are referred to.
GB2519746A 1946-08-23 1946-08-23 Manufacture of leuco sulphuric ester derivatives of vat dyestuffs Expired GB633481A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2519746A GB633481A (en) 1946-08-23 1946-08-23 Manufacture of leuco sulphuric ester derivatives of vat dyestuffs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2519746A GB633481A (en) 1946-08-23 1946-08-23 Manufacture of leuco sulphuric ester derivatives of vat dyestuffs

Publications (1)

Publication Number Publication Date
GB633481A true GB633481A (en) 1949-12-19

Family

ID=10223800

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2519746A Expired GB633481A (en) 1946-08-23 1946-08-23 Manufacture of leuco sulphuric ester derivatives of vat dyestuffs

Country Status (1)

Country Link
GB (1) GB633481A (en)

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