GB486660A - Manufacture of dyestuffs - Google Patents

Manufacture of dyestuffs

Info

Publication number
GB486660A
GB486660A GB30284/36A GB3028436A GB486660A GB 486660 A GB486660 A GB 486660A GB 30284/36 A GB30284/36 A GB 30284/36A GB 3028436 A GB3028436 A GB 3028436A GB 486660 A GB486660 A GB 486660A
Authority
GB
United Kingdom
Prior art keywords
diazotized
coupled
acid
pyrazolone
dye
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
GB30284/36A
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
Gesellschaft fuer Chemische Industrie in Basel CIBA
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 Gesellschaft fuer Chemische Industrie in Basel CIBA filed Critical Gesellschaft fuer Chemische Industrie in Basel CIBA
Publication of GB486660A publication Critical patent/GB486660A/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
    • C09B31/00—Disazo and polyazo dyes of the type A->B->C, A->B->C->D, or the like, prepared by diazotising and coupling
    • C09B31/02—Disazo dyes
    • C09B31/025—Disazo dyes containing acid groups, e.g. -COOH, -SO3H, -PO3H2, -OSO3H, -OPO2H2; Salts thereof
    • 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
    • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/02—Disazo dyes
    • C09B33/12—Disazo dyes in which the coupling component is a heterocyclic compound
    • 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
    • C09B33/00—Disazo and polyazo dyes of the types A->K<-B, A->B->K<-C, or the like, prepared by diazotising and coupling
    • C09B33/18—Trisazo or higher polyazo dyes
    • 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
    • C09B35/00—Disazo and polyazo dyes of the type A<-D->B prepared by diazotising and coupling
    • 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
    • C09B39/00—Other azo dyes prepared by diazotising and coupling
    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
    • C09B43/14—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents with phosgene or thiophosgene
    • 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/136—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents
    • C09B43/16—Preparation of azo dyes from other azo compounds by acylation of amino groups with polyfunctional acylating agents linking amino-azo or cyanuric acid residues
    • 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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
    • C09B62/08—Azo dyes
    • 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
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/465—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an acryloyl group, a quaternised or non-quaternised aminoalkyl carbonyl group or a (—N)n—CO—A—O—X or (—N)n—CO—A—Hal group, wherein A is an alkylene or alkylidene group, X is hydrogen or an acyl radical of an organic or inorganic acid, Hal is a halogen atom, and n is 0 or 1
    • C09B62/47—Azo dyes
    • C09B62/473—Monoazo dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

As diazo or coupling components in the manufacture of azo dyes, use is made of 5-pyrazolone derivatives substituted in the 1-position by a group -RXR1NHR11, where R and R1 are residues of the benzene series, R11 is hydrogen or the residue of an organic acid, and X is a simple linkage, an oxygen atom, a group -CH:CH-, -CH2-, -NHCO-, or -NHCONH-, or an amino-substituted heterocyclic ring containing carbon and nitrogen atoms, e.g. the residue of a 2 : 6-diamino-1 : 3 : 5-triazine ring, which may be substituted in the 4-position. If the dyes contain one or more free amino groups, they may be acylated or further diazotized and coupled with azo dye components. Diazo compounds which may be coupled with the pyrazolones include diazobenzene, diazonaphthalene, diazotoluene, diazoanisole, diazophenetole, diazotized aminoazobenzene, the sulphonic acids of any of these, and o- or peri-hydroxy- or carboxy-diazo compounds, e.g. those from o-aminophenols, o-aminonaphthols and their sulphonic acids, 1 : 8-aminonaphtholsulphonic acids, and anthranilic acid; the dyes prepared from o-aminophenols or o-aminocarboxylic acids or their esters or ethers, or the dyes containing a salicylic acid or other lake-forming grouping, may be converted into complex metal compounds, particularly into copper, chromium, nickel, cobalt, iron or zinc compounds, in substance or on the fibre. Coupling components which may be coupled with the diazotized pyrazolones (obtained when R11 is hydrogen) include p-cresol, resorcinol and 2-naphthol and their sulphonic acids, 1-naphthol sulphonic acids which couple in the 2-position, aminonaphthol sulphonic acids such as 2-amino-5-naphthol-7-sulphonic acid, 2-amino-8-naphthol-6-sulphonic acid, 1 - amino - 8 - naphthol - 4 : 6- and -3 : 6-disulphonic acid (acid or alkaline coupling), 2 : 3-oxynaphthoic acid, 1-acidylamino-8-naphtholsulphonic acids, and amines such as m-phenylenediamine, 2-naphthylamine and alkyl-2-naphthylamines and their sulphonic acids. The dyes are useful for dyeing textiles consisting of or containing natural or regenerated cellulose, e.g. viscose or cuprammonium artificial silk; if the dyes contain suitable substituents, they may be diazotized on the fibre and coupled with a coupling component, or treated on the fibre with a diazo compound. In the examples: (1) 1-phenyl-(41-phenyl-411-acetylamino)-3-methyl - 5 - pyrazolone (Specification 486,747) is coupled with diazotized sulphanilic acid to yield a yellow dye for cotton; (2) 1-phenyl-(41-phenyl - 411 - amino) - 3 - methyl - 5 - pyrazolone (Specification 486,747) is coupled with diazotized aminoazobenzene-p-sulphonic acid; the product dyes cotton in yellow shades, which may be converted into orange to red shades by diazotization on the fibre and development with 1 - phenyl - 3 - methyl - 5 - pyrazolone or 2 - naphthol; (3) 1 - phenyl - (41 - phenyl - 411-amino)-3-methyl-5-pyrazolone is coupled with diazotized 2-chloraniline-4-sulphonic acid, and the product is diazotized and coupled with 2 - amino - 8 - naphthol - 6 - sulphonic acid; a brown cotton dye is obtained; (4) 1-phenyl-(41-phenyl-411-amino)-3-methyl-5-pyrazolone is coupled with diazotized 2-chloraniline-4-sulphonic acid, and the product is diazotized and coupled with the monoazo dye obtainable by acid coupling of diazotized 2 : 4-dichloraniline and 1 - amino - 8 - naphthol - 3 : 6-disulphonic acid; the product dyes cotton green; similar products are obtained if the 3-methylpyrazolone is replaced by the corresponding 3-carboxypyrazolone or if the benzidine residue in the pyrazolone is replaced by a tolidine or dichlorobenzidine residue; (5) diazotized dehydrothiotoluidine is coupled with 1-phenyl-(41-phenyl-411-amino)-3-methyl-5-pyrazolone, and the product is treated with phosgene; an orange dye for cellulose fibres is obtained. Samples have been furnished, under Sect. 2(5), of products prepared as follows: (1) diazotized dehydrothio-p-toluidine monosulphonic acid is coupled with 1-phenyl-(41-phenoxy-411-amino)-3-methyl-5-pyrazolone, and the product is diazotized and coupled with 2 - amino - 5-naphthol-7-sulphonic acid; a red-brown dye is obtained; (2) 2 mols. of diazotized 2-aminobenzoic-4-sulphonic acid are coupled with 1 mol. of a dipyrazolone prepared by diazotizing 4-amino-41-nitrostilbene, converting the diazo compound into the corresponding hydrazine, condensing the latter with acetoacetic ester, reducing the nitro group, and condensing 2 mols. of the aminopyrazolone so obtained with 1 mol. of cyanuric chloride; a yellow dye is obtained; (3) diazotized dehydrothio-p-toluidine monosulphonic acid is coupled with 1-phenyl-(41-benzyl-411-amino)-3-methyl-5-pyrazolone, and the product is diazotized and coupled with 1-(41-sulphophenyl)-3-methyl-5-pyrazolone; a yellow-orange dye is obtained; (4) diazotized sulphanilic acid is coupled with the pyrazolone of sample 3, and the product is diazotized and coupled with 2-amino-5-naphthol-7-sulphonic acid; an orange-red dye is obtained; (5) diazotized sulphanilic acid is coupled with a pyrazolone obtainable by condensing 1 - (41-aminophenyl) - 3 - methyl - 5-pyrazolone with p-nitrobenzoyl chloride and reducing the nitro group; the dye so obtained is diazotized and coupled with the copper compound of the dye from diazotized 2-aminophenol-4-sulphonic acid and resorcinol; a brown dye is obtained; (6) diazotized dehydrothio-p-toluidine monosulphonic acid is coupled with the pyrazolone of sample 5, and the product is diazotized and coupled with 1-(41-sulphophenyl-3-methyl-5-pyrazolone; a yellow dye is obtained; (7) diazotized sulphanilic acid is coupled with the pyrazolone of sample 5, and the product is diazotized and coupled with 2-amino-5-naphthol-7-sulphonic acid; a red-brown dye is obtained; (8) diazotized sulphanilic acid is coupled with a pyrazolone obtainable by condensing phosgene with 1 mol. each of 1-(41-aminophenyl)-3-methyl-5-pyrazolone and p-phenylenediaminesulphonic acid; the product is diazotized and coupled with 2-amino-5-naphthol-7-sulphonic acid; an orange-brown dye is obtained; (9) diazotized dehydrothio-p-toluidine monosulphonic acid is coupled with the pyrazolone of sample 8, and the product is diazotized and coupled with 1-(41-sulphophenyl)-3-methyl-5-pyrazolone; a yellow dye is obtained; (10) diazotized sulphanilic acid is coupled with a pyrazolone obtained by condensing 1 mol. of cyanuric chloride successively with 1 mol. of p-phenylenediaminesulphonic acid and 1 mol. of 1 - (31 - aminophenyl) - 5-pyrazolone-3-carboxylic acid; the product is diazotized and coupled with 2-amino-5-naphthol-7-sulphonic acid; a brown-red dye is obtained; (11) diazotized dehydrothio - p - toluidine monosulphonic acid is coupled with the pyrazolone of sample 10, and the product is diazotized and coupled with 1-(41-sulphophenyl) - 3 - methyl - 5 - pyrazolone; an orange-yellow dye is obtained; (12) diazotized 2-aminobenzoic acid is coupled with the pyrazolone of sample 10, and the product is diazotized and coupled with the copper compound of the dye from diazotized 2-aminophenol-4-sulphonic acid and resorcinol; a yellow-brown dye is obtained; (13) diazotized 2-aminobenzoic acid is coupled with a pyrazolone obtainable by condensing 1 mol. of cyanuric chloride successively with 1 mol. of p-phenylenediaminesulphonic acid and 1 mol. of 1-(41-aminophenyl)-3-methyl-5-pyrazolone; the product is diazotized and coupled with the copper compound of the dye from diazotized 2-aminophenol-4-sulphonic acid and resorcinol; a brown dye is obtained; (14) diazotized 2-aminobenzoic-4-sulphonic acid is coupled with the pyrazolone of sample 13, and the product is diazotized and coupled with the copper compound of the dye from diazotized 2-aminophenol-4-sulphonic acid and resorcinol; (15) diazotized sulphanilic acid is coupled with the pyrazolone of sample 13, and the product is diazotized and coupled with 2-amino-5-naphthol-7-sulphonic acid; a red dye is obtained; (16) diazotized 2-aminobenzoic-4-sulphonic acid is coupled with 1-(41-phenyl-411-amino)-3-methyl-5-pyrazolone, and the product (2 mols.) is condensed with phosgene; a yellow dye is obtained; (17) diazotized dehydrothio-p-toluidine monosulphonic acid is coupled with the pyrazolone of sample 16, and the product (2 mols.) is condensed with phosgene; an orange-yellow dye is obtained; (18) diazotized 2-aminobenzoic-4-sulphonic acid is coupled with the pyrazolone of sample 16, and the product (2 mols.) is condensed with cyanuric chloride; a yellow dye is obtained; (19) diazotized 2-aminobenzoic-4-sulphonic acid is coupled with the pyrazolone of sample 16, and the product (1 mol.) is condensed with a product obtained by condensing 1 mol. of cyanuric chloride with 1 mol. of 41-amino-1 : 11-azo-4-oxybenzene-5-carboxylic acid; a yellow dye is obtained; (20) diazotized 2-aminobenzoic-4-sulphonic acid (2 mols.) is coupled with a dipyrazolone obtainable by condensing 2 mols. of the pyrazolone of sample 16 with 1 mol. of cyanuric chloride; the product is identical with sample 18; (21) diazotized sulphanilic acid (2 mols.) is coupled with a dipyrazolone obtained from the dipyrazolone of sample 20 by replacing the residual chlorine atom by a phenylamino group by reaction with aniline; a yellow dye is obtained; (22) diazotized 2-aminobenzoic-4-sulphonic p acid is coupled with 1-phenyl-(41-phenyl-411-amino)-3-methyl-5-pyrazolone, and the product is diazotized and coupled with the dye from 1 mol. each of diazotized 2 : 5-dichloraniline and 1 - amino - 8 - naphthol - 3 : 6-disulphonic acid; a green dye is obtained; (23) diazotized 2-aminobenzoic acid is coupled with the pyrazolone of sample 22, and the product is diazotized and coupled with the copper compound of the dye from diazotized 2-aminophenol-4-sulphonic acid and resorcinol; a brown dye is obtained; (24) diazotized sulphanilic acid is coupled with 1-phenyl-(41-phenyl-411-amino) -5-pyrazolone-3-carboxylic acid
GB30284/36A 1935-11-06 1936-11-06 Manufacture of dyestuffs Expired GB486660A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH486660X 1935-11-06

Publications (1)

Publication Number Publication Date
GB486660A true GB486660A (en) 1938-06-07

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2795576A (en) * 1953-08-10 1957-06-11 Ciba Ltd New monoazo-dyestuffs
GB2153835A (en) * 1984-02-10 1985-08-29 Sandoz Ltd Triazinyl azo dyestuffs and intermediates
WO2003010607A2 (en) * 2001-05-01 2003-02-06 Pragmatic Vision International Electrooptical photosensitive material and method of fabrication

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2795576A (en) * 1953-08-10 1957-06-11 Ciba Ltd New monoazo-dyestuffs
GB2153835A (en) * 1984-02-10 1985-08-29 Sandoz Ltd Triazinyl azo dyestuffs and intermediates
WO2003010607A2 (en) * 2001-05-01 2003-02-06 Pragmatic Vision International Electrooptical photosensitive material and method of fabrication
WO2003010607A3 (en) * 2001-05-01 2007-11-08 Pragmatic Vision Internat Electrooptical photosensitive material and method of fabrication

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