GB822047A - New dyestuffs containing a pyrimidine group and process for dyeing therewith - Google Patents

New dyestuffs containing a pyrimidine group and process for dyeing therewith

Info

Publication number
GB822047A
GB822047A GB2702156A GB2702156A GB822047A GB 822047 A GB822047 A GB 822047A GB 2702156 A GB2702156 A GB 2702156A GB 2702156 A GB2702156 A GB 2702156A GB 822047 A GB822047 A GB 822047A
Authority
GB
United Kingdom
Prior art keywords
group
groups
amino
dyestuffs
nitro
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
GB2702156A
Inventor
Robert Norman Heslop
Norman Legg
Jack Frankland Mawson
William Elliot Stephen
James Wardleworth
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.)
Imperial Chemical Industries Ltd
Original Assignee
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB2702156A priority Critical patent/GB822047A/en
Publication of GB822047A publication Critical patent/GB822047A/en
Priority to MY6000027A priority patent/MY6000027A/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
    • C09B62/00Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02Reactive 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
    • C09B62/20Reactive 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 pyrimidine ring

Landscapes

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

Abstract

The invention comprises as dyestuffs the 2:6 - dihalogeno - 4 - pyrimidylamino - or the 4:6 - dihalogeno - 2 - pyrimidylamino - derivatives of water-soluble coloured compounds, such as dyestuffs of the azo, anthraquinone, phthalocyanine or nitro series containing one or more water-solubilizing groups. The dyestuffs are made by interacting 2:4:6-trihalogenopyrimidines with water-soluble coloured compounds containing at least one monosubstituted or unsubstituted amino group in such amounts as correspond to at least one molecular proportion of the 2:4:6-trihalogenopyrimidine for each mono-substituted or unsubstituted amino group and isolating the dihalogenopyrimidyl derivatives, or, when the dyestuffs contain one or more azo groups also by a coupling reaction wherein either the diazonium compound or the coupling component contains at last one 2:6-dihalogeno-4 - pyrimidylamino or 4:6-dihalogeno-2-pyrimidyl amino group. The amino-containing water-soluble azo dyestuffs are made by coupling a diazotized aromatic mono- or diamine with 1 mol. of a coupling component or a tetrazotized aromatic diamine with 2 mols. of a coupling component or 1 mol. of each of two coupling components, at least one of the reactants containing at least one water-solubilizing group and the reactants being so selected that the product contains at least one monosubstituted or unsubstituted amino group. The aromatic amines may also contain azo groups. The azo dyes are also made by hydrolysis of azo or polyazo compounds containing acylamino groups, which may be made by coupling aromatic amines and coupling components one or both of which contain acylamino groups, or by reduction of azo or polyazo compounds containing nitro groups. The watersoluble anthraquinone dyestuffs described contain an unsubstituted or mono-substituted amino group in an alkylamino or arylamino group attached to an alpha-position of the anthraquinone nucleus and also contain at least one water-solubilizing group, and are made by reacting an alpha-halo or nitro-anthraquinone or the leuco derivative of a 1:4-dihydroxy-, -diamino- or -amino-hydroxy-anthraquinone with an aliphatic or aromatic diamine, or by sulphonating an amino-anthraquinone compound. The water-soluble amino-phthalocyanine dyestuffs may contain the amino or mono-substituted amino group attached directly to the benz-ring of the phthalocyanine nucleus or through a divalent bridging group many of which are specified. Those phthalocyanines containing sulphonic acid groups are made by sulphonating amino-phthalocyanines such as those described in Specifications 529,847, 569,200, 589,118, [all in Group IV], 717,137 and 724,212, or by synthesis from mixtures of sulphonated phthalic acids and substituted phthalic acid derivatives such as those described in Specifications 529,847, 569,200 and 589,118 and reducing nitro groups where necessary. Those phthalocyamines containing a -CH2NRphenylene- or a -CH2NR-alkylene linkage where R is hydrogen, alkyl or cycloalkyl are made by reacting a phthalocyanine containing chlormethyl and sulphonic acid or carboxylic acid groups, made by chlormethylation of a phthalocyamine sulphonic or carboxylic acid, with respectively (i) a primary or secondary N-alkylor cycloalkylnitro-aniline and reducing the nitro groups, or (ii) a monoacetyl alkylene diamine and hydrolysing the acetylamino group; those containing -SO2NR-alkylene- or -SO2NR-phenylene-CH2-linkages are made by reacting phthalocyamines containing -SO2Cl groups with respectively monoacetyl alkylene diamines or amino-N-benzyl acetamides and hydrolysing the acetylamino groups; those containing -CONR-phenylene- or -CONRphenylene-CH2- linkages are made by reacting a phthalocyamine containing carboxylic acid chloride groups with, respectively, (i) diaminobenzene sulphonic or carboxylic acids or nitro-amino-benzene sulphonic or carboxylic acids and reducing the nitro group, or (ii) an N - (aminobenzyl) - acetamide and hydrolysing the acetylamino group. The water-soluble nitro dyestuffs described are of the formula <FORM:0822047/IV(c)/1> where D is a naphthalene or benzene nucleus which may be further substituted and where N is ortho to the nitro group, X is hydrogen or a hydrocarbon radical which may be substituted, R is hydrogen or an organic radical attached to the nitrogen through a carbon atom, and where R may be connected to X when X is a hydrocarbon radical or to D, in the ortho position to N, to form a heterocyclic ring, the dyestuff containing at least one amino or monosubstituted amino group and at least one watersolubilizing group, and they are made by reacting an o-nitrochlorobenzene or naphthalene with the appropriate diamine. The dyestuffs colour silk, wool, regenerated protein and cellulosic textile material such as cotton, linen and viscose rayon by treating the material with an aqueous solution or a thickened printing paste of the dyestuff in conjunction with a treatment with an acid-binding agent such as sodium hydroxide, sodium carbonate or potassium phosphate which may be carried out prior to, simultaneously with or after the dyestuff treatment. The acid-binding agent may be replaced by a substance which on heating or steaming generates an acid-binding agent such as an alkali-metal bicarbonate or sodium trichloracetate. The dyestuff solution may also contain sodium chloride, sulphate or alginate, urea and water-soluble alkyl ethers of cellulose. The printing paste may also contain urea, methyl cellulose, starch, locust bean gum or sodium alginate. The dyestuffs may also be applied to silk, wool, regenerated protein, polyamide and modified polyacrylonitrile textile materials by conventional dyeing methods. Dyestuff pastes comprising dyestuffs of the invention and buffers suitable for maintaining a pH of about 6.5 such as mixtures of sodium dihydrogen phosphate and disodium hydrogen phosphate or of disodium hydrogen phosphate and potassium dihydrogen phosphate are described. Examples are given. Specifications 307,947, [Class 2 (iii)], 467,815, 503,609 and 515,637, [all in Group IV], also are referred to.
GB2702156A 1956-09-04 1956-09-04 New dyestuffs containing a pyrimidine group and process for dyeing therewith Expired GB822047A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
GB2702156A GB822047A (en) 1956-09-04 1956-09-04 New dyestuffs containing a pyrimidine group and process for dyeing therewith
MY6000027A MY6000027A (en) 1956-09-04 1960-12-31 New dyestuffs containing a pyrimidine group and process for dyeing therewith

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2702156A GB822047A (en) 1956-09-04 1956-09-04 New dyestuffs containing a pyrimidine group and process for dyeing therewith

Publications (1)

Publication Number Publication Date
GB822047A true GB822047A (en) 1959-10-21

Family

ID=10252882

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2702156A Expired GB822047A (en) 1956-09-04 1956-09-04 New dyestuffs containing a pyrimidine group and process for dyeing therewith

Country Status (2)

Country Link
GB (1) GB822047A (en)
MY (1) MY6000027A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1218636B (en) * 1960-05-13 1966-06-08 Sandoz Ag Process for the preparation of water-soluble pyrimidine dyes
DE1267769B (en) * 1959-03-13 1968-05-09 Du Pont Process for the preparation of water-soluble dis- and tetrakis-azo dyes

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1267769B (en) * 1959-03-13 1968-05-09 Du Pont Process for the preparation of water-soluble dis- and tetrakis-azo dyes
DE1218636B (en) * 1960-05-13 1966-06-08 Sandoz Ag Process for the preparation of water-soluble pyrimidine dyes

Also Published As

Publication number Publication date
MY6000027A (en) 1960-12-31

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