GB942796A - New pyrimidine dyestuffs - Google Patents

New pyrimidine dyestuffs

Info

Publication number
GB942796A
GB942796A GB2891659A GB2891659A GB942796A GB 942796 A GB942796 A GB 942796A GB 2891659 A GB2891659 A GB 2891659A GB 2891659 A GB2891659 A GB 2891659A GB 942796 A GB942796 A GB 942796A
Authority
GB
United Kingdom
Prior art keywords
dyes
group
formula
groups
residue
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
GB2891659A
Inventor
George De Winter Anderson
Gerald Booth
Victor David Poole
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
Priority claimed from GB3897356A external-priority patent/GB849772A/en
Application filed by Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB2891659A priority Critical patent/GB942796A/en
Priority to GB2216060A priority patent/GB952619A/en
Priority to DE19601419858 priority patent/DE1419858A1/en
Priority to CH953260A priority patent/CH404021A/en
Priority to CH1060265A priority patent/CH401306A/en
Priority to CH1060365A priority patent/CH408235A/en
Priority to CH1278163A priority patent/CH393588A/en
Priority to FR836639A priority patent/FR79115E/en
Priority to CH958360A priority patent/CH395383A/en
Publication of GB942796A publication Critical patent/GB942796A/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 dyes which have at least one group of formula N(R)T where R is H or an alkyl or cycloalkyl radicle, which may be substituted, T is a pyrimidine ring attached to N through a C atom of the ring and has at least one SO3H group in the form of an alkali metal, alkaline earth metal or magnesium salt, each of the SO3H groups being attached to a C atom of the pyrimidine ring. The dyes may be made by reacting dyes containing a corresponding group N(R)T1, where T1 is an appropriate halo-pyrimidine ring, with a metal salt of sulphurous acid, by conventional processes of diazotization and coupling, or by reacting dyes containing an N(R)H group with the required halopyrimidine. Group N(R)T may be attached to a carbon atom in the dye molecule which is part of an aryl residue or of an alkyl chain, which chain may be directly, or via a bridge, attached to an aryl nucleus. Preferred dyes are azo, e.g. mono- and polyazo, nitro, anthraquinone and phthalocyanine dyes. Water-solubilizing groups, e.g. alkylsulphone, sulphamyl, carboxylic acid and preferably sulphonic acid groups, may be present. Metal complexes, e.g. of Cu, Cr and Co, may also be made. Mg, Ca, Ba, K and Na are metals specified for salt formation, salts of alkali metals being preferred. Indicated as groups which may be attached to the pyrimidine residue, other than SO2H, are halogen, alkyl, aryl, carboalkoxy, nitro and cyano groups. Representative of indicated values for R are methyl and butyl, which may contain hydroxy or methoxy groups, and cyclohexyl. Bridges mentioned are O, S, NH, N alkyl, SO2, SO2NH, CONH and SO2N alkyl. Dyes of the following classes are indicated as starting materials <FORM:0942796/C3/1> where D1 is an at most dicyclic aryl radicle, which is free from azo and NHR groups, the NHR group is preferably attached to the 6, 7 or 8 position and an SO3H group may be in the 5 or 6 position; indicated for D1 are benzene or naphthalene residues free from azo groups, stilbene, diphenyl, benzthiazolylphenyl and diphenylamine residues, preferred being sulphonated phenyl or naphthyl residues with the SO3 group o to the azo link, and the NAR group may be attached to the nucleus of a benzoylamino or anilino group which is in the 6, 7 or 8 position; diazo dyes of the formula immediately above where D1 is a residue of the azobenzene, azonaphthalene or phenylazonaphthalene series; monoazo dyes of formula <FORM:0942796/C3/2> where D1 is an at most dicyclic aryl radicle, preferably disulphonaphthyl or stilbene and the benzene nucleus may be substituted; mono- or dis-azo dyes of formula HN(R)-D1-N=N-K where D1 is an arylene residue, e.g. of the azobenzene, azonaphthalene or phenylazonaphthalene series or, preferably, an at most dicyclic arylene radicle of the benzene or naphthalene series, especially a sulphonated phenyl residue, and K is the radicle of a naphthol sulphuric acid or an enolizable ketomethylene compound with OH o to the azo group; dyes of formula D1-N=N-K2-NHR where D1 is as in the first two classes indicated above and K2 is an enolizable ketamethylene residue with OH o to the azo group; the metal complexes, e.g. Cu, Cr and Co complexes, of metallizable dyes of the above classes; anthraquinones of formula <FORM:0942796/C3/3> where an SO2H group may be in the 5, 6, 7 or 8 position and Y is a bridge, preferably a divalent radicle of the benzene series, e.g. phenylene, diphenylene or 4,41-divalent stilbene or azobenzene residues, and preferably Y has one SO3H group for each benzene ring present; phtholocyanates of formula <FORM:0942796/C3/4> where Pc is preferably a copper phthalocyanine residue, o is OH and/or an amino group whieh may be substituted, Y is a bridge, n and m are 1,2 or 3 with n+m not greater than 4 and dyes of formula NO2-A-NH-B-NHR where A and B are monocyclic aryl residues with NO2 o to NH. Preferred for diazotization are amines of the benzene or naphthalene series which may have arylazo groups and preferably the coupling components are of the acylacetorylide, 5-pyrazolone, phenol, naphthol or arylamine series. Preferred classes of dyes are those which contain a sulphonic acid group and one or two groups of formula -N(R)-T1(SO3H)Hlgn where T1 is a pyrimidine ring Hlg is Cl or Br and n 1 or 2 or one or two groups of formula <FORM:0942796/C3/5> where X is H or Hlg. The dyes colour natural and artificial textile materials, e.g. cotton, viscose rayon, regenerated cellulose, wool, silk, cellulose acetate, polyamides, polyacrylonitriles and aromatic polyesters. The dyes are of particular use for cellulose materials being applied in conjunction with an acid-binding agent. Nitrogen-containing textile materials are dyed from a mildly alkaline to acid dye-bath. The dyes are generally insoluble and are usually applied as an aqueous dispersion. Numerous examples are provided of the preparation of the dyes and their use in colouring processes to produce a variety of shades. The Provisional Specification describes dyes in which T is a pyrimidine ring attached to N via a C atom and which also has at least one group of formula -SO2Z where Z is OH or a substituted or unsubstituted hydrocarbon or heterocyclic residue, provided that the dyes have at least one SO3H group. Specifications 822,047, 822,948 and 891,601 are referred to.
GB2891659A 1956-12-21 1959-08-24 New pyrimidine dyestuffs Expired GB942796A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GB2891659A GB942796A (en) 1956-12-21 1959-08-24 New pyrimidine dyestuffs
GB2216060A GB952619A (en) 1959-08-24 1960-06-24 New pyrimidine dyestuffs
DE19601419858 DE1419858A1 (en) 1956-12-21 1960-08-04 Process for the production of dyes
CH1060365A CH408235A (en) 1959-08-24 1960-08-23 Process for the production of new dyes
CH1060265A CH401306A (en) 1959-08-24 1960-08-23 Process for the production of new azo dyes
CH953260A CH404021A (en) 1959-08-24 1960-08-23 Process for the production of new dyes
CH1278163A CH393588A (en) 1959-08-24 1960-08-24 Process for the production of new azo dyes
FR836639A FR79115E (en) 1956-12-21 1960-08-24 Process for the manufacture of water-soluble organic compounds containing triazine nuclei
CH958360A CH395383A (en) 1959-08-24 1960-08-24 Process for the production of new dyes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB3897356A GB849772A (en) 1956-12-21 1956-12-21 s-triazine derivatives
GB2891659A GB942796A (en) 1956-12-21 1959-08-24 New pyrimidine dyestuffs

Publications (1)

Publication Number Publication Date
GB942796A true GB942796A (en) 1963-11-27

Family

ID=26259634

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2891659A Expired GB942796A (en) 1956-12-21 1959-08-24 New pyrimidine dyestuffs

Country Status (1)

Country Link
GB (1) GB942796A (en)

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