GB952620A - New pyrimidine azo dyestuffs - Google Patents

New pyrimidine azo dyestuffs

Info

Publication number
GB952620A
GB952620A GB2676760A GB2676760A GB952620A GB 952620 A GB952620 A GB 952620A GB 2676760 A GB2676760 A GB 2676760A GB 2676760 A GB2676760 A GB 2676760A GB 952620 A GB952620 A GB 952620A
Authority
GB
United Kingdom
Prior art keywords
group
dyes
alkylene
formula
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
GB2676760A
Inventor
George De Winter Anderson
Gerald Booth
Victor David Poole
Cyril Morris
Raymond Price
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 GB2676760A priority Critical patent/GB952620A/en
Publication of GB952620A publication Critical patent/GB952620A/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
    • C09B62/24Azo dyes

Landscapes

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

Abstract

The invention comprises azo dyes which have at least one SO3H group and at least one group of formula <FORM:0952620/C3/1> where p is 0, 1 or 2, one of m and n is 0 and the other 0 or 1, X is CO, SO2, O, S or SO when both m and n are 0 and for CO or SO2 when one of m and n is 1, R1, R2 and R3 are H or hydrocarbon or substituted hydrocarbon radicles or, when n is 1, R2 and R3 can together form an alkylene radicle and Y is <FORM:0952620/C3/2> where Z is Cl or Br, the said group being attached to a carbon atom of an aryl nucleus of the dye. The dyes may be made by conventional diazotization and coupling processes, by condensing an appropriate aminoazo dye with a trihalo-pyrimidine or by introducing the said group into the dye molecule by usual methods. Monoazo dyes are preferred. Metal complexes, preferably of copper, nickel, chromium and cobalt may be made from appropriate metallizable dyes. Indicated dyes are from the azobenzene, azonaphthalene, phenylazonaphthalene, phenylazopyrazolone and naphthylazopyrazolone series. Indicated polyazo dyes are of the A --> M --> E, A --> Z \sM A1 and E1 \sM D --> E series where A and A1 are diazotizable aryl amines, D a tetrazotizable aryl diamine, E and E1 are coupling components, M a coupling component which has a diazotizable amino group and 2 a coupling component which will couple twice. A, A1 and D may contain one or more azo groups. Representative of specified values for the R's are methyl, butyl, b -hydroxyethyl, g -sulphatopropyl, carboxymethyl, b -sulphoethyl, cyclohexyl, sulphobenzyl, tolyl, naphthyl and aryl groups containing sulpho, nitro, chloro, carboxy and alkoxy groups. Representative of the linking of R2 and R3 is N,N1-divalent piperazyl. Representative of specified values for the " alkylene " residue of the above group are ethylene, hexamethylene, b -ethyl-ethylene, b -hydroxypropylene, the 1,4-divalent residue of cyclohexane, C2H4OC2H4, C2H4SC2H4 and C2H4N(CH3)C2H4. Preferably the " alkylene " residue has 1-3 carbon atoms. Amongst specified values for the said group are SO2NHCH2CH2NH, CON(CH3)CH2CH2N(CH3), SO2CH2CH2N(C6H5), CH2SO2CH2CH2N(C6H5), COCH2NH, NHCOCH2N(CH3), CH2CH2NH-COCH2NH, NHSO2CH2CH2N(CH3), OCH2-CH2NH, SCH2CH2NH and SOCH2CH2NH. Preferred classes of dyes are those of formula <FORM:0952620/C3/3> where X, Y, R2, m, R3 and alkylene are as above, E is a coupling component residue and the benzene nucleus may be substituted and their complexes with the above metals those of formula <FORM:0952620/C3/4> where R1, R3, alkylene and Y are as above X1 is CO or SO2, one R is -N=N-E (E being as above) and the other for SO3H, COOH or OH and their complexes with the above metals, those of the formula <FORM:0952620/C3/5> where R1, alkylene, R3 and Y are as above, X1 is CO or SO2 A is a monodi- or tri-cyclic aryl radicle which may contain an azo group, the -N-X1 group is preferably in the 6, 7 or 8 position and there may be SO3H in the 5- or 6-position; and metal complexes of such dyes when metallizable, copper, chromium and cobalt complexes being preferred, those of formula A-N=N-E-N(R1)-X1-alkylene -N(R3)Y, and their metal complexes, where A is as above, X1 is CO or SO2, R1, R2, Y an alkylene being as before and E being a 5-pyrazolone residue carrying a mono- or di-cyclic radicle of the benzene series in the 1-position to which is attached the NR1 group, those of formula A-N=N-E-X1-N(R2)-alkylene -N(R3)-Y1 and their metal complexes, where A, R2, R3, Y and alkylene are as above, X1 is CO or SO2 and E is a 5-pyrazolone residue with a benzene residue, attached to X1, in the 1-position and those of formula <FORM:0952620/C3/6> where A is a di- or tri-sulphonated benzene or naphthalene radicle and R2, R3, alkylene and Y are as before. The dyes colour natural and artificial textile materials, e.g. materials of cotton, viscose rayon, regenerated cellulose, wool, silk, cellulose acetate, polyamides, polyacrylonitrile which may be modified and aromatic polyester fibres. Cellulosic materials may be coloured in conjunction with a treatment by an acid-binding agent. Wool, polyamides and other nitrogen-containing materials may be dyed from a mildly alkaline, neutral or acid dyebath. Examples are provided of the preparation of the dyes and their use in colouring cellulosic textiles, a variety of colours being obtained. Provisional Specification 26767/60 relates to water-soluble dyes which contain at least one group of formula-N(R)X where R is H, or an alkyl group which may be substituted, X is a pyrimidine ring attached to N via a carbon atom and which also has at least one group of formula SO2-Z, where Z is OH, or a substituted or unsubstituted hydrocarbon or a heterocyclic radicle, provided that the dyes have at least one SO3H group. The Specification is not restricted to azo dyes. This Specification also refers to Specifications 822,047, 822,948 885,547 and 937,182.
GB2676760A 1959-08-24 1959-08-24 New pyrimidine azo dyestuffs Expired GB952620A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2676760A GB952620A (en) 1959-08-24 1959-08-24 New pyrimidine azo dyestuffs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2676760A GB952620A (en) 1959-08-24 1959-08-24 New pyrimidine azo dyestuffs

Publications (1)

Publication Number Publication Date
GB952620A true GB952620A (en) 1964-03-18

Family

ID=10248869

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2676760A Expired GB952620A (en) 1959-08-24 1959-08-24 New pyrimidine azo dyestuffs

Country Status (1)

Country Link
GB (1) GB952620A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986004080A1 (en) * 1984-12-31 1986-07-17 Sandoz Ag Improvements in or relating to organic compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986004080A1 (en) * 1984-12-31 1986-07-17 Sandoz Ag Improvements in or relating to organic compounds

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