GB901434A - Azo dyestuffs - Google Patents

Azo dyestuffs

Info

Publication number
GB901434A
GB901434A GB750359A GB750359A GB901434A GB 901434 A GB901434 A GB 901434A GB 750359 A GB750359 A GB 750359A GB 750359 A GB750359 A GB 750359A GB 901434 A GB901434 A GB 901434A
Authority
GB
United Kingdom
Prior art keywords
groups
aryl
dyes
alkyl
group
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
GB750359A
Inventor
Peter William Barker
James Stuart Hunter
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 GB750359A priority Critical patent/GB901434A/en
Priority to DE19601419852 priority patent/DE1419852A1/en
Priority to CH245560A priority patent/CH424021A/en
Priority to CH1625765A priority patent/CH469071A/en
Priority to CH1625665A priority patent/CH410236A/en
Priority to CH1625865A priority patent/CH410237A/en
Publication of GB901434A publication Critical patent/GB901434A/en
Expired legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/38—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using reactive 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
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/18—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group
    • C09B43/24—Preparation of azo dyes from other azo compounds by acylation of hydroxyl group or of mercapto group with formation of —O—SO2—R or —O—SO3H radicals
    • 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
    • C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
    • C09B62/006—Azodyes
    • 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
    • C09B62/4401—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 with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
    • 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
    • C09B62/4401—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 with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
    • C09B62/4403—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 with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
    • C09B62/4411—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
    • C09B62/443—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 alternatively specified

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Pyridine Compounds (AREA)

Abstract

The invention comprises azo dyes which contain two or more reactive groups, at least two of the reactive groups being dissimilar. Reactive groups are groups which contain atoms or sub-groups which are capable of reacting with natural or artificial textile materials to produce chemical links. Dissimilar groups are reactive groups which have different heterocyclic nuclei or different non-homologous chains of non-metallic atoms each of which has a valency of 2. Indicated reactive groups are dihalo-triazinylamino and dihalo-pyrimidylamino, monohalo-pyrimidylamino, nitro-monohalo-pyrimidylamino, haloalkylamino, g -halo-b - hydroxypropylamino, haloalkoxy, epoxypropylamino, haloalkylaminosulphonyl, haloacyl, vinylsulphonylamino, vinylsulphonyl, haloethylsulphonyl, sulphato-b -hydroxyethylsulphonyl, thiocyano, N-(g -halo-b - hydroxy-propyl) aminocarbonyl, haloacylamino, alkyl- and aryl-sulphonyloxy-alkylsulphonyl, alkyl- and aryl-sulphonyloxy-alkylaminosulphonyl, alkyl- and aryl-sulphonyloxyalkylamino, alkyl- and aryl-sulphonyloxyalkoxy and alkyl- and aryl-sulphonyloxyalkylaminocarbonyl. The halo atoms are chlorine or bromine. The dyes may be made by conventional diazotisation and coupling processes or by treating a dye which has at least one reactive group and at least one hydroxy, mercapto, sulphinic acid, sulphamyl or primary or secondary amino group, with a compound of formula Hal Y, so that a different reactive group is formed. Dyes which contain at least two alkyl- or aryl-sulphonyloxyalkyl groups linked to the dye molecule via different atoms or groups, or one is directly attached and the other via an atom or group, may be made by treating an azo dye containing at least two hydroxyalkyl groups with an alkyl- or aryl-sulphonhalide. Indicated groups or atoms through which the hydroxyalkyl groups may be linked are O, S, NH, O-alkylene-O, SO2NH, SO2, NR1, CONH and CONR1, where R1 is a hydrocarbon group which may be substituted. Dyes free from SO3H and COOH are water-insoluble and may be applied in a disperse state. The water-insoluble dyes, which contain a dihalo-1,3,5-triazin-2-ylamino group, may be applied to polyamide, polyurethane, polyvinyl-alcohol or modified polyacrylonitrile textile materials as in Specification 825,912. The dyes colour natural and artificial textile materials such as cotton, viscose rayon, regenerated cellulose, wool, silk, cellulose acetate, polyamides, polyacrylonitriles and modifications thereof, and aryl polyesters. Water-soluble dyes are preferred for cellulosic materials especially when applied in conjunction with an acid-binding agent (see Specification 797,946). The dyeings may be after-treated to improve their wash fastness. Nitrogenous materials are coloured from a mildly alkaline, neutral or acid dyebath. A preferred class are water-insoluble dyes free from SO3H or COOH groups and which are of formula A-N=N-B where A is an aryl residue and B is an aryl residue with an amino group o or p to the azo link indicated being dyes of formula P.C2H4HNO2S-A1-N= N-B1-N(R1)CH2CHOHCH2Q where A1 is a benzenic or naphthalenic residue, P and Q are Cl or Br, R1 is H or alkyl, which may be substituted, or CH2CHOHCH2Q and B1 is phenylene or naphthylene with the N(R) group o or p to N2. A second preferred class of dyes are those of formula <FORM:0901434/IV (b)/1> where A is the residue of a water-soluble dye linked to the triazine via N, X is Cl or Br, n is 1-5, m 1 or 2, R1 is H or ZY, Z is a :b lower alkylene and Y is a chlorine, sulphato, phosphato or acylated hydroxy group, indicative of values represented by A are aminoazobenzene, naphthylazoaniline, aminophenyl-azonaphthol, aminophenylazopyrazolone, their metal, e.g. Cu, Cr, Co and Ni complexes, and X-N=N-D-N=N-E-NH(Cn-1H2n-1) where D is a divalent aryl radical, X a coupling component residue and E NH(Cn-1H2n-1) a radical of a coupling component containing an amino or alkylamino group. Examples are provided of the preparation of the dyes and their use in colouring processes to yield a variety of colours. Specifications 838,337, 842,933, 852,911 and 879,073 also are referred to.
GB750359A 1959-03-04 1959-03-04 Azo dyestuffs Expired GB901434A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB750359A GB901434A (en) 1959-03-04 1959-03-04 Azo dyestuffs
DE19601419852 DE1419852A1 (en) 1959-03-04 1960-03-03 Process for the production of azo dyes
CH245560A CH424021A (en) 1959-03-04 1960-03-04 Process for the production of new azo dyes
CH1625765A CH469071A (en) 1959-03-04 1960-03-04 Process for the production of new azo dyes
CH1625665A CH410236A (en) 1959-03-04 1960-03-04 Process for the production of new azo dyes
CH1625865A CH410237A (en) 1959-03-04 1960-03-04 Process for the production of new water-soluble azo dyes

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB750359A GB901434A (en) 1959-03-04 1959-03-04 Azo dyestuffs
GB3316259 1959-09-30

Publications (1)

Publication Number Publication Date
GB901434A true GB901434A (en) 1962-07-18

Family

ID=26241474

Family Applications (1)

Application Number Title Priority Date Filing Date
GB750359A Expired GB901434A (en) 1959-03-04 1959-03-04 Azo dyestuffs

Country Status (3)

Country Link
CH (3) CH410236A (en)
DE (1) DE1419852A1 (en)
GB (1) GB901434A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3429870A (en) * 1964-08-10 1969-02-25 Acna Reactive triazine containing azo dyestuffs
US4720542A (en) * 1979-06-20 1988-01-19 Sumitomo Chemical Company, Limited Formazan blue reactive dye
US5298607A (en) * 1978-07-06 1994-03-29 Ciba-Geigy Corporation Reactive dyes containing fluorotriazine and vinylsulfonyl radicals

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH627206A5 (en) * 1978-07-06 1981-12-31 Ciba Geigy Ag
DE2842640A1 (en) * 1978-09-29 1980-04-10 Bayer Ag REACTIVE DYES
US4378313B1 (en) * 1979-06-01 1994-05-03 Sumitomo Chemical Co Reactive yellow dye having both monochlorotriazinyl and vinylsulfone type reactive groups
JPS5848672B2 (en) * 1979-07-06 1983-10-29 住友化学工業株式会社 Dyeing method for cellulose fibers
US4341699A (en) * 1979-07-13 1982-07-27 Sumitomo Chemical Company, Limited Reactive red dye having both monochlorotriazinyl- and vinylsulfone-type reactive groups
DE3165870D1 (en) * 1980-11-26 1984-10-11 Sumitomo Chemical Co Reactive monoazo scarlet dyes
US4937326A (en) * 1980-11-26 1990-06-26 Sumitomo Chemical Company, Limited Reactive scarlet dyes having both monochlorotriazinyl and vinylsulfone type reactive groups linked via N-alkylated amino
US4841031A (en) * 1981-05-06 1989-06-20 Sumitomo Chemical Company, Limited Reactive dye having both monochlorotriazinyl and vinylsulfone type reactive groups

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3429870A (en) * 1964-08-10 1969-02-25 Acna Reactive triazine containing azo dyestuffs
US5298607A (en) * 1978-07-06 1994-03-29 Ciba-Geigy Corporation Reactive dyes containing fluorotriazine and vinylsulfonyl radicals
US4720542A (en) * 1979-06-20 1988-01-19 Sumitomo Chemical Company, Limited Formazan blue reactive dye

Also Published As

Publication number Publication date
CH410237A (en) 1966-03-31
CH424021A (en) 1966-11-15
DE1419852A1 (en) 1969-12-11
CH410236A (en) 1966-03-31

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