GB1072713A - Water-insoluble anthraquinone dyestuffs containing a reactive group - Google Patents

Water-insoluble anthraquinone dyestuffs containing a reactive group

Info

Publication number
GB1072713A
GB1072713A GB338565A GB338565A GB1072713A GB 1072713 A GB1072713 A GB 1072713A GB 338565 A GB338565 A GB 338565A GB 338565 A GB338565 A GB 338565A GB 1072713 A GB1072713 A GB 1072713A
Authority
GB
United Kingdom
Prior art keywords
hydroxypropyl
radical
alkyl
bromo
chloro
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
GB338565A
Inventor
John Anderson Blackhall
Gerald Booth
Charles Hugh Reece
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 GB338565A priority Critical patent/GB1072713A/en
Priority to DE19661644560 priority patent/DE1644560A1/en
Priority to CH103166A priority patent/CH477504A/en
Priority to CH337769A priority patent/CH478187A/en
Priority to CH337669A priority patent/CH478191A/en
Priority to FR47285A priority patent/FR1465924A/en
Publication of GB1072713A publication Critical patent/GB1072713A/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
    • 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
    • C09B62/54—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 epoxy or halohydrin group
    • C09B62/56—Anthracene 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
    • C09B62/78—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 other reactive groups
    • C09B62/80—Anthracene dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises water-insoluble anthraquinone dyestuffs and mixtures thereof of the formula <FORM:1072713/C4-C5/1> wherein one of R1 and R2 represents a g -chloro-b -hydroxypropyl, a g -bromo-b -hydroxypropyl or a b :g -epoxypropyl radical and the other of R1 and R2 represents a H, g -chloro-b -hydroxypropyl, a g -bromo-b -hydroxypropyl or a b :g -epoxypropyl radical or C1-C5 alkyl, a hydroxy-(C1-C5 alkyl or a hydroxy(C1-C5)alkoxy-(C1-C5)alkyl radical; and the anthraquinone nucleus and the benzene ring may be further substituted by Cl, Br or C1-C5 alkyl radicals. Compounds wherein R1 represents a g -chloro-b -hydroxypropyl or g -bromo-b -hydroxypropyl radical may be prepared by treating with epichlorohydrin or with epibromohydrin in a non-basic organic solvent an anthraquinone compound or the formula <FORM:1072713/C4-C5/2> wherein R1 represents a hydrogen atom or a g -chloro-b -hydroxypropyl, g -bromo-b -hydroxypropyl, b :g -epoxypropyl, C1-C5 alkyl, hydroxy(C1-C5)alkyl or a hydroxy(C1-C5)alkoxy-(C1-C5)alkyl radical, and the anthraquinone nucleus and the benzene ring may be further substituted as above. Compounds wherein R2 represents a g - chloro - b - hydroxypropyl g - bromo - b - hydroxypropyl or b :g - epoxypropyl radical may be obtained by treating with epichlorohydrin or epibromohydrin in alkaline medium an anthraquinone compound of the formula <FORM:1072713/C4-C5/3> whereby a dye in which R2 represents a b :g -epoxypropyl radical is obtained which may be converted into a dye in which R2 represents g -chloro- or -bromo-b -hydroxypropyl radical by treatment with HCl or HBr. Also, compounds in which R1 represents hydrogen and R2 represents a g -chloro- or -bromo-b -hydroxypropyl or b :g -epoxypropyl radical may be obtained by desulphonating an anthraquinone sulphonic acid of the formula <FORM:1072713/C4-C5/4> wherein R5 represents a g -chloro- or bromo-b -hydroxypropyl or b :g -epoxypropyl radical, and the anthraquinone nucleus and benzene radical may be substituted as above. Examples are given for the preparation of the dyes. They may be used for colouring wool and synthetic fibres. Anthraquinone sulphonic acids of Formula III may be obtained by reacting 1-amino-4-bromoanthraquinone-2-sulphonic acid with an amine of the formula <FORM:1072713/C4-C5/5>ALSO:Textile materials are coloured with water insoluble anthraquinone dyes of the formula: <FORM:1072713/D1-D2/1> wherein one of R1 and R2 represents a g -chloro -or-bromo-b -hydroxypropyl or a b :g - epoxy-propyl radical, and the other represents hydrogen, g -chloro-or-bromo-b -hydroxypropyl, b : g -epoxypropyl, C1-C5 alkyl, hydroxy C1-C5 alkyl or hydroxy (C1-C5) alkoxy (C1-C5) alkyl radical, and the anthraquinone nucleus and the benzene ring may be further substituted by Cl or Br atoms or C1-C5 alkyl. Specified fibres are wool, polyesters, cellulose esters, polymers and copolymers of acrylonitrile, polyolefins and polyamides. An example is given where a woven synthetic polyamide textile is dyed in the presence of an aqueous solution of NaHCO3 and a condensate of ethylene oxide and cetyl alcohol.
GB338565A 1965-01-26 1965-01-26 Water-insoluble anthraquinone dyestuffs containing a reactive group Expired GB1072713A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB338565A GB1072713A (en) 1965-01-26 1965-01-26 Water-insoluble anthraquinone dyestuffs containing a reactive group
DE19661644560 DE1644560A1 (en) 1965-01-26 1966-01-26 Process for the production of water-insoluble anthraquinone dyes
CH103166A CH477504A (en) 1965-01-26 1966-01-26 Process for the production of water-insoluble anthraquinone dyes
CH337769A CH478187A (en) 1965-01-26 1966-01-26 Process for the production of water-insoluble anthraquinone dyes
CH337669A CH478191A (en) 1965-01-26 1966-01-26 Process for the production of water-insoluble anthraquinone dyes
FR47285A FR1465924A (en) 1965-01-26 1966-01-26 Anthraquinone dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB338565A GB1072713A (en) 1965-01-26 1965-01-26 Water-insoluble anthraquinone dyestuffs containing a reactive group

Publications (1)

Publication Number Publication Date
GB1072713A true GB1072713A (en) 1967-06-21

Family

ID=9757337

Family Applications (1)

Application Number Title Priority Date Filing Date
GB338565A Expired GB1072713A (en) 1965-01-26 1965-01-26 Water-insoluble anthraquinone dyestuffs containing a reactive group

Country Status (3)

Country Link
CH (1) CH477504A (en)
DE (1) DE1644560A1 (en)
GB (1) GB1072713A (en)

Also Published As

Publication number Publication date
DE1644560A1 (en) 1971-04-08
CH477504A (en) 1969-08-31

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