GB1072713A - Water-insoluble anthraquinone dyestuffs containing a reactive group - Google Patents
Water-insoluble anthraquinone dyestuffs containing a reactive groupInfo
- 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
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.
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) |
-
1965
- 1965-01-26 GB GB338565A patent/GB1072713A/en not_active Expired
-
1966
- 1966-01-26 CH CH103166A patent/CH477504A/en not_active IP Right Cessation
- 1966-01-26 DE DE19661644560 patent/DE1644560A1/en active Pending
Also Published As
Publication number | Publication date |
---|---|
DE1644560A1 (en) | 1971-04-08 |
CH477504A (en) | 1969-08-31 |
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