GB593567A - Azo dyes - Google Patents

Azo dyes

Info

Publication number
GB593567A
GB593567A GB6135/41A GB613541A GB593567A GB 593567 A GB593567 A GB 593567A GB 6135/41 A GB6135/41 A GB 6135/41A GB 613541 A GB613541 A GB 613541A GB 593567 A GB593567 A GB 593567A
Authority
GB
United Kingdom
Prior art keywords
aniline
ethyl
methoxyethoxyethyl
nitroaniline
general formula
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
GB6135/41A
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.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
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 American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB593567A publication Critical patent/GB593567A/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
    • C09B29/00Monoazo dyes prepared by diazotising and coupling
    • C09B29/06Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
    • C09B29/08Amino benzenes

Landscapes

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

Abstract

Azo dyes are obtained by coupling a diazotized arylamine with an amine of the general formula <FORM:0593567/IV/1> wherein B represents an aryl radicle, R represents an unsubstituted alkyl radicle, R1 represents a polyalkylene glycol radicle of the general formula -(CH2)x-(O-CH2-CH2)y-, wherein x and y each represent 1, 2, 3 or 4, and X represents H, alkyl, aralkyl, hydroxyalkyl, alkoxyalkyl or polyalkoxyalkyl, i.e. a group of the general formula -(CH2)x-(O-CH2-CH2)y-OR. Specified diazo components are aniline, 2 : 5-dichloroaniline, 3- or 4-nitroaniline, 2-chloro-4-nitroaniline, 4- or 5-nitro-2-aminotoluene, 5-nitro-2-anisidine, 4-aminoacetanilide, 6 - chloro- or bromo - 2 : 4 - dinitroaniline, 2 : 6 - dichloro - 4 - nitroaniline, 2 - naphthylamine, sul - phanilic acid anthranilic acid, and 1 : 4-diamino-benzene --> the anilide of 2 : 3-hydroxynaphthoic acid (in substance or on the fibre). Specified coupling components are N-b -methoxyethoxyethyl-aniline and its N-methyl, N-ethyl, N-benzyl, N-b -hydroxyethyl, and N-b -methoxyethyl derivatives, N - b - ethoxyethoxyethyl - aniline and its N-methyl and N-ethyl p derivatives, N : N-di-(b -methoxyethoxyethyl)-aniline, N - b - methoxyethoxyethoxyethyl - N - ethyl - aniline, N-b -methoxyethoxyethoxyethoxyethyl-N-ethyl aniline, 3-chloro- or 3-methyl-N-b -methoxyethoxyethyl - aniline, N - b - methoxy - ethoxyethyl - cresidine, N - b - n - butoxyethoxy - ethyl-aniline and its N-methyl derivative, 3 - methyl - N - b - ethoxyethoxyethyl - N - ethyl - aniline and N - b - methoxyethoxyethyl - N - ethyl - 1-naphthylamine. The products free from water-solubilizing groups are applicable for colouring fibres of cellulose esters or of vinyl halide-vinyl acetate copolymers. The water-soluble products are suitable for dyeing animal fibres, e.g. wool or silk. Examples relate to the production of the dyestuffs: (1), (2) and (3), 4 - nitroaniline --> (1) N - b - methoxyethoxy - ethyl - N - ethyl - aniline, (2) N - b - ethoxyethoxy - ethyl - N - methyl - aniline, (3) N : N - di - (b - methoxyethoxyethyl)-aniline; (4) 2 - chloro - 4 - nitroaniline --> N - b - ethoxyethoxyethyl - N - ethyl - aniline; (5) 6 - bromo - 2 : 4 - dinitroaniline --> N - b - methoxyethoxyethyl - N - ethyl - 1 - naphthylamine; (6) 4 - aminoacetanilide --> N - methoxyethoxyethyl - N - ethyl - aniline; (7) the anilide of 2 : 3-hydroxynaphthoic acid (on cotton fibre) \sM 1 : 4-diaminobenzene --> N - b - methoxyethoxyethyl - N - ethyl - aniline; (8) sulphanilic acid --> N - b - methoxyethoxyethyl - N - ethyl - aniline; (9) 2 : 6 - dichloro - 4- nitro - aniline --> b - methoxyethoxyethyl - N - ethyl - aniline; (10), (11) and (12) 4-nitroaniline --> (10) N - b - methoxyethoxyethyl - N - b - methoxy - ethyl-aniline; (11) N - b - methoxyethoxyethoxy - ethyl - N - ethyl - aniline; (12) N - b - methoxy - ethoxyethoxyethoxyethyl - N -ethyl - aniline. A table is also given showing the shades obtainable with various combinations of diazo and coupling components. Amines of the above general formula are obtainable by (A) condensation of a compound of the general formula Aryl-SO2-O-(CH2)x-(O-CH2-CH2) yOR with a primary amine of the benzene or naphthalene series in presence of an agent binding acid and, if necessary, introducing the desired group X, e.g. by treatment with dimethyl sulphate, benzyl chloride or ethylene chlorohydrin; (B) condensation of an arylsulphonic acid ester as in (A) with a secondary amine of the general formula Ar-NHX of the benzene or anphthalene series; (C) condensation of a compound Hal-(CH2)x-(O-CH2-CH2)y-OR, wherein Hal represents Cl or Br, with an appropriate primary or secondary amine of the benzene or naphthalene series. The Specification as open to inspection under Sect. 91 comprises also the use as coupling components of N-b -ethoxyethoxypropylaniline, N-b - ethoxyethoxybutylaniline, N - b - methoxy - ethoxyethyl - N - b - butoxyethoxyethyl - aniline, N - b - ethoxyethoxyethyl - N - b - methoxyethylaniline, N - b - methoxyethoxyethoxyethyl - N - ethyl - aniline and N - b - ethoxyethoxyethoxyethoxyethyl - N - ethyl - aniline. This subject-matter does not appear in the Specification as accepted.
GB6135/41A 1940-07-10 1941-05-12 Azo dyes Expired GB593567A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US593567XA 1957-11-25 1957-11-25

Publications (1)

Publication Number Publication Date
GB593567A true GB593567A (en) 1947-10-21

Family

ID=22022437

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6135/41A Expired GB593567A (en) 1940-07-10 1941-05-12 Azo dyes

Country Status (2)

Country Link
BE (1) BE593567A (en)
GB (1) GB593567A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1266421B (en) * 1960-09-14 1968-04-18 Bayer Ag Process for the preparation of water-insoluble monoazo dyes
DE2801317A1 (en) * 1978-01-13 1979-07-19 Bayer Ag AZO DYES

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1266421B (en) * 1960-09-14 1968-04-18 Bayer Ag Process for the preparation of water-insoluble monoazo dyes
DE2801317A1 (en) * 1978-01-13 1979-07-19 Bayer Ag AZO DYES

Also Published As

Publication number Publication date
BE593567A (en) 1960-11-14

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