GB779781A - Water insoluble dyestuffs and a process for producing fast dyeings and prints therewith - Google Patents

Water insoluble dyestuffs and a process for producing fast dyeings and prints therewith

Info

Publication number
GB779781A
GB779781A GB15889/53A GB1588953A GB779781A GB 779781 A GB779781 A GB 779781A GB 15889/53 A GB15889/53 A GB 15889/53A GB 1588953 A GB1588953 A GB 1588953A GB 779781 A GB779781 A GB 779781A
Authority
GB
United Kingdom
Prior art keywords
dyestuff
hydroxyethylsulphone
aniline
sulphuric
methylanilino
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
GB15889/53A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst AG
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 Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB779781A publication Critical patent/GB779781A/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
    • C09B62/503—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 esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group

Landscapes

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

Abstract

2 : 4-Diaminobenzene b -chlorethylsulphone is prepared by treating 2 : 4-dinitrophenyl b -hydroxyethyl sulphide with chlorine (or an agent yielding it) in the presence of hydrochloric acid, and reducing the nitro groups in the product with iron and hydrochloric acid. p - Aminobenzene b - (N - methylanilino)-ethyl sulphone and vinyl b -(N-methylanilino) ethyl sulphone are made by condensing N-methylaniline with 4-vinylsulphonyl-aniline and divinyl sulphone respectively.ALSO:The invention comprises (1) water-insoluble dyestuffs (other than azo dyestuffs containing the residue of a yellow component) containing one or more vinylsulphone groups attached to an aromatic or aliphatic carbon atom, (2) the application of a dyestuff as in (1) to cellulose acetate or polyamide fibres or mixtures of these from a weakly alkaline bath to produce fast dyeings or prints and (3) a modification of (2) using a dyestuff containing a b -chlorethylsulphone or b - hydroxyethylsulphone sulphuric ester group which is converted into a vinylsulphone group in the dyebath. In the examples (1) cellulose acetate or polyamide fibres are dyed with the dyestuff 4 - nitro - 2 - vinylsulphonylaniline-->N - b - hydroxyethyl-N-butylaniline, (2) polyamide fibres are dyed with a dyestuff as in (1) without the nitro group, (3) the dyestuff 4 - (b - hydroxyethylsulphone sulphuric ester) - aniline-->diphenylamine is used, and (4) the dyestuff 3 - (b - hydroxyethylsulphone sulphuric ester) - aniline--> p - cresol; (5) 1 - amino - 4 - bromanthraquinone - 2 - sulphonic acid is condensed with 4 - (b - hydroxyethyl - sulphonyl) - aniline, the sulphonic acid group split off and the hydroxy group esterified with sulphuric acid; cellulose acetate is dyed with the product from a bath containing sodium phosphate and iso - octylphenol polyglycol ether; cellulose acetate and polyamide fibres are dyed with (6) 4-(b - hydroxyethylsulphone sulphuric ester) --> 2:4 - diaminobenzene b - chloroethylsulphone, (7) the dyestuff obtained by condensing 3 - nitro - 4 - chloro - benzene b - hydroxyethylsulphone with p - toluidine and dehydrating to the vinylsulphone, (8) the dyestuff 2:6 - dichloro - 4 - (b - hydroxyethylsulphone) --> m - toluidine subsequently esterified with sulphonic acid, (9) the dyestuff 2:6 - dichloro - 4 -(b - hydroxyethylsulphone sulphuric ester aniline --> p - aminobenzene b - (N - methylanilino) -ethyl sulphone, and (10) the dyestuff 2 - bromo - 4 - (b - hydroxyethylsulphone sulphuric ester) - aniline --> vinyl b - (N - methylanilino) - ethyl sulphone; (11) the dyestuff 4 - (b - hydroxyethylsulphonyl) - aniline --> m - toluidine --> o - cresol, subsequently esterified with sulphuric acid is used in the process of (5). A table and a further list of suitable dyestuffs are given.
GB15889/53A 1952-06-09 1953-06-09 Water insoluble dyestuffs and a process for producing fast dyeings and prints therewith Expired GB779781A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE779781X 1952-06-09

Publications (1)

Publication Number Publication Date
GB779781A true GB779781A (en) 1957-07-24

Family

ID=6687271

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15889/53A Expired GB779781A (en) 1952-06-09 1953-06-09 Water insoluble dyestuffs and a process for producing fast dyeings and prints therewith

Country Status (1)

Country Link
GB (1) GB779781A (en)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3005811A (en) * 1958-04-25 1961-10-24 Shell Oil Co Process for polymerizing diolefins in presence of vinyl cycloolefin
US3040024A (en) * 1957-03-07 1962-06-19 Ciba Ltd Azo-dyestuffs
US3102894A (en) * 1958-07-25 1963-09-03 Ici Ltd Anthraquinone dyestuffs
US3222119A (en) * 1959-03-10 1965-12-07 Monsanto Co Process for treating cellulosic textile materials with bis(beta-methoxyethyl) sulfone
US3226395A (en) * 1960-10-04 1965-12-28 Hoechst Ag Water-insoluble phthalocyanine dyestuffs and process for their manufacture
US3232927A (en) * 1962-12-31 1966-02-01 Gen Aniline & Film Corp Water soluble organic dyestuffs
US3365472A (en) * 1961-11-29 1968-01-23 Ciba Ltd 1-(amino and hydroxy)-4-anilino-3'-sulfo-anthraquinones substituted with a fiber reactive group at the 4'-position
US3369013A (en) * 1965-07-12 1968-02-13 Eastman Kodak Co Disazo dyes
US3415810A (en) * 1965-07-12 1968-12-10 Eastman Kodak Co Monoazo dyes for textile fibers
US3418310A (en) * 1965-10-04 1968-12-24 Eastman Kodak Co Thiadiazolyl monoazo dyes
FR2034705A1 (en) * 1969-03-06 1970-12-11 Hoechst Ag
FR2372210A1 (en) * 1976-11-25 1978-06-23 Hoechst Ag WATER-SOLUBLE AZOIC DYES USED FOR DYING AND PRINTING CELLULOSE AND POLYAMIDES
EP0617089A1 (en) * 1993-03-24 1994-09-28 Bayer Ag Fiber-reactive azo dyes

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3040024A (en) * 1957-03-07 1962-06-19 Ciba Ltd Azo-dyestuffs
US3005811A (en) * 1958-04-25 1961-10-24 Shell Oil Co Process for polymerizing diolefins in presence of vinyl cycloolefin
US3102894A (en) * 1958-07-25 1963-09-03 Ici Ltd Anthraquinone dyestuffs
US3222119A (en) * 1959-03-10 1965-12-07 Monsanto Co Process for treating cellulosic textile materials with bis(beta-methoxyethyl) sulfone
US3226395A (en) * 1960-10-04 1965-12-28 Hoechst Ag Water-insoluble phthalocyanine dyestuffs and process for their manufacture
US3365472A (en) * 1961-11-29 1968-01-23 Ciba Ltd 1-(amino and hydroxy)-4-anilino-3'-sulfo-anthraquinones substituted with a fiber reactive group at the 4'-position
US3232927A (en) * 1962-12-31 1966-02-01 Gen Aniline & Film Corp Water soluble organic dyestuffs
US3369013A (en) * 1965-07-12 1968-02-13 Eastman Kodak Co Disazo dyes
US3415810A (en) * 1965-07-12 1968-12-10 Eastman Kodak Co Monoazo dyes for textile fibers
US3418310A (en) * 1965-10-04 1968-12-24 Eastman Kodak Co Thiadiazolyl monoazo dyes
FR2034705A1 (en) * 1969-03-06 1970-12-11 Hoechst Ag
FR2372210A1 (en) * 1976-11-25 1978-06-23 Hoechst Ag WATER-SOLUBLE AZOIC DYES USED FOR DYING AND PRINTING CELLULOSE AND POLYAMIDES
EP0617089A1 (en) * 1993-03-24 1994-09-28 Bayer Ag Fiber-reactive azo dyes
US5493010A (en) * 1993-03-24 1996-02-20 Bayer Aktiengesellschaft SO2 -containing fiber-reactive azo dyestuffs

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