GB929588A - Water-soluble dyes of the anthraquinone and perylene tetracarboxylic acid diimide series - Google Patents

Water-soluble dyes of the anthraquinone and perylene tetracarboxylic acid diimide series

Info

Publication number
GB929588A
GB929588A GB684761A GB684761A GB929588A GB 929588 A GB929588 A GB 929588A GB 684761 A GB684761 A GB 684761A GB 684761 A GB684761 A GB 684761A GB 929588 A GB929588 A GB 929588A
Authority
GB
United Kingdom
Prior art keywords
acid
dyes
reacting
aniline
dihydroxy
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
GB684761A
Inventor
Hermann Weissauer
Guenter Lange
Helmut Steuerle
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik 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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB929588A publication Critical patent/GB929588A/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
    • C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
    • C09B3/22—Dibenzanthrones; Isodibenzanthrones
    • C09B3/30—Preparation from starting materials already containing the dibenzanthrone or isodibenzanthrone nucleus
    • 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
    • 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
    • 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
    • C09B62/445—Anthracene dyes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

The g -methane sulphonate and g -p-toluene sulphonate esters of 5-(b :g -dihydroxy-propoxy-)-2-methyl-aniline are made by reacting 2-methyl- 5-(b :g -epoxypropoxy)- formanilide with methane sulphonic acid and p-toluene sulphonic acid respectively. p-(b -hydroxy-g -sulphatopropoxy)-aniline is made by esterifying with sulphuric acid, p-(b :g -dihydroxy-propoxy) aniline which is prepared by hydrolysis of the corresponding acetanilide. m-(b -hydroxy-g -sulphatopropoxy) aniline is made by reacting m-(b :g -dihydroxy-propoxy)-aniline or formanilide with sulphuric acid. 2-Methyl- 5-epoxypropoxyformanilide is made by condensing 2-methyl-5-hydroxyformanilide with epichlorhydrin.ALSO:The invention comprises water-soluble dyes of the anthraquinone or perylene tetracarboxylic acid diimide series containing at least one ionic water-solubilizing group and at least one aromatic radical linked on the one hand to the radical of an anthraquinone or perylene tetracarboxylic acid diimide dye via an oxygen or nitrogen atom and on the other hand to a b :g -dihydroxypropyl radical esterified in g -position with sulphuric acid or an organic sulphonic acid, via an oxygen or sulphur atom or an amino, sulphonamido or sulphone group. Anthraquinone dyes include those of the benzanthrone, dibenzanthrone, isodibenzanthrone, pyranthrone, pyrazolanthrone, benzacridone, anthrapyridone and anthrapyrimidine series. The dyes are made by reacting with sulphuric acid, chlorsulphuric acid, acid sulphates or pyrosulphates or an organic sulphonic acid, halide or anhydride, an appropriate dye containing a b :g -dihydroxypropyl or a b :g -epoxypropyl radical or a phenol or primary or secondary amine containing such radicals and then, in the latter case, reacting the amine or phenol with a dye containing a reactive chlorine or bromine atom, a sulphonic or carboxylic acid halide group or a carboxylic anhydride, carboxylic acid imide or dihalotriazinyl group. The starting dyes containing a b :g -dihydroxypropyl or b :g -epoxypropyl radical are made by reacting an appropriate dye containing an aromatic radical attached via an oxygen or nitrogen atom and substituted by a sulphinic acid, sulphhydryl or acylatable hydroxy or amino group with glycidol or a 1-halo-2:3-dihydroxypropane, or with a halohydrin of glycerol or an epihalohydrin and converting the halohydrins to epoxy compounds from which the dihydroxy derivatives may be obtained. The starting dyes may also be made by reacting dyes containing reactive halogen atoms, sulphonic acid or carboxylic acid halide, halomethyl, carboxylic acid anhydride, carboxylic acid imide or dihalotriazinyl groups with phenols or primary or secondary aromatic amines containing b :g -dihydroxy-propyl or b :g -epoxypropyl groups. Examples are given. The dyes dye and print leather, wool, silk, polycaprolactams and adipic acid-hexamethylene diamine condensation products from an acid bath, and cellulose materials in conjunction with a treatment with an alkaline agent.
GB684761A 1960-02-27 1961-02-24 Water-soluble dyes of the anthraquinone and perylene tetracarboxylic acid diimide series Expired GB929588A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB56843A DE1160125B (en) 1960-02-27 1960-02-27 Process for the production of water-soluble dyes of the anthraquinone series

Publications (1)

Publication Number Publication Date
GB929588A true GB929588A (en) 1963-06-26

Family

ID=6971471

Family Applications (2)

Application Number Title Priority Date Filing Date
GB3030862A Expired GB929589A (en) 1960-02-27 1961-02-24 Water-soluble dyes of the anthraquinone or perylene tetracarboxylic acid diimide series
GB684761A Expired GB929588A (en) 1960-02-27 1961-02-24 Water-soluble dyes of the anthraquinone and perylene tetracarboxylic acid diimide series

Family Applications Before (1)

Application Number Title Priority Date Filing Date
GB3030862A Expired GB929589A (en) 1960-02-27 1961-02-24 Water-soluble dyes of the anthraquinone or perylene tetracarboxylic acid diimide series

Country Status (3)

Country Link
BE (1) BE600634A (en)
DE (1) DE1160125B (en)
GB (2) GB929589A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0717084A1 (en) * 1994-12-15 1996-06-19 Hoechst Aktiengesellschaft Water soluble fibre reactive anthraquinone compounds

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR976047A (en) * 1942-03-26 1951-03-13 Ig Farbenindustrie Ag Process for fixing organic substances, soluble in water, on supports and making them insoluble
GB733471A (en) * 1949-07-18 1955-07-13 Hoechst Ag A process for fixing organic compounds on fibrous materials
BE578746A (en) * 1958-05-19 1959-11-16 Ici Ltd New water-soluble dyes.
BE581359A (en) * 1959-08-04 1960-02-04 Ici Ltd New water soluble dyes

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0717084A1 (en) * 1994-12-15 1996-06-19 Hoechst Aktiengesellschaft Water soluble fibre reactive anthraquinone compounds
US5744622A (en) * 1994-12-15 1998-04-28 Hoechst Aktiengesellschaft water-soluble, fiber-reactive anthraquinone compounds

Also Published As

Publication number Publication date
DE1160125B (en) 1963-12-27
GB929589A (en) 1963-06-26
BE600634A (en) 1961-08-24

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