GB807241A - Anthraquinone dyestuffs - Google Patents

Anthraquinone dyestuffs

Info

Publication number
GB807241A
GB807241A GB2657556A GB2657556A GB807241A GB 807241 A GB807241 A GB 807241A GB 2657556 A GB2657556 A GB 2657556A GB 2657556 A GB2657556 A GB 2657556A GB 807241 A GB807241 A GB 807241A
Authority
GB
United Kingdom
Prior art keywords
anthraquinone
chloroanthraquinone
amino
alkyl
polyacrylonitrile
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
GB2657556A
Inventor
Gunter Gehrke
Ludwig Nussler
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Publication of GB807241A publication Critical patent/GB807241A/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
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/002—Dyes with anthracene nucleus not condensed with any other ring containing onium groups
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
    • 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
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/36—Dyes with acylated amino groups
    • 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
    • C09B3/02—Benzathrones
    • C09B3/06—Preparation from starting materials already containing the benzanthrone nucleus
    • C09B3/10—Amino derivatives

Landscapes

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

Abstract

Textile materials of polyacrylonitrile or copolymers thereof with a minor proportion of e.g. alkyl acrylate or vinyl acetate are dyed or printed with an anthraquinone dyestuff which contains, besides any other groups which may be present, an alkamino group of the formula <FORM:0807241/IV (c)/1> where X is a bivalent aliphatic radical of up to six carbon atoms, R1 is hydrogen or alkyl, R2 and R3 are alkyl or together form a heterocyclic ring with the tertiary nitrogen atom, or with an alkyl ammonium salt of said dyestuff. The dyes are made by reacting anthraquinone derivatives (including condensed systems such as benzanthrone, acridone, anthrapyridone or anthrapyrimidine) which contain substituents such as halogen, nitro, hydroxy, alkoxy or arylhydroxy, with amines of the formula <FORM:0807241/IV (c)/2> The anthraquinone molecule may contain other substituents such as amino, alkylamino, hydroxyalkylamino, acylamino, alkyl, hydroxy, alkoxy, mercapto, carboxamide or cyano. In examples: (1) 1-methylamino-4-bromo-anthraquinone is reacted with 1-dimethylamino-3-aminopropane, 1 - dimethylamino - 2 - aminoethane, 1 - diethylamino - 3 - aminopropane, 1-diethylamino - 4 - amino - n - pentane or N-(b -aminoethyl) piperidine and the products obtained or their quaternary ammonium salts obtained by reacting with dimethyl sulphate, diethyl sulphate, methyl toluene sulphonate or benzyl chloride, are used to dye polyacrylonitrile fibres; (2) 1-methylamino-5-chloroanthraquinone is reacted with 1-dimethylamino-3-aminopropane, and the product obtained or its salt with dimethyl sulphate is used to dye or print polyacrylonitrile fibres. Other anthraquinone starting materials listed are 1-nitroanthraquinone, 1 - amino - 4 - methoxyanthraquinone, 1 - b - hydroxyethylamino - 4 - bromoanthraquinone, 1 - hexahydroanilino - 4 - bromoanthraquinone, 1 - p - methylanilino - 4 - methoxy - anthraquinone, 1 - benzoylamino - 4-chloroanthraquinone, 1 - acetylamino - 4 - methoxyanthraquinone, 1 - amino - 5 - chloranthraquinone, 1 - methylamino - 5 - nitro - anthraquinone, 1 - b - hydroxyethylamino - 5 - chloroanthraquinone, 1 - ethylamino - 8 - chloroanthraquinone, 1.4 - diamino - 5 - nitro - anthraquinone, 1 - amino - 4 - hydroxy - 5 - chloroanthraquinone. Dyeing may be effected in an acid, alkaline or neutral bath at temperatures up to or above 100 DEG C. Example (7) describes the printing of a polyacrylonitrile material, the thickened paste containing in addition to the dyestuff, thiodiglycol, cyclohexanol, acetic acid, zinc nitrite, turkey red oil and petrol. Specification 459,594, [Group IV], is referred to.
GB2657556A 1955-08-30 1956-08-30 Anthraquinone dyestuffs Expired GB807241A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF18299A DE1150652B (en) 1955-08-30 1955-08-30 Dyeing of polyacrylonitrile fibers

Publications (1)

Publication Number Publication Date
GB807241A true GB807241A (en) 1959-01-14

Family

ID=7088896

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2657556A Expired GB807241A (en) 1955-08-30 1956-08-30 Anthraquinone dyestuffs

Country Status (4)

Country Link
CH (1) CH351575A (en)
DE (1) DE1150652B (en)
FR (1) FR1158839A (en)
GB (1) GB807241A (en)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3202682A (en) * 1961-07-27 1965-08-24 Allied Chem Synthetic pigments of the anthraquinone type
US3232934A (en) * 1959-06-25 1966-02-01 Allied Chem Omega-(1-amino-5 and 8-anthraquinonylamino)-1-ammonium alkanes of 2 to 3 carbon atoms
US3272792A (en) * 1961-12-18 1966-09-13 American Aniline Prod Quaternary ammonium salts of amino halohydrin dyestuffs
US3281434A (en) * 1963-06-19 1966-10-25 Gen Aniline & Film Corp 1, 4-dihydroxy-5-butylamino-8-(3-trimethylamino-propylamino)-anthraquinone methylsulfate
DE1267360B (en) * 1963-04-23 1968-05-02 Sandoz Ag Process for the preparation of anthraquinone dyes
DE1270712B (en) * 1960-01-08 1968-06-20 Gen Aniline & Film Corp Process for the preparation of anthraquinone dyes
US3401003A (en) * 1963-09-04 1968-09-10 Therachemic Chemisch Therapeut Diaminoanthraquinones and their use as human hair dyes
DE1281078B (en) * 1963-04-23 1968-10-24 Sandoz Ag Process for the preparation of dyes of the anthraquinone series
US3515733A (en) * 1961-04-21 1970-06-02 Sandoz Ag Basic dyes
US3546258A (en) * 1964-01-27 1970-12-08 Oreal 1,4-diamino - 5 - (p-amino phenyl) amino anthraquinones,the acid addition and quaternary ammonium salts thereof
US3844712A (en) * 1968-06-15 1974-10-29 Bayer Ag Treatment of dyed polyamides
WO2007090800A2 (en) * 2006-02-09 2007-08-16 Dystar Textilfarben Gmbh & Co Deutschland Kg Hair dye compositions

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2533428A1 (en) * 1975-07-25 1977-02-10 Bayer Ag CATIONIC COLORS
DE2906132A1 (en) 1979-02-17 1980-08-28 Bayer Ag METHOD FOR PRODUCING CATIONIC ANTHRACHINONE DYES
DD207226A5 (en) * 1980-12-24 1984-02-22 Ciba Geigy PROCESS FOR SPINNING POLYMERS OF ACRYLNITRILE

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE618006C (en) * 1933-09-03 1935-08-30 I G Farbenindustrie Akt Ges Process for coloring plastic masses from water-insoluble polymerization products of unsaturated compounds with an olefinic double bond
DE714986C (en) * 1938-07-15 1941-12-11 Ig Farbenindustrie Ag Process for the production of basic dyes of the anthraquinone series
CH259411A (en) * 1945-12-27 1949-01-31 Rhodiaceta Stable dye bath for objects or articles based on polyvinyl derivatives.

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3232934A (en) * 1959-06-25 1966-02-01 Allied Chem Omega-(1-amino-5 and 8-anthraquinonylamino)-1-ammonium alkanes of 2 to 3 carbon atoms
DE1270712B (en) * 1960-01-08 1968-06-20 Gen Aniline & Film Corp Process for the preparation of anthraquinone dyes
US3515733A (en) * 1961-04-21 1970-06-02 Sandoz Ag Basic dyes
US3202682A (en) * 1961-07-27 1965-08-24 Allied Chem Synthetic pigments of the anthraquinone type
US3272792A (en) * 1961-12-18 1966-09-13 American Aniline Prod Quaternary ammonium salts of amino halohydrin dyestuffs
DE1267360B (en) * 1963-04-23 1968-05-02 Sandoz Ag Process for the preparation of anthraquinone dyes
DE1281078B (en) * 1963-04-23 1968-10-24 Sandoz Ag Process for the preparation of dyes of the anthraquinone series
US3281434A (en) * 1963-06-19 1966-10-25 Gen Aniline & Film Corp 1, 4-dihydroxy-5-butylamino-8-(3-trimethylamino-propylamino)-anthraquinone methylsulfate
US3401003A (en) * 1963-09-04 1968-09-10 Therachemic Chemisch Therapeut Diaminoanthraquinones and their use as human hair dyes
US3546258A (en) * 1964-01-27 1970-12-08 Oreal 1,4-diamino - 5 - (p-amino phenyl) amino anthraquinones,the acid addition and quaternary ammonium salts thereof
US3844712A (en) * 1968-06-15 1974-10-29 Bayer Ag Treatment of dyed polyamides
WO2007090800A2 (en) * 2006-02-09 2007-08-16 Dystar Textilfarben Gmbh & Co Deutschland Kg Hair dye compositions
WO2007090799A2 (en) 2006-02-09 2007-08-16 Dystar Textilfarben Gmbh & Co Deutschland Kg Dyestuffs and hair dye compositions
EP1820826A1 (en) * 2006-02-09 2007-08-22 DyStar Textilfarben GmbH &amp; Co. Deutschland KG Dyestuffs and Hair Dye Compositions
WO2007090800A3 (en) * 2006-02-09 2007-12-21 Dystar Textilfarben Gmbh & Co Hair dye compositions
JP2009529582A (en) * 2006-02-09 2009-08-20 ダイスター テクスティルファルベン ゲゼルシャフト ミト ベシュレンクテル ハフツング ウント コンパニー ドイツランド コマンデイトゲゼルシャフト Dye and hair dye composition
JP2009531285A (en) * 2006-02-09 2009-09-03 ダイスター テクスティルファルベン ゲゼルシャフト ミト ベシュレンクテル ハフツング ウント コンパニー ドイツランド コマンデイトゲゼルシャフト Hair dye composition

Also Published As

Publication number Publication date
CH351575A (en) 1961-01-31
FR1158839A (en) 1958-06-19
DE1150652B (en) 1963-06-27

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