GB1475081A - Water-soluble anthraquinone dyes - Google Patents

Water-soluble anthraquinone dyes

Info

Publication number
GB1475081A
GB1475081A GB2302173A GB2302173A GB1475081A GB 1475081 A GB1475081 A GB 1475081A GB 2302173 A GB2302173 A GB 2302173A GB 2302173 A GB2302173 A GB 2302173A GB 1475081 A GB1475081 A GB 1475081A
Authority
GB
United Kingdom
Prior art keywords
group
nuclei
alkyl
alkylene
dyes
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
GB2302173A
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.)
Yorkshire Chemicals Ltd
Original Assignee
Yorkshire Chemicals Ltd
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 Yorkshire Chemicals Ltd filed Critical Yorkshire Chemicals Ltd
Priority to GB2302173A priority Critical patent/GB1475081A/en
Publication of GB1475081A publication Critical patent/GB1475081A/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
    • 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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Investigating Or Analysing Biological Materials (AREA)

Abstract

1475081 Water soluble anthraquinone dyes YORKSHIRE CHEMICALS Ltd 14 May 1974 [15 May 1973] 23021/73 Heading C4P The invention comprises water soluble basic dyes having the general formula wherein the n quaternary alkylamino groups are in α-positions in the anthraquinone nucleus, R<SP>1</SP> is alkylene, R<SP>2</SP> is alkyl, R<SP>3</SP> is alkyl or R<SP>2</SP> and R<SP>3</SP> together with the quaternary N atom represent a heterocyclic ring, R<SP>4</SP> is alkylene, R<SP>5</SP> is a substituted or unsubstituted aryl group with the proviso that R<SP>5</SP> does not represent an unsubstituted phenyl group when R<SP>4</SP> is methylene, X- is an anion which renders the dyestuff soluble in water and n is 1 or 2, and wherein the nuclei A and B, and the alkyl, aryl and alkylene groups may be optionally further substituted, but not by sulphonic or carboxylic acid groups, and in the case of nuclei A and B not by α-positioned branched chain alkylamine residues or α- halogen substituted arylamine residues and when n is 1 and nucleii A and B are further substituted, at least one of the further substituents must be present in the same nucleus as the quaternary alkylamino group and when n is 2, at least one further substituent must be present in nuclei A and/or B. They are prepared by reacting one mole of a compound of the general formula with n moles of an aralkylating agent R<SP>4</SP>R<SP>5</SP>R<SP>6</SP> where A, B, n, 12<SP>1</SP>-12<SP>5</SP> are as above and R<SP>6</SP> is an atom or group replaceable under the reaction conditions, e.g. Cl, Br, I or toluene 4-sulphonic acid ester group. The reaction takes place at 30 -150‹ C. in an organic solvent. The dyes are used to dye or print polyacrylonitrile and its copolymers, tannin-mordanted cotton, cellulose acetate, and acid-modified polyamide and polyesters.
GB2302173A 1974-05-14 1974-05-14 Water-soluble anthraquinone dyes Expired GB1475081A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB2302173A GB1475081A (en) 1974-05-14 1974-05-14 Water-soluble anthraquinone dyes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2302173A GB1475081A (en) 1974-05-14 1974-05-14 Water-soluble anthraquinone dyes

Publications (1)

Publication Number Publication Date
GB1475081A true GB1475081A (en) 1977-06-01

Family

ID=10188823

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2302173A Expired GB1475081A (en) 1974-05-14 1974-05-14 Water-soluble anthraquinone dyes

Country Status (1)

Country Link
GB (1) GB1475081A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0014899A1 (en) * 1979-02-17 1980-09-03 Bayer Ag Process for the preparation of cationic anthraquinone dyes
FR2456806A1 (en) * 1979-05-14 1980-12-12 Ici Ltd Colouring wet-spun acrylic! fibres in gel condition - using a bis. cationic anthraquinone dyestuff
US4456552A (en) * 1979-08-02 1984-06-26 American Cyanamid Company 1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof
US4614618A (en) * 1979-08-02 1986-09-30 American Cyanamid Company 1,4-bis(substituted-amino)-5,8-dihydroxy anthraquinones and leuco bases thereof
US4820738A (en) * 1977-08-15 1989-04-11 American Cyanamid Company 1,4-bis(substituted-amino)-5,8-dihydroxy-anthraquinones and leuco bases thereof
US5520707A (en) * 1995-08-07 1996-05-28 Clairol, Inc. Methods for dyeing hair with anthraquinone hair dyes having a quaternary ammonium side chain
WO2019223015A1 (en) * 2018-05-25 2019-11-28 苏州大学张家港工业技术研究院 Precursor of blue anthraquinone active disperse dye and preparation method therefor

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4820738A (en) * 1977-08-15 1989-04-11 American Cyanamid Company 1,4-bis(substituted-amino)-5,8-dihydroxy-anthraquinones and leuco bases thereof
EP0014899A1 (en) * 1979-02-17 1980-09-03 Bayer Ag Process for the preparation of cationic anthraquinone dyes
FR2456806A1 (en) * 1979-05-14 1980-12-12 Ici Ltd Colouring wet-spun acrylic! fibres in gel condition - using a bis. cationic anthraquinone dyestuff
US4456552A (en) * 1979-08-02 1984-06-26 American Cyanamid Company 1,4-Bis(substituted-amino)-5,8-dihydroxyanthraquinones and leuco bases thereof
US4614618A (en) * 1979-08-02 1986-09-30 American Cyanamid Company 1,4-bis(substituted-amino)-5,8-dihydroxy anthraquinones and leuco bases thereof
US5520707A (en) * 1995-08-07 1996-05-28 Clairol, Inc. Methods for dyeing hair with anthraquinone hair dyes having a quaternary ammonium side chain
US5891200A (en) * 1995-08-07 1999-04-06 Lim; Mu-Ill Hair dye compositions containing anthraquinone dyes having a quaternary ammonium side chain and neutral direct dyes
WO2019223015A1 (en) * 2018-05-25 2019-11-28 苏州大学张家港工业技术研究院 Precursor of blue anthraquinone active disperse dye and preparation method therefor

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee