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GB1276686A - New process for the alkylation of benzthiazole azo compounds - Google Patents

New process for the alkylation of benzthiazole azo compounds

Info

Publication number
GB1276686A
GB1276686A GB4606669A GB4606669A GB1276686A GB 1276686 A GB1276686 A GB 1276686A GB 4606669 A GB4606669 A GB 4606669A GB 4606669 A GB4606669 A GB 4606669A GB 1276686 A GB1276686 A GB 1276686A
Authority
GB
United Kingdom
Prior art keywords
benzthiazole
azo compounds
substituents
aqueous
alkylation
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
GB4606669A
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.)
Toms River Chemical Corp
Original Assignee
Toms River Chemical Corp
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 Toms River Chemical Corp filed Critical Toms River Chemical Corp
Publication of GB1276686A publication Critical patent/GB1276686A/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
    • C09B44/00Azo dyes containing onium groups
    • C09B44/005Special process features in the quaternization reaction
    • 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
    • C09B44/00Azo dyes containing onium groups
    • C09B44/10Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
    • C09B44/20Thiazoles or hydrogenated thiazoles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Coloring (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1276686 Alkylation of benzthiazole azo compounds TOMS RIVER CHEMICAL CORP 18 Sept 1969 [18 Sept 1968] 46066/69 Heading C4P Benzthiazole-azo compounds of the formula are alkylated by treatment with a dialkyl. sulphoester in aqueous medium in the presence of an alkali metal or alkaline earth metal oxide, carbonate, bicarbonate or acetate, by adding the dialkylsulphoester to an aqueous-alkaline dispersion of the dyestuff in an amount of not more than 5 moles of ester per mole of dyestuff. In the formula given above R 1 to R 8 are nonionogenic substituents, including hydrogen; R 9 and R 10 are H, aliphatic, araliphatic, aromatic or alicyclic substituents; and two neighbouring substituents among R 1 to R 10 can also form a ring. The reaction is carried out at a temperature of 5-70‹ C. and at a pH of from 4-8. Suitable dialkylsulphoesters include dimethyl-, diethyl- or dipropylsulphate, and the alkylating agent is added continuously to the aqueous-alkaline dispersion of the benzthiazole compound. The cationic dyes give blue shades on acrylic fibres and either do not stain on cotton and wool or give slight stains which are in tone with the blue colouring on acrylic fibres. Reference has been directed by the Comptroller to Specification 787,369.
GB4606669A 1968-09-18 1969-09-18 New process for the alkylation of benzthiazole azo compounds Expired GB1276686A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US76068168A 1968-09-18 1968-09-18

Publications (1)

Publication Number Publication Date
GB1276686A true GB1276686A (en) 1972-06-07

Family

ID=25059851

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4606669A Expired GB1276686A (en) 1968-09-18 1969-09-18 New process for the alkylation of benzthiazole azo compounds

Country Status (9)

Country Link
JP (1) JPS5328456B1 (en)
BE (1) BE738994A (en)
CH (1) CH559763A5 (en)
CS (1) CS178059B2 (en)
DE (1) DE1943799B2 (en)
FR (1) FR2018311B1 (en)
GB (1) GB1276686A (en)
NL (1) NL6914104A (en)
RO (1) RO56336A (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4048151A (en) * 1972-07-31 1977-09-13 Sandoz Ltd. Cationic dyes containing an optionally substituted bicyclic or polycyclic aryloxyalkyl group
GB2001666A (en) * 1977-07-22 1979-02-07 Hoechst Ag Process for the preparation of benzothiazolium azo compounds and chlorozincate salts thereof
FR2436162A1 (en) * 1978-09-15 1980-04-11 Hoechst Ag PROCESS FOR THE PREPARATION OF CHLOROZINCATES FROM THIAZOLIUM AZO DYES
US4289693A (en) * 1972-07-31 1981-09-15 Sandoz Ltd. Azo dyes having a quaternized heterocyclic diazo component radical and an optionally substituted aryloxyalkyl substituent on the amino group of the coupling component radical
US5163972A (en) * 1989-12-06 1992-11-17 Ciba-Geigy Corporation Process for the dyeing of polyacrylonitrile materials with cationic benzo-thiazolium azo dye
FR2829926A1 (en) * 2001-09-26 2003-03-28 Oreal New cationic azo compounds useful for dyeing keratinic fibers, especially human hair
WO2007087252A1 (en) * 2006-01-23 2007-08-02 Milliken & Company Laundry care compositions with thiazolium dye
US9796952B2 (en) 2012-09-25 2017-10-24 The Procter & Gamble Company Laundry care compositions with thiazolium dye

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2616412B2 (en) * 1976-04-14 1980-01-31 Bayer Ag, 5090 Leverkusen Process for the preparation of concentrated solutions of basic dyes and agents for coloring polyacrylonitrile and acid-modified polyesters or polyamides
JPS58459U (en) * 1981-06-25 1983-01-05 パイオニア株式会社 Printed board
JPH0762258A (en) * 1993-08-26 1995-03-07 Sumitomo Chem Co Ltd Benzodifuranone-containing red coloring composition and method for coloring hydrophobic material using the same
MXPA06006855A (en) * 2003-12-19 2006-08-23 Ciba Sc Holding Ag Method of coloring with capped diazotized compound and coupling component.

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1530784A (en) * 1966-06-24 1968-06-28 Ciba Geigy New basic dyes and their preparation process

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4048151A (en) * 1972-07-31 1977-09-13 Sandoz Ltd. Cationic dyes containing an optionally substituted bicyclic or polycyclic aryloxyalkyl group
US4289693A (en) * 1972-07-31 1981-09-15 Sandoz Ltd. Azo dyes having a quaternized heterocyclic diazo component radical and an optionally substituted aryloxyalkyl substituent on the amino group of the coupling component radical
GB2001666A (en) * 1977-07-22 1979-02-07 Hoechst Ag Process for the preparation of benzothiazolium azo compounds and chlorozincate salts thereof
US4638053A (en) * 1977-07-22 1987-01-20 Hoechstaktiengesellschaft Process for the preparation of chlorozincate salts of benzo thiazolium azo dyestuffs by alkylating with dialkylsulfate in aqueous medium in the presence of Zn-containing acid acceptor at pH≦7
FR2436162A1 (en) * 1978-09-15 1980-04-11 Hoechst Ag PROCESS FOR THE PREPARATION OF CHLOROZINCATES FROM THIAZOLIUM AZO DYES
US5163972A (en) * 1989-12-06 1992-11-17 Ciba-Geigy Corporation Process for the dyeing of polyacrylonitrile materials with cationic benzo-thiazolium azo dye
US5929216A (en) * 1989-12-06 1999-07-27 Ciba Specialty Chemicals Corporation Benzothiazolium containing azo dyes useful for dyeing polyacrylonitrile
US6824570B2 (en) 2001-09-26 2004-11-30 L'oreal S.A. Composition for dyeing human keratin fibres, comprising a particular monocationic monoazo dye
EP1297819A2 (en) * 2001-09-26 2003-04-02 L'oreal Composition for dyeing keratinous fibres comprising a cationic azo dye
EP1297819A3 (en) * 2001-09-26 2004-03-03 L'oreal Composition for dyeing keratinous fibres comprising a cationic azo dye
FR2829926A1 (en) * 2001-09-26 2003-03-28 Oreal New cationic azo compounds useful for dyeing keratinic fibers, especially human hair
WO2007087252A1 (en) * 2006-01-23 2007-08-02 Milliken & Company Laundry care compositions with thiazolium dye
WO2007084729A3 (en) * 2006-01-23 2007-09-20 Procter & Gamble Laundry care compositions with thiazolium dye
US7674757B2 (en) 2006-01-23 2010-03-09 Milliken & Company Laundry care compositions with thiazolium dye
US7977300B2 (en) 2006-01-23 2011-07-12 Milliken & Co. Laundry care compositions with thiazolium dye
RU2463339C2 (en) * 2006-01-23 2012-10-10 Милликен Энд Компани Washing composition with thiazole dye
US8299010B2 (en) 2006-01-23 2012-10-30 The Procter & Gamble Company Laundry care compositions with thiazolium dye
US8461095B2 (en) 2006-01-23 2013-06-11 Milliken & Company Laundry care compositions with thiazolium dye
CN101370925B (en) * 2006-01-23 2014-03-26 美利肯公司 Laundry care compositions with thiazolium dye
US9796952B2 (en) 2012-09-25 2017-10-24 The Procter & Gamble Company Laundry care compositions with thiazolium dye

Also Published As

Publication number Publication date
CS178059B2 (en) 1977-08-31
DE1943799A1 (en) 1970-04-09
DE1943799B2 (en) 1976-07-01
CH559763A5 (en) 1975-03-14
NL6914104A (en) 1970-03-20
BE738994A (en) 1970-03-17
RO56336A (en) 1974-06-01
FR2018311B1 (en) 1973-12-21
FR2018311A1 (en) 1970-05-29
JPS5328456B1 (en) 1978-08-15

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Legal Events

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