GB1047796A - Triphenylmethane dyes - Google Patents

Triphenylmethane dyes

Info

Publication number
GB1047796A
GB1047796A GB2588564A GB2588564A GB1047796A GB 1047796 A GB1047796 A GB 1047796A GB 2588564 A GB2588564 A GB 2588564A GB 2588564 A GB2588564 A GB 2588564A GB 1047796 A GB1047796 A GB 1047796A
Authority
GB
United Kingdom
Prior art keywords
alkyl
ethyl
hydrogen
aralkyl
carbon atoms
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
GB2588564A
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.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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 EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Publication of GB1047796A publication Critical patent/GB1047796A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/025—Duplicating or marking methods; Sheet materials for use therein by transferring ink from the master sheet
    • B41M5/04—Duplicating or marking methods; Sheet materials for use therein by transferring ink from the master sheet using solvent-soluble dyestuffs on the master sheets, e.g. alcohol-soluble
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/22—Amino derivatives of triarylmethanes containing OH groups bound to an aryl nucleus and their ethers and esters
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/26—Triarylmethane dyes in which at least one of the aromatic nuclei is heterocyclic
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H21/00—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties
    • D21H21/14—Non-fibrous material added to the pulp, characterised by its function, form or properties; Paper-impregnating or coating material, characterised by its function, form or properties characterised by function or properties in or on the paper
    • D21H21/28—Colorants ; Pigments or opacifying agents
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/72—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705
    • G03C1/73—Photosensitive compositions not covered by the groups G03C1/005 - G03C1/705 containing organic compounds

Abstract

The invention comprises a leuco dye of the formula <FORM:1047796/C4-C5/1> where R1 and R2 are alkyl groups containing from 1 to 12 carbon atoms, 2-cyanoethyl, 2-hydroxy-ethyl, 3-hydroxypropyl, alkoxy alkyl groups containing from 2 to 8 carbon atoms, aralkyl or aryl groups; R3 is methyl, ethyl or fluorine; X is hydrogen, hydroxy or cyano; and Q is 2-thienyl, 2-furyl, 3,4-methylenedioxy-phenyl, 2-methoxy-4-(C1 to C8)-alkoxyphenyl, 3,4-di-(C1 to C8) alkoxyphenyl or <FORM:1047796/C4-C5/2> where R4 is an alkyl, aralkyl, aryl or substituted aralkyl group containing from 1 to 8 carbon atoms, the substituents of said substituted aralkyl being fluoro, chlori, alkyl or alkoxy substituents and R5 is hydrogen or an alkyl group containing from 1 to 4 carbon atoms, and oxidized, coloured forms thereof, and a leuco dye-salt of the formula <FORM:1047796/C4-C5/3> where M is hydrogen and A an anion, or M is a metal and A is an anion or anions which satisfy the valence of M and which together with M form a Lewis acid, and n is 1 or 2. The coloured dyes which are formed by oxidation of the leuco dye or salts have the formula <FORM:1047796/C4-C5/4> The leuco compounds in which X is hydrogen may be made by condensation of (a) 2-thiophene-carboxaldehyde, 2-furaldehyde or a correspondingly substituted benzaldehyde with an N,N-disubstituted-3-methyl (or ethyl or fluoro) aniline; (b) an acetal of the aldehydes named in (a) with an N,N-disubstituted-m-toluidine; or (c) a bis-[4-N,N-disubstituted amino-2-ethyl (or fluoro or methyl phenyl] methanol with a phenyl alkyl (or aryl or aralkyl) sulphide. The corresponding methanols (X is OH) may be prepared by oxidizing the methanes in an alkaline medium or by alkaline hydrolysis of the oxidized dye, and the corresponding cyanomethanes (X is CN) may be made by treating the oxidized dye with alkali metal cyanide. Some of the dyes may be made directly from a phenone R1R2N.C6H3(CH3).CO.Q and a N,N-dialkyl-m-toluidine. The leuco compounds may be oxidized to the dyes with lead dioxide, chloranil, sodium dichromate, manganese dioxide or nitrosyl sulphuric acid. The substituted methanols and cyanomethanes are converted to the dyes by acid hydrolysis.ALSO:The invention comprises a leuco dye of the formula <FORM:1047796/C2/1> where R1 and R2 are alkyl groups containing from 1 to 12 carbon atoms, 2-cyanoethyl, 2-hydroxy-ethyl, 3-hydroxypropyl, alkoxy alkyl groups containing from 2 to 8 carbon atoms, aralkyl or aryl groups; R3 is methyl, ethyl or flourine; X is hydrogen, hydroxy or cyano; and Q is 2-thienyl, 2-furyl, 3,4-methylene-dioxyphenyl, 2 - methoxy - 4 - (C1 to C8)-alkoxyphenyl, 3,4-di-(C1 to C8) alkoxyphenyl or <FORM:1047796/C2/2> where R4 is an alkyl, aralkyl, aryl or substituted aralkyl group containing from 1 to 8 carbon atoms, the substituents of said substituted aralkyl being fluoro, chloro, alkyl or alkoxy substituents and R5 is hydrogen or an alkyl group containing from 1 to 4 carbon atoms, and a leuco dye-salt of the formula <FORM:1047796/C2/3> where M is hydrogen and A an anion, or M is a metal and A is an anion or anions which satisfy the valence of M and which together with M form a Lewis acid, and n is 1 or 2. The leuco compounds in which X is hydrogen may be made by condensation of (a) 2-thiophene - carboxaldehyde, 2 - furaldehyde or a correspondingly substituted benzaldehyde with an N,N-disubstituted-3-methyl (or ethyl or flouro) aniline; (b) an acetal of the aldehydes named in (a) with an N,N-disubstituted-m-toluidine; or (c) a bis-[4-N,N-disubstituted amino-2-ethyl (or fluoro or methyl) phenyl] methanol with a phenyl alkyl (or aryl or aralkyl) sulphide. The corresponding methanols (X is OH) may be prepared by oxidizing the methanes in an alkaline medium or by alkaline hydrolysis of the oxidized dye, and the corresponding cyanomethanes (X is CN) may be made by treating the oxidized dye with alkali metal cyanide.
GB2588564A 1963-06-26 1964-06-23 Triphenylmethane dyes Expired GB1047796A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US29064863A 1963-06-26 1963-06-26

Publications (1)

Publication Number Publication Date
GB1047796A true GB1047796A (en) 1966-11-09

Family

ID=23116960

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2588564A Expired GB1047796A (en) 1963-06-26 1964-06-23 Triphenylmethane dyes

Country Status (1)

Country Link
GB (1) GB1047796A (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3418128A (en) * 1965-01-04 1968-12-24 Dietzgen Co Eugene Photosensitive compositions comprising acid addition salts of substituted leucocyanide triphenylmethane dyes and metal perchlorates
WO2004005406A2 (en) * 2002-07-10 2004-01-15 E.I. Du Pont De Nemours And Company Charge transport compositions on the basis of triarylmethanes and their use in electronic devices
US7211118B2 (en) 2002-12-30 2007-05-01 L'oreal S.A. Composition for dyeing keratin fibers comprising a defined triheteroylmethane direct dye or leuco precursor of this dye and dyeing method using it
US7211117B2 (en) 2002-12-30 2007-05-01 L'oreal S.A. Composition for dyeing keratin fibers comprising at least one dye chosen from monoheteroyldiarylmethane direct dyes and the leuco precursors thereof and dyeing method using it
US7217297B2 (en) 2002-12-30 2007-05-15 L'oreal S.A. Composition for dyeing keratin fibers comprising a defined diheteroylarylmethane direct dye or a leuco precursor of this dye and dyeing method using it
US7288121B2 (en) 2004-02-27 2007-10-30 L'oreal S.A. Composition comprising at least one mixed dye comprising at least one chromophore chosen from compounds of the methine family and/or the carbonyl family, dyeing process and kit, and mixed dyes
US7300471B2 (en) 2004-02-27 2007-11-27 L'oreal S.A. Composition comprising at least one mixed dye based on at least one chromophore of azo or tri(hetero) arylmethane type, dyeing process and mixed dyes.
US7303591B2 (en) 2004-02-27 2007-12-04 L'oreal S.A. Composition comprising at least one mixed dye comprising at least two chromophores of (hetero) aromatic nitro or cyclic azine type, dyeing process, and mixed dyes
WO2019075140A1 (en) * 2017-10-12 2019-04-18 The Procter & Gamble Company Laundry care compositions, methods, and test kits for determining authenticity
WO2019075222A1 (en) * 2017-10-12 2019-04-18 Milliken & Company Compositions, methods, and test kits for determining authenticity
US11920039B2 (en) 2019-01-30 2024-03-05 Battelle Savannah River Alliance, Llc Malachite green based radio-chromic compounds and radiation sensing systems incorporating the compounds

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3418128A (en) * 1965-01-04 1968-12-24 Dietzgen Co Eugene Photosensitive compositions comprising acid addition salts of substituted leucocyanide triphenylmethane dyes and metal perchlorates
US7544312B2 (en) 2002-07-10 2009-06-09 Norman Herron Charge transport compositions and electronic devices made with such compositions
WO2004005406A2 (en) * 2002-07-10 2004-01-15 E.I. Du Pont De Nemours And Company Charge transport compositions on the basis of triarylmethanes and their use in electronic devices
WO2004005406A3 (en) * 2002-07-10 2004-05-21 Du Pont Charge transport compositions on the basis of triarylmethanes and their use in electronic devices
US8529796B2 (en) 2002-07-10 2013-09-10 E I Du Pont De Nemours And Company Charge transport compositions and electronic devices made with such compositions
US8293139B2 (en) 2002-07-10 2012-10-23 E I Du Pont De Nemours And Company Charge transport compositions and electronic devices made with such compositions
US8287769B2 (en) 2002-07-10 2012-10-16 E I Du Pont De Nemours And Company Charge transport compositions and electronic devices made with such compositions
US8071975B2 (en) 2002-07-10 2011-12-06 E. I. Du Pont De Nemours And Company Electronic devices made with electron transport and/or anti-quenching layers
US7217297B2 (en) 2002-12-30 2007-05-15 L'oreal S.A. Composition for dyeing keratin fibers comprising a defined diheteroylarylmethane direct dye or a leuco precursor of this dye and dyeing method using it
US7211117B2 (en) 2002-12-30 2007-05-01 L'oreal S.A. Composition for dyeing keratin fibers comprising at least one dye chosen from monoheteroyldiarylmethane direct dyes and the leuco precursors thereof and dyeing method using it
US7211118B2 (en) 2002-12-30 2007-05-01 L'oreal S.A. Composition for dyeing keratin fibers comprising a defined triheteroylmethane direct dye or leuco precursor of this dye and dyeing method using it
US7303591B2 (en) 2004-02-27 2007-12-04 L'oreal S.A. Composition comprising at least one mixed dye comprising at least two chromophores of (hetero) aromatic nitro or cyclic azine type, dyeing process, and mixed dyes
US7300471B2 (en) 2004-02-27 2007-11-27 L'oreal S.A. Composition comprising at least one mixed dye based on at least one chromophore of azo or tri(hetero) arylmethane type, dyeing process and mixed dyes.
US7288121B2 (en) 2004-02-27 2007-10-30 L'oreal S.A. Composition comprising at least one mixed dye comprising at least one chromophore chosen from compounds of the methine family and/or the carbonyl family, dyeing process and kit, and mixed dyes
WO2019075222A1 (en) * 2017-10-12 2019-04-18 Milliken & Company Compositions, methods, and test kits for determining authenticity
WO2019075140A1 (en) * 2017-10-12 2019-04-18 The Procter & Gamble Company Laundry care compositions, methods, and test kits for determining authenticity
CN111194337A (en) * 2017-10-12 2020-05-22 宝洁公司 Laundry care compositions, methods and test kits for determining authenticity
CN111448260A (en) * 2017-10-12 2020-07-24 美利肯公司 Compositions, methods and kits for determining authenticity
US10889717B2 (en) 2017-10-12 2021-01-12 Milliken & Company Compositions, methods, and test kits for determining authenticity
CN111448260B (en) * 2017-10-12 2022-04-05 美利肯公司 Compositions, methods and kits for determining authenticity
US11634663B2 (en) 2017-10-12 2023-04-25 The Procter & Gamble Company Laundry care compositions, methods, and test kits for determining authenticity
US11920039B2 (en) 2019-01-30 2024-03-05 Battelle Savannah River Alliance, Llc Malachite green based radio-chromic compounds and radiation sensing systems incorporating the compounds

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