GB944265A - Naphthotriazole brightening agents - Google Patents

Naphthotriazole brightening agents

Info

Publication number
GB944265A
GB944265A GB7833/62A GB783362A GB944265A GB 944265 A GB944265 A GB 944265A GB 7833/62 A GB7833/62 A GB 7833/62A GB 783362 A GB783362 A GB 783362A GB 944265 A GB944265 A GB 944265A
Authority
GB
United Kingdom
Prior art keywords
alkyl
bromine
chlorine
alkoxy
fluorine
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
GB7833/62A
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.)
GAF Chemicals Corp
Original Assignee
General Aniline and Film 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 General Aniline and Film Corp filed Critical General Aniline and Film Corp
Publication of GB944265A publication Critical patent/GB944265A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/22—Naphthotriazoles
    • C07D249/24—Naphthotriazoles with stilbene radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3472—Five-membered rings
    • C08K5/3475—Five-membered rings condensed with carbocyclic rings
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60—Optical bleaching or brightening
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60—Optical bleaching or brightening
    • D06L4/614—Optical bleaching or brightening in aqueous solvents
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/0004—General aspects of dyeing
    • D06P1/0012—Effecting dyeing to obtain luminescent or phosphorescent dyeings
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6426—Heterocyclic compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • D06P1/65125—Compounds containing ester groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring (AREA)

Abstract

The invention comprises fluorescent naphthotriazoles of the formula: <FORM:0944265/C2/1> wherein R1 and R2 represent hydrogen, halogen such as fluorine, chlorine and bromine, C1-4 alkyl, C1-6 alkoxy or cycloalkoxy, and R3 represents alkyl, monohydroxyalkyl, dihydroxyalkyl, trihydroxyalkyl, dialkylaminoalkyl, aryl (optionally substituted by chlorine, bromine, fluorine, alkyl or alkoxy), hexamethyleneiminoN-ethyl or morpholino-N-alkyl or piperidino-N-alkyl in which the alkyl group contains from 1 to 4 carbon atoms. The naphthotriazoles may be prepared by diazotizing a stilbene of the formula: <FORM:0944265/C2/2> coupling the product with 2-naphthylamine, oxidizing the resulting monazo dye to a triazole, converting the free carboxylic group to an acid chloride group by treatment with thionyl chloride and finally reacting the acid chloride group with an appropriate phenol, dialkylamino-alkanol, heterocyclic-substituted alkanol or mono-, di-, tri-, or tetra-hydric alcohol. Alternatively, compounds of the formula: <FORM:0944265/C2/3> may be formed from the free carboxylic acid via the acid chloride, the nitro group in the resulting ester reduced to an amino group, the resulting compound diazotized, coupled with 2-naphthylamine and finally oxidized to the required triazole.ALSO:Polyethylene terephthalate is brightened by adding to the starting mixture of dimethyl terephthalate and ethylene glycol, or to a low polymer obtained therefrom, a fluorescent naphthotriazole of the formula: <FORM:0944265/C3/1> wherein R1 and R2 represent hydrogen, halogen such as fluorine, chlorine and bromine, C1-4 alkyl, C1-6 alkoxy or cycloalkoxy, and R3 represents alkyl, monohydroxyalkyl, dihydroxyalkyl, trihydroxyalkyl, dialkylaminoalkyl, aryl (optionally substituted by chlorine, bromine, fluorine, alkyl or alkoxy), hexamethyleneimino-N-ethyl or morpholino-N-alkyl or piperidino-N-alkyl in which the alkyl group contains from 1 to 4 carbon atoms.ALSO:Monazo dyestuffs are prepared by diazotizing a stilbene of the formula <FORM:0944265/C3/1> wherein R1 and R2 represent hydrogen, halogen such as fluorine, chlorine and bromine, C1-4 alkyl, C1-6 alkoxy or cycloalkoxy, and coupling the product with 2-naphthylamine. Alternatively, further monazo dyestuffs are formed by reducing the nitro group in compounds of the formula <FORM:0944265/C3/2> wherein R3 represents alkyl, monohydroxyalkyl, dihydroxyalkyl, trihydroxyalkyl, dialkylaminoalkyl, aryl (optionally substituted by chlorine, bromine, fluorine, alkyl or alkoxy), hexamethyleneimino - N - ethyl or morpholinoN-alkyl or piperidino - N - alkyl in which the alkyl group contains from 1 to 4 carbon atoms, diazotizing the resulting amino compound and coupling it with 2-naphthylamine.ALSO:Nylon, polyethylene teraphthalate and polyacrylonitrile in the form of films, fibres and fabrics are brightened by treatment with a fluorescent naphthotriazole of the formula:- <FORM:0944265/D1-D2/1> wherein R1 and R2 represent hydrogen, halogen such as fluorine, chlorine and bromine, C1-4 alkyl, C1-6 alkoxy or cycloalkoxy, and R3 represents alkyl, monohydroxyalkyl, dihydroxyalkyl, trihydroxyalkyl, dialkylaminoalkyl, aryl (optionally substituted by chlorine, bromine, fluorine, alkyl or alkoxy), hexamethyleneimino-N-ethyl or morpholino-N-alkyl or piperidino-N-alkyl in which the alkyl group contains from 1 to 4 carbon atoms. The fluorescent naphthotriazoles may be applied to the materials to be brightened from a dimethylformamide solution to which has been added a small amount of an aqueous polyoxyethylene surfactant.
GB7833/62A 1961-03-31 1962-02-28 Naphthotriazole brightening agents Expired GB944265A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US9970261A 1961-03-31 1961-03-31

Publications (1)

Publication Number Publication Date
GB944265A true GB944265A (en) 1963-12-11

Family

ID=22276214

Family Applications (1)

Application Number Title Priority Date Filing Date
GB7833/62A Expired GB944265A (en) 1961-03-31 1962-02-28 Naphthotriazole brightening agents

Country Status (4)

Country Link
BE (1) BE615617A (en)
CH (2) CH467819A (en)
DE (1) DE1419334C3 (en)
GB (1) GB944265A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1594834B1 (en) * 1965-10-28 1971-11-11 Ciba Geigy Ag Optical brighteners

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1594834B1 (en) * 1965-10-28 1971-11-11 Ciba Geigy Ag Optical brighteners

Also Published As

Publication number Publication date
DE1419334C3 (en) 1973-09-27
CH467819A (en) 1969-01-31
CH371762A4 (en) 1965-03-31
DE1419334B2 (en) 1973-03-08
BE615617A (en) 1962-07-16
CH396826A (en) 1966-01-31
DE1419334A1 (en) 1969-04-03

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