GB1003083A - Novel 4-alkoxynaphthalimides - Google Patents

Novel 4-alkoxynaphthalimides

Info

Publication number
GB1003083A
GB1003083A GB2107/62A GB210762A GB1003083A GB 1003083 A GB1003083 A GB 1003083A GB 2107/62 A GB2107/62 A GB 2107/62A GB 210762 A GB210762 A GB 210762A GB 1003083 A GB1003083 A GB 1003083A
Authority
GB
United Kingdom
Prior art keywords
alkoxy
hydrogen
hydroxyalkyl
alkyl
aryl
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
GB2107/62A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of GB1003083A publication Critical patent/GB1003083A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/14—Aza-phenalenes, e.g. 1,8-naphthalimide
    • 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
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3437—Six-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
    • 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
    • D21H21/30—Luminescent or fluorescent substances, e.g. for optical bleaching
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/06—Dyes

Abstract

4-Alkoxynaphthalimides of formula <FORM:1003083/C3/1> where R is C1- 5-alkoxy and R1 is hydrogen alkyl, hydroxyalkyl, aminoalkyl, aralkyl, cycloalkyl, aryl, alkaryl or heterocyclic, the aryl group being optionally substituted by halogen, hydroxyalkyl, alkylamino, alkoxy or -SO3M, where M is hydrogen or an alkali metal are added as optical brightening agents to polyamides, polyesters, polyurethanes, polyvinyl chloride, polyvinylidene chloride, polyacrylonitrile or polyvinyl alcohol.ALSO:The invention comprises compounds of for mula <FORM:1003083/C2/1> where R is C1- 5 alkoxy, and R1 is hydrogen, alkyl, hydroxyalkyl, aminoalkyl, aralkyl, cycloalkyl, aryl, alkaryl or a heterocyclic group, the aryl group being optionally substituted by halogen, hydroxyalkyl, alkylamino, alkoxy or -SO3M, where M is hydrogen or alkali metal. Specified heterocyclic radicals are 2,6-dihalo-5-triazinyl, pyridyl and pyrazolyl. The compounds may be prepared by reacting a 4-alkoxy-1,8-naphthalic acid or its anhydride with a compound R1NH2 or by reacting a compound of formula <FORM:1003083/C2/2> where X is halogen, hydroxy, nitro or sulpho with an alkali metal alcoholate, or where X is hydroxy with a dialkyl sulphate or alkyl halide or where X is amino, converting this to the diazonium salt and reacting this with an alcohol ROH. Alternatively compounds in which R1 is hydrogen can be reacted with alkyl &c. halides to convert R1 into other values. The products are used as optical brightening agents. The diazonium chlorides of a number of 4-aminonaphthalimides are prepared (Example 28). The sodium salts of a number of 4-sulphonaphthalimides are prepared by reacting the sodium salt of 4-sulphonaphthalic acid with methylamine, butylamine, ethanolamine, benzylamine, cyclohexylamine, p-diethylamino-aniline, aniline, 2-ethylhexylamine and 3-dimethylaminopropylamine.ALSO:4-Alkoxynaphthalimides of formula <FORM:1003083/D1-D2/1> where R is C1-5 alkoxy, and R1 is hydrogen, alkyl, hydroxyalkyl, aminoalkyl, aralkyl, cycloalkyl, aryl, alkaryl or a heterocyclic group (particularly 2, 6-dihalo-s-triazinyl), the aryl group being optionally substituted by halogen, hydroxyalkyl, alkylamino, alkoxy, or -SO3M where M is hydrogen or an alkali metal, are used as optical brightening agents for textile materials. Specied are filaments, yarns, threads, and ribbons of cotton, capoc, linen, sisal, jute, wool, mohair, cashmere, asbestos, viscose rayon, cellulose acetate, polyamides, polyesters, polyurethanes, polyvinyl chloride, polyvinylidene chloride, polyacrylonitrile, polyvinyl alcohol and glass fibre. They may be used as aqueous or other solutions or dispersions with or without a dispersing agent. In Example 34, 4-methoxynaphthalimide is incorporated in a sodium hypochlorite bleach solution containing acetic acid and a chlorous dioxide gas generation inhibitor. Other compositions contain surfactant, carboxymethylcellulose, chlorobenzene-type carrier.
GB2107/62A 1961-01-21 1962-01-19 Novel 4-alkoxynaphthalimides Expired GB1003083A (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP194661 1961-01-21
JP240661 1961-01-26
JP240561 1961-01-26
JP478261 1961-02-12

Publications (1)

Publication Number Publication Date
GB1003083A true GB1003083A (en) 1965-09-02

Family

ID=27453513

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2107/62A Expired GB1003083A (en) 1961-01-21 1962-01-19 Novel 4-alkoxynaphthalimides

Country Status (4)

Country Link
BE (1) BE612955A (en)
CH (5) CH427811A (en)
DE (1) DE1445961C3 (en)
GB (1) GB1003083A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1288787B (en) * 1966-09-08 1969-02-06 Bayer Ag Polyamide molding compounds with compounds containing imide groups as mold release agents
US7714044B2 (en) 2003-11-14 2010-05-11 Basf Akitengesellschaft Use of 4-cyano-naphthalene-1, 8-dicarboximide derivatives and related compounds to protect organic material from the damaging effects of light
US7875720B2 (en) * 2000-04-27 2011-01-25 Nalco Company Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems
US8383656B2 (en) 2009-10-09 2013-02-26 The Ohio State University Research Foundation Thiazolidinedione energy restriction-mimetic agents
US8894881B2 (en) 2008-01-31 2014-11-25 Commissariat A L'energie Atomique Et Aux Energies Alternatives 1,8-naphthalimide derivatives as scintillation agents, in particular for discriminating between fast neutrons and gamma rays

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES459497A1 (en) * 1977-06-04 1978-04-16 Made Labor Sa N(Aminoalkyl)-naphthalimides and their derivatives
DE3618458A1 (en) * 1986-06-02 1987-12-03 Hoechst Ag NAPHTHALIMIDES CONTAINING SULFURIC ACID ESTER GROUPS, METHOD FOR THE PRODUCTION AND USE THEREOF

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1288787B (en) * 1966-09-08 1969-02-06 Bayer Ag Polyamide molding compounds with compounds containing imide groups as mold release agents
US7875720B2 (en) * 2000-04-27 2011-01-25 Nalco Company Fluorescent monomers and tagged treatment polymers containing same for use in industrial water systems
US7714044B2 (en) 2003-11-14 2010-05-11 Basf Akitengesellschaft Use of 4-cyano-naphthalene-1, 8-dicarboximide derivatives and related compounds to protect organic material from the damaging effects of light
CN1902180B (en) * 2003-11-14 2010-08-25 巴斯福股份公司 Use of 4-cyano-naphthalene-1,8-dicarboximide derivatives and related compounds to protect organic material from the damaging effects of light
US8894881B2 (en) 2008-01-31 2014-11-25 Commissariat A L'energie Atomique Et Aux Energies Alternatives 1,8-naphthalimide derivatives as scintillation agents, in particular for discriminating between fast neutrons and gamma rays
US8383656B2 (en) 2009-10-09 2013-02-26 The Ohio State University Research Foundation Thiazolidinedione energy restriction-mimetic agents

Also Published As

Publication number Publication date
CH427811A (en) 1967-01-15
CH446713A (en) 1967-11-15
CH442315A (en) 1967-08-31
BE612955A (en) 1962-05-16
DE1445961B2 (en) 1978-09-28
DE1445961A1 (en) 1969-12-11
CH409850A (en) 1965-12-15
CH461495A (en) 1968-08-31
DE1445961C3 (en) 1979-05-17

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