[go: up one dir, main page]

GB611510A - Process for improving the whiteness or colour of materials - Google Patents

Process for improving the whiteness or colour of materials

Info

Publication number
GB611510A
GB611510A GB15717/45A GB1571745A GB611510A GB 611510 A GB611510 A GB 611510A GB 15717/45 A GB15717/45 A GB 15717/45A GB 1571745 A GB1571745 A GB 1571745A GB 611510 A GB611510 A GB 611510A
Authority
GB
United Kingdom
Prior art keywords
double bonds
aromatic
residue
compounds
obtainable
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
GB15717/45A
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.)
BASF Schweiz AG
Original Assignee
Ciba AG
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 Ciba AG filed Critical Ciba AG
Publication of GB611510A publication Critical patent/GB611510A/en
Expired legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D21PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21HPULP 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
    • D21H21/00Non-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
    • D21H21/14Non-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
    • D21H21/30Luminescent or fluorescent substances, e.g. for optical bleaching
    • DTEXTILES; PAPER
    • D01NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01FCHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00General methods for the manufacture of artificial filaments or the like
    • D01F1/02Addition of substances to the spinning solution or to the melt
    • D01F1/10Other agents for modifying properties
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06LDRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60Optical bleaching or brightening

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Paper (AREA)

Abstract

Soaps and cleansing compositions contain a compound, of the general formula <FORM:0611510/III/1> (wherein A represents an aromatic nucleus which may contain substituents and of which two vicinal carbon atoms are attached to the two nitrogen atoms of the imidazole ring, R1 represents hydrogen or a substituent, e.g. an alkyl or aralkyl residue, and R represents a radical containing an uninterrupted series of at least four conjugated double bonds starting with the carbon atom of the residue R directly connected to the m carbon atom, said double bonds being present in open chains or in rings), which exhibits a blue to violet fluorescence in ultra-violet light, imparts little or no colour to material treated therewith and is sparingly soluble or insoluble in water. In examples: (2) a : b -di-(benzimidazyl-2)-ethylene, or a solution thereof in caustic soda solution or in glycol monomethyl ether, is added to a melted soap mass; (4) and (7) the same compound is added to the sodium salt of sulphonated 2-heptadecyl-N-benzyl- or -N-methyl-benzimidazole. Other washing agents specified for use with the fluorescent materials are monocarboxylic esters of 4-sulphophthalic acid with higher fatty alcohols, fatty alcohol sulphonates, and condensation products of higher fatty acids with aliphatic hydroxy- and amino-sulphonic acids. A sample has been furnished under Sect. 2 (5) of cotton fabric boiled with a solution of soap containing the di-imidazole compound obtained by condensing terephthalic aldehyde with excess of 2-methylbenzimidazole.ALSO:Artificial threads or films, e.g. of regenerated cellulose, cellulose acetate or synthetic linear superpolyamide, are improved in colour or whiteness by adding to the spinning or casting solution a compound of the general formula <FORM:0611510/IV(a)/1> (wherein A represents an aromatic nucleus which may contain substituents and of which two vicinal carbon atoms are attached to the two nitrogen atoms of the imidazole ring, R1 represents hydrogen or a substituent, e.g. an alkyl or aralkyl residue, and R represents a radical containing an uninterrupted series of at least four conjugated double bonds starting with the carbon atom of the residue R directly connected to the m -carbon atom, said double bonds being present in open chains or in rings), which exhibits a blue to violet fluorescence in ultra-violet light, imparts little or no colour to the material, and is sparingly soluble or insoluble in water. Particular classes of substances which are suitable are: (A) compounds of the above formula in which R represents an aralkenyl residue of which the alkenyl residue contains at least one double bond which forms with the double bond of the imidazole ring and those of the aryl nucleus an uninterrupted series of at least five conjugated double bonds e.g. a 2-styrylbenzimidazole obtainable by condensation of a 2-methylbenzimidazole with an aromatic aldehyde, the aryl nuclei of these components optionally containing substituents (e.g. acylated amino groups); (B) compounds of the above formula in which R represents a heterocyclic residue containing the required series of conjugated double bonds, e.g. diimidazoles of the formula <FORM:0611510/IV(a)/2> such as dibenzimidazoles (in which A represents a benzene nucleus) obtainable by known methods from o-phenylenediamines which may contain further nuclear substituents; (C) compounds of the formula <FORM:0611510/IV(a)/3> wherein R2 represents a divalent residue containing at least one double bond which forms with the >C=N- double bonds of the imidazole rings and the double bonds of the aromatic nuclei A an uninterrupted series of conjugated double bonds, e.g. (a) substituted ethylenes (in which R2 is CH=CH) obtainable by condensing aromatic o-diamines with fumaric or maleic acid or functional derivatives thereof, and (b) compounds in which R2 represents a divalent aromatic or heterocyclic residue containing at least one double bond in conjugation with the >C=N- double bonds, obtainable similarly from aromatic or heterocyclic dicarboxylic acids or their functional derivatives.ALSO:2-Styrylbenzimidazoles are prepared by condensing a 2-methylbenzimidazole with an aromatic aldehyde. Di-imidazylethylenes of the general formula <FORM:0611510/IV(b)/1> (wherein A represents an aromatic nucleus and R1 hydrogen or a substituent, e.g. benzyl) are prepared by condensing aromatic o-diamines with fumaric or maleic acid or functional derivatives thereof, e.g. o-phenylenediamine with fumaric acid to produce a : b -di(benzimidazyl-2)-ethylene, or with maleic acid or anhydride. Di-imidazyl compounds containing, in place of the -CH=CH- group in the foregoing general formula, a divalent aromatic or heterocyclic residue containing at least one double bond in conjugation with the >C=N- double bonds of the imidazole rings are obtainable similarly using aromatic or heterocyclic dicarboxylic acids or their functional derivatives in place of the fumaric or maleic compounds. A compound employed in the preparation of a sample furnished under Sect. 2 (5) was prepared by condensing terephthalic aldehyde with excess of 2-methylbenzimidazole.ALSO:Materials in the form of fibres or films are improved in colour or whiteness by applying thereto, at any desired stage in their manufacture or treatment, a compound, of the general formula <FORM:0611510/IV (c)/1> wherein A represents an aromatic nucleus which may contain substituents and of which two vicinal carbon atoms are attached to the two nitrogen atoms of the imidazole ring, R1 represents hydrogen or a substituent, e.g. an alkyl or aralkyl residue, and R represents a radial containing an uninterrupted series of at least four conjugated double bonds starting with the carbon atom of the residue R directly connected to the m -carbon atom, said double bonds being present in open chains or in rings), which exhibits a blue to violet fluorescence in ultra-violet light, imparts little or no colour to insoluble in water. Particular classes of substances which are suitable are: (a) compounds of the above formula in which R represents an aralkenyl residue of which the alkenyl residue contains at least one double bond which forms with the double bond of the imidazole ring and those of the aryl nucleus an uninterrupted series of at least five conjugated double bonds, e.g. 1 2-styrylbenzimidazole obtainable by condensation of a 2-methylbenzimidazole with an aromatic aldehyde, the aryl nuclei of these components optionally containing substituents (e.g. acylated amino groups); (b) compounds of the above formula in which R represents a heterocyclic residue containing the required series of conjugated double bonds, e.g. di-imidazoles of the formula <FORM:0611510/IV (c)/2> such as dibenzimidazoles (in which A represents a benzene nucleus) obtainable by known methods from o-phenylenediamines which may contain further nuclear substituents; (c) compounds of the formula <FORM:0611510/IV (c)/3> (wherein R2 represents a divalent residue containing at least one double bond which forms with the >C=N- double bonds of the imidazole rings and the double bonds of the aromatic nuclei A an uninterrupted series of conjugated double bonds, e.g. (a) substituted ethylenes (in which R2 is CH=CH) obtainable by condensing aromatic o-diamines with fumaric or maleic acid or functional derivatives thereof, and (b) compounds in which R2 represents a divalent aromatic or heterocyclic residue containing at least one double bond in conjugation with the >C=N- double bonds, obtainable similarly from aromatic or heterocyclic dicarboxylic acids or their functional derivatives. Compounds in which R1 represents hydrogen may be used in the form of metal (especially alkali metal) salts, in which case they may be dissolved in an alcoholic solution of an alkali hydroxide and the solution, after dilution with water, may be applied to the material to be treated, e.g. natural or regenerated cellulose, which is then rinsed, centrifuged or squeezed and dried. Alternatively the material may be impregnated with a solution of the fluorescent compound (including one in which R1 is a substituent) or a salt thereof in an organic solvent (which is then removed) or with a dispersion thereof (e.g. one obtained with the aid of a dispersing agent such as soap, a saponaceous substance, polyglycol ethers of fatty alcohols, sulphite cellulose waste liquor or condensation products of alkylnaphthalenesulphonic acids and formaldehyde). The fluorescent compounds may also be applied during the manufacture of the materials to be improved, e.g. by incorporating them in paper pulp or in a viscose solution for the production of films or threads or other spinning masses (e.g. containing a linear synthetic polyamide or cellulose acetate), or they may be used in admixture with assistants used to improve textile materials, e.g. with washing agents such as soaps, salts of sulphonated washing agents, e.g. sulphonated benzimidazoles substituted in the 2-position by higher alkyl residues, monocarboxylic esters of 4-sulphophthalic acid with higher fatty alcohols, fatty alcohol sulphonates or condensation products of higher fatty acids with aliphatic hydroxy- or amino-sulphonic acids, or with chemical bleaching agents, e.g. sodium hypochlorite, or with mercerizing liquor, or in discharge printing pastes. The process is applicable to the improvement of cellulosic materials such as cellulose or paper, textile materials of cotton, linen or regenerated cellulose, natural or artificial nitrogenous materials such as wool, silk or synthetic polyamide fibres, cellulose acetate, and synthetic materials produced by polymerization, all of which materials may be undyed or dyed or printed. Examples are given of a large number of applications of the process, the fluorescent materials used being a : b - di - (benzimidazyl - 2) - ethylene (obtai
GB15717/45A 1944-09-29 1945-06-20 Process for improving the whiteness or colour of materials Expired GB611510A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH611510X 1944-09-29

Publications (1)

Publication Number Publication Date
GB611510A true GB611510A (en) 1948-11-01

Family

ID=4523438

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15717/45A Expired GB611510A (en) 1944-09-29 1945-06-20 Process for improving the whiteness or colour of materials

Country Status (3)

Country Link
CH (2) CH253876A (en)
GB (1) GB611510A (en)
NL (1) NL61528C (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2875089A (en) * 1959-02-24 Process for the optical brightening of
US2950207A (en) * 1957-11-07 1960-08-23 American Enka Corp Production of filaments having improved whiteness
DE1094696B (en) * 1955-02-15 1960-12-15 Ciba Geigy Process for the optical brightening of materials made of polyesters
DE1302051B (en) * 1955-04-21 1969-11-13 Sterling Drug Inc Use of benzimidazolyl stilbene compounds as optical brightening agents

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE957131C (en) * 1954-07-10 1957-01-31 Ruhr Stickstoff Ag Process for lightening discolored ammonium sulphate containing metal salts from coking plants and gas stations, which is particularly used as a fertilizer
DE1011406B (en) * 1955-01-21 1957-07-04 Gelsenkirchener Bergwerks Ag Process for the production of a technical, white, color and storage-stable ammonium sulfate

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2875089A (en) * 1959-02-24 Process for the optical brightening of
DE1094696B (en) * 1955-02-15 1960-12-15 Ciba Geigy Process for the optical brightening of materials made of polyesters
DE1302051B (en) * 1955-04-21 1969-11-13 Sterling Drug Inc Use of benzimidazolyl stilbene compounds as optical brightening agents
US2950207A (en) * 1957-11-07 1960-08-23 American Enka Corp Production of filaments having improved whiteness

Also Published As

Publication number Publication date
CH246967A (en) 1947-02-15
NL61528C (en)
CH253876A (en) 1948-03-31

Similar Documents

Publication Publication Date Title
US2463264A (en) Derivatives of cyclic amidines and process of making same
GB655296A (en) Process for improving materials in the form of fibre or film and compositions of matter suitable therefor
US2995564A (en) Thiophene derivatives
US3400124A (en) Optical brightening and new compositions of matter
GB923162A (en) Process for dyeing, printing and/or optical brightening of textile materials and dye preparations therefor
GB611510A (en) Process for improving the whiteness or colour of materials
US3429877A (en) Azole compounds
US3136773A (en) New 2, 5-dibenzoxazolyl-thiophene derivatives
US2901480A (en) Process for the manufacture of new pyrpole derivatives
GB828545A (en) Process for the optical brightening of materials composed of polyester resins
US2567796A (en) Water-soluble aminostilbene derivatives and process
US2808407A (en) New imidazolium compounds
US2875089A (en) Process for the optical brightening of
GB803361A (en) A process and products for the improvement of the optical properties of organic material
CH439563A (en) Device for controlling and monitoring the ignition process on a fan burner
US2576896A (en) Compositions of matter for producing a softening effect on textiles
US2604454A (en) Detergent composition containing diimidazoles
US2878248A (en) Carboxy-esters of hydroxybenzimidazolyl-stilbenes
US3178421A (en) Novel bis-aryloxazolyl ethylene optical brightening derivatives
US2205032A (en) Dye compositions
GB929053A (en) Dyeing, fluorescent brightening and/or printing textile materials
US3629246A (en) Novel diarylene azolyl-styrene compounds and the preparation and use thereof
US2856311A (en) Process for optically brightening fibrous materials
GB653681A (en) Manufacture of new derivatives of di-imidazoles
AT162913B (en) Process for finishing fiber materials