EP0310083B1 - Process for quenching or suppressing the fluorescence of optically brightened substrates - Google Patents

Process for quenching or suppressing the fluorescence of optically brightened substrates Download PDF

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Publication number
EP0310083B1
EP0310083B1 EP88116113A EP88116113A EP0310083B1 EP 0310083 B1 EP0310083 B1 EP 0310083B1 EP 88116113 A EP88116113 A EP 88116113A EP 88116113 A EP88116113 A EP 88116113A EP 0310083 B1 EP0310083 B1 EP 0310083B1
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EP
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Prior art keywords
hydrogen
sulfo
phenyl
c4alkyl
c4alkoxy
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EP88116113A
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German (de)
French (fr)
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EP0310083A1 (en
Inventor
Gerhard Dr. Reinert
Kurt Dr. Burdeska
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Novartis AG
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Ciba Geigy AG
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/35—Heterocyclic compounds
    • D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
    • D06M13/358—Triazines
    • 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
    • D06L4/686—Fugitive optical brightening; Discharge of optical brighteners in discharge paste; Blueing; Differential optical brightening
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/35—Heterocyclic compounds
    • D06M13/352—Heterocyclic compounds having five-membered heterocyclic rings
    • 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
    • D06P1/62—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 with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/628—Compounds containing nitrogen
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/916—Natural fiber dyeing
    • Y10S8/917—Wool or silk
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
    • Y10S8/92—Synthetic fiber dyeing
    • Y10S8/924—Polyamide fiber

Definitions

  • the present invention relates to a method for quenching or suppressing the fluorescence of substrates treated with optical brighteners made of natural or synthetic polyamides with sulfonated UV absorbers, and the material treated therewith.
  • GB-A-2 174 731 discloses a process for the deletion or prevention of lightening effects on various substrates with UV absorbers, in which derivatives of the benzophenone series or of the non-sulfonated benzotriazole series are used as UV absorbers.
  • the compounds of formulas (1) to (3) given above are e.g. known from WO-A-84/02365 and WO-A-86/03528 and can be prepared by known methods.
  • UV absorbers Mixtures of UV absorbers can also be used.
  • the UV absorber is advantageously applied to the substrate from an aqueous medium.
  • the UV absorber can be impregnated and held at room or elevated temperature, for example between 20 and 90 ° C. for 30 minutes to all known methods of dyeing or printing, such as treatment in a long bath at temperatures from 20 to 140 ° C. 48 hours depending on the temperature, padding and fixing by the action of saturated steam, superheated steam, hot air, treatment with high-frequency or contact heat, are applied and fixed on the substrate.
  • the UV absorber can also be used in so-called thermal printing.
  • the UV absorber can be fixed on the substrate by mediating organic high polymers, for example in the form of aqueous or non-aqueous paints, or using the pigment printing method.
  • UV absorber The choice of application and fixing method and the amount of UV absorber depend on the substrate, the dyes used, the optical brighteners and their fastness and the properties of the UV absorbers used. In general, good extinguishing effects are obtained when the UV absorber is used in an amount of 0.1 to 5% of the weight of the goods.
  • the UV absorber is used according to the invention after the optical brightening, or before, during or after the dyeing or printing of a substrate treated with an optical brightener. This is the case, for example, with items of clothing that are washed after use will.
  • Commercial detergents or soaps for the household today mostly contain optical brighteners to make the laundry washed with them appear whiter. If textiles dyed or printed in light colors are washed with such a detergent, a different color tone results after drying than before. This is particularly objectionable for light colors such as noted, rosé, beige etc.
  • optical brightening effects are deleted or suppressed locally or over the entire surface.
  • optical brightening effects are produced by commercially available optical brighteners, for example known anionic or cationic optical brighteners and dispersion brighteners as are used in detergents.
  • optical brighteners are derivatives of bis (triazinylamino) stilbene disulfonic acid, triazolyl derivatives of stilbene sulfonic acids, bis (stilbene) compounds, pyrazoline, coumarin, bis (benzimidazolyl), bis (oxazolyl), naphthalimide, Cyanine, benzoxazolyl and oxacyanine derivatives called.
  • Textile materials consisting of natural or synthetic polyamides are used as substrates and e.g. Yarns, fabrics, knitted fabrics or fleece understood.
  • the textile materials can also consist of mixtures of polyamides with other fibers.

Description

Die vorliegende Erfindung betrifft ein Verfahren zum Löschen oder Unterdrücken der Fluoreszenz von mit optischen Aufhellern behandelten Substraten aus natürlichen oder synthetischen Polyamiden mit sulfonierten UV-Absorbern sowie das damit behandelte Material.The present invention relates to a method for quenching or suppressing the fluorescence of substrates treated with optical brighteners made of natural or synthetic polyamides with sulfonated UV absorbers, and the material treated therewith.

Verfahren zum Löschen der Fluoreszenz von mit optischen Aufhellern behandelten Substraten sind bereits bekannt. So ist z.B. aus der GB-A-2 174 731 ein Verfahren zur Löschung oder Verhinderung von Aufhelleffekten auf verschiedenen Substraten mit UV-Absorbern bekannt, bei welchem als UV-Absorber Derivate der Benzophenonreihe oder der nicht sulfonierten Benzotriazolreihe verwendet werden.Methods for quenching the fluorescence from substrates treated with optical brighteners are already known. For example, GB-A-2 174 731 discloses a process for the deletion or prevention of lightening effects on various substrates with UV absorbers, in which derivatives of the benzophenone series or of the non-sulfonated benzotriazole series are used as UV absorbers.

Es wurde nun gefunden, dass sulfonierte 2-Hydroxyphenyl-benzotriazole und 2-Hydroxyphenyl-s-triazine sich sehr gut eignen, um Fluoreszenzeffekte optisch aufgehellter Substrate zu löschen oder zu unterdrücken.It has now been found that sulfonated 2-hydroxyphenyl-benzotriazoles and 2-hydroxyphenyl-s-triazines are very suitable for quenching or suppressing fluorescence effects of optically brightened substrates.

Gegenstand der vorliegenden Erfindung ist somit ein Verfahren zum Löschen oder Unterdrücken der Fluoreszenz von mit optischen Aufhellern behandelten Substraten aus natürlichen oder synthetischen Polyamiden mit UV-Absorbern, das dadurch gekennzeichnet ist, dass man auf diese Substrate einen sulfonierten UV-Absorber der Formel

Figure imgb0001

worin

R₁
Wasserstoff, Halogen, C₁-C₁₂-Alkyl, C₅-C₆-Cycloalkyl, C₇-C₉-Phenylalkyl oder Sulfo,
R₂
Wasserstoff, C₁-C₄-Alkyl, C₁-C₄-Alkoxy, Halogen, Hydroxy oder Sulfo,
R₃
Wasserstoff, C₁-C₁₂-Alkyl, C₁-C₄-Alkoxy, Phenyl, (C₁-C₈-Alkyl)-phenyl, C₅-C₆-Cycloalkyl, C₂-C₉-Alkoxycarbonyl, Halogen, Carboxy-C₁-C₄-alkyl, C₇-C₉-Phenylalkyl oder Sulfo und
X
einen Rest der Formel
Figure imgb0002
bedeuten, worin
R₄
für Wasserstoff, Halogen, C₁-C₄-Alkyl, C₁-C₄-Alkoxy, C₂-C₉-Alkoxycarbonyl, Carboxy oder Sulfo,
R₅
für Wasserstoff oder Halogen und
R₆ und R₇
unabhängig voneinander für C₁-C₄-Alkyl, C₁-C₄-Alkoxy, C₅-C₆-Cycloalkyl, Phenyl oder durch C₁-C₄-Alkyl und Hydroxy substituiertes Phenyl
stehen,
aufbringt und fixiert.The present invention thus relates to a method for quenching or suppressing the fluorescence of substrates treated with optical brighteners from natural or synthetic polyamides with UV absorbers, which is characterized in that a sulfonated UV absorber of the formula is applied to these substrates
Figure imgb0001
wherein
R₁
Hydrogen, halogen, C₁-C₁₂-alkyl, C₅-C₆-cycloalkyl, C₇-C₉-phenylalkyl or sulfo,
R₂
Hydrogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, halogen, hydroxy or sulfo,
R₃
Hydrogen, C₁-C₁₂-alkyl, C₁-C₄-alkoxy, phenyl, (C₁-C₈-alkyl) -phenyl, C₅-C₆-cycloalkyl, C₂-C₉-alkoxycarbonyl, halogen, carboxy-C₁-C₄-alkyl, C₇- C₉-phenylalkyl or sulfo and
X
a remainder of the formula
Figure imgb0002
mean what
R₄
for hydrogen, halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₂-C₉-alkoxycarbonyl, carboxy or sulfo,
R₅
for hydrogen or halogen and
R₆ and R₇
independently of one another for C₁-C₄-alkyl, C₁-C₄-alkoxy, C₅-C₆-cycloalkyl, phenyl or phenyl substituted by C₁-C₄-alkyl and hydroxy
stand,
applies and fixes.

Als UV-Absorber der Formel (1) kommen bevorzugt in Betracht

  • A) 2-Phenylbenzotriazole der Formel
    Figure imgb0003
     worin
    R₁
    Wasserstoff, C₁-C₁₂-Alkyl, Chlor, C₅-C₆-Cycloalkyl, C₇-C₉-Phenylalkyl oder Sulfo,
    R₂
    Wasserstoff, C₁-C₄-Alkyl, C₁-C₄-Alkoxy, Chlor, Hydroxy oder Sulfo
    R₃
    C₁-C₁₂-Alkyl, C₁-C₄-Alkoxy, Phenyl, (C₁-C₈-Alkyl)-phenyl, C₅-C₆-Cycloalkyl, C₂-C₉-Alkoxycarbonyl, Chlor, Carboxyethyl oder C₇-C₉-Phenylalkyl oder Sulfo,
    R₄
    Wasserstoff, Chlor, C₁-C₄-Alkyl, C₁-C₄-Alkoxy, C₂-C₉-Alkoxycarbonyl, Carboxy oder Sulfo und
    R₅
    Wasserstoff oder Chlor
    bedeuten, wobei Carboxy- oder Sulfongruppen auch als Salze, z.B. Alkalimetall- Erdalkalimetall-, Ammonium- oder Aminsalze vorliegen können. Beispiele von Verbindungen der Formel (2) sind das Natriumsalz der 3-(2′H-benzotriazol-2′-yl)-5-tert.-butyl-4-hydroxy-, 3-(2′H-5′-chlorbenzotriazol-2′-yl)-5-tert.-butyl-4-hydroxy- und 3-(2′H-benzotriazol-2′-yl)-5-sec.-butyl-4-hydroxy-benzolsulfonsäure, und
  • B) 2-Phenyl-s-triazine der Formel
    Figure imgb0004
     worin
    R₁
    Wasserstoff, Halogen, C₁-C₄-Alkyl oder Sulfo,
    R₂
    Wasserstoff, C₁-C₄-Alkyl, C₁-C₄-Alkoxy oder Hydroxy,
    R₃
    Wasserstoff, oder Sulfo und
    R₆ und R₇
    unabhängig voneinander C₁-C₄-Alkyl, C₁-C₄-Alkoxy, C₅-C₆-Cycloalkyl, Phenyl oder durch C₁-C₄-Alkyl und Hydroxy substituiertes Phenyl bedeuten, wobei die Sulfongruppen in freier Form oder in Salzform, z.B. als Alkalimetall-, Erdalkalimetall-, Ammonium- oder Aminsalz vorliegen können. Beispiele von Verbindungen der Formel (3) sind das Natriumsalz der 3-(4′,6′-diphenyl-s-triazin-2′-yl)-4-hydroxy-6-methoxy-, 3-(4′,6′-diphenyl-s-triazin-2′-yl)-4-hydroxy-6-ethoxy- und 3-(4′,6′-diphenyl-s-triazin-2′-yl)-4-hydroxy-6-propoxy-benzolsulfonsäure.
Preferred UV absorbers of the formula (1) are suitable
  • A) 2-phenylbenzotriazoles of the formula
    Figure imgb0003
     wherein
    R₁
    Hydrogen, C₁-C₁₂-alkyl, chlorine, C₅-C₆-cycloalkyl, C₇-C₉-phenylalkyl or sulfo,
    R₂
    Hydrogen, C₁-C₄ alkyl, C₁-C₄ alkoxy, chlorine, hydroxy or sulfo
    R₃
    C₁-C₁₂-alkyl, C₁-C₄-alkoxy, phenyl, (C₁-C₈-alkyl) -phenyl, C₅-C₆-cycloalkyl, C₂-C₉-alkoxycarbonyl, chlorine, carboxyethyl or C₇-C₉-phenylalkyl or sulfo,
    R₄
    Hydrogen, chlorine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₂-C₉-alkoxycarbonyl, carboxy or sulfo and
    R₅
    Hydrogen or chlorine
    mean, carboxy or sulfone groups can also be present as salts, for example alkali metal, alkaline earth metal, ammonium or amine salts. Examples of compounds of formula (2) are the sodium salt of 3- (2'H-benzotriazol-2'-yl) -5-tert-butyl-4-hydroxy-, 3- (2'H-5'-chlorobenzotriazole -2'-yl) -5-tert-butyl-4-hydroxy- and 3- (2'H-benzotriazol-2'-yl) -5-sec.-butyl-4-hydroxy-benzenesulfonic acid, and
  • B) 2-phenyl-s-triazines of the formula
    Figure imgb0004
     wherein
    R₁
    Hydrogen, halogen, C₁-C₄-alkyl or sulfo,
    R₂
    Hydrogen, C₁-C₄-alkyl, C₁-C₄-alkoxy or hydroxy,
    R₃
    Hydrogen, or sulfo and
    R₆ and R₇
    independently of one another are C₁-C₄-alkyl, C₁-C₄-alkoxy, C₅-C₆-cycloalkyl, phenyl or phenyl substituted by C₁-C₄-alkyl and hydroxy, the sulfone groups in free form or in salt form, for example as alkali metal, alkaline earth metal -, ammonium or amine salt may be present. Examples of compounds of the formula (3) are the sodium salt of 3- (4 ′, 6′-diphenyl-s-triazin-2′-yl) -4-hydroxy-6-methoxy-, 3- (4 ′, 6 ′ -diphenyl-s-triazin-2'-yl) -4-hydroxy-6-ethoxy- and 3- (4 ', 6'-diphenyl-s-triazin-2'-yl) -4-hydroxy-6-propoxy -benzenesulfonic acid.

Die oben angegebenen Verbindungen der Formeln (1) bis (3) sind z.B. aus dem WO-A-84/02365 und WO-A-86/03528 bekannt und können nach bekannten Verfahren hergestellt werden.The compounds of formulas (1) to (3) given above are e.g. known from WO-A-84/02365 and WO-A-86/03528 and can be prepared by known methods.

Es können auch Mischungen von UV-Absorbern eingesetzt werden.Mixtures of UV absorbers can also be used.

Der UV-Absorber wird vorteilhaft aus einem wässrigen Medium auf das Substrat aufgebracht.The UV absorber is advantageously applied to the substrate from an aqueous medium.

Erfindungsgemäss kann der UV-Absorber nach allen bekannten Methoden des Färbens oder Bedruckens, wie Behandlung im langen Bad bei Temperaturen von 20 bis 140°C, Imprägnieren und Verweilen bei Raum- oder erhöhter Temperatur, beispielsweise zwischen 20 und 90°C während 30 Minuten bis 48 Stunden je nach Temperatur, Foulardieren und Fixieren durch Einwirkung von Sattdampf, überhitztem Dampf, Heissluft, Behandlung mit Hochfrequenz- oder Kontakthitze, auf dem Substrat aufgebracht und fixiert werden. Auch kann der UV-Absorber im sogenannten Thermodruck eingesetzt werden. Weiterhin kann der UV-Absorber durch Vermittlung von organischen Hochpolymeren, beispielsweise in Form von wässrigen oder nicht wässrigen Anstrichfarben oder nach der Methode des Pigmentdruckes auf dem Substrat fixiert werden.According to the invention, the UV absorber can be impregnated and held at room or elevated temperature, for example between 20 and 90 ° C. for 30 minutes to all known methods of dyeing or printing, such as treatment in a long bath at temperatures from 20 to 140 ° C. 48 hours depending on the temperature, padding and fixing by the action of saturated steam, superheated steam, hot air, treatment with high-frequency or contact heat, are applied and fixed on the substrate. The UV absorber can also be used in so-called thermal printing. Furthermore, the UV absorber can be fixed on the substrate by mediating organic high polymers, for example in the form of aqueous or non-aqueous paints, or using the pigment printing method.

Die Wahl der Applikations- und Fixiermethode und die Menge des UV-Absorbers richten sich nach dem Substrat, den verwendeten Farbstoffen, den optischen Aufhellern und deren Echtheiten und den Eigenschaften der verwendeten UV-Absorber. Im allgemeinen werden gute Löscheffekte erhalten wenn der UV-Absorber in einer Menge von 0,1 bis 5 % von Warengewicht eingesetzt wird.The choice of application and fixing method and the amount of UV absorber depend on the substrate, the dyes used, the optical brighteners and their fastness and the properties of the UV absorbers used. In general, good extinguishing effects are obtained when the UV absorber is used in an amount of 0.1 to 5% of the weight of the goods.

Wie schon erwähnt, wird der UV-Absorber erfindungsgemäss nach dem optischen Aufhellen, bzw. vor, während oder nach dem Färben oder Bedrucken eines mit einem optischen Aufheller behandelten Substrates eingesetzt. Dies ist z.B. der Fall bei Bekleidungsstücken, die nach dem Gebrauch gewaschen werden. Handelsübliche Waschmittel oder Seifen für den Haushalt enthalten heute meistens optische Aufheller, um die damit gewaschene Wäsche weisser erscheinen zu lassen. Werden nun mit einem solchen Waschmittel hellfarbig gefärbte bzw. bedruckte Textilien gewaschen, so ergibt sich nach dem Trocknen ein anderer Farbton als vorher. Dies wird besonders bei hellen Farbtönen wie bleu, rosé, beige usw. beanstandet.As already mentioned, the UV absorber is used according to the invention after the optical brightening, or before, during or after the dyeing or printing of a substrate treated with an optical brightener. This is the case, for example, with items of clothing that are washed after use will. Commercial detergents or soaps for the household today mostly contain optical brighteners to make the laundry washed with them appear whiter. If textiles dyed or printed in light colors are washed with such a detergent, a different color tone results after drying than before. This is particularly objectionable for light colors such as bleu, rosé, beige etc.

Je nach angewandten Verfahren werden die optischen Aufhellungseffekte örtlich oder auf der ganzen Fläche gelöscht oder unterdrückt. Diese optischen Aufhellungseffekte sind durch handelsübliche optische Aufheller erzeugt, beispielsweise bekannte anionische oder kationische optische Aufheller sowie Disperisonsaufheller wie sie in Waschmitteln, eingesetzt werden. Als Beispiele von solchen Aufhellern seien Derivate der Bis-(triazinylamino)-stilbendisulfonsäure, Triazolyl-Derivate von Stilbensulfonsäuren, Bis(stilben)-Verbindungen, Pyrazolin-, Cumarin-, Bis(benzimidazolyl)-, Bis(oxazolyl)-, Naphthalimid-, Cyanin-, Benzoxazolyl- und Oxacyanin-Derivate genannt.Depending on the process used, the optical brightening effects are deleted or suppressed locally or over the entire surface. These optical brightening effects are produced by commercially available optical brighteners, for example known anionic or cationic optical brighteners and dispersion brighteners as are used in detergents. Examples of such brighteners are derivatives of bis (triazinylamino) stilbene disulfonic acid, triazolyl derivatives of stilbene sulfonic acids, bis (stilbene) compounds, pyrazoline, coumarin, bis (benzimidazolyl), bis (oxazolyl), naphthalimide, Cyanine, benzoxazolyl and oxacyanine derivatives called.

Unter Substraten werden aus natürlichen oder synthetischen Polyamiden bestehende textile Materialien und unter letzteren z.B. Garne, Gewebe, Gewirke oder Vliesse verstanden. Die textilen Materialien können auch aus Mischungen von Polyamiden mit anderen Fasern bestehen.Textile materials consisting of natural or synthetic polyamides are used as substrates and e.g. Yarns, fabrics, knitted fabrics or fleece understood. The textile materials can also consist of mixtures of polyamides with other fibers.

Claims (7)

  1. A process for quenching or suppressing the fluorescence of natural or synthetic polyamide substrates treated with fluorescent whitening agents by means of UV absorbers, which process comprises applying to said substrates a sulfonated UV absorber of formula
    Figure imgb0009
     in which
    R₁   is hydrogen, halogen, C₁-C₁₂alkyl, C₅-C₆cycloalkyl, C₇-C₉phenylalkyl or sulfo,
    R₂   is hydrogen, C₁-C₄alkyl, C₁-C₄alkoxy, halogen, hydroxyl or sulfo,
    R₃   is hydrogen, C₁-C₁₂alkyl, C₁-C₄alkoxy, phenyl, (C₁-C₈alkyl)phenyl, C₅-C₆cycloalkyl, C₂-C₉alkoxycarbonyl, halogen, carboxy-C₁-C₄alkyl, C₇-C₉phenylalkyl or sulfo, and
    X   is a radical of formula
    Figure imgb0010
     in which
    R₄   is hydrogen, halogen, C₁-C₄alkyl, C₁-C₄alkoxy, C₂-C₉alkoxycarbonyl, carboxyl or sulfo,
    R₅   is hydrogen or halogen and
    R₆ and R₇   are each independently of the other C₁-C₄alkyl, C₁-C₄alkoxy, C₅-C₆cycloalkyl, phenyl or phenyl which is substituted by C₁-C₄alkyl and hydroxyl,
    and fixing said UV absorber thereon.
  2. A process according to claim 1, which comprises applying a 2-phenylbenzenetriazole, or a salt thereof, of formula
    Figure imgb0011
     as UV absorber, in which
    R₁   is hydrogen, C₁-C₁₂alkyl, chlorine, C₅-C₆cycloalkyl, C₇-C₉phenylalkyl or sulfo,
    R₂   is hydrogen, C₁-C₄alkyl, C₁-C₄alkoxy, chlorine, hydroxyl or sulfo,
    R₃   is C₁-C₁₂alkyl, C₁-C₄alkoxy, phenyl, (C₁-C₈alkyl)phenyl, C₅-C₆cycloalkyl, C₂-C₉alkoxycarbonyl, chlorine, carboxyethyl or C₇-C₉phenylalkyl or sulfo,
    R₄   is hydrogen, chlorine, C₁-C₄alkyl, C₁-C₄alkoxy, C₂-C₉alkoxycarbonyl, carboxyl or sulfo, and
    R₅   is hydrogen or chlorine.
  3. A process according to claim 2, which comprises applying the sodium salt of 3-(2'H-benzotriazol-2'-yl)-5-tert-butyl-4-hydroxybenzenesulfonic acid, 3-(2'H-5'-chlorobenzotriazol-2'-yl)-5-tert-butyl-4-hydroxybenzenesulfonic acid or 3-(2'H-benzotriazol-2'-yl)-5-sec-butyl-4-hydroxybenzenesulfonic acid.
  4. A process according to claim 1, which comprises applying a 2-phenyl-s-triazine, or a salt thereof, of formula
    Figure imgb0012
     as UV absorber, in which
    R₁   is hydrogen, halogen, C₁-C₄alkyl or sulfo,
    R₂   is hydrogen, C₁-C₄alkyl, C₁-C₄alkoxy or hydroxyl,
    R₃   is hydrogen or sulfo, and
    R₆ and R₇   are each independently of the other C₁-C₄alkyl, C₁-C₄alkoxy, C₅-C₆cycloalkyl, phenyl or phenyl which is substituted by C₁-C₄alkyl or hydroxyl.
  5. A process according to claim 4, which comprises applying the sodium salt of 3-(4',6'-diphenyl-s-triazin-2'-yl)-4-hydroxy-6-methoxybenzenesulfonic acid, 3-(4',6'-diphenyl-s-triazin-2'-yl)-4-hydroxy-6-ethoxybenzenesulfonic acid or 3-(4',6'-diphenyl-s-triazin-2'-yl)-4-hydroxy-6-propoxybenzenesulfonic acid.
  6. A process according to claim 1, wherein the UV absorber is applied to the substrate before, during or after dyeing or printing said substrate.
  7. The material treated by the process according to claim 1.
EP88116113A 1987-10-02 1988-09-29 Process for quenching or suppressing the fluorescence of optically brightened substrates Expired - Lifetime EP0310083B1 (en)

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CH385687 1987-10-02

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