EP0240461B1 - Mixtures of optical brighteners - Google Patents

Mixtures of optical brighteners Download PDF

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Publication number
EP0240461B1
EP0240461B1 EP87810176A EP87810176A EP0240461B1 EP 0240461 B1 EP0240461 B1 EP 0240461B1 EP 87810176 A EP87810176 A EP 87810176A EP 87810176 A EP87810176 A EP 87810176A EP 0240461 B1 EP0240461 B1 EP 0240461B1
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Prior art keywords
formula
compound
weight
parts
mixture according
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EP87810176A
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German (de)
French (fr)
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EP0240461A1 (en
Inventor
Heinz Dr. Hefti
Klaus Dr. Artz
Kurt Dr. Weber
Kurt Dr. Burdeska
Dieter Dr. Reinehr
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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
    • 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
    • D06L4/65—Optical bleaching or brightening with mixtures of optical brighteners

Definitions

  • Optical brighteners are often used as mixtures of two or more different types, because such mixtures show a synergistic effect in that the degree of whiteness of the mixture is higher than the degree of whiteness of the same amount of the individual components.
  • the invention therefore relates to mixtures of optical brighteners composed of 1 to 99 parts by weight of a compound of the formula 1 wherein R1 and R2 are the same or different and are -CN, -COOCH3 or -COOC2H5, and 99 to 1 part by weight of one or more compounds of the formulas 2 to 10
  • the mixtures preferably consist of 25 to 75 parts by weight of a compound of the formula 1 and 75 to 25 parts by weight of one or more of the compounds of the formulas 2 to 9, in particular the compounds of the formulas 3, 4 and 8, the preferred mixing ratio to the compound of the formula 8 20 to 50 to 80 to 50, while the preferred mixing ratio of a compound of formula 1 with a compound of formula 10 is 5 to 15 to 95 to 85, especially about 10 to 90 parts by weight.
  • R1 and R2 are preferably the same and are especially -CN or also -COOC2H5.
  • Preferred compounds of formula 10 are: 1,4-bis (2-cyanstyryl) benzene 1- (2-cyanstyryl) -4- (4-cyanstyryl) benzene 1- (2-cyanstyryl) -4- (3-cyanstyryl) benzene and 1- (3-cyanstyryl) -4- (4-cyanstyryl) benzene.
  • the compounds of the formulas 2 to 10 can also be used individually in any mixture with one another together with a compound of the formula 1 as optical brighteners, the mixing ratio of the compounds of the formulas 2 to 10 to one another being uncritical and being able to be varied depending on experience.
  • the mixtures according to the invention are obtained either by jointly dispersing compounds of the formula 1 with one or more compounds of the formulas 2 to 10 in the stated mixing ratio or else by separate dispersing of the components and mechanical mixing.
  • the optimal mixing ratio depends on the type of connection and can be easily determined by simple tests.
  • the present invention further relates to the use of mixtures of a compound of the formula 1 with one or more compounds of the formulas 2 to 10 for the optical brightening of polyester fibers and textile material containing polyester fibers, and agents for the optical brightening of polyester fibers and Textile materials containing polyester fibers, containing mixtures of a compound of formula 1 with one or more of the compounds of formulas 2 to 10.
  • the mixtures according to the invention are particularly suitable for optically brightening textile materials made of linear or modified polyesters. They can be applied to the textile material by known methods, for example by the exhaust process at 90 to 140 ° C or by the pad thermal process at 160 to 220 ° C.
  • the mixtures according to the invention are distinguished by very good dyeing behavior. In addition to a higher degree of whiteness compared to the corresponding proportions of the individual components, the mixtures have an improved brilliance of the brightenings.
  • a polyester fabric (Terylene type 540) is at 40 ° C on a dyeing machine at a liquor ratio of 1 to 20 with an aqueous bath containing 0.1% by weight of an optical brightener from a mixture of 25 parts by weight of the compound of the formula and 75 parts by weight of the compound of the formula as well as 1 g / l of a fatty alcohol polyglycol ether (Irgasol P) treated.
  • the temperature is increased to 120 ° C. within 30 minutes and left at this level for a further 30 minutes. Then you cool down to 40 ° C within 15 minutes.
  • the fabric is rinsed in flowing deionized water for 30 seconds and dried at 80 ° C.
  • the polyester fabric treated in this way has a high lightening effect.
  • a polyester fabric (Terylene type 540) is padded at room temperature with an aqueous liquor containing 1 g / l of the brightener mixture of 50 parts by weight of the compound of the formula 1 and 50 parts by weight of the compound of the formula 4 (calculated on active substance) in dispersed form and 1 ml / l Invadin JFC 200%.
  • the squeezing effect is 65%.
  • polyester fabric treated in this way has a high lightening effect.

Description

Optische Aufheller werden oft als Mischungen von zwei oder mehreren verschiedenen Typen verwendet, weil solche Mischungen einen synergistischen Effekt zeigen, indem der Weissgrad der Mischung höher ist als der Weissgrad dergleichen Menge der jeweiligen Einzelkomponenten.Optical brighteners are often used as mixtures of two or more different types, because such mixtures show a synergistic effect in that the degree of whiteness of the mixture is higher than the degree of whiteness of the same amount of the individual components.

4,4ʹ-Bis-(vinyl)-stilbenverbindungen sind bereits aus der DE-A 26 02 750 also optische Aufheller bekannt.4,4'-bis (vinyl) stilbene compounds are already known from DE-A 26 02 750, ie optical brighteners.

Es wurde nun gefunden, dass man eine deutliche Erhöhung des Weissgrades erhält, wenn man die 4,4ʹ-Bis-(vinyl)-stilbenverbindungen mit einem anderen bekannten Aufheller der unten angegebenen Struktur mischt.It has now been found that a significant increase in the degree of whiteness is obtained if the 4,4′-bis (vinyl) stilbene compounds are mixed with another known brightener of the structure given below.

Gegenstand der Erfindung sind daher Mischungen von optischen Aufhellern aus 1 bis 99 Gewichtsteilen einer Verbindung der Formel 1

Figure imgb0001
worin R₁ und R₂ gleich oder verschieden sind und -CN, -COOCH₃ oder -COOC₂H₅ bedeuten, und 99 bis 1 Gewichtsteilen einer oder mehrerer Verbindungen der Formeln 2 bis 10
Figure imgb0002
 Vorzugsweise bestehen die Mischungen aus 25 bis 75 Gewichtsteilen einer Verbindung der Formel 1 und 75 bis 25 Gewichtsteilen einer oder mehrerer der Verbindungen der Formeln 2 bis 9, insbesondere der Verbindungen der Formeln 3, 4 und 8, wobei das bevorzugte Mischungsverhältnis zur Verbindung der Formel 8 20 bis 50 zu 80 bis 50 beträgt, während das bevorzugte Mischungsverhältnis einer Verbindung der Formel 1 mit einer Verbindung der Formel 10 bei 5 bis 15 zu 95 bis 85, insbesondere bei etwa 10 zu 90 Gewichtsteilen liegt. R₁ und R₂ sind vorzugsweise gleich und bedeuten vor allem -CN oder auch -COOC₂H₅. Bevorzugte Verbindungen der Formel 10 sind:
1,4-Bis-(2-cyanstyryl)-benzol
1-(2-Cyanstyryl)-4-(4-cyanstyryl)-benzol
1-(2-Cyanstyryl)-4-(3-cyanstyryl)-benzol und
1-(3-Cyanstyryl)-4-(4-cyanstyryl)-benzol.The invention therefore relates to mixtures of optical brighteners composed of 1 to 99 parts by weight of a compound of the formula 1
Figure imgb0001
 wherein R₁ and R₂ are the same or different and are -CN, -COOCH₃ or -COOC₂H₅, and 99 to 1 part by weight of one or more compounds of the formulas 2 to 10
Figure imgb0002
 The mixtures preferably consist of 25 to 75 parts by weight of a compound of the formula 1 and 75 to 25 parts by weight of one or more of the compounds of the formulas 2 to 9, in particular the compounds of the formulas 3, 4 and 8, the preferred mixing ratio to the compound of the formula 8 20 to 50 to 80 to 50, while the preferred mixing ratio of a compound of formula 1 with a compound of formula 10 is 5 to 15 to 95 to 85, especially about 10 to 90 parts by weight. R₁ and R₂ are preferably the same and are especially -CN or also -COOC₂H₅. Preferred compounds of formula 10 are:
1,4-bis (2-cyanstyryl) benzene
1- (2-cyanstyryl) -4- (4-cyanstyryl) benzene
1- (2-cyanstyryl) -4- (3-cyanstyryl) benzene and
1- (3-cyanstyryl) -4- (4-cyanstyryl) benzene.

Die Verbindungen der Formeln 2 bis 10 können ausser einzeln auch in beliebiger Mischung untereinander zusammen mit einer Verbindung der Formel 1 als optische Aufheller verwendet werden, wobei das Mischungsverhältnis der Verbindungen der Formeln 2 bis 10 zueinander unkritisch ist und je nach Erfahrung variiert werden kann.The compounds of the formulas 2 to 10 can also be used individually in any mixture with one another together with a compound of the formula 1 as optical brighteners, the mixing ratio of the compounds of the formulas 2 to 10 to one another being uncritical and being able to be varied depending on experience.

Die erfindungsgemässen Mischungen erhält man entweder durch gemeinsames Dispergieren von Verbindungen der Formel 1 mit einer oder mehreren Verbindungen der Formeln 2 bis 10 im angegebenen Mischungsverhältnis oder aber durch getrenntes Dispergieren der Komponenten und mechanisches Mischen. Das optimale Mischungsverhältnis hängt jeweils von der Art der Verbindungen ab und lässt sich leicht durch einfache Tests ermitteln.The mixtures according to the invention are obtained either by jointly dispersing compounds of the formula 1 with one or more compounds of the formulas 2 to 10 in the stated mixing ratio or else by separate dispersing of the components and mechanical mixing. The optimal mixing ratio depends on the type of connection and can be easily determined by simple tests.

Weitere Gegenstände der vorliegenden Erfindung sind die Verwendung von Mischungen aus einer Verbindung der Formel 1 mit einer oder mehreren Verbindungen der Formeln 2 bis 10 zum optischen Aufhellen von Polyesterfasern und Polyesterfasern enthaltendem Textilmaterial sowie Mittel zum optischen Aufhellen von Polyesterfasern und Polyesterfasern enthaltenden Textilmaterialen, enthaltend Mischungen einer Verbindung der Formel 1 mit einer oder mehreren der Verbindungen der Formeln 2 bis 10.The present invention further relates to the use of mixtures of a compound of the formula 1 with one or more compounds of the formulas 2 to 10 for the optical brightening of polyester fibers and textile material containing polyester fibers, and agents for the optical brightening of polyester fibers and Textile materials containing polyester fibers, containing mixtures of a compound of formula 1 with one or more of the compounds of formulas 2 to 10.

Die erfindungsgemässen Mischungen eignen sich besonders zum optischen Aufhellen von Textilmaterialien aus linearen oder modifizierten Polyestern. Sie können nach bekannten Methoden auf das Textilgut appliziert werden, beispielsweise nach dem Ausziehverfahren bei 90 bis 140°C oder nach dem Foulardthermverfahren bei 160 bis 220°C.The mixtures according to the invention are particularly suitable for optically brightening textile materials made of linear or modified polyesters. They can be applied to the textile material by known methods, for example by the exhaust process at 90 to 140 ° C or by the pad thermal process at 160 to 220 ° C.

Die erfindungsgemässen Mischungen zeichnen sich durch sehr gutes färberisches Verhalten aus. Ausser durch einen höheren Weissgrad gegenüber den entsprechenden Anteilen der jeweiligen Einzelkomponenten weisen die Mischungen eine verbesserte Brillanz der Aufhellungen auf.The mixtures according to the invention are distinguished by very good dyeing behavior. In addition to a higher degree of whiteness compared to the corresponding proportions of the individual components, the mixtures have an improved brilliance of the brightenings.

Beispiel 1example 1

Ein Polyestergewebe (Terylene Typ 540) wird bei 40°C auf einem Färbeapparat bei einem Flottenverhältnis von 1 zu 20 mit einem wässrigen Bad, enthaltend 0.1 Gew.-% eines optischen Aufhellers aus einer Mischung von 25 Gewichtsteilen der Verbindung der Formel

Figure imgb0003
und 75 Gewichtsteilen der Verbindung der Formel
Figure imgb0004
 sowie 1 g/l eines Fettalkoholpolyglykoläthers (Irgasol P), behandelt. Innerhalb von 30 Minuten steigert man die Temperatur auf 120°C und belässt sie während weiterer 30 Minuten auf dieser Höhe. Dann kühlt man innerhalb von 15 Minuten wieder auf 40°C ab. Zur Nachbehandlung wird das Textilgut während 30 Sekunden in fliessendem deionisiertem Wasser gespült und bei 80°C getrocknet. Das derart behandelte Polyestergewebe weist einen hohen Aufhelleffekt auf.A polyester fabric (Terylene type 540) is at 40 ° C on a dyeing machine at a liquor ratio of 1 to 20 with an aqueous bath containing 0.1% by weight of an optical brightener from a mixture of 25 parts by weight of the compound of the formula
Figure imgb0003
 and 75 parts by weight of the compound of the formula
Figure imgb0004
 as well as 1 g / l of a fatty alcohol polyglycol ether (Irgasol P) treated. The temperature is increased to 120 ° C. within 30 minutes and left at this level for a further 30 minutes. Then you cool down to 40 ° C within 15 minutes. For post-treatment the fabric is rinsed in flowing deionized water for 30 seconds and dried at 80 ° C. The polyester fabric treated in this way has a high lightening effect.

Beispiel 2Example 2

Verwendet man nach der gleichen Vorschrift wie in Beispiel 1 anstelle des Aufhellers aus der Mischung der Verbindungen der Formeln (1) und (4) jeweils solche aus den Mischungen

  • a) von 25 Gewichtsteilen der Verbindung der Formel (1) und 75 Gewichtsteilen der Formel (2)
  • b) von 30 Gewichtsteilen der Verbindung der Formel (1) und 70 Gewichtsteilen der Formel (3)
  • c) von 70 Gewichtsteilen der Verbindung der Formel (1) und 30 Gewichtsteilen der Formel (6)
  • d) von 35 Gewichtsteilen der Verbindung der Formel (1) und 65 Gewichtsteilen der Verbindung der Formel (8)
  • e) von 10 Gewichtsteilen der Verbindung der Formel (1) und 90 Gewichtsteilen der Formel (10)

so erhält man ähnlich gute Aufhelleffekte.If, according to the same procedure as in Example 1, instead of the brightener from the mixture of the compounds of the formulas (1) and (4), those from the mixtures are used
  • a) 25 parts by weight of the compound of the formula (1) and 75 parts by weight of the formula (2)
  • b) from 30 parts by weight of the compound of the formula (1) and 70 parts by weight of the formula (3)
  • c) 70 parts by weight of the compound of the formula (1) and 30 parts by weight of the formula (6)
  • d) 35 parts by weight of the compound of the formula (1) and 65 parts by weight of the compound of the formula (8)
  • e) from 10 parts by weight of the compound of the formula (1) and 90 parts by weight of the formula (10)

you get similarly good lightening effects.

Beispiel 3Example 3

Man foulardiert bei Raumtemperatur ein Polyestergewebe (Terylene Typ 540) mit einer wässrigen Flotte enthaltend 1 g/l der Aufhellermischung aus 50 Gewichtsteilen der Verbindung der Formel 1 und 50 Gewichtsteilen der Verbindung der Formel 4 (berechnet auf Aktivsubstanz) in dispergierter Form und 1 ml/l Invadin JFC 200 %. Der Abquetscheffekt beträgt 65 %.A polyester fabric (Terylene type 540) is padded at room temperature with an aqueous liquor containing 1 g / l of the brightener mixture of 50 parts by weight of the compound of the formula 1 and 50 parts by weight of the compound of the formula 4 (calculated on active substance) in dispersed form and 1 ml / l Invadin JFC 200%. The squeezing effect is 65%.

Anschliessend wird während 30 Minuten bei einer Temperatur von 80°C getrocknet und daraufhin bei 200°C thermofixiert. Das so behandelte Polyestergewebe weist einen hohen Aufhelleffekt auf.It is then dried for 30 minutes at a temperature of 80 ° C and then heat set at 200 ° C. The polyester fabric treated in this way has a high lightening effect.

Beispiel 4:Example 4:

Verwendet man nach der gleichen Vorschrift wie in Beispiel 3 eine Aufhellermischung aus 75 Gewichtsteilen der Verbindung der Formel 1 und 25 Gewichtsteilen der Verbindung der Formel 4 so erhält man ähnlich gute Aufhelleffekte.If a brightener mixture of 75 parts by weight of the compound of the formula 1 and 25 parts by weight of the compound of the formula 4 is used in accordance with the same procedure as in Example 3, similarly good lightening effects are obtained.

Beispiel 5Example 5

Verwendet man nach der gleichen Vorschrift wie in Beispiel 3 eine Aufhellermischung aus 75 Gewichtsteilen der Verbindung der Formel 1 und 25 Gewichtsteilen der Verbindung der Formel 3 so erhält man ähnlich gute Aufhelleffekte.If a brightener mixture of 75 parts by weight of the compound of the formula 1 and 25 parts by weight of the compound of the formula 3 is used according to the same procedure as in Example 3, similarly good lightening effects are obtained.

Claims (14)

  1. A mixture of fluorescent whitening agents consisting of 1 to 99 parts by weight of a compound of formula 1
    Figure imgb0008
     in which R₁ and R₂ are the same or different and are -CN, -COOCH₃ or -COOC₂H₅, and 99 to 1 parts by weight of one or more compounds of formulae 2 to 10
    Figure imgb0009
    Figure imgb0010
  2. A mixture according to claim 1, which consists of 25 to 75 parts by weight of a compound of formula 1 and 75 to 25 parts by weight of one or more compounds of formulae 2 to 9.
  3. A mixture according to claim 2, which consists of a compound of formula 1 and the compound of formula 3.
  4. A mixture according to claim 2, which consists of a compound of formula 1 and the compound of formula 4.
  5. A mixture according to claim 1, which consists of 20 to 50 parts by weight of a compound of formula 1 and 80 to 50 parts by weight of the compound of formula 8.
  6. A mixture according to claim 1, which consists of 5 to 15 parts by weight of a compound of formula 1 and 95 to 85 parts by weight of a compound of formula 10.
  7. A mixture according to claim 1, wherein R₁ and R₂ in the compound of formula 1 are identical.
  8. A mixture according to claim 7, wherein R₁ and R₂ are -CN.
  9. A mixture according to claim 6, wherein the compound of formula 10 is 1,4-bis(2-cyanostyryl)benzene.
  10. A mixture according to claim 6, wherein the compound of formula 10 is 1-(2-cyanostyryl)-4-(4-cyanostyryl)benzene.
  11. A mixture according to claim 6, wherein the compound of formula 10 is 1-(2-cyanostyryl)-4-(3-cyanostyryl)benzene.
  12. A mixture according to claim 6, wherein the compound of formula 10 is 1-(3-cyanostyryl)-4-(4-cyanostyryl)benzene.
  13. Use of a mixture of a compound of formula 1 with one or more compounds of formulae 2 to 10 according to claim 1 for whitening polyester fibres and textile material containing polyester fibres.
  14. A composition for whitening polyester fibres and textile material containing polyester fibres, which composition contains a mixture according to claim 1 of a compound of formula 1 and one or more compounds of formulae 2 to 10.
EP87810176A 1986-04-02 1987-03-27 Mixtures of optical brighteners Expired - Lifetime EP0240461B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH128486 1986-04-02
CH1284/86 1986-04-02

Publications (2)

Publication Number Publication Date
EP0240461A1 EP0240461A1 (en) 1987-10-07
EP0240461B1 true EP0240461B1 (en) 1991-04-17

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EP87810176A Expired - Lifetime EP0240461B1 (en) 1986-04-02 1987-03-27 Mixtures of optical brighteners

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EP (1) EP0240461B1 (en)
JP (1) JPS62236865A (en)
BR (1) BR8701478A (en)
DE (1) DE3769352D1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0682145A2 (en) * 1994-05-12 1995-11-15 Ciba-Geigy Ag Textile treatment
US6117189A (en) * 1994-05-12 2000-09-12 Ciba Specialty Chemicals Corporation Protective method

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU5845890A (en) * 1989-06-22 1991-01-08 Fmc Corporation Thickened and gelled systems based on starch and glucomannan
DE10219993A1 (en) * 2002-05-03 2003-11-20 Basf Ag Process for lightening textile materials
DE10245705A1 (en) 2002-09-30 2004-04-01 Bayer Ag A polycarbonate or polyester carbonate containing optical brighteners
US7497971B2 (en) 2002-12-10 2009-03-03 Ciba Specialty Chemicals Corporation Mixtures of fluorescent whitening agents

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH603513A5 (en) * 1975-02-05 1978-08-15 Sandoz Ag
US4666627A (en) * 1983-05-08 1987-05-19 Ciba-Geigy Corporation 4-Heterocyclylvinyl-4-'styryl-biphenyls

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0682145A2 (en) * 1994-05-12 1995-11-15 Ciba-Geigy Ag Textile treatment
EP0682145A3 (en) * 1994-05-12 1998-08-26 Ciba SC Holding AG Textile treatment
US6117189A (en) * 1994-05-12 2000-09-12 Ciba Specialty Chemicals Corporation Protective method

Also Published As

Publication number Publication date
DE3769352D1 (en) 1991-05-23
JPS62236865A (en) 1987-10-16
BR8701478A (en) 1988-01-19
EP0240461A1 (en) 1987-10-07

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