EP1624105B1 - Agent blanchissant à base de dérivés flavonates triazinylés contenant des ammoniums-alkanols - Google Patents

Agent blanchissant à base de dérivés flavonates triazinylés contenant des ammoniums-alkanols Download PDF

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Publication number
EP1624105B1
EP1624105B1 EP05016038A EP05016038A EP1624105B1 EP 1624105 B1 EP1624105 B1 EP 1624105B1 EP 05016038 A EP05016038 A EP 05016038A EP 05016038 A EP05016038 A EP 05016038A EP 1624105 B1 EP1624105 B1 EP 1624105B1
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Prior art keywords
formula
alkyl
brightener
weight
size press
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EP05016038A
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German (de)
English (en)
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EP1624105A1 (fr
Inventor
Heinz Dr. Giesecke
Bernhard Hunke
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Kemira Oyj
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Kemira Agro Oy
Kemira Oyj
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Classifications

    • 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
    • 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
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/21—Macromolecular organic compounds of natural origin; Derivatives thereof
    • D21H17/24—Polysaccharides
    • D21H17/28—Starch
    • 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
    • D21H21/16—Sizing or water-repelling agents

Definitions

  • a sizing step is generally carried out to achieve good writability and strength, which can be done on the one hand before sheet formation in the pulp (engine sizing), on the other hand after sheet formation in the size press.
  • a combination of these two methods is possible.
  • a brightening of the paper pulp or of the paper sheet is usually carried out by optical brighteners, wherein usually in the mass application, the sizing agent and the brightener of the pulp are fed separately, while incorporated in surface sizing the brightener in the size press liquor and applied together with this on the paper sheet.
  • the combination of surface sizing and whitening of papers is widely used in the paper making industry. Especially in the paper segment Printing & Writing (Copy, Inkjet, Offset, etc.) this method is widely used. In addition to the more efficient lightening, a faster correction (online measurement) of the whiteness levels to be achieved is also possible. Furthermore, with the surface application, the wet end of additional anionic freights (whiteners) spared.
  • Triazinylflavonataufheller are already described as K or Na salts as optical brighteners in the size press method for lightening paper. However, these still have some application disadvantages, in particular in the whiteness.
  • brighteners containing more than 50% by weight, preferably more than 60% by weight, preferably more than 75% by weight, in particular more than 95% by weight, of a brightener Formula I exist.
  • the brightener of the formula (I) may additionally be present in excess alkanolamine or alkanolammonium in the form of the free bases or corresponding salts with other, inorganic or organic, anions in the size press liquor.
  • the brighteners are already prepared and / or formulated in the form of their alkanolammonium salts or mixed salts of their alkanolammonium salts with their salts of inorganic bases and are finally incorporated into size press liquors in such a form which are then applied in the described preferred pH range.
  • the use can, however, e.g. also be effected by reacting with an inorganic counterion, e.g.
  • Lithium, sodium, potassium, calcium, magnesium, or ammonium whitening agent is contacted with the salt of an inorganic or organic acid of an alkanolamine, for example, an alkanolamine hydrochloride or alkanolamine sulfate, and this mixture is then applied in a size press liquor of suitable pH, or e.g. in that this matching only happens in the size press fleet, or z.
  • an alkanolamine underlying the alkanolamine is introduced in free form at any time and at any point in the manufacturing or processing and neutralized in the course with a suitable inorganic or organic acid. This of course also applies to the opposite case, namely that first the inorganic or organic acid and only then the alkanolamine is introduced.
  • the use according to the invention is preferably carried out by introducing into the size press liquor an aqueous solution of the brightener of suitable pH, which may possibly contain additional substances, such as carrier substances, salts or setting agents.
  • carrier-free or carrier-containing formulations in smaller amounts, usually in amounts below 5 wt .-%, other auxiliaries such.
  • other auxiliaries such as dispersants, thickeners, antifreeze, preservatives, complexing agents, etc., or organic by-products from the brightener synthesis, which were not completely removed in the workup, may be included.
  • the brightener with only inorganic cations shows a saturation behavior with respect to the CIE from certain brightener addition amounts.
  • Whiteness ie larger amounts do not lead to whiteness build-up any more and can even have a negative effect on the whiteness.
  • This saturation behavior occurs when using the alkanolammonium brightener only at much higher levels, compared to the salt with only inorganic cations, on.
  • the effect of saturation is also called greening.
  • the greening border i. the point above which increasing brightener amounts cause virtually no increase in whiteness can e.g. are derived from the a * -b * diagram, where a * and b * are the color coordinates in the CIE-L * a * b * system.
  • Aqueous whitener preparations are usually characterized by the so-called E1 / 1 value.
  • E1 / 1 value the extinction of a highly diluted solution of the preparation is determined by the usual and known to the expert methods of UV / Vis spectroscopy in a 1 cm cuvette at a specific wavelength. This wavelength corresponds to the long-wavelength absorption maximum of the respective brightener molecule. For flavonate brighteners it is about 350 nm.
  • the E1 / 1 value then corresponds to the imaginary extinction value extrapolated to a 1% solution of the sample to be determined.
  • the preparations according to the invention can preferably be used in the lightening process according to the invention.
  • aqueous whitener preparations comprising at least one brightener of the formula (I), in particular (Ia).
  • the size press liquor may contain inorganic or organic salts, in addition free alkanolamine, in addition alkanolamine salts, carriers and other substances.
  • the proportion of surface sizing agent, in particular starch, based on the size press liquor is preferably from 2 to 25% by weight, in particular from 5 to 15% by weight.
  • the water content of the size press liquor is preferably at least 70% by weight.
  • Comparative Examples 2a, b corresponds to Comparative Example 1 with the difference that in addition different amounts of free triethanolamine are present
  • 229 g of the membrane-filtered aqueous concentrate from Comparative Example 1 are mixed with stirring at room temperature with a) 15.0 b) 30.0 and a) 56 gb) 41 g demineralized water and then stirred for 10 min.
  • Triethanolamine-containing brightener preparations having an E1 / 1 value of 113 in the form of yellow-brownish homogeneous liquids are obtained. This corresponds to a content of brightener of about 21% and a content of triethanolamine of a) 5% b) 10%.
  • Comparative Example 3 corresponds to Example 2 WO 00 46336 .
  • the procedure is up to and including the introduction of the crystals as described for Example 1b. After dissolution of the crystals, 15 g of polyethylene glycol 1500 are added, the mixture is stirred until dissolved and determines the E1 / 1 value. The mixture is then diluted at room temperature with demineralized water to a calculated E1 / 1 value of 113.
  • the test of the individual brightener preparations is then carried out by diluting the respective preparation as a concentration series to a further 50.0 g of the same starch solution, diluted to 100.0 g with water, thoroughly mixed, and the resulting brightener-containing size press liquors as described above Help the Apply the laboratory size press to further test paper sheets. Finally, the papers so finished in the drying cylinder at about 100 ° C dried.
  • the above concentration series refers to preparations with an E1 / 1 value of 113. If preparations with a deviating E1 / 1 value are to be tested, their E1 / 1 value deviation from the guide value 113 must additionally be compensated for by: changing the concentration series in inverse proportion (for example, at an E1 / 1 value of 105, 0.538 wt% preparation is equivalent to 0.5% preparation of E1 / 1 value 113, etc.).
  • Table 1 Brightener preparation from Comparative Example 1 Amount (%) CIE whiteness L * a * b * 0.50 138.08 95.95 2.96 -10.83 1.00 144.11 96.12 3.04 -12.13 1.50 145.80 96.28 2.87 -12.44 2.00 146.46 96.32 2.69 -12.57
  • Table 4 Brightener preparation from Example la Amount (%) CIE whiteness L * a * b * 0.50 138.12 96.05 2.95 -10.80 1.00 145.36 96.31 3.09 -12.33 1.50 146.98 96.34 2.96 -12.68 2.00 148.48 96.57 2.79 -12.92
  • Table 5 Brightener preparation from Example 1b Amount (%) CIE whiteness L * a * b * 0.50 138.33 95.96 2.98 -10.88 1.00 145.58 96.26 3.12 -12.40 1.50 147.59 96.25 3.03 -12
  • Table 5 Brightener preparation from Example 1b Amount (%) CIE whiteness L * a * b * 0.50 138.33 95.96 2.98 -10.88 1.00 145.58 96.26 3.12 -12.40 1.50 147.59 96.25 3.03 -12.86 2.00 148.26 96.46 2.80 -12.92
  • Table 6 Brightener preparation from Example 2 Amount (%) CIE whiteness L * a * b * 0.50 138.69 95.96 3.02 -10.97 1.00 145.83 96.23 3.16 -12.47 1.50 148.12 96.41 3.08 -12.92 2.00 148.74 96,39 2.86 -13.06

Landscapes

  • Paper (AREA)
  • Detergent Compositions (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Cosmetics (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Claims (6)

  1. Procédé d'azurage du papier dans la presse à encoller, caractérisé en ce qu'on utilise dans l'étape d'encollage un bain de presse encolleuse contenant un azurant de formule I
    Figure imgb0027
     dans laquelle
    les radicaux X représentent chacun indépendamment de l'autre un radical de formule
    Figure imgb0028
     ou
    Figure imgb0029
     et
    R1 est un groupe alkyle en C1-C6 et R2 est H, ou
    R1 est H et R2 est un groupe alkyle en C1-C6 et, d'une manière indépendante,
    R3 est H ou le groupe méthyle, éthyle, CH2CH2OH ou CH2CH2OCH3,
    R1' est un groupe alkyle en C1-C6 et R2' est H, ou
    R1' est H et R2' est un groupe alkyle en C1-C6 et, d'une manière indépendante,
    R3' est H ou le groupe méthyle, éthyle, CH2CH2OH ou CH2CH2OCH3, ainsi que
    R4 est un groupe alkyle en C1-C4, et
    M est H, un équivalent d'un cation inorganique, en particulier Li, Na, K, Ca, Mg ou ammonium, ou un ammonium substitué de formule II
    Figure imgb0030
     dans laquelle
    R5 à R7 représentent chacun indépendamment des autres un atome d'hydrogène, un groupe alkyle en C1-C4 ou un groupe hydroxyalkyle en C2-C4 portant éventuellement des substituants supplémentaires, et
    R8 est un groupe hydroxyalkyle en C2-C4 portant éventuellement des substituants supplémentaires,
    au moins 10 % en moles de l'ensemble des cations M correspondant à la formule II.
  2. Procédé selon la revendication 1, caractérisé en ce que le bain de presse encolleuse contient des azurants optiques qui sont constitués, pour plus de 50 % en poids, de préférence pour plus de 60 % en poids, de préférence pour plus de 75 % en poids, en particulier pour plus de 95 % en poids, d'un azurant de formule I.
  3. Procédé selon au moins l'une des revendications 1 ou 2, caractérisé en ce que R1 est H, R2 est un groupe alkyle en C1-C6 à chaîne droite, et R3 est H ;
    en outre de formule (I) dans laquelle R1' est H, R2' est un groupe alkyle en C1-C6 à chaîne droite, et R3' est H et R4 est H ou le groupe méthyle,
    où chaque M représente un mélange de cations contenant des ions alcanolammonium de formule II, le radical R5 représentant H, le radical R6 représentant H ou un groupe hydroxyalkyle en C2-C4, et les radicaux R7 et R8 représentant des groupes hydroxyalkyle en C2-C4 et des ions Na ou K.
  4. Procédé selon au moins l'une des revendications 1 à 4, caractérisé en ce qu'on utilise un azurant de formule Ia
    Figure imgb0031
     dans laquelle
    M est un mélange contenant le cation de formule II
    Figure imgb0032
     et Na+ ou K+.
  5. Préparation azurante contenant des azurants qui pour plus de 50 % en poids, de préférence pour plus de 60 % en poids, de préférence pour plus de 75 % en poids, en particulier pour plus de 95 % en poids, sont constitués d'un azurant de formule I
    Figure imgb0033
     dans laquelle
    les radicaux X représentent chacun indépendamment de l'autre un radical de formule
    Figure imgb0034
     ou
    Figure imgb0035
     et
    R1 est un groupe alkyle en C1-C6 et R2 est H, ou
    R1 est H et R2 est un groupe alkyle en C1-C6 et, d'une manière indépendante,
    R3 est H, le groupe méthyle, éthyle, CH2CH2OH ou CH2CH2OCH3,
    R1' est un groupe alkyle en C1-C6 et R2' est H, ou
    R1' est H et R2' est un groupe alkyle en C1-C6 et, d'une manière indépendante,
    R3' est H ou le groupe méthyle, éthyle, CH2CH2OH ou CH2CH2OCH3, ainsi que
    R4 est un groupe alkyle en C1-C4, et
    M est H, un équivalent d'un cation inorganique, en particulier Li, Na, K, Ca, Mg ou ammonium, ou un ammonium substitué de formule II
    Figure imgb0036
     dans laquelle
    R5 à R7 représentent chacun indépendamment des autres un atome d'hydrogène, un groupe alkyle en C1-C4 ou un groupe hydroxyalkyle en C2-C4 portant éventuellement des substituants supplémentaires, et
    R8 est un groupe hydroxyalkyle en C2-C4 portant éventuellement des substituants supplémentaires,
    au moins 10 % en moles de l'ensemble des cations M correspondant à la formule II.
  6. Bain de presse encolleuse, contenant :
    a) au moins un azurant de formule (I), en particulier (Ia), ou une préparation azurante selon la revendication 5, et
    b) au moins un agent d'encollage en surface, en particulier l'amidon.
EP05016038A 2004-08-06 2005-07-23 Agent blanchissant à base de dérivés flavonates triazinylés contenant des ammoniums-alkanols Active EP1624105B1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102004038578A DE102004038578A1 (de) 2004-08-06 2004-08-06 Alkanolammoniumhaltige Triazinylflavonataufheller

Publications (2)

Publication Number Publication Date
EP1624105A1 EP1624105A1 (fr) 2006-02-08
EP1624105B1 true EP1624105B1 (fr) 2009-03-25

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US (1) US7608168B2 (fr)
EP (1) EP1624105B1 (fr)
JP (1) JP4768349B2 (fr)
CN (1) CN1730816B (fr)
AT (1) ATE426705T1 (fr)
BR (1) BRPI0503370B1 (fr)
DE (2) DE102004038578A1 (fr)
ES (1) ES2325164T3 (fr)
PT (1) PT1624105E (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2546005A1 (fr) * 2003-11-18 2005-06-02 Ciba Specialty Chemicals Holding Inc. Pigments de blanchiment fluorescent
ATE494423T1 (de) * 2008-06-11 2011-01-15 Kemira Germany Gmbh Zusammensetzung und verfahren zur papierbleichung
EP2192230B2 (fr) † 2008-11-27 2020-01-01 Clariant Finance (BVI) Limited Compositions d'azurage optique pour impression par jet d'encre de grande qualité
CN101922124A (zh) * 2010-07-21 2010-12-22 东营市联成化工有限责任公司 一种液体增白剂的配方及生产工艺
EP2799618B1 (fr) * 2013-04-29 2016-04-27 Blankophor GmbH & Co. KG Utilisation de cellulose micronisée et agent de blanchiment fluorescent pour traitement de surface de matériaux cellulosiques

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GB896533A (en) * 1958-11-05 1962-05-16 Sandoz Ltd New stilbene derivatives and process for their manufacture
GB1211812A (en) * 1968-04-26 1970-11-11 Geigy Ag J R Asymmetrically substituted bistriazinylamino stilbene compounds
CH583212A5 (fr) * 1973-07-02 1976-12-31 Sandoz Ag
US3931422A (en) * 1974-10-04 1976-01-06 Standard Oil Company Polyester/starch paper sizing
DE3502038A1 (de) * 1985-01-23 1986-07-24 Sandoz-Patent-GmbH, 7850 Lörrach Waessrige aufhellerpraeparate und deren verwendung im papierstrich
US5478631A (en) * 1992-09-09 1995-12-26 Kanzaki Paper Mfg. Co., Ltd. Ink jet recording sheet
JP3307013B2 (ja) * 1992-09-09 2002-07-24 王子製紙株式会社 インクジェット記録用シート
GB2277749B (en) * 1993-05-08 1996-12-04 Ciba Geigy Ag Fluorescent whitening of paper
GB9412590D0 (en) * 1994-06-23 1994-08-10 Sandoz Ltd Organic compounds
JP2001518919A (ja) * 1997-03-25 2001-10-16 チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド 蛍光増白剤
US6165973A (en) * 1999-02-05 2000-12-26 Ciba Specialty Chemicals Corporation Fluorescent whitening agent, its preparation and use
BR0012946A (pt) * 1999-08-05 2002-06-11 Ciba Sc Holding Ag Uso de pigmentos embranquecedores para embranquecimento de composições de revestimento de papel
IL148105A0 (en) * 1999-09-10 2002-09-12 Ciba Specialty Holding Inc Triazinylaminostilbene derivative as fluorescent whitening agents
GB0100610D0 (en) * 2001-01-10 2001-02-21 Clariant Int Ltd Improvements in or relating to organic compounds
EP1392925A1 (fr) 2001-05-29 2004-03-03 Ciba SC Holding AG Composition de blanchiment fluorescent du papier
JP2005501981A (ja) * 2001-09-03 2005-01-20 ビーエーエスエフ アクチェンゲゼルシャフト カチオン性高分子電解質を用いて紙の白さを向上させる方法
GB0127903D0 (en) * 2001-11-21 2002-01-16 Clariant Int Ltd Improvements relating to organic compounds
DE10217677A1 (de) * 2002-04-19 2003-11-06 Bayer Ag Verwendung von Aufhellern zur Herstellung von Streichmassen

Also Published As

Publication number Publication date
ATE426705T1 (de) 2009-04-15
JP4768349B2 (ja) 2011-09-07
DE102004038578A1 (de) 2006-03-16
EP1624105A1 (fr) 2006-02-08
BRPI0503370A (pt) 2006-03-21
BRPI0503370B1 (pt) 2016-01-05
PT1624105E (pt) 2009-06-30
JP2006045761A (ja) 2006-02-16
DE502005006927D1 (de) 2009-05-07
US20060065381A1 (en) 2006-03-30
ES2325164T3 (es) 2009-08-27
CN1730816A (zh) 2006-02-08
US7608168B2 (en) 2009-10-27
CN1730816B (zh) 2011-04-13

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