EP0475905B1 - Photochemical stabilisation of wool - Google Patents

Photochemical stabilisation of wool Download PDF

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Publication number
EP0475905B1
EP0475905B1 EP91810709A EP91810709A EP0475905B1 EP 0475905 B1 EP0475905 B1 EP 0475905B1 EP 91810709 A EP91810709 A EP 91810709A EP 91810709 A EP91810709 A EP 91810709A EP 0475905 B1 EP0475905 B1 EP 0475905B1
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EP
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Prior art keywords
wool
absorber
formula
photochemical
hydrogen
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Expired - Lifetime
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EP91810709A
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German (de)
French (fr)
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EP0475905A1 (en
Inventor
Manfred Dr. Rembold
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BASF Schweiz AG
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Ciba Geigy AG
Ciba Spezialitaetenchemie Holding AG
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Classifications

    • 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
    • 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
    • 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
    • D06P1/64—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 without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6426—Heterocyclic compounds
    • 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
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/02—Material containing basic nitrogen
    • D06P3/04—Material containing basic nitrogen containing amide groups
    • D06P3/14—Wool
    • 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

Definitions

  • the present invention relates to the use of specific UV absorbers for photochemical stabilization of undyed wool or mixed fibers containing wool.
  • EP-A-0 310 083 discloses a method for quenching or suppressing fluorescence of optically brightened natural or synthetic polyamides with sulfonated UV absorbers which, in contrast to the UV absorbers used according to the invention contain one or more sulfo groups directly attached to a benzene ring.
  • US-A-3,444,164 discloses hydroxyphenyl-1,2,3-triazines which differ from those according to the invention Distinguish used hydroxyphenyl-1,2,3-triazines in that they have no hydroxyl group bonded to the alkylene group.
  • EP-A-0 417 040 describes a process for dyeing wool in the presence of a UV absorbers from the class of 2- (2'-hydroxyphenyl) -s-triazines known.
  • synthetic polyamide fibers can be made using Light stabilizers which contain compounds from the class of the sterically hindered amines, can stabilize photochemically.
  • EP-A-0 245 204 discloses the photochemical stabilization of synthetic polyamide fiber material using a combination of organic copper complex compounds, Light stabilizers and antioxidants.
  • EP-A-0 165 608 discloses substituted hydroxyphenyltriazines and their specific ones Application as UV absorber in the photographic materials.
  • the use according to the invention is characterized in that the undyed wool or wool-containing mixed fiber is treated with an aqueous solution which has at least one UV absorber of the formula wherein R 4 and R 5 , independently of one another, are C 1 -C 12 alkyl, m 1 or 2, M is hydrogen, sodium, potassium, calcium, magnesium, ammonium or tetraalkylammonium, and n 1 and n 2 are 1 or 2.
  • C 1 -C 12 alkyl examples are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl or isomers of these radicals.
  • Particularly preferred alkyl radicals contain 1 to 4 carbon atoms.
  • alkyl radicals in tetraalkylammonium are in particular independently of one another C 1 -C 4 -alkyl radicals, such as butyl, propyl, ethyl and preferably methyl.
  • Preferred compounds of the formula (3) are those in which M hydrogen; and R 4 and R 5 are methyl; mean.
  • the compounds of the formula (3) can be prepared in a manner known per se, e.g. by the processes described in EP-A-0 165 608.
  • the amount of UV absorber to be added depends on the substrate and the desired one Stabilization starts. In general, 0.1 to 5, preferably 0.3 to 3,% by weight, based on to the wool, too.
  • the compounds of the formula (3) are applied from an aqueous bath.
  • the UV absorbers can also be used to add the chemicals normally used in a dyeing process to the aqueous liquor.
  • Mineral acids such as sulfuric acid or phosphoric acid, organic acids, expediently aliphatic carboxylic acids such as formic acid, acetic acid, oxalic acid or citric acid and / or salts such as ammonium acetate, ammonium sulfate or sodium acetate can be considered as customary chemicals.
  • the acids mainly serve to adjust the pH of the liquors used according to the invention, which is between 3 and 8.
  • the treatment liquors also contain commercially available dispersing and Leveling agents and can also be conventional aids such as electrolytes, wetting agents, defoamers, Contains anti-foaming agents, thickeners or wool preservatives.
  • Special devices are for carrying out the application according to the invention not mandatory. All continuous and discontinuous treatments can be used Process with the usual equipment, such as open baths, Comb, sliver or packers, jiggers, paddles, tree dyeing machines, Circulation or jet dyeing devices or reel runners can be used. Conveniently the application according to the invention takes place in the exhaust process, wherein Normal printing dyeing machines are used.
  • the liquor ratio can be selected within a wide range e.g. 1: 5 to 1: 300, preferably 1:10 to 1:50.
  • the liquor application is expediently 30-400% by weight, preferably 75-250% by weight.
  • the fiber material is subjected to heat treatment for fixation subject.
  • the fixing process can also be carried out using the cold dwell method.
  • the heat treatment is preferably carried out by a steaming process under treatment in a steamer with possibly superheated steam at a temperature of 98 up to 105 ° C during e.g. 1 to 7, preferably 1 to 5 minutes.
  • the fixation of the Compounds of the formula (3) according to the cold residence process can be obtained by storing the impregnated and preferably rolled goods at room temperature (15 to 30 ° C), e.g. for 3 to 24 hours.
  • the duration of treatment is 15 to 60 minutes.
  • the treated fiber material is processed in the usual way rinsed and dried.
  • wool fibers with good thermal and photochemical stability.
  • the abrasion and tear resistance of the fiber improved against photochemical effects.
  • Wool comes in as the fiber material that can be treated according to the invention Consideration.
  • the wool can be finished normally or without felt.
  • the pure Wool fibers also come in mixtures of wool and synthetic polyamide or Wool / polyester blends, e.g. Jersey material made of wool / polyamide in Mixing ratio 70:30.
  • the pure or mixed fiber material in various processing forms, such as as fiber, yarn, fabric, Knitted fabric, fleece or pile material.
  • the present use is particularly advantageous for the treatment of fiber material, exposed to light and heat and e.g. as car upholstery or carpet Is used.
  • the UV absorbers used according to the invention can be in one wide pH range can be used, which also makes them suitable for application Mixtures of wool with other fibers, e.g. Wool and polyamide.

Description

Die vorliegende Erfindung betrifft die Verwendung von spezifischen UV-Absorbern zum photochemischen Stabilisieren von ungefärbter Wolle oder Wolle enthaltenden Mischfasern.The present invention relates to the use of specific UV absorbers for photochemical stabilization of undyed wool or mixed fibers containing wool.

EP-A-0 310 083 offenbart ein Verfahren zum Löschen oder Unterdrücken der Fluoreszenz von optisch aufgehellten natürlichen oder synthetischen Polyamiden mit sulfonierten UV-Absorbern, welche im Unterschied zu den erfindungsgemäss verwendeten UV-Absorbern eine oder mehrere direkt an einem Benzolring gebundene Sulfogruppe enthalten.EP-A-0 310 083 discloses a method for quenching or suppressing fluorescence of optically brightened natural or synthetic polyamides with sulfonated UV absorbers which, in contrast to the UV absorbers used according to the invention contain one or more sulfo groups directly attached to a benzene ring.

US-A-3,444,164 offenbart Hydroxyphenyl-1,2,3-Triazine, welche sich von den erfindungsgemäss verwendeten Hydroxyphenyl-1,2,3-Triazinen dadurch unterscheiden, dass sie keine auf der Alkylengruppe gebundene Hydroxylgruppe besitzen.US-A-3,444,164 discloses hydroxyphenyl-1,2,3-triazines which differ from those according to the invention Distinguish used hydroxyphenyl-1,2,3-triazines in that they have no hydroxyl group bonded to the alkylene group.

Aus der EP-A-0 417 040 ist ein Verfahren zum Färben von Wolle in Anwesenheit eines UV Absorbers aus der Klasse der 2-(2'-Hydroxyphenyl)-s-triazine bekannt.EP-A-0 417 040 describes a process for dyeing wool in the presence of a UV absorbers from the class of 2- (2'-hydroxyphenyl) -s-triazines known.

Aus der EP-A-0 409 771 ist bekannt, dass man synthetische Polyamidfaser mit Hilfe von Lichtschutzmitteln, die Verbindungen aus der Klasse der sterisch gehinderten Amine enthalten, photochemisch stabilisieren kann.From EP-A-0 409 771 it is known that synthetic polyamide fibers can be made using Light stabilizers which contain compounds from the class of the sterically hindered amines, can stabilize photochemically.

EP-A-0 245 204 offenbart die photochemische Stabilisierung von synthetischem Polyamidfasermaterial mittels einer Kombination aus organischen Kupferkomplexverbindungen, Lichtschutzmittel und Antioxidantien.EP-A-0 245 204 discloses the photochemical stabilization of synthetic polyamide fiber material using a combination of organic copper complex compounds, Light stabilizers and antioxidants.

EP-A-0 165 608 offenbart substituierte Hydroxyphenyltriazine und deren spezifische Anwendung als UV-Absorber in den photographischen Materialien.EP-A-0 165 608 discloses substituted hydroxyphenyltriazines and their specific ones Application as UV absorber in the photographic materials.

Die erfindungsgemässe Verwendung ist dadurch gekennzeichnet, dass man die ungefärbte Wolle oder Wolle enthaltende Mischfaser mit einer wässrigen Lösung behandelt, welche mindestens einen UV-Absorber der Formel

Figure 00020001
worin
R4 und R5, unabhängig voneinander, C1-C12-Alkyl, m 1 oder 2, M Wasserstoff, Natrium, Kalium, Calcium, Magnesium, Ammonium oder Tetraalkylammonium, und n1 und n2 1 oder 2, bedeuten.The use according to the invention is characterized in that the undyed wool or wool-containing mixed fiber is treated with an aqueous solution which has at least one UV absorber of the formula
Figure 00020001
wherein
R 4 and R 5 , independently of one another, are C 1 -C 12 alkyl, m 1 or 2, M is hydrogen, sodium, potassium, calcium, magnesium, ammonium or tetraalkylammonium, and n 1 and n 2 are 1 or 2.

Als Beispiele für C1-C12-Alkyl seien Methyl, Ethyl, Propyl, Butyl, Pentyl, Hexyl, Heptyl, Octyl, Nonyl, Decyl, Undecyl oder Dodecyl oder Isomere dieser Reste genannt. Besonders bevorzugte Alkylreste enthalten 1 bis 4 Kohlenstoffatome.Examples of C 1 -C 12 alkyl are methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl or isomers of these radicals. Particularly preferred alkyl radicals contain 1 to 4 carbon atoms.

Die Alkylradikale in Tetraalkylammonium sind insbesondere unabhängig voneinander C1-C4-Alkylradikale, wie Butyl, Propyl, Ethyl und vorzugsweise Methyl.The alkyl radicals in tetraalkylammonium are in particular independently of one another C 1 -C 4 -alkyl radicals, such as butyl, propyl, ethyl and preferably methyl.

Als M werden Natrium, Kalium und insbesondere Wasserstoff bevorzugt.S, potassium and especially hydrogen are preferred as M.

Bevorzugt sind Verbindungen der Formel (3), worin
M Wasserstoff; und
R4 und R5 Methyl;
bedeuten.Preferred compounds of the formula (3) are those in which
M hydrogen; and
R 4 and R 5 are methyl;
mean.

Die Verbindungen der Formel (3) können in an sich bekannter Weise hergestellt werden, z.B. nach den in der EP-A-0 165 608 beschriebenen Verfahren.The compounds of the formula (3) can be prepared in a manner known per se, e.g. by the processes described in EP-A-0 165 608.

Die Menge der zuzusetzenden UV-Absorber hängt vom Substrat und der gewünschten Stabilisierung ab. Im allgemeinen setzt man 0,1 bis 5, vorzugsweise 0,3 bis 3 Gew. %, bezogen auf die Wolle, zu. The amount of UV absorber to be added depends on the substrate and the desired one Stabilization starts. In general, 0.1 to 5, preferably 0.3 to 3,% by weight, based on to the wool, too.

Die Verbindungen der Formel (3 ) werden erfindungsgemäss aus wässrigem Bad appliziert.According to the invention, the compounds of the formula (3) are applied from an aqueous bath.

Mit den UV-Absorbern können auch die für einen Färbeprozess üblichen Chemikalien der wässrigen Flotte zugefügt werden.
Als übliche Chemikalien können Mineralsäuren, wie z.B. Schwefelsäure oder Phosphorsäure, organische Säuren, zweckmässig aliphatische Carbonsäuren wie Ameisensäure, Essigsäure, Oxalsäure oder Zitronensäure und/oder Salze wie Ammoniumacetat, Ammoniumsulfat oder Natriumacetat in Betracht kommen. Die Säuren dienen vor allem der Einstellung des pH-Wertes der erfindungsgemäss verwendeten Flotten, der zwischen 3 und 8 liegt.The UV absorbers can also be used to add the chemicals normally used in a dyeing process to the aqueous liquor.
Mineral acids such as sulfuric acid or phosphoric acid, organic acids, expediently aliphatic carboxylic acids such as formic acid, acetic acid, oxalic acid or citric acid and / or salts such as ammonium acetate, ammonium sulfate or sodium acetate can be considered as customary chemicals. The acids mainly serve to adjust the pH of the liquors used according to the invention, which is between 3 and 8.

Die Behandlungsflotten enthalten ausserdem handelsübliche Dispergier- und Egalisiermittel und können weiterhin übliche Hilfsmittel wie Elektrolyte, Netzmittel, Entschäumer, Schaumverhütungsmittel, Verdicker oder Wollschutzmittel enthalten.The treatment liquors also contain commercially available dispersing and Leveling agents and can also be conventional aids such as electrolytes, wetting agents, defoamers, Contains anti-foaming agents, thickeners or wool preservatives.

Besondere Vorrichtungen sind für die Durchführung der erfindungsgemässen Applikation nicht erforderlich. Es können für die Behandlung alle kontinuierlichen und diskontinuierlichen Verfahren mit den dafür üblichen Apparaturen, wie beispielsweise offene Bäder, Kammzug-, Stranggarn- oder Packapparate, Jigger-, Paddelapparate, Baumfärbeapparate, Zirkulations- oder Düsenfärbeapparate oder Haspelkufen verwendet werden. Zweckmässigerweise erfolgt die erfindungsgemässe Applikation im Ausziehverfahren, wobei Normaldruckfärbeapparate verwendet werden.Special devices are for carrying out the application according to the invention not mandatory. All continuous and discontinuous treatments can be used Process with the usual equipment, such as open baths, Comb, sliver or packers, jiggers, paddles, tree dyeing machines, Circulation or jet dyeing devices or reel runners can be used. Conveniently the application according to the invention takes place in the exhaust process, wherein Normal printing dyeing machines are used.

Beim Ausziehverfahren kann das Flottenverhältnis innerhalb eines weiten Bereiches gewählt werden, z.B. 1:5 bis 1:300, vorzugsweise 1:10 bis 1:50. Man arbeitet zweckmässig bei einer Temperatur von 30 bis 120°C, vorzugsweise 50 bis 98°C.In the exhaust process, the liquor ratio can be selected within a wide range e.g. 1: 5 to 1: 300, preferably 1:10 to 1:50. One works expediently at a temperature of 30 to 120 ° C, preferably 50 to 98 ° C.

Beim Kontinue-Verfahren beträgt der Flottenauftrag zweckmässig 30-400 Gew.%, vorzugsweise 75-250 Gew.%. Zur Fixierung wird das Fasermaterial einer Hitzebehandlung unterworfen. Der Fixierprozess kann auch nach der Kaltverweilmethode erfolgen.In the continuous process, the liquor application is expediently 30-400% by weight, preferably 75-250% by weight. The fiber material is subjected to heat treatment for fixation subject. The fixing process can also be carried out using the cold dwell method.

Die Hitzebehandlung erfolgt vorzugsweise durch ein Dämpfverfahren unter Behandlung in einem Dämpfer mit gegebenenfalls überhitztem Dampf bei einer Temperatur von 98 bis 105°C während z.B. 1 bis 7, vorzugsweise 1 bis 5 Minuten. Die Fixierung der Verbindungen der Formel (3) gemäss dem Kaltverweilverfahren kann durch Lagerung der imprägnierten und vorzugsweise aufgerollten Ware bei Raumtemperatur (15 bis 30°C), z.B. während 3 bis 24 Stunden erfolgen.The heat treatment is preferably carried out by a steaming process under treatment in a steamer with possibly superheated steam at a temperature of 98 up to 105 ° C during e.g. 1 to 7, preferably 1 to 5 minutes. The fixation of the Compounds of the formula (3) according to the cold residence process can be obtained by storing the impregnated and preferably rolled goods at room temperature (15 to 30 ° C), e.g. for 3 to 24 hours.

Die Behandlungsdauer beträgt 15 bis 60 Minuten.The duration of treatment is 15 to 60 minutes.

Nach Beendigung der Fixierung wird das behandelte Fasermaterial auf übliche Weise gespült und getrocknet.After the fixation is finished, the treated fiber material is processed in the usual way rinsed and dried.

Man erhält mit der erfindungsgemässen Applikation Wollfasern mit guter thermischer und photochemischer Stabilität. Ausserdem wird die Abrieb- und Reissfestigkeit der Faser gegenüber photochemischen Einwirkungen verbessert.With the application according to the invention, wool fibers with good thermal and photochemical stability. In addition, the abrasion and tear resistance of the fiber improved against photochemical effects.

Als Fasermaterial, das erfindungsgemäss behandelt werden kann, kommt Wolle in Betracht. Die Wolle kann normal oder filzfrei ausgerüstet sein. Neben den reinen Wollfasern kommen auch Fasermischungen aus Wolle und synthetischem Polyamid oder Wolle/Polyestergemische in Betracht, so z.B. Trikotmaterial aus Wolle/Polyamid im Mischungsverhältnis 70:30. Grundsätzlich kann das reine oder gemischte Fasermaterial in den verschiedensten Verarbeitungsformen vorliegen, wie z.B. als Faser, Garn, Gewebe, Gewirke, Vlies oder Flormaterial.Wool comes in as the fiber material that can be treated according to the invention Consideration. The wool can be finished normally or without felt. In addition to the pure Wool fibers also come in mixtures of wool and synthetic polyamide or Wool / polyester blends, e.g. Jersey material made of wool / polyamide in Mixing ratio 70:30. Basically, the pure or mixed fiber material in various processing forms, such as as fiber, yarn, fabric, Knitted fabric, fleece or pile material.

Die vorliegende Verwendung eignet sich besonders vorteilhaft zur Behandlung von Fasermaterial, das Licht und Hitze ausgesetzt wird und z.B. als Autopolsterstoff oder Teppich Verwendung findet. Die erfindungsgemäss verwendeten UV-Absorber können dabei in einem weiten pH-Bereich eingesetzt werden, wodurch sie auch für die Applikation bei Mischungen von Wolle mit anderen Fasern, z.B. Wolle und Polyamid, geeignet sind.The present use is particularly advantageous for the treatment of fiber material, exposed to light and heat and e.g. as car upholstery or carpet Is used. The UV absorbers used according to the invention can be in one wide pH range can be used, which also makes them suitable for application Mixtures of wool with other fibers, e.g. Wool and polyamide.

Claims (3)

  1. Use of a UV absorber of formula
    Figure 00060001
    wherein
    R4 and R5 are each independently of the other C1-C12alkyl, m is 1 or 2, M is hydrogen, sodium, potassium, calcium, magnesium, ammonium or tetraalkyl ammonium, and n1 and n2 are 1 or 2, for the photochemical stabilisation of undyed wool or of fibre blends containing undyed wool, which comprises applying the UV absorber from an aqueous solution to the fibre.
  2. Use according to claim 1, which comprises using a UV absorber of formula (3), wherein M is hydrogen, R4 and R5 are methyl, and n1 and n2 are 1 or 2.
  3. Use according to either claim 1 or claim 2, wherein the aqueous solution has a pH of 3 to 8.
EP91810709A 1990-09-13 1991-09-04 Photochemical stabilisation of wool Expired - Lifetime EP0475905B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH297390 1990-09-13
CH2973/90 1990-09-13

Publications (2)

Publication Number Publication Date
EP0475905A1 EP0475905A1 (en) 1992-03-18
EP0475905B1 true EP0475905B1 (en) 1998-01-14

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EP (1) EP0475905B1 (en)
JP (1) JP3184259B2 (en)
AU (1) AU8387591A (en)
DE (1) DE59108923D1 (en)
NZ (1) NZ239755A (en)

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EP0475905A1 (en) 1992-03-18
JPH04281070A (en) 1992-10-06
JP3184259B2 (en) 2001-07-09
US5197991A (en) 1993-03-30
AU8387591A (en) 1992-03-19
DE59108923D1 (en) 1998-02-19
NZ239755A (en) 1993-05-26

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