EP0254987B1 - Ethers-esters de la benzophénone et procédé d'amélioration de la stabilité à la lumière de colorations de polyesters par l'utilisation des éthers-esters de la benzophénone - Google Patents

Ethers-esters de la benzophénone et procédé d'amélioration de la stabilité à la lumière de colorations de polyesters par l'utilisation des éthers-esters de la benzophénone Download PDF

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Publication number
EP0254987B1
EP0254987B1 EP87110336A EP87110336A EP0254987B1 EP 0254987 B1 EP0254987 B1 EP 0254987B1 EP 87110336 A EP87110336 A EP 87110336A EP 87110336 A EP87110336 A EP 87110336A EP 0254987 B1 EP0254987 B1 EP 0254987B1
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Prior art keywords
hydrogen
benzophenone
formula
carbon atoms
alkyl
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EP87110336A
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English (en)
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EP0254987A3 (en
EP0254987A2 (fr
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Peter Dr. Neumann
Dieter Dr. Wegerle
Reinhold Krallmann
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BASF SE
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BASF SE
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Classifications

    • 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
    • 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
    • D06P1/6421—Compounds containing nitrile groups
    • 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
    • D06P1/651—Compounds without nitrogen
    • D06P1/65106—Oxygen-containing compounds
    • 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
    • Y10S8/922—Polyester fiber

Definitions

  • the invention relates to new benzophenone ether esters and a process for dyeing textile polyester material with disperse dyes using benzophenone ether esters to improve lightfastness, and to the use of these benzonphenone derivatives in dyeing textile polyester material.
  • DE-AS 1 156 760 discloses a process for improving the light fastness of polyester dyeings, in which the fibers are in a boiling aqueous dye bath which, in addition to the dye, also contains alkyl ethers of 2,2 ', 4,4'-tetrahydroxybenzophenone , treated.
  • the benzophenone derivative is drawn onto the fiber together with the dye.
  • the fiber dyed in this way has better lightfastness when exposed in an exposure device (for example a Xenotest or fadeometer) compared to a fiber dyed without the addition of the tetrahydroxybenzophenone derivative.
  • the compounds described in DE-AS 1 156 760 have a number of disadvantages: due to their inherent color, they shift the color tone, in particular in the case of brilliant colorations, and cloud the coloration to a greater or lesser extent.
  • the absorption capacity on the textile structures is not exhaustive enough, so that the wastewater from the dyeing plants is contaminated with organic compounds.
  • the compounds mentioned tend to sublimation in a thermal aftertreatment usually carried out after the dyeing process.
  • the object of the invention is to provide materials for the improvement of the light fastness of dyeings with disperse dyes on polyester, which are good for polyester, show a low tendency to sublimation and which do not or only slightly impair the dyeings, in particular with regard to their brilliance.
  • R is a hydrogen atom, methyl, fluorine, chlorine or bromine and R 2 is an alkyl radical having 1 to 4 carbon atoms, a cyclohexyl radical or a radical from the group where p and q stand for the numbers 1 or 2.
  • the invention therefore also relates to the new benzophenone derivatives of the formula III in which R is a hydrogen atom, an alkyl radical having 1 to 4 C atoms, cyan, fluorine, chlorine, bromine or trifluoromethyl, R 1 is a hydrogen atom or an alkyl radical having 1 to 6 C atoms and m is 1 or 2, for n the number 2, 3 or 4 and for R 2 an alkyl radical with 1 to 4 carbon atoms substituted by hydroxyl or C 1 - to C 4 -alkoxy, a radical from the group where R 3 , R 4 and R 5 are hydrogen atoms, alkyl or alkoxy radicals having 1 to 4 carbon atoms or one or two of the radicals R 2 to R 5 are fluorine, chlorine, bromine, cyano or trifluoromethyl and q is the number 1, 2, 3 or 4 mean, with the restriction that at least one of the radicals R 3 to R 5 must be different from hydrogen, or R 2 is an optionally substituted 5- or 6-
  • R is a hydrogen atom, methyl, fluorine, chlorine or bromine and m is 1 and R 1 is a hydrogen atom and n is 2.
  • R is a hydrogen atom, methyl, a fluorine, chlorine or bromine atom and m is the number 1
  • R 1 is a hydrogen atom
  • R 2 is a radical from the group
  • alkyl radicals for R and R 1 are methyl, ethyl, propyl, n- and tert-butyl.
  • Preferred radicals for R and R 1 are H and methyl.
  • the new compounds of the formula (III) are prepared in a manner known per se by reacting an alcohol of the formula (IV) in which R, m and n have the meanings given for R, m and n of the formula (111), with a carboxylic acid R 2 COOH, in which R 2 has the meanings given for R 2 in formula (111), in an inert solvent, in particular toluene or xylene, in the presence of an acidic catalyst, in particular sulfuric acid, p-toluenesulfonic acid or one strong acidic ion exchanger, at reflux temperatures and workup in a conventional manner.
  • an alcohol of the formula (IV) in which R, m and n have the meanings given for R, m and n of the formula (111)
  • R 2 COOH in which R 2 has the meanings given for R 2 in formula (111)
  • an inert solvent in particular toluene or xylene
  • an acidic catalyst in particular sulfuric acid, p-tol
  • textile materials made from polyesters are dyed in a conventional manner.
  • structures such as fibers, threads, flakes, foils, fabrics and knitted fabrics come into consideration as such.
  • the known dye classes such as Azo, anthraquinone, methine, quinophthalone and coumarin dyes belong, according to methods known per se, such as e.g. the high temperature process, the thermosol process or the carrier dyeing process are colored, e.g. can be found in the "Advice, dyeing and finishing of polyester fibers and polyester fiber mixtures", published by BASF Aktiengesellschaft 1974.
  • the benzophenone derivatives are added to the dyebaths in finely divided form, optionally as a powder or liquid preparation. They are used in amounts of 0.1 to 10, preferably 0.3 to 5% by weight, based on the textile material.
  • the compounds to be used according to the invention have a significantly lower intrinsic color and thus practically do not influence the hue of dyeings. While e.g. 75% of the 2,2'-dihydroxy-4,4'-dimethoxybenzophenone in the dyebath drains, the compounds to be used according to the invention reach degrees of absorption in the order of 85 to 95%. In the known compounds, the sublimation losses (30 sec., 190 ° C.) are 20 to 25%, based on the absorbed substance, in the compounds to be used according to the invention below 10%.
  • the starting compounds 2-hydroxy-4- (ß-hydroxyethoxy) -4'-chloro and 2-hydroxy-4- (ß-hydroxyethoxy) -4'-methylbenzophenone are obtained from the corresponding 2 by conventional reaction with ethylene oxide or ethylene carbonate , 4-Dihydroxy-4'-chloro- and 2,4-dihydroxy-4'-methylbenzophenone obtained.
  • 100 parts of a polyester yarn are in a dye bath containing 1500 parts of water, 0.6 parts of a mixture of the finely divided dyes 1.8 parts of a product obtained by adding 50 moles of ethylene oxide to 1 mole of sperm oil alcohol and subsequent sulfonation as a dyeing aid and 1.5 parts of the finely divided benzophenone compound of the formula contains, treats,
  • the process is started at 60 ° C., the temperature is raised to 130 ° C. in 20 minutes and dyeing is continued at this temperature for 90 minutes in an HT dyeing machine.
  • a brown coloration is obtained which, when exposed to xenotest under hot and humid conditions (e.g. temperature 75 ° C, relative air humidity 80%), is significantly more lightfast than the same coloration without the addition of the benzophenone compound.
  • 100 parts of a knitted fabric made of polyester are in a dyebath, the 2500 parts of water, 1.2 parts of a mixture of the finely divided dyes Parts of a carrier based on salicylic acid methyl ester and 2 parts of the finely divided benzophenone compound of the formula contains, treats.
  • the dyeing is carried out for 90 minutes at the boiling point and a reddish-brown coloration is obtained which, in an exposure test in a fadeometer, gives significantly better results than a similar coloration without the addition of the benzophenone compound.
  • a polyester fabric is impregnated on a three-roll pad with a dye liquor containing 25 parts of a mixture of the finely divided dyes in 1000 parts 20 parts of a 20% aqueous solution of the copolymer of acrylic acid and acrylamide, 25 parts of the finely divided benzophenone compound and contains 930 parts of water.
  • the fabric After impregnation under 60% liquor absorption, the fabric is dried at 120 ° C and thermosolated at 200 ° C for 60 seconds.
  • a gray coloration is obtained which is significantly better in light fastness than a same coloration without the addition of the benzophenone compound.
  • the dyeing is carried out for 90 minutes at the boiling point and a reddish-brown coloration is obtained which, in an exposure test in a fadeometer, gives significantly better results than a similar coloration without the addition of the benzophenone compound.
  • 100 parts of a polyester yarn are in a dye bath containing 1500 parts of water, 0.6 parts of a mixture of the finely divided dyes 1.8 parts of a product obtained by adding 50 moles of ethylene oxide to 1 mole of sperm oil alcohol and subsequent sulfonation as a dyeing aid and 1.5 parts of the finely divided benzophenone compound of the formula contains, treats.
  • the process is started at 60 ° C., the temperature is raised to 130 ° C. in 20 minutes and dyeing is carried out for a further 90 minutes at this temperature in a high-temperature dyeing machine.
  • a brown coloration is obtained which, when exposed to xenotest under hot and humid conditions (temperature 75 ° C., relative atmospheric humidity 80%), is significantly less lightfast than the same coloration without the addition of the benzophenone compound.
  • the benzophenone compound according to the invention used in this example absorbs over 90% the polyester fiber and shows only a slight sublimation loss (30 seconds, 190 ° C) of 5-6%. In terms of these properties, it behaves significantly more favorably than the known 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, whose degree of absorption is about 75% and its sublimation loss (30 seconds, 190 ° C.) is below 20-25% same coloring conditions.
  • a polyester fabric is impregnated on a three-roll pad with a dye liquor containing 25 parts of a mixture of the finely divided dyes in 1000 parts 20 parts of a 20% aqueous solution of the copolymer of acrylic acid and acrylamide, 25 parts of the finely divided benzophenone compound and contains 930 parts of water.
  • the fabric After impregnation under 60% liquor absorption, the fabric is dried at 120 ° C and thermosolated at 200 C for 60 seconds.
  • a gray coloration is obtained which is significantly better in light fastness than a same coloration without the addition of the benzophenone compound.
  • the benzophenone compound according to the invention used in this example absorbs 87-88% of the polyester resins and shows only a slight sublimation loss (30 seconds, 190 ° C.) of less than 5%. In terms of these properties, it behaves significantly more favorably than the known 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, whose degree of exhaustion is about 75% and its sublimation loss (30 seconds, 190 ° C.) is below 20-25% same coloring conditions.
  • the dyeing is carried out for 90 minutes at the boiling point and a black color is obtained which, in an exposure test in a fadeometer, gives significantly better results than a same color without the addition of the benzophenone compound.
  • the benzophenone compound according to the invention used in this example absorbs about 87% of the polyester fiber and shows only a slight sublimation loss (30 seconds, 190 ° C.) of 4-5%. In terms of these properties, it behaves significantly more favorably than the known 2,2'-dihydroxy-4,4'-dimethoxybenzophenone, whose degree of exhaustion is about 75% and its sublimation loss (30 seconds, 190 ° C.) is below 20-25% same coloring conditions.
  • 100 parts of a polyester yarn are in a dye bath containing 1500 parts of water, 0.6 parts of a mixture of the finely divided dyes 1.8 parts of a product obtained by adding 50 moles of ethylene oxide to 1 mole of sperm oil alcohol and subsequent sulfonation as a dyeing aid and 1.5 parts of the finely divided benzophenone compound of the formula contains, treats.
  • the process is started at 60 ° C., the temperature is raised to 130 ° C. in 20 minutes and dyeing is continued at this temperature for 90 minutes in an HT dyeing machine.
  • a green coloration is obtained which, when exposed to xenotest under hot and humid conditions (temperature 75 ° C., relative atmospheric humidity 80%), is significantly more lightfast than the same coloration without the addition of the benzophenone compound.
  • 100 parts of a polyester yarn are in a dye bath containing 1500 parts of water, 0.6 parts of a mixture of the finely divided dyes 1.8 parts of a by adding 50 moles of ethylene oxide to 1 mole of sperm oil alcohol and subsequent Sulfonating product obtained as a dyeing aid and 1.5 parts of the finely divided benzophenone compound of the formula contains, treats.
  • the process is started at 60 ° C., the temperature is raised to 130 ° C. in 20 minutes and dyeing is carried out for a further 90 minutes at this temperature in a high-temperature dyeing machine.
  • a violet coloration is obtained which, when exposed to xenotest under hot and humid conditions (temperature 75 ° C., relative atmospheric humidity 80%), is significantly less lightfast than the same coloration without the addition of the benzophenone compound.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Indole Compounds (AREA)

Claims (6)

1. Procédé de teinture d'une matière textile en polyester à l'aide de colorants dispersés et en recourant à l'emploi simultané de dérivés de la benzophénone pour l'amélioration de la solidité ou stabilité à la lumière, caractérisé en ce que l'on ajoute aux bains de teinture, un dérivé de la benzophénone de la formule 1 dans laquelle
R représente un atome d'hydrogène, un radical alkyle qui comporte de 1 à 4 atomes de carbone, le radical cyano, un atome de fluor, de chlore, de brome, ou le radical trifluorométhyle,
R1 représente un atome d'hydrogène ou un radical alkyle qui comporte de 1 à 6 atomes de carbone et
m est égal à 1 ou à 2,
n est égal à 2, 3 ou 4 et
R2 représente un radical alkyle qui comporte de 1 à 12 atomes de carbone, éventuellement à substitution hydroxylique ou alcoxylique en Ci à C4, un radical cycloalkyle dont le cycle comporte de 3 à 6 atomes de carbone, un radical appartenant au groupe des radicaux des formules

où R3, R4 et R5 représentent des atomes d'hydrogène, des radicaux alkyle ou alcoxy qui comportent de 1 à 4 atomes de carbone, ou bien un ou deux des symboles R3 à R5 représentent des atomes de fluor, de chlore, de brome, des radicaux cyano ou trifluorométhyle, l'un des symboles R3 à R5 représente un radical phényle ou phénoxy et q est égal à 1, 2, 3 ou 4, ou bien R2 représente un noyau hétérocyclique insaturé, pentagonal ou hexagonal, éventuellement substitué.
2. Procédé de teinture d'une matière textile en polyester, selon la revendication 1, caractérisé en ce que l'on ajoute aux bains de teinture, un dérivé de la benzophénone de la formule Il
Figure imgb0108
dans laquelle R représente un atome d'hydrogène, le radical méthyle, un atome de fluor, de chlore ou de brome et R2 représente un radical alkyle comportant de 1 à 4 atomes de carbone, un radical cyclohexyle, ou un radical appartenant au groupe des radicaux des formules
Figure imgb0109
Figure imgb0110
où p est q sont égaux à 1 ou à 2.
3. Utilisation de dérivés de la benzophénone répondant à la formule I telle que définie dans la revendication 1, en vue de la teinture d'une matière textile en polyester avec des colorants dispersés pour l'amélioration de la stabilité ou solidité à la lumière, en une proportion de 0,1 à 10% en poids, par rapport à la matière textile.
4. Utilisation de dérivés de la benzophénone de la formule Il telle que définie dans la revendication 2 pour la teinture d'une matière textile en polyester avec des colorants dispersés, selon la revendication 3.
5. Dérivés de la benzophénone de la formule III
Figure imgb0111
dans laquelle R représente un atome d'hydrogène, un radical alkyle qui comporte de 1 à 4 atomes de carbone, le radical cyano, un atome de fluor, de chlore, de brome ou le radical trifluorométhyle, R1 représente un atome d'hydrogène ou un radical alkyle qui comporte de 1 à 6 atomes de carbone et m est égal à 1 ou à 2, n est égal à 2, 3 ou 4 et R2 représente un radical alkyle qui comporte de 1 à 4 atomes de carbone, à substitution hydroxylique ou alcoxylique en C1-C4 éventuelle, un radical appartenant au groupe des radicaux des formules
Figure imgb0112
où R3, R4 et R5 représentent des atomes d'hydrogène, des radicaux alkyle ou alcoxy qui comportent de 1 à 4 atomes de carbone, ou bien un ou deux des symboles R2 à R5 représentent des atomes de fluor, de chlore, de brome, des radicaux cyano ou trifluorométhyle et q est égal à 1, 2, 3 ou 4, avec la restriction qu'au moins l'un des symboles R3 à R5 ne peut représenter de l'hydrogène, ou que R2 représente un noyau hétérocyclique insaturé, pentagonal ou hexagonal, éventuellement substitué.
6. Dérivés de la benzophénone de la formule III, selon la revendication 5, dans lesquels R représente un atome d'hydrogène, le radical méthyle, un atome de fluor, de chlore ou de brome et m est égal à 1, R1 représente un atome d'hydrogène et R2 représente un radical choisi dans le groupe des radicaux des formules
Figure imgb0113
Figure imgb0114
où p et q sont égaux à 1 ou à 2, à l'exception que R2 ne peut représenter de radical phényle lorsque R représente un atome d'hydrogène.
EP87110336A 1986-07-26 1987-07-17 Ethers-esters de la benzophénone et procédé d'amélioration de la stabilité à la lumière de colorations de polyesters par l'utilisation des éthers-esters de la benzophénone Expired - Lifetime EP0254987B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3625355 1986-07-26
DE19863625355 DE3625355A1 (de) 1986-07-26 1986-07-26 Benzophenonether-ester und ein verfahren zur verbesserung der lichtechtheit von polyesterfaerbungen unter verwendung von benzophenonether-estern

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EP0254987A2 EP0254987A2 (fr) 1988-02-03
EP0254987A3 EP0254987A3 (en) 1989-08-02
EP0254987B1 true EP0254987B1 (fr) 1992-03-04

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US (1) US4789382A (fr)
EP (1) EP0254987B1 (fr)
JP (1) JPS6345236A (fr)
DE (2) DE3625355A1 (fr)
DK (1) DK386387A (fr)
ES (1) ES2038624T3 (fr)

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DE3930516A1 (de) * 1989-09-13 1991-03-21 Riedel De Haen Ag Benzophenonether-ester, verfahren zu ihrer herstellung, sowie ihre verwendung zur verbesserung der lichtstabilitaet von polyesterfaerbungen
DE4007765A1 (de) * 1990-03-12 1991-09-19 Basf Ag Verwendung von benzophenon-derivaten als lichtschutzmittel fuer aromatische polycarbonate und aromatische polyestercarbonate
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DK386387A (da) 1988-01-27
JPS6345236A (ja) 1988-02-26
DE3625355A1 (de) 1988-02-04
EP0254987A3 (en) 1989-08-02
DK386387D0 (da) 1987-07-24
US4789382A (en) 1988-12-06
DE3777004D1 (de) 1992-04-09
EP0254987A2 (fr) 1988-02-03
ES2038624T3 (es) 1993-08-01

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