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 lightfastness of polyester dyeings, in which the fibers are treated in a boiling aqueous dye bath which, in addition to the dye, also contains alkyl ethers of 2,2 ⁇ , 4,4 ⁇ -tetrahydroxybenzophenone .
• 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 is achieved according to the invention with a process for dyeing textile polyester material with disperse dyes with simultaneous use of benzophenone derivatives to improve lightfastness, which is characterized in that the dye baths are given a benzophenone derivative of the formula I.
• R is a hydrogen atom, an alkyl radical with 1 to 4 carbon atoms, cyan, fluorine, chlorine, bromine or trifluoromethyl
• R1 is a hydrogen atom or an alkyl radical having 1 to 6 carbon atoms and for m is the number 1 or 2
• for n is the number 2, 3 or 4
• R2 an optionally substituted by hydroxy or C1- to C4-alkoxy alkyl radical having 1 to 12 carbon atoms, a cycloalkyl radical having 3 to 6 carbon atoms in the ring, a radical from the group of Formulas where R3, R4 and R5 are hydrogen atoms, alkyl or alkoxy radicals having 1 to 4 carbon atoms or one or two of the radicals R3 to R5 fluorine, chlorine, bromine, cyano or trifluoromethyl, one of the radicals R3 to R5 phenyl or phenoxy and q the Number 1, 2, 3 or 4 mean, or R2 is an optionally substituted
• R is a hydrogen atom, methyl, fluorine, chlorine or bromine and R2 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 represents a hydrogen atom, an alkyl radical having 1 to 4 C atoms, cyan, fluorine, chlorine, bromine or trifluoromethyl, R1 represents a hydrogen atom or an alkyl radical having 1 to 6 C atoms and for m the number 1 or 2, for n is the number 2, 3 or 4 and for R2 an alkyl radical with 1 to 4 carbon atoms substituted by hydroxy or C1 to C4 alkoxy, a radical from the group where R3, R4 and R5 are hydrogen atoms, alkyl or alkoxy radicals having 1 to 4 carbon atoms or one or two of the radicals R2 to R5 fluorine, chlorine, bromine, cyano or trifluoromethyl and q is the number 1, 2, 3 or 4, with the restriction that at least one of the radicals R3 to R5 must be different from hydrogen, or R2 is an optionally substituted 5- or 6-membered, unsaturated
• 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.
• 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.
• R2 radicals in the formula I are: C1 to C12 alkyl, such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, n-pentyl, 3-methylbutyl, 1-ethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, n-hexyl, n-heptyl, 1-ethylpentyl, n-octyl, 2,4,4-trimethylpentyl, n-nonyl, n-decyl, n-undecyl, 4-dodecyl, hydroxymethyl, hydroxyethyl, 2-hydroxypropyl, 2-hydroxy-2-methylpropyl, 3- Hydroxy-2-methylpropyl, 2-hydroxybutyl, methoxymethyl, methoxyethyl; Cycloalkyl,
• 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 (III), with a carboxylic acid R2COOH, in which R2 has the meanings given for R2 in formula (III), in an inert solvent, in particular toluene or xylene, in the presence of an acidic catalyst, in particular sulfuric acid, p-toluenesulfonic acid or a strongly acidic ion exchanger Reflux temperatures and workup in a conventional manner.
• 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.
• They can be dyed with the customary disperse dyes which belong to the known classes of dyes such as azo, anthraquinone, methine, quinophthalone and coumarin dyes by methods known per se, such as the high-temperature process, the thermosol process or the carrier dyeing process, how For example, the "Guide, dyeing and finishing polyester fibers and polyester fiber mixtures", published by BASF Aktiengesellschaft 1974, can be found.
• 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 of 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%.
• R and R 1 always represent a hydrogen atom.
• the starting compounds 2-hydroxy-4- ( ⁇ -hydroxyethoxy) -4 ⁇ -chloro and 2-hydroxy-4- ( ⁇ -hydroxyethoxy) -4 ⁇ -methylbenzophenone are obtained from the corresponding 2,4-dihydroxy by conventional reaction with ethylene oxide or ethylene carbonate Receive -4-chloro- and 2,4-dihydroxy-4 ⁇ -methylbenzophenone.
• 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 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 5 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 with 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.
• a dyeing is carried out analogously to Example 2 using the benzophenone compound of the formula by.
• 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 5 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.
• 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 color 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 color without the addition of the benzophenone compound.
• the benzophenone compound according to the invention used in this example absorbs more than 90% of 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 exhaustion is about 75% and whose sublimation loss (30 seconds, 190 ° C) is 20-25% under the same dyeing 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 with 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 whose sublimation loss (30 seconds, 190 ° C) is 20-25% under the same dyeing conditions.
• 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 5 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 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 whose sublimation loss (30 seconds, 190 ° C) is 20-25% under the same dyeing 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 carried out for a further 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 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 violet coloration is obtained which, when exposed to xenotest under hot and humid conditions (temperature 75 ° C., relative air humidity 80%), is clearly more lightfast than a similar 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)

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Publications (3)

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ID=6306059

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• 1986
  • 1986-07-26 DE DE19863625355 patent/DE3625355A1/de not_active Withdrawn
• 1987
  • 1987-07-10 US US07/072,032 patent/US4789382A/en not_active Expired - Fee Related
  • 1987-07-17 ES ES198787110336T patent/ES2038624T3/es not_active Expired - Lifetime
  • 1987-07-17 EP EP87110336A patent/EP0254987B1/fr not_active Expired - Lifetime
  • 1987-07-17 DE DE8787110336T patent/DE3777004D1/de not_active Expired - Lifetime
  • 1987-07-22 JP JP62181295A patent/JPS6345236A/ja active Pending
  • 1987-07-24 DK DK386387A patent/DK386387A/da not_active Application Discontinuation

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