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
  • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
  • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
  • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • D06M15/31—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated nitriles
• • 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
  • D06P3/34—Material containing ester groups
  • D06P3/52—Polyesters
  • D06P3/54—Polyesters using dispersed dyestuffs
• • 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

Definitions

• the present invention relates to a method for improving the photochemical stability of dyeings on polyester fiber materials.
• Dyed polyester fiber material is damaged when exposed to light and especially when exposed to heat.
• Such colored materials have therefore been protected against the effects of light and heat with UV absorbers of the benzophenone or benzotriazole type, but without achieving satisfactory results, because these compounds result in product loss due to their inadequate sublimation fastness, in the heat setting of the dyeings and in exposure to elevated temperatures and have resulted in insufficient protection.
• the object underlying the present invention was to find a process for improving the photochemical stability of dyeings on polyester fiber materials which has no loss of product and meets the current requirements.
• the present invention thus relates to a process for improving the photochemical stability of dyeings on polyester fiber materials with UV absorbers, which is characterized in that the fiber material is mixed with a compound of the formula before dyeing or during dyeing treated in what
• R alkyl with 1-4 C atoms, alkoxy with 1-4 C atoms, malogen or hydroxy
• R1 and R2 independently of one another alkyl with 1-18 C atoms, by hydroxy, alkoxy with 1-4 C atoms, alkylthio with 1-4 C atoms, amino or mono- or di-alkylamino with 1-4 C atoms in the alkyl part substituted alkyl with 1-18 C-atoms, phenyl, with chlorine, alkyl with 1-4 C-atoms or alkoxy with 1-4 C-atoms substituted phenyl or o-hydroxyphenyl and
• n 0, 1 or 2 mean.
• alkyl alkoxy or alkylthio radicals with 1-4 carbon atoms are radicals such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy , Isobutoxy, sec-butoxy, tert-butoxy, methylthio, ethylthio, propylthio, Isopropylthio, butylthio, isobutylthio, sec.-butylthio and tert.-butylthio.
• R1 and / or R2 is an alkyl radical with 1-18 C atoms, radicals such as methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl, pentyl, hexyl, octyl, decyl, dodecyl, tetradecyl, Hexadecyl and octadecyl.
• Alkyl radicals with 1-4 C atoms are preferred.
• alkyl radicals are substituted by a mono- or dialkylamino radical, then these are amino radicals which are mono- or disubstituted by alkyl radicals, such as methyl, ethyl, propyl or butyl.
• R3 and R4 independently of one another are alkyl with 1-4 C atoms, phenyl or phenyl substituted by alkyl with 1-4 C atoms or alkoxy with 1-4 C atoms.
• R5 alkyl with 1-4 carbon atoms or alkoxy with 1-4 carbon atoms
• R6 and R7 are independently alkyl with 1-4 carbon atoms or phenyl.
• the compounds of the formulas (1) to (3) also known as UV absorbers, are known or can be prepared in a manner known per se, for example by heating an amidine and an o-hydroxybenzene carboxylic acid ester, preferably in an approximate molar ratio of 2: 1 in boiling organic solvents [cf. US 3,896,125 and Helv. Chim. Acta 55 , 1566-1595 (1972)].
• Suitable compounds of the formulas (1), (2) and (3) are, for example 2- (2'-Hydroxy-5'-methylphenyl) -4,6-dimethyl-s-triazine: mp 131 ° C: 2- (2′-hydroxy-3 ′, 5′-dimethylphenyl) -4,6-dimethyl-s-triazine: F.
• the compounds of the formulas (1), (2) and (3) to be used as UV absorbers are in an amount of 0.05 to 7.5, preferably 0.20 to 3 and particularly 0.5 to 2% by weight of the fiber material used.
• polyester fiber material which can be dyed in the presence of the UV absorbers mentioned, there are e.g. Cellulose ester fibers, such as cellulose-21 ⁇ 2-acetate fibers and triacetate fibers and particularly linear polyester fibers.
• Linear polyester fibers are to be understood as synthetic fibers which e.g. can be obtained by condensation of terephthalic acid with ethylene glycol or of isophthalic acid or terephthalic acid with 1,4-bis (hydroxymethyl) cyclohexane, and also copolymers of terephthalic and isophthalic acid and ethylene glycol.
• the linear polyester used almost exclusively in the textile industry so far consists of terephthalic acid and ethylene glycol.
• the fiber materials can also be used as a mixed fabric among themselves or with other fibers, e.g. Mixtures of polyacrylonitrile / polyester, polyamide / polyester, polyester / cotton, polyester / viscose and polyester / wool can be used.
• the textile material to be dyed can be in various forms.
• Piece goods such as knitted fabrics or woven fabrics, are preferably used.
• the disperse dyes to be used which are only sparingly soluble in water and are present in the dye liquor for the most part in the form of a fine dispersion, can be of a wide variety Dye classes belong to, for example, the acridone, azo, anthraquinone, coumarin, methine, perinone, naphthoquinone imine, quinophthalone, styryl or nitro dyes. Mixtures of disperse dyes can also be used according to the invention.
• polyester / wool mixed fiber materials are preferably dyed with commercially available mixtures of anionic dyes and disperse dyes.
• the anionic dyes are, for example, salts of heavy metal-containing or preferably metal-free mono-, dis- or polyazo dyes including the formazan dyes and the anthraquinone, xanthene, nitro, triphenylmethane, naphthoquinoneimine and phthalocyanine dyes.
• the anionic character of these dyes can be caused by metal complex formation alone and / or preferably by acidic, salt-forming substituents, such as carboxylic acid groups, sulfuric acid and phosphonic acid ester groups, phosphonic acid groups or sulfonic acid groups.
• These dyes can also have so-called reactive groups in the molecule, which form a covalent bond with the wool.
• the 1: 1 metal complex dyes preferably have one or two sulfonic acid groups. As metal, they contain a heavy metal atom such as Copper, nickel or especially chrome.
• the 1: 2 metal complex dyes contain as the central atom a heavy metal atom such as a cobalt atom or in particular a chromium atom. Two complex-forming components are connected to the central atom, at least one of which is a dye molecule, but preferably both are dye molecules. The two dye molecules involved in the complex formation can be the same or different from one another.
• the 1: 2 metal complex dyes can contain, for example, two azomethine molecules, a disazo dye and a monoazo dye, or preferably two monoazo dye molecules.
• the azo dye molecules can be water-solubilizing Have groups such as acid amide, alkylsulfonyl or the above acid groups. Preference is given to 1: 2 cobalt or 1: 2 chromium complexes of monoazo dyes which have acid amide, alkylsulfonyl or a total of a single sulfonic acid group.
• Fiber mixtures of polyester and cotton are usually dyed with a combination of dispersion dyes and vat dyes, sulfur dyes, leuco vat ester dyes, direct dyes or reactive dyes, the polyester content being pre-, simultaneously or post-dyed with disperse dyes.
• vat dyes are non-fused and heterocyclic benzoquinones or naphthoquinones, sulfur dyes and in particular anthraquinone or indigo dyes.
• vat dyes which can be used according to the invention are listed in the Color Index, 3rd Edition (1971), Vol. 3, on pages 3649 to 3837 under the names "Sulfur Dyes” and "Vat Dyes”.
• Suitable direct dyes are, for example, the "Direct Dyes” mentioned in Color Index 3rd Edition (1971), Vol. 2, on pages 2005 to 2478.
• the leuco vat ester dyes are e.g. from vat dyes of the indigo, anthraquinone or indanthrene series by reduction e.g. with iron powder and subsequent esterification e.g. available with chlorosulfonic acid and are referred to in the Color Index, 3rd Edition (1971), Vol. 3, as "Solubilized Vat Dyes".
• Reactive dyes are understood to be the customary dyes which form a chemical bond with the cellulose, for example the "Reactive Dyes” listed on pages 3391 to 3560 in the Color Index, 3rd Edition (1971), Vol. 3.
• the amount of dyes to be added to the liquor depends on the desired color strength; In general, amounts of 0.01 to 10, preferably 0.02 to 5 percent by weight, based on the textile material used, have proven successful.
• the compounds to be used according to the invention can also be mixed with known carriers based on e.g. Di- or tri-chlorobenzene, methyl- or ethylbenzene, o-phenylphenol, benzylphenol, diphenyl ether, chlorodiphenyl, methyldiphenyl, cyclohexanone, acetophenone, alkylphenoxyethanol, mono-, di- or trichlorophenoxyethanol or -propanol, pentachlorophenoxyethanoate, in particular, or alkylphenylbenzene, alkylphenylbenzene Diphenyl, methyl diphenyl ether, dibenzyl ether, methyl benzoate, butyl benzoate and phenyl benzoate can be used.
• known carriers based on e.g. Di- or tri-chlorobenzene, methyl- or ethylbenzene, o-phenylphenol, benz
• the carriers are preferably used in an amount of 0.5 to 2 g / l of liquor or 5 to 10 percent by weight, based on the compounds to be used.
• the dyebaths can contain, in addition to the dyes and the compounds to be used according to the invention, wool protection agents, oligomer inhibitors, oxidizing agents, antifoams, emulsifiers, leveling agents, retarders and preferably dispersants.
• the dispersants are used primarily to achieve a good fine distribution of the disperse dyes. Commonly used dispersants are suitable for dyeing with disperse dyes.
• the dispersants used are preferably sulfated or phosphated adducts of 15 to 100 moles of ethylene oxide or preferably propylene oxide with polyhydric aliphatic alcohols having 2 to 6 carbon atoms, such as ethylene glycol, glycerol or pentaerythritol, or with at least two amino groups or one amino group and one hydroxyl group with amines 2 to 9 carbon atoms and alkyl sulfonates with 10 to 20 carbon atoms in the alkyl chain, alkylbenzenesulfonates with straight-chain or branched alkyl chain with 8 to 20 carbon atoms in the alkyl chain, such as, for example, nonyl or dodecylbenzenesulfonate, 1,3,5,7-tetramethyloctylbenzenesulfonate or octadecylbenzenesulfonate, and also benzene sulfonate Alkyln
• Lignin sulfonates polyphosphates and preferably formaldehyde condensation products of aromatic sulfonic acids, formaldehyde and optionally mono- or bifunctional phenols such as e.g. from cresol, ⁇ -naphtholsulfonic acid and formaldehyde, from benzenesulfonic acid, formaldehyde and naphthalenic acid, from naphthalenesulfonic acid and formaldehyde or from naphthalenesulfonic acid, dihydroxydiphenyl sulfone and formaldehyde.
• the disodium salt of di- (6-sulfonaphthyl-2-) methane is preferred.
• anionic dispersants can also be used.
• the anionic dispersants are normally in the form of their alkali metal salts, ammonium salts or amine salts. These dispersants are preferably used in an amount of 0.1 to 5 g / l of liquor.
• the dyebaths can, in addition to the auxiliaries already mentioned, also conventional additives, expediently electrolytes such as salts, e.g. sodium sulfate, ammonium sulfate, sodium or ammonium phosphates or polyphosphates, metal chlorides or nitrates such as sodium chloride, calcium chloride, magnesium chloride or Calcium nitrates, ammonium acetate or sodium acetate and / or acids, for example mineral acids such as sulfuric acid or phosphoric acid, or organic acids, suitably lower aliphatic carboxylic acids such as formic, acetic or oxalic acid and also alkalis, alkali donors or complexing agents.
• salts e.g. sodium sulfate, ammonium sulfate, sodium or ammonium phosphates or polyphosphates
• metal chlorides or nitrates such as sodium chloride, calcium chloride, magnesium chloride or Calcium nitrates, ammonium acetate or
• the acids serve primarily to adjust the pH of the liquors used according to the invention, which is generally 4 to 6.5, preferably 4.5 to 6.
• the dyeings are advantageously carried out from an aqueous liquor using the exhaust process.
• the liquor ratio can accordingly be chosen within a wide range, e.g. 1: 4 to 1: 100, preferably 1: 6 to 1:50.
• the temperature at which dyeing is carried out is at least 50 ° C and generally it is not higher than 140 ° C. It is preferably in the range from 80 to 135 ° C.
• Linear polyester fibers and cellulose triacetate fibers are preferably dyed by the so-called high-temperature process in closed and expediently also pressure-resistant apparatus at temperatures above 100 ° C., preferably between 110 and 135 ° C., and optionally under pressure.
• Circulation devices such as cross-wound or tree dyeing machines, reel runners, nozzle or drum dyeing machines, muff dyeing machines, paddles or jiggers are suitable as closed vessels.
• Cellulose-21 ⁇ 2-acetate fibers are preferably dyed at temperatures of 80-85 ° C.
• the dyeing process according to the invention can be carried out in such a way that the material to be dyed is first treated briefly with the compounds and then dyed, or preferably treated simultaneously with the compounds and the dye.
• the material to be dyed is preferably allowed to run for 5 minutes at 50 to 80 ° C. in a bath which contains the dye, the compound and, if appropriate, further additives and is adjusted to a pH of 4.5 to 5.5, the temperature increases within from 10 to 20 minutes to 100 to 110 ° C. and within a further 10 to 20 minutes to 125 to 130 ° C., and the dye liquor is left at this temperature for 15 to 90 minutes, preferably 30 minutes.
• the dyeings are completed by cooling the dye liquor to 50 to 80 ° C., rinsing the dyeings with water and, if appropriate, cleaning in a customary manner in an alkaline medium under reductive conditions. The dyeings are then rinsed and dried again.
• the dyeings are advantageously heat-treated to improve the lightfastness, e.g. Thermal insulation, subjected, which is preferably carried out at 160 to 180 ° C and for 30 to 90 seconds.
• vat dyes for the cellulose portion the goods are treated in the usual way first with hydrosulfite at a pH of 6 to 12.5 and then with oxidizing agent and finally washed out.
• polyester fiber materials are stabilized photochemically. i.e. protected against exposure, especially hot exposure, with visible and UV light.
• a particularly outstanding advantage of the method according to the invention is that, compared to previously known methods for the photochemical stabilization of polyester fiber materials, no pre- or post-treatment of the fiber material is required.
• a UV absorber 5 g of a UV absorber are mixed with 5 g of the condensation product of naphthalenesulfonic acid and formaldehyde as a dispersant, which is dissolved in 7.5 ml of water, with 20 g of quartz beads (diameter approx. 1 mm) and with a stirrer at approx. 1600 revolutions milled per minute until the particle size is below 2 ⁇ m.
• the dispersion is obtained from the quartz beads using a fine mesh sieve separated and adjusted to 20% of active substance with water. Then 0.3% carboxymethyl cellulose is stirred in to stabilize the dispersion.
• UVA UV absorber
• 39 jersey samples of 10 g each made from Diolen® are prepared, whereby 3 samples are always dyed together. 2 different concentrations are produced for each UVA, 3 samples are dyed without UVA.
• the dyeings are made in the usual way in pressure bombs in an HT apparatus.
• the fleets have the following basic composition: 2 g / l ammonium sulfate 0.5 g / l of a dispersant 0.2% CI Dispers Orange 53 [The liquors are always adjusted to pH 5 with formic acid; the dye is calculated based on the weight of the goods.]
• the dyeing is carried out in pressure bombs at a liquor ratio of 1:10 by first treating the jersey pieces at 50 ° C. for 5 minutes, then increasing the temperature to 100 ° C. in 10 minutes and then to 130 ° C. in a further 10 minutes . It is dyed at this temperature for 30 minutes, then to 50 ° C cooled, rinsed in warm water, centrifuged and dried in a forced air oven at 80 ° C. Finally, the 13 series of 3 pieces of 10 g each are divided into 3 series. While the Series 1 remains untreated, the Series 2 are treated at 180 ° C for 60 seconds and the Series 3 at 200 ° C for 60 seconds in a hot air heat setting device (e.g. that from W. Mathis, Niederhasli, Switzerland).
• a hot air heat setting device e.g. that from W. Mathis, Niederhasli, Switzerland.
• the procedure is as described in Example 2, with the exception that no dye is used.
• the heat setting is carried out under the same conditions.
• the dye batch consists of (calculated in% by weight):
• UV absorber III also shows better results for these dyeings.
• Gray dyeings with and without UV absorbers are produced on 7 skeins of 10 g each of a Terylene® staple yarn.
• the dyeing is carried out as described in Example 2, using the following dye mixture:
• Products I, III and VI are used as UV absorbers (see Table V).
• the hot light fastness properties were determined in accordance with Ford Eu Bo 50-2 (48 h and 96 h) and DIN 75.202, draft (Fakra; 96 h and 192 h). The following results are achieved:
• UV absorbers III and VI in the long-term tests give the better assessment than UV absorber I.

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• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Chemical & Material Sciences (AREA)
• Dispersion Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Coloring (AREA)
• Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
• Compositions Of Macromolecular Compounds (AREA)
• Artificial Filaments (AREA)
• Polyesters Or Polycarbonates (AREA)

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• 1988
  • 1988-02-17 US US07/156,640 patent/US4831068A/en not_active Expired - Lifetime
  • 1988-02-22 ES ES198888810105T patent/ES2032593T3/es not_active Expired - Lifetime
  • 1988-02-22 DE DE8888810105T patent/DE3870922D1/de not_active Expired - Lifetime
  • 1988-02-22 EP EP88810105A patent/EP0280653B1/de not_active Expired - Lifetime
  • 1988-02-22 AT AT88810105T patent/ATE76130T1/de not_active IP Right Cessation
  • 1988-02-26 AU AU12323/88A patent/AU610129B2/en not_active Ceased
  • 1988-02-26 JP JP63042447A patent/JPH0788634B2/ja not_active Expired - Fee Related
  • 1988-02-26 BR BR8800847A patent/BR8800847A/pt not_active IP Right Cessation
  • 1988-02-26 ZA ZA881377A patent/ZA881377B/xx unknown
  • 1988-02-27 KR KR1019880002031A patent/KR950007820B1/ko not_active IP Right Cessation

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