EP1383952A2 - Verfahren zur uv-schutzausrüstung von textilem material - Google Patents

Verfahren zur uv-schutzausrüstung von textilem material

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Publication number
EP1383952A2
EP1383952A2 EP02704685A EP02704685A EP1383952A2 EP 1383952 A2 EP1383952 A2 EP 1383952A2 EP 02704685 A EP02704685 A EP 02704685A EP 02704685 A EP02704685 A EP 02704685A EP 1383952 A2 EP1383952 A2 EP 1383952A2
Authority
EP
European Patent Office
Prior art keywords
textile material
acid
textile
component
components
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP02704685A
Other languages
German (de)
English (en)
French (fr)
Inventor
Thomas Heidenfelder
Jürgen Detering
Gerhard Wagenblast
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1383952A2 publication Critical patent/EP1383952A2/de
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/12—Water-insoluble compounds
    • C11D3/1213—Oxides or hydroxides, e.g. Al2O3, TiO2, CaO or Ca(OH)2
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/40—Dyes ; Pigments
    • C11D3/42—Brightening agents ; Blueing agents
    • 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
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
    • D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
    • D06M11/44—Oxides or hydroxides of elements of Groups 2 or 12 of the Periodic Table; Zincates; Cadmates
    • 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
    • D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
    • D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
    • D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
    • D06M11/46—Oxides or hydroxides of elements of Groups 4 or 14 of the Periodic Table; Titanates; Zirconates; Stannates; Plumbates
    • 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
    • D06M13/10—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 oxygen
    • D06M13/12—Aldehydes; Ketones
    • 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
    • D06M13/10—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 oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • 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
    • D06M13/10—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 oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/1845—Aromatic mono- or polycarboxylic acids
    • 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
    • D06M13/10—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 oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/203—Unsaturated carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/2035—Aromatic acids
    • 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
    • D06M13/10—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 oxygen
    • D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
    • 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
    • D06M13/325—Amines
    • D06M13/335—Amines having an amino group bound to a carbon atom of a six-membered aromatic ring
    • 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
    • D06M13/352—Heterocyclic compounds having five-membered heterocyclic rings
    • 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
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/25—Resistance to light or sun, i.e. protection of the textile itself as well as UV shielding materials or treatment compositions therefor; Anti-yellowing treatments

Definitions

  • the invention relates to a method for UV protective finishing of textile material, textile detergent, laundry treatment and laundry care formulations, finishing agent for UV protective finishing of textile material, the finished textile material itself and the use of zinc oxide and / or titanium dioxide together with organic UV absorbers.
  • UV radiation from sunlight on human skin are not limited to premature skin aging and the formation of skin erythema (reddening of the skin, sunburn). Exposing the skin to UV radiation for too long and too intensely increases the risk of developing skin cancer. Primarily responsible for the reddening of the skin and the increased risk of skin cancer is the UV-B portion of the UV radiation, i.e. the range from approx. 280 to approx. 315 nm. The maximum erythema effect is 308 nm.
  • Textiles scatter or absorb UV radiation and thus protect the skin as a physical barrier against the damaging effects of sunlight (“textile skin protection").
  • textile skin protection the skin-protecting effect of the textiles depends on many factors such as the type of fiber, fabric construction, fabric weight, color, moisture content or type of finishing or finishing. For example, summer clothing in the form of light and light cotton textiles offers only weak and therefore inadequate protection against UV radiation.
  • Too high a dose of UV radiation can not only cause skin damage, it is also largely responsible for the fading of colored textiles caused by sunlight. There is therefore a great interest in protecting both colored textiles and human skin from the damaging effects of UV radiation.
  • Stilbene and triazine bases as described in EP-A 682 145, GB-A 2 313 375 or EP-A 728 749.
  • the effectiveness of the agents is still in need of improvement have a number of disadvantages.
  • Significant disadvantages are their poor formulability and their poor solubility in the respective application medium.
  • sunscreens in particular from the group of phenylbenzotriazoles, dibenzoylmethanes, p-aminobenzoic acid esters, cinnamic acid esters, salicylic acid esters, nitrogen-free 2-hydroxybenzophenones, phenylbenzimidazoles and 2-cyano-3,3-diphenylacrylic acid esters, but also without mixtures here Notes on the respective mixing ratios - protect dyed textile material from fading of the color.
  • WO 96/03486 describes essentially the same sunscreens as they are mentioned in WO 97/44422 as means for protecting dyed textile material from color fading.
  • the effectiveness of these agents is also in need of improvement and has a number of disadvantages.
  • a major disadvantage is the often too low UV stability of the above-mentioned agents.
  • pigments such as titanium dioxide or zinc oxide in fibers
  • Synthetic fibers made of polyamide, polyester or polyacrylonitrile are particularly suitable for this type of UV protective equipment. Cellulose fibers are not very suitable for this.
  • JP 03/277699 describes solid detergents, especially soaps, with a zinc oxide content of 0.1 to 15% by weight.
  • the soaps show good UV absorption and have a deodorising effect.
  • WO 98/42909 describes the UV protective finish of textile fabrics by treatment with inorganic particles which can absorb, reflect or scatter UV radiation, in combination with a binder. These particles can also be used during the washing of textiles.
  • the object of the present invention is to provide improved and more photostable UV absorber systems in their effect.
  • the task is solved by a process for UV protection of textile material, in which one
  • component A Zinc oxide and / or titanium oxide as component A and (b) applying one or more organic UV absorbers as component B to the textile material.
  • Zinc oxide and / or titanium dioxide are used as component A as inorganic pigments absorbing UV radiation.
  • Component A can consist of zinc oxide or titanium dioxide either alone or from mixtures of the two pigments.
  • Titanium dioxide can be used in its three modifications rutile, anatase or brookite; it is preferably used as rutile.
  • the particle size is generally from 0.01 to 100 ⁇ m, preferably from 0.02 to 0.25 ⁇ m.
  • Zinc oxide is generally used with a particle size of 0.01 to 100 microns.
  • the particle size is preferably in the range from 0.02 to 2 ⁇ m, particularly preferably in the range from 0.08 to 0.25 ⁇ m.
  • the titanium dioxide and zinc oxide pigment particles can have a passivation layer made of inorganic oxides, in particular of silicon dioxide or aluminum oxide.
  • the pigment surface can also be specifically hydrophilized or hydrophobized by treatment with organic compounds or silicones.
  • Be used for surface modification ⁇ for example, amines, cationic polymers such as amino-containing polymers, polyols, organophosphates, alkyl phthalates, stearic acid, lauric acid or silicone oils.
  • component B which have at least one UV absorption maximum in the range from 280 to 450 nm.
  • component B contains those compounds which have at least one UV absorption maximum in the range from 290 to 375 nm.
  • component B contains compounds which have at least one UV absorption maximum in the range from 280 to 315 nm (UV-B range) with an EV value of at least 200, in particular at least 250, and at least one UV absorption maximum Range from 315 to 400 nm (UV-A range) with an E ⁇ value of at least 200, in particular at least 250.
  • Organic UV absorbers B have one or more bands in the UV absorption spectrum.
  • UV absorption maxima are to be understood here as the bands belonging to the corresponding local or absolute maxima in the UV spectrum of the respective compound, measured in conventional organic solvents such as dichloromethane or methanol at room temperature.
  • the E ⁇ value denotes the absorbance of the organic UV absorber B, which is measured in solution at a concentration of 1% by weight and a layer thickness of 1 cm.
  • Dichloromethane is usually used as the solvent, the use of other solvents customary for such UV measurements does not produce fundamentally different values.
  • the mixture according to the invention contains, as component B, those organic UV absorbers which contain an n-octanol / water
  • Log P have distribution coefficients log P of at least 1.9, in particular at least 2.5, especially at least 3.3. Log P can be determined or calculated experimentally. Both procedures are described in Chemical Reviews Volume 71, No. 5, pages 52-5-616
  • Organic UV absorbers B which are selected from the group consisting of
  • esters of p-aminobenzoic acid (III) esters of p-aminobenzoic acid, (IV) esters of cinnamic acid,
  • Typical UV-absorbing phenylbenzotriazoles (I) are:
  • Typical UV-absorbing dibenzoylmethanes are: 3- (4-isopropylphenyl) -3-phenylpropane-1,3-dione (Eusolex® 8020), l- (4-tert-butylphenyl) -3- (4-methoxyphenyl) propane-1,3-dione (Uvinul ® BMBM), 1, 3-bis (4-methoxyphenyl) propane-1, 3-dione.
  • Typical UV-absorbing esters of p-aminobenzoic acid (III) are:
  • Typical UV-absorbing esters of cinnamic acid are:
  • Typical UV-absorbing esters of salicylic acid (V) are:
  • Typical UV-absorbing phenylbenzimidazoles are:
  • Typical UV-absorbing acrylates are: 3-Imidazol-4-yl-acrylic acid, 3-imidazol-4-yl-acrylic acid ethyl ester, 2-cyano-3- (4-methoxyphenyl) acrylic acid, 2-cyano-3- (4-methoxyphenyl) acrylic acid hexyl ester.
  • Preferred acrylates are C 6 to C 18 alkyl esters or C 5 to C 8 cycloalkyl esters of 2-cyano-3,3-diphenylacrylic acid.
  • the C 6 to C 18 alcohol residue in the cyano-3,3-diphenylacrylic acid esters can be linear or mono- or polydranched, it can be of natural or synthetic origin.
  • Such alcohols can be, for example, fatty alcohols, oxo alcohols, Ziegler alcohols or Guerbet alcohols.
  • Typical examples of such compounds are n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, iso-nonyl, n-decyl, n-dodecyl, n-tridecyl, iso-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl or eicosyl ester.
  • Unsaturated alcohol residues such as the oleyl, linolyl or linolenyl residue can also occur. Mixtures of such esters can also be present.
  • C 5 - to C 8 -cycloalkanol residues in the cyano-3,3-diphenylacrylic acid esters are, for example, cyclopentyl, 2- or 3-methylcyclopentyl, cyclohexyl, 2-, 3- or 4-methylcyclohexyl, dimethylcyclohexyl, cycloheptyl or cyclooctyl radicals into consideration.
  • Linear or mono- or poly-branched C 8 to C 13 alkyl esters of 2-cyano-3,3-diphenylacrylic acid are preferred.
  • the corresponding 2-ethylhexyl ester is commercially available as Uvinul® N-539 T from BASF Aktiengesellschaft.
  • Typical UV-absorbing diarylbutadienes are in particular 4,4-diarylbutadienes of the formula (1), as described in DE-A 198 28 463 for cosmetic and pharmaceutical preparations:
  • C 2 -alkyl C 2 -C 10 alkenyl, C 3 -C 10 cycloalkyl, C 3 -C ⁇ 0 cycloalkenyl, CC ⁇ alkoxy, C 1 -C 2 o-alkoxycarbonyl, C ⁇ - C 2 alkylamino, CrC ⁇ dialkylamino, aryl, heteroaryl, optionally substituted, and water-solubilizing substituents selected from the group consisting of
  • R 3 is hydrogen, COOR 5 , COR 5 , CONR 5 R 6 , CN;
  • R 4 COOR 6 , COR 6 , CONR 5 R 6 ;
  • R 5 is hydrogen, [X] 0 -R 7 , Cj- -alkylene-SOsY, -C-C 6 -alkylene-PO 3 Y, CC 6 -alkylene- N (R 8 ) 3 + A " ;
  • Y is hydrogen, Na + , K + , Mg 2+ , Ca 2+ , Li + , Al 3+ , N (R 8 ) 4 + ;
  • R 9 is hydrogen, -CC 6 alkyl, C 2 -C 6 alkenyl; n 1 to 3;
  • Typical UV-absorbing amino-substituted hydroxybenzophenones are, in particular, those of the formula (2) as described in German patent application No. 199 17 906.9 for cosmetic and pharmaceutical preparations:
  • R ⁇ d R 2 is hydrogen, C 1 -C 20 alkyl, C 2 -C 10 alkenyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkenyl, where the substituents R 1 and R 2 together with the Nitrogen atom to which they are attached can form a 5- or 6-membered ring;
  • R 3 and R 4 Ci- jo-Al yl, C -C ⁇ 0 alkenyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkenyl, d- C 12 alkoxy, C 1 -C 2 o-alkoxycarbonyl , Ci-C ⁇ -alkylamino, Ci-C ⁇ - dialkylamino, aryl, heteroaryl, optionally substituted, and water-solubilizing substituents selected from the group consisting of a nitrile group, carboxylate, sulfonate or ammonium residues;
  • X is hydrogen, COOR 5 , CONR 6 R 7 ;
  • R 5 to R 7 are hydrogen, C 1 -C 20 alkyl, C 2 -C 10 alkenyl, C 3 -C ⁇ o cycloalkyl, C 3 -C 10 cycloalkenyl, - (YO) 0 -Z, aryl;
  • Typical UV-absorbing triazines are:
  • 2,4,6-Trianilino-4- (carbo-2'-ethylhexyl-1 '-oxy) - 1, 3, 5-triazine (Uvinul® T-150), 2-ethylhexyl-4 - ⁇ [4- ⁇ 4- [tert-butylamino] carbonyl] anilino ⁇ -6- (4 - ⁇ [2-ethylhexyl) oxy] carbonyl ⁇ anilino) -l, 3,5-triazin-2-yl] amino ⁇ benzoate,
  • organic UV absorbers B In addition to the compounds of types (I) to (XI), the following can also be used as organic UV absorbers B:
  • Particularly preferred organic UV absorbers B which together with zinc oxide and / or
  • the compounds used are titanium dioxide:
  • antioxidants and / or radical scavengers include all compounds that are usually used to stabilize food and feed but also to stabilize plastics or lubricants.
  • a list of such connections can be found e.g. in Kirk-Othmer, Encyclopedia of Chemical Technology, fourth edition, volume 3, p. 424-447 or in Ullmann's Encyclopedia of Industrial Chemistry, sixth edition, 2000 Electronic Release, chapters antioxidants and food additives.
  • Substituted phenols, hydroquinones, pyrocatechols and gallates such as 2,6-di-tert-butylphenol, 2,4,6-tri-t-butylphenol, 2,4-dimethyl-6-tert-butylphenol, 2,6- Di-tert-butyl-4-methylphenol, 2,6-di-tert-butyl-4-methoxyphenol, 3-tert-butyl-4-methoxyphenol, 2,2'-methylenebis (4-methyl-6-tert .-butylphenol), propyl, octyl and dodecyl gallate or tert-butyl hydroquinone (TBHQ), butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT),
  • TBHQ butylated hydroxyanisole
  • BHT butylated hydroxytoluene
  • Irganox® antioxidants from Ciba-Geigy
  • TBP Trihydroxybutyrophenone
  • ⁇ -tocopherol and its natural or synthetic derivatives such as acetyl- ⁇ -tocopherol,
  • Ascorbic acid and ascorbic acid derivatives in particular esterification products with long-chain fatty acids such as ascorbyl palmitate,
  • Diazabicyclooctane (DABCO) Chroman derivatives such as long-chain esters of 2,5,7,8-tetramethyl-6-hydroxychroman-2-acid,
  • aromatic amines such as ethoxyquin
  • organic sulfides such as 3,3'-thiodipropionic acid and dilaurylthiodipropionate
  • sterically hindered amines e.g. of the tetramethylpiperidine type such as Uvinul® 4049H, Uvinul® 4050H and Uvinul® 5050H from BASF AG,
  • Hydroxylamines such as those of dialkylamines and hydroxylamine ether derivatives of the tetramethylpiperidine compounds,
  • the inorganic pigments A and organic UV absorber B work together excellently as textile fiber-affine UV absorbers and reinforce each other in their effect. On the one hand, they protect human skin from damaging UV radiation when applied to textile material. On the other hand, they protect dyed textile material from color fading. Both protective effects preferably occur simultaneously.
  • Textile materials on which components A and B mount and develop their protective effect there, include in particular items of clothing, i.e. Textiles that are worn on human skin, but also house and garden items made of or with colored textiles such as awnings and parasols that are exposed to intense sunlight.
  • This textile material to be protected preferably consists of cellulose (cotton) or contains cellulose, for example clothing textiles made of cotton or of cotton-polyester mixtures.
  • the present invention also relates to the use of zinc oxide and / or titanium dioxide together with organic UV absorbers on textile material for protection the human skin from damaging UV radiation and / or to protect dyed textile material from color fading.
  • the mixture comprising components A and B is usually applied to the textile material, for example by spraying or dipping and pressing, in the form of an aqueous liquor which contains components A and B and may also contain further ingredients.
  • Components A and B can be applied to the textile material during textile finishing during the production of the textile material, during textile washing, during textile laundry pretreatment and / or after-textile treatment.
  • the UV protection factor UPF of the textile material is increased by the UV protective equipment.
  • the UN protection factor UPF (Ultraviolet Radiation Protection Factor") of textiles is tuned according to the Australian / New Zealand standard AS / NZS 4399: 1996 using an in vitro method.
  • the UV permeability of the textile object is measured.
  • the protection factor can be determined directly from the spectral transmission using the following equation:
  • ⁇ ⁇ is the spectral erythema effectiveness of UV radiation at the wavelength ⁇
  • ⁇ ⁇ is the spectral transmission of the textile object at the wavelength ⁇ .
  • the present invention also relates to a textile detergent formulation which comprises 0.01 to 20% by weight, preferably 0.1 to 10% by weight, particularly preferably 0.1 to 5 % By weight of components A and B in addition to other customary constituents.
  • the weight ratio of component A to component B is preferably from 20: 1 to 1:10, particularly preferably from 8: 1 to 1: 5 and particularly preferably from 3: 1 to 1: 1.
  • the addition of components A and B separately in the formulation or the pre-made mixture of A and B can be incorporated into the formulation.
  • Textile detergent formulations according to the invention can be solid or liquid formulations.
  • Solid detergent formulations according to the invention generally contain further customary constituents
  • component F 0 to 60% by weight of other customary ingredients such as cationic surfactants, bulking agents, enzymes, perfume, complexing agents, corrosion inhibitors, bleaching agents, bleach activators, bleaching catalysts, dye transfer inhibitors, graying inhibitors, soil release polyesters, dyes, dissolution improvers and / or disintegrant as component F,
  • customary ingredients such as cationic surfactants, bulking agents, enzymes, perfume, complexing agents, corrosion inhibitors, bleaching agents, bleach activators, bleaching catalysts, dye transfer inhibitors, graying inhibitors, soil release polyesters, dyes, dissolution improvers and / or disintegrant as component F,
  • the solid detergent formulations according to the invention are usually in the form of powder, granules, extrudate or in tablet form.
  • Liquid detergent formulations according to the invention generally contain further customary constituents
  • component C 0.1 to 40% by weight of at least one nonionic and / or anionic surfactant as component C, (d) 0 to 20% by weight of one or more inorganic builders as component D,
  • customary ingredients such as cationic surfactants, soda, enzymes, perfume, complexing agents, corrosion inhibitors, bleaching agents, bleach activators, bleaching catalysts, color transfer inhibitors, graying inhibitors, soil release polyesters, dyes, non-aqueous Solvents hydrotropes, thickeners and / or alkanolamines as component F and
  • Suitable anionic surfactants are in particular:
  • alkoxylated C to C 22 alcohols alkyl ether sulfates
  • Compounds of this type are prepared, for example, by first alkoxylating a C 8 to C 22 , preferably a C 10 to C 8 alcohol, for example a fatty alcohol, and then sulfating the alkoxylation product.
  • Ethylene oxide is preferably used for the alkoxylation;
  • linear C 8 to C 20 alkyl benzosulfonates LAS
  • LAS alkyl benzosulfonates
  • alkyl toluenesulfonates preferably linear C 8 to C 20 alkyl benzosulfonates (LAS), preferably linear C 9 to C 13 alkyl benzene sulfonates and alkyl toluenesulfonates
  • Alkanesulfonates such as C 8 - to C ⁇ -, preferably C 10 - to C 18 -alkanesulfonates,
  • Soaps such as the Na and K salts of C 8 to C 2 carboxylic acids.
  • the anionic surfactants mentioned are preferably added to the detergent in the form of salts.
  • Suitable cations in these salts are alkali metal ions such as Sodium, potassium and lithium and ammonium ions such as hydroxyethylammonium, di (hydroxyethyl) ammonium and tri (hydroxyethyl) ammonium.
  • Suitable nonionic surfactants are in particular:
  • alkoxylated C 8 to C 22 alcohols such as fatty alcohol alkoxylates or oxo alcohol alkoxylates. These can be alkoxylated with ethylene oxide, propylene oxide and / or butylene oxide. All alkoxylated alcohols which contain at least two molecules of one of the above-mentioned alkylene oxides added can be used as surfactants.
  • surfactants here come block polymers of ethylene oxide,
  • Propylene oxide and / or butylene oxide or adducts which contain the alkylene oxides mentioned in a statistical distribution.
  • the nonionic surfactants generally contain 2 to 50, preferably 3 to 20, moles of at least one alkylene oxide per mole of alcohol. These preferably contain ethylene oxide as the alkylene oxide.
  • the alcohols preferably have 10 to 18 carbon atoms.
  • the type of alkoxylation catalyst used in the preparation has a broad or narrow alkylene oxide homolog distribution
  • Alkylphenol alkoxylates such as alkylphenol ethoxylates with C 6 - to C 4 alkyl chains and 5 to 30 alkylene oxide units;
  • Alkyl polyglucosides having 8 to 22, preferably 10 to 18 carbon atoms in the alkyl chain and generally 1 to 20, preferably 1.1 to 5, glucoside units;
  • glucamides fatty acid amide alkoxylates, fatty acid alkanolamide alkoxylates and block copolymers of ethylene oxide, propylene oxide and / or butylene oxide.
  • Suitable inorganic builders are in particular:
  • zeolites Suitable zeolites are in particular zeolites A, X, B, P, MAP and HS in their Na form or in forms in which Na is partly replaced by other cations such as Li, K, Ca, Mg or ammonium; crystalline silicates such as, in particular, disilicates or layered silicates, for example ⁇ -Na 2 Si 2 O 5 or ⁇ -Na 2 Si 2 O 5.
  • the silicates can be used in the form of their alkali metal, alkaline earth metal or ammonium salts, preferably as Na, Li and Mg silicates;
  • amorphous silicates such as sodium metasilicate or amorphous disilicate
  • Carbonates and hydrogen carbonates can be used in the form of their alkali metal, alkaline earth metal or ammonium salts.
  • Na, Li and Mg carbonates or bicarbonates are preferred, in particular sodium carbonate and / or sodium bicarbonate;
  • Polyphosphates such as pentasodium triphosphate.
  • Suitable organic cobuilders are in particular low molecular weight, oligomeric or polymeric carboxylic acids.
  • Suitable low molecular weight carboxylic acids are, for example, citric acid, hydrophobically modified citric acid such as. B. agaricic acid, malic acid, tartaric acid, gluconic acid, glutaric acid, succinic acid, imidodisuccinic acid, oxydisuccinic acid, propa ⁇ tricarboxylic acid, butanetetracarboxylic acid, cyclopentanetetracarboxylic acid, alkyl and alkenyl succinic acids and aminopolycarboxylic acids such as e.g.
  • Nitrilotriacetic acid ß-alaninediacetic acid, ethylenediaminetetraacetic acid, serinediacetic acid, isoserinediacetic acid, N- (2-hydroxyethyl) iminodiacetic acid, ethylenediaminedisuccinic acid and methyl and ethylglycinediacetic acid;
  • Suitable oligomeric or polymeric carboxylic acids are, for example, homopolymers of acrylic acid, oligomaleic acids, copolymers of maleic acid with acrylic acid, methacrylic acid, C 2 -C 22 olefins such as isobutene or long-chain ⁇ -olefins, vinyl alkyl ethers with C 1 -C 8 alkyl groups, vinyl acetate, vinyl propionate, (Meth) acrylic esters of C Cs alcohols and styrene. It is preferred to use the
  • Suitable bleaching agents are, for example, adducts of hydrogen peroxide with inorganic salts such as sodium perborate monohydrate, sodium perborate tetrahydrate or sodium carbonate perhydrate or percarboxylic acids such as phthalimidopercaproic acid.
  • Suitable bleach activators are, for example, N, N, N ', N'-tetraacetylethylene diamine (TAED), sodium p-nonanoyloxybenzenesulfonate or N-methylmorpholinium acetonitrile-methyl sulfate.
  • TAED N, N, N ', N'-tetraacetylethylene diamine
  • sodium p-nonanoyloxybenzenesulfonate sodium p-nonanoyloxybenzenesulfonate or N-methylmorpholinium acetonitrile-methyl sulfate.
  • Enzymes preferably used in detergents are proteases, lipases, amylases, cellulases, oxidases or peroxidases.
  • Suitable color transfer inhibitors are, for example, homopolymers and copolymers of 1-vinylpyrrolidone, 1-vinylimidazole or 4-vinylpyridine-N-oxide. Homo- and copolymers of 4-vinylpyridine reacted with chloroacetic acid are also suitable as color transfer inhibitors.
  • the present invention furthermore relates to laundry aftertreatment and laundry care compositions which, in addition to 0.01 to 20% by weight, preferably 0.1 to 10% by weight, particularly preferably 0.1 to 5% by weight, of components A and B. contain other common ingredients.
  • the weight ratio of component A to component B is preferably from 20: 1 to 1:10, particularly preferably from 8: 1 to 1: 5, in particular from 3: 1 to 1: 1.
  • the addition of components A and B separately in the formulation or the pre-made mixture of A and B can be incorporated into the formulation.
  • the laundry aftertreatment and laundry care compositions according to the invention generally contain further customary constituents
  • Stabilizers fiber and color protection additives, viscosity modifiers, soil release additives, graying inhibitors, color transfer inhibitors, Complexing agents, corrosion protection additives, bactericides, preservatives, non-aqueous solvents, hydrotropes and / or alkanolamines as component E,
  • cationic polymers which contain amino and / or ammonium groups and are water-soluble or water-dispersible can be used as cationic polymers (component F).
  • cationic polymers are polyethyleneimines, amidated, alkoxylated and / or alkylated polyethyleneimines, crosslinked polyethyleneimines, polyamidoamines, alkoxylated and / or alkylated polyamidoamines, crosslinked polyamidoamines, crosslinked polyamidoamines grafted with ethyleneimine, amine-epichlorohydrin polycondensates, polyvinylamines, alkoxylated Polyvinylformamides, polyallylamines,
  • Polydimethyldiallylammonium chlorides polymers containing 1-vinylimidazole units such as poly-1-vinylimidazole or poly- (l-vinylimidazole-co-l-vinylpyrrolidone), polymers containing quaternary vinylimidazole units, condensates of imidazole and epichlorohydrin, basic (meth) acrylamide or (meth) acrylamide units containing polymers, basic quaternary (meth) acrylamide or (meth) acrylic ester units containing polymers and / or lysine condensates.
  • 1-vinylimidazole units such as poly-1-vinylimidazole or poly- (l-vinylimidazole-co-l-vinylpyrrolidone
  • polymers containing quaternary vinylimidazole units condensates of imidazole and epichlorohydrin
  • Cationic polymers are also understood to mean amphoteric polymers which have a net cationic charge, i.e. the polymers contain both anionic and cationic monomers in copolymerized form, but the molar proportion of the cationic units contained in the polymer is greater than that of the anionic units.
  • Preferred cationic surfactants are selected from the group of the quaternary diesterammonium salts, the quaternary tetraalkylammonium salts, the quaternary diamidoammonium salts, the amidoamine esters and imidazolium salts. These are preferably contained in the laundry detergent in an amount of 3 to 30% by weight.
  • Examples are quaternary diester ammonium salts which have two C ⁇ to C 22 alk (en) yl carbonyloxy (mono- to pentamethylene) residues and two C to C 3 alkyl or hydroxyalkyl residues on the quaternary N atom and as a counter ion for example, wear chloride, bromide, methyl sulfate or sulfate.
  • Quaternary diesterammonium further include in particular those corresponding to the trimethylene group carries a C ⁇ - to C 22 -alk (en) ylcarbonyloxytrimethylen radical, on the central carbon atom form a C ⁇ - to C 22 -alk (en) ylcarbonyloxy radical, and have three C to C 3 alkyl or hydroxyalkyl radicals on the quaternary N atom and, for example, carry chloride, bromide, methyl sulfate or sulfate as counterion.
  • Quaternary tetraalkylammonium salts are, in particular, those which have two C 1 -C 6 -alkyl radicals and two C 8 - to C 24 -alk (en) yl radicals on the quaternary N atom and, for example, chloride, bromide, methyl sulfate or sulfate as counterion wear.
  • Quaternary diamidoammonium are in particular those which have two C 8 - a substituent selected from hydrogen, methyl, ethyl and polyoxyethylene having up to 5 oxyethylene units and as fourth radical a methyl group on the quaternary nitrogen alk (en) ylcarbonylaminoethylene radicals, - to C 2 -Atom and have as counterion, for example, chloride, bromide, methyl sulfate or sulfate.
  • Amidoamino esters are, in particular, tertiary amines which, as substituents on the N atom, have a C ⁇ to C 22 alk (en) ylcarbonylamino (mono- to trimethylene) radical, a C ⁇ to C 22 alk (en) ylcarbonyloxy (mono- to trimethylene) residue and a methyl group.
  • Imidazolinium salts are in particular those in which the 2-position of the heterocycle, a C 14 - to C 1 -alk (en) yl radical, the neutral N-atom form a C 14 - to C 18 - Alk (en) ylcarbonyl (oxy or amino) ethylene radical and hydrogen, methyl or ethyl on the N atom carrying the positive charge, counterions here are, for example, chloride, bromide, methyl sulfate or sulfate.
  • the present invention also relates to the use of zinc oxide and / or titanium dioxide together with organic UV absorbers in textile detergents, laundry aftertreatment and laundry care products.
  • the present invention also relates to finishing agents for UV protective finishing of textile materials, comprising components A and B.
  • finishing agents according to the invention can be used, for example, as finishing agents in the narrower sense in the manufacture of the textiles or in the form of an aqueous one
  • Wash liquor or as a liquid textile treatment agent For example possible to treat the textiles with the finishing agent in connection with the textile production. Textiles that have not yet been treated or have been treated insufficiently with finishing agents can be treated, for example, in the home area before or after washing with a textile treatment agent which contains the inorganic pigments A and the organic UV absorbers B. However, it is also possible to treat the textiles with components (A) and (B) in the main wash cycle or after the main wash cycle in the care or fabric softener cycle, in some cases using the formulations described above.
  • Example 1 Use of the UV protection agents in the textile laundry aftertreatment in the fabric softener bath and determination of the UV protection factor UPF
  • the fabric was then checked for light stability tissue sample was placed in a table exposure apparatus SUNTEST ® CPS (Fa. Heraeus, Hanau) exposed for 4 and 24 hours (with out-door conditions with filter WG 295) at maximum radiation power of the device. After 4 and 24 hours of exposure was again the UV- Protection factor determined.
  • SUNTEST ® CPS Fe. Heraeus, Hanau
  • A 2-cyano-3,3-diphenylacrylic acid 2-ethylhexyl ester (Uvinul® N-539 T)
  • B 2-hydroxy-4- (n-octyloxy) benzophenone (Uvinul® 3008)
  • Example 2 Use in textile laundry aftertreatment in fabric softener and conditioner and determination of the light stability of the dyed cotton fabric used
  • Cotton fabric dyed with Reoxid Schwarz 5 (1/3 directional depth type) was rinsed in the fabric softener with a commercially available formulation (Downy from Lenor®, 1000 ppm based on the liquor) with the addition of a UV absorber combination according to the invention (each 200 ppm based on the liquor) treated in a liquor ratio of 1: 12.5.
  • the colored fabrics were removed and checked for light stability in the dried state.
  • the light stabilities (photostabilities) were measured as follows:
  • the samples were exposed in a table exposure device SUNTEST® (from Heraeus, Hanau) for 8 or 24 hours (under out-door conditions with filter WG 295) at maximum radiation power of the device.
  • K Absorption coefficient
  • S scattering coefficient
  • the photo stabilities were evaluated on the basis of the K / S values remaining after 8 or 24 hours of exposure, based on the K / S values before exposure (K / S in each case at the maximum of the K / S spectra The larger the value in% given in Table 2, the greater the photostability.
  • Z-COTE® from BASF AG was used as the inorganic pigment.

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  • Engineering & Computer Science (AREA)
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  • Textile Engineering (AREA)
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  • Detergent Compositions (AREA)
  • Cosmetics (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
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