EP1263919A1 - Use of optical brighteners from the class of the stilbene compounds as antimicrobially active substances - Google Patents
Use of optical brighteners from the class of the stilbene compounds as antimicrobially active substancesInfo
- Publication number
- EP1263919A1 EP1263919A1 EP01917048A EP01917048A EP1263919A1 EP 1263919 A1 EP1263919 A1 EP 1263919A1 EP 01917048 A EP01917048 A EP 01917048A EP 01917048 A EP01917048 A EP 01917048A EP 1263919 A1 EP1263919 A1 EP 1263919A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- aryl
- hydrogen
- formula
- use according
- 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- Withdrawn
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 21
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 239000013543 active substance Substances 0.000 title claims description 4
- 239000000463 material Substances 0.000 claims abstract description 23
- 239000004753 textile Substances 0.000 claims abstract description 22
- 239000003599 detergent Substances 0.000 claims abstract description 15
- 239000000835 fiber Substances 0.000 claims abstract description 15
- 230000000845 anti-microbial effect Effects 0.000 claims abstract description 11
- 238000005406 washing Methods 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- -1 C C^al yl Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 241000894006 Bacteria Species 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 244000005700 microbiome Species 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229920003043 Cellulose fiber Polymers 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 229920001817 Agar Polymers 0.000 description 8
- 239000008272 agar Substances 0.000 description 8
- PMPJQLCPEQFEJW-HPKCLRQXSA-L disodium;2-[(e)-2-[4-[4-[(e)-2-(2-sulfonatophenyl)ethenyl]phenyl]phenyl]ethenyl]benzenesulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC=C1\C=C\C1=CC=C(C=2C=CC(\C=C\C=3C(=CC=CC=3)S([O-])(=O)=O)=CC=2)C=C1 PMPJQLCPEQFEJW-HPKCLRQXSA-L 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000011734 sodium Chemical group 0.000 description 3
- 229910052724 xenon Inorganic materials 0.000 description 3
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- UKPIWNGOQCLXIR-UHFFFAOYSA-N 2-amino-6-(2-phenylethenyl)benzenesulfonic acid Chemical class NC1=CC=CC(C=CC=2C=CC=CC=2)=C1S(O)(=O)=O UKPIWNGOQCLXIR-UHFFFAOYSA-N 0.000 description 1
- YGUMVDWOQQJBGA-VAWYXSNFSA-N 5-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-[(e)-2-[4-[(4-anilino-6-morpholin-4-yl-1,3,5-triazin-2-yl)amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound C=1C=C(\C=C\C=2C(=CC(NC=3N=C(N=C(NC=4C=CC=CC=4)N=3)N3CCOCC3)=CC=2)S(O)(=O)=O)C(S(=O)(=O)O)=CC=1NC(N=C(N=1)N2CCOCC2)=NC=1NC1=CC=CC=C1 YGUMVDWOQQJBGA-VAWYXSNFSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241000139306 Platt Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004115 Sodium Silicate Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001332 colony forming effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 238000005202 decontamination Methods 0.000 description 1
- 230000003588 decontaminative effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004627 regenerated cellulose Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial 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
- C11D3/40—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
- D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
- D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
- D06L4/60—Optical bleaching or brightening
-
- 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
- D06M10/00—Physical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. ultrasonic, corona discharge, irradiation, electric currents, or magnetic fields; Physical treatment combined with treatment with chemical compounds or elements
- D06M10/001—Treatment with visible light, infrared or ultraviolet, X-rays
-
- 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
- D06M13/02—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
- D06M13/03—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons with unsaturated hydrocarbons, e.g. alkenes, or alkynes
- D06M13/07—Aromatic hydrocarbons
-
- 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
- D06M16/00—Biochemical treatment of fibres, threads, yarns, fabrics, or fibrous goods made from such materials, e.g. enzymatic
-
- 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
- C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
- C11D2111/40—Specific cleaning or washing processes
- C11D2111/46—Specific cleaning or washing processes applying energy, e.g. irradiation
Definitions
- the present invention relates to the use of a laundry detergent that comprises at least one optical brightener from the class of the stilbene compounds for the antimicrobial finishing of textile materials and to the use of these compounds as antimicrobially active substances against microorganisms.
- washing with a commercially available laundry detergent removes the soil from the textile materials and usually imparts an improved appearance to them.
- washing and drying of textiles does not always remove bacteria to the desired degree.
- a normal wash do anything to prevent subsequent contamination by undesirable bacteria.
- optical brighteners from the class of the stilbene compounds which are customarily used in the laundry detergent and textile industries have antimicrobial properties when the textile material is simultaneously irradiated with a light source.
- the present invention accordingly provides for the use of a laundry detergent that comprises at least one optical brightener from the class of the stilbene compounds for the antimicrobial finishing of textile fibre materials, which comprises washing the fibre materials with this laundry detergent and subsequently exposing the washed textile material to a light source.
- Useful optical brighteners for the invention preferably conform to the formula
- Ri is a radical of the formula — NH- ⁇ V-corR, ;
- R 3 is substituted or unsubstituted alkyl or aryl
- R 4 is M or substituted or unsubstituted alkyl or aryl
- R 5 is hydrogen; substituted or unsubstituted alkyl or aryl; or -NR 7 R 8 , wherein R 7 and R 8 are independently hydrogen; substituted or unsubstituted alkyl or aryl; or R 7 and R 8 combine with the joining nitrogen atom to form a heterocyclic radical, especially morpholino or piperidino radical;
- R 6 is hydrogen or substituted or unsubstituted alkyl or aryl
- R 2 is hydrogen; substituted or unsubstituted alkyl or aryl; a radical of the formula — N o,
- R 1 and R ⁇ are independently -OH, -CI; -NH 2 , -O-C C 4 alkyl, -O-aryl, -NH-C ⁇ alkyl,
- R 9 and R 10 are independently hydrogen, C C 4 alkyl, phenyl or a radical of the formula
- R is hydrogen, CI or SO 3 M
- R 12 is -CN, -SO 3 M, -S(C C 4 alkyl) 2 or S(aryl) 2 ;
- R 13 is hydrogen, -SO 3 M, -O-C ⁇ alkyl, -CN, -CI, -COO-C ⁇ alkyl, or CON ⁇ -C ⁇ alkyl) ⁇
- R 14 is hydrogen; -Chalky!, -CI or -SO 3 M;
- R 15 and R 16 are independently hydrogen, C ⁇ alkyl, -SO3M, -CI or -O-C ⁇ alkyl;
- R 17 is hydrogen or 0,-C ⁇ alkyl;
- R 18 is hydrogen, C 1 -C 4 alkyl, -CN, -CI, -COO-C ⁇ alkyl, -CON(C 1 -C 4 alkyl) 2 , aryl or -O-aryl;
- M is hydrogen, Na, K, Ca, Mg, ammonium, mono-, di-, tri- or tetra-C C 4 alkylammonium, mono-, di- or tri-C r C hydroxyalkylammonium or ammonium that is di- or trisubstituted with a mixture of C C 4 aIkyl and C 1 -C 4 hydroxyalkyl groups; and n-i, n 2 and n 3 are independently 0 or 1.
- Rs, Re, R7 and R a is CrC 12 alkyl, preferably C C 4 alkyl.
- Alkyl may be branched or unbranched and may be substituted by halogen, for example fluorine, chlorine or bromine, C ⁇ -C 4 alkoxy, for example methoxy or ethoxy, phenyl or carboxyl, CrC alkoxycarbonyl, for example acetyl, mono- or di-CrC 4 alkylamino or -SO 3 M.
- R7 an R 8 is preferably a phenyl or naphthyl group which may be substituted by C C 4 alkyl, for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, CrC 4 alkoxy, for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy or tert-butoxy, halogen, for example fluorine, chlorine or bromine, C 2 -C 5 alkanoylamino, for example acetylamino, propionylamino or butyrylamino, nitro, sulfo or di- C ⁇ C ⁇ Ikylated amino.
- C C 4 alkyl for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, CrC
- the compounds of the formula (1) are preferably used in neutralized form, i.e.
- M is preferably a cation of an alkali metal, especially sodium, or an amine.
- R 1 is preferably
- C C ⁇ alkyl especially methyl or ethyl
- R 7 and R 8 are each as defined above and are each preferably hydrogen, C C 4 alkyl, especially methyl or ethyl, a morpholino or piperidino radical, most particularly hydrogen, or a radical of the formula — NH wherein R 6 is as defined above and is preferably -SO 3 M substituted C ⁇ -C 4 alkyi, especially methyl- or ethyl-substituted -SO 3 M, wherein M is as defined above and is preferably sodium; and
- R 2 is preferably —n ⁇ ⁇ o , -NH 2) -N(CH 2 CH 2 OH) 2 or -N[CH 2 CH(OH)CH 3 ] 2 .
- the compounds of the formula (1) are preparable under known reaction conditions by reacting cyanuric chloride with appropriate aminostilbenesulfonic acids and with an amino compound capable of introducing an Ri group and with a compound capable of introducing an R 2 group, R, and R 2 being as defined above.
- the stilbene compounds used in the invention have a pronounced antimicrobial action, especially against pathogenic Gram-positive and Gram-negative bacteria.
- Useful textile fibre materials include undyed and dyed or printed fibre materials, for example in silk, wool, polyamide or polyurethanes, and especially cellulosic fibre materials of any kind.
- Such fibre materials include for example natural cellulose fibres, such as cotton, linen, jute and hemp, and also pulp and regenerated cellulose.
- Preferred suitable textile fibre materials are composed of cotton.
- the textile materials may be present in various forms. Preference is given to piece goods, such as formed-loop knits or wovens, or else yarn on packages, warp beams, etc.
- optical brighteners which are useful according to the invention can be incorporated into liquid and solid laundry detergents.
- the formulations thus obtained may additionally include the customary formulation auxiliaries such as dispersants, builders, protective colloids, stabilizers, preservatives, scents, pigments, enzymes and also sequestrants.
- auxiliaries such as dispersants, builders, protective colloids, stabilizers, preservatives, scents, pigments, enzymes and also sequestrants.
- Preferred dispersants are nonionic dispersants, for example fatty alcohols, ethoxylation products of fatty alcohols or fatty acids, or anionic dispersants, such as the condensation products of aromatic sulfonic acids with formaldehyde, for example those based on oxyditolylsulfonic acid or naphthalenesulfonates, or ligninsulfonates.
- Useful builders or protective colloids include for example modified polysaccharides which are derived from cellulose or heteropolysaccharides such as xanthan, carboxymethylcellulose and also aluminium silicate or magnesium silicate.
- Useful stabilizing assistants include for example ethylene glycol, propylene glycol and further dispersants.
- the textile fibre materials are subjected for example to a customary wash cycle in a wash liquor that includes the corresponding optical brightener.
- the irradiation with UV light or in daylight preferably takes place after the textiles have been removed from the wash liquor, in the moist state, and the preferred light source is sunlight. Illumination can in this case conveniently take place during the drying of the textiles.
- illumination may also be effected during this drying process, for example by means of a suitable artificial light source attached to or in the tumble dryer.
- Example 1 Wash test a) Formulation of laundry detergent powder used (in per cent of the total weight of the formulation):
- 0.06 part of the brightener of the formula (101) reported in Example 2 is placed in a mortar together with a small amount of deionized water and then pestled with a further 15 parts of deionized water. 20 parts of the laundry detergent powder specified above under a) are then added within a short time, and the pestling continues to form a homogeneous mass. The mass obtained is placed in a crucible and air dried at 60°C for about 12 hours. Following two successive sieving operations (0.8 mm mesh and then 0.315 mm mesh) the granules obtained range in size from 0.315 to 0.8 mm.
- a Linitest laboratory washing machine is used to wash 10 parts of bleached cotton fabric with 100 parts of tap water and 0.4 part of the laundry detergent obtained as per b) at 25°C for 15 minutes. After the wash, the fabric is rinsed three times under running tap water and then dried in sunlight. The fabric thus washed possesses antimicrobial activity.
- Example 2 Determination of antimicrobial activitv of Tinopal CBS-X after irradiation with light The optical brightener of the formula
- the test is used to detect antimicrobial activity by comparison with unirradiated samples.
- a bacterial mixture of Staphylococcus aureus and Escherichia coli is plated out on the agar (final concentration cfu/ml: ⁇ 10 5 ).
- the plates are fixed on cotton by means of double sided Scotch tape and are irradiated with a xenon lamp for 10 or 30 minutes.
- Unirradiated agar plattes including 100 and 500 ppm of Tinopal CBS-X and agar plates without Tinopal are incubated as controls.
- test germs All plates were incubated at 37°C for about 48 hours. After incubation, viable bacteria are counted (see Table 1). Examples of test germs:
- the table reports the number of colony-forming units of bacteria after 10 minutes' and 30 minutes' irradiation.
- Table 1 show that 100 ppm or 500 ppm Tinopal CBS-X incorporated into agar nutrient medium is effective to substantially reduce the microorganisms (mixture of Staphylococcus aureus and Escherichia coli) after 30 minutes' irradiation with a xenon lamp compared with the agar plates containing unirradiated Tinopal CBS-X and agar plates containing no Tinopal CBS-X.
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Abstract
Described is the use of a laundry detergent that includes at least one optical brightener from the class of the stilbene compounds for the antimicrobial finishing of textile fibre materials, which comprises washing the fibre materials with this laundry detergent and subsequently exposing the washed textile material to a light source.
Description
Use of optical briαhteners from the class of the stilbene compounds as antimicrobiallv active substances
The present invention relates to the use of a laundry detergent that comprises at least one optical brightener from the class of the stilbene compounds for the antimicrobial finishing of textile materials and to the use of these compounds as antimicrobially active substances against microorganisms.
Washing with a commercially available laundry detergent removes the soil from the textile materials and usually imparts an improved appearance to them. However, washing and drying of textiles does not always remove bacteria to the desired degree. Nor does a normal wash do anything to prevent subsequent contamination by undesirable bacteria.
Existing ways to make textile fibre materials germ free include for example the use of bleaches, higher temperatures or irradiation with strong sunlight during drying.
It has now been found that, surprisingly, optical brighteners from the class of the stilbene compounds which are customarily used in the laundry detergent and textile industries have antimicrobial properties when the textile material is simultaneously irradiated with a light source.
The present invention accordingly provides for the use of a laundry detergent that comprises at least one optical brightener from the class of the stilbene compounds for the antimicrobial finishing of textile fibre materials, which comprises washing the fibre materials with this laundry detergent and subsequently exposing the washed textile material to a light source.
Useful optical brighteners for the invention preferably conform to the formula
(8) , wherein
Ri is a radical of the formula — NH-Γ V-corR, ;
R3 is substituted or unsubstituted alkyl or aryl;
R4 is M or substituted or unsubstituted alkyl or aryl;
R5 . is hydrogen; substituted or unsubstituted alkyl or aryl; or -NR7R8, wherein R7 and R8 are independently hydrogen; substituted or unsubstituted alkyl or aryl; or R7 and R8 combine with the joining nitrogen atom to form a heterocyclic radical, especially morpholino or piperidino radical;
R6 is hydrogen or substituted or unsubstituted alkyl or aryl,
R2 is hydrogen; substituted or unsubstituted alkyl or aryl; a radical of the formula — N o,
-OH; -NH2; -N(CH2CH2OH)2; -N[CH2CH(OH)CH3]2l -NH-R4, -N(R4)2 or -OR4; or
R1 and R≥ are independently -OH, -CI; -NH2, -O-C C4alkyl, -O-aryl, -NH-C^alkyl,
-N C^alkyl),,, -N(C1-C4alkyl)(C1-C4hydroxyalkyl), -N(C C4hydroxyalkyl)2, or -NH-aryl, morpholino, S-C^C^alky aryl),
R9 and R10 are independently hydrogen, C C4alkyl, phenyl or a radical of the formula
R is hydrogen, CI or SO3M;
R12 is -CN, -SO3M, -S(C C4alkyl)2 or S(aryl)2;
R13 is hydrogen, -SO3M, -O-C^alkyl, -CN, -CI, -COO-C^alkyl, or CON^-C^alkyl)^
R14 is hydrogen; -Chalky!, -CI or -SO3M;
R15 and R16 are independently hydrogen, C^alkyl, -SO3M, -CI or -O-C^alkyl;
R17 is hydrogen or 0,-C^alkyl;
R18 is hydrogen, C1-C4alkyl, -CN, -CI, -COO-C^alkyl, -CON(C1-C4alkyl)2, aryl or -O-aryl;
M is hydrogen, Na, K, Ca, Mg, ammonium, mono-, di-, tri- or tetra-C C4alkylammonium, mono-, di- or tri-CrC hydroxyalkylammonium or ammonium that is di- or trisubstituted with a mixture of C C4aIkyl and C1-C4hydroxyalkyl groups; and n-i, n2 and n3 are independently 0 or 1.
(Substituted or unsubstituted) alkyl R2, R3, R . Rs, Re, R7 and Ra is CrC12alkyl, preferably C C4alkyl. Alkyl may be branched or unbranched and may be substituted by halogen, for example fluorine, chlorine or bromine, Cι-C4alkoxy, for example methoxy or ethoxy, phenyl or carboxyl, CrC alkoxycarbonyl, for example acetyl, mono- or di-CrC4alkylamino or -SO3M.
(Substituted or unsubstituted) aryl R2, R3, R4, R5. Re, R7 an R8 is preferably a phenyl or naphthyl group which may be substituted by C C4alkyl, for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, CrC4alkoxy, for example methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy or tert-butoxy, halogen, for example fluorine, chlorine or bromine, C2-C5alkanoylamino, for example acetylamino, propionylamino or butyrylamino, nitro, sulfo or di- C^C^Ikylated amino.
The compounds of the formula (1) are preferably used in neutralized form, i.e.
M is preferably a cation of an alkali metal, especially sodium, or an amine.
In the compounds of formula (1), R1 is preferably
a radical of the formula — NH— (( γ— co— R3 , wherein R3 is as defined above and is
preferably C C^alkyl, especially methyl or ethyl; or
a radical of the formula — NH— < " > wherein R5 is as defined above and is
preferably d-C4alkyl, especially methyl or ethyl, or-NR7R8, wherein R7 and R8 are each as defined above and are each preferably hydrogen, C C4alkyl, especially methyl or ethyl, a morpholino or piperidino radical, most particularly hydrogen, or a radical of the formula
— NH wherein R6 is as defined above and is preferably -SO3M
substituted Cι-C4alkyi, especially methyl- or ethyl-substituted -SO3M, wherein M is as defined above and is preferably sodium; and
R2 is preferably —n ~^o , -NH2) -N(CH2CH2OH)2 or -N[CH2CH(OH)CH3]2.
The compounds of the formula (1) are preparable under known reaction conditions by reacting cyanuric chloride with appropriate aminostilbenesulfonic acids and with an amino compound capable of introducing an Ri group and with a compound capable of introducing an R2 group, R, and R2 being as defined above.
Optical brighteners that are advantageously useful in the present invention are recited below in Table 1 by way of example:
The stilbene compounds used in the invention have a pronounced antimicrobial action, especially against pathogenic Gram-positive and Gram-negative bacteria.
They are therefore useful for the treatment, especially decontamination and also antimicrobial finishing of textile fibre materials. Useful textile fibre materials include undyed and dyed or printed fibre materials, for example in silk, wool, polyamide or polyurethanes, and especially cellulosic fibre materials of any kind. Such fibre materials include for example natural cellulose fibres, such as cotton, linen, jute and hemp, and also pulp and regenerated cellulose. Preferred suitable textile fibre materials are composed of cotton.
The textile materials may be present in various forms. Preference is given to piece goods, such as formed-loop knits or wovens, or else yarn on packages, warp beams, etc.
To provide an antimicrobial finish, the optical brighteners which are useful according to the invention can be incorporated into liquid and solid laundry detergents.
For this they are generally diluted with further auxiliaries or water to the optimum concentration for the particular use.
The formulations thus obtained may additionally include the customary formulation auxiliaries such as dispersants, builders, protective colloids, stabilizers, preservatives, scents, pigments, enzymes and also sequestrants.
Preferred dispersants are nonionic dispersants, for example fatty alcohols, ethoxylation products of fatty alcohols or fatty acids, or anionic dispersants, such as the condensation products of aromatic sulfonic acids with formaldehyde, for example those based on oxyditolylsulfonic acid or naphthalenesulfonates, or ligninsulfonates.
Useful builders or protective colloids include for example modified polysaccharides which are derived from cellulose or heteropolysaccharides such as xanthan, carboxymethylcellulose and also aluminium silicate or magnesium silicate.
Useful stabilizing assistants include for example ethylene glycol, propylene glycol and further dispersants.
For the process of the invention, the textile fibre materials are subjected for example to a customary wash cycle in a wash liquor that includes the corresponding optical brightener. The irradiation with UV light or in daylight preferably takes place after the textiles have been removed from the wash liquor, in the moist state, and the preferred light source is sunlight. Illumination can in this case conveniently take place during the drying of the textiles. When the textiles are not line dried, but are dried for example in a tumble dryer, illumination may also be effected during this drying process, for example by means of a suitable artificial light source attached to or in the tumble dryer.
The examples which follow illustrate the invention.
Example 1 : Wash test a) Formulation of laundry detergent powder used (in per cent of the total weight of the formulation):
8% of alkylbenzenesulfonate
5% of alcohol ether sulfate
2% of alcohol ethoxylate (nonionic)
30% of sodium tripolyphosphate
20% of sodium carbonate
8% of sodium silicate
18.9% of sodium sulfate
1% of enzymes
1 % of polycarboxylates
0.1% of perfume oil
6% of water
b) Preparation of laundry detergent powder which includes Tinopal CBS-X:
0.06 part of the brightener of the formula (101) reported in Example 2 is placed in a mortar together with a small amount of deionized water and then pestled with a further 15 parts of deionized water. 20 parts of the laundry detergent powder specified above under a) are then added within a short time, and the pestling continues to form a homogeneous mass. The mass obtained is placed in a crucible and air dried at 60°C for about 12 hours. Following two successive sieving operations (0.8 mm mesh and then 0.315 mm mesh) the granules obtained range in size from 0.315 to 0.8 mm.
c) Wash with the laundry detergent obtained according to b):
A Linitest laboratory washing machine is used to wash 10 parts of bleached cotton fabric with 100 parts of tap water and 0.4 part of the laundry detergent obtained as per b) at 25°C for 15 minutes. After the wash, the fabric is rinsed three times under running tap water and then dried in sunlight. The fabric thus washed possesses antimicrobial activity.
Example 2: Determination of antimicrobial activitv of Tinopal CBS-X after irradiation with light The optical brightener of the formula
is incorporated in agar plates and subsequently inoculated with bacteria and irradiated with xenon light for 10 minutes or 30 minutes.
The test is used to detect antimicrobial activity by comparison with unirradiated samples.
To this end, a 1.5% stock solution in DMSO is prepared.
0.5 and 0.1 ml of this solution are added to 15 ml of liquid agar (final concentration: 500 and 100 ppm).
After solidification and drying, a bacterial mixture of Staphylococcus aureus and Escherichia coli is plated out on the agar (final concentration cfu/ml: ~105). The plates are fixed on cotton by means of double sided Scotch tape and are irradiated with a xenon lamp for 10 or 30 minutes.
Unirradiated agar plattes including 100 and 500 ppm of Tinopal CBS-X and agar plates without Tinopal are incubated as controls.
All plates were incubated at 37°C for about 48 hours. After incubation, viable bacteria are counted (see Table 1).
Examples of test germs:
Bacteria: Staphylococcus aureus ATCC 9144
Escherichia coli NCTC 8196
Cultures 18 to 24 hours in casein soymeal peptone broth diluted 1:5000 (Staph.) and 1:10,000 (E. coli) and mixed together
The results are summarized in Table 1.
The table reports the number of colony-forming units of bacteria after 10 minutes' and 30 minutes' irradiation.
The results of Table 1 show that 100 ppm or 500 ppm Tinopal CBS-X incorporated into agar nutrient medium is effective to substantially reduce the microorganisms (mixture
of Staphylococcus aureus and Escherichia coli) after 30 minutes' irradiation with a xenon lamp compared with the agar plates containing unirradiated Tinopal CBS-X and agar plates containing no Tinopal CBS-X.
Claims
1. Use of a laundry detergent that includes at least one optical brightener from the class of the stilbene compounds for the antimicrobial finishing of textile fibre materials, which comprises washing the fibre materials with this laundry detergent and subsequently exposing the washed textile material to a light source.
2. Use according to claim 1 , wherein the washed textile materials are irradiated with UV light or in daylight in the moist state.
3. Use according to claim 1 or 2, wherein an optical brightener used is a compound of the formula
wherein
Ri is a radical of the formula
R3 is substituted or unsubstituted alkyl or aryl;
R4 is M or substituted or unsubstituted alkyl or aryl;
Rs is hydrogen; substituted or unsubstituted alkyl or aryl; or -NR7R8, wherein R7 and R8 are independently hydrogen; substituted or unsubstituted alkyl or aryl; or R7 and R8 combine with the joining nitrogen atom to form a heterocyclic radical, especially morpholino or piperidino radical;
R6 is hydrogen or substituted or unsubstituted alkyl or aryl, R2 is hydrogen; substituted or unsubstituted alkyl or aryl; a radical of the formula
- ~ > -0h|; _NH2; -N(CH2CH2OH)2; -N[CH2CH(OH)CH3]2, -NH-R4, -N(R4)2 or -OR4;
or R1 and R2 are independently -OH, -CI; -NH2, -O-C^alkyl, -O-aryl, -NH-C^alkyl,
-N(C1-C4alkyl)2, -N(C C4alkyl)(C C4hydroxyalkyl), -N(C C4hydroxyalkyl)2, or -NH-aryl, morpholino, S-C^C^alkyKaryl),
M is hydrogen, Na, K, Ca, Mg, ammonium, mono-, di-, tri- or tetra-CrC^lkylammonium, mono-, di- or tri-CrC4hydroxyalkylammonium or ammonium that is di- or trisubstituted with a mixture of d-C4alkyl and C C4hydroxyalkyl groups; and n1 and n2, are independently 0 or 1.
4. Use according to claim 1 or 2, wherein an optical brightener used is a compound of the formula
wherein
R9 and R 0 are independently hydrogen, C C alkyl, phenyl or a radical of the formula
M is as defined in claim 3.
5. Use according to claim 1 or 2, wherein an optical brightener used is a compound of the formula
wherein
R., is hydrogen, CI or SO3M;
R12 is -CN, -S03M, -S^-C^alkyl)., or S(aryl)2 and
M is as defined in claim 3.
6. Use according to claim 1 or 2, wherein an optical brightener used is a compound of the formula
wherein
R13 is hydrogen, -SO3M, -O-C C4alkyl, -CN, -CI, -COO-C^alkyl, or
CON(C C4alkyl)2; and n3 is 0 or 1 , and
M is as defined in claim 31.
7. Use according to claim 1 or 2, wherein an optical brightener used is a compound of the formula
wherein
R14 is hydrogen, C C4alkyl, CI or -SO3M;
R15 and R are independently hydrogen, 0,-C^alkyl, -SO3M, -CI or -O-C^C^alkyl and
M is as defined in claim 3.
8. Use according to claim 1 or 2, wherein an optical brightener used is a compound of the formula
9. Use according to claim 1 or 2, wherein an optical brightener used is a compound of the formula
10. Use according to claim 1 or 2, wherein an optical brightener used is a compound of the formula
wherein
R17 is hydrogen or C -C4alkyl;
R18 is hydrogen, C C^al yl, -CN, -CI, -COO-C^alkyl, -CON(C1-C4alkyl)2, aryl or -O-aryl.
11. Use according to any one of claims 1 to 10, wherein the textile fibre materials used are natural cellulose fibres
12. Use of optical brighteners from the class of the stilbene compounds as antimicrobially active substances against microorganisms.
13. Use according to claim 12, wherein the microorganisms are Gram-positive and Gram-negative bacteria.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01917048A EP1263919A1 (en) | 2000-03-08 | 2001-03-01 | Use of optical brighteners from the class of the stilbene compounds as antimicrobially active substances |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00104907 | 2000-03-08 | ||
| EP00104907 | 2000-03-08 | ||
| PCT/EP2001/002315 WO2001066681A1 (en) | 2000-03-08 | 2001-03-01 | Use of optical brighteners from the class of the stilbene compounds as antimicrobially active substances |
| EP01917048A EP1263919A1 (en) | 2000-03-08 | 2001-03-01 | Use of optical brighteners from the class of the stilbene compounds as antimicrobially active substances |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1263919A1 true EP1263919A1 (en) | 2002-12-11 |
Family
ID=8168052
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP01917048A Withdrawn EP1263919A1 (en) | 2000-03-08 | 2001-03-01 | Use of optical brighteners from the class of the stilbene compounds as antimicrobially active substances |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20030110574A1 (en) |
| EP (1) | EP1263919A1 (en) |
| AU (1) | AU2001244177A1 (en) |
| BR (1) | BR0109039A (en) |
| MX (1) | MXPA02008709A (en) |
| WO (1) | WO2001066681A1 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003020862A1 (en) * | 2001-09-04 | 2003-03-13 | Ciba Specialty Chemicals Holding Inc. | Process for inhibiting the dye transfer |
| EP2993222A1 (en) | 2014-09-03 | 2016-03-09 | Tim Bast | Detergent composition comprising rare earth metal and a stilbene brightening agent |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2157209A1 (en) * | 1971-11-18 | 1973-05-24 | Henkel & Cie Gmbh | Antimicrobial treatment of textiles - with synergistic compsn free of halogenated diphenyl urea |
| IN153407B (en) * | 1979-09-28 | 1984-07-14 | Ciba Geigy Ag | |
| DE3100470A1 (en) * | 1981-01-09 | 1982-09-02 | Bayer Ag, 5090 Leverkusen | "METHOD FOR ANTIMICROBIAL EQUIPMENT OF TEXTILES" |
| CH657864A5 (en) * | 1984-02-17 | 1986-09-30 | Ciba Geigy Ag | WATER-SOLUBLE PHTHALOCYANINE COMPOUNDS AND THE USE THEREOF AS PHOTOACTIVATORS. |
| US4978475A (en) * | 1988-02-26 | 1990-12-18 | The Procter & Gamble Company | Stable liquid detergents containing anionic surfactant and monosulfonated brightener |
| EP0364403B1 (en) * | 1988-10-13 | 1993-03-24 | Ciba-Geigy Ag | Distyryl biphenyl compounds |
| US5830526A (en) * | 1994-12-28 | 1998-11-03 | Fibermark, Inc. | Light-activated antimicrobial and antiviral materials |
| GB9726365D0 (en) * | 1997-12-13 | 1998-02-11 | Ciba Sc Holding Ag | Compounds |
-
2001
- 2001-03-01 WO PCT/EP2001/002315 patent/WO2001066681A1/en not_active Ceased
- 2001-03-01 BR BR0109039-9A patent/BR0109039A/en not_active Application Discontinuation
- 2001-03-01 US US10/220,671 patent/US20030110574A1/en not_active Abandoned
- 2001-03-01 MX MXPA02008709A patent/MXPA02008709A/en unknown
- 2001-03-01 AU AU2001244177A patent/AU2001244177A1/en not_active Abandoned
- 2001-03-01 EP EP01917048A patent/EP1263919A1/en not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| See references of WO0166681A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US20030110574A1 (en) | 2003-06-19 |
| MXPA02008709A (en) | 2003-02-24 |
| BR0109039A (en) | 2003-06-03 |
| WO2001066681A1 (en) | 2001-09-13 |
| AU2001244177A1 (en) | 2001-09-17 |
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