EP2416870A1 - Fabrics comprising a photocatalyst to produce singlet oxygen from ambient oxygen - Google Patents
Fabrics comprising a photocatalyst to produce singlet oxygen from ambient oxygenInfo
- Publication number
- EP2416870A1 EP2416870A1 EP10762408A EP10762408A EP2416870A1 EP 2416870 A1 EP2416870 A1 EP 2416870A1 EP 10762408 A EP10762408 A EP 10762408A EP 10762408 A EP10762408 A EP 10762408A EP 2416870 A1 EP2416870 A1 EP 2416870A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- photocatalyst
- substituted
- fabric
- ester
- reaction
- 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- Withdrawn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
- 239000011941 photocatalyst Substances 0.000 title claims abstract description 346
- 239000004744 fabric Substances 0.000 title claims abstract description 152
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 title claims abstract description 66
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000001301 oxygen Substances 0.000 title claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 241000894006 Bacteria Species 0.000 claims description 23
- 235000019504 cigarettes Nutrition 0.000 claims description 7
- 239000000779 smoke Substances 0.000 claims description 7
- 244000052769 pathogen Species 0.000 claims description 5
- 230000001580 bacterial effect Effects 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 194
- -1 potpourri Substances 0.000 description 128
- 238000006243 chemical reaction Methods 0.000 description 124
- 239000011248 coating agent Substances 0.000 description 45
- 238000000576 coating method Methods 0.000 description 45
- 239000008199 coating composition Substances 0.000 description 25
- 125000004185 ester group Chemical group 0.000 description 24
- 150000002148 esters Chemical class 0.000 description 24
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 24
- 239000000243 solution Substances 0.000 description 22
- 235000019645 odor Nutrition 0.000 description 20
- 238000012360 testing method Methods 0.000 description 20
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 18
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 17
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 15
- 150000002790 naphthalenes Chemical class 0.000 description 13
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 13
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 11
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 150000002987 phenanthrenes Chemical class 0.000 description 11
- 150000003220 pyrenes Chemical class 0.000 description 11
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 10
- 150000003252 quinoxalines Chemical class 0.000 description 10
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 9
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 9
- 150000002220 fluorenes Chemical class 0.000 description 9
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 9
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical class [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 9
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- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 8
- ZBQZBWKNGDEDOA-UHFFFAOYSA-N eosin B Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC([N+]([O-])=O)=C(O)C(Br)=C1OC1=C2C=C([N+]([O-])=O)C(O)=C1Br ZBQZBWKNGDEDOA-UHFFFAOYSA-N 0.000 description 8
- SEACYXSIPDVVMV-UHFFFAOYSA-L eosin Y Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 SEACYXSIPDVVMV-UHFFFAOYSA-L 0.000 description 8
- IINNWAYUJNWZRM-UHFFFAOYSA-L erythrosin B Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 IINNWAYUJNWZRM-UHFFFAOYSA-L 0.000 description 8
- SQHOAFZGYFNDQX-UHFFFAOYSA-N ethyl-[7-(ethylamino)-2,8-dimethylphenothiazin-3-ylidene]azanium;chloride Chemical compound [Cl-].S1C2=CC(=[NH+]CC)C(C)=CC2=NC2=C1C=C(NCC)C(C)=C2 SQHOAFZGYFNDQX-UHFFFAOYSA-N 0.000 description 8
- 229930003944 flavone Natural products 0.000 description 8
- 235000011949 flavones Nutrition 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 235000020944 retinol Nutrition 0.000 description 8
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 8
- 229950003937 tolonium Drugs 0.000 description 8
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 8
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 7
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 description 7
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 7
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 7
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 7
- 150000004347 all-trans-retinol derivatives Chemical class 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- UWBXIFCTIZXXLS-UHFFFAOYSA-L disodium;2,3,4,5-tetrachloro-6-(2,4,5,7-tetraiodo-3-oxido-6-oxoxanthen-9-yl)benzoate Chemical compound [Na+].[Na+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 UWBXIFCTIZXXLS-UHFFFAOYSA-L 0.000 description 7
- 150000002137 ergosterols Chemical class 0.000 description 7
- 150000002212 flavone derivatives Chemical class 0.000 description 7
- 150000008376 fluorenones Chemical class 0.000 description 7
- 239000003205 fragrance Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- GVKCHTBDSMQENH-UHFFFAOYSA-L phloxine B Chemical compound [Na+].[Na+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 GVKCHTBDSMQENH-UHFFFAOYSA-L 0.000 description 7
- 229920002635 polyurethane Polymers 0.000 description 7
- 239000004814 polyurethane Substances 0.000 description 7
- 229960003471 retinol Drugs 0.000 description 7
- 239000011607 retinol Substances 0.000 description 7
- 239000002151 riboflavin Substances 0.000 description 7
- 235000019192 riboflavin Nutrition 0.000 description 7
- 150000003287 riboflavins Chemical class 0.000 description 7
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 7
- 150000000552 thionines Chemical class 0.000 description 7
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 6
- AUNGANRZJHBGPY-UHFFFAOYSA-N D-Lyxoflavin Natural products OCC(O)C(O)C(O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-UHFFFAOYSA-N 0.000 description 6
- UCTLRSWJYQTBFZ-UHFFFAOYSA-N Dehydrocholesterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)CCCC(C)C)CCC33)C)C3=CC=C21 UCTLRSWJYQTBFZ-UHFFFAOYSA-N 0.000 description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000003466 anti-cipated effect Effects 0.000 description 6
- 229930006711 bornane-2,3-dione Natural products 0.000 description 6
- 150000001846 chrysenes Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
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- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 6
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- 238000000862 absorption spectrum Methods 0.000 description 1
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- 150000001545 azulenes Chemical class 0.000 description 1
- XZSVAMUZTKNGDN-JBRJOJLESA-L bacteriochlorophylls Chemical class [Mg+2].[N-]1C2=C(C=3C(C(C)C(=CC=4C(=C(C(C)=O)C(=C5)N=4)C)N=3)CCC(=O)OC\C=C(/C)CCCC(C)CCCC(C)CCCC(C)C)C(C(=O)OC)C([O-])=C2C(C)=C1C=C1C(CC)C(C)C5=N1 XZSVAMUZTKNGDN-JBRJOJLESA-L 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
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- 239000003139 biocide Substances 0.000 description 1
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- 238000004440 column chromatography Methods 0.000 description 1
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- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical class C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
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- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- FDHFJXKRMIVNCQ-OSIZZBRKSA-N methyl (3R,21S,22S)-16-ethenyl-11-ethyl-4-hydroxy-12,17,21,26-tetramethyl-22-[3-oxo-3-[(E,7R,11R)-3,7,11,15-tetramethylhexadec-2-enoxy]propyl]-7,23,24,25-tetrazahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaene-3-carboxylate Chemical compound CCC1=C(C2=NC1=CC3=C(C4=C([C@@H](C(=C5[C@H]([C@@H](C(=CC6=NC(=C2)C(=C6C)C=C)N5)C)CCC(=O)OC/C=C(\C)/CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C4=N3)C(=O)OC)O)C)C FDHFJXKRMIVNCQ-OSIZZBRKSA-N 0.000 description 1
- KMPBXIVQGVRHIW-UHFFFAOYSA-N methyl 9-oxofluorene-2-carboxylate Chemical compound C1=CC=C2C(=O)C3=CC(C(=O)OC)=CC=C3C2=C1 KMPBXIVQGVRHIW-UHFFFAOYSA-N 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- QBPCOMNNISRCTC-UHFFFAOYSA-L protochlorophyllide a Chemical compound [Mg+2].N1=C2C3=C([N-]4)C(CCC(O)=O)=C(C)C4=CC(C(=C4C=C)C)=NC4=CC(C(C)=C4CC)=NC4=CC1=C(C)C2=C([O-])C3C(=O)OC QBPCOMNNISRCTC-UHFFFAOYSA-L 0.000 description 1
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- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
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Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- 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
- D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
- D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
- D06M13/513—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/165—Polymer immobilised coordination complexes, e.g. organometallic complexes
- B01J31/1658—Polymer immobilised coordination complexes, e.g. organometallic complexes immobilised by covalent linkages, i.e. pendant complexes with optional linking groups, e.g. on Wang or Merrifield resins
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1825—Ligands comprising condensed ring systems, e.g. acridine, carbazole
- B01J31/183—Ligands comprising condensed ring systems, e.g. acridine, carbazole with more than one complexing nitrogen atom, e.g. phenanthroline
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/39—Photocatalytic properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/50—Catalysts, in general, characterised by their form or physical properties characterised by their shape or configuration
- B01J35/58—Fabrics or filaments
-
- 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
-
- 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
- D06M2400/00—Specific information on the treatment or the process itself not provided in D06M23/00-D06M23/18
- D06M2400/01—Creating covalent bondings between the treating agent and the fibre
Definitions
- the invention relates to fabrics comprising a photocatalyst to produce singlet oxygen from ambient oxygen.
- the fabrics further comprise a compound to react reversibly with singlet oxygen.
- air fresheners to mitigate unpleasant odors in indoor spaces.
- Such air fresheners may be in the form of candles, aerosol sprays, potpourri, gels, and mechanical or heat released products.
- products may neutralize or otherwise cover odors, they are also associated with negative health affects.
- Many common air fresheners contain chemicals that can aggravate asthma and contain hazardous or toxic chemicals such as phthalates, acetone, chloromethane, acetaldehyde, and 1 ,4-dioxane.
- phthalates such as phthalates, acetone, chloromethane, acetaldehyde, and 1 ,4-dioxane.
- a fabric comprising a photocatalyst to produce singlet oxygen from ambient oxygen is presented.
- the fabric includes a coating comprising the photocatalyst, and optionally one or more compounds to reversibly react with singlet oxygen.
- Indoor accessories are presented, wherein those indoor accessories comprise a fabric comprising a photocatalyst to produce singlet oxygen from ambient oxygen is presented.
- the fabric includes a coating comprising the photocatalyst, and optionally one or more compounds to reversibly react with singlet oxygen.
- the indoor accessories are selected from the group consisting of furniture, cushions, pillows, bedding, curtains, and floor coverings.
- FIG. IA is a cross-sectional view showing one surface of a fabric
- FIG. IB is a cross-sectional view showing two opposing surfaces of a fabric
- FIG. 1C shows a photocatalyst attached to the surface of the fabric of FIG. IA via a silyl ester linkage and a photocatalyst attached to the surface of the fabric of FIG. IA via a silyl amide linkage
- FIG. 2 is a block diagram showing a fabric laminate
- FIG. 3 illustrates a plurality of photocatalyst moieties, and optionally a plurality of singlet oxygen trap moieties, chemically bonded to a fabric;
- FIG. 4 illustrates a plurality of photocatalyst moieties, and optionally a plurality of singlet oxygen trap moieties, chemically bonded a pre-coating disposed on a fabric
- FIG. 5 illustrates a plurality of photocatalyst moieties, and optionally a plurality of singlet oxygen trap moieties, chemically bonded a first pre-coating disposed on a first surface of a fabric, and a plurality of photocatalyst moieties, and optionally a plurality of singlet oxygen trap moieties, chemically bonded a second pre-coating disposed on a second surface of the fabric.
- the present invention is described as including fabrics comprising a photocatalyst composition to produce singlet oxygen from ambient oxygen. This description should not be taken as limiting. Applicant's invention includes any substrate comprising a surface, wherein a photocatalyst to produce singlet oxygen from ambient oxygen is chemically attached to that surface. Other substrates include, without limitiation, plastic films, glass, metal, wood, paper, and combinations thereof.
- Applicant's fabric comprises a coating comprising a photocatalyst which generates a singlet oxygen from ambient oxygen, in optional combination with a singlet oxygen trap.
- a photocatalyst which generates a singlet oxygen from ambient oxygen, in optional combination with a singlet oxygen trap.
- inlet oxygen trap Applicant means a compound that reacts reversibly with singlet oxygen.
- the use of a photocatalyst to generate singlet oxygen from ambient oxygen, in combination with a singlet oxygen trap is taught in United States Pat. No. 7,259,122 (the '122 Patent), in the name of Lombardi, and is hereby incorporated herein by reference in its entirety.
- Applicant's fabric comprises Applicant's coating composition described disposed over one or more surfaces thereof.
- fabric means a flexible, planar material formed by weaving or felting or knitting or crocheting natural and/or synthetic fibers.
- Applicant's fabric generates singlet oxygen using Reaction Scheme "A”, below. Upon absorption of light, the photocatalyst undergoes electronic excitation to a singlet state followed by electron reorganization to form the excited triplet state. Triplet photocatalyst transfers energy to ambient triplet oxygen to form reactive singlet oxygen. The singlet oxygen generated ( l O 2 ), is the reactive species capable eliminating odors.
- the singlet oxygen oxidizes odoriferous compounds rendering those materials odor-free. In certain embodiments, the singlet oxygen oxidizes materials and/or pathogens that release one or more odoriferous compounds.
- Applicant's fabric comprises a Photocatalyst Composition which comprises a Photocatalyst and one or more pendant silyl ester groups.
- Such pendant silyl ester groups facilitate formation of a stable covalent attachment of Applicant's Photocatalyst Composition to a wide variety of fabric surfaces.
- Applicant react a substituted Photocatalyst with one or more of silyl ester compounds 4, 5, 6, 7, and/or 8, to covalently bond one or more pendant silyl ester functionalities II to form Applicant's Photocatalyst Composition.
- Applicant's Photocatalyst Composition comprises a substituted photocatalyst selected from the group consisting of substituted Acetonaphthones, substituted Acetophenonse, substituted Acridines, substituted Anthracenes, substituted Anthraquinones, substituted Anthrones, substituted Azulenes, substituted Benzils, substituted Benzophenones, substituted Benzopyranones, substituted Benzoquinones, substituted Flavones, substituted Camphoroquinone, substituted Chrysenes, substituted 7-Dehydrocholesterols, substituted Ergosterols, substituted Fluorenes, substituted Fluorenones, substituted Eosins, substituted Fluoresceins, substituted Phloxines, substituted Rose Bengals, substituted Erythrosins, substituted Indoles, substituted Naphthalenes, substituted Phenanthrenes, substituted Phenazines, substituted
- Examples 1 through 42 summarize the preparations of Photocatalyst Compositions 21, 22, 23, 24, 25, 27, 28, 29, 30, 32, 33, 36, 37, 39, 40, 43, 44, 46, 47, 48, 50, 51, 52, 54, 55, 56, 57, 59, 60, 62, 64, 65, 66, 68, 69, 70, 72, 73, 74, 76, 77, 78, 80, 81, 82, 84, 85, 86, 88, 89, 91, 92, 93, 94, 96, 97, 99, 100, 101, 103, 104, 106, 107, 108, 110, 111, 112, 114, 115, 116, 118, 119, 120, 122, 123, 124, 126, 127, 129, 130, 131, 133, 134, 136, 137, 138, 140, 141, 142, 144, 145, 146, 148, 149, 150, 152
- Photocatalyst Composition 28 Reaction of substituted photocatalyst 26B with epoxysilyl ester 6 gives Photocatalyst Composition 28. Reaction of substituted photocatalyst 26B with isocyanatosilyl ester 7 gives Photocatalyst Composition 27.
- Photocatalyst Composition 32 Reaction of substituted photocatalyst 31 with aminosilyl ester 4 gives Photocatalyst Composition 32. Reaction of substituted photocatalyst 31 with mercaptosilyl ester 5 gives Photocatalyst Composition 33.
- Reaction of substituted Ergosterol Photocatalyst 49 with epoxysilyl ester 6 gives substituted Ergosterol Photocatalyst Composition 50.
- Reaction of substituted Ergosterol Photocatalyst 49 with isocyanatosilyl ester 7 gives substituted Ergosterol Photocatalyst Composition 51.
- Reaction of substituted Ergosterol Pphotocatalyst 49 with chlorosilyl ester 8 gives substituted Ergosterol Photocatalyst Composition 52.
- Reaction of substituted Thionine Photocatalyst 105 with epoxysilyl ester 6 gives substituted Thionine Photocatalyst Composition 106.
- Reaction of substituted Thionine Photocatalyst 105 with isocyanatosilyl ester 7 gives substituted Thionine Photocatalyst Composition 107.
- Reaction of substituted Thionine Photocatalyst 105 with chlorosilyl ester 8 gives substituted Thionine Photocatalyst Composition 108.
- Reaction of substituted Toluidine Blue Photocatalyst 117 with epoxysilyl ester 6 gives substituted Toluidine Blue Photocatalyst Composition 118.
- Reaction of substituted Toluidine Blue Photocatalyst 117 with isocyanatosilyl ester 7 gives substituted Toluidine Blue Photocatalyst Composition 119.
- Reaction of substituted Toluidine Blue Photocatalyst 117 with chlorosilyl ester 8 gives substituted Toluidine Blue Photocatalyst Composition 120.
- Reaction of substituted Retinol Photocatalyst 139 with epoxysilyl ester 6 gives substituted Retinol Photocatalyst Composition 140.
- Reaction of substituted Retinol photocatalyst 139 with isocyanatosilyl ester 7 gives substituted Retinol Photocatalyst Composition 141.
- Reaction of substituted Retinol photocatalyst 139 with chlorosilyl ester 8 gives substituted Retinol Photocatalyst Composition 142.
- Bacteriochlorophyll B Photocatalyst 156 Reaction of substituted Bacteriochlorophyll B Photocatalyst 156 with aminosilyl ester 4 gives Bacteriochlorophyll B Photocatalyst Composition 157.
- Chlorophyll B CAS 519-62-0; ⁇ ⁇ 0.7-0.8
- Protochlorophyllide CAS 20369-67-9; ⁇ -0.7-0.8
- Tetraphenyl Porphyrin photocatalyst 182 Reaction of Tetraphenyl Porphyrin photocatalyst 182 with aminosilyl ester 4 gives Tetraphenyl -porphyrin Photocatalyst Composition 183. Reaction of Tetraphenyl porphyrin Photocatalyst 182 with mercaptosilyl ester 5 gives substituted Tetraphenyl Porphyrin Photocatalyst Composition 184.
- Example 44 is presented to further illustrate to persons skilled in the art how to make and use the invention.
- Example 44 is not intended as a limitation, however, upon the scope of Applicant's invention.
- Photocatalyst 190 (0.2 gram) was dissolved in ethanol (200 proof; 10 mL). Sonication was used. Triethylamine (0.08 g) was added to the photocatalyst 190 solution. Aminopropyl triethoxysilane, Compound 4, (0.14 g) was added to the photocatalyst solution to form Photocatalyst Composition 191. The Photocatalyst Composition 191 was stirred at room temperature in the dark for 3 hrs.
- R NH(CH 2 ) 3 Si(OCH 2 CH 3 ) 3
- 5% v/v ammonium hydroxide solution was prepared using concentrated ammonium hydroxide by mixing about 95 mL of water and 5 mL of concentrated ammonium hydroxide solution.
- Applicant prepared a coating composition comprising between about 5% to about 25% v/v of the above-described ethanol / triethylamine solution of Photocatalyst Composition 191 in ammonium hydroxide. Table 1 recites typical formulations.
- Applicant's coating composition further comprises one or more singlet oxygen traps
- those singlet oxygen trap compounds are added to the above-described ethanol / triethylamine / ammonium hydroxide mixture of Photocatalyst Composition 191.
- Applicant's singlet oxygen scavengers comprise substituted pyridones.
- Applicant's coating composition can be applied to various films and fabrics, including for example and without limitation polypropylene fabric, cotton fabric, polyester fabric, nylon fabric, and the like.
- Spunbond polypropylene sold in commerce by Kappler under the tradename Pro vent 10000 was employed as a coating substrate.
- the coating substrate was first pre-treated with a polyurethane pre- coating.
- WitCoBond UCX-281F sold in commerce by Chemtura was applied to the Provent 10000 surface in a 5% to about 10% w/w aqueous mixture.
- the polyurethane pre-coating was applied by either rolling or spraying. After application of the polyurethane pre-coating, the pre-coated Provent 10000 was allowed to dry at ambient condition overnight.
- Example 44 The coating composition of Example 44 was then applied to the polyurethane precoated Provent 10000 by either rolling or spraying.
- the treated surface was dried at 100 °C for 1 to-2 minutes.
- Applicant has discovered that the treated fabric of Example 45 is self- decontaminating with respect to various odors.
- self-decontaminating with respect to odor Applicant means that exposing the treated fabric of Example 45 to an odorant followed by exposure of that treated / exposed fabric to either sunlight or indoor lighting, effectively eliminates the odor from the treated / exposed / illuminated fabric with respect to a control / untreated fabric.
- the untreated / odorant exposed / illuminated fabric retains the odor of the odorant.
- the treated / odorant exposed / illuminated fabric does not retain the odor of the odorant.
- EXAMPLE 46 For example, the treated fabric of Example 45 self-decontaminates with respect to cigarette smoke odors. T-shirts were treated with the coating composition, using method of, Example 44 to give the treated fabric of Example 45 in the form of a T-shirt. A treated T-shirt was placed on a first hanger and suspended within a first polyethylene bag. An uncoated T-shirt control was placed on a second hanger and suspended in a second polyethylene bag.
- Cigarette smoke was introduced into both the first bag and the second bag, thereby exposing both the treated T-shirt and the control T-shirt to cigarette smoke.
- the first bag and the second bag were then sealed.
- the treated T-shirt and the control T-shirt were kept in the respective sealed polyethylene bags for one hour.
- the treated T-shirt and the untreated T-shirt were removed from the respective bags, and were exposed to indoor fluorescent lighting for two hours.
- ASTM E679-91 Standard Practice for Determination of Odor and Taste Thresholds by a Forced-Choice Ascending Concentration Series Method of Limits
- a panel of four odor assessors independently sniffed both the treated T-shirt and the untreated T-shirt.
- Each of the odor assessors reported that the untreated T-shirt retained an odor of cigarette smoke, but the treated T-shirt retained no odor of cigarette smoke.
- Example 47 the treated fabric of Example 45 self-decontaminates with respect to mercaptans.
- T-shirts were treated with the coating composition, using method of, Example 44 to give the a treated fabric of Example 45 in the form of a T-shirt.
- a treated T-shirt was placed on a first hanger and suspended within a first polyethylene bag.
- An uncoated T-shirt control was placed on a second hanger and suspended in a second polyethylene bag.
- Propane gas containing an ethyl mercaptan odorant was introduced into both the first bag and the second bag, thereby exposing both the treated T-shirt and the control T- shirt to the ethyl mercaptan odorant.
- the first bag and the second bag were then sealed.
- the treated T-shirt and the control T-shirt were kept in the respective sealed polyethylene bags for one hour.
- ethyl mercaptan is added to propane gas at a loading of 3.3 milligrams per 100 grams of liquefied propane.
- the treated T-shirt and the untreated T-shirt were removed from the respective bags, and were exposed to indoor fluorescent lighting for two hours.
- ASTM E679-91 Standard Practice for Determination of Odor and Taste Thresholds by a Forced-Choice Ascending Concentration Series Method of Limits
- a panel of four odor assessors independently sniffed both the treated T-shirt and the untreated T-shirt.
- Each of the odor assessors reported that the untreated T-shirt retained an odor of ethyl mercaptan, but the treated T-shirt retained no odor of ethyl mercaptan.
- odors are produced by various biological agents, such as for example bacteria.
- Bioburden testing was performed by Nelson Laboratories in Salt Lake City, Utah. The levels of Aerobic, Anaerobic, and Spore-forming bacteria on the surface of the treated fabric of Example 45 and an untreated test fabric comprising Pro vent 10000 were determined. Both the control fabric and the test fabric were subjected to only normal fluorescent light illumination.
- Table 2 summarizes the bioburden testing results.
- Table 2 recites data showing that Applicant's test fabric comprises a treated fabric bacterial level of 79 CFU, 30 CFU, and 151 CFU, for aerobic, anaerobic, and spore forming bacteria, respectively.
- Table 2 further recites data showing that Applicant's control fabric comprises an untreated fabric bacteria level of 189 CFU, 256 CFU, and 451 CFU, for aerobic, anaerobic, and spore forming bacteria, respectively, wherein the treated fabric bacteria level is less than the comparable untreated fabric bacteria level.
- AATCC 100 The American Association of Textile Chemists and Colorists (“AATCC”) have promulgated test method AATCC 100 which is directed to microbiological testing. AATCC 100 provides a quantitative procedure for the evaluation of the degree of antibacterial activity.
- K. pneumoniae is a gram negative, rod-shaped, bacterium comprising a thick lipopolysaccharide superficial membrane layer. K. pneumoniae is known to be resistant to many biocides and antibiotics.
- Control fabric swatches comprised untreated Provent 10000 fabric.
- Test fabric swatches comprises the treated fabric of Example 45.
- Control and test fabric swatches were inoculated with microorganisms. According to AATCC 100 antimicrobial test procedure, 1.0 mL of test organism suspension at approximately 1,000,000 CFU/mL is inoculated to test sample. The inoculation was performed such that the microbial suspension contacts only the fabric swatches. Bacteria levels on both control and test fabrics were determined at "time zero" by elution in a large volume of neutralizing broth, followed by dilution and plating.
- Aluminum phthalocyanine tetrasulfonylchloride 190 (2 g) was dissolved in 10 mL acetone. Sonication was employed to promote dissolution of the dye. Potassium carbonate (anhydrous; > 4 eq, ⁇ 1.3 g) was added to the dye solution. The resulting mixture was stirred at room temperature. Aminopropyltriethoxysilane (Silquest A-1100, Momentive Performance materials, Inc., North Greenbush, NY); 2 eq, 0.91 g) and n-dodecylamine (2 eq, 0.76 g) were mixed with 5 mL of ethanol (200 proof) yielding a clear solution.
- Example 50 The treated fabric of this Example 50 was evaluated using the AATCC 100 test procedure described hereinabove in Example 49.
- Table 5 summarizes the AATCC test results using K. pneumoniae and the fabric treated with Batch No. 1 of the coating formulation comprising Photocatalyst Composition 192, as described immediately hereinabove.
- Aluminum phthalocyanine tetrasulfonylchloride 190 (2 g) was dissolved in 10 mL acetone. Sonication was employed to promote dissolution of the dye. Potassium carbonate (anhydrous; > 4 eq, ⁇ 1.3 g) was added to the dye solution. The resulting mixture was stirred at room temperature. Aminopropyltriethoxysilane (Silquest Al 100; 2 eq, 0.91 g) and DUOMEEN C (Akzo Nobel Surface Chemistry AB, Stenungsund, Sweden, 2 eq, 0.52 g) were mixed with 5 mL of acetone yielding a clear solution.
- DUOMEEN C comprises a mixture of cocopropylenediamine (CAS [61791-63-7]), and R-NH-(CH 2 ) 3 -NH 2 , wherein R comprises Cg - C] 8 straight chain alkyl hydrocarbons.
- Example 51 The treated fabric of this Example 51 was evaluated using the AATCC 100 test procedure described hereinabove in Example 49.
- Table 6 summarizes the AATCC test results using K. pneumoniae and the fabric treated with Batch No. 1 of the coating formulation comprising Photocatalyst Composition 194, as described immediately hereinabove. TABLE 6
- IESNA Illuminating Engineering Society of North America
- IESNA is the professional organization that generates standards/guidelines concerning lighting for architectural designs and consumer goods etc.
- IESNA Recommended Practices and ANSI Standards recommend lighting levels for hospital environments (in Lux) of 500 Lux for general lighting and 1000 Lux for examination/treatment, respectively.
- Applicant's irradiation of the fabric treated with the coating of this Example 51 were that treated fabric comprises Photocatalyst Composition 194 mimics the use of that treated fabric in a hospital treatment / examination facility.
- the dark experiment was carried out in an incubator with a temperature set at 37- 38 0 C.
- the observed log reduction values were calculated relative to CFU count from the control fabric at time zero min exposure.
- the results of Table 6 demonstrate that the observed log reduction value after 10 minutes of light exposure was a combination between a light activation (log reduction of 1.673) and a dark reaction (log reduction of 2.34).
- Applicant's bioburden testing and AATCC testing quantitatively demonstrate that fabrics treated with Applicant's coating comprising one or more of Applicant's Photocatalyst Compositions are self-decontaminating with respect to surface pathogens.
- Applicant's coating composition comprises one or more embodiments of Photocatalyst Composition III in combination with one or more singlet oxygen scavengers, i.e. compounds that reversibly react with singlet oxygen.
- Applicant has found that N-substituted-2-pyridones 10 trap singlet oxygen upon irradiation in the presence of Photocatalyst Composition III and ambient oxygen to give 1 ,4-endoperoxides 15.
- Applicant has further found that such N-substituted-2-pyridonyl endoperoxides 15 efficiently release singlet oxygen over time.
- Applicant has prepared and tested N-substituted-2-pyridones 200A, 200B, 200C, 200D, 200E, 300A, 300B, 300C, 300D, and 400A to determine the efficacy of using these compounds as singlet oxygen scavengers.
- Applicant has experimentally determined quantitative data on the singlet oxygen trap- release process of N-methylester substituted pyridones 200A, 200B, 200C, 200D, 200E, and N-isoamyl-2-methylpyridones 300A, 300B, 300C, 300D, and N-isobutyl-2-methylpyridone 400A. All pyridones were purified by column chromatography prior to testing.
- TPP tetraphenyl porphyrin
- the mixture solution in a quartz cuvette was sealed with a silicone septum screw cap.
- the solution was irradiated by a Xe arc lamp (150 W) through a FSQ-RG495 filter (yellow; ⁇ > 495 nm) and a hot mirror (IR filter).
- the cuvette sample was located 2 feet away from the lamp housing.
- a fine stream oxygen (Omega micro flow meter; flow read at 10; 0.342 ml/min) was bubbled to the solution during irradiation.
- the consumptions of the pyridones were monitored by UV- Vis absorption spectroscopy at their ⁇ max 260-340 nm.
- the irradiated solution was subsequently allowed to sit in a temperature control cell holder in the dark at 40 °C for 1 min before the absorption spectrum of the solution at 40 0 C was recorded.
- the regeneration of each pyridones was monitored by recording change in its ⁇ max as a function of time.
- Equation (1) When two individual compounds have overlapped absorption bands, as shown by Equation (1) an absorbance at a particular wavelength in a mixture equals to a summation of absorbances from each individual component at that wavelength.
- a m ⁇ ibCi + ⁇ 2 bC 2 (1)
- TABLE 7 through 16 recite kinetic data for both the formation of an Endoperoxide from a substituted pyridone, and for the deposition of that Endoperoxide to regenerate singlet oxygen.
- the measured half lives for the 10 endoperoxides studied varied from about 1 hour to about 9.6 hours.
- Applicant has modified their substituted pyridone compounds to comprise pendent silyl ester groups.
- substituted pyridone 300C with N- Bromosuccinimide in chloroform gives bromonated, substituted pyridone 305C.
- Reaction of brominated, substituted pyridone 305C with mercapto silyl ester 7 gives substituted N-isoamyl pyridone 310C, wherein pyridone 31OC comprises a pendent silyl ester group.
- substituted pyridones 200B, 200C, 200D, 200E, 300B, 300D, and 400A can be modified to form substituted pyridones 210B, 210C, 210D, 210E, 31OB, 310D, and 410A, each comprising a pendent silyl ester group.
- Applicant reacted substituted pyridone 200A with amino silyl ester 4 to form pyridone 210A comprising a pendent silyl ester group.
- Applicant's coating composition comprises one or more of silyl ester substituted pyridones 210A, 210B, 215B, 210C, 215C, 210D, 215D, 210E, 215E, 310B, 310D, and/or 410A, in combination with Applicant's ethanolic / triethylamine / Photocatalyst Composition III mixture.
- the one or more N-methylester substituted pyridones silyl ester substituted pyridones 21 OA, 210B, 215B, 210C, 215C, 210D, 215D, 210E, 215E, 310B, 310D, and/or 410A are present from about 0.10 to about 50 molar excess based upon the moles of Photocatalyst III present in the coating composition.
- the resulting coating generates singlet oxygen when exposed to both ambient air and light.
- Applicant has found that both sunlight and artificial light, i.e. both incandescent and/or fluorescent, effectively cause a coating comprising one or more embodiments of Applicant's Photocatalyst Composition III to generate singlet oxygen.
- a fabric / substrate bearing a coating comprising one or more embodiments of Applicant's Photocatalyst Compositions in combination with one or more endoperoxides formed from silyl ester substituted pyridones 21 OB, 21 OC, 21 OD, 21 OE, 31 OB, 31 OD, and/or 410A, is disposed in a dark environment such that the one or more Photocatalyst Composition III moieties do not generate singlet oxygen, the one or more endoperoxides decompose to release singlet oxygen, wherein those one or more endoperoxides have the half lives recited in Tables 2 through 11.
- the substituted pyridone singlet oxygen traps used in any coating formulation are selected based upon the anticipated hours of darkness that a fabric / substrate coated with Applicant's Photocatalyst Composition / Pyridone coating will experience. For example, where a 1-2 hour period of darkness is anticipated, then the fabric / substrate will be coated with a coating comprising one or more embodiments of Applicant's Photocatalyst Composition in combination with one or more of substituted pyridone 31 OC.
- the fabric / substrate will be coated with a coating comprising one or more embodiments of Applicant's Photocatalyst Composition III in combination with one or more of substituted pyridones 310B, 310D, and/or 410A.
- the fabric / substrate will be coated with a coating comprising one or more embodiments of Applicant's Photocatalyst Composition in combination with one or more of substituted pyridones 210E, 310D, and/or 410A.
- the fabric / substrate will be coated with a coating comprising one or more embodiments of Applicant's Photocatalyst Composition in combination with one or more of substituted pyridones 21 OB, 21 OC, 21 OD, and/or 21 OE.
- a period of darkness greater than 10 hours is anticipated, then the fabric / substrate will be coated with a coating comprising one or more embodiments of Applicant's Photocatalyst Composition in combination with one or more of substituted pyridones 210B, 210C, and/or 210D.
- Applicant's coating comprises one or more photocatalysts in combination with one or more singlet oxygen trap molecules / moieties, as described above.
- Applicant's one or more photocatalysts produce singlet oxygen during daylight hours, wherein a portion of that singlet oxygen remains available to oxidize pathogens, and wherein a portion of the singlet oxygen produced is scavenged, i.e. stored, by the one or more singlet oxygen traps which then release that stored singlet oxygen throughout the nighttime hours giving Applicant's coating a time-release decontamination capability.
- Applicant's fabric comprises Applicant's coating composition described hereinabove disposed over one or more surfaces thereof.
- fabric Applicant means a flexible, planar material formed by weaving or felting or knitting or crocheting natural and/or synthetic fibers.
- fabric 1000 comprises polypropylene.
- fabric 1000 comprises polyvinylchloride.
- fabric 1000 comprises cotton.
- fabric 10010 comprises canvas.
- fabric 1000 comprises leather.
- fabric 1000 comprises wool.
- fabric 1000 comprises bamboo.
- fabric 1000 comprises silk.
- fabric 1000 comprises nylon.
- fabric 1000 comprises polyurethane.
- fabric 1000 comprises polyvinylalcohol.
- Applicant's fabric 1000 comprises a surface 1010.
- FIG. IA shows surface 1010 comprising a hydroxyl group (-OH) and an amino group (-NH 2 ).
- surface 1010 is treated with one or more of Photocatalyst Compositions 21, 22, 23, 24, 25, 27, 28, 29, 30, 32, 33, 36, 37, 39, 40, 43, 44, 46, 47, 48, 50, 51, 52, 54, 55, 56, 57, 59, 60, 62, 64, 65, 66, 68, 69, 70, 72, 73, 74, 76, 77, 78, 80, 81, 82, 84, 85, 86, 88, 89, 91, 92, 93, 94, 96, 97, 99, 100, 101, 103, 104, 106, 107, 108, 110, 111, 1 12, 114, 115, 116, 118, 119, 120, 122, 123, 124, 126, 127, 129, 130, 131, 133, 134, 136, 137, 138, 140, 141, 142, 144, 145, 146, 148, 149
- a pendant silyl ester group disposed on any one of the above- recited Photocatalyst Compositions can react with a surface hydroxyl group to chemically bond the Photocatalyst to the fabric surface via a silyl ester group. Still referring to FIG. 1C, a pendant silyl ester group disposed on any one of the above-recited Photocatalyst Compositions can react with a surface amino group to chemically bond the Photocatalyst to the fabric surface via a silyl amide group.
- surface 1010 is treated with one or more of N- substituted-2-pyridones 200A, 200B, 200C, 200D, 200E, 300A, 300B, 300C, 300D, and 400A to give fabric 300 shown in FIG. 3.
- a pendant silyl ester group disposed on any one of the above-recited N-substituted-2-pyridones can react with a surface hydroxyl group to chemically bond the N-substituted-2-pyridones to the fabric surface via a silyl ester group.
- a pendant silyl ester group disposed on any one of the above-recited N- substituted-2-pyridones can react with a surface amino group to chemically bond the N- substituted-2-pyridones to the fabric surface via a silyl amide group.
- Applicant's fabric 1000 comprises opposing surfaces 1010 and 1020.
- surfaces 1010 and 1020 are each independently treated with one or more of Photocatalyst Compositions 21, 22, 23, 24, 25, 27, 28, 29, 30, 32, 33, 36, 37, 39, 40, 43, 44, 46, 47, 48, 50, 51, 52, 54, 55, 56, 57, 59, 60, 62, 64, 65, 66, 68, 69, 70, 72, 73, 74, 76, 77, 78, 80, 81, 82, 84, 85, 86, 88, 89, 91, 92, 93, 94, 96, 97, 99, 100, 101, 103, 104, 106, 107, 108, 110, 111, 1 12, 114, 115, 116, 118, 119, 120, 122, 123, 124, 126, 127, 129, 130, 131, 133, 134, 136, 137, 138, 140, 141, 142, 144, 145, 146,
- Applicant's fabric comprises a multi-layer laminate.
- fabric laminate 2000 comprises a first fabric 2010 a second fabric 2020, and third fabric 2030.
- One or more outer surfaces of a fabric laminate, such as fabric laminate 2000 can be treated with Applicant's coating composition, wherein that coating composition comprises one or more Photocatalyst Compositions described herein, and optionally one or more oxygen trap compounds described herein.
- Applicant's fabric 300 comprises a plurality of Photocatalyst Compositions, and optionally a plurality of singlet oxygen traps, chemically bonded to a surface thereof.
- a plurality of Photocatalyst Compositions, and optionally a plurality of singlet oxygen traps are chemically bonded to more than one surface of fabric 1000.
- fabric 300 comprises Photocatalyst Composition 310 and Photocatalyst Composition 330 chemically bonded thereto, in optional combination with singlet oxygen trap 320 and singlet oxygen trap 340 chemically bonded thereto.
- singlet oxygen trap 320 comprises a first structure and singlet oxygen trap 340 comprises a second structure, wherein the first structure differs from the second structure.
- Photocatalyst Composition 310 comprises a first structure and Photocatalyst Composition 330 comprises a second structure, wherein the first structure differs from the second structure.
- Photocatalyst Composition 310 comprises one or more of
- Photocatalyst Composition 330 comprises one or more of Photocatalyst Compositions 21, 22, 23, 24, 25, 27, 28, 29, 30, 32, 33, 36, 37, 39, 40, 43, 44, 46, 47, 48, 50, 51, 52, 54, 55, 56, 57, 59, 60, 62, 64, 65, 66, 68, 69, 70, 72, 73, 74, 76, 77, 78, 80, 81, 82, 84, 85, 86, 88, 89, 91, 92, 93, 94, 96, 97, 99, 100, 101, 103, 104, 106, 107, 108, 110, 111, 112, 114, 115, 116, 118, 119, 120, 122, 123, 124, 126, 127, 129, 130, 131, 133, 134, 136, 137, 138, 140, 141, 142, 144, 145, 146,
- singlet oxygen trap 320 comprises one or more of N- substituted-2-pyridones 200A, 200B, 200C, 200D, 200E, 300A, 300B, 300C, 300D, and 400A.
- singlet oxygen trap 340 comprises one or more of N- substituted-2-pyridones 200A, 200B, 200C, 200D, 200E, 300A, 300B, 300C, 300D, and 400A.
- FIG. 4 illustrates fabric 400 wherein coating 405 is disposed on a first surface of fabric 1000.
- coating 405 comprises a polyurethane pre-coating as described in Example 43 hereinabove.
- Applicant's pre- coating 405 is treated with Applicant's coating composition which comprises a first plurality Photocatalyst Compositions 320 and a second plurality of Photocatalyst
- Applicant's pre-coating 405 is treated with Applicant's coating composition which optionally comprises a first plurality of singlet oxygen traps 310 and a second plurality of singlet oxygen traps 330.
- a pendant silyl ester group disposed on any one of the above-described Photocatalyst Compositions can react with a surface hydroxyl group to chemically bond the Photocatalyst to a surface of coating 405 via a silyl ester group.
- a pendant silyl ester group disposed on any one of the above-recited Photocatalyst Compositions can react with a surface amino group to chemically bond the Photocatalyst to a surface of coating 405 via a silyl amide group.
- a pendant silyl ester group disposed on any one of the above-recited N- substituted-2-pyridones can react with a surface hydroxyl group to chemically bond the N-substituted-2-pyridones to a surface of coating 405 via a silyl ester group.
- a pendant silyl ester group disposed on any one of the above-recited N-substituted-2-pyridones can react with a surface amino group to chemically bond the N-substituted-2-pyridones to a surface of coating 405 via a silyl amide group.
- FIG. 5 illustrates fabric 500 wherein coating 405 is disposed on a first surface of fabric 1000, and coating 505 disposed on a second surface of fabric 1000.
- coating 505 comprises a polyurethane pre-coating as described in Example 43 hereinabove.
- Applicant's pre-coating 505 is treated with Applicant's coating composition which comprises a first plurality Photocatalyst Compositions 520 and a second plurality of Photocatalyst Compositions 540.
- Applicant's pre-coating 505 is treated with Applicant's coating composition which optionally comprises a first plurality of singlet oxygen traps 510 and a second plurality of singlet oxygen traps 530.
- singlet oxygen trap 510 comprises one or more of N- substituted-2-pyridones 200A, 200B, 200C, 200D, 200E, 300A, 300B, 300C, 300D, and 400A.
- singlet oxygen trap 530 comprises one or more of N- substituted-2-pyridones 200A, 200B, 200C, 200D, 200E, 300A, 300B, 300C, 300D, and 400A.
- Photocatalyst Composition 520 comprises one or more of Photocatalyst Compositions 21, 22, 23, 24, 25, 27, 28, 29, 30, 32, 33, 36, 37, 39, 40, 43, 44, 46, 47, 48, 50, 51, 52, 54, 55, 56, 57, 59, 60, 62, 64, 65, 66, 68, 69, 70, 72, 73, 74, 76, 77, 78, 80, 81, 82, 84, 85, 86, 88, 89, 91, 92, 93, 94, 96, 97, 99, 100, 101, 103, 104, 106, 107, 108, 110, 111, 112, 114, 115, 116, 118, 119, 120, 122, 123, 124, 126, 127, 129, 130, 131, 133, 134, 136, 137, 138, 140, 141, 142, 144, 145, 146,
- Photocatalyst Composition 540 comprises one or more of Photocatalyst Compositions 21, 22, 23, 24, 25, 27, 28, 29, 30, 32, 33, 36, 37, 39, 40, 43, 44, 46, 47, 48, 50, 51, 52, 54, 55, 56, 57, 59, 60, 62, 64, 65, 66, 68, 69, 70, 72, 73, 74, 76, 77, 78, 80, 81, 82, 84, 85, 86, 88, 89, 91, 92, 93, 94, 96, 97, 99, 100, 101, 103, 104, 106, 107, 108, 110, 111, 112, 114, 115, 116, 118, 1 19, 120, 122, 123, 124, 126, 127, 129, 130, 131, 133, 134, 136, 137, 138, 140, 141, 142, 144, 145, 146,
- a pendant silyl ester group disposed on any one of the above-described Photocatalyst Compositions can react with a surface hydroxyl group to chemically bond the Photocatalyst to a surface of coating 405 via a silyl ester group.
- a pendant silyl ester group disposed on any one of the above-recited Photocatalyst Compositions can react with a surface amino group to chemically bond the Photocatalyst to a surface of coating 405 via a silyl amide group.
- a pendant silyl ester group disposed on any one of the above-recited N- substituted-2-pyridones can react with a surface hydroxyl group to chemically bond the N-substituted-2-pyridones to a surface of coating 405 via a silyl ester group.
- a pendant silyl ester group disposed on any one of the above-recited N-substituted-2-pyridones can react with a surface amino group to chemically bond the N-substituted-2-pyridones to a surface of coating 405via a silyl amide group.
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Abstract
Description
Claims
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US16740909P | 2009-04-07 | 2009-04-07 | |
US12/652,670 US8481446B2 (en) | 2003-08-29 | 2010-01-05 | Chemically-resistant coating composition |
PCT/US2010/030304 WO2010118180A1 (en) | 2009-04-07 | 2010-04-07 | Fabrics comprising a photocatalyst to produce singlet oxygen from ambient oxygen |
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CN108456215B (en) * | 2018-05-07 | 2019-12-17 | 福州大学 | controlled-release singlet oxygen endoperoxide and preparation and application thereof |
US20220386724A1 (en) * | 2019-07-01 | 2022-12-08 | Chemical Intelligence Limited | Antimicrobial dyes for healthcare apparel |
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JP3761248B2 (en) * | 1996-06-13 | 2006-03-29 | 小松精練株式会社 | Fiber fabric having deodorant, antibacterial and antifouling functions |
JP2000096430A (en) * | 1998-09-29 | 2000-04-04 | Toray Ind Inc | Multifunctional nonwoven cloth |
KR100303446B1 (en) * | 1998-10-29 | 2002-10-04 | 삼성전자 주식회사 | Manufacturing method of thin film transistor substrate for liquid crystal display device |
JP2002209724A (en) * | 2001-01-17 | 2002-07-30 | Matsuura Seisakusho:Kk | Curtain |
US7300593B2 (en) * | 2003-06-27 | 2007-11-27 | The Procter & Gamble Company | Process for purifying a lipophilic fluid |
EP2004197A4 (en) * | 2006-03-31 | 2009-08-19 | Univ North Carolina State | Light activated antiviral materials and devices and methods for decontaminating virus infected environments |
-
2010
- 2010-04-07 EP EP10762408A patent/EP2416870A4/en not_active Withdrawn
- 2010-04-07 JP JP2012504840A patent/JP5855563B2/en not_active Expired - Fee Related
- 2010-04-07 WO PCT/US2010/030304 patent/WO2010118180A1/en active Application Filing
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080171803A1 (en) * | 2003-08-29 | 2008-07-17 | Lombardi John L | Pathogen-resistant coatings |
US7259122B1 (en) * | 2004-08-30 | 2007-08-21 | John Lombardi | Chemically-resistant shelter coating |
Non-Patent Citations (1)
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See also references of WO2010118180A1 * |
Also Published As
Publication number | Publication date |
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JP2012523507A (en) | 2012-10-04 |
JP5855563B2 (en) | 2016-02-09 |
WO2010118180A1 (en) | 2010-10-14 |
EP2416870A4 (en) | 2013-02-27 |
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