WO2023216556A1 - Hydrophilic antibacterial finishing agent, antibacterial finishing method of fabric and antibacterial fabric - Google Patents
Hydrophilic antibacterial finishing agent, antibacterial finishing method of fabric and antibacterial fabric Download PDFInfo
- Publication number
- WO2023216556A1 WO2023216556A1 PCT/CN2022/134213 CN2022134213W WO2023216556A1 WO 2023216556 A1 WO2023216556 A1 WO 2023216556A1 CN 2022134213 W CN2022134213 W CN 2022134213W WO 2023216556 A1 WO2023216556 A1 WO 2023216556A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- propyl
- antibacterial
- fabric
- hydrophilic
- triethoxysilyl
- Prior art date
Links
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 82
- 239000004744 fabric Substances 0.000 title claims abstract description 66
- 238000000034 method Methods 0.000 title claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 37
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 32
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 230000008878 coupling Effects 0.000 claims abstract description 6
- 238000010168 coupling process Methods 0.000 claims abstract description 6
- 238000005859 coupling reaction Methods 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims abstract description 5
- 238000003825 pressing Methods 0.000 claims description 11
- 238000005096 rolling process Methods 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 238000002791 soaking Methods 0.000 claims description 9
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- WSFMFXQNYPNYGG-UHFFFAOYSA-M dimethyl-octadecyl-(3-trimethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OC)(OC)OC WSFMFXQNYPNYGG-UHFFFAOYSA-M 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 4
- 229960004275 glycolic acid Drugs 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 4
- HRBYCVPFYWTROV-UHFFFAOYSA-M dimethyl-octadecyl-(3-triethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OCC)(OCC)OCC HRBYCVPFYWTROV-UHFFFAOYSA-M 0.000 claims description 3
- 238000009472 formulation Methods 0.000 claims description 3
- RYJVNHWSPPNQPJ-UHFFFAOYSA-M hexadecyl-dimethyl-(3-triethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OCC)(OCC)OCC RYJVNHWSPPNQPJ-UHFFFAOYSA-M 0.000 claims description 3
- FVOCUSGXQAQFAK-UHFFFAOYSA-M hexadecyl-dimethyl-(3-trimethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OC)(OC)OC FVOCUSGXQAQFAK-UHFFFAOYSA-M 0.000 claims description 3
- PNVTUEKJNJFCDQ-UHFFFAOYSA-M icosyl-dimethyl-(3-triethoxysilylpropyl)azanium bromide Chemical compound CCCCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OCC)(OCC)OCC.[Br-] PNVTUEKJNJFCDQ-UHFFFAOYSA-M 0.000 claims description 3
- GBXKGBZMDRQPBY-UHFFFAOYSA-M icosyl-dimethyl-(3-triethoxysilylpropyl)azanium iodide Chemical compound CCCCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OCC)(OCC)OCC.[I-] GBXKGBZMDRQPBY-UHFFFAOYSA-M 0.000 claims description 3
- YDTONGIBQBOOBF-UHFFFAOYSA-M icosyl-dimethyl-(3-trimethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OC)(OC)OC YDTONGIBQBOOBF-UHFFFAOYSA-M 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 3
- 235000014655 lactic acid Nutrition 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- DNSWTOIMKAUOOF-UHFFFAOYSA-M [Br-].C(CCCCCCCCCCCCCCC)[N+](CCC[Si](OCC)(OCC)OCC)(C)C Chemical compound [Br-].C(CCCCCCCCCCCCCCC)[N+](CCC[Si](OCC)(OCC)OCC)(C)C DNSWTOIMKAUOOF-UHFFFAOYSA-M 0.000 claims description 2
- ARWVKGAXHAGCQX-UHFFFAOYSA-M [Cl-].C(C)O[Si](CCC[N+](CCCCCCCCCCCCCCCCCCCC)(C)C)(OCC)OCC Chemical compound [Cl-].C(C)O[Si](CCC[N+](CCCCCCCCCCCCCCCCCCCC)(C)C)(OCC)OCC ARWVKGAXHAGCQX-UHFFFAOYSA-M 0.000 claims description 2
- CHQRONKPYYGVTH-UHFFFAOYSA-M [I-].C(CCCCCCCCCCCCCCC)[N+](CCC[Si](OC)(OC)OC)(C)C Chemical compound [I-].C(CCCCCCCCCCCCCCC)[N+](CCC[Si](OC)(OC)OC)(C)C CHQRONKPYYGVTH-UHFFFAOYSA-M 0.000 claims description 2
- APPRERXIYLHKDD-UHFFFAOYSA-M [I-].C(CCCCCCCCCCCCCCC)[N+](CCC[Si](OCC)(OCC)OCC)(C)C Chemical compound [I-].C(CCCCCCCCCCCCCCC)[N+](CCC[Si](OCC)(OCC)OCC)(C)C APPRERXIYLHKDD-UHFFFAOYSA-M 0.000 claims description 2
- JJSVCAUWAVQOFW-UHFFFAOYSA-M [I-].C(CCCCCCCCCCCCCCCCC)[N+](CCC[Si](OCC)(OCC)OCC)(C)C Chemical compound [I-].C(CCCCCCCCCCCCCCCCC)[N+](CCC[Si](OCC)(OCC)OCC)(C)C JJSVCAUWAVQOFW-UHFFFAOYSA-M 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- YKZPFXHPXFJCOW-UHFFFAOYSA-M dimethyl-octadecyl-(3-triethoxysilylpropyl)azanium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OCC)(OCC)OCC YKZPFXHPXFJCOW-UHFFFAOYSA-M 0.000 claims description 2
- GAIQCMMCFUMPRO-UHFFFAOYSA-M dimethyl-octadecyl-(3-trimethoxysilylpropyl)azanium iodide Chemical compound [I-].C(CCCCCCCCCCCCCCCCC)[N+](CCC[Si](OC)(OC)OC)(C)C GAIQCMMCFUMPRO-UHFFFAOYSA-M 0.000 claims description 2
- YGFACYFRHZWFHE-UHFFFAOYSA-M dimethyl-octadecyl-(3-trimethoxysilylpropyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OC)(OC)OC YGFACYFRHZWFHE-UHFFFAOYSA-M 0.000 claims description 2
- UVMKWFGXKGMZFM-UHFFFAOYSA-M hexadecyl-dimethyl-(3-trimethoxysilylpropyl)azanium bromide Chemical compound [Br-].CO[Si](CCC[N+](CCCCCCCCCCCCCCCC)(C)C)(OC)OC UVMKWFGXKGMZFM-UHFFFAOYSA-M 0.000 claims description 2
- HWWLBPUPCUFZDY-UHFFFAOYSA-M icosyl-dimethyl-(3-trimethoxysilylpropyl)azanium bromide Chemical compound CCCCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OC)(OC)OC.[Br-] HWWLBPUPCUFZDY-UHFFFAOYSA-M 0.000 claims description 2
- ORCHBDAKXIDGCW-UHFFFAOYSA-M icosyl-dimethyl-(3-trimethoxysilylpropyl)azanium iodide Chemical compound CCCCCCCCCCCCCCCCCCCC[N+](C)(C)CCC[Si](OC)(OC)OC.[I-] ORCHBDAKXIDGCW-UHFFFAOYSA-M 0.000 claims description 2
- 238000005406 washing Methods 0.000 abstract description 13
- 230000036541 health Effects 0.000 abstract description 10
- 230000002045 lasting effect Effects 0.000 abstract description 3
- 230000003385 bacteriostatic effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 26
- 238000001035 drying Methods 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000004753 textile Substances 0.000 description 11
- 229920000742 Cotton Polymers 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 206010011409 Cross infection Diseases 0.000 description 1
- 206010029803 Nosocomial infection Diseases 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/53—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
- C08G65/33317—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/337—Polymers modified by chemical after-treatment with organic compounds containing other elements
-
- 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
- D06M13/244—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 sulfur or phosphorus
- D06M13/282—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 sulfur or phosphorus with compounds containing phosphorus
- D06M13/285—Phosphines; Phosphine oxides; Phosphine sulfides; Phosphinic or phosphinous acids or derivatives thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—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
- D06M13/44—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 containing nitrogen and phosphorus
-
- 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
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/47—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
- D06M13/473—Compounds containing quaternary nitrogen atoms derived from 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
- D06M13/50—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
-
- 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
- D06M13/5135—Unsaturated compounds containing silicon atoms
-
- 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
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- the present invention relates to the technical field of antibacterial finishing agents for textiles, and relates to a hydrophilic antibacterial finishing agent, a method for conducting antibacterial finishing of a fabrics, and an antibacterial fabric.
- Antibacterial sanitary finishing of the textiles is a processing technology that employs an antibacterial or bacteriostatic agent to treat a fabric, so as to obtain an antibacterial, mildew-proof, and odor-proof textile that keeps clean and sanitary. Its purpose is not only to prevent the textile from being contaminated by microorganisms, but more importantly to prevent infectious diseases, ensure the safety, health and wearing comfort of human body, and reduce the cross-infection rate of public environment, so that the textile can acquire a new function of health care and meet people's demands for hygiene and health.
- Quaternary ammonium salt antibacterial agents have been widely studied and utilized because of their low price and fast sterilization speed. 4 generations of quaternary ammonium salt antibacterial agents of typical significance have been developed internationally; among them, DC-5700, an antibacterial agent of silicone quaternary ammonium salt developed by Dow Corning is the most representative. Since the antibacterial agent of silicone quaternary ammonium salt combines a quaternary ammonium salt with a silane coupling agent in its structure, this product has accepted washing resistance and an excellent antibacterial effect at the same time. However, DC-5700 has an obvious defect in that a fabric subjected to antibacterial finishing with it is extremely hydrophobic, which limits its application scenarios. It severely limits its application in fabrics that contact with skin, such as an underwear.
- the present invention has developed a hydrophilic antibacterial finishing agent for post finishing of a fabric.
- An antibacterial fabric made by this antibacterial finishing method not only has an excellent antibacterial performance, but also has good hydrophilicity.
- hydrophilic antibacterial finishing agent including the following components in parts by weight:
- silicone hydrophilic antibacterial agent has a chemical structure as shown in the formula I below,
- R is selected from methyl, ethyl, C 3 -C 6 alkyl, vinyl, allyl or an aromatic ring substituent;
- X 1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy;
- X 2 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy;
- the r, s, t, m and n satisfy that the sum of r + s + t + 3 (m + n) is greater than or equal to 40 and less than or equal to 80.
- the aforementioned silicone coupling antibacterial agent is at least one of dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium bromide, dimethylhexadecyl [3- (trimethoxysilyl) propy
- it further includes 0.001-0.1 part of a pH regulator.
- the aforementioned pH regulator is at least one of hydrochloric acid, phosphoric acid, acetic acid, lactic acid, hydroxyacetic acid, citric acid or sulfuric acid.
- the second one of the technical solutions of the present invention is to provide a method for conducting antibacterial finishing of a fabric, which includes the following steps:
- formulation of an antibacterial finishing solution formulating a hydrophilic antibacterial finishing agent according to the aforementioned weight parts and components of the hydrophilic antibacterial finishing agent;
- the aforementioned step (1) further includes adding 0.001-0.1 part of a pH regulator to adjust the pH to 3-6.
- the third one of the technical solutions of the present invention is to provide an antibacterial fabric prepared by the aforementioned finishing method.
- the fabric prepared by soaking and finishing with the antibacterial finishing agent of the present invention has an excellent antibacterial performance and a high bacteriostasis rate against Escherichia coli.
- the bacteriostasis rate remains at the level of 99.9%after 50 times of washing, and thus the bacteriostasis performance is lasting; and meanwhile, its hydrophilic performance remains at a very high level after 50 times of washing, which thus can keep the health level of human body for a long time and maintain the wearing performance of clothes.
- the fabric material is used as the substrate, and the antibacterial finishing solution is applied onto the surface of the fabric in a soaking manner to form the hydrophilic antibacterial composite layer.
- the present invention provides a hydrophilic antibacterial finishing agent including the following components in parts by weight:
- silicone hydrophilic antibacterial agent has a chemical structure as shown in the formula I below,
- R is selected from methyl, ethyl, C 3 -C 6 alkyl, vinyl, allyl, phenyl, benzyl or an aromatic ring substituent;
- X 1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy;
- X 2 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy;
- the aforementioned silicone hydrophilic antibacterial agent is a main active ingredient of the hydrophilic antibacterial finishing agent of the present invention, and there is no ready-made product on the market currently, so it is prepared by our in the present invention.
- a method for preparing the silicone hydrophilic antibacterial agent of the present invention is as follows:
- the first reaction solvent can be at least one of xylene, p-xylene, toluene, ethylene glycol diethyl ether or DMF
- the second reaction solvent can be at least one of xylene, p-xylene, toluene, ethylene glycol diethyl ether or DMF
- the aforementioned r, s, t, m and n satisfy that the sum of r + s + t + 3 (m + n) is greater than or equal to 40 and less than or equal to 80.
- a method for preparing a compound of formula I-1 as a silicone hydrophilic antibacterial agent is as follows.
- reaction solution is cooled to room temperature, added with a proper amount of petroleum ether, cooled to 0°C to precipitate a large amount of solid, and filtered.
- the filter cake is collected to obtain 0.959 mol of a product as a white solid.
- the yield is 95.9%, and the titration purity of the product is 99.4%.
- the reaction solution is cooled to room temperature, added with a proper amount of petroleum ether, cooled to -20°C to precipitate a large amount of solid, and filtered.
- the filter cake is collected to obtain 0.911 mol of a product as a white solid.
- the yield is 95.0%
- the total yield of reaction of the two steps is 91.1%, and the titration purity of the product is 99.3%.
- Examples 2-7 a compound of formula I-2, a compound of formula I-3, a compound of formula I-4, a compound of formula I-5, a compound of formula I-6 and a compound of formula I-7 are respectively used as silicone hydrophilic antibacterial agents.
- Their preparation methods refer to that of the compound of formula I-1, and their structures are confirmed by nuclear magnetic data.
- a cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 10 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 80%. Subsequently, the fabric was placed into a drying room at 150°C and baked for 5 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
- a cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 20 for 15 minutes, and then passed through a pressing roll at a rolling over rate of 90%. Subsequently, the fabric was placed into a drying room at 160°C and baked for 4 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
- a polyester-cotton blended fabric was soaked in the finishing agent solution at a bath ratio of 1: 5 for 60 minutes, and then passed through a pressing roll at a rolling over rate of 100%. Subsequently, the fabric was placed into a drying room at 170°C and baked for 3 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
- a cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 30 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 60%. Subsequently, the fabric was placed into a drying room at 160°C and baked for 4 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
- a cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 15 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 80%. Subsequently, the fabric was placed into a drying room at 80°C and baked for 10 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
- a cotton fabric was soaked in the finishing solution at a bath ratio of 1: 10 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 100%. Subsequently, the fabric was placed into a drying room at 180°C and baked for 1 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
- a cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 20 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 50%. Subsequently, the fabric was placed into a drying room at 150°C and baked for 5 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
- Hydrophilicity a wetting time determination method was adopted: in an environment with an average temperature of 25°C and an average relative humidity of 60%, a fabric to be tested was laid flat and tightened on a beaker, and a drop of water was dripped with a rubber-tipped dropper at a distance of about 3 cm from a cloth surface, and the time was counted until the water droplet was diffused on the cloth surface until there was no mirror emission. This time was the time for diffusion of the water droplet. The hydrophilicity is better when the spreading time is shorter. The specific results were as shown in Table 1.
- the fabric prepared by soaking and finishing with the antibacterial finishing agent of the present invention had an excellent antibacterial performance and a high bacteriostasis rate against Escherichia coli.
- the bacteriostasis rate remained at the level of 99.9%after 50 times of washing, and thus the bacteriostasis performance was lasting; and meanwhile, its hydrophilic performance remained at a very high level after 50 times of washing, which thus could keep the health level of human body for a long time and maintain the wearing performance of clothes.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
A hydrophilic antibacterial finishing agent including the following components in parts by weight: 0.01-1 part of a silicone hydrophilic antibacterial agent; 1-5 parts of a silicone coupling antibacterial agent; and 94-98.99 parts of water; wherein the silicone hydrophilic antibacterial agent has a chemical structure as shown in formula I. A fabric prepared by antibacterial finishing with the antibacterial finishing agent has an excellent antibacterial performance and a lasting bacteriostatic performance; and meanwhile, its hydrophilic performance remains at a very high level after 50 times of washing, which thus can keep the health level of human body for a long time and maintain the wearing performance of clothes.
Description
FIELD OF TECHNOLOGY/Technical Field
The present invention relates to the technical field of antibacterial finishing agents for textiles, and relates to a hydrophilic antibacterial finishing agent, a method for conducting antibacterial finishing of a fabrics, and an antibacterial fabric.
In recent years, with the improvement of living standards, people's awareness of health and environmental protection has been continuously strengthened. While the beauty and comfort of textiles and clothing are gained attention, higher requirements are put forward for their health care functions. Producing textiles with antibacterial functions is one of the effective ways to protect people from or be less affected by bacteria, and thus the textiles with antibacterial functions are more and more favored by people.
Antibacterial sanitary finishing of the textiles is a processing technology that employs an antibacterial or bacteriostatic agent to treat a fabric, so as to obtain an antibacterial, mildew-proof, and odor-proof textile that keeps clean and sanitary. Its purpose is not only to prevent the textile from being contaminated by microorganisms, but more importantly to prevent infectious diseases, ensure the safety, health and wearing comfort of human body, and reduce the cross-infection rate of public environment, so that the textile can acquire a new function of health care and meet people's demands for hygiene and health.
With the improvement of living standards, people's understanding of the living environment and requirements for the quality of life are constantly improving, especially their awareness of health is constantly increasing. Since harmful bacteria are distributed very widely in nature, of many kinds and in a huge number, they seriously threaten human health. Diseases caused by infections transmitted by bacteria have become a major social problem, which causes widespread concern. An organic antibacterial agent has the characteristics of a fast sterilization speed, high antibacterial efficiency, convenient processing, a stable color and the like. They have a long history of use and play an irreplaceable role in some fields. Producing a textile with an antibacterial function by using an antibacterial finishing agent is one of the effective ways to prevent people from or be less attacked by bacteria, and thus the textiles with antibacterial functions are more and more favored by people.
Quaternary ammonium salt antibacterial agents have been widely studied and utilized because of their low price and fast sterilization speed. 4 generations of quaternary ammonium salt antibacterial agents of typical significance have been developed internationally; among them, DC-5700, an antibacterial agent of silicone quaternary ammonium salt developed by Dow Corning is the most representative. Since the antibacterial agent of silicone quaternary ammonium salt combines a quaternary ammonium salt with a silane coupling agent in its structure, this product has accepted washing resistance and an excellent antibacterial effect at the same time. However, DC-5700 has an obvious defect in that a fabric subjected to antibacterial finishing with it is extremely hydrophobic, which limits its application scenarios. It severely limits its application in fabrics that contact with skin, such as an underwear.
It is necessary to develop an antibacterial agent not only with good antibacterial property, but also with good hydrophilicity.
SUMMARY
In view of the problems existed in the prior art, the present invention has developed a hydrophilic antibacterial finishing agent for post finishing of a fabric. An antibacterial fabric made by this antibacterial finishing method not only has an excellent antibacterial performance, but also has good hydrophilicity.
One of the technical solutions of the present invention is to provide a hydrophilic antibacterial finishing agent including the following components in parts by weight:
0.01-1 part of a silicone hydrophilic antibacterial agent;
1-5 parts of a silicone coupling antibacterial agent; and
94-98.99 parts of water;
wherein the silicone hydrophilic antibacterial agent has a chemical structure as shown in the formula I below,
wherein R is selected from methyl, ethyl, C
3-C
6 alkyl, vinyl, allyl or an aromatic ring substituent; X
1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; X
2 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; r = 1-100; s = 1-100; t = 1-100; m = 1-100; and n = 1-100.
In a preferred embodiment of the present invention, the r, s, t, m and n satisfy that the sum of r + s + t + 3 (m + n) is greater than or equal to 40 and less than or equal to 80.
In a preferred embodiment of the present invention, the aforementioned silicone coupling antibacterial agent is at least one of dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium bromide, dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium bromide, dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium bromide, dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium bromide, dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium bromide, dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium bromide, dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium iodide, dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium iodide, dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium iodide, dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium iodide, dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium iodide, and dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium iodide.
In a preferred embodiment of the present invention, it further includes 0.001-0.1 part of a pH regulator.
In a preferred embodiment of the present invention, the aforementioned pH regulator is at least one of hydrochloric acid, phosphoric acid, acetic acid, lactic acid, hydroxyacetic acid, citric acid or sulfuric acid.
The second one of the technical solutions of the present invention is to provide a method for conducting antibacterial finishing of a fabric, which includes the following steps:
(1) formulation of an antibacterial finishing solution: formulating a hydrophilic antibacterial finishing agent according to the aforementioned weight parts and components of the hydrophilic antibacterial finishing agent;
(2) taking a fabric material as a substrate, and applying the antibacterial finishing solution to a surface of the fabric in a soaking manner to form a hydrophilic antibacterial composite layer, wherein a soaking bath ratio is 1: 5-1: 30, a soaking time is 3-60 minutes, and a rolling over rate of a pressing roll is 50-100%; and
(3) baking the fabric at 80-180℃ for 3-10 minutes, and naturally cooling it to room temperature.
In a preferred embodiment of the present invention, the aforementioned step (1) further includes adding 0.001-0.1 part of a pH regulator to adjust the pH to 3-6.
The third one of the technical solutions of the present invention is to provide an antibacterial fabric prepared by the aforementioned finishing method.
Beneficial effects
The fabric prepared by soaking and finishing with the antibacterial finishing agent of the present invention has an excellent antibacterial performance and a high bacteriostasis rate against Escherichia coli., the bacteriostasis rate remains at the level of 99.9%after 50 times of washing, and thus the bacteriostasis performance is lasting; and meanwhile, its hydrophilic performance remains at a very high level after 50 times of washing, which thus can keep the health level of human body for a long time and maintain the wearing performance of clothes. Furthermore, in the present invention, the fabric material is used as the substrate, and the antibacterial finishing solution is applied onto the surface of the fabric in a soaking manner to form the hydrophilic antibacterial composite layer. Other manners, such as padding, spraying and spin coating, can also used similarly for preparation, and the substrate and the hydrophilic antibacterial composite layer are connected by covalent bonds, electrostatic forces and Van der Waals forces. The scope of the present invention is expanded to include these similar methods.
DETAILED DESCRIPTION OF THE EMBODIMENTS
The following clearly and completely describes the technical solutions in the embodiments of the present invention. Apparently, the described embodiments are merely a part rather than all of the embodiments of the present invention. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without involving any inventive effort fall within the claimed scope of the present invention.
The materials, reagents, etc. used in the following embodiments are all commercially available, unless otherwise specified.
The present invention provides a hydrophilic antibacterial finishing agent including the following components in parts by weight:
0.01-1 part of a silicone hydrophilic antibacterial agent;
1-5 parts of a silicone coupling antibacterial agent; and
94-98.99 parts of water;
wherein the silicone hydrophilic antibacterial agent has a chemical structure as shown in the formula I below,
wherein R is selected from methyl, ethyl, C
3-C
6 alkyl, vinyl, allyl, phenyl, benzyl or an aromatic ring substituent; X
1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; X
2 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; r = 1-100; s = 1-100; t = 1-100; m = 1-100; and n = 1-100.
In the present invention, the aforementioned silicone hydrophilic antibacterial agent is a main active ingredient of the hydrophilic antibacterial finishing agent of the present invention, and there is no ready-made product on the market currently, so it is prepared by ourselves in the present invention.
Specifically, a method for preparing the silicone hydrophilic antibacterial agent of the present invention is as follows:
step (a) . a compound of formula 1 and a compound of formula 2 are reacted in a second reaction solvent at a reaction temperature of 100-200℃ for a reaction time of 12-72 hours to prepare a compound of formula 3, wherein R is selected from methyl, ethyl, C
3-C
6 alkyl, vinyl, allyl, phenyl, benzyl or an aromatic ring substituent; X
1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; X
2 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; r = 1-100; s =1-100; t = 1-100; m = 1-100; and n = 1-100; and
step (b) . under a condition of isolation from air, a compound of formula 3 and a compound of formula 4 are reacted in a first reaction solvent at a reaction temperature of 100-200℃ for a reaction time of 10-200 hours to obtain a hydrophilic antibacterial finishing agent with a chemical structure as shown in formula 5, wherein R is selected from methyl, ethyl, C
3-C
6 alkyl, vinyl, allyl, phenyl, benzyl or an aromatic ring substituent; X
1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; X
2 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; r = 1-100; s = 1-100; t = 1-100; m = 1-100; and n = 1-100,
wherein, the first reaction solvent can be at least one of xylene, p-xylene, toluene, ethylene glycol diethyl ether or DMF, the second reaction solvent can be at least one of xylene, p-xylene, toluene, ethylene glycol diethyl ether or DMF, and the aforementioned r, s, t, m and n satisfy that the sum of r + s + t + 3 (m + n) is greater than or equal to 40 and less than or equal to 80.
A method for preparing a compound of formula I-1 as a silicone hydrophilic antibacterial agent is as follows.
Step (a) : preparation of compound of formula 3-1
Under an N2 atm, into a 20 L reaction flask are sequentially added 5 L of xylene, 1.0 mol of a compound of formula 1-1 and 3.0 mol of a compound of formula 2-1, and stirred evenly after the addition; and the reaction solution is heated to 100℃ for reaction. The temperature is kept for 72 hours to complete the reaction.
The reaction solution is cooled to room temperature, added with a proper amount of petroleum ether, cooled to 0℃ to precipitate a large amount of solid, and filtered. The filter cake is collected to obtain 0.959 mol of a product as a white solid.
The yield is 95.9%, and the titration purity of the product is 99.4%.
1H NMR (400 MHz, CDCl
3) : δ2.65 (t, 6H) , 3.42 (t, 12H) , 3.51-3.87 (m, 172H) , 4.02 (t, 12H) , 4.42 (t, 6H) , 4.52 (s, 6H) , 4.57 (s, 6H) , 7.73-7.83 (m, 90H) .
Step (b) : preparation of compound of formula I-1
Under an N2 atm, into a 20 L reaction flask are sequentially added 5 L of xylene, 0.959 mol of a compound of formula 3-1, and 1.0 mol of a compound of formula 4-1, i.e., chloropropyl trimethoxysilane, and stirred evenly after the addition; and the reaction solution is heated to 120℃ for reaction. The temperature is kept for 48 hours to complete the reaction.
The reaction solution is cooled to room temperature, added with a proper amount of petroleum ether, cooled to -20℃ to precipitate a large amount of solid, and filtered. The filter cake is collected to obtain 0.911 mol of a product as a white solid. The yield is 95.0%,
the total yield of reaction of the two steps is 91.1%, and the titration purity of the product is 99.3%.
1H NMR (400MHz, CDCl
3) : δ0.63 (t, 2H) , 1.76 (m, 2H) , 3.28 (t, 6H) , 3.37 (t, 2H) , 3.42 (t, 12H) , 3.51-3.87 (m, 181H) , 4.02 (t, 12H) , 4.42 (t, 6H) , 4.52 (s, 6H) , 4.57 (s, 6H) , 7.73-7.83 (m, 90H) .
In Examples 2-7, a compound of formula I-2, a compound of formula I-3, a compound of formula I-4, a compound of formula I-5, a compound of formula I-6 and a compound of formula I-7 are respectively used as silicone hydrophilic antibacterial agents. Their preparation methods refer to that of the compound of formula I-1, and their structures are confirmed by nuclear magnetic data.
Example 1
The structure of a silicone hydrophilic antibacterial agent (I-1) was as follows:
0.1 part of a compound of formula I-1, 3 parts of dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium chloride and 98.9 parts of water, were added with 0.1 part of hydroxyacetic acid to adjust the pH of the system to 3-6, so as to obtain a hydrophilic antibacterial finishing agent.
A cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 10 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 80%. Subsequently, the fabric was placed into a drying room at 150℃ and baked for 5 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
Example 2
The structure of a silicone hydrophilic antibacterial agent (I-2) was as follows:
0.3 part of a compound of formula I-2, 2.8 parts of dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium chloride and 98.5 parts of water, were added with 0.08 part of acetic acid to adjust the pH of the system to 3-6, so as to obtain a hydrophilic antibacterial finishing agent.
A cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 20 for 15 minutes, and then passed through a pressing roll at a rolling over rate of 90%. Subsequently, the fabric was placed into a drying room at 160℃ and baked for 4 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
Example 3
The structure of a silicone hydrophilic antibacterial agent (I-3) was as follows:
0.5 part of a compound of formula I-3, 2.5 parts of dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium chloride and 98 parts of water, were added with 0.05 part of phosphoric acid to adjust the pH of the system to 3-6, so as to obtain a hydrophilic antibacterial finishing agent.
A polyester-cotton blended fabric was soaked in the finishing agent solution at a bath ratio of 1: 5 for 60 minutes, and then passed through a pressing roll at a rolling over rate of 100%. Subsequently, the fabric was placed into a drying room at 170℃ and baked for 3 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
Example 4
The structure of a silicone hydrophilic antibacterial agent (I-4) was as follows:
0.01 part of a compound of formula I-4, 2 parts of dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium chloride and 97 parts of water, were added with 0.04 part of citric acid to adjust the pH of the system to 3-6, so as to obtain a hydrophilic antibacterial finishing agent.
A cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 30 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 60%. Subsequently, the fabric was placed into a drying room at 160℃ and baked for 4 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
Example 5
The structure of a silicone hydrophilic antibacterial agent (I-5) was as follows:
0.8 part of a compound of formula I-5, 1.5 parts of dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium chloride and 96.5 parts of water, were added with 0.01 part of lactic acid to adjust the pH of the system to 3-6, so as to obtain a hydrophilic antibacterial finishing agent.
A cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 15 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 80%. Subsequently, the fabric was placed into a drying room at 80℃ and baked for 10 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
Example 6
The structure of a silicone hydrophilic antibacterial agent (I-6) was as follows:
0.1 part of a compound of formula I-6, 1 part of dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium bromide and 98.99 parts of water, were added with 0.005 part of hydrochloric acid to adjust the pH of the system to 3-6, so as to obtain a hydrophilic antibacterial finishing agent.
A cotton fabric was soaked in the finishing solution at a bath ratio of 1: 10 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 100%. Subsequently, the fabric was placed into a drying room at 180℃ and baked for 1 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
Example 7
The structure of a silicone hydrophilic antibacterial agent (I-7) was as follows:
1 part of a compound of formula 1-7, 5 parts of dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium iodide and 94 parts of water were utilized to obtain a hydrophilic antibacterial finishing agent.
A cotton fabric was soaked in the finishing agent solution at a bath ratio of 1: 20 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 50%. Subsequently, the fabric was placed into a drying room at 150℃ and baked for 5 minutes, and then the fabric was taken out of the drying room, and naturally cooled to room temperature to obtain a washing-resistant hydrophilic antibacterial fabric.
Comparative Example 1:
1 part of DC5700 and 99 parts of water were formulated into a solution of silicone antibacterial finishing agent, and added with hydroxyacetic acid to adjust the pH of the system to 6. A cotton fabric was soaked in the finishing solution at a bath ratio of 1: 15 for 10 minutes, and then passed through a pressing roll at a rolling over rate of 80%. Subsequently, the fabric was placed into a drying room at 150℃ and baked for 5 minutes, and then the fabric was taken out of the drying room to obtain an antibacterial fabric.
Comparative Example 2:
3 parts of DC5700 and 97 parts of water were formulated into a solution of silicone antibacterial finishing agent, and added with phosphoric acid to adjust the pH of the system to 5. A polyester-cotton blended fabric was soaked in the finishing solution at a bath ratio of 1: 20 for 60 minutes, and then passed through a pressing roll at a rolling over rate of 100%, that was, the increase in wet weight of the fabric was 100%. Subsequently, the fabric was placed into a drying room at 170℃ and baked for 2 minutes, and then the fabric was taken out of the drying room to obtain an antibacterial fabric.
Performance Test
Antibacterial property: With reference to “Textiles -Evaluation for antibacterial activity -Part 3: Shake flask method” in GB/120944.3-2008, Escherichia coli. Was selected as the strain, and the specific results were as shown in Table 1.
Hydrophilicity: a wetting time determination method was adopted: in an environment with an average temperature of 25℃ and an average relative humidity of 60%, a fabric to be tested was laid flat and tightened on a beaker, and a drop of water was dripped with a rubber-tipped dropper at a distance of about 3 cm from a cloth surface, and the time was counted until the water droplet was diffused on the cloth surface until there was no mirror emission. This time was the time for diffusion of the water droplet. The hydrophilicity is better when the spreading time is shorter. The specific results were as shown in Table 1.
Table 1 Data collation of Examples 1-7 and Comparative Examples 1-2
Therefore, It could be concluded that the fabric prepared by soaking and finishing with the antibacterial finishing agent of the present invention had an excellent antibacterial performance and a high bacteriostasis rate against Escherichia coli., the bacteriostasis rate remained at the level of 99.9%after 50 times of washing, and thus the bacteriostasis performance was lasting; and meanwhile, its hydrophilic performance remained at a very high level after 50 times of washing, which thus could keep the health level of human body for a long time and maintain the wearing performance of clothes.
Those of ordinary skills in the art can make various forms under the inspiration of this specification and without departing from the claimed scope of the claims of the present invention, and these forms are all within the claimed scope of the present invention.
Claims (8)
- A hydrophilic antibacterial finishing agent comprising the following components in parts by weight:0.01-1 part of a silicone hydrophilic antibacterial agent;1-5 parts of a silicone coupling antibacterial agent; and94-98.99 parts of water;wherein the silicone hydrophilic antibacterial agent has a chemical structure as shown in the formula I below,wherein R is selected from methyl, ethyl, C 3-C 6 alkyl, vinyl, allyl or an aromatic ring substituent; X 1 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; X 2 is selected from chlorine, bromine, iodine, p-toluenesulfonyloxy, benzenesulfonyloxy or methanesulfonyloxy; r = 1-100; s = 1-100; t = 1-100; m = 1-100; and n = 1-100.
- The hydrophilic antibacterial finishing agent according to claim 1, wherein the r, s, t, m and n satisfy that the sum of r + s + t + 3 (m + n) is greater than or equal to 40 and less than or equal to 80.
- The hydrophilic antibacterial finishing agent according to claim 1, wherein the silicone coupling antibacterial agent is at least one of dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium chloride, dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium chloride, dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium bromide, dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium bromide, dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium bromide, dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium bromide, dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium bromide, dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium bromide, dimethylhexadecyl [3- (trimethoxysilyl) propyl] ammonium iodide, dimethylhexadecyl [3- (triethoxysilyl) propyl] ammonium iodide, dimethyloctadecyl [3- (trimethoxysilyl) propyl] ammonium iodide, dimethyloctadecyl [3- (triethoxysilyl) propyl] ammonium iodide, dimethyleicosanyl [3- (trimethoxysilyl) propyl] ammonium iodide, and dimethyleicosanyl [3- (triethoxysilyl) propyl] ammonium iodide.
- The hydrophilic antibacterial finishing agent according to claim 1, further comprising 0.001-0.1 part of a pH regulator.
- The hydrophilic antibacterial finishing agent according to claim 4, wherein the pH regulator is at least one of hydrochloric acid, phosphoric acid, acetic acid, lactic acid, hydroxyacetic acid, citric acid or sulfuric acid.
- A method for conducting antibacterial finishing of a fabric, comprising the following steps:(1) formulation of an antibacterial finishing solution: formulating a hydrophilic antibacterial finishing agent according to the weight parts and components of the hydrophilic antibacterial finishing agent according to claim 1;(2) taking a fabric material as a substrate, and applying the antibacterial finishing solution to a surface of the fabric in a soaking manner to form a hydrophilic antibacterial composite layer, wherein a soaking bath ratio is 1: 5-1: 30, a soaking time is 3-60 minutes, and a rolling over rate of a pressing roll is 50-100%; and(3) baking the fabric at 80-180℃ for 3-10 minutes, and naturally cooling it to room temperature.
- The method for conducting antibacterial finishing of a fabric according to claim 6, wherein the formulation of the antibacterial finishing solution in the step (1) further comprises adding 0.001-0.1 part of a pH regulator to adjust the pH to 3-6.
- An antibacterial fabric prepared by employing the finishing method of claim 6 or 7.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202210500941.6A CN114592348B (en) | 2022-05-10 | 2022-05-10 | Hydrophilic antibacterial finishing agent, antibacterial finishing method of fabric and antibacterial fabric |
CN202210500941.6 | 2022-05-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2023216556A1 true WO2023216556A1 (en) | 2023-11-16 |
Family
ID=81821500
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2022/134213 WO2023216556A1 (en) | 2022-05-10 | 2022-11-25 | Hydrophilic antibacterial finishing agent, antibacterial finishing method of fabric and antibacterial fabric |
Country Status (2)
Country | Link |
---|---|
CN (1) | CN114592348B (en) |
WO (1) | WO2023216556A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN117988103A (en) * | 2024-02-02 | 2024-05-07 | 广东职业技术学院 | Antibacterial finishing agent for textile material, and preparation method and application thereof |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114592352B (en) * | 2022-05-10 | 2022-08-16 | 苏州百灵威超精细材料有限公司 | Hydrophilic antibacterial finishing agent and preparation method and application thereof |
CN114592348B (en) * | 2022-05-10 | 2022-08-16 | 苏州百灵威超精细材料有限公司 | Hydrophilic antibacterial finishing agent, antibacterial finishing method of fabric and antibacterial fabric |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103924444A (en) * | 2014-04-24 | 2014-07-16 | 南雄鼎成化工有限公司 | Preparation method and application of hydrophilic anti-bacteria conditioner for fabric |
WO2018095004A1 (en) * | 2016-11-24 | 2018-05-31 | 包磊 | Medical antibacterial fabric and preparation method therefor |
US20190203409A1 (en) * | 2016-09-19 | 2019-07-04 | Grasim Industries Limited | Antibacterial regenerated cellulosic fibers and process of preparation thereof |
CN111235884A (en) * | 2020-02-28 | 2020-06-05 | 稳健医疗(黄冈)有限公司 | Antibacterial finishing agent, antibacterial all-cotton spunlace non-woven fabric and product thereof |
CN114592348A (en) * | 2022-05-10 | 2022-06-07 | 苏州百灵威超精细材料有限公司 | Hydrophilic antibacterial finishing agent, antibacterial finishing method of fabric and antibacterial fabric |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007112100A2 (en) * | 2006-03-24 | 2007-10-04 | The University Of Utah Research Foundation | Highly fluorinated oils and surfactants and methods of making and using same |
CN106491633A (en) * | 2016-10-21 | 2017-03-15 | 克灵美(天津)生物科技有限公司 | A kind of good antimicrobial disinfectant of biocompatibility |
WO2019113210A1 (en) * | 2017-12-05 | 2019-06-13 | Anthos Partners, Lp | Phosphonium-based ionic drug conjugates |
CN113429559A (en) * | 2020-03-23 | 2021-09-24 | 厦门赛诺邦格生物科技股份有限公司 | Six-arm polyethylene glycol derivative with end hetero-functionalized and preparation method thereof |
CN112142947A (en) * | 2020-09-29 | 2020-12-29 | 广州恩沣新材料科技有限公司 | Preparation method and application of multifunctional moisture-absorbing quick-drying type water-based antibacterial polyurethane finishing agent |
CN113801123B (en) * | 2021-10-18 | 2022-12-09 | 苏州百灵威超精细材料有限公司 | Preparation method of 1,4,8, 11-tetraazacyclotetradecane compound and intermediate thereof |
-
2022
- 2022-05-10 CN CN202210500941.6A patent/CN114592348B/en active Active
- 2022-11-25 WO PCT/CN2022/134213 patent/WO2023216556A1/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103924444A (en) * | 2014-04-24 | 2014-07-16 | 南雄鼎成化工有限公司 | Preparation method and application of hydrophilic anti-bacteria conditioner for fabric |
US20190203409A1 (en) * | 2016-09-19 | 2019-07-04 | Grasim Industries Limited | Antibacterial regenerated cellulosic fibers and process of preparation thereof |
WO2018095004A1 (en) * | 2016-11-24 | 2018-05-31 | 包磊 | Medical antibacterial fabric and preparation method therefor |
CN111235884A (en) * | 2020-02-28 | 2020-06-05 | 稳健医疗(黄冈)有限公司 | Antibacterial finishing agent, antibacterial all-cotton spunlace non-woven fabric and product thereof |
CN114592348A (en) * | 2022-05-10 | 2022-06-07 | 苏州百灵威超精细材料有限公司 | Hydrophilic antibacterial finishing agent, antibacterial finishing method of fabric and antibacterial fabric |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN117988103A (en) * | 2024-02-02 | 2024-05-07 | 广东职业技术学院 | Antibacterial finishing agent for textile material, and preparation method and application thereof |
Also Published As
Publication number | Publication date |
---|---|
CN114592348A (en) | 2022-06-07 |
CN114592348B (en) | 2022-08-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2023216556A1 (en) | Hydrophilic antibacterial finishing agent, antibacterial finishing method of fabric and antibacterial fabric | |
CN101812086B (en) | Anti-bacterial compound and preparation method thereof | |
CN114561810B (en) | Antibacterial anti-mite fabric and preparation method thereof | |
CN101760963B (en) | Antibiotic-mould proof textile fabric and method for preparing same | |
WO2006086271A2 (en) | Methods and compositions for biocidal treatments | |
CN109930381B (en) | Preparation method of antibacterial hydrophilic washable fabric finishing agent | |
CN103924444A (en) | Preparation method and application of hydrophilic anti-bacteria conditioner for fabric | |
CN113430834A (en) | High-efficiency antibacterial fiber and preparation method thereof | |
WO2023216554A1 (en) | Hydrophilic antibacterial finishing agent, preparation method and use thereof | |
CN105054328A (en) | Manufacturing method for antibacterial material | |
CN105970614A (en) | Preparation method for antibacterial acrylic fiber | |
CN111979767A (en) | Method for preparing halamine antibacterial cotton fabric by adopting ultraviolet light grafting technology | |
CN113718522B (en) | Long-acting antibacterial composition and preparation method thereof | |
US20050011012A1 (en) | Multifunctional antimicrobial dyes | |
CN1027639C (en) | Anti-bacteria health finishing agent, and its preparing method, application and technology | |
CN108484487B (en) | Antibacterial (methyl) acrylate monomer containing quaternary pyridinium salt and carbamate structure and preparation method and application thereof | |
CN103290678A (en) | Anti-bacterial finishing agent for textiles | |
CN110564515A (en) | Essence microcapsule grafted with organic silicon quaternary ammonium salt and preparation method and application thereof | |
CN103061125A (en) | Halamine antibacterial agent containing reactive functional group, as well as preparation method and application for same | |
WO2012049978A1 (en) | Antibacterial fiber treatment agent, manufacturing method thereof, and antibacterial fiber manufacturing method | |
CN102277746B (en) | Antimicrobial emulsion used for textile fibers and application method thereof | |
CN102924496A (en) | Method for preparing anti-bacterial compound | |
CN114874261A (en) | Novel organosilicon quaternary phosphonium salt material, preparation method and antibacterial application | |
CN107604647A (en) | A kind of antibiotic ultraviolet-resistant brocade cotton | |
CN1356042A (en) | Broad-spectrum composite antibacterial agent |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 22941491 Country of ref document: EP Kind code of ref document: A1 |