CN111424427A - 一种非溶出型抗菌整理剂及其制备方法 - Google Patents
一种非溶出型抗菌整理剂及其制备方法 Download PDFInfo
- Publication number
- CN111424427A CN111424427A CN202010347924.4A CN202010347924A CN111424427A CN 111424427 A CN111424427 A CN 111424427A CN 202010347924 A CN202010347924 A CN 202010347924A CN 111424427 A CN111424427 A CN 111424427A
- Authority
- CN
- China
- Prior art keywords
- quaternary ammonium
- ammonium salt
- antibacterial
- finishing agent
- emulsifier
- 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.)
- Pending
Links
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 66
- 238000004090 dissolution Methods 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 60
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 31
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 23
- 239000000178 monomer Substances 0.000 claims abstract description 20
- 239000003999 initiator Substances 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- DEQJNIVTRAWAMD-UHFFFAOYSA-N 1,1,2,4,4,4-hexafluorobutyl prop-2-enoate Chemical compound FC(F)(F)CC(F)C(F)(F)OC(=O)C=C DEQJNIVTRAWAMD-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- RKZJBRNZFULKSP-UHFFFAOYSA-N C(C)(=O)O.C(=O)(O)CN1C=NCC1.C(CCCCCCCCCCC)[Na] Chemical compound C(C)(=O)O.C(=O)(O)CN1C=NCC1.C(CCCCCCCCCCC)[Na] RKZJBRNZFULKSP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 11
- 239000000839 emulsion Substances 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 32
- 238000010438 heat treatment Methods 0.000 claims description 31
- CASYTJWXPQRCFF-UHFFFAOYSA-N 2-chloroethyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCl CASYTJWXPQRCFF-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000012046 mixed solvent Substances 0.000 claims description 12
- 238000010992 reflux Methods 0.000 claims description 12
- 238000005303 weighing Methods 0.000 claims description 12
- 238000002156 mixing Methods 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 150000001336 alkenes Chemical class 0.000 claims description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 125000002091 cationic group Chemical group 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 8
- 239000012875 nonionic emulsifier Substances 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 6
- -1 polyoxyethylene Polymers 0.000 claims description 5
- CEFLQZWMCZPLRR-UHFFFAOYSA-N 16-bromohexadec-1-ene Chemical compound BrCCCCCCCCCCCCCCC=C CEFLQZWMCZPLRR-UHFFFAOYSA-N 0.000 claims description 4
- PNDMRFPOLBDAJX-UHFFFAOYSA-N 3,3,4-trimethylpentane-1,4-diamine Chemical class CC(C)(N)C(C)(C)CCN PNDMRFPOLBDAJX-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000011837 N,N-methylenebisacrylamide Substances 0.000 claims description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 210000003298 dental enamel Anatomy 0.000 claims description 4
- 230000001804 emulsifying effect Effects 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 4
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical group C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 4
- 238000003918 potentiometric titration Methods 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- 238000009987 spinning Methods 0.000 claims description 4
- YPLVPFUSXYSHJD-UHFFFAOYSA-N 11-bromoundec-1-ene Chemical compound BrCCCCCCCCCC=C YPLVPFUSXYSHJD-UHFFFAOYSA-N 0.000 claims description 3
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 3
- 239000011954 Ziegler–Natta catalyst Substances 0.000 claims description 3
- 235000019864 coconut oil Nutrition 0.000 claims description 3
- 239000003240 coconut oil Substances 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- 150000002191 fatty alcohols Chemical class 0.000 claims description 3
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 claims description 3
- PSEVKFKRYVAODC-UHFFFAOYSA-N 11-chloroundec-1-ene Chemical compound ClCCCCCCCCCC=C PSEVKFKRYVAODC-UHFFFAOYSA-N 0.000 claims description 2
- APJBXIMFEOFYMS-UHFFFAOYSA-N 2-methylpropan-1-amine;dihydrochloride Chemical compound Cl.Cl.CC(C)CN APJBXIMFEOFYMS-UHFFFAOYSA-N 0.000 claims description 2
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 claims description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 2
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000001587 sorbitan monostearate Substances 0.000 claims description 2
- 235000011076 sorbitan monostearate Nutrition 0.000 claims description 2
- 229940035048 sorbitan monostearate Drugs 0.000 claims description 2
- 238000002386 leaching Methods 0.000 claims 9
- 230000000845 anti-microbial effect Effects 0.000 claims 5
- 238000004659 sterilization and disinfection Methods 0.000 abstract description 12
- 239000003242 anti bacterial agent Substances 0.000 abstract description 10
- 241000588724 Escherichia coli Species 0.000 abstract description 7
- 239000000835 fiber Substances 0.000 abstract description 5
- 230000005764 inhibitory process Effects 0.000 abstract description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 4
- 241000191967 Staphylococcus aureus Species 0.000 abstract description 4
- 229910052710 silicon Inorganic materials 0.000 abstract description 4
- 239000010703 silicon Substances 0.000 abstract description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract description 2
- 230000001808 coupling effect Effects 0.000 abstract description 2
- 229910052731 fluorine Inorganic materials 0.000 abstract description 2
- 239000011737 fluorine Substances 0.000 abstract description 2
- 125000000524 functional group Chemical group 0.000 abstract description 2
- 239000011521 glass Substances 0.000 abstract description 2
- 229910010272 inorganic material Inorganic materials 0.000 abstract description 2
- 239000011147 inorganic material Substances 0.000 abstract description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 229910000077 silane Inorganic materials 0.000 abstract description 2
- 241000894006 Bacteria Species 0.000 description 14
- 238000012360 testing method Methods 0.000 description 12
- 230000001954 sterilising effect Effects 0.000 description 9
- 240000001624 Espostoa lanata Species 0.000 description 8
- 235000009161 Espostoa lanata Nutrition 0.000 description 8
- 239000000645 desinfectant Substances 0.000 description 8
- 239000004744 fabric Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000008055 phosphate buffer solution Substances 0.000 description 6
- 229920001817 Agar Polymers 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 5
- 241000282414 Homo sapiens Species 0.000 description 5
- 239000008272 agar Substances 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 4
- 239000001963 growth medium Substances 0.000 description 4
- 230000007547 defect Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000012137 tryptone Substances 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 229940041514 candida albicans extract Drugs 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- ARYZCSRUUPFYMY-UHFFFAOYSA-N methoxysilane Chemical compound CO[SiH3] ARYZCSRUUPFYMY-UHFFFAOYSA-N 0.000 description 2
- 239000013641 positive control Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000012138 yeast extract Substances 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 239000007836 KH2PO4 Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000011282 treatment 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
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
- D06M15/3568—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing silicon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
- D06M15/277—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof containing fluorine
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
本发明公开了一种非溶出型抗菌整理剂及其制备方法,按重量份数计包括:季铵盐抗菌单体、丙烯酸六氟丁酯、十二烷基羧甲基钠型咪唑啉醋酸盐、引发剂、交联剂、催化剂、乳化剂和水;本发明基于硅烷的分子偶联作用,充分利用有机硅分子上三甲氧基官能团的既可与玻璃、硅、金属等无机材质反应结合、又可与纤维树脂等有机分子直接结合并能够在一般物体表面“扎根”固定的性质,达到固化长效消毒,尤其对大肠杆菌和金黄色葡萄球菌的抑制率较高,引入丙烯酸六氟丁酯,含氟基团可以降低抗菌整理剂的表面能,相较于传统的双子季铵盐抗菌剂更不易更不易溶出,与纤维结合牢固、持久,抗菌效果明显,多次洗涤后仍具有很好的抑菌效果。
Description
技术领域
本发明涉及一种非溶出型抗菌整理剂及其制备方法。
背景技术
在人类的日常生活中,难免会接触到各种各样的微生物,这些微生物可以直接或间接的对人体产生危害,而微生物在一定的环境条件下可以迅速繁殖,这些微生物以人体分泌的汗液、油脂、皮屑或织物本身的分解物质作为营养品迅速繁殖,形成大量有害的细菌并通过空气进行传播,从而引起疾病,影响人们的日常生活。微生物的存在还会导致织物纤维大分子降解,使织物出现脆损、变色、霉变等现象,影响服装及装饰品的外观、色泽;对于一些军用物品,如降落伞、炮衣、帐篷等,则会危及安全,影响战斗力,后果不堪设想;为了解决上述问题,可行的办法将能杀灭对人体和衣物有害的抗菌药剂来处理织物。
传统的抗菌剂主要采用季铵盐化合物,季铵盐类消毒剂是指用具有消毒作用的季铵类化合物为有效成分制成的消毒剂,其是一种阳离子表面活性剂的代表,因季铵盐化合物能吸附带负电荷的细菌,具有良好的杀菌作用,在国际上使用广泛;单链季铵盐的逐渐显现出一些缺点,如杀生谱较窄,细菌对其产生了耐药性以及对细菌具有较高的MIC值等;目前,在纺织品抗菌中,首先需要考虑普通季铵盐是溶出型的,易洗脱。但是,如果将硅氧烷引入季铵盐结构中制得有机硅季铵盐,可使其性能发生巨大变化;目前已有不少研究关于双子季铵盐抗菌剂的报道,也表现出了较为优异的抗菌性能和以及杀菌范围广等特性,但其仍为小分子季铵盐,存在小分子季铵盐的共性缺点,将其应用在织物上作为抗菌整理剂的效果并不理想。
发明内容
本发明的目的是为了解决以上现有技术的不足,提出了一种非溶出型抗菌
整理剂,按重量份数计包括:
所述的季铵盐抗菌单体由以下制备方法得到:
(1)将物质的量比为2.02-2.1:1的长链卤代烯烃与四甲基-1,4-丁二胺加入带有冷凝回流装置的搪瓷反应釜中混合均匀,然后加入溶剂和阻聚剂,90-110℃下加热回流20-48h,旋去溶剂,用***萃洗去除阻聚剂和未反应的长链卤代烯烃,得到双子季铵盐;
(2)将β-氯乙基三甲氧基硅烷和混合溶剂加入到反应釜中,搅拌条件下以10℃/min的升温速率升温,当温度达到60℃时,将步骤(1)中的双子季铵盐滴加入反应釜中,2-3h滴加完毕;以10℃/min的升温速率继续升温至80℃,进行恒温回流反应,在密闭状态下反应,用电位滴定法测定氯离子的质量百分含量为54%时,停止反应;其中,所述的β-氯乙基三甲氧基硅烷、双子季铵盐和混合溶剂的摩尔比为n(β-氯乙基三甲氧基硅烷):n(双子季铵盐):n(混合溶剂)=1.0:1.1:7-10;
(3)待反应釜温度降至室温,调节产物pH为6.0,均质搅拌10min,然后过滤脱色并去除杂质,即得所述季铵盐抗菌单体。
优选地,所述的长链卤代烯烃为11-溴-1-十一烯、11-氯-1-十一烯和16-溴-1-十六烯中的任意一种。
优选地,所述的溶剂为异丙醇、丙酮和乙醇中的一种或几种。
优选地,所述的阻聚剂为对苯二酚。
优选地,所述的乳化剂由质量百分比为60~80%的非离子型乳化剂和20~40%的阳离子型乳化剂组成;所述的非离子型乳化剂为脂肪醇聚氧乙烯、椰油脂肪酸二乙醇酰胺和失水山梨醇单硬脂酸酯中的一种或几种的混合物;所述的阳离子型乳化剂为十六烷基三甲基溴化铵和十二烷基苯磺酸钠中的一种或两种。
优选地,所述的引发剂为2,2-偶氮二(2-甲基丙基咪)二盐酸盐、偶氮二异丁腈和过硫酸铵中的任意一种。
优选地,所述的交联剂为N,N-亚甲基双丙烯酰胺。
优选地,所述的催化剂为双组分齐格勒纳塔催化剂,用量为双子季铵盐用量的0.15-0.3wt%。
优选地,所述的催化剂为TiCl4-Al(C2H5)3。
一种非溶出型抗菌整理剂的制备方法,包括如下步骤:按重量份数称取引发剂、水和乳化剂,将引发剂分为二份,将第一份引发剂、水和乳化剂加入反应容器中混合均匀,然后按照重量份数分别称取季铵盐抗菌单体、丙烯酸六氟丁酯、十二烷基羧甲基钠型咪唑啉醋酸盐、交联剂和催化剂,并加入到反应容器中,乳化后得到预乳化液;将所述预乳化液升温至50-70℃时,加入第二份引发剂,继续升温,在80-105℃保温2-4h,得到所述抗菌整理剂。
当所述的长链卤代烯烃为16-溴-1-十六烯时,所述的季铵盐抗菌单体结构式为:
本发明的有益效果如下:
(1)本发明基于硅烷的分子偶联作用,充分利用有机硅分子上三甲氧基官能团的既可与玻璃、硅、金属等无机材质反应结合、又可与纤维树脂等有机分子直接结合并能够在一般物体表面“扎根”固定的性质,创新地在双子季铵盐上引入甲氧基烷基硅,将其应用在织物表面形成聚合性分子层达到固化长效消毒,而且具有较好的抗菌活性、较广的杀菌谱、较高的化学稳定性和较低的生物毒性;
(2)本发明将双子季铵盐长链与硅氧烷连接,既充分发挥了聚合双子季铵盐的较强的杀菌效力,使之在较低浓度下即可达到快速杀菌效果,尤其对大肠杆菌和金黄色葡萄球菌的抑制率较高,引入丙烯酸六氟丁酯,含氟基团可以降低抗菌整理剂的表面能,相较于传统的双子季铵盐抗菌剂更不易更不易溶出,与纤维结合牢固、持久,抗菌效果明显,多次洗涤后仍具有很好的抑菌效果,对人体安全可靠,因此可以得到广泛的应用。
具体实施方式
为了加深对本发明的理解,下面将结合实施例对本发明作进一步详述,该实施例仅用于解释本发明,并不构成对本发明保护范围的限定。
下述实施例中所使用的实验方法如无特殊说明,均为常规方法。
下述实施例中所用的材料、试剂等,如无特殊说明,均可从商业途径得到。
实施例1
一种非溶出型抗菌整理剂,按重量份数计包括:季铵盐抗菌单体65份、丙烯酸六氟丁酯32份、十二烷基羧甲基钠型咪唑啉醋酸盐12份、2,2-偶氮二(2-甲基丙基咪)二盐酸盐0.05份、N,N-亚甲基双丙烯酰胺0.1份、TiCl4-Al(C2H5)30.04份、乳化剂2份、水100份;
所述的季铵盐抗菌单体由以下制备方法得到:
(1)将物质的量比为2.05:1的11-溴-1-十一烯与四甲基-1,4-丁二胺加入带有冷凝回流装置的搪瓷反应釜中混合均匀,然后加入溶剂异丙醇和对苯二酚,95℃下加热回流24h,旋去溶剂,用***萃洗去除阻聚剂和未反应的长链卤代烯烃,得到双子季铵盐;
(2)将β-氯乙基三甲氧基硅烷和混合溶剂加入到反应釜中,搅拌条件下以10℃/min的升温速率升温,当温度达到60℃时,将步骤(1)中的双子季铵盐滴加入反应釜中,2h滴加完毕;以10℃/min的升温速率继续升温至80℃,进行恒温回流反应,在密闭状态下反应,用电位滴定法测定氯离子的质量百分含量为54%时,停止反应;其中,所述的β-氯乙基三甲氧基硅烷、双子季铵盐和混合溶剂的摩尔比为n(β-氯乙基三甲氧基硅烷):n(双子季铵盐):n(混合溶剂)=1.0:1.1:8;
(3)待反应釜温度降至室温,调节产物pH为6.0,均质搅拌10min,然后过滤脱色并去除杂质,即得所述季铵盐抗菌单体。
在上述技术方案中,所述的乳化剂由质量百分比为80%的非离子型乳化剂和20%的阳离子型乳化剂组成;所述的非离子型乳化剂为脂肪醇聚氧乙烯;所述的阳离子型乳化剂为十六烷基三甲基溴化铵。
一种非溶出型抗菌整理剂的制备方法,包括如下步骤:按重量份数称取引发剂、水和乳化剂,将引发剂分为二份,将第一份引发剂、水和乳化剂加入反应容器中混合均匀,然后按照重量份数分别称取季铵盐抗菌单体、丙烯酸六氟丁酯、十二烷基羧甲基钠型咪唑啉醋酸盐、交联剂和催化剂,并加入到反应容器中,乳化后得到预乳化液;将所述预乳化液升温至50-70℃时,加入第二份引发剂,继续升温,在80-105℃保温2-4h,得到所述抗菌整理剂。
实施例2
一种非溶出型抗菌整理剂,按重量份数计包括:季铵盐抗菌单体70份、丙烯酸六氟丁酯35份、十二烷基羧甲基钠型咪唑啉醋酸盐8份、偶氮二异丁腈0.06份、N,N-亚甲基双丙烯酰胺0.2份、TiCl4-Al(C2H5)30.08份、乳化剂5份、水120份;
所述的季铵盐抗菌单体由以下制备方法得到:
(1)将物质的量比为2.1:1的16-溴-1-十六烯与四甲基-1,4-丁二胺加入带有冷凝回流装置的搪瓷反应釜中混合均匀,然后加入溶剂异丙醇和对苯二酚,100℃下加热回流30h,旋去溶剂,用***萃洗去除阻聚剂和未反应的长链卤代烯烃,得到双子季铵盐;
(2)将β-氯乙基三甲氧基硅烷和混合溶剂加入到反应釜中,搅拌条件下以10℃/min的升温速率升温,当温度达到60℃时,将步骤(1)中的双子季铵盐滴加入反应釜中,3h滴加完毕;以10℃/min的升温速率继续升温至80℃,进行恒温回流反应,在密闭状态下反应,用电位滴定法测定氯离子的质量百分含量为54%时,停止反应;其中,所述的β-氯乙基三甲氧基硅烷、双子季铵盐和混合溶剂的摩尔比为n(β-氯乙基三甲氧基硅烷):n(双子季铵盐):n(混合溶剂)=1.0:1.1:7;
(3)待反应釜温度降至室温,调节产物pH为6.0,均质搅拌10min,然后过滤脱色并去除杂质,即得所述季铵盐抗菌单体。
在上述技术方案中,所述的乳化剂由质量百分比为80%的非离子型乳化剂和20%的阳离子型乳化剂组成;所述的非离子型乳化剂为椰油脂肪酸二乙醇酰胺;所述的阳离子型乳化剂为十二烷基苯磺酸钠。
一种非溶出型抗菌整理剂的制备方法,包括如下步骤:按重量份数称取引发剂、水和乳化剂,将引发剂分为二份,将第一份引发剂、水和乳化剂加入反应容器中混合均匀,然后按照重量份数分别称取季铵盐抗菌单体、丙烯酸六氟丁酯、十二烷基羧甲基钠型咪唑啉醋酸盐、交联剂和催化剂,并加入到反应容器中,乳化后得到预乳化液;将所述预乳化液升温至50-70℃时,加入第二份引发剂,继续升温,在80-105℃保温2-4h,得到所述抗菌整理剂。
性能测定
应用本发明的抗菌整理剂及产品浓度定型,参照中华人民共和国***2002年(消毒技术规范),即采用琼脂稀释法,用磷酸盐缓冲液(简称PBS)将该洗液进行系列稀释,即将本发明的抗菌整理剂原液1份体积分别加入9份、49份、199份和499份体积磷酸盐缓冲液(PBS)进行稀释分别得到10倍、50倍、100倍、200倍、500倍稀释液。上述各稀释液分别与MH琼脂培养基混合溶解,进行如下浓度定型实验;
(1)MH琼脂培养基:根据中华人民共和国医药行业标准YY/T0665-2008,即每1000mL水加入酸水解酪蛋白17.5g和可溶性淀粉1.5g,和牛肉浸出粉2.0g,和琼脂15g,加热至沸腾溶解,然后经高压蒸汽灭菌法处理,置于45-50℃水浴中备用;
(2)PBS缓冲液:称取NaCl 8g、KCl 0.2g、Na2HPO41.44 g、KH2PO40.24g,加入990mL水溶解,调节pH为7.4,定容至1000mL,高压灭菌后室温保存;
(3)采用大肠杆菌(ATCC8099),配制菌悬液,浓度为107cfu/ml;
(4)中和剂:采用PBS缓冲液配制0.3%卵磷脂和3%的吐温80;
(5)胰胨大豆酪蛋白培养基(TSA培养基):根据中国药典2010标准及EP/USP标准,分别称取胰胨17g、多价蛋白胨3g、酵母膏6g、氯化钠5g、磷酸氢二钾2.5g、葡萄糖2.5g,加入蒸馏水900mL,将上述各成分加热搅拌溶解,调节pH至7.4,加水定容至1000mL,高压灭菌后备用;
(6)TSA培养基琼脂平板:分别称取胰胨17g、多价蛋白胨3g、酵母膏6g、氯化钠5g、磷酸氢二钾2.5g、葡萄糖2.5g、琼脂15g,加入蒸馏水900mL,将上述各成分加热搅拌溶解,调节pH至7.4,加水定容至1000mL,高压灭菌后备用;
(7)实验用菌:大肠杆菌(菌种编号ATCC8099)悬液,金黄色葡萄球菌(菌种编号ATCC6538)悬液,浓度均为1~5×108cfu/ml;
试验方法:取消毒无菌大试管3管,在超净台,分别加入0.9ml本发明的抗菌整理剂和预先采用10、50、100、200和500倍稀释的本发明的抗菌整理剂稀释液,再分别加到9.1ml经灭菌的中和剂中,混匀作用1.0min;而后,向各管加入0.1ml试验用菌悬液,在20℃±1℃条件下相互作用,第一管、第二管和第三管作用时间分别为2.5min、5.0min和7.5min,各试验管分别吸取5.0ml样液,按活菌培养计数方法测定37℃培养后存活菌数,每管样液接种10个MH培养基琼脂平板;按活菌培养计数方法对培养的菌落进行计数;
阳性对照:用0.1ml试验用菌悬液与9.9mL TSA培养基,作为阳性对照,进行平行试验;
所有试验样本均在37℃温箱中培养,对细菌繁殖体培养48h观察最终结果;灭菌试验重复3次,计算各组的活菌浓度(cfu/ml),并换算为对数值(N),然后按下式计算杀灭对数值;其中杀灭对数值(KL)=对照组平均活菌浓度的对数值(No)-试验组活菌浓度对数值(Nx)。
(8)棉织品的抗菌耐洗试验
应用本发明的固化性季铵盐消毒液整理棉织品的抗菌耐洗试验,操作如下:
1)称重棉花团,置于本发明的消毒液中,消毒液体积为棉花质量的50倍,常温浸泡30min,直接晾干,得到整理后的棉团;
2)抗菌棉织物抑菌测试,按FZ/T73023-2006中振荡法测试抗菌整理后棉团的抑菌率,实验用菌悬液为大肠杆菌悬液,浓度为1~5×108cfu/ml;
3)对整理后的棉团按照FZ/T73023-2006洗涤标准进行多次洗涤处理,在5、10、15、20、25和30次洗涤后进行实验。
实验结果
(1)本发明的可固化季铵盐配制的消毒液对细菌的消毒杀菌效果如表1所示。结果表明,依据***《消毒技术规范》2002.11版技术规范要求,在20℃±1℃条件下本发明的抗菌整理剂,依据技术规范要求作用5.0min对大肠杆菌和金黄色葡萄球菌的杀灭对数值均大于5.0。
表1可固化季铵盐配制的消毒液对细菌的消毒杀菌效果
(2)抗菌整理耐久性分析中,本发明消毒液对整理后的棉团在大肠杆菌的抑制率如下:结果表明,本发明消毒液处理的棉团,在大肠杆菌悬液中18小时震摇,对细菌生长的抑制率达到98%;耐洗试验中,30次洗涤后的抑制率大于97%。
以上所述仅为本发明的较佳实施例而已,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (10)
1.一种非溶出型抗菌整理剂,其特征在于,按重量份数计包括:
所述的季铵盐抗菌单体由以下制备方法得到:
(1)将物质的量比为2.02-2.1:1的长链卤代烯烃与四甲基-1,4-丁二胺加入带有冷凝回流装置的搪瓷反应釜中混合均匀,然后加入溶剂和阻聚剂,90-110℃下加热回流20-48h,旋去溶剂,用***萃洗去除阻聚剂和未反应的长链卤代烯烃,得到双子季铵盐;
(2)将β-氯乙基三甲氧基硅烷和混合溶剂加入到反应釜中,搅拌条件下以10℃/min的升温速率升温,当温度达到60℃时,将步骤(1)中的双子季铵盐滴加入反应釜中,2-3h滴加完毕;以10℃/min的升温速率继续升温至80℃,进行恒温回流反应,在密闭状态下反应,用电位滴定法测定氯离子的质量百分含量为54%时,停止反应;其中,所述的β-氯乙基三甲氧基硅烷、双子季铵盐和混合溶剂的摩尔比为n(β-氯乙基三甲氧基硅烷):n(双子季铵盐):n(混合溶剂)=1.0:1.1:7-10;
(3)待反应釜温度降至室温,调节产物pH为6.0,均质搅拌10min,然后过滤脱色并去除杂质,即得所述季铵盐抗菌单体。
2.根据权利要求1所述的一种非溶出型抗菌整理剂,其特征在于,所述的长链卤代烯烃为11-溴-1-十一烯、11-氯-1-十一烯和16-溴-1-十六烯中的任意一种。
3.根据权利要求1所述的一种非溶出型抗菌整理剂,其特征在于,所述的溶剂为异丙醇、丙酮和乙醇中的一种或几种。
4.根据权利要求1所述的一种非溶出型抗菌整理剂,其特征在于,所述的阻聚剂为对苯二酚。
5.根据权利要求1所述的一种非溶出型抗菌整理剂,其特征在于,所述的乳化剂由质量百分比为60~80%的非离子型乳化剂和20~40%的阳离子型乳化剂组成;所述的非离子型乳化剂为脂肪醇聚氧乙烯、椰油脂肪酸二乙醇酰胺和失水山梨醇单硬脂酸酯中的一种或几种的混合物;所述的阳离子型乳化剂为十六烷基三甲基溴化铵和十二烷基苯磺酸钠中的一种或两种。
6.根据权利要求1所述的一种非溶出型抗菌整理剂,其特征在于,所述的引发剂为2,2-偶氮二(2-甲基丙基咪)二盐酸盐、偶氮二异丁腈和过硫酸铵中的任意一种。
7.根据权利要求1所述的一种非溶出型抗菌整理剂,其特征在于,所述的交联剂为N,N-亚甲基双丙烯酰胺。
8.根据权利要求1所述的一种非溶出型抗菌整理剂,其特征在于,所述的催化剂为双组分齐格勒纳塔催化剂,用量为双子季铵盐用量的0.15-0.3wt%。
9.根据权利要求8所述的一种非溶出型抗菌整理剂,其特征在于:所述的催化剂为TiCl4-Al(C2H5)3。
10.根据权利要求1~9任一项所述的非溶出型抗菌整理剂的制备方法,其特征在于,包括如下步骤:按重量份数称取引发剂、水和乳化剂,将引发剂分为二份,将第一份引发剂、水和乳化剂加入反应容器中混合均匀,然后按照重量份数分别称取季铵盐抗菌单体、丙烯酸六氟丁酯、十二烷基羧甲基钠型咪唑啉醋酸盐、交联剂和催化剂,并加入到反应容器中,乳化后得到预乳化液;将所述预乳化液升温至50-70℃时,加入第二份引发剂,继续升温,在80-105℃保温2-4h,得到所述抗菌整理剂。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202010347924.4A CN111424427A (zh) | 2020-04-28 | 2020-04-28 | 一种非溶出型抗菌整理剂及其制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202010347924.4A CN111424427A (zh) | 2020-04-28 | 2020-04-28 | 一种非溶出型抗菌整理剂及其制备方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN111424427A true CN111424427A (zh) | 2020-07-17 |
Family
ID=71558365
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202010347924.4A Pending CN111424427A (zh) | 2020-04-28 | 2020-04-28 | 一种非溶出型抗菌整理剂及其制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN111424427A (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113854320A (zh) * | 2021-10-18 | 2021-12-31 | 阜南县猛发工艺品有限公司 | 一种竹藤编织品用防虫防霉剂及其制备方法 |
CN116656203A (zh) * | 2023-08-02 | 2023-08-29 | 江西永通科技股份有限公司 | 一种具有防霉抗菌性能的涂料组合物及其制备方法 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1792158A (zh) * | 2005-11-30 | 2006-06-28 | 山东大学 | 一种有机硅季铵盐杀菌剂的制备方法 |
US20120125226A1 (en) * | 2010-05-07 | 2012-05-24 | Resource Development L.L.C. | Solvent-Free Organosilane Quaternary Ammonium Compositions, Method of Making and Use |
CN103535372A (zh) * | 2013-10-09 | 2014-01-29 | 江苏惠兴康科技有限公司 | 可固化复合季铵盐、制备方法及其消毒抗菌灭菌应用 |
CN105155269A (zh) * | 2015-08-09 | 2015-12-16 | 浙江康德新材料有限公司 | 一种季铵盐抗菌剂单体改性织物整理剂及其制备方法 |
CN105297439A (zh) * | 2015-11-04 | 2016-02-03 | 南通纺织丝绸产业技术研究院 | 一种含氟聚丙烯酸酯织物整理剂、制备方法及其应用 |
CN107881784A (zh) * | 2017-11-24 | 2018-04-06 | 福州大学 | 一种阳离子型含氟丙烯酸酯织物整理剂及其制备方法 |
-
2020
- 2020-04-28 CN CN202010347924.4A patent/CN111424427A/zh active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1792158A (zh) * | 2005-11-30 | 2006-06-28 | 山东大学 | 一种有机硅季铵盐杀菌剂的制备方法 |
US20120125226A1 (en) * | 2010-05-07 | 2012-05-24 | Resource Development L.L.C. | Solvent-Free Organosilane Quaternary Ammonium Compositions, Method of Making and Use |
CN103535372A (zh) * | 2013-10-09 | 2014-01-29 | 江苏惠兴康科技有限公司 | 可固化复合季铵盐、制备方法及其消毒抗菌灭菌应用 |
CN105155269A (zh) * | 2015-08-09 | 2015-12-16 | 浙江康德新材料有限公司 | 一种季铵盐抗菌剂单体改性织物整理剂及其制备方法 |
CN105297439A (zh) * | 2015-11-04 | 2016-02-03 | 南通纺织丝绸产业技术研究院 | 一种含氟聚丙烯酸酯织物整理剂、制备方法及其应用 |
CN107881784A (zh) * | 2017-11-24 | 2018-04-06 | 福州大学 | 一种阳离子型含氟丙烯酸酯织物整理剂及其制备方法 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113854320A (zh) * | 2021-10-18 | 2021-12-31 | 阜南县猛发工艺品有限公司 | 一种竹藤编织品用防虫防霉剂及其制备方法 |
CN116656203A (zh) * | 2023-08-02 | 2023-08-29 | 江西永通科技股份有限公司 | 一种具有防霉抗菌性能的涂料组合物及其制备方法 |
CN116656203B (zh) * | 2023-08-02 | 2023-10-27 | 江西永通科技股份有限公司 | 一种具有防霉抗菌性能的涂料组合物及其制备方法 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Lim et al. | Synthesis and antimicrobial activity of a water-soluble chitosan derivative with a fiber-reactive group | |
US8486428B2 (en) | Compositions and methods for making and using acyclic N-halamine-based biocidal polymeric materials and articles | |
Mirjalili et al. | Antibacterial dyeing of polyamide using turmeric as a natural dye | |
WO2020228808A1 (zh) | 表面修饰龙脑的抗菌天然纺织材料及其制备方法与应用 | |
US20080102217A1 (en) | Process for anti-microbial textiles treatment | |
CN111424427A (zh) | 一种非溶出型抗菌整理剂及其制备方法 | |
NO318855B1 (no) | Varige og genererbare mikrobiocide tekstiler | |
CN111500137B (zh) | 一种抗菌、抗病毒的乳液粘合成膜剂、制备方法及其应用 | |
CN107287899A (zh) | 棉织物的抗菌整理方法 | |
CN107604662B (zh) | 用于修饰纺织品的杀菌抗病毒组合物 | |
CN109942751A (zh) | 一种塑料抗菌材料的制备方法 | |
CN106234388B (zh) | 一种含苯并烯氟菌唑和小檗碱的农药组合物 | |
WO2021253015A1 (en) | Textile treatment compositions | |
CN111533835A (zh) | 一种具有长效抗菌的固化性季铵盐及应用 | |
CN111150705A (zh) | 一种酒精玻尿酸消毒液及其制备方法 | |
CN104594024B (zh) | 一种制备抗菌防霉纺织品的方法 | |
Rajendran et al. | Development of a versatile antimicrobial finish for textile materials for healthcare and hygiene applications | |
WO2022103649A2 (en) | Use of siliceous quaternary amines in durable antimicrobial treatment of textile for use in healthcare environment | |
JP2004509220A (ja) | 抗菌性ポリマー | |
CN101961010B (zh) | 一种吸水消毒干粉及其制备方法 | |
US3899616A (en) | Fungistatic fabric treatment | |
Vukušić et al. | Antibacterial Properties of Citric Acid Used as Easy-Care Finishing Agent. | |
CN113652868B (zh) | 一种纺织品用抗菌抗病毒助剂及其制备方法和应用 | |
CN111321592B (zh) | 一种有机抗菌整理剂、抗菌织物及其制备方法 | |
KR102459230B1 (ko) | 내세탁성이 향상된 섬유용 항균 조성물 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200717 |
|
RJ01 | Rejection of invention patent application after publication |