CN113430814A - Preparation method of composite antibacterial agent and application of composite antibacterial agent in polyester fabric - Google Patents
Preparation method of composite antibacterial agent and application of composite antibacterial agent in polyester fabric Download PDFInfo
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- CN113430814A CN113430814A CN202110857124.1A CN202110857124A CN113430814A CN 113430814 A CN113430814 A CN 113430814A CN 202110857124 A CN202110857124 A CN 202110857124A CN 113430814 A CN113430814 A CN 113430814A
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- Prior art keywords
- zinc oxide
- antibacterial agent
- nano zinc
- composite antibacterial
- halamine
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- 239000003242 anti bacterial agent Substances 0.000 title claims abstract description 76
- 239000002131 composite material Substances 0.000 title claims abstract description 76
- 239000004744 fabric Substances 0.000 title claims abstract description 71
- 229920000728 polyester Polymers 0.000 title claims abstract description 49
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims abstract description 212
- 239000011787 zinc oxide Substances 0.000 claims abstract description 106
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 85
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 238000002156 mixing Methods 0.000 claims abstract description 15
- 150000002366 halogen compounds Chemical class 0.000 claims abstract description 13
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 230000009471 action Effects 0.000 claims abstract description 6
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 27
- 239000000839 emulsion Substances 0.000 claims description 20
- 238000003756 stirring Methods 0.000 claims description 19
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 18
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000005406 washing Methods 0.000 claims description 16
- 238000001132 ultrasonic dispersion Methods 0.000 claims description 15
- 239000002245 particle Substances 0.000 claims description 14
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 13
- 239000007822 coupling agent Substances 0.000 claims description 12
- 230000001877 deodorizing effect Effects 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 12
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims description 12
- 238000002791 soaking Methods 0.000 claims description 12
- 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 11
- 230000008569 process Effects 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 9
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 9
- 238000005660 chlorination reaction Methods 0.000 claims description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 8
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 claims description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000003431 cross linking reagent Substances 0.000 claims description 6
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 4
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 4
- CRZQGDNQQAALAY-UHFFFAOYSA-N Methyl benzeneacetate Chemical compound COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 claims description 4
- 229940007550 benzyl acetate Drugs 0.000 claims description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- 229910002621 H2PtCl6 Inorganic materials 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 claims description 3
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 claims description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229940044603 styrene Drugs 0.000 claims description 2
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims description 2
- 229940086542 triethylamine Drugs 0.000 claims description 2
- 239000004599 antimicrobial Substances 0.000 claims 4
- 230000000845 anti-microbial effect Effects 0.000 claims 3
- 239000000463 material Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 23
- 239000002781 deodorant agent Substances 0.000 description 22
- 239000011259 mixed solution Substances 0.000 description 13
- 239000012046 mixed solvent Substances 0.000 description 11
- -1 Isopropyl Chemical group 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 238000004332 deodorization Methods 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 238000007598 dipping method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 238000005096 rolling process Methods 0.000 description 5
- 210000004243 sweat Anatomy 0.000 description 5
- 239000011701 zinc Substances 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 239000013068 control sample Substances 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 231100000956 nontoxicity Toxicity 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- YOCIJWAHRAJQFT-UHFFFAOYSA-N 2-bromo-2-methylpropanoyl bromide Chemical compound CC(C)(Br)C(Br)=O YOCIJWAHRAJQFT-UHFFFAOYSA-N 0.000 description 1
- DTZKVZKYSZUBAG-UHFFFAOYSA-N 2-chloro-2-methylpropanoyl chloride Chemical compound CC(C)(Cl)C(Cl)=O DTZKVZKYSZUBAG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010040904 Skin odour abnormal Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 239000002699 waste material Substances 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
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/32—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond
- D06M11/36—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with oxygen, ozone, ozonides, oxides, hydroxides or percompounds; Salts derived from anions with an amphoteric element-oxygen bond with oxides, hydroxides or mixed oxides; with salts derived from anions with an amphoteric element-oxygen bond
- D06M11/44—Oxides or hydroxides of elements of Groups 2 or 12 of the Periodic System; Zincates; Cadmates
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/07—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof
- D06M11/30—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof with oxides of halogens, oxyacids of halogens or their salts, e.g. with perchlorates
-
- 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
- D06M2101/16—Synthetic fibres, other than mineral fibres
- D06M2101/30—Synthetic polymers consisting of macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M2101/32—Polyesters
Abstract
The invention relates to the field of antibacterial fabric materials, and discloses a preparation method of a composite antibacterial agent and application of the composite antibacterial agent in polyester fabric, wherein the preparation method of the composite antibacterial agent comprises the following steps: (1) mixing amino modified nano zinc oxide with a halogen compound for reaction to obtain halogen modified amino nano zinc oxide; (2) the halogen modified amino nano zinc oxide and the antibacterial agent are mixed in an organic solvent, a catalyst is added, and a polymerization reaction is carried out under the action of the catalyst to obtain the nano zinc oxide halamine composite antibacterial agent.
Description
Technical Field
The invention relates to the field of antibacterial fabric materials, in particular to a preparation method of a composite antibacterial agent and application of the composite antibacterial agent in polyester fabrics.
Background
In the face of various global public health incidents which affect more profound and more remote, the health concept slowly deepens into the heart of the vast consumers, and the health and the safety become more important in the aspects of 'clothes and eating and housing movement' and the like. As is known, the metabolism of the body needs to perspire, and certain metabolic wastes exist in the sweat, so that the sweat has the effect of expelling toxin to a certain extent. However, the accumulation of inorganic substances in sweat can change the pH value of the skin and cause certain damage to the skin. Under the condition of proper temperature and humidity, the organic components in the sweat are accumulated on the body surface and bacteria are easy to breed, a large amount of bacteria can make the sweat send peculiar smell and stink through breeding, and serious people can even cause skin diseases, so that the demand growth trend of the antibacterial and deodorizing textile is obvious.
The antibacterial property of the textile is mainly realized by adopting a post-finishing method in the market at present, compared with the preparation of antibacterial fiber, the process is shorter, and the antibacterial property of the textile can be quickly obtained. The antibacterial agents applied to the textiles are numerous, wherein the halamine antibacterial agent achieves the efficient sterilization effect due to the fact that halogen is used as an antibacterial element, and the 'renewable' unique antibacterial property can be achieved by means of conversion between N-H and N-X bonds in the chemical structure of the halamine antibacterial agent, so that the defect that the antibacterial property of most of antibacterial agent finished fabrics gradually disappears along with the increase of the using time is overcome; the nano zinc oxide has the excellent performances of no toxicity, large specific surface area, antibacterial property, ultraviolet radiation resistance, low cost and the like. However, for polyester fabrics, the chemical reaction inertia is strong, the hygroscopicity is poor, and the prepared fabrics have poor antibacterial performance by directly using nano zinc oxide or halamine antibacterial agent for antibacterial treatment.
Disclosure of Invention
Therefore, a preparation method of the composite antibacterial agent and application of the composite antibacterial agent in polyester fabrics need to be provided, and the problems of poor antibacterial performance stability and bad deodorization performance of the antibacterial polyester fabrics prepared by the existing antibacterial agent are solved.
In order to achieve the aim, the invention provides a preparation method of a composite antibacterial agent, which comprises the following steps:
(1) mixing amino modified nano zinc oxide with a halogen compound for reaction to obtain halogen modified amino nano zinc oxide;
(2) mixing the halogen modified amino nano zinc oxide and the antibacterial agent in an organic solvent, adding a catalyst, and carrying out polymerization reaction under the action of the catalyst to obtain the nano zinc oxide halamine composite antibacterial agent.
Further, the amino modified nano zinc oxide is prepared by the following steps:
adding nano zinc oxide into ethanol and ammonia water solution, and performing ultrasonic dispersion at room temperature; adding 5-20% of aminosilane coupling agent by mass percent, fully stirring, reacting at 50-90 ℃, centrifuging, washing and drying to obtain amino modified nano zinc oxide particles, wherein the aminosilane coupling agent is one or more of 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, N-aminoethyl-3-aminopropyltriethoxysilane and N-aminoethyl-3-aminopropyltrimethoxysilane, and the nano zinc oxide is solid and must be fully mixed and dispersed with a solvent first to ensure that the nano zinc oxide particles react more fully later. The amino silane is liquid and is slowly added and stirred to react with the nano zinc oxide.
Further, the specific process in step (1) is that amino modified nano zinc oxide particles are added into an organic solvent, ultrasonic dispersion is carried out at room temperature, then halogen compound is added to obtain halogen modified amino nano zinc oxide, in step (2), halogen modified amino nano zinc oxide and the antibacterial agent are ultrasonically dispersed into the organic solvent under the ice bath condition, and then catalyst is slowly added to react to obtain the zinc oxide halamine composite antibacterial agent.
Further, the organic solvent is one or more of toluene, ethyl benzoate, methyl phenylacetate, benzyl acetate, triethylamine and styrene, and the catalyst in the step (2) is 4-methylBenzophenone, benzoyl peroxide, azobisisobutyronitrile, CuCl and SnCl2·H2PtCl6One or more of ADMH, VBDMH, ACTMIO and BADDD.
Further, the halogen compound has the following structure:
wherein R1 and R2 are independently selected from methyl, ethyl, propyl, isopropyl, butyl or isobutyl, and X1And X2Independently selected from Cl or Br.
The application of the preparation method of the composite antibacterial agent on the polyester fabric comprises the following steps:
(S1) preparing the nano zinc oxide halamine composite antibacterial agent prepared by the preparation method into zinc oxide halamine composite antibacterial emulsion;
(S2) carrying out antibacterial treatment on the polyester fabric by using the zinc oxide halamine composite antibacterial emulsion;
(S3) soaking the fabric subjected to the antibacterial treatment in a sodium hypochlorite solution for chlorination treatment, then washing with water, and drying to obtain the antibacterial deodorizing fabric.
Further, the specific process of the step (S1) is that 0.1 wt% -1.0 wt% of initiator is mixed with organic solvent, then 0.1 wt% -10 wt% of zinc oxide halamine composite antibacterial agent, emulsifier and water are added, the mixture is fully stirred for 2-20 min at the stirring speed of 500-2000 r/min at room temperature, and zinc oxide halamine composite antibacterial emulsion is obtained, wherein the HLB value of the emulsifier is LB 8-16.
Further, in the step (S1), the initiator is one or more of 4-methylbenzophenone, 2-methylpropionitrile, benzoyl peroxide and azobisisobutyronitrile, 4-azobiscyanovaleric acid, and potassium persulfate.
Further, the step (S2) is specifically that the zinc oxide halamine composite antibacterial emulsion and the cross-linking agent are mixed to form an antibacterial deodorizing mixed solution, the antibacterial deodorizing mixed solution is added into a padding machine, the polyester fabric is subjected to a two-dipping and two-rolling process in the padding machine, and the bath ratio of the polyester fabric to the antibacterial deodorizing mixed solution is 1: 10-30.
Further, the concentration of the sodium hypochlorite solution is 500-3000 ppm, and during chlorination treatment, the bath ratio of the polyester fabric to the sodium hypochlorite solution is 1: 20-60, and the soaking time is 5-30 min.
The technical scheme has the following beneficial effects:
(1) the nano zinc oxide halamine composite antibacterial agent prepared by the invention can generate peroxide and free radicals under the photocatalysis, has strong oxidizing capability, can decompose odor body, and thus has deodorization effect.
(2) According to the prepared nano zinc oxide and halamine composite antibacterial agent, after the nano zinc oxide is subjected to amino modification and halogen modification, the nano zinc oxide can be effectively subjected to polymerization reaction with the antibacterial agent, so that the nano zinc oxide is extremely uniformly dispersed, the phenomenon of nanoparticle agglomeration is avoided, the antibacterial effect of the nano zinc oxide can be effectively exerted, the antibacterial principle of a halamine polymer is realized, the fabric is endowed with good antibacterial property, and the antibacterial 'renewable' performance can be realized.
(3) In the preparation method of the antibacterial and deodorant fabric, polyester molecules of the polyester fabric can generate free radicals under the induction of the initiator, and meanwhile, the zinc oxide halamine composite antibacterial agent has a large number of double bonds and can easily generate free bonds under the induction of the initiator. Therefore, the free radicals generated by the polyester macromolecules and the free radicals generated by the composite antibacterial agent further initiate addition to form a polymer grafted to the surface of the fiber, so that the composite antibacterial agent and the polyester fiber are guaranteed to have good bonding fastness and washing resistance, and a durable antibacterial finishing effect is achieved.
(4) According to the preparation method of the antibacterial and deodorant fabric, chlorination treatment is carried out after antibacterial treatment, and N-H bonds in the zinc oxide halamine composite antibacterial agent can be converted into N-CL bonds to load active chlorine on the fabric, so that the antibacterial property and the reproducibility of the fabric are improved.
Detailed Description
In order to explain technical contents, structural features, and objects and effects of the technical means in detail, the following detailed description is given with reference to specific embodiments.
Example 1
A preparation method of a composite antibacterial agent comprises the following steps:
(1) preparing amino modified nano zinc: dissolving 2.0g of nano zinc oxide in 110ml of ethanol and ammonia water solution, and performing ultrasonic dispersion at room temperature; then, adding 20 mass percent of aminosilane coupling agent, fully stirring for 12 hours, reacting at 70 ℃ for 3 hours, and then centrifuging, washing and drying to obtain amino modified nano zinc oxide particles, wherein in the embodiment, the aminosilane coupling agent is 3-aminopropyltriethoxysilane, and the reaction is as follows:
the volume ratio of ethanol to ammonia water in the ethanol and ammonia water solution is 10:1, and the concentration of the ammonia water is 25-28%.
(2) Dissolving 3.0g of amino modified nano zinc oxide particles in 110ml of mixed solvent of toluene and triethylamine, performing ultrasonic dispersion at room temperature, adding 5% by mass of 2-bromoisobutyryl bromide to react to obtain bromine modified amino nano zinc oxide, and stirring to react for 10 hours. Obtaining bromine modified amino nano zinc oxide by centrifugal washing, wherein the reaction formula is as follows:
the volume ratio of toluene to triethylamine in the mixed solvent of toluene and triethylamine is 1: 1.
(3) 1.0g of bromine modified amino nano zinc oxide and 3.0g of ADMH antibacterial agent are sequentially added into 110ml of mixed solvent of toluene and triethylamine, ultrasonic dispersion is carried out under the ice bath condition, then 0.1% of CuCl is slowly added at room temperature as a catalyst, and the zinc oxide halamine composite antibacterial agent is obtained after reaction.
Example 2
A preparation method of a composite antibacterial agent comprises the following steps:
(1) preparing amino modified nano zinc: dissolving 2.0g of nano zinc oxide in 110ml of ethanol and ammonia water solution, and performing ultrasonic dispersion at room temperature; then, adding an aminosilane coupling agent with the mass fraction of 5% to fully stir for 6 hours, reacting at the temperature of 50 ℃ for 5 hours, and then centrifuging, washing and drying to obtain amino modified nano zinc oxide particles, wherein the aminosilane coupling agent is 3-aminopropyltrimethoxysilane:
(2) the amino modified nano zinc oxide particles and halogen compounds react in a toluene solvent, and the rest is the same as the example 1, so that the bromine modified amino nano zinc oxide is obtained, wherein the halogen compounds have the following structures:
wherein, X1And X2Are all Br, R1And R2Respectively propyl and ethyl.
(3) Adding 1.0g of bromine-modified amino nano zinc oxide and 3.0g of ACTMIO antibacterial agent into 110ml of toluene solvent in sequence, performing ultrasonic dispersion under an ice bath condition, slowly adding 0.1% of benzophenone and 4-methylbenzophenone as catalysts at room temperature, and reacting to obtain the zinc oxide halamine composite antibacterial agent.
Example 3
A preparation method of a composite antibacterial agent comprises the following steps:
(1) preparing amino modified nano zinc: dissolving 2.0g of nano zinc oxide in 110ml of ethanol and ammonia water solution, and performing ultrasonic dispersion at room temperature; then adding an aminosilane coupling agent with the mass fraction of 10% for fully stirring for 6h, reacting at the temperature of 90 ℃, and then centrifuging, washing and drying to obtain amino modified nano zinc oxide particles, wherein the aminosilane coupling agent in the embodiment is a mixture of 3-aminopropyltriethoxysilane and N-aminoethyl-3-aminopropyltriethoxysilane:
(2) reacting the amino modified nano zinc oxide particles with a halogen compound in a mixed solvent of benzyl acetate and styrene, and obtaining the bromine modified amino nano zinc oxide by the same method as the embodiment 1, wherein the halogen compound has the following structure:
wherein, X1And X2Are all Br, R1And R2Isopropyl and butyl respectively;
(3) adding 1.0g of bromine modified amino nano zinc oxide and 3.0g of BADDD antibacterial agent into 110ml of mixed solvent of benzyl acetate and styrene in sequence, ultrasonically dispersing under ice bath condition, and slowly adding 0.1% SnCl at room temperature2·H2PtCl6As a catalyst, the zinc oxide halamine composite antibacterial agent is obtained by reaction.
Example 4
A preparation method of a composite antibacterial agent comprises the following steps:
(1) preparing amino modified nano zinc: dissolving 2.0g of nano zinc oxide in 110ml of ethanol and ammonia water solution, and performing ultrasonic dispersion at room temperature; then adding an aminosilane coupling agent with the mass fraction of 10% to fully stir for 6h, reacting at 70 ℃ for 10h, and then centrifuging, washing and drying to obtain amino modified nano zinc oxide particles, wherein the aminosilane coupling agent in the embodiment is a mixture of 3-aminopropyltrimethoxysilane and N-aminoethyl-3-aminopropyltrimethoxysilane:
(2) the amino modified nano zinc oxide particles and a halogen compound react in a mixed solvent of ethyl benzoate and triethylamine, the volume ratio of ethyl benzoate to triethylamine in the mixed solvent of ethyl benzoate and triethylamine is 1:1, the rest is the same as that in the example 1, and the halogen compound has the following structure:
wherein, X1And X2Are all Br, R1And R2Respectively isobutyl and methyl;
(3) adding 1.0g of bromine-modified amino nano zinc oxide and 3.0g of VBDMH antibacterial agent into 110ml of mixed solvent of ethyl benzoate and triethylamine, performing ultrasonic dispersion under an ice bath condition, slowly adding 0.1% of benzoyl peroxide and azodiisobutyronitrile as catalysts at room temperature, and reacting to obtain the zinc oxide halamine composite antibacterial agent.
Example 5
A preparation method of a composite antibacterial agent comprises the following steps:
(1) preparing amino modified nano zinc: same as in example 1
(2) Dissolving 3.0g of amino modified nano zinc oxide particles in 110ml of mixed solvent of toluene and triethylamine, performing ultrasonic dispersion at room temperature, adding 5% by mass of 2-chloroisobutyryl chloride to react to obtain chlorine modified amino nano zinc oxide, and stirring to react for 10 hours to obtain chlorine modified amino nano zinc oxide, wherein the reaction formula is as follows:
the volume ratio of toluene to triethylamine in the mixed solvent of toluene and triethylamine is 1: 1.
(3) 1.0g of chlorine modified amino nano zinc oxide and 3.0g of ADMH antibacterial agent are sequentially added into 110ml of mixed solvent of toluene and triethylamine, ultrasonic dispersion is carried out under the ice bath condition, then 0.1% of CuCl is slowly added at room temperature as a catalyst, and the zinc oxide halamine composite antibacterial agent is obtained through reaction.
Example 6
The nano zinc oxide halamine composite antibacterial agents prepared in examples 1-5 are applied to polyester fabrics to prepare five different antibacterial and deodorant fabrics.
The method specifically comprises the following steps:
(S1) adding 0.5 wt% of dibenzoyl peroxide as an initiator into a toluene solvent, uniformly mixing, adding 10 wt% of nano zinc oxide and halamine composite antibacterial agent, 1 wt% of tween 80 and 40 wt% of water, and fully stirring at a stirring speed of 2000r/min for 20min to obtain zinc oxide and halamine composite antibacterial emulsion, wherein the HLB value of the tween 80 is 16.0;
(S2) adding 0.9 wt% of TATAT crosslinking agent into the prepared zinc oxide halamine composite antibacterial emulsion, mixing to form an antibacterial and deodorant mixed solution, adding the antibacterial and deodorant mixed solution into a padding machine, and carrying out two-dipping and two-rolling process treatment on the polyester fabric in the padding machine, wherein the bath ratio of the polyester fabric to the antibacterial and deodorant mixed solution is 1: 20;
(S3) soaking the fabric subjected to the antibacterial treatment in a sodium hypochlorite solution for chlorination treatment, wherein the concentration of the sodium hypochlorite solution is 3000ppm, and the bath ratio of the polyester fabric to the sodium hypochlorite solution is 1: and 50, soaking for 5min, washing with water, and drying to obtain the antibacterial deodorizing fabric.
Experimental samples 1-5 correspond to the antibacterial and deodorant fabrics prepared from the nano zinc oxide halamine composite antibacterial agent of examples 1-5, respectively.
Control group 1
The conventional nano zinc oxide is prepared into zinc oxide antibacterial emulsion, and then the zinc oxide antibacterial emulsion is used for padding the polyester fabric to obtain a control sample 1, wherein the adhesion amount of the zinc oxide on the fabric of the control sample 1 is small.
Control group 2
The halamine polymer is used as an antibacterial agent to prepare halamine polymer antibacterial emulsion, then the halamine polymer antibacterial emulsion is used for padding the polyester fabric, and then chlorination treatment is carried out to obtain a control sample 2.
Control group 3
Plain polyester fabric as control sample 3
The results of the tests on the antibacterial and deodorant performances of the above experimental samples 1 to 5 and the control samples 1 to 3 are shown in table 1, wherein the antibacterial performance test uses the oscillation method in GB/T20944.3-2008 to test the bacteriostatic rate, and the deodorant performance test uses the gas chromatography method in GB/T33610.3-2019 to test the concentration reduction rate of the odor chemical component.
As can be seen from Table 1, the antibacterial and deodorant fabrics prepared by the invention have greatly improved antibacterial and deodorant performances compared with common polyester fabrics, and have certain improved antibacterial ability and greatly improved deodorant performance compared with polyester fabrics prepared by nano zinc oxide or pure haloamine polymers.
TABLE 1 antibacterial and deodorant Property test Table
Example 7
The application of the nano zinc oxide halamine composite antibacterial agent prepared in the embodiment 1 to the polyester fabric comprises the following steps:
(S1), adding 0.1 wt% of 4-methyl benzophenone and 2-methyl propionitrile into a toluene solvent, uniformly mixing, adding 0.1 wt% of nano zinc oxide and ammonium halide composite antibacterial agent, 1 wt% of polyoxypropylene stearate and 40 wt% of water, and fully stirring at a stirring speed of 500r/min for 10min to obtain zinc oxide and ammonium halide composite antibacterial emulsion, wherein the HLB value of the polyoxypropylene stearate is 8.0;
(S2), adding 0.9 wt% of TATAT crosslinking agent into the prepared zinc oxide halamine composite antibacterial emulsion, mixing to form an antibacterial and deodorant mixed solution, adding the antibacterial and deodorant mixed solution into a padding machine, and carrying out two-dipping and two-rolling process treatment on the polyester fabric in the padding machine, wherein the bath ratio of the polyester fabric to the antibacterial and deodorant mixed solution is 1: 10;
(S3) soaking the antibacterial-treated fabric in a sodium hypochlorite solution for chlorination treatment, wherein the concentration of the sodium hypochlorite solution is 1500ppm, and the bath ratio of the polyester fabric to the sodium hypochlorite solution is 1:20, soaking for 20min, then washing with water, and drying to obtain the antibacterial deodorizing fabric.
Example 8
The application of the nano zinc oxide halamine composite antibacterial agent prepared in the embodiment 1 to the polyester fabric comprises the following steps:
(S1), adding 0.5 wt% of azobisisobutyronitrile and 4, 4-azobiscyanovaleric acid into a toluene solvent, uniformly mixing, adding 0.1 wt% of nano zinc oxide halamine composite antibacterial agent, 1 wt% of polyoxyethylene oleyl ether and 40 wt% of water, and fully stirring at a stirring speed of 1000r/min for 10min to obtain a zinc oxide halamine composite antibacterial emulsion, wherein the HLB value of the polyoxyethylene oleyl ether is 12.0;
(S2) adding 0.9 wt% of TATAT cross-linking agent into the prepared zinc oxide halamine composite antibacterial emulsion, mixing to form an antibacterial and deodorant mixed solution, adding the antibacterial and deodorant mixed solution into a padding machine, and carrying out two-dipping and two-rolling process treatment on the polyester fabric in the padding machine, wherein the bath ratio of the polyester fabric to the antibacterial dye solution is 1: 30;
(S3) soaking the antibacterial-treated fabric in a sodium hypochlorite solution for chlorination treatment, wherein the concentration of the sodium hypochlorite solution is 500ppm, and the bath ratio of the polyester fabric to the sodium hypochlorite solution is 1: 60, soaking for 30min, then washing and drying to obtain the antibacterial and deodorant fabric.
Example 9
The application of the nano zinc oxide halamine composite antibacterial agent prepared in the embodiment 1 to the polyester fabric comprises the following steps:
(S1), adding 0.5 wt% of potassium persulfate serving as an initiator into a toluene solvent, uniformly mixing, adding 0.1 wt% of nano zinc oxide and halamine composite antibacterial agent, 1 wt% of polyoxyethylene oleyl ether and 40 wt% of water, and fully stirring at a stirring speed of 1000r/min for 10min to obtain zinc oxide and halamine composite antibacterial emulsion, wherein the HLB value of the polyoxyethylene oleyl ether is 12.0;
(S2), adding 0.9 wt% of TATAT cross-linking agent into the prepared zinc oxide halamine composite antibacterial emulsion, mixing to form an antibacterial and deodorant mixed solution, adding the antibacterial and deodorant mixed solution into a padding machine, and carrying out two-dipping and two-rolling process treatment on the polyester fabric in the padding machine, wherein the bath ratio of the polyester fabric to the antibacterial dye solution is 1: 30;
(S3) soaking the antibacterial-treated fabric in a sodium hypochlorite solution for chlorination treatment, wherein the concentration of the sodium hypochlorite solution is 500ppm, and the bath ratio of the polyester fabric to the sodium hypochlorite solution is 1: 60, soaking for 30min, then washing and drying to obtain the antibacterial and deodorant fabric.
The prepared nano zinc oxide and halamine composite antibacterial agent has the dual antibacterial effect and deodorization capacity of nano zinc oxide and halamine polymers, and the prepared antibacterial and deodorization fabric has the excellent performances of good bonding fastness between the composite antibacterial agent and polyester fibers, no toxicity, washing resistance and regeneration. The invention can improve the antibacterial and deodorizing performance of the polyester fabric on the premise of controlling the cost, forms the differentiated competition of products, and can create great economic value and social benefit for the society and enterprises.
Therefore, the nano zinc oxide and halamine composite antibacterial agent prepared by the invention has the dual antibacterial effect and deodorization capability of nano zinc oxide and halamine polymers, and the prepared antibacterial and deodorization fabric has the excellent performances of good bonding fastness between the composite antibacterial agent and polyester fibers, no toxicity, washing resistance and regeneration. The invention can improve the antibacterial and deodorizing performance of the polyester fabric on the premise of controlling the cost, forms the differentiated competition of products, and can create great economic value and social benefit for the society and enterprises.
It is noted that, herein, relational terms such as first and second, and the like may be used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Also, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or terminal that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or terminal. Without further limitation, an element defined by the phrases "comprising … …" or "comprising … …" does not exclude the presence of additional elements in a process, method, article, or terminal that comprises the element. Further, herein, "greater than," "less than," "more than," and the like are understood to exclude the present numbers; the terms "above", "below", "within" and the like are to be understood as including the number.
Although the embodiments have been described, once the basic inventive concept is known, other variations and modifications can be made to the embodiments by those skilled in the art, so that the above embodiments are only examples of the present invention, and not intended to limit the scope of the present invention, and all equivalent structures or equivalent processes that can be used in the present specification or directly or indirectly applied to other related fields are encompassed by the present invention.
Claims (10)
1. The preparation method of the composite antibacterial agent is characterized by comprising the following steps:
(1) mixing amino modified nano zinc oxide with a halogen compound for reaction to obtain halogen modified amino nano zinc oxide;
(2) mixing the halogen modified amino nano zinc oxide and the antibacterial agent in an organic solvent, adding a catalyst, and carrying out polymerization reaction under the action of the catalyst to obtain the nano zinc oxide halamine composite antibacterial agent.
2. The method for preparing the composite antibacterial agent according to claim 1, wherein the amino modified nano zinc oxide is prepared by the following process:
adding nano zinc oxide into ethanol and ammonia water solution, and performing ultrasonic dispersion at room temperature; and adding an aminosilane coupling agent with the mass fraction of 5-20% for fully stirring, reacting at the temperature of 50-90 ℃, centrifuging, washing and drying to obtain the amino modified nano zinc oxide particles, wherein the aminosilane coupling agent is one or more of 3-aminopropyltriethoxysilane, 3-aminopropyltrimethoxysilane, N-aminoethyl-3-aminopropyltriethoxysilane and N-aminoethyl-3-aminopropyltrimethoxysilane.
3. The method for preparing a composite antibacterial agent according to claim 1, wherein the specific process in step (1) is to add the amino-modified nano zinc oxide particles into an organic solvent, perform ultrasonic dispersion at room temperature, then add a halogen compound to obtain halogen-modified amino-nano zinc oxide, and in step (2), perform ultrasonic dispersion on the halogen-modified amino-nano zinc oxide and the antibacterial agent in the organic solvent under ice bath conditions, and then slowly add a catalyst to react to obtain the zinc oxide halamine composite antibacterial agent.
4. The method for preparing a composite antibacterial agent according to claim 3, wherein the organic solvent is one or more of toluene, ethyl benzoate, methyl phenylacetate, benzyl acetate, triethylamine and styrene, and the catalyst in step (2) is 4-methylbenzophenone, benzoyl peroxide, azobisisobutyronitrile, CuCl and SnCl2·H2PtCl6One or more of ADMH, VBDMH, ACTMIO and BADDD.
5. The method of claim 1, wherein the halogen compound has the structure:
wherein R is1And R2Independently selected from methyl, ethyl, propyl, isopropyl, butyl or isobutyl, X1And X2Independently selected from Cl or Br.
6. Use of a process for the preparation of a composite antimicrobial agent according to any one of claims 1 to 5 on polyester fabrics, comprising the steps of:
(S1) preparing the nano zinc oxide halamine composite antibacterial agent prepared by the method for preparing a composite antibacterial agent according to any one of claims 1 to 5 into a zinc oxide halamine composite antibacterial emulsion;
(S2) carrying out antibacterial treatment on the polyester fabric by using the zinc oxide halamine composite antibacterial emulsion;
(S3) soaking the fabric subjected to the antibacterial treatment in a sodium hypochlorite solution for chlorination treatment, then washing with water, and drying to obtain the antibacterial deodorizing fabric.
7. The application of the method for preparing a composite antibacterial agent according to claim 6 to polyester fabric, wherein the step (S1) is specifically performed by mixing 0.1 wt% to 1.0 wt% of an initiator with an organic solvent, adding 0.1 wt% to 10 wt% of a zinc oxide halamine composite antibacterial agent, an emulsifier and water, and fully stirring at a stirring speed of 500r/min to 2000r/min for 2 min to 20min at room temperature to obtain a zinc oxide halamine composite antibacterial emulsion, wherein the emulsifier has an HLB value of LB 8-16.
8. The use of the method of claim 7 for producing a complex antimicrobial agent for polyester fabrics, wherein in step (S1), the initiator is one or more selected from the group consisting of 4-methylbenzophenone, 2-methylpropanenitrile, benzoyl peroxide, azobisisobutyronitrile, 4-azobiscyanovaleric acid, and potassium persulfate.
9. The use of the method of claim 6 for preparing a composite antimicrobial agent for polyester fabrics, wherein the step (S2) comprises mixing the zinc oxide halamine composite antimicrobial emulsion with a cross-linking agent to form an antimicrobial deodorizing mixture, adding the antimicrobial deodorizing mixture to a padding machine, and subjecting the polyester fabrics to a two-dip and two-roll process in the padding machine at a bath ratio of 1: 10-30.
10. The application of the preparation method of the composite antibacterial agent on the polyester fabric, as claimed in claim 6, is characterized in that the concentration of the sodium hypochlorite solution is 500-3000 ppm, and the bath ratio of the polyester fabric to the sodium hypochlorite solution is 1: 20-60, and the soaking time is 5-30 min.
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