CN107815871B - Preparation method of durable antibacterial fabric - Google Patents
Preparation method of durable antibacterial fabric Download PDFInfo
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- CN107815871B CN107815871B CN201711187446.XA CN201711187446A CN107815871B CN 107815871 B CN107815871 B CN 107815871B CN 201711187446 A CN201711187446 A CN 201711187446A CN 107815871 B CN107815871 B CN 107815871B
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- antibacterial
- fabric
- nano hydrogel
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- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 160
- 239000004744 fabric Substances 0.000 title claims abstract description 95
- 238000002360 preparation method Methods 0.000 title abstract description 8
- 239000000017 hydrogel Substances 0.000 claims abstract description 51
- 239000000178 monomer Substances 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 48
- 238000001035 drying Methods 0.000 claims description 36
- 238000001291 vacuum drying Methods 0.000 claims description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- 238000003756 stirring Methods 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 229920000742 Cotton Polymers 0.000 claims description 19
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 14
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 14
- 238000001914 filtration Methods 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000008367 deionised water Substances 0.000 claims description 12
- 229910021641 deionized water Inorganic materials 0.000 claims description 12
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
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- 238000004140 cleaning Methods 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 9
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical group CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 8
- 239000000835 fiber Substances 0.000 claims description 8
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 8
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 claims description 8
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical group CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 7
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical group [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 claims description 7
- -1 polyhexamethylene guanidine hydrochloride Polymers 0.000 claims description 7
- 230000001376 precipitating effect Effects 0.000 claims description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 238000005507 spraying Methods 0.000 claims description 6
- 238000009210 therapy by ultrasound Methods 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 4
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 claims description 4
- 229930064664 L-arginine Natural products 0.000 claims description 4
- 235000014852 L-arginine Nutrition 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- 239000006185 dispersion Substances 0.000 claims description 4
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 claims description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 claims description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 2
- 229960004198 guanidine Drugs 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 230000000845 anti-microbial effect Effects 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 4
- 239000004599 antimicrobial Substances 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 abstract description 11
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
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- 239000007864 aqueous solution Substances 0.000 description 5
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- 238000010438 heat treatment Methods 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 4
- 229920001661 Chitosan Polymers 0.000 description 4
- 239000008272 agar Substances 0.000 description 4
- 230000003385 bacteriostatic effect Effects 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 3
- 244000052616 bacterial pathogen Species 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
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- 238000001132 ultrasonic dispersion Methods 0.000 description 3
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- 238000011109 contamination Methods 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 208000012868 Overgrowth Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
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- 230000002411 adverse Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- HKVFISRIUUGTIB-UHFFFAOYSA-O azanium;cerium;nitrate Chemical compound [NH4+].[Ce].[O-][N+]([O-])=O HKVFISRIUUGTIB-UHFFFAOYSA-O 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
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- 238000011161 development Methods 0.000 description 1
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- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
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- 244000052769 pathogen Species 0.000 description 1
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- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
Images
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- 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
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
- C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
- C08G18/6225—Polymers of esters of acrylic or methacrylic acid
-
- 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
-
- 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
- D06M2101/10—Animal fibres
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention relates to a preparation method of a durable antibacterial fabric, which comprises the following steps: the synthesis of an antibacterial monomer, the synthesis of an antibacterial nano hydrogel, the synthesis of a surface-modified antibacterial nano hydrogel and the synthesis of a lasting antibacterial fabric. According to the invention, the nanometer hydrogel particles are combined with the fabric to endow the fabric with an antibacterial function, the method is simple and convenient in treatment process, the damage to the original performance of the fabric is small, and the antibacterial effect of the fabric finished by the method is more durable; the prepared antibacterial nano hydrogel has the advantages of simple processing technology, good biocompatibility, more obvious antibacterial effect, no toxicity to human bodies, no use of antibacterial agents and no generation of drug resistance of bacteria.
Description
Technical Field
The invention belongs to the field of modified textile preparation, and particularly relates to a preparation method of a durable antibacterial fabric.
Background
With the continuous emergence of new pathogens in recent years, the influence of microbial contamination and disease transmission caused by bacterial pathogens on human health and life is more and more serious, and the research on antibacterial is still in a slow way.
Generally speaking, the surface of a material provides a good medium for the growth of various bacterial pathogens, and the overgrowth of bacterial pathogens can have various adverse effects on human safety. The investigation data shows that the probability of microbial contamination and infection is obviously reduced after the surface of the material is subjected to antibacterial treatment. Therefore, materials used in daily life need to be subjected to antibacterial modification treatment, so that the healthy life of people is guaranteed. The most important part of the materials required by the daily life of the textile materials is closely related to the daily life of people, and the most important part is that the textile materials, particularly natural fiber textile materials, have no antibacterial effect, and the properties of chemical composition, moisture absorption, water retention and the like of the textile materials also provide an excellent breeding environment for the growth of bacteria, so that the development of antibacterial textiles is more necessary.
The research and development of antibacterial agents began in the beginning of the 80's of the 20 th century. Currently, the antibacterial agents that have been developed and used can be classified as: inorganic antibacterial agents, organic antibacterial agents and complex antibacterial agents 3. The antibacterial agent for finishing textiles is mainly divided into heavy metal ions and photocatalytic metal oxide (TiO)2) And antibacterial agents such as halogen amines, quaternary ammonium salts, guanidines, and natural (chitosan). These antibacterial agents are mostly applied to textile materials in molecular or ionic form, such as the synthesis and antibacterial performance research of the graft copolymer of cotton fiber/quaternary ammonium salt (Zuohuajiang, Royal, Wudingcai, Furan.) [ J ]]The university of Zhongshan journal (Nature science edition), 2010, 49(05):61-66) and the like use ammonium cerium nitrate as an initiator to initiate the graft polymerization of dimethylaminoethyl methacrylate (DMAEMA) on the surface of cotton fibers and quaternize the grafted DMAEMA to impart good resistance to the cotton fibersThe performance of the bacteria; preparation and antibacterial property of copper-loaded antibacterial cotton fiber of radix et rhizoma Rhei (radix et rhizoma Rhei, radix Puerariae, and Rainbow)]Journal of environmental and health, 2007, (02):103-106), etc. cotton fibers are treated with ethylenetriamine, triethylenetetramine, tetraethylenepentamine after being alkalized and epoxidized, and then subjected to Cu2+Adsorption, the modified cotton fiber shows better sterilization effect; further example is chitosan quaternary ammonium salt antibacterial finishing of Hunan engineering institute Liangsan (Liangsan, Zetian sweet, Lijun, Guoxing, Wen general. Cotton fabrics [ J]Printing, 2013,39 (20): 16-19) and the like, and glycidyl trimethyl ammonium chloride (GTMAC) is adopted to react with chitosan, so that chitosan quaternary ammonium salt HACC is synthesized and used for the antibacterial finishing of cotton fabrics, and the finished cotton fabrics have the best antibacterial finishing effect on escherichia coli bacteria and a certain antibacterial effect on staphylococcus aureus. However, in recent years, research results show that nano-sized heavy metals, compounds and antibacterial polymer nanoparticles have more excellent antibacterial activity due to the specific nano-effect of nano-sized materials, but reports of applying the nano-sized antibacterial agent to textile materials are limited to inorganic metal and metal compound nanoparticles thereof. There are few reports on the success of the application of the antibacterial polymer nanoparticles to textile materials.
Disclosure of Invention
The invention aims to solve the technical problem of providing a preparation method of a durable antibacterial fabric, which is simple, has little damage to the original performance of the fabric, and the prepared antibacterial fabric has a durable antibacterial effect.
The invention discloses a preparation method of a lasting antibacterial fabric, which comprises the following steps:
(1) dissolving an antibacterial compound containing guanidino in a solvent to obtain an antibacterial compound solution containing guanidino, adding triethylamine, stirring, dropwise adding a methacrylic anhydride solution for reaction, precipitating, and drying to obtain an antibacterial monomer, wherein the mass ratio of the antibacterial compound containing guanidino to the triethylamine to the methacrylic anhydride is (1-2) to (0.5-1.2) to (0.8-1.6), and the concentration of the antibacterial compound solution containing guanidino is 0.1-0.4 g/mL;
(2) dissolving the antibacterial monomer, the high-molecular polymer monomer and the water-soluble monomer in the step (1) in a mass ratio of (1-2): (0.2-0.4): 0.02-0.04) in a solvent, adding a cross-linking agent, adding an initiator in a nitrogen environment, stirring for reaction, filtering and drying to obtain the antibacterial nano hydrogel, wherein the mass ratio of the antibacterial monomer, the initiator and the cross-linking agent is (1-2): 0.005-0.02): 0.01-0.02), and the ratio of the antibacterial monomer to the solvent is 5g:100mL-10g:5 mL;
(3) dispersing the antibacterial nano hydrogel in the step (2) in an inert solvent to obtain an antibacterial nano hydrogel solution, performing ultrasonic treatment, adding isophorone diisocyanate, adding a catalyst, stirring for reaction, filtering, and drying to obtain a surface-modified antibacterial nano hydrogel, wherein the mass ratio of the antibacterial nano hydrogel to the isophorone diisocyanate to the catalyst is (1-5) to (7-55) to (0.3-3), and the concentration of the antibacterial nano hydrogel solution is 0.002-0.01 g/mL;
(4) and (3) dispersing the surface-modified antibacterial nano hydrogel in the step (3) in an inert solvent to obtain a surface-modified antibacterial nano hydrogel solution, performing ultrasonic treatment to obtain a dispersion solution, soaking or spraying the fabric in the dispersion solution, cleaning, and drying to obtain the durable antibacterial fabric, wherein the concentration of the surface-modified antibacterial nano hydrogel solution is 0.001-0.01 g/mL.
The guanidine-containing antibacterial compound in the step (1) is polyhexamethylene guanidine hydrochloride or L-arginine; the solvent of the methacrylic anhydride solution is dioxane; the reaction time is 8-12 h; acetone is used for precipitation; the drying is carried out in a vacuum drying oven.
And (3) in the steps (1) and (2), the solvent is deionized water.
The polymer monomer in the step (2) is methyl methacrylate, methyl acrylate, styrene or butyl methacrylate.
The water-soluble monomer in the step (2) is hydroxyethyl methacrylate, hydroxyethyl acrylate, hydroxypropyl methacrylate or hydroxypropyl acrylate.
The cross-linking agent in the step (2) is N, N-methylene bisacrylamide; the initiator is ammonium persulfate APS; the initiator is added under the condition of raising the temperature to 60-80 ℃.
The reaction time in the step (2) is 12-24 h; the drying is carried out in a vacuum drying oven at 40 ℃.
In the step (3), the stirring reaction temperature is 40-60 ℃, and the stirring reaction time is 8-12 h.
The catalyst in the step (3) is dibutyltin dilaurate; the drying is carried out in a vacuum drying oven at room temperature.
In the steps (3) and (4), the inert solvent is acetone, dioxane, petroleum ether or N, N-dimethylacetamide; the ultrasonic treatment time is 10-40 min.
The fabric in the step (4) is a natural fiber fabric or a fabric woven by fibers with active groups on the surface.
The natural fiber fabric is a cotton fabric or a silk fabric; the active group being-OH or-NH2。
The bath ratio of soaking in the step (4) is 1: 100-200; the temperature of the spraying treatment is 40-80 ℃, and the time of the spraying treatment is 6-12 h.
Acetone is used for cleaning in the step (4); the drying is carried out in a vacuum drying oven.
According to the invention, the prepared antibacterial nano hydrogel is grafted on the surfaces of textile materials such as cotton and silk in a chemical bond bonding mode, so that the textile has an antibacterial function, and the antibacterial effect is obvious and can be exerted effectively and durably through antibacterial experiment tests.
Advantageous effects
(1) The method of the invention endows the fabric with an antibacterial function by combining the nano hydrogel particles with the fabric, the method has simple and convenient treatment process, has less damage to the original performance of the fabric, and the fabric finished by the method has a more lasting antibacterial effect.
(2) The antibacterial nano hydrogel prepared by the invention has the advantages of simple processing technology, good biocompatibility, more obvious antibacterial effect, no toxicity to human bodies, no use of antibacterial agents and no generation of drug resistance of bacteria.
Drawings
FIG. 1 is a scheme showing the synthesis of antibacterial monomers in example 1;
FIG. 2 is a scheme showing the synthesis of the antibacterial nanohydrogel of example 1;
FIG. 3 is a synthesis scheme of the surface-modified antibacterial nano-hydrogel in example 1;
FIG. 4 is SEM pictures of silk fabric (A) without any treatment and silk fabric (B) after modification treatment and 10 water washes in example 1;
fig. 5 is a graph showing the results of the antibacterial activities of the antibacterial fabrics (silk fabric test sample and cotton fabric test sample, respectively) and the corresponding blank samples (silk fabric blank and cotton fabric blank, respectively) washed 10 times in examples 1 and 2.
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.
In the examples, the antibacterial experiment is slightly changed according to the method of GBT 20944.1-2007, and the specific method is as follows: preparing a bacterium solution and an agar culture medium according to a standard specified method, respectively taking 0.5mL of staphylococcus aureus and escherichia coli bacterium solution, diluting the staphylococcus aureus and escherichia coli bacterium solution by 100 times by using PBS buffer solution, then respectively inoculating 1mL of the diluted bacterium solution on the two agar culture media to prepare a staphylococcus aureus culture medium and an escherichia coli agar culture medium, and placing a sample to be tested in the agar culture medium and culturing the sample in an incubator at 37 ℃ for 18-24 hours. Quantitative calculation formula of antibacterial result
H＝(D-d)/2
Wherein H is the width of the bacteriostatic zone; d is the average diameter of the outer diameter of the antibacterial zone; d is the average diameter of the circular filter paper. The measurements were averaged four times for each sample according to the test methods specified by the standards.
Example 1
(1) Dissolving 5g of polyhexamethylene guanidine hydrochloride in 25mL of deionized water, adding 3.5mL of triethylamine, stirring to fully mix the solution, dropwise adding 8mL of dioxane solution containing 4g of methacrylic anhydride, continuously reacting for 8h, precipitating the product with acetone, and drying in a vacuum drying oven at room temperature to obtain the antibacterial monomer.
(2) Dissolving 5g of the antibacterial monomer in the step (1), 1.8g of methyl methacrylate and 0.2g of hydroxyethyl methacrylate in 100mL of deionized water in a 250mL three-neck flask, adding 0.1g N, N-methylene bisacrylamide, introducing nitrogen, stirring for 30min, heating to 70 ℃, dropwise adding 2mL of an aqueous solution containing 70mg of APS ammonium persulfate, continuously reacting for 12h, filtering and purifying the reaction product for three times, and drying at 40 ℃ in a vacuum drying oven to obtain the antibacterial nano hydrogel.
(3) And (3) dissolving 0.3g of the antibacterial nano hydrogel obtained in the step (2) in 100mL of acetone, ultrasonically dispersing for 30min, dropwise adding 2mL of isophorone diisocyanate, dropwise adding 0.1mL of dibutyltin dilaurate, stirring and reacting for 8h at 50 ℃ in a nitrogen environment, filtering a product, washing with a large amount of acetone, and drying at room temperature in a vacuum drying oven to obtain the surface-modified antibacterial nano hydrogel.
(4) And (3) dissolving 0.2g of the antibacterial nano hydrogel subjected to surface modification in the step (3) in 200mL of N, N-dimethylacetamide, ultrasonically dispersing for 15min, soaking 1g of silk fabric in the solution, finishing at 50 ℃ for 6h, cleaning the treated fabric with acetone, and drying in a vacuum drying oven at 40 ℃ to obtain the antibacterial fabric. The antibacterial fabric is taken and washed 10 times by referring to the washing procedure of FZ/T73023 and 2006 antibacterial fabric appendix C antibacterial fabric sample washing test method. And (5) performing a bacteriostasis test on the antibacterial fabric which is washed for 10 times.
FIG. 1 shows that: wherein, methacrylic anhydride reacts with one end amino group on the poly hexamethylene guanidine hydrochloride molecule to form amido bond.
FIG. 2 shows that: due to the existence of monomer hydroxyethyl methacrylate, a large number of-OH functional groups are distributed on the surface of the nano hydrogel.
FIG. 3 shows: under the action of different catalysts, two-NCO functional groups on isophorone diisocyanate have different reaction activities, under the condition of taking dibutyltin dilaurate as a catalyst, isocyanate functional groups at one end with high activity and hydroxyl on the surface of the nano hydrogel are subjected to chemical reaction, and isocyanate groups at the other end are distributed on the nano hydrogelThe surface of the glue. the-NCO functional group on the surface of the nano hydrogel has higher reaction activity and can react with-OH and-NH on the surfaces of fibers such as cotton, silk and the like2And the functional groups react to realize the graft modification of the polymer nano hydrogel and the fabric.
FIG. 4 shows that: the surface of the antibacterial fabric is also distributed with a large amount of nano hydrogel after being washed for 10 times.
Example 2
(1) Dissolving 5g of polyhexamethylene guanidine hydrochloride in 25mL of deionized water, adding 3.5mL of triethylamine, stirring to fully mix the solution, then dropwise adding 8mL of dioxane solution containing 4g of methacrylic anhydride, continuously reacting for 8h, precipitating the product with acetone, and drying at room temperature in a vacuum drying oven to obtain the antibacterial monomer.
(2) And (2) dissolving 8g of the antibacterial monomer in the step (1), 1.8g of styrene and 0.2g of hydroxyethyl methacrylate in 100mL of deionized water in a 250mL three-neck flask, adding 0.1g N, N-methylene bisacrylamide, introducing nitrogen, stirring for 30min, heating to 70 ℃, dropwise adding 2mL of an aqueous solution containing 70mg of APS ammonium persulfate, continuously reacting for 12h, filtering and purifying the reaction product for three times, and drying at 40 ℃ in a vacuum drying oven to obtain the antibacterial nano hydrogel.
(3) And (3) dissolving 0.3g of the antibacterial nano hydrogel obtained in the step (2) in 100mL of acetone, ultrasonically dispersing for 30min, dropwise adding 2mL of isophorone diisocyanate, dropwise adding 0.1mL of dibutyltin dilaurate, stirring and reacting for 8h at 50 ℃ in a nitrogen environment, filtering a product, washing with a large amount of acetone, and drying at room temperature in a vacuum drying oven to obtain the surface-modified antibacterial nano hydrogel.
(4) And (3) dissolving 0.2g of the surface-modified antibacterial nano hydrogel in the step (3) in 200mL of N, N-dimethylacetamide, ultrasonically dispersing for 15min, soaking 2g of cotton fabric in the solution, finishing for 6h at 50 ℃, cleaning the treated fabric with acetone, and drying in a vacuum drying oven at 40 ℃ to obtain the antibacterial fabric. The antibacterial fabric is taken and washed 10 times by referring to the washing procedure of FZ/T73023 and 2006 antibacterial fabric appendix C antibacterial fabric sample washing test method. And (5) carrying out bacteriostasis experiments on the antibacterial fabric washed 10 times.
FIG. 5 shows that: the antibacterial fabric (silk fabric test sample) washed 10 times in the example 1 has the bacteriostatic radius of 1.5cm for staphylococcus aureus and 1.2cm for escherichia coli, and has better antibacterial activity; in this example 2, the antibacterial fabric (cotton fabric test sample) washed 10 times has a bacteriostatic radius of 1.1cm for staphylococcus aureus and a bacteriostatic radius of 1.4cm for escherichia coli, and has a significant antibacterial effect.
Example 3
(1) Dissolving 5g L-arginine in 25mL of deionized water, adding 3.5mL of triethylamine, stirring to fully mix the solution, then dropwise adding 8mL of dioxane solution containing 4g of methacrylic anhydride, continuously reacting for 8h, precipitating the product with acetone, and drying at room temperature in a vacuum drying oven to obtain the antibacterial monomer.
(2) And (2) dissolving 5g of the antibacterial monomer in the step (1), 1.8g of styrene and 0.2g of hydroxyethyl methacrylate in 100mL of deionized water in a 250mL three-neck flask, adding 0.1g N, N-methylene bisacrylamide, introducing nitrogen, stirring for 30min, heating to 70 ℃, dropwise adding 2mL of an aqueous solution containing 70mg of APS ammonium persulfate, continuously reacting for 12h, filtering and purifying the reaction product for three times, and drying at 40 ℃ in a vacuum drying oven to obtain the antibacterial nano hydrogel.
(3) And (3) dissolving 0.3g of the antibacterial nano hydrogel obtained in the step (2) in 100mL of petroleum ether, performing ultrasonic dispersion for 30min, dropwise adding 2mL of isophorone diisocyanate, dropwise adding 0.1mL of dibutyltin dilaurate, stirring and reacting at 50 ℃ for 8h in a nitrogen environment, filtering a product, washing with a large amount of acetone, and drying at room temperature in a vacuum drying oven to obtain the surface-modified antibacterial nano hydrogel.
(4) And (3) dissolving 0.2g of the surface-modified antibacterial nano hydrogel in the step (3) in 200mL of N, N-dimethylacetamide, ultrasonically dispersing for 15min, soaking 1g of cotton fabric in the solution, finishing at 50 ℃ for 6h, cleaning the treated fabric with acetone, and drying in a vacuum drying oven to obtain the antibacterial fabric. The antibacterial fabric is washed by water for 30 times according to the washing procedure of FZ/T73023 and 2006 antibacterial fabric appendix C antibacterial fabric sample washing test method. The antibacterial fabric washed 30 times is subjected to an antibacterial experiment, and the experimental result shows that the antibacterial fabric washed 30 times has a radius of 0.8cm for inhibiting staphylococcus aureus and a radius of 0.5cm for inhibiting escherichia coli, and has good antibacterial activity.
Example 4
(1) Dissolving 5g of polyhexamethylene guanidine hydrochloride in 25mL of deionized water, adding 3.5mL of triethylamine, stirring to fully mix the solution, then dropwise adding 8mL of dioxane solution containing 4g of methacrylic anhydride, continuously reacting for 8h, precipitating the product with acetone, and drying at room temperature in a vacuum drying oven to obtain the antibacterial monomer.
(2) Dissolving 5g of the antibacterial monomer in the step (1), 1.8g of methyl methacrylate and 0.2g of hydroxyethyl methacrylate in 100mL of deionized water in a 250mL three-neck flask, adding 0.1g N, N-methylene bisacrylamide, introducing nitrogen, stirring for 30min, heating to 70 ℃, dropwise adding 2mL of an aqueous solution containing 70mg of APS ammonium persulfate, continuously reacting for 12h, filtering and purifying the reaction product for three times, and drying at 40 ℃ in a vacuum drying oven to obtain the antibacterial nano hydrogel.
(3) And (3) dissolving 0.3g of the antibacterial nano hydrogel obtained in the step (2) in 100mL of petroleum ether, performing ultrasonic dispersion for 30min, dropwise adding 2mL of isophorone diisocyanate, dropwise adding 0.1mL of dibutyltin dilaurate, stirring and reacting at 50 ℃ for 8h in a nitrogen environment, filtering a product, washing with a large amount of acetone, and drying at room temperature in a vacuum drying oven to obtain the surface-modified antibacterial nano hydrogel.
(4) And (3) dissolving 0.2g of the antibacterial nano hydrogel subjected to surface modification in the step (3) in 200mL of N, N-dimethylacetamide, ultrasonically dispersing for 15min, soaking 1g of mulberry silk fabric in the solution, finishing at 50 ℃ for 6h, cleaning the treated fabric with acetone, and drying in a vacuum drying oven at 40 ℃ to obtain the antibacterial fabric. The antibacterial fabric is taken and washed for 15 times according to the washing procedure of FZ/T73023 and 2006 antibacterial fabric appendix C antibacterial fabric sample washing test method. The antibacterial fabric washed 15 times is subjected to an antibacterial experiment, and the experimental result shows that the antibacterial fabric washed 15 times has the antibacterial radius of 1.1cm for staphylococcus aureus and the antibacterial radius of 0.9cm for escherichia coli, and has good antibacterial activity.
Example 5
(1) Dissolving 5g L-arginine in 25mL of deionized water, adding 3.5mL of triethylamine, stirring to fully mix the solution, then dropwise adding 8mL of dioxane solution containing 4g of methacrylic anhydride, continuously reacting for 8h, precipitating the product with acetone, and drying at room temperature in a vacuum drying oven to obtain the antibacterial monomer.
(2) And (2) dissolving 5g of the antibacterial monomer in the step (1), 1.8g of methyl acrylate and 0.2g of hydroxypropyl acrylate in 100mL of deionized water in a 250mL three-neck flask, adding 0.1g N, N-methylene bisacrylamide, introducing nitrogen for 30min, stirring, heating to 70 ℃, dropwise adding 2mL of an aqueous solution containing 70mg of ammonium persulfate APS, continuously reacting for 12h, filtering and purifying the reaction product for three times, and drying at 40 ℃ in a vacuum drying oven to obtain the antibacterial nano hydrogel.
(3) And (3) dissolving 0.3g of the antibacterial nano hydrogel obtained in the step (2) in 100mL of petroleum ether, performing ultrasonic dispersion for 30min, dropwise adding 2mL of isophorone diisocyanate, dropwise adding 0.1mL of dibutyltin dilaurate, stirring and reacting at 50 ℃ for 8h in a nitrogen environment, filtering a product, washing with a large amount of acetone, and drying at room temperature in a vacuum drying oven to obtain the surface-modified antibacterial nano hydrogel.
(4) And (3) dissolving 0.2g of the antibacterial nano hydrogel subjected to surface modification in the step (3) in 200mL of acetone, ultrasonically dispersing for 15min, soaking 1g of cotton fabric in the solution, finishing for 6h at 50 ℃, cleaning the treated fabric with acetone, and drying in a vacuum drying oven at 40 ℃ to obtain the antibacterial fabric. The antibacterial fabric is taken and washed 10 times by referring to the washing procedure of FZ/T73023 and 2006 antibacterial fabric appendix C antibacterial fabric sample washing test method. The antibacterial fabric washed 10 times is subjected to antibacterial experiments, and the experimental result shows that the antibacterial fabric washed 10 times has the antibacterial radius of 1.1cm for staphylococcus aureus and the antibacterial radius of 1.2cm for escherichia coli, and has good antibacterial activity.
Claims (10)
1. A method of making a durable antimicrobial fabric comprising:
(1) dissolving an antibacterial compound containing guanidino in a solvent to obtain an antibacterial compound solution containing guanidino, adding triethylamine, stirring, dropwise adding a methacrylic anhydride solution for reaction, precipitating, and drying to obtain an antibacterial monomer, wherein the mass ratio of the antibacterial compound containing guanidino to the triethylamine to the methacrylic anhydride is (1-2) to (0.5-1.2) to (0.8-1.6), and the concentration of the antibacterial compound solution containing guanidino is 0.1-0.4 g/mL;
(2) dissolving the antibacterial monomer, the high-molecular polymer monomer and the water-soluble monomer in the step (1) in a mass ratio of (1-2): (0.2-0.4): (0.02-0.04) in a solvent, adding N, N-methylene bisacrylamide, adding an initiator in a nitrogen environment, stirring for reaction, filtering and drying to obtain the antibacterial nano hydrogel, wherein the mass ratio of the antibacterial monomer, the initiator and the N, N-methylene bisacrylamide is (1-2): (0.005-0.02): (0.01-0.02), and the ratio of the antibacterial monomer to the solvent is 5g:100mL-10g:5 mL;
(3) dispersing the antibacterial nano hydrogel in the step (2) in an inert solvent to obtain an antibacterial nano hydrogel solution, performing ultrasonic treatment, adding isophorone diisocyanate, adding a catalyst, stirring for reaction, filtering, and drying to obtain a surface-modified antibacterial nano hydrogel, wherein the mass ratio of the antibacterial nano hydrogel to the isophorone diisocyanate to the catalyst is (1-5) to (7-55) to (0.3-3), and the concentration of the antibacterial nano hydrogel solution is 0.002-0.01 g/mL;
(4) and (3) dispersing the surface-modified antibacterial nano hydrogel in the step (3) in an inert solvent to obtain a surface-modified antibacterial nano hydrogel solution, performing ultrasonic treatment to obtain a dispersion solution, soaking or spraying the fabric in the dispersion solution, cleaning, and drying to obtain the durable antibacterial fabric, wherein the concentration of the surface-modified antibacterial nano hydrogel solution is 0.001-0.01 g/mL.
2. A method of preparing a durable antimicrobial fabric according to claim 1 wherein the guanidine-containing antimicrobial compound of step (1) is polyhexamethylene guanidine hydrochloride or L-arginine; the solvent of the methacrylic anhydride solution is dioxane; the reaction time is 8-12 h; acetone is used for precipitation; the drying is carried out in a vacuum drying oven.
3. A method of forming a durable antimicrobial fabric according to claim 1 wherein the solvents of steps (1) and (2) are deionized water.
4. A method of making a durable antimicrobial fabric according to claim 1 wherein said polymeric monomer in step (2) is methyl methacrylate, methyl acrylate, styrene or butyl methacrylate; the water-soluble monomer is hydroxyethyl methacrylate, hydroxyethyl acrylate, hydroxypropyl methacrylate or hydroxypropyl acrylate.
5. A method of making a durable antimicrobial fabric according to claim 1 wherein in step (2) the initiator is ammonium persulfate APS; adding initiator at 60-80 deg.c; the reaction time is 12-24 h; the drying is carried out in a vacuum drying oven at 40 ℃.
6. A method for preparing a durable antibacterial fabric according to claim 1, wherein in the step (3), the stirring reaction temperature is 40-60 ℃, and the stirring reaction time is 8-12 h; the catalyst is dibutyltin dilaurate; the drying is carried out in a vacuum drying oven at room temperature.
7. A method of producing a durable antimicrobial fabric according to claim 1 wherein in steps (3) and (4) the inert solvent is acetone, dioxane, petroleum ether or N, N-dimethylacetamide; the ultrasonic treatment time is 10-40 min.
8. A method for preparing a durable antibacterial fabric according to claim 1, wherein the fabric in the step (4) is a fabric woven from natural fibers or fibers having active groups on the surface.
9. A method of making a durable antimicrobial fabric according to claim 8 wherein said natural fiber fabric is cotton or silk fabric; the active group being-OH or-NH2。
10. The method for preparing a durable antibacterial fabric according to claim 1, wherein the bath ratio of the soaking in the step (4) is 1: 100-200; the temperature of the spraying treatment is 40-80 ℃, and the time of the spraying treatment is 6-12 h; acetone is used for cleaning; the drying is carried out in a vacuum drying oven.
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